############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section B. It has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary may be obtained from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # # Copyright International Union of Crystallography # # # ############################################################################## data_global _audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template' _journal_date_recd_electronic 2002-11-14 _journal_date_accepted 2003-03-12 _journal_name_full 'Acta Crystallographica, Section B' _journal_year 2003 _journal_volume 59 _journal_issue 3 _journal_page_first 404 _journal_page_last 415 _journal_paper_category FA _publ_contact_author_name 'Dr. Daisuke Hashizume' _publ_contact_author_address ; Molecular Characterization Division RIKEN (The Institute of Physical and Chemical Research 2-1, Hirosawa, Wako, Saitama 351-0198, Japan ; _publ_contact_author_email 'hashi@postman.riken.go.jp' _publ_contact_author_fax '81(48462)4628' _publ_contact_author_phone '81(48467)9363' _publ_section_title ; Mechanism of First Order Phase Transition of Acylurea Derivative Crystal: Observation of Intermediate Stages of Transformation with a Detailed Temperature Resolved Single Crystal Diffraction Method ; loop_ _publ_author_name _publ_author_address 'Hashizume, Daisuke' ; Department of Applied Physics and Chemistry The University of Electro-Communications Chofugaoka, Chofu, Tokyo 182-8585 Japan ; 'Miki, Naoko' ; Department of Applied Physics and Chemistry The University of Electro-Communications Chofugaoka, Chofu, Tokyo 182-8585 Japan ; 'Yamazaki, Toshiyuki' ; Department of Applied Physics and Chemistry The University of Electro-Communications Chofugaoka, Chofu, Tokyo 182-8585 Japan ; 'Aoyagi, Yosuke' ; Department of Applied Physics and Chemistry The University of Electro-Communications Chofugaoka, Chofu, Tokyo 182-8585 Japan ; 'Tomokuni, Arisato' ; Department of Chemistry Aoyama Gakuin University Chitosedai, Setagaya, Tokyo 157-8572 Japan ; 'Hiroki, Uchiyama' ; Department of Chemistry Aoyama Gakuin University Chitosedai, Setagaya, Tokyo 157-8572 Japan ; 'Tadashi, Endo' ; Department of Chemistry Aoyama Gakuin University Chitosedai, Setagaya, Tokyo 157-8572 Japan ; 'Yasui, Masanori' ; Department of Applied Physics and Chemistry The University of Electro-Communications Chofugaoka, Chofu, Tokyo 182-8585 Japan ; 'Iwasaki, Fujiko' ; Department of Applied Physics and Chemistry The University of Electro-Communications Chofugaoka, Chofu, Tokyo 182-8585 Japan ; _publ_section_synopsis ; ? ; data_ethyl98K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7038(14) _cell_length_b 12.204(3) _cell_length_c 4.9747(10) _cell_angle_alpha 93.021(11) _cell_angle_beta 90.616(7) _cell_angle_gamma 90.319(10) _cell_volume 527.64(19) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4199 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 27.485 _cell_measurement_temperature 98 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal is being low temperature phase. ; _diffrn_ambient_temperature 98 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 6068 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_sigmaI/netI 0.0133 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.857 _diffrn_measured_fraction_theta_full 0.857 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2076 _reflns_number_gt 1992 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_gt 0.1263 _refine_ls_wR_factor_ref 0.1282 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_number_reflns 2076 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refall _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0769P)^2^+0.1768P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.272 _refine_diff_density_min -0.236 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution 'SIR-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.44032(10) 0.57459(7) 0.24164(18) 0.0197(2) Uani d . 1 . . O O2 0.02166(10) 0.40706(7) 0.22035(18) 0.0195(2) Uani d . 1 . . O N1 0.19696(12) 0.53547(8) 0.3825(2) 0.0165(3) Uani d . 1 . . N H11 0.128(2) 0.5538(14) 0.506(4) 0.021(4) Uiso d . 1 . . H N2 0.25049(12) 0.41607(8) 0.0069(2) 0.0167(2) Uani d . 1 . . N H21 0.338(2) 0.4465(14) 0.003(4) 0.023(4) Uiso d . 1 . . H C1 0.33545(14) 0.59050(9) 0.4018(2) 0.0158(3) Uani d . 1 . . C C2 0.15101(14) 0.44889(9) 0.1958(2) 0.0162(3) Uani d . 1 . . C C11 0.35090(15) 0.67433(10) 0.6398(2) 0.0178(3) Uani d . 1 . . C H111 0.439(2) 0.6487(13) 0.745(3) 0.021(4) Uiso d . 1 . . H H112 0.2602(19) 0.6735(13) 0.748(3) 0.018(4) Uiso d . 1 . . H C12 0.38521(15) 0.79070(10) 0.5489(3) 0.0198(3) Uani d . 1 . . C H121 0.405(2) 0.8406(15) 0.712(4) 0.027(4) Uiso d . 1 . . H H122 0.4770(19) 0.7875(13) 0.445(3) 0.018(4) Uiso d . 1 . . H C13 0.25484(18) 0.84117(10) 0.3886(3) 0.0260(3) Uani d . 1 . . C H131 0.232(2) 0.7902(16) 0.225(4) 0.033(5) Uiso d . 1 . . H C14 0.3084(3) 0.95237(12) 0.2891(3) 0.0387(4) Uani d . 1 . . C H141 0.332(2) 1.0040(17) 0.440(4) 0.040(5) Uiso d . 1 . . H H142 0.397(3) 0.9434(18) 0.175(5) 0.047(6) Uiso d . 1 . . H H143 0.224(3) 0.9838(19) 0.185(5) 0.053(6) Uiso d . 1 . . H C15 0.10882(18) 0.85613(13) 0.5535(4) 0.0354(4) Uani d . 1 . . C H151 0.131(2) 0.9070(17) 0.722(4) 0.041(5) Uiso d . 1 . . H H152 0.065(3) 0.7830(19) 0.622(5) 0.050(6) Uiso d . 1 . . H H153 0.026(3) 0.8914(19) 0.445(5) 0.052(6) Uiso d . 1 . . H C21 0.21377(14) 0.32246(10) -0.1823(2) 0.0181(3) Uani d . 1 . . C H211 0.2767(18) 0.3308(13) -0.340(3) 0.017(4) Uiso d . 1 . . H H212 0.107(2) 0.3260(13) -0.231(3) 0.019(4) Uiso d . 1 . . H C22 0.24513(17) 0.21233(11) -0.0605(3) 0.0252(3) Uani d . 1 . . C H221 0.355(2) 0.2097(16) -0.005(4) 0.039(5) Uiso d . 1 . . H H222 0.179(2) 0.2045(15) 0.100(4) 0.033(5) Uiso d . 1 . . H H223 0.221(2) 0.1502(16) -0.196(4) 0.037(5) Uiso d . 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0159(4) 0.0238(5) 0.0191(4) -0.0018(3) 0.0033(4) -0.0007(3) O2 0.0150(4) 0.0237(5) 0.0195(4) -0.0031(3) 0.0032(3) -0.0011(3) N1 0.0139(5) 0.0198(5) 0.0155(5) -0.0004(4) 0.0037(4) -0.0015(4) N2 0.0136(5) 0.0197(5) 0.0164(5) -0.0017(4) 0.0012(4) -0.0018(4) C1 0.0158(6) 0.0165(5) 0.0154(6) 0.0006(4) -0.0010(5) 0.0030(4) C2 0.0165(6) 0.0171(5) 0.0151(5) 0.0006(4) -0.0008(4) 0.0024(4) C11 0.0169(6) 0.0210(6) 0.0153(6) -0.0003(4) 0.0001(5) -0.0010(4) C12 0.0192(6) 0.0196(6) 0.0204(6) -0.0026(4) 0.0016(5) -0.0018(4) C13 0.0374(8) 0.0186(6) 0.0215(6) 0.0000(5) -0.0086(6) -0.0014(5) C14 0.0656(12) 0.0217(7) 0.0289(8) -0.0009(7) -0.0022(8) 0.0029(6) C15 0.0244(7) 0.0270(7) 0.0544(10) 0.0034(5) -0.0106(7) -0.0002(7) C21 0.0170(6) 0.0214(6) 0.0156(6) -0.0004(4) -0.0001(5) -0.0030(4) C22 0.0274(7) 0.0213(6) 0.0267(7) 0.0014(5) 0.0014(6) -0.0010(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.2275(15) ? O2 C2 . 1.2435(15) ? N1 C1 . 1.3766(15) ? N1 C2 . 1.4224(15) ? N1 H11 . 0.880(19) ? N2 C2 . 1.3321(16) ? N2 C21 . 1.4730(15) ? N2 H21 . 0.846(18) ? C1 C11 . 1.5280(16) ? C11 C12 . 1.5417(17) ? C11 H111 . 0.984(18) ? C11 H112 . 0.961(17) ? C12 C13 . 1.5304(19) ? C12 H121 . 1.003(18) ? C12 H122 . 0.955(17) ? C13 C15 . 1.527(2) ? C13 C14 . 1.540(2) ? C13 H131 . 1.01(2) ? C14 H141 . 0.98(2) ? C14 H142 . 0.97(2) ? C14 H143 . 0.99(2) ? C15 H151 . 1.03(2) ? C15 H152 . 1.04(2) ? C15 H153 . 1.01(3) ? C21 C22 . 1.5280(18) ? C21 H211 . 0.971(16) ? C21 H212 . 0.959(17) ? C22 H221 . 0.99(2) ? C22 H222 . 0.997(19) ? C22 H223 . 1.01(2) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 128.59(10) ? C1 N1 H11 . . 116.4(11) ? C2 N1 H11 . . 114.9(11) ? C2 N2 C21 . . 120.62(11) ? C2 N2 H21 . . 119.6(12) ? C21 N2 H21 . . 119.6(12) ? O1 C1 N1 . . 123.40(11) ? O1 C1 C11 . . 121.49(11) ? N1 C1 C11 . . 115.11(10) ? O2 C2 N2 . . 123.75(11) ? O2 C2 N1 . . 118.33(11) ? N2 C2 N1 . . 117.90(11) ? C1 C11 C12 . . 112.12(10) ? C1 C11 H111 . . 104.6(10) ? C12 C11 H111 . . 109.3(9) ? C1 C11 H112 . . 110.2(10) ? C12 C11 H112 . . 111.1(10) ? H111 C11 H112 . . 109.3(14) ? C13 C12 C11 . . 114.44(11) ? C13 C12 H121 . . 107.3(10) ? C11 C12 H121 . . 108.8(10) ? C13 C12 H122 . . 110.3(10) ? C11 C12 H122 . . 107.9(9) ? H121 C12 H122 . . 107.8(14) ? C15 C13 C12 . . 112.30(12) ? C15 C13 C14 . . 110.07(13) ? C12 C13 C14 . . 109.30(13) ? C15 C13 H131 . . 109.2(11) ? C12 C13 H131 . . 107.8(11) ? C14 C13 H131 . . 108.1(11) ? C13 C14 H141 . . 110.9(12) ? C13 C14 H142 . . 110.9(13) ? H141 C14 H142 . . 109.8(18) ? C13 C14 H143 . . 108.6(13) ? H141 C14 H143 . . 107.5(18) ? H142 C14 H143 . . 109.1(19) ? C13 C15 H151 . . 109.7(11) ? C13 C15 H152 . . 113.7(13) ? H151 C15 H152 . . 106.7(17) ? C13 C15 H153 . . 110.8(13) ? H151 C15 H153 . . 107.7(18) ? H152 C15 H153 . . 108.0(18) ? N2 C21 C22 . . 112.23(10) ? N2 C21 H211 . . 106.7(9) ? C22 C21 H211 . . 110.5(9) ? N2 C21 H212 . . 108.5(10) ? C22 C21 H212 . . 109.0(10) ? H211 C21 H212 . . 109.9(14) ? C21 C22 H221 . . 108.9(12) ? C21 C22 H222 . . 109.5(11) ? H221 C22 H222 . . 109.7(17) ? C21 C22 H223 . . 110.3(12) ? H221 C22 H223 . . 109.7(17) ? H222 C22 H223 . . 108.7(15) ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 4.1(2) ? C2 N1 C1 C11 . . . . -175.84(11) ? C21 N2 C2 O2 . . . . -2.54(18) ? C21 N2 C2 N1 . . . . 176.29(10) ? C1 N1 C2 O2 . . . . 177.05(11) ? C1 N1 C2 N2 . . . . -1.85(19) ? O1 C1 C11 C12 . . . . 58.34(15) ? N1 C1 C11 C12 . . . . -121.68(12) ? C1 C11 C12 C13 . . . . 65.93(14) ? C11 C12 C13 C15 . . . . 62.45(15) ? C11 C12 C13 C14 . . . . -175.11(12) ? C2 N2 C21 C22 . . . . -81.62(14) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.846(18) 2.300(18) 2.9778(15) 137.4(16) N1 H11 O2 2_566 0.880(19) 1.942(19) 2.8222(14) 179.3(17) data_ethyl298K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8173(5) _cell_length_b 12.4339(12) _cell_length_c 5.09630(10) _cell_angle_alpha 92.912(12) _cell_angle_beta 89.876(3) _cell_angle_gamma 90.152(10) _cell_volume 558.00(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3690 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.485 _cell_measurement_temperature 298 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.109 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being low temperature phase. ; _diffrn_ambient_temperature 298 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 6494 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_av_sigmaI/netI 0.0128 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.890 _diffrn_measured_fraction_theta_full 0.890 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2292 _reflns_number_gt 2041 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_gt 0.1642 _refine_ls_wR_factor_ref 0.1709 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_number_reflns 2292 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0925P)^2^+0.1104P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.161 _refine_diff_density_min -0.205 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 98K was used as an initial model. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.43498(13) 0.57527(10) 0.2374(2) 0.0566(3) Uani d . 1 . . O O2 0.02574(12) 0.40870(10) 0.2301(2) 0.0559(3) Uani d . 1 . . O N1 0.19711(14) 0.53487(11) 0.3806(3) 0.0458(3) Uani d . 1 . . N H11 0.1303 0.5546 0.4964 0.055 Uiso calc R 1 . . H N2 0.25183(14) 0.41611(11) 0.0194(3) 0.0467(3) Uani d . 1 . . N H21 0.3377 0.4486 0.0081 0.056 Uiso calc R 1 . . H C1 0.33136(17) 0.59074(12) 0.3945(3) 0.0434(3) Uani d . 1 . . C C2 0.15267(17) 0.44949(12) 0.2036(3) 0.0435(3) Uani d . 1 . . C C11 0.34433(19) 0.67384(13) 0.6232(3) 0.0506(4) Uani d . 1 . . C H111 0.4235 0.6518 0.7407 0.061 Uiso calc R 1 . . H H112 0.2497 0.6756 0.7206 0.061 Uiso calc R 1 . . H C12 0.3802(2) 0.78742(14) 0.5365(4) 0.0593(5) Uani d . 1 . . C H122 0.4721 0.7845 0.4314 0.071 Uiso calc R 1 . . H H121 0.4003 0.8337 0.6917 0.071 Uiso calc R 1 . . H C13 0.2540(3) 0.83858(16) 0.3773(4) 0.0796(7) Uani d . 1 . . C H131 0.2317 0.7905 0.2237 0.096 Uiso calc R 1 . . H C14 0.3089(5) 0.9478(2) 0.2795(6) 0.1270(14) Uani d . 1 . . C H142 0.4010 0.9374 0.1807 0.152 Uiso calc R 1 . . H H141 0.3273 0.9970 0.4276 0.152 Uiso calc R 1 . . H H143 0.2326 0.9770 0.1696 0.152 Uiso calc R 1 . . H C15 0.1085(3) 0.8545(2) 0.5371(8) 0.1137(11) Uani d . 1 . . C H152 0.0752 0.7865 0.5975 0.136 Uiso calc R 1 . . H H153 0.0313 0.8837 0.4289 0.136 Uiso calc R 1 . . H H151 0.1275 0.9034 0.6853 0.136 Uiso calc R 1 . . H C21 0.21680(19) 0.32495(14) -0.1641(3) 0.0521(4) Uani d . 1 . . C H211 0.2769 0.3309 -0.3224 0.062 Uiso calc R 1 . . H H212 0.1107 0.3281 -0.2130 0.062 Uiso calc R 1 . . H C22 0.2482(3) 0.21723(17) -0.0493(5) 0.0752(6) Uani d . 1 . . C H223 0.2233 0.1603 -0.1764 0.090 Uiso calc R 1 . . H H222 0.1875 0.2102 0.1056 0.090 Uiso calc R 1 . . H H221 0.3536 0.2129 -0.0045 0.090 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0431(6) 0.0655(7) 0.0603(7) -0.0078(5) 0.0161(5) -0.0055(5) O2 0.0417(6) 0.0639(7) 0.0611(7) -0.0104(5) 0.0151(5) -0.0057(5) N1 0.0388(6) 0.0504(7) 0.0478(7) -0.0021(5) 0.0119(5) -0.0017(5) N2 0.0373(6) 0.0524(7) 0.0500(7) -0.0035(5) 0.0094(5) -0.0028(5) C1 0.0393(7) 0.0459(7) 0.0454(7) 0.0009(6) 0.0040(6) 0.0075(6) C2 0.0375(7) 0.0473(8) 0.0459(8) 0.0003(5) 0.0075(6) 0.0044(6) C11 0.0484(8) 0.0565(9) 0.0464(8) -0.0022(7) 0.0016(7) -0.0007(7) C12 0.0574(10) 0.0546(9) 0.0648(10) -0.0081(7) 0.0072(8) -0.0070(8) C13 0.1154(19) 0.0504(10) 0.0725(13) 0.0025(11) -0.0222(13) -0.0023(9) C14 0.222(4) 0.0612(14) 0.099(2) 0.0031(19) 0.000(2) 0.0182(14) C15 0.0764(17) 0.0853(18) 0.179(3) 0.0166(13) -0.027(2) 0.0036(19) C21 0.0456(8) 0.0586(9) 0.0512(9) 0.0001(7) 0.0038(7) -0.0056(7) C22 0.0866(15) 0.0569(11) 0.0815(14) 0.0030(10) 0.0070(12) -0.0040(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.2227(19) ? O2 C2 . 1.2375(18) ? N1 C1 . 1.3710(19) ? N1 C2 . 1.413(2) ? N1 H11 . 0.8600 ? N2 C2 . 1.3328(19) ? N2 C21 . 1.465(2) ? N2 H21 . 0.8600 ? C1 C11 . 1.522(2) ? C11 C12 . 1.533(2) ? C11 H111 . 0.9700 ? C11 H112 . 0.9700 ? C12 C13 . 1.537(3) ? C12 H122 . 0.9700 ? C12 H121 . 0.9700 ? C13 C15 . 1.526(4) ? C13 C14 . 1.547(3) ? C13 H131 . 0.9800 ? C14 H142 . 0.9600 ? C14 H141 . 0.9600 ? C14 H143 . 0.9600 ? C15 H152 . 0.9600 ? C15 H153 . 0.9600 ? C15 H151 . 0.9600 ? C21 C22 . 1.515(3) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 H223 . 0.9600 ? C22 H222 . 0.9600 ? C22 H221 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 129.32(13) ? C1 N1 H11 . . 115.3 ? C2 N1 H11 . . 115.3 ? C2 N2 C21 . . 121.00(13) ? C2 N2 H21 . . 119.5 ? C21 N2 H21 . . 119.5 ? O1 C1 N1 . . 123.17(15) ? O1 C1 C11 . . 121.57(14) ? N1 C1 C11 . . 115.25(13) ? O2 C2 N2 . . 123.65(15) ? O2 C2 N1 . . 118.60(13) ? N2 C2 N1 . . 117.74(13) ? C1 C11 C12 . . 113.22(13) ? C1 C11 H111 . . 108.9 ? C12 C11 H111 . . 108.9 ? C1 C11 H112 . . 108.9 ? C12 C11 H112 . . 108.9 ? H111 C11 H112 . . 107.7 ? C11 C12 C13 . . 114.62(16) ? C11 C12 H122 . . 108.6 ? C13 C12 H122 . . 108.6 ? C11 C12 H121 . . 108.6 ? C13 C12 H121 . . 108.6 ? H122 C12 H121 . . 107.6 ? C15 C13 C12 . . 112.0(2) ? C15 C13 C14 . . 109.9(2) ? C12 C13 C14 . . 109.8(2) ? C15 C13 H131 . . 108.4 ? C12 C13 H131 . . 108.4 ? C14 C13 H131 . . 108.4 ? C13 C14 H142 . . 109.5 ? C13 C14 H141 . . 109.5 ? H142 C14 H141 . . 109.5 ? C13 C14 H143 . . 109.5 ? H142 C14 H143 . . 109.5 ? H141 C14 H143 . . 109.5 ? C13 C15 H152 . . 109.5 ? C13 C15 H153 . . 109.5 ? H152 C15 H153 . . 109.5 ? C13 C15 H151 . . 109.5 ? H152 C15 H151 . . 109.5 ? H153 C15 H151 . . 109.5 ? N2 C21 C22 . . 112.64(15) ? N2 C21 H211 . . 109.1 ? C22 C21 H211 . . 109.1 ? N2 C21 H212 . . 109.1 ? C22 C21 H212 . . 109.1 ? H211 C21 H212 . . 107.8 ? C21 C22 H223 . . 109.5 ? C21 C22 H222 . . 109.5 ? H223 C22 H222 . . 109.5 ? C21 C22 H221 . . 109.5 ? H223 C22 H221 . . 109.5 ? H222 C22 H221 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 3.1(3) ? C2 N1 C1 C11 . . . . -176.24(14) ? C21 N2 C2 O2 . . . . -1.4(2) ? C21 N2 C2 N1 . . . . 177.30(13) ? C1 N1 C2 O2 . . . . 178.47(14) ? C1 N1 C2 N2 . . . . -0.3(2) ? O1 C1 C11 C12 . . . . 56.7(2) ? N1 C1 C11 C12 . . . . -123.93(15) ? C1 C11 C12 C13 . . . . 66.0(2) ? C11 C12 C13 C15 . . . . 62.9(2) ? C11 C12 C13 C14 . . . . -174.74(19) ? C2 N2 C21 C22 . . . . -82.8(2) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.86 2.37 3.0573(17) 136.9 N1 H11 O2 2_566 0.86 1.99 2.8525(17) 176.6 data_ethyl328K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7817(18) _cell_length_b 12.381(2) _cell_length_c 5.1113(11) _cell_angle_alpha 92.491(8) _cell_angle_beta 90.164(9) _cell_angle_gamma 89.589(9) _cell_volume 555.17(19) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3475 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.47 _cell_measurement_temperature 328 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.114 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being low temperature phase. ; _diffrn_ambient_temperature 328 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 7578 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.849 _diffrn_measured_fraction_theta_full 0.849 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2169 _reflns_number_gt 1728 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_gt 0.1475 _refine_ls_wR_factor_ref 0.1621 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_number_reflns 2169 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+0.1725P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.174 _refine_diff_density_min -0.177 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 298K was used as an initial model. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.43409(16) 0.57524(13) 0.2348(3) 0.0691(5) Uani d . 1 . . O O2 0.02639(15) 0.40900(13) 0.2335(3) 0.0688(5) Uani d . 1 . . O N1 0.19755(18) 0.53428(14) 0.3789(4) 0.0565(4) Uani d . 1 . . N H11 0.134(3) 0.5526(18) 0.491(5) 0.063(6) Uiso d . 1 . . H N2 0.25155(19) 0.41618(14) 0.0232(3) 0.0589(5) Uani d . 1 . . N H21 0.331(3) 0.4469(19) 0.017(5) 0.070(7) Uiso d . 1 . . H C1 0.3307(2) 0.59059(15) 0.3924(4) 0.0537(5) Uani d . 1 . . C C2 0.1534(2) 0.44946(16) 0.2065(4) 0.0543(5) Uani d . 1 . . C C11 0.3432(3) 0.67318(18) 0.6154(5) 0.0641(5) Uani d . 1 . . C H112 0.252(3) 0.676(2) 0.715(5) 0.081(7) Uiso d . 1 . . H H111 0.427(3) 0.650(2) 0.729(6) 0.097(9) Uiso d . 1 . . H C12 0.3788(3) 0.7864(2) 0.5310(6) 0.0760(7) Uani d . 1 . . C H121 0.400(3) 0.842(2) 0.704(6) 0.101(9) Uiso d . 1 . . H H122 0.480(4) 0.782(2) 0.415(6) 0.103(9) Uiso d . 1 . . H C13 0.2550(4) 0.8377(2) 0.3726(7) 0.0996(10) Uani d . 1 . . C H131 0.234(4) 0.790(3) 0.224(8) 0.131(12) Uiso d . 1 . . H C14 0.3084(7) 0.9468(3) 0.2766(9) 0.1566(19) Uani d . 1 . . C H143 0.2285 0.9790 0.1770 0.188 Uiso calc R 1 . . H H142 0.3968 0.9359 0.1683 0.188 Uiso calc R 1 . . H H141 0.3333 0.9939 0.4245 0.188 Uiso calc R 1 . . H C15 0.1083(4) 0.8540(3) 0.5295(11) 0.1496(18) Uani d . 1 . . C H153 0.0324 0.8869 0.4228 0.179 Uiso calc R 1 . . H H151 0.1279 0.9000 0.6817 0.179 Uiso calc R 1 . . H H152 0.0725 0.7852 0.5827 0.179 Uiso calc R 1 . . H C21 0.2176(3) 0.32596(19) -0.1566(5) 0.0652(6) Uani d . 1 . . C H212 0.111(3) 0.3305(18) -0.210(5) 0.069(6) Uiso d . 1 . . H H211 0.279(3) 0.3354(19) -0.316(5) 0.078(7) Uiso d . 1 . . H C22 0.2497(5) 0.2186(2) -0.0422(8) 0.0929(9) Uani d . 1 . . C H223 0.229(4) 0.161(3) -0.165(7) 0.110(10) Uiso d . 1 . . H H222 0.188(4) 0.209(2) 0.100(7) 0.104(10) Uiso d . 1 . . H H221 0.363(4) 0.214(3) 0.001(6) 0.114(11) Uiso d . 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0488(7) 0.0798(10) 0.0782(10) -0.0104(6) 0.0217(7) -0.0042(8) O2 0.0478(8) 0.0781(10) 0.0802(10) -0.0124(7) 0.0188(7) -0.0034(8) N1 0.0449(8) 0.0618(10) 0.0630(10) -0.0027(7) 0.0163(7) 0.0010(8) N2 0.0429(8) 0.0654(10) 0.0683(11) -0.0045(7) 0.0120(7) 0.0013(8) C1 0.0434(9) 0.0560(10) 0.0625(11) 0.0012(7) 0.0067(8) 0.0122(9) C2 0.0422(9) 0.0583(11) 0.0631(11) 0.0002(7) 0.0106(8) 0.0099(9) C11 0.0565(12) 0.0684(13) 0.0673(13) -0.0027(10) 0.0054(10) 0.0014(10) C12 0.0675(14) 0.0705(14) 0.0896(17) -0.0082(11) 0.0109(12) -0.0023(13) C13 0.133(3) 0.0673(16) 0.098(2) 0.0028(16) -0.0226(19) 0.0039(15) C14 0.258(6) 0.080(2) 0.135(3) 0.004(3) 0.005(4) 0.030(2) C15 0.089(2) 0.113(3) 0.247(6) 0.024(2) -0.025(3) 0.011(3) C21 0.0526(11) 0.0728(14) 0.0698(14) -0.0016(9) 0.0059(10) -0.0026(11) C22 0.102(2) 0.0703(17) 0.106(2) 0.0013(15) 0.0101(19) -0.0013(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.224(2) ? O2 C2 . 1.236(2) ? N1 C1 . 1.366(2) ? N1 C2 . 1.398(3) ? N1 H11 . 0.82(3) ? N2 C2 . 1.325(2) ? N2 C21 . 1.448(3) ? N2 H21 . 0.80(2) ? C1 C11 . 1.502(3) ? C11 C12 . 1.519(3) ? C11 H112 . 0.95(3) ? C11 H111 . 0.98(3) ? C12 C13 . 1.507(4) ? C12 H121 . 1.12(3) ? C12 H122 . 1.07(3) ? C13 C15 . 1.527(5) ? C13 C14 . 1.534(5) ? C13 H131 . 0.96(4) ? C14 H143 . 0.9600 ? C14 H142 . 0.9600 ? C14 H141 . 0.9600 ? C15 H153 . 0.9600 ? C15 H151 . 0.9600 ? C15 H152 . 0.9600 ? C21 C22 . 1.500(4) ? C21 H212 . 0.98(2) ? C21 H211 . 0.99(3) ? C22 H223 . 0.95(3) ? C22 H222 . 0.92(3) ? C22 H221 . 1.02(4) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 129.89(17) ? C1 N1 H11 . . 115.1(16) ? C2 N1 H11 . . 115.0(16) ? C2 N2 C21 . . 121.34(18) ? C2 N2 H21 . . 117.7(18) ? C21 N2 H21 . . 120.9(18) ? O1 C1 N1 . . 122.75(19) ? O1 C1 C11 . . 121.63(18) ? N1 C1 C11 . . 115.62(17) ? O2 C2 N2 . . 123.54(19) ? O2 C2 N1 . . 118.75(17) ? N2 C2 N1 . . 117.71(17) ? C1 C11 C12 . . 114.0(2) ? C1 C11 H112 . . 110.6(15) ? C12 C11 H112 . . 108.5(16) ? C1 C11 H111 . . 107.6(17) ? C12 C11 H111 . . 107.6(16) ? H112 C11 H111 . . 108(2) ? C13 C12 C11 . . 114.6(2) ? C13 C12 H121 . . 106.5(15) ? C11 C12 H121 . . 111.0(15) ? C13 C12 H122 . . 108.0(16) ? C11 C12 H122 . . 108.2(16) ? H121 C12 H122 . . 108(2) ? C12 C13 C15 . . 111.8(3) ? C12 C13 C14 . . 110.2(3) ? C15 C13 C14 . . 109.5(3) ? C12 C13 H131 . . 108(2) ? C15 C13 H131 . . 108(2) ? C14 C13 H131 . . 109(2) ? C13 C14 H143 . . 109.5 ? C13 C14 H142 . . 109.5 ? H143 C14 H142 . . 109.5 ? C13 C14 H141 . . 109.5 ? H143 C14 H141 . . 109.5 ? H142 C14 H141 . . 109.5 ? C13 C15 H153 . . 109.5 ? C13 C15 H151 . . 109.5 ? H153 C15 H151 . . 109.5 ? C13 C15 H152 . . 109.5 ? H153 C15 H152 . . 109.5 ? H151 C15 H152 . . 109.5 ? N2 C21 C22 . . 112.8(2) ? N2 C21 H212 . . 109.0(13) ? C22 C21 H212 . . 110.1(13) ? N2 C21 H211 . . 107.1(14) ? C22 C21 H211 . . 111.2(14) ? H212 C21 H211 . . 106(2) ? C21 C22 H223 . . 111(2) ? C21 C22 H222 . . 110(2) ? H223 C22 H222 . . 107(3) ? C21 C22 H221 . . 108.9(18) ? H223 C22 H221 . . 106(3) ? H222 C22 H221 . . 113(3) ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 3.4(3) ? C2 N1 C1 C11 . . . . -176.41(19) ? C21 N2 C2 O2 . . . . -2.0(3) ? C21 N2 C2 N1 . . . . 177.44(18) ? C1 N1 C2 O2 . . . . 178.90(19) ? C1 N1 C2 N2 . . . . -0.5(3) ? O1 C1 C11 C12 . . . . 55.6(3) ? N1 C1 C11 C12 . . . . -124.7(2) ? C1 C11 C12 C13 . . . . 65.7(3) ? C11 C12 C13 C15 . . . . 63.1(4) ? C11 C12 C13 C14 . . . . -174.8(3) ? C2 N2 C21 C22 . . . . -82.2(3) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.80(2) 2.44(3) 3.067(2) 136(2) N1 H11 O2 2_566 0.82(3) 2.04(3) 2.858(2) 177(2) data_ethyl348K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.740(2) _cell_length_b 12.357(2) _cell_length_c 5.1473(12) _cell_angle_alpha 91.509(8) _cell_angle_beta 90.236(11) _cell_angle_gamma 89.525(13) _cell_volume 555.7(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2704 _cell_measurement_theta_min 1.65 _cell_measurement_theta_max 26.93 _cell_measurement_temperature 348 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.113 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being low temperature phase. ; _diffrn_ambient_temperature 348 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 6205 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_max 0.760 _diffrn_measured_fraction_theta_full 0.760 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 1939 _reflns_number_gt 1418 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1003 _refine_ls_R_factor_gt 0.0816 _refine_ls_wR_factor_gt 0.2314 _refine_ls_wR_factor_ref 0.2549 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.065 _refine_ls_number_reflns 1939 _refine_ls_number_parameters 118 _refine_ls_number_restraints 5 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1229P)^2^+0.2315P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.269 _refine_diff_density_min -0.211 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 328K was used as an initial model. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.4329(2) 0.5747(2) 0.2314(5) 0.0846(7) Uani d . 1 . . O O2 0.0266(2) 0.4099(2) 0.2382(5) 0.0837(7) Uani d . 1 . . O N1 0.1972(3) 0.5337(2) 0.3770(5) 0.0701(7) Uani d . 1 . . N H11 0.1302 0.5530 0.4913 0.084 Uiso calc R 1 . . H N2 0.2522(3) 0.4162(2) 0.0286(5) 0.0732(7) Uani d . 1 . . N H21 0.3388 0.4483 0.0170 0.088 Uiso calc R 1 . . H C1 0.3299(3) 0.5903(2) 0.3881(6) 0.0684(8) Uani d . 1 . . C C2 0.1534(3) 0.4499(3) 0.2098(6) 0.0689(8) Uani d . 1 . . C C11 0.3418(4) 0.6722(3) 0.6063(7) 0.0805(9) Uani d D 1 . . C H112 0.4210 0.6488 0.7254 0.097 Uiso calc R 1 . . H H111 0.2459 0.6740 0.7005 0.097 Uiso calc R 1 . . H C12 0.3776(5) 0.7849(3) 0.5237(9) 0.1003(12) Uani d D 1 . . C H122 0.4711 0.7827 0.4229 0.120 Uiso calc R 1 . . H H121 0.3961 0.8299 0.6777 0.120 Uiso calc R 1 . . H C13 0.2532(6) 0.8367(4) 0.3649(10) 0.1236(17) Uani d D 1 . . C H131 0.2302 0.7897 0.2137 0.148 Uiso calc R 1 . . H C14 0.3071(11) 0.9462(5) 0.2717(15) 0.196(4) Uani d D 1 . . C H143 0.2280 0.9787 0.1692 0.235 Uiso calc R 1 . . H H142 0.3975 0.9361 0.1682 0.235 Uiso calc R 1 . . H H141 0.3298 0.9926 0.4192 0.235 Uiso calc R 1 . . H C15 0.1075(6) 0.8540(5) 0.5253(17) 0.185(3) Uani d D 1 . . C H152 0.0729 0.7856 0.5861 0.222 Uiso calc R 1 . . H H153 0.0294 0.8857 0.4191 0.222 Uiso calc R 1 . . H H151 0.1287 0.9015 0.6714 0.222 Uiso calc R 1 . . H C21 0.2180(4) 0.3277(3) -0.1486(7) 0.0808(9) Uani d D 1 . . C H211 0.2786 0.3345 -0.3046 0.097 Uiso calc R 1 . . H H212 0.1109 0.3317 -0.1981 0.097 Uiso calc R 1 . . H C22 0.2497(6) 0.2198(3) -0.0343(10) 0.1109(14) Uani d D 1 . . C H223 0.2247 0.1635 -0.1591 0.133 Uiso calc R 1 . . H H222 0.1887 0.2120 0.1187 0.133 Uiso calc R 1 . . H H221 0.3561 0.2145 0.0110 0.133 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0539(12) 0.0981(16) 0.1021(16) -0.0133(10) 0.0244(11) -0.0008(13) O2 0.0553(13) 0.0932(15) 0.1029(17) -0.0144(10) 0.0238(11) -0.0022(13) N1 0.0513(13) 0.0771(15) 0.0822(16) -0.0061(11) 0.0199(11) 0.0039(13) N2 0.0508(13) 0.0810(16) 0.0878(17) -0.0061(11) 0.0168(12) 0.0008(14) C1 0.0514(15) 0.0752(17) 0.0796(19) -0.0018(12) 0.0091(13) 0.0186(15) C2 0.0480(15) 0.0787(18) 0.0809(19) -0.0023(12) 0.0141(13) 0.0139(15) C11 0.0653(19) 0.084(2) 0.092(2) -0.0069(15) 0.0076(16) 0.0038(18) C12 0.085(3) 0.095(3) 0.121(3) -0.013(2) 0.016(2) -0.004(2) C13 0.157(5) 0.094(3) 0.120(4) 0.001(3) -0.020(3) 0.011(3) C14 0.299(11) 0.105(4) 0.186(7) -0.006(5) 0.006(7) 0.048(4) C15 0.102(4) 0.143(5) 0.312(10) 0.027(3) -0.020(5) 0.028(6) C21 0.0619(19) 0.092(2) 0.089(2) -0.0042(15) 0.0082(16) 0.0021(18) C22 0.115(3) 0.086(3) 0.131(4) 0.001(2) 0.007(3) 0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.222(4) ? O2 C2 . 1.228(3) ? N1 C1 . 1.359(4) ? N1 C2 . 1.385(4) ? N1 H11 . 0.8600 ? N2 C2 . 1.330(4) ? N2 C21 . 1.439(4) ? N2 H21 . 0.8600 ? C1 C11 . 1.496(5) ? C11 C12 . 1.503(5) ? C11 H112 . 0.9700 ? C11 H111 . 0.9700 ? C12 C13 . 1.506(7) ? C12 H122 . 0.9700 ? C12 H121 . 0.9700 ? C13 C14 . 1.526(8) ? C13 C15 . 1.531(9) ? C13 H131 . 0.9800 ? C14 H143 . 0.9600 ? C14 H142 . 0.9600 ? C14 H141 . 0.9600 ? C15 H152 . 0.9600 ? C15 H153 . 0.9600 ? C15 H151 . 0.9600 ? C21 C22 . 1.495(5) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 H223 . 0.9600 ? C22 H222 . 0.9600 ? C22 H221 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 129.9(3) ? C1 N1 H11 . . 115.1 ? C2 N1 H11 . . 115.1 ? C2 N2 C21 . . 121.7(3) ? C2 N2 H21 . . 119.2 ? C21 N2 H21 . . 119.2 ? O1 C1 N1 . . 122.3(3) ? O1 C1 C11 . . 122.2(3) ? N1 C1 C11 . . 115.5(3) ? O2 C2 N2 . . 123.6(3) ? O2 C2 N1 . . 118.4(3) ? N2 C2 N1 . . 118.0(3) ? C1 C11 C12 . . 114.6(3) ? C1 C11 H112 . . 108.6 ? C12 C11 H112 . . 108.6 ? C1 C11 H111 . . 108.6 ? C12 C11 H111 . . 108.6 ? H112 C11 H111 . . 107.6 ? C11 C12 C13 . . 114.1(3) ? C11 C12 H122 . . 108.7 ? C13 C12 H122 . . 108.7 ? C11 C12 H121 . . 108.7 ? C13 C12 H121 . . 108.7 ? H122 C12 H121 . . 107.6 ? C12 C13 C14 . . 109.6(5) ? C12 C13 C15 . . 111.0(4) ? C14 C13 C15 . . 108.8(5) ? C12 C13 H131 . . 109.1 ? C14 C13 H131 . . 109.1 ? C15 C13 H131 . . 109.1 ? C13 C14 H143 . . 109.5 ? C13 C14 H142 . . 109.5 ? H143 C14 H142 . . 109.5 ? C13 C14 H141 . . 109.5 ? H143 C14 H141 . . 109.5 ? H142 C14 H141 . . 109.5 ? C13 C15 H152 . . 109.5 ? C13 C15 H153 . . 109.5 ? H152 C15 H153 . . 109.5 ? C13 C15 H151 . . 109.5 ? H152 C15 H151 . . 109.5 ? H153 C15 H151 . . 109.5 ? N2 C21 C22 . . 112.6(3) ? N2 C21 H211 . . 109.1 ? C22 C21 H211 . . 109.1 ? N2 C21 H212 . . 109.1 ? C22 C21 H212 . . 109.1 ? H211 C21 H212 . . 107.8 ? C21 C22 H223 . . 109.5 ? C21 C22 H222 . . 109.5 ? H223 C22 H222 . . 109.5 ? C21 C22 H221 . . 109.5 ? H223 C22 H221 . . 109.5 ? H222 C22 H221 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 3.0(5) ? C2 N1 C1 C11 . . . . -176.5(3) ? C21 N2 C2 O2 . . . . -1.0(5) ? C21 N2 C2 N1 . . . . 178.3(3) ? C1 N1 C2 O2 . . . . 179.3(3) ? C1 N1 C2 N2 . . . . 0.1(5) ? O1 C1 C11 C12 . . . . 55.3(4) ? N1 C1 C11 C12 . . . . -125.3(3) ? C1 C11 C12 C13 . . . . 65.7(5) ? C11 C12 C13 C14 . . . . -175.0(4) ? C11 C12 C13 C15 . . . . 64.8(6) ? C2 N2 C21 C22 . . . . -82.8(4) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.86 2.39 3.069(3) 136.8 N1 H11 O2 2_566 0.86 2.00 2.859(3) 177.2 data_ethyl350K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7514(15) _cell_length_b 12.460(2) _cell_length_c 5.1254(9) _cell_angle_alpha 91.510(5) _cell_angle_beta 90.273(9) _cell_angle_gamma 89.642(8) _cell_volume 558.69(16) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4431 _cell_measurement_theta_min 2.855 _cell_measurement_theta_max 27.425 _cell_measurement_temperature 350 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.107 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being low temperature phase. ; _diffrn_ambient_temperature 350 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 6495 _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_av_sigmaI/netI 0.0130 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.826 _diffrn_measured_fraction_theta_full 0.826 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2118 _reflns_number_gt 1790 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1347 _refine_ls_R_factor_gt 0.1195 _refine_ls_wR_factor_gt 0.2409 _refine_ls_wR_factor_ref 0.2498 _refine_ls_goodness_of_fit_ref 1.344 _refine_ls_restrained_S_all 1.348 _refine_ls_number_reflns 2118 _refine_ls_number_parameters 118 _refine_ls_number_restraints 6 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+0.4679P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.201 _refine_diff_density_min -0.217 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 348K was used as an initial model. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.4331(3) 0.5744(2) 0.2313(6) 0.0800(9) Uani d . 1 . . O O2 0.0270(3) 0.4095(2) 0.2386(6) 0.0797(9) Uani d . 1 . . O N1 0.1970(3) 0.5338(3) 0.3786(7) 0.0657(9) Uani d . 1 . . N H11 0.1304 0.5529 0.4939 0.079 Uiso calc R 1 . . H N2 0.2526(4) 0.4162(3) 0.0302(7) 0.0683(9) Uani d D 1 . . N H12 0.3392 0.4478 0.0190 0.082 Uiso calc R 1 . . H C1 0.3300(4) 0.5901(3) 0.3871(8) 0.0623(10) Uani d . 1 . . C C2 0.1535(4) 0.4499(3) 0.2105(8) 0.0633(10) Uani d D 1 . . C C11 0.3413(5) 0.6722(3) 0.6048(9) 0.0775(12) Uani d D 1 . . C H112 0.4203 0.6496 0.7252 0.093 Uiso calc R 1 . . H H111 0.2453 0.6739 0.6988 0.093 Uiso calc R 1 . . H C12 0.3767(6) 0.7844(4) 0.5202(11) 0.1012(17) Uani d D 1 . . C H122 0.3968 0.8289 0.6746 0.121 Uiso calc R 1 . . H H121 0.4694 0.7820 0.4172 0.121 Uiso calc R 1 . . H C13 0.2530(8) 0.8371(5) 0.3637(13) 0.123(2) Uani d D 1 . . C H131 0.2292 0.7913 0.2107 0.148 Uiso calc R 1 . . H C14 0.3071(13) 0.9459(5) 0.2724(18) 0.201(5) Uani d D 1 . . C H143 0.2277 0.9788 0.1718 0.242 Uiso calc R 1 . . H H142 0.3966 0.9362 0.1666 0.242 Uiso calc R 1 . . H H141 0.3310 0.9911 0.4214 0.242 Uiso calc R 1 . . H C15 0.1083(8) 0.8548(7) 0.523(2) 0.192(4) Uani d D 1 . . C H152 0.0741 0.7873 0.5872 0.230 Uiso calc R 1 . . H H153 0.0301 0.8852 0.4154 0.230 Uiso calc R 1 . . H H151 0.1294 0.9030 0.6681 0.230 Uiso calc R 1 . . H C21 0.2183(5) 0.3279(4) -0.1466(9) 0.0788(12) Uani d D 1 . . C H211 0.2785 0.3348 -0.3037 0.095 Uiso calc R 1 . . H H212 0.1113 0.3317 -0.1959 0.095 Uiso calc R 1 . . H C22 0.2505(7) 0.2204(4) -0.0324(12) 0.1091(18) Uani d D 1 . . C H223 0.2262 0.1647 -0.1586 0.131 Uiso calc R 1 . . H H222 0.1891 0.2121 0.1205 0.131 Uiso calc R 1 . . H H221 0.3567 0.2155 0.0141 0.131 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0511(15) 0.095(2) 0.094(2) -0.0123(14) 0.0241(15) -0.0030(17) O2 0.0525(16) 0.092(2) 0.095(2) -0.0142(14) 0.0228(14) -0.0050(17) N1 0.0484(17) 0.073(2) 0.076(2) -0.0032(14) 0.0209(15) -0.0020(17) N2 0.0504(17) 0.074(2) 0.080(2) -0.0057(15) 0.0134(16) -0.0016(18) C1 0.049(2) 0.067(2) 0.072(2) 0.0016(17) 0.0082(18) 0.0141(19) C2 0.0451(19) 0.071(2) 0.075(3) 0.0033(17) 0.0150(18) 0.010(2) C11 0.064(3) 0.082(3) 0.087(3) -0.006(2) 0.010(2) 0.004(2) C12 0.087(4) 0.097(4) 0.120(4) -0.012(3) 0.026(3) -0.005(3) C13 0.145(6) 0.105(4) 0.120(5) 0.005(4) -0.020(4) 0.015(4) C14 0.316(14) 0.098(5) 0.192(9) -0.006(7) 0.019(9) 0.047(6) C15 0.109(6) 0.147(7) 0.321(14) 0.029(5) -0.021(7) 0.029(8) C21 0.060(2) 0.092(3) 0.084(3) -0.003(2) 0.010(2) -0.001(3) C22 0.114(4) 0.086(4) 0.127(5) 0.002(3) 0.010(4) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.219(4) ? O2 C2 . 1.230(4) ? N1 C1 . 1.362(5) ? N1 C2 . 1.391(5) ? N1 H11 . 0.8600 ? N2 C2 . 1.329(5) ? N2 C21 . 1.438(5) ? N2 H12 . 0.8600 ? C1 C11 . 1.496(6) ? C11 C12 . 1.510(7) ? C11 H112 . 0.9700 ? C11 H111 . 0.9700 ? C12 C13 . 1.502(9) ? C12 H122 . 0.9700 ? C12 H121 . 0.9700 ? C13 C15 . 1.523(11) ? C13 C14 . 1.524(10) ? C13 H131 . 0.9800 ? C14 H143 . 0.9600 ? C14 H142 . 0.9600 ? C14 H141 . 0.9600 ? C15 H152 . 0.9600 ? C15 H153 . 0.9600 ? C15 H151 . 0.9600 ? C21 C22 . 1.501(7) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 H223 . 0.9600 ? C22 H222 . 0.9600 ? C22 H221 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 129.3(3) ? C1 N1 H11 . . 115.3 ? C2 N1 H11 . . 115.3 ? C2 N2 C21 . . 121.6(3) ? C2 N2 H12 . . 119.2 ? C21 N2 H12 . . 119.2 ? O1 C1 N1 . . 122.8(4) ? O1 C1 C11 . . 122.3(4) ? N1 C1 C11 . . 115.0(3) ? O2 C2 N2 . . 123.3(4) ? O2 C2 N1 . . 118.7(3) ? N2 C2 N1 . . 118.0(3) ? C1 C11 C12 . . 114.8(4) ? C1 C11 H112 . . 108.6 ? C12 C11 H112 . . 108.6 ? C1 C11 H111 . . 108.6 ? C12 C11 H111 . . 108.6 ? H112 C11 H111 . . 107.5 ? C13 C12 C11 . . 115.0(4) ? C13 C12 H122 . . 108.5 ? C11 C12 H122 . . 108.5 ? C13 C12 H121 . . 108.5 ? C11 C12 H121 . . 108.5 ? H122 C12 H121 . . 107.5 ? C12 C13 C15 . . 111.6(6) ? C12 C13 C14 . . 110.0(6) ? C15 C13 C14 . . 108.2(7) ? C12 C13 H131 . . 109.0 ? C15 C13 H131 . . 109.0 ? C14 C13 H131 . . 109.0 ? C13 C14 H143 . . 109.5 ? C13 C14 H142 . . 109.5 ? H143 C14 H142 . . 109.5 ? C13 C14 H141 . . 109.5 ? H143 C14 H141 . . 109.5 ? H142 C14 H141 . . 109.5 ? C13 C15 H152 . . 109.5 ? C13 C15 H153 . . 109.5 ? H152 C15 H153 . . 109.5 ? C13 C15 H151 . . 109.5 ? H152 C15 H151 . . 109.5 ? H153 C15 H151 . . 109.5 ? N2 C21 C22 . . 113.1(4) ? N2 C21 H211 . . 109.0 ? C22 C21 H211 . . 109.0 ? N2 C21 H212 . . 109.0 ? C22 C21 H212 . . 109.0 ? H211 C21 H212 . . 107.8 ? C21 C22 H223 . . 109.5 ? C21 C22 H222 . . 109.5 ? H223 C22 H222 . . 109.5 ? C21 C22 H221 . . 109.5 ? H223 C22 H221 . . 109.5 ? H222 C22 H221 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 2.3(7) ? C2 N1 C1 C11 . . . . -176.9(4) ? C21 N2 C2 O2 . . . . -0.4(6) ? C21 N2 C2 N1 . . . . 178.3(4) ? C1 N1 C2 O2 . . . . 179.4(4) ? C1 N1 C2 N2 . . . . 0.7(6) ? O1 C1 C11 C12 . . . . 55.4(6) ? N1 C1 C11 C12 . . . . -125.3(4) ? C1 C11 C12 C13 . . . . 66.8(6) ? C11 C12 C13 C15 . . . . 64.3(7) ? C11 C12 C13 C14 . . . . -175.6(5) ? C2 N2 C21 C22 . . . . -83.5(5) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H12 O1 2_665 0.86 2.39 3.070(4) 136.9 N1 H11 O2 2_566 0.86 1.99 2.853(4) 177.5 data_ethyl352K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7503(15) _cell_length_b 12.4205(13) _cell_length_c 5.0998(3) _cell_angle_alpha 90.921(8) _cell_angle_beta 89.723(12) _cell_angle_gamma 89.714(10) _cell_volume 554.18(12) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2561 _cell_measurement_theta_min 1.64 _cell_measurement_theta_max 27.165 _cell_measurement_temperature 352 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.116 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being low temperature phase. ; _diffrn_ambient_temperature 352 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 6495 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.773 _diffrn_measured_fraction_theta_full 0.773 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 1968 _reflns_number_gt 1242 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1531 _refine_ls_R_factor_gt 0.1090 _refine_ls_wR_factor_gt 0.3116 _refine_ls_wR_factor_ref 0.3573 _refine_ls_goodness_of_fit_ref 2.279 _refine_ls_restrained_S_all 2.288 _refine_ls_number_reflns 1968 _refine_ls_number_parameters 118 _refine_ls_number_restraints 5 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.245 _refine_diff_density_min -0.272 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 350K was used as an initial model. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.4334(3) 0.5747(3) 0.2302(6) 0.0916(10) Uani d . 1 . . O O2 0.0271(3) 0.4095(2) 0.2407(6) 0.0884(10) Uani d . 1 . . O N1 0.1975(4) 0.5334(3) 0.3774(6) 0.0736(10) Uani d . 1 . . N H11 0.1306 0.5514 0.4943 0.088 Uiso calc R 1 . . H N2 0.2528(4) 0.4164(3) 0.0297(6) 0.0762(10) Uani d . 1 . . N H21 0.3397 0.4480 0.0171 0.091 Uiso calc R 1 . . H C1 0.3279(4) 0.5905(3) 0.3858(8) 0.0713(10) Uani d . 1 . . C C2 0.1544(5) 0.4503(3) 0.2098(8) 0.0745(10) Uani d . 1 . . C C11 0.3418(5) 0.6719(3) 0.6031(9) 0.0841(12) Uani d D 1 . . C H112 0.4200 0.6475 0.7228 0.101 Uiso calc R 1 . . H H111 0.2460 0.6746 0.6992 0.101 Uiso calc R 1 . . H C12 0.3806(6) 0.7842(4) 0.5206(11) 0.1075(17) Uani d D 1 . . C H122 0.4733 0.7820 0.4156 0.129 Uiso calc R 1 . . H H121 0.4004 0.8281 0.6756 0.129 Uiso calc R 1 . . H C13 0.2535(8) 0.8365(5) 0.3631(12) 0.131(2) Uani d D 1 . . C H131 0.2308 0.7903 0.2109 0.157 Uiso calc R 1 . . H C14 0.3088(15) 0.9449(6) 0.2663(19) 0.220(6) Uani d D 1 . . C H142 0.4007 0.9348 0.1651 0.264 Uiso calc R 1 . . H H141 0.3291 0.9916 0.4139 0.264 Uiso calc R 1 . . H H143 0.2315 0.9768 0.1589 0.264 Uiso calc R 1 . . H C15 0.1084(8) 0.8520(7) 0.524(2) 0.188(4) Uani d D 1 . . C H152 0.0739 0.7835 0.5849 0.225 Uiso calc R 1 . . H H153 0.0308 0.8839 0.4178 0.225 Uiso calc R 1 . . H H151 0.1289 0.8984 0.6722 0.225 Uiso calc R 1 . . H C21 0.2191(5) 0.3275(4) -0.1474(9) 0.0883(13) Uani d D 1 . . C H211 0.2798 0.3347 -0.3057 0.106 Uiso calc R 1 . . H H212 0.1122 0.3313 -0.1964 0.106 Uiso calc R 1 . . H C22 0.2506(8) 0.2200(4) -0.0318(13) 0.1205(19) Uani d D 1 . . C H223 0.2263 0.1644 -0.1575 0.145 Uiso calc R 1 . . H H222 0.1890 0.2115 0.1227 0.145 Uiso calc R 1 . . H H221 0.3567 0.2150 0.0136 0.145 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0625(17) 0.104(2) 0.108(2) -0.0180(14) 0.0261(15) -0.0071(17) O2 0.0576(17) 0.101(2) 0.106(2) -0.0170(13) 0.0298(14) -0.0096(16) N1 0.0580(18) 0.081(2) 0.0813(19) -0.0088(14) 0.0220(14) -0.0016(16) N2 0.0542(18) 0.085(2) 0.089(2) -0.0068(14) 0.0168(15) -0.0017(17) C1 0.0460(18) 0.081(2) 0.087(2) 0.0021(15) 0.0141(15) 0.017(2) C2 0.055(2) 0.082(2) 0.086(2) -0.0021(16) 0.0158(17) 0.010(2) C11 0.071(3) 0.082(2) 0.098(3) -0.0082(19) 0.010(2) 0.004(2) C12 0.084(3) 0.103(4) 0.135(4) -0.012(3) 0.024(3) -0.009(3) C13 0.162(7) 0.108(4) 0.123(5) 0.003(4) -0.011(4) 0.011(3) C14 0.34(2) 0.125(6) 0.193(9) 0.002(7) 0.005(10) 0.047(6) C15 0.105(6) 0.165(7) 0.294(12) 0.022(5) -0.012(7) 0.029(7) C21 0.067(3) 0.096(3) 0.101(3) -0.008(2) 0.018(2) -0.005(2) C22 0.133(5) 0.098(4) 0.130(5) 0.008(3) 0.007(4) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.228(4) ? O2 C2 . 1.237(5) ? N1 C1 . 1.346(5) ? N1 C2 . 1.384(5) ? N1 H11 . 0.8600 ? N2 C2 . 1.319(5) ? N2 C21 . 1.448(5) ? N2 H21 . 0.8600 ? C1 C11 . 1.494(6) ? C11 C12 . 1.503(6) ? C11 H112 . 0.9700 ? C11 H111 . 0.9700 ? C12 C13 . 1.524(8) ? C12 H122 . 0.9700 ? C12 H121 . 0.9700 ? C13 C15 . 1.519(11) ? C13 C14 . 1.522(10) ? C13 H131 . 0.9800 ? C14 H142 . 0.9600 ? C14 H141 . 0.9600 ? C14 H143 . 0.9600 ? C15 H152 . 0.9600 ? C15 H153 . 0.9600 ? C15 H151 . 0.9600 ? C21 C22 . 1.493(7) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 H223 . 0.9600 ? C22 H222 . 0.9600 ? C22 H221 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 130.1(3) ? C1 N1 H11 . . 114.9 ? C2 N1 H11 . . 114.9 ? C2 N2 C21 . . 122.0(4) ? C2 N2 H21 . . 119.0 ? C21 N2 H21 . . 119.0 ? O1 C1 N1 . . 122.4(4) ? O1 C1 C11 . . 120.8(4) ? N1 C1 C11 . . 116.7(3) ? O2 C2 N2 . . 123.1(4) ? O2 C2 N1 . . 118.5(3) ? N2 C2 N1 . . 118.4(4) ? C1 C11 C12 . . 115.6(4) ? C1 C11 H112 . . 108.4 ? C12 C11 H112 . . 108.4 ? C1 C11 H111 . . 108.4 ? C12 C11 H111 . . 108.4 ? H112 C11 H111 . . 107.4 ? C11 C12 C13 . . 112.7(4) ? C11 C12 H122 . . 109.1 ? C13 C12 H122 . . 109.1 ? C11 C12 H121 . . 109.1 ? C13 C12 H121 . . 109.1 ? H122 C12 H121 . . 107.8 ? C15 C13 C14 . . 109.7(8) ? C15 C13 C12 . . 112.0(5) ? C14 C13 C12 . . 108.9(6) ? C15 C13 H131 . . 108.7 ? C14 C13 H131 . . 108.7 ? C12 C13 H131 . . 108.7 ? C13 C14 H142 . . 109.5 ? C13 C14 H141 . . 109.5 ? H142 C14 H141 . . 109.5 ? C13 C14 H143 . . 109.5 ? H142 C14 H143 . . 109.5 ? H141 C14 H143 . . 109.5 ? C13 C15 H152 . . 109.5 ? C13 C15 H153 . . 109.5 ? H152 C15 H153 . . 109.5 ? C13 C15 H151 . . 109.5 ? H152 C15 H151 . . 109.5 ? H153 C15 H151 . . 109.5 ? N2 C21 C22 . . 113.2(4) ? N2 C21 H211 . . 108.9 ? C22 C21 H211 . . 108.9 ? N2 C21 H212 . . 108.9 ? C22 C21 H212 . . 108.9 ? H211 C21 H212 . . 107.8 ? C21 C22 H223 . . 109.5 ? C21 C22 H222 . . 109.5 ? H223 C22 H222 . . 109.5 ? C21 C22 H221 . . 109.5 ? H223 C22 H221 . . 109.5 ? H222 C22 H221 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 0.6(6) ? C2 N1 C1 C11 . . . . -176.8(3) ? C21 N2 C2 O2 . . . . -0.2(6) ? C21 N2 C2 N1 . . . . 177.8(3) ? C1 N1 C2 O2 . . . . 179.9(4) ? C1 N1 C2 N2 . . . . 1.8(6) ? O1 C1 C11 C12 . . . . 55.9(5) ? N1 C1 C11 C12 . . . . -126.7(4) ? C1 C11 C12 C13 . . . . 66.3(6) ? C11 C12 C13 C15 . . . . 63.9(8) ? C11 C12 C13 C14 . . . . -174.6(6) ? C2 N2 C21 C22 . . . . -83.5(5) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.86 2.36 3.047(4) 137.0 N1 H11 O2 2_566 0.86 1.98 2.840(4) 178.6 data_ethyl354K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7270(4) _cell_length_b 12.6010(13) _cell_length_c 5.1459(3) _cell_angle_alpha 91.317(9) _cell_angle_beta 90.331(11) _cell_angle_gamma 89.001(9) _cell_volume 565.65(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4364 _cell_measurement_theta_min 2.865 _cell_measurement_theta_max 27.455 _cell_measurement_temperature 354 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.094 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being low temperature phase. ; _diffrn_ambient_temperature 354 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 6513 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.815 _diffrn_measured_fraction_theta_full 0.815 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2122 _reflns_number_gt 1551 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1465 _refine_ls_R_factor_gt 0.1175 _refine_ls_wR_factor_gt 0.2594 _refine_ls_wR_factor_ref 0.2768 _refine_ls_goodness_of_fit_ref 1.305 _refine_ls_restrained_S_all 1.309 _refine_ls_number_reflns 2122 _refine_ls_number_parameters 118 _refine_ls_number_restraints 5 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0663P)^2^+0.4317P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.221 _refine_diff_density_min -0.222 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 352K was used as an initial model. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.4326(3) 0.5747(3) 0.2307(7) 0.0861(10) Uani d . 1 . . O O2 0.0267(3) 0.4098(3) 0.2401(7) 0.0852(10) Uani d . 1 . . O N1 0.1973(4) 0.5339(3) 0.3778(7) 0.0709(10) Uani d . 1 . . N H11 0.1303 0.5531 0.4923 0.085 Uiso calc R 1 . . H N2 0.2522(4) 0.4164(3) 0.0306(7) 0.0712(10) Uani d . 1 . . N H21 0.3383 0.4480 0.0169 0.085 Uiso calc R 1 . . H C1 0.3297(4) 0.5903(3) 0.3861(9) 0.0666(11) Uani d . 1 . . C C2 0.1532(4) 0.4496(3) 0.2123(9) 0.0661(11) Uani d . 1 . . C C11 0.3404(5) 0.6721(4) 0.6014(10) 0.0811(13) Uani d D 1 . . C H112 0.4189 0.6492 0.7229 0.097 Uiso calc R 1 . . H H111 0.2437 0.6747 0.6937 0.097 Uiso calc R 1 . . H C12 0.3767(7) 0.7834(4) 0.5180(13) 0.112(2) Uani d D 1 . . C H121 0.3964 0.8268 0.6723 0.134 Uiso calc R 1 . . H H122 0.4702 0.7803 0.4168 0.134 Uiso calc R 1 . . H C13 0.2538(8) 0.8369(5) 0.3608(14) 0.131(2) Uani d D 1 . . C H131 0.2307 0.7922 0.2078 0.157 Uiso calc R 1 . . H C14 0.3074(14) 0.9447(6) 0.271(2) 0.219(5) Uani d D 1 . . C H143 0.2279 0.9777 0.1698 0.262 Uiso calc R 1 . . H H142 0.3976 0.9350 0.1663 0.262 Uiso calc R 1 . . H H141 0.3305 0.9890 0.4195 0.262 Uiso calc R 1 . . H C15 0.1081(9) 0.8545(7) 0.518(2) 0.209(5) Uani d D 1 . . C H152 0.0748 0.7879 0.5821 0.250 Uiso calc R 1 . . H H153 0.0296 0.8843 0.4088 0.250 Uiso calc R 1 . . H H151 0.1280 0.9024 0.6613 0.250 Uiso calc R 1 . . H C21 0.2180(5) 0.3283(4) -0.1443(10) 0.0819(13) Uani d D 1 . . C H211 0.2783 0.3345 -0.3009 0.098 Uiso calc R 1 . . H H212 0.1107 0.3328 -0.1938 0.098 Uiso calc R 1 . . H C22 0.2503(8) 0.2210(4) -0.0295(13) 0.116(2) Uani d D 1 . . C H223 0.2251 0.1663 -0.1547 0.140 Uiso calc R 1 . . H H222 0.1893 0.2134 0.1234 0.140 Uiso calc R 1 . . H H221 0.3569 0.2150 0.0157 0.140 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0583(17) 0.102(2) 0.098(2) -0.0109(15) 0.0267(16) -0.0047(19) O2 0.0544(16) 0.100(2) 0.102(2) -0.0142(15) 0.0237(15) -0.0063(18) N1 0.0523(18) 0.079(2) 0.082(2) -0.0025(16) 0.0237(17) 0.001(2) N2 0.0510(18) 0.082(2) 0.081(2) -0.0032(16) 0.0158(16) -0.0026(19) C1 0.053(2) 0.071(3) 0.077(3) 0.0035(18) 0.0116(19) 0.016(2) C2 0.049(2) 0.074(3) 0.076(3) 0.0056(18) 0.0106(19) 0.014(2) C11 0.068(3) 0.083(3) 0.092(3) -0.003(2) 0.014(2) 0.005(3) C12 0.098(4) 0.106(4) 0.132(5) -0.011(3) 0.028(4) -0.010(4) C13 0.151(7) 0.113(5) 0.129(6) 0.014(5) -0.017(5) 0.025(4) C14 0.342(16) 0.108(6) 0.208(10) -0.001(8) 0.033(10) 0.045(6) C15 0.120(7) 0.166(8) 0.340(16) 0.035(6) -0.023(9) 0.032(9) C21 0.062(2) 0.098(3) 0.086(3) -0.002(2) 0.012(2) 0.000(3) C22 0.121(5) 0.092(4) 0.136(5) 0.003(3) 0.012(4) -0.001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.217(5) ? O2 C2 . 1.232(5) ? N1 C1 . 1.367(5) ? N1 C2 . 1.403(6) ? N1 H11 . 0.8600 ? N2 C2 . 1.332(5) ? N2 C21 . 1.447(6) ? N2 H21 . 0.8600 ? C1 C11 . 1.499(6) ? C11 C12 . 1.516(7) ? C11 H112 . 0.9700 ? C11 H111 . 0.9700 ? C12 C13 . 1.500(9) ? C12 H121 . 0.9700 ? C12 H122 . 0.9700 ? C13 C15 . 1.520(11) ? C13 C14 . 1.527(11) ? C13 H131 . 0.9800 ? C14 H143 . 0.9600 ? C14 H142 . 0.9600 ? C14 H141 . 0.9600 ? C15 H152 . 0.9600 ? C15 H153 . 0.9600 ? C15 H151 . 0.9600 ? C21 C22 . 1.510(8) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 H223 . 0.9600 ? C22 H222 . 0.9600 ? C22 H221 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 130.3(3) ? C1 N1 H11 . . 114.9 ? C2 N1 H11 . . 114.9 ? C2 N2 C21 . . 121.4(4) ? C2 N2 H21 . . 119.3 ? C21 N2 H21 . . 119.3 ? O1 C1 N1 . . 122.4(4) ? O1 C1 C11 . . 122.1(4) ? N1 C1 C11 . . 115.5(4) ? O2 C2 N2 . . 123.0(4) ? O2 C2 N1 . . 119.4(4) ? N2 C2 N1 . . 117.6(3) ? C1 C11 C12 . . 115.6(4) ? C1 C11 H112 . . 108.4 ? C12 C11 H112 . . 108.4 ? C1 C11 H111 . . 108.4 ? C12 C11 H111 . . 108.4 ? H112 C11 H111 . . 107.4 ? C13 C12 C11 . . 115.0(5) ? C13 C12 H121 . . 108.5 ? C11 C12 H121 . . 108.5 ? C13 C12 H122 . . 108.5 ? C11 C12 H122 . . 108.5 ? H121 C12 H122 . . 107.5 ? C12 C13 C15 . . 111.4(6) ? C12 C13 C14 . . 110.5(7) ? C15 C13 C14 . . 108.2(8) ? C12 C13 H131 . . 108.9 ? C15 C13 H131 . . 108.9 ? C14 C13 H131 . . 108.9 ? C13 C14 H143 . . 109.5 ? C13 C14 H142 . . 109.5 ? H143 C14 H142 . . 109.5 ? C13 C14 H141 . . 109.5 ? H143 C14 H141 . . 109.5 ? H142 C14 H141 . . 109.5 ? C13 C15 H152 . . 109.5 ? C13 C15 H153 . . 109.5 ? H152 C15 H153 . . 109.5 ? C13 C15 H151 . . 109.5 ? H152 C15 H151 . . 109.5 ? H153 C15 H151 . . 109.5 ? N2 C21 C22 . . 113.7(4) ? N2 C21 H211 . . 108.8 ? C22 C21 H211 . . 108.8 ? N2 C21 H212 . . 108.8 ? C22 C21 H212 . . 108.8 ? H211 C21 H212 . . 107.7 ? C21 C22 H223 . . 109.5 ? C21 C22 H222 . . 109.5 ? H223 C22 H222 . . 109.5 ? C21 C22 H221 . . 109.5 ? H223 C22 H221 . . 109.5 ? H222 C22 H221 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 2.7(7) ? C2 N1 C1 C11 . . . . -176.8(4) ? C21 N2 C2 O2 . . . . -1.5(7) ? C21 N2 C2 N1 . . . . 178.4(4) ? C1 N1 C2 O2 . . . . 179.8(4) ? C1 N1 C2 N2 . . . . -0.1(6) ? O1 C1 C11 C12 . . . . 54.2(6) ? N1 C1 C11 C12 . . . . -126.4(4) ? C1 C11 C12 C13 . . . . 66.9(6) ? C11 C12 C13 C15 . . . . 64.0(8) ? C11 C12 C13 C14 . . . . -175.8(6) ? C2 N2 C21 C22 . . . . -82.3(5) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.86 2.39 3.073(4) 137.1 N1 H11 O2 2_566 0.86 1.99 2.850(5) 177.3 data_ethyl356K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.726(3) _cell_length_b 12.460(3) _cell_length_c 5.1382(12) _cell_angle_alpha 91.423(6) _cell_angle_beta 90.143(10) _cell_angle_gamma 89.297(11) _cell_volume 558.5(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2070 _cell_measurement_theta_min 2.335 _cell_measurement_theta_max 27.48 _cell_measurement_temperature 356 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.80 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.108 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being low temperature phase. ; _diffrn_ambient_temperature 356 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 6409 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_max 0.668 _diffrn_measured_fraction_theta_full 0.668 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 1713 _reflns_number_gt 1306 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0991 _refine_ls_R_factor_gt 0.0792 _refine_ls_wR_factor_gt 0.2200 _refine_ls_wR_factor_ref 0.2495 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.087 _refine_ls_number_reflns 1713 _refine_ls_number_parameters 118 _refine_ls_number_restraints 5 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1254P)^2^+0.2162P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.228 _refine_diff_density_min -0.243 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 354K was used as an initial model. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.4321(3) 0.5743(2) 0.2297(5) 0.0906(8) Uani d . 1 . . O O2 0.0271(3) 0.4103(2) 0.2409(5) 0.0873(8) Uani d . 1 . . O N1 0.1970(3) 0.5337(2) 0.3769(5) 0.0726(8) Uani d . 1 . . N H11 0.1302 0.5527 0.4923 0.087 Uiso calc R 1 . . H N2 0.2523(3) 0.4164(2) 0.0323(5) 0.0759(8) Uani d . 1 . . N H21 0.3390 0.4479 0.0207 0.091 Uiso calc R 1 . . H C1 0.3290(4) 0.5900(3) 0.3840(6) 0.0721(9) Uani d . 1 . . C C2 0.1537(4) 0.4496(3) 0.2106(6) 0.0708(8) Uani d . 1 . . C C11 0.3411(4) 0.6720(3) 0.5999(7) 0.0851(10) Uani d D 1 . . C H112 0.4200 0.6487 0.7200 0.102 Uiso calc R 1 . . H H111 0.2448 0.6746 0.6940 0.102 Uiso calc R 1 . . H C12 0.3775(5) 0.7834(3) 0.5164(10) 0.1125(14) Uani d D 1 . . C H122 0.4708 0.7803 0.4140 0.135 Uiso calc R 1 . . H H121 0.3975 0.8276 0.6705 0.135 Uiso calc R 1 . . H C13 0.2533(7) 0.8369(4) 0.3592(11) 0.138(2) Uani d D 1 . . C H131 0.2304 0.7911 0.2066 0.165 Uiso calc R 1 . . H C14 0.3084(12) 0.9448(5) 0.2669(17) 0.217(4) Uani d D 1 . . C H143 0.2299 0.9777 0.1636 0.260 Uiso calc R 1 . . H H142 0.3993 0.9343 0.1639 0.260 Uiso calc R 1 . . H H141 0.3309 0.9905 0.4149 0.260 Uiso calc R 1 . . H C15 0.1063(8) 0.8539(6) 0.5178(19) 0.205(4) Uani d D 1 . . C H152 0.0722 0.7861 0.5793 0.246 Uiso calc R 1 . . H H153 0.0283 0.8849 0.4100 0.246 Uiso calc R 1 . . H H151 0.1262 0.9014 0.6637 0.246 Uiso calc R 1 . . H C21 0.2181(4) 0.3286(3) -0.1433(7) 0.0846(10) Uani d D 1 . . C H211 0.2787 0.3350 -0.3000 0.102 Uiso calc R 1 . . H H212 0.1109 0.3328 -0.1926 0.102 Uiso calc R 1 . . H C22 0.2501(7) 0.2215(3) -0.0277(10) 0.1194(15) Uani d D 1 . . C H223 0.2260 0.1656 -0.1528 0.143 Uiso calc R 1 . . H H222 0.1882 0.2137 0.1248 0.143 Uiso calc R 1 . . H H221 0.3564 0.2163 0.0189 0.143 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0631(14) 0.1048(18) 0.1040(17) -0.0101(12) 0.0276(13) -0.0024(14) O2 0.0605(15) 0.0961(16) 0.1052(18) -0.0090(11) 0.0257(12) -0.0039(13) N1 0.0594(15) 0.0782(17) 0.0803(16) -0.0007(12) 0.0216(12) 0.0030(13) N2 0.0572(15) 0.0836(18) 0.0868(18) -0.0003(12) 0.0171(12) 0.0004(14) C1 0.0579(18) 0.0747(19) 0.085(2) 0.0035(14) 0.0125(15) 0.0196(16) C2 0.0550(17) 0.0787(19) 0.079(2) 0.0058(14) 0.0136(14) 0.0123(16) C11 0.078(2) 0.082(2) 0.095(2) -0.0011(17) 0.0099(18) 0.0000(18) C12 0.100(3) 0.103(3) 0.135(4) -0.010(2) 0.025(3) -0.006(3) C13 0.165(6) 0.107(3) 0.142(4) 0.012(3) -0.021(4) 0.016(3) C14 0.333(14) 0.110(4) 0.210(8) -0.003(6) 0.015(8) 0.047(5) C15 0.122(6) 0.162(6) 0.331(12) 0.038(4) -0.011(7) 0.022(7) C21 0.065(2) 0.097(2) 0.091(2) 0.0017(17) 0.0127(16) -0.0025(19) C22 0.134(4) 0.092(3) 0.132(4) 0.007(3) 0.007(3) 0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.211(4) ? O2 C2 . 1.225(4) ? N1 C1 . 1.357(4) ? N1 C2 . 1.390(4) ? N1 H11 . 0.8600 ? N2 C2 . 1.314(4) ? N2 C21 . 1.435(4) ? N2 H21 . 0.8600 ? C1 C11 . 1.494(5) ? C11 C12 . 1.501(6) ? C11 H112 . 0.9700 ? C11 H111 . 0.9700 ? C12 C13 . 1.509(8) ? C12 H122 . 0.9700 ? C12 H121 . 0.9700 ? C13 C14 . 1.520(9) ? C13 C15 . 1.532(10) ? C13 H131 . 0.9800 ? C14 H143 . 0.9600 ? C14 H142 . 0.9600 ? C14 H141 . 0.9600 ? C15 H152 . 0.9600 ? C15 H153 . 0.9600 ? C15 H151 . 0.9600 ? C21 C22 . 1.497(6) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 H223 . 0.9600 ? C22 H222 . 0.9600 ? C22 H221 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 129.6(3) ? C1 N1 H11 . . 115.2 ? C2 N1 H11 . . 115.2 ? C2 N2 C21 . . 121.3(3) ? C2 N2 H21 . . 119.3 ? C21 N2 H21 . . 119.3 ? O1 C1 N1 . . 122.9(3) ? O1 C1 C11 . . 121.7(3) ? N1 C1 C11 . . 115.5(3) ? O2 C2 N2 . . 124.1(3) ? O2 C2 N1 . . 118.2(3) ? N2 C2 N1 . . 117.7(3) ? C1 C11 C12 . . 115.1(3) ? C1 C11 H112 . . 108.5 ? C12 C11 H112 . . 108.5 ? C1 C11 H111 . . 108.5 ? C12 C11 H111 . . 108.5 ? H112 C11 H111 . . 107.5 ? C11 C12 C13 . . 114.7(4) ? C11 C12 H122 . . 108.6 ? C13 C12 H122 . . 108.6 ? C11 C12 H121 . . 108.6 ? C13 C12 H121 . . 108.6 ? H122 C12 H121 . . 107.6 ? C12 C13 C14 . . 109.9(6) ? C12 C13 C15 . . 111.6(5) ? C14 C13 C15 . . 109.2(6) ? C12 C13 H131 . . 108.7 ? C14 C13 H131 . . 108.7 ? C15 C13 H131 . . 108.7 ? C13 C14 H143 . . 109.5 ? C13 C14 H142 . . 109.5 ? H143 C14 H142 . . 109.5 ? C13 C14 H141 . . 109.5 ? H143 C14 H141 . . 109.5 ? H142 C14 H141 . . 109.5 ? C13 C15 H152 . . 109.5 ? C13 C15 H153 . . 109.5 ? H152 C15 H153 . . 109.5 ? C13 C15 H151 . . 109.5 ? H152 C15 H151 . . 109.5 ? H153 C15 H151 . . 109.5 ? N2 C21 C22 . . 112.7(3) ? N2 C21 H211 . . 109.0 ? C22 C21 H211 . . 109.0 ? N2 C21 H212 . . 109.0 ? C22 C21 H212 . . 109.0 ? H211 C21 H212 . . 107.8 ? C21 C22 H223 . . 109.5 ? C21 C22 H222 . . 109.5 ? H223 C22 H222 . . 109.5 ? C21 C22 H221 . . 109.5 ? H223 C22 H221 . . 109.5 ? H222 C22 H221 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 2.0(5) ? C2 N1 C1 C11 . . . . -176.7(3) ? C21 N2 C2 O2 . . . . -0.5(5) ? C21 N2 C2 N1 . . . . 178.6(3) ? C1 N1 C2 O2 . . . . 180.0(3) ? C1 N1 C2 N2 . . . . 0.8(5) ? O1 C1 C11 C12 . . . . 55.1(5) ? N1 C1 C11 C12 . . . . -126.2(3) ? C1 C11 C12 C13 . . . . 66.6(5) ? C11 C12 C13 C14 . . . . -175.2(5) ? C11 C12 C13 C15 . . . . 63.5(6) ? C2 N2 C21 C22 . . . . -83.1(4) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.86 2.39 3.073(4) 137.0 N1 H11 O2 2_566 0.86 1.98 2.844(4) 177.3 data_ethyl358K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7438(6) _cell_length_b 12.5269(10) _cell_length_c 5.1573(4) _cell_angle_alpha 90.802(6) _cell_angle_beta 90.388(7) _cell_angle_gamma 89.224(3) _cell_volume 564.77(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2719 _cell_measurement_theta_min 3.95 _cell_measurement_theta_max 27.385 _cell_measurement_temperature 358 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 1.00 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.095 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being low temperature phase. ; _diffrn_ambient_temperature 358 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 6499 _diffrn_reflns_av_R_equivalents 0.058 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.41 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_max 0.931 _diffrn_measured_fraction_theta_full 0.931 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2397 _reflns_number_gt 1516 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1360 _refine_ls_R_factor_gt 0.1033 _refine_ls_wR_factor_gt 0.2800 _refine_ls_wR_factor_ref 0.2975 _refine_ls_goodness_of_fit_ref 1.829 _refine_ls_restrained_S_all 1.839 _refine_ls_number_reflns 2397 _refine_ls_number_parameters 118 _refine_ls_number_restraints 5 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.360 _refine_diff_density_min -0.278 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 356K was used as an initial model. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.4322(2) 0.57411(19) 0.2289(5) 0.0866(7) Uani d . 1 . . O O2 0.0270(2) 0.40995(18) 0.2426(5) 0.0839(7) Uani d . 1 . . O N1 0.1973(2) 0.53358(18) 0.3763(5) 0.0685(7) Uani d . 1 . . N H11 0.1306 0.5524 0.4905 0.082 Uiso calc R 1 . . H N2 0.2522(3) 0.4163(2) 0.0331(5) 0.0731(7) Uani d . 1 . . N H21 0.3389 0.4474 0.0215 0.088 Uiso calc R 1 . . H C1 0.3293(3) 0.5898(2) 0.3831(6) 0.0685(8) Uani d . 1 . . C C2 0.1542(3) 0.4499(2) 0.2113(6) 0.0677(7) Uani d . 1 . . C C11 0.3410(4) 0.6723(2) 0.6002(7) 0.0828(9) Uani d D 1 . . C H112 0.2446 0.6749 0.6923 0.099 Uiso calc R 1 . . H H111 0.4194 0.6489 0.7215 0.099 Uiso calc R 1 . . H C12 0.3775(5) 0.7827(3) 0.5155(9) 0.1082(13) Uani d D 1 . . C H122 0.4706 0.7795 0.4142 0.130 Uiso calc R 1 . . H H121 0.3976 0.8264 0.6683 0.130 Uiso calc R 1 . . H C13 0.2537(6) 0.8362(4) 0.3571(10) 0.1355(18) Uani d D 1 . . C H131 0.2316 0.7911 0.2050 0.163 Uiso calc R 1 . . H C14 0.3083(11) 0.9447(5) 0.2640(17) 0.222(4) Uani d D 1 . . C H143 0.2295 0.9776 0.1607 0.267 Uiso calc R 1 . . H H142 0.3988 0.9349 0.1619 0.267 Uiso calc R 1 . . H H141 0.3306 0.9897 0.4113 0.267 Uiso calc R 1 . . H C15 0.1067(7) 0.8530(6) 0.5095(17) 0.204(4) Uani d D 1 . . C H153 0.0307 0.8861 0.4009 0.244 Uiso calc R 1 . . H H151 0.1263 0.8981 0.6577 0.244 Uiso calc R 1 . . H H152 0.0704 0.7852 0.5662 0.244 Uiso calc R 1 . . H C21 0.2184(4) 0.3287(3) -0.1431(7) 0.0823(9) Uani d D 1 . . C H211 0.2797 0.3354 -0.2980 0.099 Uiso calc R 1 . . H H212 0.1117 0.3333 -0.1946 0.099 Uiso calc R 1 . . H C22 0.2493(5) 0.2215(3) -0.0267(10) 0.1145(14) Uani d D 1 . . C H223 0.2248 0.1665 -0.1510 0.137 Uiso calc R 1 . . H H222 0.1876 0.2138 0.1249 0.137 Uiso calc R 1 . . H H221 0.3555 0.2157 0.0205 0.137 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0643(12) 0.0974(15) 0.0986(16) -0.0124(10) 0.0275(11) -0.0013(12) O2 0.0601(12) 0.0913(14) 0.1009(16) -0.0127(9) 0.0233(10) -0.0026(12) N1 0.0559(12) 0.0734(14) 0.0766(15) -0.0013(10) 0.0194(10) 0.0026(12) N2 0.0567(13) 0.0770(15) 0.0859(17) -0.0015(10) 0.0183(11) -0.0011(12) C1 0.0560(14) 0.0729(16) 0.0771(18) 0.0034(11) 0.0139(12) 0.0141(13) C2 0.0534(13) 0.0737(16) 0.0764(18) 0.0043(11) 0.0155(12) 0.0136(14) C11 0.0733(18) 0.0785(19) 0.097(2) 0.0010(14) 0.0112(16) 0.0006(17) C12 0.104(3) 0.094(3) 0.127(3) -0.011(2) 0.027(2) -0.009(2) C13 0.163(5) 0.101(3) 0.142(4) 0.008(3) -0.022(4) 0.014(3) C14 0.351(13) 0.109(4) 0.208(8) -0.010(5) 0.035(8) 0.048(5) C15 0.132(5) 0.145(5) 0.332(11) 0.029(4) -0.038(7) 0.009(6) C21 0.0658(17) 0.091(2) 0.090(2) 0.0008(14) 0.0127(15) -0.0019(17) C22 0.120(3) 0.089(3) 0.134(3) 0.006(2) 0.009(3) 0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.217(3) ? O2 C2 . 1.238(3) ? N1 C1 . 1.361(4) ? N1 C2 . 1.395(4) ? N1 H11 . 0.8600 ? N2 C2 . 1.322(4) ? N2 C21 . 1.447(4) ? N2 H21 . 0.8600 ? C1 C11 . 1.516(5) ? C11 C12 . 1.495(5) ? C11 H112 . 0.9700 ? C11 H111 . 0.9700 ? C12 C13 . 1.508(7) ? C12 H122 . 0.9700 ? C12 H121 . 0.9700 ? C13 C15 . 1.522(9) ? C13 C14 . 1.531(8) ? C13 H131 . 0.9800 ? C14 H143 . 0.9600 ? C14 H142 . 0.9600 ? C14 H141 . 0.9600 ? C15 H153 . 0.9600 ? C15 H151 . 0.9600 ? C15 H152 . 0.9600 ? C21 C22 . 1.498(5) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 H223 . 0.9600 ? C22 H222 . 0.9600 ? C22 H221 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 129.5(2) ? C1 N1 H11 . . 115.2 ? C2 N1 H11 . . 115.2 ? C2 N2 C21 . . 122.1(2) ? C2 N2 H21 . . 118.9 ? C21 N2 H21 . . 118.9 ? O1 C1 N1 . . 122.6(3) ? O1 C1 C11 . . 122.1(3) ? N1 C1 C11 . . 115.3(2) ? O2 C2 N2 . . 123.5(3) ? O2 C2 N1 . . 118.2(3) ? N2 C2 N1 . . 118.3(2) ? C12 C11 C1 . . 115.1(3) ? C12 C11 H112 . . 108.5 ? C1 C11 H112 . . 108.5 ? C12 C11 H111 . . 108.5 ? C1 C11 H111 . . 108.5 ? H112 C11 H111 . . 107.5 ? C11 C12 C13 . . 114.6(3) ? C11 C12 H122 . . 108.6 ? C13 C12 H122 . . 108.6 ? C11 C12 H121 . . 108.6 ? C13 C12 H121 . . 108.6 ? H122 C12 H121 . . 107.6 ? C12 C13 C15 . . 112.2(5) ? C12 C13 C14 . . 110.0(5) ? C15 C13 C14 . . 108.7(6) ? C12 C13 H131 . . 108.6 ? C15 C13 H131 . . 108.6 ? C14 C13 H131 . . 108.6 ? C13 C14 H143 . . 109.5 ? C13 C14 H142 . . 109.5 ? H143 C14 H142 . . 109.5 ? C13 C14 H141 . . 109.5 ? H143 C14 H141 . . 109.5 ? H142 C14 H141 . . 109.5 ? C13 C15 H153 . . 109.5 ? C13 C15 H151 . . 109.5 ? H153 C15 H151 . . 109.5 ? C13 C15 H152 . . 109.5 ? H153 C15 H152 . . 109.5 ? H151 C15 H152 . . 109.5 ? N2 C21 C22 . . 112.9(3) ? N2 C21 H211 . . 109.0 ? C22 C21 H211 . . 109.0 ? N2 C21 H212 . . 109.0 ? C22 C21 H212 . . 109.0 ? H211 C21 H212 . . 107.8 ? C21 C22 H223 . . 109.5 ? C21 C22 H222 . . 109.5 ? H223 C22 H222 . . 109.5 ? C21 C22 H221 . . 109.5 ? H223 C22 H221 . . 109.5 ? H222 C22 H221 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 2.1(5) ? C2 N1 C1 C11 . . . . -176.8(3) ? C21 N2 C2 O2 . . . . 0.1(4) ? C21 N2 C2 N1 . . . . 178.8(2) ? C1 N1 C2 O2 . . . . 179.5(3) ? C1 N1 C2 N2 . . . . 0.8(4) ? O1 C1 C11 C12 . . . . 54.6(4) ? N1 C1 C11 C12 . . . . -126.5(3) ? C1 C11 C12 C13 . . . . 66.9(5) ? C11 C12 C13 C15 . . . . 63.1(6) ? C11 C12 C13 C14 . . . . -175.7(5) ? C2 N2 C21 C22 . . . . -82.7(4) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.86 2.40 3.085(3) 137.1 N1 H11 O2 2_566 0.86 2.00 2.861(3) 177.7 data_ethyl360K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7564(14) _cell_length_b 12.5792(14) _cell_length_c 5.1472(6) _cell_angle_alpha 90.683(10) _cell_angle_beta 90.707(6) _cell_angle_gamma 89.216(6) _cell_volume 566.82(13) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2770 _cell_measurement_theta_min 2.815 _cell_measurement_theta_max 27.3 _cell_measurement_temperature 360 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 1.00 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.091 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being low temperature phase. ; _diffrn_ambient_temperature 360 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 6442 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.43 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_max 0.923 _diffrn_measured_fraction_theta_full 0.923 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2389 _reflns_number_gt 1518 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1332 _refine_ls_R_factor_gt 0.0998 _refine_ls_wR_factor_gt 0.2768 _refine_ls_wR_factor_ref 0.3155 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.043 _refine_ls_number_reflns 2389 _refine_ls_number_parameters 118 _refine_ls_number_restraints 5 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1605P)^2^+0.2211P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.305 _refine_diff_density_min -0.286 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 358K was used as an initial model. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.4323(3) 0.5741(2) 0.2286(6) 0.0901(8) Uani d . 1 . . O O2 0.0268(3) 0.4099(2) 0.2428(5) 0.0870(8) Uani d . 1 . . O N1 0.1970(3) 0.5334(2) 0.3761(6) 0.0710(8) Uani d . 1 . . N H11 0.1304 0.5521 0.4898 0.085 Uiso calc R 1 . . H N2 0.2524(3) 0.4167(2) 0.0336(6) 0.0747(8) Uani d . 1 . . N H21 0.3385 0.4483 0.0205 0.090 Uiso calc R 1 . . H C1 0.3288(4) 0.5898(3) 0.3835(7) 0.0698(9) Uani d . 1 . . C C2 0.1541(4) 0.4501(3) 0.2124(7) 0.0712(9) Uani d . 1 . . C C11 0.3405(5) 0.6718(3) 0.5965(8) 0.0845(10) Uani d D 1 . . C H112 0.4188 0.6486 0.7190 0.101 Uiso calc R 1 . . H H111 0.2443 0.6743 0.6881 0.101 Uiso calc R 1 . . H C12 0.3769(6) 0.7824(4) 0.5126(11) 0.1170(16) Uani d D 1 . . C H121 0.4692 0.7795 0.4104 0.140 Uiso calc R 1 . . H H122 0.3979 0.8254 0.6662 0.140 Uiso calc R 1 . . H C13 0.2526(7) 0.8365(4) 0.3553(13) 0.140(2) Uani d D 1 . . C H131 0.2293 0.7922 0.2024 0.168 Uiso calc R 1 . . H C14 0.3085(14) 0.9442(5) 0.264(2) 0.233(5) Uani d D 1 . . C H143 0.2299 0.9782 0.1622 0.279 Uiso calc R 1 . . H H142 0.3982 0.9340 0.1610 0.279 Uiso calc R 1 . . H H141 0.3327 0.9881 0.4127 0.279 Uiso calc R 1 . . H C15 0.1069(8) 0.8536(7) 0.509(2) 0.218(5) Uani d D 1 . . C H153 0.0310 0.8877 0.4020 0.261 Uiso calc R 1 . . H H151 0.1281 0.8977 0.6588 0.261 Uiso calc R 1 . . H H152 0.0699 0.7862 0.5650 0.261 Uiso calc R 1 . . H C21 0.2183(4) 0.3289(3) -0.1393(8) 0.0845(10) Uani d D 1 . . C H211 0.2780 0.3356 -0.2956 0.101 Uiso calc R 1 . . H H212 0.1113 0.3331 -0.1895 0.101 Uiso calc R 1 . . H C22 0.2504(7) 0.2222(4) -0.0241(11) 0.1191(16) Uani d D 1 . . C H223 0.2252 0.1676 -0.1486 0.143 Uiso calc R 1 . . H H222 0.1899 0.2141 0.1285 0.143 Uiso calc R 1 . . H H221 0.3567 0.2165 0.0220 0.143 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0673(14) 0.1010(18) 0.1031(18) -0.0140(12) 0.0296(13) -0.0023(14) O2 0.0617(14) 0.0968(17) 0.1034(19) -0.0135(11) 0.0254(12) -0.0052(14) N1 0.0581(14) 0.0739(16) 0.0816(17) -0.0041(11) 0.0225(12) 0.0009(13) N2 0.0576(14) 0.0799(17) 0.0870(19) -0.0035(12) 0.0198(13) -0.0010(14) C1 0.0573(16) 0.0748(19) 0.078(2) -0.0007(13) 0.0135(14) 0.0148(15) C2 0.0556(16) 0.0758(19) 0.083(2) 0.0048(13) 0.0173(14) 0.0131(16) C11 0.079(2) 0.080(2) 0.095(3) 0.0000(17) 0.0101(19) 0.0035(19) C12 0.110(3) 0.106(3) 0.135(4) -0.014(3) 0.026(3) -0.008(3) C13 0.162(6) 0.111(4) 0.148(5) 0.011(4) -0.020(4) 0.018(3) C14 0.371(16) 0.107(5) 0.222(9) -0.005(6) 0.024(10) 0.049(5) C15 0.125(6) 0.169(7) 0.357(14) 0.028(5) -0.041(8) 0.009(8) C21 0.068(2) 0.093(2) 0.093(2) -0.0001(17) 0.0115(18) -0.004(2) C22 0.129(4) 0.089(3) 0.139(4) 0.004(3) 0.012(3) -0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.227(4) ? O2 C2 . 1.243(4) ? N1 C1 . 1.363(4) ? N1 C2 . 1.390(5) ? N1 H11 . 0.8600 ? N2 C2 . 1.328(4) ? N2 C21 . 1.443(5) ? N2 H21 . 0.8600 ? C1 C11 . 1.499(5) ? C11 C12 . 1.502(6) ? C11 H112 . 0.9700 ? C11 H111 . 0.9700 ? C12 C13 . 1.508(8) ? C12 H121 . 0.9700 ? C12 H122 . 0.9700 ? C13 C15 . 1.522(11) ? C13 C14 . 1.527(10) ? C13 H131 . 0.9800 ? C14 H143 . 0.9600 ? C14 H142 . 0.9600 ? C14 H141 . 0.9600 ? C15 H153 . 0.9600 ? C15 H151 . 0.9600 ? C15 H152 . 0.9600 ? C21 C22 . 1.495(6) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 H223 . 0.9600 ? C22 H222 . 0.9600 ? C22 H221 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 129.7(3) ? C1 N1 H11 . . 115.2 ? C2 N1 H11 . . 115.2 ? C2 N2 C21 . . 121.6(3) ? C2 N2 H21 . . 119.2 ? C21 N2 H21 . . 119.2 ? O1 C1 N1 . . 122.5(3) ? O1 C1 C11 . . 121.9(3) ? N1 C1 C11 . . 115.6(3) ? O2 C2 N2 . . 123.4(3) ? O2 C2 N1 . . 118.4(3) ? N2 C2 N1 . . 118.2(3) ? C1 C11 C12 . . 115.9(3) ? C1 C11 H112 . . 108.3 ? C12 C11 H112 . . 108.3 ? C1 C11 H111 . . 108.3 ? C12 C11 H111 . . 108.3 ? H112 C11 H111 . . 107.4 ? C11 C12 C13 . . 114.7(4) ? C11 C12 H121 . . 108.6 ? C13 C12 H121 . . 108.6 ? C11 C12 H122 . . 108.6 ? C13 C12 H122 . . 108.6 ? H121 C12 H122 . . 107.6 ? C12 C13 C15 . . 112.3(6) ? C12 C13 C14 . . 109.5(6) ? C15 C13 C14 . . 108.9(7) ? C12 C13 H131 . . 108.7 ? C15 C13 H131 . . 108.7 ? C14 C13 H131 . . 108.7 ? C13 C14 H143 . . 109.5 ? C13 C14 H142 . . 109.5 ? H143 C14 H142 . . 109.5 ? C13 C14 H141 . . 109.5 ? H143 C14 H141 . . 109.5 ? H142 C14 H141 . . 109.5 ? C13 C15 H153 . . 109.5 ? C13 C15 H151 . . 109.5 ? H153 C15 H151 . . 109.5 ? C13 C15 H152 . . 109.5 ? H153 C15 H152 . . 109.5 ? H151 C15 H152 . . 109.5 ? N2 C21 C22 . . 113.8(4) ? N2 C21 H211 . . 108.8 ? C22 C21 H211 . . 108.8 ? N2 C21 H212 . . 108.8 ? C22 C21 H212 . . 108.8 ? H211 C21 H212 . . 107.7 ? C21 C22 H223 . . 109.5 ? C21 C22 H222 . . 109.5 ? H223 C22 H222 . . 109.5 ? C21 C22 H221 . . 109.5 ? H223 C22 H221 . . 109.5 ? H222 C22 H221 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 2.1(6) ? C2 N1 C1 C11 . . . . -177.0(3) ? C21 N2 C2 O2 . . . . -0.7(5) ? C21 N2 C2 N1 . . . . 178.3(3) ? C1 N1 C2 O2 . . . . 179.6(3) ? C1 N1 C2 N2 . . . . 0.5(5) ? O1 C1 C11 C12 . . . . 54.4(5) ? N1 C1 C11 C12 . . . . -126.5(4) ? C1 C11 C12 C13 . . . . 67.5(6) ? C11 C12 C13 C15 . . . . 63.5(7) ? C11 C12 C13 C14 . . . . -175.5(6) ? C2 N2 C21 C22 . . . . -82.8(4) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.86 2.41 3.092(4) 137.0 N1 H11 O2 2_566 0.86 2.01 2.867(3) 177.9 data_ethyl362K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6700(10) _cell_length_b 12.5515(9) _cell_length_c 5.1490(5) _cell_angle_alpha 90.036(7) _cell_angle_beta 91.078(4) _cell_angle_gamma 88.834(4) _cell_volume 560.11(9) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2412 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 27.425 _cell_measurement_temperature 362 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 1.00 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.104 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being low temperature phase. ; _diffrn_ambient_temperature 362 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 6484 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_max 0.920 _diffrn_measured_fraction_theta_full 0.920 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2361 _reflns_number_gt 1478 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1277 _refine_ls_R_factor_gt 0.0938 _refine_ls_wR_factor_gt 0.2883 _refine_ls_wR_factor_ref 0.3316 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.064 _refine_ls_number_reflns 2361 _refine_ls_number_parameters 118 _refine_ls_number_restraints 5 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1819P)^2^+0.1580P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.367 _refine_diff_density_min -0.341 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 360K was used as an initial model. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.4317(3) 0.5740(2) 0.2258(5) 0.0949(9) Uani d . 1 . . O O2 0.0275(3) 0.4100(2) 0.2453(5) 0.0914(9) Uani d . 1 . . O N1 0.1969(3) 0.5334(2) 0.3743(6) 0.0748(8) Uani d . 1 . . N H11 0.1295 0.5524 0.4868 0.090 Uiso calc R 1 . . H N2 0.2531(3) 0.4165(2) 0.0370(6) 0.0797(9) Uani d . 1 . . N H21 0.3405 0.4471 0.0254 0.096 Uiso calc R 1 . . H C1 0.3285(3) 0.5898(3) 0.3805(7) 0.0746(9) Uani d . 1 . . C C2 0.1545(4) 0.4502(3) 0.2152(7) 0.0743(9) Uani d . 1 . . C C11 0.3404(5) 0.6710(3) 0.5935(8) 0.0920(11) Uani d D 1 . . C H112 0.4198 0.6471 0.7166 0.110 Uiso calc R 1 . . H H111 0.2434 0.6736 0.6845 0.110 Uiso calc R 1 . . H C12 0.3768(6) 0.7819(4) 0.5084(11) 0.1242(17) Uani d D 1 . . C H121 0.3985 0.8246 0.6615 0.149 Uiso calc R 1 . . H H122 0.4697 0.7789 0.4064 0.149 Uiso calc R 1 . . H C13 0.2523(8) 0.8363(4) 0.3527(13) 0.152(2) Uani d D 1 . . C H131 0.2281 0.7923 0.2006 0.183 Uiso calc R 1 . . H C14 0.3107(14) 0.9435(6) 0.260(2) 0.251(6) Uani d D 1 . . C H143 0.2318 0.9787 0.1563 0.301 Uiso calc R 1 . . H H142 0.4010 0.9322 0.1577 0.301 Uiso calc R 1 . . H H141 0.3358 0.9870 0.4075 0.301 Uiso calc R 1 . . H C15 0.1059(8) 0.8539(7) 0.507(2) 0.227(5) Uani d D 1 . . C H153 0.0287 0.8887 0.3991 0.273 Uiso calc R 1 . . H H151 0.1280 0.8976 0.6555 0.273 Uiso calc R 1 . . H H152 0.0686 0.7864 0.5635 0.273 Uiso calc R 1 . . H C21 0.2176(4) 0.3298(3) -0.1379(8) 0.0913(11) Uani d D 1 . . C H211 0.2779 0.3365 -0.2936 0.110 Uiso calc R 1 . . H H212 0.1094 0.3346 -0.1887 0.110 Uiso calc R 1 . . H C22 0.2508(6) 0.2234(4) -0.0178(11) 0.1232(16) Uani d D 1 . . C H223 0.2254 0.1684 -0.1399 0.148 Uiso calc R 1 . . H H222 0.1900 0.2159 0.1348 0.148 Uiso calc R 1 . . H H221 0.3583 0.2176 0.0291 0.148 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0658(13) 0.1088(19) 0.1116(19) -0.0130(12) 0.0314(13) -0.0022(14) O2 0.0629(13) 0.0996(17) 0.1131(19) -0.0112(11) 0.0291(12) -0.0031(14) N1 0.0582(14) 0.0805(17) 0.0866(17) -0.0030(11) 0.0229(12) 0.0022(13) N2 0.0590(14) 0.0865(18) 0.0943(19) 0.0009(12) 0.0211(13) 0.0013(15) C1 0.0584(15) 0.0772(19) 0.089(2) 0.0043(13) 0.0159(14) 0.0167(16) C2 0.0570(15) 0.0818(19) 0.085(2) 0.0020(13) 0.0165(14) 0.0119(16) C11 0.080(2) 0.089(2) 0.107(3) -0.0002(18) 0.0159(19) 0.000(2) C12 0.117(4) 0.109(3) 0.148(4) -0.010(3) 0.034(3) -0.007(3) C13 0.177(6) 0.112(4) 0.166(6) 0.012(4) -0.020(5) 0.023(4) C14 0.389(17) 0.115(5) 0.250(11) -0.002(7) 0.047(11) 0.062(6) C15 0.129(6) 0.163(7) 0.387(15) 0.039(5) -0.026(8) 0.019(8) C21 0.072(2) 0.100(3) 0.102(3) 0.0020(18) 0.0164(18) -0.004(2) C22 0.129(4) 0.096(3) 0.144(4) 0.005(3) 0.010(3) 0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.222(4) ? O2 C2 . 1.232(4) ? N1 C1 . 1.355(4) ? N1 C2 . 1.378(5) ? N1 H11 . 0.8600 ? N2 C2 . 1.329(4) ? N2 C21 . 1.447(5) ? N2 H21 . 0.8600 ? C1 C11 . 1.500(5) ? C11 C12 . 1.501(6) ? C11 H112 . 0.9700 ? C11 H111 . 0.9700 ? C12 C13 . 1.487(8) ? C12 H121 . 0.9700 ? C12 H122 . 0.9700 ? C13 C15 . 1.522(11) ? C13 C14 . 1.527(11) ? C13 H131 . 0.9800 ? C14 H143 . 0.9600 ? C14 H142 . 0.9600 ? C14 H141 . 0.9600 ? C15 H153 . 0.9600 ? C15 H151 . 0.9600 ? C15 H152 . 0.9600 ? C21 C22 . 1.492(6) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 H223 . 0.9600 ? C22 H222 . 0.9600 ? C22 H221 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 129.8(3) ? C1 N1 H11 . . 115.1 ? C2 N1 H11 . . 115.1 ? C2 N2 C21 . . 121.9(3) ? C2 N2 H21 . . 119.0 ? C21 N2 H21 . . 119.0 ? O1 C1 N1 . . 122.1(4) ? O1 C1 C11 . . 122.4(3) ? N1 C1 C11 . . 115.5(3) ? O2 C2 N2 . . 122.9(4) ? O2 C2 N1 . . 118.7(3) ? N2 C2 N1 . . 118.4(3) ? C1 C11 C12 . . 115.6(4) ? C1 C11 H112 . . 108.4 ? C12 C11 H112 . . 108.4 ? C1 C11 H111 . . 108.4 ? C12 C11 H111 . . 108.4 ? H112 C11 H111 . . 107.4 ? C13 C12 C11 . . 114.7(4) ? C13 C12 H121 . . 108.6 ? C11 C12 H121 . . 108.6 ? C13 C12 H122 . . 108.6 ? C11 C12 H122 . . 108.6 ? H121 C12 H122 . . 107.6 ? C12 C13 C15 . . 112.3(6) ? C12 C13 C14 . . 108.8(7) ? C15 C13 C14 . . 109.5(7) ? C12 C13 H131 . . 108.7 ? C15 C13 H131 . . 108.7 ? C14 C13 H131 . . 108.7 ? C13 C14 H143 . . 109.5 ? C13 C14 H142 . . 109.5 ? H143 C14 H142 . . 109.5 ? C13 C14 H141 . . 109.5 ? H143 C14 H141 . . 109.5 ? H142 C14 H141 . . 109.5 ? C13 C15 H153 . . 109.5 ? C13 C15 H151 . . 109.5 ? H153 C15 H151 . . 109.5 ? C13 C15 H152 . . 109.5 ? H153 C15 H152 . . 109.5 ? H151 C15 H152 . . 109.5 ? N2 C21 C22 . . 112.2(4) ? N2 C21 H211 . . 109.2 ? C22 C21 H211 . . 109.2 ? N2 C21 H212 . . 109.2 ? C22 C21 H212 . . 109.2 ? H211 C21 H212 . . 107.9 ? C21 C22 H223 . . 109.5 ? C21 C22 H222 . . 109.5 ? H223 C22 H222 . . 109.5 ? C21 C22 H221 . . 109.5 ? H223 C22 H221 . . 109.5 ? H222 C22 H221 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 2.6(5) ? C2 N1 C1 C11 . . . . -175.9(3) ? C21 N2 C2 O2 . . . . 0.6(5) ? C21 N2 C2 N1 . . . . -179.9(3) ? C1 N1 C2 O2 . . . . 179.7(3) ? C1 N1 C2 N2 . . . . 0.2(5) ? O1 C1 C11 C12 . . . . 54.3(5) ? N1 C1 C11 C12 . . . . -127.2(4) ? C1 C11 C12 C13 . . . . 67.6(6) ? C11 C12 C13 C15 . . . . 63.7(8) ? C11 C12 C13 C14 . . . . -175.0(6) ? C2 N2 C21 C22 . . . . -83.2(4) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.86 2.39 3.077(4) 137.0 N1 H11 O2 2_566 0.86 2.01 2.866(3) 177.5 data_ethyl364K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7109(12) _cell_length_b 12.6454(10) _cell_length_c 5.1787(6) _cell_angle_alpha 90.134(7) _cell_angle_beta 90.557(4) _cell_angle_gamma 88.953(4) _cell_volume 570.32(11) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2832 _cell_measurement_theta_min 2.815 _cell_measurement_theta_max 27.465 _cell_measurement_temperature 364 _exptl_crystal_description 'triclinic' _exptl_crystal_colour 'P -1' _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 1.00 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.085 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being low temperature phase. ; _diffrn_ambient_temperature 364 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 7726 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.956 _diffrn_measured_fraction_theta_full 0.956 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2503 _reflns_number_gt 1474 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1327 _refine_ls_R_factor_gt 0.0914 _refine_ls_wR_factor_gt 0.2586 _refine_ls_wR_factor_ref 0.3005 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.061 _refine_ls_number_reflns 2503 _refine_ls_number_parameters 118 _refine_ls_number_restraints 5 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1424P)^2^+0.1845P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.327 _refine_diff_density_min -0.335 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 362K was used as an initial model. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.4319(3) 0.5736(2) 0.2249(5) 0.0986(9) Uani d . 1 . . O O2 0.0272(2) 0.4103(2) 0.2467(5) 0.0946(8) Uani d . 1 . . O N1 0.1969(3) 0.5332(2) 0.3748(5) 0.0782(8) Uani d . 1 . . N H11 0.1299 0.5519 0.4879 0.094 Uiso calc R 1 . . H N2 0.2527(3) 0.4164(2) 0.0378(5) 0.0816(8) Uani d . 1 . . N H21 0.3394 0.4473 0.0241 0.098 Uiso calc R 1 . . H C1 0.3282(3) 0.5898(3) 0.3795(7) 0.0773(9) Uani d . 1 . . C C2 0.1543(3) 0.4501(3) 0.2157(7) 0.0770(9) Uani d . 1 . . C C11 0.3393(4) 0.6712(3) 0.5878(8) 0.0947(11) Uani d D 1 . . C H112 0.4174 0.6478 0.7108 0.114 Uiso calc R 1 . . H H111 0.2423 0.6741 0.6781 0.114 Uiso calc R 1 . . H C12 0.3765(6) 0.7815(4) 0.5040(12) 0.1366(19) Uani d D 1 . . C H121 0.3983 0.8236 0.6563 0.164 Uiso calc R 1 . . H H122 0.4690 0.7784 0.4012 0.164 Uiso calc R 1 . . H C13 0.2526(8) 0.8360(5) 0.3510(13) 0.164(2) Uani d D 1 . . C H131 0.2278 0.7921 0.2005 0.197 Uiso calc R 1 . . H C14 0.3093(14) 0.9432(6) 0.256(2) 0.268(6) Uani d D 1 . . C H143 0.2300 0.9774 0.1545 0.321 Uiso calc R 1 . . H H142 0.3988 0.9324 0.1516 0.321 Uiso calc R 1 . . H H141 0.3345 0.9869 0.4013 0.321 Uiso calc R 1 . . H C15 0.1066(9) 0.8549(7) 0.506(2) 0.254(5) Uani d D 1 . . C H153 0.0311 0.8906 0.3998 0.305 Uiso calc R 1 . . H H151 0.1294 0.8977 0.6542 0.305 Uiso calc R 1 . . H H152 0.0674 0.7882 0.5612 0.305 Uiso calc R 1 . . H C21 0.2184(4) 0.3296(3) -0.1327(8) 0.0941(11) Uani d D 1 . . C H211 0.2785 0.3363 -0.2883 0.113 Uiso calc R 1 . . H H212 0.1108 0.3342 -0.1821 0.113 Uiso calc R 1 . . H C22 0.2509(6) 0.2236(4) -0.0161(11) 0.1308(17) Uani d D 1 . . C H223 0.2256 0.1694 -0.1385 0.157 Uiso calc R 1 . . H H222 0.1902 0.2157 0.1362 0.157 Uiso calc R 1 . . H H221 0.3579 0.2177 0.0291 0.157 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0688(13) 0.1134(18) 0.1148(19) -0.0135(12) 0.0318(13) -0.0016(14) O2 0.0659(13) 0.1035(17) 0.1153(19) -0.0122(11) 0.0291(12) -0.0042(14) N1 0.0613(14) 0.0823(16) 0.0916(18) -0.0019(11) 0.0244(12) 0.0028(14) N2 0.0597(14) 0.0895(18) 0.0961(19) -0.0029(12) 0.0200(13) 0.0002(15) C1 0.0602(16) 0.0814(19) 0.090(2) 0.0025(13) 0.0160(14) 0.0168(16) C2 0.0569(15) 0.086(2) 0.088(2) 0.0057(14) 0.0179(14) 0.0129(17) C11 0.083(2) 0.087(2) 0.115(3) -0.0018(17) 0.0169(19) 0.002(2) C12 0.124(4) 0.118(4) 0.169(5) -0.011(3) 0.040(3) -0.007(3) C13 0.175(6) 0.133(4) 0.183(6) 0.019(4) -0.013(5) 0.039(4) C14 0.416(18) 0.120(5) 0.268(11) -0.021(7) 0.024(11) 0.065(6) C15 0.138(6) 0.191(8) 0.432(16) 0.044(5) -0.026(8) 0.027(9) C21 0.073(2) 0.103(3) 0.106(3) 0.0018(17) 0.0162(18) -0.001(2) C22 0.135(4) 0.100(3) 0.157(4) 0.007(3) 0.013(3) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.226(4) ? O2 C2 . 1.236(4) ? N1 C1 . 1.360(4) ? N1 C2 . 1.388(5) ? N1 H11 . 0.8600 ? N2 C2 . 1.329(4) ? N2 C21 . 1.440(5) ? N2 H21 . 0.8600 ? C1 C11 . 1.494(5) ? C11 C12 . 1.503(6) ? C11 H112 . 0.9700 ? C11 H111 . 0.9700 ? C12 C13 . 1.492(8) ? C12 H121 . 0.9700 ? C12 H122 . 0.9700 ? C13 C15 . 1.525(11) ? C13 C14 . 1.536(10) ? C13 H131 . 0.9800 ? C14 H143 . 0.9600 ? C14 H142 . 0.9600 ? C14 H141 . 0.9600 ? C15 H153 . 0.9600 ? C15 H151 . 0.9600 ? C15 H152 . 0.9600 ? C21 C22 . 1.493(6) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 H223 . 0.9600 ? C22 H222 . 0.9600 ? C22 H221 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 129.9(3) ? C1 N1 H11 . . 115.0 ? C2 N1 H11 . . 115.0 ? C2 N2 C21 . . 121.9(3) ? C2 N2 H21 . . 119.1 ? C21 N2 H21 . . 119.1 ? O1 C1 N1 . . 122.0(3) ? O1 C1 C11 . . 122.3(3) ? N1 C1 C11 . . 115.7(3) ? O2 C2 N2 . . 123.0(3) ? O2 C2 N1 . . 118.7(3) ? N2 C2 N1 . . 118.3(3) ? C1 C11 C12 . . 116.5(4) ? C1 C11 H112 . . 108.2 ? C12 C11 H112 . . 108.2 ? C1 C11 H111 . . 108.2 ? C12 C11 H111 . . 108.2 ? H112 C11 H111 . . 107.3 ? C13 C12 C11 . . 114.6(4) ? C13 C12 H121 . . 108.6 ? C11 C12 H121 . . 108.6 ? C13 C12 H122 . . 108.6 ? C11 C12 H122 . . 108.6 ? H121 C12 H122 . . 107.6 ? C12 C13 C15 . . 112.7(6) ? C12 C13 C14 . . 109.7(6) ? C15 C13 C14 . . 108.4(7) ? C12 C13 H131 . . 108.6 ? C15 C13 H131 . . 108.6 ? C14 C13 H131 . . 108.6 ? C13 C14 H143 . . 109.5 ? C13 C14 H142 . . 109.5 ? H143 C14 H142 . . 109.5 ? C13 C14 H141 . . 109.5 ? H143 C14 H141 . . 109.5 ? H142 C14 H141 . . 109.5 ? C13 C15 H153 . . 109.5 ? C13 C15 H151 . . 109.5 ? H153 C15 H151 . . 109.5 ? C13 C15 H152 . . 109.5 ? H153 C15 H152 . . 109.5 ? H151 C15 H152 . . 109.5 ? N2 C21 C22 . . 113.5(4) ? N2 C21 H211 . . 108.9 ? C22 C21 H211 . . 108.9 ? N2 C21 H212 . . 108.9 ? C22 C21 H212 . . 108.9 ? H211 C21 H212 . . 107.7 ? C21 C22 H223 . . 109.5 ? C21 C22 H222 . . 109.5 ? H223 C22 H222 . . 109.5 ? C21 C22 H221 . . 109.5 ? H223 C22 H221 . . 109.5 ? H222 C22 H221 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 1.9(5) ? C2 N1 C1 C11 . . . . -176.9(3) ? C21 N2 C2 O2 . . . . -0.4(5) ? C21 N2 C2 N1 . . . . 179.1(3) ? C1 N1 C2 O2 . . . . -179.9(3) ? C1 N1 C2 N2 . . . . 0.6(5) ? O1 C1 C11 C12 . . . . 53.8(5) ? N1 C1 C11 C12 . . . . -127.3(4) ? C1 C11 C12 C13 . . . . 68.3(6) ? C11 C12 C13 C15 . . . . 64.2(8) ? C11 C12 C13 C14 . . . . -174.8(6) ? C2 N2 C21 C22 . . . . -83.0(4) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.86 2.39 3.083(3) 137.4 N1 H11 O2 2_566 0.86 2.00 2.860(3) 177.9 data_ethyl366K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7157(12) _cell_length_b 12.6307(7) _cell_length_c 5.1642(7) _cell_angle_alpha 89.780(10) _cell_angle_beta 90.522(6) _cell_angle_gamma 88.757(5) _cell_volume 568.34(11) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2373 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 27.39 _cell_measurement_temperature 366 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 1.00 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.088 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being low temperature phase. ; _diffrn_ambient_temperature 366 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 6593 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_max 0.912 _diffrn_measured_fraction_theta_full 0.912 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2383 _reflns_number_gt 1377 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1455 _refine_ls_R_factor_gt 0.1004 _refine_ls_wR_factor_gt 0.2914 _refine_ls_wR_factor_ref 0.3424 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.058 _refine_ls_number_reflns 2383 _refine_ls_number_parameters 118 _refine_ls_number_restraints 5 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1637P)^2^+0.2294P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.319 _refine_diff_density_min -0.351 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 364K was used as an initial model. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.4312(3) 0.5736(2) 0.2226(6) 0.1031(10) Uani d . 1 . . O O2 0.0275(3) 0.4105(2) 0.2482(6) 0.0982(10) Uani d . 1 . . O N1 0.1970(3) 0.5329(2) 0.3746(6) 0.0805(9) Uani d . 1 . . N H11 0.1307 0.5513 0.4892 0.097 Uiso calc R 1 . . H N2 0.2532(3) 0.4167(2) 0.0410(7) 0.0849(10) Uani d . 1 . . N H21 0.3401 0.4471 0.0282 0.102 Uiso calc R 1 . . H C1 0.3274(4) 0.5894(3) 0.3763(8) 0.0797(10) Uani d . 1 . . C C2 0.1540(4) 0.4501(3) 0.2168(8) 0.0822(11) Uani d . 1 . . C C11 0.3390(5) 0.6702(3) 0.5821(10) 0.1012(13) Uani d D 1 . . C H111 0.4173 0.6465 0.7051 0.121 Uiso calc R 1 . . H H112 0.2423 0.6733 0.6734 0.121 Uiso calc R 1 . . H C12 0.3760(7) 0.7804(4) 0.4976(15) 0.154(3) Uani d D 1 . . C H121 0.3992 0.8220 0.6500 0.185 Uiso calc R 1 . . H H122 0.4675 0.7773 0.3922 0.185 Uiso calc R 1 . . H C13 0.2512(9) 0.8357(6) 0.3477(17) 0.176(3) Uani d D 1 . . C H131 0.2261 0.7926 0.1964 0.212 Uiso calc R 1 . . H C14 0.3096(17) 0.9424(7) 0.252(3) 0.299(8) Uani d D 1 . . C H143 0.2313 0.9775 0.1498 0.358 Uiso calc R 1 . . H H142 0.3994 0.9309 0.1489 0.358 Uiso calc R 1 . . H H141 0.3349 0.9857 0.3983 0.358 Uiso calc R 1 . . H C15 0.1057(10) 0.8541(9) 0.503(3) 0.271(6) Uani d D 1 . . C H153 0.0293 0.8889 0.3954 0.325 Uiso calc R 1 . . H H151 0.1278 0.8977 0.6496 0.325 Uiso calc R 1 . . H H152 0.0680 0.7874 0.5609 0.325 Uiso calc R 1 . . H C21 0.2180(5) 0.3301(4) -0.1300(9) 0.1003(13) Uani d D 1 . . C H211 0.2777 0.3365 -0.2867 0.120 Uiso calc R 1 . . H H212 0.1102 0.3348 -0.1785 0.120 Uiso calc R 1 . . H C22 0.2515(7) 0.2241(4) -0.0079(13) 0.135(2) Uani d D 1 . . C H223 0.2260 0.1692 -0.1277 0.162 Uiso calc R 1 . . H H222 0.1915 0.2169 0.1459 0.162 Uiso calc R 1 . . H H221 0.3586 0.2183 0.0363 0.162 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0734(16) 0.117(2) 0.120(2) -0.0134(14) 0.0366(15) -0.0011(17) O2 0.0680(15) 0.107(2) 0.121(2) -0.0110(13) 0.0309(14) -0.0051(16) N1 0.0627(16) 0.0837(19) 0.096(2) -0.0030(13) 0.0232(14) -0.0002(16) N2 0.0622(16) 0.092(2) 0.101(2) -0.0023(14) 0.0219(15) -0.0020(17) C1 0.0637(18) 0.082(2) 0.093(2) 0.0011(15) 0.0165(17) 0.0163(18) C2 0.0587(17) 0.091(2) 0.097(3) 0.0060(16) 0.0196(17) 0.016(2) C11 0.089(3) 0.089(3) 0.126(4) -0.001(2) 0.020(2) 0.004(2) C12 0.145(5) 0.119(4) 0.201(7) -0.007(4) 0.053(5) -0.008(4) C13 0.181(7) 0.140(5) 0.207(8) 0.017(5) -0.013(6) 0.043(5) C14 0.47(2) 0.117(6) 0.308(15) -0.035(9) 0.053(15) 0.050(7) C15 0.140(8) 0.223(10) 0.45(2) 0.056(7) -0.018(10) 0.008(11) C21 0.077(2) 0.113(3) 0.112(3) 0.000(2) 0.018(2) -0.004(3) C22 0.138(5) 0.102(3) 0.166(5) 0.004(3) 0.013(4) 0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.222(4) ? O2 C2 . 1.233(4) ? N1 C1 . 1.355(5) ? N1 C2 . 1.385(5) ? N1 H11 . 0.8600 ? N2 C2 . 1.323(5) ? N2 C21 . 1.445(5) ? N2 H21 . 0.8600 ? C1 C11 . 1.481(6) ? C11 C12 . 1.499(7) ? C11 H111 . 0.9700 ? C11 H112 . 0.9700 ? C12 C13 . 1.490(10) ? C12 H121 . 0.9700 ? C12 H122 . 0.9700 ? C13 C15 . 1.520(13) ? C13 C14 . 1.532(13) ? C13 H131 . 0.9800 ? C14 H143 . 0.9600 ? C14 H142 . 0.9600 ? C14 H141 . 0.9600 ? C15 H153 . 0.9600 ? C15 H151 . 0.9600 ? C15 H152 . 0.9600 ? C21 C22 . 1.500(7) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 H223 . 0.9600 ? C22 H222 . 0.9600 ? C22 H221 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 129.9(3) ? C1 N1 H11 . . 115.0 ? C2 N1 H11 . . 115.0 ? C2 N2 C21 . . 121.2(3) ? C2 N2 H21 . . 119.4 ? C21 N2 H21 . . 119.4 ? O1 C1 N1 . . 122.6(4) ? O1 C1 C11 . . 121.6(4) ? N1 C1 C11 . . 115.7(3) ? O2 C2 N2 . . 123.4(4) ? O2 C2 N1 . . 118.9(3) ? N2 C2 N1 . . 117.6(3) ? C1 C11 C12 . . 116.8(5) ? C1 C11 H111 . . 108.1 ? C12 C11 H111 . . 108.1 ? C1 C11 H112 . . 108.1 ? C12 C11 H112 . . 108.1 ? H111 C11 H112 . . 107.3 ? C13 C12 C11 . . 114.5(5) ? C13 C12 H121 . . 108.6 ? C11 C12 H121 . . 108.6 ? C13 C12 H122 . . 108.6 ? C11 C12 H122 . . 108.6 ? H121 C12 H122 . . 107.6 ? C12 C13 C15 . . 113.4(7) ? C12 C13 C14 . . 108.9(8) ? C15 C13 C14 . . 109.2(9) ? C12 C13 H131 . . 108.4 ? C15 C13 H131 . . 108.4 ? C14 C13 H131 . . 108.4 ? C13 C14 H143 . . 109.5 ? C13 C14 H142 . . 109.5 ? H143 C14 H142 . . 109.5 ? C13 C14 H141 . . 109.5 ? H143 C14 H141 . . 109.5 ? H142 C14 H141 . . 109.5 ? C13 C15 H153 . . 109.5 ? C13 C15 H151 . . 109.5 ? H153 C15 H151 . . 109.5 ? C13 C15 H152 . . 109.5 ? H153 C15 H152 . . 109.5 ? H151 C15 H152 . . 109.5 ? N2 C21 C22 . . 112.4(4) ? N2 C21 H211 . . 109.1 ? C22 C21 H211 . . 109.1 ? N2 C21 H212 . . 109.1 ? C22 C21 H212 . . 109.1 ? H211 C21 H212 . . 107.9 ? C21 C22 H223 . . 109.5 ? C21 C22 H222 . . 109.5 ? H223 C22 H222 . . 109.5 ? C21 C22 H221 . . 109.5 ? H223 C22 H221 . . 109.5 ? H222 C22 H221 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 1.1(6) ? C2 N1 C1 C11 . . . . -177.2(4) ? C21 N2 C2 O2 . . . . 0.4(6) ? C21 N2 C2 N1 . . . . 179.5(3) ? C1 N1 C2 O2 . . . . -179.3(3) ? C1 N1 C2 N2 . . . . 1.6(6) ? O1 C1 C11 C12 . . . . 53.9(6) ? N1 C1 C11 C12 . . . . -127.7(4) ? C1 C11 C12 C13 . . . . 69.0(7) ? C11 C12 C13 C15 . . . . 63.5(10) ? C11 C12 C13 C14 . . . . -174.6(7) ? C2 N2 C21 C22 . . . . -83.6(5) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.86 2.40 3.085(4) 137.3 N1 H11 O2 2_566 0.86 2.00 2.855(4) 177.9 data_ethyl368K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6912(5) _cell_length_b 12.7757(6) _cell_length_c 5.15870(10) _cell_angle_alpha 88.386(2) _cell_angle_beta 91.168(6) _cell_angle_gamma 88.4630(19) _cell_volume 572.24(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2775 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 27.465 _cell_measurement_temperature 368 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 1.00 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.081 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being high temperature phase. ; _diffrn_ambient_temperature 368 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 7417 _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_max 0.868 _diffrn_measured_fraction_theta_full 0.868 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2283 _reflns_number_gt 1212 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1569 _refine_ls_R_factor_gt 0.0989 _refine_ls_wR_factor_gt 0.2561 _refine_ls_wR_factor_ref 0.3081 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.069 _refine_ls_number_reflns 2283 _refine_ls_number_parameters 131 _refine_ls_number_restraints 17 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1263P)^2^+0.2311P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.241 _refine_diff_density_min -0.276 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 366K was used as an initial model. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.4310(3) 0.5728(2) 0.2201(6) 0.1095(11) Uani d . 1 A . O O2 0.0279(3) 0.4107(2) 0.2539(6) 0.1050(10) Uani d . 1 A . O N1 0.1966(3) 0.5326(2) 0.3729(6) 0.0858(10) Uani d . 1 A . N H11 0.1302 0.5513 0.4852 0.103 Uiso calc R 1 . . H N2 0.2532(3) 0.4167(3) 0.0458(7) 0.0928(10) Uani d D 1 A . N H21 0.3403 0.4466 0.0329 0.111 Uiso calc R 1 . . H C1 0.3272(4) 0.5884(3) 0.3710(7) 0.0866(11) Uani d D 1 . . C C2 0.1542(4) 0.4496(3) 0.2198(8) 0.0861(11) Uani d . 1 . . C C11A 0.3370(5) 0.6696(3) 0.5749(9) 0.1098(14) Uani d PD 0.874(6) A 1 C H111 0.4138 0.6454 0.7035 0.132 Uiso calc PR 0.874(6) A 1 H H112 0.2388 0.6729 0.6609 0.132 Uiso calc PR 0.874(6) A 1 H C12A 0.3760(7) 0.7806(4) 0.4893(15) 0.158(3) Uani d PD 0.874(6) A 1 C H121 0.4671 0.7782 0.3839 0.190 Uiso calc PR 0.874(6) A 1 H H122 0.3993 0.8208 0.6412 0.190 Uiso calc PR 0.874(6) A 1 H C13A 0.2445(9) 0.8353(6) 0.3344(16) 0.179(4) Uani d PD 0.874(6) A 1 C H131 0.2167 0.7941 0.1839 0.214 Uiso calc PR 0.874(6) A 1 H C14A 0.3006(18) 0.9430(6) 0.245(3) 0.288(8) Uani d PD 0.874(6) A 1 C H142 0.3886 0.9340 0.1373 0.433 Uiso calc PR 0.874(6) A 1 H H141 0.3286 0.9824 0.3935 0.433 Uiso calc PR 0.874(6) A 1 H H143 0.2198 0.9799 0.1477 0.433 Uiso calc PR 0.874(6) A 1 H C15A 0.1029(11) 0.8553(9) 0.500(3) 0.265(6) Uani d PD 0.874(6) A 1 C H153 0.0226 0.8887 0.3940 0.397 Uiso calc PR 0.874(6) A 1 H H151 0.1296 0.8998 0.6394 0.397 Uiso calc PR 0.874(6) A 1 H H152 0.0678 0.7898 0.5688 0.397 Uiso calc PR 0.874(6) A 1 H C11B 0.3370(5) 0.6696(3) 0.5749(9) 0.1098(14) Uani d PD 0.126(6) A 2 C H113 0.4414 0.6943 0.5864 0.132 Uiso calc PR 0.126(6) A 2 H H114 0.3120 0.6385 0.7419 0.132 Uiso calc PR 0.126(6) A 2 H C12B 0.226(2) 0.7623(11) 0.511(5) 0.158(3) Uani d PD 0.126(6) A 2 C H123 0.1857 0.7549 0.3363 0.190 Uiso calc PR 0.126(6) A 2 H H124 0.1400 0.7581 0.6276 0.190 Uiso calc PR 0.126(6) A 2 H C13B 0.293(4) 0.8711(8) 0.531(7) 0.179(4) Uani d PD 0.126(6) A 2 C H132 0.2095 0.9233 0.5035 0.214 Uiso calc PR 0.126(6) A 2 H C14B 0.411(8) 0.888(4) 0.317(11) 0.288(8) Uani d PD 0.126(6) A 2 C H144 0.4524 0.9566 0.3303 0.433 Uiso calc PR 0.126(6) A 2 H H145 0.3611 0.8819 0.1507 0.433 Uiso calc PR 0.126(6) A 2 H H146 0.4925 0.8361 0.3371 0.433 Uiso calc PR 0.126(6) A 2 H C15B 0.368(6) 0.888(3) 0.797(10) 0.265(6) Uani d PD 0.126(6) A 2 C H154 0.3793 0.9611 0.8222 0.397 Uiso calc PR 0.126(6) A 2 H H155 0.4667 0.8526 0.8076 0.397 Uiso calc PR 0.126(6) A 2 H H156 0.3031 0.8593 0.9295 0.397 Uiso calc PR 0.126(6) A 2 H C21 0.2181(5) 0.3309(3) -0.1245(9) 0.1067(14) Uani d D 1 . . C H211 0.2772 0.3384 -0.2811 0.128 Uiso calc R 1 A . H H212 0.1099 0.3358 -0.1742 0.128 Uiso calc R 1 . . H C22 0.2527(7) 0.2252(4) -0.0027(12) 0.145(2) Uani d D 1 A . C H223 0.2259 0.1722 -0.1225 0.174 Uiso calc R 1 . . H H222 0.1940 0.2169 0.1517 0.174 Uiso calc R 1 . . H H221 0.3605 0.2187 0.0409 0.174 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0768(16) 0.125(2) 0.129(2) -0.0137(14) 0.0384(16) -0.0026(18) O2 0.0712(16) 0.116(2) 0.129(2) -0.0131(14) 0.0339(15) -0.0055(17) N1 0.0638(16) 0.091(2) 0.103(2) -0.0010(14) 0.0245(15) 0.0014(18) N2 0.0661(17) 0.104(2) 0.109(2) -0.0023(15) 0.0234(16) -0.0014(19) C1 0.068(2) 0.085(2) 0.106(3) 0.0029(17) 0.0175(19) 0.017(2) C2 0.0628(19) 0.092(2) 0.102(3) 0.0040(17) 0.0193(19) 0.016(2) C11A 0.092(3) 0.099(3) 0.139(4) 0.001(2) 0.022(3) 0.004(3) C12A 0.151(6) 0.120(5) 0.209(8) -0.018(4) 0.075(6) -0.013(5) C13A 0.201(9) 0.152(7) 0.178(8) 0.009(6) -0.019(7) 0.049(6) C14A 0.48(2) 0.098(6) 0.287(14) -0.008(8) 0.042(14) 0.056(7) C15A 0.151(8) 0.209(10) 0.432(19) 0.052(7) 0.029(10) -0.005(11) C11B 0.092(3) 0.099(3) 0.139(4) 0.001(2) 0.022(3) 0.004(3) C12B 0.151(6) 0.120(5) 0.209(8) -0.018(4) 0.075(6) -0.013(5) C13B 0.201(9) 0.152(7) 0.178(8) 0.009(6) -0.019(7) 0.049(6) C14B 0.48(2) 0.098(6) 0.287(14) -0.008(8) 0.042(14) 0.056(7) C15B 0.151(8) 0.209(10) 0.432(19) 0.052(7) 0.029(10) -0.005(11) C21 0.085(3) 0.113(3) 0.123(3) 0.002(2) 0.021(2) 0.000(3) C22 0.150(5) 0.115(4) 0.169(5) 0.005(3) 0.017(4) 0.000(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.219(4) ? O2 C2 . 1.231(4) ? N1 C1 . 1.356(5) ? N1 C2 . 1.393(5) ? N1 H11 . 0.8600 ? N2 C2 . 1.326(5) ? N2 C21 . 1.459(6) ? N2 H21 . 0.8600 ? C1 C11A . 1.501(6) ? C11A C12A . 1.522(6) ? C11A H111 . 0.9700 ? C11A H112 . 0.9700 ? C11A C12B . 1.530(18) ? C12A C13A . 1.524(10) ? C12A H121 . 0.9700 ? C12A H122 . 0.9700 ? C13A C15A . 1.531(14) ? C13A C14A . 1.533(12) ? C13A H131 . 0.9800 ? C14A H142 . 0.9600 ? C14A H141 . 0.9600 ? C14A H143 . 0.9600 ? C15A H153 . 0.9600 ? C15A H151 . 0.9600 ? C15A H152 . 0.9600 ? C12B C13B . 1.53(2) ? C12B H123 . 0.9700 ? C12B H124 . 0.9700 ? C13B C15B . 1.53(6) ? C13B C14B . 1.53(7) ? C13B H132 . 0.9800 ? C14B H144 . 0.9600 ? C14B H145 . 0.9600 ? C14B H146 . 0.9600 ? C15B H154 . 0.9600 ? C15B H155 . 0.9600 ? C15B H156 . 0.9600 ? C21 C22 . 1.493(7) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 H223 . 0.9600 ? C22 H222 . 0.9600 ? C22 H221 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 129.5(3) ? C1 N1 H11 . . 115.2 ? C2 N1 H11 . . 115.2 ? C2 N2 C21 . . 121.6(3) ? C2 N2 H21 . . 119.2 ? C21 N2 H21 . . 119.2 ? O1 C1 N1 . . 123.1(4) ? O1 C1 C11A . . 122.0(4) ? N1 C1 C11A . . 114.8(3) ? O2 C2 N2 . . 123.7(4) ? O2 C2 N1 . . 118.5(3) ? N2 C2 N1 . . 117.8(3) ? C1 C11A C12A . . 118.0(4) ? C1 C11A H111 . . 107.8 ? C12A C11A H111 . . 107.8 ? C1 C11A H112 . . 107.8 ? C12A C11A H112 . . 107.8 ? H111 C11A H112 . . 107.2 ? C11A C12A C13A . . 112.2(5) ? C11A C12A H121 . . 109.2 ? C13A C12A H121 . . 109.2 ? C11A C12A H122 . . 109.2 ? C13A C12A H122 . . 109.2 ? H121 C12A H122 . . 107.9 ? C12A C13A C15A . . 112.2(7) ? C12A C13A C14A . . 107.4(7) ? C15A C13A C14A . . 106.7(10) ? C12A C13A H131 . . 110.1 ? C15A C13A H131 . . 110.1 ? C14A C13A H131 . . 110.1 ? C13A C14A H142 . . 109.5 ? C13A C14A H141 . . 109.5 ? H142 C14A H141 . . 109.5 ? C13A C14A H143 . . 109.5 ? H142 C14A H143 . . 109.5 ? H141 C14A H143 . . 109.5 ? C13A C15A H153 . . 109.5 ? C13A C15A H151 . . 109.5 ? H153 C15A H151 . . 109.5 ? C13A C15A H152 . . 109.5 ? H153 C15A H152 . . 109.5 ? H151 C15A H152 . . 109.5 ? C13B C12B H123 . . 108.3 ? C13B C12B H124 . . 108.3 ? H123 C12B H124 . . 107.4 ? C12B C13B C15B . . 111.8(7) ? C12B C13B C14B . . 109.9(7) ? C15B C13B C14B . . 110.4(7) ? C12B C13B H132 . . 108.2 ? C15B C13B H132 . . 108.2 ? C14B C13B H132 . . 108.2 ? C13B C14B H144 . . 109.5 ? C13B C14B H145 . . 109.5 ? H144 C14B H145 . . 109.5 ? C13B C14B H146 . . 109.5 ? H144 C14B H146 . . 109.5 ? H145 C14B H146 . . 109.5 ? C13B C15B H154 . . 109.5 ? C13B C15B H155 . . 109.5 ? H154 C15B H155 . . 109.5 ? C13B C15B H156 . . 109.5 ? H154 C15B H156 . . 109.5 ? H155 C15B H156 . . 109.5 ? N2 C21 C22 . . 113.3(4) ? N2 C21 H211 . . 108.9 ? C22 C21 H211 . . 108.9 ? N2 C21 H212 . . 108.9 ? C22 C21 H212 . . 108.9 ? H211 C21 H212 . . 107.7 ? C21 C22 H223 . . 109.5 ? C21 C22 H222 . . 109.5 ? H223 C22 H222 . . 109.5 ? C21 C22 H221 . . 109.5 ? H223 C22 H221 . . 109.5 ? H222 C22 H221 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 1.4(6) ? C2 N1 C1 C11A . . . . -177.0(4) ? C21 N2 C2 O2 . . . . 0.9(6) ? C21 N2 C2 N1 . . . . -179.4(3) ? C1 N1 C2 O2 . . . . -179.4(4) ? C1 N1 C2 N2 . . . . 0.9(6) ? O1 C1 C11A C12A . . . . 52.5(6) ? N1 C1 C11A C12A . . . . -129.1(5) ? C1 C11A C12A C13A . . . . 70.6(7) ? C11A C12A C13A C15A . . . . 66.5(9) ? C11A C12A C13A C14A . . . . -176.5(7) ? C2 N2 C21 C22 . . . . -84.0(5) ? C2 N1 C1 C11B . . . . -177.0(4) ? O1 C1 C11B C12B . . . . 109.5(13) ? N1 C1 C11B C12B . . . . -72.0(13) ? C1 C11B C12B C13B . . . . -132.0(18) ? C11B C12B C13B C15B . . . . -55(3) ? C11B C12B C13B C14B . . . . 68(3) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.86 2.41 3.098(4) 137.1 N1 H11 O2 2_566 0.86 2.00 2.863(4) 177.8 data_ethyl370K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.605(2) _cell_length_b 12.855(2) _cell_length_c 5.1699(10) _cell_angle_alpha 87.263(16) _cell_angle_beta 92.266(9) _cell_angle_gamma 88.060(8) _cell_volume 570.39(19) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2605 _cell_measurement_theta_min 2.895 _cell_measurement_theta_max 27.445 _cell_measurement_temperature 370 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 1.00 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.084 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being high temperature phase. ; _diffrn_ambient_temperature 370 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 9055 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.863 _diffrn_measured_fraction_theta_full 0.863 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2263 _reflns_number_gt 1016 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1977 _refine_ls_R_factor_gt 0.1160 _refine_ls_wR_factor_gt 0.3094 _refine_ls_wR_factor_ref 0.3859 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_number_reflns 2263 _refine_ls_number_parameters 131 _refine_ls_number_restraints 17 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1627P)^2^+0.2588P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.278 _refine_diff_density_min -0.271 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 368K was used as an initial model. The minor part of the disordered 3-methylbutyl group was deleted to avoid some viases for disorder analysis. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.4305(4) 0.5716(3) 0.2153(8) 0.1207(14) Uani d . 1 A . O O2 0.0278(4) 0.4110(3) 0.2582(8) 0.1167(14) Uani d . 1 A . O N1 0.1965(4) 0.5326(3) 0.3720(8) 0.0955(13) Uani d . 1 A . N H11 0.1305 0.5508 0.4836 0.115 Uiso calc R 1 . . H N2 0.2530(4) 0.4165(3) 0.0519(8) 0.1012(14) Uani d D 1 A . N H21 0.3406 0.4461 0.0375 0.121 Uiso calc R 1 . . H C1 0.3268(5) 0.5873(4) 0.3646(10) 0.0971(15) Uani d D 1 . . C C2 0.1552(5) 0.4504(4) 0.2223(11) 0.0985(15) Uani d . 1 . . C C11A 0.3352(7) 0.6690(4) 0.5612(11) 0.124(2) Uani d PD 0.813(8) A 1 C H111 0.4121 0.6450 0.6949 0.148 Uiso calc PR 0.813(8) A 1 H H112 0.2355 0.6728 0.6420 0.148 Uiso calc PR 0.813(8) A 1 H C12A 0.3745(11) 0.7794(5) 0.472(2) 0.177(4) Uani d PD 0.813(8) A 1 C H121 0.4654 0.7767 0.3666 0.212 Uiso calc PR 0.813(8) A 1 H H122 0.3997 0.8191 0.6216 0.212 Uiso calc PR 0.813(8) A 1 H C13A 0.2393(13) 0.8341(8) 0.314(2) 0.190(5) Uani d PD 0.813(8) A 1 C H131 0.2089 0.7940 0.1649 0.228 Uiso calc PR 0.813(8) A 1 H C14A 0.292(3) 0.9422(9) 0.226(4) 0.333(12) Uani d PD 0.813(8) A 1 C H142 0.3805 0.9348 0.1191 0.499 Uiso calc PR 0.813(8) A 1 H H141 0.3210 0.9802 0.3748 0.499 Uiso calc PR 0.813(8) A 1 H H143 0.2090 0.9793 0.1283 0.499 Uiso calc PR 0.813(8) A 1 H C15A 0.0990(16) 0.8579(13) 0.477(4) 0.307(10) Uani d PD 0.813(8) A 1 C H153 0.0174 0.8920 0.3691 0.461 Uiso calc PR 0.813(8) A 1 H H151 0.1291 0.9026 0.6126 0.461 Uiso calc PR 0.813(8) A 1 H H152 0.0623 0.7940 0.5525 0.461 Uiso calc PR 0.813(8) A 1 H C11B 0.3352(7) 0.6690(4) 0.5612(11) 0.124(2) Uani d PD 0.187(8) A 2 C H113 0.4408 0.6926 0.5774 0.148 Uiso calc PR 0.187(8) A 2 H H114 0.3077 0.6393 0.7286 0.148 Uiso calc PR 0.187(8) A 2 H C12B 0.224(2) 0.7617(10) 0.482(5) 0.177(4) Uani d PD 0.187(8) A 2 C H123 0.1895 0.7551 0.3029 0.212 Uiso calc PR 0.187(8) A 2 H H124 0.1336 0.7572 0.5866 0.212 Uiso calc PR 0.187(8) A 2 H C13B 0.290(4) 0.8698(8) 0.507(7) 0.190(5) Uani d PD 0.187(8) A 2 C H132 0.2034 0.9212 0.4914 0.228 Uiso calc PR 0.187(8) A 2 H C14B 0.399(8) 0.893(4) 0.286(10) 0.333(12) Uani d PD 0.187(8) A 2 C H144 0.4386 0.9616 0.3013 0.499 Uiso calc PR 0.187(8) A 2 H H145 0.3428 0.8897 0.1230 0.499 Uiso calc PR 0.187(8) A 2 H H146 0.4843 0.8427 0.2957 0.499 Uiso calc PR 0.187(8) A 2 H C15B 0.376(5) 0.881(3) 0.769(9) 0.307(10) Uani d PD 0.187(8) A 2 C H154 0.3904 0.9533 0.7959 0.461 Uiso calc PR 0.187(8) A 2 H H155 0.4749 0.8445 0.7707 0.461 Uiso calc PR 0.187(8) A 2 H H156 0.3148 0.8518 0.9044 0.461 Uiso calc PR 0.187(8) A 2 H C21 0.2180(6) 0.3318(4) -0.1106(12) 0.1171(19) Uani d D 1 . . C H211 0.2776 0.3384 -0.2656 0.140 Uiso calc R 1 A . H H212 0.1085 0.3371 -0.1638 0.140 Uiso calc R 1 . . H C22 0.2534(9) 0.2264(5) 0.0197(17) 0.167(3) Uani d D 1 A . C H223 0.2272 0.1734 -0.0975 0.200 Uiso calc R 1 . . H H222 0.1934 0.2187 0.1717 0.200 Uiso calc R 1 . . H H221 0.3622 0.2198 0.0684 0.200 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.080(2) 0.146(3) 0.139(3) -0.0148(19) 0.037(2) -0.006(2) O2 0.077(2) 0.129(3) 0.147(3) -0.0122(18) 0.034(2) -0.011(2) N1 0.070(2) 0.100(3) 0.117(3) -0.0018(19) 0.025(2) -0.001(2) N2 0.071(2) 0.114(3) 0.120(3) -0.003(2) 0.023(2) -0.004(3) C1 0.070(3) 0.098(3) 0.123(4) 0.000(2) 0.017(3) 0.008(3) C2 0.062(2) 0.114(4) 0.119(4) 0.005(2) 0.027(2) 0.016(3) C11A 0.095(4) 0.110(4) 0.166(6) -0.002(3) 0.021(3) 0.002(4) C12A 0.168(9) 0.138(7) 0.231(11) -0.024(6) 0.088(9) 0.000(7) C13A 0.191(11) 0.173(9) 0.197(12) -0.007(8) -0.029(9) 0.054(9) C14A 0.54(4) 0.117(9) 0.34(2) 0.007(13) 0.04(2) 0.053(11) C15A 0.143(11) 0.246(16) 0.53(3) 0.046(10) 0.048(14) -0.045(17) C11B 0.095(4) 0.110(4) 0.166(6) -0.002(3) 0.021(3) 0.002(4) C12B 0.168(9) 0.138(7) 0.231(11) -0.024(6) 0.088(9) 0.000(7) C13B 0.191(11) 0.173(9) 0.197(12) -0.007(8) -0.029(9) 0.054(9) C14B 0.54(4) 0.117(9) 0.34(2) 0.007(13) 0.04(2) 0.053(11) C15B 0.143(11) 0.246(16) 0.53(3) 0.046(10) 0.048(14) -0.045(17) C21 0.088(3) 0.125(4) 0.138(5) 0.006(3) 0.016(3) -0.004(4) C22 0.153(7) 0.126(5) 0.222(9) 0.008(5) 0.020(6) -0.018(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.221(6) ? O2 C2 . 1.241(6) ? N1 C1 . 1.345(6) ? N1 C2 . 1.386(7) ? N1 H11 . 0.8600 ? N2 C2 . 1.321(6) ? N2 C21 . 1.440(7) ? N2 H21 . 0.8600 ? C1 C11A . 1.497(7) ? C11A C12A . 1.525(9) ? C11A H111 . 0.9700 ? C11A H112 . 0.9700 ? C11A C12B . 1.530(17) ? C12A C13A . 1.526(14) ? C12A H121 . 0.9700 ? C12A H122 . 0.9700 ? C13A C15A . 1.53(2) ? C13A C14A . 1.532(18) ? C13A H131 . 0.9800 ? C14A H142 . 0.9600 ? C14A H141 . 0.9600 ? C14A H143 . 0.9600 ? C15A H153 . 0.9600 ? C15A H151 . 0.9600 ? C15A H152 . 0.9600 ? C12B C13B . 1.53(2) ? C12B H123 . 0.9700 ? C12B H124 . 0.9700 ? C13B C15B . 1.53(6) ? C13B C14B . 1.53(7) ? C13B H132 . 0.9800 ? C14B H144 . 0.9600 ? C14B H145 . 0.9600 ? C14B H146 . 0.9600 ? C15B H154 . 0.9600 ? C15B H155 . 0.9600 ? C15B H156 . 0.9600 ? C21 C22 . 1.500(9) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 H223 . 0.9600 ? C22 H222 . 0.9600 ? C22 H221 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 128.1(4) ? C1 N1 H11 . . 115.9 ? C2 N1 H11 . . 115.9 ? C2 N2 C21 . . 122.3(4) ? C2 N2 H21 . . 118.9 ? C21 N2 H21 . . 118.9 ? O1 C1 N1 . . 123.7(5) ? O1 C1 C11A . . 122.6(5) ? N1 C1 C11A . . 113.7(4) ? O2 C2 N2 . . 122.9(6) ? O2 C2 N1 . . 117.9(4) ? N2 C2 N1 . . 119.2(4) ? C1 C11A C12A . . 118.6(6) ? C1 C11A H111 . . 107.7 ? C12A C11A H111 . . 107.7 ? C1 C11A H112 . . 107.7 ? C12A C11A H112 . . 107.7 ? H111 C11A H112 . . 107.1 ? C11A C12A C13A . . 111.5(7) ? C11A C12A H121 . . 109.3 ? C13A C12A H121 . . 109.3 ? C11A C12A H122 . . 109.3 ? C13A C12A H122 . . 109.3 ? H121 C12A H122 . . 108.0 ? C12A C13A C15A . . 112.9(10) ? C12A C13A C14A . . 107.4(11) ? C15A C13A C14A . . 103.6(14) ? C12A C13A H131 . . 110.9 ? C15A C13A H131 . . 110.9 ? C14A C13A H131 . . 110.9 ? C13A C14A H142 . . 109.5 ? C13A C14A H141 . . 109.5 ? H142 C14A H141 . . 109.5 ? C13A C14A H143 . . 109.5 ? H142 C14A H143 . . 109.5 ? H141 C14A H143 . . 109.5 ? C13A C15A H153 . . 109.5 ? C13A C15A H151 . . 109.5 ? H153 C15A H151 . . 109.5 ? C13A C15A H152 . . 109.5 ? H153 C15A H152 . . 109.5 ? H151 C15A H152 . . 109.5 ? C13B C12B H123 . . 108.2 ? C13B C12B H124 . . 108.2 ? H123 C12B H124 . . 107.4 ? C12B C13B C15B . . 112.2(7) ? C12B C13B C14B . . 109.9(7) ? C15B C13B C14B . . 110.3(7) ? C12B C13B H132 . . 108.1 ? C15B C13B H132 . . 108.1 ? C14B C13B H132 . . 108.1 ? C13B C14B H144 . . 109.5 ? C13B C14B H145 . . 109.5 ? H144 C14B H145 . . 109.5 ? C13B C14B H146 . . 109.5 ? H144 C14B H146 . . 109.5 ? H145 C14B H146 . . 109.5 ? C13B C15B H154 . . 109.5 ? C13B C15B H155 . . 109.5 ? H154 C15B H155 . . 109.5 ? C13B C15B H156 . . 109.5 ? H154 C15B H156 . . 109.5 ? H155 C15B H156 . . 109.5 ? N2 C21 C22 . . 113.4(5) ? N2 C21 H211 . . 108.9 ? C22 C21 H211 . . 108.9 ? N2 C21 H212 . . 108.9 ? C22 C21 H212 . . 108.9 ? H211 C21 H212 . . 107.7 ? C21 C22 H223 . . 109.5 ? C21 C22 H222 . . 109.5 ? H223 C22 H222 . . 109.5 ? C21 C22 H221 . . 109.5 ? H223 C22 H221 . . 109.5 ? H222 C22 H221 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 0.7(8) ? C2 N1 C1 C11A . . . . -178.1(5) ? C21 N2 C2 O2 . . . . 1.3(8) ? C21 N2 C2 N1 . . . . -179.8(5) ? C1 N1 C2 O2 . . . . -179.2(4) ? C1 N1 C2 N2 . . . . 1.8(8) ? O1 C1 C11A C12A . . . . 50.8(8) ? N1 C1 C11A C12A . . . . -130.3(6) ? C1 C11A C12A C13A . . . . 72.2(10) ? C11A C12A C13A C15A . . . . 68.4(13) ? C11A C12A C13A C14A . . . . -178.0(11) ? C2 N2 C21 C22 . . . . -83.3(6) ? C2 N1 C1 C11B . . . . -178.1(5) ? O1 C1 C11B C12B . . . . 107.1(13) ? N1 C1 C11B C12B . . . . -74.1(12) ? C1 C11B C12B C13B . . . . -134.6(18) ? C11B C12B C13B C15B . . . . -47(3) ? C11B C12B C13B C14B . . . . 76(3) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.86 2.42 3.107(5) 137.7 N1 H11 O2 2_566 0.86 2.01 2.870(5) 178.0 data_ethyl372K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6137(18) _cell_length_b 12.994(3) _cell_length_c 5.1906(11) _cell_angle_alpha 86.197(10) _cell_angle_beta 91.616(12) _cell_angle_gamma 88.099(6) _cell_volume 579.1(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2962 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 27.48 _cell_measurement_temperature 372 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.068 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being high temperature phase. ; _diffrn_ambient_temperature 372 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 8178 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.868 _diffrn_measured_fraction_theta_full 0.868 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2312 _reflns_number_gt 1114 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1865 _refine_ls_R_factor_gt 0.1244 _refine_ls_wR_factor_gt 0.3045 _refine_ls_wR_factor_ref 0.3336 _refine_ls_goodness_of_fit_ref 1.753 _refine_ls_restrained_S_all 1.772 _refine_ls_number_reflns 2312 _refine_ls_number_parameters 131 _refine_ls_number_restraints 17 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.387 _refine_diff_density_min -0.293 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 370K was used as an initial model. The minor part of the disordered 3-methylbutyl group was deleted to avoid some viases for disorder analysis. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.4299(3) 0.5710(2) 0.2076(6) 0.1290(10) Uani d . 1 A . O O2 0.0275(2) 0.41152(19) 0.2663(5) 0.1204(9) Uani d . 1 A . O N1 0.1962(3) 0.5315(2) 0.3685(6) 0.1017(9) Uani d . 1 A . N H11 0.1302 0.5501 0.4793 0.122 Uiso calc R 1 . . H N2 0.2536(3) 0.4159(2) 0.0604(6) 0.1066(10) Uani d D 1 A . N H21 0.3419 0.4445 0.0464 0.128 Uiso calc R 1 . . H C1 0.3266(4) 0.5868(2) 0.3546(7) 0.1013(11) Uani d D 1 . . C C2 0.1551(4) 0.4493(3) 0.2288(7) 0.1005(10) Uani d . 1 . . C C11A 0.3342(5) 0.6684(2) 0.5442(8) 0.1283(14) Uani d PD 0.774(6) A 1 C H111 0.4095 0.6449 0.6797 0.154 Uiso calc PR 0.774(6) A 1 H H112 0.2338 0.6734 0.6235 0.154 Uiso calc PR 0.774(6) A 1 H C12A 0.3760(7) 0.7768(3) 0.4458(17) 0.203(4) Uani d PD 0.774(6) A 1 C H121 0.4117 0.8143 0.5903 0.243 Uiso calc PR 0.774(6) A 1 H H122 0.4606 0.7720 0.3273 0.243 Uiso calc PR 0.774(6) A 1 H C13A 0.2389(8) 0.8363(6) 0.3087(18) 0.219(5) Uani d PD 0.774(6) A 1 C H131 0.2028 0.7964 0.1663 0.263 Uiso calc PR 0.774(6) A 1 H C14A 0.284(2) 0.9425(7) 0.195(3) 0.382(11) Uani d PD 0.774(6) A 1 C H142 0.3715 0.9348 0.0870 0.574 Uiso calc PR 0.774(6) A 1 H H141 0.3097 0.9854 0.3320 0.574 Uiso calc PR 0.774(6) A 1 H H143 0.1976 0.9739 0.0932 0.574 Uiso calc PR 0.774(6) A 1 H C15A 0.0997(13) 0.8609(12) 0.471(3) 0.343(8) Uani d PD 0.774(6) A 1 C H153 0.0187 0.8947 0.3623 0.515 Uiso calc PR 0.774(6) A 1 H H151 0.1302 0.9055 0.6023 0.515 Uiso calc PR 0.774(6) A 1 H H152 0.0623 0.7981 0.5506 0.515 Uiso calc PR 0.774(6) A 1 H C11B 0.3342(5) 0.6684(2) 0.5442(8) 0.1283(14) Uani d PD 0.226(6) A 2 C H113 0.4411 0.6872 0.5726 0.154 Uiso calc PR 0.226(6) A 2 H H114 0.2940 0.6429 0.7082 0.154 Uiso calc PR 0.226(6) A 2 H C12B 0.2364(14) 0.7629(5) 0.434(3) 0.203(4) Uani d PD 0.226(6) A 2 C H123 0.2284 0.7604 0.2479 0.243 Uiso calc PR 0.226(6) A 2 H H124 0.1322 0.7575 0.4991 0.243 Uiso calc PR 0.226(6) A 2 H C13B 0.2968(16) 0.8678(6) 0.495(2) 0.219(5) Uani d PD 0.226(6) A 2 C H132 0.2084 0.9173 0.4930 0.263 Uiso calc PR 0.226(6) A 2 H C14B 0.408(3) 0.904(2) 0.287(4) 0.382(11) Uani d PD 0.226(6) A 2 C H144 0.4415 0.9723 0.3196 0.574 Uiso calc PR 0.226(6) A 2 H H145 0.3566 0.9061 0.1206 0.574 Uiso calc PR 0.226(6) A 2 H H146 0.4974 0.8577 0.2904 0.574 Uiso calc PR 0.226(6) A 2 H C15B 0.378(3) 0.8645(19) 0.761(3) 0.343(8) Uani d PD 0.226(6) A 2 C H154 0.3968 0.9336 0.8066 0.515 Uiso calc PR 0.226(6) A 2 H H155 0.4755 0.8264 0.7572 0.515 Uiso calc PR 0.226(6) A 2 H H156 0.3137 0.8314 0.8874 0.515 Uiso calc PR 0.226(6) A 2 H C21 0.2183(4) 0.3335(3) -0.1002(8) 0.1250(14) Uani d D 1 . . C H211 0.2782 0.3406 -0.2555 0.150 Uiso calc R 1 A . H H212 0.1091 0.3391 -0.1519 0.150 Uiso calc R 1 . . H C22 0.2530(7) 0.2286(4) 0.0324(12) 0.171(2) Uani d D 1 A . C H223 0.2273 0.1765 -0.0827 0.205 Uiso calc R 1 . . H H222 0.1925 0.2205 0.1845 0.205 Uiso calc R 1 . . H H221 0.3615 0.2219 0.0803 0.205 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0883(14) 0.142(2) 0.160(2) -0.0232(14) 0.0507(15) -0.0064(17) O2 0.0841(14) 0.1289(19) 0.153(2) -0.0235(13) 0.0434(14) -0.0172(16) N1 0.0761(14) 0.110(2) 0.121(2) -0.0094(14) 0.0330(14) -0.0047(17) N2 0.0749(15) 0.114(2) 0.134(2) -0.0090(14) 0.0292(16) -0.0123(18) C1 0.0783(18) 0.100(2) 0.124(3) -0.0042(16) 0.0224(18) 0.017(2) C2 0.0698(17) 0.112(2) 0.118(3) -0.0006(17) 0.0233(18) 0.007(2) C11A 0.104(3) 0.111(3) 0.171(4) -0.009(2) 0.025(3) -0.006(3) C12A 0.182(7) 0.128(5) 0.304(10) -0.031(5) 0.103(8) -0.009(5) C13A 0.230(9) 0.173(7) 0.241(11) -0.039(6) -0.060(8) 0.074(7) C14A 0.63(3) 0.120(7) 0.385(19) -0.002(10) 0.07(2) 0.054(8) C15A 0.177(9) 0.357(17) 0.51(2) 0.045(10) 0.075(12) -0.105(15) C11B 0.104(3) 0.111(3) 0.171(4) -0.009(2) 0.025(3) -0.006(3) C12B 0.182(7) 0.128(5) 0.304(10) -0.031(5) 0.103(8) -0.009(5) C13B 0.230(9) 0.173(7) 0.241(11) -0.039(6) -0.060(8) 0.074(7) C14B 0.63(3) 0.120(7) 0.385(19) -0.002(10) 0.07(2) 0.054(8) C15B 0.177(9) 0.357(17) 0.51(2) 0.045(10) 0.075(12) -0.105(15) C21 0.101(2) 0.131(3) 0.144(4) -0.004(2) 0.031(2) -0.008(3) C22 0.178(5) 0.141(4) 0.193(5) 0.007(3) 0.006(4) -0.014(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.210(4) ? O2 C2 . 1.233(4) ? N1 C1 . 1.354(4) ? N1 C2 . 1.381(5) ? N1 H11 . 0.8600 ? N2 C2 . 1.319(4) ? N2 C21 . 1.436(5) ? N2 H21 . 0.8600 ? C1 C11A . 1.496(5) ? C11A C12A . 1.523(6) ? C11A H111 . 0.9700 ? C11A H112 . 0.9700 ? C11A C12B . 1.534(10) ? C12A C13A . 1.522(9) ? C12A H121 . 0.9700 ? C12A H122 . 0.9700 ? C13A C15A . 1.522(16) ? C13A C14A . 1.530(14) ? C13A H131 . 0.9800 ? C14A H142 . 0.9600 ? C14A H141 . 0.9600 ? C14A H143 . 0.9600 ? C15A H153 . 0.9600 ? C15A H151 . 0.9600 ? C15A H152 . 0.9600 ? C12B C13B . 1.525(12) ? C12B H123 . 0.9700 ? C12B H124 . 0.9700 ? C13B C15B . 1.53(2) ? C13B C14B . 1.53(3) ? C13B H132 . 0.9800 ? C14B H144 . 0.9600 ? C14B H145 . 0.9600 ? C14B H146 . 0.9600 ? C15B H154 . 0.9600 ? C15B H155 . 0.9600 ? C15B H156 . 0.9600 ? C21 C22 . 1.502(6) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 H223 . 0.9600 ? C22 H222 . 0.9600 ? C22 H221 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 128.7(3) ? C1 N1 H11 . . 115.7 ? C2 N1 H11 . . 115.7 ? C2 N2 C21 . . 122.2(3) ? C2 N2 H21 . . 118.9 ? C21 N2 H21 . . 118.9 ? O1 C1 N1 . . 123.8(3) ? O1 C1 C11A . . 122.4(3) ? N1 C1 C11A . . 113.8(3) ? O2 C2 N2 . . 123.4(4) ? O2 C2 N1 . . 118.3(3) ? N2 C2 N1 . . 118.3(3) ? C1 C11A C12A . . 118.2(4) ? C1 C11A H111 . . 107.8 ? C12A C11A H111 . . 107.8 ? C1 C11A H112 . . 107.8 ? C12A C11A H112 . . 107.8 ? H111 C11A H112 . . 107.1 ? C13A C12A C11A . . 112.3(5) ? C13A C12A H121 . . 109.1 ? C11A C12A H121 . . 109.1 ? C13A C12A H122 . . 109.1 ? C11A C12A H122 . . 109.1 ? H121 C12A H122 . . 107.9 ? C12A C13A C15A . . 117.0(8) ? C12A C13A C14A . . 112.3(9) ? C15A C13A C14A . . 103.3(11) ? C12A C13A H131 . . 108.0 ? C15A C13A H131 . . 108.0 ? C14A C13A H131 . . 108.0 ? C13A C14A H142 . . 109.5 ? C13A C14A H141 . . 109.5 ? H142 C14A H141 . . 109.5 ? C13A C14A H143 . . 109.5 ? H142 C14A H143 . . 109.5 ? H141 C14A H143 . . 109.5 ? C13A C15A H153 . . 109.5 ? C13A C15A H151 . . 109.5 ? H153 C15A H151 . . 109.5 ? C13A C15A H152 . . 109.5 ? H153 C15A H152 . . 109.5 ? H151 C15A H152 . . 109.5 ? C13B C12B H123 . . 108.3 ? C13B C12B H124 . . 108.3 ? H123 C12B H124 . . 107.4 ? C12B C13B C15B . . 112.0(7) ? C12B C13B C14B . . 109.5(7) ? C15B C13B C14B . . 109.9(7) ? C12B C13B H132 . . 108.4 ? C15B C13B H132 . . 108.4 ? C14B C13B H132 . . 108.4 ? C13B C14B H144 . . 109.5 ? C13B C14B H145 . . 109.5 ? H144 C14B H145 . . 109.5 ? C13B C14B H146 . . 109.5 ? H144 C14B H146 . . 109.5 ? H145 C14B H146 . . 109.5 ? C13B C15B H154 . . 109.5 ? C13B C15B H155 . . 109.5 ? H154 C15B H155 . . 109.5 ? C13B C15B H156 . . 109.5 ? H154 C15B H156 . . 109.5 ? H155 C15B H156 . . 109.5 ? N2 C21 C22 . . 112.8(4) ? N2 C21 H211 . . 109.0 ? C22 C21 H211 . . 109.0 ? N2 C21 H212 . . 109.0 ? C22 C21 H212 . . 109.0 ? H211 C21 H212 . . 107.8 ? C21 C22 H223 . . 109.5 ? C21 C22 H222 . . 109.5 ? H223 C22 H222 . . 109.5 ? C21 C22 H221 . . 109.5 ? H223 C22 H221 . . 109.5 ? H222 C22 H221 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 0.6(6) ? C2 N1 C1 C11A . . . . -177.8(3) ? C21 N2 C2 O2 . . . . 1.7(5) ? C21 N2 C2 N1 . . . . -177.6(3) ? C1 N1 C2 O2 . . . . -177.8(3) ? C1 N1 C2 N2 . . . . 1.6(5) ? O1 C1 C11A C12A . . . . 49.9(5) ? N1 C1 C11A C12A . . . . -131.7(4) ? C1 C11A C12A C13A . . . . 78.5(7) ? C11A C12A C13A C15A . . . . 64.5(11) ? C11A C12A C13A C14A . . . . -176.3(9) ? C2 N2 C21 C22 . . . . -84.1(5) ? C2 N1 C1 C11B . . . . -177.8(3) ? O1 C1 C11B C12B . . . . 100.4(7) ? N1 C1 C11B C12B . . . . -81.1(7) ? C1 C11B C12B C13B . . . . -145.1(10) ? C11B C12B C13B C15B . . . . -33.4(17) ? C11B C12B C13B C14B . . . . 88.8(17) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.86 2.41 3.100(3) 137.9 N1 H11 O2 2_566 0.86 2.00 2.855(4) 177.8 data_ethyl374K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-3-(4-methylpentanoyl)urea ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 N2 O2' _chemical_formula_sum 'C9 H18 N2 O2' _chemical_formula_weight 186.25 _chemical_melting_point 375 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6337(14) _cell_length_b 13.1782(16) _cell_length_c 5.2242(18) _cell_angle_alpha 85.948(12) _cell_angle_beta 91.71(2) _cell_angle_gamma 88.030(13) _cell_volume 592.2(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1921 _cell_measurement_theta_min 1.55 _cell_measurement_theta_max 27.435 _cell_measurement_temperature 374 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.044 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystal was being high temperature phase. ; _diffrn_ambient_temperature 374 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 8267 _diffrn_reflns_av_R_equivalents 0.041 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_max 0.724 _diffrn_measured_fraction_theta_full 0.724 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 1962 _reflns_number_gt 826 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.2397 _refine_ls_R_factor_gt 0.1519 _refine_ls_wR_factor_gt 0.3442 _refine_ls_wR_factor_ref 0.3786 _refine_ls_goodness_of_fit_ref 1.846 _refine_ls_restrained_S_all 1.846 _refine_ls_number_reflns 1962 _refine_ls_number_parameters 131 _refine_ls_number_restraints 17 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.220 _refine_diff_density_min -0.222 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 372K was used as an initial model. The minor part of the disordered 3-methylbutyl group was deleted to avoid some viases for disorder analysis. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.4309(4) 0.5705(3) 0.2056(8) 0.1487(15) Uani d . 1 A . O O2 0.0265(4) 0.4115(2) 0.2684(8) 0.1411(15) Uani d . 1 A . O N1 0.1966(4) 0.5311(3) 0.3691(9) 0.1209(14) Uani d . 1 A . N H11 0.1319 0.5483 0.4816 0.145 Uiso calc R 1 . . H N2 0.2533(4) 0.4162(3) 0.0625(9) 0.1289(16) Uani d D 1 A . N H21 0.3412 0.4442 0.0446 0.155 Uiso calc R 1 . . H C1 0.3248(5) 0.5871(3) 0.3521(10) 0.1222(18) Uani d D 1 . . C C2 0.1557(5) 0.4510(4) 0.2330(11) 0.1156(17) Uani d . 1 . . C C11A 0.3332(6) 0.6684(3) 0.5374(11) 0.148(2) Uani d PD 0.765(6) A 1 C H111 0.4093 0.6458 0.6715 0.178 Uiso calc PR 0.765(6) A 1 H H112 0.2335 0.6734 0.6174 0.178 Uiso calc PR 0.765(6) A 1 H C12A 0.3736(9) 0.7748(5) 0.435(2) 0.227(5) Uani d PD 0.765(6) A 1 C H122 0.4541 0.7692 0.3107 0.272 Uiso calc PR 0.765(6) A 1 H H121 0.4154 0.8108 0.5758 0.272 Uiso calc PR 0.765(6) A 1 H C13A 0.2368(10) 0.8371(7) 0.309(2) 0.248(7) Uani d PD 0.765(6) A 1 C H131 0.2004 0.7995 0.1650 0.298 Uiso calc PR 0.765(6) A 1 H C14A 0.277(2) 0.9430(8) 0.194(3) 0.366(14) Uani d PD 0.765(6) A 1 C H142 0.3645 0.9369 0.0865 0.549 Uiso calc PR 0.765(6) A 1 H H141 0.3021 0.9855 0.3304 0.549 Uiso calc PR 0.765(6) A 1 H H143 0.1898 0.9728 0.0944 0.549 Uiso calc PR 0.765(6) A 1 H C15A 0.0940(18) 0.8608(14) 0.463(5) 0.396(14) Uani d PD 0.765(6) A 1 C H153 0.0151 0.8944 0.3507 0.594 Uiso calc PR 0.765(6) A 1 H H151 0.1215 0.9043 0.5954 0.594 Uiso calc PR 0.765(6) A 1 H H152 0.0556 0.7985 0.5390 0.594 Uiso calc PR 0.765(6) A 1 H C11B 0.3332(6) 0.6684(3) 0.5374(11) 0.148(2) Uani d PD 0.235(6) A 2 C H113 0.4389 0.6904 0.5526 0.178 Uiso calc PR 0.235(6) A 2 H H114 0.3028 0.6415 0.7054 0.178 Uiso calc PR 0.235(6) A 2 H C12B 0.2253(14) 0.7593(6) 0.444(3) 0.227(5) Uani d PD 0.235(6) A 2 C H123 0.2134 0.7607 0.2588 0.272 Uiso calc PR 0.235(6) A 2 H H124 0.1240 0.7490 0.5149 0.272 Uiso calc PR 0.235(6) A 2 H C13B 0.2811(16) 0.8627(6) 0.517(2) 0.248(7) Uani d PD 0.235(6) A 2 C H132 0.1928 0.9117 0.5045 0.298 Uiso calc PR 0.235(6) A 2 H C14B 0.403(3) 0.900(2) 0.328(4) 0.366(14) Uani d PD 0.235(6) A 2 C H144 0.4330 0.9665 0.3660 0.549 Uiso calc PR 0.235(6) A 2 H H145 0.3604 0.9014 0.1562 0.549 Uiso calc PR 0.235(6) A 2 H H146 0.4923 0.8537 0.3447 0.549 Uiso calc PR 0.235(6) A 2 H C15B 0.350(4) 0.856(2) 0.791(3) 0.396(14) Uani d PD 0.235(6) A 2 C H154 0.3691 0.9235 0.8409 0.594 Uiso calc PR 0.235(6) A 2 H H155 0.4452 0.8164 0.7993 0.594 Uiso calc PR 0.235(6) A 2 H H156 0.2777 0.8247 0.9059 0.594 Uiso calc PR 0.235(6) A 2 H C21 0.2164(6) 0.3329(4) -0.0932(10) 0.143(2) Uani d D 1 . . C H211 0.2718 0.3396 -0.2520 0.172 Uiso calc R 1 A . H H212 0.1062 0.3359 -0.1364 0.172 Uiso calc R 1 . . H C22 0.2604(9) 0.2311(4) 0.0485(16) 0.204(4) Uani d D 1 A . C H223 0.2366 0.1772 -0.0590 0.245 Uiso calc R 1 . . H H222 0.2031 0.2235 0.2029 0.245 Uiso calc R 1 . . H H221 0.3695 0.2281 0.0914 0.245 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.102(2) 0.168(3) 0.182(3) -0.029(2) 0.051(2) -0.024(3) O2 0.094(2) 0.140(3) 0.196(4) -0.0257(18) 0.052(2) -0.027(2) N1 0.083(2) 0.124(3) 0.160(4) -0.021(2) 0.039(3) -0.018(3) N2 0.087(2) 0.132(3) 0.173(4) -0.013(2) 0.039(3) -0.026(3) C1 0.084(3) 0.116(3) 0.165(5) 0.003(3) 0.027(3) 0.007(3) C2 0.064(2) 0.138(4) 0.142(5) 0.003(3) 0.015(3) 0.010(3) C11A 0.115(4) 0.119(4) 0.213(6) -0.017(3) 0.030(4) -0.018(4) C12A 0.187(9) 0.172(7) 0.325(14) -0.015(7) 0.108(11) 0.005(8) C13A 0.204(11) 0.269(12) 0.248(14) -0.030(10) -0.074(11) 0.118(12) C14A 0.62(4) 0.131(9) 0.34(2) -0.042(13) -0.03(2) 0.072(10) C15A 0.181(13) 0.35(2) 0.68(4) 0.033(13) 0.10(2) -0.17(2) C11B 0.115(4) 0.119(4) 0.213(6) -0.017(3) 0.030(4) -0.018(4) C12B 0.187(9) 0.172(7) 0.325(14) -0.015(7) 0.108(11) 0.005(8) C13B 0.204(11) 0.269(12) 0.248(14) -0.030(10) -0.074(11) 0.118(12) C14B 0.62(4) 0.131(9) 0.34(2) -0.042(13) -0.03(2) 0.072(10) C15B 0.181(13) 0.35(2) 0.68(4) 0.033(13) 0.10(2) -0.17(2) C21 0.103(4) 0.149(4) 0.178(6) 0.000(3) 0.037(4) -0.007(4) C22 0.192(7) 0.147(5) 0.278(10) -0.009(5) 0.043(8) -0.039(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.234(6) ? O2 C2 . 1.261(6) ? N1 C1 . 1.353(6) ? N1 C2 . 1.364(7) ? N1 H11 . 0.8600 ? N2 C2 . 1.338(6) ? N2 C21 . 1.450(7) ? N2 H21 . 0.8600 ? C1 C11A . 1.496(7) ? C11A C12A . 1.521(9) ? C11A H111 . 0.9700 ? C11A H112 . 0.9700 ? C11A C12B . 1.53(11) ? C12A C13A . 1.521(12) ? C12A H122 . 0.9700 ? C12A H121 . 0.9700 ? C13A C15A . 1.53(2) ? C13A C14A . 1.534(16) ? C13A H131 . 0.9800 ? C14A H142 . 0.9600 ? C14A H141 . 0.9600 ? C14A H143 . 0.9600 ? C15A H153 . 0.9600 ? C15A H151 . 0.9600 ? C15A H152 . 0.9600 ? C12B C13B . 1.530(13) ? C12B H123 . 0.9700 ? C12B H124 . 0.9700 ? C13B C15B . 1.53(2) ? C13B C14B . 1.53(3) ? C13B H132 . 0.9800 ? C14B H144 . 0.9600 ? C14B H145 . 0.9600 ? C14B H146 . 0.9600 ? C15B H154 . 0.9600 ? C15B H155 . 0.9600 ? C15B H156 . 0.9600 ? C21 C22 . 1.517(8) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 H223 . 0.9600 ? C22 H222 . 0.9600 ? C22 H221 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 129.1(4) ? C1 N1 H11 . . 115.5 ? C2 N1 H11 . . 115.5 ? C2 N2 C21 . . 122.5(4) ? C2 N2 H21 . . 118.8 ? C21 N2 H21 . . 118.8 ? O1 C1 N1 . . 123.6(4) ? O1 C1 C11A . . 121.8(4) ? N1 C1 C11A . . 114.5(4) ? O2 C2 N2 . . 121.1(6) ? O2 C2 N1 . . 119.6(4) ? N2 C2 N1 . . 119.3(4) ? C1 C11A C12A . . 118.1(6) ? C1 C11A H111 . . 107.8 ? C12A C11A H111 . . 107.8 ? C1 C11A H112 . . 107.8 ? C12A C11A H112 . . 107.8 ? H111 C11A H112 . . 107.1 ? C11A C12A C13A . . 113.9(6) ? C11A C12A H122 . . 108.8 ? C13A C12A H122 . . 108.8 ? C11A C12A H121 . . 108.8 ? C13A C12A H121 . . 108.8 ? H122 C12A H121 . . 107.7 ? C12A C13A C15A . . 120.4(12) ? C12A C13A C14A . . 114.5(10) ? C15A C13A C14A . . 102.2(13) ? C12A C13A H131 . . 106.3 ? C15A C13A H131 . . 106.3 ? C14A C13A H131 . . 106.3 ? C13A C14A H142 . . 109.5 ? C13A C14A H141 . . 109.5 ? H142 C14A H141 . . 109.5 ? C13A C14A H143 . . 109.5 ? H142 C14A H143 . . 109.5 ? H141 C14A H143 . . 109.5 ? C13A C15A H153 . . 109.5 ? C13A C15A H151 . . 109.5 ? H153 C15A H151 . . 109.5 ? C13A C15A H152 . . 109.5 ? H153 C15A H152 . . 109.5 ? H151 C15A H152 . . 109.5 ? C13B C12B H123 . . 108.6 ? C13B C12B H124 . . 108.6 ? H123 C12B H124 . . 107.6 ? C12B C13B C15B . . 111.2(7) ? C12B C13B C14B . . 109.3(7) ? C15B C13B C14B . . 109.9(7) ? C12B C13B H132 . . 108.8 ? C15B C13B H132 . . 108.8 ? C14B C13B H132 . . 108.8 ? C13B C14B H144 . . 109.5 ? C13B C14B H145 . . 109.5 ? H144 C14B H145 . . 109.5 ? C13B C14B H146 . . 109.5 ? H144 C14B H146 . . 109.5 ? H145 C14B H146 . . 109.5 ? C13B C15B H154 . . 109.5 ? C13B C15B H155 . . 109.5 ? H154 C15B H155 . . 109.5 ? C13B C15B H156 . . 109.5 ? H154 C15B H156 . . 109.5 ? H155 C15B H156 . . 109.5 ? N2 C21 C22 . . 110.9(5) ? N2 C21 H211 . . 109.5 ? C22 C21 H211 . . 109.5 ? N2 C21 H212 . . 109.5 ? C22 C21 H212 . . 109.5 ? H211 C21 H212 . . 108.0 ? C21 C22 H223 . . 109.5 ? C21 C22 H222 . . 109.5 ? H223 C22 H222 . . 109.5 ? C21 C22 H221 . . 109.5 ? H223 C22 H221 . . 109.5 ? H222 C22 H221 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . -2.0(9) ? C2 N1 C1 C11A . . . . -178.7(5) ? C21 N2 C2 O2 . . . . 1.0(7) ? C21 N2 C2 N1 . . . . -178.6(5) ? C1 N1 C2 O2 . . . . -176.5(5) ? C1 N1 C2 N2 . . . . 3.1(8) ? O1 C1 C11A C12A . . . . 51.0(7) ? N1 C1 C11A C12A . . . . -132.3(6) ? C1 C11A C12A C13A . . . . 81.4(10) ? C11A C12A C13A C15A . . . . 60.1(16) ? C11A C12A C13A C14A . . . . -177.4(11) ? C2 N2 C21 C22 . . . . -86.2(6) ? C2 N1 C1 C11B . . . . -178.7(5) ? O1 C1 C11B C12B . . . . 106.2(9) ? N1 C1 C11B C12B . . . . -77.1(8) ? C1 C11B C12B C13B . . . . -148.3(10) ? C11B C12B C13B C15B . . . . -40.8(18) ? C11B C12B C13B C14B . . . . 80.6(18) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H21 O1 2_665 0.86 2.40 3.107(5) 139.2 N1 H11 O2 2_566 0.86 2.00 2.862(5) 177.5 data_propyl98K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(4-methylpentanoyl)-3-propylurea ; _chemical_name_common ? _chemical_formula_moiety 'C10 H20 N2 O2' _chemical_formula_sum 'C10 H20 N2 O2' _chemical_formula_weight 200.28 _chemical_melting_point 381 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5437(19) _cell_length_b 13.205(4) _cell_length_c 4.8457(13) _cell_angle_alpha 92.029(14) _cell_angle_beta 98.767(9) _cell_angle_gamma 78.875(17) _cell_volume 592.2(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3224 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.48 _cell_measurement_temperature 98 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.123 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 98 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 6949 _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_max 0.797 _diffrn_measured_fraction_theta_full 0.797 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2162 _reflns_number_gt 1775 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_gt 0.1534 _refine_ls_wR_factor_ref 0.1677 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_number_reflns 2162 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refall _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+0.7784P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.308 _refine_diff_density_min -0.251 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution 'SIR-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.11921(18) 0.55649(14) -0.0569(4) 0.0314(4) Uani d . 1 . . O O2 0.40312(18) 0.41157(13) 0.6112(3) 0.0297(4) Uani d . 1 . . O N1 0.3321(2) 0.52101(15) 0.2434(4) 0.0245(4) Uani d . 1 . . N H11 0.422(4) 0.542(2) 0.292(6) 0.042(8) Uiso d . 1 . . H N2 0.1782(2) 0.41817(16) 0.3633(4) 0.0271(5) Uani d . 1 . . N H21 0.115(4) 0.445(2) 0.224(7) 0.041(8) Uiso d . 1 . . H C1 0.2423(2) 0.57155(18) 0.0234(5) 0.0248(5) Uani d . 1 . . C C2 0.3061(2) 0.44630(17) 0.4180(5) 0.0246(5) Uani d . 1 . . C C11 0.3039(3) 0.65149(18) -0.1090(5) 0.0252(5) Uani d . 1 . . C H111 0.414(3) 0.626(2) -0.111(6) 0.042(8) Uiso d . 1 . . H H112 0.255(3) 0.662(2) -0.304(6) 0.029(7) Uiso d . 1 . . H C12 0.2811(3) 0.75336(19) 0.0561(5) 0.0296(5) Uani d . 1 . . C H121 0.336(3) 0.744(2) 0.247(6) 0.034(7) Uiso d . 1 . . H H122 0.174(4) 0.773(2) 0.079(7) 0.049(9) Uiso d . 1 . . H C13 0.3259(3) 0.84217(19) -0.0817(6) 0.0318(6) Uani d . 1 . . C H131 0.268(3) 0.851(2) -0.267(6) 0.037(8) Uiso d . 1 . . H C14 0.2853(4) 0.9422(2) 0.0804(8) 0.0484(8) Uani d . 1 . . C H141 0.177(4) 0.960(3) 0.084(7) 0.059(10) Uiso d . 1 . . H H142 0.308(4) 1.002(3) -0.020(8) 0.064(11) Uiso d . 1 . . H H143 0.336(4) 0.935(3) 0.277(9) 0.070(11) Uiso d . 1 . . H C15 0.4853(3) 0.8202(3) -0.1093(8) 0.0471(8) Uani d . 1 . . C H151 0.512(5) 0.880(3) -0.185(8) 0.079(13) Uiso d . 1 . . H H152 0.539(4) 0.809(3) 0.077(7) 0.051(10) Uiso d . 1 . . H H153 0.510(4) 0.755(3) -0.239(7) 0.061(10) Uiso d . 1 . . H C21 0.1370(3) 0.34246(19) 0.5315(5) 0.0270(5) Uani d . 1 . . C H211 0.204(3) 0.333(2) 0.707(6) 0.032(7) Uiso d . 1 . . H H212 0.037(3) 0.369(2) 0.581(6) 0.032(7) Uiso d . 1 . . H C22 0.1387(3) 0.2395(2) 0.3795(6) 0.0338(6) Uani d . 1 . . C H221 0.241(4) 0.210(2) 0.341(7) 0.045(8) Uiso d . 1 . . H H222 0.080(4) 0.252(3) 0.189(7) 0.057(10) Uiso d . 1 . . H C23 0.0812(4) 0.1644(2) 0.5410(7) 0.0403(7) Uani d . 1 . . C H231 0.136(4) 0.153(3) 0.729(7) 0.049(9) Uiso d . 1 . . H H232 0.084(4) 0.096(3) 0.456(7) 0.063(11) Uiso d . 1 . . H H233 -0.019(4) 0.195(3) 0.572(7) 0.053(10) Uiso d . 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0236(9) 0.0398(10) 0.0299(9) -0.0107(7) -0.0062(7) 0.0047(7) O2 0.0252(9) 0.0352(9) 0.0268(9) -0.0087(7) -0.0067(7) 0.0045(7) N1 0.0221(10) 0.0286(10) 0.0233(10) -0.0094(8) -0.0014(8) 0.0010(7) N2 0.0236(11) 0.0332(11) 0.0244(10) -0.0108(8) -0.0041(8) 0.0038(8) C1 0.0228(12) 0.0285(12) 0.0220(11) -0.0052(9) 0.0005(9) -0.0030(9) C2 0.0241(12) 0.0287(11) 0.0207(11) -0.0082(9) -0.0010(9) -0.0036(8) C11 0.0259(12) 0.0287(11) 0.0209(11) -0.0068(9) 0.0002(9) 0.0006(8) C12 0.0344(14) 0.0294(12) 0.0263(12) -0.0087(10) 0.0061(10) -0.0019(9) C13 0.0337(14) 0.0298(13) 0.0320(13) -0.0092(10) 0.0008(11) 0.0021(10) C14 0.062(2) 0.0305(15) 0.0533(19) -0.0095(14) 0.0100(17) -0.0029(13) C15 0.0377(17) 0.0450(17) 0.064(2) -0.0187(13) 0.0093(15) 0.0040(15) C21 0.0249(12) 0.0323(12) 0.0243(11) -0.0099(9) -0.0009(10) 0.0029(9) C22 0.0367(15) 0.0318(13) 0.0360(14) -0.0095(11) 0.0122(12) -0.0016(10) C23 0.0489(18) 0.0333(14) 0.0438(17) -0.0143(12) 0.0148(14) -0.0007(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.231(3) ? O2 C2 . 1.244(3) ? N1 C1 . 1.367(3) ? N1 C2 . 1.403(3) ? N1 H11 . 0.95(3) ? N2 C2 . 1.329(3) ? N2 C21 . 1.458(3) ? N2 H21 . 0.87(3) ? C1 C11 . 1.508(3) ? C11 C12 . 1.537(3) ? C11 H111 . 1.04(3) ? C11 H112 . 0.99(3) ? C12 C13 . 1.530(3) ? C12 H121 . 0.99(3) ? C12 H122 . 1.03(3) ? C13 C15 . 1.518(4) ? C13 C14 . 1.528(4) ? C13 H131 . 0.98(3) ? C14 H141 . 1.01(4) ? C14 H142 . 1.02(4) ? C14 H143 . 1.00(4) ? C15 H151 . 0.97(4) ? C15 H152 . 0.97(4) ? C15 H153 . 1.06(4) ? C21 C22 . 1.522(4) ? C21 H211 . 0.98(3) ? C21 H212 . 1.01(3) ? C22 C23 . 1.515(4) ? C22 H221 . 1.03(3) ? C22 H222 . 1.00(4) ? C23 H231 . 0.98(3) ? C23 H232 . 0.98(4) ? C23 H233 . 1.00(4) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 128.9(2) ? C1 N1 H11 . . 116.0(18) ? C2 N1 H11 . . 115.0(18) ? C2 N2 C21 . . 122.3(2) ? C2 N2 H21 . . 120(2) ? C21 N2 H21 . . 117(2) ? O1 C1 N1 . . 123.6(2) ? O1 C1 C11 . . 122.0(2) ? N1 C1 C11 . . 114.4(2) ? O2 C2 N2 . . 125.0(2) ? O2 C2 N1 . . 118.1(2) ? N2 C2 N1 . . 116.9(2) ? C1 C11 C12 . . 110.1(2) ? C1 C11 H111 . . 110.4(17) ? C12 C11 H111 . . 108.8(17) ? C1 C11 H112 . . 108.5(15) ? C12 C11 H112 . . 110.3(16) ? H111 C11 H112 . . 109(2) ? C13 C12 C11 . . 113.5(2) ? C13 C12 H121 . . 108.4(16) ? C11 C12 H121 . . 110.0(16) ? C13 C12 H122 . . 109.8(18) ? C11 C12 H122 . . 108.3(18) ? H121 C12 H122 . . 107(2) ? C15 C13 C14 . . 111.3(3) ? C15 C13 C12 . . 112.3(2) ? C14 C13 C12 . . 109.7(2) ? C15 C13 H131 . . 109.7(17) ? C14 C13 H131 . . 107.0(17) ? C12 C13 H131 . . 106.6(17) ? C13 C14 H141 . . 111(2) ? C13 C14 H142 . . 110(2) ? H141 C14 H142 . . 105(3) ? C13 C14 H143 . . 110(2) ? H141 C14 H143 . . 109(3) ? H142 C14 H143 . . 113(3) ? C13 C15 H151 . . 110(3) ? C13 C15 H152 . . 107(2) ? H151 C15 H152 . . 108(3) ? C13 C15 H153 . . 111(2) ? H151 C15 H153 . . 110(3) ? H152 C15 H153 . . 111(3) ? N2 C21 C22 . . 111.7(2) ? N2 C21 H211 . . 108.6(16) ? C22 C21 H211 . . 110.1(16) ? N2 C21 H212 . . 110.0(16) ? C22 C21 H212 . . 109.3(16) ? H211 C21 H212 . . 107(2) ? C23 C22 C21 . . 111.7(2) ? C23 C22 H221 . . 111.5(17) ? C21 C22 H221 . . 109.3(17) ? C23 C22 H222 . . 111(2) ? C21 C22 H222 . . 109(2) ? H221 C22 H222 . . 104(3) ? C22 C23 H231 . . 111.7(19) ? C22 C23 H232 . . 115(2) ? H231 C23 H232 . . 106(3) ? C22 C23 H233 . . 109.7(19) ? H231 C23 H233 . . 104(3) ? H232 C23 H233 . . 110(3) ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . -0.7(4) ? C2 N1 C1 C11 . . . . 177.0(2) ? C21 N2 C2 O2 . . . . 0.8(4) ? C21 N2 C2 N1 . . . . -179.1(2) ? C1 N1 C2 O2 . . . . -178.6(2) ? C1 N1 C2 N2 . . . . 1.3(4) ? O1 C1 C11 C12 . . . . 94.6(3) ? N1 C1 C11 C12 . . . . -83.1(3) ? C1 C11 C12 C13 . . . . -173.8(2) ? C11 C12 C13 C15 . . . . -61.3(3) ? C11 C12 C13 C14 . . . . 174.3(2) ? C2 N2 C21 C22 . . . . -106.1(3) ? N2 C21 C22 C23 . . . . -174.1(2) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H11 O2 2_666 0.95(3) 1.88(3) 2.820(3) 178(3) N2 H21 O1 2_565 0.87(3) 2.26(3) 2.959(3) 137(3) data_propyl298K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(4-methylpentanoyl)-3-propylurea ; _chemical_name_common ? _chemical_formula_moiety 'C10 H20 N2 O2' _chemical_formula_sum 'C10 H20 N2 O2' _chemical_formula_weight 200.28 _chemical_melting_point 381 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.547(4) _cell_length_b 13.688(6) _cell_length_c 5.1166(16) _cell_angle_alpha 90.902(14) _cell_angle_beta 97.109(8) _cell_angle_gamma 80.47(2) _cell_volume 654.3(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3480 _cell_measurement_theta_min 1.51 _cell_measurement_theta_max 27.23 _cell_measurement_temperature 298 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.017 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 10255 _diffrn_reflns_av_R_equivalents 0.071 _diffrn_reflns_av_sigmaI/netI 0.0579 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.827 _diffrn_measured_fraction_theta_full 0.827 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2485 _reflns_number_gt 1178 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1872 _refine_ls_R_factor_gt 0.1166 _refine_ls_wR_factor_gt 0.3131 _refine_ls_wR_factor_ref 0.3767 _refine_ls_goodness_of_fit_ref 1.972 _refine_ls_restrained_S_all 1.975 _refine_ls_number_reflns 2485 _refine_ls_number_parameters 127 _refine_ls_number_restraints 6 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.335 _refine_diff_density_min -0.319 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 98K was used as an initial model. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.1236(3) 0.5584(3) -0.0332(6) 0.1050(12) Uani d . 1 . . O O2 0.3975(3) 0.4154(2) 0.5961(6) 0.0975(11) Uani d . 1 . . O N1 0.3307(3) 0.5232(2) 0.2512(6) 0.0836(11) Uani d . 1 . . N H11 0.4137 0.5401 0.2863 0.100 Uiso calc R 1 . . H N2 0.1742(3) 0.4212(3) 0.3621(7) 0.0911(12) Uani d . 1 . . N H21 0.1154 0.4484 0.2325 0.109 Uiso calc R 1 . . H C1 0.2437(4) 0.5731(3) 0.0441(8) 0.0811(11) Uani d . 1 . . C C2 0.3029(4) 0.4485(3) 0.4130(8) 0.0808(11) Uani d . 1 . . C C11 0.3108(4) 0.6517(3) -0.0726(8) 0.0900(13) Uani d D 1 . . C H111 0.2751 0.6597 -0.2582 0.108 Uiso calc R 1 . . H H112 0.4137 0.6310 -0.0575 0.108 Uiso calc R 1 . . H C12 0.2772(5) 0.7513(3) 0.0675(10) 0.1093(16) Uani d D 1 . . C H121 0.1747 0.7661 0.0737 0.131 Uiso calc R 1 . . H H122 0.3230 0.7439 0.2478 0.131 Uiso calc R 1 . . H C13 0.3234(6) 0.8397(3) -0.0551(13) 0.134(2) Uani d D 1 . . C H131 0.2810 0.8447 -0.2399 0.160 Uiso calc R 1 . . H C14 0.2702(10) 0.9370(4) 0.0806(19) 0.217(5) Uani d D 1 . . C H141 0.1681 0.9456 0.0758 0.261 Uiso calc R 1 . . H H143 0.2956 0.9914 -0.0094 0.261 Uiso calc R 1 . . H H142 0.3137 0.9351 0.2604 0.261 Uiso calc R 1 . . H C15 0.4856(6) 0.8229(6) -0.049(2) 0.209(4) Uani d D 1 . . C H151 0.5138 0.8783 -0.1293 0.251 Uiso calc R 1 . . H H152 0.5156 0.7636 -0.1440 0.251 Uiso calc R 1 . . H H153 0.5297 0.8161 0.1304 0.251 Uiso calc R 1 . . H C21 0.1313(4) 0.3472(3) 0.5193(8) 0.0930(14) Uani d D 1 . . C H211 0.0317 0.3671 0.5449 0.112 Uiso calc R 1 . . H H212 0.1878 0.3433 0.6910 0.112 Uiso calc R 1 . . H C22 0.1503(6) 0.2446(3) 0.3913(11) 0.1219(18) Uani d D 1 . . C H221 0.0991 0.2492 0.2148 0.146 Uiso calc R 1 . . H H222 0.2510 0.2224 0.3769 0.146 Uiso calc R 1 . . H C23 0.0952(7) 0.1689(4) 0.5501(15) 0.150(2) Uani d D 1 . . C H232 0.1068 0.1061 0.4624 0.180 Uiso calc R 1 . . H H231 -0.0043 0.1908 0.5653 0.180 Uiso calc R 1 . . H H233 0.1485 0.1622 0.7225 0.180 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0711(15) 0.133(3) 0.109(2) -0.0320(15) -0.0182(15) 0.031(2) O2 0.0768(16) 0.109(2) 0.104(2) -0.0281(15) -0.0173(16) 0.0273(17) N1 0.0662(16) 0.100(3) 0.085(2) -0.0257(16) -0.0085(15) 0.0091(18) N2 0.0703(17) 0.112(3) 0.093(2) -0.0310(17) -0.0100(16) 0.0215(19) C1 0.0654(17) 0.098(3) 0.080(2) -0.0186(18) -0.0014(17) 0.002(2) C2 0.0667(19) 0.091(3) 0.085(2) -0.0214(18) -0.0011(19) 0.006(2) C11 0.087(2) 0.099(3) 0.086(2) -0.019(2) 0.011(2) 0.009(2) C12 0.111(3) 0.100(4) 0.124(4) -0.023(3) 0.036(3) 0.007(3) C13 0.147(5) 0.102(4) 0.160(5) -0.031(3) 0.037(4) 0.018(4) C14 0.271(12) 0.101(5) 0.298(11) -0.032(6) 0.105(10) 0.005(6) C15 0.153(6) 0.157(6) 0.347(13) -0.075(5) 0.080(8) 0.006(8) C21 0.080(2) 0.105(3) 0.096(3) -0.027(2) 0.003(2) 0.017(3) C22 0.122(4) 0.106(4) 0.144(4) -0.024(3) 0.035(4) 0.006(3) C23 0.165(6) 0.110(4) 0.183(6) -0.029(4) 0.045(5) 0.016(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.213(5) ? O2 C2 . 1.252(4) ? N1 C1 . 1.377(5) ? N1 C2 . 1.404(6) ? N1 H11 . 0.8600 ? N2 C2 . 1.337(5) ? N2 C21 . 1.444(6) ? N2 H21 . 0.8600 ? C1 C11 . 1.506(6) ? C11 C12 . 1.534(6) ? C11 H111 . 0.9700 ? C11 H112 . 0.9700 ? C12 C13 . 1.524(7) ? C12 H121 . 0.9700 ? C12 H122 . 0.9700 ? C13 C15 . 1.524(8) ? C13 C14 . 1.532(9) ? C13 H131 . 0.9800 ? C14 H141 . 0.9600 ? C14 H143 . 0.9600 ? C14 H142 . 0.9600 ? C15 H151 . 0.9600 ? C15 H152 . 0.9600 ? C15 H153 . 0.9600 ? C21 C22 . 1.533(6) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 C23 . 1.524(9) ? C22 H221 . 0.9700 ? C22 H222 . 0.9700 ? C23 H232 . 0.9600 ? C23 H231 . 0.9600 ? C23 H233 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 129.2(3) ? C1 N1 H11 . . 115.4 ? C2 N1 H11 . . 115.4 ? C2 N2 C21 . . 121.7(3) ? C2 N2 H21 . . 119.2 ? C21 N2 H21 . . 119.2 ? O1 C1 N1 . . 124.3(4) ? O1 C1 C11 . . 122.7(4) ? N1 C1 C11 . . 112.9(3) ? O2 C2 N2 . . 125.5(4) ? O2 C2 N1 . . 118.1(3) ? N2 C2 N1 . . 116.4(3) ? C1 C11 C12 . . 111.3(3) ? C1 C11 H111 . . 109.4 ? C12 C11 H111 . . 109.4 ? C1 C11 H112 . . 109.4 ? C12 C11 H112 . . 109.4 ? H111 C11 H112 . . 108.0 ? C13 C12 C11 . . 116.1(4) ? C13 C12 H121 . . 108.3 ? C11 C12 H121 . . 108.3 ? C13 C12 H122 . . 108.3 ? C11 C12 H122 . . 108.3 ? H121 C12 H122 . . 107.4 ? C12 C13 C15 . . 109.9(4) ? C12 C13 C14 . . 111.9(4) ? C15 C13 C14 . . 111.1(6) ? C12 C13 H131 . . 107.9 ? C15 C13 H131 . . 107.9 ? C14 C13 H131 . . 107.9 ? C13 C14 H141 . . 109.5 ? C13 C14 H143 . . 109.5 ? H141 C14 H143 . . 109.5 ? C13 C14 H142 . . 109.5 ? H141 C14 H142 . . 109.5 ? H143 C14 H142 . . 109.5 ? C13 C15 H151 . . 109.5 ? C13 C15 H152 . . 109.5 ? H151 C15 H152 . . 109.5 ? C13 C15 H153 . . 109.5 ? H151 C15 H153 . . 109.5 ? H152 C15 H153 . . 109.5 ? N2 C21 C22 . . 112.4(3) ? N2 C21 H211 . . 109.1 ? C22 C21 H211 . . 109.1 ? N2 C21 H212 . . 109.1 ? C22 C21 H212 . . 109.1 ? H211 C21 H212 . . 107.9 ? C23 C22 C21 . . 111.7(4) ? C23 C22 H221 . . 109.3 ? C21 C22 H221 . . 109.3 ? C23 C22 H222 . . 109.3 ? C21 C22 H222 . . 109.3 ? H221 C22 H222 . . 107.9 ? C22 C23 H232 . . 109.5 ? C22 C23 H231 . . 109.5 ? H232 C23 H231 . . 109.5 ? C22 C23 H233 . . 109.5 ? H232 C23 H233 . . 109.5 ? H231 C23 H233 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . -0.4(7) ? C2 N1 C1 C11 . . . . 177.4(4) ? C21 N2 C2 O2 . . . . -0.5(7) ? C21 N2 C2 N1 . . . . -178.3(4) ? C1 N1 C2 O2 . . . . -178.0(4) ? C1 N1 C2 N2 . . . . -0.1(6) ? O1 C1 C11 C12 . . . . 89.0(5) ? N1 C1 C11 C12 . . . . -88.8(5) ? C1 C11 C12 C13 . . . . -172.6(4) ? C11 C12 C13 C15 . . . . -62.5(8) ? C11 C12 C13 C14 . . . . 173.6(6) ? C2 N2 C21 C22 . . . . -98.4(5) ? N2 C21 C22 C23 . . . . -176.1(5) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H11 O2 2_666 0.86 2.02 2.873(4) 174.2 N2 H21 O1 2_565 0.86 2.40 3.092(4) 138.2 data_propyl348K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(4-methylpentanoyl)-3-propylurea ; _chemical_name_common ? _chemical_formula_moiety 'C10 H20 N2 O2' _chemical_formula_sum 'C10 H20 N2 O2' _chemical_formula_weight 200.28 _chemical_melting_point 381 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.405(2) _cell_length_b 13.3600(19) _cell_length_c 5.1686(8) _cell_angle_alpha 93.609(13) _cell_angle_beta 98.144(12) _cell_angle_gamma 79.387(10) _cell_volume 631.46(19) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1956 _cell_measurement_theta_min 2.215 _cell_measurement_theta_max 25.73 _cell_measurement_temperature 348 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.053 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 348 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'RIGAKU RAXIS-RAPID' _diffrn_measurement_method 'Oscillation method' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 10152 _diffrn_reflns_av_R_equivalents 0.078 _diffrn_reflns_av_sigmaI/netI 0.0527 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.543 _diffrn_measured_fraction_theta_full 0.543 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 5 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 1576 _reflns_number_gt 861 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.2108 _refine_ls_R_factor_gt 0.1401 _refine_ls_wR_factor_gt 0.3401 _refine_ls_wR_factor_ref 0.3910 _refine_ls_goodness_of_fit_ref 2.045 _refine_ls_restrained_S_all 2.046 _refine_ls_number_reflns 1576 _refine_ls_number_parameters 127 _refine_ls_number_restraints 6 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.229 _refine_diff_density_min -0.183 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_structure_solution ; The final structure at 298K was used as an initial model. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.1244(5) 0.5604(4) -0.0247(11) 0.123(2) Uani d . 1 . . O O2 0.3953(5) 0.4151(4) 0.5898(11) 0.118(2) Uani d . 1 . . O N1 0.3332(5) 0.5239(4) 0.2559(12) 0.0920(18) Uani d . 1 . . N H11 0.4181 0.5404 0.2946 0.110 Uiso calc R 1 . . H N2 0.1729(6) 0.4231(4) 0.3557(12) 0.105(2) Uani d . 1 . . N H21 0.1135 0.4495 0.2256 0.126 Uiso calc R 1 . . H C1 0.2465(7) 0.5732(5) 0.0567(14) 0.089(2) Uani d . 1 . . C C2 0.3033(7) 0.4487(5) 0.4096(16) 0.095(2) Uani d . 1 . . C C11 0.3133(8) 0.6498(5) -0.0617(16) 0.110(2) Uani d D 1 . . C H111 0.2753 0.6552 -0.2458 0.132 Uiso calc R 1 . . H H112 0.4183 0.6279 -0.0472 0.132 Uiso calc R 1 . . H C12 0.2778(9) 0.7532(5) 0.0799(19) 0.138(3) Uani d D 1 . . C H121 0.3301 0.7499 0.2558 0.166 Uiso calc R 1 . . H H122 0.1741 0.7682 0.0937 0.166 Uiso calc R 1 . . H C13 0.3184(12) 0.8392(6) -0.060(2) 0.170(4) Uani d D 1 . . C H131 0.2765 0.8399 -0.2447 0.204 Uiso calc R 1 . . H C14 0.267(2) 0.9396(8) 0.084(4) 0.308(11) Uani d D 1 . . C H141 0.1620 0.9515 0.0729 0.370 Uiso calc R 1 . . H H142 0.2964 0.9943 0.0063 0.370 Uiso calc R 1 . . H H143 0.3085 0.9361 0.2648 0.370 Uiso calc R 1 . . H C15 0.4845(12) 0.8228(9) -0.028(3) 0.266(9) Uani d D 1 . . C H151 0.5149 0.8774 -0.1057 0.319 Uiso calc R 1 . . H H152 0.5213 0.7592 -0.1127 0.319 Uiso calc R 1 . . H H153 0.5220 0.8215 0.1548 0.319 Uiso calc R 1 . . H C21 0.1277(8) 0.3497(5) 0.5162(16) 0.118(3) Uani d D 1 . . C H211 0.0241 0.3686 0.5281 0.141 Uiso calc R 1 . . H H212 0.1800 0.3513 0.6917 0.141 Uiso calc R 1 . . H C22 0.1598(12) 0.2423(5) 0.393(2) 0.162(4) Uani d D 1 . . C H221 0.2640 0.2210 0.3921 0.194 Uiso calc R 1 . . H H222 0.1121 0.2410 0.2142 0.194 Uiso calc R 1 . . H C23 0.1023(15) 0.1705(7) 0.556(2) 0.192(5) Uani d D 1 . . C H231 0.1530 0.1702 0.7306 0.231 Uiso calc R 1 . . H H232 0.1181 0.1028 0.4782 0.231 Uiso calc R 1 . . H H233 -0.0003 0.1935 0.5604 0.231 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.079(3) 0.154(5) 0.132(4) -0.029(3) -0.020(3) 0.023(3) O2 0.090(3) 0.129(4) 0.131(4) -0.038(3) -0.031(3) 0.030(3) N1 0.068(3) 0.103(4) 0.106(4) -0.030(3) -0.005(3) 0.007(4) N2 0.079(3) 0.118(4) 0.122(5) -0.039(3) -0.009(3) 0.022(4) C1 0.068(4) 0.106(5) 0.088(5) -0.014(3) -0.007(4) 0.007(4) C2 0.067(4) 0.101(5) 0.114(6) -0.024(4) -0.007(4) -0.006(4) C11 0.102(5) 0.121(6) 0.110(6) -0.028(4) 0.013(5) 0.005(5) C12 0.121(6) 0.128(7) 0.180(9) -0.039(5) 0.049(6) 0.001(7) C13 0.173(10) 0.123(7) 0.227(13) -0.043(7) 0.048(9) 0.006(8) C14 0.39(2) 0.117(9) 0.46(3) -0.067(11) 0.16(2) 0.018(13) C15 0.194(14) 0.175(11) 0.46(3) -0.078(10) 0.069(16) 0.046(15) C21 0.081(4) 0.150(7) 0.122(6) -0.037(4) -0.004(4) 0.001(6) C22 0.195(10) 0.124(7) 0.181(11) -0.063(7) 0.036(9) -0.015(8) C23 0.255(14) 0.126(7) 0.216(13) -0.063(8) 0.062(11) 0.011(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.206(8) ? O2 C2 . 1.224(9) ? N1 C1 . 1.345(8) ? N1 C2 . 1.410(10) ? N1 H11 . 0.8600 ? N2 C2 . 1.320(9) ? N2 C21 . 1.479(11) ? N2 H21 . 0.8600 ? C1 C11 . 1.496(11) ? C11 C12 . 1.526(10) ? C11 H111 . 0.9700 ? C11 H112 . 0.9700 ? C12 C13 . 1.528(14) ? C12 H121 . 0.9700 ? C12 H122 . 0.9700 ? C13 C15 . 1.524(15) ? C13 C14 . 1.526(16) ? C13 H131 . 0.9800 ? C14 H141 . 0.9600 ? C14 H142 . 0.9600 ? C14 H143 . 0.9600 ? C15 H151 . 0.9600 ? C15 H152 . 0.9600 ? C15 H153 . 0.9600 ? C21 C22 . 1.528(10) ? C21 H211 . 0.9700 ? C21 H212 . 0.9700 ? C22 C23 . 1.529(17) ? C22 H221 . 0.9700 ? C22 H222 . 0.9700 ? C23 H231 . 0.9600 ? C23 H232 . 0.9600 ? C23 H233 . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 128.5(5) ? C1 N1 H11 . . 115.7 ? C2 N1 H11 . . 115.7 ? C2 N2 C21 . . 120.9(7) ? C2 N2 H21 . . 119.6 ? C21 N2 H21 . . 119.6 ? O1 C1 N1 . . 125.1(7) ? O1 C1 C11 . . 120.6(7) ? N1 C1 C11 . . 114.3(6) ? O2 C2 N2 . . 124.4(8) ? O2 C2 N1 . . 118.8(6) ? N2 C2 N1 . . 116.8(7) ? C1 C11 C12 . . 109.5(6) ? C1 C11 H111 . . 109.8 ? C12 C11 H111 . . 109.8 ? C1 C11 H112 . . 109.8 ? C12 C11 H112 . . 109.8 ? H111 C11 H112 . . 108.2 ? C11 C12 C13 . . 112.5(7) ? C11 C12 H121 . . 109.1 ? C13 C12 H121 . . 109.1 ? C11 C12 H122 . . 109.1 ? C13 C12 H122 . . 109.1 ? H121 C12 H122 . . 107.8 ? C15 C13 C14 . . 107.1(11) ? C15 C13 C12 . . 106.7(7) ? C14 C13 C12 . . 108.1(7) ? C15 C13 H131 . . 111.6 ? C14 C13 H131 . . 111.6 ? C12 C13 H131 . . 111.6 ? C13 C14 H141 . . 109.5 ? C13 C14 H142 . . 109.5 ? H141 C14 H142 . . 109.5 ? C13 C14 H143 . . 109.5 ? H141 C14 H143 . . 109.5 ? H142 C14 H143 . . 109.5 ? C13 C15 H151 . . 109.5 ? C13 C15 H152 . . 109.5 ? H151 C15 H152 . . 109.5 ? C13 C15 H153 . . 109.5 ? H151 C15 H153 . . 109.5 ? H152 C15 H153 . . 109.5 ? N2 C21 C22 . . 110.0(6) ? N2 C21 H211 . . 109.7 ? C22 C21 H211 . . 109.7 ? N2 C21 H212 . . 109.7 ? C22 C21 H212 . . 109.7 ? H211 C21 H212 . . 108.2 ? C21 C22 C23 . . 108.0(7) ? C21 C22 H221 . . 110.1 ? C23 C22 H221 . . 110.1 ? C21 C22 H222 . . 110.1 ? C23 C22 H222 . . 110.1 ? H221 C22 H222 . . 108.4 ? C22 C23 H231 . . 109.5 ? C22 C23 H232 . . 109.5 ? H231 C23 H232 . . 109.5 ? C22 C23 H233 . . 109.5 ? H231 C23 H233 . . 109.5 ? H232 C23 H233 . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 . . . . 0.1(11) ? C2 N1 C1 C11 . . . . 179.4(6) ? C21 N2 C2 O2 . . . . 0.2(11) ? C21 N2 C2 N1 . . . . -176.2(6) ? C1 N1 C2 O2 . . . . -177.4(6) ? C1 N1 C2 N2 . . . . -0.8(10) ? O1 C1 C11 C12 . . . . 89.5(9) ? N1 C1 C11 C12 . . . . -89.8(8) ? C1 C11 C12 C13 . . . . -169.7(8) ? C11 C12 C13 C15 . . . . -69.9(11) ? C11 C12 C13 C14 . . . . 175.2(11) ? C2 N2 C21 C22 . . . . -93.9(8) ? N2 C21 C22 C23 . . . . -176.4(8) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H11 O2 2_666 0.86 1.96 2.815(7) 174.8 N2 H21 O1 2_565 0.86 2.35 3.043(8) 137.5