/*
 * International Union of Pure and Applied Chemistry (IUPAC)
 * International Chemical Identifier (InChI)
 * Version 1
 * Software version 1.01
 * July 21, 2006
 * Developed at NIST
 */

#ifndef __EXTR_CT_H__
#define __EXTR_CT_H__

#include "mode.h"
#include "ichisize.h"

struct AtData {
     char element[3];
     int maxvalence;
};

 

#define NUM_CHEM_ELEMENTS 127   /* well above number of known chem. elements */


#define               AT_ISO_SORT_KEY_MULT  32  /* up to 32 identical hydrogen isotopes */
                                                /* (similar to T_GROUP_ISOWT_MULT) */
                                                /* changed from 16 9-12-2003 */
typedef long          AT_ISO_SORT_KEY;          /* signed, should hold up to 4096*max_iso_diff */
                                                /* (similar to T_GROUP_ISOWT) */
/*
   = num_1H + AT_ISO_SORT_KEY_MULT*(num_D + AT_ISO_SORT_KEY_MULT*(num_T+AT_ISO_SORT_KEY_MULT*iso_atw_diff))
*/

/* typedef signed   char AT_ISOTOPIC; */ /* + or - */
typedef struct tagStereoCarb {
    AT_NUMB        at_num;
    U_CHAR         parity;
} AT_STEREO_CARB;
typedef struct tagStereoDble {
    AT_NUMB        at_num1;
    AT_NUMB        at_num2;
    U_CHAR         parity;
} AT_STEREO_DBLE;

typedef struct tagIsotopicAtom {
    AT_NUMB        at_num;
    NUM_H          num_1H;
    NUM_H          num_D;
    NUM_H          num_T;
    NUM_H          iso_atw_diff;
} AT_ISOTOPIC;

typedef AT_NUMB AT_STEREO;

#define BYTE_BITS         8       /* number of bits in one byte */

#define BOND_MASK         0xf     /* 4 bits */
#define BOND_BITS         4       /* 3 or 4 does not matter; 2 is too small for BOND_TAUTOM */
#define BOND_ADD          (BOND_BITS==2?-1:0) /* subtract 1 from bonds stored in CT */


typedef struct tagAtom {
    char elname[ATOM_EL_LEN];
    AT_NUMB    neighbor[MAXVAL]; /* changed to unsigned 2-2-95. D.Ch. */
    AT_NUMB    init_rank;        /* also used in remove_terminal_HDT() to save orig. at. number */
    AT_NUMB    orig_at_number;
    AT_NUMB    orig_compt_at_numb;
    /* low 3 bits=bond type;
       high 5 bits (in case of cut-vertex atom) = an attached part number
    */
    U_CHAR bond_type[MAXVAL];
    U_CHAR el_number;  /* periodic table number = charge of the nucleus = number of the protons */
    /* U_CHAR hill_type; */  /* number in psudo hill order */
    S_CHAR valence;
    S_CHAR chem_bonds_valence; /* 8-24-00 to treat tautomer centerpoints, etc. */
    S_CHAR num_H;              /* first not including D, T; add_DT_to_num_H() includes. */
    S_CHAR num_iso_H[NUM_H_ISOTOPES];   /* num 1H, 2H(D), 3H(T) */
    S_CHAR cFlags;
    S_CHAR iso_atw_diff;        /* abs(iso_atw_diff) < 127 or 31 - ??? */
    AT_ISO_SORT_KEY iso_sort_key;  /* = num_1H + AT_ISO_SORT_KEY_MULT^1*num_D
                                               + AT_ISO_SORT_KEY_MULT^2*num_T
                                               + AT_ISO_SORT_KEY_MULT^3*iso_atw_diff
                                    */
    S_CHAR charge;
    S_CHAR radical; /* 1=>doublet(.), 2=> triplet as singlet (:) ???? why are they same ???? */
    S_CHAR marked;
    
    AT_NUMB endpoint;  /* tautomer analysis. If != 0 then the hydrogens & (-)charge are in the tautomer group. */

    /*
       Pairs stereo_bond_neighbor[] and stereo_bond_neighbor2[], etc
       initially refer to non-isotopic and isotopic cases, respectively.
       To use same stereo processing code these arrays are swapped when
       switching from non-isotopic to isotopic processing and back.
    */
    AT_NUMB stereo_bond_neighbor[MAX_NUM_STEREO_BONDS];  /* Original number of an opposite atom */
    AT_NUMB stereo_bond_neighbor2[MAX_NUM_STEREO_BONDS]; /*     (stereo bond neighbor) +1; */
    S_CHAR  stereo_bond_ord[MAX_NUM_STEREO_BONDS];    /* Ordering number of a bond/neighbor in the direction to the */
    S_CHAR  stereo_bond_ord2[MAX_NUM_STEREO_BONDS];   /* stereo bond opposite atom (important for cumulenes); */
    S_CHAR  stereo_bond_z_prod[MAX_NUM_STEREO_BONDS];  /* Relative  atom-neighbors */
    S_CHAR  stereo_bond_z_prod2[MAX_NUM_STEREO_BONDS]; /* double bond planes orientation; */
    S_CHAR  stereo_bond_parity[MAX_NUM_STEREO_BONDS];  /* parity + MULT_STEREOBOND*chain_length, */
    S_CHAR  stereo_bond_parity2[MAX_NUM_STEREO_BONDS]; /* where: */
              /*
                 parity (Mask 0x07=BITS_PARITY):
                
                 0   = AB_PARITY_NONE = not a stereo bond
                 1/2 = AB_PARITY_ODD/EVEN = bond parity defined from initial ranks
                 3   = AB_PARITY_UNKN = geometry is unknown to the user
                 4   = AB_PARITY_UNDF = not enough geometry info to find the parity
                 6   = AB_PARITY_CALC = calculate later from the neighbor ranks; some ot them can be
                       replaced with AB_PARITY_ODD/EVEN after equivalence ranks have been determined
                
                 length (Mask 0x38=MASK_CUMULENE_LEN, length=stereo_bond_parity[i]/MULT_STEREOBOND):
                
                 0   => double or alternating stereogenic bond
                 1   => cumulene with 2 double bonds (stereogenic center)
                 2   => cumulene with 3 double bonds (stereogenic bond)
                 length <= (MAX_CUMULENE_LEN=2)
                 bit KNOWN_PARITIES_EQL =  0x40: all pairs of const. equ. atoms are connected by stereo bonds
                                                and these bonds have identical parities
              */

    S_CHAR parity; /* -- Mask 0x07=BITS_PARITY: --
                   0 = AB_PARITY_NONE => no parity; also parity&0x38 = 0
                   1 = AB_PARITY_ODD  => odd parity
                   2 = AB_PARITY_EVEN => even parity
                   3 = AB_PARITY_UNKN => user marked as unknown parity
                   4 = AB_PARITY_UNDF => parity cannot be defined because of symmetry or not well defined geometry
                  */
    S_CHAR parity2;        /* parity including parity due to isotopic terminal H */
    /* bit msks: 0x07 => known parity (1,2,3,4) or AB_PARITY_CALC=6, AB_PARITY_IISO = 6 */
    /*           0x40 => KNOWN_PARITIES_EQL */
    S_CHAR stereo_atom_parity; /* similar to stereo_bond_parity[]: known in advance AB_PARITY_* value + KNOWN_PARITIES_EQL bit */
    S_CHAR stereo_atom_parity2;
    S_CHAR final_parity;   /* defined by equivalence ranks */
    S_CHAR final_parity2;  /* defined by equivalence ranks, incl. due to terminal isotopic H */
    S_CHAR bAmbiguousStereo;
    S_CHAR bHasStereoOrEquToStereo;
    S_CHAR bHasStereoOrEquToStereo2;
#if( FIND_RING_SYSTEMS == 1 )
    S_CHAR    bCutVertex;
    AT_NUMB   nRingSystem;
    AT_NUMB   nNumAtInRingSystem;
    AT_NUMB   nBlockSystem;
#if( FIND_RINS_SYSTEMS_DISTANCES == 1 )
    AT_NUMB   nDistanceFromTerminal;
#endif
#endif
    S_CHAR z_dir[3];

} sp_ATOM ;

#define BOND_SINGLE BOND_TYPE_SINGLE  /* 1 */
#define BOND_DOUBLE BOND_TYPE_DOUBLE  /* 2 */
#define BOND_TRIPLE BOND_TYPE_TRIPLE  /* 3 */
#define BOND_ALTERN BOND_TYPE_ALTERN  /* 4 single/double */

#define BOND_ALT_123             5  /* single/double/triple */
#define BOND_ALT_13              6  /* single/triple */
#define BOND_ALT_23              7  /* double/triple */
#define BOND_TAUTOM              8
#define BOND_ALT12NS             9
#define BOND_NUMDIF              9  /* number of different kinds of bonds */

#define BOND_TYPE_MASK        0x0f

#define BOND_MARK_ALL         0xf0  /* complement to BOND_TYPE_MASK */

#define BOND_MARK_ALT12       0x10
#define BOND_MARK_ALT123      0x20
#define BOND_MARK_ALT13       0x30
#define BOND_MARK_ALT23       0x40
#define BOND_MARK_ALT12NS     0x50  /* 1 or 2, non-stereo */
#define BOND_MARK_MASK        0x70

#define ACTUAL_ORDER(PBNS, IAT,IBOND, BTYPE)  ( ((PBNS) && (PBNS)->edge && (PBNS)->vert &&\
    ((BTYPE)==BOND_ALT_123 || (BTYPE)==BOND_ALT_13 || (BTYPE)==BOND_ALT_23))? (PBNS)->edge[(PBNS)->vert[IAT].iedge[IBOND]].flow+BOND_TYPE_SINGLE:(BTYPE))


#define BITS_PARITY        0x07  /* mask to retrieve half-bond parity */
#define MASK_CUMULENE_LEN  0x38  /* mask to retrieve (cumulene chain length - 1)*MULT_STEREOBOND */
#define KNOWN_PARITIES_EQL 0x40  /* parity is same for all pairs of constit. equivalent atoms */
#define MAX_CUMULENE_LEN   2     /* max number of bonds in a cumulene chain - 1 */

#define MULT_STEREOBOND    0x08  /* multiplier for cumulene chain length
                                    odd length => chiral, even length => stereogenic bond */

#define MAKE_BITS_CUMULENE_LEN(X)   ((X)*MULT_STEREOBOND)
#define GET_BITS_CUMULENE_LEN(X)    ((X)&MASK_CUMULENE_LEN)
#define BOND_CHAIN_LEN(X)           (GET_BITS_CUMULENE_LEN(X)/MULT_STEREOBOND) /* 0 => double bond, 1 => allene, 2 => cumulene,..*/
#define IS_ALLENE_CHAIN(X)          ((GET_BITS_CUMULENE_LEN(X)/MULT_STEREOBOND)%2)

/* atom or bond parity value definitions */
#define AB_PARITY_NONE   0  /* 0 => no parity; also parity&0x38 = 0 */
#define AB_PARITY_ODD    1  /* 1 => odd parity */
#define AB_PARITY_EVEN   2  /* 2 => even parity */
#define AB_PARITY_UNKN   3  /* 3 => user marked as unknown parity */
#define AB_PARITY_UNDF   4  /* 4 => parity cannot be defined because of symmetry or not well defined geometry */
#define AB_PARITY_IISO   5  /* 5 => no parity because of identical atoms */
#define AB_PARITY_CALC   6  /* 6 => calculate parity later */
#define AB_PARITY_0D     8  /* 8 => bit signifies 0D case -- not used */

#define AB_INV_PARITY_BITS (AB_PARITY_ODD ^ AB_PARITY_EVEN)


#define AB_MAX_KNOWN_PARITY        4 /* precalculated from const. equivalence parities */
#define AB_MIN_KNOWN_PARITY        1

#define AB_MAX_PART_DEFINED_PARITY 3 /* 1, 2, 3 => defined parities, uncluding 'unknown' */
#define AB_MIN_PART_DEFINED_PARITY 1 /* min(AB_PARITY_ODD, AB_PARITY_EVEN, AB_PARITY_UNKN) */

#define AB_MAX_WELL_DEFINED_PARITY 2 /* 1, 2 => well defined parities, uncluding 'unknown' */
#define AB_MIN_WELL_DEFINED_PARITY 1 /* min(AB_PARITY_ODD, AB_PARITY_EVEN) */

#define AB_MIN_ILL_DEFINED_PARITY  3
#define AB_MAX_ILL_DEFINED_PARITY  4

#define AB_MAX_ANY_PARITY          4
#define AB_MIN_ANY_PARITY          1

#define AMBIGUOUS_STEREO           1
#define AMBIGUOUS_STEREO_ATOM      2
#define AMBIGUOUS_STEREO_BOND      4
#define AMBIGUOUS_STEREO_ATOM_ISO  8
#define AMBIGUOUS_STEREO_BOND_ISO  16
#define AMBIGUOUS_STEREO_ERROR     32


#define MIN_DOT_PROD 50          /* min value of at->stereo_bond_z_prod[i] to define parity */

#define ATOM_PARITY_VAL(X)          (X)
#define ATOM_PARITY_PART_DEF(X)     (AB_MIN_PART_DEFINED_PARITY <= (X) && (X) <= AB_MAX_PART_DEFINED_PARITY)
#define ATOM_PARITY_ILL_DEF(X)      (AB_MIN_ILL_DEFINED_PARITY <= (X) && (X) <= AB_MAX_ILL_DEFINED_PARITY)
#define ATOM_PARITY_KNOWN(X)        (AB_MIN_KNOWN_PARITY <= (X) && (X) <= AB_MAX_KNOWN_PARITY)
#define ATOM_PARITY_WELL_DEF(X)     (AB_MIN_WELL_DEFINED_PARITY <= (X) && (X) <= AB_MAX_WELL_DEFINED_PARITY)
#define ATOM_PARITY_NOT_UNKN(X)     (ATOM_PARITY_KNOWN(X) && (X) != AB_PARITY_UNKN)

#define PARITY_VAL(X)               ((X) & BITS_PARITY)
#define PARITY_PART_DEF(X)          (AB_MIN_PART_DEFINED_PARITY <= PARITY_VAL(X) && PARITY_VAL(X) <= AB_MAX_PART_DEFINED_PARITY)
#define PARITY_ILL_DEF(X)           (AB_MIN_ILL_DEFINED_PARITY <= PARITY_VAL(X) && PARITY_VAL(X) <= AB_MAX_ILL_DEFINED_PARITY)
#define PARITY_KNOWN(X)             (AB_MIN_KNOWN_PARITY <= PARITY_VAL(X) && PARITY_VAL(X) <= AB_MAX_KNOWN_PARITY)
#define PARITY_WELL_DEF(X)          (AB_MIN_WELL_DEFINED_PARITY <= PARITY_VAL(X) && PARITY_VAL(X) <= AB_MAX_WELL_DEFINED_PARITY)
#define PARITY_CALCULATE(X)         (AB_PARITY_CALC == PARITY_VAL(X))
#define BOND_PARITY_PART_DEFINED(X) (PARITY_PART_DEF(X) || PARITY_CALCULATE(X))
#define BOND_PARITY_PART_KNOWN(X)   (PARITY_KNOWN(X) || PARITY_CALCULATE(X))
#define ALL_BUT_PARITY(X)           ((X)&~BITS_PARITY)

#define ALWAYS_SET_STEREO_PARITY           0
#define NO_ISOLATED_NON_6RING_AROM_BOND    0  /* for Yuri */
#define SAVE_6_AROM_CENTERS                0  /* for Yuri */

#endif /* __EXTR_CT_H__ */


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