# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 23 11:50:25 2021
#   Inital geometry file: a 74 line input string
#   Ligand name: N-(4-hydroxyphenyl)-1-methyl-1H-pyrazole-4-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cn1cc(cn1)C(=O)Nc2ccc(O)cc2
#
data_comp_list
loop_
_chem_comp.id
_chem_comp.three_letter_code
_chem_comp.name
_chem_comp.group
_chem_comp.number_atoms_all
_chem_comp.number_atoms_nh
_chem_comp.desc_level
_chem_comp.initial_date
_chem_comp.modified_date
_chem_comp.source
 WS4  WS4  N-(4-hydroxyphenyl)-1-methyl-1H-pyrazole-4-carboxamide  ligand  27  16  .  2022-03-29  2022-03-29
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_WS4
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.type_energy
_chem_comp_atom.charge
_chem_comp_atom.partial_charge
_chem_comp_atom.x
_chem_comp_atom.y
_chem_comp_atom.z
 WS4  N1   N  N     0  -0.270  -0.3287  10.8103   -7.7535
 WS4  C4   C  CR6   0   0.346   3.1449  10.1089  -12.1769
 WS4  C5   C  CR16  0  -0.290   4.0110   9.0406  -12.3958
 WS4  C6   C  CR16  0  -0.376   4.8333   9.0241  -13.5132
 WS4  C7   C  CR16  0  -0.329   3.1364  11.1574  -13.0967
 WS4  C8   C  CR16  0  -0.327   3.9647  11.1482  -14.2042
 WS4  C10  C  CR15  0   0.102   0.2339   8.7570   -8.3806
 WS4  O1   O  O     0  -0.476   1.9751   8.0221  -10.5528
 WS4  C3   C  C     0   0.492   1.7599   9.2050  -10.3332
 WS4  C2   C  CR5   0  -0.296   0.8783   9.6285   -9.2384
 WS4  C1   C  CR15  0  -0.078   0.4803  10.9034   -8.7864
 WS4  N    N  NR5   0  -0.265  -0.4654   9.5031   -7.5230
 WS4  C    C  CH3   0  -0.519  -1.2999   9.0317   -6.4395
 WS4  N2   N  NH1   0  -0.760   2.3053  10.2150  -11.0564
 WS4  C9   C  CR6   0   0.341   4.8205  10.0727  -14.4262
 WS4  O    O  OH1   0  -0.635   5.6068  10.1018  -15.5230
 WS4  H1   H  HCR6  0   0.274   4.0657   8.2174  -11.7017
 WS4  H2   H  HCR6  0   0.272   5.4984   8.1809  -13.6621
 WS4  H3   H  HCR6  0   0.270   2.4710  11.9994  -12.9448
 WS4  H4   H  HCR6  0   0.267   3.9427  11.9760  -14.9017
 WS4  H5   H  HCR5  0   0.301   0.2368   7.6800   -8.3345
 WS4  H6   H  HCR5  0   0.266   0.7476  11.8787   -9.1663
 WS4  H7   H  HCH3  0   0.271  -1.7225   9.8945   -5.9356
 WS4  H8   H  HCH3  0   0.265  -2.1071   8.4109   -6.8227
 WS4  H9   H  HCH3  0   0.266  -0.7115   8.4557   -5.7287
 WS4  H10  H  HNH1  0   0.414   2.0041  11.1520  -10.8405
 WS4  H11  H  HOH1  0   0.474   6.1543   9.3100  -15.5627

loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.type
_chem_comp_bond.value_dist
_chem_comp_bond.value_dist_esd
_chem_comp_bond.value_dist_neutron
 WS4  O    C9   single    1.350  0.020  1.350
 WS4  C9   C8   aromatic  1.392  0.020  1.392
 WS4  C9   C6   aromatic  1.390  0.020  1.390
 WS4  C8   C7   aromatic  1.383  0.020  1.383
 WS4  C6   C5   aromatic  1.387  0.020  1.387
 WS4  C7   C4   aromatic  1.395  0.020  1.395
 WS4  C5   C4   aromatic  1.393  0.020  1.393
 WS4  C4   N2   single    1.404  0.020  1.404
 WS4  N2   C3   single    1.357  0.020  1.357
 WS4  O1   C3   double    1.222  0.020  1.222
 WS4  C3   C2   single    1.468  0.020  1.468
 WS4  C2   C1   aromatic  1.410  0.020  1.410
 WS4  C2   C10  aromatic  1.382  0.020  1.382
 WS4  C1   N1   aromatic  1.315  0.020  1.315
 WS4  C10  N    aromatic  1.335  0.020  1.335
 WS4  N1   N    aromatic  1.334  0.020  1.334
 WS4  N    C    single    1.447  0.020  1.447
 WS4  C5   H1   single    0.930  0.020  1.080
 WS4  C6   H2   single    0.930  0.020  1.080
 WS4  C7   H3   single    0.930  0.020  1.080
 WS4  C8   H4   single    0.930  0.020  1.080
 WS4  C10  H5   single    0.930  0.020  1.080
 WS4  C1   H6   single    0.930  0.020  1.080
 WS4  C    H7   single    0.970  0.020  1.090
 WS4  C    H8   single    0.970  0.020  1.090
 WS4  C    H9   single    0.970  0.020  1.090
 WS4  N2   H10  single    0.860  0.020  1.020
 WS4  O    H11  single    0.850  0.020  0.980

loop_
_chem_comp_angle.comp_id
_chem_comp_angle.atom_id_1
_chem_comp_angle.atom_id_2
_chem_comp_angle.atom_id_3
_chem_comp_angle.value_angle
_chem_comp_angle.value_angle_esd
 WS4  N    N1   C1   105.55  3.000
 WS4  N2   C4   C7   117.76  3.000
 WS4  N2   C4   C5   123.73  3.000
 WS4  C7   C4   C5   118.48  3.000
 WS4  H1   C5   C6   118.64  3.000
 WS4  H1   C5   C4   121.07  3.000
 WS4  C6   C5   C4   120.29  3.000
 WS4  H2   C6   C9   120.13  3.000
 WS4  H2   C6   C5   118.91  3.000
 WS4  C9   C6   C5   120.96  3.000
 WS4  H3   C7   C8   119.02  3.000
 WS4  H3   C7   C4   119.69  3.000
 WS4  C8   C7   C4   121.29  3.000
 WS4  H4   C8   C9   120.02  3.000
 WS4  H4   C8   C7   119.91  3.000
 WS4  C9   C8   C7   120.07  3.000
 WS4  H5   C10  N    122.17  3.000
 WS4  H5   C10  C2   130.94  3.000
 WS4  N    C10  C2   106.89  3.000
 WS4  N2   C3   C2   115.10  3.000
 WS4  C2   C3   O1   121.26  3.000
 WS4  N2   C3   O1   123.64  3.000
 WS4  C1   C2   C3   132.02  3.000
 WS4  C1   C2   C10  103.86  3.000
 WS4  C3   C2   C10  124.12  3.000
 WS4  H6   C1   C2   129.33  3.000
 WS4  H6   C1   N1   119.49  3.000
 WS4  C2   C1   N1   111.18  3.000
 WS4  C    N    C10  126.97  3.000
 WS4  C    N    N1   120.51  3.000
 WS4  C10  N    N1   112.52  3.000
 WS4  H9   C    H8   109.23  3.000
 WS4  H9   C    H7   109.16  3.000
 WS4  H8   C    H7   109.17  3.000
 WS4  H9   C    N    110.48  3.000
 WS4  H8   C    N    110.50  3.000
 WS4  H7   C    N    108.27  3.000
 WS4  H10  N2   C3   117.25  3.000
 WS4  H10  N2   C4   114.84  3.000
 WS4  C3   N2   C4   127.55  3.000
 WS4  O    C9   C8   118.10  3.000
 WS4  C8   C9   C6   118.91  3.000
 WS4  O    C9   C6   122.98  3.000
 WS4  H11  O    C9   110.29  3.000

loop_
_chem_comp_tor.comp_id
_chem_comp_tor.id
_chem_comp_tor.atom_id_1
_chem_comp_tor.atom_id_2
_chem_comp_tor.atom_id_3
_chem_comp_tor.atom_id_4
_chem_comp_tor.value_angle
_chem_comp_tor.value_angle_esd
_chem_comp_tor.period
 WS4  CONST_01  C10  C2   C1   N1      0.00   0.0  0
 WS4  CONST_02  C2   C10  N    N1      0.00   0.0  0
 WS4  CONST_03  C9   C8   C7   C4      0.00   0.0  0
 WS4  CONST_04  C9   C6   C5   C4      0.00   0.0  0
 WS4  CONST_05  C8   C9   C6   C5      0.00   0.0  0
 WS4  CONST_06  C8   C7   C4   C5      0.00   0.0  0
 WS4  CONST_07  C7   C8   C9   C6      0.00   0.0  0
 WS4  CONST_08  C7   C4   C5   C6      0.00   0.0  0
 WS4  CONST_09  C1   N1   N    C10     0.00   0.0  0
 WS4  CONST_10  N    N1   C1   C2      0.00   0.0  0
 WS4  CONST_11  N    C10  C2   C1      0.00   0.0  0
 WS4  CONST_12  C3   C2   C1   N1    180.00   0.0  0
 WS4  CONST_13  O    C9   C6   C5    180.00   0.0  0
 WS4  CONST_14  N2   C4   C5   C6    180.00   0.0  0
 WS4  CONST_15  O    C9   C8   C7    180.00   0.0  0
 WS4  CONST_16  N2   C4   C7   C8    180.00   0.0  0
 WS4  CONST_17  N    C10  C2   C3    180.00   0.0  0
 WS4  CONST_18  C    N    C10  C2    180.00   0.0  0
 WS4  CONST_19  C    N    N1   C1    180.00   0.0  0
 WS4  CONST_20  H5   C10  N    N1    180.00   0.0  0
 WS4  CONST_21  H4   C8   C7   C4    180.00   0.0  0
 WS4  CONST_22  H2   C6   C5   C4    180.00   0.0  0
 WS4  CONST_23  H3   C7   C4   C5    180.00   0.0  0
 WS4  CONST_24  H1   C5   C4   C7    180.00   0.0  0
 WS4  CONST_25  H6   C1   C2   C10   180.00   0.0  0
 WS4  CONST_26  C2   C3   N2   C4    180.00   0.0  0
 WS4  CONST_30  O1   C3   N2   C4      0.00   0.0  0
 WS4  Var_01    N2   C3   C2   C10  -179.53  30.0  2
 WS4  Var_02    H7   C    N    N1     -0.10  30.0  2

loop_
_chem_comp_plane_atom.comp_id
_chem_comp_plane_atom.plane_id
_chem_comp_plane_atom.atom_id
_chem_comp_plane_atom.dist_esd
 WS4  plan-1  N1   0.020
 WS4  plan-1  C10  0.020
 WS4  plan-1  C3   0.020
 WS4  plan-1  C2   0.020
 WS4  plan-1  C1   0.020
 WS4  plan-1  N    0.020
 WS4  plan-1  C    0.020
 WS4  plan-1  H5   0.020
 WS4  plan-1  H6   0.020
 WS4  plan-2  C4   0.020
 WS4  plan-2  C5   0.020
 WS4  plan-2  C6   0.020
 WS4  plan-2  C7   0.020
 WS4  plan-2  C8   0.020
 WS4  plan-2  N2   0.020
 WS4  plan-2  C9   0.020
 WS4  plan-2  O    0.020
 WS4  plan-2  H1   0.020
 WS4  plan-2  H2   0.020
 WS4  plan-2  H3   0.020
 WS4  plan-2  H4   0.020
 WS4  plan-3  C4   0.020
 WS4  plan-3  O1   0.020
 WS4  plan-3  C3   0.020
 WS4  plan-3  C2   0.020
 WS4  plan-3  N2   0.020
 WS4  plan-3  H10  0.020

