# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 23 14:23:32 2021
#   Inital geometry file: a 62 line input string
#   Ligand name: 1-phenyl-1H-pyrazole-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1cnn(c1)c2ccccc2
#
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
 ZZA  ZZA  '1-phenyl-1H-pyrazole-4-carboxylic acid'  ligand  22  14  .  2021-08-25  2022-11-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_ZZA
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
 ZZA  O1   O  OH1   0  -0.597  4.7475  12.2305   4.7354
 ZZA  C2   C  C     0   0.473  4.3549  13.4779   4.5061
 ZZA  O3   O  O     0  -0.446  3.9202  14.2137   5.3615
 ZZA  C4   C  CR5   0  -0.319  4.5102  13.8544   3.1068
 ZZA  C5   C  CR15  0  -0.012  5.0118  13.1122   2.0161
 ZZA  N6   N  N     0  -0.266  4.9957  13.8229   0.9151
 ZZA  N7   N  NR5   0  -0.398  4.4924  15.0160   1.2641
 ZZA  C8   C  CR15  0   0.094  4.1906  15.0820   2.5690
 ZZA  C9   C  CR6   0   0.371  4.3524  16.0378   0.2985
 ZZA  C10  C  CR16  0  -0.308  3.3480  16.9876   0.4383
 ZZA  C11  C  CR16  0  -0.249  3.2317  18.0000  -0.5027
 ZZA  C12  C  CR16  0  -0.255  4.0977  18.0555  -1.5860
 ZZA  C13  C  CR16  0  -0.248  5.0886  17.0922  -1.7226
 ZZA  C14  C  CR16  0  -0.291  5.2253  16.0831  -0.7816
 ZZA  H1   H  HOH1  0   0.488  4.6371  12.0146   5.6733
 ZZA  H5   H  HCR5  0   0.282  5.3737  12.0956   2.0027
 ZZA  H8   H  HCR5  0   0.318  3.8012  15.9736   3.0317
 ZZA  H10  H  HCR6  0   0.283  2.6474  16.9354   1.2612
 ZZA  H14  H  HCR6  0   0.279  6.0065  15.3431  -0.8839
 ZZA  H11  H  HCR6  0   0.269  2.4491  18.7384  -0.3920
 ZZA  H12  H  HCR6  0   0.265  3.9986  18.8423  -2.3215
 ZZA  H13  H  HCR6  0   0.267  5.7687  17.1275  -2.5631

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
 ZZA  O1   C2   single    1.328  0.020  1.328
 ZZA  C2   O3   double    1.209  0.020  1.209
 ZZA  C2   C4   single    1.457  0.020  1.457
 ZZA  C4   C5   aromatic  1.411  0.020  1.411
 ZZA  C4   C8   aromatic  1.378  0.020  1.378
 ZZA  C5   N6   aromatic  1.311  0.020  1.311
 ZZA  N6   N7   aromatic  1.341  0.020  1.341
 ZZA  N7   C8   aromatic  1.341  0.020  1.341
 ZZA  N7   C9   single    1.413  0.020  1.413
 ZZA  C9   C10  aromatic  1.389  0.020  1.389
 ZZA  C9   C14  aromatic  1.389  0.020  1.389
 ZZA  C10  C11  aromatic  1.387  0.020  1.387
 ZZA  C11  C12  aromatic  1.388  0.020  1.388
 ZZA  C12  C13  aromatic  1.389  0.020  1.389
 ZZA  C13  C14  aromatic  1.386  0.020  1.386
 ZZA  O1   H1   single    0.850  0.020  0.980
 ZZA  C5   H5   single    0.930  0.020  1.080
 ZZA  C8   H8   single    0.930  0.020  1.080
 ZZA  C10  H10  single    0.930  0.020  1.080
 ZZA  C14  H14  single    0.930  0.020  1.080
 ZZA  C11  H11  single    0.930  0.020  1.080
 ZZA  C12  H12  single    0.930  0.020  1.080
 ZZA  C13  H13  single    0.930  0.020  1.080

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
 ZZA  H1   O1   C2   110.05  3.000
 ZZA  C4   C2   O3   124.08  3.000
 ZZA  C4   C2   O1   112.14  3.000
 ZZA  O3   C2   O1   123.77  3.000
 ZZA  C8   C4   C5   104.44  3.000
 ZZA  C8   C4   C2   125.46  3.000
 ZZA  C5   C4   C2   130.09  3.000
 ZZA  H5   C5   N6   120.30  3.000
 ZZA  H5   C5   C4   128.62  3.000
 ZZA  N6   C5   C4   111.08  3.000
 ZZA  N7   N6   C5   105.58  3.000
 ZZA  C9   N7   C8   127.39  3.000
 ZZA  C9   N7   N6   120.18  3.000
 ZZA  C8   N7   N6   112.42  3.000
 ZZA  H8   C8   N7   122.68  3.000
 ZZA  H8   C8   C4   130.81  3.000
 ZZA  N7   C8   C4   106.48  3.000
 ZZA  C14  C9   C10  120.67  3.000
 ZZA  C14  C9   N7   119.51  3.000
 ZZA  C10  C9   N7   119.82  3.000
 ZZA  H10  C10  C11  119.79  3.000
 ZZA  H10  C10  C9   120.77  3.000
 ZZA  C11  C10  C9   119.43  3.000
 ZZA  H11  C11  C12  120.27  3.000
 ZZA  H11  C11  C10  119.31  3.000
 ZZA  C12  C11  C10  120.42  3.000
 ZZA  H12  C12  C13  120.21  3.000
 ZZA  H12  C12  C11  120.17  3.000
 ZZA  C13  C12  C11  119.61  3.000
 ZZA  H13  C13  C14  119.28  3.000
 ZZA  H13  C13  C12  120.15  3.000
 ZZA  C14  C13  C12  120.56  3.000
 ZZA  H14  C14  C13  120.35  3.000
 ZZA  H14  C14  C9   120.35  3.000
 ZZA  C13  C14  C9   119.30  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
 ZZA  CONST_01  N7   N6   C5   C4     0.00   0.0  0
 ZZA  CONST_02  N6   N7   C8   C4     0.00   0.0  0
 ZZA  CONST_03  C9   N7   C8   C4   180.00   0.0  0
 ZZA  CONST_04  N7   C8   C4   C5     0.00   0.0  0
 ZZA  CONST_05  C8   N7   N6   C5     0.00   0.0  0
 ZZA  CONST_06  C9   N7   N6   C5   180.00   0.0  0
 ZZA  CONST_07  C8   C4   C5   N6     0.00   0.0  0
 ZZA  CONST_10  C11  C10  C9   N7   180.00   0.0  0
 ZZA  CONST_11  C13  C14  C9   N7   180.00   0.0  0
 ZZA  CONST_14  C12  C11  C10  C9     0.00   0.0  0
 ZZA  CONST_15  C12  C13  C14  C9     0.00   0.0  0
 ZZA  CONST_16  C13  C14  C9   C10    0.00   0.0  0
 ZZA  CONST_17  C13  C12  C11  C10    0.00   0.0  0
 ZZA  CONST_18  C14  C9   C10  C11    0.00   0.0  0
 ZZA  CONST_19  C14  C13  C12  C11    0.00   0.0  0
 ZZA  CONST_20  N6   C5   C4   C2   180.00   0.0  0
 ZZA  CONST_21  N7   C8   C4   C2   180.00   0.0  0
 ZZA  CONST_22  H8   C8   C4   C5   180.00   0.0  0
 ZZA  CONST_23  H5   C5   N6   N7   180.00   0.0  0
 ZZA  CONST_24  H10  C10  C9   N7     0.00   0.0  0
 ZZA  CONST_25  H14  C14  C9   N7     0.00   0.0  0
 ZZA  CONST_26  H11  C11  C10  C9   180.00   0.0  0
 ZZA  CONST_27  H13  C13  C14  C9   180.00   0.0  0
 ZZA  CONST_28  H12  C12  C11  C10  180.00   0.0  0
 ZZA  CONST_29  H1   O1   C2   C4   180.00   0.0  0
 ZZA  Var_01    C5   C4   C2   O1    -0.75  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
 ZZA  plan-1  C2   0.020
 ZZA  plan-1  C4   0.020
 ZZA  plan-1  C5   0.020
 ZZA  plan-1  N6   0.020
 ZZA  plan-1  N7   0.020
 ZZA  plan-1  C8   0.020
 ZZA  plan-1  C9   0.020
 ZZA  plan-1  H5   0.020
 ZZA  plan-1  H8   0.020
 ZZA  plan-2  N7   0.020
 ZZA  plan-2  C9   0.020
 ZZA  plan-2  C10  0.020
 ZZA  plan-2  C11  0.020
 ZZA  plan-2  C12  0.020
 ZZA  plan-2  C13  0.020
 ZZA  plan-2  C14  0.020
 ZZA  plan-2  H10  0.020
 ZZA  plan-2  H14  0.020
 ZZA  plan-2  H11  0.020
 ZZA  plan-2  H12  0.020
 ZZA  plan-2  H13  0.020
 ZZA  plan-3  O1   0.020
 ZZA  plan-3  C2   0.020
 ZZA  plan-3  O3   0.020
 ZZA  plan-3  C4   0.020
 ZZA  plan-3  H1   0.020

