# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Mar 20 23:21:29 2022
#   Inital geometry file: a 78 line input string
#   Ligand name: 5-cyclopropyl-1-phenyl-pyrazole-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1cnn(c2ccccc2)c1C3CC3
#
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
 QHN  QHN  '5-cyclopropyl-1-phenyl-pyrazole-4-carboxylic acid'  ligand  28  17  .  2022-08-10  2023-02-15
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_QHN
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
 QHN  C1   C  C      0   0.345  -39.2092  -16.8037  11.5312
 QHN  C10  C  CR16   0  -0.258  -39.3449  -19.0795   4.8961
 QHN  C11  C  CR16   0  -0.254  -39.1494  -18.1442   3.8889
 QHN  C12  C  CR16   0  -0.254  -38.8078  -16.8395   4.2203
 QHN  C13  C  CR16   0  -0.282  -38.6730  -16.4659   5.5489
 QHN  C2   C  CR5    0  -0.394  -38.8459  -16.7588  10.0723
 QHN  C3   C  CR5    0   0.451  -39.4834  -17.3133   8.9761
 QHN  C4   C  CH1    0  -0.324  -40.7732  -18.0209   8.8548
 QHN  C5   C  CH2    0  -0.480  -41.7924  -17.5725   7.8450
 QHN  C6   C  CH2    0  -0.461  -42.0347  -17.3521   9.3023
 QHN  C7   C  CR15   0  -0.064  -37.7026  -16.1417   9.5301
 QHN  C8   C  CR6    0   0.330  -38.8696  -17.4082   6.5522
 QHN  C9   C  CR16   0  -0.264  -39.1962  -18.7189   6.2275
 QHN  N1   N  NR5    0  -0.451  -38.6981  -17.0265   7.9004
 QHN  N2   N  N      0  -0.289  -37.6157  -16.3091   8.2297
 QHN  O1   O  O      0  -0.586  -40.0849  -17.6183  11.8814
 QHN  O2   O  OC    -1  -0.600  -38.5690  -16.0244  12.2676
 QHN  H10  H  HCR6   0   0.260  -38.6525  -16.1039   3.4419
 QHN  H11  H  HCR6   0   0.266  -38.4166  -15.4473   5.8075
 QHN  H1   H  HCH1   0   0.277  -40.7268  -19.0907   9.0325
 QHN  H3   H  HCH2   0   0.250  -41.5607  -16.7087   7.2343
 QHN  H2   H  HCH2   0   0.251  -42.3577  -18.3383   7.3297
 QHN  H5   H  HCH2   0   0.243  -41.9601  -16.3410   9.6806
 QHN  H4   H  HCH2   0   0.248  -42.7737  -17.9618   9.8054
 QHN  H6   H  HCR5   0   0.249  -36.9361  -15.5928  10.0565
 QHN  H7   H  HCR6   0   0.272  -39.3212  -19.4603   7.0053
 QHN  H8   H  HCR6   0   0.260  -39.5999  -20.1013   4.6474
 QHN  H9   H  HCR6   0   0.258  -39.2578  -18.4317   2.8514

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
 QHN  C11  C12  aromatic  1.389  0.020  1.389
 QHN  C11  C10  aromatic  1.388  0.020  1.388
 QHN  C12  C13  aromatic  1.387  0.020  1.387
 QHN  C10  C9   aromatic  1.387  0.020  1.387
 QHN  C13  C8   aromatic  1.390  0.020  1.390
 QHN  C9   C8   aromatic  1.389  0.020  1.389
 QHN  C8   N1   single    1.412  0.020  1.412
 QHN  C5   C4   single    1.503  0.020  1.503
 QHN  C5   C6   single    1.494  0.020  1.494
 QHN  N1   N2   aromatic  1.340  0.020  1.340
 QHN  N1   C3   aromatic  1.362  0.020  1.362
 QHN  N2   C7   aromatic  1.314  0.020  1.314
 QHN  C4   C3   single    1.476  0.020  1.476
 QHN  C4   C6   single    1.496  0.020  1.496
 QHN  C3   C2   aromatic  1.384  0.020  1.384
 QHN  C7   C2   aromatic  1.408  0.020  1.408
 QHN  C2   C1   single    1.504  0.020  1.504
 QHN  C1   O1   deloc     1.246  0.020  1.246
 QHN  C1   O2   deloc     1.249  0.020  1.249
 QHN  C10  H8   single    0.930  0.020  1.080
 QHN  C11  H9   single    0.930  0.020  1.080
 QHN  C12  H10  single    0.930  0.020  1.080
 QHN  C13  H11  single    0.930  0.020  1.080
 QHN  C4   H1   single    0.970  0.020  1.090
 QHN  C5   H3   single    0.970  0.020  1.090
 QHN  C5   H2   single    0.970  0.020  1.090
 QHN  C6   H5   single    0.970  0.020  1.090
 QHN  C6   H4   single    0.970  0.020  1.090
 QHN  C7   H6   single    0.930  0.020  1.080
 QHN  C9   H7   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
 QHN  O2   C1   O1   127.04  3.000
 QHN  O2   C1   C2   115.44  3.000
 QHN  O1   C1   C2   117.50  3.000
 QHN  H8   C10  C9   119.42  3.000
 QHN  H8   C10  C11  120.17  3.000
 QHN  C9   C10  C11  120.40  3.000
 QHN  H9   C11  C12  120.20  3.000
 QHN  H9   C11  C10  120.17  3.000
 QHN  C12  C11  C10  119.63  3.000
 QHN  H10  C12  C13  119.48  3.000
 QHN  H10  C12  C11  120.15  3.000
 QHN  C13  C12  C11  120.37  3.000
 QHN  H11  C13  C8   119.94  3.000
 QHN  H11  C13  C12  120.38  3.000
 QHN  C8   C13  C12  119.68  3.000
 QHN  C7   C2   C3   104.16  3.000
 QHN  C7   C2   C1   125.65  3.000
 QHN  C3   C2   C1   130.16  3.000
 QHN  N1   C3   C4   122.66  3.000
 QHN  C4   C3   C2   131.27  3.000
 QHN  N1   C3   C2   106.00  3.000
 QHN  H1   C4   C6   115.31  3.000
 QHN  H1   C4   C5   115.66  3.000
 QHN  C6   C4   C5    59.73  3.000
 QHN  H1   C4   C3   114.93  3.000
 QHN  C6   C4   C3   119.86  3.000
 QHN  C5   C4   C3   120.31  3.000
 QHN  H2   C5   H3   114.05  3.000
 QHN  H2   C5   C6   118.95  3.000
 QHN  H3   C5   C6   117.86  3.000
 QHN  H2   C5   C4   117.57  3.000
 QHN  H3   C5   C4   118.15  3.000
 QHN  C6   C5   C4    59.91  3.000
 QHN  H4   C6   H5   114.27  3.000
 QHN  H4   C6   C5   118.77  3.000
 QHN  H5   C6   C5   117.88  3.000
 QHN  H4   C6   C4   117.58  3.000
 QHN  H5   C6   C4   117.65  3.000
 QHN  C5   C6   C4    60.36  3.000
 QHN  H6   C7   N2   120.02  3.000
 QHN  H6   C7   C2   127.70  3.000
 QHN  N2   C7   C2   112.28  3.000
 QHN  N1   C8   C9   120.45  3.000
 QHN  N1   C8   C13  119.26  3.000
 QHN  C9   C8   C13  120.26  3.000
 QHN  H7   C9   C8   120.38  3.000
 QHN  H7   C9   C10  119.97  3.000
 QHN  C8   C9   C10  119.65  3.000
 QHN  N2   N1   C8   118.53  3.000
 QHN  N2   N1   C3   112.60  3.000
 QHN  C8   N1   C3   128.84  3.000
 QHN  N1   N2   C7   104.95  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
 QHN  CONST_01  C13  C12  C11  C10     0.00   0.0  0
 QHN  CONST_02  C13  C8   C9   C10     0.00   0.0  0
 QHN  CONST_03  N1   C8   C9   C10   180.00   0.0  0
 QHN  CONST_04  C8   C13  C12  C11     0.00   0.0  0
 QHN  CONST_05  C8   C9   C10  C11     0.00   0.0  0
 QHN  CONST_06  C9   C10  C11  C12     0.00   0.0  0
 QHN  CONST_07  C9   C8   C13  C12     0.00   0.0  0
 QHN  CONST_08  N1   C8   C13  C12   180.00   0.0  0
 QHN  CONST_11  C8   N1   C3   C2    180.00   0.0  0
 QHN  CONST_12  N2   N1   C3   C2      0.00   0.0  0
 QHN  CONST_13  N1   N2   C7   C2      0.00   0.0  0
 QHN  CONST_15  C7   N2   N1   C3      0.00   0.0  0
 QHN  CONST_16  N2   C7   C2   C3      0.00   0.0  0
 QHN  CONST_17  C8   N1   N2   C7    180.00   0.0  0
 QHN  CONST_18  N1   C3   C2   C7      0.00   0.0  0
 QHN  CONST_20  C8   N1   C3   C4      0.00   0.0  0
 QHN  CONST_21  N2   N1   C3   C4    180.00   0.0  0
 QHN  CONST_22  C7   C2   C3   C4    180.00   0.0  0
 QHN  CONST_23  N1   C3   C2   C1    180.00   0.0  0
 QHN  CONST_24  C4   C3   C2   C1      0.00   0.0  0
 QHN  CONST_25  N2   C7   C2   C1    180.00   0.0  0
 QHN  CONST_26  H10  C12  C11  C10   180.00   0.0  0
 QHN  CONST_27  H11  C13  C12  C11   180.00   0.0  0
 QHN  CONST_28  H7   C9   C10  C11   180.00   0.0  0
 QHN  CONST_29  H8   C10  C11  C12   180.00   0.0  0
 QHN  CONST_30  H9   C11  C12  C13   180.00   0.0  0
 QHN  CONST_31  H6   C7   C2   C3    180.00   0.0  0
 QHN  Var_01    C5   C4   C3   C2    127.17  30.0  2
 QHN  Var_02    C6   C5   C4   C3   -109.06  30.0  1
 QHN  Var_03    O1   C1   C2   C3     12.85  30.0  2

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 QHN  chir_01  C4  C5  C3  C6  both

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
 QHN  plan-1  C1   0.020
 QHN  plan-1  C2   0.020
 QHN  plan-1  C3   0.020
 QHN  plan-1  C4   0.020
 QHN  plan-1  C7   0.020
 QHN  plan-1  C8   0.020
 QHN  plan-1  N1   0.020
 QHN  plan-1  N2   0.020
 QHN  plan-1  H6   0.020
 QHN  plan-2  C10  0.020
 QHN  plan-2  C11  0.020
 QHN  plan-2  C12  0.020
 QHN  plan-2  C13  0.020
 QHN  plan-2  C8   0.020
 QHN  plan-2  C9   0.020
 QHN  plan-2  N1   0.020
 QHN  plan-2  H10  0.020
 QHN  plan-2  H11  0.020
 QHN  plan-2  H7   0.020
 QHN  plan-2  H8   0.020
 QHN  plan-2  H9   0.020
 QHN  plan-3  C1   0.020
 QHN  plan-3  C2   0.020
 QHN  plan-3  O1   0.020
 QHN  plan-3  O2   0.020

