# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 18:06:37 2020
#   Inital geometry file: a 113 line input string
#   Ligand name: 3-(4'-hydroxybiphenyl-4-yl)-2,4-dihydroindeno[1,2-c]pyrazol-6-ol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1ccc(cc1)c2ccc(cc2)c3[nH]nc4c3Cc5cc(O)ccc45
#
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
 H9K  H9K  3-(4'-hydroxybiphenyl-4-yl)-2,4-dihydroindeno[1,2-c]pyrazol-6-ol  ligand  42  26  .  2021-08-11  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_H9K
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
 H9K  O2   O  OH1   0  -0.633   7.3707  -2.5151  -0.0267
 H9K  C19  C  CR6   0   0.362   6.4595  -1.5213  -0.0282
 H9K  C18  C  CR16  0  -0.408   5.1115  -1.8886  -0.0197
 H9K  C20  C  CR16  0  -0.390   6.8259  -0.1747  -0.0373
 H9K  C21  C  CR16  0  -0.303   5.8558   0.8189  -0.0397
 H9K  C22  C  CR56  0   0.083   4.5184   0.4592  -0.0321
 H9K  C14  C  CR55  0   0.164   3.2823   1.2234  -0.0327
 H9K  N2   N  N     0  -0.278   2.9269   2.4918  -0.0452
 H9K  N1   N  NR15  0  -0.542   1.5927   2.4362  -0.0444
 H9K  C17  C  CR56  0   0.052   4.1515  -0.8982  -0.0217
 H9K  C16  C  CH2   0  -0.569   2.6431  -1.0718  -0.0135
 H9K  C15  C  CR55  0  -0.133   2.1862   0.3515  -0.0215
 H9K  C13  C  CR5   0   0.387   1.0808   1.1745  -0.0300
 H9K  C10  C  CR6   0   0.050  -0.3458   0.8791  -0.0312
 H9K  C9   C  CR16  0  -0.339  -0.7732  -0.4477   0.0512
 H9K  C8   C  CR16  0  -0.294  -2.1186  -0.7663   0.0422
 H9K  C11  C  CR16  0  -0.280  -1.3208   1.8746  -0.1170
 H9K  C12  C  CR16  0  -0.305  -2.6665   1.5525  -0.1200
 H9K  C7   C  CR6   0   0.087  -3.0974   0.2266  -0.0440
 H9K  C4   C  CR6   0   0.072  -4.5316  -0.1127  -0.0576
 H9K  C3   C  CR16  0  -0.300  -5.4491   0.6474  -0.7875
 H9K  C2   C  CR16  0  -0.322  -6.7958   0.3329  -0.8095
 H9K  C5   C  CR16  0  -0.300  -5.0237  -1.2069   0.6546
 H9K  C6   C  CR16  0  -0.369  -6.3696  -1.5340   0.6430
 H9K  C1   C  CR6   0   0.346  -7.2680  -0.7645  -0.0922
 H9K  O1   O  OH1   0  -0.629  -8.5859  -1.0322  -0.1456
 H9K  H14  H  HOH1  0   0.474   8.2636  -2.1530  -0.0373
 H9K  H13  H  HCR6  0   0.260   4.8382  -2.9375  -0.0117
 H9K  H15  H  HCR6  0   0.271   7.8751   0.0990  -0.0436
 H9K  H16  H  HCR6  0   0.255   6.1535   1.8597  -0.0479
 H9K  H1   H  HNR5  0   0.419   1.0768   3.3016  -0.0450
 H9K  H12  H  HCH2  0   0.277   2.3018  -1.6386  -0.8843
 H9K  H11  H  HCH2  0   0.276   2.3124  -1.6249   0.8701
 H9K  H8   H  HCR6  0   0.269  -0.0492  -1.2492   0.1158
 H9K  H7   H  HCR6  0   0.257  -2.4064  -1.8093   0.0842
 H9K  H9   H  HCR6  0   0.245  -1.0496   2.9208  -0.1788
 H9K  H10  H  HCR6  0   0.258  -3.3909   2.3554  -0.1633
 H9K  H4   H  HCR6  0   0.256  -5.1081   1.4938  -1.3705
 H9K  H3   H  HCR6  0   0.266  -7.4843   0.9305  -1.3936
 H9K  H5   H  HCR6  0   0.258  -4.3513  -1.8104   1.2514
 H9K  H6   H  HCR6  0   0.274  -6.7184  -2.3880   1.2128
 H9K  H2   H  HOH1  0   0.476  -8.7935  -1.8114   0.3819

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
 H9K  N2   N1   aromatic  1.335  0.020  1.335
 H9K  N2   C14  aromatic  1.317  0.020  1.317
 H9K  C21  C20  aromatic  1.389  0.020  1.389
 H9K  C21  C22  aromatic  1.385  0.020  1.385
 H9K  N1   C13  aromatic  1.362  0.020  1.362
 H9K  C14  C22  aromatic  1.453  0.020  1.453
 H9K  C14  C15  aromatic  1.401  0.020  1.401
 H9K  C20  C19  aromatic  1.396  0.020  1.396
 H9K  C22  C17  aromatic  1.406  0.020  1.406
 H9K  C13  C15  aromatic  1.378  0.020  1.378
 H9K  C13  C10  single    1.457  0.020  1.457
 H9K  C15  C16  single    1.495  0.020  1.495
 H9K  C19  O2   single    1.348  0.020  1.348
 H9K  C19  C18  aromatic  1.397  0.020  1.397
 H9K  C17  C16  single    1.518  0.020  1.518
 H9K  C17  C18  aromatic  1.379  0.020  1.379
 H9K  C9   C10  aromatic  1.396  0.020  1.396
 H9K  C9   C8   aromatic  1.383  0.020  1.383
 H9K  C10  C11  aromatic  1.396  0.020  1.396
 H9K  C8   C7   aromatic  1.397  0.020  1.397
 H9K  C11  C12  aromatic  1.384  0.020  1.384
 H9K  C7   C12  aromatic  1.396  0.020  1.396
 H9K  C7   C4   single    1.474  0.020  1.474
 H9K  C4   C3   aromatic  1.397  0.020  1.397
 H9K  C4   C5   aromatic  1.395  0.020  1.395
 H9K  C3   C2   aromatic  1.383  0.020  1.383
 H9K  C5   C6   aromatic  1.385  0.020  1.385
 H9K  C2   C1   aromatic  1.393  0.020  1.393
 H9K  C6   C1   aromatic  1.393  0.020  1.393
 H9K  C1   O1   single    1.346  0.020  1.346
 H9K  O2   H14  single    0.850  0.020  0.980
 H9K  C18  H13  single    0.930  0.020  1.080
 H9K  C20  H15  single    0.930  0.020  1.080
 H9K  C21  H16  single    0.930  0.020  1.080
 H9K  N1   H1   single    0.860  0.020  1.020
 H9K  C16  H12  single    0.970  0.020  1.090
 H9K  C16  H11  single    0.970  0.020  1.090
 H9K  C9   H8   single    0.930  0.020  1.080
 H9K  C8   H7   single    0.930  0.020  1.080
 H9K  C11  H9   single    0.930  0.020  1.080
 H9K  C12  H10  single    0.930  0.020  1.080
 H9K  C3   H4   single    0.930  0.020  1.080
 H9K  C2   H3   single    0.930  0.020  1.080
 H9K  C5   H5   single    0.930  0.020  1.080
 H9K  C6   H6   single    0.930  0.020  1.080
 H9K  O1   H2   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
 H9K  H14  O2   C19  110.44  3.000
 H9K  C20  C19  C18  120.46  3.000
 H9K  C18  C19  O2   117.27  3.000
 H9K  C20  C19  O2   122.27  3.000
 H9K  H13  C18  C17  121.29  3.000
 H9K  H13  C18  C19  119.85  3.000
 H9K  C17  C18  C19  118.86  3.000
 H9K  H15  C20  C21  119.70  3.000
 H9K  H15  C20  C19  119.84  3.000
 H9K  C21  C20  C19  120.47  3.000
 H9K  H16  C21  C22  121.01  3.000
 H9K  H16  C21  C20  119.72  3.000
 H9K  C22  C21  C20  119.26  3.000
 H9K  C17  C22  C14  106.60  3.000
 H9K  C17  C22  C21  120.17  3.000
 H9K  C14  C22  C21  133.23  3.000
 H9K  C15  C14  N2   112.85  3.000
 H9K  C15  C14  C22  109.78  3.000
 H9K  N2   C14  C22  137.37  3.000
 H9K  N1   N2   C14  103.26  3.000
 H9K  H1   N1   C13  127.11  3.000
 H9K  H1   N1   N2   118.41  3.000
 H9K  C13  N1   N2   114.47  3.000
 H9K  C16  C17  C22  111.69  3.000
 H9K  C16  C17  C18  127.54  3.000
 H9K  C22  C17  C18  120.77  3.000
 H9K  H11  C16  H12  106.67  3.000
 H9K  H11  C16  C15  113.17  3.000
 H9K  H12  C16  C15  113.19  3.000
 H9K  H11  C16  C17  111.26  3.000
 H9K  H12  C16  C17  111.40  3.000
 H9K  C15  C16  C17  101.23  3.000
 H9K  C13  C15  C16  144.47  3.000
 H9K  C16  C15  C14  110.70  3.000
 H9K  C13  C15  C14  104.83  3.000
 H9K  C10  C13  C15  131.64  3.000
 H9K  C10  C13  N1   123.78  3.000
 H9K  C15  C13  N1   104.59  3.000
 H9K  C11  C10  C9   117.87  3.000
 H9K  C11  C10  C13  122.64  3.000
 H9K  C9   C10  C13  119.49  3.000
 H9K  H8   C9   C8   118.74  3.000
 H9K  H8   C9   C10  120.17  3.000
 H9K  C8   C9   C10  121.09  3.000
 H9K  H7   C8   C7   120.05  3.000
 H9K  H7   C8   C9   118.71  3.000
 H9K  C7   C8   C9   121.23  3.000
 H9K  H9   C11  C12  117.93  3.000
 H9K  H9   C11  C10  121.18  3.000
 H9K  C12  C11  C10  120.89  3.000
 H9K  H10  C12  C7   120.01  3.000
 H9K  H10  C12  C11  118.58  3.000
 H9K  C7   C12  C11  121.40  3.000
 H9K  C4   C7   C12  121.23  3.000
 H9K  C4   C7   C8   121.25  3.000
 H9K  C12  C7   C8   117.52  3.000
 H9K  C5   C4   C3   117.49  3.000
 H9K  C5   C4   C7   121.27  3.000
 H9K  C3   C4   C7   121.24  3.000
 H9K  H4   C3   C2   118.41  3.000
 H9K  H4   C3   C4   119.98  3.000
 H9K  C2   C3   C4   121.60  3.000
 H9K  H3   C2   C1   119.79  3.000
 H9K  H3   C2   C3   120.15  3.000
 H9K  C1   C2   C3   120.06  3.000
 H9K  H5   C5   C6   118.45  3.000
 H9K  H5   C5   C4   119.96  3.000
 H9K  C6   C5   C4   121.58  3.000
 H9K  H6   C6   C1   120.34  3.000
 H9K  H6   C6   C5   119.61  3.000
 H9K  C1   C6   C5   120.05  3.000
 H9K  O1   C1   C6   122.87  3.000
 H9K  O1   C1   C2   117.90  3.000
 H9K  C6   C1   C2   119.23  3.000
 H9K  H2   O1   C1   110.49  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
 H9K  CONST_01  C22  C21  C20  C19    0.00   0.0  0
 H9K  CONST_02  C22  C17  C18  C19    0.00   0.0  0
 H9K  CONST_03  C21  C20  C19  C18    0.00   0.0  0
 H9K  CONST_04  C21  C22  C17  C18    0.00   0.0  0
 H9K  CONST_05  C14  C22  C17  C18  180.00   0.0  0
 H9K  CONST_06  C14  C22  C21  C20  180.00   0.0  0
 H9K  CONST_07  C17  C22  C21  C20    0.00   0.0  0
 H9K  CONST_08  C17  C18  C19  C20    0.00   0.0  0
 H9K  CONST_09  N2   C14  C22  C21    0.00   0.0  0
 H9K  CONST_10  C15  C14  C22  C21  180.00   0.0  0
 H9K  CONST_11  N1   N2   C14  C22  180.00   0.0  0
 H9K  CONST_12  C13  C15  C14  C22  180.00   0.0  0
 H9K  CONST_13  C13  N1   N2   C14    0.00   0.0  0
 H9K  CONST_14  N1   C13  C15  C14    0.00   0.0  0
 H9K  CONST_15  C10  C13  C15  C14  180.00   0.0  0
 H9K  CONST_16  C15  C13  N1   N2     0.00   0.0  0
 H9K  CONST_17  C10  C13  N1   N2   180.00   0.0  0
 H9K  CONST_18  C17  C22  C14  N2   180.00   0.0  0
 H9K  CONST_19  C13  C15  C14  N2     0.00   0.0  0
 H9K  CONST_20  C15  C14  N2   N1     0.00   0.0  0
 H9K  CONST_21  C9   C10  C13  N1   180.00   0.0  0
 H9K  CONST_22  C11  C10  C13  N1     0.00   0.0  0
 H9K  CONST_23  C15  C14  C22  C17    0.00   0.0  0
 H9K  CONST_24  C9   C10  C13  C15    0.00   0.0  0
 H9K  CONST_25  C11  C10  C13  C15  180.00   0.0  0
 H9K  CONST_26  C8   C9   C10  C13  180.00   0.0  0
 H9K  CONST_27  C12  C11  C10  C13  180.00   0.0  0
 H9K  CONST_28  C7   C8   C9   C10    0.00   0.0  0
 H9K  CONST_29  C7   C12  C11  C10    0.00   0.0  0
 H9K  CONST_30  C12  C11  C10  C9     0.00   0.0  0
 H9K  CONST_31  C12  C7   C8   C9     0.00   0.0  0
 H9K  CONST_32  C4   C7   C8   C9   180.00   0.0  0
 H9K  CONST_33  C11  C10  C9   C8     0.00   0.0  0
 H9K  CONST_34  C11  C12  C7   C8     0.00   0.0  0
 H9K  CONST_37  C4   C7   C12  C11  180.00   0.0  0
 H9K  CONST_40  C2   C3   C4   C7   180.00   0.0  0
 H9K  CONST_41  C6   C5   C4   C7   180.00   0.0  0
 H9K  CONST_42  C1   C2   C3   C4     0.00   0.0  0
 H9K  CONST_43  C1   C6   C5   C4     0.00   0.0  0
 H9K  CONST_44  C6   C5   C4   C3     0.00   0.0  0
 H9K  CONST_45  C6   C1   C2   C3     0.00   0.0  0
 H9K  CONST_46  C5   C4   C3   C2     0.00   0.0  0
 H9K  CONST_47  C5   C6   C1   C2     0.00   0.0  0
 H9K  CONST_48  C10  C13  C15  C16    0.00   0.0  0
 H9K  CONST_49  C21  C20  C19  O2   180.00   0.0  0
 H9K  CONST_50  C17  C18  C19  O2   180.00   0.0  0
 H9K  CONST_51  O1   C1   C2   C3   180.00   0.0  0
 H9K  CONST_52  O1   C1   C6   C5   180.00   0.0  0
 H9K  CONST_53  H16  C21  C20  C19  180.00   0.0  0
 H9K  CONST_54  H15  C20  C19  C18  180.00   0.0  0
 H9K  CONST_55  H13  C18  C19  C20  180.00   0.0  0
 H9K  CONST_56  H1   N1   N2   C14  180.00   0.0  0
 H9K  CONST_57  H8   C9   C10  C13    0.00   0.0  0
 H9K  CONST_58  H9   C11  C10  C13    0.00   0.0  0
 H9K  CONST_59  H7   C8   C9   C10  180.00   0.0  0
 H9K  CONST_60  H10  C12  C11  C10  180.00   0.0  0
 H9K  CONST_61  H4   C3   C4   C7     0.00   0.0  0
 H9K  CONST_62  H5   C5   C4   C7     0.00   0.0  0
 H9K  CONST_63  H3   C2   C3   C4   180.00   0.0  0
 H9K  CONST_64  H6   C6   C5   C4   180.00   0.0  0
 H9K  Var_01    H12  C16  C17  C18  -59.37  30.0  1

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
 H9K  plan-1  C13  0.020
 H9K  plan-1  C10  0.020
 H9K  plan-1  C9   0.020
 H9K  plan-1  C8   0.020
 H9K  plan-1  C11  0.020
 H9K  plan-1  C12  0.020
 H9K  plan-1  C7   0.020
 H9K  plan-1  C4   0.020
 H9K  plan-1  H8   0.020
 H9K  plan-1  H7   0.020
 H9K  plan-1  H9   0.020
 H9K  plan-1  H10  0.020
 H9K  plan-2  C7   0.020
 H9K  plan-2  C4   0.020
 H9K  plan-2  C3   0.020
 H9K  plan-2  C2   0.020
 H9K  plan-2  C5   0.020
 H9K  plan-2  C6   0.020
 H9K  plan-2  C1   0.020
 H9K  plan-2  O1   0.020
 H9K  plan-2  H4   0.020
 H9K  plan-2  H3   0.020
 H9K  plan-2  H5   0.020
 H9K  plan-2  H6   0.020
 H9K  plan-3  O2   0.020
 H9K  plan-3  C19  0.020
 H9K  plan-3  C18  0.020
 H9K  plan-3  C20  0.020
 H9K  plan-3  C21  0.020
 H9K  plan-3  C22  0.020
 H9K  plan-3  C14  0.020
 H9K  plan-3  N2   0.020
 H9K  plan-3  N1   0.020
 H9K  plan-3  C17  0.020
 H9K  plan-3  C16  0.020
 H9K  plan-3  C15  0.020
 H9K  plan-3  C13  0.020
 H9K  plan-3  C10  0.020
 H9K  plan-3  H13  0.020
 H9K  plan-3  H15  0.020
 H9K  plan-3  H16  0.020
 H9K  plan-3  H1   0.020

