# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 25 05:23:05 2022
#   Inital geometry file: a 134 line input string
#   Ligand name: 6-(2-fluoro-6-methoxyphenyl)-1-[4-(4-methylpiperazin-1-yl)phenyl]-1H-pyrazolo[4,3-c]pyridine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cccc(F)c1c2cc3n(ncc3cn2)c4ccc(cc4)N5CCN(C)CC5
#
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
 XHV  XHV  6-(2-fluoro-6-methoxyphenyl)-1-[4-(4-methylpiperazin-1-yl)phenyl]-1H-pyrazolo[4,3-c]pyridine  ligand  55  31  .  2022-08-11  2022-08-11
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_XHV
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
 XHV  C1   C  CH3   0  -0.517  -40.2283  11.6900  19.2036
 XHV  C4   C  CH2   0  -0.277  -41.8606  12.3849  20.8050
 XHV  C5   C  CH2   0  -0.313  -43.1408  13.1680  21.0298
 XHV  C7   C  CH2   0  -0.307  -43.8338  12.5801  18.7975
 XHV  C8   C  CH2   0  -0.282  -42.5474  11.7980  18.6218
 XHV  C11  C  CR16  0  -0.266  -47.9047  12.6422  20.1769
 XHV  C12  C  CR6   0   0.291  -48.1966  13.4561  21.2658
 XHV  C17  C  CR15  0  -0.104  -51.6116  14.0968  21.3693
 XHV  C18  C  CR56  0  -0.189  -51.4359  13.8601  22.7588
 XHV  C19  C  CR16  0  -0.120  -52.2350  13.8202  23.9030
 XHV  C21  C  CR6   0   0.219  -50.4182  13.2604  25.1988
 XHV  C23  C  CR56  0   0.523  -50.0683  13.5851  22.8956
 XHV  C24  C  CR6   0  -0.280  -49.9335  12.9290  26.5609
 XHV  C27  C  CR16  0  -0.433  -49.9359  11.4141  28.4691
 XHV  C30  C  CR6   0   0.399  -49.0312  13.7623  27.2417
 XHV  C32  C  CH3   0  -0.438  -47.7330  15.7501  27.1975
 XHV  N2   N  NT    0  -0.410  -41.4811  12.3796  19.4090
 XHV  N6   N  NT    0  -0.518  -44.2103  12.6487  20.2017
 XHV  C9   C  CR6   0   0.388  -45.5194  12.9576  20.5324
 XHV  C10  C  CR16  0  -0.335  -46.5947  12.4035  19.8143
 XHV  C13  C  CR16  0  -0.284  -47.1558  14.0386  21.9703
 XHV  C14  C  CR16  0  -0.363  -45.8395  13.7938  21.6117
 XHV  N15  N  NR5   0  -0.513  -49.5352  13.6767  21.6528
 XHV  N16  N  N     0  -0.228  -50.4757  13.9814  20.7383
 XHV  N20  N  N     0  -0.423  -51.7364  13.5331  25.0842
 XHV  C22  C  CR16  0  -0.329  -49.5316  13.2638  24.1429
 XHV  C25  C  CR6   0   0.544  -50.3597  11.7819  27.2062
 XHV  F26  F  F     0  -0.303  -51.2116  10.9742  26.5584
 XHV  C28  C  CR16  0  -0.229  -49.0407  12.2513  29.1132
 XHV  C29  C  CR16  0  -0.395  -48.5846  13.4188  28.5164
 XHV  O31  O  O2    0  -0.456  -48.6638  14.8750  26.5901
 XHV  H1   H  HCH3  0   0.233  -39.4372  12.1722  19.7798
 XHV  H2   H  HCH3  0   0.192  -40.2639  10.6308  19.5023
 XHV  H3   H  HCH3  0   0.233  -39.9464  11.7302  18.1504
 XHV  H4   H  HCH2  0   0.194  -41.9958  11.3596  21.1923
 XHV  H5   H  HCH2  0   0.241  -41.0658  12.8478  21.3945
 XHV  H6   H  HCH2  0   0.218  -42.9623  14.2361  20.8371
 XHV  H7   H  HCH2  0   0.253  -43.4078  13.0645  22.0816
 XHV  H8   H  HCH2  0   0.221  -43.7051  13.5911  18.3856
 XHV  H9   H  HCH2  0   0.256  -44.6111  12.0909  18.2158
 XHV  H10  H  HCH2  0   0.194  -42.7247  10.7423  18.8925
 XHV  H11  H  HCH2  0   0.241  -42.2697  11.8184  17.5653
 XHV  H12  H  HCR6  0   0.267  -48.7051  12.1772  19.6161
 XHV  H13  H  HCR5  0   0.280  -52.5156  14.3458  20.8347
 XHV  H14  H  HCR6  0   0.269  -53.2990  14.0261  23.8492
 XHV  H15  H  HCR6  0   0.275  -50.2919  10.5011  28.9268
 XHV  H16  H  HCH3  0   0.261  -47.5738  16.5623  26.4929
 XHV  H17  H  HCH3  0   0.232  -48.1133  16.1656  28.1340
 XHV  H18  H  HCH3  0   0.232  -46.7771  15.2570  27.3898
 XHV  H20  H  HCR6  0   0.267  -46.4150  11.7404  18.9797
 XHV  H21  H  HCR6  0   0.276  -47.3580  14.7100  22.7957
 XHV  H22  H  HCR6  0   0.273  -45.0658  14.2887  22.1803
 XHV  H23  H  HCR6  0   0.286  -48.4877  13.0236  24.2879
 XHV  H24  H  HCR6  0   0.271  -48.6877  11.9932  30.1027
 XHV  H25  H  HCR6  0   0.284  -47.8917  14.0489  29.0559

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
 XHV  C8   C7   single    1.516  0.020  1.516
 XHV  C8   N2   single    1.447  0.020  1.447
 XHV  C7   N6   single    1.455  0.020  1.455
 XHV  C1   N2   single    1.445  0.020  1.445
 XHV  N2   C4   single    1.447  0.020  1.447
 XHV  C10  C11  aromatic  1.380  0.020  1.380
 XHV  C10  C9   aromatic  1.407  0.020  1.407
 XHV  C11  C12  aromatic  1.390  0.020  1.390
 XHV  N6   C9   single    1.385  0.020  1.385
 XHV  N6   C5   single    1.449  0.020  1.449
 XHV  C9   C14  aromatic  1.402  0.020  1.402
 XHV  C4   C5   single    1.517  0.020  1.517
 XHV  N16  C17  aromatic  1.305  0.020  1.305
 XHV  N16  N15  aromatic  1.347  0.020  1.347
 XHV  C12  N15  single    1.411  0.020  1.411
 XHV  C12  C13  aromatic  1.385  0.020  1.385
 XHV  C17  C18  aromatic  1.420  0.020  1.420
 XHV  N15  C23  aromatic  1.355  0.020  1.355
 XHV  C14  C13  aromatic  1.386  0.020  1.386
 XHV  C18  C23  aromatic  1.402  0.020  1.402
 XHV  C18  C19  aromatic  1.396  0.020  1.396
 XHV  C23  C22  aromatic  1.395  0.020  1.395
 XHV  C19  N20  aromatic  1.314  0.020  1.314
 XHV  C22  C21  aromatic  1.379  0.020  1.379
 XHV  N20  C21  aromatic  1.351  0.020  1.351
 XHV  C21  C24  single    1.483  0.020  1.483
 XHV  O31  C32  single    1.415  0.020  1.415
 XHV  O31  C30  single    1.341  0.020  1.341
 XHV  C24  C30  aromatic  1.404  0.020  1.404
 XHV  C24  C25  aromatic  1.383  0.020  1.383
 XHV  F26  C25  single    1.341  0.020  1.341
 XHV  C30  C29  aromatic  1.394  0.020  1.394
 XHV  C25  C27  aromatic  1.382  0.020  1.382
 XHV  C29  C28  aromatic  1.388  0.020  1.388
 XHV  C27  C28  aromatic  1.385  0.020  1.385
 XHV  C1   H1   single    0.970  0.020  1.090
 XHV  C1   H2   single    0.970  0.020  1.090
 XHV  C1   H3   single    0.970  0.020  1.090
 XHV  C4   H4   single    0.970  0.020  1.090
 XHV  C4   H5   single    0.970  0.020  1.090
 XHV  C5   H6   single    0.970  0.020  1.090
 XHV  C5   H7   single    0.970  0.020  1.090
 XHV  C7   H8   single    0.970  0.020  1.090
 XHV  C7   H9   single    0.970  0.020  1.090
 XHV  C8   H10  single    0.970  0.020  1.090
 XHV  C8   H11  single    0.970  0.020  1.090
 XHV  C11  H12  single    0.930  0.020  1.080
 XHV  C17  H13  single    0.930  0.020  1.080
 XHV  C19  H14  single    0.930  0.020  1.080
 XHV  C27  H15  single    0.930  0.020  1.080
 XHV  C32  H16  single    0.970  0.020  1.090
 XHV  C32  H17  single    0.970  0.020  1.090
 XHV  C32  H18  single    0.970  0.020  1.090
 XHV  C10  H20  single    0.930  0.020  1.080
 XHV  C13  H21  single    0.930  0.020  1.080
 XHV  C14  H22  single    0.930  0.020  1.080
 XHV  C22  H23  single    0.930  0.020  1.080
 XHV  C28  H24  single    0.930  0.020  1.080
 XHV  C29  H25  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
 XHV  H3   C1   H2   107.80  3.000
 XHV  H3   C1   H1   107.83  3.000
 XHV  H2   C1   H1   107.78  3.000
 XHV  H3   C1   N2   110.11  3.000
 XHV  H2   C1   N2   113.11  3.000
 XHV  H1   C1   N2   110.04  3.000
 XHV  H5   C4   H4   107.05  3.000
 XHV  H5   C4   N2   109.35  3.000
 XHV  H4   C4   N2   111.54  3.000
 XHV  H5   C4   C5   108.38  3.000
 XHV  H4   C4   C5   108.90  3.000
 XHV  N2   C4   C5   111.48  3.000
 XHV  H7   C5   H6   107.52  3.000
 XHV  H7   C5   N6   109.68  3.000
 XHV  H6   C5   N6   111.57  3.000
 XHV  H7   C5   C4   107.49  3.000
 XHV  H6   C5   C4   109.77  3.000
 XHV  N6   C5   C4   110.68  3.000
 XHV  H9   C7   H8   107.28  3.000
 XHV  H9   C7   N6   110.64  3.000
 XHV  H8   C7   N6   110.39  3.000
 XHV  H9   C7   C8   108.22  3.000
 XHV  H8   C7   C8   109.38  3.000
 XHV  N6   C7   C8   110.84  3.000
 XHV  H11  C8   H10  107.21  3.000
 XHV  H11  C8   N2   109.34  3.000
 XHV  H10  C8   N2   111.66  3.000
 XHV  H11  C8   C7   108.55  3.000
 XHV  H10  C8   C7   109.19  3.000
 XHV  N2   C8   C7   110.78  3.000
 XHV  H12  C11  C10  119.44  3.000
 XHV  H12  C11  C12  120.14  3.000
 XHV  C10  C11  C12  120.41  3.000
 XHV  N15  C12  C13  120.51  3.000
 XHV  C13  C12  C11  119.13  3.000
 XHV  N15  C12  C11  120.36  3.000
 XHV  H13  C17  N16  120.67  3.000
 XHV  H13  C17  C18  128.80  3.000
 XHV  N16  C17  C18  110.53  3.000
 XHV  C23  C18  C19  118.22  3.000
 XHV  C19  C18  C17  137.36  3.000
 XHV  C23  C18  C17  104.41  3.000
 XHV  H14  C19  N20  117.27  3.000
 XHV  H14  C19  C18  121.01  3.000
 XHV  N20  C19  C18  121.72  3.000
 XHV  C22  C21  N20  124.19  3.000
 XHV  N20  C21  C24  116.22  3.000
 XHV  C22  C21  C24  119.59  3.000
 XHV  C22  C23  N15  133.15  3.000
 XHV  C22  C23  C18  120.51  3.000
 XHV  N15  C23  C18  106.32  3.000
 XHV  C25  C24  C30  117.63  3.000
 XHV  C25  C24  C21  120.86  3.000
 XHV  C30  C24  C21  121.50  3.000
 XHV  H15  C27  C28  121.76  3.000
 XHV  H15  C27  C25  120.70  3.000
 XHV  C28  C27  C25  117.55  3.000
 XHV  O31  C30  C29  124.15  3.000
 XHV  C29  C30  C24  120.20  3.000
 XHV  O31  C30  C24  115.65  3.000
 XHV  H18  C32  H17  108.98  3.000
 XHV  H18  C32  H16  108.86  3.000
 XHV  H17  C32  H16  108.81  3.000
 XHV  H18  C32  O31  111.84  3.000
 XHV  H17  C32  O31  111.97  3.000
 XHV  H16  C32  O31  106.28  3.000
 XHV  C8   N2   C4   109.45  3.000
 XHV  C4   N2   C1   111.50  3.000
 XHV  C8   N2   C1   111.70  3.000
 XHV  C9   N6   C7   119.04  3.000
 XHV  C9   N6   C5   118.77  3.000
 XHV  C7   N6   C5   112.17  3.000
 XHV  C14  C9   C10  116.95  3.000
 XHV  C14  C9   N6   122.17  3.000
 XHV  C10  C9   N6   120.85  3.000
 XHV  H20  C10  C9   120.57  3.000
 XHV  H20  C10  C11  117.82  3.000
 XHV  C9   C10  C11  121.56  3.000
 XHV  H21  C13  C14  118.94  3.000
 XHV  H21  C13  C12  120.53  3.000
 XHV  C14  C13  C12  120.51  3.000
 XHV  H22  C14  C13  117.59  3.000
 XHV  H22  C14  C9   120.98  3.000
 XHV  C13  C14  C9   121.41  3.000
 XHV  N16  N15  C23  111.30  3.000
 XHV  C23  N15  C12  127.89  3.000
 XHV  N16  N15  C12  120.78  3.000
 XHV  N15  N16  C17  107.44  3.000
 XHV  C21  N20  C19  119.38  3.000
 XHV  H23  C22  C23  122.85  3.000
 XHV  H23  C22  C21  121.18  3.000
 XHV  C23  C22  C21  115.97  3.000
 XHV  F26  C25  C27  118.43  3.000
 XHV  C27  C25  C24  123.54  3.000
 XHV  F26  C25  C24  118.02  3.000
 XHV  H24  C28  C29  119.12  3.000
 XHV  H24  C28  C27  119.48  3.000
 XHV  C29  C28  C27  121.39  3.000
 XHV  H25  C29  C28  119.10  3.000
 XHV  H25  C29  C30  121.21  3.000
 XHV  C28  C29  C30  119.69  3.000
 XHV  C32  O31  C30  119.01  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
 XHV  CONST_01  C14  C9   C10  C11     0.00   0.0  0
 XHV  CONST_04  C14  C13  C12  C11     0.00   0.0  0
 XHV  CONST_05  C9   C10  C11  C12     0.00   0.0  0
 XHV  CONST_06  C17  N16  N15  C12   180.00   0.0  0
 XHV  CONST_07  C18  C23  N15  C12   180.00   0.0  0
 XHV  CONST_08  C22  C23  N15  C12     0.00   0.0  0
 XHV  CONST_09  C9   C14  C13  C12     0.00   0.0  0
 XHV  CONST_10  C23  N15  N16  C17     0.00   0.0  0
 XHV  CONST_11  N15  C23  C18  C17     0.00   0.0  0
 XHV  CONST_12  C22  C23  C18  C17   180.00   0.0  0
 XHV  CONST_13  N20  C19  C18  C17   180.00   0.0  0
 XHV  CONST_14  N15  N16  C17  C18     0.00   0.0  0
 XHV  CONST_15  N16  N15  C23  C18     0.00   0.0  0
 XHV  CONST_16  C21  C22  C23  C18     0.00   0.0  0
 XHV  CONST_17  C21  N20  C19  C18     0.00   0.0  0
 XHV  CONST_18  N16  C17  C18  C19   180.00   0.0  0
 XHV  CONST_19  N15  C23  C18  C19   180.00   0.0  0
 XHV  CONST_20  C22  C23  C18  C19     0.00   0.0  0
 XHV  CONST_21  C22  C21  N20  C19     0.00   0.0  0
 XHV  CONST_22  C24  C21  N20  C19   180.00   0.0  0
 XHV  CONST_23  N15  C23  C22  C21   180.00   0.0  0
 XHV  CONST_24  C29  C30  C24  C21   180.00   0.0  0
 XHV  CONST_25  C27  C25  C24  C21   180.00   0.0  0
 XHV  CONST_27  N16  C17  C18  C23     0.00   0.0  0
 XHV  CONST_28  N20  C19  C18  C23     0.00   0.0  0
 XHV  CONST_29  N20  C21  C22  C23     0.00   0.0  0
 XHV  CONST_30  C24  C21  C22  C23   180.00   0.0  0
 XHV  CONST_31  C28  C29  C30  C24     0.00   0.0  0
 XHV  CONST_32  C28  C27  C25  C24     0.00   0.0  0
 XHV  CONST_33  C30  C24  C25  C27     0.00   0.0  0
 XHV  CONST_34  C30  C29  C28  C27     0.00   0.0  0
 XHV  CONST_37  N15  C12  C11  C10   180.00   0.0  0
 XHV  CONST_38  C13  C12  C11  C10     0.00   0.0  0
 XHV  CONST_39  C13  C14  C9   C10     0.00   0.0  0
 XHV  CONST_41  N15  C12  C13  C14   180.00   0.0  0
 XHV  CONST_42  C22  C23  N15  N16   180.00   0.0  0
 XHV  CONST_45  C29  C30  C24  C25     0.00   0.0  0
 XHV  CONST_46  C29  C28  C27  C25     0.00   0.0  0
 XHV  CONST_47  N6   C9   C10  C11   180.00   0.0  0
 XHV  CONST_48  C13  C14  C9   N6    180.00   0.0  0
 XHV  CONST_49  O31  C30  C24  C21     0.00   0.0  0
 XHV  CONST_50  F26  C25  C24  C21     0.00   0.0  0
 XHV  CONST_51  F26  C25  C24  C30   180.00   0.0  0
 XHV  CONST_52  O31  C30  C24  C25   180.00   0.0  0
 XHV  CONST_53  C28  C27  C25  F26   180.00   0.0  0
 XHV  CONST_54  O31  C30  C29  C28   180.00   0.0  0
 XHV  CONST_55  H21  C13  C12  C11   180.00   0.0  0
 XHV  CONST_56  H20  C10  C11  C12   180.00   0.0  0
 XHV  CONST_57  H22  C14  C13  C12   180.00   0.0  0
 XHV  CONST_58  H14  C19  C18  C17     0.00   0.0  0
 XHV  CONST_59  H23  C22  C23  C18   180.00   0.0  0
 XHV  CONST_60  H13  C17  C18  C19     0.00   0.0  0
 XHV  CONST_61  H25  C29  C30  C24   180.00   0.0  0
 XHV  CONST_62  H15  C27  C25  C24   180.00   0.0  0
 XHV  CONST_63  H24  C28  C29  C30   180.00   0.0  0
 XHV  CONST_64  H12  C11  C10  C9    180.00   0.0  0
 XHV  Var_01    C7   C8   N2   C4     58.96  30.0  1
 XHV  Var_02    C7   N6   C5   C4    -53.22  30.0  1
 XHV  Var_03    C8   C7   N6   C5     53.94  30.0  1
 XHV  Var_04    C10  C9   N6   C5   -175.63  30.0  2
 XHV  Var_05    C8   N2   C4   C5    -58.73  30.0  1
 XHV  Var_06    N6   C7   C8   N2    -56.73  30.0  1
 XHV  Var_07    N6   C5   C4   N2     55.87  30.0  1
 XHV  Var_08    C29  C30  O31  C32     2.07  30.0  2
 XHV  Var_09    H1   C1   N2   C4    -59.27  30.0  3
 XHV  Var_10    H16  C32  O31  C30   179.08  30.0  3

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
 XHV  plan-1  C21  0.020
 XHV  plan-1  C24  0.020
 XHV  plan-1  C27  0.020
 XHV  plan-1  C30  0.020
 XHV  plan-1  C25  0.020
 XHV  plan-1  F26  0.020
 XHV  plan-1  C28  0.020
 XHV  plan-1  C29  0.020
 XHV  plan-1  O31  0.020
 XHV  plan-1  H15  0.020
 XHV  plan-1  H24  0.020
 XHV  plan-1  H25  0.020
 XHV  plan-2  C11  0.020
 XHV  plan-2  C12  0.020
 XHV  plan-2  N6   0.020
 XHV  plan-2  C9   0.020
 XHV  plan-2  C10  0.020
 XHV  plan-2  C13  0.020
 XHV  plan-2  C14  0.020
 XHV  plan-2  N15  0.020
 XHV  plan-2  H12  0.020
 XHV  plan-2  H20  0.020
 XHV  plan-2  H21  0.020
 XHV  plan-2  H22  0.020
 XHV  plan-3  C12  0.020
 XHV  plan-3  C17  0.020
 XHV  plan-3  C18  0.020
 XHV  plan-3  C19  0.020
 XHV  plan-3  C21  0.020
 XHV  plan-3  C23  0.020
 XHV  plan-3  C24  0.020
 XHV  plan-3  N15  0.020
 XHV  plan-3  N16  0.020
 XHV  plan-3  N20  0.020
 XHV  plan-3  C22  0.020
 XHV  plan-3  H13  0.020
 XHV  plan-3  H14  0.020
 XHV  plan-3  H23  0.020

