# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 21:48:50 2021
#   Inital geometry file: a 129 line input string
#   Ligand name: 4-[[5-[7-chloranyl-3-(1~{H}-indazol-6-yl)benzotriazol-5-yl]pyrazol-1-yl]methyl]benzenecarbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Clc1cc(cc2n(nnc12)c3ccc4cn[nH]c4c3)c5ccnn5Cc6ccc(cc6)C#N
#
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
 O1H  O1H  4-[[5-[7-chloranyl-3-(1~{H}-indazol-6-yl)benzotriazol-5-yl]pyrazol-1-yl]methyl]benzenecarbonitrile  ligand  48  33  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_O1H
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
 O1H  N1   N   NR5   0  -0.323  29.8953  29.2616  -3.8051
 O1H  N3   N   N     0  -0.291  26.8472  33.2468   0.0055
 O1H  C4   C   CR15  0  -0.545  30.5353  28.1487  -2.0351
 O1H  C5   C   CR15  0  -0.068  30.9377  27.5231  -3.2257
 O1H  C6   C   CH2   0  -0.370  29.2453  30.2000  -4.6991
 O1H  C7   C   CR6   0   0.092  27.7690  30.3066  -4.4145
 O1H  C8   C   CR16  0  -0.257  26.9778  29.1603  -4.3956
 O1H  C10  C   CR6   0  -0.002  25.0606  30.4854  -3.8239
 O1H  C13  C   CR16  0  -0.278  27.1913  31.5406  -4.1405
 O1H  C15  C   CR56  0   0.389  27.2759  31.1212  -0.5469
 O1H  C17  C   CR6   0   0.316  25.0602  30.2834   0.2457
 O1H  C20  C   CR15  0  -0.119  21.9505  27.5878   0.6055
 O1H  C21  C   CR56  0  -0.083  23.1736  28.3106   0.6074
 O1H  C22  C   CR16  0  -0.317  24.4927  28.0623   1.0045
 O1H  N2   N   NS    0  -0.254  22.5365  30.6506  -3.3163
 O1H  C11  C   CSP   0   0.065  23.6651  30.5766  -3.5384
 O1H  C9   C   CR16  0  -0.228  25.6301  29.2412  -4.1014
 O1H  C12  C   CR16  0  -0.228  25.8424  31.6386  -3.8438
 O1H  N    N   N     0  -0.269  30.5381  28.2012  -4.2851
 O1H  C3   C   CR5   0   0.418  29.8625  29.2740  -2.4517
 O1H  C2   C   CR6   0  -0.001  29.1615  30.3349  -1.7147
 O1H  C1   C   CR16  0  -0.264  29.6969  31.6445  -1.7185
 O1H  C14  C   CR16  0  -0.281  27.9547  30.0451  -1.1128
 O1H  N5   N   NR5   0  -0.512  26.0613  31.2608   0.0474
 O1H  N4   N   N     0  -0.045  25.8460  32.5404   0.3558
 O1H  C16  C   CR56  0   0.219  27.7686  32.4246  -0.5661
 O1H  C    C   CR6   0  -0.102  29.0097  32.6874  -1.1502
 O1H  CL   CL  CL    0  -0.082  29.6261  34.2908  -1.1632
 O1H  C23  C   CR16  0  -0.307  25.4287  29.0526   0.8267
 O1H  C19  C   CR56  0   0.442  22.8359  29.5549   0.0455
 O1H  C18  C   CR16  0  -0.320  23.7745  30.5689  -0.1506
 O1H  N7   N   N     0  -0.220  20.9863  28.3121   0.0970
 O1H  N6   N   NR15  0  -0.548  21.5168  29.4900  -0.2356
 O1H  H1   H   HCR5  0   0.272  30.7130  27.8355  -1.0200
 O1H  H2   H   HCR5  0   0.266  31.4985  26.6086  -3.3446
 O1H  H4   H   HCH2  0   0.307  29.4182  29.8318  -5.7097
 O1H  H3   H   HCH2  0   0.287  29.7192  31.1796  -4.6276
 O1H  H5   H   HCR6  0   0.270  27.4146  28.1926  -4.6097
 O1H  H8   H   HCR6  0   0.276  27.8023  32.4345  -4.1454
 O1H  H12  H   HCR5  0   0.275  21.7623  26.5836   0.9526
 O1H  H13  H   HCR6  0   0.270  24.7747  27.1183   1.4510
 O1H  H6   H   HCR6  0   0.284  25.0189  28.3493  -4.0875
 O1H  H7   H   HCR6  0   0.285  25.4000  32.6015  -3.6270
 O1H  H    H   HCR6  0   0.294  30.6574  31.8256  -2.1824
 O1H  H9   H   HCR6  0   0.292  27.5459  29.0448  -1.1342
 O1H  H14  H   HCR6  0   0.284  26.4492  28.8968   1.1503
 O1H  H10  H   HCR6  0   0.292  23.5111  31.5167  -0.5986
 O1H  H11  H   HNR5  0   0.420  20.9408  30.1948  -0.6666

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
 O1H  N2   C11  triple    1.153  0.020  1.153
 O1H  C11  C10  single    1.427  0.020  1.427
 O1H  C12  C10  aromatic  1.393  0.020  1.393
 O1H  C12  C13  aromatic  1.385  0.020  1.385
 O1H  C10  C9   aromatic  1.396  0.020  1.396
 O1H  C13  C7   aromatic  1.390  0.020  1.390
 O1H  C9   C8   aromatic  1.382  0.020  1.382
 O1H  C7   C8   aromatic  1.393  0.020  1.393
 O1H  C7   C6   single    1.507  0.020  1.507
 O1H  C6   N1   single    1.450  0.020  1.450
 O1H  N    N1   aromatic  1.330  0.020  1.330
 O1H  N    C5   aromatic  1.320  0.020  1.320
 O1H  N1   C3   aromatic  1.354  0.020  1.354
 O1H  C5   C4   aromatic  1.404  0.020  1.404
 O1H  C3   C4   aromatic  1.376  0.020  1.376
 O1H  C3   C2   single    1.470  0.020  1.470
 O1H  C2   C1   aromatic  1.415  0.020  1.415
 O1H  C2   C14  aromatic  1.379  0.020  1.379
 O1H  C1   C    aromatic  1.372  0.020  1.372
 O1H  C14  C15  aromatic  1.392  0.020  1.392
 O1H  C    CL   single    1.718  0.020  1.718
 O1H  C    C16  aromatic  1.397  0.020  1.397
 O1H  C15  C16  aromatic  1.394  0.020  1.394
 O1H  C15  N5   aromatic  1.359  0.020  1.359
 O1H  C16  N3   aromatic  1.361  0.020  1.361
 O1H  N5   C17  single    1.413  0.020  1.413
 O1H  N5   N4   aromatic  1.334  0.020  1.334
 O1H  N3   N4   aromatic  1.274  0.020  1.274
 O1H  C17  C18  aromatic  1.375  0.020  1.375
 O1H  C17  C23  aromatic  1.410  0.020  1.410
 O1H  C18  C19  aromatic  1.396  0.020  1.396
 O1H  C23  C22  aromatic  1.374  0.020  1.374
 O1H  C22  C21  aromatic  1.400  0.020  1.400
 O1H  C19  C21  aromatic  1.406  0.020  1.406
 O1H  C19  N6   aromatic  1.350  0.020  1.350
 O1H  C21  C20  aromatic  1.421  0.020  1.421
 O1H  N6   N7   aromatic  1.334  0.020  1.334
 O1H  C20  N7   aromatic  1.309  0.020  1.309
 O1H  C4   H1   single    0.930  0.020  1.080
 O1H  C5   H2   single    0.930  0.020  1.080
 O1H  C6   H4   single    0.970  0.020  1.090
 O1H  C6   H3   single    0.970  0.020  1.090
 O1H  C8   H5   single    0.930  0.020  1.080
 O1H  C13  H8   single    0.930  0.020  1.080
 O1H  C20  H12  single    0.930  0.020  1.080
 O1H  C22  H13  single    0.930  0.020  1.080
 O1H  C9   H6   single    0.930  0.020  1.080
 O1H  C12  H7   single    0.930  0.020  1.080
 O1H  C1   H    single    0.930  0.020  1.080
 O1H  C14  H9   single    0.930  0.020  1.080
 O1H  C23  H14  single    0.930  0.020  1.080
 O1H  C18  H10  single    0.930  0.020  1.080
 O1H  N6   H11  single    0.860  0.020  1.020

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
 O1H  C3   N1   N    112.32  3.000
 O1H  C3   N1   C6   126.84  3.000
 O1H  N    N1   C6   120.68  3.000
 O1H  C16  N3   N4   108.21  3.000
 O1H  H1   C4   C3   127.15  3.000
 O1H  H1   C4   C5   128.49  3.000
 O1H  C3   C4   C5   104.35  3.000
 O1H  H2   C5   N    120.28  3.000
 O1H  H2   C5   C4   128.32  3.000
 O1H  N    C5   C4   111.41  3.000
 O1H  H3   C6   H4   107.18  3.000
 O1H  H3   C6   C7   110.47  3.000
 O1H  H4   C6   C7   110.77  3.000
 O1H  H3   C6   N1   110.25  3.000
 O1H  H4   C6   N1   106.38  3.000
 O1H  C7   C6   N1   111.62  3.000
 O1H  C13  C7   C8   119.46  3.000
 O1H  C8   C7   C6   120.05  3.000
 O1H  C13  C7   C6   120.48  3.000
 O1H  H5   C8   C9   119.19  3.000
 O1H  H5   C8   C7   120.23  3.000
 O1H  C9   C8   C7   120.58  3.000
 O1H  C12  C10  C9   120.38  3.000
 O1H  C9   C10  C11  119.71  3.000
 O1H  C12  C10  C11  119.90  3.000
 O1H  H8   C13  C12  119.49  3.000
 O1H  H8   C13  C7   119.83  3.000
 O1H  C12  C13  C7   120.67  3.000
 O1H  C16  C15  N5   103.05  3.000
 O1H  N5   C15  C14  133.84  3.000
 O1H  C16  C15  C14  123.02  3.000
 O1H  C18  C17  C23  122.97  3.000
 O1H  C23  C17  N5   118.45  3.000
 O1H  C18  C17  N5   118.57  3.000
 O1H  H12  C20  N7   120.77  3.000
 O1H  H12  C20  C21  128.55  3.000
 O1H  N7   C20  C21  110.68  3.000
 O1H  C19  C21  C22  119.77  3.000
 O1H  C19  C21  C20  104.06  3.000
 O1H  C22  C21  C20  136.17  3.000
 O1H  H13  C22  C23  120.31  3.000
 O1H  H13  C22  C21  121.17  3.000
 O1H  C23  C22  C21  118.51  3.000
 O1H  N2   C11  C10  180.00  3.000
 O1H  H6   C9   C10  120.12  3.000
 O1H  H6   C9   C8   120.38  3.000
 O1H  C10  C9   C8   119.50  3.000
 O1H  H7   C12  C13  120.30  3.000
 O1H  H7   C12  C10  120.29  3.000
 O1H  C13  C12  C10  119.41  3.000
 O1H  C5   N    N1   105.45  3.000
 O1H  C2   C3   C4   132.22  3.000
 O1H  C2   C3   N1   121.29  3.000
 O1H  C4   C3   N1   106.46  3.000
 O1H  C14  C2   C1   121.79  3.000
 O1H  C14  C2   C3   118.97  3.000
 O1H  C1   C2   C3   119.10  3.000
 O1H  H    C1   C    119.67  3.000
 O1H  H    C1   C2   119.47  3.000
 O1H  C    C1   C2   120.86  3.000
 O1H  H9   C14  C2   121.12  3.000
 O1H  H9   C14  C15  122.61  3.000
 O1H  C2   C14  C15  116.20  3.000
 O1H  N4   N5   C17  121.12  3.000
 O1H  N4   N5   C15  110.11  3.000
 O1H  C17  N5   C15  128.56  3.000
 O1H  N5   N4   N3   109.96  3.000
 O1H  C    C16  C15  119.73  3.000
 O1H  C15  C16  N3   108.66  3.000
 O1H  C    C16  N3   131.58  3.000
 O1H  CL   C    C16  119.85  3.000
 O1H  C16  C    C1   118.37  3.000
 O1H  CL   C    C1   121.77  3.000
 O1H  H14  C23  C22  120.01  3.000
 O1H  H14  C23  C17  119.70  3.000
 O1H  C22  C23  C17  120.28  3.000
 O1H  N6   C19  C18  131.51  3.000
 O1H  N6   C19  C21  105.97  3.000
 O1H  C18  C19  C21  122.51  3.000
 O1H  H10  C18  C19  122.10  3.000
 O1H  H10  C18  C17  121.95  3.000
 O1H  C19  C18  C17  115.94  3.000
 O1H  N6   N7   C20  107.01  3.000
 O1H  H11  N6   N7   119.81  3.000
 O1H  H11  N6   C19  127.89  3.000
 O1H  N7   N6   C19  112.28  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
 O1H  CONST_01  C4   C5   N    N1     0.00   0.0  0
 O1H  CONST_02  C5   C4   C3   N1     0.00   0.0  0
 O1H  CONST_05  C1   C    C16  N3   180.00   0.0  0
 O1H  CONST_06  C14  C15  C16  N3   180.00   0.0  0
 O1H  CONST_07  N5   C15  C16  N3     0.00   0.0  0
 O1H  CONST_08  C15  N5   N4   N3     0.00   0.0  0
 O1H  CONST_09  C17  N5   N4   N3   180.00   0.0  0
 O1H  CONST_10  N    N1   C3   C4     0.00   0.0  0
 O1H  CONST_13  C3   N1   N    C5     0.00   0.0  0
 O1H  CONST_14  C2   C3   C4   C5   180.00   0.0  0
 O1H  CONST_15  C10  C12  C13  C7     0.00   0.0  0
 O1H  CONST_16  C10  C9   C8   C7     0.00   0.0  0
 O1H  CONST_17  C12  C10  C9   C8     0.00   0.0  0
 O1H  CONST_18  C12  C13  C7   C8     0.00   0.0  0
 O1H  CONST_19  C9   C10  C12  C13    0.00   0.0  0
 O1H  CONST_20  C9   C8   C7   C13    0.00   0.0  0
 O1H  CONST_21  C3   C2   C14  C15  180.00   0.0  0
 O1H  CONST_22  C1   C2   C14  C15    0.00   0.0  0
 O1H  CONST_23  C1   C    C16  C15    0.00   0.0  0
 O1H  CONST_24  N4   N3   C16  C15    0.00   0.0  0
 O1H  CONST_27  C14  C15  N5   C17    0.00   0.0  0
 O1H  CONST_28  C16  C15  N5   C17  180.00   0.0  0
 O1H  CONST_29  C21  C19  C18  C17    0.00   0.0  0
 O1H  CONST_30  N6   C19  C18  C17  180.00   0.0  0
 O1H  CONST_31  C21  C22  C23  C17    0.00   0.0  0
 O1H  CONST_32  C23  C22  C21  C20  180.00   0.0  0
 O1H  CONST_33  C18  C19  C21  C20  180.00   0.0  0
 O1H  CONST_34  N6   C19  C21  C20    0.00   0.0  0
 O1H  CONST_35  C19  N6   N7   C20    0.00   0.0  0
 O1H  CONST_36  N7   N6   C19  C21    0.00   0.0  0
 O1H  CONST_37  N6   N7   C20  C21    0.00   0.0  0
 O1H  CONST_38  N5   C17  C23  C22  180.00   0.0  0
 O1H  CONST_39  C18  C17  C23  C22    0.00   0.0  0
 O1H  CONST_40  C18  C19  C21  C22    0.00   0.0  0
 O1H  CONST_41  N6   C19  C21  C22  180.00   0.0  0
 O1H  CONST_42  N7   C20  C21  C22  180.00   0.0  0
 O1H  CONST_43  C2   C3   N1   N    180.00   0.0  0
 O1H  CONST_44  C3   C4   C5   N      0.00   0.0  0
 O1H  CONST_45  C    C1   C2   C3   180.00   0.0  0
 O1H  CONST_46  C16  C    C1   C2     0.00   0.0  0
 O1H  CONST_47  C16  C15  C14  C2     0.00   0.0  0
 O1H  CONST_48  N5   C15  C14  C2   180.00   0.0  0
 O1H  CONST_49  C    C1   C2   C14    0.00   0.0  0
 O1H  CONST_50  C    C16  C15  C14    0.00   0.0  0
 O1H  CONST_51  N4   N5   C15  C14  180.00   0.0  0
 O1H  CONST_52  C    C16  C15  N5   180.00   0.0  0
 O1H  CONST_53  C19  C18  C17  N5   180.00   0.0  0
 O1H  CONST_54  C16  N3   N4   N5     0.00   0.0  0
 O1H  CONST_55  C16  C15  N5   N4     0.00   0.0  0
 O1H  CONST_58  C    C16  N3   N4   180.00   0.0  0
 O1H  CONST_59  C19  C18  C17  C23    0.00   0.0  0
 O1H  CONST_60  C19  C21  C22  C23    0.00   0.0  0
 O1H  CONST_61  N7   C20  C21  C19    0.00   0.0  0
 O1H  CONST_62  N7   N6   C19  C18  180.00   0.0  0
 O1H  CONST_63  CL   C    C16  N3     0.00   0.0  0
 O1H  CONST_64  C6   N1   C3   C4   180.00   0.0  0
 O1H  CONST_65  C6   N1   N    C5   180.00   0.0  0
 O1H  CONST_66  C12  C13  C7   C6   180.00   0.0  0
 O1H  CONST_67  C9   C8   C7   C6   180.00   0.0  0
 O1H  CONST_68  C2   C3   N1   C6     0.00   0.0  0
 O1H  CONST_69  C11  C10  C9   C8   180.00   0.0  0
 O1H  CONST_70  C11  C10  C12  C13  180.00   0.0  0
 O1H  CONST_71  CL   C    C16  C15  180.00   0.0  0
 O1H  CONST_72  CL   C    C1   C2   180.00   0.0  0
 O1H  CONST_73  H2   C5   N    N1   180.00   0.0  0
 O1H  CONST_74  H1   C4   C3   N1   180.00   0.0  0
 O1H  CONST_75  H7   C12  C13  C7   180.00   0.0  0
 O1H  CONST_76  H6   C9   C8   C7   180.00   0.0  0
 O1H  CONST_77  H8   C13  C7   C8   180.00   0.0  0
 O1H  CONST_78  H5   C8   C9   C10  180.00   0.0  0
 O1H  CONST_79  H13  C22  C23  C17  180.00   0.0  0
 O1H  CONST_80  H11  N6   N7   C20  180.00   0.0  0
 O1H  CONST_81  H14  C23  C22  C21  180.00   0.0  0
 O1H  CONST_82  H10  C18  C19  C21  180.00   0.0  0
 O1H  CONST_83  H12  C20  C21  C22    0.00   0.0  0
 O1H  CONST_84  H    C1   C2   C3     0.00   0.0  0
 O1H  CONST_85  H9   C14  C2   C3     0.00   0.0  0
 O1H  Var_01    C13  C7   C6   N1   124.39  30.0  2
 O1H  Var_02    N    N1   C6   C7   120.85  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
 O1H  plan-1  N1   0.020
 O1H  plan-1  C4   0.020
 O1H  plan-1  C5   0.020
 O1H  plan-1  C6   0.020
 O1H  plan-1  N    0.020
 O1H  plan-1  C3   0.020
 O1H  plan-1  C2   0.020
 O1H  plan-1  H1   0.020
 O1H  plan-1  H2   0.020
 O1H  plan-2  C6   0.020
 O1H  plan-2  C7   0.020
 O1H  plan-2  C8   0.020
 O1H  plan-2  C10  0.020
 O1H  plan-2  C13  0.020
 O1H  plan-2  N2   0.020
 O1H  plan-2  C11  0.020
 O1H  plan-2  C9   0.020
 O1H  plan-2  C12  0.020
 O1H  plan-2  H5   0.020
 O1H  plan-2  H8   0.020
 O1H  plan-2  H6   0.020
 O1H  plan-2  H7   0.020
 O1H  plan-3  N3   0.020
 O1H  plan-3  C15  0.020
 O1H  plan-3  C17  0.020
 O1H  plan-3  C3   0.020
 O1H  plan-3  C2   0.020
 O1H  plan-3  C1   0.020
 O1H  plan-3  C14  0.020
 O1H  plan-3  N5   0.020
 O1H  plan-3  N4   0.020
 O1H  plan-3  C16  0.020
 O1H  plan-3  C    0.020
 O1H  plan-3  CL   0.020
 O1H  plan-3  H    0.020
 O1H  plan-3  H9   0.020
 O1H  plan-4  C17  0.020
 O1H  plan-4  C20  0.020
 O1H  plan-4  C21  0.020
 O1H  plan-4  C22  0.020
 O1H  plan-4  N5   0.020
 O1H  plan-4  C23  0.020
 O1H  plan-4  C19  0.020
 O1H  plan-4  C18  0.020
 O1H  plan-4  N7   0.020
 O1H  plan-4  N6   0.020
 O1H  plan-4  H12  0.020
 O1H  plan-4  H13  0.020
 O1H  plan-4  H14  0.020
 O1H  plan-4  H10  0.020
 O1H  plan-4  H11  0.020

