# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 13 04:56:46 2020
#   Inital geometry file: a 111 line input string
#   Ligand name: 5-[(5-azanyl-3-methyl-pyrazol-1-yl)methyl]-~{N}-[1-[(2-chloranyl-6-fluoranyl-phenyl)methyl]pyrazol-3-yl]-1,3,4-thiadiazol-2-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1cc(N)n(Cc2sc(Nc3ccn(Cc4c(F)cccc4Cl)n3)nn2)n1
#
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
 9WH  9WH  5-[(5-azanyl-3-methyl-pyrazol-1-yl)methyl]-~{N}-[1-[(2-chloranyl-6-fluoranyl-phenyl)methyl]pyrazol-3-yl]-1,3,4-thiadiazol-2-amine  ligand  44  28  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_9WH
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
 9WH  N12  N   NH1   0  -0.744   0.1748  -0.2391  -0.1363
 9WH  C13  C   CR5   0   0.498  -0.9580  -1.0353  -0.2074
 9WH  C15  C   CR15  0   0.066  -2.4874  -2.5927  -0.1150
 9WH  C21  C   CR16  0  -0.395  -6.2396   0.2972   1.5654
 9WH  C22  C   CR16  0  -0.255  -6.3809   1.6082   1.1368
 9WH  C24  C   CR6   0  -0.081  -5.1646   1.0975  -0.8604
 9WH  C02  C   CR5   0   0.293   6.7716   0.0201  -1.3579
 9WH  C03  C   CR15  0  -0.570   6.9574   1.3044  -0.8067
 9WH  C04  C   CR5   0   0.567   6.3075   1.2635   0.4095
 9WH  N05  N   NH2   0  -0.857   6.2075   2.1960   1.4182
 9WH  N06  N   NR5   0  -0.337   5.8027   0.0127   0.5257
 9WH  C08  C   CR5   0   0.096   3.5934  -0.7284   1.1949
 9WH  N09  N   N     0  -0.228   2.8941  -1.7720   1.4487
 9WH  N10  N   N     0  -0.327   1.6167  -1.7038   1.0132
 9WH  C11  C   CR5   0   0.338   1.3574  -0.5824   0.4099
 9WH  C14  C   CR15  0  -0.543  -1.1861  -2.3442   0.2582
 9WH  N16  N   NR5   0  -0.263  -2.9369  -1.4989  -0.7476
 9WH  C18  C   CR6   0  -0.006  -5.0025  -0.2308  -0.4730
 9WH  C19  C   CR6   0   0.545  -5.5560  -0.5813   0.7521
 9WH  F20  F   F     0  -0.305  -5.4132  -1.8509   1.1593
 9WH  C23  C   CR16  0  -0.218  -5.8464   2.0159  -0.0747
 9WH  N26  N   N     0  -0.325  -2.0197  -0.5333  -0.8084
 9WH  S27  S   S2    0   0.169   2.7158   0.5016   0.3356
 9WH  N28  N   N     0  -0.328   6.0650  -0.7476  -0.5567
 9WH  H37  H   HNH1  0   0.424   0.0933   0.6671  -0.5713
 9WH  H39  H   HCR5  0   0.297  -3.1034  -3.4665   0.0228
 9WH  H40  H   HCH2  0   0.289  -4.1658  -0.9469  -2.3176
 9WH  H41  H   HCH2  0   0.296  -4.7900  -2.2093  -1.2832
 9WH  H42  H   HCR6  0   0.289  -6.6511  -0.0369   2.5081
 9WH  H43  H   HCR6  0   0.283  -6.9134   2.3200   1.7522
 9WH  H31  H   HCH3  0   0.245   8.3446  -0.3728  -2.7560
 9WH  H30  H   HCH3  0   0.244   7.0153  -1.5327  -2.8049
 9WH  H29  H   HCH3  0   0.245   6.8194   0.0769  -3.4987
 9WH  H32  H   HCR5  0   0.259   7.4823   2.1431  -1.2343
 9WH  H34  H   HNH2  0   0.393   6.5940   3.0893   1.1548
 9WH  H33  H   HNH2  0   0.386   5.2809   2.3298   1.7975
 9WH  H35  H   HCH2  0   0.308   5.4256  -1.5000   1.9013
 9WH  H36  H   HCH2  0   0.299   5.0868   0.1305   2.4586
 9WH  H38  H   HCR5  0   0.280  -0.5114  -2.9978   0.7787
 9WH  H44  H   HCR6  0   0.287  -5.9570   3.0388  -0.4057
 9WH  C17  C   CH2   0  -0.378  -4.2587  -1.2594  -1.2800
 9WH  C07  C   CH2   0  -0.393   5.0189  -0.5356   1.5965
 9WH  CL1  CL  CL    0  -0.109  -4.5144   1.6489  -2.3673
 9WH  C01  C   CH3   0  -0.735   7.2626  -0.4807  -2.6724

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
 9WH  C01  C02  single    1.490  0.020  1.490
 9WH  N28  C02  aromatic  1.316  0.020  1.316
 9WH  N28  N06  aromatic  1.348  0.020  1.348
 9WH  C02  C03  aromatic  1.410  0.020  1.410
 9WH  N09  N10  aromatic  1.351  0.020  1.351
 9WH  N09  C08  aromatic  1.282  0.020  1.282
 9WH  C07  N06  single    1.436  0.020  1.436
 9WH  C07  C08  single    1.494  0.020  1.494
 9WH  N06  C04  aromatic  1.354  0.020  1.354
 9WH  N10  C11  aromatic  1.299  0.020  1.299
 9WH  C08  S27  aromatic  1.738  0.020  1.738
 9WH  C03  C04  aromatic  1.380  0.020  1.380
 9WH  C04  N05  single    1.377  0.020  1.377
 9WH  C11  S27  aromatic  1.740  0.020  1.740
 9WH  C11  N12  single    1.347  0.020  1.347
 9WH  N12  C13  single    1.386  0.020  1.386
 9WH  C13  N26  aromatic  1.319  0.020  1.319
 9WH  C13  C14  aromatic  1.408  0.020  1.408
 9WH  N26  N16  aromatic  1.333  0.020  1.333
 9WH  C14  C15  aromatic  1.376  0.020  1.376
 9WH  C23  C22  aromatic  1.385  0.020  1.385
 9WH  C23  C24  aromatic  1.388  0.020  1.388
 9WH  C22  C21  aromatic  1.386  0.020  1.386
 9WH  CL1  C24  single    1.731  0.020  1.731
 9WH  C24  C18  aromatic  1.393  0.020  1.393
 9WH  C21  C19  aromatic  1.379  0.020  1.379
 9WH  N16  C15  aromatic  1.341  0.020  1.341
 9WH  N16  C17  single    1.445  0.020  1.445
 9WH  C18  C19  aromatic  1.389  0.020  1.389
 9WH  C18  C17  single    1.504  0.020  1.504
 9WH  C19  F20  single    1.341  0.020  1.341
 9WH  N12  H37  single    0.860  0.020  1.020
 9WH  C15  H39  single    0.930  0.020  1.080
 9WH  C17  H40  single    0.970  0.020  1.090
 9WH  C17  H41  single    0.970  0.020  1.090
 9WH  C21  H42  single    0.930  0.020  1.080
 9WH  C22  H43  single    0.930  0.020  1.080
 9WH  C01  H31  single    0.970  0.020  1.090
 9WH  C01  H30  single    0.970  0.020  1.090
 9WH  C01  H29  single    0.970  0.020  1.090
 9WH  C03  H32  single    0.930  0.020  1.080
 9WH  N05  H34  single    0.890  0.020  1.040
 9WH  N05  H33  single    0.890  0.020  1.040
 9WH  C07  H35  single    0.970  0.020  1.090
 9WH  C07  H36  single    0.970  0.020  1.090
 9WH  C14  H38  single    0.930  0.020  1.080
 9WH  C23  H44  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
 9WH  H37  N12  C11  118.34  3.000
 9WH  H37  N12  C13  115.34  3.000
 9WH  C11  N12  C13  126.28  3.000
 9WH  N26  C13  C14  111.96  3.000
 9WH  C14  C13  N12  130.49  3.000
 9WH  N26  C13  N12  117.54  3.000
 9WH  H39  C15  N16  122.00  3.000
 9WH  H39  C15  C14  130.69  3.000
 9WH  N16  C15  C14  107.31  3.000
 9WH  H42  C21  C19  120.40  3.000
 9WH  H42  C21  C22  121.52  3.000
 9WH  C19  C21  C22  118.08  3.000
 9WH  H43  C22  C23  119.61  3.000
 9WH  H43  C22  C21  119.78  3.000
 9WH  C23  C22  C21  120.61  3.000
 9WH  CL1  C24  C23  117.81  3.000
 9WH  CL1  C24  C18  120.13  3.000
 9WH  C23  C24  C18  122.06  3.000
 9WH  N28  C02  C03  111.36  3.000
 9WH  C03  C02  C01  127.42  3.000
 9WH  N28  C02  C01  121.21  3.000
 9WH  H32  C03  C04  127.02  3.000
 9WH  H32  C03  C02  128.16  3.000
 9WH  C04  C03  C02  104.81  3.000
 9WH  N06  C04  N05  122.38  3.000
 9WH  N05  C04  C03  131.29  3.000
 9WH  N06  C04  C03  106.18  3.000
 9WH  H33  N05  H34  109.41  3.000
 9WH  H33  N05  C04  115.55  3.000
 9WH  H34  N05  C04  112.37  3.000
 9WH  N28  N06  C07  119.31  3.000
 9WH  C07  N06  C04  128.34  3.000
 9WH  N28  N06  C04  112.30  3.000
 9WH  S27  C08  N09  113.49  3.000
 9WH  S27  C08  C07  121.56  3.000
 9WH  N09  C08  C07  124.94  3.000
 9WH  N10  N09  C08  114.26  3.000
 9WH  C11  N10  N09  112.45  3.000
 9WH  S27  C11  N10  113.69  3.000
 9WH  S27  C11  N12  120.63  3.000
 9WH  N10  C11  N12  125.69  3.000
 9WH  H38  C14  C15  127.99  3.000
 9WH  H38  C14  C13  128.63  3.000
 9WH  C15  C14  C13  103.38  3.000
 9WH  N26  N16  C17  119.50  3.000
 9WH  C17  N16  C15  128.00  3.000
 9WH  N26  N16  C15  112.44  3.000
 9WH  C19  C18  C24  116.07  3.000
 9WH  C19  C18  C17  119.84  3.000
 9WH  C24  C18  C17  124.08  3.000
 9WH  F20  C19  C18  117.66  3.000
 9WH  F20  C19  C21  118.49  3.000
 9WH  C18  C19  C21  123.85  3.000
 9WH  H44  C23  C24  120.22  3.000
 9WH  H44  C23  C22  120.45  3.000
 9WH  C24  C23  C22  119.33  3.000
 9WH  N16  N26  C13  104.91  3.000
 9WH  C11  S27  C08   86.11  3.000
 9WH  N06  N28  C02  105.33  3.000
 9WH  H41  C17  H40  106.84  3.000
 9WH  H41  C17  C18  110.91  3.000
 9WH  H40  C17  C18  110.95  3.000
 9WH  H41  C17  N16  107.64  3.000
 9WH  H40  C17  N16  108.73  3.000
 9WH  C18  C17  N16  111.59  3.000
 9WH  H36  C07  H35  107.21  3.000
 9WH  H36  C07  C08  110.52  3.000
 9WH  H35  C07  C08  108.49  3.000
 9WH  H36  C07  N06  108.79  3.000
 9WH  H35  C07  N06  110.04  3.000
 9WH  C08  C07  N06  111.70  3.000
 9WH  H29  C01  H30  108.02  3.000
 9WH  H29  C01  H31  107.13  3.000
 9WH  H30  C01  H31  108.15  3.000
 9WH  H29  C01  C02  111.26  3.000
 9WH  H30  C01  C02  110.94  3.000
 9WH  H31  C01  C02  111.18  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
 9WH  CONST_01  C15  N16  N26  C13     0.00   0.0  0
 9WH  CONST_02  N16  C15  C14  C13     0.00   0.0  0
 9WH  CONST_03  N26  C13  C14  C15     0.00   0.0  0
 9WH  CONST_04  C24  C23  C22  C21     0.00   0.0  0
 9WH  CONST_05  C24  C18  C19  C21     0.00   0.0  0
 9WH  CONST_06  C18  C24  C23  C22     0.00   0.0  0
 9WH  CONST_07  C18  C19  C21  C22     0.00   0.0  0
 9WH  CONST_08  C04  N06  N28  C02     0.00   0.0  0
 9WH  CONST_09  N06  C04  C03  C02     0.00   0.0  0
 9WH  CONST_10  N06  N28  C02  C03     0.00   0.0  0
 9WH  CONST_11  N28  N06  C04  C03     0.00   0.0  0
 9WH  CONST_12  N28  C02  C03  C04     0.00   0.0  0
 9WH  CONST_13  C11  N10  N09  C08     0.00   0.0  0
 9WH  CONST_14  N10  C11  S27  C08     0.00   0.0  0
 9WH  CONST_15  S27  C11  N10  N09     0.00   0.0  0
 9WH  CONST_16  C11  S27  C08  N09     0.00   0.0  0
 9WH  CONST_17  S27  C08  N09  N10     0.00   0.0  0
 9WH  CONST_18  N16  N26  C13  C14     0.00   0.0  0
 9WH  CONST_19  N26  N16  C15  C14     0.00   0.0  0
 9WH  CONST_20  C23  C22  C21  C19     0.00   0.0  0
 9WH  CONST_21  C23  C24  C18  C19     0.00   0.0  0
 9WH  CONST_22  N09  N10  C11  N12   180.00   0.0  0
 9WH  CONST_23  C08  S27  C11  N12   180.00   0.0  0
 9WH  CONST_24  N16  N26  C13  N12   180.00   0.0  0
 9WH  CONST_25  C15  C14  C13  N12   180.00   0.0  0
 9WH  CONST_26  C17  N16  N26  C13   180.00   0.0  0
 9WH  CONST_27  C14  C15  N16  C17   180.00   0.0  0
 9WH  CONST_28  C23  C24  C18  C17   180.00   0.0  0
 9WH  CONST_29  C21  C19  C18  C17   180.00   0.0  0
 9WH  CONST_30  CL1  C24  C23  C22   180.00   0.0  0
 9WH  CONST_31  F20  C19  C21  C22   180.00   0.0  0
 9WH  CONST_32  F20  C19  C18  C24   180.00   0.0  0
 9WH  CONST_33  N06  N28  C02  C01   180.00   0.0  0
 9WH  CONST_34  C04  C03  C02  C01   180.00   0.0  0
 9WH  CONST_35  C07  N06  N28  C02   180.00   0.0  0
 9WH  CONST_36  N05  C04  C03  C02   180.00   0.0  0
 9WH  CONST_37  C07  N06  C04  C03   180.00   0.0  0
 9WH  CONST_38  N28  N06  C04  N05   180.00   0.0  0
 9WH  CONST_39  N10  N09  C08  C07   180.00   0.0  0
 9WH  CONST_40  C11  S27  C08  C07   180.00   0.0  0
 9WH  CONST_41  CL1  C24  C18  C19   180.00   0.0  0
 9WH  CONST_42  H39  C15  C14  C13   180.00   0.0  0
 9WH  CONST_43  H44  C23  C22  C21   180.00   0.0  0
 9WH  CONST_44  H43  C22  C23  C24   180.00   0.0  0
 9WH  CONST_45  H32  C03  C04  N06   180.00   0.0  0
 9WH  CONST_46  H38  C14  C15  N16   180.00   0.0  0
 9WH  CONST_47  H42  C21  C19  C18   180.00   0.0  0
 9WH  CONST_48  H34  N05  C04  C03     0.00   0.0  0
 9WH  Var_01    N10  C11  N12  C13    -3.03  30.0  2
 9WH  Var_02    C18  C17  N16  C15   109.43  30.0  2
 9WH  Var_03    N16  C17  C18  C24   102.04  30.0  2
 9WH  Var_04    C08  C07  N06  C04   107.79  30.0  2
 9WH  Var_05    N09  C08  C07  N06   135.66  30.0  2
 9WH  Var_06    N26  C13  N12  C11  -178.58  30.0  2
 9WH  Var_07    H31  C01  C02  C03    56.34  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
 9WH  plan-1  N12  0.020
 9WH  plan-1  C13  0.020
 9WH  plan-1  C15  0.020
 9WH  plan-1  C14  0.020
 9WH  plan-1  N16  0.020
 9WH  plan-1  N26  0.020
 9WH  plan-1  H39  0.020
 9WH  plan-1  H38  0.020
 9WH  plan-1  C17  0.020
 9WH  plan-2  N12  0.020
 9WH  plan-2  C08  0.020
 9WH  plan-2  N09  0.020
 9WH  plan-2  N10  0.020
 9WH  plan-2  C11  0.020
 9WH  plan-2  S27  0.020
 9WH  plan-2  C07  0.020
 9WH  plan-3  C02  0.020
 9WH  plan-3  C03  0.020
 9WH  plan-3  C04  0.020
 9WH  plan-3  N05  0.020
 9WH  plan-3  N06  0.020
 9WH  plan-3  N28  0.020
 9WH  plan-3  H32  0.020
 9WH  plan-3  C07  0.020
 9WH  plan-3  C01  0.020
 9WH  plan-4  C21  0.020
 9WH  plan-4  C22  0.020
 9WH  plan-4  C24  0.020
 9WH  plan-4  C18  0.020
 9WH  plan-4  C19  0.020
 9WH  plan-4  F20  0.020
 9WH  plan-4  C23  0.020
 9WH  plan-4  H42  0.020
 9WH  plan-4  H43  0.020
 9WH  plan-4  H44  0.020
 9WH  plan-4  C17  0.020
 9WH  plan-4  CL1  0.020
 9WH  plan-5  C04  0.020
 9WH  plan-5  N05  0.020
 9WH  plan-5  H34  0.020
 9WH  plan-5  H33  0.020

