# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Mar 20 14:18:02 2022
#   Inital geometry file: a 92 line input string
#   Ligand name: 4-azanyl-6-[1-[[3,4-bis(fluoranyl)phenyl]methyl]pyrazol-4-yl]pyrimidine-5-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Nc1ncnc(c2cnn(Cc3ccc(F)c(F)c3)c2)c1C#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
 Q0H  Q0H  4-azanyl-6-[1-[[3,4-bis(fluoranyl)phenyl]methyl]pyrazol-4-yl]pyrimidine-5-carbonitrile  ligand  33  23  .  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_Q0H
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
 Q0H  C10  C  CR5   0  -0.212  19.8344  15.3327  34.3645
 Q0H  N12  N  NR5   0  -0.271  20.3190  14.8880  36.4475
 Q0H  C13  C  CH2   0  -0.404  20.6864  14.2286  37.6861
 Q0H  C15  C  CR16  0  -0.445  22.5828  15.3323  38.9107
 Q0H  C17  C  CR6   0   0.391  24.8616  14.7234  38.4670
 Q0H  C20  C  CR16  0  -0.279  23.0932  13.6228  37.3022
 Q0H  C02  C  CR6   0   0.549  19.0169  14.3198  30.8065
 Q0H  C03  C  CR6   0  -0.173  19.3144  14.1628  32.1872
 Q0H  C04  C  CSP   0  -0.018  19.3916  12.8568  32.7198
 Q0H  N05  N  NS    0  -0.243  19.4454  11.7716  33.1098
 Q0H  C06  C  CR6   0   0.340  19.5119  15.3193  32.9509
 Q0H  N07  N  N     0  -0.468  19.4065  16.5234  32.3800
 Q0H  C08  C  CR16  0   0.070  19.1155  16.5587  31.0919
 Q0H  N09  N  N     0  -0.449  18.9188  15.5433  30.2771
 Q0H  C11  C  CR15  0   0.043  20.0627  14.3083  35.2725
 Q0H  C14  C  CR6   0   0.132  22.1539  14.3917  37.9802
 Q0H  C16  C  CR6   0   0.412  23.9326  15.4892  39.1491
 Q0H  C19  C  CR16  0  -0.391  24.4494  13.7866  37.5418
 Q0H  F21  F  F     0  -0.304  24.3620  16.3865  40.0418
 Q0H  N22  N  N     0  -0.260  20.2870  16.2208  36.3875
 Q0H  C23  C  CR15  0  -0.029  19.9943  16.5049  35.1411
 Q0H  H1   H  HCH2  0   0.298  20.0761  14.6439  38.4872
 Q0H  H2   H  HCH2  0   0.296  20.4256  13.1759  37.5811
 Q0H  H3   H  HCR6  0   0.292  21.8723  15.9431  39.4542
 Q0H  H4   H  HCR6  0   0.274  22.7703  12.8844  36.5790
 Q0H  H5   H  HNH2  0   0.414  18.6235  13.4464  29.0261
 Q0H  H6   H  HNH2  0   0.423  18.8965  12.3272  30.3056
 Q0H  H7   H  HCR6  0   0.266  19.0296  17.5460  30.6496
 Q0H  H8   H  HCR5  0   0.303  20.0662  13.2356  35.1793
 Q0H  H9   H  HCR6  0   0.294  25.1842  13.1892  37.0181
 Q0H  H10  H  HCR5  0   0.269  19.8952  17.5285  34.8167
 Q0H  F18  F  F     0  -0.303  26.1616  14.9019  38.7174
 Q0H  N01  N  NH2   0  -0.817  18.8241  13.2824  29.9988

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
 Q0H  N01  C02  single    1.329  0.020  1.329
 Q0H  N09  C02  aromatic  1.337  0.020  1.337
 Q0H  N09  C08  aromatic  1.317  0.020  1.317
 Q0H  C02  C03  aromatic  1.421  0.020  1.421
 Q0H  C08  N07  aromatic  1.321  0.020  1.321
 Q0H  C03  C04  single    1.412  0.020  1.412
 Q0H  C03  C06  aromatic  1.400  0.020  1.400
 Q0H  N07  C06  aromatic  1.337  0.020  1.337
 Q0H  C04  N05  triple    1.154  0.020  1.154
 Q0H  C06  C10  single    1.450  0.020  1.450
 Q0H  C10  C23  aromatic  1.415  0.020  1.415
 Q0H  C10  C11  aromatic  1.388  0.020  1.388
 Q0H  C23  N22  aromatic  1.311  0.020  1.311
 Q0H  C11  N12  aromatic  1.335  0.020  1.335
 Q0H  N22  N12  aromatic  1.335  0.020  1.335
 Q0H  N12  C13  single    1.451  0.020  1.451
 Q0H  C20  C19  aromatic  1.387  0.020  1.387
 Q0H  C20  C14  aromatic  1.390  0.020  1.390
 Q0H  C19  C17  aromatic  1.380  0.020  1.380
 Q0H  C13  C14  single    1.506  0.020  1.506
 Q0H  C14  C15  aromatic  1.391  0.020  1.391
 Q0H  C17  F18  single    1.336  0.020  1.336
 Q0H  C17  C16  aromatic  1.384  0.020  1.384
 Q0H  C15  C16  aromatic  1.380  0.020  1.380
 Q0H  C16  F21  single    1.337  0.020  1.337
 Q0H  C13  H1   single    0.970  0.020  1.090
 Q0H  C13  H2   single    0.970  0.020  1.090
 Q0H  C15  H3   single    0.930  0.020  1.080
 Q0H  C20  H4   single    0.930  0.020  1.080
 Q0H  N01  H5   single    0.860  0.020  1.020
 Q0H  N01  H6   single    0.860  0.020  1.020
 Q0H  C08  H7   single    0.930  0.020  1.080
 Q0H  C11  H8   single    0.930  0.020  1.080
 Q0H  C19  H9   single    0.930  0.020  1.080
 Q0H  C23  H10  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
 Q0H  C23  C10  C11  103.52  3.000
 Q0H  C11  C10  C06  131.88  3.000
 Q0H  C23  C10  C06  124.60  3.000
 Q0H  N22  N12  C11  112.92  3.000
 Q0H  N22  N12  C13  119.90  3.000
 Q0H  C11  N12  C13  127.07  3.000
 Q0H  H2   C13  H1   107.76  3.000
 Q0H  H2   C13  C14  110.91  3.000
 Q0H  H1   C13  C14  111.16  3.000
 Q0H  H2   C13  N12  107.24  3.000
 Q0H  H1   C13  N12  108.23  3.000
 Q0H  C14  C13  N12  111.37  3.000
 Q0H  H3   C15  C16  119.40  3.000
 Q0H  H3   C15  C14  120.98  3.000
 Q0H  C16  C15  C14  119.62  3.000
 Q0H  C19  C17  F18  120.47  3.000
 Q0H  F18  C17  C16  119.15  3.000
 Q0H  C19  C17  C16  120.38  3.000
 Q0H  H4   C20  C19  119.18  3.000
 Q0H  H4   C20  C14  120.08  3.000
 Q0H  C19  C20  C14  120.74  3.000
 Q0H  N09  C02  C03  120.09  3.000
 Q0H  C03  C02  N01  122.32  3.000
 Q0H  N09  C02  N01  117.59  3.000
 Q0H  C06  C03  C04  123.40  3.000
 Q0H  C06  C03  C02  117.92  3.000
 Q0H  C04  C03  C02  118.68  3.000
 Q0H  N05  C04  C03  180.00  3.000
 Q0H  N07  C06  C03  120.00  3.000
 Q0H  N07  C06  C10  115.19  3.000
 Q0H  C03  C06  C10  124.81  3.000
 Q0H  C08  N07  C06  117.25  3.000
 Q0H  H7   C08  N09  115.95  3.000
 Q0H  H7   C08  N07  116.05  3.000
 Q0H  N09  C08  N07  128.00  3.000
 Q0H  C08  N09  C02  116.73  3.000
 Q0H  H8   C11  N12  120.54  3.000
 Q0H  H8   C11  C10  132.79  3.000
 Q0H  N12  C11  C10  106.67  3.000
 Q0H  C20  C14  C15  119.46  3.000
 Q0H  C15  C14  C13  120.30  3.000
 Q0H  C20  C14  C13  120.22  3.000
 Q0H  F21  C16  C17  119.02  3.000
 Q0H  F21  C16  C15  120.40  3.000
 Q0H  C17  C16  C15  120.58  3.000
 Q0H  H9   C19  C20  121.01  3.000
 Q0H  H9   C19  C17  119.77  3.000
 Q0H  C20  C19  C17  119.22  3.000
 Q0H  C23  N22  N12  105.33  3.000
 Q0H  H10  C23  N22  120.80  3.000
 Q0H  H10  C23  C10  127.65  3.000
 Q0H  N22  C23  C10  111.55  3.000
 Q0H  H6   N01  H5   117.64  3.000
 Q0H  H6   N01  C02  123.06  3.000
 Q0H  H5   N01  C02  119.28  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
 Q0H  CONST_01  C02  C03  C06  C10  180.00   0.0  0
 Q0H  CONST_02  C08  N07  C06  C10  180.00   0.0  0
 Q0H  CONST_03  N12  N22  C23  C10    0.00   0.0  0
 Q0H  CONST_04  N22  N12  C11  C10    0.00   0.0  0
 Q0H  CONST_05  C06  C10  C11  N12  180.00   0.0  0
 Q0H  CONST_06  C23  C10  C11  N12    0.00   0.0  0
 Q0H  CONST_07  C19  C20  C14  C15    0.00   0.0  0
 Q0H  CONST_08  C19  C17  C16  C15    0.00   0.0  0
 Q0H  CONST_09  C14  C20  C19  C17    0.00   0.0  0
 Q0H  CONST_10  C14  C15  C16  C17    0.00   0.0  0
 Q0H  CONST_11  C16  C17  C19  C20    0.00   0.0  0
 Q0H  CONST_12  C16  C15  C14  C20    0.00   0.0  0
 Q0H  CONST_13  N07  C08  N09  C02    0.00   0.0  0
 Q0H  CONST_14  N07  C06  C03  C02    0.00   0.0  0
 Q0H  CONST_15  C08  N09  C02  C03    0.00   0.0  0
 Q0H  CONST_16  C08  N07  C06  C03    0.00   0.0  0
 Q0H  CONST_17  C23  C10  C06  C03  180.00   0.0  0
 Q0H  CONST_18  C11  C10  C06  C03    0.00   0.0  0
 Q0H  CONST_19  N09  C02  C03  C06    0.00   0.0  0
 Q0H  CONST_20  N09  C08  N07  C06    0.00   0.0  0
 Q0H  CONST_21  N22  C23  C10  C06  180.00   0.0  0
 Q0H  CONST_22  C23  C10  C06  N07    0.00   0.0  0
 Q0H  CONST_23  C11  C10  C06  N07  180.00   0.0  0
 Q0H  CONST_24  N22  C23  C10  C11    0.00   0.0  0
 Q0H  CONST_25  C23  N22  N12  C11    0.00   0.0  0
 Q0H  CONST_26  C04  C03  C06  C10    0.00   0.0  0
 Q0H  CONST_27  C13  N12  C11  C10  180.00   0.0  0
 Q0H  CONST_28  C23  N22  N12  C13  180.00   0.0  0
 Q0H  CONST_29  C19  C20  C14  C13  180.00   0.0  0
 Q0H  CONST_30  C16  C15  C14  C13  180.00   0.0  0
 Q0H  CONST_31  F18  C17  C16  C15  180.00   0.0  0
 Q0H  CONST_32  F18  C17  C19  C20  180.00   0.0  0
 Q0H  CONST_33  C08  N09  C02  N01  180.00   0.0  0
 Q0H  CONST_34  C06  C03  C02  N01  180.00   0.0  0
 Q0H  CONST_35  N09  C02  C03  C04  180.00   0.0  0
 Q0H  CONST_36  N07  C06  C03  C04  180.00   0.0  0
 Q0H  CONST_37  F21  C16  C15  C14  180.00   0.0  0
 Q0H  CONST_38  F21  C16  C17  C19  180.00   0.0  0
 Q0H  CONST_39  H10  C23  N22  N12  180.00   0.0  0
 Q0H  CONST_40  H4   C20  C14  C15  180.00   0.0  0
 Q0H  CONST_41  H3   C15  C16  C17  180.00   0.0  0
 Q0H  CONST_42  H7   C08  N09  C02  180.00   0.0  0
 Q0H  CONST_43  H8   C11  C10  C06    0.00   0.0  0
 Q0H  CONST_44  H9   C19  C20  C14  180.00   0.0  0
 Q0H  CONST_45  H5   N01  C02  C03  180.00   0.0  0
 Q0H  CONST_46  H6   N01  C02  C03    0.00   0.0  0
 Q0H  Var_01    C20  C14  C13  N12  -77.27  30.0  2
 Q0H  Var_02    C14  C13  N12  C11  104.53  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
 Q0H  plan-1  C10  0.020
 Q0H  plan-1  N12  0.020
 Q0H  plan-1  C13  0.020
 Q0H  plan-1  C06  0.020
 Q0H  plan-1  C11  0.020
 Q0H  plan-1  N22  0.020
 Q0H  plan-1  C23  0.020
 Q0H  plan-1  H8   0.020
 Q0H  plan-1  H10  0.020
 Q0H  plan-2  C13  0.020
 Q0H  plan-2  C15  0.020
 Q0H  plan-2  C17  0.020
 Q0H  plan-2  C20  0.020
 Q0H  plan-2  C14  0.020
 Q0H  plan-2  C16  0.020
 Q0H  plan-2  C19  0.020
 Q0H  plan-2  F21  0.020
 Q0H  plan-2  H3   0.020
 Q0H  plan-2  H4   0.020
 Q0H  plan-2  H9   0.020
 Q0H  plan-2  F18  0.020
 Q0H  plan-3  C10  0.020
 Q0H  plan-3  C02  0.020
 Q0H  plan-3  C03  0.020
 Q0H  plan-3  C04  0.020
 Q0H  plan-3  N05  0.020
 Q0H  plan-3  C06  0.020
 Q0H  plan-3  N07  0.020
 Q0H  plan-3  C08  0.020
 Q0H  plan-3  N09  0.020
 Q0H  plan-3  H7   0.020
 Q0H  plan-3  N01  0.020
 Q0H  plan-4  C02  0.020
 Q0H  plan-4  H5   0.020
 Q0H  plan-4  H6   0.020
 Q0H  plan-4  N01  0.020

