# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Mar 23 14:28:06 2020
#   Inital geometry file: a 118 line input string
#   Ligand name: 5-(4-cyanobenzyl)-N-(4-fluorophenyl)-7-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1cc(Cc2ccc(cc2)C#N)nc3n1ncc3C(=O)Nc4ccc(F)cc4
#
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
 1OB  1OB  5-(4-cyanobenzyl)-N-(4-fluorophenyl)-7-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxamide  ligand  43  29  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_1OB
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
 1OB  C1   C  CR16  0  -0.287  -2.0985   3.1450  -1.2610
 1OB  C2   C  CR16  0  -0.227  -1.0026   3.9880  -1.2681
 1OB  C3   C  CR6   0  -0.010  -0.4873   4.4516  -0.0577
 1OB  C4   C  CR16  0  -0.225  -1.0756   4.0732   1.1486
 1OB  C5   C  CR16  0  -0.286  -2.1707   3.2288   1.1352
 1OB  C6   C  CR6   0   0.173  -2.6912   2.7534  -0.0641
 1OB  C7   C  CH2   0  -0.611  -3.8565   1.8119  -0.0685
 1OB  C8   C  CR6   0   0.273  -3.4524   0.3603  -0.0497
 1OB  C9   C  CR16  0  -0.485  -4.4712  -0.6131  -0.1227
 1OB  C10  C  CR6   0   0.648  -4.1209  -1.9357  -0.1158
 1OB  N11  N  N     0  -0.422  -2.7993  -2.2236  -0.0335
 1OB  C12  C  CR56  0   0.627  -1.8502  -1.2248   0.0466
 1OB  N13  N  N     0  -0.425  -2.1783   0.0667   0.0337
 1OB  C14  C  CR5   0  -0.391  -0.6281  -1.8990   0.1059
 1OB  C15  C  CR15  0  -0.027  -0.9812  -3.2597   0.0595
 1OB  N16  N  N     0  -0.287  -2.2784  -3.4600  -0.0201
 1OB  C17  C  C     0   0.502   0.6916  -1.2763   0.2376
 1OB  O18  O  O     0  -0.451   0.8339  -0.1299   0.6266
 1OB  N19  N  NH1   0  -0.768   1.7281  -2.0928  -0.1087
 1OB  C20  C  CR6   0   0.380   3.1022  -1.8571  -0.0240
 1OB  C21  C  CR16  0  -0.304   3.6796  -0.6865   0.4725
 1OB  C22  C  CR16  0  -0.400   5.0616  -0.5584   0.5226
 1OB  C23  C  CR6   0   0.506   5.8622  -1.5885   0.0774
 1OB  C24  C  CR16  0  -0.396   5.3190  -2.7565  -0.4207
 1OB  C25  C  CR16  0  -0.345   3.9421  -2.8830  -0.4672
 1OB  F26  F  F     0  -0.319   7.1995  -1.4555   0.1297
 1OB  O27  O  OH1   0  -0.564  -4.9106  -2.9802  -0.1832
 1OB  C28  C  CSP   0   0.052   0.6437   5.3207  -0.0543
 1OB  N29  N  NS    0  -0.256   1.5597   6.0205  -0.0538
 1OB  H1   H  HCR6  0   0.265  -2.4975   2.7870  -2.2018
 1OB  H2   H  HCR6  0   0.279  -0.5472   4.2849  -2.2030
 1OB  H3   H  HCR6  0   0.279  -0.6769   4.4365   2.0861
 1OB  H4   H  HCR6  0   0.264  -2.6258   2.9364   2.0734
 1OB  H5   H  HCH2  0   0.295  -4.5027   1.9944   0.7947
 1OB  H6   H  HCH2  0   0.292  -4.4832   1.9796  -0.9486
 1OB  H7   H  HCR6  0   0.305  -5.5119  -0.3263  -0.1909
 1OB  H9   H  HCR5  0   0.283  -0.3256  -4.1175   0.1042
 1OB  H10  H  HNH1  0   0.418   1.4860  -2.9819  -0.5173
 1OB  H11  H  HCR6  0   0.289   3.0711   0.1309   0.8203
 1OB  H12  H  HCR6  0   0.281   5.5027   0.3502   0.9108
 1OB  H13  H  HCR6  0   0.283   5.9544  -3.5605  -0.7680
 1OB  H14  H  HCR6  0   0.280   3.5145  -3.7994  -0.8558
 1OB  H8   H  HOH1  0   0.508  -5.8367  -2.7076  -0.2349

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
 1OB  O18  C17  double    1.219  0.020  1.219
 1OB  C15  N16  aromatic  1.315  0.020  1.315
 1OB  C15  C14  aromatic  1.407  0.020  1.407
 1OB  C25  C24  aromatic  1.383  0.020  1.383
 1OB  C25  C20  aromatic  1.398  0.020  1.398
 1OB  C24  C23  aromatic  1.381  0.020  1.381
 1OB  C17  C14  single    1.465  0.020  1.465
 1OB  C17  N19  single    1.364  0.020  1.364
 1OB  N16  N11  aromatic  1.342  0.020  1.342
 1OB  C14  C12  aromatic  1.397  0.020  1.397
 1OB  C20  N19  single    1.397  0.020  1.397
 1OB  C20  C21  aromatic  1.396  0.020  1.396
 1OB  C23  F26  single    1.345  0.020  1.345
 1OB  C23  C22  aromatic  1.379  0.020  1.379
 1OB  N11  C12  aromatic  1.380  0.020  1.380
 1OB  N11  C10  aromatic  1.355  0.020  1.355
 1OB  C12  N13  aromatic  1.333  0.020  1.333
 1OB  C21  C22  aromatic  1.389  0.020  1.389
 1OB  O27  C10  single    1.311  0.020  1.311
 1OB  C10  C9   aromatic  1.368  0.020  1.368
 1OB  N13  C8   aromatic  1.310  0.020  1.310
 1OB  C9   C8   aromatic  1.411  0.020  1.411
 1OB  C8   C7   single    1.507  0.020  1.507
 1OB  C7   C6   single    1.498  0.020  1.498
 1OB  C1   C6   aromatic  1.392  0.020  1.392
 1OB  C1   C2   aromatic  1.383  0.020  1.383
 1OB  C6   C5   aromatic  1.391  0.020  1.391
 1OB  C2   C3   aromatic  1.395  0.020  1.395
 1OB  C5   C4   aromatic  1.383  0.020  1.383
 1OB  C3   C4   aromatic  1.394  0.020  1.394
 1OB  C3   C28  single    1.426  0.020  1.426
 1OB  C28  N29  triple    1.153  0.020  1.153
 1OB  C1   H1   single    0.930  0.020  1.080
 1OB  C2   H2   single    0.930  0.020  1.080
 1OB  C4   H3   single    0.930  0.020  1.080
 1OB  C5   H4   single    0.930  0.020  1.080
 1OB  C7   H5   single    0.970  0.020  1.090
 1OB  C7   H6   single    0.970  0.020  1.090
 1OB  C9   H7   single    0.930  0.020  1.080
 1OB  C15  H9   single    0.930  0.020  1.080
 1OB  N19  H10  single    0.860  0.020  1.020
 1OB  C21  H11  single    0.930  0.020  1.080
 1OB  C22  H12  single    0.930  0.020  1.080
 1OB  C24  H13  single    0.930  0.020  1.080
 1OB  C25  H14  single    0.930  0.020  1.080
 1OB  O27  H8   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
 1OB  H1   C1   C6   119.82  3.000
 1OB  H1   C1   C2   119.28  3.000
 1OB  C6   C1   C2   120.90  3.000
 1OB  H2   C2   C3   120.23  3.000
 1OB  H2   C2   C1   120.37  3.000
 1OB  C3   C2   C1   119.41  3.000
 1OB  C28  C3   C4   119.85  3.000
 1OB  C28  C3   C2   119.84  3.000
 1OB  C4   C3   C2   120.31  3.000
 1OB  H3   C4   C5   120.36  3.000
 1OB  H3   C4   C3   120.21  3.000
 1OB  C5   C4   C3   119.43  3.000
 1OB  H4   C5   C6   119.83  3.000
 1OB  H4   C5   C4   119.29  3.000
 1OB  C6   C5   C4   120.88  3.000
 1OB  C7   C6   C5   120.55  3.000
 1OB  C5   C6   C1   119.07  3.000
 1OB  C7   C6   C1   120.37  3.000
 1OB  H6   C7   H5   105.73  3.000
 1OB  H6   C7   C8   108.15  3.000
 1OB  H5   C7   C8   108.02  3.000
 1OB  H6   C7   C6   110.60  3.000
 1OB  H5   C7   C6   110.64  3.000
 1OB  C8   C7   C6   113.38  3.000
 1OB  N13  C8   C9   123.42  3.000
 1OB  C9   C8   C7   118.06  3.000
 1OB  N13  C8   C7   118.52  3.000
 1OB  H7   C9   C10  120.19  3.000
 1OB  H7   C9   C8   121.00  3.000
 1OB  C10  C9   C8   118.80  3.000
 1OB  O27  C10  N11  114.92  3.000
 1OB  O27  C10  C9   127.99  3.000
 1OB  N11  C10  C9   117.09  3.000
 1OB  N16  N11  C12  113.54  3.000
 1OB  C12  N11  C10  121.36  3.000
 1OB  N16  N11  C10  125.10  3.000
 1OB  C14  C12  N13  133.12  3.000
 1OB  N13  C12  N11  122.11  3.000
 1OB  C14  C12  N11  104.76  3.000
 1OB  C12  N13  C8   117.21  3.000
 1OB  C17  C14  C15  129.81  3.000
 1OB  C17  C14  C12  125.92  3.000
 1OB  C15  C14  C12  104.23  3.000
 1OB  H9   C15  N16  118.70  3.000
 1OB  H9   C15  C14  127.90  3.000
 1OB  N16  C15  C14  113.39  3.000
 1OB  C15  N16  N11  104.08  3.000
 1OB  N19  C17  O18  123.73  3.000
 1OB  N19  C17  C14  114.03  3.000
 1OB  O18  C17  C14  122.24  3.000
 1OB  H10  N19  C20  114.19  3.000
 1OB  H10  N19  C17  116.64  3.000
 1OB  C20  N19  C17  129.12  3.000
 1OB  C25  C20  C21  118.65  3.000
 1OB  C21  C20  N19  124.74  3.000
 1OB  C25  C20  N19  116.61  3.000
 1OB  H11  C21  C22  118.73  3.000
 1OB  H11  C21  C20  121.17  3.000
 1OB  C22  C21  C20  120.11  3.000
 1OB  H12  C22  C23  120.43  3.000
 1OB  H12  C22  C21  119.74  3.000
 1OB  C23  C22  C21  119.83  3.000
 1OB  F26  C23  C24  119.26  3.000
 1OB  F26  C23  C22  119.41  3.000
 1OB  C24  C23  C22  121.33  3.000
 1OB  H13  C24  C25  120.38  3.000
 1OB  H13  C24  C23  120.87  3.000
 1OB  C25  C24  C23  118.74  3.000
 1OB  H14  C25  C24  118.83  3.000
 1OB  H14  C25  C20  119.82  3.000
 1OB  C24  C25  C20  121.35  3.000
 1OB  H8   O27  C10  110.80  3.000
 1OB  N29  C28  C3   180.00  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
 1OB  CONST_01  C4   C5   C6   C1     0.00   0.0  0
 1OB  CONST_02  C4   C3   C2   C1     0.00   0.0  0
 1OB  CONST_03  C5   C6   C1   C2     0.00   0.0  0
 1OB  CONST_04  C5   C4   C3   C2     0.00   0.0  0
 1OB  CONST_05  C6   C1   C2   C3     0.00   0.0  0
 1OB  CONST_06  C6   C5   C4   C3     0.00   0.0  0
 1OB  CONST_07  C14  C12  N13  C8   180.00   0.0  0
 1OB  CONST_08  N11  C12  N13  C8     0.00   0.0  0
 1OB  CONST_09  N11  C10  C9   C8     0.00   0.0  0
 1OB  CONST_10  N16  N11  C10  C9   180.00   0.0  0
 1OB  CONST_11  C12  N11  C10  C9     0.00   0.0  0
 1OB  CONST_12  C12  N13  C8   C9     0.00   0.0  0
 1OB  CONST_13  C15  N16  N11  C10  180.00   0.0  0
 1OB  CONST_14  C14  C12  N11  C10  180.00   0.0  0
 1OB  CONST_15  N13  C12  N11  C10    0.00   0.0  0
 1OB  CONST_16  N13  C8   C9   C10    0.00   0.0  0
 1OB  CONST_17  C14  C15  N16  N11    0.00   0.0  0
 1OB  CONST_18  C15  C14  C12  N11    0.00   0.0  0
 1OB  CONST_19  N16  C15  C14  C12    0.00   0.0  0
 1OB  CONST_20  C15  N16  N11  C12    0.00   0.0  0
 1OB  CONST_21  C15  C14  C12  N13  180.00   0.0  0
 1OB  CONST_22  N16  N11  C12  N13  180.00   0.0  0
 1OB  CONST_23  N16  N11  C12  C14    0.00   0.0  0
 1OB  CONST_24  C23  C24  C25  C20    0.00   0.0  0
 1OB  CONST_25  C23  C22  C21  C20    0.00   0.0  0
 1OB  CONST_26  C24  C25  C20  C21    0.00   0.0  0
 1OB  CONST_27  C24  C23  C22  C21    0.00   0.0  0
 1OB  CONST_28  C25  C24  C23  C22    0.00   0.0  0
 1OB  CONST_29  C25  C20  C21  C22    0.00   0.0  0
 1OB  CONST_30  C28  C3   C2   C1   180.00   0.0  0
 1OB  CONST_31  C7   C6   C1   C2   180.00   0.0  0
 1OB  CONST_32  C7   C6   C5   C4   180.00   0.0  0
 1OB  CONST_33  C28  C3   C4   C5   180.00   0.0  0
 1OB  CONST_34  C12  N13  C8   C7   180.00   0.0  0
 1OB  CONST_35  C10  C9   C8   C7   180.00   0.0  0
 1OB  CONST_36  O27  C10  C9   C8   180.00   0.0  0
 1OB  CONST_37  C17  C14  C12  N11  180.00   0.0  0
 1OB  CONST_38  O27  C10  N11  C12  180.00   0.0  0
 1OB  CONST_39  C17  C14  C12  N13    0.00   0.0  0
 1OB  CONST_40  C17  C14  C15  N16  180.00   0.0  0
 1OB  CONST_41  O27  C10  N11  N16    0.00   0.0  0
 1OB  CONST_42  C24  C25  C20  N19  180.00   0.0  0
 1OB  CONST_43  C22  C21  C20  N19  180.00   0.0  0
 1OB  CONST_44  F26  C23  C22  C21  180.00   0.0  0
 1OB  CONST_45  F26  C23  C24  C25  180.00   0.0  0
 1OB  CONST_46  H4   C5   C6   C1   180.00   0.0  0
 1OB  CONST_47  H3   C4   C3   C2   180.00   0.0  0
 1OB  CONST_48  H1   C1   C2   C3   180.00   0.0  0
 1OB  CONST_49  H2   C2   C3   C4   180.00   0.0  0
 1OB  CONST_50  H9   C15  N16  N11  180.00   0.0  0
 1OB  CONST_51  H7   C9   C10  N11  180.00   0.0  0
 1OB  CONST_52  H13  C24  C25  C20  180.00   0.0  0
 1OB  CONST_53  H12  C22  C21  C20  180.00   0.0  0
 1OB  CONST_54  H14  C25  C20  C21  180.00   0.0  0
 1OB  CONST_55  H11  C21  C22  C23  180.00   0.0  0
 1OB  CONST_56  C20  N19  C17  C14  180.00   0.0  0
 1OB  CONST_57  C25  C20  N19  C17  180.00   0.0  0
 1OB  CONST_58  C21  C20  N19  C17    0.00   0.0  0
 1OB  CONST_59  H10  N19  C20  C21  180.00   0.0  0
 1OB  CONST_60  C20  N19  C17  O18    0.00   0.0  0
 1OB  Var_01    C8   C7   C6   C1    87.61  30.0  2
 1OB  Var_02    N13  C8   C7   C6     3.28  30.0  3
 1OB  Var_03    O18  C17  C14  C12   18.04  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
 1OB  plan-1  C1   0.020
 1OB  plan-1  C2   0.020
 1OB  plan-1  C3   0.020
 1OB  plan-1  C4   0.020
 1OB  plan-1  C5   0.020
 1OB  plan-1  C6   0.020
 1OB  plan-1  C7   0.020
 1OB  plan-1  C28  0.020
 1OB  plan-1  N29  0.020
 1OB  plan-1  H1   0.020
 1OB  plan-1  H2   0.020
 1OB  plan-1  H3   0.020
 1OB  plan-1  H4   0.020
 1OB  plan-2  N19  0.020
 1OB  plan-2  C20  0.020
 1OB  plan-2  C21  0.020
 1OB  plan-2  C22  0.020
 1OB  plan-2  C23  0.020
 1OB  plan-2  C24  0.020
 1OB  plan-2  C25  0.020
 1OB  plan-2  F26  0.020
 1OB  plan-2  H11  0.020
 1OB  plan-2  H12  0.020
 1OB  plan-2  H13  0.020
 1OB  plan-2  H14  0.020
 1OB  plan-3  C7   0.020
 1OB  plan-3  C8   0.020
 1OB  plan-3  C9   0.020
 1OB  plan-3  C10  0.020
 1OB  plan-3  N11  0.020
 1OB  plan-3  C12  0.020
 1OB  plan-3  N13  0.020
 1OB  plan-3  C14  0.020
 1OB  plan-3  C15  0.020
 1OB  plan-3  N16  0.020
 1OB  plan-3  C17  0.020
 1OB  plan-3  O27  0.020
 1OB  plan-3  H7   0.020
 1OB  plan-3  H9   0.020
 1OB  plan-4  C14  0.020
 1OB  plan-4  C17  0.020
 1OB  plan-4  O18  0.020
 1OB  plan-4  N19  0.020
 1OB  plan-4  C20  0.020
 1OB  plan-4  H10  0.020

