# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Mar 23 09:58:17 2020
#   Inital geometry file: a 109 line input string
#   Ligand name: N-(4-fluorophenyl)-7-hydroxy-5-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1cc(nc2n1ncc2C(=O)Nc3ccc(F)cc3)C4CCNCC4
#
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
 1OA  1OA  N-(4-fluorophenyl)-7-hydroxy-5-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide  ligand  44  26  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_1OA
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
 1OA  C1   C  CR16  0  -0.303  -4.0211   1.0418  -0.0950
 1OA  C2   C  CR16  0  -0.400  -5.3071   1.5670  -0.0885
 1OA  C3   C  CR6   0   0.506  -6.3910   0.7268  -0.2277
 1OA  C4   C  CR16  0  -0.395  -6.2282  -0.6365  -0.3776
 1OA  C5   C  CR16  0  -0.346  -4.9469  -1.1577  -0.3795
 1OA  C6   C  CR6   0   0.380  -3.8263  -0.3335  -0.2384
 1OA  N7   N  NH1   0  -0.773  -2.5811  -0.9664  -0.2573
 1OA  C8   C  C     0   0.507  -1.3470  -0.4445  -0.0029
 1OA  O9   O  O     0  -0.462  -1.1526   0.7405   0.2151
 1OA  C10  C  CR5   0  -0.393  -0.2605  -1.4241  -0.0076
 1OA  C11  C  CR15  0  -0.030  -0.3023  -2.8292  -0.0751
 1OA  N12  N  N     0  -0.286   0.8841  -3.3919  -0.0294
 1OA  N13  N  N     0  -0.426   1.7332  -2.3559   0.0684
 1OA  C14  C  CR56  0   0.630   1.1040  -1.1265   0.0896
 1OA  N15  N  N     0  -0.444   1.7850   0.0120   0.1785
 1OA  C16  C  CR6   0   0.314   3.0961  -0.0679   0.2582
 1OA  C17  C  CR16  0  -0.505   3.7907  -1.2933   0.2488
 1OA  C18  C  CR6   0   0.651   3.0798  -2.4602   0.1471
 1OA  O19  O  OH1   0  -0.563   3.5440  -3.6860   0.1185
 1OA  C20  C  CH1   0  -0.338   3.8762   1.2145   0.3081
 1OA  C21  C  CH2   0  -0.426   4.0838   1.7511  -1.1166
 1OA  C22  C  CH2   0  -0.318   4.8491   3.0723  -1.0812
 1OA  N23  N  NH1   0  -0.574   4.2486   4.0819  -0.2253
 1OA  C24  C  CH2   0  -0.321   4.0307   3.5802   1.1223
 1OA  C25  C  CH2   0  -0.422   3.2211   2.2867   1.1789
 1OA  F26  F  F     0  -0.319  -7.6333   1.2420  -0.2198
 1OA  H1   H  HCR6  0   0.289  -3.1865   1.7140   0.0079
 1OA  H2   H  HCR6  0   0.281  -5.4520   2.6338   0.0219
 1OA  H3   H  HCR6  0   0.283  -7.0841  -1.2888  -0.4882
 1OA  H4   H  HCR6  0   0.280  -4.8184  -2.2278  -0.4899
 1OA  H5   H  HNH1  0   0.418  -2.6284  -1.9527  -0.4571
 1OA  H6   H  HCR5  0   0.279  -1.1691  -3.4704  -0.1478
 1OA  H7   H  HCR6  0   0.302   4.8695  -1.3213   0.3179
 1OA  H9   H  HCH1  0   0.248   4.8654   0.9895   0.7242
 1OA  H10  H  HCH2  0   0.238   4.6271   1.0218  -1.7237
 1OA  H11  H  HCH2  0   0.226   3.1081   1.9018  -1.5907
 1OA  H12  H  HCH2  0   0.217   5.8682   2.8863  -0.7242
 1OA  H13  H  HCH2  0   0.239   4.9423   3.4762  -2.0914
 1OA  H14  H  HNH1  0   0.338   3.3556   4.3543  -0.6211
 1OA  H16  H  HCH2  0   0.215   5.0103   3.4147   1.5847
 1OA  H17  H  HCH2  0   0.237   3.5373   4.3565   1.7106
 1OA  H18  H  HCH2  0   0.228   2.2031   2.4738   0.8274
 1OA  H19  H  HCH2  0   0.232   3.1437   1.9393   2.2127
 1OA  H8   H  HOH1  0   0.508   4.5096  -3.6887   0.1713

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
 1OA  N12  C11  aromatic  1.314  0.020  1.314
 1OA  N12  N13  aromatic  1.343  0.020  1.343
 1OA  C11  C10  aromatic  1.407  0.020  1.407
 1OA  O19  C18  single    1.311  0.020  1.311
 1OA  N13  C18  aromatic  1.353  0.020  1.353
 1OA  N13  C14  aromatic  1.381  0.020  1.381
 1OA  C18  C17  aromatic  1.370  0.020  1.370
 1OA  C10  C14  aromatic  1.400  0.020  1.400
 1OA  C10  C8   single    1.463  0.020  1.463
 1OA  O9   C8   double    1.220  0.020  1.220
 1OA  C14  N15  aromatic  1.330  0.020  1.330
 1OA  C8   N7   single    1.364  0.020  1.364
 1OA  C17  C16  aromatic  1.409  0.020  1.409
 1OA  N15  C16  aromatic  1.316  0.020  1.316
 1OA  N7   C6   single    1.397  0.020  1.397
 1OA  C16  C20  single    1.502  0.020  1.502
 1OA  C5   C6   aromatic  1.398  0.020  1.398
 1OA  C5   C4   aromatic  1.383  0.020  1.383
 1OA  C6   C1   aromatic  1.396  0.020  1.396
 1OA  C20  C25  single    1.529  0.020  1.529
 1OA  C20  C21  single    1.537  0.020  1.537
 1OA  C25  C24  single    1.527  0.020  1.527
 1OA  C4   C3   aromatic  1.381  0.020  1.381
 1OA  C1   C2   aromatic  1.389  0.020  1.389
 1OA  C21  C22  single    1.527  0.020  1.527
 1OA  C3   C2   aromatic  1.378  0.020  1.378
 1OA  C3   F26  single    1.345  0.020  1.345
 1OA  C24  N23  single    1.454  0.020  1.454
 1OA  C22  N23  single    1.453  0.020  1.453
 1OA  C1   H1   single    0.930  0.020  1.080
 1OA  C2   H2   single    0.930  0.020  1.080
 1OA  C4   H3   single    0.930  0.020  1.080
 1OA  C5   H4   single    0.930  0.020  1.080
 1OA  N7   H5   single    0.860  0.020  1.020
 1OA  C11  H6   single    0.930  0.020  1.080
 1OA  C17  H7   single    0.930  0.020  1.080
 1OA  C20  H9   single    0.970  0.020  1.090
 1OA  C21  H10  single    0.970  0.020  1.090
 1OA  C21  H11  single    0.970  0.020  1.090
 1OA  C22  H12  single    0.970  0.020  1.090
 1OA  C22  H13  single    0.970  0.020  1.090
 1OA  N23  H14  single    0.890  0.020  1.040
 1OA  C24  H16  single    0.970  0.020  1.090
 1OA  C24  H17  single    0.970  0.020  1.090
 1OA  C25  H18  single    0.970  0.020  1.090
 1OA  C25  H19  single    0.970  0.020  1.090
 1OA  O19  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
 1OA  H1   C1   C6   121.10  3.000
 1OA  H1   C1   C2   118.77  3.000
 1OA  C6   C1   C2   120.13  3.000
 1OA  H2   C2   C3   120.39  3.000
 1OA  H2   C2   C1   119.81  3.000
 1OA  C3   C2   C1   119.81  3.000
 1OA  F26  C3   C4   119.19  3.000
 1OA  F26  C3   C2   119.49  3.000
 1OA  C4   C3   C2   121.32  3.000
 1OA  H3   C4   C5   120.36  3.000
 1OA  H3   C4   C3   120.87  3.000
 1OA  C5   C4   C3   118.77  3.000
 1OA  H4   C5   C6   119.83  3.000
 1OA  H4   C5   C4   118.83  3.000
 1OA  C6   C5   C4   121.35  3.000
 1OA  N7   C6   C5   116.49  3.000
 1OA  C5   C6   C1   118.63  3.000
 1OA  N7   C6   C1   124.88  3.000
 1OA  H5   N7   C8   117.01  3.000
 1OA  H5   N7   C6   113.85  3.000
 1OA  C8   N7   C6   129.10  3.000
 1OA  C10  C8   O9   122.17  3.000
 1OA  O9   C8   N7   123.30  3.000
 1OA  C10  C8   N7   114.53  3.000
 1OA  C14  C10  C11  104.15  3.000
 1OA  C14  C10  C8   125.54  3.000
 1OA  C11  C10  C8   130.29  3.000
 1OA  H6   C11  N12  118.20  3.000
 1OA  H6   C11  C10  128.27  3.000
 1OA  N12  C11  C10  113.52  3.000
 1OA  N13  N12  C11  104.07  3.000
 1OA  C18  N13  C14  121.41  3.000
 1OA  C14  N13  N12  113.56  3.000
 1OA  C18  N13  N12  125.03  3.000
 1OA  N15  C14  N13  122.00  3.000
 1OA  N15  C14  C10  133.30  3.000
 1OA  N13  C14  C10  104.70  3.000
 1OA  C16  N15  C14  117.54  3.000
 1OA  C20  C16  C17  119.13  3.000
 1OA  C20  C16  N15  117.89  3.000
 1OA  C17  C16  N15  122.94  3.000
 1OA  H7   C17  C18  120.02  3.000
 1OA  H7   C17  C16  120.93  3.000
 1OA  C18  C17  C16  119.05  3.000
 1OA  O19  C18  C17  127.90  3.000
 1OA  C17  C18  N13  117.07  3.000
 1OA  O19  C18  N13  115.04  3.000
 1OA  H8   O19  C18  110.79  3.000
 1OA  H9   C20  C25  108.32  3.000
 1OA  H9   C20  C21  107.56  3.000
 1OA  C25  C20  C21  109.94  3.000
 1OA  H9   C20  C16  107.82  3.000
 1OA  C21  C20  C16  109.72  3.000
 1OA  C25  C20  C16  113.28  3.000
 1OA  H11  C21  H10  107.11  3.000
 1OA  H11  C21  C22  109.72  3.000
 1OA  H10  C21  C22  109.93  3.000
 1OA  H11  C21  C20  109.21  3.000
 1OA  H10  C21  C20  110.43  3.000
 1OA  C22  C21  C20  110.38  3.000
 1OA  H13  C22  H12  106.55  3.000
 1OA  H13  C22  N23  108.85  3.000
 1OA  H12  C22  N23  108.07  3.000
 1OA  H13  C22  C21  109.96  3.000
 1OA  H12  C22  C21  109.07  3.000
 1OA  N23  C22  C21  114.05  3.000
 1OA  H14  N23  C24  108.81  3.000
 1OA  H14  N23  C22  108.69  3.000
 1OA  C24  N23  C22  111.59  3.000
 1OA  H17  C24  H16  106.50  3.000
 1OA  H17  C24  C25  110.04  3.000
 1OA  H16  C24  C25  109.29  3.000
 1OA  H17  C24  N23  108.77  3.000
 1OA  H16  C24  N23  108.01  3.000
 1OA  C25  C24  N23  113.95  3.000
 1OA  H19  C25  H18  107.01  3.000
 1OA  H19  C25  C24  109.98  3.000
 1OA  H18  C25  C24  109.69  3.000
 1OA  H19  C25  C20  110.25  3.000
 1OA  H18  C25  C20  109.63  3.000
 1OA  C24  C25  C20  110.23  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
 1OA  CONST_01  C4   C5   C6   C1     0.00   0.0  0
 1OA  CONST_02  C4   C3   C2   C1     0.00   0.0  0
 1OA  CONST_03  C5   C6   C1   C2     0.00   0.0  0
 1OA  CONST_04  C5   C4   C3   C2     0.00   0.0  0
 1OA  CONST_05  C6   C5   C4   C3     0.00   0.0  0
 1OA  CONST_06  C6   C1   C2   C3     0.00   0.0  0
 1OA  CONST_07  N13  N12  C11  C10    0.00   0.0  0
 1OA  CONST_08  N12  N13  C14  C10    0.00   0.0  0
 1OA  CONST_09  C18  N13  C14  C10  180.00   0.0  0
 1OA  CONST_10  C16  N15  C14  C10  180.00   0.0  0
 1OA  CONST_11  C18  N13  N12  C11  180.00   0.0  0
 1OA  CONST_12  C14  N13  N12  C11    0.00   0.0  0
 1OA  CONST_13  N13  C14  C10  C11    0.00   0.0  0
 1OA  CONST_14  N15  C14  C10  C11  180.00   0.0  0
 1OA  CONST_15  C14  C10  C11  N12    0.00   0.0  0
 1OA  CONST_16  C17  C18  N13  N12  180.00   0.0  0
 1OA  CONST_17  N15  C14  N13  N12  180.00   0.0  0
 1OA  CONST_18  C16  C17  C18  N13    0.00   0.0  0
 1OA  CONST_19  C16  N15  C14  N13    0.00   0.0  0
 1OA  CONST_20  C17  C18  N13  C14    0.00   0.0  0
 1OA  CONST_21  C17  C16  N15  C14    0.00   0.0  0
 1OA  CONST_22  C18  N13  C14  N15    0.00   0.0  0
 1OA  CONST_23  C18  C17  C16  N15    0.00   0.0  0
 1OA  CONST_24  C20  C16  N15  C14  180.00   0.0  0
 1OA  CONST_25  C20  C16  C17  C18  180.00   0.0  0
 1OA  CONST_26  F26  C3   C2   C1   180.00   0.0  0
 1OA  CONST_27  N7   C6   C1   C2   180.00   0.0  0
 1OA  CONST_28  N7   C6   C5   C4   180.00   0.0  0
 1OA  CONST_29  F26  C3   C4   C5   180.00   0.0  0
 1OA  CONST_30  N12  C11  C10  C8   180.00   0.0  0
 1OA  CONST_31  N13  C14  C10  C8   180.00   0.0  0
 1OA  CONST_32  N15  C14  C10  C8     0.00   0.0  0
 1OA  CONST_33  O19  C18  N13  N12    0.00   0.0  0
 1OA  CONST_34  O19  C18  N13  C14  180.00   0.0  0
 1OA  CONST_35  O19  C18  C17  C16  180.00   0.0  0
 1OA  CONST_36  H4   C5   C6   C1   180.00   0.0  0
 1OA  CONST_37  H3   C4   C3   C2   180.00   0.0  0
 1OA  CONST_38  H1   C1   C2   C3   180.00   0.0  0
 1OA  CONST_39  H2   C2   C3   C4   180.00   0.0  0
 1OA  CONST_40  H6   C11  N12  N13  180.00   0.0  0
 1OA  CONST_41  H7   C17  C18  N13  180.00   0.0  0
 1OA  CONST_42  C10  C8   N7   C6   180.00   0.0  0
 1OA  CONST_43  C8   N7   C6   C1     0.00   0.0  0
 1OA  CONST_44  C8   N7   C6   C5   180.00   0.0  0
 1OA  CONST_45  H5   N7   C6   C1   180.00   0.0  0
 1OA  CONST_46  O9   C8   N7   C6     0.00   0.0  0
 1OA  Var_01    N23  C24  C25  C20   55.12  30.0  1
 1OA  Var_02    N23  C22  C21  C20  -54.16  30.0  1
 1OA  Var_03    C24  N23  C22  C21   53.76  30.0  1
 1OA  Var_04    C25  C24  N23  C22  -54.21  30.0  1
 1OA  Var_05    C11  C10  C8   N7    -8.47  30.0  2

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 1OA  chir_01  C20  C16  C25  C21  positiv

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
 1OA  plan-1  C1   0.020
 1OA  plan-1  C2   0.020
 1OA  plan-1  C3   0.020
 1OA  plan-1  C4   0.020
 1OA  plan-1  C5   0.020
 1OA  plan-1  C6   0.020
 1OA  plan-1  N7   0.020
 1OA  plan-1  F26  0.020
 1OA  plan-1  H1   0.020
 1OA  plan-1  H2   0.020
 1OA  plan-1  H3   0.020
 1OA  plan-1  H4   0.020
 1OA  plan-2  C8   0.020
 1OA  plan-2  C10  0.020
 1OA  plan-2  C11  0.020
 1OA  plan-2  N12  0.020
 1OA  plan-2  N13  0.020
 1OA  plan-2  C14  0.020
 1OA  plan-2  N15  0.020
 1OA  plan-2  C16  0.020
 1OA  plan-2  C17  0.020
 1OA  plan-2  C18  0.020
 1OA  plan-2  O19  0.020
 1OA  plan-2  C20  0.020
 1OA  plan-2  H6   0.020
 1OA  plan-2  H7   0.020
 1OA  plan-3  C6   0.020
 1OA  plan-3  N7   0.020
 1OA  plan-3  C8   0.020
 1OA  plan-3  O9   0.020
 1OA  plan-3  C10  0.020
 1OA  plan-3  H5   0.020

