# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 15:34:29 2021
#   Inital geometry file: a 125 line input string
#   Ligand name: 5-fluoranyl-2-[5-[[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]amino]-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]benzenecarbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CN1CCC(CC1)n2cc(Nc3ncc4nnn(c5ccc(F)cc5C#N)c4n3)cn2
#
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
 OXW  OXW  5-fluoranyl-2-[5-[[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]amino]-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]benzenecarbonitrile  ligand  50  31  .  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_OXW
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
 OXW  C1   C  CR6   0   0.619  25.3804   2.4875  -64.4625
 OXW  C3   C  CR16  0  -0.012  27.2237   1.2688  -65.0965
 OXW  N6   N  N     0  -0.489  25.5849   2.4130  -63.1513
 OXW  C9   C  CR6   0   0.366  26.7202   1.7999  -60.3687
 OXW  C10  C  CR6   0   0.025  26.5435   0.8319  -59.3774
 OXW  C11  C  CR16  0  -0.415  26.0654   1.1943  -58.1214
 OXW  C12  C  CR6   0   0.566  25.7490   2.5172  -57.8946
 OXW  C13  C  CR16  0  -0.407  25.9000   3.4867  -58.8682
 OXW  C14  C  CR16  0  -0.262  26.3971   3.1222  -60.1083
 OXW  C19  C  CR15  0  -0.100  22.2559   4.5240  -64.6633
 OXW  C22  C  CH1   0  -0.056  21.5372   5.0818  -61.2938
 OXW  C24  C  CH2   0  -0.284  19.7394   4.5996  -59.6361
 OXW  N25  N  NT    0  -0.407  20.7223   4.5615  -58.5701
 OXW  C27  C  CH2   0  -0.481  22.5371   5.0472  -60.1481
 OXW  C30  C  CSP   0   0.067  26.8128  -0.5457  -59.6349
 OXW  N2   N  N     0  -0.461  26.1562   1.9417  -65.4386
 OXW  C4   C  CR56  0   0.015  27.5439   1.1260  -63.7417
 OXW  C5   C  CR56  0   0.568  26.6707   1.7299  -62.8494
 OXW  N7   N  NR5   0  -0.531  27.1955   1.4371  -61.6386
 OXW  N8   N  N     0  -0.276  28.5363   0.5149  -63.0351
 OXW  N15  N  N     0  -0.061  28.3282   0.7043  -61.7991
 OXW  N16  N  NR5   0  -0.298  22.1430   4.7198  -62.5662
 OXW  C17  C  CR15  0   0.056  23.2473   3.9717  -62.7731
 OXW  C18  C  CR5   0   0.046  23.3588   3.8243  -64.1422
 OXW  N20  N  N     0  -0.270  21.5344   5.0536  -63.6931
 OXW  N21  N  NH1   0  -0.748  24.3094   3.1643  -64.9088
 OXW  C23  C  CH2   0  -0.432  20.3501   4.1835  -60.9653
 OXW  C26  C  CH2   0  -0.275  21.8411   5.4386  -58.8523
 OXW  C28  C  CH3   0  -0.519  20.1244   4.8673  -57.2903
 OXW  F29  F  F     0  -0.295  25.2835   2.8690  -56.6962
 OXW  N31  N  NS    0  -0.224  26.9969  -1.6675  -59.8149
 OXW  H1   H  HCR6  0   0.302  27.8308   0.8413  -65.8866
 OXW  H2   H  HCR6  0   0.318  25.9331   0.4526  -57.3460
 OXW  H3   H  HCR6  0   0.310  25.6544   4.5189  -58.6570
 OXW  H4   H  HCR6  0   0.312  26.5424   3.8765  -60.8690
 OXW  H5   H  HCR5  0   0.272  21.9804   4.6569  -65.6991
 OXW  H6   H  HCH1  0   0.258  21.1802   6.1093  -61.4117
 OXW  H7   H  HCH2  0   0.191  19.2951   5.6063  -59.7403
 OXW  H8   H  HCH2  0   0.243  18.9210   3.9220  -59.3833
 OXW  H10  H  HCH2  0   0.231  22.9465   4.0397  -60.0306
 OXW  H11  H  HCH2  0   0.257  23.3692   5.7294  -60.3358
 OXW  H12  H  HCR5  0   0.292  23.8632   3.6099  -61.9725
 OXW  H13  H  HNH1  0   0.417  24.1915   3.1903  -65.9098
 OXW  H14  H  HCH2  0   0.249  19.5960   4.2480  -61.7515
 OXW  H15  H  HCH2  0   0.230  20.6860   3.1442  -60.9095
 OXW  H16  H  HCH2  0   0.240  22.5556   5.3729  -58.0287
 OXW  H17  H  HCH2  0   0.194  21.5257   6.4958  -58.9122
 OXW  H18  H  HCH3  0   0.233  20.8677   4.7762  -56.4969
 OXW  H19  H  HCH3  0   0.192  19.7031   5.8837  -57.2402
 OXW  H20  H  HCH3  0   0.233  19.3187   4.1638  -57.0750

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
 OXW  N2   C3   aromatic  1.307  0.020  1.307
 OXW  N2   C1   aromatic  1.361  0.020  1.361
 OXW  C3   C4   aromatic  1.399  0.020  1.399
 OXW  N21  C1   single    1.343  0.020  1.343
 OXW  N21  C18  single    1.388  0.020  1.388
 OXW  C19  C18  aromatic  1.406  0.020  1.406
 OXW  C19  N20  aromatic  1.320  0.020  1.320
 OXW  C1   N6   aromatic  1.329  0.020  1.329
 OXW  C18  C17  aromatic  1.381  0.020  1.381
 OXW  C4   N8   aromatic  1.363  0.020  1.363
 OXW  C4   C5   aromatic  1.387  0.020  1.387
 OXW  N20  N16  aromatic  1.323  0.020  1.323
 OXW  N6   C5   aromatic  1.318  0.020  1.318
 OXW  N8   N15  aromatic  1.268  0.020  1.268
 OXW  C5   N7   aromatic  1.352  0.020  1.352
 OXW  C17  N16  aromatic  1.350  0.020  1.350
 OXW  N16  C22  single    1.455  0.020  1.455
 OXW  N15  N7   aromatic  1.359  0.020  1.359
 OXW  N7   C9   single    1.404  0.020  1.404
 OXW  C22  C23  single    1.525  0.020  1.525
 OXW  C22  C27  single    1.521  0.020  1.521
 OXW  C23  C24  single    1.521  0.020  1.521
 OXW  C9   C14  aromatic  1.386  0.020  1.386
 OXW  C9   C10  aromatic  1.397  0.020  1.397
 OXW  C14  C13  aromatic  1.385  0.020  1.385
 OXW  C27  C26  single    1.522  0.020  1.522
 OXW  C24  N25  single    1.450  0.020  1.450
 OXW  C10  C30  single    1.427  0.020  1.427
 OXW  C10  C11  aromatic  1.392  0.020  1.392
 OXW  C30  N31  triple    1.151  0.020  1.151
 OXW  C13  C12  aromatic  1.382  0.020  1.382
 OXW  C26  N25  single    1.449  0.020  1.449
 OXW  N25  C28  single    1.445  0.020  1.445
 OXW  C11  C12  aromatic  1.379  0.020  1.379
 OXW  C12  F29  single    1.333  0.020  1.333
 OXW  C3   H1   single    0.930  0.020  1.080
 OXW  C11  H2   single    0.930  0.020  1.080
 OXW  C13  H3   single    0.930  0.020  1.080
 OXW  C14  H4   single    0.930  0.020  1.080
 OXW  C19  H5   single    0.930  0.020  1.080
 OXW  C22  H6   single    0.970  0.020  1.090
 OXW  C24  H7   single    0.970  0.020  1.090
 OXW  C24  H8   single    0.970  0.020  1.090
 OXW  C27  H10  single    0.970  0.020  1.090
 OXW  C27  H11  single    0.970  0.020  1.090
 OXW  C17  H12  single    0.930  0.020  1.080
 OXW  N21  H13  single    0.860  0.020  1.020
 OXW  C23  H14  single    0.970  0.020  1.090
 OXW  C23  H15  single    0.970  0.020  1.090
 OXW  C26  H16  single    0.970  0.020  1.090
 OXW  C26  H17  single    0.970  0.020  1.090
 OXW  C28  H18  single    0.970  0.020  1.090
 OXW  C28  H19  single    0.970  0.020  1.090
 OXW  C28  H20  single    0.970  0.020  1.090

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
 OXW  N21  C1   N2   114.72  3.000
 OXW  N21  C1   N6   118.60  3.000
 OXW  N2   C1   N6   126.67  3.000
 OXW  H1   C3   C4   122.49  3.000
 OXW  H1   C3   N2   118.00  3.000
 OXW  C4   C3   N2   119.51  3.000
 OXW  C5   N6   C1   112.45  3.000
 OXW  N7   C9   C14  119.71  3.000
 OXW  C14  C9   C10  119.89  3.000
 OXW  N7   C9   C10  120.39  3.000
 OXW  C30  C10  C11  118.61  3.000
 OXW  C11  C10  C9   120.23  3.000
 OXW  C30  C10  C9   121.13  3.000
 OXW  H2   C11  C12  120.81  3.000
 OXW  H2   C11  C10  120.71  3.000
 OXW  C12  C11  C10  118.48  3.000
 OXW  F29  C12  C13  119.10  3.000
 OXW  F29  C12  C11  118.76  3.000
 OXW  C13  C12  C11  122.14  3.000
 OXW  H3   C13  C14  120.49  3.000
 OXW  H3   C13  C12  120.46  3.000
 OXW  C14  C13  C12  119.03  3.000
 OXW  H4   C14  C13  119.65  3.000
 OXW  H4   C14  C9   120.14  3.000
 OXW  C13  C14  C9   120.21  3.000
 OXW  H5   C19  N20  121.07  3.000
 OXW  H5   C19  C18  128.07  3.000
 OXW  N20  C19  C18  110.85  3.000
 OXW  H6   C22  C23  108.82  3.000
 OXW  H6   C22  N16  105.98  3.000
 OXW  C23  C22  N16  111.47  3.000
 OXW  H6   C22  C27  108.48  3.000
 OXW  C23  C22  C27  109.64  3.000
 OXW  N16  C22  C27  112.29  3.000
 OXW  H8   C24  H7   106.60  3.000
 OXW  H8   C24  C23  109.48  3.000
 OXW  H7   C24  C23  109.16  3.000
 OXW  H8   C24  N25  108.75  3.000
 OXW  H7   C24  N25  111.44  3.000
 OXW  C23  C24  N25  111.29  3.000
 OXW  C28  N25  C26  111.33  3.000
 OXW  C28  N25  C24  111.40  3.000
 OXW  C26  N25  C24  111.35  3.000
 OXW  H11  C27  H10  107.98  3.000
 OXW  H11  C27  C26  109.51  3.000
 OXW  H10  C27  C26  108.45  3.000
 OXW  H11  C27  C22  110.93  3.000
 OXW  H10  C27  C22  110.36  3.000
 OXW  C26  C27  C22  109.56  3.000
 OXW  N31  C30  C10  180.00  3.000
 OXW  C3   N2   C1   118.96  3.000
 OXW  N8   C4   C5   108.67  3.000
 OXW  C5   C4   C3   115.75  3.000
 OXW  N8   C4   C3   135.58  3.000
 OXW  N7   C5   C4   103.74  3.000
 OXW  N7   C5   N6   129.60  3.000
 OXW  C4   C5   N6   126.66  3.000
 OXW  N15  N7   C5   109.56  3.000
 OXW  N15  N7   C9   121.91  3.000
 OXW  C5   N7   C9   128.53  3.000
 OXW  N15  N8   C4   108.60  3.000
 OXW  N8   N15  N7   109.43  3.000
 OXW  N20  N16  C17  112.68  3.000
 OXW  C17  N16  C22  127.78  3.000
 OXW  N20  N16  C22  119.36  3.000
 OXW  H12  C17  C18  131.09  3.000
 OXW  H12  C17  N16  122.83  3.000
 OXW  C18  C17  N16  106.08  3.000
 OXW  N21  C18  C17  130.79  3.000
 OXW  C17  C18  C19  104.53  3.000
 OXW  N21  C18  C19  124.68  3.000
 OXW  N16  N20  C19  105.86  3.000
 OXW  H13  N21  C18  117.13  3.000
 OXW  H13  N21  C1   115.86  3.000
 OXW  C18  N21  C1   127.02  3.000
 OXW  H15  C23  H14  107.77  3.000
 OXW  H15  C23  C24  109.80  3.000
 OXW  H14  C23  C24  109.63  3.000
 OXW  H15  C23  C22  109.38  3.000
 OXW  H14  C23  C22  110.37  3.000
 OXW  C24  C23  C22  109.87  3.000
 OXW  H17  C26  H16  106.56  3.000
 OXW  H17  C26  C27  109.29  3.000
 OXW  H16  C26  C27  109.11  3.000
 OXW  H17  C26  N25  111.67  3.000
 OXW  H16  C26  N25  108.77  3.000
 OXW  C27  C26  N25  111.30  3.000
 OXW  H20  C28  H19  107.67  3.000
 OXW  H20  C28  H18  107.80  3.000
 OXW  H19  C28  H18  107.74  3.000
 OXW  H20  C28  N25  110.11  3.000
 OXW  H19  C28  N25  113.19  3.000
 OXW  H18  C28  N25  110.15  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
 OXW  CONST_01  C4   C3   N2   C1     0.00   0.0  0
 OXW  CONST_02  C4   C5   N6   C1     0.00   0.0  0
 OXW  CONST_03  N7   C5   N6   C1   180.00   0.0  0
 OXW  CONST_04  N6   C1   N2   C3     0.00   0.0  0
 OXW  CONST_05  N15  N8   C4   C3   180.00   0.0  0
 OXW  CONST_06  N6   C5   C4   C3     0.00   0.0  0
 OXW  CONST_07  N7   C5   C4   C3   180.00   0.0  0
 OXW  CONST_08  N8   C4   C5   N6   180.00   0.0  0
 OXW  CONST_09  N15  N7   C5   N6   180.00   0.0  0
 OXW  CONST_10  C9   N7   C5   N6     0.00   0.0  0
 OXW  CONST_11  C4   C5   N7   C9   180.00   0.0  0
 OXW  CONST_12  N8   N15  N7   C9   180.00   0.0  0
 OXW  CONST_13  C12  C13  C14  C9     0.00   0.0  0
 OXW  CONST_14  C12  C11  C10  C9     0.00   0.0  0
 OXW  CONST_17  C13  C14  C9   C10    0.00   0.0  0
 OXW  CONST_18  C13  C12  C11  C10    0.00   0.0  0
 OXW  CONST_19  N7   C9   C10  C11  180.00   0.0  0
 OXW  CONST_20  C14  C9   C10  C11    0.00   0.0  0
 OXW  CONST_21  C14  C13  C12  C11    0.00   0.0  0
 OXW  CONST_22  N7   C9   C14  C13  180.00   0.0  0
 OXW  CONST_25  N16  C17  C18  C19    0.00   0.0  0
 OXW  CONST_26  C17  N16  N20  C19    0.00   0.0  0
 OXW  CONST_27  N8   C4   C3   N2   180.00   0.0  0
 OXW  CONST_28  C5   C4   C3   N2     0.00   0.0  0
 OXW  CONST_29  C5   N6   C1   N2     0.00   0.0  0
 OXW  CONST_30  N7   N15  N8   C4     0.00   0.0  0
 OXW  CONST_31  N15  N7   C5   C4     0.00   0.0  0
 OXW  CONST_32  N15  N8   C4   C5     0.00   0.0  0
 OXW  CONST_33  N8   N15  N7   C5     0.00   0.0  0
 OXW  CONST_34  N8   C4   C5   N7     0.00   0.0  0
 OXW  CONST_35  C18  C19  N20  N16    0.00   0.0  0
 OXW  CONST_36  N20  C19  C18  C17    0.00   0.0  0
 OXW  CONST_37  N20  N16  C17  C18    0.00   0.0  0
 OXW  CONST_38  C22  N16  N20  C19  180.00   0.0  0
 OXW  CONST_39  C18  C17  N16  C22  180.00   0.0  0
 OXW  CONST_40  N21  C1   N2   C3   180.00   0.0  0
 OXW  CONST_41  F29  C12  C11  C10  180.00   0.0  0
 OXW  CONST_42  C30  C10  C11  C12  180.00   0.0  0
 OXW  CONST_43  C30  C10  C9   C14  180.00   0.0  0
 OXW  CONST_44  F29  C12  C13  C14  180.00   0.0  0
 OXW  CONST_45  N7   C9   C10  C30    0.00   0.0  0
 OXW  CONST_46  N21  C1   N6   C5   180.00   0.0  0
 OXW  CONST_47  N21  C18  C17  N16  180.00   0.0  0
 OXW  CONST_48  N21  C18  C19  N20  180.00   0.0  0
 OXW  CONST_49  H1   C3   N2   C1   180.00   0.0  0
 OXW  CONST_50  H3   C13  C14  C9   180.00   0.0  0
 OXW  CONST_51  H2   C11  C10  C9   180.00   0.0  0
 OXW  CONST_52  H4   C14  C9   C10  180.00   0.0  0
 OXW  CONST_53  H12  C17  C18  C19  180.00   0.0  0
 OXW  CONST_54  H5   C19  N20  N16  180.00   0.0  0
 OXW  Var_01    N25  C24  C23  C22  -57.01  30.0  1
 OXW  Var_02    N25  C26  C27  C22   57.74  30.0  1
 OXW  Var_03    C27  C26  N25  C24  -59.43  30.0  1
 OXW  Var_04    C26  N25  C24  C23   59.01  30.0  1
 OXW  Var_05    C19  C18  N21  C1   179.75  30.0  2
 OXW  Var_06    C18  N21  C1   N6     0.32  30.0  1
 OXW  Var_07    H18  C28  N25  C24  176.71  30.0  3

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
 OXW  chir_01  C22  N16  C23  C27  negativ

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
 OXW  plan-1  C19  0.020
 OXW  plan-1  C22  0.020
 OXW  plan-1  N16  0.020
 OXW  plan-1  C17  0.020
 OXW  plan-1  C18  0.020
 OXW  plan-1  N20  0.020
 OXW  plan-1  N21  0.020
 OXW  plan-1  H5   0.020
 OXW  plan-1  H12  0.020
 OXW  plan-2  C9   0.020
 OXW  plan-2  C10  0.020
 OXW  plan-2  C11  0.020
 OXW  plan-2  C12  0.020
 OXW  plan-2  C13  0.020
 OXW  plan-2  C14  0.020
 OXW  plan-2  C30  0.020
 OXW  plan-2  N7   0.020
 OXW  plan-2  F29  0.020
 OXW  plan-2  N31  0.020
 OXW  plan-2  H2   0.020
 OXW  plan-2  H3   0.020
 OXW  plan-2  H4   0.020
 OXW  plan-3  C1   0.020
 OXW  plan-3  C3   0.020
 OXW  plan-3  N6   0.020
 OXW  plan-3  C9   0.020
 OXW  plan-3  N2   0.020
 OXW  plan-3  C4   0.020
 OXW  plan-3  C5   0.020
 OXW  plan-3  N7   0.020
 OXW  plan-3  N8   0.020
 OXW  plan-3  N15  0.020
 OXW  plan-3  N21  0.020
 OXW  plan-3  H1   0.020

