# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 14:25:20 2021
#   Inital geometry file: a 146 line input string
#   Ligand name: (~{E})-3-[4-chloranyl-2-[(5-methyl-1,2,3,4-tetrazol-2-yl)methyl]phenyl]-1-[(2~{R})-4-[(4-fluorophenyl)methyl]-2-methyl-piperazin-1-yl]prop-2-en-1-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@@H]1CN(CCN1C(=O)/C=C/c2ccc(Cl)cc2Cn3nnc(C)n3)Cc4ccc(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
 O9W  O9W  (~{E})-3-[4-chloranyl-2-[(5-methyl-1,2,3,4-tetrazol-2-yl)methyl]phenyl]-1-[(2~{R})-4-[(4-fluorophenyl)methyl]-2-methyl-piperazin-1-yl]prop-2-en-1-one  ligand  59  33  .  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_O9W
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
 O9W  C1   C   CR16  0  -0.219  -35.0331  17.5336  -11.0482
 O9W  C2   C   CR6   0  -0.038  -33.8168  17.0524  -10.6046
 O9W  C3   C   CR16  0  -0.202  -33.5816  16.8564   -9.2518
 O9W  C11  C   CH2   0  -0.268  -40.7392  21.6888   -8.0538
 O9W  C12  C   CH1   0  -0.142  -39.2669  21.4205   -7.7526
 O9W  C13  C   CH3   0  -0.650  -38.4613  22.7004   -7.5679
 O9W  C14  C   CH2   0  -0.408  -42.7285  22.7879   -7.1801
 O9W  C15  C   CR6   0   0.109  -43.7733  21.7964   -7.6415
 O9W  C16  C   CR16  0  -0.284  -43.9134  21.4738   -8.9897
 O9W  C17  C   CR6   0   0.512  -45.6349  19.9159   -8.4693
 O9W  C18  C   CR16  0  -0.401  -45.5368  20.2125   -7.1240
 O9W  C19  C   CR16  0  -0.401  -44.8406  20.5328   -9.4160
 O9W  C20  C   CR16  0  -0.281  -44.6012  21.1560   -6.7225
 O9W  C23  C   C1    0  -0.400  -37.4130  19.2172   -7.6182
 O9W  C29  C   CR5   0   0.402  -37.1289  21.6369  -11.5962
 O9W  C4   C   CR16  0  -0.293  -34.5825  17.1708   -8.3537
 O9W  C5   C   CR6   0   0.076  -35.8071  17.7051   -8.7669
 O9W  C6   C   C1    0  -0.267  -36.7723  18.0517   -7.7132
 O9W  N7   N   NT    0  -0.481  -39.1665  20.5435   -6.5854
 O9W  C8   C   CH2   0  -0.300  -39.9546  20.9596   -5.4346
 O9W  C9   C   CH2   0  -0.296  -41.3891  21.2634   -5.8263
 O9W  N10  N   NT    0  -0.401  -41.4138  22.2349   -6.8986
 O9W  O22  O   O     0  -0.506  -38.3172  18.7581   -5.4886
 O9W  F24  F   F     0  -0.318  -46.5378  19.0048   -8.8712
 O9W  CL1  CL  CL    0  -0.117  -32.5849  16.6595  -11.7535
 O9W  N27  N   NR5   0  -0.069  -37.2901  19.6117  -11.3264
 O9W  N28  N   N     0  -0.282  -37.1997  20.7255  -10.6450
 O9W  N30  N   N     0  -0.336  -37.1684  21.0621  -12.8102
 O9W  N31  N   N     0  -0.065  -37.2688  19.7869  -12.6135
 O9W  C33  C   CR6   0   0.093  -36.0355  17.8632  -10.1393
 O9W  H1   H   HCR6  0   0.283  -35.2142  17.6424  -12.1106
 O9W  H2   H   HCR6  0   0.288  -32.6376  16.4605   -8.9039
 O9W  H3   H   HCH2  0   0.244  -40.7951  22.4002   -8.8814
 O9W  H4   H   HCH2  0   0.216  -41.2019  20.7495   -8.3986
 O9W  H5   H   HCH1  0   0.262  -38.8855  20.8937   -8.6249
 O9W  H6   H   HCH3  0   0.235  -37.4086  22.4769   -7.3909
 O9W  H7   H   HCH3  0   0.231  -38.5261  23.3163   -8.4657
 O9W  H8   H   HCH3  0   0.235  -38.8307  23.2945   -6.7332
 O9W  H9   H   HCH2  0   0.255  -42.6028  23.5647   -7.9386
 O9W  H10  H   HCH2  0   0.254  -43.0798  23.2857   -6.2725
 O9W  H11  H   HCR6  0   0.263  -43.2975  21.9707   -9.7297
 O9W  H12  H   HCR6  0   0.278  -46.1801  19.7228   -6.4046
 O9W  H13  H   HCR6  0   0.277  -44.9461  20.2898  -10.4653
 O9W  H14  H   HCR6  0   0.262  -44.5259  21.4013   -5.6699
 O9W  H15  H   H     0   0.305  -37.2187  19.9894   -8.3496
 O9W  H16  H   HCH2  0   0.312  -38.1486  18.3130   -9.9646
 O9W  H17  H   HCH2  0   0.322  -37.6685  17.6159  -11.5041
 O9W  H18  H   HCR6  0   0.274  -34.4037  17.0165   -7.2971
 O9W  H19  H   H     0   0.279  -36.9140  17.3049   -6.9381
 O9W  H20  H   HCH2  0   0.268  -39.9414  20.1704   -4.6888
 O9W  H21  H   HCH2  0   0.242  -39.5027  21.8482   -4.9824
 O9W  H22  H   HCH2  0   0.245  -41.9071  21.6661   -4.9530
 O9W  H23  H   HCH2  0   0.205  -41.8933  20.3236   -6.1041
 O9W  H25  H   HCH3  0   0.268  -36.7311  23.6084  -12.2670
 O9W  H26  H   HCH3  0   0.266  -38.0014  23.5021  -11.0513
 O9W  H27  H   HCH3  0   0.267  -36.3185  23.3190  -10.5714
 O9W  C26  C   CH2   0  -0.437  -37.3607  18.2975  -10.7131
 O9W  C32  C   CH3   0  -0.732  -37.0369  23.0963  -11.3580
 O9W  C21  C   C     0   0.564  -38.3346  19.4825   -6.4793

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
 O9W  N30  N31  aromatic  1.294  0.020  1.294
 O9W  N30  C29  aromatic  1.344  0.020  1.344
 O9W  N31  N27  aromatic  1.299  0.020  1.299
 O9W  CL1  C2   single    1.730  0.020  1.730
 O9W  C29  C32  single    1.482  0.020  1.482
 O9W  C29  N28  aromatic  1.319  0.020  1.319
 O9W  N27  N28  aromatic  1.309  0.020  1.309
 O9W  N27  C26  single    1.452  0.020  1.452
 O9W  C1   C2   aromatic  1.381  0.020  1.381
 O9W  C1   C33  aromatic  1.393  0.020  1.393
 O9W  C2   C3   aromatic  1.387  0.020  1.387
 O9W  C26  C33  single    1.508  0.020  1.508
 O9W  F24  C17  single    1.344  0.020  1.344
 O9W  C19  C17  aromatic  1.381  0.020  1.381
 O9W  C19  C16  aromatic  1.388  0.020  1.388
 O9W  C33  C5   aromatic  1.400  0.020  1.400
 O9W  C17  C18  aromatic  1.381  0.020  1.381
 O9W  C3   C4   aromatic  1.381  0.020  1.381
 O9W  C16  C15  aromatic  1.393  0.020  1.393
 O9W  C5   C4   aromatic  1.399  0.020  1.399
 O9W  C5   C6   single    1.470  0.020  1.470
 O9W  C18  C20  aromatic  1.388  0.020  1.388
 O9W  C15  C20  aromatic  1.393  0.020  1.393
 O9W  C15  C14  single    1.513  0.020  1.513
 O9W  C11  C12  single    1.527  0.020  1.527
 O9W  C11  N10  single    1.445  0.020  1.445
 O9W  C6   C23  double    1.333  0.020  1.333
 O9W  C23  C21  single    1.489  0.020  1.489
 O9W  C12  C13  single    1.524  0.020  1.524
 O9W  C12  N7   single    1.463  0.020  1.463
 O9W  C14  N10  single    1.454  0.020  1.454
 O9W  N10  C9   single    1.447  0.020  1.447
 O9W  C21  N7   single    1.352  0.020  1.352
 O9W  C21  O22  double    1.227  0.020  1.227
 O9W  N7   C8   single    1.456  0.020  1.456
 O9W  C9   C8   single    1.518  0.020  1.518
 O9W  C1   H1   single    0.930  0.020  1.080
 O9W  C3   H2   single    0.930  0.020  1.080
 O9W  C11  H3   single    0.970  0.020  1.090
 O9W  C11  H4   single    0.970  0.020  1.090
 O9W  C12  H5   single    0.970  0.020  1.090
 O9W  C13  H6   single    0.970  0.020  1.090
 O9W  C13  H7   single    0.970  0.020  1.090
 O9W  C13  H8   single    0.970  0.020  1.090
 O9W  C14  H9   single    0.970  0.020  1.090
 O9W  C14  H10  single    0.970  0.020  1.090
 O9W  C16  H11  single    0.930  0.020  1.080
 O9W  C18  H12  single    0.930  0.020  1.080
 O9W  C19  H13  single    0.930  0.020  1.080
 O9W  C20  H14  single    0.930  0.020  1.080
 O9W  C23  H15  single    0.930  0.020  1.080
 O9W  C26  H16  single    0.970  0.020  1.090
 O9W  C26  H17  single    0.970  0.020  1.090
 O9W  C4   H18  single    0.930  0.020  1.080
 O9W  C6   H19  single    0.930  0.020  1.080
 O9W  C8   H20  single    0.970  0.020  1.090
 O9W  C8   H21  single    0.970  0.020  1.090
 O9W  C9   H22  single    0.970  0.020  1.090
 O9W  C9   H23  single    0.970  0.020  1.090
 O9W  C32  H25  single    0.970  0.020  1.090
 O9W  C32  H26  single    0.970  0.020  1.090
 O9W  C32  H27  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
 O9W  H1   C1   C33  119.74  3.000
 O9W  H1   C1   C2   119.82  3.000
 O9W  C33  C1   C2   120.44  3.000
 O9W  CL1  C2   C3   119.67  3.000
 O9W  C3   C2   C1   120.78  3.000
 O9W  CL1  C2   C1   119.54  3.000
 O9W  H2   C3   C4   120.46  3.000
 O9W  H2   C3   C2   120.91  3.000
 O9W  C4   C3   C2   118.63  3.000
 O9W  H4   C11  H3   107.24  3.000
 O9W  H4   C11  N10  112.09  3.000
 O9W  H3   C11  N10  109.61  3.000
 O9W  H4   C11  C12  108.46  3.000
 O9W  H3   C11  C12  108.25  3.000
 O9W  N10  C11  C12  111.04  3.000
 O9W  H5   C12  N7   108.98  3.000
 O9W  H5   C12  C13  108.58  3.000
 O9W  N7   C12  C13  111.74  3.000
 O9W  H5   C12  C11  105.37  3.000
 O9W  N7   C12  C11  109.20  3.000
 O9W  C13  C12  C11  112.71  3.000
 O9W  H8   C13  H7   107.62  3.000
 O9W  H8   C13  H6   108.35  3.000
 O9W  H7   C13  H6   107.85  3.000
 O9W  H8   C13  C12  111.83  3.000
 O9W  H7   C13  C12  110.07  3.000
 O9W  H6   C13  C12  110.97  3.000
 O9W  H10  C14  H9   106.83  3.000
 O9W  H10  C14  N10  107.64  3.000
 O9W  H9   C14  N10  107.50  3.000
 O9W  H10  C14  C15  109.25  3.000
 O9W  H9   C14  C15  109.49  3.000
 O9W  N10  C14  C15  115.75  3.000
 O9W  C20  C15  C16  118.18  3.000
 O9W  C20  C15  C14  120.71  3.000
 O9W  C16  C15  C14  121.09  3.000
 O9W  H11  C16  C19  118.74  3.000
 O9W  H11  C16  C15  119.84  3.000
 O9W  C19  C16  C15  121.42  3.000
 O9W  F24  C17  C19  118.95  3.000
 O9W  C19  C17  C18  122.07  3.000
 O9W  F24  C17  C18  118.98  3.000
 O9W  H12  C18  C20  121.06  3.000
 O9W  H12  C18  C17  120.54  3.000
 O9W  C20  C18  C17  118.40  3.000
 O9W  H13  C19  C17  120.55  3.000
 O9W  H13  C19  C16  121.00  3.000
 O9W  C17  C19  C16  118.45  3.000
 O9W  H14  C20  C18  118.80  3.000
 O9W  H14  C20  C15  119.71  3.000
 O9W  C18  C20  C15  121.49  3.000
 O9W  H15  C23  C6   119.32  3.000
 O9W  H15  C23  C21  120.09  3.000
 O9W  C6   C23  C21  120.51  3.000
 O9W  C32  C29  N30  124.64  3.000
 O9W  C32  C29  N28  124.60  3.000
 O9W  N30  C29  N28  110.75  3.000
 O9W  H18  C4   C5   119.17  3.000
 O9W  H18  C4   C3   118.85  3.000
 O9W  C5   C4   C3   121.97  3.000
 O9W  C33  C5   C6   124.66  3.000
 O9W  C6   C5   C4   116.94  3.000
 O9W  C33  C5   C4   118.40  3.000
 O9W  H19  C6   C5   115.79  3.000
 O9W  H19  C6   C23  119.19  3.000
 O9W  C5   C6   C23  124.93  3.000
 O9W  C8   N7   C21  119.69  3.000
 O9W  C8   N7   C12  114.97  3.000
 O9W  C21  N7   C12  125.09  3.000
 O9W  H21  C8   H20  107.53  3.000
 O9W  H21  C8   C9   109.53  3.000
 O9W  H20  C8   C9   109.53  3.000
 O9W  H21  C8   N7   109.58  3.000
 O9W  H20  C8   N7   109.18  3.000
 O9W  C9   C8   N7   111.40  3.000
 O9W  H23  C9   H22  107.39  3.000
 O9W  H23  C9   N10  112.21  3.000
 O9W  H22  C9   N10  109.68  3.000
 O9W  H23  C9   C8   109.07  3.000
 O9W  H22  C9   C8   108.40  3.000
 O9W  N10  C9   C8   109.99  3.000
 O9W  C9   N10  C14  114.48  3.000
 O9W  C9   N10  C11  109.31  3.000
 O9W  C14  N10  C11  114.28  3.000
 O9W  N31  N27  N28  113.57  3.000
 O9W  N28  N27  C26  123.62  3.000
 O9W  N31  N27  C26  122.78  3.000
 O9W  N27  N28  C29  102.48  3.000
 O9W  N31  N30  C29  106.65  3.000
 O9W  N30  N31  N27  106.54  3.000
 O9W  C5   C33  C26  123.28  3.000
 O9W  C5   C33  C1   119.71  3.000
 O9W  C26  C33  C1   116.89  3.000
 O9W  H17  C26  H16  107.72  3.000
 O9W  H17  C26  C33  110.15  3.000
 O9W  H16  C26  C33  112.28  3.000
 O9W  H17  C26  N27  105.87  3.000
 O9W  H16  C26  N27  108.26  3.000
 O9W  C33  C26  N27  112.25  3.000
 O9W  H27  C32  H26  107.72  3.000
 O9W  H27  C32  H25  108.80  3.000
 O9W  H26  C32  H25  107.98  3.000
 O9W  H27  C32  C29  111.03  3.000
 O9W  H26  C32  C29  110.91  3.000
 O9W  H25  C32  C29  110.31  3.000
 O9W  O22  C21  N7   122.35  3.000
 O9W  O22  C21  C23  120.23  3.000
 O9W  N7   C21  C23  117.42  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
 O9W  CONST_01  C4   C3   C2   C1      0.00   0.0  0
 O9W  CONST_02  C4   C5   C33  C1      0.00   0.0  0
 O9W  CONST_03  C5   C33  C1   C2      0.00   0.0  0
 O9W  CONST_04  C5   C4   C3   C2      0.00   0.0  0
 O9W  CONST_05  C33  C1   C2   C3      0.00   0.0  0
 O9W  CONST_06  C33  C5   C4   C3      0.00   0.0  0
 O9W  CONST_07  C17  C19  C16  C15     0.00   0.0  0
 O9W  CONST_08  C17  C18  C20  C15     0.00   0.0  0
 O9W  CONST_09  C18  C17  C19  C16     0.00   0.0  0
 O9W  CONST_10  C18  C20  C15  C16     0.00   0.0  0
 O9W  CONST_11  C20  C18  C17  C19     0.00   0.0  0
 O9W  CONST_12  C20  C15  C16  C19     0.00   0.0  0
 O9W  CONST_13  N27  N31  N30  C29     0.00   0.0  0
 O9W  CONST_14  N31  N27  N28  C29     0.00   0.0  0
 O9W  CONST_15  N30  C29  N28  N27     0.00   0.0  0
 O9W  CONST_16  N31  N30  C29  N28     0.00   0.0  0
 O9W  CONST_17  N30  N31  N27  N28     0.00   0.0  0
 O9W  CONST_18  C6   C5   C33  C1    180.00   0.0  0
 O9W  CONST_19  C26  C33  C1   C2    180.00   0.0  0
 O9W  CONST_20  C6   C5   C4   C3    180.00   0.0  0
 O9W  CONST_21  C19  C16  C15  C14   180.00   0.0  0
 O9W  CONST_22  C18  C20  C15  C14   180.00   0.0  0
 O9W  CONST_23  F24  C17  C19  C16   180.00   0.0  0
 O9W  CONST_24  F24  C17  C18  C20   180.00   0.0  0
 O9W  CONST_25  N30  N31  N27  C26   180.00   0.0  0
 O9W  CONST_26  C29  N28  N27  C26   180.00   0.0  0
 O9W  CONST_27  C4   C5   C33  C26   180.00   0.0  0
 O9W  CONST_28  CL1  C2   C3   C4    180.00   0.0  0
 O9W  CONST_29  C33  C1   C2   CL1   180.00   0.0  0
 O9W  CONST_30  C32  C29  N28  N27   180.00   0.0  0
 O9W  CONST_31  C32  C29  N30  N31   180.00   0.0  0
 O9W  CONST_32  H2   C3   C2   C1    180.00   0.0  0
 O9W  CONST_33  H18  C4   C3   C2    180.00   0.0  0
 O9W  CONST_34  H1   C1   C2   C3    180.00   0.0  0
 O9W  CONST_35  H13  C19  C16  C15   180.00   0.0  0
 O9W  CONST_36  H12  C18  C20  C15   180.00   0.0  0
 O9W  CONST_37  H14  C20  C15  C16   180.00   0.0  0
 O9W  CONST_38  H11  C16  C19  C17   180.00   0.0  0
 O9W  CONST_39  C23  C21  N7   C12     0.00   0.0  0
 O9W  CONST_40  O22  C21  N7   C12   180.00   0.0  0
 O9W  CONST_41  C8   N7   C21  C23   180.00   0.0  0
 O9W  CONST_42  O22  C21  N7   C8      0.00   0.0  0
 O9W  Var_01    C8   C9   N10  C11    61.47  30.0  1
 O9W  Var_02    C9   N10  C11  C12   -63.03  30.0  1
 O9W  Var_03    C9   C8   N7   C12    49.80  30.0  1
 O9W  Var_04    N10  C9   C8   N7    -54.40  30.0  1
 O9W  Var_05    N27  C26  C33  C1    -71.07  30.0  2
 O9W  Var_06    C15  C14  N10  C11    64.94  30.0  2
 O9W  Var_07    N10  C14  C15  C16   -87.47  30.0  2
 O9W  Var_08    C33  C26  N27  N28   -73.15  30.0  2
 O9W  Var_09    C33  C5   C6   C23   -50.08  30.0  2
 O9W  Var_10    H25  C32  C29  N28   165.17  30.0  2
 O9W  Var_11    C5   C6   C23  C21  -177.73   0.0  2
 O9W  Var_12    N7   C21  C23  C6   -165.96  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
 O9W  chir_01  C12  C11  C13  N7  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
 O9W  plan-1  C29  0.020
 O9W  plan-1  N27  0.020
 O9W  plan-1  N28  0.020
 O9W  plan-1  N30  0.020
 O9W  plan-1  N31  0.020
 O9W  plan-1  C26  0.020
 O9W  plan-1  C32  0.020
 O9W  plan-2  C1   0.020
 O9W  plan-2  C2   0.020
 O9W  plan-2  C3   0.020
 O9W  plan-2  C4   0.020
 O9W  plan-2  C5   0.020
 O9W  plan-2  C6   0.020
 O9W  plan-2  CL1  0.020
 O9W  plan-2  C33  0.020
 O9W  plan-2  H1   0.020
 O9W  plan-2  H2   0.020
 O9W  plan-2  H18  0.020
 O9W  plan-2  C26  0.020
 O9W  plan-3  C14  0.020
 O9W  plan-3  C15  0.020
 O9W  plan-3  C16  0.020
 O9W  plan-3  C17  0.020
 O9W  plan-3  C18  0.020
 O9W  plan-3  C19  0.020
 O9W  plan-3  C20  0.020
 O9W  plan-3  F24  0.020
 O9W  plan-3  H11  0.020
 O9W  plan-3  H12  0.020
 O9W  plan-3  H13  0.020
 O9W  plan-3  H14  0.020
 O9W  plan-4  C12  0.020
 O9W  plan-4  C23  0.020
 O9W  plan-4  N7   0.020
 O9W  plan-4  C8   0.020
 O9W  plan-4  O22  0.020
 O9W  plan-4  C21  0.020
 O9W  plan-5  C23  0.020
 O9W  plan-5  C5   0.020
 O9W  plan-5  C6   0.020
 O9W  plan-5  H15  0.020
 O9W  plan-5  H19  0.020
 O9W  plan-5  C21  0.020

