# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May  4 06:26:36 2020
#   Inital geometry file: a 120 line input string
#   Ligand name: 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC1(CCN(CCCC(=O)c2ccc(F)cc2)CC1)c3ccc(Cl)cc3
#
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
 GMJ  GMJ  4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one  ligand  49  26  .  2021-08-10  2021-08-10  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_GMJ
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
 GMJ  C10  C   CH2   0  -0.443  -1.9876   0.1408   0.0708
 GMJ  C11  C   CH2   0  -0.247  -1.0658  -1.0656  -0.0528
 GMJ  C01  C   CR16  0  -0.276  -6.3379  -0.8010  -0.2546
 GMJ  C02  C   CR16  0  -0.395  -7.6874  -1.0756  -0.4062
 GMJ  C03  C   CR6   0   0.536  -8.5756  -0.0176  -0.4218
 GMJ  C04  C   CR16  0  -0.398  -8.1630   1.2964  -0.2880
 GMJ  C05  C   CR16  0  -0.244  -6.8125   1.5508  -0.1334
 GMJ  C06  C   CR6   0  -0.021  -5.8816   0.5097  -0.1163
 GMJ  C07  C   C     0   0.387  -4.4357   0.8339   0.0439
 GMJ  C09  C   CH2   0  -0.591  -3.4410  -0.2968  -0.0219
 GMJ  C13  C   CH2   0  -0.279   1.1171  -1.8763  -0.5786
 GMJ  C14  C   CH2   0  -0.435   2.5735  -1.5082  -0.8130
 GMJ  C15  C   CT    0   0.158   3.2126  -0.8806   0.4283
 GMJ  C16  C   CH2   0  -0.469   2.3169   0.2734   0.8956
 GMJ  C17  C   CH2   0  -0.281   0.8725  -0.1696   1.0773
 GMJ  C18  C   CR6   0   0.144   4.6152  -0.3849   0.1025
 GMJ  C19  C   CR16  0  -0.338   5.7388  -0.9224   0.7218
 GMJ  C20  C   CR16  0  -0.190   7.0178  -0.4742   0.4158
 GMJ  C21  C   CR6   0  -0.059   7.1785   0.5213  -0.5308
 GMJ  C22  C   CR16  0  -0.195   6.0796   1.0728  -1.1716
 GMJ  C23  C   CR16  0  -0.320   4.8119   0.6164  -0.8493
 GMJ  N12  N   NT    0  -0.427   0.3401  -0.7235  -0.1549
 GMJ  O08  O   O     0  -0.399  -4.0819   1.9820   0.2136
 GMJ  CL1  CL  CL    0  -0.136   8.7715   1.0838  -0.9259
 GMJ  H1   H   HCH2  0   0.235  -1.8231   0.6630   1.0149
 GMJ  H2   H   HCH2  0   0.229  -1.7571   0.8476  -0.7297
 GMJ  H3   H   HCH2  0   0.187  -1.2521  -1.7627   0.7839
 GMJ  H4   H   HCH2  0   0.225  -1.3365  -1.6068  -0.9643
 GMJ  H5   H   HCR6  0   0.278  -5.6465  -1.6318  -0.2448
 GMJ  H6   H   HCR6  0   0.289  -8.0399  -2.0926  -0.5127
 GMJ  H7   H   HCR6  0   0.288  -8.8845   2.1022  -0.3060
 GMJ  H8   H   HCR6  0   0.272  -6.4784   2.5739  -0.0281
 GMJ  H9   H   HCH2  0   0.270  -3.6092  -0.8494  -0.9528
 GMJ  H10  H   HCH2  0   0.275  -3.6742  -1.0105   0.7767
 GMJ  H11  H   HCH2  0   0.236   0.6972  -2.2513  -1.5153
 GMJ  H12  H   HCH2  0   0.194   1.0510  -2.7030   0.1479
 GMJ  H13  H   HCH2  0   0.244   3.1376  -2.3950  -1.1136
 GMJ  H14  H   HCH2  0   0.236   2.6317  -0.7962  -1.6395
 GMJ  H15  H   HCH2  0   0.246   2.6979   0.6851   1.8360
 GMJ  H16  H   HCH2  0   0.238   2.3461   1.0854   0.1656
 GMJ  H17  H   HCH2  0   0.191   0.7966  -0.8898   1.9104
 GMJ  H18  H   HCH2  0   0.243   0.2843   0.7024   1.3680
 GMJ  H19  H   HCR6  0   0.256   5.6364  -1.7097   1.4553
 GMJ  H20  H   HCR6  0   0.277   7.8760  -0.9049   0.9137
 GMJ  H21  H   HCR6  0   0.278   6.2053   1.8483  -1.9149
 GMJ  H22  H   HCR6  0   0.260   3.9674   1.0576  -1.3642
 GMJ  H24  H   HOH1  0   0.448   3.3749  -1.4846   2.2769
 GMJ  O25  O   OH1   0  -0.671   3.2491  -1.8920   1.4126
 GMJ  F26  F   F     0  -0.306  -9.8804  -0.2707  -0.5734

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
 GMJ  CL1  C21  single    1.735  0.020  1.735
 GMJ  C21  C20  aromatic  1.383  0.020  1.383
 GMJ  C21  C22  aromatic  1.386  0.020  1.386
 GMJ  C20  C19  aromatic  1.389  0.020  1.389
 GMJ  C22  C23  aromatic  1.385  0.020  1.385
 GMJ  C19  C18  aromatic  1.391  0.020  1.391
 GMJ  C23  C18  aromatic  1.395  0.020  1.395
 GMJ  C18  C15  single    1.523  0.020  1.523
 GMJ  C16  C15  single    1.534  0.020  1.534
 GMJ  C16  C17  single    1.522  0.020  1.522
 GMJ  C15  O25  single    1.412  0.020  1.412
 GMJ  C15  C14  single    1.531  0.020  1.531
 GMJ  C14  C13  single    1.520  0.020  1.520
 GMJ  C17  N12  single    1.452  0.020  1.452
 GMJ  C13  N12  single    1.453  0.020  1.453
 GMJ  N12  C11  single    1.451  0.020  1.451
 GMJ  C11  C10  single    1.523  0.020  1.523
 GMJ  C10  C09  single    1.521  0.020  1.521
 GMJ  C09  C07  single    1.507  0.020  1.507
 GMJ  O08  C07  double    1.213  0.020  1.213
 GMJ  C07  C06  single    1.490  0.020  1.490
 GMJ  C06  C05  aromatic  1.397  0.020  1.397
 GMJ  C06  C01  aromatic  1.395  0.020  1.395
 GMJ  C05  C04  aromatic  1.383  0.020  1.383
 GMJ  C01  C02  aromatic  1.385  0.020  1.385
 GMJ  C04  C03  aromatic  1.384  0.020  1.384
 GMJ  C02  C03  aromatic  1.381  0.020  1.381
 GMJ  C03  F26  single    1.338  0.020  1.338
 GMJ  C10  H1   single    0.970  0.020  1.090
 GMJ  C10  H2   single    0.970  0.020  1.090
 GMJ  C11  H3   single    0.970  0.020  1.090
 GMJ  C11  H4   single    0.970  0.020  1.090
 GMJ  C01  H5   single    0.930  0.020  1.080
 GMJ  C02  H6   single    0.930  0.020  1.080
 GMJ  C04  H7   single    0.930  0.020  1.080
 GMJ  C05  H8   single    0.930  0.020  1.080
 GMJ  C09  H9   single    0.970  0.020  1.090
 GMJ  C09  H10  single    0.970  0.020  1.090
 GMJ  C13  H11  single    0.970  0.020  1.090
 GMJ  C13  H12  single    0.970  0.020  1.090
 GMJ  C14  H13  single    0.970  0.020  1.090
 GMJ  C14  H14  single    0.970  0.020  1.090
 GMJ  C16  H15  single    0.970  0.020  1.090
 GMJ  C16  H16  single    0.970  0.020  1.090
 GMJ  C17  H17  single    0.970  0.020  1.090
 GMJ  C17  H18  single    0.970  0.020  1.090
 GMJ  C19  H19  single    0.930  0.020  1.080
 GMJ  C20  H20  single    0.930  0.020  1.080
 GMJ  C22  H21  single    0.930  0.020  1.080
 GMJ  C23  H22  single    0.930  0.020  1.080
 GMJ  O25  H24  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
 GMJ  H2   C10  H1   107.00  3.000
 GMJ  H2   C10  C09  110.07  3.000
 GMJ  H1   C10  C09  109.54  3.000
 GMJ  H2   C10  C11  108.99  3.000
 GMJ  H1   C10  C11  110.98  3.000
 GMJ  C09  C10  C11  110.22  3.000
 GMJ  H4   C11  H3   106.09  3.000
 GMJ  H4   C11  N12  107.33  3.000
 GMJ  H3   C11  N12  111.44  3.000
 GMJ  H4   C11  C10  108.04  3.000
 GMJ  H3   C11  C10  109.65  3.000
 GMJ  N12  C11  C10  113.92  3.000
 GMJ  H5   C01  C06  120.81  3.000
 GMJ  H5   C01  C02  118.15  3.000
 GMJ  C06  C01  C02  121.05  3.000
 GMJ  H6   C02  C03  120.63  3.000
 GMJ  H6   C02  C01  120.97  3.000
 GMJ  C03  C02  C01  118.40  3.000
 GMJ  F26  C03  C04  118.78  3.000
 GMJ  F26  C03  C02  118.91  3.000
 GMJ  C04  C03  C02  122.31  3.000
 GMJ  H7   C04  C05  121.08  3.000
 GMJ  H7   C04  C03  120.45  3.000
 GMJ  C05  C04  C03  118.46  3.000
 GMJ  H8   C05  C06  119.87  3.000
 GMJ  H8   C05  C04  119.11  3.000
 GMJ  C06  C05  C04  121.01  3.000
 GMJ  C07  C06  C05  119.06  3.000
 GMJ  C05  C06  C01  118.77  3.000
 GMJ  C07  C06  C01  122.17  3.000
 GMJ  O08  C07  C09  121.57  3.000
 GMJ  O08  C07  C06  120.25  3.000
 GMJ  C09  C07  C06  118.18  3.000
 GMJ  H10  C09  H9   104.95  3.000
 GMJ  H10  C09  C07  108.43  3.000
 GMJ  H9   C09  C07  108.31  3.000
 GMJ  H10  C09  C10  110.26  3.000
 GMJ  H9   C09  C10  110.10  3.000
 GMJ  C07  C09  C10  114.34  3.000
 GMJ  H12  C13  H11  106.52  3.000
 GMJ  H12  C13  N12  111.75  3.000
 GMJ  H11  C13  N12  108.46  3.000
 GMJ  H12  C13  C14  109.91  3.000
 GMJ  H11  C13  C14  108.60  3.000
 GMJ  N12  C13  C14  111.41  3.000
 GMJ  H14  C14  H13  107.04  3.000
 GMJ  H14  C14  C15  108.91  3.000
 GMJ  H13  C14  C15  109.88  3.000
 GMJ  H14  C14  C13  109.00  3.000
 GMJ  H13  C14  C13  109.89  3.000
 GMJ  C15  C14  C13  111.98  3.000
 GMJ  O25  C15  C18  111.01  3.000
 GMJ  O25  C15  C16  109.98  3.000
 GMJ  C18  C15  C16  110.98  3.000
 GMJ  O25  C15  C14  106.41  3.000
 GMJ  C16  C15  C14  108.16  3.000
 GMJ  C18  C15  C14  110.15  3.000
 GMJ  H16  C16  H15  106.57  3.000
 GMJ  H16  C16  C17  108.76  3.000
 GMJ  H15  C16  C17  109.70  3.000
 GMJ  H16  C16  C15  109.89  3.000
 GMJ  H15  C16  C15  109.96  3.000
 GMJ  C17  C16  C15  111.81  3.000
 GMJ  H18  C17  H17  106.46  3.000
 GMJ  H18  C17  N12  109.47  3.000
 GMJ  H17  C17  N12  111.49  3.000
 GMJ  H18  C17  C16  108.10  3.000
 GMJ  H17  C17  C16  110.20  3.000
 GMJ  N12  C17  C16  110.96  3.000
 GMJ  C23  C18  C19  117.84  3.000
 GMJ  C23  C18  C15  120.62  3.000
 GMJ  C19  C18  C15  121.53  3.000
 GMJ  H19  C19  C20  118.14  3.000
 GMJ  H19  C19  C18  120.47  3.000
 GMJ  C20  C19  C18  121.39  3.000
 GMJ  H20  C20  C21  120.63  3.000
 GMJ  H20  C20  C19  120.04  3.000
 GMJ  C21  C20  C19  119.33  3.000
 GMJ  CL1  C21  C22  119.57  3.000
 GMJ  C22  C21  C20  120.70  3.000
 GMJ  CL1  C21  C20  119.73  3.000
 GMJ  H21  C22  C23  120.16  3.000
 GMJ  H21  C22  C21  120.72  3.000
 GMJ  C23  C22  C21  119.12  3.000
 GMJ  H22  C23  C22  117.95  3.000
 GMJ  H22  C23  C18  120.44  3.000
 GMJ  C22  C23  C18  121.61  3.000
 GMJ  C17  N12  C13  110.73  3.000
 GMJ  C13  N12  C11  110.59  3.000
 GMJ  C17  N12  C11  112.68  3.000
 GMJ  H24  O25  C15  109.01  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
 GMJ  CONST_01  C04  C05  C06  C01     0.00   0.0  0
 GMJ  CONST_02  C04  C03  C02  C01     0.00   0.0  0
 GMJ  CONST_03  C05  C06  C01  C02     0.00   0.0  0
 GMJ  CONST_04  C05  C04  C03  C02     0.00   0.0  0
 GMJ  CONST_05  C06  C05  C04  C03     0.00   0.0  0
 GMJ  CONST_06  C06  C01  C02  C03     0.00   0.0  0
 GMJ  CONST_07  C21  C20  C19  C18     0.00   0.0  0
 GMJ  CONST_08  C21  C22  C23  C18     0.00   0.0  0
 GMJ  CONST_09  C22  C21  C20  C19     0.00   0.0  0
 GMJ  CONST_10  C22  C23  C18  C19     0.00   0.0  0
 GMJ  CONST_11  C23  C22  C21  C20     0.00   0.0  0
 GMJ  CONST_12  C23  C18  C19  C20     0.00   0.0  0
 GMJ  CONST_13  C20  C19  C18  C15   180.00   0.0  0
 GMJ  CONST_14  C22  C23  C18  C15   180.00   0.0  0
 GMJ  CONST_15  F26  C03  C02  C01   180.00   0.0  0
 GMJ  CONST_16  C07  C06  C01  C02   180.00   0.0  0
 GMJ  CONST_17  C07  C06  C05  C04   180.00   0.0  0
 GMJ  CONST_18  F26  C03  C04  C05   180.00   0.0  0
 GMJ  CONST_19  CL1  C21  C20  C19   180.00   0.0  0
 GMJ  CONST_20  CL1  C21  C22  C23   180.00   0.0  0
 GMJ  CONST_21  H8   C05  C06  C01   180.00   0.0  0
 GMJ  CONST_22  H7   C04  C03  C02   180.00   0.0  0
 GMJ  CONST_23  H5   C01  C02  C03   180.00   0.0  0
 GMJ  CONST_24  H6   C02  C03  C04   180.00   0.0  0
 GMJ  CONST_25  H19  C19  C18  C15     0.00   0.0  0
 GMJ  CONST_26  H22  C23  C18  C15     0.00   0.0  0
 GMJ  CONST_27  H20  C20  C19  C18   180.00   0.0  0
 GMJ  CONST_28  H21  C22  C23  C18   180.00   0.0  0
 GMJ  Var_01    C16  C17  N12  C13    59.90  30.0  1
 GMJ  Var_02    C17  N12  C13  C14   -59.49  30.0  1
 GMJ  Var_03    N12  C17  C16  C15   -57.61  30.0  1
 GMJ  Var_04    N12  C13  C14  C15    56.62  30.0  1
 GMJ  Var_05    C09  C07  C06  C01     3.33  30.0  2
 GMJ  Var_06    C06  C07  C09  C10   176.61  30.0  3
 GMJ  Var_07    N12  C11  C10  C09   172.19  30.0  1
 GMJ  Var_08    C07  C09  C10  C11  -178.08  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
 GMJ  chir_01  C15  C16  C18  C14  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
 GMJ  plan-1  C01  0.020
 GMJ  plan-1  C02  0.020
 GMJ  plan-1  C03  0.020
 GMJ  plan-1  C04  0.020
 GMJ  plan-1  C05  0.020
 GMJ  plan-1  C06  0.020
 GMJ  plan-1  C07  0.020
 GMJ  plan-1  H5   0.020
 GMJ  plan-1  H6   0.020
 GMJ  plan-1  H7   0.020
 GMJ  plan-1  H8   0.020
 GMJ  plan-1  F26  0.020
 GMJ  plan-2  C15  0.020
 GMJ  plan-2  C18  0.020
 GMJ  plan-2  C19  0.020
 GMJ  plan-2  C20  0.020
 GMJ  plan-2  C21  0.020
 GMJ  plan-2  C22  0.020
 GMJ  plan-2  C23  0.020
 GMJ  plan-2  CL1  0.020
 GMJ  plan-2  H19  0.020
 GMJ  plan-2  H20  0.020
 GMJ  plan-2  H21  0.020
 GMJ  plan-2  H22  0.020
 GMJ  plan-3  C06  0.020
 GMJ  plan-3  C07  0.020
 GMJ  plan-3  C09  0.020
 GMJ  plan-3  O08  0.020

