# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  9 12:05:46 2020
#   Inital geometry file: a 159 line input string
#   Ligand name: 2-chloro-4-{1'-[(2R)-2-hydroxy-3-methyl-2-(trifluoromethyl)butanoyl]-4,4'-bipiperidin-1-yl}-N,N-dimethylbenzamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)[C@@](O)(C(=O)N1CCC(CC1)C2CCN(CC2)c3ccc(c(Cl)c3)C(=O)N(C)C)C(F)(F)F
#
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
 668  668  2-chloro-4-{1'-[(2R)-2-hydroxy-3-methyl-2-(trifluoromethyl)butanoyl]-4,4'-bipiperidin-1-yl}-N,N-dimethylbenzamide  ligand  70  35  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_668
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
 668  F2   F   F     0  -0.296  -7.2793  -1.8128   0.3018
 668  C24  C   CT    0   1.047  -6.7571  -1.0094  -0.6248
 668  F    F   F     0  -0.308  -5.6810  -1.6397  -1.1248
 668  F1   F   F     0  -0.298  -7.6363  -0.9209  -1.6229
 668  C3   C   CT    0  -0.054  -6.3716   0.3657  -0.0537
 668  O    O   OH1   0  -0.659  -6.1673   1.1625  -1.1809
 668  C1   C   CH1   0  -0.265  -7.4792   0.9709   0.8573
 668  C2   C   CH3   0  -0.692  -7.0278   2.3293   1.4006
 668  C    C   CH3   0  -0.664  -8.8269   1.1382   0.1577
 668  C4   C   C     0   0.515  -5.1156   0.1349   0.8433
 668  O1   O   O     0  -0.469  -5.3054  -0.3740   1.9372
 668  N    N   NT    0  -0.444  -3.9072   0.6063   0.4657
 668  C9   C   CH2   0  -0.322  -2.8570   0.6652   1.4753
 668  C8   C   CH2   0  -0.427  -1.9032  -0.5157   1.3882
 668  C7   C   CH1   0  -0.239  -1.2721  -0.6148  -0.0012
 668  C6   C   CH2   0  -0.421  -2.3748  -0.5607  -1.0592
 668  C5   C   CH2   0  -0.342  -3.3392   0.6083  -0.8814
 668  C10  C   CH1   0  -0.241  -0.4141  -1.8818  -0.1647
 668  C14  C   CH2   0  -0.443   0.3476  -1.9263  -1.4904
 668  C13  C   CH2   0  -0.313   1.4674  -0.8972  -1.5652
 668  N1   N   NT    0  -0.515   2.3832  -1.0322  -0.4448
 668  C12  C   CH2   0  -0.305   1.7306  -1.0260   0.8605
 668  C11  C   CH2   0  -0.452   0.6306  -2.0699   0.9360
 668  C15  C   CR6   0   0.387   3.6578  -0.5189  -0.5597
 668  C23  C   CR16  0  -0.295   4.6182  -0.7656   0.4374
 668  C22  C   CR6   0  -0.045   5.9040  -0.2831   0.3120
 668  CL   CL  CL    0  -0.119   7.0398  -0.6709   1.5682
 668  C18  C   CR6   0  -0.042   6.3233   0.4563  -0.7889
 668  C17  C   CR16  0  -0.268   5.3804   0.6705  -1.7874
 668  C16  C   CR16  0  -0.353   4.0763   0.2232  -1.6771
 668  C19  C   C     0   0.495   7.7356   0.9035  -0.9951
 668  O2   O   O     0  -0.490   8.3900   0.4259  -1.9152
 668  N2   N   NT    0  -0.420   8.2358   1.8227  -0.1541
 668  C21  C   CH3   0  -0.522   9.6368   2.1770  -0.2593
 668  C20  C   CH3   0  -0.529   7.4548   2.5932   0.7891
 668  H1   H   HOH1  0   0.470  -5.8630   2.0351  -0.9082
 668  H2   H   HCH1  0   0.259  -7.6147   0.3041   1.7074
 668  H3   H   HCH3  0   0.222  -6.9634   3.0890   0.6180
 668  H4   H   HCH3  0   0.255  -7.7614   2.6906   2.1206
 668  H5   H   HCH3  0   0.246  -6.0680   2.2942   1.9168
 668  H6   H   HCH3  0   0.237  -9.3036   0.1938  -0.0989
 668  H7   H   HCH3  0   0.236  -9.5078   1.6590   0.8321
 668  H8   H   HCH3  0   0.226  -8.7452   1.7405  -0.7478
 668  H9   H   HCH2  0   0.244  -2.3021   1.5923   1.2990
 668  H10  H   HCH2  0   0.263  -3.3009   0.7381   2.4648
 668  H11  H   HCH2  0   0.242  -1.1375  -0.3812   2.1553
 668  H12  H   HCH2  0   0.226  -2.4371  -1.4405   1.6311
 668  H13  H   HCH1  0   0.221  -0.6379   0.2724  -0.1303
 668  H14  H   HCH2  0   0.245  -1.9506  -0.4811  -2.0625
 668  H15  H   HCH2  0   0.220  -2.9448  -1.4955  -1.0336
 668  H16  H   HCH2  0   0.280  -4.1115   0.5567  -1.6375
 668  H17  H   HCH2  0   0.242  -2.8106   1.5558  -1.0210
 668  H18  H   HCH1  0   0.230  -1.0988  -2.7377  -0.1344
 668  H19  H   HCH2  0   0.236   0.7826  -2.9228  -1.6097
 668  H20  H   HCH2  0   0.244  -0.3127  -1.7789  -2.3462
 668  H21  H   HCH2  0   0.256   2.0141  -1.0652  -2.4931
 668  H22  H   HCH2  0   0.220   1.0556   0.1212  -1.6223
 668  H23  H   HCH2  0   0.260   2.4579  -1.2303   1.6418
 668  H24  H   HCH2  0   0.225   1.3244  -0.0266   1.0741
 668  H25  H   HCH2  0   0.245   0.1859  -2.0435   1.9318
 668  H26  H   HCH2  0   0.237   1.0802  -3.0616   0.8289
 668  H27  H   HCR6  0   0.285   4.3767  -1.3702   1.2996
 668  H28  H   HCR6  0   0.266   5.6639   1.2349  -2.6671
 668  H29  H   HCR6  0   0.275   3.3857   0.4678  -2.4706
 668  H30  H   HCH3  0   0.241   9.8196   2.9096  -1.0499
 668  H31  H   HCH3  0   0.247   9.9622   2.6061   0.6861
 668  H32  H   HCH3  0   0.250  10.2453   1.2985  -0.4610
 668  H33  H   HCH3  0   0.262   6.3929   2.3987   0.6740
 668  H34  H   HCH3  0   0.243   7.7403   2.3663   1.8170
 668  H35  H   HCH3  0   0.253   7.6168   3.6581   0.6158

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
 668  O    C3   single    1.395  0.020  1.395
 668  F    C24  single    1.344  0.020  1.344
 668  F2   C24  single    1.333  0.020  1.333
 668  C24  C3   single    1.538  0.020  1.538
 668  C24  F1   single    1.333  0.020  1.333
 668  O1   C4   double    1.221  0.020  1.221
 668  C3   C4   single    1.561  0.020  1.561
 668  C3   C1   single    1.557  0.020  1.557
 668  C4   N    single    1.351  0.020  1.351
 668  C2   C1   single    1.531  0.020  1.531
 668  C1   C    single    1.528  0.020  1.528
 668  N    C9   single    1.458  0.020  1.458
 668  N    C5   single    1.462  0.020  1.462
 668  C9   C8   single    1.520  0.020  1.520
 668  C5   C6   single    1.526  0.020  1.526
 668  C8   C7   single    1.529  0.020  1.529
 668  C6   C7   single    1.529  0.020  1.529
 668  C7   C10  single    1.539  0.020  1.539
 668  C10  C11  single    1.529  0.020  1.529
 668  C10  C14  single    1.530  0.020  1.530
 668  C11  C12  single    1.518  0.020  1.518
 668  C14  C13  single    1.523  0.020  1.523
 668  C12  N1   single    1.459  0.020  1.459
 668  C13  N1   single    1.453  0.020  1.453
 668  N1   C15  single    1.379  0.020  1.379
 668  C15  C23  aromatic  1.406  0.020  1.406
 668  C15  C16  aromatic  1.405  0.020  1.405
 668  C23  C22  aromatic  1.379  0.020  1.379
 668  C16  C17  aromatic  1.383  0.020  1.383
 668  C22  CL   single    1.737  0.020  1.737
 668  C22  C18  aromatic  1.391  0.020  1.391
 668  C17  C18  aromatic  1.390  0.020  1.390
 668  C18  C19  single    1.496  0.020  1.496
 668  C20  N2   single    1.447  0.020  1.447
 668  C19  N2   single    1.342  0.020  1.342
 668  C19  O2   double    1.226  0.020  1.226
 668  N2   C21  single    1.449  0.020  1.449
 668  O    H1   single    0.850  0.020  0.980
 668  C1   H2   single    0.970  0.020  1.090
 668  C2   H3   single    0.970  0.020  1.090
 668  C2   H4   single    0.970  0.020  1.090
 668  C2   H5   single    0.970  0.020  1.090
 668  C    H6   single    0.970  0.020  1.090
 668  C    H7   single    0.970  0.020  1.090
 668  C    H8   single    0.970  0.020  1.090
 668  C9   H9   single    0.970  0.020  1.090
 668  C9   H10  single    0.970  0.020  1.090
 668  C8   H11  single    0.970  0.020  1.090
 668  C8   H12  single    0.970  0.020  1.090
 668  C7   H13  single    0.970  0.020  1.090
 668  C6   H14  single    0.970  0.020  1.090
 668  C6   H15  single    0.970  0.020  1.090
 668  C5   H16  single    0.970  0.020  1.090
 668  C5   H17  single    0.970  0.020  1.090
 668  C10  H18  single    0.970  0.020  1.090
 668  C14  H19  single    0.970  0.020  1.090
 668  C14  H20  single    0.970  0.020  1.090
 668  C13  H21  single    0.970  0.020  1.090
 668  C13  H22  single    0.970  0.020  1.090
 668  C12  H23  single    0.970  0.020  1.090
 668  C12  H24  single    0.970  0.020  1.090
 668  C11  H25  single    0.970  0.020  1.090
 668  C11  H26  single    0.970  0.020  1.090
 668  C23  H27  single    0.930  0.020  1.080
 668  C17  H28  single    0.930  0.020  1.080
 668  C16  H29  single    0.930  0.020  1.080
 668  C21  H30  single    0.970  0.020  1.090
 668  C21  H31  single    0.970  0.020  1.090
 668  C21  H32  single    0.970  0.020  1.090
 668  C20  H33  single    0.970  0.020  1.090
 668  C20  H34  single    0.970  0.020  1.090
 668  C20  H35  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
 668  C3   C24  F1   112.58  3.000
 668  F1   C24  F    106.30  3.000
 668  C3   C24  F    110.91  3.000
 668  F1   C24  F2   107.59  3.000
 668  C3   C24  F2   112.27  3.000
 668  F    C24  F2   106.84  3.000
 668  C4   C3   C1   107.08  3.000
 668  C1   C3   O    110.79  3.000
 668  C4   C3   O    115.53  3.000
 668  C1   C3   C24  112.74  3.000
 668  C4   C3   C24  106.43  3.000
 668  O    C3   C24  104.31  3.000
 668  H1   O    C3   109.55  3.000
 668  H2   C1   C    108.35  3.000
 668  H2   C1   C2   107.64  3.000
 668  C    C1   C2   108.99  3.000
 668  H2   C1   C3   107.91  3.000
 668  C    C1   C3   113.72  3.000
 668  C2   C1   C3   110.05  3.000
 668  H5   C2   H4   106.89  3.000
 668  H5   C2   H3   108.04  3.000
 668  H4   C2   H3   106.40  3.000
 668  H5   C2   C1   113.51  3.000
 668  H4   C2   C1   109.28  3.000
 668  H3   C2   C1   112.34  3.000
 668  H8   C    H7   107.24  3.000
 668  H8   C    H6   108.43  3.000
 668  H7   C    H6   106.66  3.000
 668  H8   C    C1   112.00  3.000
 668  H7   C    C1   108.65  3.000
 668  H6   C    C1   113.53  3.000
 668  N    C4   O1   122.33  3.000
 668  N    C4   C3   120.51  3.000
 668  O1   C4   C3   116.83  3.000
 668  C5   N    C9   110.99  3.000
 668  C5   N    C4   127.27  3.000
 668  C9   N    C4   117.70  3.000
 668  H10  C9   H9   107.26  3.000
 668  H10  C9   C8   111.13  3.000
 668  H9   C9   C8   109.30  3.000
 668  H10  C9   N    109.81  3.000
 668  H9   C9   N    106.73  3.000
 668  C8   C9   N    112.39  3.000
 668  H12  C8   H11  106.86  3.000
 668  H12  C8   C7   110.36  3.000
 668  H11  C8   C7   110.90  3.000
 668  H12  C8   C9   109.71  3.000
 668  H11  C8   C9   107.70  3.000
 668  C7   C8   C9   111.18  3.000
 668  H13  C7   C10  109.31  3.000
 668  H13  C7   C6   107.85  3.000
 668  C10  C7   C6   110.96  3.000
 668  H13  C7   C8   107.02  3.000
 668  C10  C7   C8   112.33  3.000
 668  C6   C7   C8   109.19  3.000
 668  H15  C6   H14  106.61  3.000
 668  H15  C6   C5   108.80  3.000
 668  H14  C6   C5   107.26  3.000
 668  H15  C6   C7   109.20  3.000
 668  H14  C6   C7   110.98  3.000
 668  C5   C6   C7   113.72  3.000
 668  H17  C5   H16  107.28  3.000
 668  H17  C5   C6   110.08  3.000
 668  H16  C5   C6   109.46  3.000
 668  H17  C5   N    107.85  3.000
 668  H16  C5   N    111.50  3.000
 668  C6   C5   N    110.60  3.000
 668  H18  C10  C11  108.10  3.000
 668  H18  C10  C14  108.19  3.000
 668  C11  C10  C14  106.27  3.000
 668  H18  C10  C7   106.95  3.000
 668  C14  C10  C7   113.19  3.000
 668  C11  C10  C7   113.94  3.000
 668  H20  C14  H19  106.16  3.000
 668  H20  C14  C13  108.38  3.000
 668  H19  C14  C13  108.53  3.000
 668  H20  C14  C10  112.00  3.000
 668  H19  C14  C10  108.61  3.000
 668  C13  C14  C10  112.90  3.000
 668  H22  C13  H21  106.63  3.000
 668  H22  C13  N1   111.22  3.000
 668  H21  C13  N1   109.02  3.000
 668  H22  C13  C14  110.66  3.000
 668  H21  C13  C14  107.85  3.000
 668  N1   C13  C14  111.27  3.000
 668  C15  N1   C12  119.10  3.000
 668  C15  N1   C13  118.93  3.000
 668  C12  N1   C13  114.04  3.000
 668  H24  C12  H23  106.16  3.000
 668  H24  C12  C11  110.34  3.000
 668  H23  C12  C11  108.65  3.000
 668  H24  C12  N1   110.05  3.000
 668  H23  C12  N1   110.06  3.000
 668  C11  C12  N1   111.44  3.000
 668  H26  C11  H25  106.19  3.000
 668  H26  C11  C12  108.70  3.000
 668  H25  C11  C12  108.91  3.000
 668  H26  C11  C10  108.77  3.000
 668  H25  C11  C10  112.06  3.000
 668  C12  C11  C10  112.00  3.000
 668  C16  C15  C23  116.94  3.000
 668  C16  C15  N1   122.56  3.000
 668  C23  C15  N1   120.46  3.000
 668  H27  C23  C22  118.48  3.000
 668  H27  C23  C15  120.75  3.000
 668  C22  C23  C15  120.72  3.000
 668  C18  C22  CL   119.60  3.000
 668  C18  C22  C23  122.62  3.000
 668  CL   C22  C23  117.75  3.000
 668  C19  C18  C17  119.70  3.000
 668  C19  C18  C22  123.56  3.000
 668  C17  C18  C22  116.49  3.000
 668  H28  C17  C16  118.70  3.000
 668  H28  C17  C18  119.10  3.000
 668  C16  C17  C18  122.17  3.000
 668  H29  C16  C17  118.10  3.000
 668  H29  C16  C15  120.89  3.000
 668  C17  C16  C15  121.00  3.000
 668  N2   C19  O2   122.55  3.000
 668  O2   C19  C18  119.41  3.000
 668  N2   C19  C18  118.04  3.000
 668  C20  N2   C21  116.04  3.000
 668  C21  N2   C19  118.83  3.000
 668  C20  N2   C19  124.88  3.000
 668  H32  C21  H31  108.20  3.000
 668  H32  C21  H30  108.29  3.000
 668  H31  C21  H30  108.30  3.000
 668  H32  C21  N2   110.91  3.000
 668  H31  C21  N2   108.81  3.000
 668  H30  C21  N2   112.21  3.000
 668  H35  C20  H34  108.29  3.000
 668  H35  C20  H33  107.65  3.000
 668  H34  C20  H33  108.59  3.000
 668  H35  C20  N2   109.64  3.000
 668  H34  C20  N2   111.24  3.000
 668  H33  C20  N2   111.31  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
 668  CONST_01  C18  C22  C23  C15     0.00   0.0  0
 668  CONST_02  C18  C17  C16  C15     0.00   0.0  0
 668  CONST_03  C17  C16  C15  C23     0.00   0.0  0
 668  CONST_04  C17  C18  C22  C23     0.00   0.0  0
 668  CONST_05  C16  C15  C23  C22     0.00   0.0  0
 668  CONST_06  C16  C17  C18  C22     0.00   0.0  0
 668  CONST_07  C22  C23  C15  N1    180.00   0.0  0
 668  CONST_08  C17  C16  C15  N1    180.00   0.0  0
 668  CONST_09  CL   C22  C23  C15   180.00   0.0  0
 668  CONST_10  C19  C18  C22  C23   180.00   0.0  0
 668  CONST_11  C17  C18  C22  CL    180.00   0.0  0
 668  CONST_12  C19  C18  C17  C16   180.00   0.0  0
 668  CONST_13  H27  C23  C15  N1      0.00   0.0  0
 668  CONST_14  H29  C16  C15  N1      0.00   0.0  0
 668  CONST_15  H28  C17  C16  C15   180.00   0.0  0
 668  CONST_18  C9   N    C4   O1      0.00   0.0  0
 668  CONST_20  C20  N2   C19  C18     0.00   0.0  0
 668  CONST_21  C21  N2   C19  C18   180.00   0.0  0
 668  CONST_22  C20  N2   C19  O2    180.00   0.0  0
 668  CONST_23  C21  N2   C19  O2      0.00   0.0  0
 668  Var_01    C7   C8   C9   N      56.80  30.0  1
 668  Var_02    C7   C6   C5   N     -54.39  30.0  1
 668  Var_03    C6   C5   N    C9     57.49  30.0  1
 668  Var_04    C5   N    C9   C8    -59.99  30.0  1
 668  Var_05    N1   C12  C11  C10   -56.63  30.0  1
 668  Var_06    N1   C13  C14  C10    54.96  30.0  1
 668  Var_07    C12  N1   C13  C14   -52.53  30.0  1
 668  Var_08    C11  C12  N1   C13    53.70  30.0  1
 668  Var_09    C23  C15  N1   C13  -172.56  30.0  2
 668  Var_10    N2   C19  C18  C22   -67.68  30.0  2
 668  Var_11    H3   C2   C1   C3     68.31  30.0  3
 668  Var_12    H6   C    C1   C3     67.27  30.0  3
 668  Var_13    H33  C20  N2   C19    -4.99  30.0  3
 668  Var_14    H30  C21  N2   C19    81.91  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
 668  chir_01  C3   C24  C4   C1   positiv
 668  chir_02  C7   C8   C6   C10  positiv
 668  chir_03  C10  C14  C11  C7   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
 668  plan-1  C3   0.020
 668  plan-1  C4   0.020
 668  plan-1  O1   0.020
 668  plan-1  N    0.020
 668  plan-1  C9   0.020
 668  plan-1  C5   0.020
 668  plan-2  N1   0.020
 668  plan-2  C15  0.020
 668  plan-2  C23  0.020
 668  plan-2  C22  0.020
 668  plan-2  CL   0.020
 668  plan-2  C18  0.020
 668  plan-2  C17  0.020
 668  plan-2  C16  0.020
 668  plan-2  C19  0.020
 668  plan-2  H27  0.020
 668  plan-2  H28  0.020
 668  plan-2  H29  0.020
 668  plan-3  C18  0.020
 668  plan-3  C19  0.020
 668  plan-3  O2   0.020
 668  plan-3  N2   0.020
 668  plan-3  C21  0.020
 668  plan-3  C20  0.020

