# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  9 06:19:01 2020
#   Inital geometry file: a 113 line input string
#   Ligand name: 6,8-dichloro-4-phenyl-2-(piperidin-1-yl)quinoline-3-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1c(nc2c(Cl)cc(Cl)cc2c1c3ccccc3)N4CCCCC4
#
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
 65Z  65Z  '6,8-dichloro-4-phenyl-2-(piperidin-1-yl)quinoline-3-carboxylic acid'  ligand  44  27  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_65Z
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
 65Z  N1   N   NT     0  -0.485   2.8913  -0.2246  -0.0085
 65Z  C2   C   CH2    0  -0.295   3.6708  -1.3542  -0.4836
 65Z  C3   C   CH2    0  -0.433   4.9434  -0.8546  -1.1580
 65Z  C4   C   CH2    0  -0.445   5.7547   0.0487  -0.2372
 65Z  C5   C   CH2    0  -0.426   4.8808   1.1724   0.3089
 65Z  C6   C   CH2    0  -0.327   3.6246   0.5983   0.9406
 65Z  C7   C   CR6    0  -0.059  -3.1161  -1.9772  -0.2960
 65Z  C8   C   CR16   0  -0.201  -2.2707  -3.0744  -0.5085
 65Z  C9   C   CR6    0  -0.128  -0.9153  -2.8751  -0.4916
 65Z  C10  C   CR16   0  -0.299  -2.6214  -0.7193  -0.0764
 65Z  C11  C   CR66   0   0.026  -1.2296  -0.5170  -0.0532
 65Z  C12  C   CR66   0   0.277  -0.3461  -1.6003  -0.2548
 65Z  N13  N   N      0  -0.489   0.9872  -1.4695  -0.2129
 65Z  C14  C   CR6    0   0.493   1.5283  -0.2882  -0.0224
 65Z  C15  C   CR6    0  -0.191   0.7276   0.9059   0.1152
 65Z  C16  C   CR6    0   0.165  -0.6307   0.7690   0.1239
 65Z  C19  C   C      0   0.357   1.3210   2.3109   0.0635
 65Z  O20  O   OC    -1  -0.583   1.2000   3.0141   1.0795
 65Z  O21  O   O      0  -0.569   1.8425   2.6085  -1.0233
 65Z  C22  C   CR6    0   0.002  -1.5130   1.9586   0.2163
 65Z  C23  C   CR16   0  -0.269  -1.7965   2.7014  -0.9250
 65Z  C24  C   CR16   0  -0.263  -3.2162   4.1612   0.3569
 65Z  C25  C   CR16   0  -0.250  -2.9406   3.4176   1.4980
 65Z  C26  C   CR16   0  -0.246  -2.6424   3.8008  -0.8546
 65Z  C27  C   CR16   0  -0.263  -2.0922   2.3222   1.4278
 65Z  H1   H   HCH2   0   0.209   3.9255  -2.0233   0.3508
 65Z  H2   H   HCH2   0   0.256   3.0738  -1.9369  -1.1807
 65Z  H3   H   HCH2   0   0.232   5.5353  -1.7167  -1.4750
 65Z  H4   H   HCH2   0   0.219   4.6679  -0.3064  -2.0638
 65Z  H5   H   HCH2   0   0.211   6.1417  -0.5425   0.5998
 65Z  H6   H   HCH2   0   0.233   6.6219   0.4525  -0.7639
 65Z  H7   H   HCH2   0   0.229   5.4250   1.7538   1.0567
 65Z  H8   H   HCH2   0   0.224   4.5955   1.8581  -0.4927
 65Z  H9   H   HCH2   0   0.264   2.9959   1.3833   1.3476
 65Z  H10  H   HCH2   0   0.225   3.9127  -0.0330   1.7948
 65Z  H11  H   HCR6   0   0.297  -2.6816  -4.0585  -0.6866
 65Z  H12  H   HCR6   0   0.278  -3.2947   0.1138   0.0715
 65Z  H14  H   HCR6   0   0.249  -1.3556   2.4176  -1.8725
 65Z  H15  H   HCR6   0   0.255  -3.8778   5.0159   0.4120
 65Z  H16  H   HCR6   0   0.255  -3.3854   3.6933   2.4456
 65Z  H17  H   HCR6   0   0.255  -2.8547   4.3736  -1.7483
 65Z  H18  H   HCR6   0   0.247  -1.8770   1.7471   2.3198
 65Z  CL1  CL  CL     0  -0.108   0.1393  -4.2147  -0.7621
 65Z  CL2  CL  CL     0  -0.126  -4.8296  -2.2392  -0.3226

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
 65Z  CL2  C7   single    1.734  0.020  1.734
 65Z  C8   C7   aromatic  1.401  0.020  1.401
 65Z  C8   C9   aromatic  1.370  0.020  1.370
 65Z  C7   C10  aromatic  1.369  0.020  1.369
 65Z  CL1  C9   single    1.726  0.020  1.726
 65Z  C9   C12  aromatic  1.416  0.020  1.416
 65Z  C10  C11  aromatic  1.407  0.020  1.407
 65Z  C12  C11  aromatic  1.412  0.020  1.412
 65Z  C12  N13  aromatic  1.340  0.020  1.340
 65Z  C11  C16  aromatic  1.430  0.020  1.430
 65Z  N13  C14  aromatic  1.313  0.020  1.313
 65Z  C23  C26  aromatic  1.389  0.020  1.389
 65Z  C23  C22  aromatic  1.391  0.020  1.391
 65Z  C16  C22  single    1.484  0.020  1.484
 65Z  C16  C15  aromatic  1.365  0.020  1.365
 65Z  C26  C24  aromatic  1.388  0.020  1.388
 65Z  C22  C27  aromatic  1.391  0.020  1.391
 65Z  C24  C25  aromatic  1.390  0.020  1.390
 65Z  C27  C25  aromatic  1.387  0.020  1.387
 65Z  C14  C15  aromatic  1.444  0.020  1.444
 65Z  C14  N1   single    1.365  0.020  1.365
 65Z  C15  C19  single    1.526  0.020  1.526
 65Z  C2   N1   single    1.452  0.020  1.452
 65Z  C2   C3   single    1.524  0.020  1.524
 65Z  N1   C6   single    1.455  0.020  1.455
 65Z  C19  O21  deloc     1.242  0.020  1.242
 65Z  C19  O20  deloc     1.242  0.020  1.242
 65Z  C6   C5   single    1.519  0.020  1.519
 65Z  C3   C4   single    1.524  0.020  1.524
 65Z  C4   C5   single    1.525  0.020  1.525
 65Z  C2   H1   single    0.970  0.020  1.090
 65Z  C2   H2   single    0.970  0.020  1.090
 65Z  C3   H3   single    0.970  0.020  1.090
 65Z  C3   H4   single    0.970  0.020  1.090
 65Z  C4   H5   single    0.970  0.020  1.090
 65Z  C4   H6   single    0.970  0.020  1.090
 65Z  C5   H7   single    0.970  0.020  1.090
 65Z  C5   H8   single    0.970  0.020  1.090
 65Z  C6   H9   single    0.970  0.020  1.090
 65Z  C6   H10  single    0.970  0.020  1.090
 65Z  C8   H11  single    0.930  0.020  1.080
 65Z  C10  H12  single    0.930  0.020  1.080
 65Z  C23  H14  single    0.930  0.020  1.080
 65Z  C24  H15  single    0.930  0.020  1.080
 65Z  C25  H16  single    0.930  0.020  1.080
 65Z  C26  H17  single    0.930  0.020  1.080
 65Z  C27  H18  single    0.930  0.020  1.080

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
 65Z  C14  N1   C6   122.45  3.000
 65Z  C6   N1   C2   112.51  3.000
 65Z  C14  N1   C2   119.77  3.000
 65Z  H2   C2   H1   106.71  3.000
 65Z  H2   C2   C3   110.51  3.000
 65Z  H1   C2   C3   109.98  3.000
 65Z  H2   C2   N1   109.39  3.000
 65Z  H1   C2   N1   110.45  3.000
 65Z  C3   C2   N1   109.75  3.000
 65Z  H4   C3   H3   106.95  3.000
 65Z  H4   C3   C4   109.72  3.000
 65Z  H3   C3   C4   110.77  3.000
 65Z  H4   C3   C2   108.67  3.000
 65Z  H3   C3   C2   108.78  3.000
 65Z  C4   C3   C2   111.80  3.000
 65Z  H6   C4   H5   106.70  3.000
 65Z  H6   C4   C5   110.82  3.000
 65Z  H5   C4   C5   109.06  3.000
 65Z  H6   C4   C3   110.52  3.000
 65Z  H5   C4   C3   109.26  3.000
 65Z  C5   C4   C3   110.38  3.000
 65Z  H8   C5   H7   107.35  3.000
 65Z  H8   C5   C6   109.05  3.000
 65Z  H7   C5   C6   109.18  3.000
 65Z  H8   C5   C4   110.45  3.000
 65Z  H7   C5   C4   110.60  3.000
 65Z  C6   C5   C4   110.15  3.000
 65Z  H10  C6   H9   105.99  3.000
 65Z  H10  C6   C5   108.85  3.000
 65Z  H9   C6   C5   111.21  3.000
 65Z  H10  C6   N1   108.29  3.000
 65Z  H9   C6   N1   111.23  3.000
 65Z  C5   C6   N1   111.07  3.000
 65Z  CL2  C7   C10  119.89  3.000
 65Z  C10  C7   C8   121.71  3.000
 65Z  CL2  C7   C8   118.40  3.000
 65Z  H11  C8   C9   120.69  3.000
 65Z  H11  C8   C7   120.55  3.000
 65Z  C9   C8   C7   118.75  3.000
 65Z  CL1  C9   C12  118.64  3.000
 65Z  C12  C9   C8   122.05  3.000
 65Z  CL1  C9   C8   119.31  3.000
 65Z  H12  C10  C11  120.20  3.000
 65Z  H12  C10  C7   120.31  3.000
 65Z  C11  C10  C7   119.48  3.000
 65Z  C16  C11  C12  116.46  3.000
 65Z  C16  C11  C10  123.08  3.000
 65Z  C12  C11  C10  120.42  3.000
 65Z  N13  C12  C11  122.89  3.000
 65Z  N13  C12  C9   119.53  3.000
 65Z  C11  C12  C9   117.57  3.000
 65Z  C14  N13  C12  120.14  3.000
 65Z  C15  C14  N13  121.95  3.000
 65Z  C15  C14  N1   120.95  3.000
 65Z  N13  C14  N1   117.06  3.000
 65Z  C19  C15  C16  118.64  3.000
 65Z  C19  C15  C14  122.85  3.000
 65Z  C16  C15  C14  117.99  3.000
 65Z  C22  C16  C15  120.77  3.000
 65Z  C15  C16  C11  120.41  3.000
 65Z  C22  C16  C11  118.67  3.000
 65Z  O21  C19  O20  128.42  3.000
 65Z  O20  C19  C15  117.12  3.000
 65Z  O21  C19  C15  114.44  3.000
 65Z  C27  C22  C23  119.35  3.000
 65Z  C27  C22  C16  120.75  3.000
 65Z  C23  C22  C16  119.88  3.000
 65Z  H14  C23  C26  119.98  3.000
 65Z  H14  C23  C22  119.67  3.000
 65Z  C26  C23  C22  120.35  3.000
 65Z  H15  C24  C26  120.14  3.000
 65Z  H15  C24  C25  120.13  3.000
 65Z  C26  C24  C25  119.73  3.000
 65Z  H16  C25  C27  119.78  3.000
 65Z  H16  C25  C24  120.07  3.000
 65Z  C27  C25  C24  120.15  3.000
 65Z  H17  C26  C24  120.14  3.000
 65Z  H17  C26  C23  119.76  3.000
 65Z  C24  C26  C23  120.09  3.000
 65Z  H18  C27  C25  119.94  3.000
 65Z  H18  C27  C22  119.72  3.000
 65Z  C25  C27  C22  120.33  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
 65Z  CONST_01  C12  C9   C8   C7     0.00   0.0  0
 65Z  CONST_02  C12  C11  C10  C7     0.00   0.0  0
 65Z  CONST_03  C16  C11  C10  C7   180.00   0.0  0
 65Z  CONST_04  C11  C10  C7   C8     0.00   0.0  0
 65Z  CONST_05  C11  C12  C9   C8     0.00   0.0  0
 65Z  CONST_06  N13  C12  C9   C8   180.00   0.0  0
 65Z  CONST_07  C10  C7   C8   C9     0.00   0.0  0
 65Z  CONST_08  C10  C11  C12  C9     0.00   0.0  0
 65Z  CONST_09  C16  C11  C12  C9   180.00   0.0  0
 65Z  CONST_10  C14  N13  C12  C9   180.00   0.0  0
 65Z  CONST_11  N13  C12  C11  C10  180.00   0.0  0
 65Z  CONST_12  C22  C16  C11  C10    0.00   0.0  0
 65Z  CONST_13  C15  C16  C11  C10  180.00   0.0  0
 65Z  CONST_14  C14  N13  C12  C11    0.00   0.0  0
 65Z  CONST_17  C14  C15  C16  C11    0.00   0.0  0
 65Z  CONST_18  C22  C16  C11  C12  180.00   0.0  0
 65Z  CONST_19  C15  C16  C11  C12    0.00   0.0  0
 65Z  CONST_20  C15  C14  N13  C12    0.00   0.0  0
 65Z  CONST_21  C16  C11  C12  N13    0.00   0.0  0
 65Z  CONST_22  C16  C15  C14  N13    0.00   0.0  0
 65Z  CONST_23  C22  C16  C15  C14  180.00   0.0  0
 65Z  CONST_26  C26  C23  C22  C16  180.00   0.0  0
 65Z  CONST_27  C25  C27  C22  C16  180.00   0.0  0
 65Z  CONST_28  C24  C26  C23  C22    0.00   0.0  0
 65Z  CONST_29  C24  C25  C27  C22    0.00   0.0  0
 65Z  CONST_30  C25  C24  C26  C23    0.00   0.0  0
 65Z  CONST_31  C25  C27  C22  C23    0.00   0.0  0
 65Z  CONST_32  C27  C22  C23  C26    0.00   0.0  0
 65Z  CONST_33  C27  C25  C24  C26    0.00   0.0  0
 65Z  CONST_34  C12  N13  C14  N1   180.00   0.0  0
 65Z  CONST_35  C16  C15  C14  N1   180.00   0.0  0
 65Z  CONST_36  C19  C15  C14  N1     0.00   0.0  0
 65Z  CONST_37  CL1  C9   C8   C7   180.00   0.0  0
 65Z  CONST_38  CL2  C7   C8   C9   180.00   0.0  0
 65Z  CONST_39  CL2  C7   C10  C11  180.00   0.0  0
 65Z  CONST_40  CL1  C9   C12  C11  180.00   0.0  0
 65Z  CONST_41  C19  C15  C16  C11  180.00   0.0  0
 65Z  CONST_42  CL1  C9   C12  N13    0.00   0.0  0
 65Z  CONST_43  C19  C15  C14  N13  180.00   0.0  0
 65Z  CONST_44  C22  C16  C15  C19    0.00   0.0  0
 65Z  CONST_45  H12  C10  C7   C8   180.00   0.0  0
 65Z  CONST_46  H11  C8   C7   C10  180.00   0.0  0
 65Z  CONST_47  H14  C23  C22  C16    0.00   0.0  0
 65Z  CONST_48  H18  C27  C22  C16    0.00   0.0  0
 65Z  CONST_49  H17  C26  C23  C22  180.00   0.0  0
 65Z  CONST_50  H16  C25  C27  C22  180.00   0.0  0
 65Z  CONST_51  H15  C24  C26  C23  180.00   0.0  0
 65Z  Var_01    C4   C3   C2   N1    55.22  30.0  1
 65Z  Var_02    C4   C5   C6   N1   -56.34  30.0  1
 65Z  Var_03    N13  C14  N1   C2    13.43  30.0  2
 65Z  Var_04    C5   C6   N1   C2    60.56  30.0  1
 65Z  Var_05    C5   C4   C3   C2   -52.92  30.0  1
 65Z  Var_06    C14  N1   C2   C3   145.95  30.0  1
 65Z  Var_07    C6   C5   C4   C3    52.72  30.0  1
 65Z  Var_08    O21  C19  C15  C14   63.40  30.0  2

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
 65Z  plan-1  C16  0.020
 65Z  plan-1  C22  0.020
 65Z  plan-1  C23  0.020
 65Z  plan-1  C24  0.020
 65Z  plan-1  C25  0.020
 65Z  plan-1  C26  0.020
 65Z  plan-1  C27  0.020
 65Z  plan-1  H14  0.020
 65Z  plan-1  H15  0.020
 65Z  plan-1  H16  0.020
 65Z  plan-1  H17  0.020
 65Z  plan-1  H18  0.020
 65Z  plan-2  N1   0.020
 65Z  plan-2  C7   0.020
 65Z  plan-2  C8   0.020
 65Z  plan-2  C9   0.020
 65Z  plan-2  C10  0.020
 65Z  plan-2  C11  0.020
 65Z  plan-2  C12  0.020
 65Z  plan-2  N13  0.020
 65Z  plan-2  C14  0.020
 65Z  plan-2  C15  0.020
 65Z  plan-2  C16  0.020
 65Z  plan-2  C19  0.020
 65Z  plan-2  C22  0.020
 65Z  plan-2  H11  0.020
 65Z  plan-2  H12  0.020
 65Z  plan-2  CL1  0.020
 65Z  plan-2  CL2  0.020
 65Z  plan-3  C15  0.020
 65Z  plan-3  C19  0.020
 65Z  plan-3  O20  0.020
 65Z  plan-3  O21  0.020

