# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr  6 17:32:57 2020
#   Inital geometry file: a 83 line input string
#   Ligand name: 2-(3-bromophenyl)-8-fluoroquinoline-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1cc(nc2c(F)cccc12)c3cccc(Br)c3
#
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
 5DN  5DN  '2-(3-bromophenyl)-8-fluoroquinoline-4-carboxylic acid'  ligand  29  21  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_5DN
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
 5DN  O01  O   OC    -1  -0.578  -3.7837  -3.1052  -0.9486
 5DN  C02  C   C      0   0.381  -4.0164  -2.1402  -0.2028
 5DN  O03  O   O      0  -0.580  -5.0214  -1.9468   0.5027
 5DN  C04  C   CR6    0   0.030  -2.9089  -1.0879  -0.1149
 5DN  C05  C   CR16   0  -0.380  -1.6078  -1.5151  -0.1389
 5DN  C06  C   CR6    0   0.242  -0.5408  -0.5994   0.0010
 5DN  C07  C   CR6    0   0.068   0.8687  -1.0549   0.0197
 5DN  C08  C   CR16   0  -0.322   1.2114  -2.3804   0.2819
 5DN  C09  C   CR16   0  -0.232   2.5406  -2.7746   0.2968
 5DN  C10  C   CR16   0  -0.237   3.5544  -1.8616   0.0493
 5DN  C11  C   CR6    0  -0.091   3.2062  -0.5427  -0.2083
 5DN  BR   BR  BR     0  -0.045   4.5700   0.7206  -0.5512
 5DN  C13  C   CR16   0  -0.259   1.8864  -0.1296  -0.2221
 5DN  N14  N   N      0  -0.457  -0.7453   0.6898   0.1018
 5DN  C15  C   CR66   0   0.015  -2.0087   1.1476   0.0845
 5DN  C16  C   CR6    0   0.508  -2.2081   2.5475   0.1577
 5DN  F17  F   F      0  -0.302  -1.1209   3.3220   0.2388
 5DN  C18  C   CR16   0  -0.432  -3.4455   3.1107   0.1415
 5DN  C19  C   CR16   0  -0.236  -4.5710   2.2678   0.0525
 5DN  C20  C   CR16   0  -0.345  -4.4368   0.9079  -0.0127
 5DN  C21  C   CR66   0   0.079  -3.1530   0.3104   0.0019
 5DN  H2   H   HCR6   0   0.264  -1.4093  -2.5687  -0.2751
 5DN  H3   H   HCR6   0   0.263   0.4491  -3.1177   0.4932
 5DN  H4   H   HCR6   0   0.274   2.7936  -3.8045   0.5097
 5DN  H5   H   HCR6   0   0.283   4.5887  -2.1775   0.0621
 5DN  H6   H   HCR6   0   0.277   1.6268   0.9010  -0.4216
 5DN  H7   H   HCR6   0   0.283  -3.5605   4.1853   0.1939
 5DN  H8   H   HCR6   0   0.268  -5.5565   2.7137   0.0368
 5DN  H9   H   HCR6   0   0.263  -5.3121   0.2806  -0.0726

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
 5DN  O03  C02  deloc     1.243  0.020  1.243
 5DN  C02  O01  deloc     1.242  0.020  1.242
 5DN  C02  C04  single    1.530  0.020  1.530
 5DN  C20  C19  aromatic  1.368  0.020  1.368
 5DN  C20  C21  aromatic  1.416  0.020  1.416
 5DN  C19  C18  aromatic  1.409  0.020  1.409
 5DN  C04  C21  aromatic  1.424  0.020  1.424
 5DN  C04  C05  aromatic  1.370  0.020  1.370
 5DN  C21  C15  aromatic  1.420  0.020  1.420
 5DN  C05  C06  aromatic  1.413  0.020  1.413
 5DN  C18  C16  aromatic  1.360  0.020  1.360
 5DN  C15  C16  aromatic  1.416  0.020  1.416
 5DN  C15  N14  aromatic  1.344  0.020  1.344
 5DN  C16  F17  single    1.337  0.020  1.337
 5DN  C06  N14  aromatic  1.309  0.020  1.309
 5DN  C06  C07  single    1.481  0.020  1.481
 5DN  C08  C07  aromatic  1.394  0.020  1.394
 5DN  C08  C09  aromatic  1.387  0.020  1.387
 5DN  C07  C13  aromatic  1.397  0.020  1.397
 5DN  C09  C10  aromatic  1.387  0.020  1.387
 5DN  C13  C11  aromatic  1.383  0.020  1.383
 5DN  C10  C11  aromatic  1.388  0.020  1.388
 5DN  C11  BR   single    1.890  0.020  1.890
 5DN  C05  H2   single    0.930  0.020  1.080
 5DN  C08  H3   single    0.930  0.020  1.080
 5DN  C09  H4   single    0.930  0.020  1.080
 5DN  C10  H5   single    0.930  0.020  1.080
 5DN  C13  H6   single    0.930  0.020  1.080
 5DN  C18  H7   single    0.930  0.020  1.080
 5DN  C19  H8   single    0.930  0.020  1.080
 5DN  C20  H9   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
 5DN  C04  C02  O03  116.46  3.000
 5DN  C04  C02  O01  115.67  3.000
 5DN  O03  C02  O01  127.84  3.000
 5DN  C21  C04  C05  118.07  3.000
 5DN  C05  C04  C02  118.17  3.000
 5DN  C21  C04  C02  123.76  3.000
 5DN  H2   C05  C06  120.37  3.000
 5DN  H2   C05  C04  118.73  3.000
 5DN  C06  C05  C04  120.89  3.000
 5DN  N14  C06  C07  116.78  3.000
 5DN  C07  C06  C05  121.36  3.000
 5DN  N14  C06  C05  121.86  3.000
 5DN  C13  C07  C08  118.91  3.000
 5DN  C13  C07  C06  119.17  3.000
 5DN  C08  C07  C06  121.92  3.000
 5DN  H3   C08  C09  118.68  3.000
 5DN  H3   C08  C07  120.78  3.000
 5DN  C09  C08  C07  120.53  3.000
 5DN  H4   C09  C10  119.41  3.000
 5DN  H4   C09  C08  119.80  3.000
 5DN  C10  C09  C08  120.78  3.000
 5DN  H5   C10  C11  121.31  3.000
 5DN  H5   C10  C09  120.31  3.000
 5DN  C11  C10  C09  118.38  3.000
 5DN  C13  C11  BR   119.15  3.000
 5DN  BR   C11  C10  119.18  3.000
 5DN  C13  C11  C10  121.67  3.000
 5DN  H6   C13  C11  121.04  3.000
 5DN  H6   C13  C07  119.23  3.000
 5DN  C11  C13  C07  119.73  3.000
 5DN  C15  N14  C06  118.77  3.000
 5DN  C21  C15  C16  118.19  3.000
 5DN  C16  C15  N14  117.94  3.000
 5DN  C21  C15  N14  123.87  3.000
 5DN  C18  C16  F17  120.04  3.000
 5DN  F17  C16  C15  117.47  3.000
 5DN  C18  C16  C15  122.48  3.000
 5DN  H7   C18  C19  120.82  3.000
 5DN  H7   C18  C16  120.50  3.000
 5DN  C19  C18  C16  118.68  3.000
 5DN  H8   C19  C20  119.89  3.000
 5DN  H8   C19  C18  118.82  3.000
 5DN  C20  C19  C18  121.29  3.000
 5DN  H9   C20  C21  119.40  3.000
 5DN  H9   C20  C19  120.08  3.000
 5DN  C21  C20  C19  120.52  3.000
 5DN  C20  C21  C15  118.84  3.000
 5DN  C15  C21  C04  116.45  3.000
 5DN  C20  C21  C04  124.67  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
 5DN  CONST_01  C19  C20  C21  C04  180.00   0.0  0
 5DN  CONST_02  C16  C15  C21  C04  180.00   0.0  0
 5DN  CONST_03  N14  C15  C21  C04    0.00   0.0  0
 5DN  CONST_04  N14  C06  C05  C04    0.00   0.0  0
 5DN  CONST_05  C07  C06  C05  C04  180.00   0.0  0
 5DN  CONST_06  C20  C21  C04  C05  180.00   0.0  0
 5DN  CONST_07  C15  C21  C04  C05    0.00   0.0  0
 5DN  CONST_08  C15  N14  C06  C05    0.00   0.0  0
 5DN  CONST_11  C21  C04  C05  C06    0.00   0.0  0
 5DN  CONST_12  C21  C15  N14  C06    0.00   0.0  0
 5DN  CONST_13  C16  C15  N14  C06  180.00   0.0  0
 5DN  CONST_14  C09  C08  C07  C06  180.00   0.0  0
 5DN  CONST_15  C11  C13  C07  C06  180.00   0.0  0
 5DN  CONST_16  C15  N14  C06  C07  180.00   0.0  0
 5DN  CONST_17  C10  C09  C08  C07    0.00   0.0  0
 5DN  CONST_18  C10  C11  C13  C07    0.00   0.0  0
 5DN  CONST_20  C11  C13  C07  C08    0.00   0.0  0
 5DN  CONST_21  C11  C10  C09  C08    0.00   0.0  0
 5DN  CONST_22  C13  C07  C08  C09    0.00   0.0  0
 5DN  CONST_23  C13  C11  C10  C09    0.00   0.0  0
 5DN  CONST_25  C20  C21  C15  N14  180.00   0.0  0
 5DN  CONST_26  C18  C16  C15  N14  180.00   0.0  0
 5DN  CONST_27  C19  C20  C21  C15    0.00   0.0  0
 5DN  CONST_28  C19  C18  C16  C15    0.00   0.0  0
 5DN  CONST_29  C20  C19  C18  C16    0.00   0.0  0
 5DN  CONST_30  C20  C21  C15  C16    0.00   0.0  0
 5DN  CONST_31  C21  C20  C19  C18    0.00   0.0  0
 5DN  CONST_32  C21  C15  C16  C18    0.00   0.0  0
 5DN  CONST_33  C20  C21  C04  C02    0.00   0.0  0
 5DN  CONST_34  C15  C21  C04  C02  180.00   0.0  0
 5DN  CONST_35  C06  C05  C04  C02  180.00   0.0  0
 5DN  CONST_36  BR   C11  C13  C07  180.00   0.0  0
 5DN  CONST_37  BR   C11  C10  C09  180.00   0.0  0
 5DN  CONST_38  F17  C16  C15  N14    0.00   0.0  0
 5DN  CONST_39  C19  C18  C16  F17  180.00   0.0  0
 5DN  CONST_40  C21  C15  C16  F17  180.00   0.0  0
 5DN  CONST_41  H9   C20  C21  C04    0.00   0.0  0
 5DN  CONST_42  H3   C08  C07  C06    0.00   0.0  0
 5DN  CONST_43  H6   C13  C07  C06    0.00   0.0  0
 5DN  CONST_44  H2   C05  C06  C07    0.00   0.0  0
 5DN  CONST_45  H4   C09  C08  C07  180.00   0.0  0
 5DN  CONST_46  H5   C10  C09  C08  180.00   0.0  0
 5DN  CONST_47  H7   C18  C16  C15  180.00   0.0  0
 5DN  CONST_48  H8   C19  C18  C16  180.00   0.0  0
 5DN  Var_01    C21  C04  C02  O01  143.67  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
 5DN  plan-1  C06  0.020
 5DN  plan-1  C07  0.020
 5DN  plan-1  C08  0.020
 5DN  plan-1  C09  0.020
 5DN  plan-1  C10  0.020
 5DN  plan-1  C11  0.020
 5DN  plan-1  BR   0.020
 5DN  plan-1  C13  0.020
 5DN  plan-1  H3   0.020
 5DN  plan-1  H4   0.020
 5DN  plan-1  H5   0.020
 5DN  plan-1  H6   0.020
 5DN  plan-2  C02  0.020
 5DN  plan-2  C04  0.020
 5DN  plan-2  C05  0.020
 5DN  plan-2  C06  0.020
 5DN  plan-2  C07  0.020
 5DN  plan-2  N14  0.020
 5DN  plan-2  C15  0.020
 5DN  plan-2  C16  0.020
 5DN  plan-2  F17  0.020
 5DN  plan-2  C18  0.020
 5DN  plan-2  C19  0.020
 5DN  plan-2  C20  0.020
 5DN  plan-2  C21  0.020
 5DN  plan-2  H2   0.020
 5DN  plan-2  H7   0.020
 5DN  plan-2  H8   0.020
 5DN  plan-2  H9   0.020
 5DN  plan-3  O01  0.020
 5DN  plan-3  C02  0.020
 5DN  plan-3  O03  0.020
 5DN  plan-3  C04  0.020

