# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 26 16:42:19 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  30  21  .  2021-08-04  2022-11-17
;
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   OH1   0  -0.579  -3.7550  -3.1874  -0.5677
 5DN  C02  C   C     0   0.499  -4.0208  -2.0866   0.1126
 5DN  O03  O   O     0  -0.420  -5.0283  -1.9123   0.7491
 5DN  C04  C   CR6   0   0.062  -2.9085  -1.0927   0.0265
 5DN  C05  C   CR16  0  -0.351  -1.6192  -1.5482   0.0166
 5DN  C06  C   CR6   0   0.260  -0.5405  -0.6299   0.0265
 5DN  C07  C   CR6   0   0.068   0.8700  -1.0834   0.0389
 5DN  C08  C   CR16  0  -0.338   1.2199  -2.4320   0.0842
 5DN  C09  C   CR16  0  -0.227   2.5526  -2.8145   0.0934
 5DN  C10  C   CR16  0  -0.236   3.5637  -1.8673   0.0578
 5DN  C11  C   CR6   0  -0.090   3.2092  -0.5256   0.0130
 5DN  BR   BR  BR    0  -0.040   4.5677   0.7864  -0.0355
 5DN  C13  C   CR16  0  -0.249   1.8863  -0.1250   0.0032
 5DN  N14  N   N     0  -0.450  -0.7502   0.6596   0.0225
 5DN  C15  C   CR66  0   0.019  -2.0061   1.1324   0.0066
 5DN  C16  C   CR6   0   0.522  -2.1857   2.5359  -0.0246
 5DN  F17  F   F     0  -0.295  -1.0895   3.2964  -0.0263
 5DN  C18  C   CR16  0  -0.427  -3.4177   3.1100  -0.0604
 5DN  C19  C   CR16  0  -0.230  -4.5520   2.2766  -0.0664
 5DN  C20  C   CR16  0  -0.349  -4.4377   0.9131  -0.0277
 5DN  C21  C   CR66  0   0.116  -3.1613   0.3076   0.0164
 5DN  H1   H   HOH1  0   0.495  -4.4621  -3.8393  -0.4420
 5DN  H2   H   HCR6  0   0.291  -1.4311  -2.6108   0.0211
 5DN  H3   H   HCR6  0   0.268   0.4679  -3.2070   0.1143
 5DN  H4   H   HCR6  0   0.277   2.8073  -3.8651   0.1298
 5DN  H5   H   HCR6  0   0.285   4.6007  -2.1746   0.0649
 5DN  H6   H   HCR6  0   0.281   1.6224   0.9229  -0.0323
 5DN  H7   H   HCR6  0   0.291  -3.5220   4.1864  -0.0888
 5DN  H8   H   HCR6  0   0.279  -5.5327   2.7310  -0.1040
 5DN  H9   H   HCR6  0   0.269  -5.3313   0.3092  -0.0348

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  double    1.204  0.020  1.204
 5DN  C02  O01  single    1.321  0.020  1.321
 5DN  C02  C04  single    1.494  0.020  1.494
 5DN  C20  C19  aromatic  1.369  0.020  1.369
 5DN  C20  C21  aromatic  1.413  0.020  1.413
 5DN  C19  C18  aromatic  1.408  0.020  1.408
 5DN  C04  C21  aromatic  1.423  0.020  1.423
 5DN  C04  C05  aromatic  1.367  0.020  1.367
 5DN  C21  C15  aromatic  1.419  0.020  1.419
 5DN  C05  C06  aromatic  1.417  0.020  1.417
 5DN  C18  C16  aromatic  1.360  0.020  1.360
 5DN  C15  C16  aromatic  1.415  0.020  1.415
 5DN  C15  N14  aromatic  1.342  0.020  1.342
 5DN  C16  F17  single    1.334  0.020  1.334
 5DN  C06  N14  aromatic  1.307  0.020  1.307
 5DN  C06  C07  single    1.482  0.020  1.482
 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  1.386  0.020  1.386
 5DN  C13  C11  aromatic  1.382  0.020  1.382
 5DN  C10  C11  aromatic  1.388  0.020  1.388
 5DN  C11  BR   single    1.889  0.020  1.889
 5DN  O01  H1   single    0.850  0.020  0.980
 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  H1   O01  C02  110.28  3.000
 5DN  C04  C02  O03  123.84  3.000
 5DN  C04  C02  O01  112.01  3.000
 5DN  O03  C02  O01  124.13  3.000
 5DN  C21  C04  C05  119.68  3.000
 5DN  C05  C04  C02  118.73  3.000
 5DN  C21  C04  C02  121.52  3.000
 5DN  H2   C05  C06  120.36  3.000
 5DN  H2   C05  C04  119.50  3.000
 5DN  C06  C05  C04  120.13  3.000
 5DN  N14  C06  C07  117.05  3.000
 5DN  C07  C06  C05  121.78  3.000
 5DN  N14  C06  C05  121.17  3.000
 5DN  C13  C07  C08  118.81  3.000
 5DN  C13  C07  C06  118.83  3.000
 5DN  C08  C07  C06  122.36  3.000
 5DN  H3   C08  C09  118.10  3.000
 5DN  H3   C08  C07  121.35  3.000
 5DN  C09  C08  C07  120.55  3.000
 5DN  H4   C09  C10  119.53  3.000
 5DN  H4   C09  C08  119.64  3.000
 5DN  C10  C09  C08  120.83  3.000
 5DN  H5   C10  C11  121.31  3.000
 5DN  H5   C10  C09  120.34  3.000
 5DN  C11  C10  C09  118.36  3.000
 5DN  C13  C11  BR   119.13  3.000
 5DN  BR   C11  C10  119.23  3.000
 5DN  C13  C11  C10  121.65  3.000
 5DN  H6   C13  C11  120.98  3.000
 5DN  H6   C13  C07  119.21  3.000
 5DN  C11  C13  C07  119.81  3.000
 5DN  C15  N14  C06  119.86  3.000
 5DN  C21  C15  C16  118.24  3.000
 5DN  C16  C15  N14  117.93  3.000
 5DN  C21  C15  N14  123.83  3.000
 5DN  C18  C16  F17  120.24  3.000
 5DN  F17  C16  C15  117.46  3.000
 5DN  C18  C16  C15  122.30  3.000
 5DN  H7   C18  C19  120.75  3.000
 5DN  H7   C18  C16  120.54  3.000
 5DN  C19  C18  C16  118.70  3.000
 5DN  H8   C19  C20  119.68  3.000
 5DN  H8   C19  C18  118.82  3.000
 5DN  C20  C19  C18  121.49  3.000
 5DN  H9   C20  C21  120.57  3.000
 5DN  H9   C20  C19  119.23  3.000
 5DN  C21  C20  C19  120.20  3.000
 5DN  C20  C21  C15  119.07  3.000
 5DN  C15  C21  C04  115.30  3.000
 5DN  C20  C21  C04  125.60  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_09  C08  C07  C06  C05    0.00   0.0  0
 5DN  CONST_10  C13  C07  C06  C05  180.00   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_19  N14  C06  C07  C08  180.00   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_24  N14  C06  C07  C13    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  CONST_49  H1   O01  C02  C04  180.00   0.0  0
 5DN  Var_01    C21  C04  C02  O01  146.12  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
 5DN  plan-3  H1   0.020

