# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Mar 19 18:26:21 2022
#   Inital geometry file: a 88 line input string
#   Ligand name: {4-[(6-chloroquinoxalin-2-yl)oxy]phenyl}acetic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)Cc1ccc(Oc2cnc3cc(Cl)ccc3n2)cc1
#
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
 OWD  OWD  '{4-[(6-chloroquinoxalin-2-yl)oxy]phenyl}acetic acid'  ligand  32  22  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_OWD
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
 OWD  C10   C   CR6    0   0.438   1.9762  -58.8904  52.4351
 OWD  N12   N   N      0  -0.372   2.9197  -57.2069  53.8181
 OWD  C13   C   CR66   0   0.221   2.3379  -56.3052  52.9821
 OWD  C15   C   CR6    0  -0.045   1.9136  -54.0294  52.3857
 OWD  C17   C   CR16   0  -0.207   1.1483  -54.4469  51.2821
 OWD  C21   C   CR16   0  -0.291   1.8402  -60.9505  50.0017
 OWD  C22   C   CR16   0  -0.312   1.1380  -61.4910  48.9333
 OWD  C02   C   C      0   0.417  -1.0234  -63.9430  47.8815
 OWD  C05   C   CR6    0   0.179  -0.2192  -61.7900  49.0296
 OWD  C06   C   CR16   0  -0.311  -0.8573  -61.5324  50.2412
 OWD  C07   C   CR16   0  -0.295  -0.1746  -60.9883  51.3190
 OWD  C08   C   CR6    0   0.326   1.1738  -60.7051  51.1885
 OWD  C11   C   CR16   0  -0.135   2.7494  -58.4623  53.5612
 OWD  C14   C   CR16   0  -0.261   2.5035  -54.9306  53.2302
 OWD  C18   C   CR16   0  -0.311   0.9845  -55.7839  51.0333
 OWD  C19   C   CR66   0   0.253   1.5768  -56.7414  51.8773
 OWD  N20   N   N      0  -0.430   1.4115  -58.0638  51.6226
 OWD  O01   O   OC    -1  -0.592  -0.7624  -64.5235  48.9494
 OWD  O03   O   O      0  -0.612  -1.3643  -64.4590  46.8001
 OWD  O09   O   O2     0  -0.512   1.8773  -60.2136  52.2762
 OWD  CL16  CL  CL     0  -0.115   2.1039  -52.3331  52.6673
 OWD  H1    H   HCR6   0   0.289   0.6917  -53.7116  50.6336
 OWD  H2    H   HCR6   0   0.264   2.8953  -60.7247  49.9095
 OWD  H3    H   HCR6   0   0.249   1.6610  -61.6807  48.0033
 OWD  H4    H   HCH2   0   0.235  -0.5160  -62.0573  46.9325
 OWD  H5    H   HCH2   0   0.245  -1.9897  -62.0234  47.8689
 OWD  H6    H   HCR6   0   0.247  -1.9134  -61.7506  50.3454
 OWD  H7    H   HCR6   0   0.264  -0.6848  -60.7906  52.2534
 OWD  H8    H   HCR6   0   0.291   3.2071  -59.1958  54.2166
 OWD  H9    H   HCR6   0   0.289   3.0926  -54.6157  54.0813
 OWD  H10   H   HCR6   0   0.278   0.3990  -56.1186  50.1872
 OWD  C04   C   CH2    0  -0.688  -0.9571  -62.3887  47.8755

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
 OWD  O03  C02   deloc     1.246  0.020  1.246
 OWD  C02  C04   single    1.556  0.020  1.556
 OWD  C02  O01   deloc     1.243  0.020  1.243
 OWD  C04  C05   single    1.495  0.020  1.495
 OWD  C22  C05   aromatic  1.393  0.020  1.393
 OWD  C22  C21   aromatic  1.388  0.020  1.388
 OWD  C05  C06   aromatic  1.393  0.020  1.393
 OWD  C21  C08   aromatic  1.383  0.020  1.383
 OWD  C06  C07   aromatic  1.387  0.020  1.387
 OWD  C18  C17   aromatic  1.370  0.020  1.370
 OWD  C18  C19   aromatic  1.407  0.020  1.407
 OWD  C17  C15   aromatic  1.406  0.020  1.406
 OWD  C08  C07   aromatic  1.384  0.020  1.384
 OWD  C08  O09   single    1.386  0.020  1.386
 OWD  N20  C19   aromatic  1.357  0.020  1.357
 OWD  N20  C10   aromatic  1.289  0.020  1.289
 OWD  C19  C13   aromatic  1.411  0.020  1.411
 OWD  C15  CL16  single    1.730  0.020  1.730
 OWD  C15  C14   aromatic  1.369  0.020  1.369
 OWD  O09  C10   single    1.336  0.020  1.336
 OWD  C10  C11   aromatic  1.432  0.020  1.432
 OWD  C13  C14   aromatic  1.407  0.020  1.407
 OWD  C13  N12   aromatic  1.360  0.020  1.360
 OWD  C11  N12   aromatic  1.293  0.020  1.293
 OWD  C17  H1    single    0.930  0.020  1.080
 OWD  C21  H2    single    0.930  0.020  1.080
 OWD  C22  H3    single    0.930  0.020  1.080
 OWD  C04  H4    single    0.970  0.020  1.090
 OWD  C04  H5    single    0.970  0.020  1.090
 OWD  C06  H6    single    0.930  0.020  1.080
 OWD  C07  H7    single    0.930  0.020  1.080
 OWD  C11  H8    single    0.930  0.020  1.080
 OWD  C14  H9    single    0.930  0.020  1.080
 OWD  C18  H10   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
 OWD  O09   C10  N20  121.83  3.000
 OWD  O09   C10  C11  115.44  3.000
 OWD  N20   C10  C11  122.73  3.000
 OWD  C11   N12  C13  117.73  3.000
 OWD  C19   C13  C14  120.25  3.000
 OWD  C14   C13  N12  119.28  3.000
 OWD  C19   C13  N12  120.47  3.000
 OWD  CL16  C15  C14  119.85  3.000
 OWD  C14   C15  C17  121.55  3.000
 OWD  CL16  C15  C17  118.60  3.000
 OWD  H1    C17  C18  120.28  3.000
 OWD  H1    C17  C15  119.90  3.000
 OWD  C18   C17  C15  119.82  3.000
 OWD  H2    C21  C08  120.37  3.000
 OWD  H2    C21  C22  120.56  3.000
 OWD  C08   C21  C22  119.07  3.000
 OWD  H3    C22  C05  119.47  3.000
 OWD  H3    C22  C21  118.99  3.000
 OWD  C05   C22  C21  121.54  3.000
 OWD  O03   C02  O01  127.57  3.000
 OWD  O01   C02  C04  117.45  3.000
 OWD  O03   C02  C04  114.97  3.000
 OWD  C06   C05  C04  121.29  3.000
 OWD  C06   C05  C22  117.82  3.000
 OWD  C04   C05  C22  120.89  3.000
 OWD  H6    C06  C07  118.95  3.000
 OWD  H6    C06  C05  119.53  3.000
 OWD  C07   C06  C05  121.52  3.000
 OWD  H7    C07  C08  120.20  3.000
 OWD  H7    C07  C06  120.68  3.000
 OWD  C08   C07  C06  119.12  3.000
 OWD  O09   C08  C07  119.55  3.000
 OWD  O09   C08  C21  119.47  3.000
 OWD  C07   C08  C21  120.93  3.000
 OWD  H8    C11  N12  118.75  3.000
 OWD  H8    C11  C10  120.06  3.000
 OWD  N12   C11  C10  121.19  3.000
 OWD  H9    C14  C15  121.90  3.000
 OWD  H9    C14  C13  119.16  3.000
 OWD  C15   C14  C13  118.94  3.000
 OWD  H10   C18  C19  119.10  3.000
 OWD  H10   C18  C17  120.57  3.000
 OWD  C19   C18  C17  120.33  3.000
 OWD  N20   C19  C18  119.96  3.000
 OWD  N20   C19  C13  120.94  3.000
 OWD  C18   C19  C13  119.10  3.000
 OWD  C19   N20  C10  116.95  3.000
 OWD  C08   O09  C10  118.82  3.000
 OWD  H5    C04  H4   105.92  3.000
 OWD  H5    C04  C05  109.66  3.000
 OWD  H4    C04  C05  110.22  3.000
 OWD  H5    C04  C02  107.04  3.000
 OWD  H4    C04  C02  108.88  3.000
 OWD  C05   C04  C02  114.72  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
 OWD  CONST_01  C18   C19  N20  C10   180.00   0.0  0
 OWD  CONST_02  C13   C19  N20  C10     0.00   0.0  0
 OWD  CONST_03  C13   N12  C11  C10     0.00   0.0  0
 OWD  CONST_04  C18   C19  C13  N12   180.00   0.0  0
 OWD  CONST_05  N20   C19  C13  N12     0.00   0.0  0
 OWD  CONST_06  C15   C14  C13  N12   180.00   0.0  0
 OWD  CONST_07  N20   C10  C11  N12     0.00   0.0  0
 OWD  CONST_08  C17   C18  C19  C13     0.00   0.0  0
 OWD  CONST_09  C17   C15  C14  C13     0.00   0.0  0
 OWD  CONST_10  C19   C18  C17  C15     0.00   0.0  0
 OWD  CONST_11  C19   C13  C14  C15     0.00   0.0  0
 OWD  CONST_12  N20   C19  C18  C17   180.00   0.0  0
 OWD  CONST_13  C06   C05  C22  C21     0.00   0.0  0
 OWD  CONST_14  C06   C07  C08  C21     0.00   0.0  0
 OWD  CONST_15  C07   C06  C05  C22     0.00   0.0  0
 OWD  CONST_16  C07   C08  C21  C22     0.00   0.0  0
 OWD  CONST_17  C08   C21  C22  C05     0.00   0.0  0
 OWD  CONST_18  C08   C07  C06  C05     0.00   0.0  0
 OWD  CONST_19  C19   N20  C10  C11     0.00   0.0  0
 OWD  CONST_20  C19   C13  N12  C11     0.00   0.0  0
 OWD  CONST_21  C14   C13  N12  C11   180.00   0.0  0
 OWD  CONST_22  C18   C17  C15  C14     0.00   0.0  0
 OWD  CONST_23  C18   C19  C13  C14     0.00   0.0  0
 OWD  CONST_24  N20   C19  C13  C14   180.00   0.0  0
 OWD  CONST_25  O09   C10  C11  N12   180.00   0.0  0
 OWD  CONST_26  CL16  C15  C14  C13   180.00   0.0  0
 OWD  CONST_27  C04   C05  C22  C21   180.00   0.0  0
 OWD  CONST_28  O09   C08  C21  C22   180.00   0.0  0
 OWD  CONST_29  C07   C06  C05  C04   180.00   0.0  0
 OWD  CONST_30  O09   C08  C07  C06   180.00   0.0  0
 OWD  CONST_31  CL16  C15  C17  C18   180.00   0.0  0
 OWD  CONST_32  O09   C10  N20  C19   180.00   0.0  0
 OWD  CONST_33  H9    C14  C13  N12     0.00   0.0  0
 OWD  CONST_34  H10   C18  C19  C13   180.00   0.0  0
 OWD  CONST_35  H8    C11  N12  C13   180.00   0.0  0
 OWD  CONST_36  H7    C07  C08  C21   180.00   0.0  0
 OWD  CONST_37  H6    C06  C05  C22   180.00   0.0  0
 OWD  CONST_38  H2    C21  C22  C05   180.00   0.0  0
 OWD  CONST_39  H3    C22  C05  C06   180.00   0.0  0
 OWD  CONST_40  H1    C17  C15  C14   180.00   0.0  0
 OWD  Var_01    C21   C08  O09  C10    90.36  30.0  2
 OWD  Var_02    N20   C10  O09  C08     1.57  30.0  2
 OWD  Var_03    C02   C04  C05  C22    93.05  30.0  2
 OWD  Var_04    O03   C02  C04  C05  -164.78  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
 OWD  plan-1  C21   0.020
 OWD  plan-1  C22   0.020
 OWD  plan-1  C05   0.020
 OWD  plan-1  C06   0.020
 OWD  plan-1  C07   0.020
 OWD  plan-1  C08   0.020
 OWD  plan-1  O09   0.020
 OWD  plan-1  H2    0.020
 OWD  plan-1  H3    0.020
 OWD  plan-1  H6    0.020
 OWD  plan-1  H7    0.020
 OWD  plan-1  C04   0.020
 OWD  plan-2  C10   0.020
 OWD  plan-2  N12   0.020
 OWD  plan-2  C13   0.020
 OWD  plan-2  C15   0.020
 OWD  plan-2  C17   0.020
 OWD  plan-2  C11   0.020
 OWD  plan-2  C14   0.020
 OWD  plan-2  C18   0.020
 OWD  plan-2  C19   0.020
 OWD  plan-2  N20   0.020
 OWD  plan-2  O09   0.020
 OWD  plan-2  CL16  0.020
 OWD  plan-2  H1    0.020
 OWD  plan-2  H8    0.020
 OWD  plan-2  H9    0.020
 OWD  plan-2  H10   0.020
 OWD  plan-3  C02   0.020
 OWD  plan-3  O01   0.020
 OWD  plan-3  O03   0.020
 OWD  plan-3  C04   0.020

