# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 05:21:47 2021
#   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  33  22  .  2022-03-23  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

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   1.9630  -58.9440  52.4342
 OWD  N12   N   N     0  -0.375   2.8848  -57.2620  53.8297
 OWD  C13   C   CR66  0   0.222   2.3248  -56.3608  52.9788
 OWD  C15   C   CR6   0  -0.045   1.9272  -54.0862  52.3625
 OWD  C17   C   CR16  0  -0.208   1.1880  -54.5038  51.2413
 OWD  C21   C   CR16  0  -0.288   1.7785  -60.8717  49.9595
 OWD  C22   C   CR16  0  -0.293   1.0711  -61.4056  48.8933
 OWD  C02   C   C     0   0.558  -0.8059  -63.8792  47.6546
 OWD  C05   C   CR6   0   0.133  -0.2497  -61.8192  49.0425
 OWD  C06   C   CR16  0  -0.297  -0.8524  -61.6870  50.2884
 OWD  C07   C   CR16  0  -0.293  -0.1595  -61.1511  51.3645
 OWD  C08   C   CR6   0   0.339   1.1528  -60.7515  51.1885
 OWD  C11   C   CR16  0  -0.132   2.7157  -58.5179  53.5736
 OWD  C14   C   CR16  0  -0.261   2.4915  -54.9861  53.2255
 OWD  C18   C   CR16  0  -0.312   1.0198  -55.8409  50.9961
 OWD  C19   C   CR66  0   0.253   1.5848  -56.7973  51.8597
 OWD  N20   N   N     0  -0.427   1.4156  -58.1199  51.6089
 OWD  O01   O   OH1   0  -0.580  -0.4374  -64.5247  48.7505
 OWD  O03   O   O     0  -0.451  -0.9993  -64.4229  46.5957
 OWD  O09   O   O2    0  -0.513   1.8571  -60.2689  52.2757
 OWD  CL16  CL  CL    0  -0.115   2.1194  -52.3895  52.6424
 OWD  H1    H   HCR6  0   0.290   0.7548  -53.7694  50.5762
 OWD  H2    H   HCR6  0   0.274   2.8056  -60.5551  49.8310
 OWD  H3    H   HCR6  0   0.263   1.5583  -61.4955  47.9299
 OWD  H4    H   HCH2  0   0.297  -0.7313  -61.8906  46.9494
 OWD  H5    H   HCH2  0   0.308  -2.0754  -62.2440  48.0060
 OWD  H6    H   HCR6  0   0.262  -1.8801  -61.9993  50.4269
 OWD  H7    H   HCR6  0   0.273  -0.6368  -61.0506  52.3308
 OWD  H8    H   HCR6  0   0.294   3.1553  -59.2512  54.2408
 OWD  H9    H   HCR6  0   0.292   3.0592  -54.6701  54.0904
 OWD  H10   H   HCR6  0   0.281   0.4556  -56.1758  50.1358
 OWD  H11   H   HOH1  0   0.481  -0.3637  -65.4733  48.5646
 OWD  C04   C   CH2   0  -0.669  -0.9990  -62.3977  47.8772

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   double    1.206  0.020  1.206
 OWD  C02  C04   single    1.511  0.020  1.511
 OWD  C02  O01   single    1.324  0.020  1.324
 OWD  C04  C05   single    1.501  0.020  1.501
 OWD  C22  C05   aromatic  1.392  0.020  1.392
 OWD  C22  C21   aromatic  1.386  0.020  1.386
 OWD  C05  C06   aromatic  1.390  0.020  1.390
 OWD  C21  C08   aromatic  1.384  0.020  1.384
 OWD  C06  C07   aromatic  1.388  0.020  1.388
 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  1.383  0.020  1.383
 OWD  C08  O09   single    1.382  0.020  1.382
 OWD  N20  C19   aromatic  1.357  0.020  1.357
 OWD  N20  C10   aromatic  1.288  0.020  1.288
 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    1.339  0.020  1.339
 OWD  C10  C11   aromatic  1.430  0.020  1.430
 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
 OWD  O01  H11   single    0.850  0.020  0.980

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  121.58  3.000
 OWD  O09   C10  C11  115.52  3.000
 OWD  N20   C10  C11  122.90  3.000
 OWD  C11   N12  C13  117.76  3.000
 OWD  C19   C13  C14  120.24  3.000
 OWD  C14   C13  N12  119.27  3.000
 OWD  C19   C13  N12  120.48  3.000
 OWD  CL16  C15  C14  119.80  3.000
 OWD  C14   C15  C17  121.61  3.000
 OWD  CL16  C15  C17  118.59  3.000
 OWD  H1    C17  C18  120.24  3.000
 OWD  H1    C17  C15  119.95  3.000
 OWD  C18   C17  C15  119.81  3.000
 OWD  H2    C21  C08  120.58  3.000
 OWD  H2    C21  C22  120.37  3.000
 OWD  C08   C21  C22  119.05  3.000
 OWD  H3    C22  C05  119.82  3.000
 OWD  H3    C22  C21  119.10  3.000
 OWD  C05   C22  C21  121.07  3.000
 OWD  O03   C02  O01  123.47  3.000
 OWD  O01   C02  C04  113.06  3.000
 OWD  O03   C02  C04  123.44  3.000
 OWD  C06   C05  C04  121.05  3.000
 OWD  C06   C05  C22  118.63  3.000
 OWD  C04   C05  C22  120.32  3.000
 OWD  H6    C06  C07  119.08  3.000
 OWD  H6    C06  C05  119.91  3.000
 OWD  C07   C06  C05  121.01  3.000
 OWD  H7    C07  C08  120.34  3.000
 OWD  H7    C07  C06  120.53  3.000
 OWD  C08   C07  C06  119.13  3.000
 OWD  O09   C08  C07  118.96  3.000
 OWD  O09   C08  C21  119.89  3.000
 OWD  C07   C08  C21  121.11  3.000
 OWD  H8    C11  N12  118.81  3.000
 OWD  H8    C11  C10  120.12  3.000
 OWD  N12   C11  C10  121.07  3.000
 OWD  H9    C14  C15  121.90  3.000
 OWD  H9    C14  C13  119.21  3.000
 OWD  C15   C14  C13  118.89  3.000
 OWD  H10   C18  C19  119.15  3.000
 OWD  H10   C18  C17  120.56  3.000
 OWD  C19   C18  C17  120.29  3.000
 OWD  N20   C19  C18  119.94  3.000
 OWD  N20   C19  C13  120.90  3.000
 OWD  C18   C19  C13  119.16  3.000
 OWD  C19   N20  C10  116.88  3.000
 OWD  H11   O01  C02  109.84  3.000
 OWD  C08   O09  C10  118.62  3.000
 OWD  H5    C04  H4   106.03  3.000
 OWD  H5    C04  C05  110.19  3.000
 OWD  H4    C04  C05  111.02  3.000
 OWD  H5    C04  C02  106.30  3.000
 OWD  H4    C04  C02  107.41  3.000
 OWD  C05   C04  C02  115.37  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  CONST_41  H11   O01  C02  C04   180.00   0.0  0
 OWD  Var_01    C21   C08  O09  C10    83.71  30.0  1
 OWD  Var_02    N20   C10  O09  C08     0.70  30.0  2
 OWD  Var_03    C02   C04  C05  C22    85.45  30.0  3
 OWD  Var_04    O03   C02  C04  C05  -158.02  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  H11   0.020
 OWD  plan-3  C04   0.020

