# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr 29 00:49:03 2020
#   Inital geometry file: a 121 line input string
#   Ligand name: 3-[2-(4-fluorophenyl)-3-(methylcarbamoyl)-1-benzofuran-5-yl]benzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CNC(=O)c1c(oc2ccc(cc12)c3cccc(c3)C(O)=O)c4ccc(F)cc4
#
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
 8XS  8XS  '3-[2-(4-fluorophenyl)-3-(methylcarbamoyl)-1-benzofuran-5-yl]benzoic acid'  ligand  45  29  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_8XS
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
 8XS  C13  C  CR16  0  -0.330   4.5064  -0.4135   0.2677
 8XS  C17  C  CR16  0  -0.321   1.8650  -1.7266  -0.2879
 8XS  C19  C  CR16  0  -0.269  -4.5046  -1.8708  -0.3396
 8XS  C20  C  CR16  0  -0.308  -4.7418   0.3942   0.4238
 8XS  C22  C  CR6   0   0.528  -6.6676  -0.9516   0.0415
 8XS  C23  C  CR16  0  -0.397  -5.8809  -2.0207  -0.3402
 8XS  C24  C  CR16  0  -0.393  -6.1190   0.2572   0.4248
 8XS  C11  C  CR6   0  -0.060   5.7996   0.0954   0.1895
 8XS  C12  C  CR6   0   0.111   3.4507   0.2021  -0.3981
 8XS  C27  C  CR16  0  -0.301   3.7204   1.3446  -1.1538
 8XS  C1   C  CR5   0  -0.186  -1.6105   0.5407  -0.0267
 8XS  C2   C  CR5   0   0.440  -2.4611  -0.5215   0.0106
 8XS  C3   C  CR56  0   0.137  -0.2873  -0.0069  -0.1376
 8XS  O4   O  O     0  -0.471  -1.7660  -1.6906  -0.0487
 8XS  C5   C  CR56  0   0.358  -0.4556  -1.3886  -0.1336
 8XS  C6   C  C     0   0.399  -1.8885   2.0032  -0.0946
 8XS  C7   C  CR16  0  -0.422   0.9936   0.5317  -0.2247
 8XS  C8   C  C     0   0.535   6.8711  -0.6093   0.9382
 8XS  C9   C  CR6   0   0.082   2.0777  -0.3349  -0.3015
 8XS  C10  C  CR6   0  -0.024  -3.9115  -0.6615   0.0386
 8XS  C14  C  CR16  0  -0.324   0.5991  -2.2792  -0.2040
 8XS  O15  O  O     0  -0.462  -1.7708   2.6183  -1.1437
 8XS  O16  O  O     0  -0.437   6.6883  -1.6097   1.5903
 8XS  N18  N  NH1   0  -0.607  -2.2136   2.5782   1.0676
 8XS  O21  O  OH1   0  -0.593   8.0545  -0.0253   0.8210
 8XS  C26  C  CR16  0  -0.275   6.0507   1.2396  -0.5650
 8XS  C28  C  CR16  0  -0.226   5.0056   1.8573  -1.2337
 8XS  C29  C  CH3   0  -0.519  -2.4611   3.9968   1.1901
 8XS  H31  H  HCR6  0   0.265   4.3208  -1.2904   0.8747
 8XS  H33  H  HCR6  0   0.265   2.7144  -2.3925  -0.3654
 8XS  H35  H  HCR6  0   0.274  -3.8990  -2.7106  -0.6501
 8XS  H36  H  HCR6  0   0.267  -4.3264   1.3372   0.7472
 8XS  H38  H  HCR6  0   0.288  -6.3313  -2.9573  -0.6407
 8XS  H39  H  HCR6  0   0.288  -6.7528   1.0796   0.7286
 8XS  H41  H  HCR6  0   0.267   2.9222   1.8296  -1.7017
 8XS  H30  H  HCR6  0   0.261   1.1418   1.6043  -0.2134
 8XS  H32  H  HCR6  0   0.278   0.4499  -3.3504  -0.2044
 8XS  H34  H  HNH1  0   0.415  -2.2098   2.0163   1.9032
 8XS  H37  H  HOH1  0   0.489   8.7168  -0.5128   1.3333
 8XS  H40  H  HCR6  0   0.270   7.0467   1.6526  -0.6395
 8XS  H42  H  HCR6  0   0.269   5.1940   2.7415  -1.8278
 8XS  H44  H  HCH3  0   0.257  -2.7117   4.2110   2.2243
 8XS  H45  H  HCH3  0   0.245  -1.5833   4.5825   0.9159
 8XS  H43  H  HCH3  0   0.246  -3.2940   4.3101   0.5608
 8XS  F25  F  F     0  -0.308  -7.9994  -1.0906   0.0424

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
 8XS  C29  N18  single    1.445  0.020  1.445
 8XS  O15  C6   double    1.222  0.020  1.222
 8XS  N18  C6   single    1.337  0.020  1.337
 8XS  C6   C1   single    1.490  0.020  1.490
 8XS  C28  C27  aromatic  1.386  0.020  1.386
 8XS  C28  C26  aromatic  1.386  0.020  1.386
 8XS  C23  C19  aromatic  1.384  0.020  1.384
 8XS  C23  C22  aromatic  1.381  0.020  1.381
 8XS  C19  C10  aromatic  1.399  0.020  1.399
 8XS  C27  C12  aromatic  1.396  0.020  1.396
 8XS  C1   C3   aromatic  1.436  0.020  1.436
 8XS  C1   C2   aromatic  1.361  0.020  1.361
 8XS  C7   C3   aromatic  1.392  0.020  1.392
 8XS  C7   C9   aromatic  1.390  0.020  1.390
 8XS  C26  C11  aromatic  1.393  0.020  1.393
 8XS  C3   C5   aromatic  1.392  0.020  1.392
 8XS  F25  C22  single    1.339  0.020  1.339
 8XS  C22  C24  aromatic  1.382  0.020  1.382
 8XS  C12  C9   single    1.477  0.020  1.477
 8XS  C12  C13  aromatic  1.392  0.020  1.392
 8XS  C10  C2   single    1.457  0.020  1.457
 8XS  C10  C20  aromatic  1.397  0.020  1.397
 8XS  C2   O4   aromatic  1.361  0.020  1.361
 8XS  C9   C17  aromatic  1.408  0.020  1.408
 8XS  C11  C13  aromatic  1.392  0.020  1.392
 8XS  C11  C8   single    1.485  0.020  1.485
 8XS  O16  C8   double    1.208  0.020  1.208
 8XS  C5   O4   aromatic  1.347  0.020  1.347
 8XS  C5   C14  aromatic  1.382  0.020  1.382
 8XS  C24  C20  aromatic  1.384  0.020  1.384
 8XS  C8   O21  single    1.325  0.020  1.325
 8XS  C17  C14  aromatic  1.384  0.020  1.384
 8XS  C13  H31  single    0.930  0.020  1.080
 8XS  C17  H33  single    0.930  0.020  1.080
 8XS  C19  H35  single    0.930  0.020  1.080
 8XS  C20  H36  single    0.930  0.020  1.080
 8XS  C23  H38  single    0.930  0.020  1.080
 8XS  C24  H39  single    0.930  0.020  1.080
 8XS  C27  H41  single    0.930  0.020  1.080
 8XS  C7   H30  single    0.930  0.020  1.080
 8XS  C14  H32  single    0.930  0.020  1.080
 8XS  N18  H34  single    0.860  0.020  1.020
 8XS  O21  H37  single    0.850  0.020  0.980
 8XS  C26  H40  single    0.930  0.020  1.080
 8XS  C28  H42  single    0.930  0.020  1.080
 8XS  C29  H44  single    0.970  0.020  1.090
 8XS  C29  H45  single    0.970  0.020  1.090
 8XS  C29  H43  single    0.970  0.020  1.090

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
 8XS  H31  C13  C12  119.77  3.000
 8XS  H31  C13  C11  119.14  3.000
 8XS  C12  C13  C11  121.07  3.000
 8XS  H33  C17  C14  118.47  3.000
 8XS  H33  C17  C9   119.28  3.000
 8XS  C14  C17  C9   122.24  3.000
 8XS  H35  C19  C10  120.78  3.000
 8XS  H35  C19  C23  118.21  3.000
 8XS  C10  C19  C23  121.01  3.000
 8XS  H36  C20  C10  120.91  3.000
 8XS  H36  C20  C24  117.97  3.000
 8XS  C10  C20  C24  121.11  3.000
 8XS  F25  C22  C24  119.05  3.000
 8XS  C24  C22  C23  121.85  3.000
 8XS  F25  C22  C23  119.10  3.000
 8XS  H38  C23  C22  120.65  3.000
 8XS  H38  C23  C19  120.52  3.000
 8XS  C22  C23  C19  118.84  3.000
 8XS  H39  C24  C22  120.69  3.000
 8XS  H39  C24  C20  120.52  3.000
 8XS  C22  C24  C20  118.79  3.000
 8XS  C26  C11  C8   122.19  3.000
 8XS  C8   C11  C13  117.94  3.000
 8XS  C26  C11  C13  119.87  3.000
 8XS  C9   C12  C27  120.82  3.000
 8XS  C9   C12  C13  120.86  3.000
 8XS  C27  C12  C13  118.32  3.000
 8XS  H41  C27  C28  119.26  3.000
 8XS  H41  C27  C12  119.87  3.000
 8XS  C28  C27  C12  120.86  3.000
 8XS  C6   C1   C3   122.85  3.000
 8XS  C3   C1   C2   106.27  3.000
 8XS  C6   C1   C2   130.58  3.000
 8XS  C10  C2   O4   115.24  3.000
 8XS  O4   C2   C1   110.48  3.000
 8XS  C10  C2   C1   134.21  3.000
 8XS  C7   C3   C5   119.70  3.000
 8XS  C5   C3   C1   105.48  3.000
 8XS  C7   C3   C1   134.82  3.000
 8XS  C5   O4   C2   107.86  3.000
 8XS  C14  C5   O4   126.93  3.000
 8XS  C14  C5   C3   123.17  3.000
 8XS  O4   C5   C3   109.90  3.000
 8XS  N18  C6   O15  123.60  3.000
 8XS  N18  C6   C1   115.33  3.000
 8XS  O15  C6   C1   121.01  3.000
 8XS  H30  C7   C9   120.76  3.000
 8XS  H30  C7   C3   120.56  3.000
 8XS  C9   C7   C3   118.67  3.000
 8XS  O21  C8   O16  123.23  3.000
 8XS  O21  C8   C11  113.00  3.000
 8XS  O16  C8   C11  123.78  3.000
 8XS  C7   C9   C12  120.12  3.000
 8XS  C12  C9   C17  120.02  3.000
 8XS  C7   C9   C17  119.86  3.000
 8XS  C2   C10  C20  121.61  3.000
 8XS  C20  C10  C19  118.40  3.000
 8XS  C2   C10  C19  119.98  3.000
 8XS  H32  C14  C5   122.21  3.000
 8XS  H32  C14  C17  121.44  3.000
 8XS  C5   C14  C17  116.35  3.000
 8XS  H34  N18  C29  118.55  3.000
 8XS  H34  N18  C6   118.72  3.000
 8XS  C29  N18  C6   122.52  3.000
 8XS  H37  O21  C8   110.00  3.000
 8XS  H40  C26  C28  119.43  3.000
 8XS  H40  C26  C11  121.15  3.000
 8XS  C28  C26  C11  119.43  3.000
 8XS  H42  C28  C26  119.86  3.000
 8XS  H42  C28  C27  119.70  3.000
 8XS  C26  C28  C27  120.44  3.000
 8XS  H43  C29  H45  108.40  3.000
 8XS  H43  C29  H44  108.48  3.000
 8XS  H45  C29  H44  108.63  3.000
 8XS  H43  C29  N18  111.35  3.000
 8XS  H45  C29  N18  111.59  3.000
 8XS  H44  C29  N18  108.30  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
 8XS  CONST_01  C28  C27  C12  C13     0.00   0.0  0
 8XS  CONST_04  C28  C26  C11  C13     0.00   0.0  0
 8XS  CONST_05  C3   C7   C9   C17     0.00   0.0  0
 8XS  CONST_07  C3   C5   C14  C17     0.00   0.0  0
 8XS  CONST_08  O4   C5   C14  C17   180.00   0.0  0
 8XS  CONST_09  C24  C22  C23  C19     0.00   0.0  0
 8XS  CONST_12  C24  C20  C10  C19     0.00   0.0  0
 8XS  CONST_13  C23  C19  C10  C20     0.00   0.0  0
 8XS  CONST_16  C23  C22  C24  C20     0.00   0.0  0
 8XS  CONST_17  C10  C19  C23  C22     0.00   0.0  0
 8XS  CONST_18  C10  C20  C24  C22     0.00   0.0  0
 8XS  CONST_19  C2   C10  C19  C23   180.00   0.0  0
 8XS  CONST_20  C2   C10  C20  C24   180.00   0.0  0
 8XS  CONST_21  C27  C28  C26  C11     0.00   0.0  0
 8XS  CONST_22  C27  C12  C13  C11     0.00   0.0  0
 8XS  CONST_23  C9   C12  C13  C11   180.00   0.0  0
 8XS  CONST_24  C26  C28  C27  C12     0.00   0.0  0
 8XS  CONST_25  C3   C7   C9   C12   180.00   0.0  0
 8XS  CONST_26  C14  C17  C9   C12   180.00   0.0  0
 8XS  CONST_27  C26  C11  C13  C12     0.00   0.0  0
 8XS  CONST_29  C9   C7   C3   C1    180.00   0.0  0
 8XS  CONST_30  O4   C5   C3   C1      0.00   0.0  0
 8XS  CONST_31  C14  C5   C3   C1    180.00   0.0  0
 8XS  CONST_32  C5   O4   C2   C1      0.00   0.0  0
 8XS  CONST_33  C7   C3   C1   C2    180.00   0.0  0
 8XS  CONST_34  C5   C3   C1   C2      0.00   0.0  0
 8XS  CONST_35  C3   C5   O4   C2      0.00   0.0  0
 8XS  CONST_36  C14  C5   O4   C2    180.00   0.0  0
 8XS  CONST_37  C10  C2   C1   C3    180.00   0.0  0
 8XS  CONST_38  O4   C2   C1   C3      0.00   0.0  0
 8XS  CONST_39  C7   C3   C5   O4    180.00   0.0  0
 8XS  CONST_40  C9   C7   C3   C5      0.00   0.0  0
 8XS  CONST_41  C10  C2   O4   C5    180.00   0.0  0
 8XS  CONST_42  C9   C17  C14  C5      0.00   0.0  0
 8XS  CONST_43  C14  C5   C3   C7      0.00   0.0  0
 8XS  CONST_44  C14  C17  C9   C7      0.00   0.0  0
 8XS  CONST_45  C28  C27  C12  C9    180.00   0.0  0
 8XS  CONST_46  F25  C22  C23  C19   180.00   0.0  0
 8XS  CONST_47  F25  C22  C24  C20   180.00   0.0  0
 8XS  CONST_48  C8   C11  C13  C12   180.00   0.0  0
 8XS  CONST_49  C6   C1   C2   O4    180.00   0.0  0
 8XS  CONST_50  C6   C1   C3   C5    180.00   0.0  0
 8XS  CONST_51  C7   C3   C1   C6      0.00   0.0  0
 8XS  CONST_52  C10  C2   C1   C6      0.00   0.0  0
 8XS  CONST_53  C28  C26  C11  C8    180.00   0.0  0
 8XS  CONST_54  H41  C27  C12  C13   180.00   0.0  0
 8XS  CONST_55  H40  C26  C11  C13   180.00   0.0  0
 8XS  CONST_56  H30  C7   C9   C17   180.00   0.0  0
 8XS  CONST_57  H36  C20  C10  C19   180.00   0.0  0
 8XS  CONST_58  H35  C19  C10  C20   180.00   0.0  0
 8XS  CONST_59  H39  C24  C22  C23   180.00   0.0  0
 8XS  CONST_60  H38  C23  C22  C24   180.00   0.0  0
 8XS  CONST_61  H42  C28  C26  C11   180.00   0.0  0
 8XS  CONST_62  H33  C17  C9   C12     0.00   0.0  0
 8XS  CONST_63  H31  C13  C12  C27   180.00   0.0  0
 8XS  CONST_64  H32  C14  C5   C3    180.00   0.0  0
 8XS  CONST_65  C29  N18  C6   C1    180.00   0.0  0
 8XS  CONST_66  H34  N18  C6   C1      0.00   0.0  0
 8XS  CONST_67  H37  O21  C8   C11   180.00   0.0  0
 8XS  CONST_68  C29  N18  C6   O15     0.00   0.0  0
 8XS  Var_01    O16  C8   C11  C13     1.35  30.0  2
 8XS  Var_02    O15  C6   C1   C2   -102.55  30.0  2
 8XS  Var_03    H44  C29  N18  C6    179.57  30.0  3

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
 8XS  plan-1  C19  0.020
 8XS  plan-1  C20  0.020
 8XS  plan-1  C22  0.020
 8XS  plan-1  C23  0.020
 8XS  plan-1  C24  0.020
 8XS  plan-1  C2   0.020
 8XS  plan-1  C10  0.020
 8XS  plan-1  H35  0.020
 8XS  plan-1  H36  0.020
 8XS  plan-1  H38  0.020
 8XS  plan-1  H39  0.020
 8XS  plan-1  F25  0.020
 8XS  plan-2  C13  0.020
 8XS  plan-2  C11  0.020
 8XS  plan-2  C12  0.020
 8XS  plan-2  C27  0.020
 8XS  plan-2  C8   0.020
 8XS  plan-2  C9   0.020
 8XS  plan-2  C26  0.020
 8XS  plan-2  C28  0.020
 8XS  plan-2  H31  0.020
 8XS  plan-2  H41  0.020
 8XS  plan-2  H40  0.020
 8XS  plan-2  H42  0.020
 8XS  plan-3  C17  0.020
 8XS  plan-3  C12  0.020
 8XS  plan-3  C1   0.020
 8XS  plan-3  C2   0.020
 8XS  plan-3  C3   0.020
 8XS  plan-3  O4   0.020
 8XS  plan-3  C5   0.020
 8XS  plan-3  C6   0.020
 8XS  plan-3  C7   0.020
 8XS  plan-3  C9   0.020
 8XS  plan-3  C10  0.020
 8XS  plan-3  C14  0.020
 8XS  plan-3  H33  0.020
 8XS  plan-3  H30  0.020
 8XS  plan-3  H32  0.020
 8XS  plan-4  C1   0.020
 8XS  plan-4  C6   0.020
 8XS  plan-4  O15  0.020
 8XS  plan-4  N18  0.020
 8XS  plan-4  C29  0.020
 8XS  plan-4  H34  0.020
 8XS  plan-5  C11  0.020
 8XS  plan-5  C8   0.020
 8XS  plan-5  O16  0.020
 8XS  plan-5  O21  0.020
 8XS  plan-5  H37  0.020

