# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 18 17:59:56 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  44  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  -0.363   4.5736  -0.5165  -0.4697
 8XS  C17  C  CR16   0  -0.323   1.9356  -1.7053   0.3379
 8XS  C19  C  CR16   0  -0.264  -4.5052  -1.5174   0.8207
 8XS  C20  C  CR16   0  -0.274  -4.5693   0.2201  -0.8429
 8XS  C22  C  CR6    0   0.531  -6.5804  -0.8189  -0.1122
 8XS  C23  C  CR16   0  -0.399  -5.8832  -1.6386   0.7549
 8XS  C24  C  CR16   0  -0.394  -5.9471   0.1099  -0.9160
 8XS  C11  C  CR6    0  -0.080   5.8833  -0.0489  -0.5002
 8XS  C12  C  CR6    0   0.108   3.5568   0.1906   0.1717
 8XS  C27  C  CR16   0  -0.321   3.8763   1.3980   0.7949
 8XS  C1   C  CR5    0  -0.185  -1.5236   0.5899   0.0219
 8XS  C2   C  CR5    0   0.432  -2.3809  -0.4659   0.1000
 8XS  C3   C  CR56   0   0.148  -0.1978   0.0325   0.0921
 8XS  O4   O  O      0  -0.457  -1.7030  -1.6322   0.2392
 8XS  C5   C  CR56   0   0.336  -0.3833  -1.3392   0.2408
 8XS  C6   C  C      0   0.424  -1.8065   2.0382  -0.0971
 8XS  C7   C  CR16   0  -0.426   1.0960   0.5488   0.0671
 8XS  C8   C  C      0   0.399   6.9719  -0.8443  -1.2133
 8XS  C9   C  CR6    0   0.085   2.1710  -0.3244   0.1919
 8XS  C10  C  CR6    0  -0.050  -3.8328  -0.5828   0.0302
 8XS  C14  C  CR16   0  -0.327   0.6592  -2.2381   0.3651
 8XS  O15  O  O      0  -0.485  -1.1044   2.7563  -0.7989
 8XS  O16  O  O      0  -0.592   6.6218  -1.9121  -1.7512
 8XS  N18  N  NH1    0  -0.621  -2.8357   2.5032   0.6211
 8XS  O21  O  OC    -1  -0.593   8.1185  -0.3577  -1.1952
 8XS  C26  C  CR16   0  -0.305   6.1765   1.1590   0.1273
 8XS  C28  C  CR16   0  -0.231   5.1777   1.8768   0.7697
 8XS  C29  C  CH3    0  -0.518  -3.2458   3.8868   0.5786
 8XS  H31  H  HCR6   0   0.241   4.3432  -1.4455  -0.9759
 8XS  H33  H  HCR6   0   0.262   2.7771  -2.3758   0.4521
 8XS  H35  H  HCR6   0   0.275  -3.9588  -2.1515   1.5062
 8XS  H36  H  HCR6   0   0.276  -4.0680   0.9228  -1.4947
 8XS  H38  H  HCR6   0   0.289  -6.4057  -2.3590   1.3700
 8XS  H39  H  HCR6   0   0.289  -6.5162   0.7258  -1.5992
 8XS  H41  H  HCR6   0   0.252   3.1115   1.9561   1.3213
 8XS  H30  H  HCR6   0   0.255   1.2589   1.6087  -0.0721
 8XS  H32  H  HCR6   0   0.275   0.4923  -3.2999   0.4858
 8XS  H34  H  HNH1   0   0.409  -3.3154   1.8846   1.2533
 8XS  H40  H  HCR6   0   0.244   7.1905   1.5355   0.1140
 8XS  H42  H  HCR6   0   0.250   5.4136   2.8116   1.2625
 8XS  H44  H  HCH3   0   0.253  -4.1223   4.0023   1.2092
 8XS  H45  H  HCH3   0   0.241  -2.4644   4.5523   0.9477
 8XS  H43  H  HCH3   0   0.242  -3.5077   4.1936  -0.4340
 8XS  F25  F  F      0  -0.307  -7.9125  -0.9346  -0.1830

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    1.444  0.020  1.444
 8XS  O15  C6   double    1.225  0.020  1.225
 8XS  N18  C6   single    1.338  0.020  1.338
 8XS  C6   C1   single    1.481  0.020  1.481
 8XS  C28  C27  aromatic  1.387  0.020  1.387
 8XS  C28  C26  aromatic  1.388  0.020  1.388
 8XS  C23  C19  aromatic  1.385  0.020  1.385
 8XS  C23  C22  aromatic  1.382  0.020  1.382
 8XS  C19  C10  aromatic  1.397  0.020  1.397
 8XS  C27  C12  aromatic  1.396  0.020  1.396
 8XS  C1   C3   aromatic  1.440  0.020  1.440
 8XS  C1   C2   aromatic  1.362  0.020  1.362
 8XS  C7   C3   aromatic  1.393  0.020  1.393
 8XS  C7   C9   aromatic  1.391  0.020  1.391
 8XS  C26  C11  aromatic  1.392  0.020  1.392
 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    1.479  0.020  1.479
 8XS  C12  C13  aromatic  1.395  0.020  1.395
 8XS  C10  C2   single    1.458  0.020  1.458
 8XS  C10  C20  aromatic  1.396  0.020  1.396
 8XS  C2   O4   aromatic  1.356  0.020  1.356
 8XS  C9   C17  aromatic  1.408  0.020  1.408
 8XS  C11  C13  aromatic  1.391  0.020  1.391
 8XS  C11  C8   single    1.525  0.020  1.525
 8XS  O16  C8   deloc     1.246  0.020  1.246
 8XS  C5   O4   aromatic  1.352  0.020  1.352
 8XS  C5   C14  aromatic  1.382  0.020  1.382
 8XS  C24  C20  aromatic  1.384  0.020  1.384
 8XS  C8   O21  deloc     1.246  0.020  1.246
 8XS  C17  C14  aromatic  1.383  0.020  1.383
 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  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  119.66  3.000
 8XS  H31  C13  C11  118.59  3.000
 8XS  C12  C13  C11  121.74  3.000
 8XS  H33  C17  C14  118.48  3.000
 8XS  H33  C17  C9   119.25  3.000
 8XS  C14  C17  C9   122.26  3.000
 8XS  H35  C19  C10  120.51  3.000
 8XS  H35  C19  C23  118.77  3.000
 8XS  C10  C19  C23  120.71  3.000
 8XS  H36  C20  C10  120.40  3.000
 8XS  H36  C20  C24  118.77  3.000
 8XS  C10  C20  C24  120.82  3.000
 8XS  F25  C22  C24  118.90  3.000
 8XS  C24  C22  C23  122.17  3.000
 8XS  F25  C22  C23  118.94  3.000
 8XS  H38  C23  C22  120.53  3.000
 8XS  H38  C23  C19  120.79  3.000
 8XS  C22  C23  C19  118.68  3.000
 8XS  H39  C24  C22  120.59  3.000
 8XS  H39  C24  C20  120.78  3.000
 8XS  C22  C24  C20  118.62  3.000
 8XS  C26  C11  C8   120.85  3.000
 8XS  C8   C11  C13  120.46  3.000
 8XS  C26  C11  C13  118.69  3.000
 8XS  C9   C12  C27  120.65  3.000
 8XS  C9   C12  C13  120.86  3.000
 8XS  C27  C12  C13  118.49  3.000
 8XS  H41  C27  C28  119.56  3.000
 8XS  H41  C27  C12  120.07  3.000
 8XS  C28  C27  C12  120.35  3.000
 8XS  C6   C1   C3   123.96  3.000
 8XS  C3   C1   C2   106.06  3.000
 8XS  C6   C1   C2   129.98  3.000
 8XS  C10  C2   O4   115.70  3.000
 8XS  O4   C2   C1   110.97  3.000
 8XS  C10  C2   C1   133.31  3.000
 8XS  C7   C3   C5   119.39  3.000
 8XS  C5   C3   C1   105.31  3.000
 8XS  C7   C3   C1   135.29  3.000
 8XS  C5   O4   C2   107.56  3.000
 8XS  C14  C5   O4   126.55  3.000
 8XS  C14  C5   C3   123.36  3.000
 8XS  O4   C5   C3   110.09  3.000
 8XS  N18  C6   O15  122.99  3.000
 8XS  N18  C6   C1   116.34  3.000
 8XS  O15  C6   C1   120.66  3.000
 8XS  H30  C7   C9   120.71  3.000
 8XS  H30  C7   C3   120.36  3.000
 8XS  C9   C7   C3   118.92  3.000
 8XS  O21  C8   O16  126.85  3.000
 8XS  O21  C8   C11  116.52  3.000
 8XS  O16  C8   C11  116.63  3.000
 8XS  C7   C9   C12  120.31  3.000
 8XS  C12  C9   C17  119.97  3.000
 8XS  C7   C9   C17  119.72  3.000
 8XS  C2   C10  C20  120.60  3.000
 8XS  C20  C10  C19  119.00  3.000
 8XS  C2   C10  C19  120.39  3.000
 8XS  H32  C14  C5   122.15  3.000
 8XS  H32  C14  C17  121.51  3.000
 8XS  C5   C14  C17  116.34  3.000
 8XS  H34  N18  C29  118.19  3.000
 8XS  H34  N18  C6   119.35  3.000
 8XS  C29  N18  C6   122.38  3.000
 8XS  H40  C26  C28  120.02  3.000
 8XS  H40  C26  C11  119.59  3.000
 8XS  C28  C26  C11  120.39  3.000
 8XS  H42  C28  C26  120.04  3.000
 8XS  H42  C28  C27  119.62  3.000
 8XS  C26  C28  C27  120.34  3.000
 8XS  H43  C29  H45  108.35  3.000
 8XS  H43  C29  H44  108.39  3.000
 8XS  H45  C29  H44  108.48  3.000
 8XS  H43  C29  N18  111.43  3.000
 8XS  H45  C29  N18  111.80  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  C29  N18  C6   O15     0.00   0.0  0
 8XS  Var_01    O16  C8   C11  C13    -0.06  30.0  2
 8XS  Var_02    O15  C6   C1   C2   -142.09  30.0  2
 8XS  Var_03    H44  C29  N18  C6    177.56  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

