# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu May 21 15:18:37 2020
#   Inital geometry file: a 108 line input string
#   Ligand name: 4-(2,7-difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)benzene-1,3-dicarboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1ccc(c(c1)C(O)=O)C2=C3C=C(F)C(=O)C=C3Oc4cc(O)c(F)cc24
#
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
 ORE  ORE  '4-(2,7-difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)benzene-1,3-dicarboxylic acid'  ligand  40  30  .  2021-08-19  2021-08-19  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_ORE
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
 ORE  O7   O  OH1   0  -0.578  21.3629  29.0620  43.3145
 ORE  C21  C  C     0   0.555  22.3304  28.1572  43.3666
 ORE  O6   O  O     0  -0.419  23.0410  28.1028  44.3357
 ORE  C17  C  CR6   0  -0.081  22.4949  27.2333  42.2066
 ORE  C18  C  CR16  0  -0.292  21.4685  26.9565  41.3172
 ORE  C19  C  CR6   0  -0.068  21.6490  26.0698  40.2589
 ORE  C20  C  C     0   0.515  20.4674  25.8447  39.3775
 ORE  O5   O  O     0  -0.422  19.3777  26.3028  39.6150
 ORE  O4   O  OH1   0  -0.588  20.7405  25.1068  38.3201
 ORE  C16  C  CR16  0  -0.232  23.7211  26.5951  42.0464
 ORE  C15  C  CR16  0  -0.239  23.9145  25.7211  40.9944
 ORE  C14  C  CR6   0  -0.019  22.8903  25.4477  40.0917
 ORE  C10  C  CR6   0   0.265  23.2172  24.4922  39.0064
 ORE  C9   C  CR66  0  -0.030  23.0959  23.1435  39.1951
 ORE  C8   C  CR16  0  -0.495  22.5748  22.5549  40.3947
 ORE  C7   C  CR6   0   0.439  22.4825  21.2226  40.4973
 ORE  F2   F  F     0  -0.304  21.9971  20.6605  41.6058
 ORE  C6   C  CR6   0   0.263  22.8865  20.2799  39.4454
 ORE  O3   O  OC    0  -0.471  22.7784  19.0672  39.6084
 ORE  C4   C  CR66  0   0.428  23.4943  22.2469  38.1439
 ORE  C5   C  CR16  0  -0.545  23.4007  20.8959  38.2534
 ORE  C11  C  CR66  0   0.026  23.7559  24.9898  37.7840
 ORE  C12  C  CR16  0  -0.510  23.9343  26.3572  37.5106
 ORE  C13  C  CR6   0   0.508  24.4544  26.7467  36.3138
 ORE  F1   F  F     0  -0.304  24.6316  28.0439  36.0438
 ORE  C3   C  CR66  0   0.375  24.1252  24.0708  36.7989
 ORE  O2   O  O     0  -0.466  23.9826  22.7507  36.9973
 ORE  C2   C  CR16  0  -0.468  24.6539  24.4683  35.5800
 ORE  C1   C  CR6   0   0.233  24.8247  25.8177  35.3230
 ORE  O1   O  OH1   0  -0.596  25.3233  26.3047  34.1917
 ORE  HO7  H  HOH1  0   0.497  20.9249  29.1139  42.4553
 ORE  H18  H  HCR6  0   0.279  20.4887  27.4035  41.4303
 ORE  HO4  H  HOH1  0   0.497  19.9452  24.9825  37.7787
 ORE  H16  H  HCR6  0   0.289  24.5314  26.7858  42.7364
 ORE  H15  H  HCR6  0   0.286  24.8752  25.2387  40.8724
 ORE  H8   H  HCR6  0   0.289  22.2575  23.1866  41.2142
 ORE  H5   H  HCR6  0   0.283  23.7152  20.2597  37.4359
 ORE  H12  H  HCR6  0   0.293  23.6687  27.1074  38.2440
 ORE  H2   H  HCR6  0   0.315  24.9288  23.7259  34.8404
 ORE  HO1  H  HOH1  0   0.493  25.5521  25.5940  33.5798

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
 ORE  O7   C21  single    1.326  0.020  1.326
 ORE  O7   HO7  single    0.850  0.020  0.980
 ORE  C21  O6   double    1.203  0.020  1.203
 ORE  C21  C17  single    1.492  0.020  1.492
 ORE  C17  C18  aromatic  1.386  0.020  1.386
 ORE  C17  C16  aromatic  1.392  0.020  1.392
 ORE  C18  C19  aromatic  1.392  0.020  1.392
 ORE  C18  H18  single    0.930  0.020  1.080
 ORE  C19  C20  single    1.491  0.020  1.491
 ORE  C19  C14  aromatic  1.398  0.020  1.398
 ORE  C20  O5   double    1.206  0.020  1.206
 ORE  C20  O4   single    1.318  0.020  1.318
 ORE  O4   HO4  single    0.850  0.020  0.980
 ORE  C16  C15  aromatic  1.381  0.020  1.381
 ORE  C16  H16  single    0.930  0.020  1.080
 ORE  C15  C14  aromatic  1.392  0.020  1.392
 ORE  C15  H15  single    0.930  0.020  1.080
 ORE  C14  C10  single    1.482  0.020  1.482
 ORE  C10  C9   aromatic  1.367  0.020  1.367
 ORE  C10  C11  aromatic  1.425  0.020  1.425
 ORE  C9   C8   aromatic  1.434  0.020  1.434
 ORE  C9   C4   aromatic  1.438  0.020  1.438
 ORE  C8   C7   aromatic  1.339  0.020  1.339
 ORE  C8   H8   single    0.930  0.020  1.080
 ORE  C7   F2   single    1.334  0.020  1.334
 ORE  C7   C6   aromatic  1.469  0.020  1.469
 ORE  C6   O3   double    1.228  0.020  1.228
 ORE  C6   C5   aromatic  1.437  0.020  1.437
 ORE  C4   C5   aromatic  1.359  0.020  1.359
 ORE  C4   O2   aromatic  1.344  0.020  1.344
 ORE  C5   H5   single    0.930  0.020  1.080
 ORE  C11  C12  aromatic  1.406  0.020  1.406
 ORE  C11  C3   aromatic  1.397  0.020  1.397
 ORE  C12  C13  aromatic  1.362  0.020  1.362
 ORE  C12  H12  single    0.930  0.020  1.080
 ORE  C13  F1   single    1.337  0.020  1.337
 ORE  C13  C1   aromatic  1.408  0.020  1.408
 ORE  C3   O2   aromatic  1.343  0.020  1.343
 ORE  C3   C2   aromatic  1.387  0.020  1.387
 ORE  C2   C1   aromatic  1.384  0.020  1.384
 ORE  C2   H2   single    0.930  0.020  1.080
 ORE  C1   O1   single    1.329  0.020  1.329
 ORE  O1   HO1  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
 ORE  HO7  O7   C21  113.75  3.000
 ORE  C17  C21  O6   122.22  3.000
 ORE  C17  C21  O7   118.20  3.000
 ORE  O6   C21  O7   119.58  3.000
 ORE  C16  C17  C18  119.15  3.000
 ORE  C16  C17  C21  118.08  3.000
 ORE  C18  C17  C21  122.74  3.000
 ORE  H18  C18  C19  117.36  3.000
 ORE  H18  C18  C17  121.37  3.000
 ORE  C19  C18  C17  121.26  3.000
 ORE  C14  C19  C20  124.44  3.000
 ORE  C14  C19  C18  119.29  3.000
 ORE  C20  C19  C18  116.27  3.000
 ORE  O4   C20  O5   123.91  3.000
 ORE  O4   C20  C19  113.24  3.000
 ORE  O5   C20  C19  122.85  3.000
 ORE  HO4  O4   C20  110.47  3.000
 ORE  H16  C16  C15  119.52  3.000
 ORE  H16  C16  C17  120.39  3.000
 ORE  C15  C16  C17  120.08  3.000
 ORE  H15  C15  C14  119.51  3.000
 ORE  H15  C15  C16  119.49  3.000
 ORE  C14  C15  C16  121.00  3.000
 ORE  C10  C14  C15  116.04  3.000
 ORE  C10  C14  C19  124.75  3.000
 ORE  C15  C14  C19  119.21  3.000
 ORE  C11  C10  C9   119.75  3.000
 ORE  C11  C10  C14  119.09  3.000
 ORE  C9   C10  C14  121.01  3.000
 ORE  C4   C9   C8   117.14  3.000
 ORE  C4   C9   C10  119.31  3.000
 ORE  C8   C9   C10  123.54  3.000
 ORE  H8   C8   C7   120.16  3.000
 ORE  H8   C8   C9   120.01  3.000
 ORE  C7   C8   C9   119.82  3.000
 ORE  C6   C7   F2   115.12  3.000
 ORE  C6   C7   C8   124.37  3.000
 ORE  F2   C7   C8   120.51  3.000
 ORE  C5   C6   O3   124.39  3.000
 ORE  C5   C6   C7   114.66  3.000
 ORE  O3   C6   C7   120.95  3.000
 ORE  O2   C4   C5   117.80  3.000
 ORE  O2   C4   C9   119.38  3.000
 ORE  C5   C4   C9   122.82  3.000
 ORE  H5   C5   C4   120.23  3.000
 ORE  H5   C5   C6   118.58  3.000
 ORE  C4   C5   C6   121.19  3.000
 ORE  C3   C11  C12  117.98  3.000
 ORE  C3   C11  C10  118.36  3.000
 ORE  C12  C11  C10  123.66  3.000
 ORE  H12  C12  C13  119.40  3.000
 ORE  H12  C12  C11  120.75  3.000
 ORE  C13  C12  C11  119.85  3.000
 ORE  C1   C13  F1   117.60  3.000
 ORE  C1   C13  C12  122.01  3.000
 ORE  F1   C13  C12  120.38  3.000
 ORE  C2   C3   O2   116.89  3.000
 ORE  C2   C3   C11  122.14  3.000
 ORE  O2   C3   C11  120.97  3.000
 ORE  C3   O2   C4   122.22  3.000
 ORE  H2   C2   C1   120.66  3.000
 ORE  H2   C2   C3   120.02  3.000
 ORE  C1   C2   C3   119.32  3.000
 ORE  O1   C1   C2   124.17  3.000
 ORE  O1   C1   C13  117.13  3.000
 ORE  C2   C1   C13  118.70  3.000
 ORE  HO1  O1   C1   111.02  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
 ORE  CONST_01  C14  C19  C18  C17    0.00   0.0  0
 ORE  CONST_02  C14  C15  C16  C17    0.00   0.0  0
 ORE  CONST_03  C15  C16  C17  C18    0.00   0.0  0
 ORE  CONST_04  C15  C14  C19  C18    0.00   0.0  0
 ORE  CONST_05  C10  C14  C19  C18  180.00   0.0  0
 ORE  CONST_06  C16  C17  C18  C19    0.00   0.0  0
 ORE  CONST_07  C16  C15  C14  C19    0.00   0.0  0
 ORE  CONST_10  C10  C14  C15  C16  180.00   0.0  0
 ORE  CONST_13  C8   C9   C10  C14    0.00   0.0  0
 ORE  CONST_14  C4   C9   C10  C14  180.00   0.0  0
 ORE  CONST_15  C12  C11  C10  C14    0.00   0.0  0
 ORE  CONST_16  C3   C11  C10  C14  180.00   0.0  0
 ORE  CONST_17  C7   C8   C9   C10  180.00   0.0  0
 ORE  CONST_18  C5   C4   C9   C10  180.00   0.0  0
 ORE  CONST_19  O2   C4   C9   C10    0.00   0.0  0
 ORE  CONST_20  C13  C12  C11  C10  180.00   0.0  0
 ORE  CONST_21  O2   C3   C11  C10    0.00   0.0  0
 ORE  CONST_22  C2   C3   C11  C10  180.00   0.0  0
 ORE  CONST_23  C12  C11  C10  C9   180.00   0.0  0
 ORE  CONST_24  C3   C11  C10  C9     0.00   0.0  0
 ORE  CONST_25  C6   C7   C8   C9     0.00   0.0  0
 ORE  CONST_26  C6   C5   C4   C9     0.00   0.0  0
 ORE  CONST_27  C3   O2   C4   C9     0.00   0.0  0
 ORE  CONST_28  C11  C10  C9   C8   180.00   0.0  0
 ORE  CONST_29  C5   C4   C9   C8     0.00   0.0  0
 ORE  CONST_30  O2   C4   C9   C8   180.00   0.0  0
 ORE  CONST_31  C5   C6   C7   C8     0.00   0.0  0
 ORE  CONST_32  C4   C9   C8   C7     0.00   0.0  0
 ORE  CONST_33  C4   C5   C6   C7     0.00   0.0  0
 ORE  CONST_34  O2   C4   C5   C6   180.00   0.0  0
 ORE  CONST_35  C11  C10  C9   C4     0.00   0.0  0
 ORE  CONST_36  C11  C3   O2   C4     0.00   0.0  0
 ORE  CONST_37  C2   C3   O2   C4   180.00   0.0  0
 ORE  CONST_38  C3   O2   C4   C5   180.00   0.0  0
 ORE  CONST_39  C1   C13  C12  C11    0.00   0.0  0
 ORE  CONST_40  C1   C2   C3   C11    0.00   0.0  0
 ORE  CONST_41  O2   C3   C11  C12  180.00   0.0  0
 ORE  CONST_42  C2   C3   C11  C12    0.00   0.0  0
 ORE  CONST_43  C2   C1   C13  C12    0.00   0.0  0
 ORE  CONST_44  C3   C11  C12  C13    0.00   0.0  0
 ORE  CONST_45  C3   C2   C1   C13    0.00   0.0  0
 ORE  CONST_46  C1   C2   C3   O2   180.00   0.0  0
 ORE  CONST_47  C19  C18  C17  C21  180.00   0.0  0
 ORE  CONST_48  C15  C16  C17  C21  180.00   0.0  0
 ORE  CONST_49  C20  C19  C18  C17  180.00   0.0  0
 ORE  CONST_50  C15  C14  C19  C20  180.00   0.0  0
 ORE  CONST_51  C10  C14  C19  C20    0.00   0.0  0
 ORE  CONST_52  F2   C7   C8   C9   180.00   0.0  0
 ORE  CONST_53  O3   C6   C7   C8   180.00   0.0  0
 ORE  CONST_54  C5   C6   C7   F2   180.00   0.0  0
 ORE  CONST_55  C4   C5   C6   O3   180.00   0.0  0
 ORE  CONST_56  F1   C13  C12  C11  180.00   0.0  0
 ORE  CONST_57  O1   C1   C13  C12  180.00   0.0  0
 ORE  CONST_58  C2   C1   C13  F1   180.00   0.0  0
 ORE  CONST_59  O1   C1   C2   C3   180.00   0.0  0
 ORE  CONST_60  H15  C15  C16  C17  180.00   0.0  0
 ORE  CONST_61  H16  C16  C17  C18  180.00   0.0  0
 ORE  CONST_62  H18  C18  C17  C16  180.00   0.0  0
 ORE  CONST_63  H8   C8   C9   C10    0.00   0.0  0
 ORE  CONST_64  H12  C12  C11  C10    0.00   0.0  0
 ORE  CONST_65  H5   C5   C4   C9   180.00   0.0  0
 ORE  CONST_66  H2   C2   C3   C11  180.00   0.0  0
 ORE  CONST_67  HO7  O7   C21  C17    0.00   0.0  0
 ORE  CONST_68  HO4  O4   C20  C19  180.00   0.0  0
 ORE  Var_01    C18  C17  C21  O7   -22.49  30.0  2
 ORE  Var_02    O5   C20  C19  C18   -6.24  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
 ORE  plan-1  C21  0.020
 ORE  plan-1  C17  0.020
 ORE  plan-1  C18  0.020
 ORE  plan-1  C19  0.020
 ORE  plan-1  C20  0.020
 ORE  plan-1  C16  0.020
 ORE  plan-1  C15  0.020
 ORE  plan-1  C14  0.020
 ORE  plan-1  C10  0.020
 ORE  plan-1  H18  0.020
 ORE  plan-1  H16  0.020
 ORE  plan-1  H15  0.020
 ORE  plan-2  C10  0.020
 ORE  plan-2  C11  0.020
 ORE  plan-2  C12  0.020
 ORE  plan-2  C13  0.020
 ORE  plan-2  F1   0.020
 ORE  plan-2  C3   0.020
 ORE  plan-2  O2   0.020
 ORE  plan-2  C2   0.020
 ORE  plan-2  C1   0.020
 ORE  plan-2  O1   0.020
 ORE  plan-2  H12  0.020
 ORE  plan-2  H2   0.020
 ORE  plan-3  C10  0.020
 ORE  plan-3  C9   0.020
 ORE  plan-3  C8   0.020
 ORE  plan-3  C7   0.020
 ORE  plan-3  F2   0.020
 ORE  plan-3  C6   0.020
 ORE  plan-3  O3   0.020
 ORE  plan-3  C4   0.020
 ORE  plan-3  C5   0.020
 ORE  plan-3  O2   0.020
 ORE  plan-3  H8   0.020
 ORE  plan-3  H5   0.020
 ORE  plan-4  O7   0.020
 ORE  plan-4  C21  0.020
 ORE  plan-4  O6   0.020
 ORE  plan-4  C17  0.020
 ORE  plan-4  HO7  0.020
 ORE  plan-5  C19  0.020
 ORE  plan-5  C20  0.020
 ORE  plan-5  O5   0.020
 ORE  plan-5  O4   0.020
 ORE  plan-5  HO4  0.020

