# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 27 12:52:53 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  38  30  .  2021-08-17  2021-08-17  
;
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  OC    -1  -0.590  21.1926  28.8075  43.4114
 ORE  C21  C  C      0   0.398  22.2987  28.2380  43.3503
 ORE  O6   O  O      0  -0.593  23.2615  28.3885  44.1263
 ORE  C17  C  CR6    0  -0.082  22.4980  27.2525  42.2041
 ORE  C18  C  CR16   0  -0.340  21.4987  27.0382  41.2625
 ORE  C19  C  CR6    0  -0.088  21.6619  26.1504  40.2053
 ORE  C20  C  C      0   0.408  20.5596  25.9296  39.1868
 ORE  O5   O  O      0  -0.577  19.4990  26.5584  39.3406
 ORE  O4   O  OC    -1  -0.566  20.8324  25.1210  38.2759
 ORE  C16  C  CR16   0  -0.286  23.6885  26.5421  42.0757
 ORE  C15  C  CR16   0  -0.264  23.8685  25.6449  41.0354
 ORE  C14  C  CR6    0  -0.063  22.8609  25.4478  40.0945
 ORE  C10  C  CR6    0   0.316  23.1347  24.4979  38.9922
 ORE  C9   C  CR6    0  -0.059  23.0579  23.1379  39.1883
 ORE  C8   C  C1     0  -0.488  22.5328  22.5477  40.3818
 ORE  C7   C  C      0   0.421  22.4683  21.2129  40.5002
 ORE  F2   F  F      0  -0.314  21.9732  20.6558  41.6133
 ORE  C6   C  C      0   0.255  22.9064  20.2688  39.4708
 ORE  O3   O  OC     0  -0.497  22.8271  19.0507  39.6455
 ORE  C4   C  CR6    0   0.418  23.4834  22.2424  38.1581
 ORE  C5   C  C1     0  -0.555  23.4192  20.8860  38.2824
 ORE  C11  C  CR66   0   0.029  23.7127  24.9799  37.7752
 ORE  C12  C  CR16   0  -0.505  23.8936  26.3443  37.4958
 ORE  C13  C  CR6    0   0.502  24.4495  26.7301  36.3135
 ORE  F1   F  F      0  -0.308  24.6283  28.0289  36.0410
 ORE  C3   C  CR66   0   0.366  24.1165  24.0584  36.8095
 ORE  O2   O  O      0  -0.471  23.9802  22.7364  37.0087
 ORE  C2   C  CR16   0  -0.472  24.6812  24.4510  35.6027
 ORE  C1   C  CR6    0   0.227  24.8540  25.7982  35.3408
 ORE  O1   O  OH1    0  -0.602  25.3876  26.2799  34.2197
 ORE  H18  H  HCR6   0   0.238  20.5635  27.5750  41.3463
 ORE  H16  H  HCR6   0   0.248  24.4815  26.6904  42.7965
 ORE  H15  H  HCR6   0   0.250  24.7993  25.0965  40.9522
 ORE  H8   H  H      0   0.283  22.1840  23.1840  41.1848
 ORE  H5   H  H      0   0.272  23.7622  20.2509  37.4750
 ORE  H12  H  HCR6   0   0.290  23.5971  27.0935  38.2182
 ORE  H2   H  HCR6   0   0.308  24.9835  23.7040  34.8782
 ORE  HO1  H  HOH1   0   0.490  25.6397  25.5635  33.6243

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  deloc     1.246  0.020  1.246
 ORE  C21  O6   deloc     1.246  0.020  1.246
 ORE  C21  C17  single    1.525  0.020  1.525
 ORE  C17  C18  aromatic  1.390  0.020  1.390
 ORE  C17  C16  aromatic  1.392  0.020  1.392
 ORE  C18  C19  aromatic  1.390  0.020  1.390
 ORE  C18  H18  single    0.930  0.020  1.080
 ORE  C19  C20  single    1.517  0.020  1.517
 ORE  C19  C14  aromatic  1.394  0.020  1.394
 ORE  C20  O5   deloc     1.243  0.020  1.243
 ORE  C20  O4   deloc     1.248  0.020  1.248
 ORE  C16  C15  aromatic  1.386  0.020  1.386
 ORE  C16  H16  single    0.930  0.020  1.080
 ORE  C15  C14  aromatic  1.393  0.020  1.393
 ORE  C15  H15  single    0.930  0.020  1.080
 ORE  C14  C10  single    1.481  0.020  1.481
 ORE  C10  C9   aromatic  1.376  0.020  1.376
 ORE  C10  C11  aromatic  1.431  0.020  1.431
 ORE  C9   C8   aromatic  1.431  0.020  1.431
 ORE  C9   C4   aromatic  1.430  0.020  1.430
 ORE  C8   C7   aromatic  1.342  0.020  1.342
 ORE  C8   H8   single    0.930  0.020  1.080
 ORE  C7   F2   single    1.340  0.020  1.340
 ORE  C7   C6   aromatic  1.464  0.020  1.464
 ORE  C6   O3   double    1.233  0.020  1.233
 ORE  C6   C5   aromatic  1.434  0.020  1.434
 ORE  C4   C5   aromatic  1.364  0.020  1.364
 ORE  C4   O2   aromatic  1.346  0.020  1.346
 ORE  C5   H5   single    0.930  0.020  1.080
 ORE  C11  C12  aromatic  1.404  0.020  1.404
 ORE  C11  C3   aromatic  1.395  0.020  1.395
 ORE  C12  C13  aromatic  1.362  0.020  1.362
 ORE  C12  H12  single    0.930  0.020  1.080
 ORE  C13  F1   single    1.339  0.020  1.339
 ORE  C13  C1   aromatic  1.406  0.020  1.406
 ORE  C3   O2   aromatic  1.344  0.020  1.344
 ORE  C3   C2   aromatic  1.389  0.020  1.389
 ORE  C2   C1   aromatic  1.383  0.020  1.383
 ORE  C2   H2   single    0.930  0.020  1.080
 ORE  C1   O1   single    1.332  0.020  1.332
 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  C17  C21  O6   116.45  3.000
 ORE  C17  C21  O7   116.65  3.000
 ORE  O6   C21  O7   126.91  3.000
 ORE  C16  C17  C18  118.28  3.000
 ORE  C16  C17  C21  120.72  3.000
 ORE  C18  C17  C21  121.00  3.000
 ORE  H18  C18  C19  118.52  3.000
 ORE  H18  C18  C17  119.52  3.000
 ORE  C19  C18  C17  121.96  3.000
 ORE  C14  C19  C20  119.88  3.000
 ORE  C14  C19  C18  118.90  3.000
 ORE  C20  C19  C18  121.21  3.000
 ORE  O4   C20  O5   127.21  3.000
 ORE  O4   C20  C19  115.18  3.000
 ORE  O5   C20  C19  117.61  3.000
 ORE  H16  C16  C15  119.60  3.000
 ORE  H16  C16  C17  119.70  3.000
 ORE  C15  C16  C17  120.71  3.000
 ORE  H15  C15  C14  119.87  3.000
 ORE  H15  C15  C16  119.80  3.000
 ORE  C14  C15  C16  120.33  3.000
 ORE  C10  C14  C15  117.39  3.000
 ORE  C10  C14  C19  122.79  3.000
 ORE  C15  C14  C19  119.82  3.000
 ORE  C11  C10  C9   118.46  3.000
 ORE  C11  C10  C14  119.46  3.000
 ORE  C9   C10  C14  121.17  3.000
 ORE  C4   C9   C8   116.85  3.000
 ORE  C4   C9   C10  119.98  3.000
 ORE  C8   C9   C10  123.15  3.000
 ORE  H8   C8   C7   120.26  3.000
 ORE  H8   C8   C9   119.63  3.000
 ORE  C7   C8   C9   120.10  3.000
 ORE  C6   C7   F2   115.26  3.000
 ORE  C6   C7   C8   124.42  3.000
 ORE  F2   C7   C8   120.32  3.000
 ORE  C5   C6   O3   124.44  3.000
 ORE  C5   C6   C7   114.34  3.000
 ORE  O3   C6   C7   121.22  3.000
 ORE  O2   C4   C5   117.40  3.000
 ORE  O2   C4   C9   119.68  3.000
 ORE  C5   C4   C9   122.91  3.000
 ORE  H5   C5   C4   120.03  3.000
 ORE  H5   C5   C6   118.60  3.000
 ORE  C4   C5   C6   121.37  3.000
 ORE  C3   C11  C12  117.83  3.000
 ORE  C3   C11  C10  118.91  3.000
 ORE  C12  C11  C10  123.26  3.000
 ORE  H12  C12  C13  119.68  3.000
 ORE  H12  C12  C11  120.30  3.000
 ORE  C13  C12  C11  120.02  3.000
 ORE  C1   C13  F1   117.61  3.000
 ORE  C1   C13  C12  122.00  3.000
 ORE  F1   C13  C12  120.39  3.000
 ORE  C2   C3   O2   116.62  3.000
 ORE  C2   C3   C11  122.18  3.000
 ORE  O2   C3   C11  121.20  3.000
 ORE  C3   O2   C4   121.67  3.000
 ORE  H2   C2   C1   120.66  3.000
 ORE  H2   C2   C3   119.96  3.000
 ORE  C1   C2   C3   119.38  3.000
 ORE  O1   C1   C2   124.17  3.000
 ORE  O1   C1   C13  117.24  3.000
 ORE  C2   C1   C13  118.59  3.000
 ORE  HO1  O1   C1   110.82  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  Var_01    C18  C17  C21  O7     1.66  30.0  2
 ORE  Var_02    O5   C20  C19  C18   -0.87  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-5  C19  0.020
 ORE  plan-5  C20  0.020
 ORE  plan-5  O5   0.020
 ORE  plan-5  O4   0.020

