# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Mar  9 09:04:27 2022
#   Inital geometry file: a 91 line input string
#   Ligand name: (1,8-dihydroxy-9-oxo-9,10-dihydroanthracen-2-yl)acetic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)Cc1ccc2Cc3cccc(O)c3C(=O)c2c1O
#
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
 ADL  ADL  '(1,8-dihydroxy-9-oxo-9,10-dihydroanthracen-2-yl)acetic acid'  ligand  32  21  .  2022-03-11  2022-03-11
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_ADL
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
 ADL  C1    C  CR16   0  -0.220   0.6976   0.2949  -4.9978
 ADL  C2    C  CR16   0  -0.337   1.5984   0.2610  -3.9414
 ADL  C3    C  CR66   0   0.093   1.1427   0.0561  -2.6495
 ADL  C4    C  CR66   0  -0.189  -0.2287  -0.1178  -2.4109
 ADL  C5    C  CR6    0   0.383  -1.1380  -0.0827  -3.4982
 ADL  C6    C  CR16   0  -0.361  -0.6586   0.1256  -4.7882
 ADL  C7    C  CR6    0   0.468  -0.7230  -0.3357  -1.0578
 ADL  C8    C  CR66   0  -0.180   0.2038  -0.3699   0.0615
 ADL  C9    C  CR66   0   0.071   1.5811  -0.1980  -0.1558
 ADL  C10   C  C      0  -0.592   2.1316   0.0219  -1.5288
 ADL  C11   C  CR6    0   0.356  -0.2805  -0.5753   1.3762
 ADL  C12   C  CR6    0   0.054   0.5995  -0.6169   2.4629
 ADL  C13   C  CR16   0  -0.291   1.9483  -0.4477   2.2042
 ADL  C14   C  CR16   0  -0.327   2.4441  -0.2392   0.9212
 ADL  C15   C  CH2    0  -0.672   0.0728  -0.8267   3.8445
 ADL  C16   C  C      0   0.423  -0.6945   0.3878   4.4235
 ADL  O1    O  OH1    0  -0.625  -2.4491  -0.2429  -3.3384
 ADL  O2    O  O      0  -0.553  -1.9474  -0.4955  -0.8647
 ADL  O3    O  OH1    0  -0.621  -1.5750  -0.7470   1.6342
 ADL  O5    O  O      0  -0.600  -0.5854   1.4728   3.8261
 ADL  O4    O  OC    -1  -0.625  -1.3365   0.1673   5.4695
 ADL  HC1   H  HCR6   0   0.269   1.0600   0.4563  -6.0049
 ADL  HC2   H  HCR6   0   0.257   2.6571   0.3940  -4.1240
 ADL  HC6   H  HCR6   0   0.270  -1.3566   0.1514  -5.6148
 ADL  H101  H  H      0   0.292   2.7008   0.9567  -1.5364
 ADL  H102  H  H      0   0.293   2.8704  -0.7575  -1.7393
 ADL  HC13  H  HCR6   0   0.256   2.6434  -0.4795   3.0352
 ADL  HC14  H  HCR6   0   0.251   3.5085  -0.1131   0.7664
 ADL  H151  H  HCH2   0   0.251   0.9103  -1.0401   4.5165
 ADL  H152  H  HCH2   0   0.238  -0.5721  -1.7083   3.8888
 ADL  HO1   H  HOH1   0   0.485  -2.6183  -0.3814  -2.3789
 ADL  HO3   H  HOH1   0   0.484  -2.0616  -0.7044   0.7811

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
 ADL  C1   C2    aromatic  1.389  0.020  1.389
 ADL  C1   C6    aromatic  1.383  0.020  1.383
 ADL  C1   HC1   single    0.930  0.020  1.080
 ADL  C2   C3    aromatic  1.385  0.020  1.385
 ADL  C2   HC2   single    0.930  0.020  1.080
 ADL  C3   C4    aromatic  1.403  0.020  1.403
 ADL  C3   C10   single    1.495  0.020  1.495
 ADL  C4   C5    aromatic  1.418  0.020  1.418
 ADL  C4   C7    single    1.457  0.020  1.457
 ADL  C5   C6    aromatic  1.392  0.020  1.392
 ADL  C5   O1    single    1.330  0.020  1.330
 ADL  C6   HC6   single    0.930  0.020  1.080
 ADL  C7   C8    single    1.454  0.020  1.454
 ADL  C7   O2    double    1.250  0.020  1.250
 ADL  C8   C9    aromatic  1.405  0.020  1.405
 ADL  C8   C11   aromatic  1.416  0.020  1.416
 ADL  C9   C10   single    1.496  0.020  1.496
 ADL  C9   C14   aromatic  1.381  0.020  1.381
 ADL  C10  H101  single    0.970  0.020  1.090
 ADL  C10  H102  single    0.970  0.020  1.090
 ADL  C11  C12   aromatic  1.399  0.020  1.399
 ADL  C11  O3    single    1.331  0.020  1.331
 ADL  C12  C13   aromatic  1.384  0.020  1.384
 ADL  C12  C15   single    1.493  0.020  1.493
 ADL  C13  C14   aromatic  1.391  0.020  1.391
 ADL  C13  HC13  single    0.930  0.020  1.080
 ADL  C14  HC14  single    0.930  0.020  1.080
 ADL  C15  C16   single    1.549  0.020  1.549
 ADL  C15  H151  single    0.970  0.020  1.090
 ADL  C15  H152  single    0.970  0.020  1.090
 ADL  C16  O5    deloc     1.243  0.020  1.243
 ADL  C16  O4    deloc     1.247  0.020  1.247
 ADL  O1   HO1   single    0.850  0.020  0.980
 ADL  O3   HO3   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
 ADL  HC1   C1   C6    119.19  3.000
 ADL  HC1   C1   C2    119.62  3.000
 ADL  C6    C1   C2    121.19  3.000
 ADL  HC2   C2   C3    119.82  3.000
 ADL  HC2   C2   C1    120.20  3.000
 ADL  C3    C2   C1    119.98  3.000
 ADL  C10   C3   C4    121.09  3.000
 ADL  C10   C3   C2    119.01  3.000
 ADL  C4    C3   C2    119.91  3.000
 ADL  C7    C4   C5    119.89  3.000
 ADL  C7    C4   C3    120.54  3.000
 ADL  C5    C4   C3    119.57  3.000
 ADL  O1    C5   C6    117.96  3.000
 ADL  O1    C5   C4    122.47  3.000
 ADL  C6    C5   C4    119.57  3.000
 ADL  HC6   C6   C5    119.29  3.000
 ADL  HC6   C6   C1    120.93  3.000
 ADL  C5    C6   C1    119.78  3.000
 ADL  O2    C7   C8    120.18  3.000
 ADL  O2    C7   C4    119.67  3.000
 ADL  C8    C7   C4    120.15  3.000
 ADL  C11   C8   C9    119.77  3.000
 ADL  C11   C8   C7    120.02  3.000
 ADL  C9    C8   C7    120.21  3.000
 ADL  C14   C9   C10   119.37  3.000
 ADL  C14   C9   C8    119.24  3.000
 ADL  C10   C9   C8    121.39  3.000
 ADL  H102  C10  H101  104.83  3.000
 ADL  H102  C10  C9    108.69  3.000
 ADL  H101  C10  C9    108.87  3.000
 ADL  H102  C10  C3    108.58  3.000
 ADL  H101  C10  C3    108.62  3.000
 ADL  C9    C10  C3    116.62  3.000
 ADL  O3    C11  C12   117.21  3.000
 ADL  O3    C11  C8    122.09  3.000
 ADL  C12   C11  C8    120.69  3.000
 ADL  C15   C12  C13   122.27  3.000
 ADL  C15   C12  C11   120.07  3.000
 ADL  C13   C12  C11   117.66  3.000
 ADL  HC13  C13  C14   118.87  3.000
 ADL  HC13  C13  C12   118.57  3.000
 ADL  C14   C13  C12   122.56  3.000
 ADL  HC14  C14  C13   119.97  3.000
 ADL  HC14  C14  C9    119.96  3.000
 ADL  C13   C14  C9    120.07  3.000
 ADL  H152  C15  H151  105.62  3.000
 ADL  H152  C15  C16   108.96  3.000
 ADL  H151  C15  C16   107.60  3.000
 ADL  H152  C15  C12   111.03  3.000
 ADL  H151  C15  C12   108.99  3.000
 ADL  C16   C15  C12   114.23  3.000
 ADL  O4    C16  O5    127.05  3.000
 ADL  O4    C16  C15   115.47  3.000
 ADL  O5    C16  C15   117.46  3.000
 ADL  HO1   O1   C5    107.66  3.000
 ADL  HO3   O3   C11   107.91  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
 ADL  CONST_01  C4    C3   C2   C1     0.00   0.0  0
 ADL  CONST_02  C4    C5   C6   C1     0.00   0.0  0
 ADL  CONST_03  C5    C6   C1   C2     0.00   0.0  0
 ADL  CONST_04  C5    C4   C3   C2     0.00   0.0  0
 ADL  CONST_05  C6    C1   C2   C3     0.00   0.0  0
 ADL  CONST_06  C6    C5   C4   C3     0.00   0.0  0
 ADL  CONST_07  C13   C14  C9   C8     0.00   0.0  0
 ADL  CONST_08  C13   C12  C11  C8     0.00   0.0  0
 ADL  CONST_09  C12   C11  C8   C9     0.00   0.0  0
 ADL  CONST_10  C12   C13  C14  C9     0.00   0.0  0
 ADL  CONST_11  C14   C9   C8   C11    0.00   0.0  0
 ADL  CONST_12  C14   C13  C12  C11    0.00   0.0  0
 ADL  CONST_13  O1    C5   C6   C1   180.00   0.0  0
 ADL  CONST_14  O1    C5   C4   C3   180.00   0.0  0
 ADL  CONST_15  O1    C5   C4   C7     0.00   0.0  0
 ADL  CONST_16  O3    C11  C8   C7     0.00   0.0  0
 ADL  CONST_17  C15   C12  C11  C8   180.00   0.0  0
 ADL  CONST_18  O3    C11  C8   C9   180.00   0.0  0
 ADL  CONST_19  O3    C11  C12  C13  180.00   0.0  0
 ADL  CONST_20  C15   C12  C13  C14  180.00   0.0  0
 ADL  CONST_21  HC6   C6   C1   C2   180.00   0.0  0
 ADL  CONST_22  HC1   C1   C2   C3   180.00   0.0  0
 ADL  CONST_23  HC2   C2   C3   C4   180.00   0.0  0
 ADL  CONST_24  HC14  C14  C9   C8   180.00   0.0  0
 ADL  CONST_25  HC13  C13  C14  C9   180.00   0.0  0
 ADL  Var_01    C9    C10  C3   C2   179.80  30.0  1
 ADL  Var_02    C8    C7   C4   C3     0.24  30.0  1
 ADL  Var_03    C8    C9   C10  C3     0.32  30.0  1
 ADL  Var_04    C9    C8   C7   C4    -0.23  30.0  1
 ADL  Var_05    C16   C15  C12  C11  -71.53  30.0  2
 ADL  Var_06    O5    C16  C15  C12  -13.34  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
 ADL  plan-1  C4    0.020
 ADL  plan-1  C7    0.020
 ADL  plan-1  C8    0.020
 ADL  plan-1  O2    0.020
 ADL  plan-2  C1    0.020
 ADL  plan-2  C2    0.020
 ADL  plan-2  C3    0.020
 ADL  plan-2  C4    0.020
 ADL  plan-2  C5    0.020
 ADL  plan-2  C6    0.020
 ADL  plan-2  C7    0.020
 ADL  plan-2  C10   0.020
 ADL  plan-2  O1    0.020
 ADL  plan-2  HC1   0.020
 ADL  plan-2  HC2   0.020
 ADL  plan-2  HC6   0.020
 ADL  plan-3  C7    0.020
 ADL  plan-3  C8    0.020
 ADL  plan-3  C9    0.020
 ADL  plan-3  C10   0.020
 ADL  plan-3  C11   0.020
 ADL  plan-3  C12   0.020
 ADL  plan-3  C13   0.020
 ADL  plan-3  C14   0.020
 ADL  plan-3  C15   0.020
 ADL  plan-3  O3    0.020
 ADL  plan-3  HC13  0.020
 ADL  plan-3  HC14  0.020
 ADL  plan-4  C15   0.020
 ADL  plan-4  C16   0.020
 ADL  plan-4  O5    0.020
 ADL  plan-4  O4    0.020

