# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Mar 19 04:31:23 2022
#   Inital geometry file: a 92 line input string
#   Ligand name: (1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)Cc1ccc2C(=O)c3cccc(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
 OAL  OAL  '(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetic acid'  ligand  31  22  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_OAL
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
 OAL  C1    C  CR16   0  -0.218   0.4667   0.3608  -4.8751
 OAL  C2    C  CR16   0  -0.308   1.3859   0.2694  -3.8309
 OAL  C3    C  CR6    0  -0.035   0.9340   0.0569  -2.5438
 OAL  C4    C  CR6    0  -0.177  -0.4426  -0.0676  -2.2785
 OAL  C5    C  CR6    0   0.385  -1.3608   0.0228  -3.3432
 OAL  C6    C  CR16   0  -0.332  -0.8848   0.2395  -4.6418
 OAL  C7    C  C      0   0.467  -0.9223  -0.2853  -0.9183
 OAL  C8    C  CR6    0  -0.171   0.0312  -0.3714   0.1768
 OAL  C9    C  CR6    0  -0.055   1.4152  -0.2561  -0.0711
 OAL  C10   C  C      0   0.318   1.9242  -0.0412  -1.4412
 OAL  C11   C  CR6    0   0.370  -0.4236  -0.5653   1.4927
 OAL  C12   C  CR6    0   0.076   0.4939  -0.6518   2.5602
 OAL  C13   C  CR16   0  -0.291   1.8382  -0.5419   2.2720
 OAL  C14   C  CR16   0  -0.294   2.3091  -0.3445   0.9744
 OAL  C15   C  CH2    0  -0.677  -0.0070  -0.8264   3.9519
 OAL  C16   C  C      0   0.430  -0.6531   0.4610   4.5326
 OAL  O1    O  OH1    0  -0.614  -2.6729  -0.0885  -3.1811
 OAL  O2    O  O      0  -0.529  -2.1433  -0.3950  -0.7014
 OAL  O3    O  OH1    0  -0.607  -1.7086  -0.6851   1.7969
 OAL  O5    O  O      0  -0.596  -0.4896   1.5146   3.8940
 OAL  O4    O  OC    -1  -0.617  -1.2579   0.3144   5.6107
 OAL  O6    O  O      0  -0.379   3.1145   0.0540  -1.6656
 OAL  HC1   H  HCR6   0   0.280   0.8178   0.5290  -5.8843
 OAL  HC2   H  HCR6   0   0.272   2.4437   0.3658  -4.0289
 OAL  HC6   H  HCR6   0   0.285  -1.5959   0.3091  -5.4548
 OAL  HC13  H  HCR6   0   0.266   2.5522  -0.6081   3.0837
 OAL  HC14  H  HCR6   0   0.267   3.3717  -0.2614   0.7948
 OAL  H151  H  HCH2   0   0.258   0.8272  -1.1074   4.6016
 OAL  H152  H  HCH2   0   0.249  -0.7258  -1.6470   4.0130
 OAL  HO1   H  HOH1   0   0.489  -2.8522  -0.2394  -2.2272
 OAL  HO3   H  HOH1   0   0.488  -2.2312  -0.6149   0.9688

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
 OAL  C1   C2    aromatic  1.394  0.020  1.394
 OAL  C1   C6    aromatic  1.377  0.020  1.377
 OAL  C1   HC1   single    0.930  0.020  1.080
 OAL  C2   C3    aromatic  1.381  0.020  1.381
 OAL  C2   HC2   single    0.930  0.020  1.080
 OAL  C3   C4    aromatic  1.407  0.020  1.407
 OAL  C3   C10   single    1.485  0.020  1.485
 OAL  C4   C5    aromatic  1.409  0.020  1.409
 OAL  C4   C7    single    1.459  0.020  1.459
 OAL  C5   C6    aromatic  1.400  0.020  1.400
 OAL  C5   O1    single    1.327  0.020  1.327
 OAL  C6   HC6   single    0.930  0.020  1.080
 OAL  C7   C8    single    1.455  0.020  1.455
 OAL  C7   O2    double    1.245  0.020  1.245
 OAL  C8   C9    aromatic  1.411  0.020  1.411
 OAL  C8   C11   aromatic  1.406  0.020  1.406
 OAL  C9   C10   single    1.477  0.020  1.477
 OAL  C9   C14   aromatic  1.378  0.020  1.378
 OAL  C10  O6    double    1.215  0.020  1.215
 OAL  C11  C12   aromatic  1.410  0.020  1.410
 OAL  C11  O3    single    1.326  0.020  1.326
 OAL  C12  C13   aromatic  1.379  0.020  1.379
 OAL  C12  C15   single    1.489  0.020  1.489
 OAL  C13  C14   aromatic  1.394  0.020  1.394
 OAL  C13  HC13  single    0.930  0.020  1.080
 OAL  C14  HC14  single    0.930  0.020  1.080
 OAL  C15  C16   single    1.553  0.020  1.553
 OAL  C15  H151  single    0.970  0.020  1.090
 OAL  C15  H152  single    0.970  0.020  1.090
 OAL  C16  O5    deloc     1.243  0.020  1.243
 OAL  C16  O4    deloc     1.245  0.020  1.245
 OAL  O1   HO1   single    0.850  0.020  0.980
 OAL  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
 OAL  HC1   C1   C6    119.37  3.000
 OAL  HC1   C1   C2    119.67  3.000
 OAL  C6    C1   C2    120.96  3.000
 OAL  HC2   C2   C3    120.33  3.000
 OAL  HC2   C2   C1    120.16  3.000
 OAL  C3    C2   C1    119.51  3.000
 OAL  C10   C3   C4    120.42  3.000
 OAL  C10   C3   C2    118.95  3.000
 OAL  C4    C3   C2    120.63  3.000
 OAL  C7    C4   C5    120.00  3.000
 OAL  C7    C4   C3    120.70  3.000
 OAL  C5    C4   C3    119.30  3.000
 OAL  O1    C5   C6    117.55  3.000
 OAL  O1    C5   C4    123.15  3.000
 OAL  C6    C5   C4    119.30  3.000
 OAL  HC6   C6   C5    118.91  3.000
 OAL  HC6   C6   C1    120.79  3.000
 OAL  C5    C6   C1    120.30  3.000
 OAL  O2    C7   C8    120.43  3.000
 OAL  O2    C7   C4    119.88  3.000
 OAL  C8    C7   C4    119.70  3.000
 OAL  C11   C8   C9    119.55  3.000
 OAL  C11   C8   C7    120.06  3.000
 OAL  C9    C8   C7    120.39  3.000
 OAL  C14   C9   C10   119.30  3.000
 OAL  C14   C9   C8    119.84  3.000
 OAL  C10   C9   C8    120.86  3.000
 OAL  O6    C10  C9    121.35  3.000
 OAL  O6    C10  C3    120.72  3.000
 OAL  C9    C10  C3    117.93  3.000
 OAL  O3    C11  C12   116.83  3.000
 OAL  O3    C11  C8    122.73  3.000
 OAL  C12   C11  C8    120.44  3.000
 OAL  C15   C12  C13   122.17  3.000
 OAL  C15   C12  C11   119.72  3.000
 OAL  C13   C12  C11   118.10  3.000
 OAL  HC13  C13  C14   118.91  3.000
 OAL  HC13  C13  C12   118.75  3.000
 OAL  C14   C13  C12   122.33  3.000
 OAL  HC14  C14  C13   119.83  3.000
 OAL  HC14  C14  C9    120.44  3.000
 OAL  C13   C14  C9    119.73  3.000
 OAL  H152  C15  H151  105.99  3.000
 OAL  H152  C15  C16   109.15  3.000
 OAL  H151  C15  C16   107.95  3.000
 OAL  H152  C15  C12   111.19  3.000
 OAL  H151  C15  C12   109.18  3.000
 OAL  C16   C15  C12   113.08  3.000
 OAL  O4    C16  O5    127.50  3.000
 OAL  O4    C16  C15   115.36  3.000
 OAL  O5    C16  C15   117.12  3.000
 OAL  HO1   O1   C5    108.18  3.000
 OAL  HO3   O3   C11   108.42  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
 OAL  CONST_01  C4    C3   C2   C1     0.00   0.0  0
 OAL  CONST_02  C4    C5   C6   C1     0.00   0.0  0
 OAL  CONST_03  C5    C6   C1   C2     0.00   0.0  0
 OAL  CONST_04  C5    C4   C3   C2     0.00   0.0  0
 OAL  CONST_05  C6    C1   C2   C3     0.00   0.0  0
 OAL  CONST_06  C6    C5   C4   C3     0.00   0.0  0
 OAL  CONST_07  C13   C14  C9   C8     0.00   0.0  0
 OAL  CONST_08  C13   C12  C11  C8     0.00   0.0  0
 OAL  CONST_09  C12   C11  C8   C9     0.00   0.0  0
 OAL  CONST_10  C12   C13  C14  C9     0.00   0.0  0
 OAL  CONST_11  C14   C9   C8   C11    0.00   0.0  0
 OAL  CONST_12  C14   C13  C12  C11    0.00   0.0  0
 OAL  CONST_13  O1    C5   C6   C1   180.00   0.0  0
 OAL  CONST_14  O1    C5   C4   C3   180.00   0.0  0
 OAL  CONST_15  O1    C5   C4   C7     0.00   0.0  0
 OAL  CONST_16  O3    C11  C8   C7     0.00   0.0  0
 OAL  CONST_17  C15   C12  C11  C8   180.00   0.0  0
 OAL  CONST_18  O3    C11  C8   C9   180.00   0.0  0
 OAL  CONST_19  O3    C11  C12  C13  180.00   0.0  0
 OAL  CONST_20  C15   C12  C13  C14  180.00   0.0  0
 OAL  CONST_21  HC6   C6   C1   C2   180.00   0.0  0
 OAL  CONST_22  HC1   C1   C2   C3   180.00   0.0  0
 OAL  CONST_23  HC2   C2   C3   C4   180.00   0.0  0
 OAL  CONST_24  HC14  C14  C9   C8   180.00   0.0  0
 OAL  CONST_25  HC13  C13  C14  C9   180.00   0.0  0
 OAL  Var_01    C16   C15  C12  C11  -73.05  30.0  2
 OAL  Var_02    O5    C16  C15  C12  -11.44  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
 OAL  plan-1  C1    0.020
 OAL  plan-1  C2    0.020
 OAL  plan-1  C3    0.020
 OAL  plan-1  C4    0.020
 OAL  plan-1  C5    0.020
 OAL  plan-1  C6    0.020
 OAL  plan-1  C7    0.020
 OAL  plan-1  C8    0.020
 OAL  plan-1  C9    0.020
 OAL  plan-1  C10   0.020
 OAL  plan-1  C11   0.020
 OAL  plan-1  C12   0.020
 OAL  plan-1  C13   0.020
 OAL  plan-1  C14   0.020
 OAL  plan-1  C15   0.020
 OAL  plan-1  O1    0.020
 OAL  plan-1  O2    0.020
 OAL  plan-1  O3    0.020
 OAL  plan-1  O6    0.020
 OAL  plan-1  HC1   0.020
 OAL  plan-1  HC2   0.020
 OAL  plan-1  HC6   0.020
 OAL  plan-1  HC13  0.020
 OAL  plan-1  HC14  0.020
 OAL  plan-2  C15   0.020
 OAL  plan-2  C16   0.020
 OAL  plan-2  O5    0.020
 OAL  plan-2  O4    0.020

