# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Jul 31 13:46:53 2022
#   Inital geometry file: a 91 line input string
#   Ligand name: 3-amino-4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Nc1c(O)c2C(=O)c3ccccc3C(=O)c2cc1[S](O)(=O)=O
#
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
 I8Y  I8Y  "3-amino-4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid"  ligand  30  22  .  2022-08-10  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_I8Y
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
 I8Y  C1   C  CR6    0   0.319  31.1837   9.3224  2.8551
 I8Y  C2   C  CR6    0   0.329  31.2291  10.5713  2.1692
 I8Y  C3   C  CR16   0  -0.334  29.7462  10.3639  4.5100
 I8Y  C7   C  CR66   0  -0.010  29.9069  14.1133  2.4685
 I8Y  C9   C  CR16   0  -0.234  29.2944  16.4325  2.2753
 I8Y  C10  C  CR16   0  -0.229  28.5420  16.3294  3.4394
 I8Y  C12  C  CR66   0  -0.026  29.1538  14.0092  3.6429
 I8Y  C13  C  CR6    0   0.307  29.0694  12.7282  4.3949
 I8Y  C6   C  CR6    0   0.384  30.6346  12.9464  1.9324
 I8Y  C5   C  CR66   0  -0.189  30.5487  11.6810  2.6593
 I8Y  C4   C  CR66   0  -0.047  29.7936  11.5765  3.8502
 I8Y  O5   O  OS     0  -0.741  31.6310   7.1463  4.9771
 I8Y  O    O  OS     0  -0.720  29.6860   8.0165  6.2098
 I8Y  O4   O  OS    -1  -0.736  29.3742   6.8744  4.0451
 I8Y  C    C  CR6    0  -0.300  30.4234   9.2504  4.0284
 I8Y  O2   O  O      0  -0.390  28.4192  12.6584  5.4229
 I8Y  C11  C  CR16   0  -0.274  28.4734  15.1246  4.1201
 I8Y  C8   C  CR16   0  -0.269  29.9745  15.3282  1.7910
 I8Y  O3   O  O      0  -0.444  31.2928  13.0478  0.8987
 I8Y  O1   O  OH1    0  -0.620  31.9607  10.5910  1.0583
 I8Y  N    N  NH2    0  -0.844  31.8478   8.2718  2.3223
 I8Y  H3   H  HCR6   0   0.271  29.1725  10.2792  5.4223
 I8Y  H5   H  HCR6   0   0.274  29.3493  17.3741  1.7456
 I8Y  H6   H  HCR6   0   0.274  28.0095  17.1919  3.8175
 I8Y  H7   H  HCR6   0   0.270  27.8890  15.0493  5.0268
 I8Y  H4   H  HCR6   0   0.272  30.5586  15.4079  0.8845
 I8Y  H2   H  HOH1   0   0.486  31.9202  11.5049  0.6916
 I8Y  H    H  HNH2   0   0.398  32.5257   8.4573  1.6021
 I8Y  H1   H  HNH2   0   0.397  32.0754   7.5077  2.9410
 I8Y  S    S  S      0   1.423  30.2563   7.6837  4.8976

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
 I8Y  O    S    deloc     1.469  0.020  1.469
 I8Y  C    S    single    1.799  0.020  1.799
 I8Y  C    C1   aromatic  1.400  0.020  1.400
 I8Y  N    C1   single    1.352  0.020  1.352
 I8Y  C1   C2   aromatic  1.426  0.020  1.426
 I8Y  O1   C2   single    1.330  0.020  1.330
 I8Y  C3   C    aromatic  1.389  0.020  1.389
 I8Y  C4   C3   aromatic  1.381  0.020  1.381
 I8Y  C4   C5   aromatic  1.414  0.020  1.414
 I8Y  C2   C5   aromatic  1.391  0.020  1.391
 I8Y  C5   C6   single    1.462  0.020  1.462
 I8Y  C6   C7   single    1.476  0.020  1.476
 I8Y  C7   C8   aromatic  1.393  0.020  1.393
 I8Y  C8   C9   aromatic  1.384  0.020  1.384
 I8Y  C9   C10  aromatic  1.390  0.020  1.390
 I8Y  C10  C11  aromatic  1.385  0.020  1.385
 I8Y  C11  C12  aromatic  1.391  0.020  1.391
 I8Y  C7   C12  aromatic  1.399  0.020  1.399
 I8Y  C12  C13  single    1.488  0.020  1.488
 I8Y  C13  C4   single    1.465  0.020  1.465
 I8Y  O2   C13  double    1.218  0.020  1.218
 I8Y  O3   C6   double    1.230  0.020  1.230
 I8Y  O4   S    deloc     1.470  0.020  1.470
 I8Y  S    O5   deloc     1.478  0.020  1.478
 I8Y  C3   H3   single    0.930  0.020  1.080
 I8Y  C9   H5   single    0.930  0.020  1.080
 I8Y  C10  H6   single    0.930  0.020  1.080
 I8Y  C11  H7   single    0.930  0.020  1.080
 I8Y  C8   H4   single    0.930  0.020  1.080
 I8Y  O1   H2   single    0.850  0.020  0.980
 I8Y  N    H    single    0.860  0.020  1.020
 I8Y  N    H1   single    0.890  0.020  1.040

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
 I8Y  N    C1   C    123.84  3.000
 I8Y  N    C1   C2   118.39  3.000
 I8Y  C    C1   C2   117.75  3.000
 I8Y  O1   C2   C5   123.47  3.000
 I8Y  C5   C2   C1   120.92  3.000
 I8Y  O1   C2   C1   115.61  3.000
 I8Y  H3   C3   C    119.23  3.000
 I8Y  H3   C3   C4   119.35  3.000
 I8Y  C    C3   C4   121.42  3.000
 I8Y  C8   C7   C6   119.28  3.000
 I8Y  C8   C7   C12  119.96  3.000
 I8Y  C6   C7   C12  120.76  3.000
 I8Y  H5   C9   C8   119.87  3.000
 I8Y  H5   C9   C10  120.14  3.000
 I8Y  C8   C9   C10  119.98  3.000
 I8Y  H6   C10  C11  119.81  3.000
 I8Y  H6   C10  C9   120.00  3.000
 I8Y  C11  C10  C9   120.19  3.000
 I8Y  C11  C12  C13  119.29  3.000
 I8Y  C13  C12  C7   121.26  3.000
 I8Y  C11  C12  C7   119.45  3.000
 I8Y  O2   C13  C4   122.16  3.000
 I8Y  O2   C13  C12  120.40  3.000
 I8Y  C4   C13  C12  117.44  3.000
 I8Y  O3   C6   C5   121.39  3.000
 I8Y  O3   C6   C7   120.26  3.000
 I8Y  C5   C6   C7   118.34  3.000
 I8Y  C4   C5   C6   120.95  3.000
 I8Y  C6   C5   C2   119.12  3.000
 I8Y  C4   C5   C2   119.93  3.000
 I8Y  C5   C4   C13  121.25  3.000
 I8Y  C13  C4   C3   119.70  3.000
 I8Y  C5   C4   C3   119.05  3.000
 I8Y  S    C    C3   119.02  3.000
 I8Y  C3   C    C1   120.93  3.000
 I8Y  S    C    C1   120.01  3.000
 I8Y  H7   C11  C12  119.75  3.000
 I8Y  H7   C11  C10  119.95  3.000
 I8Y  C12  C11  C10  120.30  3.000
 I8Y  H4   C8   C9   119.99  3.000
 I8Y  H4   C8   C7   119.89  3.000
 I8Y  C9   C8   C7   120.12  3.000
 I8Y  H2   O1   C2   107.57  3.000
 I8Y  H1   N    H    115.24  3.000
 I8Y  H1   N    C1   117.22  3.000
 I8Y  H    N    C1   118.00  3.000
 I8Y  C    S    O4   104.77  3.000
 I8Y  O4   S    O    114.20  3.000
 I8Y  C    S    O    105.69  3.000
 I8Y  O4   S    O5   112.90  3.000
 I8Y  C    S    O5   104.84  3.000
 I8Y  O    S    O5   113.29  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
 I8Y  CONST_01  C4   C3   C    C1      0.00   0.0  0
 I8Y  CONST_02  C4   C5   C2   C1      0.00   0.0  0
 I8Y  CONST_03  C3   C    C1   C2      0.00   0.0  0
 I8Y  CONST_04  C3   C4   C5   C2      0.00   0.0  0
 I8Y  CONST_05  C7   C6   C5   C2    180.00   0.0  0
 I8Y  CONST_06  C12  C13  C4   C3    180.00   0.0  0
 I8Y  CONST_07  C4   C5   C6   C7      0.00   0.0  0
 I8Y  CONST_08  C10  C9   C8   C7      0.00   0.0  0
 I8Y  CONST_09  C10  C11  C12  C7      0.00   0.0  0
 I8Y  CONST_10  C4   C13  C12  C7      0.00   0.0  0
 I8Y  CONST_11  C12  C7   C8   C9      0.00   0.0  0
 I8Y  CONST_12  C12  C11  C10  C9      0.00   0.0  0
 I8Y  CONST_13  C5   C6   C7   C12     0.00   0.0  0
 I8Y  CONST_14  C5   C4   C13  C12     0.00   0.0  0
 I8Y  CONST_15  C    C3   C4   C5      0.00   0.0  0
 I8Y  CONST_16  C    C1   C2   C5      0.00   0.0  0
 I8Y  CONST_17  C8   C7   C6   C5    180.00   0.0  0
 I8Y  CONST_18  C11  C12  C13  C4    180.00   0.0  0
 I8Y  CONST_19  C8   C9   C10  C11     0.00   0.0  0
 I8Y  CONST_20  C8   C7   C12  C11     0.00   0.0  0
 I8Y  CONST_21  S    C    C1   C2    180.00   0.0  0
 I8Y  CONST_22  O3   C6   C5   C2      0.00   0.0  0
 I8Y  CONST_23  N    C1   C    C3    180.00   0.0  0
 I8Y  CONST_24  O2   C13  C4   C3      0.00   0.0  0
 I8Y  CONST_25  O2   C13  C12  C7    180.00   0.0  0
 I8Y  CONST_26  O3   C6   C7   C12   180.00   0.0  0
 I8Y  CONST_27  O1   C2   C5   C6      0.00   0.0  0
 I8Y  CONST_28  O2   C13  C4   C5    180.00   0.0  0
 I8Y  CONST_29  N    C1   C2   C5    180.00   0.0  0
 I8Y  CONST_30  S    C    C3   C4    180.00   0.0  0
 I8Y  CONST_31  O1   C2   C5   C4    180.00   0.0  0
 I8Y  CONST_32  O3   C6   C5   C4    180.00   0.0  0
 I8Y  CONST_33  O1   C2   C1   C     180.00   0.0  0
 I8Y  CONST_34  C11  C12  C13  O2      0.00   0.0  0
 I8Y  CONST_35  O3   C6   C7   C8      0.00   0.0  0
 I8Y  CONST_36  H3   C3   C    C1    180.00   0.0  0
 I8Y  CONST_37  H5   C9   C8   C7    180.00   0.0  0
 I8Y  CONST_38  H7   C11  C12  C7    180.00   0.0  0
 I8Y  CONST_39  H7   C11  C10  C9    180.00   0.0  0
 I8Y  CONST_40  H4   C8   C9   C10   180.00   0.0  0
 I8Y  CONST_41  H6   C10  C11  C12   180.00   0.0  0
 I8Y  CONST_42  H4   C8   C7   C12   180.00   0.0  0
 I8Y  CONST_43  H7   C11  C12  C13     0.00   0.0  0
 I8Y  CONST_44  H3   C3   C4   C13     0.00   0.0  0
 I8Y  CONST_45  H4   C8   C7   C6      0.00   0.0  0
 I8Y  CONST_46  H3   C3   C4   C5    180.00   0.0  0
 I8Y  CONST_47  H5   C9   C10  C11   180.00   0.0  0
 I8Y  CONST_48  H6   C10  C9   C8    180.00   0.0  0
 I8Y  CONST_49  H    N    C1   C2      0.00   0.0  0
 I8Y  CONST_51  H    N    C1   C     180.00   0.0  0
 I8Y  Var_01    O    S    C    C1    167.09  30.0  2
 I8Y  Var_02    O4   S    C    C1    -71.95  30.0  2
 I8Y  Var_03    O5   S    C    C1     47.14  30.0  2
 I8Y  Var_04    O    S    C    C3    -15.44  30.0  2
 I8Y  Var_05    O4   S    C    C3    105.51  30.0  2
 I8Y  Var_06    O5   S    C    C3   -135.39  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
 I8Y  plan-1  C1   0.020
 I8Y  plan-1  C2   0.020
 I8Y  plan-1  C3   0.020
 I8Y  plan-1  C7   0.020
 I8Y  plan-1  C9   0.020
 I8Y  plan-1  C10  0.020
 I8Y  plan-1  C12  0.020
 I8Y  plan-1  C13  0.020
 I8Y  plan-1  C6   0.020
 I8Y  plan-1  C5   0.020
 I8Y  plan-1  C4   0.020
 I8Y  plan-1  C    0.020
 I8Y  plan-1  O2   0.020
 I8Y  plan-1  C11  0.020
 I8Y  plan-1  C8   0.020
 I8Y  plan-1  O3   0.020
 I8Y  plan-1  O1   0.020
 I8Y  plan-1  N    0.020
 I8Y  plan-1  H3   0.020
 I8Y  plan-1  H5   0.020
 I8Y  plan-1  H6   0.020
 I8Y  plan-1  H7   0.020
 I8Y  plan-1  H4   0.020
 I8Y  plan-1  S    0.020
 I8Y  plan-2  C1   0.020
 I8Y  plan-2  N    0.020
 I8Y  plan-2  H    0.020
 I8Y  plan-2  H1   0.020

