# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 28 22:28:47 2020
#   Inital geometry file: a 88 line input string
#   Ligand name: 1-amino-4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Nc1c(cc(O)c2C(=O)c3ccccc3C(=O)c12)C(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
 91L  91L  '1-amino-4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid'  ligand  30  21  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_91L
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
 91L  C01  C  CR6   0  -0.165   2.6716   0.0307  -0.0455
 91L  C02  C  C     0   0.592   4.0929   0.4625  -0.0676
 91L  C05  C  CR6   0   0.371   1.6054   0.9957  -0.0047
 91L  C07  C  CR66  0  -0.146   0.2733   0.5020   0.0121
 91L  C08  C  CR6   0   0.366  -0.8516   1.4293   0.0523
 91L  C10  C  CR66  0  -0.010  -2.2308   0.8792   0.0670
 91L  C11  C  CR16  0  -0.276  -3.3105   1.7577   0.1046
 91L  C12  C  CR16  0  -0.228  -4.6059   1.2692   0.1188
 91L  C13  C  CR16  0  -0.236  -4.8409  -0.1018   0.0957
 91L  C14  C  CR16  0  -0.268  -3.7754  -0.9826   0.0585
 91L  C15  C  CR66  0  -0.007  -2.4698  -0.4949   0.0441
 91L  C16  C  CR6   0   0.393  -1.3422  -1.4327   0.0057
 91L  C18  C  CR66  0  -0.213   0.0238  -0.8970  -0.0095
 91L  C19  C  CR6   0   0.374   1.0797  -1.8042  -0.0475
 91L  C21  C  CR16  0  -0.355   2.3911  -1.3133  -0.0649
 91L  N06  N  NH2   0  -0.861   1.8756   2.3015   0.0160
 91L  O03  O  OH1   0  -0.586   4.9412  -0.5501  -0.1052
 91L  O04  O  O     0  -0.449   4.4642   1.6163  -0.0531
 91L  O09  O  O     0  -0.437  -0.7127   2.6493   0.0744
 91L  O17  O  O     0  -0.450  -1.5463  -2.6458  -0.0136
 91L  O20  O  OH1   0  -0.624   0.9339  -3.1283  -0.0687
 91L  H1   H  HCR6  0   0.272  -3.1390   2.8247   0.1227
 91L  H2   H  HCR6  0   0.277  -5.4377   1.9599   0.1485
 91L  H3   H  HCR6  0   0.276  -5.8544  -0.4795   0.1063
 91L  H4   H  HCR6  0   0.274  -3.9524  -2.0491   0.0409
 91L  H5   H  HCR6  0   0.300   3.1906  -2.0407  -0.0944
 91L  H6   H  HNH2  0   0.420   1.1128   2.9572   0.0503
 91L  H7   H  HNH2  0   0.416   2.8318   2.6142   0.0069
 91L  H8   H  HOH1  0   0.495   5.8516  -0.2181  -0.1176
 91L  H9   H  HOH1  0   0.484  -0.0319  -3.3171  -0.0536

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
 91L  C12  C11  aromatic  1.384  0.020  1.384
 91L  C12  C13  aromatic  1.391  0.020  1.391
 91L  C11  C10  aromatic  1.393  0.020  1.393
 91L  O09  C08  double    1.228  0.020  1.228
 91L  C13  C14  aromatic  1.383  0.020  1.383
 91L  C10  C08  single    1.485  0.020  1.485
 91L  C10  C15  aromatic  1.395  0.020  1.395
 91L  N06  C05  single    1.334  0.020  1.334
 91L  C08  C07  single    1.458  0.020  1.458
 91L  C14  C15  aromatic  1.394  0.020  1.394
 91L  C05  C07  aromatic  1.421  0.020  1.421
 91L  C05  C01  aromatic  1.439  0.020  1.439
 91L  C15  C16  single    1.467  0.020  1.467
 91L  C07  C18  aromatic  1.421  0.020  1.421
 91L  O04  C02  double    1.212  0.020  1.212
 91L  C02  C01  single    1.486  0.020  1.486
 91L  C02  O03  single    1.322  0.020  1.322
 91L  C01  C21  aromatic  1.373  0.020  1.373
 91L  C18  C16  single    1.467  0.020  1.467
 91L  C18  C19  aromatic  1.393  0.020  1.393
 91L  C16  O17  double    1.230  0.020  1.230
 91L  C21  C19  aromatic  1.400  0.020  1.400
 91L  C19  O20  single    1.332  0.020  1.332
 91L  C11  H1   single    0.930  0.020  1.080
 91L  C12  H2   single    0.930  0.020  1.080
 91L  C13  H3   single    0.930  0.020  1.080
 91L  C14  H4   single    0.930  0.020  1.080
 91L  C21  H5   single    0.930  0.020  1.080
 91L  N06  H6   single    0.860  0.020  1.020
 91L  N06  H7   single    0.860  0.020  1.020
 91L  O03  H8   single    0.850  0.020  0.980
 91L  O20  H9   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
 91L  C21  C01  C05  120.37  3.000
 91L  C21  C01  C02  118.67  3.000
 91L  C05  C01  C02  120.97  3.000
 91L  O04  C02  O03  122.22  3.000
 91L  O03  C02  C01  113.07  3.000
 91L  O04  C02  C01  124.72  3.000
 91L  N06  C05  C07  122.01  3.000
 91L  C07  C05  C01  117.53  3.000
 91L  N06  C05  C01  120.47  3.000
 91L  C18  C07  C08  119.40  3.000
 91L  C18  C07  C05  120.43  3.000
 91L  C08  C07  C05  120.17  3.000
 91L  O09  C08  C10  118.23  3.000
 91L  C10  C08  C07  118.76  3.000
 91L  O09  C08  C07  123.02  3.000
 91L  C15  C10  C11  119.28  3.000
 91L  C15  C10  C08  121.60  3.000
 91L  C11  C10  C08  119.13  3.000
 91L  H1   C11  C12  119.78  3.000
 91L  H1   C11  C10  120.01  3.000
 91L  C12  C11  C10  120.21  3.000
 91L  H2   C12  C13  119.99  3.000
 91L  H2   C12  C11  119.64  3.000
 91L  C13  C12  C11  120.37  3.000
 91L  H3   C13  C14  119.99  3.000
 91L  H3   C13  C12  120.15  3.000
 91L  C14  C13  C12  119.87  3.000
 91L  H4   C14  C15  119.89  3.000
 91L  H4   C14  C13  120.17  3.000
 91L  C15  C14  C13  119.94  3.000
 91L  C16  C15  C14  119.78  3.000
 91L  C16  C15  C10  119.89  3.000
 91L  C14  C15  C10  120.33  3.000
 91L  O17  C16  C18  120.95  3.000
 91L  O17  C16  C15  120.21  3.000
 91L  C18  C16  C15  118.84  3.000
 91L  C19  C18  C16  117.92  3.000
 91L  C19  C18  C07  120.57  3.000
 91L  C16  C18  C07  121.51  3.000
 91L  O20  C19  C21  116.78  3.000
 91L  O20  C19  C18  124.40  3.000
 91L  C21  C19  C18  118.82  3.000
 91L  H5   C21  C19  117.20  3.000
 91L  H5   C21  C01  120.51  3.000
 91L  C19  C21  C01  122.29  3.000
 91L  H7   N06  H6   121.21  3.000
 91L  H7   N06  C05  119.78  3.000
 91L  H6   N06  C05  119.00  3.000
 91L  H8   O03  C02  109.93  3.000
 91L  H9   O20  C19  107.32  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
 91L  CONST_01  C18  C07  C05  C01    0.00   0.0  0
 91L  CONST_02  C18  C19  C21  C01    0.00   0.0  0
 91L  CONST_03  C19  C18  C07  C05    0.00   0.0  0
 91L  CONST_04  C19  C21  C01  C05    0.00   0.0  0
 91L  CONST_05  C21  C01  C05  C07    0.00   0.0  0
 91L  CONST_06  C21  C19  C18  C07    0.00   0.0  0
 91L  CONST_07  C13  C12  C11  C10    0.00   0.0  0
 91L  CONST_08  C13  C14  C15  C10    0.00   0.0  0
 91L  CONST_09  C14  C13  C12  C11    0.00   0.0  0
 91L  CONST_10  C14  C15  C10  C11    0.00   0.0  0
 91L  CONST_11  C15  C10  C11  C12    0.00   0.0  0
 91L  CONST_12  C15  C14  C13  C12    0.00   0.0  0
 91L  CONST_13  O20  C19  C21  C01  180.00   0.0  0
 91L  CONST_14  C07  C05  C01  C02  180.00   0.0  0
 91L  CONST_15  C19  C21  C01  C02  180.00   0.0  0
 91L  CONST_16  O20  C19  C18  C07  180.00   0.0  0
 91L  CONST_17  N06  C05  C07  C08    0.00   0.0  0
 91L  CONST_18  O20  C19  C18  C16    0.00   0.0  0
 91L  CONST_19  N06  C05  C07  C18  180.00   0.0  0
 91L  CONST_20  N06  C05  C01  C21  180.00   0.0  0
 91L  CONST_21  H5   C21  C01  C05  180.00   0.0  0
 91L  CONST_22  H1   C11  C10  C08    0.00   0.0  0
 91L  CONST_23  H2   C12  C11  C10  180.00   0.0  0
 91L  CONST_24  H4   C14  C15  C10  180.00   0.0  0
 91L  CONST_25  H3   C13  C12  C11  180.00   0.0  0
 91L  CONST_26  H6   N06  C05  C01  180.00   0.0  0
 91L  CONST_27  H7   N06  C05  C01    0.00   0.0  0
 91L  CONST_28  H8   O03  C02  C01  180.00   0.0  0
 91L  Var_01    O04  C02  C01  C05    0.04  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
 91L  plan-1  C01  0.020
 91L  plan-1  C02  0.020
 91L  plan-1  C05  0.020
 91L  plan-1  C07  0.020
 91L  plan-1  C08  0.020
 91L  plan-1  C10  0.020
 91L  plan-1  C11  0.020
 91L  plan-1  C12  0.020
 91L  plan-1  C13  0.020
 91L  plan-1  C14  0.020
 91L  plan-1  C15  0.020
 91L  plan-1  C16  0.020
 91L  plan-1  C18  0.020
 91L  plan-1  C19  0.020
 91L  plan-1  C21  0.020
 91L  plan-1  N06  0.020
 91L  plan-1  O09  0.020
 91L  plan-1  O17  0.020
 91L  plan-1  O20  0.020
 91L  plan-1  H1   0.020
 91L  plan-1  H2   0.020
 91L  plan-1  H3   0.020
 91L  plan-1  H4   0.020
 91L  plan-1  H5   0.020
 91L  plan-2  C05  0.020
 91L  plan-2  N06  0.020
 91L  plan-2  H6   0.020
 91L  plan-2  H7   0.020
 91L  plan-3  C01  0.020
 91L  plan-3  C02  0.020
 91L  plan-3  O03  0.020
 91L  plan-3  O04  0.020
 91L  plan-3  H8   0.020

