# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed May  6 17:23:35 2020
#   Inital geometry file: a 84 line input string
#   Ligand name: 4,5-dihydroxy-1-nitroanthracene-9,10-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1cccc2C(=O)c3c(ccc(O)c3C(=O)c12)[N+]([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
 HNA  HNA  4,5-dihydroxy-1-nitroanthracene-9,10-dione  ligand  28  21  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_HNA
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
 HNA  C1    C  CR6    0   0.406  -0.9872   2.4390   0.1600
 HNA  C2    C  CR66   0  -0.198  -0.2868   1.2155   0.1421
 HNA  C3    C  CR66   0  -0.015  -0.9924   0.0012   0.1207
 HNA  C4    C  CR6    0   0.195  -2.3720   0.0348   0.0953
 HNA  C5    C  CR16   0  -0.221  -3.0714   1.2356   0.1300
 HNA  C6    C  CR16   0  -0.347  -2.3872   2.4249   0.1606
 HNA  C13   C  CR6    0   0.337  -0.2587  -1.2888   0.2100
 HNA  C14   C  CR66   0  -0.018   1.2118  -1.2628   0.0684
 HNA  C15   C  CR66   0  -0.168   1.9021  -0.0365   0.0381
 HNA  C16   C  CR6    0   0.480   1.1767   1.2201   0.1121
 HNA  C22   C  CR6    0   0.393   3.3064  -0.0386  -0.0661
 HNA  C23   C  CR16   0  -0.325   3.9822  -1.2628  -0.1543
 HNA  C24   C  CR16   0  -0.216   3.2829  -2.4475  -0.1289
 HNA  C25   C  CR16   0  -0.302   1.8928  -2.4597  -0.0094
 HNA  O16   O  O      0  -0.513   1.7867   2.3002   0.1265
 HNA  O13   O  O      0  -0.359  -0.8586  -2.3205   0.4166
 HNA  O1    O  OH1    0  -0.599  -0.3917   3.6164   0.1815
 HNA  O22   O  OH1    0  -0.606   4.0374   1.0657  -0.0884
 HNA  N4    N  N      1   0.328  -3.1841  -1.1746  -0.0055
 HNA  O4B   O  O     -1  -0.359  -3.2111  -1.7347  -1.0705
 HNA  O4A   O  O      0  -0.358  -3.8273  -1.4831   0.9656
 HNA  HC5   H  HCR6   0   0.315  -4.1531   1.2414   0.1185
 HNA  HC6   H  HCR6   0   0.305  -2.9264   3.3622   0.1812
 HNA  HC23  H  HCR6   0   0.291   5.0609  -1.2603  -0.2407
 HNA  HC24  H  HCR6   0   0.286   3.8214  -3.3827  -0.2007
 HNA  HC25  H  HCR6   0   0.280   1.3583  -3.3984   0.0160
 HNA  HO1   H  HOH1   0   0.496   0.5810   3.4753   0.1735
 HNA  HO22  H  HOH1   0   0.492   3.4430   1.8405  -0.0123

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
 HNA  C1   C2    aromatic  1.410  0.020  1.410
 HNA  C1   C6    aromatic  1.400  0.020  1.400
 HNA  C1   O1    single    1.320  0.020  1.320
 HNA  C2   C3    aromatic  1.405  0.020  1.405
 HNA  C2   C16   single    1.464  0.020  1.464
 HNA  C3   C4    aromatic  1.380  0.020  1.380
 HNA  C3   C13   single    1.487  0.020  1.487
 HNA  C4   C5    aromatic  1.390  0.020  1.390
 HNA  C4   N4    single    1.460  0.020  1.460
 HNA  C5   C6    aromatic  1.372  0.020  1.372
 HNA  C5   HC5   single    0.930  0.020  1.080
 HNA  C6   HC6   single    0.930  0.020  1.080
 HNA  C13  C14   single    1.478  0.020  1.478
 HNA  C13  O13   double    1.211  0.020  1.211
 HNA  C14  C15   aromatic  1.408  0.020  1.408
 HNA  C14  C25   aromatic  1.379  0.020  1.379
 HNA  C15  C16   single    1.453  0.020  1.453
 HNA  C15  C22   aromatic  1.408  0.020  1.408
 HNA  C16  O16   double    1.241  0.020  1.241
 HNA  C22  C23   aromatic  1.401  0.020  1.401
 HNA  C22  O22   single    1.325  0.020  1.325
 HNA  C23  C24   aromatic  1.376  0.020  1.376
 HNA  C23  HC23  single    0.930  0.020  1.080
 HNA  C24  C25   aromatic  1.395  0.020  1.395
 HNA  C24  HC24  single    0.930  0.020  1.080
 HNA  C25  HC25  single    0.930  0.020  1.080
 HNA  O1   HO1   single    0.850  0.020  0.980
 HNA  O22  HO22  single    0.850  0.020  0.980
 HNA  N4   O4B   single    1.204  0.020  1.204
 HNA  N4   O4A   double    1.205  0.020  1.205

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
 HNA  O1    C1   C6   117.40  3.000
 HNA  O1    C1   C2   123.39  3.000
 HNA  C6    C1   C2   119.21  3.000
 HNA  C16   C2   C3   120.31  3.000
 HNA  C16   C2   C1   119.62  3.000
 HNA  C3    C2   C1   120.06  3.000
 HNA  C13   C3   C4   121.03  3.000
 HNA  C13   C3   C2   120.08  3.000
 HNA  C4    C3   C2   118.77  3.000
 HNA  N4    C4   C5   115.93  3.000
 HNA  N4    C4   C3   122.47  3.000
 HNA  C5    C4   C3   121.57  3.000
 HNA  HC5   C5   C6   119.61  3.000
 HNA  HC5   C5   C4   120.50  3.000
 HNA  C6    C5   C4   119.88  3.000
 HNA  HC6   C6   C5   120.19  3.000
 HNA  HC6   C6   C1   119.33  3.000
 HNA  C5    C6   C1   120.48  3.000
 HNA  O13   C13  C14  121.62  3.000
 HNA  O13   C13  C3   120.33  3.000
 HNA  C14   C13  C3   118.04  3.000
 HNA  C25   C14  C15  120.84  3.000
 HNA  C25   C14  C13  118.79  3.000
 HNA  C15   C14  C13  120.36  3.000
 HNA  C22   C15  C16  120.20  3.000
 HNA  C22   C15  C14  119.30  3.000
 HNA  C16   C15  C14  120.50  3.000
 HNA  O16   C16  C15  120.54  3.000
 HNA  O16   C16  C2   119.62  3.000
 HNA  C15   C16  C2   119.83  3.000
 HNA  O22   C22  C23  117.46  3.000
 HNA  O22   C22  C15  123.40  3.000
 HNA  C23   C22  C15  119.14  3.000
 HNA  HC23  C23  C24  120.67  3.000
 HNA  HC23  C23  C22  118.93  3.000
 HNA  C24   C23  C22  120.40  3.000
 HNA  HC24  C24  C25  119.61  3.000
 HNA  HC24  C24  C23  119.36  3.000
 HNA  C25   C24  C23  121.03  3.000
 HNA  HC25  C25  C24  120.16  3.000
 HNA  HC25  C25  C14  120.55  3.000
 HNA  C24   C25  C14  119.29  3.000
 HNA  HO1   O1   C1   108.56  3.000
 HNA  HO22  O22  C22  108.86  3.000
 HNA  O4A   N4   O4B  125.60  3.000
 HNA  O4A   N4   C4   116.95  3.000
 HNA  O4B   N4   C4   117.32  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
 HNA  CONST_01  C4    C3   C2   C1     0.00  0.0  0
 HNA  CONST_02  C4    C5   C6   C1     0.00  0.0  0
 HNA  CONST_03  C5    C6   C1   C2     0.00  0.0  0
 HNA  CONST_04  C5    C4   C3   C2     0.00  0.0  0
 HNA  CONST_05  C6    C1   C2   C3     0.00  0.0  0
 HNA  CONST_06  C6    C5   C4   C3     0.00  0.0  0
 HNA  CONST_07  C23   C22  C15  C14    0.00  0.0  0
 HNA  CONST_08  C23   C24  C25  C14    0.00  0.0  0
 HNA  CONST_09  C24   C25  C14  C15    0.00  0.0  0
 HNA  CONST_10  C24   C23  C22  C15    0.00  0.0  0
 HNA  CONST_11  C25   C14  C15  C22    0.00  0.0  0
 HNA  CONST_12  C25   C24  C23  C22    0.00  0.0  0
 HNA  CONST_13  N4    C4   C3   C2   180.00  0.0  0
 HNA  CONST_14  O1    C1   C2   C3   180.00  0.0  0
 HNA  CONST_15  O1    C1   C6   C5   180.00  0.0  0
 HNA  CONST_16  N4    C4   C5   C6   180.00  0.0  0
 HNA  CONST_17  N4    C4   C3   C13    0.00  0.0  0
 HNA  CONST_18  O22   C22  C15  C14  180.00  0.0  0
 HNA  CONST_19  O1    C1   C2   C16    0.00  0.0  0
 HNA  CONST_20  O22   C22  C15  C16    0.00  0.0  0
 HNA  CONST_21  O22   C22  C23  C24  180.00  0.0  0
 HNA  CONST_22  HC5   C5   C6   C1   180.00  0.0  0
 HNA  CONST_23  HC6   C6   C1   C2   180.00  0.0  0
 HNA  CONST_24  HC25  C25  C14  C13    0.00  0.0  0
 HNA  CONST_25  HC24  C24  C25  C14  180.00  0.0  0
 HNA  CONST_26  HC23  C23  C22  C15  180.00  0.0  0

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
 HNA  plan-1  C1    0.020
 HNA  plan-1  C2    0.020
 HNA  plan-1  C3    0.020
 HNA  plan-1  C4    0.020
 HNA  plan-1  C5    0.020
 HNA  plan-1  C6    0.020
 HNA  plan-1  C13   0.020
 HNA  plan-1  C14   0.020
 HNA  plan-1  C15   0.020
 HNA  plan-1  C16   0.020
 HNA  plan-1  C22   0.020
 HNA  plan-1  C23   0.020
 HNA  plan-1  C24   0.020
 HNA  plan-1  C25   0.020
 HNA  plan-1  O16   0.020
 HNA  plan-1  O13   0.020
 HNA  plan-1  O1    0.020
 HNA  plan-1  O22   0.020
 HNA  plan-1  N4    0.020
 HNA  plan-1  HC5   0.020
 HNA  plan-1  HC6   0.020
 HNA  plan-1  HC23  0.020
 HNA  plan-1  HC24  0.020
 HNA  plan-1  HC25  0.020
 HNA  plan-2  C4    0.020
 HNA  plan-2  N4    0.020
 HNA  plan-2  O4B   0.020
 HNA  plan-2  O4A   0.020

