# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 16 20:56:31 2020
#   Inital geometry file: a 125 line input string
#   Ligand name: 1-amino-4-[(3-methylphenyl)amino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1cccc(Nc2cc(c(N)c3C(=O)c4ccccc4C(=O)c23)[S](O)(=O)=O)c1
#
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
 8E9  8E9  '1-amino-4-[(3-methylphenyl)amino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid'  ligand  44  29  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_8E9
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
 8E9  O16   O  O      0  -0.373  -2.2871   0.4159  -1.1978
 8E9  C10   C  C      0   0.321  -1.4004   1.0159  -0.6212
 8E9  C14   C  C      0  -0.011  -1.6367   2.3981  -0.1563
 8E9  C5    C  C1     0  -0.279  -2.9322   2.9113  -0.1603
 8E9  C6    C  C1     0  -0.237  -3.1661   4.2026   0.2778
 8E9  C7    C  C1     0  -0.235  -2.1064   4.9946   0.7088
 8E9  C8    C  C1     0  -0.277  -0.8168   4.4927   0.7044
 8E9  C13   C  C      0  -0.008  -0.5765   3.1880   0.2777
 8E9  C9    C  C      0   0.365   0.8102   2.6679   0.2706
 8E9  O9    O  O      0  -0.440   1.7206   3.4429   0.5517
 8E9  C11   C  CR6    0  -0.132  -0.0709   0.4144  -0.3767
 8E9  C12   C  CR6    0  -0.170   1.0361   1.2598  -0.0521
 8E9  C1    C  CR6    0   0.379   2.3600   0.7521  -0.0461
 8E9  N1    N  NH2    0  -0.859   3.4359   1.5047   0.2393
 8E9  C4    C  CR6    0   0.368   0.1306  -0.9475  -0.5913
 8E9  C3    C  CR16   0  -0.343   1.4539  -1.4305  -0.5856
 8E9  C2    C  CR6    0  -0.300   2.5304  -0.6329  -0.3435
 8E9  S2    S  S      0   1.425   4.1562  -1.4049  -0.2704
 8E9  OS2   O  OS     0  -0.736   4.5053  -1.3977   1.1565
 8E9  OS1   O  OS    -1  -0.721   3.9856  -2.7494  -0.8360
 8E9  OS3   O  OS     0  -0.741   5.0266  -0.5349  -1.0871
 8E9  N4    N  NH1    0  -0.795  -0.8548  -1.8906  -0.8266
 8E9  C1'   C  CR6    0   0.393  -2.0106  -2.1143  -0.0923
 8E9  C6'   C  CR16   0  -0.322  -2.2900  -1.4725   1.1140
 8E9  C5'   C  CR16   0  -0.240  -3.4500  -1.7870   1.8040
 8E9  C4'   C  CR16   0  -0.328  -4.3422  -2.7333   1.3200
 8E9  C3'   C  CR6    0   0.105  -4.0742  -3.3861   0.1178
 8E9  C7'   C  CH3    0  -0.723  -5.0373  -4.3914  -0.4451
 8E9  C2'   C  CR16   0  -0.396  -2.9127  -3.0667  -0.5738
 8E9  H5    H  H      0   0.268  -3.7554   2.2965  -0.4975
 8E9  H6    H  H      0   0.272  -4.1740   4.5956   0.2840
 8E9  H7    H  H      0   0.272  -2.2902   6.0056   1.0470
 8E9  H8    H  H      0   0.268   0.0053   5.1132   1.0334
 8E9  H11N  H  HNH2   0   0.394   4.3487   1.1704  -0.0233
 8E9  H12N  H  HNH2   0   0.414   3.3049   2.4971   0.3440
 8E9  H3    H  HCR6   0   0.291   1.6105  -2.4866  -0.7675
 8E9  H4    H  HNH1   0   0.398  -0.5449  -2.6887  -1.3592
 8E9  H6'   H  HCR6   0   0.260  -1.6054  -0.7465   1.5329
 8E9  H2'   H  HCR6   0   0.252  -2.6967  -3.5678  -1.5119
 8E9  H5'   H  HCR6   0   0.250  -3.6537  -1.2888   2.7435
 8E9  H4'   H  HCR6   0   0.240  -5.2415  -2.9683   1.8762
 8E9  H7'1  H  HCH3   0   0.248  -5.7795  -3.9053  -1.0815
 8E9  H7'2  H  HCH3   0   0.242  -4.5283  -5.1381  -1.0541
 8E9  H7'3  H  HCH3   0   0.243  -5.5800  -4.9109   0.3439

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
 8E9  O16  C10   double    1.216  0.020  1.216
 8E9  C10  C14   single    1.477  0.020  1.477
 8E9  C10  C11   single    1.480  0.020  1.480
 8E9  C14  C5    aromatic  1.393  0.020  1.393
 8E9  C14  C13   aromatic  1.392  0.020  1.392
 8E9  C5   C6    aromatic  1.383  0.020  1.383
 8E9  C6   C7    aromatic  1.391  0.020  1.391
 8E9  C7   C8    aromatic  1.384  0.020  1.384
 8E9  C8   C13   aromatic  1.394  0.020  1.394
 8E9  C13  C9    single    1.481  0.020  1.481
 8E9  C9   O9    double    1.228  0.020  1.228
 8E9  C9   C12   single    1.462  0.020  1.462
 8E9  C11  C12   aromatic  1.430  0.020  1.430
 8E9  C11  C4    aromatic  1.393  0.020  1.393
 8E9  C12  C1    aromatic  1.418  0.020  1.418
 8E9  C1   N1    single    1.344  0.020  1.344
 8E9  C1   C2    aromatic  1.427  0.020  1.427
 8E9  C4   C3    aromatic  1.409  0.020  1.409
 8E9  C4   N4    single    1.384  0.020  1.384
 8E9  C3   C2    aromatic  1.361  0.020  1.361
 8E9  C2   S2    single    1.801  0.020  1.801
 8E9  S2   OS2   deloc     1.469  0.020  1.469
 8E9  S2   OS1   deloc     1.469  0.020  1.469
 8E9  S2   OS3   deloc     1.477  0.020  1.477
 8E9  N4   C1'   single    1.387  0.020  1.387
 8E9  C1'  C6'   aromatic  1.395  0.020  1.395
 8E9  C1'  C2'   aromatic  1.397  0.020  1.397
 8E9  C6'  C5'   aromatic  1.386  0.020  1.386
 8E9  C5'  C4'   aromatic  1.388  0.020  1.388
 8E9  C4'  C3'   aromatic  1.394  0.020  1.394
 8E9  C3'  C7'   single    1.502  0.020  1.502
 8E9  C3'  C2'   aromatic  1.389  0.020  1.389
 8E9  C5   H5    single    0.930  0.020  1.080
 8E9  C6   H6    single    0.930  0.020  1.080
 8E9  C7   H7    single    0.930  0.020  1.080
 8E9  C8   H8    single    0.930  0.020  1.080
 8E9  N1   H11N  single    0.890  0.020  1.040
 8E9  N1   H12N  single    0.890  0.020  1.040
 8E9  C3   H3    single    0.930  0.020  1.080
 8E9  N4   H4    single    0.890  0.020  1.040
 8E9  C6'  H6'   single    0.930  0.020  1.080
 8E9  C2'  H2'   single    0.930  0.020  1.080
 8E9  C5'  H5'   single    0.930  0.020  1.080
 8E9  C4'  H4'   single    0.930  0.020  1.080
 8E9  C7'  H7'1  single    0.970  0.020  1.090
 8E9  C7'  H7'2  single    0.970  0.020  1.090
 8E9  C7'  H7'3  single    0.970  0.020  1.090

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
 8E9  C11   C10  C14   118.17  3.000
 8E9  C11   C10  O16   122.21  3.000
 8E9  C14   C10  O16   119.62  3.000
 8E9  C13   C14  C5    120.01  3.000
 8E9  C13   C14  C10   120.49  3.000
 8E9  C5    C14  C10   119.50  3.000
 8E9  H5    C5   C6    120.05  3.000
 8E9  H5    C5   C14   119.94  3.000
 8E9  C6    C5   C14   120.00  3.000
 8E9  H6    C6   C7    120.06  3.000
 8E9  H6    C6   C5    119.89  3.000
 8E9  C7    C6   C5    120.04  3.000
 8E9  H7    C7   C8    119.89  3.000
 8E9  H7    C7   C6    119.96  3.000
 8E9  C8    C7   C6    120.15  3.000
 8E9  H8    C8   C13   119.95  3.000
 8E9  H8    C8   C7    119.96  3.000
 8E9  C13   C8   C7    120.08  3.000
 8E9  C9    C13  C8    119.45  3.000
 8E9  C9    C13  C14   120.83  3.000
 8E9  C8    C13  C14   119.71  3.000
 8E9  C12   C9   O9    122.94  3.000
 8E9  C12   C9   C13   118.94  3.000
 8E9  O9    C9   C13   118.12  3.000
 8E9  C4    C11  C12   120.05  3.000
 8E9  C4    C11  C10   120.12  3.000
 8E9  C12   C11  C10   119.52  3.000
 8E9  C1    C12  C11   120.80  3.000
 8E9  C1    C12  C9    119.22  3.000
 8E9  C11   C12  C9    119.98  3.000
 8E9  C2    C1   N1    119.49  3.000
 8E9  C2    C1   C12   117.27  3.000
 8E9  N1    C1   C12   123.23  3.000
 8E9  H12N  N1   H11N  118.20  3.000
 8E9  H12N  N1   C1    118.04  3.000
 8E9  H11N  N1   C1    118.98  3.000
 8E9  N4    C4   C3    115.84  3.000
 8E9  N4    C4   C11   126.10  3.000
 8E9  C3    C4   C11   118.06  3.000
 8E9  H3    C3   C2    119.14  3.000
 8E9  H3    C3   C4    118.00  3.000
 8E9  C2    C3   C4    122.86  3.000
 8E9  S2    C2   C3    118.02  3.000
 8E9  S2    C2   C1    121.02  3.000
 8E9  C3    C2   C1    120.75  3.000
 8E9  OS3   S2   OS1   113.25  3.000
 8E9  OS3   S2   OS2   113.21  3.000
 8E9  OS1   S2   OS2   113.97  3.000
 8E9  OS3   S2   C2    104.89  3.000
 8E9  OS1   S2   C2    105.78  3.000
 8E9  OS2   S2   C2    104.59  3.000
 8E9  H4    N4   C1'   114.07  3.000
 8E9  H4    N4   C4    114.23  3.000
 8E9  C1'   N4   C4    127.80  3.000
 8E9  C2'   C1'  C6'   118.84  3.000
 8E9  C2'   C1'  N4    117.73  3.000
 8E9  C6'   C1'  N4    123.40  3.000
 8E9  H6'   C6'  C5'   119.27  3.000
 8E9  H6'   C6'  C1'   121.12  3.000
 8E9  C5'   C6'  C1'   119.60  3.000
 8E9  H5'   C5'  C4'   119.70  3.000
 8E9  H5'   C5'  C6'   119.02  3.000
 8E9  C4'   C5'  C6'   121.28  3.000
 8E9  H4'   C4'  C3'   120.06  3.000
 8E9  H4'   C4'  C5'   120.18  3.000
 8E9  C3'   C4'  C5'   119.77  3.000
 8E9  C2'   C3'  C7'   120.24  3.000
 8E9  C2'   C3'  C4'   118.85  3.000
 8E9  C7'   C3'  C4'   120.89  3.000
 8E9  H7'3  C7'  H7'2  108.10  3.000
 8E9  H7'3  C7'  H7'1  107.20  3.000
 8E9  H7'2  C7'  H7'1  107.27  3.000
 8E9  H7'3  C7'  C3'   111.55  3.000
 8E9  H7'2  C7'  C3'   111.63  3.000
 8E9  H7'1  C7'  C3'   110.88  3.000
 8E9  H2'   C2'  C3'   119.39  3.000
 8E9  H2'   C2'  C1'   118.95  3.000
 8E9  C3'   C2'  C1'   121.67  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
 8E9  CONST_01  C7    C6   C5   C14    0.00   0.0  0
 8E9  CONST_02  C7    C8   C13  C14    0.00   0.0  0
 8E9  CONST_03  C8    C13  C14  C5     0.00   0.0  0
 8E9  CONST_04  C8    C7   C6   C5     0.00   0.0  0
 8E9  CONST_05  C13   C14  C5   C6     0.00   0.0  0
 8E9  CONST_06  C13   C8   C7   C6     0.00   0.0  0
 8E9  CONST_07  C2    C1   C12  C11    0.00   0.0  0
 8E9  CONST_08  C2    C3   C4   C11    0.00   0.0  0
 8E9  CONST_09  C3    C4   C11  C12    0.00   0.0  0
 8E9  CONST_10  C3    C2   C1   C12    0.00   0.0  0
 8E9  CONST_11  C4    C11  C12  C1     0.00   0.0  0
 8E9  CONST_12  C4    C3   C2   C1     0.00   0.0  0
 8E9  CONST_13  C4'   C5'  C6'  C1'    0.00   0.0  0
 8E9  CONST_14  C4'   C3'  C2'  C1'    0.00   0.0  0
 8E9  CONST_15  C3'   C2'  C1'  C6'    0.00   0.0  0
 8E9  CONST_16  C3'   C4'  C5'  C6'    0.00   0.0  0
 8E9  CONST_17  C2'   C1'  C6'  C5'    0.00   0.0  0
 8E9  CONST_18  C2'   C3'  C4'  C5'    0.00   0.0  0
 8E9  CONST_19  N4    C4   C11  C10    0.00   0.0  0
 8E9  CONST_20  N1    C1   C12  C9     0.00   0.0  0
 8E9  CONST_21  N1    C1   C12  C11  180.00   0.0  0
 8E9  CONST_22  N4    C4   C11  C12  180.00   0.0  0
 8E9  CONST_23  S2    C2   C1   C12  180.00   0.0  0
 8E9  CONST_24  C3    C2   C1   N1   180.00   0.0  0
 8E9  CONST_25  S2    C2   C3   C4   180.00   0.0  0
 8E9  CONST_26  N4    C4   C3   C2   180.00   0.0  0
 8E9  CONST_27  C5'   C6'  C1'  N4   180.00   0.0  0
 8E9  CONST_28  C3'   C2'  C1'  N4   180.00   0.0  0
 8E9  CONST_29  C7'   C3'  C2'  C1'  180.00   0.0  0
 8E9  CONST_30  C7'   C3'  C4'  C5'  180.00   0.0  0
 8E9  CONST_31  H5    C5   C14  C10    0.00   0.0  0
 8E9  CONST_32  H6    C6   C5   C14  180.00   0.0  0
 8E9  CONST_33  H8    C8   C13  C14  180.00   0.0  0
 8E9  CONST_34  H7    C7   C6   C5   180.00   0.0  0
 8E9  CONST_35  H3    C3   C4   C11  180.00   0.0  0
 8E9  CONST_36  H5'   C5'  C6'  C1'  180.00   0.0  0
 8E9  CONST_37  H2'   C2'  C1'  C6'  180.00   0.0  0
 8E9  CONST_38  H4'   C4'  C5'  C6'  180.00   0.0  0
 8E9  CONST_39  H6'   C6'  C5'  C4'  180.00   0.0  0
 8E9  CONST_41  H12N  N1   C1   C12    0.00   0.0  0
 8E9  Var_01    C1'   N4   C4   C11  -50.57  30.0  2
 8E9  Var_02    C6'   C1'  N4   C4    -6.55  30.0  2
 8E9  Var_03    OS2   S2   C2   C1    68.15  30.0  2
 8E9  Var_04    H7'1  C7'  C3'  C4'   88.61  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
 8E9  plan-1  N4    0.020
 8E9  plan-1  C1'   0.020
 8E9  plan-1  C6'   0.020
 8E9  plan-1  C5'   0.020
 8E9  plan-1  C4'   0.020
 8E9  plan-1  C3'   0.020
 8E9  plan-1  C7'   0.020
 8E9  plan-1  C2'   0.020
 8E9  plan-1  H6'   0.020
 8E9  plan-1  H2'   0.020
 8E9  plan-1  H5'   0.020
 8E9  plan-1  H4'   0.020
 8E9  plan-2  O16   0.020
 8E9  plan-2  C10   0.020
 8E9  plan-2  C14   0.020
 8E9  plan-2  C5    0.020
 8E9  plan-2  C6    0.020
 8E9  plan-2  C7    0.020
 8E9  plan-2  C8    0.020
 8E9  plan-2  C13   0.020
 8E9  plan-2  C9    0.020
 8E9  plan-2  O9    0.020
 8E9  plan-2  C11   0.020
 8E9  plan-2  C12   0.020
 8E9  plan-2  C1    0.020
 8E9  plan-2  N1    0.020
 8E9  plan-2  C4    0.020
 8E9  plan-2  C3    0.020
 8E9  plan-2  C2    0.020
 8E9  plan-2  S2    0.020
 8E9  plan-2  N4    0.020
 8E9  plan-2  H5    0.020
 8E9  plan-2  H6    0.020
 8E9  plan-2  H7    0.020
 8E9  plan-2  H8    0.020
 8E9  plan-2  H3    0.020
 8E9  plan-3  C1    0.020
 8E9  plan-3  N1    0.020
 8E9  plan-3  H11N  0.020
 8E9  plan-3  H12N  0.020

