# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  2 09:02:03 2020
#   Inital geometry file: a 166 line input string
#   Ligand name: N-[9-(2-carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]-N-ethylethanaminium
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCN(CC)c1ccc2c(OC3=CC(C=CC3=C2c4ccccc4C(O)=O)=[N+](CC)CC)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
 RHB  RHB  N-[9-(2-carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]-N-ethylethanaminium  ligand  63  33  .  2021-08-23  2021-08-23  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_RHB
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
 RHB  O2   O  OC    -1  -0.570  -0.2228  -3.9621  -2.8263
 RHB  C26  C  C      0   0.416  -0.1674  -3.0797  -1.9566
 RHB  C19  C  CR6    0  -0.104  -0.1579  -3.5115  -0.5047
 RHB  C14  C  CR6    0  -0.037  -0.0777  -2.5392   0.4883
 RHB  C15  C  CR16   0  -0.279  -0.0673  -2.9043   1.8317
 RHB  C16  C  CR16   0  -0.246  -0.1372  -4.2433   2.1872
 RHB  C17  C  CR16   0  -0.247  -0.2169  -5.2185   1.2014
 RHB  C18  C  CR16   0  -0.289  -0.2264  -4.8501  -0.1352
 RHB  C9   C  CR6    0   0.319  -0.0021  -1.0944   0.1654
 RHB  C8   C  CR66   0  -0.034  -1.1622  -0.3041   0.1821
 RHB  C13  C  CR16   0  -0.310  -2.4696  -0.8230   0.3056
 RHB  C12  C  CR16   0  -0.336  -3.5669  -0.0187   0.3000
 RHB  C11  C  CR6    0   0.442  -3.4448   1.4000   0.1612
 RHB  N1   N  NT     0  -0.485  -4.5301   2.1926   0.1613
 RHB  C35  C  CH2    0  -0.349  -4.4225   3.6427   0.0993
 RHB  C36  C  CH3    0  -0.658  -4.3144   4.1706  -1.3240
 RHB  C22  C  CH2    0  -0.351  -5.8834   1.6564   0.2152
 RHB  C23  C  CH3    0  -0.656  -6.3673   1.4046   1.6349
 RHB  C10  C  CR16   0  -0.490  -2.1449   1.9300   0.0319
 RHB  C7   C  CR66   0   0.423  -1.0533   1.0931   0.0441
 RHB  O1   O  O      0  -0.472   0.1529   1.6740  -0.0848
 RHB  C1   C  CR66   0   0.422   1.2883   0.9552  -0.0288
 RHB  C2   C  CR66   0  -0.034   1.2417  -0.4453   0.1113
 RHB  C6   C  CR16   0  -0.490   2.4679   1.6593  -0.0980
 RHB  C5   C  CR6    0   0.442   3.7026   0.9828  -0.0226
 RHB  C4   C  CR16   0  -0.336   3.6670  -0.4414   0.1057
 RHB  C3   C  CR16   0  -0.310   2.4849  -1.1127   0.1662
 RHB  N2   N  N      1  -0.485   4.8697   1.6478  -0.0685
 RHB  C24  C  CH2    0  -0.350   4.9245   3.0825  -0.3052
 RHB  C25  C  CH3    0  -0.658   4.7564   3.9073   0.9626
 RHB  C33  C  CH2    0  -0.352   6.1525   0.9852   0.1203
 RHB  C34  C  CH3    0  -0.655   6.7487   0.4622  -1.1778
 RHB  O3   O  O      0  -0.557  -0.1146  -1.8431  -2.1313
 RHB  H1   H  HCR6   0   0.260  -0.0076  -2.1424   2.5991
 RHB  H2   H  HCR6   0   0.263  -0.1306  -4.5214   3.2330
 RHB  H3   H  HCR6   0   0.259  -0.2718  -6.2641   1.4755
 RHB  H4   H  HCR6   0   0.255  -0.2872  -5.6057  -0.9072
 RHB  H5   H  HCR6   0   0.272  -2.6001  -1.8913   0.4153
 RHB  H6   H  HCR6   0   0.282  -4.5368  -0.4773   0.4169
 RHB  H7   H  HCH2   0   0.272  -5.3112   4.0542   0.5784
 RHB  H8   H  HCH2   0   0.260  -3.5799   3.9802   0.7037
 RHB  H9   H  HCH3   0   0.239  -4.2638   5.2593  -1.3156
 RHB  H10  H  HCH3   0   0.234  -3.4228   3.7977  -1.8288
 RHB  H11  H  HCH3   0   0.235  -5.1830   3.8795  -1.9152
 RHB  H12  H  HCH2   0   0.271  -6.5358   2.3783  -0.2764
 RHB  H13  H  HCH2   0   0.261  -5.9473   0.7488  -0.3847
 RHB  H14  H  HCH3   0   0.235  -6.3426   2.3202   2.2265
 RHB  H15  H  HCH3   0   0.239  -7.3949   1.0418   1.6202
 RHB  H16  H  HCH3   0   0.232  -5.7543   0.6593   2.1416
 RHB  H17  H  HCR6   0   0.290  -1.9731   2.9894  -0.0884
 RHB  H18  H  HCR6   0   0.291   2.4131   2.7348  -0.1813
 RHB  H19  H  HCR6   0   0.282   4.5795  -1.0167   0.1425
 RHB  H20  H  HCH2   0   0.272   5.8922   3.2990  -0.7585
 RHB  H21  H  HCH2   0   0.260   4.1805   3.3613  -1.0525
 RHB  H22  H  HCH3   0   0.234   3.7904   3.7314   1.4353
 RHB  H23  H  HCH3   0   0.234   5.5353   3.6756   1.6894
 RHB  H24  H  HCH3   0   0.239   4.8262   4.9689   0.7258
 RHB  H25  H  HCH2   0   0.270   6.8278   1.7119   0.5733
 RHB  H26  H  HCH2   0   0.261   6.0503   0.1841   0.8516
 RHB  H27  H  HCH3   0   0.234   6.8931   1.2682  -1.8984
 RHB  H28  H  HCH3   0   0.239   7.7205   0.0073  -0.9866
 RHB  H29  H  HCH3   0   0.232   6.1092  -0.2910  -1.6376
 RHB  H31  H  HCR6   0   0.272   2.4984  -2.1911   0.2532

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
 RHB  C26  O3   deloc     1.250  0.020  1.250
 RHB  C26  O2   deloc     1.240  0.020  1.240
 RHB  C19  C26  single    1.515  0.020  1.515
 RHB  C14  C19  aromatic  1.392  0.020  1.392
 RHB  C14  C9   single    1.482  0.020  1.482
 RHB  C15  C14  aromatic  1.392  0.020  1.392
 RHB  C15  H1   single    0.930  0.020  1.080
 RHB  C16  C17  aromatic  1.389  0.020  1.389
 RHB  C16  C15  aromatic  1.387  0.020  1.387
 RHB  C16  H2   single    0.930  0.020  1.080
 RHB  C17  C18  aromatic  1.387  0.020  1.387
 RHB  C17  H3   single    0.930  0.020  1.080
 RHB  C18  C19  aromatic  1.390  0.020  1.390
 RHB  C18  H4   single    0.930  0.020  1.080
 RHB  C9   C2   double    1.404  0.020  1.404
 RHB  C8   C9   single    1.404  0.020  1.404
 RHB  C8   C7   aromatic  1.408  0.020  1.408
 RHB  C13  C8   aromatic  1.412  0.020  1.412
 RHB  C13  H5   single    0.930  0.020  1.080
 RHB  C12  C13  aromatic  1.361  0.020  1.361
 RHB  C12  C11  aromatic  1.431  0.020  1.431
 RHB  C12  H6   single    0.930  0.020  1.080
 RHB  C11  C10  aromatic  1.410  0.020  1.410
 RHB  N1   C11  single    1.344  0.020  1.344
 RHB  N1   C22  single    1.457  0.020  1.457
 RHB  C35  N1   single    1.455  0.020  1.455
 RHB  C35  H7   single    0.970  0.020  1.090
 RHB  C35  H8   single    0.970  0.020  1.090
 RHB  C36  C35  single    1.522  0.020  1.522
 RHB  C36  H9   single    0.970  0.020  1.090
 RHB  C36  H10  single    0.970  0.020  1.090
 RHB  C36  H11  single    0.970  0.020  1.090
 RHB  C22  C23  single    1.521  0.020  1.521
 RHB  C22  H12  single    0.970  0.020  1.090
 RHB  C22  H13  single    0.970  0.020  1.090
 RHB  C23  H14  single    0.970  0.020  1.090
 RHB  C23  H15  single    0.970  0.020  1.090
 RHB  C23  H16  single    0.970  0.020  1.090
 RHB  C10  C7   aromatic  1.376  0.020  1.376
 RHB  C10  H17  single    0.930  0.020  1.080
 RHB  C7   O1   single    1.345  0.020  1.345
 RHB  O1   C1   single    1.345  0.020  1.345
 RHB  C1   C6   double    1.375  0.020  1.375
 RHB  C2   C3   single    1.412  0.020  1.412
 RHB  C2   C1   single    1.408  0.020  1.408
 RHB  C6   C5   single    1.410  0.020  1.410
 RHB  C6   H18  single    0.930  0.020  1.080
 RHB  C5   N2   double    1.344  0.020  1.344
 RHB  C4   C5   single    1.430  0.020  1.430
 RHB  C4   H19  single    0.930  0.020  1.080
 RHB  C3   C4   double    1.361  0.020  1.361
 RHB  C3   H31  single    0.930  0.020  1.080
 RHB  N2   C33  single    1.456  0.020  1.456
 RHB  N2   C24  single    1.455  0.020  1.455
 RHB  C24  C25  single    1.522  0.020  1.522
 RHB  C24  H20  single    0.970  0.020  1.090
 RHB  C24  H21  single    0.970  0.020  1.090
 RHB  C25  H22  single    0.970  0.020  1.090
 RHB  C25  H23  single    0.970  0.020  1.090
 RHB  C25  H24  single    0.970  0.020  1.090
 RHB  C33  C34  single    1.521  0.020  1.521
 RHB  C33  H25  single    0.970  0.020  1.090
 RHB  C33  H26  single    0.970  0.020  1.090
 RHB  C34  H27  single    0.970  0.020  1.090
 RHB  C34  H28  single    0.970  0.020  1.090
 RHB  C34  H29  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
 RHB  O3   C26  C19  114.57  3.000
 RHB  C19  C26  O2   118.00  3.000
 RHB  O3   C26  O2   127.43  3.000
 RHB  C18  C19  C14  119.06  3.000
 RHB  C18  C19  C26  121.93  3.000
 RHB  C14  C19  C26  119.01  3.000
 RHB  C9   C14  C15  117.74  3.000
 RHB  C15  C14  C19  120.37  3.000
 RHB  C9   C14  C19  121.89  3.000
 RHB  H1   C15  C16  120.01  3.000
 RHB  C16  C15  C14  120.01  3.000
 RHB  H1   C15  C14  119.98  3.000
 RHB  H2   C16  C17  120.39  3.000
 RHB  H2   C16  C15  119.70  3.000
 RHB  C17  C16  C15  119.91  3.000
 RHB  H3   C17  C18  120.04  3.000
 RHB  H3   C17  C16  120.09  3.000
 RHB  C18  C17  C16  119.87  3.000
 RHB  H4   C18  C17  120.17  3.000
 RHB  H4   C18  C19  119.05  3.000
 RHB  C17  C18  C19  120.78  3.000
 RHB  C2   C9   C8   118.18  3.000
 RHB  C8   C9   C14  120.26  3.000
 RHB  C2   C9   C14  120.28  3.000
 RHB  C7   C8   C13  116.41  3.000
 RHB  C13  C8   C9   124.01  3.000
 RHB  C7   C8   C9   119.57  3.000
 RHB  H5   C13  C12  119.14  3.000
 RHB  C12  C13  C8   121.95  3.000
 RHB  H5   C13  C8   118.91  3.000
 RHB  H6   C12  C11  120.57  3.000
 RHB  H6   C12  C13  118.24  3.000
 RHB  C11  C12  C13  121.18  3.000
 RHB  C10  C11  N1   121.53  3.000
 RHB  N1   C11  C12  121.06  3.000
 RHB  C10  C11  C12  117.41  3.000
 RHB  C22  N1   C35  115.92  3.000
 RHB  C35  N1   C11  121.86  3.000
 RHB  C22  N1   C11  122.22  3.000
 RHB  H8   C35  H7   105.63  3.000
 RHB  H8   C35  C36  110.86  3.000
 RHB  H7   C35  C36  109.75  3.000
 RHB  C36  C35  N1   113.00  3.000
 RHB  H8   C35  N1   109.99  3.000
 RHB  H7   C35  N1   107.28  3.000
 RHB  H11  C36  H10  108.00  3.000
 RHB  H11  C36  H9   107.93  3.000
 RHB  H10  C36  H9   107.89  3.000
 RHB  H11  C36  C35  110.98  3.000
 RHB  H10  C36  C35  111.87  3.000
 RHB  H9   C36  C35  110.04  3.000
 RHB  H13  C22  H12  105.55  3.000
 RHB  H13  C22  C23  110.93  3.000
 RHB  H12  C22  C23  109.89  3.000
 RHB  H13  C22  N1   109.92  3.000
 RHB  H12  C22  N1   107.19  3.000
 RHB  C23  C22  N1   113.02  3.000
 RHB  H16  C23  H15  107.99  3.000
 RHB  H16  C23  H14  108.01  3.000
 RHB  H15  C23  H14  107.95  3.000
 RHB  H16  C23  C22  111.61  3.000
 RHB  H15  C23  C22  110.03  3.000
 RHB  H14  C23  C22  111.12  3.000
 RHB  H17  C10  C7   118.13  3.000
 RHB  H17  C10  C11  121.71  3.000
 RHB  C7   C10  C11  120.15  3.000
 RHB  O1   C7   C10  116.62  3.000
 RHB  O1   C7   C8   120.48  3.000
 RHB  C10  C7   C8   122.90  3.000
 RHB  C1   O1   C7   121.49  3.000
 RHB  C6   C1   C2   122.85  3.000
 RHB  C2   C1   O1   120.51  3.000
 RHB  C6   C1   O1   116.64  3.000
 RHB  C3   C2   C1   116.41  3.000
 RHB  C1   C2   C9   119.53  3.000
 RHB  C3   C2   C9   124.05  3.000
 RHB  H18  C6   C5   121.75  3.000
 RHB  H18  C6   C1   118.04  3.000
 RHB  C5   C6   C1   120.18  3.000
 RHB  N2   C5   C4   121.15  3.000
 RHB  C4   C5   C6   117.43  3.000
 RHB  N2   C5   C6   121.42  3.000
 RHB  H19  C4   C3   118.03  3.000
 RHB  C3   C4   C5   121.12  3.000
 RHB  H19  C4   C5   120.85  3.000
 RHB  H31  C3   C4   118.98  3.000
 RHB  H31  C3   C2   119.02  3.000
 RHB  C4   C3   C2   122.00  3.000
 RHB  C33  N2   C24  115.88  3.000
 RHB  C24  N2   C5   121.74  3.000
 RHB  C33  N2   C5   122.37  3.000
 RHB  H21  C24  H20  105.65  3.000
 RHB  H21  C24  C25  110.91  3.000
 RHB  H20  C24  C25  109.68  3.000
 RHB  H21  C24  N2   109.74  3.000
 RHB  H20  C24  N2   107.27  3.000
 RHB  C25  C24  N2   113.25  3.000
 RHB  H24  C25  H23  107.82  3.000
 RHB  H24  C25  H22  107.95  3.000
 RHB  H23  C25  H22  108.05  3.000
 RHB  H24  C25  C24  109.87  3.000
 RHB  H23  C25  C24  111.18  3.000
 RHB  H22  C25  C24  111.83  3.000
 RHB  H26  C33  H25  105.62  3.000
 RHB  H26  C33  C34  110.90  3.000
 RHB  H25  C33  C34  109.93  3.000
 RHB  H26  C33  N2   109.81  3.000
 RHB  H25  C33  N2   107.23  3.000
 RHB  C34  C33  N2   113.02  3.000
 RHB  H29  C34  H28  107.99  3.000
 RHB  H29  C34  H27  108.04  3.000
 RHB  H28  C34  H27  107.83  3.000
 RHB  H29  C34  C33  111.58  3.000
 RHB  H28  C34  C33  110.08  3.000
 RHB  H27  C34  C33  111.20  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
 RHB  CONST_01  C16  C15  C14  C19     0.00   0.0  0
 RHB  CONST_02  C16  C17  C18  C19     0.00   0.0  0
 RHB  CONST_03  C17  C18  C19  C14     0.00   0.0  0
 RHB  CONST_04  C17  C16  C15  C14     0.00   0.0  0
 RHB  CONST_05  C18  C19  C14  C15     0.00   0.0  0
 RHB  CONST_06  C18  C17  C16  C15     0.00   0.0  0
 RHB  CONST_07  C11  C10  C7   C8      0.00   0.0  0
 RHB  CONST_08  C11  C12  C13  C8      0.00   0.0  0
 RHB  CONST_09  C10  C7   C8   C13     0.00   0.0  0
 RHB  CONST_10  C10  C11  C12  C13     0.00   0.0  0
 RHB  CONST_11  C7   C8   C13  C12     0.00   0.0  0
 RHB  CONST_12  C7   C10  C11  C12     0.00   0.0  0
 RHB  CONST_13  C9   C14  C15  C16   180.00   0.0  0
 RHB  CONST_14  C9   C14  C19  C18   180.00   0.0  0
 RHB  CONST_15  C9   C14  C19  C26     0.00   0.0  0
 RHB  CONST_16  C15  C14  C19  C26   180.00   0.0  0
 RHB  CONST_17  C17  C18  C19  C26   180.00   0.0  0
 RHB  CONST_18  N1   C11  C12  C13   180.00   0.0  0
 RHB  CONST_19  C7   C10  C11  N1    180.00   0.0  0
 RHB  CONST_20  H1   C15  C14  C19   180.00   0.0  0
 RHB  CONST_21  H3   C17  C18  C19   180.00   0.0  0
 RHB  CONST_22  H4   C18  C19  C14   180.00   0.0  0
 RHB  CONST_23  H2   C16  C15  C14   180.00   0.0  0
 RHB  CONST_24  H5   C13  C8   C9      0.00   0.0  0
 RHB  CONST_25  H17  C10  C7   C8    180.00   0.0  0
 RHB  CONST_26  H6   C12  C13  C8    180.00   0.0  0
 RHB  CONST_27  C22  N1   C11  C12     0.00   0.0  0
 RHB  CONST_28  C35  N1   C11  C12   180.00   0.0  0
 RHB  CONST_29  C10  C11  N1   C35     0.00   0.0  0
 RHB  CONST_30  C10  C11  N1   C22   180.00   0.0  0
 RHB  Var_01    C2   C9   C14  C19   -96.27  30.0  2
 RHB  Var_02    C3   C2   C9   C14     9.11  30.0  1
 RHB  Var_03    C7   C8   C9   C14   171.84  30.0  1
 RHB  Var_04    C6   C1   O1   C7   -176.49  30.0  1
 RHB  Var_05    C14  C19  C26  O2    179.13  30.0  2
 RHB  Var_06    C33  N2   C5   C6    174.70  30.0  2
 RHB  Var_07    C23  C22  N1   C11    86.39  30.0  3
 RHB  Var_08    C36  C35  N1   C11    85.66  30.0  3
 RHB  Var_09    C34  C33  N2   C5     89.26  30.0  3
 RHB  Var_10    C25  C24  N2   C5     85.31  30.0  3
 RHB  Var_11    H14  C23  C22  N1     58.31  30.0  3
 RHB  Var_12    H9   C36  C35  N1    178.47  30.0  3
 RHB  Var_13    H27  C34  C33  N2     58.63  30.0  3
 RHB  Var_14    H22  C25  C24  N2    -61.28  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
 RHB  plan-1  C26  0.020
 RHB  plan-1  C19  0.020
 RHB  plan-1  C14  0.020
 RHB  plan-1  C15  0.020
 RHB  plan-1  C16  0.020
 RHB  plan-1  C17  0.020
 RHB  plan-1  C18  0.020
 RHB  plan-1  C9   0.020
 RHB  plan-1  H1   0.020
 RHB  plan-1  H2   0.020
 RHB  plan-1  H3   0.020
 RHB  plan-1  H4   0.020
 RHB  plan-2  C9   0.020
 RHB  plan-2  C8   0.020
 RHB  plan-2  C13  0.020
 RHB  plan-2  C12  0.020
 RHB  plan-2  C11  0.020
 RHB  plan-2  N1   0.020
 RHB  plan-2  C10  0.020
 RHB  plan-2  C7   0.020
 RHB  plan-2  O1   0.020
 RHB  plan-2  H5   0.020
 RHB  plan-2  H6   0.020
 RHB  plan-2  H17  0.020
 RHB  plan-3  C9   0.020
 RHB  plan-3  O1   0.020
 RHB  plan-3  C1   0.020
 RHB  plan-3  C2   0.020
 RHB  plan-3  C6   0.020
 RHB  plan-3  C5   0.020
 RHB  plan-3  C4   0.020
 RHB  plan-3  C3   0.020
 RHB  plan-3  N2   0.020
 RHB  plan-3  H18  0.020
 RHB  plan-3  H19  0.020
 RHB  plan-3  H31  0.020
 RHB  plan-4  C11  0.020
 RHB  plan-4  N1   0.020
 RHB  plan-4  C35  0.020
 RHB  plan-4  C22  0.020
 RHB  plan-5  O2   0.020
 RHB  plan-5  C26  0.020
 RHB  plan-5  C19  0.020
 RHB  plan-5  O3   0.020

