# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Mar 10 09:12:44 2022
#   Inital geometry file: a 83 line input string
#   Ligand name: 1,3-bis(oxidanylidene)benzo[de]isoquinoline-6,7-dicarboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1ccc2C(=O)NC(=O)c3ccc(C(O)=O)c1c23
#
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
 EQL  EQL  '1,3-bis(oxidanylidene)benzo[de]isoquinoline-6,7-dicarboxylic acid'  ligand  26  21  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_EQL
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
 EQL  C4   C  CR66   0  -0.191  258.7706  22.0693  -18.6547
 EQL  C14  C  C      0   0.370  258.0110  18.4285  -15.2349
 EQL  C5   C  C      0   0.286  258.5905  20.7080  -18.3100
 EQL  C6   C  CR66   0   0.124  258.6299  20.3033  -16.9463
 EQL  C11  C  CR6    0   0.531  258.7249  22.4999  -20.0574
 EQL  C7   C  CR66   0  -0.191  258.3711  19.7528  -19.3311
 EQL  C8   C  CR16   0  -0.276  258.1929  18.4304  -19.0032
 EQL  C9   C  CR16   0  -0.304  258.1752  18.0365  -17.6646
 EQL  C10  C  CR6    0  -0.098  258.3417  18.9400  -16.6366
 EQL  C12  C  CR6    0   0.531  258.3419  20.1575  -20.7421
 EQL  C13  C  C      0   0.370  259.3807  20.9533  -14.5290
 EQL  N1   N  NR16   0  -0.737  258.5172  21.5019  -20.9824
 EQL  C3   C  CR16   0  -0.276  258.9827  23.0020  -17.6687
 EQL  C1   C  CR6    0  -0.096  258.9564  21.2816  -15.9595
 EQL  C2   C  CR16   0  -0.304  259.0788  22.6024  -16.3350
 EQL  O1   O  O      0  -0.430  258.8566  23.6527  -20.4201
 EQL  O2   O  O      0  -0.430  258.1778  19.3887  -21.6692
 EQL  O3   O  O      0  -0.583  260.2362  20.0547  -14.4464
 EQL  O4   O  OC    -1  -0.581  257.1979  19.1320  -14.6110
 EQL  O5   O  OC    -1  -0.588  258.9284  21.6761  -13.6269
 EQL  O6   O  O      0  -0.588  258.4907  17.3297  -14.9121
 EQL  H1   H  HCR6   0   0.265  258.0372  17.6949  -19.7816
 EQL  H2   H  HCR6   0   0.257  257.9844  16.9979  -17.4294
 EQL  H3   H  HNR6   0   0.414  258.4898  21.7905  -21.9535
 EQL  H4   H  HCR6   0   0.265  259.1058  24.0456  -17.9270
 EQL  H5   H  HCR6   0   0.257  259.2981  23.3474  -15.5818

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
 EQL  O2   C12  double    1.216  0.020  1.216
 EQL  N1   C12  single    1.377  0.020  1.377
 EQL  N1   C11  single    1.376  0.020  1.376
 EQL  C12  C7   single    1.468  0.020  1.468
 EQL  O1   C11  double    1.216  0.020  1.216
 EQL  C11  C4   single    1.468  0.020  1.468
 EQL  C7   C8   aromatic  1.374  0.020  1.374
 EQL  C7   C5   aromatic  1.415  0.020  1.415
 EQL  C8   C9   aromatic  1.396  0.020  1.396
 EQL  C4   C5   aromatic  1.416  0.020  1.416
 EQL  C4   C3   aromatic  1.374  0.020  1.374
 EQL  C5   C6   aromatic  1.423  0.020  1.423
 EQL  C3   C2   aromatic  1.396  0.020  1.396
 EQL  C9   C10  aromatic  1.379  0.020  1.379
 EQL  C6   C10  aromatic  1.427  0.020  1.427
 EQL  C6   C1   aromatic  1.427  0.020  1.427
 EQL  C10  C14  single    1.528  0.020  1.528
 EQL  C2   C1   aromatic  1.379  0.020  1.379
 EQL  C1   C13  single    1.528  0.020  1.528
 EQL  C14  O6   deloc     1.242  0.020  1.242
 EQL  C14  O4   deloc     1.243  0.020  1.243
 EQL  C13  O3   deloc     1.243  0.020  1.243
 EQL  C13  O5   deloc     1.241  0.020  1.241
 EQL  C8   H1   single    0.930  0.020  1.080
 EQL  C9   H2   single    0.930  0.020  1.080
 EQL  N1   H3   single    0.860  0.020  1.020
 EQL  C3   H4   single    0.930  0.020  1.080
 EQL  C2   H5   single    0.930  0.020  1.080

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
 EQL  C3   C4   C11  119.44  3.000
 EQL  C3   C4   C5   119.85  3.000
 EQL  C11  C4   C5   120.72  3.000
 EQL  O6   C14  O4   128.54  3.000
 EQL  O4   C14  C10  114.36  3.000
 EQL  O6   C14  C10  116.81  3.000
 EQL  C7   C5   C6   120.25  3.000
 EQL  C6   C5   C4   120.22  3.000
 EQL  C7   C5   C4   119.54  3.000
 EQL  C1   C6   C10  123.42  3.000
 EQL  C1   C6   C5   118.29  3.000
 EQL  C10  C6   C5   118.29  3.000
 EQL  O1   C11  N1   120.22  3.000
 EQL  O1   C11  C4   124.05  3.000
 EQL  N1   C11  C4   115.73  3.000
 EQL  C12  C7   C8   119.47  3.000
 EQL  C8   C7   C5   119.84  3.000
 EQL  C12  C7   C5   120.69  3.000
 EQL  H1   C8   C9   119.76  3.000
 EQL  H1   C8   C7   120.08  3.000
 EQL  C9   C8   C7   120.14  3.000
 EQL  H2   C9   C10  119.23  3.000
 EQL  H2   C9   C8   118.80  3.000
 EQL  C10  C9   C8   121.92  3.000
 EQL  C9   C10  C6   119.24  3.000
 EQL  C6   C10  C14  124.22  3.000
 EQL  C9   C10  C14  116.00  3.000
 EQL  O2   C12  N1   120.11  3.000
 EQL  N1   C12  C7   115.75  3.000
 EQL  O2   C12  C7   124.15  3.000
 EQL  O5   C13  O3   128.55  3.000
 EQL  O5   C13  C1   117.01  3.000
 EQL  O3   C13  C1   114.11  3.000
 EQL  H3   N1   C12  116.22  3.000
 EQL  H3   N1   C11  116.21  3.000
 EQL  C12  N1   C11  127.58  3.000
 EQL  H4   C3   C2   119.76  3.000
 EQL  H4   C3   C4   120.07  3.000
 EQL  C2   C3   C4   120.14  3.000
 EQL  C2   C1   C13  115.86  3.000
 EQL  C13  C1   C6   124.30  3.000
 EQL  C2   C1   C6   119.25  3.000
 EQL  H5   C2   C1   119.21  3.000
 EQL  H5   C2   C3   118.83  3.000
 EQL  C1   C2   C3   121.91  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
 EQL  CONST_01  C8   C7   C5   C4    180.00   0.0  0
 EQL  CONST_02  C10  C6   C5   C4    180.00   0.0  0
 EQL  CONST_03  C1   C6   C5   C4      0.00   0.0  0
 EQL  CONST_04  C1   C2   C3   C4      0.00   0.0  0
 EQL  CONST_05  C9   C8   C7   C5      0.00   0.0  0
 EQL  CONST_06  C2   C3   C4   C5      0.00   0.0  0
 EQL  CONST_07  C9   C10  C6   C5      0.00   0.0  0
 EQL  CONST_08  C2   C1   C6   C5      0.00   0.0  0
 EQL  CONST_09  C8   C7   C5   C6      0.00   0.0  0
 EQL  CONST_10  C3   C4   C5   C6      0.00   0.0  0
 EQL  CONST_11  C8   C9   C10  C6      0.00   0.0  0
 EQL  CONST_12  C3   C2   C1   C6      0.00   0.0  0
 EQL  CONST_13  C10  C9   C8   C7      0.00   0.0  0
 EQL  CONST_14  C3   C4   C5   C7    180.00   0.0  0
 EQL  CONST_15  C10  C6   C5   C7      0.00   0.0  0
 EQL  CONST_16  C1   C6   C5   C7    180.00   0.0  0
 EQL  CONST_17  C1   C6   C10  C9    180.00   0.0  0
 EQL  CONST_18  C2   C1   C6   C10   180.00   0.0  0
 EQL  CONST_19  C12  N1   C11  C4      0.00   0.0  0
 EQL  CONST_20  C8   C9   C10  C14   180.00   0.0  0
 EQL  CONST_25  C3   C2   C1   C13   180.00   0.0  0
 EQL  CONST_26  O1   C11  N1   C12   180.00   0.0  0
 EQL  CONST_27  H5   C2   C3   C4    180.00   0.0  0
 EQL  CONST_28  H1   C8   C7   C5    180.00   0.0  0
 EQL  CONST_29  H4   C3   C4   C5    180.00   0.0  0
 EQL  CONST_30  H2   C9   C10  C6    180.00   0.0  0
 EQL  CONST_31  H3   N1   C11  C4    180.00   0.0  0
 EQL  Var_01    O6   C14  C10  C6   -140.56  30.0  2
 EQL  Var_02    O3   C13  C1   C6     46.16  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
 EQL  plan-1  C4   0.020
 EQL  plan-1  C14  0.020
 EQL  plan-1  C5   0.020
 EQL  plan-1  C6   0.020
 EQL  plan-1  C11  0.020
 EQL  plan-1  C7   0.020
 EQL  plan-1  C8   0.020
 EQL  plan-1  C9   0.020
 EQL  plan-1  C10  0.020
 EQL  plan-1  C12  0.020
 EQL  plan-1  C13  0.020
 EQL  plan-1  N1   0.020
 EQL  plan-1  C3   0.020
 EQL  plan-1  C1   0.020
 EQL  plan-1  C2   0.020
 EQL  plan-1  O1   0.020
 EQL  plan-1  O2   0.020
 EQL  plan-1  H1   0.020
 EQL  plan-1  H2   0.020
 EQL  plan-1  H3   0.020
 EQL  plan-1  H4   0.020
 EQL  plan-1  H5   0.020
 EQL  plan-2  C14  0.020
 EQL  plan-2  C10  0.020
 EQL  plan-2  O4   0.020
 EQL  plan-2  O6   0.020
 EQL  plan-3  C13  0.020
 EQL  plan-3  C1   0.020
 EQL  plan-3  O3   0.020
 EQL  plan-3  O5   0.020

