# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr 24 11:19:18 2020
#   Inital geometry file: a 125 line input string
#   Ligand name: 3,3-bis(4-hydroxyphenyl)-6-nitro-1H,3H-benzo[de]isochromen-1-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1ccc(cc1)C2(OC(=O)c3cccc4c3c2ccc4[N+]([O-])=O)c5ccc(O)cc5
#
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
 MR2  MR2  3,3-bis(4-hydroxyphenyl)-6-nitro-1H,3H-benzo[de]isochromen-1-one  ligand  46  31  .  2021-08-14  2021-08-14  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_MR2
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
 MR2  C1   C  CR6    0   0.555  -0.0916   1.2090   2.3461
 MR2  C2   C  CR66   0  -0.195  -1.3941   1.1327   1.6560
 MR2  C3   C  CR16   0  -0.273  -2.4468   1.8831   2.1135
 MR2  C4   C  CR16   0  -0.235  -3.7262   1.6847   1.5770
 MR2  C5   C  CR16   0  -0.287  -3.9511   0.7314   0.6196
 MR2  C6   C  CR66   0   0.127  -2.8859  -0.0516   0.1144
 MR2  C7   C  CR6    0   0.185  -3.0049  -1.0899  -0.8481
 MR2  C8   C  CR16   0  -0.264  -1.9365  -1.8429  -1.2456
 MR2  C9   C  CR16   0  -0.316  -0.6521  -1.5481  -0.7642
 MR2  C10  C  CR66   0   0.032  -0.4694  -0.5370   0.1371
 MR2  C11  C  C      0   0.190  -1.5843   0.1769   0.6310
 MR2  C12  C  CR6    0   0.129   0.9038  -0.0416   0.5322
 MR2  C13  C  CR6    0   0.046   1.3068   1.1425  -0.3415
 MR2  C14  C  CR16   0  -0.250   2.3194   1.9950   0.0970
 MR2  C15  C  CR16   0  -0.372   2.7394   3.0664  -0.6709
 MR2  C16  C  CR6    0   0.352   2.1569   3.3061  -1.9143
 MR2  C17  C  CR16   0  -0.326   1.1546   2.4555  -2.3689
 MR2  C18  C  CR16   0  -0.264   0.7392   1.3898  -1.5866
 MR2  C19  C  CR6    0   0.058   1.9254  -1.1620   0.5078
 MR2  C20  C  CR16   0  -0.277   2.9071  -1.2457  -0.4688
 MR2  C21  C  CR16   0  -0.374   3.8003  -2.3079  -0.4996
 MR2  C22  C  CR6    0   0.353   3.7240  -3.3104   0.4601
 MR2  C23  C  CR16   0  -0.327   2.7366  -3.2404   1.4441
 MR2  C24  C  CR16   0  -0.254   1.8503  -2.1810   1.4586
 MR2  N1   N  N      1   0.325  -4.2791  -1.3865  -1.4847
 MR2  O1   O  O      0  -0.467   0.8841   0.4166   1.8993
 MR2  O2   O  O      0  -0.408   0.1055   1.8721   3.3309
 MR2  O3   O  OH1    0  -0.627   2.5226   4.3318  -2.7027
 MR2  O4   O  OH1    0  -0.627   4.5648  -4.3595   0.4880
 MR2  O5   O  O     -1  -0.364  -4.5456  -2.5457  -1.6905
 MR2  O6   O  O      0  -0.370  -4.9858  -0.4580  -1.7996
 MR2  H3   H  HCR6   0   0.285  -2.3030   2.6043   2.9061
 MR2  H4   H  HCR6   0   0.284  -4.5542   2.2744   1.9450
 MR2  H5   H  HCR6   0   0.276  -4.9601   0.5880   0.2674
 MR2  H8   H  HCR6   0   0.308  -2.0569  -2.6352  -1.9707
 MR2  H9   H  HCR6   0   0.285   0.1882  -2.1100  -1.1472
 MR2  H14  H  HCR6   0   0.266   2.7995   1.8290   1.0526
 MR2  H15  H  HCR6   0   0.276   3.5252   3.7145  -0.2998
 MR2  H17  H  HCR6   0   0.269   0.6961   2.6298  -3.3339
 MR2  H18  H  HCR6   0   0.255  -0.0440   0.7539  -1.9772
 MR2  H20  H  HCR6   0   0.264   2.9903  -0.4838  -1.2319
 MR2  H21  H  HCR6   0   0.275   4.5574  -2.3474  -1.2740
 MR2  H23  H  HCR6   0   0.268   2.6666  -4.0192   2.1931
 MR2  H24  H  HCR6   0   0.260   1.0865  -2.1594   2.2258
 MR2  HO3  H  HOH1   0   0.477   3.2092   4.8575  -2.2769
 MR2  HO4  H  HOH1   0   0.476   5.1936  -4.3062  -0.2405

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
 MR2  C1   C2   single    1.476  0.020  1.476
 MR2  C1   O1   single    1.334  0.020  1.334
 MR2  C1   O2   double    1.203  0.020  1.203
 MR2  C2   C3   aromatic  1.371  0.020  1.371
 MR2  C2   C11  aromatic  1.414  0.020  1.414
 MR2  C3   C4   aromatic  1.401  0.020  1.401
 MR2  C3   H3   single    0.930  0.020  1.080
 MR2  C4   C5   aromatic  1.370  0.020  1.370
 MR2  C4   H4   single    0.930  0.020  1.080
 MR2  C5   C6   aromatic  1.415  0.020  1.415
 MR2  C5   H5   single    0.930  0.020  1.080
 MR2  C6   C7   aromatic  1.421  0.020  1.421
 MR2  C6   C11  aromatic  1.419  0.020  1.419
 MR2  C7   C8   aromatic  1.366  0.020  1.366
 MR2  C7   N1   single    1.455  0.020  1.455
 MR2  C8   C9   aromatic  1.403  0.020  1.403
 MR2  C8   H8   single    0.930  0.020  1.080
 MR2  C9   C10  aromatic  1.367  0.020  1.367
 MR2  C9   H9   single    0.930  0.020  1.080
 MR2  C10  C11  aromatic  1.413  0.020  1.413
 MR2  C10  C12  single    1.512  0.020  1.512
 MR2  C12  C13  single    1.526  0.020  1.526
 MR2  C12  C19  single    1.516  0.020  1.516
 MR2  C12  O1   single    1.442  0.020  1.442
 MR2  C13  C14  aromatic  1.394  0.020  1.394
 MR2  C13  C18  aromatic  1.390  0.020  1.390
 MR2  C14  C15  aromatic  1.383  0.020  1.383
 MR2  C14  H14  single    0.930  0.020  1.080
 MR2  C15  C16  aromatic  1.394  0.020  1.394
 MR2  C15  H15  single    0.930  0.020  1.080
 MR2  C16  C17  aromatic  1.391  0.020  1.391
 MR2  C16  O3   single    1.344  0.020  1.344
 MR2  C17  C18  aromatic  1.386  0.020  1.386
 MR2  C17  H17  single    0.930  0.020  1.080
 MR2  C18  H18  single    0.930  0.020  1.080
 MR2  C19  C20  aromatic  1.387  0.020  1.387
 MR2  C19  C24  aromatic  1.396  0.020  1.396
 MR2  C20  C21  aromatic  1.388  0.020  1.388
 MR2  C20  H20  single    0.930  0.020  1.080
 MR2  C21  C22  aromatic  1.390  0.020  1.390
 MR2  C21  H21  single    0.930  0.020  1.080
 MR2  C22  C23  aromatic  1.396  0.020  1.396
 MR2  C22  O4   single    1.345  0.020  1.345
 MR2  C23  C24  aromatic  1.381  0.020  1.381
 MR2  C23  H23  single    0.930  0.020  1.080
 MR2  C24  H24  single    0.930  0.020  1.080
 MR2  N1   O5   single    1.207  0.020  1.207
 MR2  N1   O6   double    1.209  0.020  1.209
 MR2  O3   HO3  single    0.850  0.020  0.980
 MR2  O4   HO4  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
 MR2  O2   C1   O1   118.80  3.000
 MR2  O2   C1   C2   123.75  3.000
 MR2  O1   C1   C2   117.26  3.000
 MR2  C11  C2   C3   120.55  3.000
 MR2  C11  C2   C1   119.50  3.000
 MR2  C3   C2   C1   119.55  3.000
 MR2  H3   C3   C4   119.77  3.000
 MR2  H3   C3   C2   120.49  3.000
 MR2  C4   C3   C2   119.71  3.000
 MR2  H4   C4   C5   119.46  3.000
 MR2  H4   C4   C3   119.45  3.000
 MR2  C5   C4   C3   121.06  3.000
 MR2  H5   C5   C6   120.94  3.000
 MR2  H5   C5   C4   118.33  3.000
 MR2  C6   C5   C4   120.73  3.000
 MR2  C11  C6   C7   116.18  3.000
 MR2  C11  C6   C5   118.12  3.000
 MR2  C7   C6   C5   125.67  3.000
 MR2  N1   C7   C8   116.44  3.000
 MR2  N1   C7   C6   121.25  3.000
 MR2  C8   C7   C6   122.30  3.000
 MR2  H8   C8   C9   119.10  3.000
 MR2  H8   C8   C7   120.80  3.000
 MR2  C9   C8   C7   120.02  3.000
 MR2  H9   C9   C10  120.95  3.000
 MR2  H9   C9   C8   118.74  3.000
 MR2  C10  C9   C8   120.27  3.000
 MR2  C12  C10  C11  117.36  3.000
 MR2  C12  C10  C9   122.41  3.000
 MR2  C11  C10  C9   119.92  3.000
 MR2  C10  C11  C6   121.01  3.000
 MR2  C10  C11  C2   119.25  3.000
 MR2  C6   C11  C2   119.74  3.000
 MR2  O1   C12  C19  105.02  3.000
 MR2  O1   C12  C13  107.45  3.000
 MR2  C19  C12  C13  112.72  3.000
 MR2  O1   C12  C10  109.84  3.000
 MR2  C19  C12  C10  111.44  3.000
 MR2  C13  C12  C10  110.15  3.000
 MR2  C18  C13  C14  117.99  3.000
 MR2  C18  C13  C12  122.88  3.000
 MR2  C14  C13  C12  119.09  3.000
 MR2  H14  C14  C15  118.31  3.000
 MR2  H14  C14  C13  120.40  3.000
 MR2  C15  C14  C13  121.29  3.000
 MR2  H15  C15  C16  120.36  3.000
 MR2  H15  C15  C14  119.54  3.000
 MR2  C16  C15  C14  120.10  3.000
 MR2  O3   C16  C17  118.09  3.000
 MR2  O3   C16  C15  122.73  3.000
 MR2  C17  C16  C15  119.18  3.000
 MR2  H17  C17  C18  120.01  3.000
 MR2  H17  C17  C16  119.87  3.000
 MR2  C18  C17  C16  120.12  3.000
 MR2  H18  C18  C17  117.72  3.000
 MR2  H18  C18  C13  120.95  3.000
 MR2  C17  C18  C13  121.33  3.000
 MR2  C24  C19  C20  118.27  3.000
 MR2  C24  C19  C12  119.49  3.000
 MR2  C20  C19  C12  122.18  3.000
 MR2  H20  C20  C21  118.29  3.000
 MR2  H20  C20  C19  120.58  3.000
 MR2  C21  C20  C19  121.13  3.000
 MR2  H21  C21  C22  120.36  3.000
 MR2  H21  C21  C20  119.55  3.000
 MR2  C22  C21  C20  120.09  3.000
 MR2  O4   C22  C23  117.83  3.000
 MR2  O4   C22  C21  122.87  3.000
 MR2  C23  C22  C21  119.30  3.000
 MR2  H23  C23  C24  120.19  3.000
 MR2  H23  C23  C22  119.82  3.000
 MR2  C24  C23  C22  119.98  3.000
 MR2  H24  C24  C23  118.38  3.000
 MR2  H24  C24  C19  120.40  3.000
 MR2  C23  C24  C19  121.22  3.000
 MR2  O6   N1   O5   124.35  3.000
 MR2  O6   N1   C7   118.00  3.000
 MR2  O5   N1   C7   117.62  3.000
 MR2  C12  O1   C1   121.09  3.000
 MR2  HO3  O3   C16  110.53  3.000
 MR2  HO4  O4   C22  110.43  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
 MR2  CONST_01  C5   C4   C3   C2     0.00   0.0  0
 MR2  CONST_02  C5   C6   C11  C2     0.00   0.0  0
 MR2  CONST_03  C7   C6   C11  C2   180.00   0.0  0
 MR2  CONST_04  C9   C10  C11  C2   180.00   0.0  0
 MR2  CONST_05  C6   C11  C2   C3     0.00   0.0  0
 MR2  CONST_06  C10  C11  C2   C3   180.00   0.0  0
 MR2  CONST_07  C6   C5   C4   C3     0.00   0.0  0
 MR2  CONST_08  C11  C2   C3   C4     0.00   0.0  0
 MR2  CONST_09  C7   C6   C5   C4   180.00   0.0  0
 MR2  CONST_10  C11  C6   C5   C4     0.00   0.0  0
 MR2  CONST_11  C8   C7   C6   C5   180.00   0.0  0
 MR2  CONST_12  C10  C11  C6   C5   180.00   0.0  0
 MR2  CONST_13  C9   C8   C7   C6     0.00   0.0  0
 MR2  CONST_14  C9   C10  C11  C6     0.00   0.0  0
 MR2  CONST_15  C10  C11  C6   C7     0.00   0.0  0
 MR2  CONST_16  C10  C9   C8   C7     0.00   0.0  0
 MR2  CONST_17  C11  C6   C7   C8     0.00   0.0  0
 MR2  CONST_18  C11  C10  C9   C8     0.00   0.0  0
 MR2  CONST_19  C16  C15  C14  C13    0.00   0.0  0
 MR2  CONST_20  C16  C17  C18  C13    0.00   0.0  0
 MR2  CONST_21  C17  C18  C13  C14    0.00   0.0  0
 MR2  CONST_22  C17  C16  C15  C14    0.00   0.0  0
 MR2  CONST_23  C18  C13  C14  C15    0.00   0.0  0
 MR2  CONST_24  C18  C17  C16  C15    0.00   0.0  0
 MR2  CONST_25  C22  C21  C20  C19    0.00   0.0  0
 MR2  CONST_26  C22  C23  C24  C19    0.00   0.0  0
 MR2  CONST_27  C23  C24  C19  C20    0.00   0.0  0
 MR2  CONST_28  C23  C22  C21  C20    0.00   0.0  0
 MR2  CONST_29  C24  C19  C20  C21    0.00   0.0  0
 MR2  CONST_30  C24  C23  C22  C21    0.00   0.0  0
 MR2  CONST_31  C15  C14  C13  C12  180.00   0.0  0
 MR2  CONST_32  C17  C18  C13  C12  180.00   0.0  0
 MR2  CONST_33  C21  C20  C19  C12  180.00   0.0  0
 MR2  CONST_34  C23  C24  C19  C12  180.00   0.0  0
 MR2  CONST_35  N1   C7   C6   C5     0.00   0.0  0
 MR2  CONST_36  N1   C7   C8   C9   180.00   0.0  0
 MR2  CONST_37  N1   C7   C6   C11  180.00   0.0  0
 MR2  CONST_38  O3   C16  C15  C14  180.00   0.0  0
 MR2  CONST_39  O3   C16  C17  C18  180.00   0.0  0
 MR2  CONST_40  O4   C22  C21  C20  180.00   0.0  0
 MR2  CONST_41  O4   C22  C23  C24  180.00   0.0  0
 MR2  CONST_42  H3   C3   C2   C1     0.00   0.0  0
 MR2  CONST_43  H4   C4   C3   C2   180.00   0.0  0
 MR2  CONST_44  H5   C5   C4   C3   180.00   0.0  0
 MR2  CONST_45  H8   C8   C7   C6   180.00   0.0  0
 MR2  CONST_46  H9   C9   C8   C7   180.00   0.0  0
 MR2  CONST_47  H14  C14  C13  C12    0.00   0.0  0
 MR2  CONST_48  H18  C18  C13  C12    0.00   0.0  0
 MR2  CONST_49  H20  C20  C19  C12    0.00   0.0  0
 MR2  CONST_50  H24  C24  C19  C12    0.00   0.0  0
 MR2  CONST_51  H15  C15  C14  C13  180.00   0.0  0
 MR2  CONST_52  H17  C17  C18  C13  180.00   0.0  0
 MR2  CONST_53  H21  C21  C20  C19  180.00   0.0  0
 MR2  CONST_54  H23  C23  C24  C19  180.00   0.0  0
 MR2  Var_01    C10  C12  O1   C1   -46.23  30.0  1
 MR2  Var_02    O1   C1   C2   C3   177.14  30.0  1
 MR2  Var_03    C14  C13  C12  C10  160.71  30.0  2
 MR2  Var_04    C20  C19  C12  C10  108.06  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
 MR2  plan-1  C12  0.020
 MR2  plan-1  C13  0.020
 MR2  plan-1  C14  0.020
 MR2  plan-1  C15  0.020
 MR2  plan-1  C16  0.020
 MR2  plan-1  C17  0.020
 MR2  plan-1  C18  0.020
 MR2  plan-1  O3   0.020
 MR2  plan-1  H14  0.020
 MR2  plan-1  H15  0.020
 MR2  plan-1  H17  0.020
 MR2  plan-1  H18  0.020
 MR2  plan-2  C12  0.020
 MR2  plan-2  C19  0.020
 MR2  plan-2  C20  0.020
 MR2  plan-2  C21  0.020
 MR2  plan-2  C22  0.020
 MR2  plan-2  C23  0.020
 MR2  plan-2  C24  0.020
 MR2  plan-2  O4   0.020
 MR2  plan-2  H20  0.020
 MR2  plan-2  H21  0.020
 MR2  plan-2  H23  0.020
 MR2  plan-2  H24  0.020
 MR2  plan-3  C1   0.020
 MR2  plan-3  C2   0.020
 MR2  plan-3  C3   0.020
 MR2  plan-3  C4   0.020
 MR2  plan-3  C5   0.020
 MR2  plan-3  C6   0.020
 MR2  plan-3  C7   0.020
 MR2  plan-3  C8   0.020
 MR2  plan-3  C9   0.020
 MR2  plan-3  C10  0.020
 MR2  plan-3  C11  0.020
 MR2  plan-3  C12  0.020
 MR2  plan-3  N1   0.020
 MR2  plan-3  H3   0.020
 MR2  plan-3  H4   0.020
 MR2  plan-3  H5   0.020
 MR2  plan-3  H8   0.020
 MR2  plan-3  H9   0.020
 MR2  plan-4  C7   0.020
 MR2  plan-4  N1   0.020
 MR2  plan-4  O5   0.020
 MR2  plan-4  O6   0.020
 MR2  plan-5  C1   0.020
 MR2  plan-5  C2   0.020
 MR2  plan-5  O1   0.020
 MR2  plan-5  O2   0.020

