# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu May  7 13:33:33 2020
#   Inital geometry file: a 109 line input string
#   Ligand name: 2-(3-bromophenyl)-6-[(2-hydroxyethyl)amino]-1H-benzo[de]isoquinoline-1,3(2H)-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OCCNc1ccc2C(=O)N(C(=O)c3cccc1c23)c4cccc(Br)c4
#
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
 VGI  VGI  2-(3-bromophenyl)-6-[(2-hydroxyethyl)amino]-1H-benzo[de]isoquinoline-1,3(2H)-dione  ligand  41  26  .  2021-08-24  2021-08-24  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_VGI
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
 VGI  C14   C   CR16  0  -0.231  -3.0328   0.1280  -0.1114
 VGI  C15   C   CR6   0  -0.121  -4.3916   0.1837   0.1579
 VGI  BR1   BR  BR    0  -0.036  -5.5707   0.7891  -1.1853
 VGI  C16   C   CR16  0  -0.222  -4.8998  -0.1969   1.3914
 VGI  C17   C   CR16  0  -0.261  -4.0214  -0.6405   2.3702
 VGI  C18   C   CR16  0  -0.255  -2.6585  -0.7027   2.1223
 VGI  C13   C   CR6   0   0.323  -2.1761  -0.3183   0.8825
 VGI  N2    N   NR6   0  -0.725  -0.7753  -0.3828   0.6131
 VGI  C9    C   CR6   0   0.534  -0.0232   0.7677   0.8710
 VGI  O1    O   O     0  -0.443  -0.5817   1.7562   1.3073
 VGI  C12   C   CR6   0   0.545  -0.2826  -1.5822   0.1238
 VGI  O2    O   O     0  -0.431  -1.0322  -2.5178  -0.0673
 VGI  C8    C   CR66  0  -0.160   1.1624  -1.6407  -0.1370
 VGI  C10   C   CR16  0  -0.284   1.7114  -2.8137  -0.6083
 VGI  C11   C   CR16  0  -0.249   3.0827  -2.8961  -0.8523
 VGI  C7    C   CR16  0  -0.298   3.8876  -1.8035  -0.6310
 VGI  C1    C   CR66  0   0.045   3.3611  -0.5858  -0.1639
 VGI  C2    C   C     0   0.298   1.9712  -0.5085   0.0974
 VGI  C3    C   CR66  0  -0.202   1.3974   0.6826   0.5913
 VGI  C4    C   CR16  0  -0.278   2.2164   1.7767   0.8109
 VGI  C5    C   CR16  0  -0.388   3.5763   1.7377   0.5556
 VGI  C6    C   CR6   0   0.392   4.1854   0.5775   0.0677
 VGI  N1    N   NH1   0  -0.684   5.5044   0.5269  -0.1685
 VGI  C19   C   CH2   0  -0.304   6.4053   1.6470  -0.0205
 VGI  C20   C   CH2   0  -0.185   7.8400   1.1743  -0.1033
 VGI  O3    O   OH1   0  -0.671   8.0359   0.5519  -1.3540
 VGI  H14   H   HCR6  0   0.287  -2.6356   0.4247  -1.0733
 VGI  H16   H   HCR6  0   0.285  -5.9610  -0.1533   1.5956
 VGI  H17   H   HCR6  0   0.278  -4.4078  -0.9403   3.3347
 VGI  H18   H   HCR6  0   0.273  -1.9761  -1.0479   2.8877
 VGI  H10   H   HCR6  0   0.275   1.0793  -3.6733  -0.7852
 VGI  H11   H   HCR6  0   0.275   3.5130  -3.8199  -1.2119
 VGI  H7    H   HCR6  0   0.261   4.9467  -1.9159  -0.8213
 VGI  H4    H   HCR6  0   0.271   1.7874   2.6965   1.1860
 VGI  H5    H   HCR6  0   0.283   4.1619   2.6285   0.7305
 VGI  H1    H   HNH1  0   0.403   5.8705  -0.2440  -0.7027
 VGI  H191  H   HCH2  0   0.247   6.2127   2.4127  -0.7812
 VGI  H192  H   HCH2  0   0.254   6.2636   2.1165   0.9549
 VGI  H201  H   HCH2  0   0.222   8.4936   2.0437   0.0312
 VGI  H202  H   HCH2  0   0.217   8.0393   0.4838   0.7243
 VGI  H3    H   HOH1  0   0.463   8.8647   0.0656  -1.3264

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
 VGI  C14  C15   aromatic  1.386  0.020  1.386
 VGI  C14  C13   aromatic  1.386  0.020  1.386
 VGI  C15  BR1   single    1.887  0.020  1.887
 VGI  C15  C16   aromatic  1.387  0.020  1.387
 VGI  C16  C17   aromatic  1.388  0.020  1.388
 VGI  C17  C18   aromatic  1.387  0.020  1.387
 VGI  C18  C13   aromatic  1.385  0.020  1.385
 VGI  C13  N2    single    1.428  0.020  1.428
 VGI  N2   C9    single    1.398  0.020  1.398
 VGI  N2   C12   single    1.386  0.020  1.386
 VGI  C9   O1    double    1.216  0.020  1.216
 VGI  C9   C3    single    1.450  0.020  1.450
 VGI  C12  O2    double    1.214  0.020  1.214
 VGI  C12  C8    single    1.470  0.020  1.470
 VGI  C8   C10   aromatic  1.378  0.020  1.378
 VGI  C8   C2    aromatic  1.411  0.020  1.411
 VGI  C10  C11   aromatic  1.395  0.020  1.395
 VGI  C11  C7    aromatic  1.375  0.020  1.375
 VGI  C7   C1    aromatic  1.406  0.020  1.406
 VGI  C1   C2    aromatic  1.416  0.020  1.416
 VGI  C1   C6    aromatic  1.444  0.020  1.444
 VGI  C2   C3    aromatic  1.411  0.020  1.411
 VGI  C3   C4    aromatic  1.384  0.020  1.384
 VGI  C4   C5    aromatic  1.384  0.020  1.384
 VGI  C5   C6    aromatic  1.398  0.020  1.398
 VGI  C6   N1    single    1.341  0.020  1.341
 VGI  N1   C19   single    1.445  0.020  1.445
 VGI  C19  C20   single    1.513  0.020  1.513
 VGI  C20  O3    single    1.411  0.020  1.411
 VGI  C14  H14   single    0.930  0.020  1.080
 VGI  C16  H16   single    0.930  0.020  1.080
 VGI  C17  H17   single    0.930  0.020  1.080
 VGI  C18  H18   single    0.930  0.020  1.080
 VGI  C10  H10   single    0.930  0.020  1.080
 VGI  C11  H11   single    0.930  0.020  1.080
 VGI  C7   H7    single    0.930  0.020  1.080
 VGI  C4   H4    single    0.930  0.020  1.080
 VGI  C5   H5    single    0.930  0.020  1.080
 VGI  N1   H1    single    0.860  0.020  1.020
 VGI  C19  H191  single    0.970  0.020  1.090
 VGI  C19  H192  single    0.970  0.020  1.090
 VGI  C20  H201  single    0.970  0.020  1.090
 VGI  C20  H202  single    0.970  0.020  1.090
 VGI  O3   H3    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
 VGI  H14   C14  C13   119.93  3.000
 VGI  H14   C14  C15   121.43  3.000
 VGI  C13   C14  C15   118.65  3.000
 VGI  C16   C15  BR1   119.47  3.000
 VGI  C16   C15  C14   121.39  3.000
 VGI  BR1   C15  C14   119.14  3.000
 VGI  H16   C16  C17   120.05  3.000
 VGI  H16   C16  C15   121.08  3.000
 VGI  C17   C16  C15   118.87  3.000
 VGI  H17   C17  C18   119.88  3.000
 VGI  H17   C17  C16   119.44  3.000
 VGI  C18   C17  C16   120.68  3.000
 VGI  H18   C18  C13   120.15  3.000
 VGI  H18   C18  C17   120.51  3.000
 VGI  C13   C18  C17   119.34  3.000
 VGI  N2    C13  C18   119.88  3.000
 VGI  N2    C13  C14   119.05  3.000
 VGI  C18   C13  C14   121.07  3.000
 VGI  C12   N2   C9    125.87  3.000
 VGI  C12   N2   C13   117.03  3.000
 VGI  C9    N2   C13   117.10  3.000
 VGI  C3    C9   O1    124.51  3.000
 VGI  C3    C9   N2    116.29  3.000
 VGI  O1    C9   N2    119.20  3.000
 VGI  C8    C12  O2    123.27  3.000
 VGI  C8    C12  N2    116.53  3.000
 VGI  O2    C12  N2    120.20  3.000
 VGI  C2    C8   C10   120.76  3.000
 VGI  C2    C8   C12   120.15  3.000
 VGI  C10   C8   C12   119.10  3.000
 VGI  H10   C10  C11   119.93  3.000
 VGI  H10   C10  C8    119.97  3.000
 VGI  C11   C10  C8    120.10  3.000
 VGI  H11   C11  C7    119.99  3.000
 VGI  H11   C11  C10   119.99  3.000
 VGI  C7    C11  C10   120.02  3.000
 VGI  H7    C7   C1    120.98  3.000
 VGI  H7    C7   C11   117.53  3.000
 VGI  C1    C7   C11   121.49  3.000
 VGI  C6    C1   C2    119.11  3.000
 VGI  C6    C1   C7    122.48  3.000
 VGI  C2    C1   C7    118.41  3.000
 VGI  C3    C2   C1    120.63  3.000
 VGI  C3    C2   C8    120.15  3.000
 VGI  C1    C2   C8    119.21  3.000
 VGI  C4    C3   C2    118.82  3.000
 VGI  C4    C3   C9    120.17  3.000
 VGI  C2    C3   C9    121.01  3.000
 VGI  H4    C4   C5    118.51  3.000
 VGI  H4    C4   C3    119.49  3.000
 VGI  C5    C4   C3    121.99  3.000
 VGI  H5    C5   C6    120.30  3.000
 VGI  H5    C5   C4    118.65  3.000
 VGI  C6    C5   C4    121.04  3.000
 VGI  N1    C6   C5    121.42  3.000
 VGI  N1    C6   C1    120.18  3.000
 VGI  C5    C6   C1    118.40  3.000
 VGI  H1    N1   C19   114.91  3.000
 VGI  H1    N1   C6    118.69  3.000
 VGI  C19   N1   C6    124.47  3.000
 VGI  H192  C19  H191  107.26  3.000
 VGI  H192  C19  C20   107.84  3.000
 VGI  H191  C19  C20   110.30  3.000
 VGI  H192  C19  N1    110.11  3.000
 VGI  H191  C19  N1    111.15  3.000
 VGI  C20   C19  N1    110.08  3.000
 VGI  H202  C20  H201  107.38  3.000
 VGI  H202  C20  O3    111.48  3.000
 VGI  H201  C20  O3    112.08  3.000
 VGI  H202  C20  C19   109.15  3.000
 VGI  H201  C20  C19   108.12  3.000
 VGI  O3    C20  C19   108.55  3.000
 VGI  H3    O3   C20   108.52  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
 VGI  CONST_01  C17  C16  C15  C14    0.00   0.0  0
 VGI  CONST_02  C17  C18  C13  C14    0.00   0.0  0
 VGI  CONST_03  C18  C13  C14  C15    0.00   0.0  0
 VGI  CONST_04  C18  C17  C16  C15    0.00   0.0  0
 VGI  CONST_05  C13  C14  C15  C16    0.00   0.0  0
 VGI  CONST_06  C13  C18  C17  C16    0.00   0.0  0
 VGI  CONST_07  C7   C11  C10  C8     0.00   0.0  0
 VGI  CONST_08  C7   C1   C2   C8     0.00   0.0  0
 VGI  CONST_09  C6   C1   C2   C8   180.00   0.0  0
 VGI  CONST_10  C4   C3   C2   C8   180.00   0.0  0
 VGI  CONST_11  C1   C2   C8   C10    0.00   0.0  0
 VGI  CONST_12  C3   C2   C8   C10  180.00   0.0  0
 VGI  CONST_13  C1   C7   C11  C10    0.00   0.0  0
 VGI  CONST_14  C2   C8   C10  C11    0.00   0.0  0
 VGI  CONST_15  C2   C1   C7   C11    0.00   0.0  0
 VGI  CONST_16  C6   C1   C7   C11  180.00   0.0  0
 VGI  CONST_17  C3   C2   C1   C7   180.00   0.0  0
 VGI  CONST_18  C5   C6   C1   C7   180.00   0.0  0
 VGI  CONST_19  C4   C3   C2   C1     0.00   0.0  0
 VGI  CONST_20  C4   C5   C6   C1     0.00   0.0  0
 VGI  CONST_21  C5   C6   C1   C2     0.00   0.0  0
 VGI  CONST_22  C5   C4   C3   C2     0.00   0.0  0
 VGI  CONST_23  C6   C1   C2   C3     0.00   0.0  0
 VGI  CONST_24  C6   C5   C4   C3     0.00   0.0  0
 VGI  CONST_25  N2   C13  C14  C15  180.00   0.0  0
 VGI  CONST_26  N2   C13  C18  C17  180.00   0.0  0
 VGI  CONST_27  C3   C9   N2   C13  180.00   0.0  0
 VGI  CONST_28  C3   C9   N2   C12    0.00   0.0  0
 VGI  CONST_29  C13  C14  C15  BR1  180.00   0.0  0
 VGI  CONST_30  C17  C16  C15  BR1  180.00   0.0  0
 VGI  CONST_31  N1   C6   C1   C7     0.00   0.0  0
 VGI  CONST_32  N1   C6   C1   C2   180.00   0.0  0
 VGI  CONST_33  N1   C6   C5   C4   180.00   0.0  0
 VGI  CONST_34  O1   C9   N2   C13    0.00   0.0  0
 VGI  CONST_35  C12  N2   C9   O1   180.00   0.0  0
 VGI  CONST_36  H16  C16  C15  C14  180.00   0.0  0
 VGI  CONST_37  H18  C18  C13  C14  180.00   0.0  0
 VGI  CONST_38  H17  C17  C16  C15  180.00   0.0  0
 VGI  CONST_39  H14  C14  C15  C16  180.00   0.0  0
 VGI  CONST_40  H4   C4   C3   C9     0.00   0.0  0
 VGI  CONST_41  H10  C10  C8   C12    0.00   0.0  0
 VGI  CONST_42  H11  C11  C10  C8   180.00   0.0  0
 VGI  CONST_43  H7   C7   C11  C10  180.00   0.0  0
 VGI  CONST_44  H5   C5   C6   C1   180.00   0.0  0
 VGI  CONST_45  C19  N1   C6   C1   180.00   0.0  0
 VGI  CONST_46  C19  N1   C6   C5     0.00   0.0  0
 VGI  CONST_47  H1   N1   C6   C1     0.00   0.0  0
 VGI  Var_01    C9   N2   C13  C14   88.41  30.0  2
 VGI  Var_02    C20  C19  N1   C6   168.94  30.0  3
 VGI  Var_03    O3   C20  C19  N1    59.23  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
 VGI  plan-1  C14  0.020
 VGI  plan-1  C15  0.020
 VGI  plan-1  BR1  0.020
 VGI  plan-1  C16  0.020
 VGI  plan-1  C17  0.020
 VGI  plan-1  C18  0.020
 VGI  plan-1  C13  0.020
 VGI  plan-1  N2   0.020
 VGI  plan-1  H14  0.020
 VGI  plan-1  H16  0.020
 VGI  plan-1  H17  0.020
 VGI  plan-1  H18  0.020
 VGI  plan-2  C13  0.020
 VGI  plan-2  N2   0.020
 VGI  plan-2  C9   0.020
 VGI  plan-2  O1   0.020
 VGI  plan-2  C12  0.020
 VGI  plan-2  O2   0.020
 VGI  plan-2  C8   0.020
 VGI  plan-2  C10  0.020
 VGI  plan-2  C11  0.020
 VGI  plan-2  C7   0.020
 VGI  plan-2  C1   0.020
 VGI  plan-2  C2   0.020
 VGI  plan-2  C3   0.020
 VGI  plan-2  C4   0.020
 VGI  plan-2  C5   0.020
 VGI  plan-2  C6   0.020
 VGI  plan-2  N1   0.020
 VGI  plan-2  H10  0.020
 VGI  plan-2  H11  0.020
 VGI  plan-2  H7   0.020
 VGI  plan-2  H4   0.020
 VGI  plan-2  H5   0.020
 VGI  plan-3  C6   0.020
 VGI  plan-3  N1   0.020
 VGI  plan-3  C19  0.020
 VGI  plan-3  H1   0.020

