# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 11 08:20:00 2022
#   Inital geometry file: a 118 line input string
#   Ligand name: 3,3-bis(3-bromo-4-hydroxyphenyl)-7-chloro-1H,3H-benzo[de]isochromen-1-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1ccc(cc1Br)C2(OC(=O)c3ccc(Cl)c4cccc2c34)c5ccc(O)c(Br)c5
#
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
 GA9  GA9  3,3-bis(3-bromo-4-hydroxyphenyl)-7-chloro-1H,3H-benzo[de]isochromen-1-one  ligand  44  31  .  2022-03-18  2023-02-15
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_GA9
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
 GA9  C1   C   CR6   0   0.554  -0.1381  -1.4850   2.3636
 GA9  C2   C   CR66  0  -0.197  -1.0228  -2.2777   1.4941
 GA9  C3   C   CR16  0  -0.305  -1.8135  -3.2597   2.0356
 GA9  C4   C   CR16  0  -0.208  -2.5350  -4.1273   1.2054
 GA9  C5   C   CR6   0  -0.139  -2.4199  -4.0213  -0.1554
 GA9  C6   C   CR66  0   0.223  -1.6183  -3.0241  -0.7663
 GA9  C7   C   CR16  0  -0.317  -1.4637  -2.8805  -2.1631
 GA9  C8   C   CR16  0  -0.234  -0.6794  -1.8813  -2.6688
 GA9  C9   C   CR16  0  -0.292  -0.0422  -0.9617  -1.8150
 GA9  C10  C   CR66  0   0.016  -0.1814  -1.0663  -0.4575
 GA9  C11  C   C     0   0.188  -0.9410  -2.1215   0.0911
 GA9  C12  C   CR6   0   0.126   0.3333  -0.0119   0.4954
 GA9  C13  C   CR6   0   0.053  -0.7269   1.0514   0.7661
 GA9  C14  C   CR16  0  -0.245  -1.8472   1.2122  -0.0365
 GA9  C15  C   CR6   0  -0.205  -2.7712   2.2103   0.2350
 GA9  C16  C   CR6   0   0.401  -2.6047   3.0738   1.3152
 GA9  C17  C   CR16  0  -0.371  -1.4771   2.9067   2.1193
 GA9  C18  C   CR16  0  -0.247  -0.5558   1.9156   1.8474
 GA9  C19  C   CR6   0   0.062   1.6348   0.5867  -0.0075
 GA9  C20  C   CR16  0  -0.231   2.7750  -0.2134  -0.0260
 GA9  C21  C   CR6   0  -0.207   3.9684   0.2804  -0.5157
 GA9  C22  C   CR6   0   0.402   4.0632   1.5847  -1.0100
 GA9  C23  C   CR16  0  -0.372   2.9185   2.3733  -0.9984
 GA9  C24  C   CR16  0  -0.275   1.7220   1.8798  -0.5018
 GA9  O1   O   O     0  -0.469   0.6678  -0.6016   1.7673
 GA9  O2   O   O     0  -0.409  -0.0361  -1.6479   3.5518
 GA9  O4   O   OH1   0  -0.604   5.2441   2.0111  -1.4693
 GA9  O3   O   OH1   0  -0.603  -3.5246   4.0178   1.5354
 GA9  BR1  BR  BR    0  -0.025  -4.2844   2.4060  -0.8677
 GA9  BR2  BR  BR    0  -0.025   5.5020  -0.8121  -0.5259
 GA9  CL3  CL  CL    0  -0.096  -3.2843  -5.1391  -1.1445
 GA9  H3   H   HCR6  0   0.286  -1.8719  -3.3909   3.1075
 GA9  H4   H   HCR6  0   0.296  -3.1571  -4.8947   1.6440
 GA9  H7   H   HCR6  0   0.267  -1.9635  -3.5621  -2.8367
 GA9  H8   H   HCR6  0   0.276  -0.5573  -1.7810  -3.7385
 GA9  H9   H   HCR6  0   0.273   0.5372  -0.1567  -2.2479
 GA9  H14  H   HCR6  0   0.278  -2.0107   0.5625  -0.8856
 GA9  H17  H   HCR6  0   0.288  -1.3244   3.5653   2.9663
 GA9  H18  H   HCR6  0   0.275   0.3079   1.8255   2.4929
 GA9  H20  H   HCR6  0   0.280   2.7313  -1.2328   0.3359
 GA9  H23  H   HCR6  0   0.287   2.9630   3.3872  -1.3791
 GA9  H24  H   HCR6  0   0.269   0.8557   2.5263  -0.5112
 GA9  HO4  H   HOH1  0   0.486   5.1755   2.9206  -1.7833
 GA9  HO3  H   HOH1  0   0.486  -3.2910   4.5428   2.3102

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
 GA9  C1   C2   single    1.472  0.020  1.472
 GA9  C1   O1   single    1.336  0.020  1.336
 GA9  C1   O2   double    1.204  0.020  1.204
 GA9  C2   C3   aromatic  1.372  0.020  1.372
 GA9  C2   C11  aromatic  1.414  0.020  1.414
 GA9  C3   C4   aromatic  1.401  0.020  1.401
 GA9  C3   H3   single    0.930  0.020  1.080
 GA9  C4   C5   aromatic  1.370  0.020  1.370
 GA9  C4   H4   single    0.930  0.020  1.080
 GA9  C5   C6   aromatic  1.418  0.020  1.418
 GA9  C5   CL3  single    1.725  0.020  1.725
 GA9  C6   C7   aromatic  1.413  0.020  1.413
 GA9  C6   C11  aromatic  1.417  0.020  1.417
 GA9  C7   C8   aromatic  1.367  0.020  1.367
 GA9  C7   H7   single    0.930  0.020  1.080
 GA9  C8   C9   aromatic  1.407  0.020  1.407
 GA9  C8   H8   single    0.930  0.020  1.080
 GA9  C9   C10  aromatic  1.369  0.020  1.369
 GA9  C9   H9   single    0.930  0.020  1.080
 GA9  C10  C11  aromatic  1.411  0.020  1.411
 GA9  C10  C12  single    1.512  0.020  1.512
 GA9  C12  C13  single    1.526  0.020  1.526
 GA9  C12  C19  single    1.518  0.020  1.518
 GA9  C12  O1   single    1.441  0.020  1.441
 GA9  C13  C14  aromatic  1.387  0.020  1.387
 GA9  C13  C18  aromatic  1.395  0.020  1.395
 GA9  C14  C15  aromatic  1.387  0.020  1.387
 GA9  C14  H14  single    0.930  0.020  1.080
 GA9  C15  C16  aromatic  1.393  0.020  1.393
 GA9  C15  BR1  single    1.883  0.020  1.883
 GA9  C16  C17  aromatic  1.395  0.020  1.395
 GA9  C16  O3   single    1.336  0.020  1.336
 GA9  C17  C18  aromatic  1.380  0.020  1.380
 GA9  C17  H17  single    0.930  0.020  1.080
 GA9  C18  H18  single    0.930  0.020  1.080
 GA9  C19  C20  aromatic  1.393  0.020  1.393
 GA9  C19  C24  aromatic  1.387  0.020  1.387
 GA9  C20  C21  aromatic  1.381  0.020  1.381
 GA9  C20  H20  single    0.930  0.020  1.080
 GA9  C21  C22  aromatic  1.398  0.020  1.398
 GA9  C21  BR2  single    1.883  0.020  1.883
 GA9  C22  C23  aromatic  1.390  0.020  1.390
 GA9  C22  O4   single    1.337  0.020  1.337
 GA9  C23  C24  aromatic  1.386  0.020  1.386
 GA9  C23  H23  single    0.930  0.020  1.080
 GA9  C24  H24  single    0.930  0.020  1.080
 GA9  O4   HO4  single    0.850  0.020  0.980
 GA9  O3   HO3  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
 GA9  O2   C1   O1   118.61  3.000
 GA9  O2   C1   C2   124.14  3.000
 GA9  O1   C1   C2   117.06  3.000
 GA9  C11  C2   C3   120.27  3.000
 GA9  C11  C2   C1   119.45  3.000
 GA9  C3   C2   C1   119.91  3.000
 GA9  H3   C3   C4   118.98  3.000
 GA9  H3   C3   C2   120.60  3.000
 GA9  C4   C3   C2   120.40  3.000
 GA9  H4   C4   C5   120.43  3.000
 GA9  H4   C4   C3   119.71  3.000
 GA9  C5   C4   C3   119.84  3.000
 GA9  CL3  C5   C6   119.48  3.000
 GA9  CL3  C5   C4   118.52  3.000
 GA9  C6   C5   C4   122.00  3.000
 GA9  C11  C6   C7   118.76  3.000
 GA9  C11  C6   C5   117.22  3.000
 GA9  C7   C6   C5   124.01  3.000
 GA9  H7   C7   C8   119.71  3.000
 GA9  H7   C7   C6   120.10  3.000
 GA9  C8   C7   C6   120.18  3.000
 GA9  H8   C8   C9   119.24  3.000
 GA9  H8   C8   C7   119.89  3.000
 GA9  C9   C8   C7   120.86  3.000
 GA9  H9   C9   C10  120.54  3.000
 GA9  H9   C9   C8   119.06  3.000
 GA9  C10  C9   C8   120.38  3.000
 GA9  C12  C10  C11  117.37  3.000
 GA9  C12  C10  C9   122.50  3.000
 GA9  C11  C10  C9   119.84  3.000
 GA9  C10  C11  C6   119.89  3.000
 GA9  C10  C11  C2   119.97  3.000
 GA9  C6   C11  C2   120.15  3.000
 GA9  O1   C12  C19  104.75  3.000
 GA9  O1   C12  C13  106.85  3.000
 GA9  C19  C12  C13  112.31  3.000
 GA9  O1   C12  C10  110.49  3.000
 GA9  C19  C12  C10  110.98  3.000
 GA9  C13  C12  C10  111.19  3.000
 GA9  C18  C13  C14  118.41  3.000
 GA9  C18  C13  C12  118.95  3.000
 GA9  C14  C13  C12  122.63  3.000
 GA9  H14  C14  C15  119.02  3.000
 GA9  H14  C14  C13  120.44  3.000
 GA9  C15  C14  C13  120.54  3.000
 GA9  BR1  C15  C16  119.07  3.000
 GA9  BR1  C15  C14  119.71  3.000
 GA9  C16  C15  C14  121.21  3.000
 GA9  O3   C16  C17  123.10  3.000
 GA9  O3   C16  C15  118.91  3.000
 GA9  C17  C16  C15  117.99  3.000
 GA9  H17  C17  C18  119.75  3.000
 GA9  H17  C17  C16  119.45  3.000
 GA9  C18  C17  C16  120.80  3.000
 GA9  H18  C18  C17  118.36  3.000
 GA9  H18  C18  C13  120.59  3.000
 GA9  C17  C18  C13  121.05  3.000
 GA9  C24  C19  C20  118.63  3.000
 GA9  C24  C19  C12  122.65  3.000
 GA9  C20  C19  C12  118.66  3.000
 GA9  H20  C20  C21  119.35  3.000
 GA9  H20  C20  C19  120.22  3.000
 GA9  C21  C20  C19  120.43  3.000
 GA9  BR2  C21  C22  118.96  3.000
 GA9  BR2  C21  C20  119.88  3.000
 GA9  C22  C21  C20  121.16  3.000
 GA9  O4   C22  C23  123.32  3.000
 GA9  O4   C22  C21  118.61  3.000
 GA9  C23  C22  C21  118.07  3.000
 GA9  H23  C23  C24  119.62  3.000
 GA9  H23  C23  C22  119.60  3.000
 GA9  C24  C23  C22  120.78  3.000
 GA9  H24  C24  C23  118.40  3.000
 GA9  H24  C24  C19  120.68  3.000
 GA9  C23  C24  C19  120.92  3.000
 GA9  C12  O1   C1   121.62  3.000
 GA9  HO4  O4   C22  110.47  3.000
 GA9  HO3  O3   C16  110.49  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
 GA9  CONST_01  C5   C4   C3   C2     0.00   0.0  0
 GA9  CONST_02  C5   C6   C11  C2     0.00   0.0  0
 GA9  CONST_03  C7   C6   C11  C2   180.00   0.0  0
 GA9  CONST_04  C9   C10  C11  C2   180.00   0.0  0
 GA9  CONST_05  C6   C11  C2   C3     0.00   0.0  0
 GA9  CONST_06  C10  C11  C2   C3   180.00   0.0  0
 GA9  CONST_07  C6   C5   C4   C3     0.00   0.0  0
 GA9  CONST_08  C11  C2   C3   C4     0.00   0.0  0
 GA9  CONST_09  C7   C6   C5   C4   180.00   0.0  0
 GA9  CONST_10  C11  C6   C5   C4     0.00   0.0  0
 GA9  CONST_11  C8   C7   C6   C5   180.00   0.0  0
 GA9  CONST_12  C10  C11  C6   C5   180.00   0.0  0
 GA9  CONST_13  C9   C8   C7   C6     0.00   0.0  0
 GA9  CONST_14  C9   C10  C11  C6     0.00   0.0  0
 GA9  CONST_15  C10  C11  C6   C7     0.00   0.0  0
 GA9  CONST_16  C10  C9   C8   C7     0.00   0.0  0
 GA9  CONST_17  C11  C6   C7   C8     0.00   0.0  0
 GA9  CONST_18  C11  C10  C9   C8     0.00   0.0  0
 GA9  CONST_19  C16  C15  C14  C13    0.00   0.0  0
 GA9  CONST_20  C16  C17  C18  C13    0.00   0.0  0
 GA9  CONST_21  C17  C18  C13  C14    0.00   0.0  0
 GA9  CONST_22  C17  C16  C15  C14    0.00   0.0  0
 GA9  CONST_23  C18  C13  C14  C15    0.00   0.0  0
 GA9  CONST_24  C18  C17  C16  C15    0.00   0.0  0
 GA9  CONST_25  C22  C21  C20  C19    0.00   0.0  0
 GA9  CONST_26  C22  C23  C24  C19    0.00   0.0  0
 GA9  CONST_27  C23  C24  C19  C20    0.00   0.0  0
 GA9  CONST_28  C23  C22  C21  C20    0.00   0.0  0
 GA9  CONST_29  C24  C19  C20  C21    0.00   0.0  0
 GA9  CONST_30  C24  C23  C22  C21    0.00   0.0  0
 GA9  CONST_31  C15  C14  C13  C12  180.00   0.0  0
 GA9  CONST_32  C17  C18  C13  C12  180.00   0.0  0
 GA9  CONST_33  C21  C20  C19  C12  180.00   0.0  0
 GA9  CONST_34  C23  C24  C19  C12  180.00   0.0  0
 GA9  CONST_35  CL3  C5   C4   C3   180.00   0.0  0
 GA9  CONST_36  CL3  C5   C6   C7     0.00   0.0  0
 GA9  CONST_37  CL3  C5   C6   C11  180.00   0.0  0
 GA9  CONST_38  BR1  C15  C14  C13  180.00   0.0  0
 GA9  CONST_39  O3   C16  C15  C14  180.00   0.0  0
 GA9  CONST_40  BR1  C15  C16  C17  180.00   0.0  0
 GA9  CONST_41  O3   C16  C17  C18  180.00   0.0  0
 GA9  CONST_42  BR2  C21  C20  C19  180.00   0.0  0
 GA9  CONST_43  O4   C22  C21  C20  180.00   0.0  0
 GA9  CONST_44  BR2  C21  C22  C23  180.00   0.0  0
 GA9  CONST_45  O4   C22  C23  C24  180.00   0.0  0
 GA9  CONST_46  H3   C3   C2   C1     0.00   0.0  0
 GA9  CONST_47  H4   C4   C3   C2   180.00   0.0  0
 GA9  CONST_48  H7   C7   C6   C5     0.00   0.0  0
 GA9  CONST_49  H8   C8   C7   C6   180.00   0.0  0
 GA9  CONST_50  H9   C9   C8   C7   180.00   0.0  0
 GA9  CONST_51  H14  C14  C13  C12    0.00   0.0  0
 GA9  CONST_52  H18  C18  C13  C12    0.00   0.0  0
 GA9  CONST_53  H20  C20  C19  C12    0.00   0.0  0
 GA9  CONST_54  H24  C24  C19  C12    0.00   0.0  0
 GA9  CONST_55  H17  C17  C18  C13  180.00   0.0  0
 GA9  CONST_56  H23  C23  C24  C19  180.00   0.0  0
 GA9  Var_01    C10  C12  O1   C1   -44.52  30.0  1
 GA9  Var_02    O1   C1   C2   C3   175.93  30.0  1
 GA9  Var_03    C14  C13  C12  C10  -16.31  30.0  2
 GA9  Var_04    C20  C19  C12  C10  -68.37  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
 GA9  plan-1  C12  0.020
 GA9  plan-1  C13  0.020
 GA9  plan-1  C14  0.020
 GA9  plan-1  C15  0.020
 GA9  plan-1  C16  0.020
 GA9  plan-1  C17  0.020
 GA9  plan-1  C18  0.020
 GA9  plan-1  O3   0.020
 GA9  plan-1  BR1  0.020
 GA9  plan-1  H14  0.020
 GA9  plan-1  H17  0.020
 GA9  plan-1  H18  0.020
 GA9  plan-2  C12  0.020
 GA9  plan-2  C19  0.020
 GA9  plan-2  C20  0.020
 GA9  plan-2  C21  0.020
 GA9  plan-2  C22  0.020
 GA9  plan-2  C23  0.020
 GA9  plan-2  C24  0.020
 GA9  plan-2  O4   0.020
 GA9  plan-2  BR2  0.020
 GA9  plan-2  H20  0.020
 GA9  plan-2  H23  0.020
 GA9  plan-2  H24  0.020
 GA9  plan-3  C1   0.020
 GA9  plan-3  C2   0.020
 GA9  plan-3  C3   0.020
 GA9  plan-3  C4   0.020
 GA9  plan-3  C5   0.020
 GA9  plan-3  C6   0.020
 GA9  plan-3  C7   0.020
 GA9  plan-3  C8   0.020
 GA9  plan-3  C9   0.020
 GA9  plan-3  C10  0.020
 GA9  plan-3  C11  0.020
 GA9  plan-3  C12  0.020
 GA9  plan-3  CL3  0.020
 GA9  plan-3  H3   0.020
 GA9  plan-3  H4   0.020
 GA9  plan-3  H7   0.020
 GA9  plan-3  H8   0.020
 GA9  plan-3  H9   0.020
 GA9  plan-4  C1   0.020
 GA9  plan-4  C2   0.020
 GA9  plan-4  O1   0.020
 GA9  plan-4  O2   0.020

