# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Mar  9 11:02:08 2022
#   Inital geometry file: a 127 line input string
#   Ligand name: 1-(3,4-dihydroxy-5-nitrophenyl)-3-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}propan-1-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1cc(cc(c1O)[N+]([O-])=O)C(=O)CCN2CCN(CC2)c3cccc(c3)C(F)(F)F
#
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
 BIA  BIA  1-(3,4-dihydroxy-5-nitrophenyl)-3-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}propan-1-one  ligand  51  31  .  2022-03-15  2023-02-02
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_BIA
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
 BIA  N2    N  NR6    0  -0.519   3.3547  -1.2108  -0.1560
 BIA  C3    C  CR16   0  -0.388  -4.1197   0.8626  -0.6690
 BIA  C4    C  CR16   0  -0.352   5.4368  -1.7542  -1.3204
 BIA  C6    C  C      0   0.397  -3.2311  -1.2358   0.4342
 BIA  C7    C  CR6    0   0.346  -5.1555   1.7092  -0.9924
 BIA  O8    O  O      0  -0.396  -3.4633  -2.2446   1.0659
 BIA  O9    O  OH1    0  -0.621  -4.9009   2.8192  -1.7011
 BIA  C10   C  CR16   0  -0.226   6.7822  -1.5082  -1.5399
 BIA  C11   C  CR6    0  -0.009  -4.3403  -0.3075   0.0698
 BIA  C12   C  C      0  -0.297   1.1349  -0.4398   0.5434
 BIA  C16   C  C      0  -0.281   1.4200  -2.6955  -0.0866
 BIA  O17   O  O      0  -0.420  -8.9196   0.6267   0.3136
 BIA  O18   O  O     -1  -0.354  -8.1501  -1.1284   1.2406
 BIA  C19   C  CR16   0  -0.356  -5.6209  -0.6168   0.4808
 BIA  C21   C  C      0  -0.319   2.7377  -2.3722  -0.7644
 BIA  N23   N  NR6    0  -0.431   0.5167  -1.5640  -0.1301
 BIA  C24   C  CR6    0  -0.172   6.7120   0.3205  -0.0200
 BIA  C25   C  C      0  -0.306   2.4475  -0.0713  -0.1189
 BIA  C26   C  CR16   0  -0.363   5.3675   0.0785   0.2191
 BIA  C27   C  CH2    0  -0.245  -0.7890  -1.8996   0.4058
 BIA  C28   C  CR6    0   0.219  -6.6726   0.2334   0.1580
 BIA  C31   C  CR6    0   0.398   4.6945  -0.9655  -0.4287
 BIA  C32   C  CR6    0   0.262  -6.4699   1.4081  -0.5814
 BIA  C37   C  CR16   0  -0.326   7.4393  -0.4683  -0.9017
 BIA  H3    H  HCR6   0   0.291  -3.1270   1.1306  -1.0065
 BIA  H4    H  HCR6   0   0.278   4.9723  -2.5645  -1.8638
 BIA  H5    H  HOH1   0   0.495  -8.2681   1.9875  -0.6154
 BIA  H9    H  HOH1   0   0.483  -5.7075   3.3252  -1.8590
 BIA  H10   H  HCR6   0   0.264   7.3245  -2.1344  -2.2360
 BIA  H121  H  H      0   0.248   0.4830   0.4341   0.4942
 BIA  H122  H  H      0   0.201   1.3113  -0.6550   1.6115
 BIA  H161  H  H      0   0.198   1.6205  -3.0215   0.9482
 BIA  H162  H  H      0   0.246   0.9667  -3.5404  -0.6090
 BIA  H19   H  HCR6   0   0.299  -5.8062  -1.5150   1.0516
 BIA  H211  H  H      0   0.255   3.3902  -3.2377  -0.6472
 BIA  H212  H  H      0   0.218   2.5713  -2.2261  -1.8421
 BIA  H221  H  HCH2   0   0.279  -1.8223  -0.7547  -1.0889
 BIA  H222  H  HCH2   0   0.280  -1.6061   0.1143   0.4059
 BIA  H251  H  H      0   0.258   2.8881   0.7494   0.4426
 BIA  H252  H  H      0   0.222   2.2499   0.2953  -1.1364
 BIA  H26   H  HCR6   0   0.278   4.8382   0.6932   0.9358
 BIA  H271  H  HCH2   0   0.207  -0.7660  -2.0074   1.5016
 BIA  H272  H  HCH2   0   0.242  -1.0744  -2.8730   0.0022
 BIA  H37   H  HCR6   0   0.264   8.4867  -0.2890  -1.0969
 BIA  C33   C  CT     0   1.046   7.3553   1.4576   0.7107
 BIA  C22   C  CH2    0  -0.618  -1.8364  -0.8755  -0.0010
 BIA  N14   N  N      1   0.364  -7.9966  -0.1201   0.6039
 BIA  O5    O  OH1    0  -0.603  -7.3971   2.2813  -0.9437
 BIA  F37   F  F      0  -0.303   8.6588   1.5764   0.4430
 BIA  F38   F  F      0  -0.316   6.7860   2.6332   0.4017
 BIA  F39   F  F      0  -0.316   7.2419   1.3234   2.0414

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
 BIA  N2   C21   single    1.449  0.020  1.449
 BIA  N2   C25   single    1.457  0.020  1.457
 BIA  N2   C31   single    1.389  0.020  1.389
 BIA  C3   C7    aromatic  1.376  0.020  1.376
 BIA  C3   C11   aromatic  1.401  0.020  1.401
 BIA  C3   H3    single    0.930  0.020  1.080
 BIA  C4   C10   aromatic  1.385  0.020  1.385
 BIA  C4   C31   aromatic  1.403  0.020  1.403
 BIA  C4   H4    single    0.930  0.020  1.080
 BIA  O5   C32   single    1.324  0.020  1.324
 BIA  O5   H5    single    0.850  0.020  0.980
 BIA  C6   O8    double    1.213  0.020  1.213
 BIA  C6   C11   single    1.492  0.020  1.492
 BIA  C6   C22   single    1.505  0.020  1.505
 BIA  C7   O9    single    1.341  0.020  1.341
 BIA  C7   C32   aromatic  1.410  0.020  1.410
 BIA  O9   H9    single    0.850  0.020  0.980
 BIA  C10  C37   aromatic  1.386  0.020  1.386
 BIA  C10  H10   single    0.930  0.020  1.080
 BIA  C11  C19   aromatic  1.380  0.020  1.380
 BIA  C12  N23   single    1.449  0.020  1.449
 BIA  C12  C25   single    1.516  0.020  1.516
 BIA  C12  H121  single    0.970  0.020  1.090
 BIA  C12  H122  single    0.970  0.020  1.090
 BIA  N14  O17   double    1.222  0.020  1.222
 BIA  N14  O18   single    1.202  0.020  1.202
 BIA  N14  C28   single    1.441  0.020  1.441
 BIA  C16  C21   single    1.517  0.020  1.517
 BIA  C16  N23   single    1.449  0.020  1.449
 BIA  C16  H161  single    0.970  0.020  1.090
 BIA  C16  H162  single    0.970  0.020  1.090
 BIA  C19  C28   aromatic  1.390  0.020  1.390
 BIA  C19  H19   single    0.930  0.020  1.080
 BIA  C21  H211  single    0.970  0.020  1.090
 BIA  C21  H212  single    0.970  0.020  1.090
 BIA  C22  C27   single    1.520  0.020  1.520
 BIA  C22  H221  single    0.970  0.020  1.090
 BIA  C22  H222  single    0.970  0.020  1.090
 BIA  N23  C27   single    1.451  0.020  1.451
 BIA  C24  C26   aromatic  1.387  0.020  1.387
 BIA  C24  C33   single    1.497  0.020  1.497
 BIA  C24  C37   aromatic  1.389  0.020  1.389
 BIA  C25  H251  single    0.970  0.020  1.090
 BIA  C25  H252  single    0.970  0.020  1.090
 BIA  C26  C31   aromatic  1.401  0.020  1.401
 BIA  C26  H26   single    0.930  0.020  1.080
 BIA  C27  H271  single    0.970  0.020  1.090
 BIA  C27  H272  single    0.970  0.020  1.090
 BIA  C28  C32   aromatic  1.403  0.020  1.403
 BIA  C33  F37   single    1.336  0.020  1.336
 BIA  C33  F38   single    1.342  0.020  1.342
 BIA  C33  F39   single    1.342  0.020  1.342
 BIA  C37  H37   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
 BIA  C31   N2   C25   117.87  3.000
 BIA  C31   N2   C21   118.02  3.000
 BIA  C25   N2   C21   111.86  3.000
 BIA  H3    C3   C11   121.04  3.000
 BIA  H3    C3   C7    117.69  3.000
 BIA  C11   C3   C7    121.27  3.000
 BIA  H4    C4   C31   120.92  3.000
 BIA  H4    C4   C10   118.10  3.000
 BIA  C31   C4   C10   120.98  3.000
 BIA  C22   C6   C11   118.01  3.000
 BIA  C22   C6   O8    121.82  3.000
 BIA  C11   C6   O8    120.17  3.000
 BIA  C32   C7   O9    120.51  3.000
 BIA  C32   C7   C3    120.12  3.000
 BIA  O9    C7   C3    119.37  3.000
 BIA  H9    O9   C7    111.20  3.000
 BIA  H10   C10  C37   119.53  3.000
 BIA  H10   C10  C4    119.08  3.000
 BIA  C37   C10  C4    121.39  3.000
 BIA  C19   C11  C6    118.54  3.000
 BIA  C19   C11  C3    119.36  3.000
 BIA  C6    C11  C3    122.10  3.000
 BIA  H122  C12  H121  107.17  3.000
 BIA  H122  C12  C25   109.38  3.000
 BIA  H121  C12  C25   107.63  3.000
 BIA  H122  C12  N23   111.52  3.000
 BIA  H121  C12  N23   110.21  3.000
 BIA  C25   C12  N23   110.79  3.000
 BIA  H162  C16  H161  107.19  3.000
 BIA  H162  C16  N23   109.34  3.000
 BIA  H161  C16  N23   111.86  3.000
 BIA  H162  C16  C21   108.17  3.000
 BIA  H161  C16  C21   108.92  3.000
 BIA  N23   C16  C21   111.21  3.000
 BIA  H19   C19  C28   120.09  3.000
 BIA  H19   C19  C11   120.19  3.000
 BIA  C28   C19  C11   119.71  3.000
 BIA  H212  C21  H211  107.53  3.000
 BIA  H212  C21  C16   109.55  3.000
 BIA  H211  C21  C16   107.62  3.000
 BIA  H212  C21  N2    111.67  3.000
 BIA  H211  C21  N2    109.65  3.000
 BIA  C16   C21  N2    110.68  3.000
 BIA  C27   N23  C16   111.68  3.000
 BIA  C27   N23  C12   113.06  3.000
 BIA  C16   N23  C12   109.03  3.000
 BIA  C37   C24  C33   121.08  3.000
 BIA  C37   C24  C26   121.21  3.000
 BIA  C33   C24  C26   117.71  3.000
 BIA  H252  C25  H251  107.40  3.000
 BIA  H252  C25  C12   109.25  3.000
 BIA  H251  C25  C12   107.98  3.000
 BIA  H252  C25  N2    110.43  3.000
 BIA  H251  C25  N2    110.55  3.000
 BIA  C12   C25  N2    111.12  3.000
 BIA  H26   C26  C31   119.63  3.000
 BIA  H26   C26  C24   119.29  3.000
 BIA  C31   C26  C24   121.06  3.000
 BIA  H272  C27  H271  106.62  3.000
 BIA  H272  C27  N23   107.76  3.000
 BIA  H271  C27  N23   111.81  3.000
 BIA  H272  C27  C22   108.76  3.000
 BIA  H271  C27  C22   110.27  3.000
 BIA  N23   C27  C22   111.43  3.000
 BIA  C32   C28  C19   121.69  3.000
 BIA  C32   C28  N14   120.08  3.000
 BIA  C19   C28  N14   118.23  3.000
 BIA  C26   C31  C4    117.31  3.000
 BIA  C26   C31  N2    120.27  3.000
 BIA  C4    C31  N2    122.40  3.000
 BIA  C28   C32  C7    117.85  3.000
 BIA  C28   C32  O5    126.53  3.000
 BIA  C7    C32  O5    115.61  3.000
 BIA  H37   C37  C24   121.88  3.000
 BIA  H37   C37  C10   120.07  3.000
 BIA  C24   C37  C10   118.05  3.000
 BIA  F39   C33  F38   106.26  3.000
 BIA  F39   C33  F37   106.86  3.000
 BIA  F38   C33  F37   106.84  3.000
 BIA  F39   C33  C24   111.82  3.000
 BIA  F38   C33  C24   111.76  3.000
 BIA  F37   C33  C24   112.90  3.000
 BIA  H222  C22  H221  105.48  3.000
 BIA  H222  C22  C27   111.39  3.000
 BIA  H221  C22  C27   109.35  3.000
 BIA  H222  C22  C6    107.70  3.000
 BIA  H221  C22  C6    109.01  3.000
 BIA  C27   C22  C6    113.57  3.000
 BIA  C28   N14  O18   119.13  3.000
 BIA  C28   N14  O17   118.06  3.000
 BIA  O18   N14  O17   122.81  3.000
 BIA  H5    O5   C32   109.53  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
 BIA  CONST_01  C28  C32  C7   C3      0.00   0.0  0
 BIA  CONST_02  C28  C19  C11  C3      0.00   0.0  0
 BIA  CONST_03  C24  C37  C10  C4      0.00   0.0  0
 BIA  CONST_04  C24  C26  C31  C4      0.00   0.0  0
 BIA  CONST_05  C19  C11  C3   C7      0.00   0.0  0
 BIA  CONST_06  C19  C28  C32  C7      0.00   0.0  0
 BIA  CONST_07  C26  C31  C4   C10     0.00   0.0  0
 BIA  CONST_08  C26  C24  C37  C10     0.00   0.0  0
 BIA  CONST_09  C32  C7   C3   C11     0.00   0.0  0
 BIA  CONST_10  C32  C28  C19  C11     0.00   0.0  0
 BIA  CONST_11  C37  C10  C4   C31     0.00   0.0  0
 BIA  CONST_12  C37  C24  C26  C31     0.00   0.0  0
 BIA  CONST_13  C10  C4   C31  N2    180.00   0.0  0
 BIA  CONST_14  C24  C26  C31  N2    180.00   0.0  0
 BIA  CONST_15  O5   C32  C7   C3    180.00   0.0  0
 BIA  CONST_16  C19  C28  C32  O5    180.00   0.0  0
 BIA  CONST_17  C7   C3   C11  C6    180.00   0.0  0
 BIA  CONST_18  C28  C19  C11  C6    180.00   0.0  0
 BIA  CONST_19  N14  C28  C32  C7    180.00   0.0  0
 BIA  CONST_20  C11  C3   C7   O9    180.00   0.0  0
 BIA  CONST_21  C28  C32  C7   O9    180.00   0.0  0
 BIA  CONST_22  C33  C24  C37  C10   180.00   0.0  0
 BIA  CONST_23  N14  C28  C19  C11   180.00   0.0  0
 BIA  CONST_24  C33  C24  C26  C31   180.00   0.0  0
 BIA  CONST_25  H4   C4   C31  N2      0.00   0.0  0
 BIA  CONST_26  H26  C26  C31  N2      0.00   0.0  0
 BIA  CONST_27  H19  C19  C11  C3    180.00   0.0  0
 BIA  CONST_28  H37  C37  C10  C4    180.00   0.0  0
 BIA  CONST_29  H3   C3   C11  C19   180.00   0.0  0
 BIA  CONST_30  H10  C10  C37  C24   180.00   0.0  0
 BIA  CONST_31  C19  C28  N14  O17   180.00   0.0  0
 BIA  CONST_32  C32  C28  N14  O17     0.00   0.0  0
 BIA  CONST_33  C19  C28  N14  O18     0.00   0.0  0
 BIA  CONST_34  C32  C28  N14  O18   180.00   0.0  0
 BIA  Var_01    N23  C16  C21  N2     56.95  30.0  1
 BIA  Var_02    N23  C12  C25  N2    -56.54  30.0  1
 BIA  Var_03    C21  N2   C31  C4      3.57  30.0  1
 BIA  Var_04    C21  C16  N23  C12   -59.58  30.0  1
 BIA  Var_05    C25  C12  N23  C16    59.19  30.0  1
 BIA  Var_06    O8   C6   C11  C3   -179.42  30.0  2
 BIA  Var_07    C22  C27  N23  C12    73.21  30.0  3
 BIA  Var_08    F37  C33  C24  C26   177.92  30.0  2
 BIA  Var_09    N23  C27  C22  C6    175.26  30.0  3
 BIA  Var_10    C27  C22  C6   C11  -179.17  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
 BIA  plan-1  C3   0.020
 BIA  plan-1  C6   0.020
 BIA  plan-1  C7   0.020
 BIA  plan-1  O9   0.020
 BIA  plan-1  C11  0.020
 BIA  plan-1  C19  0.020
 BIA  plan-1  C28  0.020
 BIA  plan-1  C32  0.020
 BIA  plan-1  H3   0.020
 BIA  plan-1  H19  0.020
 BIA  plan-1  N14  0.020
 BIA  plan-1  O5   0.020
 BIA  plan-2  N2   0.020
 BIA  plan-2  C4   0.020
 BIA  plan-2  C10  0.020
 BIA  plan-2  C24  0.020
 BIA  plan-2  C26  0.020
 BIA  plan-2  C31  0.020
 BIA  plan-2  C37  0.020
 BIA  plan-2  H4   0.020
 BIA  plan-2  H10  0.020
 BIA  plan-2  H26  0.020
 BIA  plan-2  H37  0.020
 BIA  plan-2  C33  0.020
 BIA  plan-3  O17  0.020
 BIA  plan-3  O18  0.020
 BIA  plan-3  C28  0.020
 BIA  plan-3  N14  0.020
 BIA  plan-4  C6   0.020
 BIA  plan-4  O8   0.020
 BIA  plan-4  C11  0.020
 BIA  plan-4  C22  0.020

