# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 11:56:45 2020
#   Inital geometry file: a 93 line input string
#   Ligand name: 1-methylethyl (2S)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxaline-1(2H)-carboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC[C@@H]1N(C(=O)OC(C)C)c2cc(F)ccc2NC1=O
#
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
 HBQ  HBQ  '1-methylethyl (2S)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxaline-1(2H)-carboxylate'  ligand  37  20  .  2022-07-25  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_HBQ
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
 HBQ  C1    C  C     0   0.539  -2.7350   0.6733  5.5615
 HBQ  C2    C  CH1   0  -0.274  -2.9444  -0.7420  5.0489
 HBQ  C3    C  CR6   0   0.346  -1.8148  -0.1373  2.9932
 HBQ  C4    C  CR6   0   0.334  -1.2755   0.9693  3.6521
 HBQ  C5    C  CR16  0  -0.314  -0.1481   1.6023  3.1457
 HBQ  C6    C  CR16  0  -0.420   0.4497   1.1482  1.9822
 HBQ  C7    C  CR6   0   0.527  -0.0864   0.0365  1.3626
 HBQ  C8    C  CR16  0  -0.458  -1.1956  -0.6240  1.8479
 HBQ  C9    C  CH2   0  -0.417  -1.8985  -1.7172  5.6029
 HBQ  C10   C  CH3   0  -0.671  -1.9278  -1.8515  7.1183
 HBQ  C12   C  CH1   0   0.014  -5.9869  -2.4967  2.9192
 HBQ  C13   C  CH3   0  -0.676  -5.5756  -3.8663  2.4140
 HBQ  C14   C  CH3   0  -0.670  -7.0833  -2.5633  3.9609
 HBQ  F1    F  F     0  -0.318   0.4995  -0.4339  0.2484
 HBQ  N1    N  NT    0  -0.606  -2.9396  -0.7310  3.5880
 HBQ  N2    N  NH1   0  -0.721  -1.8953   1.4251  4.8128
 HBQ  O1    O  O     0  -0.455  -3.2597   1.0856  6.5779
 HBQ  O2    O  O2    0  -0.480  -4.8625  -1.8567  3.5665
 HBQ  O3    O  O     0  -0.493  -4.0107  -1.1347  1.6190
 HBQ  H2    H  HCH1  0   0.311  -3.9274  -1.0500  5.3942
 HBQ  H5    H  HCR6  0   0.286   0.2599   2.4612  3.6627
 HBQ  H6    H  HCR6  0   0.285   1.3199   1.6457  1.5759
 HBQ  H8    H  HCR6  0   0.292  -1.5645  -1.5004  1.3366
 HBQ  H91   H  HCH2  0   0.238  -0.8982  -1.4251  5.2727
 HBQ  H92   H  HCH2  0   0.253  -2.1062  -2.6881  5.1475
 HBQ  H101  H  HCH3  0   0.232  -1.6390  -0.9301  7.6230
 HBQ  H102  H  HCH3  0   0.228  -2.9208  -2.1299  7.4735
 HBQ  H103  H  HCH3  0   0.239  -1.2326  -2.6283  7.4349
 HBQ  H12   H  HCH1  0   0.244  -6.3143  -1.8742  2.0838
 HBQ  H131  H  HCH3  0   0.240  -6.4331  -4.3595  1.9563
 HBQ  H132  H  HCH3  0   0.244  -4.7912  -3.8024  1.6611
 HBQ  H133  H  HCH3  0   0.232  -5.2241  -4.4955  3.2334
 HBQ  H141  H  HCH3  0   0.238  -7.9683  -3.0282  3.5282
 HBQ  H142  H  HCH3  0   0.243  -7.3645  -1.5691  4.3077
 HBQ  H143  H  HCH3  0   0.232  -6.7781  -3.1603  4.8217
 HBQ  HN2   H  HNH1  0   0.414  -1.6612   2.3477  5.1541
 HBQ  C11   C  C     0   0.762  -3.9585  -1.2416  2.8224

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
 HBQ  C1   O1    double    1.216  0.020  1.216
 HBQ  C1   N2    single    1.353  0.020  1.353
 HBQ  C1   C2    single    1.520  0.020  1.520
 HBQ  C2   C9    single    1.534  0.020  1.534
 HBQ  C2   N1    single    1.461  0.020  1.461
 HBQ  C2   H2    single    0.970  0.020  1.090
 HBQ  C3   C4    aromatic  1.396  0.020  1.396
 HBQ  C3   N1    single    1.404  0.020  1.404
 HBQ  C3   C8    aromatic  1.390  0.020  1.390
 HBQ  C4   N2    single    1.393  0.020  1.393
 HBQ  C4   C5    aromatic  1.389  0.020  1.389
 HBQ  C5   C6    aromatic  1.385  0.020  1.385
 HBQ  C5   H5    single    0.930  0.020  1.080
 HBQ  C6   C7    aromatic  1.381  0.020  1.381
 HBQ  C6   H6    single    0.930  0.020  1.080
 HBQ  C7   C8    aromatic  1.379  0.020  1.379
 HBQ  C7   F1    single    1.344  0.020  1.344
 HBQ  C8   H8    single    0.930  0.020  1.080
 HBQ  C9   C10   single    1.522  0.020  1.522
 HBQ  C9   H91   single    0.970  0.020  1.090
 HBQ  C9   H92   single    0.970  0.020  1.090
 HBQ  C10  H101  single    0.970  0.020  1.090
 HBQ  C10  H102  single    0.970  0.020  1.090
 HBQ  C10  H103  single    0.970  0.020  1.090
 HBQ  C11  N1    single    1.373  0.020  1.373
 HBQ  C11  O3    double    1.209  0.020  1.209
 HBQ  C11  O2    single    1.323  0.020  1.323
 HBQ  C12  O2    single    1.447  0.020  1.447
 HBQ  C12  C14   single    1.514  0.020  1.514
 HBQ  C12  C13   single    1.517  0.020  1.517
 HBQ  C12  H12   single    0.970  0.020  1.090
 HBQ  C13  H131  single    0.970  0.020  1.090
 HBQ  C13  H132  single    0.970  0.020  1.090
 HBQ  C13  H133  single    0.970  0.020  1.090
 HBQ  C14  H141  single    0.970  0.020  1.090
 HBQ  C14  H142  single    0.970  0.020  1.090
 HBQ  C14  H143  single    0.970  0.020  1.090
 HBQ  N2   HN2   single    0.860  0.020  1.020

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
 HBQ  O1    C1   N2    122.81  3.000
 HBQ  N2    C1   C2    114.60  3.000
 HBQ  O1    C1   C2    122.57  3.000
 HBQ  H2    C2   N1    108.84  3.000
 HBQ  H2    C2   C9    108.78  3.000
 HBQ  N1    C2   C9    111.34  3.000
 HBQ  H2    C2   C1    106.35  3.000
 HBQ  N1    C2   C1    109.25  3.000
 HBQ  C9    C2   C1    112.11  3.000
 HBQ  N1    C3   C8    123.91  3.000
 HBQ  C8    C3   C4    119.62  3.000
 HBQ  N1    C3   C4    116.40  3.000
 HBQ  N2    C4   C5    121.08  3.000
 HBQ  C5    C4   C3    120.18  3.000
 HBQ  N2    C4   C3    118.74  3.000
 HBQ  H5    C5   C6    119.92  3.000
 HBQ  H5    C5   C4    119.58  3.000
 HBQ  C6    C5   C4    120.50  3.000
 HBQ  H6    C6   C7    120.94  3.000
 HBQ  H6    C6   C5    120.81  3.000
 HBQ  C7    C6   C5    118.25  3.000
 HBQ  F1    C7   C8    118.34  3.000
 HBQ  F1    C7   C6    118.98  3.000
 HBQ  C8    C7   C6    122.67  3.000
 HBQ  H8    C8   C7    119.80  3.000
 HBQ  H8    C8   C3    121.48  3.000
 HBQ  C7    C8   C3    118.72  3.000
 HBQ  H92   C9   H91   106.59  3.000
 HBQ  H92   C9   C10   109.46  3.000
 HBQ  H91   C9   C10   110.00  3.000
 HBQ  H92   C9   C2    106.55  3.000
 HBQ  H91   C9   C2    110.18  3.000
 HBQ  C10   C9   C2    113.75  3.000
 HBQ  H103  C10  H102  107.71  3.000
 HBQ  H103  C10  H101  107.41  3.000
 HBQ  H102  C10  H101  107.84  3.000
 HBQ  H103  C10  C9    109.88  3.000
 HBQ  H102  C10  C9    111.36  3.000
 HBQ  H101  C10  C9    112.43  3.000
 HBQ  H12   C12  O2    108.85  3.000
 HBQ  H12   C12  C14   109.53  3.000
 HBQ  O2    C12  C14   105.93  3.000
 HBQ  H12   C12  C13   109.95  3.000
 HBQ  C14   C12  C13   112.70  3.000
 HBQ  O2    C12  C13   109.74  3.000
 HBQ  H133  C13  H132  108.72  3.000
 HBQ  H133  C13  H131  107.93  3.000
 HBQ  H132  C13  H131  107.63  3.000
 HBQ  H133  C13  C12   110.97  3.000
 HBQ  H132  C13  C12   111.87  3.000
 HBQ  H131  C13  C12   109.58  3.000
 HBQ  H143  C14  H142  108.68  3.000
 HBQ  H143  C14  H141  107.88  3.000
 HBQ  H142  C14  H141  107.82  3.000
 HBQ  H143  C14  C12   111.37  3.000
 HBQ  H142  C14  C12   111.45  3.000
 HBQ  H141  C14  C12   109.51  3.000
 HBQ  C11   N1   C3    121.04  3.000
 HBQ  C11   N1   C2    123.53  3.000
 HBQ  C3    N1   C2    115.43  3.000
 HBQ  HN2   N2   C4    118.49  3.000
 HBQ  HN2   N2   C1    117.63  3.000
 HBQ  C4    N2   C1    123.75  3.000
 HBQ  C12   O2   C11   119.03  3.000
 HBQ  O3    C11  O2    124.85  3.000
 HBQ  O2    C11  N1    111.50  3.000
 HBQ  O3    C11  N1    123.65  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
 HBQ  CONST_01  C6    C5   C4   C3      0.00   0.0  0
 HBQ  CONST_02  C6    C7   C8   C3      0.00   0.0  0
 HBQ  CONST_03  C7    C8   C3   C4      0.00   0.0  0
 HBQ  CONST_04  C7    C6   C5   C4      0.00   0.0  0
 HBQ  CONST_05  C8    C3   C4   C5      0.00   0.0  0
 HBQ  CONST_06  C8    C7   C6   C5      0.00   0.0  0
 HBQ  CONST_07  C4    N2   C1   C2      0.00   0.0  0
 HBQ  CONST_08  F1    C7   C8   C3    180.00   0.0  0
 HBQ  CONST_09  F1    C7   C6   C5    180.00   0.0  0
 HBQ  CONST_10  O1    C1   N2   C4    180.00   0.0  0
 HBQ  CONST_11  H5    C5   C4   C3    180.00   0.0  0
 HBQ  CONST_12  H8    C8   C3   C4    180.00   0.0  0
 HBQ  CONST_13  H6    C6   C5   C4    180.00   0.0  0
 HBQ  CONST_14  HN2   N2   C1   C2    180.00   0.0  0
 HBQ  Var_01    C3    C4   N2   C1     19.77  30.0  1
 HBQ  Var_02    C4    C3   N1   C2    -35.86  30.0  1
 HBQ  Var_03    O3    C11  N1   C2    173.58  30.0  2
 HBQ  Var_04    N1    C11  O2   C12  -177.90  30.0  2
 HBQ  Var_05    H101  C10  C9   C2    -66.06  30.0  3
 HBQ  Var_06    C14   C12  O2   C11  -156.23  30.0  2
 HBQ  Var_07    H141  C14  C12  C13   -60.65  30.0  3
 HBQ  Var_08    H131  C13  C12  C14    60.35  30.0  3

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 HBQ  chir_01  C2  C1  C9  N1  positiv

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
 HBQ  plan-1  C1   0.020
 HBQ  plan-1  C2   0.020
 HBQ  plan-1  C4   0.020
 HBQ  plan-1  N2   0.020
 HBQ  plan-1  O1   0.020
 HBQ  plan-1  HN2  0.020
 HBQ  plan-2  C3   0.020
 HBQ  plan-2  C4   0.020
 HBQ  plan-2  C5   0.020
 HBQ  plan-2  C6   0.020
 HBQ  plan-2  C7   0.020
 HBQ  plan-2  C8   0.020
 HBQ  plan-2  F1   0.020
 HBQ  plan-2  N1   0.020
 HBQ  plan-2  N2   0.020
 HBQ  plan-2  H5   0.020
 HBQ  plan-2  H6   0.020
 HBQ  plan-2  H8   0.020
 HBQ  plan-3  N1   0.020
 HBQ  plan-3  O2   0.020
 HBQ  plan-3  O3   0.020
 HBQ  plan-3  C11  0.020

