# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  2 13:43:16 2020
#   Inital geometry file: a 125 line input string
#   Ligand name: 2-chloro-N-[(3S)-1-{2-[(2-hydroxyethyl)amino]-2-oxoethyl}-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OCCNC(=O)CN1C(=O)[C@H](Cc2ccccc12)NC(=O)c3[nH]c4sc(Cl)cc4c3
#
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
 FRX  FRX  2-chloro-N-[(3S)-1-{2-[(2-hydroxyethyl)amino]-2-oxoethyl}-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide  ligand  49  30  .  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_FRX
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
 FRX  O26   O   O     0  -0.477  -1.9458   -4.9544  -1.9424
 FRX  C22   C   C     0   0.542  -0.8949   -4.6102  -2.4565
 FRX  N22   N   NH1   0  -0.621  -0.7765   -4.1876  -3.7213
 FRX  C24   C   CH2   0  -0.340  -1.8731   -4.1929  -4.6644
 FRX  C25   C   CH2   0  -0.169  -2.0545   -5.5306  -5.3658
 FRX  O25   O   OH1   0  -0.663  -0.9115   -5.9341  -6.0829
 FRX  C21   C   CH2   0  -0.492   0.4179   -4.6493  -1.6801
 FRX  N17   N   NT    0  -0.573   0.1844   -4.6627  -0.2580
 FRX  C19   C   C     0   0.557   0.0025   -5.8708   0.3475
 FRX  O19   O   O     0  -0.453   0.1563   -6.9252  -0.2370
 FRX  C17   C   CR6   0   0.376  -0.0145   -3.4434   0.4200
 FRX  C31   C   CR16  0  -0.314  -0.2994   -2.2670  -0.2677
 FRX  C30   C   CR16  0  -0.264  -0.4452   -1.0746   0.4283
 FRX  C29   C   CR16  0  -0.254  -0.3202   -1.0448   1.8081
 FRX  C16   C   CR6   0   0.068   0.1158   -3.4206   1.8117
 FRX  C28   C   CR16  0  -0.337  -0.0468   -2.2229   2.4900
 FRX  C15   C   CH2   0  -0.492   0.4062   -4.7118   2.5089
 FRX  C13   C   CH1   0  -0.198  -0.3901   -5.8103   1.8139
 FRX  N11   N   NH1   0  -0.675  -0.2247   -7.1098   2.4010
 FRX  C11   C   C     0   0.502  -0.9258   -7.4951   3.4811
 FRX  O13   O   O     0  -0.498  -1.7252   -6.7660   4.0577
 FRX  C7    C   CR5   0   0.239  -0.6842   -8.8646   3.9532
 FRX  N8    N   NR15  0  -0.687  -1.3790   -9.3053   5.0546
 FRX  C3    C   CR55  0   0.091  -1.0086  -10.5707   5.3029
 FRX  C4    C   CR55  0   0.118  -0.0649  -10.9769   4.3679
 FRX  C6    C   CR15  0  -0.442   0.1382   -9.8763   3.5032
 FRX  C5    C   CR15  0  -0.187   0.3612  -12.3233   4.5898
 FRX  S2    S   S2    0   0.276  -1.4035  -11.7792   6.4579
 FRX  C1    C   CR5   0  -0.259  -0.2704  -12.8544   5.6609
 FRX  CL    CL  CL    0  -0.078  -0.0778  -14.4290   6.2954
 FRX  HN22  H   HNH1  0   0.407   0.1399   -3.9559  -4.0692
 FRX  H241  H   HCH2  0   0.258  -1.6862   -3.4059  -5.3971
 FRX  H242  H   HCH2  0   0.250  -2.7957   -3.9292  -4.1467
 FRX  H251  H   HCH2  0   0.210  -2.9425   -5.4649  -6.0068
 FRX  H252  H   HCH2  0   0.224  -2.2509   -6.3066  -4.6234
 FRX  HO25  H   HOH1  0   0.448  -0.7728   -5.3113  -6.8029
 FRX  H211  H   HCH2  0   0.324   0.9540   -5.5555  -1.9628
 FRX  H212  H   HCH2  0   0.300   1.0680   -3.8123  -1.9372
 FRX  H31   H   HCR6  0   0.270  -0.4125   -2.2531  -1.3428
 FRX  H30   H   HCR6  0   0.262  -0.6672   -0.1688  -0.1200
 FRX  H29   H   HCR6  0   0.258  -0.4404   -0.1167   2.3506
 FRX  H28   H   HCR6  0   0.256   0.0447   -2.2162   3.5695
 FRX  H151  H   HCH2  0   0.269   1.4749   -4.9474   2.4651
 FRX  H152  H   HCH2  0   0.280   0.1281   -4.6528   3.5606
 FRX  H13   H   HCH1  0   0.303  -1.4525   -5.5370   1.8486
 FRX  HN11  H   HNH1  0   0.409   0.3884   -7.7608   1.9360
 FRX  HN8   H   HNR5  0   0.422  -2.0490   -8.7520   5.5657
 FRX  H6    H   HCR5  0   0.267   0.8075   -9.8359   2.6580
 FRX  H5    H   HCR5  0   0.287   1.0862  -12.8598   3.9957

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
 FRX  O26  C22   double    1.220  0.020  1.220
 FRX  C22  C21   single    1.526  0.020  1.526
 FRX  C22  N22   single    1.339  0.020  1.339
 FRX  N22  C24   single    1.446  0.020  1.446
 FRX  N22  HN22  single    0.860  0.020  1.020
 FRX  C24  C25   single    1.521  0.020  1.521
 FRX  C24  H241  single    0.970  0.020  1.090
 FRX  C24  H242  single    0.970  0.020  1.090
 FRX  C25  O25   single    1.408  0.020  1.408
 FRX  C25  H251  single    0.970  0.020  1.090
 FRX  C25  H252  single    0.970  0.020  1.090
 FRX  O25  HO25  single    0.850  0.020  0.980
 FRX  C21  N17   single    1.441  0.020  1.441
 FRX  C21  H211  single    0.970  0.020  1.090
 FRX  C21  H212  single    0.970  0.020  1.090
 FRX  N17  C17   single    1.409  0.020  1.409
 FRX  N17  C19   single    1.364  0.020  1.364
 FRX  C19  C13   single    1.519  0.020  1.519
 FRX  C19  O19   double    1.215  0.020  1.215
 FRX  C17  C16   aromatic  1.398  0.020  1.398
 FRX  C17  C31   aromatic  1.392  0.020  1.392
 FRX  C31  C30   aromatic  1.388  0.020  1.388
 FRX  C31  H31   single    0.930  0.020  1.080
 FRX  C30  C29   aromatic  1.386  0.020  1.386
 FRX  C30  H30   single    0.930  0.020  1.080
 FRX  C29  C28   aromatic  1.388  0.020  1.388
 FRX  C29  H29   single    0.930  0.020  1.080
 FRX  C16  C28   aromatic  1.386  0.020  1.386
 FRX  C16  C15   single    1.496  0.020  1.496
 FRX  C28  H28   single    0.930  0.020  1.080
 FRX  C15  C13   single    1.524  0.020  1.524
 FRX  C15  H151  single    0.970  0.020  1.090
 FRX  C15  H152  single    0.970  0.020  1.090
 FRX  C13  N11   single    1.435  0.020  1.435
 FRX  C13  H13   single    0.970  0.020  1.090
 FRX  N11  C11   single    1.344  0.020  1.344
 FRX  N11  HN11  single    0.860  0.020  1.020
 FRX  C11  C7    single    1.469  0.020  1.469
 FRX  C11  O13   double    1.226  0.020  1.226
 FRX  C7   C6    aromatic  1.379  0.020  1.379
 FRX  C7   N8    aromatic  1.375  0.020  1.375
 FRX  N8   C3    aromatic  1.342  0.020  1.342
 FRX  N8   HN8   single    0.860  0.020  1.020
 FRX  C3   C4    aromatic  1.389  0.020  1.389
 FRX  C3   S2    aromatic  1.718  0.020  1.718
 FRX  C4   C5    aromatic  1.430  0.020  1.430
 FRX  C4   C6    aromatic  1.414  0.020  1.414
 FRX  C6   H6    single    0.930  0.020  1.080
 FRX  C5   C1    aromatic  1.352  0.020  1.352
 FRX  C5   H5    single    0.930  0.020  1.080
 FRX  S2   C1    aromatic  1.754  0.020  1.754
 FRX  C1   CL    single    1.709  0.020  1.709

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
 FRX  C21   C22  N22   114.38  3.000
 FRX  N22   C22  O26   124.30  3.000
 FRX  C21   C22  O26   121.32  3.000
 FRX  HN22  N22  C24   117.74  3.000
 FRX  HN22  N22  C22   118.64  3.000
 FRX  C24   N22  C22   123.22  3.000
 FRX  H242  C24  H241  106.82  3.000
 FRX  H242  C24  C25   109.31  3.000
 FRX  H241  C24  C25   110.18  3.000
 FRX  H242  C24  N22   109.34  3.000
 FRX  H241  C24  N22   107.78  3.000
 FRX  C25   C24  N22   113.22  3.000
 FRX  H252  C25  H251  107.12  3.000
 FRX  H252  C25  O25   106.77  3.000
 FRX  H251  C25  O25   112.12  3.000
 FRX  H252  C25  C24   109.45  3.000
 FRX  H251  C25  C24   108.25  3.000
 FRX  O25   C25  C24   112.95  3.000
 FRX  HO25  O25  C25   108.22  3.000
 FRX  H212  C21  H211  106.48  3.000
 FRX  H212  C21  N17   109.66  3.000
 FRX  H211  C21  N17   109.14  3.000
 FRX  H212  C21  C22   111.92  3.000
 FRX  H211  C21  C22   108.21  3.000
 FRX  N17   C21  C22   111.28  3.000
 FRX  C17   N17  C19   122.28  3.000
 FRX  C19   N17  C21   117.91  3.000
 FRX  C17   N17  C21   119.31  3.000
 FRX  C13   C19  O19   122.11  3.000
 FRX  O19   C19  N17   122.56  3.000
 FRX  C13   C19  N17   115.33  3.000
 FRX  C16   C17  C31   119.81  3.000
 FRX  C31   C17  N17   121.49  3.000
 FRX  C16   C17  N17   118.68  3.000
 FRX  H31   C31  C30   118.45  3.000
 FRX  H31   C31  C17   121.57  3.000
 FRX  C30   C31  C17   119.98  3.000
 FRX  H30   C30  C29   120.34  3.000
 FRX  H30   C30  C31   119.12  3.000
 FRX  C29   C30  C31   120.54  3.000
 FRX  H29   C29  C28   120.23  3.000
 FRX  H29   C29  C30   120.52  3.000
 FRX  C28   C29  C30   119.24  3.000
 FRX  C15   C16  C28   122.72  3.000
 FRX  C15   C16  C17   117.91  3.000
 FRX  C28   C16  C17   119.37  3.000
 FRX  H28   C28  C16   118.89  3.000
 FRX  H28   C28  C29   120.05  3.000
 FRX  C16   C28  C29   121.06  3.000
 FRX  H152  C15  H151  107.42  3.000
 FRX  H152  C15  C13   110.23  3.000
 FRX  H151  C15  C13   109.66  3.000
 FRX  H152  C15  C16   110.71  3.000
 FRX  H151  C15  C16   110.88  3.000
 FRX  C13   C15  C16   107.95  3.000
 FRX  H13   C13  N11   108.91  3.000
 FRX  H13   C13  C15   108.16  3.000
 FRX  N11   C13  C15   113.94  3.000
 FRX  H13   C13  C19   106.89  3.000
 FRX  N11   C13  C19   109.20  3.000
 FRX  C15   C13  C19   109.50  3.000
 FRX  HN11  N11  C11   120.19  3.000
 FRX  HN11  N11  C13   117.78  3.000
 FRX  C11   N11  C13   121.87  3.000
 FRX  C7    C11  O13   120.71  3.000
 FRX  O13   C11  N11   123.20  3.000
 FRX  C7    C11  N11   116.09  3.000
 FRX  C6    C7   N8    109.12  3.000
 FRX  N8    C7   C11   118.25  3.000
 FRX  C6    C7   C11   132.63  3.000
 FRX  HN8   N8   C3    127.40  3.000
 FRX  HN8   N8   C7    124.48  3.000
 FRX  C3    N8   C7    108.12  3.000
 FRX  S2    C3   C4    113.77  3.000
 FRX  S2    C3   N8    136.43  3.000
 FRX  C4    C3   N8    109.81  3.000
 FRX  C5    C4   C6    141.72  3.000
 FRX  C6    C4   C3    106.35  3.000
 FRX  C5    C4   C3    111.93  3.000
 FRX  H6    C6   C4    126.67  3.000
 FRX  H6    C6   C7    126.73  3.000
 FRX  C4    C6   C7    106.60  3.000
 FRX  H5    C5   C1    123.66  3.000
 FRX  H5    C5   C4    125.63  3.000
 FRX  C1    C5   C4    110.71  3.000
 FRX  C1    S2   C3     88.69  3.000
 FRX  CL    C1   S2    117.98  3.000
 FRX  CL    C1   C5    127.12  3.000
 FRX  S2    C1   C5    114.90  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
 FRX  CONST_01  C29   C28  C16  C17    0.00   0.0  0
 FRX  CONST_02  C29   C30  C31  C17    0.00   0.0  0
 FRX  CONST_03  C28   C16  C17  C31    0.00   0.0  0
 FRX  CONST_04  C28   C29  C30  C31    0.00   0.0  0
 FRX  CONST_05  C16   C17  C31  C30    0.00   0.0  0
 FRX  CONST_06  C16   C28  C29  C30    0.00   0.0  0
 FRX  CONST_07  C3    C4   C6   C7     0.00   0.0  0
 FRX  CONST_08  C5    C4   C6   C7   180.00   0.0  0
 FRX  CONST_09  C4    C3   N8   C7     0.00   0.0  0
 FRX  CONST_10  S2    C3   N8   C7   180.00   0.0  0
 FRX  CONST_11  C4    C6   C7   N8     0.00   0.0  0
 FRX  CONST_12  C5    C4   C3   N8   180.00   0.0  0
 FRX  CONST_13  C6    C4   C3   N8     0.00   0.0  0
 FRX  CONST_14  C1    S2   C3   N8   180.00   0.0  0
 FRX  CONST_15  C6    C7   N8   C3     0.00   0.0  0
 FRX  CONST_16  C1    C5   C4   C3     0.00   0.0  0
 FRX  CONST_17  C5    C1   S2   C3     0.00   0.0  0
 FRX  CONST_18  C1    S2   C3   C4     0.00   0.0  0
 FRX  CONST_19  S2    C1   C5   C4     0.00   0.0  0
 FRX  CONST_20  S2    C3   C4   C6   180.00   0.0  0
 FRX  CONST_21  C1    C5   C4   C6   180.00   0.0  0
 FRX  CONST_22  S2    C3   C4   C5     0.00   0.0  0
 FRX  CONST_23  C13   C19  N17  C17    0.00   0.0  0
 FRX  CONST_24  C4    C6   C7   C11  180.00   0.0  0
 FRX  CONST_25  C3    N8   C7   C11  180.00   0.0  0
 FRX  CONST_26  CL    C1   S2   C3   180.00   0.0  0
 FRX  CONST_27  CL    C1   C5   C4   180.00   0.0  0
 FRX  CONST_28  C13   C19  N17  C21  180.00   0.0  0
 FRX  CONST_29  C17   N17  C19  O19  180.00   0.0  0
 FRX  CONST_30  H31   C31  C17  N17    0.00   0.0  0
 FRX  CONST_31  H28   C28  C16  C17  180.00   0.0  0
 FRX  CONST_32  H30   C30  C31  C17  180.00   0.0  0
 FRX  CONST_33  H29   C29  C30  C31  180.00   0.0  0
 FRX  CONST_34  H6    C6   C7   N8   180.00   0.0  0
 FRX  CONST_35  H5    C5   C4   C3   180.00   0.0  0
 FRX  CONST_36  HN8   N8   C3   C4   180.00   0.0  0
 FRX  CONST_37  C7    C11  N11  C13  180.00   0.0  0
 FRX  CONST_38  O19   C19  N17  C21    0.00   0.0  0
 FRX  CONST_39  O13   C11  N11  C13    0.00   0.0  0
 FRX  CONST_40  HN11  N11  C11  C7     0.00   0.0  0
 FRX  CONST_41  C24   N22  C22  O26    0.00   0.0  0
 FRX  CONST_42  C21   C22  N22  C24  180.00   0.0  0
 FRX  CONST_43  HN22  N22  C22  O26  180.00   0.0  0
 FRX  Var_01    C16   C17  N17  C19   25.12  30.0  1
 FRX  Var_02    C13   C15  C16  C17  -38.44  30.0  1
 FRX  Var_03    C17   N17  C21  C22  -84.60  30.0  3
 FRX  Var_04    C6    C7   C11  N11   -0.18  30.0  2
 FRX  Var_05    N17   C21  C22  O26  -20.25  30.0  3
 FRX  Var_06    C25   C24  N22  C22  -84.88  30.0  3
 FRX  Var_07    O25   C25  C24  N22  -58.99  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
 FRX  chir_01  C13  C19  C15  N11  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
 FRX  plan-1  C11   0.020
 FRX  plan-1  C7    0.020
 FRX  plan-1  N8    0.020
 FRX  plan-1  C3    0.020
 FRX  plan-1  C4    0.020
 FRX  plan-1  C6    0.020
 FRX  plan-1  C5    0.020
 FRX  plan-1  S2    0.020
 FRX  plan-1  C1    0.020
 FRX  plan-1  CL    0.020
 FRX  plan-1  HN8   0.020
 FRX  plan-1  H6    0.020
 FRX  plan-1  H5    0.020
 FRX  plan-2  N17   0.020
 FRX  plan-2  C17   0.020
 FRX  plan-2  C31   0.020
 FRX  plan-2  C30   0.020
 FRX  plan-2  C29   0.020
 FRX  plan-2  C16   0.020
 FRX  plan-2  C28   0.020
 FRX  plan-2  C15   0.020
 FRX  plan-2  H31   0.020
 FRX  plan-2  H30   0.020
 FRX  plan-2  H29   0.020
 FRX  plan-2  H28   0.020
 FRX  plan-3  O26   0.020
 FRX  plan-3  C22   0.020
 FRX  plan-3  N22   0.020
 FRX  plan-3  C24   0.020
 FRX  plan-3  C21   0.020
 FRX  plan-3  HN22  0.020
 FRX  plan-4  C13   0.020
 FRX  plan-4  N11   0.020
 FRX  plan-4  C11   0.020
 FRX  plan-4  O13   0.020
 FRX  plan-4  C7    0.020
 FRX  plan-4  HN11  0.020
 FRX  plan-5  C21   0.020
 FRX  plan-5  N17   0.020
 FRX  plan-5  C19   0.020
 FRX  plan-5  O19   0.020
 FRX  plan-5  C17   0.020
 FRX  plan-5  C13   0.020

