# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 16 21:59:53 2020
#   Inital geometry file: a 118 line input string
#   Ligand name: 5-cyclopropyl-2-(5-pyrazin-2-yl-1,2,4-oxadiazol-3-yl)benzo[b][1,4]benzothiazepin-6-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O=C1N(C2CC2)c3ccc(cc3Sc4ccccc14)c5noc(n5)c6cnccn6
#
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
 8FN  8FN  5-cyclopropyl-2-(5-pyrazin-2-yl-1,2,4-oxadiazol-3-yl)benzo[b][1,4]benzothiazepin-6-one  ligand  45  30  .  2022-09-16  2023-02-02
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_8FN
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
 8FN  O1   O  O     0  -0.446  -5.3396   1.3223  -0.8303
 8FN  O2   O  O     0  -0.329   3.8862  -1.2602   1.0437
 8FN  N1   N  NT    0  -0.568  -3.2001   1.4823  -0.1676
 8FN  N3   N  N     0  -0.141   2.5333  -1.2128   1.1968
 8FN  N4   N  N     0  -0.349   7.8969  -0.7396   0.0364
 8FN  N5   N  N     0  -0.349   5.8803   0.8012  -1.0855
 8FN  C1   C  CR16  0  -0.245  -4.9366  -2.6861  -1.8835
 8FN  C2   C  CR16  0  -0.244  -4.4186  -3.5017  -0.8868
 8FN  C3   C  CR16  0  -0.233  -3.7868  -2.9373   0.2111
 8FN  C4   C  CR6   0  -0.162  -3.6782  -1.5562   0.3151
 8FN  C5   C  CR6   0   0.007  -4.2197  -0.7268  -0.6672
 8FN  C6   C  CR16  0  -0.272  -4.8504  -1.3085  -1.7654
 8FN  C7   C  C     0   0.516  -4.2966   0.7611  -0.5517
 8FN  C8   C  CR6   0   0.383  -1.8865   0.9836  -0.0687
 8FN  C9   C  CR16  0  -0.248  -0.8655   1.6010  -0.7845
 8FN  C12  C  CR16  0  -0.284  -0.2486  -0.4712   0.9495
 8FN  C13  C  CR6   0  -0.158  -1.5630  -0.0601   0.7998
 8FN  C14  C  CR5   0   0.343   2.1605  -0.2489   0.4056
 8FN  C15  C  CR5   0   0.567   4.2152  -0.3188   0.1719
 8FN  C16  C  CR6   0   0.051   5.6201  -0.1414  -0.1867
 8FN  C10  C  CR16  0  -0.291   0.4479   1.2004  -0.6278
 8FN  C11  C  CR6   0   0.001   0.7695   0.1647   0.2458
 8FN  S1   S  S2    0   0.092  -2.8467  -0.8573   1.7157
 8FN  N2   N  N     0  -0.447   3.1946   0.3406  -0.2593
 8FN  C19  C  CR16  0  -0.112   7.1440   0.9721  -1.4215
 8FN  C18  C  CR16  0  -0.074   8.1568   0.1982  -0.8595
 8FN  C17  C  CR16  0  -0.047   6.6287  -0.9154   0.3785
 8FN  C20  C  CH1   0  -0.117  -3.3636   2.9124  -0.0858
 8FN  C22  C  CH2   0  -0.478  -4.1578   3.4753   1.0462
 8FN  C21  C  CH2   0  -0.498  -2.6707   3.6350   1.0226
 8FN  H2   H  HCR6  0   0.273  -4.4959  -4.5777  -0.9673
 8FN  H3   H  HCR6  0   0.276  -3.3659  -3.5668   0.9839
 8FN  H4   H  HCR6  0   0.270  -5.2800  -0.6779  -2.5325
 8FN  H5   H  HCR6  0   0.282  -1.0949   2.4092  -1.4660
 8FN  H6   H  HCR6  0   0.277  -0.0273  -1.2898   1.6218
 8FN  H7   H  HCR6  0   0.273   1.2243   1.6948  -1.1952
 8FN  H8   H  HCR6  0   0.289   7.3704   1.7374  -2.1531
 8FN  H9   H  HCR6  0   0.294   9.1900   0.3488  -1.1463
 8FN  H10  H  HCR6  0   0.292   6.4196  -1.6835   1.1129
 8FN  H11  H  HCH1  0   0.283  -3.4373   3.4191  -1.0425
 8FN  H12  H  HCH2  0   0.261  -4.7851   4.3320   0.8386
 8FN  H13  H  HCH2  0   0.260  -4.5730   2.7774   1.7617
 8FN  H14  H  HCH2  0   0.263  -2.0914   3.0528   1.7286
 8FN  H15  H  HCH2  0   0.266  -2.2490   4.6040   0.7908
 8FN  H1   H  HCR6  0   0.270  -5.4182  -3.1220  -2.7482

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
 8FN  O2   N3   aromatic  1.362  0.020  1.362
 8FN  O2   C15  aromatic  1.325  0.020  1.325
 8FN  N5   C19  aromatic  1.319  0.020  1.319
 8FN  N5   C16  aromatic  1.328  0.020  1.328
 8FN  N3   C14  aromatic  1.302  0.020  1.302
 8FN  C19  C18  aromatic  1.393  0.020  1.393
 8FN  C15  C16  single    1.461  0.020  1.461
 8FN  C15  N2   aromatic  1.289  0.020  1.289
 8FN  C16  C17  aromatic  1.391  0.020  1.391
 8FN  C14  N2   aromatic  1.363  0.020  1.363
 8FN  C14  C11  single    1.460  0.020  1.460
 8FN  C18  N4   aromatic  1.323  0.020  1.323
 8FN  C10  C9   aromatic  1.382  0.020  1.382
 8FN  C10  C11  aromatic  1.393  0.020  1.393
 8FN  C9   C8   aromatic  1.391  0.020  1.391
 8FN  C11  C12  aromatic  1.391  0.020  1.391
 8FN  C17  N4   aromatic  1.325  0.020  1.325
 8FN  C12  C13  aromatic  1.385  0.020  1.385
 8FN  C8   N1   single    1.409  0.020  1.409
 8FN  C8   C13  aromatic  1.396  0.020  1.396
 8FN  C20  N1   single    1.442  0.020  1.442
 8FN  C20  C21  single    1.494  0.020  1.494
 8FN  C20  C22  single    1.493  0.020  1.493
 8FN  N1   C7   single    1.367  0.020  1.367
 8FN  C13  S1   single    1.767  0.020  1.767
 8FN  C21  C22  single    1.496  0.020  1.496
 8FN  C6   C1   aromatic  1.385  0.020  1.385
 8FN  C6   C5   aromatic  1.394  0.020  1.394
 8FN  C7   C5   single    1.494  0.020  1.494
 8FN  C7   O1   double    1.217  0.020  1.217
 8FN  C1   C2   aromatic  1.388  0.020  1.388
 8FN  C5   C4   aromatic  1.395  0.020  1.395
 8FN  C2   C3   aromatic  1.387  0.020  1.387
 8FN  C4   C3   aromatic  1.389  0.020  1.389
 8FN  C4   S1   single    1.772  0.020  1.772
 8FN  C1   H1   single    0.930  0.020  1.080
 8FN  C2   H2   single    0.930  0.020  1.080
 8FN  C3   H3   single    0.930  0.020  1.080
 8FN  C6   H4   single    0.930  0.020  1.080
 8FN  C9   H5   single    0.930  0.020  1.080
 8FN  C12  H6   single    0.930  0.020  1.080
 8FN  C10  H7   single    0.930  0.020  1.080
 8FN  C19  H8   single    0.930  0.020  1.080
 8FN  C18  H9   single    0.930  0.020  1.080
 8FN  C17  H10  single    0.930  0.020  1.080
 8FN  C20  H11  single    0.970  0.020  1.090
 8FN  C22  H12  single    0.970  0.020  1.090
 8FN  C22  H13  single    0.970  0.020  1.090
 8FN  C21  H14  single    0.970  0.020  1.090
 8FN  C21  H15  single    0.970  0.020  1.090

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
 8FN  C15  O2   N3   107.21  3.000
 8FN  C20  N1   C8   116.94  3.000
 8FN  C20  N1   C7   116.62  3.000
 8FN  C8   N1   C7   125.51  3.000
 8FN  C14  N3   O2   104.00  3.000
 8FN  C17  N4   C18  117.19  3.000
 8FN  C19  N5   C16  116.88  3.000
 8FN  H1   C1   C6   119.78  3.000
 8FN  H1   C1   C2   120.23  3.000
 8FN  C6   C1   C2   119.99  3.000
 8FN  H2   C2   C3   119.75  3.000
 8FN  H2   C2   C1   120.28  3.000
 8FN  C3   C2   C1   119.96  3.000
 8FN  H3   C3   C4   119.64  3.000
 8FN  H3   C3   C2   120.39  3.000
 8FN  C4   C3   C2   119.97  3.000
 8FN  S1   C4   C5   120.27  3.000
 8FN  S1   C4   C3   119.20  3.000
 8FN  C5   C4   C3   120.53  3.000
 8FN  C7   C5   C6   116.95  3.000
 8FN  C7   C5   C4   123.88  3.000
 8FN  C6   C5   C4   118.84  3.000
 8FN  H4   C6   C5   119.68  3.000
 8FN  H4   C6   C1   119.63  3.000
 8FN  C5   C6   C1   120.69  3.000
 8FN  C5   C7   N1   120.37  3.000
 8FN  C5   C7   O1   119.06  3.000
 8FN  N1   C7   O1   120.56  3.000
 8FN  C13  C8   C9   118.80  3.000
 8FN  C13  C8   N1   121.64  3.000
 8FN  C9   C8   N1   119.41  3.000
 8FN  H5   C9   C10  119.31  3.000
 8FN  H5   C9   C8   119.99  3.000
 8FN  C10  C9   C8   120.69  3.000
 8FN  H6   C12  C11  120.68  3.000
 8FN  H6   C12  C13  119.05  3.000
 8FN  C11  C12  C13  120.27  3.000
 8FN  S1   C13  C12  119.96  3.000
 8FN  S1   C13  C8   119.44  3.000
 8FN  C12  C13  C8   120.60  3.000
 8FN  N2   C14  C11  123.14  3.000
 8FN  C11  C14  N3   123.31  3.000
 8FN  N2   C14  N3   113.54  3.000
 8FN  N2   C15  C16  128.10  3.000
 8FN  N2   C15  O2   112.77  3.000
 8FN  C16  C15  O2   119.13  3.000
 8FN  C17  C16  C15  122.00  3.000
 8FN  C17  C16  N5   121.85  3.000
 8FN  C15  C16  N5   116.15  3.000
 8FN  H7   C10  C11  120.23  3.000
 8FN  H7   C10  C9   119.36  3.000
 8FN  C11  C10  C9   120.41  3.000
 8FN  C10  C11  C14  119.96  3.000
 8FN  C10  C11  C12  119.22  3.000
 8FN  C14  C11  C12  120.82  3.000
 8FN  C13  S1   C4    96.27  3.000
 8FN  C15  N2   C14  102.48  3.000
 8FN  H8   C19  C18  120.88  3.000
 8FN  H8   C19  N5   117.66  3.000
 8FN  C18  C19  N5   121.46  3.000
 8FN  H9   C18  C19  120.64  3.000
 8FN  H9   C18  N4   117.75  3.000
 8FN  C19  C18  N4   121.61  3.000
 8FN  H10  C17  C16  122.01  3.000
 8FN  H10  C17  N4   116.99  3.000
 8FN  C16  C17  N4   121.00  3.000
 8FN  H11  C20  C21  117.38  3.000
 8FN  H11  C20  C22  117.15  3.000
 8FN  C21  C20  C22   60.11  3.000
 8FN  H11  C20  N1   114.89  3.000
 8FN  C22  C20  N1   118.51  3.000
 8FN  C21  C20  N1   117.99  3.000
 8FN  H13  C22  H12  114.52  3.000
 8FN  H13  C22  C21  117.43  3.000
 8FN  H12  C22  C21  119.27  3.000
 8FN  H13  C22  C20  117.53  3.000
 8FN  H12  C22  C20  117.48  3.000
 8FN  C21  C22  C20   59.96  3.000
 8FN  H15  C21  H14  114.37  3.000
 8FN  H15  C21  C22  119.11  3.000
 8FN  H14  C21  C22  117.65  3.000
 8FN  H15  C21  C20  117.08  3.000
 8FN  H14  C21  C20  118.16  3.000
 8FN  C22  C21  C20   59.92  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
 8FN  CONST_01  N2   C14  N3   O2      0.00   0.0  0
 8FN  CONST_02  C11  C14  N3   O2    180.00   0.0  0
 8FN  CONST_03  N5   C16  C15  O2    180.00   0.0  0
 8FN  CONST_04  C17  C16  C15  O2      0.00   0.0  0
 8FN  CONST_05  C14  N2   C15  O2      0.00   0.0  0
 8FN  CONST_06  C16  C15  O2   N3    180.00   0.0  0
 8FN  CONST_07  N2   C15  O2   N3      0.00   0.0  0
 8FN  CONST_08  C15  N2   C14  N3      0.00   0.0  0
 8FN  CONST_09  C10  C11  C14  N3    180.00   0.0  0
 8FN  CONST_10  C12  C11  C14  N3      0.00   0.0  0
 8FN  CONST_11  N5   C19  C18  N4      0.00   0.0  0
 8FN  CONST_12  N5   C16  C17  N4      0.00   0.0  0
 8FN  CONST_13  C15  C16  C17  N4    180.00   0.0  0
 8FN  CONST_14  N2   C15  C16  N5      0.00   0.0  0
 8FN  CONST_15  C4   C5   C6   C1      0.00   0.0  0
 8FN  CONST_16  C4   C3   C2   C1      0.00   0.0  0
 8FN  CONST_17  C5   C6   C1   C2      0.00   0.0  0
 8FN  CONST_18  C5   C4   C3   C2      0.00   0.0  0
 8FN  CONST_19  C6   C1   C2   C3      0.00   0.0  0
 8FN  CONST_20  C6   C5   C4   C3      0.00   0.0  0
 8FN  CONST_21  C11  C10  C9   C8      0.00   0.0  0
 8FN  CONST_22  C11  C12  C13  C8      0.00   0.0  0
 8FN  CONST_23  C14  C11  C10  C9    180.00   0.0  0
 8FN  CONST_24  C12  C11  C10  C9      0.00   0.0  0
 8FN  CONST_25  C12  C13  C8   C9      0.00   0.0  0
 8FN  CONST_26  N2   C14  C11  C12   180.00   0.0  0
 8FN  CONST_27  C14  C11  C12  C13   180.00   0.0  0
 8FN  CONST_28  C10  C11  C12  C13     0.00   0.0  0
 8FN  CONST_29  C10  C9   C8   C13     0.00   0.0  0
 8FN  CONST_30  C15  O2   N3   C14     0.00   0.0  0
 8FN  CONST_31  C16  C15  N2   C14   180.00   0.0  0
 8FN  CONST_32  C19  N5   C16  C15   180.00   0.0  0
 8FN  CONST_33  C11  C14  N2   C15   180.00   0.0  0
 8FN  CONST_34  C18  C19  N5   C16     0.00   0.0  0
 8FN  CONST_35  C18  N4   C17  C16     0.00   0.0  0
 8FN  CONST_36  N2   C14  C11  C10     0.00   0.0  0
 8FN  CONST_37  C17  C16  C15  N2    180.00   0.0  0
 8FN  CONST_38  C17  C16  N5   C19     0.00   0.0  0
 8FN  CONST_39  C17  N4   C18  C19     0.00   0.0  0
 8FN  CONST_40  C8   N1   C7   C5      0.00   0.0  0
 8FN  CONST_41  C20  N1   C7   C5    180.00   0.0  0
 8FN  CONST_42  C8   N1   C7   O1    180.00   0.0  0
 8FN  CONST_43  C20  N1   C7   O1      0.00   0.0  0
 8FN  CONST_44  H5   C9   C8   N1      0.00   0.0  0
 8FN  CONST_45  H8   C19  C18  N4    180.00   0.0  0
 8FN  CONST_46  H9   C18  C19  N5    180.00   0.0  0
 8FN  CONST_47  H10  C17  C16  N5    180.00   0.0  0
 8FN  CONST_48  H3   C3   C2   C1    180.00   0.0  0
 8FN  CONST_49  H4   C6   C1   C2    180.00   0.0  0
 8FN  CONST_50  H1   C1   C2   C3    180.00   0.0  0
 8FN  CONST_51  H2   C2   C3   C4    180.00   0.0  0
 8FN  CONST_52  H7   C10  C9   C8    180.00   0.0  0
 8FN  CONST_53  H6   C12  C13  C8    180.00   0.0  0
 8FN  Var_01    C22  C21  C20  N1   -108.55  30.0  1
 8FN  Var_02    C6   C5   C7   N1   -138.41  30.0  1
 8FN  Var_03    C12  C13  S1   C4   -114.63  30.0  1
 8FN  Var_04    C9   C8   N1   C7    123.62  30.0  1
 8FN  Var_05    C21  C20  N1   C7    142.38  30.0  1

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
 8FN  chir_01  C20  N1  C21  C22  both

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
 8FN  plan-1  O2   0.020
 8FN  plan-1  N3   0.020
 8FN  plan-1  C14  0.020
 8FN  plan-1  C15  0.020
 8FN  plan-1  C16  0.020
 8FN  plan-1  C11  0.020
 8FN  plan-1  N2   0.020
 8FN  plan-2  C1   0.020
 8FN  plan-2  C2   0.020
 8FN  plan-2  C3   0.020
 8FN  plan-2  C4   0.020
 8FN  plan-2  C5   0.020
 8FN  plan-2  C6   0.020
 8FN  plan-2  C7   0.020
 8FN  plan-2  S1   0.020
 8FN  plan-2  H2   0.020
 8FN  plan-2  H3   0.020
 8FN  plan-2  H4   0.020
 8FN  plan-2  H1   0.020
 8FN  plan-3  N1   0.020
 8FN  plan-3  C8   0.020
 8FN  plan-3  C9   0.020
 8FN  plan-3  C12  0.020
 8FN  plan-3  C13  0.020
 8FN  plan-3  C14  0.020
 8FN  plan-3  C10  0.020
 8FN  plan-3  C11  0.020
 8FN  plan-3  S1   0.020
 8FN  plan-3  H5   0.020
 8FN  plan-3  H6   0.020
 8FN  plan-3  H7   0.020
 8FN  plan-4  N4   0.020
 8FN  plan-4  N5   0.020
 8FN  plan-4  C15  0.020
 8FN  plan-4  C16  0.020
 8FN  plan-4  C19  0.020
 8FN  plan-4  C18  0.020
 8FN  plan-4  C17  0.020
 8FN  plan-4  H8   0.020
 8FN  plan-4  H9   0.020
 8FN  plan-4  H10  0.020
 8FN  plan-5  O1   0.020
 8FN  plan-5  N1   0.020
 8FN  plan-5  C5   0.020
 8FN  plan-5  C7   0.020
 8FN  plan-5  C8   0.020
 8FN  plan-5  C20  0.020

