# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr 17 17:15:55 2020
#   Inital geometry file: a 129 line input string
#   Ligand name: 4-{2-[(cyclopropylmethyl)amino]-5-(ethylsulfonyl)phenyl}-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC[S](=O)(=O)c1ccc(NCC2CC2)c(c1)C3=CN(C)C(=O)c4[nH]ccc34
#
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
 8O1  8O1  4-{2-[(cyclopropylmethyl)amino]-5-(ethylsulfonyl)phenyl}-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one  ligand  50  27  .  2022-09-16  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_8O1
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
 8O1  C4    C  CR16  0  -0.282   1.4503  -0.2169   0.3210
 8O1  C5    C  CR15  0  -0.010  -1.1319  -3.3161  -2.2072
 8O1  C6    C  CR56  0   0.193  -1.1615  -1.7128  -0.6482
 8O1  C7    C  CR6   0  -0.035   0.1789   0.2946   0.1511
 8O1  C8    C  CR6   0   0.380   0.0133   1.6787  -0.1269
 8O1  C10   C  CR56  0   0.130  -2.2711  -2.5334  -0.4815
 8O1  C13   C  CR6   0   0.523  -3.2790  -2.3631   0.5174
 8O1  C15   C  CH2   0  -0.491  -3.6791   4.9848  -0.3697
 8O1  C17   C  CH3   0  -0.671   6.0719  -1.1485  -1.2036
 8O1  C20   C  CH2   0  -0.583   4.6716  -0.5601  -1.2100
 8O1  C1    C  CR16  0  -0.356   1.1604   2.4963  -0.1661
 8O1  C2    C  CR16  0  -0.228   2.4195   1.9671   0.0167
 8O1  C3    C  CR15  0  -0.457  -0.4356  -2.2191  -1.7544
 8O1  C9    C  CR6   0  -0.214   2.5715   0.6056   0.2515
 8O1  C11   C  CR16  0  -0.011  -1.9311  -0.4622   1.2046
 8O1  C12   C  CR6   0  -0.137  -0.9847  -0.6124   0.2452
 8O1  C14   C  CH2   0  -0.485  -3.9637   3.6516   0.2517
 8O1  C16   C  CH1   0  -0.290  -2.9624   3.7678  -0.8601
 8O1  C19   C  CH2   0  -0.273  -1.5016   3.5922  -0.5569
 8O1  N21   N  NR15  0  -0.643  -2.2322  -3.4979  -1.4398
 8O1  N22   N  NR6   0  -0.531  -3.0224  -1.2829   1.3436
 8O1  N23   N  NH1   0  -0.689  -1.2128   2.1912  -0.3494
 8O1  O24   O  O     0  -0.511  -4.2684  -3.0812   0.6462
 8O1  O25   O  OS    0  -0.681   4.0599  -1.3071   1.2471
 8O1  O26   O  OS    0  -0.681   5.0868   0.9616   0.9067
 8O1  S27   S  S     0   1.202   4.1718  -0.0854   0.4460
 8O1  H4    H  HCR6  0   0.274   1.5611  -1.2742   0.5284
 8O1  H5    H  HCR5  0   0.288  -0.9153  -3.9801  -3.0281
 8O1  H151  H  HCH2  0   0.249  -3.1161   5.7054   0.2107
 8O1  H173  H  HCH3  0   0.248   6.8089  -0.4249  -0.8597
 8O1  H172  H  HCH3  0   0.247   6.1319  -2.0360  -0.5759
 8O1  H171  H  HCH3  0   0.263   6.3387  -1.4387  -2.2185
 8O1  H1    H  HCR6  0   0.280   1.0641   3.5574  -0.3490
 8O1  H2    H  HCR6  0   0.278   3.2778   2.6243  -0.0229
 8O1  H3    H  HCR5  0   0.251   0.4803  -1.8328  -2.1717
 8O1  H11   H  HCR6  0   0.302  -1.8669   0.3298   1.9390
 8O1  H142  H  HCH2  0   0.249  -3.5930   3.4660   1.2529
 8O1  H141  H  HCH2  0   0.255  -4.9113   3.1766   0.0329
 8O1  H16   H  HCH1  0   0.270  -3.2717   3.3815  -1.8260
 8O1  H191  H  HCH2  0   0.244  -0.9033   3.9855  -1.3854
 8O1  H192  H  HCH2  0   0.233  -1.2289   4.1728   0.3328
 8O1  H21   H  HNR5  0   0.416  -2.9157  -4.2277  -1.5623
 8O1  H23   H  HNH1  0   0.398  -1.9987   1.5633  -0.3248
 8O1  H201  H  HCH2  0   0.294   4.6089   0.3356  -1.8292
 8O1  H202  H  HCH2  0   0.291   3.9314  -1.2769  -1.5687
 8O1  C18   C  CH3   0  -0.543  -3.9637  -0.9558   2.4063
 8O1  H152  H  HCH2  0   0.256  -4.4327   5.4241  -1.0098
 8O1  H183  H  HCH3  0   0.273  -4.6982  -1.7463   2.5043
 8O1  H181  H  HCH3  0   0.261  -3.4343  -0.8500   3.3509
 8O1  H182  H  HCH3  0   0.256  -4.4804  -0.0230   2.1828

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
 8O1  C4   C7    aromatic  1.381  0.020  1.381
 8O1  C4   C9    aromatic  1.392  0.020  1.392
 8O1  C5   C3    aromatic  1.376  0.020  1.376
 8O1  C5   N21   aromatic  1.354  0.020  1.354
 8O1  C6   C10   aromatic  1.390  0.020  1.390
 8O1  C6   C3    aromatic  1.417  0.020  1.417
 8O1  C6   C12   single    1.428  0.020  1.428
 8O1  C7   C8    aromatic  1.421  0.020  1.421
 8O1  C7   C12   single    1.478  0.020  1.478
 8O1  C8   C1    aromatic  1.409  0.020  1.409
 8O1  C8   N23   single    1.347  0.020  1.347
 8O1  C10  C13   single    1.429  0.020  1.429
 8O1  C10  N21   aromatic  1.360  0.020  1.360
 8O1  C13  N22   single    1.384  0.020  1.384
 8O1  C13  O24   double    1.229  0.020  1.229
 8O1  C15  C14   single    1.498  0.020  1.498
 8O1  C15  C16   single    1.495  0.020  1.495
 8O1  C17  C20   single    1.519  0.020  1.519
 8O1  C20  S27   single    1.794  0.020  1.794
 8O1  C1   C2    aromatic  1.378  0.020  1.378
 8O1  C2   C9    aromatic  1.390  0.020  1.390
 8O1  C9   S27   single    1.754  0.020  1.754
 8O1  C11  C12   double    1.356  0.020  1.356
 8O1  C11  N22   single    1.373  0.020  1.373
 8O1  C14  C16   single    1.501  0.020  1.501
 8O1  C16  C19   single    1.502  0.020  1.502
 8O1  C18  N22   single    1.457  0.020  1.457
 8O1  C19  N23   single    1.445  0.020  1.445
 8O1  O25  S27   double    1.465  0.020  1.465
 8O1  O26  S27   double    1.465  0.020  1.465
 8O1  C4   H4    single    0.930  0.020  1.080
 8O1  C5   H5    single    0.930  0.020  1.080
 8O1  C15  H152  single    0.970  0.020  1.090
 8O1  C15  H151  single    0.970  0.020  1.090
 8O1  C17  H173  single    0.970  0.020  1.090
 8O1  C17  H172  single    0.970  0.020  1.090
 8O1  C17  H171  single    0.970  0.020  1.090
 8O1  C20  H201  single    0.970  0.020  1.090
 8O1  C20  H202  single    0.970  0.020  1.090
 8O1  C1   H1    single    0.930  0.020  1.080
 8O1  C2   H2    single    0.930  0.020  1.080
 8O1  C3   H3    single    0.930  0.020  1.080
 8O1  C11  H11   single    0.930  0.020  1.080
 8O1  C14  H142  single    0.970  0.020  1.090
 8O1  C14  H141  single    0.970  0.020  1.090
 8O1  C16  H16   single    0.970  0.020  1.090
 8O1  C18  H183  single    0.970  0.020  1.090
 8O1  C18  H181  single    0.970  0.020  1.090
 8O1  C18  H182  single    0.970  0.020  1.090
 8O1  C19  H191  single    0.970  0.020  1.090
 8O1  C19  H192  single    0.970  0.020  1.090
 8O1  N21  H21   single    0.860  0.020  1.020
 8O1  N23  H23   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
 8O1  H4    C4   C9    120.25  3.000
 8O1  H4    C4   C7    118.64  3.000
 8O1  C9    C4   C7    121.10  3.000
 8O1  H5    C5   N21   120.82  3.000
 8O1  H5    C5   C3    129.80  3.000
 8O1  N21   C5   C3    109.38  3.000
 8O1  C12   C6   C3    134.45  3.000
 8O1  C12   C6   C10   118.59  3.000
 8O1  C3    C6   C10   106.96  3.000
 8O1  C12   C7   C8    121.20  3.000
 8O1  C12   C7   C4    119.32  3.000
 8O1  C8    C7   C4    119.48  3.000
 8O1  N23   C8   C1    121.03  3.000
 8O1  N23   C8   C7    120.58  3.000
 8O1  C1    C8   C7    118.39  3.000
 8O1  N21   C10  C13   126.66  3.000
 8O1  N21   C10  C6    108.14  3.000
 8O1  C13   C10  C6    125.20  3.000
 8O1  O24   C13  N22   122.86  3.000
 8O1  O24   C13  C10   124.84  3.000
 8O1  N22   C13  C10   112.30  3.000
 8O1  H151  C15  H152  114.13  3.000
 8O1  H151  C15  C16   117.92  3.000
 8O1  H152  C15  C16   118.06  3.000
 8O1  H151  C15  C14   117.94  3.000
 8O1  H152  C15  C14   118.32  3.000
 8O1  C16   C15  C14    60.18  3.000
 8O1  H171  C17  H172  107.86  3.000
 8O1  H171  C17  H173  107.80  3.000
 8O1  H172  C17  H173  108.81  3.000
 8O1  H171  C17  C20   108.98  3.000
 8O1  H172  C17  C20   111.65  3.000
 8O1  H173  C17  C20   111.59  3.000
 8O1  H202  C20  H201  108.29  3.000
 8O1  H202  C20  S27   106.76  3.000
 8O1  H201  C20  S27   106.91  3.000
 8O1  H202  C20  C17   111.86  3.000
 8O1  H201  C20  C17   111.93  3.000
 8O1  S27   C20  C17   110.83  3.000
 8O1  H1    C1   C2    118.74  3.000
 8O1  H1    C1   C8    120.11  3.000
 8O1  C2    C1   C8    121.15  3.000
 8O1  H2    C2   C9    120.96  3.000
 8O1  H2    C2   C1    119.13  3.000
 8O1  C9    C2   C1    119.91  3.000
 8O1  H3    C3   C6    127.55  3.000
 8O1  H3    C3   C5    126.03  3.000
 8O1  C6    C3   C5    106.42  3.000
 8O1  S27   C9   C2    120.29  3.000
 8O1  S27   C9   C4    119.77  3.000
 8O1  C2    C9   C4    119.93  3.000
 8O1  H11   C11  N22   114.59  3.000
 8O1  H11   C11  C12   121.33  3.000
 8O1  N22   C11  C12   124.08  3.000
 8O1  C11   C12  C7    121.77  3.000
 8O1  C11   C12  C6    116.20  3.000
 8O1  C7    C12  C6    122.02  3.000
 8O1  H141  C14  H142  114.27  3.000
 8O1  H141  C14  C16   117.93  3.000
 8O1  H142  C14  C16   118.00  3.000
 8O1  H141  C14  C15   118.23  3.000
 8O1  H142  C14  C15   118.08  3.000
 8O1  C16   C14  C15    59.80  3.000
 8O1  H16   C16  C19   114.53  3.000
 8O1  H16   C16  C14   116.21  3.000
 8O1  C19   C16  C14   119.35  3.000
 8O1  H16   C16  C15   116.43  3.000
 8O1  C19   C16  C15   119.68  3.000
 8O1  C14   C16  C15    60.01  3.000
 8O1  H192  C19  H191  106.72  3.000
 8O1  H192  C19  N23   110.30  3.000
 8O1  H191  C19  N23   110.34  3.000
 8O1  H192  C19  C16   110.10  3.000
 8O1  H191  C19  C16   109.67  3.000
 8O1  N23   C19  C16   109.67  3.000
 8O1  H21   N21  C10   125.45  3.000
 8O1  H21   N21  C5    125.44  3.000
 8O1  C10   N21  C5    109.11  3.000
 8O1  C18   N22  C11   116.96  3.000
 8O1  C18   N22  C13   119.40  3.000
 8O1  C11   N22  C13   123.62  3.000
 8O1  H23   N23  C19   116.89  3.000
 8O1  H23   N23  C8    117.99  3.000
 8O1  C19   N23  C8    125.05  3.000
 8O1  O26   S27  O25   118.15  3.000
 8O1  O26   S27  C9    108.86  3.000
 8O1  O25   S27  C9    108.63  3.000
 8O1  O26   S27  C20   107.79  3.000
 8O1  O25   S27  C20   107.78  3.000
 8O1  C9    S27  C20   104.84  3.000
 8O1  H182  C18  H181  109.00  3.000
 8O1  H182  C18  H183  108.77  3.000
 8O1  H181  C18  H183  108.80  3.000
 8O1  H182  C18  N22   110.43  3.000
 8O1  H181  C18  N22   109.92  3.000
 8O1  H183  C18  N22   109.88  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
 8O1  CONST_01  C1    C8   C7   C4     0.00   0.0  0
 8O1  CONST_02  C1    C2   C9   C4     0.00   0.0  0
 8O1  CONST_03  C10   C6   C3   C5     0.00   0.0  0
 8O1  CONST_04  C6    C10  N21  C5     0.00   0.0  0
 8O1  CONST_05  N21   C5   C3   C6     0.00   0.0  0
 8O1  CONST_06  C2    C9   C4   C7     0.00   0.0  0
 8O1  CONST_07  C2    C1   C8   C7     0.00   0.0  0
 8O1  CONST_08  C9    C4   C7   C8     0.00   0.0  0
 8O1  CONST_09  C9    C2   C1   C8     0.00   0.0  0
 8O1  CONST_10  C3    C5   N21  C10    0.00   0.0  0
 8O1  CONST_11  N21   C10  C6   C3     0.00   0.0  0
 8O1  CONST_12  C12   C7   C8   C1   180.00   0.0  0
 8O1  CONST_13  C12   C7   C4   C9   180.00   0.0  0
 8O1  CONST_14  C11   N22  C13  C10    0.00   0.0  0
 8O1  CONST_15  N23   C8   C7   C4   180.00   0.0  0
 8O1  CONST_16  S27   C9   C4   C7   180.00   0.0  0
 8O1  CONST_17  S27   C9   C2   C1   180.00   0.0  0
 8O1  CONST_18  N23   C8   C1   C2   180.00   0.0  0
 8O1  CONST_19  N23   C8   C7   C12    0.00   0.0  0
 8O1  CONST_20  C18   N22  C13  C10  180.00   0.0  0
 8O1  CONST_21  O24   C13  N22  C11  180.00   0.0  0
 8O1  CONST_22  H2    C2   C9   C4   180.00   0.0  0
 8O1  CONST_23  H21   N21  C10  C6   180.00   0.0  0
 8O1  CONST_24  H5    C5   C3   C6   180.00   0.0  0
 8O1  CONST_25  H1    C1   C8   C7   180.00   0.0  0
 8O1  CONST_26  H4    C4   C7   C8   180.00   0.0  0
 8O1  CONST_27  H3    C3   C6   C10  180.00   0.0  0
 8O1  CONST_28  C19   N23  C8   C7   180.00   0.0  0
 8O1  CONST_29  C19   N23  C8   C1     0.00   0.0  0
 8O1  CONST_30  O24   C13  N22  C18    0.00   0.0  0
 8O1  CONST_31  H23   N23  C8   C7     0.00   0.0  0
 8O1  Var_01    C6    C12  C7   C4   -61.38  30.0  2
 8O1  Var_02    C19   C16  C14  C15  109.35  30.0  1
 8O1  Var_03    C20   S27  C9   C4    89.11  30.0  2
 8O1  Var_04    C16   C19  N23  C8   176.37  30.0  2
 8O1  Var_05    N23   C19  C16  C15  145.10  30.0  3
 8O1  Var_06    H183  C18  N22  C13    9.44  30.0  3
 8O1  Var_07    C9    S27  C20  C17  178.51  30.0  3
 8O1  Var_08    H173  C17  C20  S27  -61.87  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
 8O1  chir_01  C16  C15  C14  C19  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
 8O1  plan-1  C4   0.020
 8O1  plan-1  C7   0.020
 8O1  plan-1  C8   0.020
 8O1  plan-1  C1   0.020
 8O1  plan-1  C2   0.020
 8O1  plan-1  C9   0.020
 8O1  plan-1  C12  0.020
 8O1  plan-1  N23  0.020
 8O1  plan-1  S27  0.020
 8O1  plan-1  H4   0.020
 8O1  plan-1  H1   0.020
 8O1  plan-1  H2   0.020
 8O1  plan-2  C5   0.020
 8O1  plan-2  C6   0.020
 8O1  plan-2  C7   0.020
 8O1  plan-2  C10  0.020
 8O1  plan-2  C13  0.020
 8O1  plan-2  C3   0.020
 8O1  plan-2  C11  0.020
 8O1  plan-2  C12  0.020
 8O1  plan-2  N21  0.020
 8O1  plan-2  N22  0.020
 8O1  plan-2  O24  0.020
 8O1  plan-2  H5   0.020
 8O1  plan-2  H3   0.020
 8O1  plan-2  H11  0.020
 8O1  plan-2  H21  0.020
 8O1  plan-2  C18  0.020
 8O1  plan-3  C8   0.020
 8O1  plan-3  C19  0.020
 8O1  plan-3  N23  0.020
 8O1  plan-3  H23  0.020

