# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr 15 12:58:49 2020
#   Inital geometry file: a 104 line input string
#   Ligand name: 4-(2-chlorophenyl)-8-(2-hydroxyethyl)-6-methylpyrrolo[3,4-e]indole-1,3(2H,6H)-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cn1cc(CCO)c2c1cc(c3ccccc3Cl)c4C(=O)NC(=O)c24
#
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
 809  809  4-(2-chlorophenyl)-8-(2-hydroxyethyl)-6-methylpyrrolo[3,4-e]indole-1,3(2H,6H)-dione  ligand  40  25  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_809
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
 809  O1    O   O     0  -0.396  -2.5446   2.6271   0.0862
 809  C5    C   CR5   0   0.524  -1.4454   2.1526  -0.0608
 809  N1    N   NR15  0  -0.741  -0.2963   2.8770  -0.2998
 809  C6    C   CR5   0   0.551   0.8250   2.0802  -0.4304
 809  O2    O   O     0  -0.396   1.9372   2.4774  -0.6712
 809  C3    C   CR56  0  -0.124   0.3493   0.6910  -0.2310
 809  C4    C   CR56  0  -0.144  -1.0220   0.7285  -0.0299
 809  C13   C   CR56  0   0.102  -1.7499  -0.4465   0.1521
 809  C15   C   CR5   0  -0.053  -3.1075  -0.8295   0.3906
 809  C17   C   CH2   0  -0.562  -4.3372   0.0121   0.5033
 809  C19   C   CH2   0  -0.136  -4.8719   0.4199  -0.8616
 809  O3    O   OH1   0  -0.674  -6.0178   1.2217  -0.6716
 809  C16   C   CR15  0  -0.058  -3.0907  -2.1953   0.4720
 809  N2    N   NR5   0  -0.527  -1.8312  -2.6910   0.3016
 809  C18   C   CH3   0  -0.534  -1.4529  -4.0841   0.3390
 809  C14   C   CR56  0   0.396  -0.9838  -1.6488   0.1032
 809  C1    C   CR16  0  -0.359   0.3927  -1.6850  -0.0988
 809  C2    C   CR6   0   0.040   1.0867  -0.4949  -0.2617
 809  C7    C   CR6   0   0.141   2.5517  -0.5281  -0.4641
 809  C12   C   CR16  0  -0.309   3.0793  -1.0990  -1.6198
 809  C8    C   CR6   0  -0.099   3.4471  -0.0498   0.4900
 809  CL1   CL  CL    0  -0.130   2.8490   0.6266   1.9688
 809  C9    C   CR16  0  -0.200   4.8179  -0.1216   0.3028
 809  C10   C   CR16  0  -0.273   5.3184  -0.6850  -0.8623
 809  C11   C   CR16  0  -0.232   4.4490  -1.1775  -1.8239
 809  HN1   H   HNR5  0   0.424  -0.2805   3.8834  -0.3864
 809  H17   H   HCH2  0   0.242  -5.1074  -0.5563   1.0310
 809  H17A  H   HCH2  0   0.243  -4.1351   0.9045   1.0964
 809  H19   H   HCH2  0   0.195  -4.0922   0.9559  -1.4162
 809  H19A  H   HCH2  0   0.190  -5.1067  -0.4866  -1.4349
 809  HO3   H   HOH1  0   0.453  -6.3786   1.4395  -1.5354
 809  H16   H   HCR5  0   0.298  -3.9189  -2.8661   0.6460
 809  H18   H   HCH3  0   0.260  -1.0338  -4.3981  -0.6159
 809  H18A  H   HCH3  0   0.260  -0.7202  -4.2656   1.1246
 809  H18B  H   HCH3  0   0.271  -2.3347  -4.6839   0.5440
 809  H1    H   HCR6  0   0.280   0.9283  -2.6263  -0.1153
 809  H12   H   HCR6  0   0.262   2.4000  -1.4793  -2.3723
 809  H9    H   HCR6  0   0.280   5.4898   0.2535   1.0629
 809  H10   H   HCR6  0   0.269   6.3886  -0.7405  -1.0105
 809  H11   H   HCR6  0   0.265   4.8333  -1.6216  -2.7321

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
 809  O1   C5    double    1.206  0.020  1.206
 809  C5   N1    single    1.379  0.020  1.379
 809  C5   C4    single    1.486  0.020  1.486
 809  N1   C6    single    1.382  0.020  1.382
 809  C6   O2    double    1.205  0.020  1.205
 809  C6   C3    single    1.482  0.020  1.482
 809  C3   C4    aromatic  1.386  0.020  1.386
 809  C3   C2    aromatic  1.397  0.020  1.397
 809  C4   C13   aromatic  1.394  0.020  1.394
 809  C13  C15   aromatic  1.431  0.020  1.431
 809  C13  C14   aromatic  1.426  0.020  1.426
 809  C15  C17   single    1.494  0.020  1.494
 809  C15  C16   aromatic  1.368  0.020  1.368
 809  C17  C19   single    1.522  0.020  1.522
 809  C19  O3    single    1.411  0.020  1.411
 809  C16  N2    aromatic  1.364  0.020  1.364
 809  N2   C18   single    1.444  0.020  1.444
 809  N2   C14   aromatic  1.358  0.020  1.358
 809  C14  C1    aromatic  1.392  0.020  1.392
 809  C1   C2    aromatic  1.387  0.020  1.387
 809  C2   C7    single    1.479  0.020  1.479
 809  C7   C12   aromatic  1.393  0.020  1.393
 809  C7   C8    aromatic  1.393  0.020  1.393
 809  C12  C11   aromatic  1.387  0.020  1.387
 809  C8   CL1   single    1.733  0.020  1.733
 809  C8   C9    aromatic  1.385  0.020  1.385
 809  C9   C10   aromatic  1.388  0.020  1.388
 809  C10  C11   aromatic  1.387  0.020  1.387
 809  N1   HN1   single    0.860  0.020  1.020
 809  C17  H17   single    0.970  0.020  1.090
 809  C17  H17A  single    0.970  0.020  1.090
 809  C19  H19   single    0.970  0.020  1.090
 809  C19  H19A  single    0.970  0.020  1.090
 809  O3   HO3   single    0.850  0.020  0.980
 809  C16  H16   single    0.930  0.020  1.080
 809  C18  H18   single    0.970  0.020  1.090
 809  C18  H18A  single    0.970  0.020  1.090
 809  C18  H18B  single    0.970  0.020  1.090
 809  C1   H1    single    0.930  0.020  1.080
 809  C12  H12   single    0.930  0.020  1.080
 809  C9   H9    single    0.930  0.020  1.080
 809  C10  H10   single    0.930  0.020  1.080
 809  C11  H11   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
 809  C4    C5   N1    105.64  3.000
 809  C4    C5   O1    129.35  3.000
 809  N1    C5   O1    125.01  3.000
 809  HN1   N1   C6    123.62  3.000
 809  HN1   N1   C5    123.44  3.000
 809  C6    N1   C5    112.93  3.000
 809  C3    C6   O2    129.20  3.000
 809  C3    C6   N1    105.51  3.000
 809  O2    C6   N1    125.29  3.000
 809  C2    C3   C4    123.25  3.000
 809  C2    C3   C6    128.57  3.000
 809  C4    C3   C6    108.16  3.000
 809  C13   C4   C3    120.83  3.000
 809  C13   C4   C5    131.43  3.000
 809  C3    C4   C5    107.74  3.000
 809  C14   C13  C15   106.84  3.000
 809  C14   C13  C4    115.18  3.000
 809  C15   C13  C4    137.98  3.000
 809  C16   C15  C17   124.59  3.000
 809  C16   C15  C13   105.40  3.000
 809  C17   C15  C13   130.00  3.000
 809  H17A  C17  H17   107.08  3.000
 809  H17A  C17  C19   109.50  3.000
 809  H17   C17  C19   108.96  3.000
 809  H17A  C17  C15   110.45  3.000
 809  H17   C17  C15   108.87  3.000
 809  C19   C17  C15   111.87  3.000
 809  H19A  C19  H19   106.95  3.000
 809  H19A  C19  O3    111.45  3.000
 809  H19   C19  O3    111.57  3.000
 809  H19A  C19  C17   108.80  3.000
 809  H19   C19  C17   109.56  3.000
 809  O3    C19  C17   108.47  3.000
 809  HO3   O3   C19   108.21  3.000
 809  H16   C16  N2    120.16  3.000
 809  H16   C16  C15   128.33  3.000
 809  N2    C16  C15   111.50  3.000
 809  C14   N2   C18   125.51  3.000
 809  C14   N2   C16   108.39  3.000
 809  C18   N2   C16   126.10  3.000
 809  H18B  C18  H18A  108.54  3.000
 809  H18B  C18  H18   108.59  3.000
 809  H18A  C18  H18   108.99  3.000
 809  H18B  C18  N2    108.96  3.000
 809  H18A  C18  N2    110.83  3.000
 809  H18   C18  N2    110.87  3.000
 809  C1    C14  N2    128.20  3.000
 809  C1    C14  C13   123.93  3.000
 809  N2    C14  C13   107.87  3.000
 809  H1    C1   C2    119.76  3.000
 809  H1    C1   C14   120.93  3.000
 809  C2    C1   C14   119.31  3.000
 809  C7    C2   C1    119.48  3.000
 809  C7    C2   C3    123.02  3.000
 809  C1    C2   C3    117.50  3.000
 809  C8    C7   C12   117.74  3.000
 809  C8    C7   C2    122.35  3.000
 809  C12   C7   C2    119.86  3.000
 809  H12   C12  C11   119.83  3.000
 809  H12   C12  C7    118.88  3.000
 809  C11   C12  C7    121.29  3.000
 809  C9    C8   CL1   118.50  3.000
 809  C9    C8   C7    121.71  3.000
 809  CL1   C8   C7    119.78  3.000
 809  H9    C9   C10   120.45  3.000
 809  H9    C9   C8    120.12  3.000
 809  C10   C9   C8    119.43  3.000
 809  H10   C10  C11   120.46  3.000
 809  H10   C10  C9    119.52  3.000
 809  C11   C10  C9    120.02  3.000
 809  H11   C11  C10   120.35  3.000
 809  H11   C11  C12   119.85  3.000
 809  C10   C11  C12   119.80  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
 809  CONST_01  C15  C13  C4   C3    180.00   0.0  0
 809  CONST_02  C14  C13  C4   C3      0.00   0.0  0
 809  CONST_03  C14  C1   C2   C3      0.00   0.0  0
 809  CONST_06  C1   C2   C3   C4      0.00   0.0  0
 809  CONST_07  C7   C2   C3   C4    180.00   0.0  0
 809  CONST_08  C16  C15  C13  C4    180.00   0.0  0
 809  CONST_09  N2   C14  C13  C4    180.00   0.0  0
 809  CONST_10  C1   C14  C13  C4      0.00   0.0  0
 809  CONST_11  C2   C3   C4   C13     0.00   0.0  0
 809  CONST_12  N2   C16  C15  C13     0.00   0.0  0
 809  CONST_13  C16  N2   C14  C13     0.00   0.0  0
 809  CONST_14  C2   C1   C14  C13     0.00   0.0  0
 809  CONST_15  N2   C14  C13  C15     0.00   0.0  0
 809  CONST_16  C1   C14  C13  C15   180.00   0.0  0
 809  CONST_17  C14  N2   C16  C15     0.00   0.0  0
 809  CONST_18  C14  C13  C15  C16     0.00   0.0  0
 809  CONST_19  C1   C14  N2   C16   180.00   0.0  0
 809  CONST_20  C2   C1   C14  N2    180.00   0.0  0
 809  CONST_21  C7   C2   C1   C14   180.00   0.0  0
 809  CONST_24  C11  C12  C7   C2    180.00   0.0  0
 809  CONST_25  C9   C8   C7   C2    180.00   0.0  0
 809  CONST_26  C10  C11  C12  C7      0.00   0.0  0
 809  CONST_27  C10  C9   C8   C7      0.00   0.0  0
 809  CONST_28  C9   C8   C7   C12     0.00   0.0  0
 809  CONST_29  C9   C10  C11  C12     0.00   0.0  0
 809  CONST_30  C11  C12  C7   C8      0.00   0.0  0
 809  CONST_31  C11  C10  C9   C8      0.00   0.0  0
 809  CONST_32  C7   C2   C3   C6      0.00   0.0  0
 809  CONST_33  C4   C5   N1   C6      0.00   0.0  0
 809  CONST_34  C17  C15  C13  C4      0.00   0.0  0
 809  CONST_35  C18  N2   C14  C13   180.00   0.0  0
 809  CONST_36  C18  N2   C16  C15   180.00   0.0  0
 809  CONST_37  C14  C13  C15  C17   180.00   0.0  0
 809  CONST_38  N2   C16  C15  C17   180.00   0.0  0
 809  CONST_39  C1   C14  N2   C18     0.00   0.0  0
 809  CONST_40  CL1  C8   C7   C2      0.00   0.0  0
 809  CONST_41  CL1  C8   C7   C12   180.00   0.0  0
 809  CONST_42  C10  C9   C8   CL1   180.00   0.0  0
 809  CONST_43  C6   N1   C5   O1    180.00   0.0  0
 809  CONST_44  H1   C1   C2   C3    180.00   0.0  0
 809  CONST_45  H16  C16  C15  C13   180.00   0.0  0
 809  CONST_46  H12  C12  C7   C2      0.00   0.0  0
 809  CONST_47  H11  C11  C12  C7    180.00   0.0  0
 809  CONST_48  H9   C9   C8   C7    180.00   0.0  0
 809  CONST_49  H10  C10  C11  C12   180.00   0.0  0
 809  CONST_50  HN1  N1   C5   C4    180.00   0.0  0
 809  Var_01    C19  C17  C15  C13    79.69  30.0  2
 809  Var_02    H18  C18  N2   C16   118.45  30.0  2
 809  Var_03    O3   C19  C17  C15  -179.29  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
 809  plan-1  C2   0.020
 809  plan-1  C7   0.020
 809  plan-1  C12  0.020
 809  plan-1  C8   0.020
 809  plan-1  CL1  0.020
 809  plan-1  C9   0.020
 809  plan-1  C10  0.020
 809  plan-1  C11  0.020
 809  plan-1  H12  0.020
 809  plan-1  H9   0.020
 809  plan-1  H10  0.020
 809  plan-1  H11  0.020
 809  plan-2  O1   0.020
 809  plan-2  C5   0.020
 809  plan-2  N1   0.020
 809  plan-2  C6   0.020
 809  plan-2  O2   0.020
 809  plan-2  C3   0.020
 809  plan-2  C4   0.020
 809  plan-2  C13  0.020
 809  plan-2  C15  0.020
 809  plan-2  C17  0.020
 809  plan-2  C16  0.020
 809  plan-2  N2   0.020
 809  plan-2  C18  0.020
 809  plan-2  C14  0.020
 809  plan-2  C1   0.020
 809  plan-2  C2   0.020
 809  plan-2  C7   0.020
 809  plan-2  HN1  0.020
 809  plan-2  H16  0.020
 809  plan-2  H1   0.020

