# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 00:16:11 2021
#   Inital geometry file: a 131 line input string
#   Ligand name: [2,4-bis(oxidanyl)phenyl]-[(1~{R})-6,7-dimethoxy-1-pyridin-3-yl-3,4-dihydro-1~{H}-isoquinolin-2-yl]methanone
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc2CCN([C@@H](c3cccnc3)c2cc1OC)C(=O)c4ccc(O)cc4O
#
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
 NN8  NN8  '[2,4-bis(oxidanyl)phenyl]-[(1~{R})-6,7-dimethoxy-1-pyridin-3-yl-3,4-dihydro-1~{H}-isoquinolin-2-yl]methanone'  ligand  52  30  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_NN8
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
 NN8  C4   C  CR6   0   0.051  31.7429  -32.5849   7.7110
 NN8  C14  C  CR16  0  -0.093  31.2212  -32.3740  12.5108
 NN8  C5   C  CR6   0   0.091  30.8501  -32.5328   8.7636
 NN8  C6   C  CR16  0  -0.411  29.6291  -31.8655   8.6103
 NN8  C11  C  CR16  0  -0.186  32.0148  -30.8667  10.8563
 NN8  C7   C  CR6   0   0.314  29.2916  -31.2564   7.4198
 NN8  C8   C  CH3   0  -0.439  27.1921  -30.5239   8.2259
 NN8  C9   C  CH1   0  -0.263  31.1479  -33.1518  10.1097
 NN8  C10  C  CR6   0   0.060  31.4680  -32.1062  11.1656
 NN8  C12  C  CR16  0  -0.320  32.3110  -29.9799  11.8801
 NN8  C13  C  CR16  0  -0.072  32.0324  -30.3574  13.1835
 NN8  N1   N  N     0  -0.402  31.4908  -31.5295  13.4971
 NN8  N2   N  NT    0  -0.453  32.2303  -34.1248   9.9785
 NN8  C3   C  CR16  0  -0.433  31.4014  -31.9711   6.4987
 NN8  C1   C  CH3   0  -0.438  30.6726  -30.6987   4.1023
 NN8  C2   C  CR6   0   0.316  30.2002  -31.3107   6.3382
 NN8  O2   O  O2    0  -0.464  28.1415  -30.5988   7.1826
 NN8  C15  C  C     0   0.585  32.1549  -35.2935  10.6459
 NN8  O3   O  O     0  -0.534  31.2728  -35.4867  11.4958
 NN8  C16  C  CR6   0  -0.222  33.1280  -36.3750  10.3778
 NN8  C17  C  CR16  0  -0.255  33.6596  -36.6449   9.1137
 NN8  C18  C  CR16  0  -0.358  34.5366  -37.6822   8.8889
 NN8  C19  C  CR6   0   0.385  34.9115  -38.4964   9.9621
 NN8  O4   O  OH1   0  -0.622  35.7806  -39.4860   9.7154
 NN8  C20  C  CR16  0  -0.478  34.3691  -38.2842  11.2217
 NN8  C21  C  CR6   0   0.368  33.4545  -37.2555  11.4292
 NN8  O5   O  OH1   0  -0.631  32.9242  -37.1408  12.6492
 NN8  C22  C  CH2   0  -0.371  33.3942  -33.5970   9.2849
 NN8  C23  C  CH2   0  -0.502  33.0601  -33.3004   7.8357
 NN8  H13  H  HCR6  0   0.264  30.7803  -33.3220  12.7970
 NN8  H5   H  HCR6  0   0.278  28.9481  -31.8398   9.4516
 NN8  H10  H  HCR6  0   0.275  32.1981  -30.5857   9.8264
 NN8  H8   H  HCH3  0   0.261  26.3424  -29.9716   7.8325
 NN8  H6   H  HCH3  0   0.228  26.8526  -31.5139   8.5425
 NN8  H7   H  HCH3  0   0.228  27.5819  -29.9911   9.0977
 NN8  H9   H  HCH1  0   0.298  30.2602  -33.6925  10.4385
 NN8  H11  H  HCR6  0   0.272  32.7425  -29.0109  11.6701
 NN8  H12  H  HCR6  0   0.265  32.2470  -29.6851  14.0067
 NN8  H4   H  HCR6  0   0.278  32.1115  -32.0223   5.6830
 NN8  H3   H  HCH3  0   0.261  30.1716  -30.1452   3.3119
 NN8  H1   H  HCH3  0   0.228  31.6223  -30.2068   4.3282
 NN8  H2   H  HCH3  0   0.228  30.8766  -31.7123   3.7468
 NN8  H14  H  HCR6  0   0.281  33.3599  -36.0417   8.2676
 NN8  H15  H  HCR6  0   0.268  34.9249  -37.8719   7.8973
 NN8  H16  H  HOH1  0   0.480  35.9570  -39.9933  10.5164
 NN8  H17  H  HCR6  0   0.280  34.6239  -38.9360  12.0504
 NN8  H18  H  HOH1  0   0.475  32.1606  -36.5301  12.5772
 NN8  H20  H  HCH2  0   0.294  34.2371  -34.2754   9.3732
 NN8  H19  H  HCH2  0   0.278  33.6952  -32.6756   9.7922
 NN8  H21  H  HCH2  0   0.260  33.0275  -34.2259   7.2523
 NN8  H22  H  HCH2  0   0.262  33.8609  -32.6986   7.4007
 NN8  O1   O  O2    0  -0.464  29.7987  -30.6934   5.2127

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
 NN8  C1   O1   single    1.413  0.020  1.413
 NN8  O1   C2   single    1.345  0.020  1.345
 NN8  C2   C3   aromatic  1.380  0.020  1.380
 NN8  C2   C7   aromatic  1.414  0.020  1.414
 NN8  C3   C4   aromatic  1.401  0.020  1.401
 NN8  O2   C7   single    1.346  0.020  1.346
 NN8  O2   C8   single    1.413  0.020  1.413
 NN8  C7   C6   aromatic  1.379  0.020  1.379
 NN8  C4   C23  single    1.504  0.020  1.504
 NN8  C4   C5   aromatic  1.381  0.020  1.381
 NN8  C23  C22  single    1.516  0.020  1.516
 NN8  C6   C5   aromatic  1.400  0.020  1.400
 NN8  C5   C9   single    1.511  0.020  1.511
 NN8  C18  C17  aromatic  1.377  0.020  1.377
 NN8  C18  C19  aromatic  1.398  0.020  1.398
 NN8  C17  C16  aromatic  1.398  0.020  1.398
 NN8  C22  N2   single    1.454  0.020  1.454
 NN8  O4   C19  single    1.340  0.020  1.340
 NN8  C19  C20  aromatic  1.388  0.020  1.388
 NN8  N2   C9   single    1.461  0.020  1.461
 NN8  N2   C15  single    1.348  0.020  1.348
 NN8  C9   C10  single    1.520  0.020  1.520
 NN8  C16  C15  single    1.479  0.020  1.479
 NN8  C16  C21  aromatic  1.410  0.020  1.410
 NN8  C15  O3   double    1.240  0.020  1.240
 NN8  C11  C10  aromatic  1.390  0.020  1.390
 NN8  C11  C12  aromatic  1.387  0.020  1.387
 NN8  C10  C14  aromatic  1.394  0.020  1.394
 NN8  C20  C21  aromatic  1.392  0.020  1.392
 NN8  C21  O5   single    1.335  0.020  1.335
 NN8  C12  C13  aromatic  1.385  0.020  1.385
 NN8  C14  N1   aromatic  1.326  0.020  1.326
 NN8  C13  N1   aromatic  1.329  0.020  1.329
 NN8  C14  H13  single    0.930  0.020  1.080
 NN8  C6   H5   single    0.930  0.020  1.080
 NN8  C11  H10  single    0.930  0.020  1.080
 NN8  C8   H8   single    0.970  0.020  1.090
 NN8  C8   H6   single    0.970  0.020  1.090
 NN8  C8   H7   single    0.970  0.020  1.090
 NN8  C9   H9   single    0.970  0.020  1.090
 NN8  C12  H11  single    0.930  0.020  1.080
 NN8  C13  H12  single    0.930  0.020  1.080
 NN8  C3   H4   single    0.930  0.020  1.080
 NN8  C1   H3   single    0.970  0.020  1.090
 NN8  C1   H1   single    0.970  0.020  1.090
 NN8  C1   H2   single    0.970  0.020  1.090
 NN8  C17  H14  single    0.930  0.020  1.080
 NN8  C18  H15  single    0.930  0.020  1.080
 NN8  O4   H16  single    0.850  0.020  0.980
 NN8  C20  H17  single    0.930  0.020  1.080
 NN8  O5   H18  single    0.850  0.020  0.980
 NN8  C22  H20  single    0.970  0.020  1.090
 NN8  C22  H19  single    0.970  0.020  1.090
 NN8  C23  H21  single    0.970  0.020  1.090
 NN8  C23  H22  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
 NN8  C23  C4   C3   119.57  3.000
 NN8  C23  C4   C5   121.39  3.000
 NN8  C3   C4   C5   119.03  3.000
 NN8  H13  C14  N1   116.31  3.000
 NN8  H13  C14  C10  119.67  3.000
 NN8  N1   C14  C10  124.02  3.000
 NN8  C9   C5   C6   117.69  3.000
 NN8  C9   C5   C4   122.41  3.000
 NN8  C6   C5   C4   119.89  3.000
 NN8  H5   C6   C7   120.42  3.000
 NN8  H5   C6   C5   118.35  3.000
 NN8  C7   C6   C5   121.23  3.000
 NN8  H10  C11  C12  120.00  3.000
 NN8  H10  C11  C10  120.64  3.000
 NN8  C12  C11  C10  119.35  3.000
 NN8  O2   C7   C2   115.67  3.000
 NN8  O2   C7   C6   125.24  3.000
 NN8  C2   C7   C6   119.09  3.000
 NN8  H7   C8   H6   108.73  3.000
 NN8  H7   C8   H8   108.64  3.000
 NN8  H6   C8   H8   108.79  3.000
 NN8  H7   C8   O2   112.02  3.000
 NN8  H6   C8   O2   111.99  3.000
 NN8  H8   C8   O2   106.56  3.000
 NN8  H9   C9   N2   107.46  3.000
 NN8  H9   C9   C10  107.65  3.000
 NN8  N2   C9   C10  111.37  3.000
 NN8  H9   C9   C5   108.14  3.000
 NN8  C10  C9   C5   112.24  3.000
 NN8  N2   C9   C5   109.80  3.000
 NN8  C9   C10  C11  122.81  3.000
 NN8  C11  C10  C14  117.13  3.000
 NN8  C9   C10  C14  120.07  3.000
 NN8  H11  C12  C13  120.48  3.000
 NN8  H11  C12  C11  121.00  3.000
 NN8  C13  C12  C11  118.52  3.000
 NN8  H12  C13  N1   116.65  3.000
 NN8  H12  C13  C12  120.37  3.000
 NN8  N1   C13  C12  122.98  3.000
 NN8  C13  N1   C14  117.98  3.000
 NN8  C22  N2   C15  126.56  3.000
 NN8  C15  N2   C9   119.43  3.000
 NN8  C22  N2   C9   113.21  3.000
 NN8  H4   C3   C2   120.39  3.000
 NN8  H4   C3   C4   118.12  3.000
 NN8  C2   C3   C4   121.49  3.000
 NN8  H2   C1   H1   108.79  3.000
 NN8  H2   C1   H3   108.76  3.000
 NN8  H1   C1   H3   108.76  3.000
 NN8  H2   C1   O1   111.99  3.000
 NN8  H1   C1   O1   111.92  3.000
 NN8  H3   C1   O1   106.52  3.000
 NN8  O1   C2   C3   125.22  3.000
 NN8  C3   C2   C7   119.26  3.000
 NN8  O1   C2   C7   115.52  3.000
 NN8  C8   O2   C7   118.04  3.000
 NN8  C16  C15  O3   118.57  3.000
 NN8  O3   C15  N2   120.95  3.000
 NN8  C16  C15  N2   120.48  3.000
 NN8  C21  C16  C17  117.76  3.000
 NN8  C21  C16  C15  118.28  3.000
 NN8  C17  C16  C15  123.73  3.000
 NN8  H14  C17  C18  117.97  3.000
 NN8  H14  C17  C16  119.64  3.000
 NN8  C18  C17  C16  122.38  3.000
 NN8  H15  C18  C19  120.34  3.000
 NN8  H15  C18  C17  120.70  3.000
 NN8  C19  C18  C17  118.96  3.000
 NN8  C20  C19  O4   122.24  3.000
 NN8  C20  C19  C18  120.19  3.000
 NN8  O4   C19  C18  117.56  3.000
 NN8  H16  O4   C19  110.75  3.000
 NN8  H17  C20  C21  118.98  3.000
 NN8  H17  C20  C19  120.65  3.000
 NN8  C21  C20  C19  120.33  3.000
 NN8  O5   C21  C20  117.43  3.000
 NN8  O5   C21  C16  122.40  3.000
 NN8  C20  C21  C16  120.17  3.000
 NN8  H18  O5   C21  107.20  3.000
 NN8  H19  C22  H20  105.96  3.000
 NN8  H19  C22  C23  109.81  3.000
 NN8  H20  C22  C23  111.78  3.000
 NN8  H19  C22  N2   107.74  3.000
 NN8  H20  C22  N2   110.85  3.000
 NN8  C23  C22  N2   110.52  3.000
 NN8  H22  C23  H21  105.99  3.000
 NN8  H22  C23  C22  109.08  3.000
 NN8  H21  C23  C22  110.52  3.000
 NN8  H22  C23  C4   110.31  3.000
 NN8  H21  C23  C4   109.38  3.000
 NN8  C22  C23  C4   111.42  3.000
 NN8  C2   O1   C1   118.12  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
 NN8  CONST_01  C7   C2   C3   C4      0.00   0.0  0
 NN8  CONST_02  C7   C6   C5   C4      0.00   0.0  0
 NN8  CONST_03  C12  C11  C10  C14     0.00   0.0  0
 NN8  CONST_04  C12  C13  N1   C14     0.00   0.0  0
 NN8  CONST_05  C2   C3   C4   C5      0.00   0.0  0
 NN8  CONST_06  C2   C7   C6   C5      0.00   0.0  0
 NN8  CONST_07  C3   C2   C7   C6      0.00   0.0  0
 NN8  CONST_08  C3   C4   C5   C6      0.00   0.0  0
 NN8  CONST_09  N1   C14  C10  C11     0.00   0.0  0
 NN8  CONST_10  N1   C13  C12  C11     0.00   0.0  0
 NN8  CONST_11  C13  C12  C11  C10     0.00   0.0  0
 NN8  CONST_12  C13  N1   C14  C10     0.00   0.0  0
 NN8  CONST_13  C19  C18  C17  C16     0.00   0.0  0
 NN8  CONST_14  C19  C20  C21  C16     0.00   0.0  0
 NN8  CONST_15  C20  C19  C18  C17     0.00   0.0  0
 NN8  CONST_16  C20  C21  C16  C17     0.00   0.0  0
 NN8  CONST_17  C21  C16  C17  C18     0.00   0.0  0
 NN8  CONST_18  C21  C20  C19  C18     0.00   0.0  0
 NN8  CONST_19  C12  C11  C10  C9    180.00   0.0  0
 NN8  CONST_20  N1   C14  C10  C9    180.00   0.0  0
 NN8  CONST_21  O1   C2   C3   C4    180.00   0.0  0
 NN8  CONST_22  O2   C7   C6   C5    180.00   0.0  0
 NN8  CONST_23  O1   C2   C7   C6    180.00   0.0  0
 NN8  CONST_24  O2   C7   C2   C3    180.00   0.0  0
 NN8  CONST_25  C18  C17  C16  C15   180.00   0.0  0
 NN8  CONST_26  C20  C21  C16  C15   180.00   0.0  0
 NN8  CONST_27  O4   C19  C18  C17   180.00   0.0  0
 NN8  CONST_28  O5   C21  C16  C17   180.00   0.0  0
 NN8  CONST_29  O5   C21  C20  C19   180.00   0.0  0
 NN8  CONST_30  C21  C20  C19  O4    180.00   0.0  0
 NN8  CONST_31  C16  C15  N2   C9    180.00   0.0  0
 NN8  CONST_33  H5   C6   C5   C4    180.00   0.0  0
 NN8  CONST_34  H10  C11  C10  C14   180.00   0.0  0
 NN8  CONST_35  H12  C13  N1   C14   180.00   0.0  0
 NN8  CONST_36  H4   C3   C4   C5    180.00   0.0  0
 NN8  CONST_37  H13  C14  C10  C11   180.00   0.0  0
 NN8  CONST_38  H11  C12  C11  C10   180.00   0.0  0
 NN8  CONST_39  H15  C18  C17  C16   180.00   0.0  0
 NN8  CONST_40  H17  C20  C21  C16   180.00   0.0  0
 NN8  CONST_41  H14  C17  C18  C19   180.00   0.0  0
 NN8  CONST_42  O3   C15  N2   C9      0.00   0.0  0
 NN8  Var_01    N2   C22  C23  C4     44.97  30.0  1
 NN8  Var_02    C22  C23  C4   C5    -14.71  30.0  1
 NN8  Var_03    C23  C22  N2   C9    -66.31  30.0  1
 NN8  Var_04    C17  C16  C15  N2    -35.52  30.0  2
 NN8  Var_05    C2   C7   O2   C8    179.46  30.0  2
 NN8  Var_06    H8   C8   O2   C7   -179.26  30.0  3
 NN8  Var_07    H3   C1   O1   C2   -179.35  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
 NN8  chir_01  C9  C5  N2  C10  negativ

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
 NN8  plan-1  C14  0.020
 NN8  plan-1  C11  0.020
 NN8  plan-1  C9   0.020
 NN8  plan-1  C10  0.020
 NN8  plan-1  C12  0.020
 NN8  plan-1  C13  0.020
 NN8  plan-1  N1   0.020
 NN8  plan-1  H13  0.020
 NN8  plan-1  H10  0.020
 NN8  plan-1  H11  0.020
 NN8  plan-1  H12  0.020
 NN8  plan-2  C15  0.020
 NN8  plan-2  C16  0.020
 NN8  plan-2  C17  0.020
 NN8  plan-2  C18  0.020
 NN8  plan-2  C19  0.020
 NN8  plan-2  O4   0.020
 NN8  plan-2  C20  0.020
 NN8  plan-2  C21  0.020
 NN8  plan-2  O5   0.020
 NN8  plan-2  H14  0.020
 NN8  plan-2  H15  0.020
 NN8  plan-2  H17  0.020
 NN8  plan-3  C4   0.020
 NN8  plan-3  C5   0.020
 NN8  plan-3  C6   0.020
 NN8  plan-3  C7   0.020
 NN8  plan-3  C9   0.020
 NN8  plan-3  C3   0.020
 NN8  plan-3  C2   0.020
 NN8  plan-3  O2   0.020
 NN8  plan-3  C23  0.020
 NN8  plan-3  H5   0.020
 NN8  plan-3  H4   0.020
 NN8  plan-3  O1   0.020
 NN8  plan-4  C9   0.020
 NN8  plan-4  N2   0.020
 NN8  plan-4  C15  0.020
 NN8  plan-4  O3   0.020
 NN8  plan-4  C16  0.020
 NN8  plan-4  C22  0.020

