# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr  1 03:26:36 2020
#   Inital geometry file: a 150 line input string
#   Ligand name: 3-chloro-5-({6-[2-(3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]-3-(dimethylamino)-2-oxo-1,2-dihydropyridin-4-yl}oxy)benzonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CN(C)C1=C(Oc2cc(Cl)cc(c2)C#N)C=C(CC(=O)N3CCc4ccccc4C3)NC1=O
#
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
 3OB  3OB  3-chloro-5-({6-[2-(3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]-3-(dimethylamino)-2-oxo-1,2-dihydropyridin-4-yl}oxy)benzonitrile  ligand  56  33  .  2021-08-04  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_3OB
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
 3OB  C1    C   CR6   0   0.007  -6.2289   0.7550  -0.5056
 3OB  C2    C   CR16  0  -0.226  -6.0878   1.2911   0.7718
 3OB  C3    C   CR6   0  -0.021  -4.8067   1.4155   1.2797
 3OB  C4    C   CR16  0  -0.255  -3.6920   1.0254   0.5584
 3OB  C5    C   CR6   0   0.416  -3.8689   0.4631  -0.6995
 3OB  C6    C   CR16  0  -0.316  -5.1322   0.3345  -1.2507
 3OB  O7    O   O2    0  -0.504  -2.8080   0.1221  -1.4794
 3OB  C8    C   CSP   0   0.065  -7.5383   0.6262  -1.0630
 3OB  CL9   CL  CL    0  -0.102  -4.5892   2.0827   2.8576
 3OB  C10   C   CR6   0   0.456  -1.7328  -0.5037  -0.9322
 3OB  C11   C   CR16  0  -0.517  -0.4693  -0.0189  -1.3372
 3OB  C12   C   CR6   0   0.471   0.6388  -0.6277  -0.8446
 3OB  N13   N   NR16  0  -0.709   0.5012  -1.6789  -0.0052
 3OB  C14   C   CR6   0   0.518  -0.6945  -2.2328   0.4134
 3OB  C15   C   CR6   0  -0.024  -1.8790  -1.5752  -0.0892
 3OB  N16   N   NT    0  -0.463  -3.1619  -2.0476   0.2167
 3OB  O17   O   O     0  -0.497  -0.6945  -3.2154   1.1493
 3OB  C18   C   CH3   0  -0.514  -3.6355  -3.1448  -0.5971
 3OB  C19   C   CH3   0  -0.510  -3.5244  -2.1469   1.6125
 3OB  C20   C   CH2   0  -0.727   2.0273  -0.1920  -1.1754
 3OB  N21   N   NS    0  -0.242  -8.5937   0.5232  -1.5118
 3OB  C22   C   C     0   0.585   2.6059   0.6704  -0.0567
 3OB  O23   O   O     0  -0.480   1.9614   0.8712   0.9604
 3OB  N24   N   NT    0  -0.457   3.8229   1.2075  -0.2671
 3OB  C25   C   CH2   0  -0.357   4.7164   0.8587  -1.3498
 3OB  C26   C   CH2   0  -0.497   5.4803   1.0334   1.4933
 3OB  C27   C   CH2   0  -0.348   4.4939   1.9495   0.7862
 3OB  C28   C   CR6   0   0.082   6.3291   0.2691   0.5082
 3OB  C29   C   CR6   0   0.043   5.9596   0.1711  -0.8341
 3OB  C30   C   CR16  0  -0.298   6.7585  -0.5455  -1.7222
 3OB  C31   C   CR16  0  -0.271   7.9178  -1.1691  -1.2901
 3OB  C32   C   CR16  0  -0.263   8.2889  -1.0767   0.0466
 3OB  C33   C   CR16  0  -0.309   7.4974  -0.3633   0.9324
 3OB  H2    H   HCR6  0   0.302  -6.9510   1.6027   1.3420
 3OB  H4    H   HCR6  0   0.314  -2.7010   1.1470   0.9763
 3OB  H6    H   HCR6  0   0.296  -5.2613  -0.0926  -2.2358
 3OB  H11   H   HCR6  0   0.284  -0.3874   0.8233  -2.0084
 3OB  HN13  H   HNR6  0   0.417   1.3375  -2.1310   0.3418
 3OB  H18   H   HCH3  0   0.210  -3.2047  -4.1141  -0.3142
 3OB  H18A  H   HCH3  0   0.229  -4.7213  -3.2215  -0.5062
 3OB  H18B  H   HCH3  0   0.237  -3.4064  -2.9630  -1.6468
 3OB  H19   H   HCH3  0   0.231  -3.0947  -1.3171   2.1733
 3OB  H19A  H   HCH3  0   0.228  -4.6108  -2.0754   1.7052
 3OB  H19B  H   HCH3  0   0.212  -3.2047  -3.0806   2.0877
 3OB  H20   H   HCH2  0   0.310   2.6614  -1.0673  -1.3454
 3OB  H20A  H   HCH2  0   0.321   2.0155   0.3669  -2.1125
 3OB  H25   H   HCH2  0   0.283   4.2161   0.2275  -2.0803
 3OB  H25A  H   HCH2  0   0.273   4.9994   1.7742  -1.8803
 3OB  H26   H   HCH2  0   0.253   6.1178   1.6195   2.1590
 3OB  H26A  H   HCH2  0   0.264   4.9331   0.3299   2.1281
 3OB  H27   H   HCH2  0   0.266   5.0190   2.7869   0.3199
 3OB  H27A  H   HCH2  0   0.280   3.7660   2.3630   1.4789
 3OB  H30   H   HCR6  0   0.266   6.4639  -0.6184  -2.7631
 3OB  H31   H   HCR6  0   0.263   8.5260  -1.7276  -1.9897
 3OB  H32   H   HCR6  0   0.261   9.1933  -1.5579   0.3960
 3OB  H33   H   HCR6  0   0.263   7.7888  -0.2888   1.9740

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
 3OB  C1   C2    aromatic  1.393  0.020  1.393
 3OB  C1   C6    aromatic  1.391  0.020  1.391
 3OB  C1   C8    single    1.429  0.020  1.429
 3OB  C2   C3    aromatic  1.384  0.020  1.384
 3OB  C3   C4    aromatic  1.384  0.020  1.384
 3OB  C3   CL9   single    1.727  0.020  1.727
 3OB  C4   C5    aromatic  1.389  0.020  1.389
 3OB  C5   C6    aromatic  1.384  0.020  1.384
 3OB  C5   O7    single    1.360  0.020  1.360
 3OB  O7   C10   single    1.359  0.020  1.359
 3OB  C8   N21   triple    1.152  0.020  1.152
 3OB  C10  C11   single    1.413  0.020  1.413
 3OB  C10  C15   double    1.371  0.020  1.371
 3OB  C11  C12   double    1.357  0.020  1.357
 3OB  C12  N13   single    1.352  0.020  1.352
 3OB  C12  C20   single    1.492  0.020  1.492
 3OB  N13  C14   single    1.383  0.020  1.383
 3OB  C14  C15   single    1.445  0.020  1.445
 3OB  C14  O17   double    1.228  0.020  1.228
 3OB  C15  N16   single    1.401  0.020  1.401
 3OB  N16  C18   single    1.446  0.020  1.446
 3OB  N16  C19   single    1.445  0.020  1.445
 3OB  C20  C22   single    1.526  0.020  1.526
 3OB  C22  O23   double    1.221  0.020  1.221
 3OB  C22  N24   single    1.347  0.020  1.347
 3OB  N24  C25   single    1.446  0.020  1.446
 3OB  N24  C27   single    1.453  0.020  1.453
 3OB  C25  C29   single    1.511  0.020  1.511
 3OB  C26  C27   single    1.521  0.020  1.521
 3OB  C26  C28   single    1.508  0.020  1.508
 3OB  C28  C29   aromatic  1.396  0.020  1.396
 3OB  C28  C33   aromatic  1.395  0.020  1.395
 3OB  C29  C30   aromatic  1.393  0.020  1.393
 3OB  C30  C31   aromatic  1.385  0.020  1.385
 3OB  C31  C32   aromatic  1.390  0.020  1.390
 3OB  C32  C33   aromatic  1.386  0.020  1.386
 3OB  C2   H2    single    0.930  0.020  1.080
 3OB  C4   H4    single    0.930  0.020  1.080
 3OB  C6   H6    single    0.930  0.020  1.080
 3OB  C11  H11   single    0.930  0.020  1.080
 3OB  N13  HN13  single    0.860  0.020  1.020
 3OB  C18  H18   single    0.970  0.020  1.090
 3OB  C18  H18A  single    0.970  0.020  1.090
 3OB  C18  H18B  single    0.970  0.020  1.090
 3OB  C19  H19   single    0.970  0.020  1.090
 3OB  C19  H19A  single    0.970  0.020  1.090
 3OB  C19  H19B  single    0.970  0.020  1.090
 3OB  C20  H20   single    0.970  0.020  1.090
 3OB  C20  H20A  single    0.970  0.020  1.090
 3OB  C25  H25   single    0.970  0.020  1.090
 3OB  C25  H25A  single    0.970  0.020  1.090
 3OB  C26  H26   single    0.970  0.020  1.090
 3OB  C26  H26A  single    0.970  0.020  1.090
 3OB  C27  H27   single    0.970  0.020  1.090
 3OB  C27  H27A  single    0.970  0.020  1.090
 3OB  C30  H30   single    0.930  0.020  1.080
 3OB  C31  H31   single    0.930  0.020  1.080
 3OB  C32  H32   single    0.930  0.020  1.080
 3OB  C33  H33   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
 3OB  C8    C1   C6    119.10  3.000
 3OB  C8    C1   C2    119.04  3.000
 3OB  C6    C1   C2    121.86  3.000
 3OB  H2    C2   C3    121.34  3.000
 3OB  H2    C2   C1    120.94  3.000
 3OB  C3    C2   C1    117.72  3.000
 3OB  CL9   C3   C4    118.93  3.000
 3OB  CL9   C3   C2    119.12  3.000
 3OB  C4    C3   C2    121.95  3.000
 3OB  H4    C4   C5    120.77  3.000
 3OB  H4    C4   C3    120.31  3.000
 3OB  C5    C4   C3    118.92  3.000
 3OB  O7    C5   C6    117.40  3.000
 3OB  O7    C5   C4    121.42  3.000
 3OB  C6    C5   C4    120.96  3.000
 3OB  H6    C6   C5    120.55  3.000
 3OB  H6    C6   C1    120.88  3.000
 3OB  C5    C6   C1    118.57  3.000
 3OB  C10   O7   C5    120.11  3.000
 3OB  N21   C8   C1    180.00  3.000
 3OB  C15   C10  C11   122.67  3.000
 3OB  C15   C10  O7    121.53  3.000
 3OB  C11   C10  O7    115.73  3.000
 3OB  H11   C11  C12   120.90  3.000
 3OB  H11   C11  C10   120.90  3.000
 3OB  C12   C11  C10   118.19  3.000
 3OB  C20   C12  N13   117.34  3.000
 3OB  C20   C12  C11   123.25  3.000
 3OB  N13   C12  C11   119.41  3.000
 3OB  HN13  N13  C14   115.59  3.000
 3OB  HN13  N13  C12   118.42  3.000
 3OB  C14   N13  C12   125.97  3.000
 3OB  O17   C14  C15   124.95  3.000
 3OB  O17   C14  N13   120.14  3.000
 3OB  C15   C14  N13   114.91  3.000
 3OB  N16   C15  C14   121.41  3.000
 3OB  N16   C15  C10   119.70  3.000
 3OB  C14   C15  C10   118.82  3.000
 3OB  C19   N16  C18   114.16  3.000
 3OB  C19   N16  C15   117.63  3.000
 3OB  C18   N16  C15   115.65  3.000
 3OB  H18B  C18  H18A  107.50  3.000
 3OB  H18B  C18  H18   108.24  3.000
 3OB  H18A  C18  H18   107.86  3.000
 3OB  H18B  C18  N16   110.29  3.000
 3OB  H18A  C18  N16   109.39  3.000
 3OB  H18   C18  N16   113.36  3.000
 3OB  H19B  C19  H19A  108.01  3.000
 3OB  H19B  C19  H19   108.10  3.000
 3OB  H19A  C19  H19   107.37  3.000
 3OB  H19B  C19  N16   113.84  3.000
 3OB  H19A  C19  N16   109.07  3.000
 3OB  H19   C19  N16   110.22  3.000
 3OB  H20A  C20  H20   106.42  3.000
 3OB  H20A  C20  C22   110.13  3.000
 3OB  H20   C20  C22   110.25  3.000
 3OB  H20A  C20  C12   109.26  3.000
 3OB  H20   C20  C12   109.88  3.000
 3OB  C22   C20  C12   110.80  3.000
 3OB  N24   C22  O23   122.80  3.000
 3OB  N24   C22  C20   116.96  3.000
 3OB  O23   C22  C20   120.23  3.000
 3OB  C27   N24  C25   112.37  3.000
 3OB  C27   N24  C22   120.52  3.000
 3OB  C25   N24  C22   125.38  3.000
 3OB  H25A  C25  H25   106.18  3.000
 3OB  H25A  C25  C29   109.45  3.000
 3OB  H25   C25  C29   110.10  3.000
 3OB  H25A  C25  N24   108.70  3.000
 3OB  H25   C25  N24   111.02  3.000
 3OB  C29   C25  N24   111.25  3.000
 3OB  H26A  C26  H26   106.45  3.000
 3OB  H26A  C26  C28   109.54  3.000
 3OB  H26   C26  C28   109.97  3.000
 3OB  H26A  C26  C27   109.43  3.000
 3OB  H26   C26  C27   109.80  3.000
 3OB  C28   C26  C27   111.51  3.000
 3OB  H27A  C27  H27   107.59  3.000
 3OB  H27A  C27  C26   111.55  3.000
 3OB  H27   C27  C26   110.38  3.000
 3OB  H27A  C27  N24   110.32  3.000
 3OB  H27   C27  N24   107.70  3.000
 3OB  C26   C27  N24   109.21  3.000
 3OB  C33   C28  C29   118.85  3.000
 3OB  C33   C28  C26   120.17  3.000
 3OB  C29   C28  C26   120.98  3.000
 3OB  C30   C29  C28   119.83  3.000
 3OB  C30   C29  C25   119.22  3.000
 3OB  C28   C29  C25   120.93  3.000
 3OB  H30   C30  C31   119.77  3.000
 3OB  H30   C30  C29   119.40  3.000
 3OB  C31   C30  C29   120.83  3.000
 3OB  H31   C31  C32   120.38  3.000
 3OB  H31   C31  C30   120.06  3.000
 3OB  C32   C31  C30   119.56  3.000
 3OB  H32   C32  C33   119.98  3.000
 3OB  H32   C32  C31   120.26  3.000
 3OB  C33   C32  C31   119.75  3.000
 3OB  H33   C33  C32   119.73  3.000
 3OB  H33   C33  C28   119.10  3.000
 3OB  C32   C33  C28   121.17  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
 3OB  CONST_01  C4    C3   C2   C1      0.00   0.0  0
 3OB  CONST_02  C4    C5   C6   C1      0.00   0.0  0
 3OB  CONST_03  C5    C6   C1   C2      0.00   0.0  0
 3OB  CONST_04  C5    C4   C3   C2      0.00   0.0  0
 3OB  CONST_05  C6    C1   C2   C3      0.00   0.0  0
 3OB  CONST_06  C6    C5   C4   C3      0.00   0.0  0
 3OB  CONST_07  C31   C30  C29  C28     0.00   0.0  0
 3OB  CONST_08  C31   C32  C33  C28     0.00   0.0  0
 3OB  CONST_09  C32   C33  C28  C29     0.00   0.0  0
 3OB  CONST_10  C32   C31  C30  C29     0.00   0.0  0
 3OB  CONST_11  C33   C28  C29  C30     0.00   0.0  0
 3OB  CONST_12  C33   C32  C31  C30     0.00   0.0  0
 3OB  CONST_13  C15   C14  N13  C12     0.00   0.0  0
 3OB  CONST_14  CL9   C3   C2   C1    180.00   0.0  0
 3OB  CONST_15  O7    C5   C6   C1    180.00   0.0  0
 3OB  CONST_16  C8    C1   C2   C3    180.00   0.0  0
 3OB  CONST_17  O7    C5   C4   C3    180.00   0.0  0
 3OB  CONST_18  CL9   C3   C4   C5    180.00   0.0  0
 3OB  CONST_19  C8    C1   C6   C5    180.00   0.0  0
 3OB  CONST_20  O17   C14  N13  C12   180.00   0.0  0
 3OB  CONST_21  H6    C6   C1   C2    180.00   0.0  0
 3OB  CONST_22  H4    C4   C3   C2    180.00   0.0  0
 3OB  CONST_23  H2    C2   C3   C4    180.00   0.0  0
 3OB  CONST_24  H30   C30  C29  C25     0.00   0.0  0
 3OB  CONST_25  H33   C33  C28  C26     0.00   0.0  0
 3OB  CONST_26  H32   C32  C33  C28   180.00   0.0  0
 3OB  CONST_27  H31   C31  C30  C29   180.00   0.0  0
 3OB  CONST_28  HN13  N13  C14  C15   180.00   0.0  0
 3OB  CONST_29  C25   N24  C22  C20     0.00   0.0  0
 3OB  CONST_30  C27   N24  C22  C20   180.00   0.0  0
 3OB  CONST_31  C25   N24  C22  O23   180.00   0.0  0
 3OB  CONST_32  C27   N24  C22  O23     0.00   0.0  0
 3OB  Var_01    C28   C29  C25  N24   -18.19  30.0  1
 3OB  Var_02    C28   C26  C27  N24    47.54  30.0  1
 3OB  Var_03    C26   C27  N24  C25   -68.28  30.0  1
 3OB  Var_04    C29   C25  N24  C27    51.81  30.0  1
 3OB  Var_05    C29   C28  C26  C27   -16.35  30.0  1
 3OB  Var_06    C11   C10  O7   C5   -135.75  30.0  3
 3OB  Var_07    C18   N16  C15  C10    94.94  30.0  2
 3OB  Var_08    C22   C20  C12  C11    99.38  30.0  3
 3OB  Var_09    N24   C22  C20  C12  -175.62  30.0  3
 3OB  Var_10    H18   C18  N16  C15    77.65  30.0  3
 3OB  Var_11    H19   C19  N16  C15    36.79  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
 3OB  plan-1  C1    0.020
 3OB  plan-1  C2    0.020
 3OB  plan-1  C3    0.020
 3OB  plan-1  C4    0.020
 3OB  plan-1  C5    0.020
 3OB  plan-1  C6    0.020
 3OB  plan-1  O7    0.020
 3OB  plan-1  C8    0.020
 3OB  plan-1  CL9   0.020
 3OB  plan-1  N21   0.020
 3OB  plan-1  H2    0.020
 3OB  plan-1  H4    0.020
 3OB  plan-1  H6    0.020
 3OB  plan-2  O7    0.020
 3OB  plan-2  C10   0.020
 3OB  plan-2  C11   0.020
 3OB  plan-2  C12   0.020
 3OB  plan-2  N13   0.020
 3OB  plan-2  C14   0.020
 3OB  plan-2  C15   0.020
 3OB  plan-2  N16   0.020
 3OB  plan-2  O17   0.020
 3OB  plan-2  C20   0.020
 3OB  plan-2  H11   0.020
 3OB  plan-2  HN13  0.020
 3OB  plan-3  C25   0.020
 3OB  plan-3  C26   0.020
 3OB  plan-3  C28   0.020
 3OB  plan-3  C29   0.020
 3OB  plan-3  C30   0.020
 3OB  plan-3  C31   0.020
 3OB  plan-3  C32   0.020
 3OB  plan-3  C33   0.020
 3OB  plan-3  H30   0.020
 3OB  plan-3  H31   0.020
 3OB  plan-3  H32   0.020
 3OB  plan-3  H33   0.020
 3OB  plan-4  C20   0.020
 3OB  plan-4  C22   0.020
 3OB  plan-4  O23   0.020
 3OB  plan-4  N24   0.020
 3OB  plan-4  C25   0.020
 3OB  plan-4  C27   0.020

