# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr  7 15:44:01 2020
#   Inital geometry file: a 118 line input string
#   Ligand name: ~{N}-(2,4-dimethoxyphenyl)-5-(1-methylpyrazol-4-yl)isoquinolin-3-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1ccc(Nc2cc3c(cccc3c4cnn(C)c4)cn2)c(OC)c1
#
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
 5OQ  5OQ  ~{N}-(2,4-dimethoxyphenyl)-5-(1-methylpyrazol-4-yl)isoquinolin-3-amine  ligand  47  27  .  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_5OQ
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
 5OQ  C1   C  CR16  0  -0.260   3.9175   3.2469  -0.7838
 5OQ  C2   C  CR16  0  -0.321   2.5786   3.5132  -0.7960
 5OQ  C3   C  CR66  0  -0.028   1.6599   2.4929  -0.4685
 5OQ  C4   C  CR66  0   0.233   2.1061   1.1900  -0.1222
 5OQ  C5   C  CR6   0   0.060   3.5151   0.9378  -0.0940
 5OQ  C10  C  CR16  0  -0.547   1.1290   0.2231   0.1542
 5OQ  C11  C  CR6   0   0.534  -0.2138   0.5659   0.1002
 5OQ  C12  C  CR16  0  -0.089   0.2691   2.7132  -0.4896
 5OQ  C13  C  CR6   0   0.241  -2.5583  -0.2054   0.3366
 5OQ  C14  C  CR16  0  -0.269  -3.2083   0.8654   0.9257
 5OQ  C6   C  CR5   0  -0.187   4.0563  -0.3766   0.2608
 5OQ  C16  C  CR6   0   0.390  -5.3540   0.0155   0.2693
 5OQ  C15  C  CR16  0  -0.414  -4.5933   0.9975   0.8885
 5OQ  C20  C  CH3   0  -0.434  -7.3965   1.1137   0.7616
 5OQ  O1   O  O2    0  -0.475  -6.6994   0.0326   0.1775
 5OQ  C17  C  CR16  0  -0.485  -4.7230  -1.0883  -0.3105
 5OQ  C18  C  CR6   0   0.346  -3.3419  -1.1958  -0.2890
 5OQ  O    O  O2    0  -0.470  -2.6597  -2.2212  -0.8315
 5OQ  C19  C  CH3   0  -0.437  -3.3801  -3.2861  -1.4194
 5OQ  N3   N  NH1   0  -0.769  -1.1697  -0.3736   0.3726
 5OQ  N2   N  N     0  -0.445  -0.6305   1.8081  -0.2185
 5OQ  C    C  CR16  0  -0.331   4.3724   1.9603  -0.4253
 5OQ  C8   C  CR15  0  -0.097   3.7649  -1.2084   1.3614
 5OQ  N1   N  N     0  -0.282   4.5134  -2.2947   1.3606
 5OQ  N    N  NR5   0  -0.264   5.2860  -2.1918   0.2844
 5OQ  C9   C  CH3   0  -0.506   6.1999  -3.2546  -0.0589
 5OQ  C7   C  CR15  0   0.022   5.0515  -1.0651  -0.4059
 5OQ  H1   H  HCR6  0   0.258   4.6371   4.0151  -1.0328
 5OQ  H2   H  HCR6  0   0.257   2.2070   4.4963  -1.0586
 5OQ  H3   H  HCR6  0   0.264   1.4108  -0.7923   0.3979
 5OQ  H4   H  HCR6  0   0.265  -0.1004   3.7004  -0.7547
 5OQ  H5   H  HCR6  0   0.263  -2.6286   1.6259   1.4279
 5OQ  H6   H  HCR6  0   0.274  -5.0446   1.8606   1.3565
 5OQ  H7   H  HCH3  0   0.226  -7.2374   1.1672   1.8418
 5OQ  H8   H  HCH3  0   0.226  -7.1146   2.0717   0.3166
 5OQ  H9   H  HCH3  0   0.258  -8.4530   0.9396   0.5725
 5OQ  H10  H  HCR6  0   0.285  -5.3355  -1.8429  -0.7866
 5OQ  H11  H  HCH3  0   0.262  -2.6407  -4.0053  -1.7623
 5OQ  H12  H  HCH3  0   0.231  -4.0431  -3.7745  -0.7006
 5OQ  H13  H  HCH3  0   0.230  -3.9721  -2.9542  -2.2763
 5OQ  H14  H  HNH1  0   0.399  -0.8369  -1.3202   0.4603
 5OQ  H15  H  HCR6  0   0.253   5.4399   1.7788  -0.3932
 5OQ  H16  H  HCR5  0   0.261   3.0577  -1.0372   2.1593
 5OQ  H17  H  HCH3  0   0.259   5.6604  -4.1240  -0.4315
 5OQ  H18  H  HCH3  0   0.258   6.8791  -2.9028  -0.8298
 5OQ  H19  H  HCH3  0   0.262   6.7777  -3.5404   0.8169
 5OQ  H20  H  HCR5  0   0.291   5.5814  -0.8306  -1.3156

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
 5OQ  C9   N    single    1.443  0.020  1.443
 5OQ  C    C1   aromatic  1.411  0.020  1.411
 5OQ  C    C5   aromatic  1.375  0.020  1.375
 5OQ  C1   C2   aromatic  1.365  0.020  1.365
 5OQ  C7   N    aromatic  1.342  0.020  1.342
 5OQ  C7   C6   aromatic  1.382  0.020  1.382
 5OQ  N    N1   aromatic  1.329  0.020  1.329
 5OQ  C6   C5   single    1.465  0.020  1.465
 5OQ  C6   C8   aromatic  1.410  0.020  1.410
 5OQ  C5   C4   aromatic  1.432  0.020  1.432
 5OQ  C2   C3   aromatic  1.411  0.020  1.411
 5OQ  N1   C8   aromatic  1.319  0.020  1.319
 5OQ  C4   C3   aromatic  1.420  0.020  1.420
 5OQ  C4   C10  aromatic  1.402  0.020  1.402
 5OQ  C3   C12  aromatic  1.408  0.020  1.408
 5OQ  C10  C11  aromatic  1.387  0.020  1.387
 5OQ  C12  N2   aromatic  1.305  0.020  1.305
 5OQ  C11  N2   aromatic  1.348  0.020  1.348
 5OQ  C11  N3   single    1.368  0.020  1.368
 5OQ  C14  C15  aromatic  1.392  0.020  1.392
 5OQ  C14  C13  aromatic  1.384  0.020  1.384
 5OQ  C15  C16  aromatic  1.388  0.020  1.388
 5OQ  N3   C13  single    1.399  0.020  1.399
 5OQ  C13  C18  aromatic  1.409  0.020  1.409
 5OQ  C20  O1   single    1.413  0.020  1.413
 5OQ  C16  O1   single    1.349  0.020  1.349
 5OQ  C16  C17  aromatic  1.397  0.020  1.397
 5OQ  C18  C17  aromatic  1.385  0.020  1.385
 5OQ  C18  O    single    1.346  0.020  1.346
 5OQ  O    C19  single    1.414  0.020  1.414
 5OQ  C1   H1   single    0.930  0.020  1.080
 5OQ  C2   H2   single    0.930  0.020  1.080
 5OQ  C10  H3   single    0.930  0.020  1.080
 5OQ  C12  H4   single    0.930  0.020  1.080
 5OQ  C14  H5   single    0.930  0.020  1.080
 5OQ  C15  H6   single    0.930  0.020  1.080
 5OQ  C20  H7   single    0.970  0.020  1.090
 5OQ  C20  H8   single    0.970  0.020  1.090
 5OQ  C20  H9   single    0.970  0.020  1.090
 5OQ  C17  H10  single    0.930  0.020  1.080
 5OQ  C19  H11  single    0.970  0.020  1.090
 5OQ  C19  H12  single    0.970  0.020  1.090
 5OQ  C19  H13  single    0.970  0.020  1.090
 5OQ  N3   H14  single    0.860  0.020  1.020
 5OQ  C    H15  single    0.930  0.020  1.080
 5OQ  C8   H16  single    0.930  0.020  1.080
 5OQ  C9   H17  single    0.970  0.020  1.090
 5OQ  C9   H18  single    0.970  0.020  1.090
 5OQ  C9   H19  single    0.970  0.020  1.090
 5OQ  C7   H20  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
 5OQ  H1   C1   C    119.44  3.000
 5OQ  H1   C1   C2   120.79  3.000
 5OQ  C    C1   C2   119.76  3.000
 5OQ  H2   C2   C3   119.27  3.000
 5OQ  H2   C2   C1   121.04  3.000
 5OQ  C3   C2   C1   119.69  3.000
 5OQ  C12  C3   C4   117.22  3.000
 5OQ  C12  C3   C2   121.76  3.000
 5OQ  C4   C3   C2   121.01  3.000
 5OQ  C10  C4   C5   124.09  3.000
 5OQ  C10  C4   C3   117.50  3.000
 5OQ  C5   C4   C3   118.40  3.000
 5OQ  C    C5   C6   119.68  3.000
 5OQ  C6   C5   C4   121.76  3.000
 5OQ  C    C5   C4   118.55  3.000
 5OQ  H3   C10  C11  119.54  3.000
 5OQ  H3   C10  C4   120.68  3.000
 5OQ  C11  C10  C4   119.78  3.000
 5OQ  N2   C11  N3   117.64  3.000
 5OQ  N3   C11  C10  119.94  3.000
 5OQ  N2   C11  C10  122.42  3.000
 5OQ  H4   C12  N2   116.51  3.000
 5OQ  H4   C12  C3   118.78  3.000
 5OQ  N2   C12  C3   124.71  3.000
 5OQ  N3   C13  C18  118.60  3.000
 5OQ  C18  C13  C14  118.13  3.000
 5OQ  N3   C13  C14  123.23  3.000
 5OQ  H5   C14  C15  118.67  3.000
 5OQ  H5   C14  C13  119.37  3.000
 5OQ  C15  C14  C13  121.96  3.000
 5OQ  C7   C6   C8   103.38  3.000
 5OQ  C8   C6   C5   129.93  3.000
 5OQ  C7   C6   C5   126.61  3.000
 5OQ  C17  C16  O1   115.61  3.000
 5OQ  C17  C16  C15  119.77  3.000
 5OQ  O1   C16  C15  124.62  3.000
 5OQ  H6   C15  C16  121.96  3.000
 5OQ  H6   C15  C14  118.68  3.000
 5OQ  C16  C15  C14  119.35  3.000
 5OQ  H9   C20  H8   108.67  3.000
 5OQ  H9   C20  H7   108.73  3.000
 5OQ  H8   C20  H7   108.77  3.000
 5OQ  H9   C20  O1   106.56  3.000
 5OQ  H8   C20  O1   112.02  3.000
 5OQ  H7   C20  O1   111.98  3.000
 5OQ  C20  O1   C16  118.28  3.000
 5OQ  H10  C17  C18  121.13  3.000
 5OQ  H10  C17  C16  118.54  3.000
 5OQ  C18  C17  C16  120.33  3.000
 5OQ  O    C18  C17  123.93  3.000
 5OQ  O    C18  C13  115.63  3.000
 5OQ  C17  C18  C13  120.44  3.000
 5OQ  C19  O    C18  118.89  3.000
 5OQ  H13  C19  H12  108.83  3.000
 5OQ  H13  C19  H11  108.78  3.000
 5OQ  H12  C19  H11  108.93  3.000
 5OQ  H13  C19  O    111.92  3.000
 5OQ  H12  C19  O    111.85  3.000
 5OQ  H11  C19  O    106.43  3.000
 5OQ  H14  N3   C13  116.31  3.000
 5OQ  H14  N3   C11  115.59  3.000
 5OQ  C13  N3   C11  127.29  3.000
 5OQ  C12  N2   C11  118.37  3.000
 5OQ  H15  C    C5   118.86  3.000
 5OQ  H15  C    C1   118.56  3.000
 5OQ  C5   C    C1   122.57  3.000
 5OQ  H16  C8   N1   120.17  3.000
 5OQ  H16  C8   C6   128.21  3.000
 5OQ  N1   C8   C6   111.59  3.000
 5OQ  N    N1   C8   105.46  3.000
 5OQ  C7   N    C9   127.35  3.000
 5OQ  C7   N    N1   112.33  3.000
 5OQ  C9   N    N1   120.25  3.000
 5OQ  H19  C9   H18  108.94  3.000
 5OQ  H19  C9   H17  109.21  3.000
 5OQ  H18  C9   H17  109.00  3.000
 5OQ  H19  C9   N    109.78  3.000
 5OQ  H18  C9   N    109.05  3.000
 5OQ  H17  C9   N    110.84  3.000
 5OQ  H20  C7   N    122.04  3.000
 5OQ  H20  C7   C6   130.73  3.000
 5OQ  N    C7   C6   107.22  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
 5OQ  CONST_01  C6   C5   C    C1    180.00   0.0  0
 5OQ  CONST_02  C4   C5   C    C1      0.00   0.0  0
 5OQ  CONST_03  C4   C3   C2   C1      0.00   0.0  0
 5OQ  CONST_04  C12  C3   C2   C1    180.00   0.0  0
 5OQ  CONST_05  C5   C    C1   C2      0.00   0.0  0
 5OQ  CONST_06  C5   C4   C3   C2      0.00   0.0  0
 5OQ  CONST_07  C10  C4   C3   C2    180.00   0.0  0
 5OQ  CONST_08  N2   C12  C3   C2    180.00   0.0  0
 5OQ  CONST_09  C    C1   C2   C3      0.00   0.0  0
 5OQ  CONST_10  C    C5   C4   C3      0.00   0.0  0
 5OQ  CONST_11  C6   C5   C4   C3    180.00   0.0  0
 5OQ  CONST_12  C11  C10  C4   C3      0.00   0.0  0
 5OQ  CONST_13  C11  N2   C12  C3      0.00   0.0  0
 5OQ  CONST_16  N2   C12  C3   C4      0.00   0.0  0
 5OQ  CONST_17  N2   C11  C10  C4      0.00   0.0  0
 5OQ  CONST_18  N    C7   C6   C5    180.00   0.0  0
 5OQ  CONST_19  N1   C8   C6   C5    180.00   0.0  0
 5OQ  CONST_20  C12  C3   C4   C5    180.00   0.0  0
 5OQ  CONST_21  C11  C10  C4   C5    180.00   0.0  0
 5OQ  CONST_22  C    C5   C4   C10   180.00   0.0  0
 5OQ  CONST_23  C6   C5   C4   C10     0.00   0.0  0
 5OQ  CONST_24  C12  C3   C4   C10     0.00   0.0  0
 5OQ  CONST_25  C12  N2   C11  C10     0.00   0.0  0
 5OQ  CONST_26  C16  C15  C14  C13     0.00   0.0  0
 5OQ  CONST_27  C16  C17  C18  C13     0.00   0.0  0
 5OQ  CONST_28  C17  C16  C15  C14     0.00   0.0  0
 5OQ  CONST_29  C17  C18  C13  C14     0.00   0.0  0
 5OQ  CONST_30  N1   N    C7   C6      0.00   0.0  0
 5OQ  CONST_31  N    N1   C8   C6      0.00   0.0  0
 5OQ  CONST_32  C18  C13  C14  C15     0.00   0.0  0
 5OQ  CONST_33  C18  C17  C16  C15     0.00   0.0  0
 5OQ  CONST_36  N    C7   C6   C8      0.00   0.0  0
 5OQ  CONST_37  C7   N    N1   C8      0.00   0.0  0
 5OQ  CONST_38  C7   C6   C8   N1      0.00   0.0  0
 5OQ  CONST_39  N3   C11  C10  C4    180.00   0.0  0
 5OQ  CONST_40  N3   C11  N2   C12   180.00   0.0  0
 5OQ  CONST_41  O1   C16  C15  C14   180.00   0.0  0
 5OQ  CONST_42  O    C18  C13  C14   180.00   0.0  0
 5OQ  CONST_43  C9   N    C7   C6    180.00   0.0  0
 5OQ  CONST_44  O    C18  C17  C16   180.00   0.0  0
 5OQ  CONST_45  N3   C13  C14  C15   180.00   0.0  0
 5OQ  CONST_46  C18  C17  C16  O1    180.00   0.0  0
 5OQ  CONST_47  N3   C13  C18  C17   180.00   0.0  0
 5OQ  CONST_48  C9   N    N1   C8    180.00   0.0  0
 5OQ  CONST_49  H15  C    C1   C2    180.00   0.0  0
 5OQ  CONST_50  H4   C12  C3   C2      0.00   0.0  0
 5OQ  CONST_51  H1   C1   C2   C3    180.00   0.0  0
 5OQ  CONST_52  H3   C10  C4   C3    180.00   0.0  0
 5OQ  CONST_53  H2   C2   C3   C4    180.00   0.0  0
 5OQ  CONST_54  H20  C7   C6   C5      0.00   0.0  0
 5OQ  CONST_55  H16  C8   C6   C5      0.00   0.0  0
 5OQ  CONST_56  H6   C15  C14  C13   180.00   0.0  0
 5OQ  CONST_57  H10  C17  C18  C13   180.00   0.0  0
 5OQ  CONST_58  H5   C14  C15  C16   180.00   0.0  0
 5OQ  Var_01    C13  N3   C11  C10  -178.55  30.0  2
 5OQ  Var_02    C14  C13  N3   C11   -47.39  30.0  2
 5OQ  Var_03    C17  C16  O1   C20   179.11  30.0  2
 5OQ  Var_04    H17  C9   N    N1     71.81  30.0  2
 5OQ  Var_05    H7   C20  O1   C16   -61.54  30.0  3
 5OQ  Var_06    H11  C19  O    C18  -178.40  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
 5OQ  plan-1  C5   0.020
 5OQ  plan-1  C6   0.020
 5OQ  plan-1  C8   0.020
 5OQ  plan-1  N1   0.020
 5OQ  plan-1  N    0.020
 5OQ  plan-1  C9   0.020
 5OQ  plan-1  C7   0.020
 5OQ  plan-1  H16  0.020
 5OQ  plan-1  H20  0.020
 5OQ  plan-2  C13  0.020
 5OQ  plan-2  C14  0.020
 5OQ  plan-2  C16  0.020
 5OQ  plan-2  C15  0.020
 5OQ  plan-2  O1   0.020
 5OQ  plan-2  C17  0.020
 5OQ  plan-2  C18  0.020
 5OQ  plan-2  O    0.020
 5OQ  plan-2  N3   0.020
 5OQ  plan-2  H5   0.020
 5OQ  plan-2  H6   0.020
 5OQ  plan-2  H10  0.020
 5OQ  plan-3  C1   0.020
 5OQ  plan-3  C2   0.020
 5OQ  plan-3  C3   0.020
 5OQ  plan-3  C4   0.020
 5OQ  plan-3  C5   0.020
 5OQ  plan-3  C10  0.020
 5OQ  plan-3  C11  0.020
 5OQ  plan-3  C12  0.020
 5OQ  plan-3  C6   0.020
 5OQ  plan-3  N3   0.020
 5OQ  plan-3  N2   0.020
 5OQ  plan-3  C    0.020
 5OQ  plan-3  H1   0.020
 5OQ  plan-3  H2   0.020
 5OQ  plan-3  H3   0.020
 5OQ  plan-3  H4   0.020
 5OQ  plan-3  H15  0.020

