# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr 22 19:43:36 2020
#   Inital geometry file: a 136 line input string
#   Ligand name: 6-(3-aminopropyl)-4-(3-hydroxyphenyl)-9-(1H-pyrazol-4-yl)benzo[h]isoquinolin-1(2H)-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: NCCCc1cc2C(=CNC(=O)c2c3cc(ccc13)c4c[nH]nc4)c5cccc(O)c5
#
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
 M54  M54  6-(3-aminopropyl)-4-(3-hydroxyphenyl)-9-(1H-pyrazol-4-yl)benzo[h]isoquinolin-1(2H)-one  ligand  53  31  .  2021-08-14  2021-08-14  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_M54
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
 M54  C     C  CR6   0   0.164  -3.7145  -0.0513   0.2312
 M54  C1    C  CR16  0  -0.339  -3.4590  -1.3943   0.5690
 M54  C2    C  CR16  0  -0.312  -2.1732  -1.8480   0.6557
 M54  C3    C  CR16  0  -0.482  -2.6449   0.7883  -0.0059
 M54  C4    C  CR66  0   0.177  -1.3026   0.3553   0.0723
 M54  C5    C  CR66  0   0.006  -1.0681  -1.0050   0.4145
 M54  C6    C  CR6   0   0.179   0.2681  -1.5004   0.5242
 M54  C7    C  CR16  0  -0.477   1.3068  -0.6553   0.2851
 M54  C8    C  CR66  0  -0.236  -0.1760   1.2235  -0.1752
 M54  C9    C  CR66  0   0.262   1.1234   0.7032  -0.0786
 M54  C10   C  CR6   0  -0.093   2.2769   1.5314  -0.3145
 M54  C11   C  CR16  0   0.014   2.0677   2.8363  -0.5908
 M54  N     N  NR16  0  -0.673   0.8159   3.3412  -0.6701
 M54  C12   C  CR6   0   0.524  -0.3512   2.6375  -0.5063
 M54  O     O  O     0  -0.489  -1.4138   3.2390  -0.6420
 M54  C13   C  CR5   0  -0.102  -5.0836   0.4459   0.1348
 M54  C14   C  CR15  0  -0.006  -6.2607  -0.2740   0.2371
 M54  N15   N  NR15  0  -0.428  -7.2605   0.6022   0.0801
 M54  N16   N  N     0  -0.259  -6.8416   1.8465  -0.1164
 M54  C17   C  CR15  0  -0.121  -5.5268   1.7696  -0.0874
 M54  C18   C  CH2   0  -0.557   0.5563  -2.9362   0.8592
 M54  C19   C  CH2   0  -0.428   0.3849  -3.8687  -0.3425
 M54  C20   C  CH2   0  -0.275   0.7067  -5.3125   0.0098
 M54  N21   N  NH2   0  -0.800   0.5115  -6.1819  -1.1408
 M54  C22   C  CR6   0   0.023   3.6634   1.0146  -0.2644
 M54  C23   C  CR16  0  -0.317   4.1043   0.0635  -1.1866
 M54  C24   C  CR16  0  -0.392   6.3022   0.1080  -0.1912
 M54  C25   C  CR6   0   0.372   5.8667   1.0570   0.7283
 M54  C26   C  CR16  0  -0.229   5.4156  -0.3809  -1.1410
 M54  C27   C  CR16  0  -0.381   4.5468   1.5050   0.6898
 M54  O28   O  OH1   0  -0.633   6.6696   1.5716   1.6802
 M54  H1    H  HCR6  0   0.247  -4.2743  -2.0786   0.7661
 M54  H2    H  HCR6  0   0.254  -2.0091  -2.8832   0.9201
 M54  H3    H  HCR6  0   0.271  -2.8352   1.8148  -0.2650
 M54  H7    H  HCR6  0   0.254   2.3159  -1.0316   0.3867
 M54  H11   H  HCR6  0   0.309   2.8695   3.5368  -0.7751
 M54  HN    H  HNR6  0   0.422   0.7086   4.3220  -0.8888
 M54  H14   H  HCR5  0   0.290  -6.4532  -1.3214   0.4012
 M54  HN15  H  HNR5  0   0.425  -8.2477   0.4014   0.1004
 M54  H17   H  HCR5  0   0.258  -4.9332   2.6617  -0.2220
 M54  H181  H  HCH2  0   0.260   1.5862  -3.0094   1.2158
 M54  H182  H  HCH2  0   0.247  -0.0722  -3.2775   1.6866
 M54  H191  H  HCH2  0   0.229  -0.6359  -3.8154  -0.7291
 M54  H192  H  HCH2  0   0.229   1.0416  -3.5313  -1.1509
 M54  H201  H  HCH2  0   0.192   1.7221  -5.3583   0.4302
 M54  H202  H  HCH2  0   0.216   0.0329  -5.6425   0.8056
 M54  H211  H  HNH2  0   0.338   1.2177  -5.9783  -1.8377
 M54  H212  H  HNH2  0   0.347   0.6710  -7.1429  -0.8671
 M54  H23   H  HCR6  0   0.252   3.4265  -0.3201  -1.9385
 M54  H24   H  HCR6  0   0.272   7.3253  -0.2495  -0.1673
 M54  H26   H  HCR6  0   0.261   5.7607  -1.1144  -1.8582
 M54  H27   H  HCR6  0   0.259   4.2108   2.2328   1.4188
 M54  HO28  H  HOH1  0   0.475   7.5513   1.1873   1.6209

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
 M54  N16  N15   aromatic  1.328  0.020  1.328
 M54  N16  C17   aromatic  1.317  0.020  1.317
 M54  N15  C14   aromatic  1.339  0.020  1.339
 M54  C17  C13   aromatic  1.414  0.020  1.414
 M54  O    C12   double    1.228  0.020  1.228
 M54  C14  C13   aromatic  1.384  0.020  1.384
 M54  C13  C     single    1.460  0.020  1.460
 M54  C12  N     single    1.373  0.020  1.373
 M54  C12  C8    single    1.463  0.020  1.463
 M54  N    C11   single    1.352  0.020  1.352
 M54  C3   C     aromatic  1.380  0.020  1.380
 M54  C3   C4    aromatic  1.413  0.020  1.413
 M54  C    C1    aromatic  1.408  0.020  1.408
 M54  C8   C4    aromatic  1.444  0.020  1.444
 M54  C8   C9    aromatic  1.403  0.020  1.403
 M54  C11  C10   double    1.350  0.020  1.350
 M54  C4   C5    aromatic  1.422  0.020  1.422
 M54  C1   C2    aromatic  1.366  0.020  1.366
 M54  C23  C26   aromatic  1.385  0.020  1.385
 M54  C23  C22   aromatic  1.396  0.020  1.396
 M54  C10  C9    single    1.439  0.020  1.439
 M54  C10  C22   single    1.480  0.020  1.480
 M54  C9   C7    aromatic  1.418  0.020  1.418
 M54  C5   C2    aromatic  1.411  0.020  1.411
 M54  C5   C6    aromatic  1.429  0.020  1.429
 M54  C26  C24   aromatic  1.388  0.020  1.388
 M54  C22  C27   aromatic  1.390  0.020  1.390
 M54  C7   C6    aromatic  1.360  0.020  1.360
 M54  C6   C18   single    1.502  0.020  1.502
 M54  C18  C19   single    1.531  0.020  1.531
 M54  C24  C25   aromatic  1.391  0.020  1.391
 M54  C27  C25   aromatic  1.394  0.020  1.394
 M54  C25  O28   single    1.347  0.020  1.347
 M54  C19  C20   single    1.521  0.020  1.521
 M54  C20  N21   single    1.455  0.020  1.455
 M54  C1   H1    single    0.930  0.020  1.080
 M54  C2   H2    single    0.930  0.020  1.080
 M54  C3   H3    single    0.930  0.020  1.080
 M54  C7   H7    single    0.930  0.020  1.080
 M54  C11  H11   single    0.930  0.020  1.080
 M54  N    HN    single    0.860  0.020  1.020
 M54  C14  H14   single    0.930  0.020  1.080
 M54  N15  HN15  single    0.860  0.020  1.020
 M54  C17  H17   single    0.930  0.020  1.080
 M54  C18  H181  single    0.970  0.020  1.090
 M54  C18  H182  single    0.970  0.020  1.090
 M54  C19  H191  single    0.970  0.020  1.090
 M54  C19  H192  single    0.970  0.020  1.090
 M54  C20  H201  single    0.970  0.020  1.090
 M54  C20  H202  single    0.970  0.020  1.090
 M54  N21  H211  single    0.890  0.020  1.040
 M54  N21  H212  single    0.890  0.020  1.040
 M54  C23  H23   single    0.930  0.020  1.080
 M54  C24  H24   single    0.930  0.020  1.080
 M54  C26  H26   single    0.930  0.020  1.080
 M54  C27  H27   single    0.930  0.020  1.080
 M54  O28  HO28  single    0.850  0.020  0.980

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
 M54  C13   C    C3    120.55  3.000
 M54  C3    C    C1    118.73  3.000
 M54  C13   C    C1    120.72  3.000
 M54  H1    C1   C2    119.16  3.000
 M54  H1    C1   C     120.66  3.000
 M54  C2    C1   C     120.18  3.000
 M54  H2    C2   C5    119.68  3.000
 M54  H2    C2   C1    118.45  3.000
 M54  C5    C2   C1    121.87  3.000
 M54  H3    C3   C4    118.29  3.000
 M54  H3    C3   C     119.00  3.000
 M54  C4    C3   C     122.71  3.000
 M54  C8    C4   C5    119.19  3.000
 M54  C5    C4   C3    117.60  3.000
 M54  C8    C4   C3    123.21  3.000
 M54  C6    C5   C4    120.28  3.000
 M54  C6    C5   C2    120.80  3.000
 M54  C4    C5   C2    118.91  3.000
 M54  C18   C6   C7    119.11  3.000
 M54  C18   C6   C5    121.85  3.000
 M54  C7    C6   C5    119.02  3.000
 M54  H7    C7   C9    118.55  3.000
 M54  H7    C7   C6    118.67  3.000
 M54  C9    C7   C6    122.78  3.000
 M54  C12   C8   C9    119.01  3.000
 M54  C9    C8   C4    119.21  3.000
 M54  C12   C8   C4    121.78  3.000
 M54  C10   C9   C8    121.17  3.000
 M54  C10   C9   C7    119.30  3.000
 M54  C8    C9   C7    119.51  3.000
 M54  C22   C10  C11   119.30  3.000
 M54  C22   C10  C9    122.96  3.000
 M54  C11   C10  C9    117.73  3.000
 M54  H11   C11  N     115.78  3.000
 M54  H11   C11  C10   123.13  3.000
 M54  N     C11  C10   121.09  3.000
 M54  HN    N    C12   115.66  3.000
 M54  HN    N    C11   118.26  3.000
 M54  C12   N    C11   126.07  3.000
 M54  O     C12  N     118.12  3.000
 M54  N     C12  C8    114.88  3.000
 M54  O     C12  C8    127.00  3.000
 M54  C17   C13  C14   103.42  3.000
 M54  C14   C13  C     128.02  3.000
 M54  C17   C13  C     128.56  3.000
 M54  H14   C14  N15   121.38  3.000
 M54  H14   C14  C13   131.99  3.000
 M54  N15   C14  C13   106.63  3.000
 M54  HN15  N15  N16   119.93  3.000
 M54  HN15  N15  C14   126.79  3.000
 M54  N16   N15  C14   113.28  3.000
 M54  C17   N16  N15   104.89  3.000
 M54  H17   C17  N16   119.84  3.000
 M54  H17   C17  C13   128.38  3.000
 M54  N16   C17  C13   111.78  3.000
 M54  H182  C18  H181  105.90  3.000
 M54  H182  C18  C19   109.85  3.000
 M54  H181  C18  C19   108.73  3.000
 M54  H182  C18  C6    110.90  3.000
 M54  H181  C18  C6    108.52  3.000
 M54  C19   C18  C6    112.68  3.000
 M54  H192  C19  H191  106.50  3.000
 M54  H192  C19  C20   109.68  3.000
 M54  H191  C19  C20   109.02  3.000
 M54  H192  C19  C18   108.95  3.000
 M54  H191  C19  C18   110.65  3.000
 M54  C20   C19  C18   111.89  3.000
 M54  H202  C20  H201  106.14  3.000
 M54  H202  C20  N21   108.21  3.000
 M54  H201  C20  N21   113.65  3.000
 M54  H202  C20  C19   108.94  3.000
 M54  H201  C20  C19   108.87  3.000
 M54  N21   C20  C19   110.83  3.000
 M54  H212  N21  H211  105.49  3.000
 M54  H212  N21  C20   109.42  3.000
 M54  H211  N21  C20   109.30  3.000
 M54  C27   C22  C23   119.54  3.000
 M54  C27   C22  C10   119.69  3.000
 M54  C23   C22  C10   120.74  3.000
 M54  H23   C23  C26   120.12  3.000
 M54  H23   C23  C22   120.16  3.000
 M54  C26   C23  C22   119.72  3.000
 M54  H24   C24  C26   120.11  3.000
 M54  H24   C24  C25   120.39  3.000
 M54  C26   C24  C25   119.50  3.000
 M54  O28   C25  C27   117.44  3.000
 M54  O28   C25  C24   122.74  3.000
 M54  C27   C25  C24   119.82  3.000
 M54  H26   C26  C24   119.24  3.000
 M54  H26   C26  C23   119.83  3.000
 M54  C24   C26  C23   120.93  3.000
 M54  H27   C27  C25   119.39  3.000
 M54  H27   C27  C22   120.12  3.000
 M54  C25   C27  C22   120.49  3.000
 M54  HO28  O28  C25   110.45  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
 M54  CONST_01  N16   C17  C13  C    180.00   0.0  0
 M54  CONST_02  N15   C14  C13  C    180.00   0.0  0
 M54  CONST_03  C8    C4   C3   C    180.00   0.0  0
 M54  CONST_04  C5    C4   C3   C      0.00   0.0  0
 M54  CONST_05  C5    C2   C1   C      0.00   0.0  0
 M54  CONST_06  C17   C13  C    C1   180.00   0.0  0
 M54  CONST_07  C14   C13  C    C1     0.00   0.0  0
 M54  CONST_08  C4    C3   C    C1     0.00   0.0  0
 M54  CONST_09  C4    C5   C2   C1     0.00   0.0  0
 M54  CONST_10  C6    C5   C2   C1   180.00   0.0  0
 M54  CONST_11  C13   C    C1   C2   180.00   0.0  0
 M54  CONST_12  C3    C    C1   C2     0.00   0.0  0
 M54  CONST_13  C3    C4   C5   C2     0.00   0.0  0
 M54  CONST_14  C8    C4   C5   C2   180.00   0.0  0
 M54  CONST_15  C7    C6   C5   C2   180.00   0.0  0
 M54  CONST_16  C17   C13  C    C3     0.00   0.0  0
 M54  CONST_17  C14   C13  C    C3   180.00   0.0  0
 M54  CONST_18  C9    C8   C4   C3   180.00   0.0  0
 M54  CONST_19  C6    C5   C4   C3   180.00   0.0  0
 M54  CONST_20  C13   C    C3   C4   180.00   0.0  0
 M54  CONST_21  C7    C9   C8   C4     0.00   0.0  0
 M54  CONST_22  C7    C6   C5   C4     0.00   0.0  0
 M54  CONST_23  C9    C8   C4   C5     0.00   0.0  0
 M54  CONST_24  C9    C7   C6   C5     0.00   0.0  0
 M54  CONST_25  C8    C4   C5   C6     0.00   0.0  0
 M54  CONST_26  C8    C9   C7   C6     0.00   0.0  0
 M54  CONST_27  N15   N16  C17  C13    0.00   0.0  0
 M54  CONST_28  N16   N15  C14  C13    0.00   0.0  0
 M54  CONST_29  C17   N16  N15  C14    0.00   0.0  0
 M54  CONST_30  N16   C17  C13  C14    0.00   0.0  0
 M54  CONST_31  C17   C13  C14  N15    0.00   0.0  0
 M54  CONST_32  C24   C26  C23  C22    0.00   0.0  0
 M54  CONST_33  C24   C25  C27  C22    0.00   0.0  0
 M54  CONST_34  C25   C24  C26  C23    0.00   0.0  0
 M54  CONST_35  C25   C27  C22  C23    0.00   0.0  0
 M54  CONST_36  C27   C22  C23  C26    0.00   0.0  0
 M54  CONST_37  C27   C25  C24  C26    0.00   0.0  0
 M54  CONST_38  C26   C23  C22  C10  180.00   0.0  0
 M54  CONST_39  C25   C27  C22  C10  180.00   0.0  0
 M54  CONST_40  C11   N    C12  C8     0.00   0.0  0
 M54  CONST_41  C18   C6   C5   C2     0.00   0.0  0
 M54  CONST_42  C18   C6   C5   C4   180.00   0.0  0
 M54  CONST_43  C18   C6   C7   C9   180.00   0.0  0
 M54  CONST_44  O28   C25  C27  C22  180.00   0.0  0
 M54  CONST_45  O28   C25  C24  C26  180.00   0.0  0
 M54  CONST_46  O     C12  N    C11  180.00   0.0  0
 M54  CONST_47  H17   C17  C13  C      0.00   0.0  0
 M54  CONST_48  H14   C14  C13  C      0.00   0.0  0
 M54  CONST_49  H2    C2   C1   C    180.00   0.0  0
 M54  CONST_50  H3    C3   C    C1   180.00   0.0  0
 M54  CONST_51  H1    C1   C    C3   180.00   0.0  0
 M54  CONST_52  H7    C7   C6   C5   180.00   0.0  0
 M54  CONST_53  H23   C23  C22  C10    0.00   0.0  0
 M54  CONST_54  H27   C27  C22  C10    0.00   0.0  0
 M54  CONST_55  HN15  N15  C14  C13  180.00   0.0  0
 M54  CONST_56  H26   C26  C23  C22  180.00   0.0  0
 M54  CONST_57  H24   C24  C26  C23  180.00   0.0  0
 M54  CONST_58  HN    N    C12  C8   180.00   0.0  0
 M54  Var_01    C23   C22  C10  C9    64.65  30.0  2
 M54  Var_02    C19   C18  C6   C5    78.42  30.0  2
 M54  Var_03    C20   C19  C18  C6   178.90  30.0  3
 M54  Var_04    N21   C20  C19  C18  178.90  30.0  3
 M54  Var_05    H211  N21  C20  C19   68.71  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
 M54  plan-1  C     0.020
 M54  plan-1  C13   0.020
 M54  plan-1  C14   0.020
 M54  plan-1  N15   0.020
 M54  plan-1  N16   0.020
 M54  plan-1  C17   0.020
 M54  plan-1  H14   0.020
 M54  plan-1  HN15  0.020
 M54  plan-1  H17   0.020
 M54  plan-2  C10   0.020
 M54  plan-2  C22   0.020
 M54  plan-2  C23   0.020
 M54  plan-2  C24   0.020
 M54  plan-2  C25   0.020
 M54  plan-2  C26   0.020
 M54  plan-2  C27   0.020
 M54  plan-2  O28   0.020
 M54  plan-2  H23   0.020
 M54  plan-2  H24   0.020
 M54  plan-2  H26   0.020
 M54  plan-2  H27   0.020
 M54  plan-3  C     0.020
 M54  plan-3  C1    0.020
 M54  plan-3  C2    0.020
 M54  plan-3  C3    0.020
 M54  plan-3  C4    0.020
 M54  plan-3  C5    0.020
 M54  plan-3  C6    0.020
 M54  plan-3  C7    0.020
 M54  plan-3  C8    0.020
 M54  plan-3  C9    0.020
 M54  plan-3  C10   0.020
 M54  plan-3  C11   0.020
 M54  plan-3  N     0.020
 M54  plan-3  C12   0.020
 M54  plan-3  O     0.020
 M54  plan-3  C13   0.020
 M54  plan-3  C18   0.020
 M54  plan-3  C22   0.020
 M54  plan-3  H1    0.020
 M54  plan-3  H2    0.020
 M54  plan-3  H3    0.020
 M54  plan-3  H7    0.020
 M54  plan-3  H11   0.020
 M54  plan-3  HN    0.020

