# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 28 22:10:26 2020
#   Inital geometry file: a 138 line input string
#   Ligand name: 1-(propan-2-yl)-3-({3-[3-(trifluoromethyl)phenyl]isoquinolin-8-yl}ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)n1nc(C#Cc2cccc3cc(ncc23)c4cccc(c4)C(F)(F)F)c5c(N)ncnc15
#
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
 EU4  EU4  1-(propan-2-yl)-3-({3-[3-(trifluoromethyl)phenyl]isoquinolin-8-yl}ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine  ligand  54  35  .  2021-08-08  2021-08-08  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_EU4
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
 EU4  C10  C  CR66  0  -0.019   0.4866   2.1499   0.0793
 EU4  N12  N  N     0  -0.435   2.1528   0.4326  -0.0182
 EU4  C13  C  CR6   0   0.261   3.1340   1.3672   0.0123
 EU4  C15  C  CR66  0   0.256   1.4975   3.1337   0.1138
 EU4  C17  C  CR16  0  -0.236  -0.1817   4.8583   0.2113
 EU4  C20  C  CR16  0  -0.320   4.7418  -0.5282  -0.0305
 EU4  C21  C  CR6   0  -0.168   6.0314  -1.0389  -0.0631
 EU4  C22  C  CR16  0  -0.289   7.1277  -0.1865  -0.1036
 EU4  C24  C  CR16  0  -0.338   5.6286   1.6961  -0.0661
 EU4  C01  C  CH3   0  -0.651  -4.1901  -4.1841  -1.1110
 EU4  C02  C  CH1   0  -0.121  -4.9268  -3.5473   0.0573
 EU4  C03  C  CH3   0  -0.649  -4.4420  -4.0619   1.4047
 EU4  C06  C  CR5   0   0.122  -3.8471  -0.1954   0.0108
 EU4  C07  C  CSP   0   0.079  -2.7902   0.7406   0.0502
 EU4  C09  C  CR6   0  -0.086  -0.8813   2.5433   0.1117
 EU4  C11  C  CR16  0  -0.120   0.9055   0.8025   0.0131
 EU4  C14  C  CR16  0  -0.417   2.8396   2.7069   0.0786
 EU4  C16  C  CR16  0  -0.318   1.1382   4.4995   0.1813
 EU4  C18  C  CR16  0  -0.336  -1.1952   3.8842   0.1770
 EU4  C19  C  CR6   0   0.090   4.5201   0.8487  -0.0290
 EU4  C23  C  CR16  0  -0.218   6.9142   1.1832  -0.1035
 EU4  C29  C  CR56  0  -0.282  -5.2380   0.0640  -0.0788
 EU4  C30  C  CR56  0   0.565  -5.8272  -1.1975  -0.0799
 EU4  C32  C  CR16  0   0.056  -7.8500  -0.3425  -0.2208
 EU4  C34  C  CR6   0   0.448  -6.1186   1.1657  -0.1617
 EU4  F26  F  F     0  -0.308   7.3945  -2.8889   0.4515
 EU4  F27  F  F     0  -0.307   5.2651  -3.1911   0.5180
 EU4  F28  F  F     0  -0.315   6.2622  -2.9756  -1.3736
 EU4  N04  N  NR5   0  -0.363  -4.8209  -2.0939   0.0014
 EU4  N05  N  N     0  -0.258  -3.6318  -1.4963   0.0582
 EU4  N31  N  N     0  -0.464  -7.1373  -1.4485  -0.1491
 EU4  N33  N  N     0  -0.475  -7.4292   0.9225  -0.2318
 EU4  N35  N  NH2   0  -0.816  -5.6964   2.4272  -0.1712
 EU4  H1   H  HCR6  0   0.277  -0.4585   5.9025   0.2639
 EU4  H2   H  HCR6  0   0.272   3.8876  -1.1900  -0.0032
 EU4  H3   H  HCR6  0   0.276   8.1389  -0.5696  -0.1328
 EU4  H4   H  HCR6  0   0.265   5.5078   2.7706  -0.0684
 EU4  H5   H  HCH3  0   0.243  -4.5528  -3.8010  -2.0645
 EU4  H6   H  HCH3  0   0.235  -3.1169  -4.0034  -1.0496
 EU4  H7   H  HCH3  0   0.241  -4.3499  -5.2618  -1.0968
 EU4  H8   H  HCH1  0   0.268  -5.9938  -3.7516  -0.0415
 EU4  H9   H  HCH3  0   0.234  -3.3760  -3.8761   1.5362
 EU4  H10  H  HCH3  0   0.242  -4.9800  -3.5891   2.2262
 EU4  H11  H  HCH3  0   0.241  -4.6064  -5.1372   1.4677
 EU4  H12  H  HCR6  0   0.267   0.1619   0.0119  -0.0143
 EU4  H13  H  HCR6  0   0.277   3.6153   3.4594   0.1061
 EU4  H14  H  HCR6  0   0.272   1.9154   5.2520   0.2077
 EU4  H15  H  HCR6  0   0.273  -2.2319   4.1923   0.2032
 EU4  H16  H  HCR6  0   0.274   7.7582   1.8585  -0.1324
 EU4  H17  H  HCR6  0   0.258  -8.9256  -0.4714  -0.2788
 EU4  H18  H  HNH2  0   0.413  -4.7197   2.6606  -0.1280
 EU4  H19  H  HNH2  0   0.410  -6.3594   3.1802  -0.2447
 EU4  C08  C  CSP   0   0.140  -1.9134   1.5701   0.0772
 EU4  C25  C  CT    0   1.055   6.2375  -2.5211  -0.1106

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
 EU4  F27  C25  single    1.338  0.020  1.338
 EU4  F26  C25  single    1.338  0.020  1.338
 EU4  C25  F28  single    1.342  0.020  1.342
 EU4  C25  C21  single    1.497  0.020  1.497
 EU4  C22  C21  aromatic  1.389  0.020  1.389
 EU4  C22  C23  aromatic  1.386  0.020  1.386
 EU4  C21  C20  aromatic  1.387  0.020  1.387
 EU4  C23  C24  aromatic  1.385  0.020  1.385
 EU4  C20  C19  aromatic  1.395  0.020  1.395
 EU4  C24  C19  aromatic  1.396  0.020  1.396
 EU4  C19  C13  single    1.480  0.020  1.480
 EU4  C13  N12  aromatic  1.355  0.020  1.355
 EU4  C13  C14  aromatic  1.373  0.020  1.373
 EU4  N12  C11  aromatic  1.301  0.020  1.301
 EU4  C14  C15  aromatic  1.409  0.020  1.409
 EU4  C11  C10  aromatic  1.413  0.020  1.413
 EU4  C15  C10  aromatic  1.411  0.020  1.411
 EU4  C15  C16  aromatic  1.414  0.020  1.414
 EU4  C10  C09  aromatic  1.424  0.020  1.424
 EU4  C01  C02  single    1.521  0.020  1.521
 EU4  C16  C17  aromatic  1.368  0.020  1.368
 EU4  C09  C08  single    1.419  0.020  1.419
 EU4  C09  C18  aromatic  1.379  0.020  1.379
 EU4  C08  C07  triple    1.207  0.020  1.207
 EU4  N05  C06  aromatic  1.319  0.020  1.319
 EU4  N05  N04  aromatic  1.332  0.020  1.332
 EU4  C07  C06  single    1.412  0.020  1.412
 EU4  C02  C03  single    1.522  0.020  1.522
 EU4  C02  N04  single    1.458  0.020  1.458
 EU4  C06  C29  aromatic  1.418  0.020  1.418
 EU4  N04  C30  aromatic  1.350  0.020  1.350
 EU4  C29  C30  aromatic  1.392  0.020  1.392
 EU4  C29  C34  aromatic  1.413  0.020  1.413
 EU4  C30  N31  aromatic  1.336  0.020  1.336
 EU4  C34  N35  single    1.330  0.020  1.330
 EU4  C34  N33  aromatic  1.335  0.020  1.335
 EU4  N31  C32  aromatic  1.318  0.020  1.318
 EU4  C17  C18  aromatic  1.406  0.020  1.406
 EU4  N33  C32  aromatic  1.333  0.020  1.333
 EU4  C17  H1   single    0.930  0.020  1.080
 EU4  C20  H2   single    0.930  0.020  1.080
 EU4  C22  H3   single    0.930  0.020  1.080
 EU4  C24  H4   single    0.930  0.020  1.080
 EU4  C01  H5   single    0.970  0.020  1.090
 EU4  C01  H6   single    0.970  0.020  1.090
 EU4  C01  H7   single    0.970  0.020  1.090
 EU4  C02  H8   single    0.970  0.020  1.090
 EU4  C03  H9   single    0.970  0.020  1.090
 EU4  C03  H10  single    0.970  0.020  1.090
 EU4  C03  H11  single    0.970  0.020  1.090
 EU4  C11  H12  single    0.930  0.020  1.080
 EU4  C14  H13  single    0.930  0.020  1.080
 EU4  C16  H14  single    0.930  0.020  1.080
 EU4  C18  H15  single    0.930  0.020  1.080
 EU4  C23  H16  single    0.930  0.020  1.080
 EU4  C32  H17  single    0.930  0.020  1.080
 EU4  N35  H18  single    0.860  0.020  1.020
 EU4  N35  H19  single    0.860  0.020  1.020

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
 EU4  C11  C10  C09  123.33  3.000
 EU4  C09  C10  C15  119.68  3.000
 EU4  C11  C10  C15  116.99  3.000
 EU4  C11  N12  C13  119.83  3.000
 EU4  C19  C13  C14  122.94  3.000
 EU4  C14  C13  N12  121.23  3.000
 EU4  C19  C13  N12  115.83  3.000
 EU4  C16  C15  C14  122.41  3.000
 EU4  C16  C15  C10  119.51  3.000
 EU4  C14  C15  C10  118.08  3.000
 EU4  H1   C17  C18  119.04  3.000
 EU4  H1   C17  C16  120.08  3.000
 EU4  C18  C17  C16  120.87  3.000
 EU4  H2   C20  C19  118.61  3.000
 EU4  H2   C20  C21  120.65  3.000
 EU4  C19  C20  C21  120.74  3.000
 EU4  C25  C21  C22  119.86  3.000
 EU4  C22  C21  C20  120.55  3.000
 EU4  C25  C21  C20  119.55  3.000
 EU4  H3   C22  C23  119.59  3.000
 EU4  H3   C22  C21  121.41  3.000
 EU4  C23  C22  C21  118.99  3.000
 EU4  H4   C24  C23  118.15  3.000
 EU4  H4   C24  C19  120.97  3.000
 EU4  C23  C24  C19  120.88  3.000
 EU4  H7   C01  H6   107.92  3.000
 EU4  H7   C01  H5   108.07  3.000
 EU4  H6   C01  H5   108.59  3.000
 EU4  H7   C01  C02  109.45  3.000
 EU4  H6   C01  C02  111.36  3.000
 EU4  H5   C01  C02  111.33  3.000
 EU4  H8   C02  N04  104.73  3.000
 EU4  H8   C02  C03  109.18  3.000
 EU4  N04  C02  C03  110.36  3.000
 EU4  H8   C02  C01  109.01  3.000
 EU4  N04  C02  C01  110.65  3.000
 EU4  C03  C02  C01  112.60  3.000
 EU4  H11  C03  H10  108.06  3.000
 EU4  H11  C03  H9   107.98  3.000
 EU4  H10  C03  H9   108.53  3.000
 EU4  H11  C03  C02  109.69  3.000
 EU4  H10  C03  C02  111.31  3.000
 EU4  H9   C03  C02  111.15  3.000
 EU4  N05  C06  C29  110.05  3.000
 EU4  C29  C06  C07  127.93  3.000
 EU4  N05  C06  C07  122.02  3.000
 EU4  C08  C07  C06  180.00  3.000
 EU4  C18  C09  C08  120.18  3.000
 EU4  C18  C09  C10  119.24  3.000
 EU4  C08  C09  C10  120.58  3.000
 EU4  H12  C11  N12  116.68  3.000
 EU4  H12  C11  C10  119.52  3.000
 EU4  N12  C11  C10  123.81  3.000
 EU4  H13  C14  C15  118.17  3.000
 EU4  H13  C14  C13  121.76  3.000
 EU4  C15  C14  C13  120.07  3.000
 EU4  H14  C16  C17  120.66  3.000
 EU4  H14  C16  C15  119.37  3.000
 EU4  C17  C16  C15  119.97  3.000
 EU4  H15  C18  C09  119.75  3.000
 EU4  H15  C18  C17  119.53  3.000
 EU4  C09  C18  C17  120.72  3.000
 EU4  C24  C19  C20  118.24  3.000
 EU4  C24  C19  C13  122.12  3.000
 EU4  C20  C19  C13  119.64  3.000
 EU4  H16  C23  C24  119.61  3.000
 EU4  H16  C23  C22  119.79  3.000
 EU4  C24  C23  C22  120.60  3.000
 EU4  C34  C29  C30  116.28  3.000
 EU4  C34  C29  C06  139.28  3.000
 EU4  C30  C29  C06  104.44  3.000
 EU4  N31  C30  N04  127.55  3.000
 EU4  N31  C30  C29  125.82  3.000
 EU4  N04  C30  C29  106.63  3.000
 EU4  H17  C32  N33  115.16  3.000
 EU4  H17  C32  N31  116.07  3.000
 EU4  N33  C32  N31  128.77  3.000
 EU4  N35  C34  N33  118.95  3.000
 EU4  N33  C34  C29  118.22  3.000
 EU4  N35  C34  C29  122.83  3.000
 EU4  N05  N04  C30  111.72  3.000
 EU4  C30  N04  C02  127.58  3.000
 EU4  N05  N04  C02  120.69  3.000
 EU4  N04  N05  C06  107.17  3.000
 EU4  C32  N31  C30  112.06  3.000
 EU4  C34  N33  C32  118.84  3.000
 EU4  H19  N35  H18  118.01  3.000
 EU4  H19  N35  C34  120.08  3.000
 EU4  H18  N35  C34  121.89  3.000
 EU4  C09  C08  C07  180.00  3.000
 EU4  F28  C25  F27  106.61  3.000
 EU4  F28  C25  F26  106.64  3.000
 EU4  F27  C25  F26  107.07  3.000
 EU4  F28  C25  C21  111.56  3.000
 EU4  F26  C25  C21  112.20  3.000
 EU4  F27  C25  C21  112.38  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
 EU4  CONST_01  C13  N12  C11  C10    0.00   0.0  0
 EU4  CONST_02  C13  C14  C15  C10    0.00   0.0  0
 EU4  CONST_03  C17  C16  C15  C10    0.00   0.0  0
 EU4  CONST_04  C17  C18  C09  C10    0.00   0.0  0
 EU4  CONST_05  C20  C19  C13  N12    0.00   0.0  0
 EU4  CONST_06  C24  C19  C13  N12  180.00   0.0  0
 EU4  CONST_07  C15  C14  C13  N12    0.00   0.0  0
 EU4  CONST_08  C15  C10  C11  N12    0.00   0.0  0
 EU4  CONST_09  C09  C10  C11  N12  180.00   0.0  0
 EU4  CONST_10  C21  C20  C19  C13  180.00   0.0  0
 EU4  CONST_11  C23  C24  C19  C13  180.00   0.0  0
 EU4  CONST_12  C16  C15  C14  C13  180.00   0.0  0
 EU4  CONST_13  C19  C13  C14  C15  180.00   0.0  0
 EU4  CONST_14  C18  C09  C10  C15    0.00   0.0  0
 EU4  CONST_15  C18  C17  C16  C15    0.00   0.0  0
 EU4  CONST_16  C14  C15  C16  C17  180.00   0.0  0
 EU4  CONST_17  C23  C22  C21  C20    0.00   0.0  0
 EU4  CONST_18  C23  C24  C19  C20    0.00   0.0  0
 EU4  CONST_19  C14  C13  C19  C20  180.00   0.0  0
 EU4  CONST_20  C24  C23  C22  C21    0.00   0.0  0
 EU4  CONST_21  C24  C19  C20  C21    0.00   0.0  0
 EU4  CONST_22  C19  C20  C21  C22    0.00   0.0  0
 EU4  CONST_23  C19  C24  C23  C22    0.00   0.0  0
 EU4  CONST_24  C14  C13  C19  C24    0.00   0.0  0
 EU4  CONST_25  C30  N04  N05  C06    0.00   0.0  0
 EU4  CONST_26  N04  C30  C29  C06    0.00   0.0  0
 EU4  CONST_27  N31  C30  C29  C06  180.00   0.0  0
 EU4  CONST_28  N33  C34  C29  C06  180.00   0.0  0
 EU4  CONST_29  C14  C15  C10  C09  180.00   0.0  0
 EU4  CONST_30  C16  C15  C10  C09    0.00   0.0  0
 EU4  CONST_31  C16  C17  C18  C09    0.00   0.0  0
 EU4  CONST_32  C19  C13  N12  C11  180.00   0.0  0
 EU4  CONST_33  C14  C13  N12  C11    0.00   0.0  0
 EU4  CONST_34  C14  C15  C10  C11    0.00   0.0  0
 EU4  CONST_35  C16  C15  C10  C11  180.00   0.0  0
 EU4  CONST_36  C18  C09  C10  C11  180.00   0.0  0
 EU4  CONST_37  N04  N05  C06  C29    0.00   0.0  0
 EU4  CONST_38  N05  N04  C30  C29    0.00   0.0  0
 EU4  CONST_39  C32  N31  C30  C29    0.00   0.0  0
 EU4  CONST_40  C32  N33  C34  C29    0.00   0.0  0
 EU4  CONST_41  N05  C06  C29  C30    0.00   0.0  0
 EU4  CONST_42  N33  C34  C29  C30    0.00   0.0  0
 EU4  CONST_43  N33  C32  N31  C30    0.00   0.0  0
 EU4  CONST_44  N04  C30  N31  C32  180.00   0.0  0
 EU4  CONST_45  N05  C06  C29  C34  180.00   0.0  0
 EU4  CONST_46  N04  C30  C29  C34  180.00   0.0  0
 EU4  CONST_47  N31  C30  C29  C34    0.00   0.0  0
 EU4  CONST_48  N31  C32  N33  C34    0.00   0.0  0
 EU4  CONST_49  N31  C30  N04  N05  180.00   0.0  0
 EU4  CONST_50  C08  C09  C10  C15  180.00   0.0  0
 EU4  CONST_51  C08  C09  C18  C17  180.00   0.0  0
 EU4  CONST_52  C06  N05  N04  C02  180.00   0.0  0
 EU4  CONST_53  C29  C30  N04  C02  180.00   0.0  0
 EU4  CONST_54  N31  C30  N04  C02    0.00   0.0  0
 EU4  CONST_55  N35  C34  C29  C06    0.00   0.0  0
 EU4  CONST_56  N04  N05  C06  C07  180.00   0.0  0
 EU4  CONST_57  C30  C29  C06  C07  180.00   0.0  0
 EU4  CONST_58  C34  C29  C06  C07    0.00   0.0  0
 EU4  CONST_59  C11  C10  C09  C08    0.00   0.0  0
 EU4  CONST_60  C25  C21  C20  C19  180.00   0.0  0
 EU4  CONST_61  C25  C21  C22  C23  180.00   0.0  0
 EU4  CONST_62  N35  C34  C29  C30  180.00   0.0  0
 EU4  CONST_63  N35  C34  N33  C32  180.00   0.0  0
 EU4  CONST_64  H13  C14  C15  C10  180.00   0.0  0
 EU4  CONST_65  H14  C16  C15  C10  180.00   0.0  0
 EU4  CONST_66  H15  C18  C09  C10  180.00   0.0  0
 EU4  CONST_67  H2   C20  C19  C13    0.00   0.0  0
 EU4  CONST_68  H4   C24  C19  C13    0.00   0.0  0
 EU4  CONST_69  H12  C11  N12  C13  180.00   0.0  0
 EU4  CONST_70  H1   C17  C16  C15  180.00   0.0  0
 EU4  CONST_71  H3   C22  C21  C20  180.00   0.0  0
 EU4  CONST_72  H16  C23  C22  C21  180.00   0.0  0
 EU4  CONST_73  H17  C32  N31  C30  180.00   0.0  0
 EU4  CONST_74  H18  N35  C34  C29    0.00   0.0  0
 EU4  CONST_75  H19  N35  C34  C29  180.00   0.0  0
 EU4  Var_01    F27  C25  C21  C20  -30.91  30.0  2
 EU4  Var_02    N05  N04  C02  C01  -60.87  30.0  2
 EU4  Var_03    H5   C01  C02  N04  -55.96  30.0  3
 EU4  Var_04    H9   C03  C02  N04  -65.56  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
 EU4  plan-1  C13  0.020
 EU4  plan-1  C20  0.020
 EU4  plan-1  C21  0.020
 EU4  plan-1  C22  0.020
 EU4  plan-1  C24  0.020
 EU4  plan-1  C19  0.020
 EU4  plan-1  C23  0.020
 EU4  plan-1  H2   0.020
 EU4  plan-1  H3   0.020
 EU4  plan-1  H4   0.020
 EU4  plan-1  H16  0.020
 EU4  plan-1  C25  0.020
 EU4  plan-2  C02  0.020
 EU4  plan-2  C06  0.020
 EU4  plan-2  C07  0.020
 EU4  plan-2  C29  0.020
 EU4  plan-2  C30  0.020
 EU4  plan-2  C32  0.020
 EU4  plan-2  C34  0.020
 EU4  plan-2  N04  0.020
 EU4  plan-2  N05  0.020
 EU4  plan-2  N31  0.020
 EU4  plan-2  N33  0.020
 EU4  plan-2  N35  0.020
 EU4  plan-2  H17  0.020
 EU4  plan-2  C08  0.020
 EU4  plan-3  C10  0.020
 EU4  plan-3  N12  0.020
 EU4  plan-3  C13  0.020
 EU4  plan-3  C15  0.020
 EU4  plan-3  C17  0.020
 EU4  plan-3  C07  0.020
 EU4  plan-3  C09  0.020
 EU4  plan-3  C11  0.020
 EU4  plan-3  C14  0.020
 EU4  plan-3  C16  0.020
 EU4  plan-3  C18  0.020
 EU4  plan-3  C19  0.020
 EU4  plan-3  H1   0.020
 EU4  plan-3  H12  0.020
 EU4  plan-3  H13  0.020
 EU4  plan-3  H14  0.020
 EU4  plan-3  H15  0.020
 EU4  plan-3  C08  0.020
 EU4  plan-4  C34  0.020
 EU4  plan-4  N35  0.020
 EU4  plan-4  H18  0.020
 EU4  plan-4  H19  0.020

