# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Mar  8 14:17:31 2022
#   Inital geometry file: a 135 line input string
#   Ligand name: 3-[3-(3-methyl-6-{[(1S)-1-phenylethyl]amino}-1H-pyrazolo[4,3-c]pyridin-1-yl)phenyl]propanamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H](Nc1cc2n(nc(C)c2cn1)c3cccc(CCC(N)=O)c3)c4ccccc4
#
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
 2FR  2FR  3-[3-(3-methyl-6-{[(1S)-1-phenylethyl]amino}-1H-pyrazolo[4,3-c]pyridin-1-yl)phenyl]propanamide  ligand  55  30  .  2022-03-10  2022-03-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_2FR
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
 2FR  C30   C  CR16  0  -0.327   5.1880   2.4718  -0.8566
 2FR  C28   C  CR16  0  -0.268   7.5905   2.3912  -0.9526
 2FR  C27   C  CR16  0  -0.238   7.5732   1.2409  -0.1732
 2FR  C26   C  CR16  0  -0.312   6.3674   0.7147   0.2673
 2FR  C24   C  CH3   0  -0.651   3.7397   0.8330   1.9378
 2FR  C23   C  CH1   0  -0.190   3.8445   0.7596   0.4129
 2FR  N21   N  NH2   0  -0.805  -8.5706   0.6783   0.2032
 2FR  C16   C  CR6   0   0.136  -3.7276   1.3750   0.0429
 2FR  C17   C  CR16  0  -0.352  -3.0398   0.1905  -0.1989
 2FR  C20   C  C     0   0.528  -7.5455   1.1786  -0.5048
 2FR  C15   C  CR16  0  -0.318  -3.1871   2.2979   0.9348
 2FR  C12   C  CR6   0   0.365  -1.8378  -0.0734   0.4481
 2FR  C13   C  CR16  0  -0.331  -1.3116   0.8445   1.3516
 2FR  C14   C  CR16  0  -0.235  -1.9883   2.0327   1.5800
 2FR  C10   C  CR5   0   0.246  -1.0266  -3.3786  -0.2452
 2FR  C4    C  CR56  0   0.567   0.1714  -1.4980   0.0581
 2FR  C5    C  CR56  0  -0.245   0.3050  -2.8667  -0.2198
 2FR  C6    C  CR16  0  -0.114   1.5890  -3.3675  -0.4113
 2FR  C3    C  CR16  0  -0.481   1.2816  -0.6624   0.1171
 2FR  C2    C  CR6   0   0.505   2.5165  -1.2790  -0.0943
 2FR  O22   O  O     0  -0.494  -7.6991   1.7814  -1.5573
 2FR  C19   C  CH2   0  -0.577  -6.1800   0.9282   0.1048
 2FR  C18   C  CH2   0  -0.506  -5.0467   1.6352  -0.6302
 2FR  N8    N  NR5   0  -0.536  -1.1631  -1.2781   0.1894
 2FR  N9    N  N     0  -0.274  -1.8759  -2.4211  -0.0065
 2FR  N1    N  N     0  -0.471   2.6548  -2.6042  -0.3441
 2FR  N7    N  NH1   0  -0.663   3.6869  -0.5888  -0.0975
 2FR  C25   C  CR6   0   0.169   5.1603   1.3231  -0.0735
 2FR  C29   C  CR16  0  -0.237   6.3942   3.0067  -1.2923
 2FR  H30   H  HCR6  0   0.253   4.2571   2.9562  -1.1272
 2FR  H28   H  HCR6  0   0.257   8.5319   2.8047  -1.2901
 2FR  H27   H  HCR6  0   0.257   8.5020   0.7538   0.0945
 2FR  H26   H  HCR6  0   0.256   6.3764  -0.1770   0.8850
 2FR  H24   H  HCH3  0   0.237   3.8437   1.8639   2.2767
 2FR  H24A  H  HCH3  0   0.238   2.7757   0.4618   2.2883
 2FR  H24B  H  HCH3  0   0.231   4.5225   0.2386   2.4103
 2FR  H23   H  HCH1  0   0.263   3.0517   1.3761  -0.0190
 2FR  HN21  H  HNH2  0   0.398  -9.5154   0.7649  -0.1333
 2FR  HN2A  H  HNH2  0   0.405  -8.4282   0.1780   1.0635
 2FR  H17   H  HCR6  0   0.261  -3.4416  -0.5319  -0.8988
 2FR  H15   H  HCR6  0   0.252  -3.7070   3.2290   1.1258
 2FR  H13   H  HCR6  0   0.272  -0.3983   0.6312   1.8900
 2FR  H14   H  HCR6  0   0.262  -1.5790   2.7499   2.2792
 2FR  H11   H  HCH3  0   0.253  -0.9994  -5.4606   0.2239
 2FR  H11A  H  HCH3  0   0.257  -2.5393  -4.8722  -0.4113
 2FR  H11B  H  HCH3  0   0.254  -1.1599  -5.1088  -1.4892
 2FR  H6    H  HCR6  0   0.265   1.7546  -4.4191  -0.6245
 2FR  H3    H  HCR6  0   0.282   1.1970   0.3988   0.2957
 2FR  H19   H  HCH2  0   0.274  -6.1969   1.2343   1.1548
 2FR  H19A  H  HCH2  0   0.278  -6.0075  -0.1521   0.1164
 2FR  H18   H  HCH2  0   0.251  -5.2369   2.7095  -0.6559
 2FR  H18A  H  HCH2  0   0.252  -5.0084   1.2960  -1.6667
 2FR  HN7   H  HNH1  0   0.385   4.5104  -1.1703  -0.1274
 2FR  H29   H  HCR6  0   0.257   6.3966   3.9027  -1.8996
 2FR  C11   C  CH3   0  -0.742  -1.4583  -4.7787  -0.4931

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
 2FR  C30  C25   aromatic  1.391  0.020  1.391
 2FR  C30  C29   aromatic  1.390  0.020  1.390
 2FR  C28  C27   aromatic  1.390  0.020  1.390
 2FR  C28  C29   aromatic  1.388  0.020  1.388
 2FR  C27  C26   aromatic  1.387  0.020  1.387
 2FR  C26  C25   aromatic  1.394  0.020  1.394
 2FR  C24  C23   single    1.530  0.020  1.530
 2FR  C23  N7    single    1.450  0.020  1.450
 2FR  C23  C25   single    1.512  0.020  1.512
 2FR  N21  C20   single    1.343  0.020  1.343
 2FR  C16  C17   aromatic  1.391  0.020  1.391
 2FR  C16  C15   aromatic  1.393  0.020  1.393
 2FR  C16  C18   single    1.504  0.020  1.504
 2FR  C17  C12   aromatic  1.390  0.020  1.390
 2FR  C20  O22   double    1.223  0.020  1.223
 2FR  C20  C19   single    1.516  0.020  1.516
 2FR  C15  C14   aromatic  1.387  0.020  1.387
 2FR  C12  C13   aromatic  1.391  0.020  1.391
 2FR  C12  N8    single    1.405  0.020  1.405
 2FR  C13  C14   aromatic  1.386  0.020  1.386
 2FR  C11  C10   single    1.486  0.020  1.486
 2FR  C10  C5    aromatic  1.427  0.020  1.427
 2FR  C10  N9    aromatic  1.302  0.020  1.302
 2FR  C4   C5    aromatic  1.403  0.020  1.403
 2FR  C4   C3    aromatic  1.391  0.020  1.391
 2FR  C4   N8    aromatic  1.359  0.020  1.359
 2FR  C5   C6    aromatic  1.392  0.020  1.392
 2FR  C6   N1    aromatic  1.313  0.020  1.313
 2FR  C3   C2    aromatic  1.396  0.020  1.396
 2FR  C2   N1    aromatic  1.356  0.020  1.356
 2FR  C2   N7    single    1.359  0.020  1.359
 2FR  C19  C18   single    1.525  0.020  1.525
 2FR  N8   N9    aromatic  1.361  0.020  1.361
 2FR  C30  H30   single    0.930  0.020  1.080
 2FR  C28  H28   single    0.930  0.020  1.080
 2FR  C27  H27   single    0.930  0.020  1.080
 2FR  C26  H26   single    0.930  0.020  1.080
 2FR  C24  H24   single    0.970  0.020  1.090
 2FR  C24  H24A  single    0.970  0.020  1.090
 2FR  C24  H24B  single    0.970  0.020  1.090
 2FR  C23  H23   single    0.970  0.020  1.090
 2FR  N21  HN21  single    0.860  0.020  1.020
 2FR  N21  HN2A  single    0.860  0.020  1.020
 2FR  C17  H17   single    0.930  0.020  1.080
 2FR  C15  H15   single    0.930  0.020  1.080
 2FR  C13  H13   single    0.930  0.020  1.080
 2FR  C14  H14   single    0.930  0.020  1.080
 2FR  C11  H11   single    0.970  0.020  1.090
 2FR  C11  H11A  single    0.970  0.020  1.090
 2FR  C11  H11B  single    0.970  0.020  1.090
 2FR  C6   H6    single    0.930  0.020  1.080
 2FR  C3   H3    single    0.930  0.020  1.080
 2FR  C19  H19   single    0.970  0.020  1.090
 2FR  C19  H19A  single    0.970  0.020  1.090
 2FR  C18  H18   single    0.970  0.020  1.090
 2FR  C18  H18A  single    0.970  0.020  1.090
 2FR  N7   HN7   single    0.890  0.020  1.040
 2FR  C29  H29   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
 2FR  H30   C30  C29   119.69  3.000
 2FR  H30   C30  C25   119.52  3.000
 2FR  C29   C30  C25   120.79  3.000
 2FR  H28   C28  C29   120.27  3.000
 2FR  H28   C28  C27   120.14  3.000
 2FR  C29   C28  C27   119.59  3.000
 2FR  H27   C27  C26   119.77  3.000
 2FR  H27   C27  C28   120.04  3.000
 2FR  C26   C27  C28   120.19  3.000
 2FR  H26   C26  C25   120.34  3.000
 2FR  H26   C26  C27   119.04  3.000
 2FR  C25   C26  C27   120.63  3.000
 2FR  H24B  C24  H24A  108.04  3.000
 2FR  H24B  C24  H24   108.19  3.000
 2FR  H24A  C24  H24   107.83  3.000
 2FR  H24B  C24  C23   110.88  3.000
 2FR  H24A  C24  C23   111.37  3.000
 2FR  H24   C24  C23   110.40  3.000
 2FR  H23   C23  C25   107.09  3.000
 2FR  H23   C23  N7    107.85  3.000
 2FR  C25   C23  N7    109.14  3.000
 2FR  H23   C23  C24   108.47  3.000
 2FR  C25   C23  C24   111.24  3.000
 2FR  N7    C23  C24   112.82  3.000
 2FR  HN2A  N21  HN21  117.50  3.000
 2FR  HN2A  N21  C20   121.91  3.000
 2FR  HN21  N21  C20   120.55  3.000
 2FR  C18   C16  C15   120.83  3.000
 2FR  C18   C16  C17   120.22  3.000
 2FR  C15   C16  C17   118.93  3.000
 2FR  H17   C17  C12   119.66  3.000
 2FR  H17   C17  C16   119.80  3.000
 2FR  C12   C17  C16   120.55  3.000
 2FR  C19   C20  O22   122.73  3.000
 2FR  C19   C20  N21   114.46  3.000
 2FR  O22   C20  N21   122.80  3.000
 2FR  H15   C15  C14   119.80  3.000
 2FR  H15   C15  C16   119.75  3.000
 2FR  C14   C15  C16   120.44  3.000
 2FR  N8    C12  C13   120.25  3.000
 2FR  N8    C12  C17   119.49  3.000
 2FR  C13   C12  C17   120.26  3.000
 2FR  H13   C13  C14   119.95  3.000
 2FR  H13   C13  C12   120.83  3.000
 2FR  C14   C13  C12   119.20  3.000
 2FR  H14   C14  C13   119.34  3.000
 2FR  H14   C14  C15   120.06  3.000
 2FR  C13   C14  C15   120.60  3.000
 2FR  N9    C10  C5    109.98  3.000
 2FR  N9    C10  C11   122.28  3.000
 2FR  C5    C10  C11   127.74  3.000
 2FR  N8    C4   C3    133.05  3.000
 2FR  N8    C4   C5    105.69  3.000
 2FR  C3    C4   C5    121.23  3.000
 2FR  C6    C5   C4    117.79  3.000
 2FR  C6    C5   C10   136.85  3.000
 2FR  C4    C5   C10   105.35  3.000
 2FR  H6    C6   N1    116.71  3.000
 2FR  H6    C6   C5    121.09  3.000
 2FR  N1    C6   C5    122.20  3.000
 2FR  H3    C3   C2    121.90  3.000
 2FR  H3    C3   C4    122.35  3.000
 2FR  C2    C3   C4    115.74  3.000
 2FR  N7    C2   N1    114.10  3.000
 2FR  N7    C2   C3    122.53  3.000
 2FR  N1    C2   C3    123.35  3.000
 2FR  H19A  C19  H19   105.58  3.000
 2FR  H19A  C19  C18   110.23  3.000
 2FR  H19   C19  C18   110.15  3.000
 2FR  H19A  C19  C20   108.02  3.000
 2FR  H19   C19  C20   109.02  3.000
 2FR  C18   C19  C20   113.52  3.000
 2FR  H18A  C18  H18   106.84  3.000
 2FR  H18A  C18  C19   109.87  3.000
 2FR  H18   C18  C19   109.77  3.000
 2FR  H18A  C18  C16   109.91  3.000
 2FR  H18   C18  C16   109.50  3.000
 2FR  C19   C18  C16   110.86  3.000
 2FR  N9    N8   C4    111.38  3.000
 2FR  N9    N8   C12   119.68  3.000
 2FR  C4    N8   C12   128.91  3.000
 2FR  N8    N9   C10   107.60  3.000
 2FR  C2    N1   C6    119.67  3.000
 2FR  HN7   N7   C2    114.23  3.000
 2FR  HN7   N7   C23   117.24  3.000
 2FR  C2    N7   C23   124.41  3.000
 2FR  C23   C25  C26   120.82  3.000
 2FR  C23   C25  C30   120.43  3.000
 2FR  C26   C25  C30   118.75  3.000
 2FR  H29   C29  C28   120.17  3.000
 2FR  H29   C29  C30   119.77  3.000
 2FR  C28   C29  C30   120.06  3.000
 2FR  H11B  C11  H11A  108.32  3.000
 2FR  H11B  C11  H11   107.22  3.000
 2FR  H11A  C11  H11   108.35  3.000
 2FR  H11B  C11  C10   110.97  3.000
 2FR  H11A  C11  C10   110.92  3.000
 2FR  H11   C11  C10   110.93  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
 2FR  CONST_01  C27   C26  C25  C30     0.00   0.0  0
 2FR  CONST_02  C27   C28  C29  C30     0.00   0.0  0
 2FR  CONST_03  C25   C26  C27  C28     0.00   0.0  0
 2FR  CONST_04  C25   C30  C29  C28     0.00   0.0  0
 2FR  CONST_05  C29   C28  C27  C26     0.00   0.0  0
 2FR  CONST_06  C29   C30  C25  C26     0.00   0.0  0
 2FR  CONST_07  C13   C12  C17  C16     0.00   0.0  0
 2FR  CONST_08  N8    C12  C17  C16   180.00   0.0  0
 2FR  CONST_09  C13   C14  C15  C16     0.00   0.0  0
 2FR  CONST_10  C14   C15  C16  C17     0.00   0.0  0
 2FR  CONST_11  C14   C13  C12  C17     0.00   0.0  0
 2FR  CONST_14  C12   C17  C16  C15     0.00   0.0  0
 2FR  CONST_15  C12   C13  C14  C15     0.00   0.0  0
 2FR  CONST_16  C5    C4   N8   C12   180.00   0.0  0
 2FR  CONST_17  C3    C4   N8   C12     0.00   0.0  0
 2FR  CONST_18  C10   N9   N8   C12   180.00   0.0  0
 2FR  CONST_21  N8    C12  C13  C14   180.00   0.0  0
 2FR  CONST_22  C3    C4   C5   C10   180.00   0.0  0
 2FR  CONST_23  N8    C4   C5   C10     0.00   0.0  0
 2FR  CONST_24  N1    C6   C5   C10   180.00   0.0  0
 2FR  CONST_25  C4    N8   N9   C10     0.00   0.0  0
 2FR  CONST_26  N9    C10  C5   C4      0.00   0.0  0
 2FR  CONST_27  N1    C6   C5   C4      0.00   0.0  0
 2FR  CONST_28  N1    C2   C3   C4      0.00   0.0  0
 2FR  CONST_29  N8    N9   C10  C5      0.00   0.0  0
 2FR  CONST_30  C2    C3   C4   C5      0.00   0.0  0
 2FR  CONST_31  N9    N8   C4   C5      0.00   0.0  0
 2FR  CONST_32  C2    N1   C6   C5      0.00   0.0  0
 2FR  CONST_33  N9    C10  C5   C6    180.00   0.0  0
 2FR  CONST_34  C3    C4   C5   C6      0.00   0.0  0
 2FR  CONST_35  N8    C4   C5   C6    180.00   0.0  0
 2FR  CONST_36  C3    C2   N1   C6      0.00   0.0  0
 2FR  CONST_37  N9    N8   C4   C3    180.00   0.0  0
 2FR  CONST_38  N8    C4   C3   C2    180.00   0.0  0
 2FR  CONST_39  C23   C25  C26  C27   180.00   0.0  0
 2FR  CONST_40  C29   C30  C25  C23   180.00   0.0  0
 2FR  CONST_41  C18   C16  C17  C12   180.00   0.0  0
 2FR  CONST_42  C18   C16  C15  C14   180.00   0.0  0
 2FR  CONST_43  C4    C5   C10  C11   180.00   0.0  0
 2FR  CONST_44  C6    C5   C10  C11     0.00   0.0  0
 2FR  CONST_45  N8    N9   C10  C11   180.00   0.0  0
 2FR  CONST_46  N7    C2   C3   C4    180.00   0.0  0
 2FR  CONST_47  N7    C2   N1   C6    180.00   0.0  0
 2FR  CONST_48  H26   C26  C25  C30   180.00   0.0  0
 2FR  CONST_49  H28   C28  C29  C30   180.00   0.0  0
 2FR  CONST_50  H30   C30  C29  C28   180.00   0.0  0
 2FR  CONST_51  H29   C29  C28  C27   180.00   0.0  0
 2FR  CONST_52  H14   C14  C15  C16   180.00   0.0  0
 2FR  CONST_53  H15   C15  C16  C17   180.00   0.0  0
 2FR  CONST_54  H13   C13  C12  C17   180.00   0.0  0
 2FR  CONST_55  H17   C17  C16  C15   180.00   0.0  0
 2FR  CONST_56  H6    C6   C5   C10     0.00   0.0  0
 2FR  CONST_57  H3    C3   C4   C5    180.00   0.0  0
 2FR  CONST_58  H27   C27  C26  C25   180.00   0.0  0
 2FR  CONST_60  N1    C2   N7   C23   180.00   0.0  0
 2FR  CONST_61  HN7   N7   C2   C3    180.00   0.0  0
 2FR  CONST_62  HN21  N21  C20  O22     0.00   0.0  0
 2FR  CONST_63  HN2A  N21  C20  O22   180.00   0.0  0
 2FR  Var_01    C19   C18  C16  C17    81.25  30.0  2
 2FR  Var_02    H11   C11  C10  C5     57.33  30.0  2
 2FR  Var_03    C20   C19  C18  C16   178.57  30.0  1
 2FR  Var_04    C18   C19  C20  N21  -173.58  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
 2FR  chir_01  C23  C24  N7  C25  positiv

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
 2FR  plan-1  C30   0.020
 2FR  plan-1  C28   0.020
 2FR  plan-1  C27   0.020
 2FR  plan-1  C26   0.020
 2FR  plan-1  C23   0.020
 2FR  plan-1  C25   0.020
 2FR  plan-1  C29   0.020
 2FR  plan-1  H30   0.020
 2FR  plan-1  H28   0.020
 2FR  plan-1  H27   0.020
 2FR  plan-1  H26   0.020
 2FR  plan-1  H29   0.020
 2FR  plan-2  C16   0.020
 2FR  plan-2  C17   0.020
 2FR  plan-2  C15   0.020
 2FR  plan-2  C12   0.020
 2FR  plan-2  C13   0.020
 2FR  plan-2  C14   0.020
 2FR  plan-2  C18   0.020
 2FR  plan-2  N8    0.020
 2FR  plan-2  H17   0.020
 2FR  plan-2  H15   0.020
 2FR  plan-2  H13   0.020
 2FR  plan-2  H14   0.020
 2FR  plan-3  C12   0.020
 2FR  plan-3  C10   0.020
 2FR  plan-3  C4    0.020
 2FR  plan-3  C5    0.020
 2FR  plan-3  C6    0.020
 2FR  plan-3  C3    0.020
 2FR  plan-3  C2    0.020
 2FR  plan-3  N8    0.020
 2FR  plan-3  N9    0.020
 2FR  plan-3  N1    0.020
 2FR  plan-3  N7    0.020
 2FR  plan-3  H6    0.020
 2FR  plan-3  H3    0.020
 2FR  plan-3  C11   0.020
 2FR  plan-4  N21   0.020
 2FR  plan-4  C20   0.020
 2FR  plan-4  O22   0.020
 2FR  plan-4  C19   0.020
 2FR  plan-4  HN21  0.020
 2FR  plan-4  HN2A  0.020
 2FR  plan-5  C23   0.020
 2FR  plan-5  C2    0.020
 2FR  plan-5  N7    0.020
 2FR  plan-5  HN7   0.020

