# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri May  8 06:38:40 2020
#   Inital geometry file: a 128 line input string
#   Ligand name: (2R)-2-{[6-(furan-3-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-yl]oxy}-2-phenylethanamine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: NC[C@H](Oc1cnc(c2cocc2)c(c1)c3c[nH]c4ncccc34)c5ccccc5
#
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
 IE8  IE8  (2R)-2-{[6-(furan-3-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-yl]oxy}-2-phenylethanamine  ligand  50  30  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_IE8
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
 IE8  C    C  CH2   0  -0.289   4.0252   1.9549   1.5982
 IE8  N    N  NH2   0  -0.794   2.9810   2.8356   2.0873
 IE8  O    O  O2    0  -0.492   2.6066   0.0325   1.4939
 IE8  C1   C  CH1   0  -0.061   3.4402   0.8756   0.6986
 IE8  N1   N  N     0  -0.416   0.0303  -2.1155   0.2049
 IE8  O1   O  O     0  -0.394  -3.6577  -3.3268  -1.2996
 IE8  C2   C  CR6   0   0.291   1.4255  -0.3433   0.9556
 IE8  N2   N  NR15  0  -0.664  -2.9308   2.9587  -0.7444
 IE8  C3   C  CR16  0  -0.167   1.1678  -1.6888   0.7241
 IE8  N3   N  N     0  -0.427  -5.0979   2.5940   0.1981
 IE8  C4   C  CR6   0   0.164  -0.9287  -1.2459  -0.1117
 IE8  C5   C  CR5   0  -0.048  -2.1141  -1.8242  -0.7518
 IE8  C6   C  CR15  0  -0.389  -2.9796  -1.2643  -1.7504
 IE8  C7   C  CR15  0   0.013  -3.8867  -2.2207  -2.0411
 IE8  C8   C  CR15  0  -0.010  -2.5830  -3.0811  -0.5318
 IE8  C9   C  CR6   0   0.026  -0.7898   0.1298   0.1441
 IE8  C10  C  CR16  0  -0.285   0.4194   0.5676   0.6756
 IE8  C11  C  CR5   0  -0.087  -1.8634   1.1000  -0.0832
 IE8  C12  C  CR15  0  -0.037  -1.7476   2.2819  -0.7657
 IE8  C13  C  CR56  0   0.469  -3.8451   2.2388  -0.0362
 IE8  C14  C  CR16  0  -0.092  -5.7969   1.7352   0.9257
 IE8  C15  C  CR16  0  -0.343  -5.2842   0.5349   1.4314
 IE8  C16  C  CR16  0  -0.241  -3.9726   0.1802   1.1715
 IE8  C17  C  CR56  0  -0.015  -3.2104   1.0561   0.4037
 IE8  C18  C  CR6   0   0.130   4.5137   0.0590   0.0252
 IE8  C19  C  CR16  0  -0.308   4.8750   0.3354  -1.2890
 IE8  C20  C  CR16  0  -0.241   5.8946  -0.3757  -1.9090
 IE8  C21  C  CR16  0  -0.266   6.5617  -1.3776  -1.2178
 IE8  C22  C  CR16  0  -0.240   6.2032  -1.6627   0.0942
 IE8  C23  C  CR16  0  -0.298   5.1864  -0.9490   0.7126
 IE8  H    H  HCH2  0   0.215   4.8124   2.4688   1.0313
 IE8  HA   H  HCH2  0   0.233   4.5201   1.4765   2.4477
 IE8  HN   H  HNH2  0   0.355   3.3447   3.4092   2.8367
 IE8  HNA  H  HNH2  0   0.345   2.7122   3.4788   1.3533
 IE8  H1   H  HCH1  0   0.246   2.8390   1.3691  -0.0764
 IE8  H3   H  HCR6  0   0.264   1.9165  -2.4363   0.9670
 IE8  H6   H  HCR5  0   0.265  -2.9203  -0.2872  -2.1995
 IE8  H7   H  HCR5  0   0.283  -4.7187  -2.2581  -2.7252
 IE8  H8   H  HCR5  0   0.282  -2.2618  -3.8709   0.1280
 IE8  H10  H  HCR6  0   0.272   0.5594   1.6163   0.9121
 IE8  H12  H  HCR5  0   0.295  -0.8935   2.6853  -1.2865
 IE8  H14  H  HCR6  0   0.256  -6.8272   2.0041   1.1289
 IE8  H15  H  HCR6  0   0.263  -5.9243  -0.1056   2.0221
 IE8  H16  H  HCR6  0   0.254  -3.5601  -0.7458   1.5508
 IE8  H19  H  HCR6  0   0.252   4.3526   1.1109  -1.8375
 IE8  H20  H  HCR6  0   0.257   6.1612  -0.1512  -2.9337
 IE8  H21  H  HCR6  0   0.256   7.3536  -1.9364  -1.6998
 IE8  H22  H  HCR6  0   0.256   6.7164  -2.4448   0.6388
 IE8  H23  H  HCR6  0   0.252   4.9150  -1.1855   1.7337
 IE8  HN2  H  HNR5  0   0.413  -3.1013   3.8467  -1.1876

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
 IE8  C    N    single    1.451  0.020  1.451
 IE8  C    C1   single    1.522  0.020  1.522
 IE8  O    C1   single    1.428  0.020  1.428
 IE8  O    C2   single    1.351  0.020  1.351
 IE8  C1   C18  single    1.508  0.020  1.508
 IE8  N1   C3   aromatic  1.321  0.020  1.321
 IE8  N1   C4   aromatic  1.333  0.020  1.333
 IE8  O1   C7   aromatic  1.351  0.020  1.351
 IE8  O1   C8   aromatic  1.343  0.020  1.343
 IE8  C2   C3   aromatic  1.389  0.020  1.389
 IE8  C2   C10  aromatic  1.386  0.020  1.386
 IE8  N2   C12  aromatic  1.363  0.020  1.363
 IE8  N2   C13  aromatic  1.362  0.020  1.362
 IE8  N3   C13  aromatic  1.323  0.020  1.323
 IE8  N3   C14  aromatic  1.325  0.020  1.325
 IE8  C4   C5   single    1.466  0.020  1.466
 IE8  C4   C9   aromatic  1.406  0.020  1.406
 IE8  C5   C6   aromatic  1.435  0.020  1.435
 IE8  C5   C8   aromatic  1.359  0.020  1.359
 IE8  C6   C7   aromatic  1.350  0.020  1.350
 IE8  C9   C10  aromatic  1.392  0.020  1.392
 IE8  C9   C11  single    1.465  0.020  1.465
 IE8  C11  C12  aromatic  1.370  0.020  1.370
 IE8  C11  C17  aromatic  1.433  0.020  1.433
 IE8  C13  C17  aromatic  1.412  0.020  1.412
 IE8  C14  C15  aromatic  1.400  0.020  1.400
 IE8  C15  C16  aromatic  1.383  0.020  1.383
 IE8  C16  C17  aromatic  1.392  0.020  1.392
 IE8  C18  C19  aromatic  1.391  0.020  1.391
 IE8  C18  C23  aromatic  1.393  0.020  1.393
 IE8  C19  C20  aromatic  1.389  0.020  1.389
 IE8  C20  C21  aromatic  1.388  0.020  1.388
 IE8  C21  C22  aromatic  1.390  0.020  1.390
 IE8  C22  C23  aromatic  1.388  0.020  1.388
 IE8  C    H    single    0.970  0.020  1.090
 IE8  C    HA   single    0.970  0.020  1.090
 IE8  N    HN   single    0.890  0.020  1.040
 IE8  N    HNA  single    0.890  0.020  1.040
 IE8  C1   H1   single    0.970  0.020  1.090
 IE8  N2   HN2  single    0.860  0.020  1.020
 IE8  C3   H3   single    0.930  0.020  1.080
 IE8  C6   H6   single    0.930  0.020  1.080
 IE8  C7   H7   single    0.930  0.020  1.080
 IE8  C8   H8   single    0.930  0.020  1.080
 IE8  C10  H10  single    0.930  0.020  1.080
 IE8  C12  H12  single    0.930  0.020  1.080
 IE8  C14  H14  single    0.930  0.020  1.080
 IE8  C15  H15  single    0.930  0.020  1.080
 IE8  C16  H16  single    0.930  0.020  1.080
 IE8  C19  H19  single    0.930  0.020  1.080
 IE8  C20  H20  single    0.930  0.020  1.080
 IE8  C21  H21  single    0.930  0.020  1.080
 IE8  C22  H22  single    0.930  0.020  1.080
 IE8  C23  H23  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
 IE8  HA   C    H    106.35  3.000
 IE8  HA   C    C1   108.84  3.000
 IE8  H    C    C1   107.60  3.000
 IE8  HA   C    N    109.24  3.000
 IE8  H    C    N    113.95  3.000
 IE8  C1   C    N    110.67  3.000
 IE8  HNA  N    HN   105.81  3.000
 IE8  HNA  N    C    109.41  3.000
 IE8  HN   N    C    109.58  3.000
 IE8  C2   O    C1   116.91  3.000
 IE8  H1   C1   C18  108.55  3.000
 IE8  H1   C1   O    109.81  3.000
 IE8  C18  C1   O    110.16  3.000
 IE8  H1   C1   C    108.00  3.000
 IE8  C18  C1   C    111.99  3.000
 IE8  O    C1   C    108.30  3.000
 IE8  C4   N1   C3   120.14  3.000
 IE8  C8   O1   C7   107.43  3.000
 IE8  C10  C2   C3   117.92  3.000
 IE8  C10  C2   O    122.16  3.000
 IE8  C3   C2   O    119.86  3.000
 IE8  HN2  N2   C13  125.53  3.000
 IE8  HN2  N2   C12  125.30  3.000
 IE8  C13  N2   C12  109.16  3.000
 IE8  H3   C3   C2   120.11  3.000
 IE8  H3   C3   N1   117.34  3.000
 IE8  C2   C3   N1   122.55  3.000
 IE8  C14  N3   C13  115.01  3.000
 IE8  C9   C4   C5   123.04  3.000
 IE8  C9   C4   N1   121.60  3.000
 IE8  C5   C4   N1   115.35  3.000
 IE8  C8   C5   C6   105.39  3.000
 IE8  C8   C5   C4   124.96  3.000
 IE8  C6   C5   C4   129.60  3.000
 IE8  H6   C6   C7   126.16  3.000
 IE8  H6   C6   C5   127.66  3.000
 IE8  C7   C6   C5   106.18  3.000
 IE8  H7   C7   C6   132.84  3.000
 IE8  H7   C7   O1   116.79  3.000
 IE8  C6   C7   O1   110.36  3.000
 IE8  H8   C8   C5   132.34  3.000
 IE8  H8   C8   O1   117.01  3.000
 IE8  C5   C8   O1   110.64  3.000
 IE8  C11  C9   C10  119.19  3.000
 IE8  C11  C9   C4   123.18  3.000
 IE8  C10  C9   C4   117.59  3.000
 IE8  H10  C10  C9   120.00  3.000
 IE8  H10  C10  C2   119.87  3.000
 IE8  C9   C10  C2   120.08  3.000
 IE8  C17  C11  C12  105.97  3.000
 IE8  C17  C11  C9   128.03  3.000
 IE8  C12  C11  C9   125.93  3.000
 IE8  H12  C12  C11  129.07  3.000
 IE8  H12  C12  N2   120.61  3.000
 IE8  C11  C12  N2   110.32  3.000
 IE8  C17  C13  N3   126.52  3.000
 IE8  C17  C13  N2   107.63  3.000
 IE8  N3   C13  N2   125.85  3.000
 IE8  H14  C14  C15  119.54  3.000
 IE8  H14  C14  N3   116.33  3.000
 IE8  C15  C14  N3   124.13  3.000
 IE8  H15  C15  C16  120.80  3.000
 IE8  H15  C15  C14  119.25  3.000
 IE8  C16  C15  C14  119.95  3.000
 IE8  H16  C16  C17  121.53  3.000
 IE8  H16  C16  C15  120.99  3.000
 IE8  C17  C16  C15  117.48  3.000
 IE8  C16  C17  C13  116.92  3.000
 IE8  C16  C17  C11  136.17  3.000
 IE8  C13  C17  C11  106.91  3.000
 IE8  C23  C18  C19  118.99  3.000
 IE8  C23  C18  C1   121.02  3.000
 IE8  C19  C18  C1   119.96  3.000
 IE8  H19  C19  C20  119.61  3.000
 IE8  H19  C19  C18  119.68  3.000
 IE8  C20  C19  C18  120.71  3.000
 IE8  H20  C20  C21  120.18  3.000
 IE8  H20  C20  C19  119.81  3.000
 IE8  C21  C20  C19  120.00  3.000
 IE8  H21  C21  C22  120.21  3.000
 IE8  H21  C21  C20  120.17  3.000
 IE8  C22  C21  C20  119.62  3.000
 IE8  H22  C22  C23  119.65  3.000
 IE8  H22  C22  C21  120.07  3.000
 IE8  C23  C22  C21  120.28  3.000
 IE8  H23  C23  C22  119.45  3.000
 IE8  H23  C23  C18  120.15  3.000
 IE8  C22  C23  C18  120.40  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
 IE8  CONST_01  C10  C2   C3   N1     0.00   0.0  0
 IE8  CONST_04  C10  C9   C4   N1     0.00   0.0  0
 IE8  CONST_05  C11  C9   C4   N1   180.00   0.0  0
 IE8  CONST_06  C5   C6   C7   O1     0.00   0.0  0
 IE8  CONST_07  C4   C5   C8   O1   180.00   0.0  0
 IE8  CONST_08  C6   C5   C8   O1     0.00   0.0  0
 IE8  CONST_09  C4   N1   C3   C2     0.00   0.0  0
 IE8  CONST_10  C4   C9   C10  C2     0.00   0.0  0
 IE8  CONST_11  C11  C9   C10  C2   180.00   0.0  0
 IE8  CONST_12  C9   C11  C12  N2   180.00   0.0  0
 IE8  CONST_13  C17  C11  C12  N2     0.00   0.0  0
 IE8  CONST_14  C14  N3   C13  N2   180.00   0.0  0
 IE8  CONST_15  C11  C17  C13  N2     0.00   0.0  0
 IE8  CONST_16  C16  C17  C13  N2   180.00   0.0  0
 IE8  CONST_17  C5   C4   N1   C3   180.00   0.0  0
 IE8  CONST_18  C9   C4   N1   C3     0.00   0.0  0
 IE8  CONST_19  C9   C10  C2   C3     0.00   0.0  0
 IE8  CONST_20  C12  N2   C13  N3   180.00   0.0  0
 IE8  CONST_21  C11  C17  C13  N3   180.00   0.0  0
 IE8  CONST_22  C16  C17  C13  N3     0.00   0.0  0
 IE8  CONST_23  C16  C15  C14  N3     0.00   0.0  0
 IE8  CONST_24  C7   C6   C5   C4   180.00   0.0  0
 IE8  CONST_27  C10  C9   C4   C5   180.00   0.0  0
 IE8  CONST_28  C11  C9   C4   C5     0.00   0.0  0
 IE8  CONST_29  C7   O1   C8   C5     0.00   0.0  0
 IE8  CONST_31  C8   O1   C7   C6     0.00   0.0  0
 IE8  CONST_32  C8   C5   C6   C7     0.00   0.0  0
 IE8  CONST_34  C13  C17  C11  C9   180.00   0.0  0
 IE8  CONST_35  C16  C17  C11  C9     0.00   0.0  0
 IE8  CONST_38  C13  N2   C12  C11    0.00   0.0  0
 IE8  CONST_39  C15  C16  C17  C11  180.00   0.0  0
 IE8  CONST_40  C17  C13  N2   C12    0.00   0.0  0
 IE8  CONST_41  C13  C17  C11  C12    0.00   0.0  0
 IE8  CONST_42  C16  C17  C11  C12  180.00   0.0  0
 IE8  CONST_43  C15  C14  N3   C13    0.00   0.0  0
 IE8  CONST_44  C15  C16  C17  C13    0.00   0.0  0
 IE8  CONST_45  C17  C13  N3   C14    0.00   0.0  0
 IE8  CONST_46  C17  C16  C15  C14    0.00   0.0  0
 IE8  CONST_47  C21  C20  C19  C18    0.00   0.0  0
 IE8  CONST_48  C21  C22  C23  C18    0.00   0.0  0
 IE8  CONST_49  C22  C23  C18  C19    0.00   0.0  0
 IE8  CONST_50  C22  C21  C20  C19    0.00   0.0  0
 IE8  CONST_51  C23  C18  C19  C20    0.00   0.0  0
 IE8  CONST_52  C23  C22  C21  C20    0.00   0.0  0
 IE8  CONST_53  N1   C3   C2   O    180.00   0.0  0
 IE8  CONST_54  C9   C10  C2   O    180.00   0.0  0
 IE8  CONST_55  C20  C19  C18  C1   180.00   0.0  0
 IE8  CONST_56  C22  C23  C18  C1   180.00   0.0  0
 IE8  CONST_57  H6   C6   C7   O1   180.00   0.0  0
 IE8  CONST_58  H10  C10  C2   C3   180.00   0.0  0
 IE8  CONST_59  HN2  N2   C13  N3     0.00   0.0  0
 IE8  CONST_60  H15  C15  C14  N3   180.00   0.0  0
 IE8  CONST_61  H3   C3   N1   C4   180.00   0.0  0
 IE8  CONST_62  H8   C8   C5   C4     0.00   0.0  0
 IE8  CONST_63  H7   C7   C6   C5   180.00   0.0  0
 IE8  CONST_64  H12  C12  C11  C9     0.00   0.0  0
 IE8  CONST_65  H16  C16  C17  C11    0.00   0.0  0
 IE8  CONST_66  H14  C14  N3   C13  180.00   0.0  0
 IE8  CONST_67  H20  C20  C19  C18  180.00   0.0  0
 IE8  CONST_68  H22  C22  C23  C18  180.00   0.0  0
 IE8  CONST_69  H23  C23  C18  C19  180.00   0.0  0
 IE8  CONST_70  H21  C21  C20  C19  180.00   0.0  0
 IE8  CONST_71  H19  C19  C20  C21  180.00   0.0  0
 IE8  Var_01    C3   C2   O    C1   117.91  30.0  2
 IE8  Var_02    HN   N    C    C1   167.34  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
 IE8  chir_01  C1  C  O  C18  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
 IE8  plan-1  O1   0.020
 IE8  plan-1  C4   0.020
 IE8  plan-1  C5   0.020
 IE8  plan-1  C6   0.020
 IE8  plan-1  C7   0.020
 IE8  plan-1  C8   0.020
 IE8  plan-1  H6   0.020
 IE8  plan-1  H7   0.020
 IE8  plan-1  H8   0.020
 IE8  plan-2  O    0.020
 IE8  plan-2  N1   0.020
 IE8  plan-2  C2   0.020
 IE8  plan-2  C3   0.020
 IE8  plan-2  C4   0.020
 IE8  plan-2  C5   0.020
 IE8  plan-2  C9   0.020
 IE8  plan-2  C10  0.020
 IE8  plan-2  C11  0.020
 IE8  plan-2  H3   0.020
 IE8  plan-2  H10  0.020
 IE8  plan-3  C1   0.020
 IE8  plan-3  C18  0.020
 IE8  plan-3  C19  0.020
 IE8  plan-3  C20  0.020
 IE8  plan-3  C21  0.020
 IE8  plan-3  C22  0.020
 IE8  plan-3  C23  0.020
 IE8  plan-3  H19  0.020
 IE8  plan-3  H20  0.020
 IE8  plan-3  H21  0.020
 IE8  plan-3  H22  0.020
 IE8  plan-3  H23  0.020
 IE8  plan-4  N2   0.020
 IE8  plan-4  N3   0.020
 IE8  plan-4  C9   0.020
 IE8  plan-4  C11  0.020
 IE8  plan-4  C12  0.020
 IE8  plan-4  C13  0.020
 IE8  plan-4  C14  0.020
 IE8  plan-4  C15  0.020
 IE8  plan-4  C16  0.020
 IE8  plan-4  C17  0.020
 IE8  plan-4  H12  0.020
 IE8  plan-4  H14  0.020
 IE8  plan-4  H15  0.020
 IE8  plan-4  H16  0.020
 IE8  plan-4  HN2  0.020

