# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr  4 21:11:22 2020
#   Inital geometry file: a 122 line input string
#   Ligand name: 5-{2-(ethylcarbamoyl)-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-1H-pyrrolo[2,3-b]pyridin-5-yl}pyridine-3-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCNC(=O)c1[nH]c2ncc(c3cncc(c3)C(O)=O)c(n4ccc(n4)C(F)(F)F)c2c1
#
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
 0R9  0R9  '5-{2-(ethylcarbamoyl)-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-1H-pyrrolo[2,3-b]pyridin-5-yl}pyridine-3-carboxylic acid'  ligand  46  32  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_0R9
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
 0R9  C1   C  CH3    0  -0.699   8.7429   1.2131   0.2554
 0R9  C2   C  CH2    0  -0.264   7.8318   0.0081   0.3837
 0R9  N3   N  NH1    0  -0.649   6.4411   0.4054   0.2580
 0R9  C4   C  C      0   0.535   5.4333  -0.4476   0.4905
 0R9  O5   O  O      0  -0.481   5.5956  -1.6084   0.8390
 0R9  C6   C  CR5    0   0.257   4.0650   0.0869   0.3033
 0R9  C7   C  CR15   0  -0.427   2.9375  -0.6577   0.0876
 0R9  C8   C  CR56   0  -0.006   1.8687   0.2664  -0.0606
 0R9  C9   C  CR6    0   0.349   0.4935   0.1949  -0.2749
 0R9  C10  C  CR6    0  -0.037  -0.2434   1.3700  -0.3185
 0R9  C11  C  CR16   0  -0.117   0.4436   2.5833  -0.1131
 0R9  N12  N  N      0  -0.413   1.7411   2.6980   0.0928
 0R9  C13  C  CR56   0   0.475   2.4138   1.5596   0.1007
 0R9  N14  N  NR15   0  -0.728   3.7480   1.4228   0.3029
 0R9  C15  C  CR6    0  -0.011  -1.6906   1.4062  -0.5993
 0R9  C16  C  CR16   0  -0.214  -2.5760   2.0696   0.2399
 0R9  C17  C  CR6    0  -0.181  -3.9291   2.1085  -0.0688
 0R9  C18  C  CR16   0  -0.087  -4.3341   1.4621  -1.2305
 0R9  N19  N  N      0  -0.400  -3.5032   0.8287  -2.0525
 0R9  C20  C  CR16   0  -0.086  -2.2167   0.8069  -1.7421
 0R9  C21  C  C      0   0.403  -4.9276   2.8204   0.8343
 0R9  O22  O  O      0  -0.588  -4.4636   3.3407   1.8653
 0R9  O23  O  OC    -1  -0.589  -6.1139   2.8156   0.4582
 0R9  N24  N  NR5    0  -0.410  -0.1217  -1.0642  -0.4242
 0R9  C25  C  CR15   0   0.043   0.2228  -2.0394  -1.3003
 0R9  C26  C  CR15   0  -0.515  -0.6688  -3.0611  -1.1165
 0R9  C27  C  CR5    0   0.023  -1.5116  -2.5901  -0.0948
 0R9  N28  N  N      0  -0.269  -1.1742  -1.3882   0.3147
 0R9  C29  C  CT     0   1.067  -2.6434  -3.3118   0.5421
 0R9  F30  F  F      0  -0.310  -3.3393  -4.0061  -0.3660
 0R9  F31  F  F      0  -0.315  -2.2173  -4.1960   1.4560
 0R9  F32  F  F      0  -0.302  -3.4851  -2.4832   1.1580
 0R9  H1   H  HCH3   0   0.235   8.6326   1.6991  -0.7152
 0R9  H2   H  HCH3   0   0.237   8.5406   1.9493   1.0335
 0R9  H3   H  HCH3   0   0.247   9.7814   0.8998   0.3506
 0R9  H4   H  HCH2   0   0.239   8.0821  -0.7373  -0.3764
 0R9  H5   H  HCH2   0   0.244   7.9756  -0.4670   1.3548
 0R9  H6   H  HNH1   0   0.402   6.2545   1.2744  -0.2174
 0R9  H7   H  HCR5   0   0.273   2.8984  -1.7330   0.0269
 0R9  H8   H  HCR6   0   0.273  -0.1221   3.5083  -0.1455
 0R9  H9   H  HNR5   0   0.420   4.3607   2.1855   0.5481
 0R9  H10  H  HCR6   0   0.256  -2.2198   2.5458   1.1451
 0R9  H11  H  HCR6   0   0.256  -5.3813   1.4616  -1.5087
 0R9  H12  H  HCR6   0   0.253  -1.5614   0.2976  -2.4426
 0R9  H14  H  HCR5   0   0.320   1.0415  -1.9232  -1.9914
 0R9  H15  H  HCR5   0   0.289  -0.7083  -3.9988  -1.6444

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
 0R9  C1   C2   single    1.516  0.020  1.516
 0R9  C2   N3   single    1.452  0.020  1.452
 0R9  N3   C4   single    1.341  0.020  1.341
 0R9  O5   C4   double    1.223  0.020  1.223
 0R9  C4   C6   single    1.481  0.020  1.481
 0R9  C6   N14  aromatic  1.373  0.020  1.373
 0R9  C6   C7   aromatic  1.368  0.020  1.368
 0R9  N14  C13  aromatic  1.356  0.020  1.356
 0R9  C7   C8   aromatic  1.421  0.020  1.421
 0R9  C13  N12  aromatic  1.322  0.020  1.322
 0R9  C13  C8   aromatic  1.413  0.020  1.413
 0R9  N12  C11  aromatic  1.319  0.020  1.319
 0R9  C8   C9   aromatic  1.394  0.020  1.394
 0R9  C25  N24  aromatic  1.355  0.020  1.355
 0R9  C25  C26  aromatic  1.368  0.020  1.368
 0R9  C11  C10  aromatic  1.409  0.020  1.409
 0R9  C9   N24  single    1.409  0.020  1.409
 0R9  C9   C10  aromatic  1.388  0.020  1.388
 0R9  N24  N28  aromatic  1.326  0.020  1.326
 0R9  C10  C15  single    1.475  0.020  1.475
 0R9  C26  C27  aromatic  1.406  0.020  1.406
 0R9  C20  C15  aromatic  1.394  0.020  1.394
 0R9  C20  N19  aromatic  1.324  0.020  1.324
 0R9  C15  C16  aromatic  1.389  0.020  1.389
 0R9  N28  C27  aromatic  1.314  0.020  1.314
 0R9  C27  C29  single    1.486  0.020  1.486
 0R9  N19  C18  aromatic  1.329  0.020  1.329
 0R9  C16  C17  aromatic  1.388  0.020  1.388
 0R9  C18  C17  aromatic  1.390  0.020  1.390
 0R9  F30  C29  single    1.338  0.020  1.338
 0R9  C29  F31  single    1.341  0.020  1.341
 0R9  C29  F32  single    1.332  0.020  1.332
 0R9  C17  C21  single    1.523  0.020  1.523
 0R9  C21  O22  deloc     1.245  0.020  1.245
 0R9  C21  O23  deloc     1.245  0.020  1.245
 0R9  C1   H1   single    0.970  0.020  1.090
 0R9  C1   H2   single    0.970  0.020  1.090
 0R9  C1   H3   single    0.970  0.020  1.090
 0R9  C2   H4   single    0.970  0.020  1.090
 0R9  C2   H5   single    0.970  0.020  1.090
 0R9  N3   H6   single    0.860  0.020  1.020
 0R9  C7   H7   single    0.930  0.020  1.080
 0R9  C11  H8   single    0.930  0.020  1.080
 0R9  N14  H9   single    0.860  0.020  1.020
 0R9  C16  H10  single    0.930  0.020  1.080
 0R9  C18  H11  single    0.930  0.020  1.080
 0R9  C20  H12  single    0.930  0.020  1.080
 0R9  C25  H14  single    0.930  0.020  1.080
 0R9  C26  H15  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
 0R9  H3   C1   H2   107.99  3.000
 0R9  H3   C1   H1   107.60  3.000
 0R9  H2   C1   H1   108.39  3.000
 0R9  H3   C1   C2   109.70  3.000
 0R9  H2   C1   C2   111.40  3.000
 0R9  H1   C1   C2   111.63  3.000
 0R9  H5   C2   H4   106.96  3.000
 0R9  H5   C2   N3   108.82  3.000
 0R9  H4   C2   N3   110.22  3.000
 0R9  H5   C2   C1   110.01  3.000
 0R9  H4   C2   C1   110.20  3.000
 0R9  N3   C2   C1   110.54  3.000
 0R9  H6   N3   C4   119.41  3.000
 0R9  H6   N3   C2   117.01  3.000
 0R9  C4   N3   C2   122.07  3.000
 0R9  C6   C4   O5   120.09  3.000
 0R9  C6   C4   N3   116.30  3.000
 0R9  O5   C4   N3   123.62  3.000
 0R9  N14  C6   C7   109.83  3.000
 0R9  C7   C6   C4   125.79  3.000
 0R9  N14  C6   C4   124.37  3.000
 0R9  H7   C7   C8   128.02  3.000
 0R9  H7   C7   C6   125.57  3.000
 0R9  C8   C7   C6   106.40  3.000
 0R9  C13  C8   C9   116.44  3.000
 0R9  C9   C8   C7   136.47  3.000
 0R9  C13  C8   C7   107.06  3.000
 0R9  N24  C9   C10  121.43  3.000
 0R9  C10  C9   C8   119.03  3.000
 0R9  N24  C9   C8   119.53  3.000
 0R9  C15  C10  C11  119.01  3.000
 0R9  C15  C10  C9   123.22  3.000
 0R9  C11  C10  C9   117.75  3.000
 0R9  H8   C11  N12  116.33  3.000
 0R9  H8   C11  C10  118.40  3.000
 0R9  N12  C11  C10  125.25  3.000
 0R9  C13  N12  C11  115.25  3.000
 0R9  N14  C13  N12  126.02  3.000
 0R9  N12  C13  C8   126.24  3.000
 0R9  N14  C13  C8   107.71  3.000
 0R9  H9   N14  C13  123.89  3.000
 0R9  H9   N14  C6   126.54  3.000
 0R9  C13  N14  C6   108.98  3.000
 0R9  C20  C15  C16  117.41  3.000
 0R9  C16  C15  C10  121.49  3.000
 0R9  C20  C15  C10  121.07  3.000
 0R9  H10  C16  C17  119.61  3.000
 0R9  H10  C16  C15  120.36  3.000
 0R9  C17  C16  C15  120.03  3.000
 0R9  C21  C17  C18  121.47  3.000
 0R9  C21  C17  C16  121.34  3.000
 0R9  C18  C17  C16  117.18  3.000
 0R9  H11  C18  N19  116.43  3.000
 0R9  H11  C18  C17  119.77  3.000
 0R9  N19  C18  C17  123.81  3.000
 0R9  C20  N19  C18  118.05  3.000
 0R9  H12  C20  N19  116.29  3.000
 0R9  H12  C20  C15  120.19  3.000
 0R9  N19  C20  C15  123.52  3.000
 0R9  O23  C21  O22  127.40  3.000
 0R9  O23  C21  C17  116.35  3.000
 0R9  O22  C21  C17  116.25  3.000
 0R9  N28  N24  C25  112.71  3.000
 0R9  N28  N24  C9   120.38  3.000
 0R9  C25  N24  C9   126.89  3.000
 0R9  H14  C25  C26  131.42  3.000
 0R9  H14  C25  N24  122.01  3.000
 0R9  C26  C25  N24  106.54  3.000
 0R9  H15  C26  C27  128.77  3.000
 0R9  H15  C26  C25  127.46  3.000
 0R9  C27  C26  C25  103.77  3.000
 0R9  C29  C27  N28  120.42  3.000
 0R9  C29  C27  C26  127.26  3.000
 0R9  N28  C27  C26  112.28  3.000
 0R9  C27  N28  N24  104.69  3.000
 0R9  F32  C29  F31  107.21  3.000
 0R9  F32  C29  F30  107.93  3.000
 0R9  F31  C29  F30  106.59  3.000
 0R9  F32  C29  C27  112.17  3.000
 0R9  F31  C29  C27  111.74  3.000
 0R9  F30  C29  C27  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
 0R9  CONST_01  N12  C13  N14  C6    180.00   0.0  0
 0R9  CONST_02  C8   C13  N14  C6      0.00   0.0  0
 0R9  CONST_03  C13  C8   C7   C6      0.00   0.0  0
 0R9  CONST_04  C9   C8   C7   C6    180.00   0.0  0
 0R9  CONST_05  C13  N14  C6   C7      0.00   0.0  0
 0R9  CONST_06  N14  C13  C8   C7      0.00   0.0  0
 0R9  CONST_07  N12  C13  C8   C7    180.00   0.0  0
 0R9  CONST_08  N24  C9   C8   C7      0.00   0.0  0
 0R9  CONST_09  C10  C9   C8   C7    180.00   0.0  0
 0R9  CONST_10  N14  C6   C7   C8      0.00   0.0  0
 0R9  CONST_11  C11  N12  C13  C8      0.00   0.0  0
 0R9  CONST_14  C11  C10  C9   C8      0.00   0.0  0
 0R9  CONST_15  C15  C10  C9   C8    180.00   0.0  0
 0R9  CONST_16  N14  C13  C8   C9    180.00   0.0  0
 0R9  CONST_17  N12  C13  C8   C9      0.00   0.0  0
 0R9  CONST_18  C26  C25  N24  C9    180.00   0.0  0
 0R9  CONST_19  C27  N28  N24  C9    180.00   0.0  0
 0R9  CONST_20  N12  C11  C10  C9      0.00   0.0  0
 0R9  CONST_23  C13  N12  C11  C10     0.00   0.0  0
 0R9  CONST_24  C13  C8   C9   C10     0.00   0.0  0
 0R9  CONST_27  N19  C20  C15  C10   180.00   0.0  0
 0R9  CONST_28  C17  C16  C15  C10   180.00   0.0  0
 0R9  CONST_29  N14  C13  N12  C11   180.00   0.0  0
 0R9  CONST_30  N24  C9   C10  C11   180.00   0.0  0
 0R9  CONST_33  C15  C10  C11  N12   180.00   0.0  0
 0R9  CONST_34  N24  C9   C8   C13   180.00   0.0  0
 0R9  CONST_35  N24  C9   C10  C15     0.00   0.0  0
 0R9  CONST_36  C18  N19  C20  C15     0.00   0.0  0
 0R9  CONST_37  C18  C17  C16  C15     0.00   0.0  0
 0R9  CONST_38  N19  C20  C15  C16     0.00   0.0  0
 0R9  CONST_39  N19  C18  C17  C16     0.00   0.0  0
 0R9  CONST_40  C20  C15  C16  C17     0.00   0.0  0
 0R9  CONST_41  C20  N19  C18  C17     0.00   0.0  0
 0R9  CONST_42  C27  C26  C25  N24     0.00   0.0  0
 0R9  CONST_43  C26  C27  N28  N24     0.00   0.0  0
 0R9  CONST_44  C27  N28  N24  C25     0.00   0.0  0
 0R9  CONST_45  N28  C27  C26  C25     0.00   0.0  0
 0R9  CONST_46  N28  N24  C25  C26     0.00   0.0  0
 0R9  CONST_47  C13  N14  C6   C4    180.00   0.0  0
 0R9  CONST_48  C8   C7   C6   C4    180.00   0.0  0
 0R9  CONST_49  C21  C17  C16  C15   180.00   0.0  0
 0R9  CONST_50  C21  C17  C18  N19   180.00   0.0  0
 0R9  CONST_51  C29  C27  N28  N24   180.00   0.0  0
 0R9  CONST_52  C29  C27  C26  C25   180.00   0.0  0
 0R9  CONST_53  H9   N14  C6   C7    180.00   0.0  0
 0R9  CONST_54  H7   C7   C8   C9      0.00   0.0  0
 0R9  CONST_55  H14  C25  N24  C9      0.00   0.0  0
 0R9  CONST_56  H8   C11  C10  C9    180.00   0.0  0
 0R9  CONST_57  H12  C20  C15  C10     0.00   0.0  0
 0R9  CONST_58  H10  C16  C15  C10     0.00   0.0  0
 0R9  CONST_59  H11  C18  C17  C16   180.00   0.0  0
 0R9  CONST_60  H15  C26  C25  N24   180.00   0.0  0
 0R9  CONST_61  C6   C4   N3   C2    180.00   0.0  0
 0R9  CONST_62  H6   N3   C4   C6      0.00   0.0  0
 0R9  CONST_63  O5   C4   N3   C2      0.00   0.0  0
 0R9  Var_01    N14  C6   C4   N3    -19.93  30.0  2
 0R9  Var_02    O22  C21  C17  C16    -1.10  30.0  2
 0R9  Var_03    F30  C29  C27  C26   -39.74  30.0  2
 0R9  Var_04    C4   N3   C2   C1   -172.02  30.0  3
 0R9  Var_05    H1   C1   C2   N3    -60.78  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
 0R9  plan-1  C9   0.020
 0R9  plan-1  N24  0.020
 0R9  plan-1  C25  0.020
 0R9  plan-1  C26  0.020
 0R9  plan-1  C27  0.020
 0R9  plan-1  N28  0.020
 0R9  plan-1  C29  0.020
 0R9  plan-1  H14  0.020
 0R9  plan-1  H15  0.020
 0R9  plan-2  C10  0.020
 0R9  plan-2  C15  0.020
 0R9  plan-2  C16  0.020
 0R9  plan-2  C17  0.020
 0R9  plan-2  C18  0.020
 0R9  plan-2  N19  0.020
 0R9  plan-2  C20  0.020
 0R9  plan-2  C21  0.020
 0R9  plan-2  H10  0.020
 0R9  plan-2  H11  0.020
 0R9  plan-2  H12  0.020
 0R9  plan-3  C4   0.020
 0R9  plan-3  C6   0.020
 0R9  plan-3  C7   0.020
 0R9  plan-3  C8   0.020
 0R9  plan-3  C9   0.020
 0R9  plan-3  C10  0.020
 0R9  plan-3  C11  0.020
 0R9  plan-3  N12  0.020
 0R9  plan-3  C13  0.020
 0R9  plan-3  N14  0.020
 0R9  plan-3  C15  0.020
 0R9  plan-3  N24  0.020
 0R9  plan-3  H7   0.020
 0R9  plan-3  H8   0.020
 0R9  plan-3  H9   0.020
 0R9  plan-4  C2   0.020
 0R9  plan-4  N3   0.020
 0R9  plan-4  C4   0.020
 0R9  plan-4  O5   0.020
 0R9  plan-4  C6   0.020
 0R9  plan-4  H6   0.020
 0R9  plan-5  C17  0.020
 0R9  plan-5  C21  0.020
 0R9  plan-5  O22  0.020
 0R9  plan-5  O23  0.020

