# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 19 20:31:22 2020
#   Inital geometry file: a 92 line input string
#   Ligand name: 4-(3-chlorophenyl)-~{N}-ethyl-1~{H}-pyrrolo[2,3-b]pyridine-2-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCNC(=O)c1[nH]c2nccc(c3cccc(Cl)c3)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
 C9Q  C9Q  4-(3-chlorophenyl)-~{N}-ethyl-1~{H}-pyrrolo[2,3-b]pyridine-2-carboxamide  ligand  35  21  .  2021-08-07  2021-08-07  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_C9Q
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
 C9Q  C1   C   CR16  0  -0.409  -1.2734  -2.9145   0.2738
 C9Q  C2   C   CR6   0   0.151  -1.1432  -1.5650  -0.0219
 C9Q  C3   C   CR56  0  -0.010   0.1677  -1.0748  -0.1177
 C9Q  C7   C   CH2   0  -0.263   5.4638   1.7232  -0.1727
 C9Q  C8   C   CH3   0  -0.700   6.7473   1.1140   0.3567
 C9Q  C9   C   CR56  0   0.469   1.2210  -1.9894   0.1177
 C9Q  C10  C   CR16  0  -0.072  -0.1427  -3.7144   0.4726
 C9Q  C11  C   CR6   0   0.059  -2.3239  -0.7074  -0.2235
 C9Q  C12  C   CR16  0  -0.271  -2.3742   0.5638   0.3476
 C9Q  C13  C   CR6   0  -0.024  -3.4985   1.3509   0.1653
 C9Q  C14  C   CR16  0  -0.219  -4.5817   0.9086  -0.5778
 C9Q  C15  C   CR16  0  -0.247  -4.5259  -0.3568  -1.1444
 C9Q  C16  C   CR16  0  -0.291  -3.4111  -1.1616  -0.9693
 C9Q  C4   C   CR15  0  -0.463   0.7745   0.1714  -0.4389
 C9Q  C5   C   CR5   0   0.251   2.1275  -0.0174  -0.3666
 C9Q  CL1  CL  CL    0  -0.125  -3.5509   2.9239   0.8918
 C9Q  C6   C   C     0   0.528   3.1612   1.0159  -0.5934
 C9Q  O1   O   O     0  -0.484   2.8951   2.0253  -1.2317
 C9Q  N2   N   NR15  0  -0.727   2.3942  -1.3192  -0.0192
 C9Q  N1   N   NH1   0  -0.650   4.3704   0.7741  -0.0647
 C9Q  N3   N   N     0  -0.427   1.1037  -3.2768   0.4023
 C9Q  H1   H   HCR6  0   0.267  -2.2520  -3.3633   0.3810
 C9Q  H2   H   HCH2  0   0.237   5.2248   2.6377   0.3777
 C9Q  H3   H   HCH2  0   0.243   5.5864   2.0047  -1.2191
 C9Q  H4   H   HCH3  0   0.234   6.6533   0.8323   1.4065
 C9Q  H5   H   HCH3  0   0.237   7.0308   0.2277  -0.2114
 C9Q  H6   H   HCH3  0   0.247   7.5587   1.8360   0.2803
 C9Q  H7   H   HCR6  0   0.264  -0.2730  -4.7644   0.7078
 C9Q  H8   H   HCR6  0   0.286  -1.5530   0.9266   0.9514
 C9Q  H9   H   HCR6  0   0.284  -5.4512   1.5369  -0.7135
 C9Q  H10  H   HCR6  0   0.273  -5.3615  -0.7133  -1.7316
 C9Q  H11  H   HCR6  0   0.266  -3.3779  -2.1394  -1.4319
 C9Q  H12  H   HCR5  0   0.267   0.2894   1.1023  -0.6830
 C9Q  H13  H   HNR5  0   0.416   3.2996  -1.7622  -0.0032
 C9Q  H14  H   HNH1  0   0.402   4.4744   0.0376   0.6153

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
 C9Q  C8   C7   single    1.516  0.020  1.516
 C9Q  C7   N1   single    1.452  0.020  1.452
 C9Q  N1   C6   single    1.342  0.020  1.342
 C9Q  O1   C6   double    1.224  0.020  1.224
 C9Q  C6   C5   single    1.479  0.020  1.479
 C9Q  CL1  C13  single    1.733  0.020  1.733
 C9Q  C5   N2   aromatic  1.373  0.020  1.373
 C9Q  C5   C4   aromatic  1.368  0.020  1.368
 C9Q  N2   C9   aromatic  1.358  0.020  1.358
 C9Q  C4   C3   aromatic  1.423  0.020  1.423
 C9Q  C13  C12  aromatic  1.385  0.020  1.385
 C9Q  C13  C14  aromatic  1.386  0.020  1.386
 C9Q  C12  C11  aromatic  1.395  0.020  1.395
 C9Q  C9   C3   aromatic  1.415  0.020  1.415
 C9Q  C9   N3   aromatic  1.324  0.020  1.324
 C9Q  C3   C2   aromatic  1.403  0.020  1.403
 C9Q  N3   C10  aromatic  1.323  0.020  1.323
 C9Q  C2   C11  single    1.473  0.020  1.473
 C9Q  C2   C1   aromatic  1.388  0.020  1.388
 C9Q  C14  C15  aromatic  1.388  0.020  1.388
 C9Q  C11  C16  aromatic  1.394  0.020  1.394
 C9Q  C10  C1   aromatic  1.399  0.020  1.399
 C9Q  C15  C16  aromatic  1.386  0.020  1.386
 C9Q  C1   H1   single    0.930  0.020  1.080
 C9Q  C7   H2   single    0.970  0.020  1.090
 C9Q  C7   H3   single    0.970  0.020  1.090
 C9Q  C8   H4   single    0.970  0.020  1.090
 C9Q  C8   H5   single    0.970  0.020  1.090
 C9Q  C8   H6   single    0.970  0.020  1.090
 C9Q  C10  H7   single    0.930  0.020  1.080
 C9Q  C12  H8   single    0.930  0.020  1.080
 C9Q  C14  H9   single    0.930  0.020  1.080
 C9Q  C15  H10  single    0.930  0.020  1.080
 C9Q  C16  H11  single    0.930  0.020  1.080
 C9Q  C4   H12  single    0.930  0.020  1.080
 C9Q  N2   H13  single    0.860  0.020  1.020
 C9Q  N1   H14  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
 C9Q  H1   C1   C10  118.67  3.000
 C9Q  H1   C1   C2   120.62  3.000
 C9Q  C10  C1   C2   120.69  3.000
 C9Q  C11  C2   C3   122.42  3.000
 C9Q  C11  C2   C1   121.34  3.000
 C9Q  C3   C2   C1   116.24  3.000
 C9Q  C4   C3   C9   106.64  3.000
 C9Q  C9   C3   C2   117.28  3.000
 C9Q  C4   C3   C2   136.06  3.000
 C9Q  H3   C7   H2   106.95  3.000
 C9Q  H3   C7   N1   108.95  3.000
 C9Q  H2   C7   N1   110.16  3.000
 C9Q  H3   C7   C8   110.09  3.000
 C9Q  H2   C7   C8   110.19  3.000
 C9Q  N1   C7   C8   110.42  3.000
 C9Q  H6   C8   H5   107.98  3.000
 C9Q  H6   C8   H4   107.63  3.000
 C9Q  H5   C8   H4   108.29  3.000
 C9Q  H6   C8   C7   109.88  3.000
 C9Q  H5   C8   C7   111.40  3.000
 C9Q  H4   C8   C7   111.52  3.000
 C9Q  N3   C9   N2   125.33  3.000
 C9Q  N3   C9   C3   126.77  3.000
 C9Q  N2   C9   C3   107.90  3.000
 C9Q  H7   C10  N3   116.44  3.000
 C9Q  H7   C10  C1   119.17  3.000
 C9Q  N3   C10  C1   124.38  3.000
 C9Q  C16  C11  C12  119.19  3.000
 C9Q  C16  C11  C2   120.56  3.000
 C9Q  C12  C11  C2   120.24  3.000
 C9Q  H8   C12  C13  119.95  3.000
 C9Q  H8   C12  C11  120.45  3.000
 C9Q  C13  C12  C11  119.58  3.000
 C9Q  CL1  C13  C14  119.38  3.000
 C9Q  C14  C13  C12  121.59  3.000
 C9Q  CL1  C13  C12  119.03  3.000
 C9Q  H9   C14  C15  120.73  3.000
 C9Q  H9   C14  C13  120.68  3.000
 C9Q  C15  C14  C13  118.59  3.000
 C9Q  H10  C15  C16  119.90  3.000
 C9Q  H10  C15  C14  119.42  3.000
 C9Q  C16  C15  C14  120.68  3.000
 C9Q  H11  C16  C15  119.69  3.000
 C9Q  H11  C16  C11  119.93  3.000
 C9Q  C15  C16  C11  120.37  3.000
 C9Q  H12  C4   C5   125.19  3.000
 C9Q  H12  C4   C3   128.00  3.000
 C9Q  C5   C4   C3   106.80  3.000
 C9Q  N2   C5   C6   124.42  3.000
 C9Q  N2   C5   C4   109.65  3.000
 C9Q  C6   C5   C4   125.92  3.000
 C9Q  N1   C6   O1   123.38  3.000
 C9Q  O1   C6   C5   120.29  3.000
 C9Q  N1   C6   C5   116.33  3.000
 C9Q  H13  N2   C5   126.51  3.000
 C9Q  H13  N2   C9   123.87  3.000
 C9Q  C5   N2   C9   109.00  3.000
 C9Q  H14  N1   C6   119.38  3.000
 C9Q  H14  N1   C7   116.75  3.000
 C9Q  C6   N1   C7   122.11  3.000
 C9Q  C10  N3   C9   114.62  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
 C9Q  CONST_01  C4   C3   C2   C1    180.00   0.0  0
 C9Q  CONST_02  C9   C3   C2   C1      0.00   0.0  0
 C9Q  CONST_05  C9   N3   C10  C1      0.00   0.0  0
 C9Q  CONST_06  C5   C4   C3   C2    180.00   0.0  0
 C9Q  CONST_07  N2   C9   C3   C2    180.00   0.0  0
 C9Q  CONST_08  N3   C9   C3   C2      0.00   0.0  0
 C9Q  CONST_09  C13  C12  C11  C2    180.00   0.0  0
 C9Q  CONST_10  C15  C16  C11  C2    180.00   0.0  0
 C9Q  CONST_11  N3   C10  C1   C2      0.00   0.0  0
 C9Q  CONST_12  N2   C5   C4   C3      0.00   0.0  0
 C9Q  CONST_13  C5   N2   C9   C3      0.00   0.0  0
 C9Q  CONST_14  C10  N3   C9   C3      0.00   0.0  0
 C9Q  CONST_17  C10  C1   C2   C3      0.00   0.0  0
 C9Q  CONST_18  C4   C5   N2   C9      0.00   0.0  0
 C9Q  CONST_19  C5   C4   C3   C9      0.00   0.0  0
 C9Q  CONST_20  C11  C2   C3   C9    180.00   0.0  0
 C9Q  CONST_21  N2   C9   N3   C10   180.00   0.0  0
 C9Q  CONST_22  C11  C2   C1   C10   180.00   0.0  0
 C9Q  CONST_23  C14  C13  C12  C11     0.00   0.0  0
 C9Q  CONST_24  C4   C3   C2   C11     0.00   0.0  0
 C9Q  CONST_25  C14  C15  C16  C11     0.00   0.0  0
 C9Q  CONST_26  C15  C14  C13  C12     0.00   0.0  0
 C9Q  CONST_27  C15  C16  C11  C12     0.00   0.0  0
 C9Q  CONST_28  C16  C11  C12  C13     0.00   0.0  0
 C9Q  CONST_29  C16  C15  C14  C13     0.00   0.0  0
 C9Q  CONST_30  N2   C9   C3   C4      0.00   0.0  0
 C9Q  CONST_31  N3   C9   C3   C4    180.00   0.0  0
 C9Q  CONST_32  N3   C9   N2   C5    180.00   0.0  0
 C9Q  CONST_33  C6   C5   C4   C3    180.00   0.0  0
 C9Q  CONST_34  C6   C5   N2   C9    180.00   0.0  0
 C9Q  CONST_35  CL1  C13  C12  C11   180.00   0.0  0
 C9Q  CONST_36  CL1  C13  C14  C15   180.00   0.0  0
 C9Q  CONST_37  H12  C4   C3   C2      0.00   0.0  0
 C9Q  CONST_38  H8   C12  C11  C2      0.00   0.0  0
 C9Q  CONST_39  H11  C16  C11  C2      0.00   0.0  0
 C9Q  CONST_40  H7   C10  C1   C2    180.00   0.0  0
 C9Q  CONST_41  H13  N2   C9   C3    180.00   0.0  0
 C9Q  CONST_42  H1   C1   C2   C3    180.00   0.0  0
 C9Q  CONST_43  H10  C15  C16  C11   180.00   0.0  0
 C9Q  CONST_44  H9   C14  C13  C12   180.00   0.0  0
 C9Q  CONST_45  C5   C6   N1   C7    180.00   0.0  0
 C9Q  CONST_46  H14  N1   C6   C5      0.00   0.0  0
 C9Q  CONST_47  O1   C6   N1   C7      0.00   0.0  0
 C9Q  Var_01    N1   C6   C5   C4    158.83  30.0  2
 C9Q  Var_02    C6   N1   C7   C8   -172.78  30.0  3
 C9Q  Var_03    H4   C8   C7   N1    -60.21  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
 C9Q  plan-1  C2   0.020
 C9Q  plan-1  C11  0.020
 C9Q  plan-1  C12  0.020
 C9Q  plan-1  C13  0.020
 C9Q  plan-1  C14  0.020
 C9Q  plan-1  C15  0.020
 C9Q  plan-1  C16  0.020
 C9Q  plan-1  CL1  0.020
 C9Q  plan-1  H8   0.020
 C9Q  plan-1  H9   0.020
 C9Q  plan-1  H10  0.020
 C9Q  plan-1  H11  0.020
 C9Q  plan-2  C1   0.020
 C9Q  plan-2  C2   0.020
 C9Q  plan-2  C3   0.020
 C9Q  plan-2  C9   0.020
 C9Q  plan-2  C10  0.020
 C9Q  plan-2  C11  0.020
 C9Q  plan-2  C4   0.020
 C9Q  plan-2  C5   0.020
 C9Q  plan-2  C6   0.020
 C9Q  plan-2  N2   0.020
 C9Q  plan-2  N3   0.020
 C9Q  plan-2  H1   0.020
 C9Q  plan-2  H7   0.020
 C9Q  plan-2  H12  0.020
 C9Q  plan-2  H13  0.020
 C9Q  plan-3  C7   0.020
 C9Q  plan-3  C5   0.020
 C9Q  plan-3  C6   0.020
 C9Q  plan-3  O1   0.020
 C9Q  plan-3  N1   0.020
 C9Q  plan-3  H14  0.020

