# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 27 16:21:45 2020
#   Inital geometry file: a 102 line input string
#   Ligand name: 6-chloro-5-[6-(dimethylamino)-2-methoxypyridin-3-yl]-1H-indole-3-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1nc(ccc1c2cc3c([nH]cc3C(O)=O)cc2Cl)N(C)C
#
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
 75O  75O  '6-chloro-5-[6-(dimethylamino)-2-methoxypyridin-3-yl]-1H-indole-3-carboxylic acid'  ligand  40  24  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_75O
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
 75O  N3   N   NR15  0  -0.678  -4.3380   1.4815  -0.2642
 75O  C4   C   CR16  0  -0.425   2.7716  -1.5147  -1.2388
 75O  N2   N   N     0  -0.516   3.2046  -0.1752   0.6877
 75O  C7   C   CR6   0   0.491   1.9619   0.2429   0.6681
 75O  C6   C   CR6   0  -0.153   1.0163  -0.1409  -0.2934
 75O  C9   C   CR6   0   0.172  -0.3711   0.3580  -0.2840
 75O  C13  C   CR16  0  -0.242  -1.9618   2.2066  -0.5251
 75O  C8   C   CH3   0  -0.410   2.4997   1.5492   2.5627
 75O  C16  C   CR5   0  -0.205  -4.0235  -0.6954   0.0796
 75O  C1   C   CH3   0  -0.534   5.5092  -2.2440  -1.1914
 75O  C2   C   CH3   0  -0.515   5.8156  -0.7912   0.8024
 75O  C3   C   CR6   0   0.532   3.6358  -1.0437  -0.2351
 75O  C5   C   CR16  0  -0.169   1.4694  -1.0492  -1.2399
 75O  O1   O   O2    0  -0.462   1.5474   1.0769   1.6236
 75O  C10  C   CR16  0  -0.432  -1.4171  -0.5300  -0.0813
 75O  C11  C   CR56  0   0.126  -2.7380  -0.0792  -0.0945
 75O  C12  C   CR56  0   0.339  -2.9823   1.2889  -0.3082
 75O  C14  C   CR6   0  -0.130  -0.6732   1.7166  -0.5140
 75O  CL1  CL  CL    0  -0.132   0.6171   2.8276  -0.8429
 75O  C15  C   CR15  0   0.017  -4.9593   0.3080  -0.0357
 75O  C17  C   C     0   0.458  -4.2822  -2.1018   0.3212
 75O  O2   O   OH1   0  -0.606  -5.5801  -2.3752   0.4493
 75O  O3   O   O     0  -0.456  -3.4202  -2.9506   0.3989
 75O  H1   H   HNR5  0   0.426  -4.8095   2.3628  -0.3938
 75O  H2   H   HCR6  0   0.265   3.0961  -2.2063  -2.0015
 75O  H3   H   HCR6  0   0.288  -2.1669   3.2530  -0.7065
 75O  H4   H   HCH3  0   0.225   3.2902   2.1267   2.0814
 75O  H5   H   HCH3  0   0.241   1.9502   2.1937   3.2442
 75O  H6   H   HCH3  0   0.226   2.9588   0.7361   3.1259
 75O  H7   H   HCH3  0   0.257   6.5233  -2.5201  -0.9151
 75O  H8   H   HCH3  0   0.243   4.9521  -3.1696  -1.3441
 75O  H9   H   HCH3  0   0.231   5.5528  -1.7139  -2.1483
 75O  H10  H   HCH3  0   0.224   6.0972   0.2175   0.4847
 75O  H11  H   HCH3  0   0.248   5.3544  -0.7133   1.7840
 75O  H12  H   HCH3  0   0.238   6.7229  -1.3830   0.8990
 75O  H13  H   HCR6  0   0.255   0.7885  -1.3924  -2.0098
 75O  H14  H   HCR6  0   0.251  -1.1934  -1.5722   0.0987
 75O  H15  H   HCR5  0   0.308  -6.0343   0.2613   0.0298
 75O  H16  H   HOH1  0   0.483  -5.7013  -3.3243   0.5973
 75O  N1   N   NT    0  -0.481   4.9301  -1.4451  -0.1371

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
 75O  C8   O1   single    1.418  0.020  1.418
 75O  O1   C7   single    1.334  0.020  1.334
 75O  C7   N2   aromatic  1.311  0.020  1.311
 75O  C7   C6   aromatic  1.402  0.020  1.402
 75O  C1   N1   single    1.444  0.020  1.444
 75O  N2   C3   aromatic  1.339  0.020  1.339
 75O  N3   C15  aromatic  1.347  0.020  1.347
 75O  N3   C12  aromatic  1.370  0.020  1.370
 75O  C13  C12  aromatic  1.389  0.020  1.389
 75O  C13  C14  aromatic  1.379  0.020  1.379
 75O  C15  C16  aromatic  1.377  0.020  1.377
 75O  C12  C11  aromatic  1.406  0.020  1.406
 75O  CL1  C14  single    1.734  0.020  1.734
 75O  C14  C9   aromatic  1.411  0.020  1.411
 75O  C16  C11  aromatic  1.436  0.020  1.436
 75O  C16  C17  single    1.450  0.020  1.450
 75O  C11  C10  aromatic  1.396  0.020  1.396
 75O  O3   C17  double    1.212  0.020  1.212
 75O  C17  O2   single    1.333  0.020  1.333
 75O  C9   C10  aromatic  1.387  0.020  1.387
 75O  C9   C6   single    1.474  0.020  1.474
 75O  C6   C5   aromatic  1.388  0.020  1.388
 75O  C3   N1   single    1.359  0.020  1.359
 75O  C3   C4   aromatic  1.406  0.020  1.406
 75O  N1   C2   single    1.447  0.020  1.447
 75O  C5   C4   aromatic  1.383  0.020  1.383
 75O  N3   H1   single    0.860  0.020  1.020
 75O  C4   H2   single    0.930  0.020  1.080
 75O  C13  H3   single    0.930  0.020  1.080
 75O  C8   H4   single    0.970  0.020  1.090
 75O  C8   H5   single    0.970  0.020  1.090
 75O  C8   H6   single    0.970  0.020  1.090
 75O  C1   H7   single    0.970  0.020  1.090
 75O  C1   H8   single    0.970  0.020  1.090
 75O  C1   H9   single    0.970  0.020  1.090
 75O  C2   H10  single    0.970  0.020  1.090
 75O  C2   H11  single    0.970  0.020  1.090
 75O  C2   H12  single    0.970  0.020  1.090
 75O  C5   H13  single    0.930  0.020  1.080
 75O  C10  H14  single    0.930  0.020  1.080
 75O  C15  H15  single    0.930  0.020  1.080
 75O  O2   H16  single    0.850  0.020  0.980

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
 75O  H1   N3   C15  124.59  3.000
 75O  H1   N3   C12  125.57  3.000
 75O  C15  N3   C12  109.83  3.000
 75O  H2   C4   C5   119.88  3.000
 75O  H2   C4   C3   122.29  3.000
 75O  C5   C4   C3   117.82  3.000
 75O  C3   N2   C7   120.12  3.000
 75O  O1   C7   C6   116.91  3.000
 75O  C6   C7   N2   124.20  3.000
 75O  O1   C7   N2   118.88  3.000
 75O  C5   C6   C9   122.21  3.000
 75O  C5   C6   C7   115.25  3.000
 75O  C9   C6   C7   122.52  3.000
 75O  C14  C9   C10  118.62  3.000
 75O  C10  C9   C6   119.60  3.000
 75O  C14  C9   C6   121.76  3.000
 75O  H3   C13  C14  121.49  3.000
 75O  H3   C13  C12  121.73  3.000
 75O  C14  C13  C12  116.77  3.000
 75O  H6   C8   H5   109.34  3.000
 75O  H6   C8   H4   108.51  3.000
 75O  H5   C8   H4   109.21  3.000
 75O  H6   C8   O1   112.11  3.000
 75O  H5   C8   O1   105.85  3.000
 75O  H4   C8   O1   111.76  3.000
 75O  C17  C16  C15  126.82  3.000
 75O  C17  C16  C11  126.58  3.000
 75O  C15  C16  C11  106.59  3.000
 75O  H9   C1   H8   107.98  3.000
 75O  H9   C1   H7   107.94  3.000
 75O  H8   C1   H7   107.25  3.000
 75O  H9   C1   N1   112.72  3.000
 75O  H8   C1   N1   111.52  3.000
 75O  H7   C1   N1   109.22  3.000
 75O  H12  C2   H11  108.22  3.000
 75O  H12  C2   H10  108.22  3.000
 75O  H11  C2   H10  107.77  3.000
 75O  H12  C2   N1   108.80  3.000
 75O  H11  C2   N1   111.03  3.000
 75O  H10  C2   N1   112.67  3.000
 75O  N1   C3   N2   116.67  3.000
 75O  N1   C3   C4   122.56  3.000
 75O  N2   C3   C4   120.76  3.000
 75O  H13  C5   C6   119.12  3.000
 75O  H13  C5   C4   119.05  3.000
 75O  C6   C5   C4   121.82  3.000
 75O  C8   O1   C7   118.27  3.000
 75O  H14  C10  C11  120.58  3.000
 75O  H14  C10  C9   119.05  3.000
 75O  C11  C10  C9   120.37  3.000
 75O  C12  C11  C10  118.69  3.000
 75O  C10  C11  C16  135.02  3.000
 75O  C12  C11  C16  106.28  3.000
 75O  C11  C12  C13  122.60  3.000
 75O  C11  C12  N3   107.69  3.000
 75O  C13  C12  N3   129.71  3.000
 75O  CL1  C14  C13  117.79  3.000
 75O  CL1  C14  C9   119.25  3.000
 75O  C13  C14  C9   122.94  3.000
 75O  H15  C15  C16  129.88  3.000
 75O  H15  C15  N3   120.52  3.000
 75O  C16  C15  N3   109.60  3.000
 75O  O3   C17  O2   122.88  3.000
 75O  O2   C17  C16  112.88  3.000
 75O  O3   C17  C16  124.25  3.000
 75O  H16  O2   C17  109.74  3.000
 75O  C3   N1   C2   119.76  3.000
 75O  C2   N1   C1   118.59  3.000
 75O  C3   N1   C1   119.53  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
 75O  CONST_01  C11  C16  C15  N3      0.00   0.0  0
 75O  CONST_02  C14  C13  C12  N3    180.00   0.0  0
 75O  CONST_03  C16  C11  C12  N3      0.00   0.0  0
 75O  CONST_04  C10  C11  C12  N3    180.00   0.0  0
 75O  CONST_05  C7   N2   C3   C4      0.00   0.0  0
 75O  CONST_06  C7   C6   C5   C4      0.00   0.0  0
 75O  CONST_07  C9   C6   C5   C4    180.00   0.0  0
 75O  CONST_08  C9   C6   C7   N2    180.00   0.0  0
 75O  CONST_09  C5   C6   C7   N2      0.00   0.0  0
 75O  CONST_10  C5   C4   C3   N2      0.00   0.0  0
 75O  CONST_13  C3   N2   C7   C6      0.00   0.0  0
 75O  CONST_14  C13  C14  C9   C6    180.00   0.0  0
 75O  CONST_15  C11  C10  C9   C6    180.00   0.0  0
 75O  CONST_16  C3   C4   C5   C6      0.00   0.0  0
 75O  CONST_17  C12  C13  C14  C9      0.00   0.0  0
 75O  CONST_18  C12  C11  C10  C9      0.00   0.0  0
 75O  CONST_19  C16  C11  C10  C9    180.00   0.0  0
 75O  CONST_20  C15  N3   C12  C13   180.00   0.0  0
 75O  CONST_21  C16  C11  C12  C13   180.00   0.0  0
 75O  CONST_22  C10  C11  C12  C13     0.00   0.0  0
 75O  CONST_23  C10  C9   C14  C13     0.00   0.0  0
 75O  CONST_24  C12  N3   C15  C16     0.00   0.0  0
 75O  CONST_27  C15  C16  C11  C10   180.00   0.0  0
 75O  CONST_28  C15  N3   C12  C11     0.00   0.0  0
 75O  CONST_29  C14  C13  C12  C11     0.00   0.0  0
 75O  CONST_30  C14  C9   C10  C11     0.00   0.0  0
 75O  CONST_31  C15  C16  C11  C12     0.00   0.0  0
 75O  CONST_32  C17  C16  C15  N3    180.00   0.0  0
 75O  CONST_33  N1   C3   N2   C7    180.00   0.0  0
 75O  CONST_34  CL1  C14  C9   C6      0.00   0.0  0
 75O  CONST_35  O1   C7   C6   C9      0.00   0.0  0
 75O  CONST_36  C5   C4   C3   N1    180.00   0.0  0
 75O  CONST_37  O1   C7   N2   C3    180.00   0.0  0
 75O  CONST_38  O1   C7   C6   C5    180.00   0.0  0
 75O  CONST_39  C17  C16  C11  C10     0.00   0.0  0
 75O  CONST_40  CL1  C14  C9   C10   180.00   0.0  0
 75O  CONST_41  CL1  C14  C13  C12   180.00   0.0  0
 75O  CONST_42  C17  C16  C11  C12   180.00   0.0  0
 75O  CONST_43  H3   C13  C12  N3      0.00   0.0  0
 75O  CONST_44  H2   C4   C3   N2    180.00   0.0  0
 75O  CONST_45  H13  C5   C6   C7    180.00   0.0  0
 75O  CONST_46  H14  C10  C9   C6      0.00   0.0  0
 75O  CONST_47  H1   N3   C12  C13     0.00   0.0  0
 75O  CONST_48  H15  C15  C16  C11   180.00   0.0  0
 75O  CONST_49  C1   N1   C3   C4      0.00   0.0  0
 75O  CONST_50  C2   N1   C3   C4    180.00   0.0  0
 75O  CONST_51  C1   N1   C3   N2    180.00   0.0  0
 75O  CONST_52  C2   N1   C3   N2      0.00   0.0  0
 75O  CONST_53  H16  O2   C17  C16   180.00   0.0  0
 75O  Var_01    O3   C17  C16  C11    -0.50  30.0  2
 75O  Var_02    H4   C8   O1   C7     61.87  30.0  3
 75O  Var_03    H7   C1   N1   C3   -176.55  30.0  3
 75O  Var_04    H10  C2   N1   C3    -72.61  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
 75O  plan-1  C4   0.020
 75O  plan-1  N2   0.020
 75O  plan-1  C7   0.020
 75O  plan-1  C6   0.020
 75O  plan-1  C9   0.020
 75O  plan-1  C3   0.020
 75O  plan-1  C5   0.020
 75O  plan-1  O1   0.020
 75O  plan-1  H2   0.020
 75O  plan-1  H13  0.020
 75O  plan-1  N1   0.020
 75O  plan-2  N3   0.020
 75O  plan-2  C6   0.020
 75O  plan-2  C9   0.020
 75O  plan-2  C13  0.020
 75O  plan-2  C16  0.020
 75O  plan-2  C10  0.020
 75O  plan-2  C11  0.020
 75O  plan-2  C12  0.020
 75O  plan-2  C14  0.020
 75O  plan-2  CL1  0.020
 75O  plan-2  C15  0.020
 75O  plan-2  C17  0.020
 75O  plan-2  H1   0.020
 75O  plan-2  H3   0.020
 75O  plan-2  H14  0.020
 75O  plan-2  H15  0.020
 75O  plan-3  C1   0.020
 75O  plan-3  C2   0.020
 75O  plan-3  C3   0.020
 75O  plan-3  N1   0.020
 75O  plan-4  C16  0.020
 75O  plan-4  C17  0.020
 75O  plan-4  O2   0.020
 75O  plan-4  O3   0.020
 75O  plan-4  H16  0.020

