# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 26 15:38:05 2020
#   Inital geometry file: a 75 line input string
#   Ligand name: 6-[(carboxycarbonyl)amino]-1H-indole-5-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)C(=O)Nc1cc2[nH]ccc2cc1C(O)=O
#
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
 OAI  OAI  '6-[(carboxycarbonyl)amino]-1H-indole-5-carboxylic acid'  ligand  24  18  .  2021-08-17  2021-08-17  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_OAI
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
 OAI  C1   C  CR56   0   0.388   1.2206  -0.0512  -2.1233
 OAI  C2   C  CR16   0  -0.418   1.2581  -0.0629  -0.7323
 OAI  C3   C  CR6    0   0.306   0.0515  -0.0493  -0.0401
 OAI  C4   C  CR6    0  -0.228  -1.1926  -0.0229  -0.7516
 OAI  C5   C  CR16   0  -0.397  -1.1804  -0.0120  -2.1364
 OAI  C6   C  CR56   0   0.076   0.0159  -0.0263  -2.8506
 OAI  C9   C  CR15   0  -0.419   0.3658  -0.0216  -4.2395
 OAI  C10  C  CR15   0  -0.040   1.7278  -0.0435  -4.2961
 OAI  N11  N  NR15   0  -0.688   2.2420  -0.0615  -3.0255
 OAI  N12  N  NH1    0  -0.743   0.0002  -0.0599   1.3546
 OAI  C13  C  C      0   0.335   1.0097  -0.0742   2.2467
 OAI  C14  C  C      0   0.334   0.5311  -0.0804   3.7321
 OAI  O15  O  O      0  -0.579  -0.6974  -0.0789   3.9199
 OAI  O16  O  OC    -1  -0.583   1.4411  -0.0862   4.5711
 OAI  O17  O  O      0  -0.488   2.2016  -0.0814   1.9727
 OAI  C18  C  C      0   0.449  -2.5573  -0.0050  -0.0727
 OAI  O19  O  O      0  -0.600  -2.5897  -0.0259   1.1831
 OAI  O20  O  OC    -1  -0.576  -3.5570   0.0291  -0.8090
 OAI  H2   H  HCR6   0   0.278   2.1978  -0.0827  -0.2051
 OAI  H5   H  HCR6   0   0.237  -2.1258   0.0089  -2.6618
 OAI  H9   H  HCR5   0   0.244  -0.3067  -0.0043  -5.0823
 OAI  H10  H  HCR5   0   0.276   2.3857  -0.0474  -5.1501
 OAI  H11  H  HNR5   0   0.406   3.2228  -0.0756  -2.8020
 OAI  H12  H  HNH1   0   0.430  -0.9666  -0.0537   1.7140

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
 OAI  C1   C2   aromatic  1.392  0.020  1.392
 OAI  C1   C6   aromatic  1.407  0.020  1.407
 OAI  C1   N11  aromatic  1.363  0.020  1.363
 OAI  C2   C3   aromatic  1.391  0.020  1.391
 OAI  C2   H2   single    0.930  0.020  1.080
 OAI  C3   C4   aromatic  1.433  0.020  1.433
 OAI  C3   N12  single    1.396  0.020  1.396
 OAI  C4   C5   aromatic  1.385  0.020  1.385
 OAI  C4   C18  single    1.524  0.020  1.524
 OAI  C5   C6   aromatic  1.393  0.020  1.393
 OAI  C5   H5   single    0.930  0.020  1.080
 OAI  C6   C9   aromatic  1.432  0.020  1.432
 OAI  C9   C10  aromatic  1.363  0.020  1.363
 OAI  C9   H9   single    0.930  0.020  1.080
 OAI  C10  N11  aromatic  1.371  0.020  1.371
 OAI  C10  H10  single    0.930  0.020  1.080
 OAI  N11  H11  single    0.860  0.020  1.020
 OAI  N12  C13  single    1.347  0.020  1.347
 OAI  N12  H12  single    0.860  0.020  1.020
 OAI  C13  C14  single    1.561  0.020  1.561
 OAI  C13  O17  double    1.223  0.020  1.223
 OAI  C14  O15  deloc     1.243  0.020  1.243
 OAI  C14  O16  deloc     1.238  0.020  1.238
 OAI  C18  O19  deloc     1.256  0.020  1.256
 OAI  C18  O20  deloc     1.242  0.020  1.242

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
 OAI  N11  C1   C6   107.43  3.000
 OAI  N11  C1   C2   129.90  3.000
 OAI  C6   C1   C2   122.67  3.000
 OAI  H2   C2   C3   120.87  3.000
 OAI  H2   C2   C1   120.84  3.000
 OAI  C3   C2   C1   118.29  3.000
 OAI  N12  C3   C4   117.66  3.000
 OAI  N12  C3   C2   121.94  3.000
 OAI  C4   C3   C2   120.40  3.000
 OAI  C18  C4   C5   116.94  3.000
 OAI  C18  C4   C3   123.79  3.000
 OAI  C5   C4   C3   119.27  3.000
 OAI  H5   C5   C6   120.11  3.000
 OAI  H5   C5   C4   118.56  3.000
 OAI  C6   C5   C4   121.33  3.000
 OAI  C9   C6   C5   134.97  3.000
 OAI  C9   C6   C1   106.98  3.000
 OAI  C5   C6   C1   118.05  3.000
 OAI  H9   C9   C10  126.22  3.000
 OAI  H9   C9   C6   127.27  3.000
 OAI  C10  C9   C6   106.51  3.000
 OAI  H10  C10  N11  120.35  3.000
 OAI  H10  C10  C9   129.99  3.000
 OAI  N11  C10  C9   109.66  3.000
 OAI  H11  N11  C10  124.88  3.000
 OAI  H11  N11  C1   125.71  3.000
 OAI  C10  N11  C1   109.41  3.000
 OAI  H12  N12  C13  118.14  3.000
 OAI  H12  N12  C3   112.50  3.000
 OAI  C13  N12  C3   129.36  3.000
 OAI  O17  C13  C14  120.81  3.000
 OAI  O17  C13  N12  125.59  3.000
 OAI  C14  C13  N12  113.61  3.000
 OAI  O16  C14  O15  128.63  3.000
 OAI  O16  C14  C13  114.82  3.000
 OAI  O15  C14  C13  116.56  3.000
 OAI  O20  C18  O19  124.90  3.000
 OAI  O20  C18  C4   117.19  3.000
 OAI  O19  C18  C4   117.91  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
 OAI  CONST_01  C4   C3   C2   C1     0.00   0.0  0
 OAI  CONST_02  C4   C5   C6   C1     0.00   0.0  0
 OAI  CONST_03  C10  C9   C6   C1     0.00   0.0  0
 OAI  CONST_04  C9   C10  N11  C1     0.00   0.0  0
 OAI  CONST_05  C5   C6   C1   C2     0.00   0.0  0
 OAI  CONST_06  C9   C6   C1   C2   180.00   0.0  0
 OAI  CONST_07  C10  N11  C1   C2   180.00   0.0  0
 OAI  CONST_08  C5   C4   C3   C2     0.00   0.0  0
 OAI  CONST_09  C6   C1   C2   C3     0.00   0.0  0
 OAI  CONST_10  N11  C1   C2   C3   180.00   0.0  0
 OAI  CONST_11  C6   C5   C4   C3     0.00   0.0  0
 OAI  CONST_12  C9   C6   C5   C4   180.00   0.0  0
 OAI  CONST_13  N11  C1   C6   C5   180.00   0.0  0
 OAI  CONST_14  C10  C9   C6   C5   180.00   0.0  0
 OAI  CONST_15  C10  N11  C1   C6     0.00   0.0  0
 OAI  CONST_16  N11  C10  C9   C6     0.00   0.0  0
 OAI  CONST_17  N11  C1   C6   C9     0.00   0.0  0
 OAI  CONST_18  N12  C3   C2   C1   180.00   0.0  0
 OAI  CONST_19  C18  C4   C3   C2   180.00   0.0  0
 OAI  CONST_20  N12  C3   C4   C5   180.00   0.0  0
 OAI  CONST_21  C18  C4   C5   C6   180.00   0.0  0
 OAI  CONST_22  H5   C5   C6   C1   180.00   0.0  0
 OAI  CONST_23  H9   C9   C6   C1   180.00   0.0  0
 OAI  CONST_24  H10  C10  N11  C1   180.00   0.0  0
 OAI  CONST_25  H11  N11  C1   C2     0.00   0.0  0
 OAI  CONST_26  H2   C2   C3   C4   180.00   0.0  0
 OAI  CONST_27  C13  N12  C3   C2     0.00   0.0  0
 OAI  CONST_28  C13  N12  C3   C4   180.00   0.0  0
 OAI  CONST_29  H12  N12  C3   C2   180.00   0.0  0
 OAI  CONST_30  C14  C13  N12  C3   180.00   0.0  0
 OAI  CONST_31  O17  C13  N12  C3     0.00   0.0  0
 OAI  Var_01    O19  C18  C4   C3    -0.62  30.0  2
 OAI  Var_02    O15  C14  C13  N12    0.37  30.0  2

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
 OAI  plan-1  C1   0.020
 OAI  plan-1  C2   0.020
 OAI  plan-1  C3   0.020
 OAI  plan-1  C4   0.020
 OAI  plan-1  C5   0.020
 OAI  plan-1  C6   0.020
 OAI  plan-1  C9   0.020
 OAI  plan-1  C10  0.020
 OAI  plan-1  N11  0.020
 OAI  plan-1  N12  0.020
 OAI  plan-1  C18  0.020
 OAI  plan-1  H2   0.020
 OAI  plan-1  H5   0.020
 OAI  plan-1  H9   0.020
 OAI  plan-1  H10  0.020
 OAI  plan-1  H11  0.020
 OAI  plan-2  C3   0.020
 OAI  plan-2  N12  0.020
 OAI  plan-2  C13  0.020
 OAI  plan-2  C14  0.020
 OAI  plan-2  O17  0.020
 OAI  plan-2  H12  0.020
 OAI  plan-3  C13  0.020
 OAI  plan-3  C14  0.020
 OAI  plan-3  O15  0.020
 OAI  plan-3  O16  0.020
 OAI  plan-4  C4   0.020
 OAI  plan-4  C18  0.020
 OAI  plan-4  O19  0.020
 OAI  plan-4  O20  0.020

