# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May 19 14:31:06 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  26  18  .  2021-08-17  2023-02-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

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   0.413   1.2001  -0.0524  -2.1320
 OAI  C2   C  CR16  0  -0.396   1.2511  -0.0580  -0.7418
 OAI  C3   C  CR6   0   0.363   0.0548  -0.0288  -0.0435
 OAI  C4   C  CR6   0  -0.196  -1.1921   0.0068  -0.7511
 OAI  C5   C  CR16  0  -0.366  -1.2014   0.0118  -2.1426
 OAI  C6   C  CR56  0   0.077  -0.0115  -0.0176  -2.8542
 OAI  C9   C  CR15  0  -0.401   0.3278  -0.0228  -4.2438
 OAI  C10  C  CR15  0  -0.025   1.6876  -0.0597  -4.3053
 OAI  N11  N  NR15  0  -0.684   2.2094  -0.0776  -3.0367
 OAI  N12  N  NH1   0  -0.764   0.0214  -0.0325   1.3528
 OAI  C13  C  C     0   0.436   1.0478  -0.0613   2.2170
 OAI  C14  C  C     0   0.465   0.5532  -0.0535   3.6713
 OAI  O15  O  O     0  -0.410  -0.6107  -0.0277   3.9736
 OAI  O16  O  OH1   0  -0.565   1.5630  -0.0787   4.5074
 OAI  O17  O  O     0  -0.436   2.2354  -0.0903   1.9688
 OAI  C18  C  C     0   0.585  -2.4825   0.0383  -0.0371
 OAI  O19  O  O     0  -0.472  -2.6113   0.0351   1.1739
 OAI  O20  O  OH1   0  -0.588  -3.5333   0.0717  -0.8405
 OAI  H2   H  HCR6  0   0.298   2.1985  -0.0854  -0.2296
 OAI  H5   H  HCR6  0   0.270  -2.1381   0.0392  -2.6809
 OAI  H9   H  HCR5  0   0.257  -0.3506  -0.0018  -5.0811
 OAI  H10  H  HCR5  0   0.288   2.3417  -0.0758  -5.1617
 OAI  H11  H  HNR5  0   0.417   3.1922  -0.1017  -2.8194
 OAI  H12  H  HNH1  0   0.447  -0.9186  -0.0111   1.7493
 OAI  H16  H  HOH1  0   0.496   1.2434  -0.0741   5.4231
 OAI  H20  H  HOH1  0   0.491  -4.3465   0.0900  -0.3141

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  1.391  0.020  1.391
 OAI  C1   C6   aromatic  1.411  0.020  1.411
 OAI  C1   N11  aromatic  1.356  0.020  1.356
 OAI  C2   C3   aromatic  1.386  0.020  1.386
 OAI  C2   H2   single    0.930  0.020  1.080
 OAI  C3   C4   aromatic  1.434  0.020  1.434
 OAI  C3   N12  single    1.397  0.020  1.397
 OAI  C4   C5   aromatic  1.392  0.020  1.392
 OAI  C4   C18  single    1.475  0.020  1.475
 OAI  C5   C6   aromatic  1.387  0.020  1.387
 OAI  C5   H5   single    0.930  0.020  1.080
 OAI  C6   C9   aromatic  1.430  0.020  1.430
 OAI  C9   C10  aromatic  1.362  0.020  1.362
 OAI  C9   H9   single    0.930  0.020  1.080
 OAI  C10  N11  aromatic  1.372  0.020  1.372
 OAI  C10  H10  single    0.930  0.020  1.080
 OAI  N11  H11  single    0.860  0.020  1.020
 OAI  N12  C13  single    1.342  0.020  1.342
 OAI  N12  H12  single    0.860  0.020  1.020
 OAI  C13  C14  single    1.536  0.020  1.536
 OAI  C13  O17  double    1.214  0.020  1.214
 OAI  C14  O15  double    1.203  0.020  1.203
 OAI  C14  O16  single    1.311  0.020  1.311
 OAI  O16  H16  single    0.850  0.020  0.980
 OAI  C18  O19  double    1.218  0.020  1.218
 OAI  C18  O20  single    1.323  0.020  1.323
 OAI  O20  H20  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
 OAI  N11  C1   C6   107.35  3.000
 OAI  N11  C1   C2   129.76  3.000
 OAI  C6   C1   C2   122.89  3.000
 OAI  H2   C2   C3   121.34  3.000
 OAI  H2   C2   C1   120.50  3.000
 OAI  C3   C2   C1   118.16  3.000
 OAI  N12  C3   C4   118.20  3.000
 OAI  N12  C3   C2   121.63  3.000
 OAI  C4   C3   C2   120.17  3.000
 OAI  C18  C4   C5   118.56  3.000
 OAI  C18  C4   C3   121.49  3.000
 OAI  C5   C4   C3   119.95  3.000
 OAI  H5   C5   C6   119.25  3.000
 OAI  H5   C5   C4   120.26  3.000
 OAI  C6   C5   C4   120.49  3.000
 OAI  C9   C6   C5   134.60  3.000
 OAI  C9   C6   C1   107.06  3.000
 OAI  C5   C6   C1   118.34  3.000
 OAI  H9   C9   C10  126.44  3.000
 OAI  H9   C9   C6   127.25  3.000
 OAI  C10  C9   C6   106.31  3.000
 OAI  H10  C10  N11  120.25  3.000
 OAI  H10  C10  C9   129.97  3.000
 OAI  N11  C10  C9   109.78  3.000
 OAI  H11  N11  C10  124.83  3.000
 OAI  H11  N11  C1   125.67  3.000
 OAI  C10  N11  C1   109.50  3.000
 OAI  H12  N12  C13  117.05  3.000
 OAI  H12  N12  C3   114.23  3.000
 OAI  C13  N12  C3   128.72  3.000
 OAI  O17  C13  C14  120.59  3.000
 OAI  O17  C13  N12  128.11  3.000
 OAI  C14  C13  N12  111.30  3.000
 OAI  O16  C14  O15  125.83  3.000
 OAI  O16  C14  C13  110.83  3.000
 OAI  O15  C14  C13  123.34  3.000
 OAI  H16  O16  C14  110.37  3.000
 OAI  O20  C18  O19  121.33  3.000
 OAI  O20  C18  C4   113.66  3.000
 OAI  O19  C18  C4   125.01  3.000
 OAI  H20  O20  C18  109.70  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  CONST_32  H20  O20  C18  C4   180.00   0.0  0
 OAI  CONST_33  H16  O16  C14  C13  180.00   0.0  0
 OAI  Var_01    O19  C18  C4   C3    -0.13  30.0  2
 OAI  Var_02    O15  C14  C13  N12    0.15  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-3  H16  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
 OAI  plan-4  H20  0.020

