# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 29 03:28:41 2022
#   Inital geometry file: a 107 line input string
#   Ligand name: 3-(3-hydroxy-3-oxopropyl)-5-(2-methylpropyl)-7-nitro-1~{H}-indole-2-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)Cc1cc2c(CCC(O)=O)c([nH]c2c(c1)[N+]([O-])=O)C(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
 0GI  0GI  "3-(3-hydroxy-3-oxopropyl)-5-(2-methylpropyl)-7-nitro-1H-indole-2-carboxylic acid"  ligand  40  24  .  2022-09-22  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_0GI
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
 0GI  C10  C  CH2    0  -0.522  -13.2865   8.9794  -7.4294
 0GI  C13  C  CH2    0  -0.490  -18.8546   8.1002  -6.9388
 0GI  C15  C  CH3    0  -0.653  -18.8115  10.6344  -6.9704
 0GI  C1   C  CR6    0   0.126  -17.6042   7.9719  -6.1147
 0GI  C2   C  CR16   0  -0.382  -17.6951   7.5800  -4.7789
 0GI  C3   C  CR6    0   0.229  -16.5730   7.5122  -3.9647
 0GI  C4   C  CR56   0   0.350  -15.3168   7.8497  -4.4897
 0GI  C5   C  CR56   0   0.020  -15.2180   8.2436  -5.8491
 0GI  C6   C  CR16   0  -0.406  -16.3594   8.2942  -6.6428
 0GI  C7   C  CR5    0   0.090  -13.1728   8.3044  -4.9354
 0GI  C8   C  CR5    0   0.032  -13.8376   8.5255  -6.1150
 0GI  C9   C  C      0   0.364  -11.7229   8.4186  -4.5354
 0GI  C11  C  CH2    0  -0.530  -13.3037  10.5026  -7.6161
 0GI  C12  C  C      0   0.408  -14.7209  11.0708  -7.8134
 0GI  C14  C  CH1    0  -0.225  -19.6376   9.3916  -6.6620
 0GI  C16  C  CH3    0  -0.653  -20.9371   9.3924  -7.4583
 0GI  N1   N  NR15   0  -0.699  -14.0745   7.8967  -3.9759
 0GI  N2   N  N      1   0.335  -16.7137   7.0998  -2.6000
 0GI  O1   O  O      0  -0.570  -10.9274   8.8372  -5.3946
 0GI  O2   O  OC    -1  -0.594  -11.4725   8.0779  -3.3618
 0GI  O3   O  OC    -1  -0.608  -15.1456  11.8818  -6.9664
 0GI  O4   O  O      0  -0.617  -15.3353  10.6647  -8.8261
 0GI  O5   O  O     -1  -0.410  -15.7097   7.0657  -1.9141
 0GI  O6   O  O      0  -0.393  -17.8114   6.8029  -2.1819
 0GI  H1   H  HCH2   0   0.217  -13.8557   8.5206  -8.2414
 0GI  H2   H  HCH2   0   0.234  -12.2624   8.6228  -7.5248
 0GI  H3   H  HCH2   0   0.239  -19.5105   7.2453  -6.7495
 0GI  H4   H  HCH2   0   0.234  -18.5991   8.0649  -8.0024
 0GI  H5   H  HCH3   0   0.227  -17.9257  10.7062  -6.3392
 0GI  H6   H  HCH3   0   0.209  -18.4736  10.6312  -8.0097
 0GI  H7   H  HCH3   0   0.225  -19.4005  11.5399  -6.8153
 0GI  H8   H  HCR6   0   0.277  -18.6639   7.3243  -4.3704
 0GI  H9   H  HCR6   0   0.250  -16.2794   8.6195  -7.6734
 0GI  H10  H  HCH2   0   0.212  -12.7093  10.7384  -8.5053
 0GI  H11  H  HCH2   0   0.196  -12.8037  10.9711  -6.7657
 0GI  H12  H  HCH1   0   0.219  -19.8913   9.4046  -5.5953
 0GI  H13  H  HCH3   0   0.226  -21.5330  10.2808  -7.2432
 0GI  H14  H  HCH3   0   0.214  -20.7349   9.3822  -8.5323
 0GI  H15  H  HCH3   0   0.223  -21.5482   8.5178  -7.2281
 0GI  H16  H  HNR5   0   0.396  -13.8004   7.6723  -3.0344

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
 0GI  O4   C12  deloc     1.252  0.020  1.252
 0GI  O3   C12  deloc     1.247  0.020  1.247
 0GI  C12  C11  single    1.540  0.020  1.540
 0GI  C11  C10  single    1.535  0.020  1.535
 0GI  C16  C14  single    1.524  0.020  1.524
 0GI  C10  C8   single    1.496  0.020  1.496
 0GI  C13  C14  single    1.535  0.020  1.535
 0GI  C13  C1   single    1.503  0.020  1.503
 0GI  C6   C1   aromatic  1.390  0.020  1.390
 0GI  C6   C5   aromatic  1.391  0.020  1.391
 0GI  C15  C14  single    1.524  0.020  1.524
 0GI  C1   C2   aromatic  1.395  0.020  1.395
 0GI  C8   C5   aromatic  1.434  0.020  1.434
 0GI  C8   C7   aromatic  1.372  0.020  1.372
 0GI  C5   C4   aromatic  1.419  0.020  1.419
 0GI  O1   C9   deloc     1.243  0.020  1.243
 0GI  C2   C3   aromatic  1.388  0.020  1.388
 0GI  C7   C9   single    1.508  0.020  1.508
 0GI  C7   N1   aromatic  1.378  0.020  1.378
 0GI  C4   C3   aromatic  1.403  0.020  1.403
 0GI  C4   N1   aromatic  1.345  0.020  1.345
 0GI  C9   O2   deloc     1.247  0.020  1.247
 0GI  C3   N2   single    1.433  0.020  1.433
 0GI  N2   O6   double    1.212  0.020  1.212
 0GI  N2   O5   single    1.216  0.020  1.216
 0GI  C10  H1   single    0.970  0.020  1.090
 0GI  C10  H2   single    0.970  0.020  1.090
 0GI  C13  H3   single    0.970  0.020  1.090
 0GI  C13  H4   single    0.970  0.020  1.090
 0GI  C15  H5   single    0.970  0.020  1.090
 0GI  C15  H6   single    0.970  0.020  1.090
 0GI  C15  H7   single    0.970  0.020  1.090
 0GI  C2   H8   single    0.930  0.020  1.080
 0GI  C6   H9   single    0.930  0.020  1.080
 0GI  C11  H10  single    0.970  0.020  1.090
 0GI  C11  H11  single    0.970  0.020  1.090
 0GI  C14  H12  single    0.970  0.020  1.090
 0GI  C16  H13  single    0.970  0.020  1.090
 0GI  C16  H14  single    0.970  0.020  1.090
 0GI  C16  H15  single    0.970  0.020  1.090
 0GI  N1   H16  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
 0GI  H2   C10  H1   106.70  3.000
 0GI  H2   C10  C11  108.97  3.000
 0GI  H1   C10  C11  108.69  3.000
 0GI  H2   C10  C8   108.92  3.000
 0GI  H1   C10  C8   109.49  3.000
 0GI  C11  C10  C8   113.82  3.000
 0GI  H4   C13  H3   106.44  3.000
 0GI  H4   C13  C14  108.74  3.000
 0GI  H3   C13  C14  108.68  3.000
 0GI  H4   C13  C1   109.63  3.000
 0GI  H3   C13  C1   109.70  3.000
 0GI  C14  C13  C1   113.40  3.000
 0GI  H7   C15  H6   107.73  3.000
 0GI  H7   C15  H5   107.55  3.000
 0GI  H6   C15  H5   107.43  3.000
 0GI  H7   C15  C14  110.82  3.000
 0GI  H6   C15  C14  110.96  3.000
 0GI  H5   C15  C14  112.15  3.000
 0GI  C6   C1   C2   119.16  3.000
 0GI  C2   C1   C13  119.66  3.000
 0GI  C6   C1   C13  121.12  3.000
 0GI  H8   C2   C3   119.40  3.000
 0GI  H8   C2   C1   119.09  3.000
 0GI  C3   C2   C1   121.51  3.000
 0GI  N2   C3   C4   120.92  3.000
 0GI  N2   C3   C2   119.57  3.000
 0GI  C4   C3   C2   119.52  3.000
 0GI  N1   C4   C5   106.98  3.000
 0GI  N1   C4   C3   133.83  3.000
 0GI  C5   C4   C3   119.19  3.000
 0GI  C8   C5   C6   132.61  3.000
 0GI  C8   C5   C4   107.42  3.000
 0GI  C6   C5   C4   119.98  3.000
 0GI  H9   C6   C5   119.54  3.000
 0GI  H9   C6   C1   119.80  3.000
 0GI  C5   C6   C1   120.63  3.000
 0GI  N1   C7   C9   117.81  3.000
 0GI  N1   C7   C8   109.22  3.000
 0GI  C9   C7   C8   132.97  3.000
 0GI  C7   C8   C5   105.98  3.000
 0GI  C7   C8   C10  128.75  3.000
 0GI  C5   C8   C10  125.27  3.000
 0GI  O2   C9   O1   127.85  3.000
 0GI  O2   C9   C7   114.94  3.000
 0GI  O1   C9   C7   117.21  3.000
 0GI  H11  C11  H10  106.94  3.000
 0GI  H11  C11  C12  111.28  3.000
 0GI  H10  C11  C12  108.42  3.000
 0GI  H11  C11  C10  109.02  3.000
 0GI  H10  C11  C10  107.84  3.000
 0GI  C12  C11  C10  113.09  3.000
 0GI  O4   C12  O3   126.37  3.000
 0GI  O3   C12  C11  117.80  3.000
 0GI  O4   C12  C11  115.83  3.000
 0GI  H12  C14  C16  108.12  3.000
 0GI  H12  C14  C15  108.22  3.000
 0GI  C16  C14  C15  110.86  3.000
 0GI  H12  C14  C13  107.66  3.000
 0GI  C15  C14  C13  111.90  3.000
 0GI  C16  C14  C13  109.94  3.000
 0GI  H15  C16  H14  107.66  3.000
 0GI  H15  C16  H13  107.76  3.000
 0GI  H14  C16  H13  107.60  3.000
 0GI  H15  C16  C14  111.52  3.000
 0GI  H14  C16  C14  110.84  3.000
 0GI  H13  C16  C14  111.29  3.000
 0GI  H16  N1   C7   122.64  3.000
 0GI  H16  N1   C4   126.96  3.000
 0GI  C7   N1   C4   110.40  3.000
 0GI  O6   N2   O5   123.12  3.000
 0GI  O5   N2   C3   117.66  3.000
 0GI  O6   N2   C3   119.23  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
 0GI  CONST_01  C8   C5   C6   C1    180.00   0.0  0
 0GI  CONST_02  C4   C5   C6   C1      0.00   0.0  0
 0GI  CONST_03  C4   C3   C2   C1      0.00   0.0  0
 0GI  CONST_04  C5   C6   C1   C2      0.00   0.0  0
 0GI  CONST_05  C5   C4   C3   C2      0.00   0.0  0
 0GI  CONST_06  N1   C4   C3   C2    180.00   0.0  0
 0GI  CONST_07  C6   C1   C2   C3      0.00   0.0  0
 0GI  CONST_08  C6   C5   C4   C3      0.00   0.0  0
 0GI  CONST_09  C8   C5   C4   C3    180.00   0.0  0
 0GI  CONST_10  C7   N1   C4   C3    180.00   0.0  0
 0GI  CONST_11  C7   C8   C5   C4      0.00   0.0  0
 0GI  CONST_12  C8   C7   N1   C4      0.00   0.0  0
 0GI  CONST_13  N1   C7   C8   C5      0.00   0.0  0
 0GI  CONST_14  C7   N1   C4   C5      0.00   0.0  0
 0GI  CONST_15  C7   C8   C5   C6    180.00   0.0  0
 0GI  CONST_16  N1   C4   C5   C6    180.00   0.0  0
 0GI  CONST_17  N1   C4   C5   C8      0.00   0.0  0
 0GI  CONST_18  C6   C5   C8   C10     0.00   0.0  0
 0GI  CONST_19  C4   C5   C8   C10   180.00   0.0  0
 0GI  CONST_20  N1   C7   C8   C10   180.00   0.0  0
 0GI  CONST_21  C5   C6   C1   C13   180.00   0.0  0
 0GI  CONST_22  C3   C2   C1   C13   180.00   0.0  0
 0GI  CONST_23  N2   C3   C2   C1    180.00   0.0  0
 0GI  CONST_24  C9   C7   N1   C4    180.00   0.0  0
 0GI  CONST_25  C9   C7   C8   C5    180.00   0.0  0
 0GI  CONST_26  N2   C3   C4   C5    180.00   0.0  0
 0GI  CONST_27  N2   C3   C4   N1      0.00   0.0  0
 0GI  CONST_28  H9   C6   C1   C2    180.00   0.0  0
 0GI  CONST_29  H16  N1   C4   C3      0.00   0.0  0
 0GI  CONST_30  H9   C6   C5   C4    180.00   0.0  0
 0GI  CONST_31  H8   C2   C3   C4    180.00   0.0  0
 0GI  CONST_32  H16  N1   C4   C5    180.00   0.0  0
 0GI  CONST_33  H8   C2   C1   C6    180.00   0.0  0
 0GI  CONST_34  H9   C6   C5   C8      0.00   0.0  0
 0GI  CONST_35  H16  N1   C7   C8    180.00   0.0  0
 0GI  CONST_36  O6   N2   C3   C2      0.00   0.0  0
 0GI  CONST_37  O5   N2   C3   C2    180.00   0.0  0
 0GI  CONST_38  O6   N2   C3   C4    180.00   0.0  0
 0GI  CONST_39  O5   N2   C3   C4      0.00   0.0  0
 0GI  Var_01    C14  C13  C1   C2     77.98  30.0  2
 0GI  Var_02    C11  C10  C8   C5     87.98  30.0  3
 0GI  Var_03    C14  C13  C1   C6    -99.14  30.0  2
 0GI  Var_04    C11  C10  C8   C7    -91.38  30.0  3
 0GI  Var_05    O1   C9   C7   C8      2.96  30.0  2
 0GI  Var_06    O2   C9   C7   C8   -177.24  30.0  2
 0GI  Var_07    O1   C9   C7   N1   -177.27  30.0  2
 0GI  Var_08    O2   C9   C7   N1      2.54  30.0  2
 0GI  Var_09    H3   C13  C1   C2    -43.74  30.0  2
 0GI  Var_10    H4   C13  C1   C2   -160.28  30.0  2
 0GI  Var_11    H1   C10  C8   C5    -33.89  30.0  3
 0GI  Var_12    H2   C10  C8   C5   -150.22  30.0  3
 0GI  Var_13    H3   C13  C1   C6    139.14  30.0  2
 0GI  Var_14    H4   C13  C1   C6     22.60  30.0  2
 0GI  Var_15    H1   C10  C8   C7    146.75  30.0  3
 0GI  Var_16    H2   C10  C8   C7     30.42  30.0  3
 0GI  Var_17    C1   C13  C14  C15    60.56  30.0  1
 0GI  Var_18    C16  C14  C13  C1   -175.79  30.0  3
 0GI  Var_19    C12  C11  C10  C8    -71.07  30.0  1
 0GI  Var_20    H12  C14  C13  C1    -58.24  30.0  3
 0GI  Var_21    H10  C11  C10  C8    169.05  30.0  1
 0GI  Var_22    H11  C11  C10  C8     53.29  30.0  1
 0GI  Var_23    O4   C12  C11  C10   -61.99  30.0  2
 0GI  Var_24    O3   C12  C11  C10   118.13  30.0  2
 0GI  Var_25    H13  C16  C14  C13   177.42  30.0  3
 0GI  Var_26    H14  C16  C14  C13   -62.87  30.0  3
 0GI  Var_27    H15  C16  C14  C13    57.07  30.0  3
 0GI  Var_28    H5   C15  C14  C13   -62.62  30.0  3
 0GI  Var_29    H6   C15  C14  C13    57.54  30.0  3
 0GI  Var_30    H7   C15  C14  C13   177.17  30.0  3
 0GI  Var_31    H13  C16  C14  C15   -58.32  30.0  3
 0GI  Var_32    H14  C16  C14  C15    61.39  30.0  3
 0GI  Var_33    H15  C16  C14  C15  -178.68  30.0  3
 0GI  Var_34    H3   C13  C14  C15  -177.16  30.0  1
 0GI  Var_35    H4   C13  C14  C15   -61.68  30.0  1
 0GI  Var_36    H1   C10  C11  C12    51.24  30.0  3
 0GI  Var_37    H2   C10  C11  C12   167.16  30.0  3
 0GI  Var_38    H3   C13  C14  C16   -53.51  30.0  1
 0GI  Var_39    H4   C13  C14  C16    61.97  30.0  1
 0GI  Var_40    H5   C15  C14  C16   174.25  30.0  3
 0GI  Var_41    H6   C15  C14  C16   -65.59  30.0  3
 0GI  Var_42    H7   C15  C14  C16    54.04  30.0  3
 0GI  Var_43    H10  C11  C12  O3   -122.33  30.0  3
 0GI  Var_44    H11  C11  C12  O3     -4.99  30.0  3
 0GI  Var_45    H10  C11  C12  O4     57.56  30.0  3
 0GI  Var_46    H11  C11  C12  O4    174.90  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
 0GI  plan-1  C10  0.020
 0GI  plan-1  C13  0.020
 0GI  plan-1  C1   0.020
 0GI  plan-1  C2   0.020
 0GI  plan-1  C3   0.020
 0GI  plan-1  C4   0.020
 0GI  plan-1  C5   0.020
 0GI  plan-1  C6   0.020
 0GI  plan-1  C7   0.020
 0GI  plan-1  C8   0.020
 0GI  plan-1  C9   0.020
 0GI  plan-1  N1   0.020
 0GI  plan-1  N2   0.020
 0GI  plan-1  H8   0.020
 0GI  plan-1  H9   0.020
 0GI  plan-1  H16  0.020
 0GI  plan-2  C3   0.020
 0GI  plan-2  N2   0.020
 0GI  plan-2  O5   0.020
 0GI  plan-2  O6   0.020
 0GI  plan-3  C7   0.020
 0GI  plan-3  C9   0.020
 0GI  plan-3  O1   0.020
 0GI  plan-3  O2   0.020
 0GI  plan-4  C11  0.020
 0GI  plan-4  C12  0.020
 0GI  plan-4  O3   0.020
 0GI  plan-4  O4   0.020

