# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr  7 05:05:28 2020
#   Inital geometry file: a 135 line input string
#   Ligand name: ethyl 6-{[5-(cyclopropylcarbamoyl)-2-methylphenyl]carbamoyl}-1H-indole-1-carboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCOC(=O)n1ccc2ccc(cc12)C(=O)Nc3cc(ccc3C)C(=O)NC4CC4
#
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
 1RA  1RA  'ethyl 6-{[5-(cyclopropylcarbamoyl)-2-methylphenyl]carbamoyl}-1H-indole-1-carboxylate'  ligand  53  30  .  2022-09-22  2023-02-02
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_1RA
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
 1RA  C1   C  CR6   0   0.056   2.9352   2.2873  -1.1067
 1RA  N10  N  NH1   0  -0.656   6.4405  -0.9252   0.6318
 1RA  C11  C  CH1   0  -0.080   7.2615  -1.9786   1.1304
 1RA  C12  C  CH2   0  -0.512   8.6670  -2.0495   0.6286
 1RA  C13  C  CH2   0  -0.483   7.6662  -3.0806   0.2051
 1RA  N14  N  NH1   0  -0.772   0.9591   1.4687   0.0031
 1RA  C16  C  C     0   0.539   0.0274   0.4788   0.0532
 1RA  O17  O  O     0  -0.459   0.2769  -0.6802  -0.2285
 1RA  C18  C  CR6   0  -0.063  -1.3418   0.9078   0.4624
 1RA  C19  C  CR16  0  -0.309  -2.3978   0.0910   0.0719
 1RA  C2   C  CR6   0   0.338   2.3160   1.3071  -0.3175
 1RA  C20  C  CR16  0  -0.320  -2.8457   2.4074   1.6290
 1RA  C21  C  CR16  0  -0.305  -1.5696   2.0541   1.2415
 1RA  C22  C  CR56  0   0.056  -3.9164   1.6091   1.2318
 1RA  C23  C  CR56  0   0.390  -3.6777   0.4588   0.4559
 1RA  N24  N  NR5   0  -0.653  -4.9145  -0.1375   0.2245
 1RA  C25  C  CR15  0  -0.002  -5.8951   0.6288   0.8455
 1RA  C26  C  CR15  0  -0.386  -5.3285   1.6884   1.4612
 1RA  C27  C  C     0   0.785  -5.1290  -1.2991  -0.5019
 1RA  O28  O  O     0  -0.462  -4.2453  -1.9101  -1.0450
 1RA  O29  O  O2    0  -0.465  -6.4030  -1.6217  -0.5048
 1RA  C3   C  CR16  0  -0.307   3.0453   0.2249   0.1599
 1RA  C30  C  CH2   0  -0.179  -6.7919  -2.8062  -1.2284
 1RA  C31  C  CH3   0  -0.689  -8.2767  -2.9873  -1.0391
 1RA  C4   C  CR6   0  -0.049   4.4000   0.1044  -0.1268
 1RA  C5   C  CR16  0  -0.291   5.0230   1.0713  -0.9094
 1RA  C6   C  CR16  0  -0.290   4.2898   2.1456  -1.3852
 1RA  C7   C  CH3   0  -0.754   2.1638   3.4546  -1.6447
 1RA  C8   C  C     0   0.529   5.1241  -1.0909   0.4030
 1RA  O9   O  O     0  -0.481   4.5443  -2.1462   0.6131
 1RA  H1   H  HNH1  0   0.406   6.8261   0.0053   0.6189
 1RA  H2   H  HCH1  0   0.268   7.0925  -2.2431   2.1699
 1RA  H3   H  HCH2  0   0.258   8.9734  -1.3145  -0.1053
 1RA  H4   H  HCH2  0   0.259   9.4385  -2.3291   1.3337
 1RA  H5   H  HCH2  0   0.256   7.7430  -4.0784   0.6165
 1RA  H6   H  HCH2  0   0.256   7.3008  -3.0386  -0.8125
 1RA  H7   H  HNH1  0   0.417   0.6292   2.4184   0.0688
 1RA  H8   H  HCR6  0   0.280  -2.2074  -0.7921  -0.5166
 1RA  H9   H  HCR6  0   0.264  -3.0098   3.2845   2.2408
 1RA  H10  H  HCR6  0   0.260  -0.7446   2.6667   1.5815
 1RA  H11  H  HCR5  0   0.308  -6.9324   0.3466   0.7937
 1RA  H12  H  HCR5  0   0.267  -5.8518   2.4480   2.0191
 1RA  H13  H  HCR6  0   0.269   2.5698  -0.5186   0.7817
 1RA  H14  H  HCH2  0   0.246  -6.5403  -2.6821  -2.2825
 1RA  H15  H  HCH2  0   0.245  -6.2397  -3.6641  -0.8419
 1RA  H16  H  HCH3  0   0.240  -8.8389  -2.1363  -1.4229
 1RA  H17  H  HCH3  0   0.244  -8.5948  -3.8734  -1.5874
 1RA  H18  H  HCH3  0   0.240  -8.5324  -3.1323   0.0100
 1RA  H19  H  HCR6  0   0.259   6.0679   0.9867  -1.1790
 1RA  H20  H  HCR6  0   0.260   4.7785   2.8881  -2.0034
 1RA  H21  H  HCH3  0   0.255   1.8226   4.1203  -0.8477
 1RA  H22  H  HCH3  0   0.265   2.7810   4.0501  -2.3145
 1RA  H23  H  HCH3  0   0.256   1.2798   3.1328  -2.1980

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
 1RA  C6   C5   aromatic  1.385  0.020  1.385
 1RA  C6   C1   aromatic  1.390  0.020  1.390
 1RA  C7   C1   single    1.499  0.020  1.499
 1RA  C5   C4   aromatic  1.391  0.020  1.391
 1RA  C1   C2   aromatic  1.402  0.020  1.402
 1RA  C12  C13  single    1.498  0.020  1.498
 1RA  C12  C11  single    1.494  0.020  1.494
 1RA  N10  C11  single    1.426  0.020  1.426
 1RA  N10  C8   single    1.346  0.020  1.346
 1RA  C4   C8   single    1.495  0.020  1.495
 1RA  C4   C3   aromatic  1.390  0.020  1.390
 1RA  C13  C11  single    1.495  0.020  1.495
 1RA  C2   C3   aromatic  1.390  0.020  1.390
 1RA  C2   N14  single    1.404  0.020  1.404
 1RA  C8   O9   double    1.222  0.020  1.222
 1RA  N14  C16  single    1.360  0.020  1.360
 1RA  C16  O17  double    1.218  0.020  1.218
 1RA  C16  C18  single    1.492  0.020  1.492
 1RA  C21  C18  aromatic  1.405  0.020  1.405
 1RA  C21  C20  aromatic  1.380  0.020  1.380
 1RA  C18  C19  aromatic  1.391  0.020  1.391
 1RA  C20  C22  aromatic  1.393  0.020  1.393
 1RA  C19  C23  aromatic  1.386  0.020  1.386
 1RA  C22  C23  aromatic  1.408  0.020  1.408
 1RA  C22  C26  aromatic  1.433  0.020  1.433
 1RA  C23  N24  aromatic  1.392  0.020  1.392
 1RA  C26  C25  aromatic  1.350  0.020  1.350
 1RA  C31  C30  single    1.508  0.020  1.508
 1RA  O29  C30  single    1.442  0.020  1.442
 1RA  O29  C27  single    1.314  0.020  1.314
 1RA  N24  C25  aromatic  1.391  0.020  1.391
 1RA  N24  C27  single    1.387  0.020  1.387
 1RA  C27  O28  double    1.204  0.020  1.204
 1RA  N10  H1   single    0.860  0.020  1.020
 1RA  C11  H2   single    0.970  0.020  1.090
 1RA  C12  H3   single    0.970  0.020  1.090
 1RA  C12  H4   single    0.970  0.020  1.090
 1RA  C13  H5   single    0.970  0.020  1.090
 1RA  C13  H6   single    0.970  0.020  1.090
 1RA  N14  H7   single    0.860  0.020  1.020
 1RA  C19  H8   single    0.930  0.020  1.080
 1RA  C20  H9   single    0.930  0.020  1.080
 1RA  C21  H10  single    0.930  0.020  1.080
 1RA  C25  H11  single    0.930  0.020  1.080
 1RA  C26  H12  single    0.930  0.020  1.080
 1RA  C3   H13  single    0.930  0.020  1.080
 1RA  C30  H14  single    0.970  0.020  1.090
 1RA  C30  H15  single    0.970  0.020  1.090
 1RA  C31  H16  single    0.970  0.020  1.090
 1RA  C31  H17  single    0.970  0.020  1.090
 1RA  C31  H18  single    0.970  0.020  1.090
 1RA  C5   H19  single    0.930  0.020  1.080
 1RA  C6   H20  single    0.930  0.020  1.080
 1RA  C7   H21  single    0.970  0.020  1.090
 1RA  C7   H22  single    0.970  0.020  1.090
 1RA  C7   H23  single    0.970  0.020  1.090

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
 1RA  C7   C1   C6   120.59  3.000
 1RA  C7   C1   C2   121.26  3.000
 1RA  C6   C1   C2   118.15  3.000
 1RA  H1   N10  C8   119.06  3.000
 1RA  H1   N10  C11  117.82  3.000
 1RA  C8   N10  C11  122.11  3.000
 1RA  H2   C11  C13  117.08  3.000
 1RA  H2   C11  C12  117.15  3.000
 1RA  C13  C11  C12   60.16  3.000
 1RA  H2   C11  N10  115.16  3.000
 1RA  C13  C11  N10  118.96  3.000
 1RA  C12  C11  N10  117.35  3.000
 1RA  H4   C12  H3   114.54  3.000
 1RA  H4   C12  C13  118.87  3.000
 1RA  H3   C12  C13  117.69  3.000
 1RA  H4   C12  C11  117.66  3.000
 1RA  H3   C12  C11  117.49  3.000
 1RA  C13  C12  C11   59.94  3.000
 1RA  H6   C13  H5   114.67  3.000
 1RA  H6   C13  C12  117.69  3.000
 1RA  H5   C13  C12  118.67  3.000
 1RA  H6   C13  C11  117.52  3.000
 1RA  H5   C13  C11  117.63  3.000
 1RA  C12  C13  C11   59.90  3.000
 1RA  H7   N14  C2   116.10  3.000
 1RA  H7   N14  C16  117.34  3.000
 1RA  C2   N14  C16  125.93  3.000
 1RA  C18  C16  O17  121.65  3.000
 1RA  C18  C16  N14  115.43  3.000
 1RA  O17  C16  N14  122.91  3.000
 1RA  C21  C18  C19  120.79  3.000
 1RA  C19  C18  C16  116.79  3.000
 1RA  C21  C18  C16  122.39  3.000
 1RA  H8   C19  C23  122.12  3.000
 1RA  H8   C19  C18  120.01  3.000
 1RA  C23  C19  C18  117.87  3.000
 1RA  C3   C2   N14  121.23  3.000
 1RA  N14  C2   C1   118.36  3.000
 1RA  C3   C2   C1   120.39  3.000
 1RA  H9   C20  C22  120.60  3.000
 1RA  H9   C20  C21  120.45  3.000
 1RA  C22  C20  C21  118.95  3.000
 1RA  H10  C21  C20  118.16  3.000
 1RA  H10  C21  C18  120.83  3.000
 1RA  C20  C21  C18  120.98  3.000
 1RA  C26  C22  C23  107.49  3.000
 1RA  C26  C22  C20  132.84  3.000
 1RA  C23  C22  C20  119.66  3.000
 1RA  N24  C23  C22  106.91  3.000
 1RA  N24  C23  C19  131.34  3.000
 1RA  C22  C23  C19  121.74  3.000
 1RA  C27  N24  C25  125.89  3.000
 1RA  C27  N24  C23  125.68  3.000
 1RA  C25  N24  C23  108.43  3.000
 1RA  H11  C25  C26  129.21  3.000
 1RA  H11  C25  N24  120.91  3.000
 1RA  C26  C25  N24  109.88  3.000
 1RA  H12  C26  C25  125.82  3.000
 1RA  H12  C26  C22  126.90  3.000
 1RA  C25  C26  C22  107.29  3.000
 1RA  O29  C27  O28  125.87  3.000
 1RA  O28  C27  N24  123.22  3.000
 1RA  O29  C27  N24  110.90  3.000
 1RA  C30  O29  C27  117.67  3.000
 1RA  H13  C3   C4   119.23  3.000
 1RA  H13  C3   C2   120.20  3.000
 1RA  C4   C3   C2   120.54  3.000
 1RA  H15  C30  H14  108.37  3.000
 1RA  H15  C30  C31  111.07  3.000
 1RA  H14  C30  C31  111.23  3.000
 1RA  H15  C30  O29  109.38  3.000
 1RA  H14  C30  O29  109.23  3.000
 1RA  C31  C30  O29  107.54  3.000
 1RA  H18  C31  H17  107.92  3.000
 1RA  H18  C31  H16  108.78  3.000
 1RA  H17  C31  H16  107.89  3.000
 1RA  H18  C31  C30  111.59  3.000
 1RA  H17  C31  C30  108.79  3.000
 1RA  H16  C31  C30  111.73  3.000
 1RA  C8   C4   C5   122.56  3.000
 1RA  C8   C4   C3   117.93  3.000
 1RA  C5   C4   C3   119.49  3.000
 1RA  H19  C5   C6   119.08  3.000
 1RA  H19  C5   C4   121.20  3.000
 1RA  C6   C5   C4   119.69  3.000
 1RA  H20  C6   C5   119.28  3.000
 1RA  H20  C6   C1   118.97  3.000
 1RA  C5   C6   C1   121.74  3.000
 1RA  H23  C7   H22  107.98  3.000
 1RA  H23  C7   H21  107.24  3.000
 1RA  H22  C7   H21  107.02  3.000
 1RA  H23  C7   C1   111.66  3.000
 1RA  H22  C7   C1   110.80  3.000
 1RA  H21  C7   C1   111.91  3.000
 1RA  O9   C8   C4   121.44  3.000
 1RA  O9   C8   N10  122.74  3.000
 1RA  C4   C8   N10  115.82  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
 1RA  CONST_01  C4   C5   C6   C1      0.00   0.0  0
 1RA  CONST_02  C4   C3   C2   C1      0.00   0.0  0
 1RA  CONST_03  C22  C20  C21  C18     0.00   0.0  0
 1RA  CONST_04  C22  C23  C19  C18     0.00   0.0  0
 1RA  CONST_05  N24  C23  C19  C18   180.00   0.0  0
 1RA  CONST_06  C20  C21  C18  C19     0.00   0.0  0
 1RA  CONST_07  C20  C22  C23  C19     0.00   0.0  0
 1RA  CONST_08  C26  C22  C23  C19   180.00   0.0  0
 1RA  CONST_09  C25  N24  C23  C19   180.00   0.0  0
 1RA  CONST_10  C5   C6   C1   C2      0.00   0.0  0
 1RA  CONST_11  C5   C4   C3   C2      0.00   0.0  0
 1RA  CONST_12  N24  C23  C22  C20   180.00   0.0  0
 1RA  CONST_13  C25  C26  C22  C20   180.00   0.0  0
 1RA  CONST_14  C23  C19  C18  C21     0.00   0.0  0
 1RA  CONST_15  C23  C22  C20  C21     0.00   0.0  0
 1RA  CONST_16  C26  C22  C20  C21   180.00   0.0  0
 1RA  CONST_17  C25  N24  C23  C22     0.00   0.0  0
 1RA  CONST_18  N24  C25  C26  C22     0.00   0.0  0
 1RA  CONST_19  C25  C26  C22  C23     0.00   0.0  0
 1RA  CONST_20  C26  C25  N24  C23     0.00   0.0  0
 1RA  CONST_21  C26  C22  C23  N24     0.00   0.0  0
 1RA  CONST_22  C6   C5   C4   C3      0.00   0.0  0
 1RA  CONST_23  C6   C1   C2   C3      0.00   0.0  0
 1RA  CONST_24  C6   C1   C2   N14   180.00   0.0  0
 1RA  CONST_25  C4   C3   C2   N14   180.00   0.0  0
 1RA  CONST_26  C20  C21  C18  C16   180.00   0.0  0
 1RA  CONST_27  C23  C19  C18  C16   180.00   0.0  0
 1RA  CONST_28  C27  N24  C23  C19     0.00   0.0  0
 1RA  CONST_29  C8   C4   C3   C2    180.00   0.0  0
 1RA  CONST_30  C27  N24  C23  C22   180.00   0.0  0
 1RA  CONST_31  C27  N24  C25  C26   180.00   0.0  0
 1RA  CONST_32  C7   C1   C2   C3    180.00   0.0  0
 1RA  CONST_33  C7   C1   C6   C5    180.00   0.0  0
 1RA  CONST_34  C8   C4   C5   C6    180.00   0.0  0
 1RA  CONST_35  H19  C5   C6   C1    180.00   0.0  0
 1RA  CONST_36  H13  C3   C2   C1    180.00   0.0  0
 1RA  CONST_37  H9   C20  C21  C18   180.00   0.0  0
 1RA  CONST_38  H10  C21  C18  C19   180.00   0.0  0
 1RA  CONST_39  H20  C6   C1   C2    180.00   0.0  0
 1RA  CONST_40  H12  C26  C22  C20     0.00   0.0  0
 1RA  CONST_41  H8   C19  C18  C21   180.00   0.0  0
 1RA  CONST_42  H11  C25  C26  C22   180.00   0.0  0
 1RA  CONST_43  C4   C8   N10  C11   180.00   0.0  0
 1RA  CONST_44  C2   N14  C16  C18   180.00   0.0  0
 1RA  CONST_48  O9   C8   N10  C11     0.00   0.0  0
 1RA  CONST_49  C2   N14  C16  O17     0.00   0.0  0
 1RA  CONST_50  H1   N10  C8   C4      0.00   0.0  0
 1RA  Var_01    C13  C12  C11  N10  -109.38  30.0  1
 1RA  Var_02    H5   C13  C12  C11  -107.09  30.0  1
 1RA  Var_03    C5   C4   C8   N10    29.20  30.0  2
 1RA  Var_04    C8   N10  C11  C12   144.52  30.0  2
 1RA  Var_05    C21  C18  C16  N14   -24.79  30.0  2
 1RA  Var_06    O29  C27  N24  C23   178.19  30.0  2
 1RA  Var_07    H21  C7   C1   C2     66.50  30.0  2
 1RA  Var_08    C31  C30  O29  C27   177.94  30.0  3
 1RA  Var_09    H16  C31  C30  O29    60.42  30.0  3

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 1RA  chir_01  C11  C12  N10  C13  both

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
 1RA  plan-1  N24  0.020
 1RA  plan-1  C27  0.020
 1RA  plan-1  O28  0.020
 1RA  plan-1  O29  0.020
 1RA  plan-2  C1   0.020
 1RA  plan-2  N14  0.020
 1RA  plan-2  C2   0.020
 1RA  plan-2  C3   0.020
 1RA  plan-2  C4   0.020
 1RA  plan-2  C5   0.020
 1RA  plan-2  C6   0.020
 1RA  plan-2  C7   0.020
 1RA  plan-2  C8   0.020
 1RA  plan-2  H13  0.020
 1RA  plan-2  H19  0.020
 1RA  plan-2  H20  0.020
 1RA  plan-3  C16  0.020
 1RA  plan-3  C18  0.020
 1RA  plan-3  C19  0.020
 1RA  plan-3  C20  0.020
 1RA  plan-3  C21  0.020
 1RA  plan-3  C22  0.020
 1RA  plan-3  C23  0.020
 1RA  plan-3  N24  0.020
 1RA  plan-3  C25  0.020
 1RA  plan-3  C26  0.020
 1RA  plan-3  C27  0.020
 1RA  plan-3  H8   0.020
 1RA  plan-3  H9   0.020
 1RA  plan-3  H10  0.020
 1RA  plan-3  H11  0.020
 1RA  plan-3  H12  0.020
 1RA  plan-4  N10  0.020
 1RA  plan-4  C11  0.020
 1RA  plan-4  C4   0.020
 1RA  plan-4  C8   0.020
 1RA  plan-4  O9   0.020
 1RA  plan-4  H1   0.020
 1RA  plan-5  N14  0.020
 1RA  plan-5  C16  0.020
 1RA  plan-5  O17  0.020
 1RA  plan-5  C18  0.020
 1RA  plan-5  C2   0.020
 1RA  plan-5  H7   0.020

