# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 18 11:35:44 2020
#   Inital geometry file: a 137 line input string
#   Ligand name: (2~{S})-~{N}1-(1-aminocarbonylindol-3-yl)-~{N}2-[3-(trifluoromethyloxy)phenyl]pyrrolidine-1,2-dicarboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: NC(=O)n1cc(NC(=O)N2CCC[C@H]2C(=O)Nc3cccc(OC(F)(F)F)c3)c4ccccc14
#
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
 8RW  8RW  (2~{S})-~{N}1-(1-aminocarbonylindol-3-yl)-~{N}2-[3-(trifluoromethyloxy)phenyl]pyrrolidine-1,2-dicarboxamide  ligand  54  34  .  2021-08-06  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_8RW
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
 8RW  C4   C  CH2   0  -0.473  -0.8873  -5.0307  -0.5296
 8RW  C14  C  CR16  0  -0.268  -6.9711   1.4426  -1.4946
 8RW  C5   C  CH2   0  -0.302  -1.6792  -3.7671  -0.8377
 8RW  C6   C  C     0   0.764  -1.5215  -1.5683   0.3762
 8RW  C11  C  CR56  0  -0.028  -4.6353   0.2889  -0.5835
 8RW  C7   C  CR5   0   0.238  -3.3975  -0.0360   0.0744
 8RW  C8   C  CR15  0  -0.081  -3.1173   0.9761   0.9336
 8RW  C10  C  CR56  0   0.376  -5.0708   1.5225  -0.0688
 8RW  C12  C  CR16  0  -0.336  -5.3828  -0.3740  -1.5568
 8RW  C13  C  CR16  0  -0.262  -6.5513   0.2091  -2.0057
 8RW  N1   N  NT    0  -0.533  -1.0296  -2.7700   0.0012
 8RW  N2   N  NH1   0  -0.801  -2.7156  -1.2132  -0.1867
 8RW  C3   C  CH2   0  -0.476   0.5185  -4.5051  -0.2611
 8RW  N3   N  NR5   0  -0.636  -4.1284   1.9383   0.8563
 8RW  C1   C  C     0   0.550   1.3390  -2.1567   0.1145
 8RW  C2   C  CH1   0  -0.171   0.2712  -3.1811   0.4790
 8RW  N4   N  NH2   0  -0.836  -3.0305   3.4792   2.1888
 8RW  O2   O  O     0  -0.488  -5.2169   3.7593   1.6831
 8RW  C15  C  CR16  0  -0.287  -6.2463   2.1158  -0.5268
 8RW  O3   O  O     0  -0.526  -0.9310  -0.8462   1.1715
 8RW  N5   N  NH1   0  -0.748   2.3094  -2.0304   1.0520
 8RW  C16  C  CR6   0   0.390   3.4627  -1.2471   1.0237
 8RW  C17  C  CR16  0  -0.343   4.2304  -1.2068   2.1907
 8RW  C18  C  CR16  0  -0.242   5.3971  -0.4671   2.2404
 8RW  C19  C  CR16  0  -0.323   5.8284   0.2567   1.1369
 8RW  C20  C  CR6   0   0.346   5.0541   0.2069  -0.0062
 8RW  O4   O  O2    0  -0.526   5.4965   0.8682  -1.1486
 8RW  C21  C  CT    0   1.072   5.1030   2.1331  -1.3355
 8RW  F1   F  F     0  -0.299   5.4873   2.9464  -0.3498
 8RW  F2   F  F     0  -0.277   5.6483   2.5602  -2.4636
 8RW  F3   F  F     0  -0.299   3.7779   2.2541  -1.4388
 8RW  C22  C  CR16  0  -0.382   3.8828  -0.5261  -0.0940
 8RW  H1   H  HCH2  0   0.249  -1.2911  -5.5153   0.3611
 8RW  H2   H  HCH2  0   0.262  -0.9200  -5.7474  -1.3482
 8RW  H3   H  HCR6  0   0.258  -7.8882   1.8843  -1.8618
 8RW  H4   H  HCH2  0   0.252  -1.6121  -3.5003  -1.8972
 8RW  H5   H  HCH2  0   0.257  -2.7336  -3.8818  -0.5779
 8RW  H6   H  HCR5  0   0.304  -2.3093   1.0742   1.6333
 8RW  H7   H  HCR6  0   0.249  -5.0646  -1.3270  -1.9616
 8RW  H8   H  HCR6  0   0.257  -7.1467  -0.2889  -2.7591
 8RW  H9   H  HNH1  0   0.423  -3.1222  -1.8077  -0.8899
 8RW  H10  H  HCH2  0   0.270   1.1307  -5.1865   0.3264
 8RW  H11  H  HCH2  0   0.256   1.0318  -4.3196  -1.2067
 8RW  H12  H  HCH1  0   0.281   0.2523  -3.3468   1.5620
 8RW  H13  H  HNH2  0   0.416  -2.1345   3.1357   1.8884
 8RW  H14  H  HNH2  0   0.415  -3.0202   4.3573   2.6810
 8RW  H15  H  HCR6  0   0.275  -6.5919   3.0629  -0.1463
 8RW  H16  H  HNH1  0   0.421   2.1679  -2.5429   1.9097
 8RW  H17  H  HCR6  0   0.280   3.9131  -1.7668   3.0623
 8RW  H18  H  HCR6  0   0.274   5.9795  -0.4515   3.1515
 8RW  H19  H  HCR6  0   0.280   6.7468   0.8267   1.1665
 8RW  H20  H  HCR6  0   0.301   3.3274  -0.5471  -1.0176
 8RW  O1   O  O     0  -0.457   1.3264  -1.5736  -0.9512
 8RW  C9   C  C     0   0.683  -4.1819   3.1269   1.5886

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
 8RW  F2   C21  single    1.324  0.020  1.324
 8RW  N4   C9   single    1.345  0.020  1.345
 8RW  F3   C21  single    1.335  0.020  1.335
 8RW  O2   C9   double    1.217  0.020  1.217
 8RW  C21  O4   single    1.338  0.020  1.338
 8RW  C21  F1   single    1.334  0.020  1.334
 8RW  C9   N3   single    1.397  0.020  1.397
 8RW  O4   C20  single    1.392  0.020  1.392
 8RW  N3   C8   aromatic  1.398  0.020  1.398
 8RW  N3   C10  aromatic  1.384  0.020  1.384
 8RW  C8   C7   aromatic  1.357  0.020  1.357
 8RW  C22  C20  aromatic  1.385  0.020  1.385
 8RW  C22  C16  aromatic  1.395  0.020  1.395
 8RW  C20  C19  aromatic  1.382  0.020  1.382
 8RW  O3   C6   double    1.226  0.020  1.226
 8RW  C10  C15  aromatic  1.394  0.020  1.394
 8RW  C10  C11  aromatic  1.406  0.020  1.406
 8RW  C7   N2   single    1.385  0.020  1.385
 8RW  C7   C11  aromatic  1.439  0.020  1.439
 8RW  N5   C16  single    1.394  0.020  1.394
 8RW  N5   C1   single    1.355  0.020  1.355
 8RW  C6   N2   single    1.367  0.020  1.367
 8RW  C6   N1   single    1.352  0.020  1.352
 8RW  C15  C14  aromatic  1.384  0.020  1.384
 8RW  C16  C17  aromatic  1.397  0.020  1.397
 8RW  C2   N1   single    1.445  0.020  1.445
 8RW  C2   C1   single    1.524  0.020  1.524
 8RW  C2   C3   single    1.537  0.020  1.537
 8RW  C19  C18  aromatic  1.388  0.020  1.388
 8RW  C11  C12  aromatic  1.395  0.020  1.395
 8RW  N1   C5   single    1.456  0.020  1.456
 8RW  C1   O1   double    1.215  0.020  1.215
 8RW  C3   C4   single    1.525  0.020  1.525
 8RW  C4   C5   single    1.523  0.020  1.523
 8RW  C14  C13  aromatic  1.400  0.020  1.400
 8RW  C17  C18  aromatic  1.382  0.020  1.382
 8RW  C12  C13  aromatic  1.381  0.020  1.381
 8RW  C4   H1   single    0.970  0.020  1.090
 8RW  C4   H2   single    0.970  0.020  1.090
 8RW  C14  H3   single    0.930  0.020  1.080
 8RW  C5   H4   single    0.970  0.020  1.090
 8RW  C5   H5   single    0.970  0.020  1.090
 8RW  C8   H6   single    0.930  0.020  1.080
 8RW  C12  H7   single    0.930  0.020  1.080
 8RW  C13  H8   single    0.930  0.020  1.080
 8RW  N2   H9   single    0.860  0.020  1.020
 8RW  C3   H10  single    0.970  0.020  1.090
 8RW  C3   H11  single    0.970  0.020  1.090
 8RW  C2   H12  single    0.970  0.020  1.090
 8RW  N4   H13  single    0.890  0.020  1.040
 8RW  N4   H14  single    0.890  0.020  1.040
 8RW  C15  H15  single    0.930  0.020  1.080
 8RW  N5   H16  single    0.860  0.020  1.020
 8RW  C17  H17  single    0.930  0.020  1.080
 8RW  C18  H18  single    0.930  0.020  1.080
 8RW  C19  H19  single    0.930  0.020  1.080
 8RW  C22  H20  single    0.930  0.020  1.080

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
 8RW  H2   C4   H1   108.08  3.000
 8RW  H2   C4   C3   112.78  3.000
 8RW  H1   C4   C3   110.52  3.000
 8RW  H2   C4   C5   112.24  3.000
 8RW  H1   C4   C5   109.94  3.000
 8RW  C3   C4   C5   103.24  3.000
 8RW  H3   C14  C15  118.86  3.000
 8RW  H3   C14  C13  119.34  3.000
 8RW  C15  C14  C13  121.80  3.000
 8RW  H5   C5   H4   108.36  3.000
 8RW  H5   C5   N1   111.45  3.000
 8RW  H4   C5   N1   111.31  3.000
 8RW  H5   C5   C4   111.52  3.000
 8RW  H4   C5   C4   111.49  3.000
 8RW  N1   C5   C4   102.69  3.000
 8RW  O3   C6   N2   122.34  3.000
 8RW  N2   C6   N1   115.76  3.000
 8RW  O3   C6   N1   121.90  3.000
 8RW  C12  C11  C10  120.43  3.000
 8RW  C12  C11  C7   132.28  3.000
 8RW  C10  C11  C7   107.29  3.000
 8RW  N2   C7   C8   130.66  3.000
 8RW  N2   C7   C11  121.95  3.000
 8RW  C8   C7   C11  107.38  3.000
 8RW  H6   C8   N3   121.17  3.000
 8RW  H6   C8   C7   129.53  3.000
 8RW  N3   C8   C7   109.21  3.000
 8RW  C15  C10  N3   131.73  3.000
 8RW  C15  C10  C11  120.96  3.000
 8RW  N3   C10  C11  107.30  3.000
 8RW  H7   C12  C13  119.91  3.000
 8RW  H7   C12  C11  121.43  3.000
 8RW  C13  C12  C11  118.66  3.000
 8RW  H8   C13  C12  119.85  3.000
 8RW  H8   C13  C14  119.67  3.000
 8RW  C12  C13  C14  120.48  3.000
 8RW  C2   N1   C6   119.26  3.000
 8RW  C2   N1   C5   113.40  3.000
 8RW  C6   N1   C5   127.33  3.000
 8RW  H9   N2   C7   115.77  3.000
 8RW  H9   N2   C6   119.15  3.000
 8RW  C7   N2   C6   124.96  3.000
 8RW  H11  C3   H10  108.03  3.000
 8RW  H11  C3   C2   110.27  3.000
 8RW  H10  C3   C2   111.71  3.000
 8RW  H11  C3   C4   109.85  3.000
 8RW  H10  C3   C4   113.45  3.000
 8RW  C2   C3   C4   103.50  3.000
 8RW  C10  N3   C9   125.43  3.000
 8RW  C10  N3   C8   108.82  3.000
 8RW  C9   N3   C8   125.75  3.000
 8RW  N5   C1   C2   113.51  3.000
 8RW  C2   C1   O1   121.68  3.000
 8RW  N5   C1   O1   124.72  3.000
 8RW  H12  C2   C1   110.49  3.000
 8RW  H12  C2   C3   110.39  3.000
 8RW  C1   C2   C3   110.56  3.000
 8RW  H12  C2   N1   110.75  3.000
 8RW  C3   C2   N1   103.34  3.000
 8RW  C1   C2   N1   111.12  3.000
 8RW  H14  N4   H13  115.78  3.000
 8RW  H14  N4   C9   117.09  3.000
 8RW  H13  N4   C9   122.68  3.000
 8RW  H15  C15  C10  121.90  3.000
 8RW  H15  C15  C14  120.43  3.000
 8RW  C10  C15  C14  117.67  3.000
 8RW  H16  N5   C16  114.74  3.000
 8RW  H16  N5   C1   116.12  3.000
 8RW  C16  N5   C1   129.09  3.000
 8RW  C22  C16  C17  119.26  3.000
 8RW  C17  C16  N5   116.98  3.000
 8RW  C22  C16  N5   123.76  3.000
 8RW  H17  C17  C18  119.65  3.000
 8RW  H17  C17  C16  119.74  3.000
 8RW  C18  C17  C16  120.61  3.000
 8RW  H18  C18  C19  119.66  3.000
 8RW  H18  C18  C17  119.51  3.000
 8RW  C19  C18  C17  120.83  3.000
 8RW  H19  C19  C20  121.18  3.000
 8RW  H19  C19  C18  121.12  3.000
 8RW  C20  C19  C18  117.70  3.000
 8RW  C22  C20  O4   117.92  3.000
 8RW  C22  C20  C19  123.07  3.000
 8RW  O4   C20  C19  118.93  3.000
 8RW  C21  O4   C20  118.06  3.000
 8RW  F3   C21  F2   108.29  3.000
 8RW  F3   C21  F1   106.73  3.000
 8RW  F2   C21  F1   108.31  3.000
 8RW  F1   C21  O4   112.85  3.000
 8RW  F3   C21  O4   112.87  3.000
 8RW  F2   C21  O4   107.63  3.000
 8RW  H20  C22  C20  120.04  3.000
 8RW  H20  C22  C16  121.42  3.000
 8RW  C20  C22  C16  118.53  3.000
 8RW  O2   C9   N4   123.87  3.000
 8RW  O2   C9   N3   121.03  3.000
 8RW  N4   C9   N3   115.08  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
 8RW  CONST_01  N3   C10  C15  C14  180.00   0.0  0
 8RW  CONST_02  C11  C10  C15  C14    0.00   0.0  0
 8RW  CONST_03  C11  C12  C13  C14    0.00   0.0  0
 8RW  CONST_04  C8   N3   C10  C11    0.00   0.0  0
 8RW  CONST_05  N3   C8   C7   C11    0.00   0.0  0
 8RW  CONST_06  C10  N3   C8   C7     0.00   0.0  0
 8RW  CONST_07  N3   C10  C11  C7     0.00   0.0  0
 8RW  CONST_08  C15  C10  C11  C7   180.00   0.0  0
 8RW  CONST_09  C13  C12  C11  C7   180.00   0.0  0
 8RW  CONST_10  C15  C10  N3   C8   180.00   0.0  0
 8RW  CONST_11  C10  C11  C7   C8     0.00   0.0  0
 8RW  CONST_12  C12  C11  C7   C8   180.00   0.0  0
 8RW  CONST_13  C13  C14  C15  C10    0.00   0.0  0
 8RW  CONST_14  C13  C12  C11  C10    0.00   0.0  0
 8RW  CONST_15  N3   C10  C11  C12  180.00   0.0  0
 8RW  CONST_16  C15  C10  C11  C12    0.00   0.0  0
 8RW  CONST_17  C15  C14  C13  C12    0.00   0.0  0
 8RW  CONST_18  C19  C20  C22  C16    0.00   0.0  0
 8RW  CONST_19  C19  C18  C17  C16    0.00   0.0  0
 8RW  CONST_20  C20  C22  C16  C17    0.00   0.0  0
 8RW  CONST_21  C20  C19  C18  C17    0.00   0.0  0
 8RW  CONST_22  C22  C20  C19  C18    0.00   0.0  0
 8RW  CONST_23  C22  C16  C17  C18    0.00   0.0  0
 8RW  CONST_24  C9   N3   C10  C11  180.00   0.0  0
 8RW  CONST_25  C9   N3   C8   C7   180.00   0.0  0
 8RW  CONST_26  C15  C10  N3   C9     0.00   0.0  0
 8RW  CONST_27  N2   C7   C11  C10  180.00   0.0  0
 8RW  CONST_28  N2   C7   C11  C12    0.00   0.0  0
 8RW  CONST_29  N3   C8   C7   N2   180.00   0.0  0
 8RW  CONST_30  C20  C22  C16  N5   180.00   0.0  0
 8RW  CONST_31  C18  C17  C16  N5   180.00   0.0  0
 8RW  CONST_32  O4   C20  C22  C16  180.00   0.0  0
 8RW  CONST_33  O4   C20  C19  C18  180.00   0.0  0
 8RW  CONST_34  H7   C12  C13  C14  180.00   0.0  0
 8RW  CONST_35  H15  C15  C10  C11  180.00   0.0  0
 8RW  CONST_36  H6   C8   C7   C11  180.00   0.0  0
 8RW  CONST_37  H8   C13  C12  C11  180.00   0.0  0
 8RW  CONST_38  H3   C14  C15  C10  180.00   0.0  0
 8RW  CONST_39  H18  C18  C17  C16  180.00   0.0  0
 8RW  CONST_40  H20  C22  C16  C17  180.00   0.0  0
 8RW  CONST_41  H19  C19  C18  C17  180.00   0.0  0
 8RW  CONST_42  H17  C17  C18  C19  180.00   0.0  0
 8RW  CONST_43  O3   C6   N1   C5   180.00   0.0  0
 8RW  CONST_46  O3   C6   N1   C2     0.00   0.0  0
 8RW  CONST_47  C16  N5   C1   C2   180.00   0.0  0
 8RW  CONST_48  C8   C7   N2   C6     0.00   0.0  0
 8RW  CONST_49  C11  C7   N2   C6   180.00   0.0  0
 8RW  CONST_50  N1   C6   N2   C7   180.00   0.0  0
 8RW  CONST_51  C22  C16  N5   C1     0.00   0.0  0
 8RW  CONST_52  C17  C16  N5   C1   180.00   0.0  0
 8RW  CONST_53  N2   C6   N1   C5     0.00   0.0  0
 8RW  CONST_54  N4   C9   N3   C8     0.00   0.0  0
 8RW  CONST_55  N4   C9   N3   C10  180.00   0.0  0
 8RW  CONST_56  C2   N1   C6   N2   180.00   0.0  0
 8RW  CONST_57  H9   N2   C7   C11    0.00   0.0  0
 8RW  CONST_58  H16  N5   C16  C17    0.00   0.0  0
 8RW  CONST_59  O3   C6   N2   C7     0.00   0.0  0
 8RW  CONST_60  C16  N5   C1   O1     0.00   0.0  0
 8RW  CONST_62  H14  N4   C9   N3   180.00   0.0  0
 8RW  Var_01    C2   N1   C5   C4    16.57  30.0  1
 8RW  Var_02    C2   C3   C4   C5    37.13  30.0  1
 8RW  Var_03    C3   C4   C5   N1   -32.69  30.0  1
 8RW  Var_04    C22  C20  O4   C21   91.66  30.0  2
 8RW  Var_05    F2   C21  O4   C20  179.36  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
 8RW  chir_01  C2  N1  C1  C3  positiv

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
 8RW  plan-1  N5   0.020
 8RW  plan-1  C16  0.020
 8RW  plan-1  C17  0.020
 8RW  plan-1  C18  0.020
 8RW  plan-1  C19  0.020
 8RW  plan-1  C20  0.020
 8RW  plan-1  O4   0.020
 8RW  plan-1  C22  0.020
 8RW  plan-1  H17  0.020
 8RW  plan-1  H18  0.020
 8RW  plan-1  H19  0.020
 8RW  plan-1  H20  0.020
 8RW  plan-2  C1   0.020
 8RW  plan-2  C2   0.020
 8RW  plan-2  N5   0.020
 8RW  plan-2  C16  0.020
 8RW  plan-2  H16  0.020
 8RW  plan-2  O1   0.020
 8RW  plan-3  C14  0.020
 8RW  plan-3  C11  0.020
 8RW  plan-3  C7   0.020
 8RW  plan-3  C8   0.020
 8RW  plan-3  C10  0.020
 8RW  plan-3  C12  0.020
 8RW  plan-3  C13  0.020
 8RW  plan-3  N2   0.020
 8RW  plan-3  N3   0.020
 8RW  plan-3  N4   0.020
 8RW  plan-3  O2   0.020
 8RW  plan-3  C15  0.020
 8RW  plan-3  H3   0.020
 8RW  plan-3  H6   0.020
 8RW  plan-3  H7   0.020
 8RW  plan-3  H8   0.020
 8RW  plan-3  H13  0.020
 8RW  plan-3  H14  0.020
 8RW  plan-3  H15  0.020
 8RW  plan-3  C9   0.020
 8RW  plan-4  C5   0.020
 8RW  plan-4  C6   0.020
 8RW  plan-4  C7   0.020
 8RW  plan-4  N1   0.020
 8RW  plan-4  N2   0.020
 8RW  plan-4  C2   0.020
 8RW  plan-4  O3   0.020
 8RW  plan-4  H9   0.020

