# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Mar 23 18:08:49 2022
#   Inital geometry file: a 114 line input string
#   Ligand name: 3-(2-chlorophenyl)-4-ethyl-5-(1~{H}-indol-4-yl)-1~{H}-pyrrole-2-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCc1c([nH]c(C(O)=O)c1c2ccccc2Cl)c3cccc4[nH]ccc34
#
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
 U9E  U9E  '3-(2-chlorophenyl)-4-ethyl-5-(1~{H}-indol-4-yl)-1~{H}-pyrrole-2-carboxylic acid'  ligand  42  26  .  2022-03-29  2022-03-29
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_U9E
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
 U9E  C13  C   CR56   0   0.032   7.8321   6.4844  11.5620
 U9E  C18  C   CR16   0  -0.270   5.7844   8.0232  10.4724
 U9E  C17  C   CR16   0  -0.317   7.0862   8.3909  10.1949
 U9E  C16  C   CR56   0   0.352   8.0989   7.6108  10.7504
 U9E  C15  C   CR15   0  -0.025  10.0515   6.7786  11.4289
 U9E  C19  C   CR16   0  -0.339   5.4947   6.9037  11.2649
 U9E  C21  C   CH3    0  -0.653   6.6440   2.2490  10.5063
 U9E  C11  C   CR5    0   0.259   6.1690   4.9577  12.6479
 U9E  C12  C   CR6    0   0.009   6.4974   6.1129  11.8120
 U9E  C4   C   CR6    0  -0.142   7.2125   0.9832  14.4994
 U9E  C5   C   CR16   0  -0.198   7.3578  -0.3779  14.7337
 U9E  C6   C   CR16   0  -0.281   6.3237  -1.2388  14.4037
 U9E  C7   C   CR16   0  -0.236   5.1562  -0.7327  13.8464
 U9E  C8   C   CR16   0  -0.313   5.0336   0.6281  13.6219
 U9E  C3   C   CR6    0   0.164   6.0567   1.5233  13.9391
 U9E  C2   C   CR5    0  -0.020   5.9167   2.9573  13.6487
 U9E  C1   C   CR5    0  -0.030   6.5942   3.6410  12.6013
 U9E  C9   C   CR5    0   0.093   5.0991   3.8680  14.2927
 U9E  C10  C   C      0   0.342   4.1894   3.7643  15.4829
 U9E  O2   O   O      0  -0.578   4.1091   2.6527  16.0350
 U9E  O1   O   OC    -1  -0.605   3.6009   4.8207  15.7969
 U9E  N1   N   NR15   0  -0.660   5.2672   5.0582  13.6619
 U9E  C14  C   CR15   0  -0.451   9.0986   5.9783  11.9894
 U9E  N2   N   NR15   0  -0.681   9.4541   7.7543  10.6840
 U9E  H1   H   HCR6   0   0.247   4.9680   8.6042  10.0633
 U9E  H2   H   HCR6   0   0.256   7.3098   9.2533   9.5799
 U9E  H3   H   HCR5   0   0.279  11.1257   6.7293  11.5073
 U9E  H4   H   HCR6   0   0.240   4.4582   6.6407  11.4379
 U9E  H5   H   HCH2   0   0.223   8.1625   2.3126  12.0298
 U9E  H6   H   HCH2   0   0.241   8.0668   3.7565  11.0605
 U9E  H7   H   HCH3   0   0.222   7.2967   1.7803   9.7680
 U9E  H8   H   HCH3   0   0.222   6.0359   1.4647  10.9585
 U9E  H9   H   HCH3   0   0.218   5.9718   2.9260   9.9774
 U9E  H10  H   HCR6   0   0.272   8.2695  -0.7592  15.1737
 U9E  H11  H   HCR6   0   0.260   6.4329  -2.3002  14.5831
 U9E  H12  H   HCR6   0   0.255   4.3433  -1.3981  13.5870
 U9E  H13  H   HCR6   0   0.244   4.1273   1.0216  13.1802
 U9E  H15  H   HNR5   0   0.389   4.8207   5.9067  13.9731
 U9E  H16  H   HCR5   0   0.247   9.2804   5.1344  12.6353
 U9E  H17  H   HNR5   0   0.408   9.9402   8.4758  10.1778
 U9E  CL1  CL  CL     0  -0.141   8.5258   2.0298  14.9475
 U9E  C20  C   CH2    0  -0.536   7.4569   3.0020  11.5590

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
 U9E  C17  C18  aromatic  1.381  0.020  1.381
 U9E  C17  C16  aromatic  1.394  0.020  1.394
 U9E  C18  C19  aromatic  1.402  0.020  1.402
 U9E  C21  C20  single    1.528  0.020  1.528
 U9E  C16  N2   aromatic  1.364  0.020  1.364
 U9E  C16  C13  aromatic  1.414  0.020  1.414
 U9E  N2   C15  aromatic  1.365  0.020  1.365
 U9E  C19  C12  aromatic  1.389  0.020  1.389
 U9E  C20  C1   single    1.496  0.020  1.496
 U9E  C15  C14  aromatic  1.365  0.020  1.365
 U9E  C13  C12  aromatic  1.408  0.020  1.408
 U9E  C13  C14  aromatic  1.429  0.020  1.429
 U9E  C12  C11  single    1.463  0.020  1.463
 U9E  C1   C11  aromatic  1.384  0.020  1.384
 U9E  C1   C2   aromatic  1.423  0.020  1.423
 U9E  C11  N1   aromatic  1.361  0.020  1.361
 U9E  C8   C7   aromatic  1.385  0.020  1.385
 U9E  C8   C3   aromatic  1.396  0.020  1.396
 U9E  C2   C3   single    1.470  0.020  1.470
 U9E  C2   C9   aromatic  1.383  0.020  1.383
 U9E  C7   C6   aromatic  1.389  0.020  1.389
 U9E  C3   C4   aromatic  1.393  0.020  1.393
 U9E  N1   C9   aromatic  1.357  0.020  1.357
 U9E  C6   C5   aromatic  1.385  0.020  1.385
 U9E  C9   C10  single    1.502  0.020  1.502
 U9E  C4   C5   aromatic  1.389  0.020  1.389
 U9E  C4   CL1  single    1.738  0.020  1.738
 U9E  O2   C10  deloc     1.244  0.020  1.244
 U9E  C10  O1   deloc     1.249  0.020  1.249
 U9E  C18  H1   single    0.930  0.020  1.080
 U9E  C17  H2   single    0.930  0.020  1.080
 U9E  C15  H3   single    0.930  0.020  1.080
 U9E  C19  H4   single    0.930  0.020  1.080
 U9E  C20  H5   single    0.970  0.020  1.090
 U9E  C20  H6   single    0.970  0.020  1.090
 U9E  C21  H7   single    0.970  0.020  1.090
 U9E  C21  H8   single    0.970  0.020  1.090
 U9E  C21  H9   single    0.970  0.020  1.090
 U9E  C5   H10  single    0.930  0.020  1.080
 U9E  C6   H11  single    0.930  0.020  1.080
 U9E  C7   H12  single    0.930  0.020  1.080
 U9E  C8   H13  single    0.930  0.020  1.080
 U9E  N1   H15  single    0.860  0.020  1.020
 U9E  C14  H16  single    0.930  0.020  1.080
 U9E  N2   H17  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
 U9E  C14  C13  C12  133.91  3.000
 U9E  C14  C13  C16  106.66  3.000
 U9E  C12  C13  C16  119.42  3.000
 U9E  H1   C18  C19  119.11  3.000
 U9E  H1   C18  C17  119.49  3.000
 U9E  C19  C18  C17  121.40  3.000
 U9E  H2   C17  C16  121.48  3.000
 U9E  H2   C17  C18  121.39  3.000
 U9E  C16  C17  C18  117.12  3.000
 U9E  N2   C16  C17  130.05  3.000
 U9E  N2   C16  C13  107.41  3.000
 U9E  C17  C16  C13  122.52  3.000
 U9E  H3   C15  N2   120.55  3.000
 U9E  H3   C15  C14  129.71  3.000
 U9E  N2   C15  C14  109.74  3.000
 U9E  H4   C19  C12  119.31  3.000
 U9E  H4   C19  C18  118.81  3.000
 U9E  C12  C19  C18  121.87  3.000
 U9E  H9   C21  H8   107.69  3.000
 U9E  H9   C21  H7   107.89  3.000
 U9E  H8   C21  H7   107.77  3.000
 U9E  H9   C21  C20  110.85  3.000
 U9E  H8   C21  C20  111.42  3.000
 U9E  H7   C21  C20  111.07  3.000
 U9E  N1   C11  C1   107.39  3.000
 U9E  N1   C11  C12  121.08  3.000
 U9E  C1   C11  C12  131.50  3.000
 U9E  C11  C12  C19  120.83  3.000
 U9E  C11  C12  C13  121.50  3.000
 U9E  C19  C12  C13  117.65  3.000
 U9E  C3   C4   C5   122.31  3.000
 U9E  C5   C4   CL1  117.88  3.000
 U9E  C3   C4   CL1  119.80  3.000
 U9E  H10  C5   C6   120.46  3.000
 U9E  H10  C5   C4   120.15  3.000
 U9E  C6   C5   C4   119.39  3.000
 U9E  H11  C6   C7   120.58  3.000
 U9E  H11  C6   C5   119.65  3.000
 U9E  C7   C6   C5   119.77  3.000
 U9E  H12  C7   C8   119.93  3.000
 U9E  H12  C7   C6   120.23  3.000
 U9E  C8   C7   C6   119.84  3.000
 U9E  H13  C8   C3   118.25  3.000
 U9E  H13  C8   C7   119.84  3.000
 U9E  C3   C8   C7   121.90  3.000
 U9E  C2   C3   C8   120.73  3.000
 U9E  C2   C3   C4   122.46  3.000
 U9E  C8   C3   C4   116.79  3.000
 U9E  C9   C2   C1   107.93  3.000
 U9E  C9   C2   C3   127.36  3.000
 U9E  C1   C2   C3   124.68  3.000
 U9E  C2   C1   C11  106.62  3.000
 U9E  C2   C1   C20  125.61  3.000
 U9E  C11  C1   C20  127.35  3.000
 U9E  N1   C9   C10  120.26  3.000
 U9E  C10  C9   C2   132.98  3.000
 U9E  N1   C9   C2   106.72  3.000
 U9E  O1   C10  O2   127.86  3.000
 U9E  O1   C10  C9   115.22  3.000
 U9E  O2   C10  C9   116.92  3.000
 U9E  H15  N1   C9   122.66  3.000
 U9E  H15  N1   C11  125.86  3.000
 U9E  C9   N1   C11  111.33  3.000
 U9E  H16  C14  C15  125.96  3.000
 U9E  H16  C14  C13  127.29  3.000
 U9E  C15  C14  C13  106.75  3.000
 U9E  H17  N2   C15  125.13  3.000
 U9E  H17  N2   C16  125.42  3.000
 U9E  C15  N2   C16  109.45  3.000
 U9E  H6   C20  H5   105.79  3.000
 U9E  H6   C20  C1   110.20  3.000
 U9E  H5   C20  C1   109.97  3.000
 U9E  H6   C20  C21  108.87  3.000
 U9E  H5   C20  C21  109.23  3.000
 U9E  C1   C20  C21  112.55  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
 U9E  CONST_01  C18  C17  C16  C13     0.00   0.0  0
 U9E  CONST_02  C15  N2   C16  C13     0.00   0.0  0
 U9E  CONST_03  C18  C19  C12  C13     0.00   0.0  0
 U9E  CONST_06  N2   C15  C14  C13     0.00   0.0  0
 U9E  CONST_07  N2   C16  C17  C18   180.00   0.0  0
 U9E  CONST_08  C11  C12  C19  C18   180.00   0.0  0
 U9E  CONST_09  C12  C19  C18  C17     0.00   0.0  0
 U9E  CONST_10  C15  N2   C16  C17   180.00   0.0  0
 U9E  CONST_11  C12  C13  C16  C17     0.00   0.0  0
 U9E  CONST_12  C14  C13  C16  C17   180.00   0.0  0
 U9E  CONST_13  C19  C18  C17  C16     0.00   0.0  0
 U9E  CONST_14  C14  C15  N2   C16     0.00   0.0  0
 U9E  CONST_15  C19  C12  C13  C16     0.00   0.0  0
 U9E  CONST_16  C11  C12  C13  C16   180.00   0.0  0
 U9E  CONST_17  C15  C14  C13  C16     0.00   0.0  0
 U9E  CONST_18  C12  C13  C14  C15   180.00   0.0  0
 U9E  CONST_19  C14  C13  C12  C19   180.00   0.0  0
 U9E  CONST_22  C14  C13  C12  C11     0.00   0.0  0
 U9E  CONST_23  C3   C2   C1   C11   180.00   0.0  0
 U9E  CONST_24  C9   C2   C1   C11     0.00   0.0  0
 U9E  CONST_25  C2   C9   N1   C11     0.00   0.0  0
 U9E  CONST_26  N2   C16  C13  C12   180.00   0.0  0
 U9E  CONST_27  C2   C1   C11  C12   180.00   0.0  0
 U9E  CONST_28  C9   N1   C11  C12   180.00   0.0  0
 U9E  CONST_29  C7   C8   C3   C4      0.00   0.0  0
 U9E  CONST_32  C7   C6   C5   C4      0.00   0.0  0
 U9E  CONST_33  C8   C7   C6   C5      0.00   0.0  0
 U9E  CONST_34  C8   C3   C4   C5      0.00   0.0  0
 U9E  CONST_35  C2   C3   C4   C5    180.00   0.0  0
 U9E  CONST_36  C3   C8   C7   C6      0.00   0.0  0
 U9E  CONST_37  C3   C4   C5   C6      0.00   0.0  0
 U9E  CONST_38  C2   C3   C8   C7    180.00   0.0  0
 U9E  CONST_41  N1   C9   C2   C3    180.00   0.0  0
 U9E  CONST_42  N1   C11  C1   C2      0.00   0.0  0
 U9E  CONST_43  C9   N1   C11  C1      0.00   0.0  0
 U9E  CONST_44  N1   C9   C2   C1      0.00   0.0  0
 U9E  CONST_45  N2   C16  C13  C14     0.00   0.0  0
 U9E  CONST_46  C12  C11  C1   C20     0.00   0.0  0
 U9E  CONST_47  N1   C11  C1   C20   180.00   0.0  0
 U9E  CONST_48  C3   C2   C1   C20     0.00   0.0  0
 U9E  CONST_49  C9   C2   C1   C20   180.00   0.0  0
 U9E  CONST_50  C10  C9   N1   C11   180.00   0.0  0
 U9E  CONST_51  C8   C3   C4   CL1   180.00   0.0  0
 U9E  CONST_52  C2   C3   C4   CL1     0.00   0.0  0
 U9E  CONST_53  C6   C5   C4   CL1   180.00   0.0  0
 U9E  CONST_54  C10  C9   C2   C3      0.00   0.0  0
 U9E  CONST_55  C10  C9   C2   C1    180.00   0.0  0
 U9E  CONST_56  H2   C17  C16  C13   180.00   0.0  0
 U9E  CONST_57  H17  N2   C16  C13   180.00   0.0  0
 U9E  CONST_58  H4   C19  C12  C13   180.00   0.0  0
 U9E  CONST_59  H3   C15  C14  C13   180.00   0.0  0
 U9E  CONST_60  H1   C18  C17  C16   180.00   0.0  0
 U9E  CONST_61  H16  C14  C13  C16   180.00   0.0  0
 U9E  CONST_62  H15  N1   C11  C12     0.00   0.0  0
 U9E  CONST_63  H13  C8   C3   C4    180.00   0.0  0
 U9E  CONST_64  H11  C6   C5   C4    180.00   0.0  0
 U9E  CONST_65  H12  C7   C6   C5    180.00   0.0  0
 U9E  CONST_66  H10  C5   C6   C7    180.00   0.0  0
 U9E  Var_01    C11  C1   C20  C21   -97.49  30.0  2
 U9E  Var_02    O2   C10  C9   C2     -0.63  30.0  2
 U9E  Var_03    H7   C21  C20  C1   -179.12  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
 U9E  plan-1  C11  0.020
 U9E  plan-1  C12  0.020
 U9E  plan-1  C3   0.020
 U9E  plan-1  C2   0.020
 U9E  plan-1  C1   0.020
 U9E  plan-1  C9   0.020
 U9E  plan-1  C10  0.020
 U9E  plan-1  N1   0.020
 U9E  plan-1  H15  0.020
 U9E  plan-1  C20  0.020
 U9E  plan-2  C4   0.020
 U9E  plan-2  C5   0.020
 U9E  plan-2  C6   0.020
 U9E  plan-2  C7   0.020
 U9E  plan-2  C8   0.020
 U9E  plan-2  C3   0.020
 U9E  plan-2  C2   0.020
 U9E  plan-2  H10  0.020
 U9E  plan-2  H11  0.020
 U9E  plan-2  H12  0.020
 U9E  plan-2  H13  0.020
 U9E  plan-2  CL1  0.020
 U9E  plan-3  C13  0.020
 U9E  plan-3  C18  0.020
 U9E  plan-3  C17  0.020
 U9E  plan-3  C16  0.020
 U9E  plan-3  C15  0.020
 U9E  plan-3  C19  0.020
 U9E  plan-3  C11  0.020
 U9E  plan-3  C12  0.020
 U9E  plan-3  C14  0.020
 U9E  plan-3  N2   0.020
 U9E  plan-3  H1   0.020
 U9E  plan-3  H2   0.020
 U9E  plan-3  H3   0.020
 U9E  plan-3  H4   0.020
 U9E  plan-3  H16  0.020
 U9E  plan-3  H17  0.020
 U9E  plan-4  C9   0.020
 U9E  plan-4  C10  0.020
 U9E  plan-4  O2   0.020
 U9E  plan-4  O1   0.020

