# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Mar 22 18:29:46 2020
#   Inital geometry file: a 94 line input string
#   Ligand name: N-[(1S)-1-(2-chloro-6-fluorophenyl)ethyl]-5-cyano-1-methyl-1H-pyrrole-2-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H](NC(=O)c1ccc(C#N)n1C)c2c(F)cccc2Cl
#
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
 1HX  1HX  N-[(1S)-1-(2-chloro-6-fluorophenyl)ethyl]-5-cyano-1-methyl-1H-pyrrole-2-carboxamide  ligand  34  21  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_1HX
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
 1HX  C4   C   CR6   0   0.020  -2.2223   0.0215   0.4028
 1HX  C6   C   CR16  0  -0.215  -3.8959  -0.2626  -1.3493
 1HX  C1   C   CR16  0  -0.263  -3.8602   1.0945  -1.6217
 1HX  C3   C   CR6   0   0.523  -2.2433   1.3777   0.0953
 1HX  C2   C   CR16  0  -0.394  -3.0286   1.9313  -0.8940
 1HX  C5   C   CR6   0  -0.104  -3.0826  -0.7764  -0.3490
 1HX  C7   C   CH1   0  -0.139  -1.3220  -0.5246   1.4936
 1HX  CL2  CL  CL    0  -0.116  -3.1797  -2.4817  -0.0434
 1HX  F20  F   F     0  -0.307  -1.4548   2.2033   0.8019
 1HX  C10  C   CH3   0  -0.675  -1.8230  -0.1687   2.8877
 1HX  N8   N   NH1   0  -0.647   0.0454  -0.0760   1.3273
 1HX  O11  O   O     0  -0.468   0.4401  -1.3328  -0.5046
 1HX  C12  C   CR5   0   0.256   2.1120   0.1971   0.1962
 1HX  C16  C   CR15  0  -0.357   2.4328   1.4917   0.5725
 1HX  C15  C   CR15  0  -0.298   3.7611   1.7178   0.2054
 1HX  C14  C   CR5   0   0.294   4.2078   0.5478  -0.3807
 1HX  C18  C   CSP   0   0.007   5.4901   0.2755  -0.8996
 1HX  N19  N   NS    0  -0.242   6.5468   0.0779  -1.3188
 1HX  N13  N   NR5   0  -0.508   3.1977  -0.3715  -0.3863
 1HX  C17  C   CH3   0  -0.525   3.3099  -1.7231  -0.9080
 1HX  H1   H   HCR6  0   0.283  -4.5474  -0.9181  -1.9098
 1HX  H2   H   HCR6  0   0.280  -4.4858   1.5030  -2.4035
 1HX  H3   H   HCR6  0   0.286  -2.9897   2.9951  -1.0870
 1HX  H4   H   HCH1  0   0.274  -1.3199  -1.6112   1.4108
 1HX  H5   H   HCH3  0   0.254  -2.8382  -0.5380   3.0223
 1HX  H6   H   HCH3  0   0.254  -1.1916  -0.6372   3.6424
 1HX  H7   H   HCH3  0   0.241  -1.8282   0.9068   3.0617
 1HX  H8   H   HNH1  0   0.412   0.4195   0.5849   1.9891
 1HX  H9   H   HCR5  0   0.276   1.7671   2.2049   1.0323
 1HX  H10  H   HCR5  0   0.281   4.3407   2.6167   0.3382
 1HX  H11  H   HCH3  0   0.270   2.7818  -1.8199  -1.8524
 1HX  H12  H   HCH3  0   0.266   4.3597  -1.9536  -1.0643
 1HX  H13  H   HCH3  0   0.271   2.9086  -2.4370  -0.1954
 1HX  C9   C   C     0   0.509   0.8043  -0.4862   0.2982

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
 1HX  C10  C7   single    1.524  0.020  1.524
 1HX  C7   N8   single    1.449  0.020  1.449
 1HX  C7   C4   single    1.516  0.020  1.516
 1HX  CL2  C5   single    1.735  0.020  1.735
 1HX  N8   C9   single    1.343  0.020  1.343
 1HX  C16  C15  aromatic  1.397  0.020  1.397
 1HX  C16  C12  aromatic  1.386  0.020  1.386
 1HX  C4   C5   aromatic  1.394  0.020  1.394
 1HX  C4   C3   aromatic  1.391  0.020  1.391
 1HX  C5   C6   aromatic  1.388  0.020  1.388
 1HX  C9   C12  single    1.479  0.020  1.479
 1HX  C9   O11  double    1.222  0.020  1.222
 1HX  C15  C14  aromatic  1.383  0.020  1.383
 1HX  F20  C3   single    1.343  0.020  1.343
 1HX  C12  N13  aromatic  1.357  0.020  1.357
 1HX  C3   C2   aromatic  1.379  0.020  1.379
 1HX  C6   C1   aromatic  1.385  0.020  1.385
 1HX  C14  N13  aromatic  1.366  0.020  1.366
 1HX  C14  C18  single    1.410  0.020  1.410
 1HX  C2   C1   aromatic  1.386  0.020  1.386
 1HX  N13  C17  single    1.453  0.020  1.453
 1HX  C18  N19  triple    1.154  0.020  1.154
 1HX  C6   H1   single    0.930  0.020  1.080
 1HX  C1   H2   single    0.930  0.020  1.080
 1HX  C2   H3   single    0.930  0.020  1.080
 1HX  C7   H4   single    0.970  0.020  1.090
 1HX  C10  H5   single    0.970  0.020  1.090
 1HX  C10  H6   single    0.970  0.020  1.090
 1HX  C10  H7   single    0.970  0.020  1.090
 1HX  N8   H8   single    0.860  0.020  1.020
 1HX  C16  H9   single    0.930  0.020  1.080
 1HX  C15  H10  single    0.930  0.020  1.080
 1HX  C17  H11  single    0.970  0.020  1.090
 1HX  C17  H12  single    0.970  0.020  1.090
 1HX  C17  H13  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
 1HX  C7   C4   C5   123.26  3.000
 1HX  C5   C4   C3   115.45  3.000
 1HX  C7   C4   C3   121.29  3.000
 1HX  H1   C6   C5   120.16  3.000
 1HX  H1   C6   C1   120.52  3.000
 1HX  C5   C6   C1   119.31  3.000
 1HX  H2   C1   C2   119.90  3.000
 1HX  H2   C1   C6   119.84  3.000
 1HX  C2   C1   C6   120.26  3.000
 1HX  F20  C3   C2   117.72  3.000
 1HX  C2   C3   C4   123.96  3.000
 1HX  F20  C3   C4   118.32  3.000
 1HX  H3   C2   C3   120.15  3.000
 1HX  H3   C2   C1   121.44  3.000
 1HX  C3   C2   C1   118.42  3.000
 1HX  CL2  C5   C6   117.26  3.000
 1HX  C6   C5   C4   122.59  3.000
 1HX  CL2  C5   C4   120.15  3.000
 1HX  H4   C7   N8   107.35  3.000
 1HX  H4   C7   C10  107.64  3.000
 1HX  N8   C7   C10  110.07  3.000
 1HX  H4   C7   C4   107.80  3.000
 1HX  N8   C7   C4   111.49  3.000
 1HX  C10  C7   C4   112.27  3.000
 1HX  H7   C10  H6   108.45  3.000
 1HX  H7   C10  H5   108.11  3.000
 1HX  H6   C10  H5   107.99  3.000
 1HX  H7   C10  C7   112.23  3.000
 1HX  H6   C10  C7   110.04  3.000
 1HX  H5   C10  C7   109.91  3.000
 1HX  H8   N8   C9   119.61  3.000
 1HX  H8   N8   C7   118.57  3.000
 1HX  C9   N8   C7   121.79  3.000
 1HX  N13  C12  C16  108.83  3.000
 1HX  N13  C12  C9   122.92  3.000
 1HX  C16  C12  C9   128.14  3.000
 1HX  H9   C16  C15  126.31  3.000
 1HX  H9   C16  C12  126.20  3.000
 1HX  C15  C16  C12  107.46  3.000
 1HX  H10  C15  C14  125.75  3.000
 1HX  H10  C15  C16  127.89  3.000
 1HX  C14  C15  C16  106.36  3.000
 1HX  N13  C14  C18  122.76  3.000
 1HX  C18  C14  C15  127.83  3.000
 1HX  N13  C14  C15  109.41  3.000
 1HX  N19  C18  C14  180.00  3.000
 1HX  C17  N13  C14  124.78  3.000
 1HX  C17  N13  C12  127.27  3.000
 1HX  C14  N13  C12  107.94  3.000
 1HX  H13  C17  H12  108.19  3.000
 1HX  H13  C17  H11  109.41  3.000
 1HX  H12  C17  H11  109.02  3.000
 1HX  H13  C17  N13  110.33  3.000
 1HX  H12  C17  N13  108.89  3.000
 1HX  H11  C17  N13  110.95  3.000
 1HX  C12  C9   O11  122.56  3.000
 1HX  O11  C9   N8   123.13  3.000
 1HX  C12  C9   N8   114.30  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
 1HX  CONST_01  C1   C6   C5   C4     0.00   0.0  0
 1HX  CONST_02  C1   C2   C3   C4     0.00   0.0  0
 1HX  CONST_03  C3   C4   C5   C6     0.00   0.0  0
 1HX  CONST_04  C3   C2   C1   C6     0.00   0.0  0
 1HX  CONST_05  C5   C4   C3   C2     0.00   0.0  0
 1HX  CONST_06  C5   C6   C1   C2     0.00   0.0  0
 1HX  CONST_07  C14  C15  C16  C12    0.00   0.0  0
 1HX  CONST_08  C15  C14  N13  C12    0.00   0.0  0
 1HX  CONST_09  N13  C14  C15  C16    0.00   0.0  0
 1HX  CONST_10  C14  N13  C12  C16    0.00   0.0  0
 1HX  CONST_11  N13  C12  C16  C15    0.00   0.0  0
 1HX  CONST_12  C7   C4   C5   C6   180.00   0.0  0
 1HX  CONST_13  CL2  C5   C6   C1   180.00   0.0  0
 1HX  CONST_14  F20  C3   C2   C1   180.00   0.0  0
 1HX  CONST_15  CL2  C5   C4   C3   180.00   0.0  0
 1HX  CONST_16  C7   C4   C3   C2   180.00   0.0  0
 1HX  CONST_17  F20  C3   C4   C5   180.00   0.0  0
 1HX  CONST_18  C15  C16  C12  C9   180.00   0.0  0
 1HX  CONST_19  C14  N13  C12  C9   180.00   0.0  0
 1HX  CONST_20  C18  C14  N13  C12  180.00   0.0  0
 1HX  CONST_21  C18  C14  C15  C16  180.00   0.0  0
 1HX  CONST_22  C17  N13  C12  C16  180.00   0.0  0
 1HX  CONST_23  C17  N13  C14  C15  180.00   0.0  0
 1HX  CONST_24  H1   C6   C5   C4   180.00   0.0  0
 1HX  CONST_25  H3   C2   C3   C4   180.00   0.0  0
 1HX  CONST_26  H2   C1   C2   C3   180.00   0.0  0
 1HX  CONST_27  H10  C15  C16  C12  180.00   0.0  0
 1HX  CONST_28  H9   C16  C15  C14  180.00   0.0  0
 1HX  CONST_29  C12  C9   N8   C7   180.00   0.0  0
 1HX  CONST_30  H8   N8   C9   C12    0.00   0.0  0
 1HX  CONST_31  O11  C9   N8   C7     0.00   0.0  0
 1HX  Var_01    C16  C12  C9   N8   -30.66  30.0  2
 1HX  Var_02    H11  C17  N13  C12   74.79  30.0  2

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
 1HX  chir_01  C7  C10  N8  C4  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
 1HX  plan-1  C12  0.020
 1HX  plan-1  C16  0.020
 1HX  plan-1  C15  0.020
 1HX  plan-1  C14  0.020
 1HX  plan-1  C18  0.020
 1HX  plan-1  N19  0.020
 1HX  plan-1  N13  0.020
 1HX  plan-1  C17  0.020
 1HX  plan-1  H9   0.020
 1HX  plan-1  H10  0.020
 1HX  plan-1  C9   0.020
 1HX  plan-2  C4   0.020
 1HX  plan-2  C6   0.020
 1HX  plan-2  C1   0.020
 1HX  plan-2  C3   0.020
 1HX  plan-2  C2   0.020
 1HX  plan-2  C5   0.020
 1HX  plan-2  C7   0.020
 1HX  plan-2  CL2  0.020
 1HX  plan-2  F20  0.020
 1HX  plan-2  H1   0.020
 1HX  plan-2  H2   0.020
 1HX  plan-2  H3   0.020
 1HX  plan-3  C7   0.020
 1HX  plan-3  N8   0.020
 1HX  plan-3  O11  0.020
 1HX  plan-3  C12  0.020
 1HX  plan-3  H8   0.020
 1HX  plan-3  C9   0.020

