# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed May  6 00:55:00 2020
#   Inital geometry file: a 91 line input string
#   Ligand name: 4-(4-chlorophenoxy)-N-[(3S)-2-oxotetrahydrofuran-3-yl]butanamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Clc1ccc(OCCCC(=O)N[C@H]2CCOC2=O)cc1
#
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
 HLC  HLC  4-(4-chlorophenoxy)-N-[(3S)-2-oxotetrahydrofuran-3-yl]butanamide  ligand  36  20  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_HLC
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
 HLC  N1   N   NH1   0  -0.640  -3.7910  -0.6426  -0.2680
 HLC  C1   C   C     0   0.579  -5.6703   0.5394   0.7974
 HLC  O1   O   O     0  -0.424  -5.0603   1.2972   1.4977
 HLC  C2   C   CH2   0  -0.185  -7.4230  -0.6994   0.0217
 HLC  O2   O   O2    0  -0.437  -6.9549   0.2600   0.9903
 HLC  C3   C   CH2   0  -0.499  -6.1665  -1.3729  -0.5092
 HLC  O3   O   O2    0  -0.473   2.0650   0.7752  -0.3546
 HLC  C4   C   CH1   0  -0.246  -5.1548  -0.2402  -0.4061
 HLC  O4   O   O     0  -0.488  -2.9052   1.0519  -1.4661
 HLC  C5   C   C     0   0.574  -2.7557   0.0409  -0.7990
 HLC  C6   C   CH2   0  -0.596  -1.3984  -0.5762  -0.5416
 HLC  C7   C   CH2   0  -0.457  -0.2735   0.4482  -0.5575
 HLC  C8   C   CH2   0  -0.174   1.0607  -0.2262  -0.3161
 HLC  C9   C   CR6   0   0.396   3.3450   0.4274  -0.1368
 HLC  C10  C   CR16  0  -0.349   4.2824   1.4622  -0.1837
 HLC  C11  C   CR16  0  -0.198   5.6235   1.2064   0.0289
 HLC  C12  C   CR6   0  -0.067   6.0407  -0.0919   0.2915
 HLC  C13  C   CR16  0  -0.197   5.1252  -1.1266   0.3401
 HLC  C14  C   CR16  0  -0.385   3.7760  -0.8708   0.1257
 HLC  H1   H   HNH1  0   0.407  -3.5981  -1.4353   0.3241
 HLC  H2   H   HCH2  0   0.267  -8.1074  -1.3782   0.5244
 HLC  H3   H   HCH2  0   0.254  -7.9621  -0.1657  -0.7625
 HLC  H4   H   HCH2  0   0.269  -5.8739  -2.2074   0.1329
 HLC  H5   H   HCH2  0   0.283  -6.2939  -1.7459  -1.5228
 HLC  H6   H   HCH1  0   0.318  -5.2407   0.4204  -1.2749
 HLC  H7   H   HCH2  0   0.262  -1.4066  -1.1215   0.4058
 HLC  H8   H   HCH2  0   0.282  -1.2321  -1.3274  -1.3214
 HLC  H9   H   HCH2  0   0.246  -0.2536   0.9653  -1.5182
 HLC  H10  H   HCH2  0   0.245  -0.4433   1.2006   0.2162
 HLC  H11  H   HCH2  0   0.226   1.2498  -0.9869  -1.0831
 HLC  H12  H   HCH2  0   0.226   1.0631  -0.7307   0.6572
 HLC  H13  H   HCR6  0   0.273   3.9526   2.4727  -0.3889
 HLC  H14  H   HCR6  0   0.281   6.3385   2.0169  -0.0098
 HLC  H15  H   HCR6  0   0.282   5.4484  -2.1384   0.5444
 HLC  H16  H   HCR6  0   0.289   3.0842  -1.7003   0.1681
 HLC  CL1  CL  CL    0  -0.140   7.7253  -0.4142   0.5608

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
 HLC  N1   C4   single    1.429  0.020  1.429
 HLC  N1   C5   single    1.349  0.020  1.349
 HLC  N1   H1   single    0.860  0.020  1.020
 HLC  C1   O1   double    1.199  0.020  1.199
 HLC  C1   O2   single    1.329  0.020  1.329
 HLC  C1   C4   single    1.524  0.020  1.524
 HLC  C2   O2   single    1.441  0.020  1.441
 HLC  C2   C3   single    1.521  0.020  1.521
 HLC  C2   H2   single    0.970  0.020  1.090
 HLC  C2   H3   single    0.970  0.020  1.090
 HLC  C3   C4   single    1.522  0.020  1.522
 HLC  C3   H4   single    0.970  0.020  1.090
 HLC  C3   H5   single    0.970  0.020  1.090
 HLC  O3   C8   single    1.419  0.020  1.419
 HLC  O3   C9   single    1.344  0.020  1.344
 HLC  C4   H6   single    0.970  0.020  1.090
 HLC  O4   C5   double    1.220  0.020  1.220
 HLC  C5   C6   single    1.513  0.020  1.513
 HLC  C6   C7   single    1.522  0.020  1.522
 HLC  C6   H7   single    0.970  0.020  1.090
 HLC  C6   H8   single    0.970  0.020  1.090
 HLC  C7   C8   single    1.514  0.020  1.514
 HLC  C7   H9   single    0.970  0.020  1.090
 HLC  C7   H10  single    0.970  0.020  1.090
 HLC  C8   H11  single    0.970  0.020  1.090
 HLC  C8   H12  single    0.970  0.020  1.090
 HLC  C9   C10  aromatic  1.397  0.020  1.397
 HLC  C9   C14  aromatic  1.393  0.020  1.393
 HLC  C10  C11  aromatic  1.382  0.020  1.382
 HLC  C10  H13  single    0.930  0.020  1.080
 HLC  C11  C12  aromatic  1.389  0.020  1.389
 HLC  C11  H14  single    0.930  0.020  1.080
 HLC  C12  C13  aromatic  1.382  0.020  1.382
 HLC  C12  CL1  single    1.736  0.020  1.736
 HLC  C13  C14  aromatic  1.390  0.020  1.390
 HLC  C13  H15  single    0.930  0.020  1.080
 HLC  C14  H16  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
 HLC  H1   N1   C5   118.85  3.000
 HLC  H1   N1   C4   117.45  3.000
 HLC  C5   N1   C4   123.48  3.000
 HLC  C4   C1   O2   109.52  3.000
 HLC  C4   C1   O1   127.79  3.000
 HLC  O2   C1   O1   122.69  3.000
 HLC  H3   C2   H2   109.07  3.000
 HLC  H3   C2   C3   111.96  3.000
 HLC  H2   C2   C3   113.89  3.000
 HLC  H3   C2   O2   108.53  3.000
 HLC  H2   C2   O2   108.01  3.000
 HLC  C3   C2   O2   105.12  3.000
 HLC  C2   O2   C1   110.88  3.000
 HLC  H5   C3   H4   108.48  3.000
 HLC  H5   C3   C4   113.34  3.000
 HLC  H4   C3   C4   110.52  3.000
 HLC  H5   C3   C2   112.35  3.000
 HLC  H4   C3   C2   110.74  3.000
 HLC  C4   C3   C2   101.30  3.000
 HLC  C9   O3   C8   119.15  3.000
 HLC  H6   C4   C3   110.06  3.000
 HLC  H6   C4   C1   106.95  3.000
 HLC  C3   C4   C1   102.08  3.000
 HLC  H6   C4   N1   108.76  3.000
 HLC  C3   C4   N1   115.56  3.000
 HLC  C1   C4   N1   113.00  3.000
 HLC  C6   C5   O4   122.73  3.000
 HLC  C6   C5   N1   114.50  3.000
 HLC  O4   C5   N1   122.73  3.000
 HLC  H8   C6   H7   106.03  3.000
 HLC  H8   C6   C7   110.00  3.000
 HLC  H7   C6   C7   110.52  3.000
 HLC  H8   C6   C5   107.14  3.000
 HLC  H7   C6   C5   110.13  3.000
 HLC  C7   C6   C5   112.76  3.000
 HLC  H10  C7   H9   107.46  3.000
 HLC  H10  C7   C8   109.31  3.000
 HLC  H9   C7   C8   109.59  3.000
 HLC  H10  C7   C6   109.96  3.000
 HLC  H9   C7   C6   109.98  3.000
 HLC  C8   C7   C6   110.48  3.000
 HLC  H12  C8   H11  107.54  3.000
 HLC  H12  C8   C7   110.39  3.000
 HLC  H11  C8   C7   110.45  3.000
 HLC  H12  C8   O3   110.33  3.000
 HLC  H11  C8   O3   110.40  3.000
 HLC  C7   C8   O3   107.76  3.000
 HLC  C14  C9   C10  119.28  3.000
 HLC  C14  C9   O3   124.49  3.000
 HLC  C10  C9   O3   116.22  3.000
 HLC  H13  C10  C11  119.85  3.000
 HLC  H13  C10  C9   119.56  3.000
 HLC  C11  C10  C9   120.59  3.000
 HLC  H14  C11  C12  120.58  3.000
 HLC  H14  C11  C10  119.83  3.000
 HLC  C12  C11  C10  119.59  3.000
 HLC  CL1  C12  C13  119.88  3.000
 HLC  CL1  C12  C11  119.63  3.000
 HLC  C13  C12  C11  120.49  3.000
 HLC  H15  C13  C14  119.43  3.000
 HLC  H15  C13  C12  120.59  3.000
 HLC  C14  C13  C12  119.98  3.000
 HLC  H16  C14  C13  118.29  3.000
 HLC  H16  C14  C9   121.65  3.000
 HLC  C13  C14  C9   120.06  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
 HLC  CONST_01  C12  C11  C10  C9      0.00   0.0  0
 HLC  CONST_02  C12  C13  C14  C9      0.00   0.0  0
 HLC  CONST_03  C13  C14  C9   C10     0.00   0.0  0
 HLC  CONST_04  C13  C12  C11  C10     0.00   0.0  0
 HLC  CONST_05  C14  C9   C10  C11     0.00   0.0  0
 HLC  CONST_06  C14  C13  C12  C11     0.00   0.0  0
 HLC  CONST_07  C11  C10  C9   O3    180.00   0.0  0
 HLC  CONST_08  C13  C14  C9   O3    180.00   0.0  0
 HLC  CONST_09  CL1  C12  C11  C10   180.00   0.0  0
 HLC  CONST_10  CL1  C12  C13  C14   180.00   0.0  0
 HLC  CONST_11  H14  C11  C10  C9    180.00   0.0  0
 HLC  CONST_12  H15  C13  C14  C9    180.00   0.0  0
 HLC  CONST_13  H16  C14  C9   C10   180.00   0.0  0
 HLC  CONST_14  H13  C10  C11  C12   180.00   0.0  0
 HLC  CONST_15  O4   C5   N1   C4      0.00   0.0  0
 HLC  CONST_16  C6   C5   N1   C4    180.00   0.0  0
 HLC  CONST_17  H1   N1   C5   O4    180.00   0.0  0
 HLC  Var_01    C3   C2   O2   C1     19.72  30.0  1
 HLC  Var_02    C4   C1   O2   C2      1.12  30.0  1
 HLC  Var_03    C4   C3   C2   O2    -31.44  30.0  1
 HLC  Var_04    C10  C9   O3   C8   -179.75  30.0  2
 HLC  Var_05    H11  C8   O3   C9    -60.74  30.0  3
 HLC  Var_06    C7   C6   C5   N1   -153.65  30.0  3
 HLC  Var_07    C6   C7   C8   O3    179.49  30.0  2
 HLC  Var_08    C8   C7   C6   C5   -179.13  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
 HLC  chir_01  C4  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
 HLC  plan-1  O3   0.020
 HLC  plan-1  C9   0.020
 HLC  plan-1  C10  0.020
 HLC  plan-1  C11  0.020
 HLC  plan-1  C12  0.020
 HLC  plan-1  C13  0.020
 HLC  plan-1  C14  0.020
 HLC  plan-1  H13  0.020
 HLC  plan-1  H14  0.020
 HLC  plan-1  H15  0.020
 HLC  plan-1  H16  0.020
 HLC  plan-1  CL1  0.020
 HLC  plan-2  N1   0.020
 HLC  plan-2  C4   0.020
 HLC  plan-2  O4   0.020
 HLC  plan-2  C5   0.020
 HLC  plan-2  C6   0.020
 HLC  plan-2  H1   0.020
 HLC  plan-3  C1   0.020
 HLC  plan-3  O1   0.020
 HLC  plan-3  O2   0.020
 HLC  plan-3  C4   0.020

