# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed May  6 21:00:17 2020
#   Inital geometry file: a 121 line input string
#   Ligand name: N-{4-[(2S)-3-{[2-(3,4-dichlorophenyl)ethyl]amino}-2-hydroxypropoxy]phenyl}methanesulfonamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[S](=O)(=O)Nc1ccc(OC[C@@H](O)CNCCc2ccc(Cl)c(Cl)c2)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
 HYS  HYS  N-{4-[(2S)-3-{[2-(3,4-dichlorophenyl)ethyl]amino}-2-hydroxypropoxy]phenyl}methanesulfonamide  ligand  49  27  .  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_HYS
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
 HYS  C01  C   CR6   0   0.023   7.4581  -0.5431   0.5373
 HYS  C02  C   CR6   0  -0.021   7.9962  -0.5201  -0.7442
 HYS  C03  C   CR16  0  -0.199   7.4005   0.2622  -1.7219
 HYS  C04  C   CR16  0  -0.307   6.2767   1.0117  -1.4179
 HYS  C05  C   CR6   0   0.126   5.7272   0.9974  -0.1389
 HYS  C06  C   CR16  0  -0.271   6.3326   0.2105   0.8343
 HYS  C07  C   CH2   0  -0.530   4.4775   1.7696   0.1704
 HYS  C08  C   CH2   0  -0.246   3.2330   0.9099  -0.0377
 HYS  N09  N   NH1   0  -0.599   2.0288   1.6689   0.2303
 HYS  C10  C   CH2   0  -0.281   0.8283   0.8856   0.0347
 HYS  C11  C   CH1   0  -0.031  -0.4292   1.6915   0.3425
 HYS  C12  C   CH2   0  -0.191  -1.6510   0.8657  -0.0278
 HYS  O13  O   O2    0  -0.470  -2.8066   1.6424   0.2204
 HYS  C14  C   CR6   0   0.394  -4.0099   1.1259  -0.0865
 HYS  C15  C   CR16  0  -0.348  -5.1207   1.9119   0.2279
 HYS  C16  C   CR16  0  -0.263  -6.3954   1.4609  -0.0547
 HYS  C17  C   CR6   0   0.244  -6.5904   0.2300  -0.6781
 HYS  C18  C   CR16  0  -0.238  -5.4862  -0.5453  -0.9997
 HYS  C19  C   CR16  0  -0.384  -4.2029  -0.1131  -0.6942
 HYS  N20  N   NC1   0  -0.820  -7.8966  -0.2161  -1.0131
 HYS  S21  S   S     0   1.317  -8.6106  -1.4170  -0.1129
 HYS  C22  C   CH3   0  -0.796  -8.8386  -0.7559   1.5213
 HYS  O23  O   OS    0  -0.667  -9.9138  -1.6396  -0.7167
 HYS  O24  O   OS    0  -0.658  -7.6614  -2.5137  -0.0266
 HYS  O25  O   OH1   0  -0.654  -0.4753   2.1456   1.6721
 HYS  CL1  CL  CL    0  -0.102   9.3962  -1.4483  -1.1303
 HYS  CL2  CL  CL    0  -0.101   8.1818  -1.5025   1.7735
 HYS  H1   H   HCR6  0   0.287   7.8184   0.2848  -2.7191
 HYS  H2   H   HCR6  0   0.265   5.8235   1.6203  -2.1904
 HYS  H3   H   HCR6  0   0.279   5.9294   0.1844   1.8389
 HYS  H4   H   HCH2  0   0.252   4.4970   2.1332   1.1998
 HYS  H5   H   HCH2  0   0.250   4.4258   2.6464  -0.4809
 HYS  H6   H   HCH2  0   0.200   3.2535   0.4849  -1.0541
 HYS  H7   H   HCH2  0   0.227   3.2656   0.0586   0.6496
 HYS  H8   H   HNH1  0   0.341   2.0028   2.4661  -0.3964
 HYS  H10  H   HCH2  0   0.204   0.7490   0.4779  -0.9856
 HYS  H11  H   HCH2  0   0.226   0.8657   0.0179   0.7041
 HYS  H12  H   HCH1  0   0.235  -0.4295   2.5927  -0.2815
 HYS  H13  H   HCH2  0   0.230  -1.5900   0.5854  -1.0849
 HYS  H14  H   HCH2  0   0.226  -1.6797  -0.0601   0.5623
 HYS  H15  H   HCR6  0   0.269  -4.9773   2.8745   0.7023
 HYS  H16  H   HCR6  0   0.271  -7.2479   2.0773   0.2046
 HYS  H17  H   HCR6  0   0.269  -5.6183  -1.4917  -1.5051
 HYS  H18  H   HCR6  0   0.284  -3.3692  -0.7500  -0.9562
 HYS  H19  H   HNC1  0   0.419  -8.5544   0.5221  -1.2423
 HYS  H20  H   HCH3  0   0.292  -7.8757  -0.4528   1.9268
 HYS  H21  H   HCH3  0   0.295  -9.5154   0.0938   1.4735
 HYS  H22  H   HCH3  0   0.309  -9.2679  -1.5406   2.1422
 HYS  H23  H   HOH1  0   0.444  -0.3484   1.3916   2.2584

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
 HYS  C22  S21  single    1.778  0.020  1.778
 HYS  N09  C10  single    1.447  0.020  1.447
 HYS  N09  C08  single    1.448  0.020  1.448
 HYS  C10  C11  single    1.525  0.020  1.525
 HYS  C08  C07  single    1.527  0.020  1.527
 HYS  C11  C12  single    1.520  0.020  1.520
 HYS  C11  O25  single    1.406  0.020  1.406
 HYS  C18  C19  aromatic  1.388  0.020  1.388
 HYS  C18  C17  aromatic  1.387  0.020  1.387
 HYS  C19  C14  aromatic  1.393  0.020  1.393
 HYS  S21  O24  double    1.453  0.020  1.453
 HYS  S21  O23  double    1.453  0.020  1.453
 HYS  S21  N20  single    1.662  0.020  1.662
 HYS  C12  O13  single    1.414  0.020  1.414
 HYS  C04  C03  aromatic  1.385  0.020  1.385
 HYS  C04  C05  aromatic  1.392  0.020  1.392
 HYS  N20  C17  single    1.420  0.020  1.420
 HYS  C17  C16  aromatic  1.394  0.020  1.394
 HYS  C07  C05  single    1.501  0.020  1.501
 HYS  C14  O13  single    1.345  0.020  1.345
 HYS  C14  C15  aromatic  1.397  0.020  1.397
 HYS  C03  C02  aromatic  1.387  0.020  1.387
 HYS  C05  C06  aromatic  1.390  0.020  1.390
 HYS  C02  CL1  single    1.723  0.020  1.723
 HYS  C02  C01  aromatic  1.390  0.020  1.390
 HYS  C06  C01  aromatic  1.387  0.020  1.387
 HYS  C01  CL2  single    1.724  0.020  1.724
 HYS  C16  C15  aromatic  1.381  0.020  1.381
 HYS  C03  H1   single    0.930  0.020  1.080
 HYS  C04  H2   single    0.930  0.020  1.080
 HYS  C06  H3   single    0.930  0.020  1.080
 HYS  C07  H4   single    0.970  0.020  1.090
 HYS  C07  H5   single    0.970  0.020  1.090
 HYS  C08  H6   single    0.970  0.020  1.090
 HYS  C08  H7   single    0.970  0.020  1.090
 HYS  N09  H8   single    0.890  0.020  1.040
 HYS  C10  H10  single    0.970  0.020  1.090
 HYS  C10  H11  single    0.970  0.020  1.090
 HYS  C11  H12  single    0.970  0.020  1.090
 HYS  C12  H13  single    0.970  0.020  1.090
 HYS  C12  H14  single    0.970  0.020  1.090
 HYS  C15  H15  single    0.930  0.020  1.080
 HYS  C16  H16  single    0.930  0.020  1.080
 HYS  C18  H17  single    0.930  0.020  1.080
 HYS  C19  H18  single    0.930  0.020  1.080
 HYS  N20  H19  single    0.890  0.020  1.040
 HYS  C22  H20  single    0.970  0.020  1.090
 HYS  C22  H21  single    0.970  0.020  1.090
 HYS  C22  H22  single    0.970  0.020  1.090
 HYS  O25  H23  single    0.850  0.020  0.980

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
 HYS  CL2  C01  C06  119.31  3.000
 HYS  CL2  C01  C02  120.51  3.000
 HYS  C06  C01  C02  120.18  3.000
 HYS  CL1  C02  C03  119.66  3.000
 HYS  CL1  C02  C01  120.80  3.000
 HYS  C03  C02  C01  119.54  3.000
 HYS  H1   C03  C04  120.31  3.000
 HYS  H1   C03  C02  119.73  3.000
 HYS  C04  C03  C02  119.95  3.000
 HYS  H2   C04  C05  119.74  3.000
 HYS  H2   C04  C03  119.16  3.000
 HYS  C05  C04  C03  121.10  3.000
 HYS  C07  C05  C06  120.63  3.000
 HYS  C06  C05  C04  118.49  3.000
 HYS  C07  C05  C04  120.83  3.000
 HYS  H3   C06  C05  120.06  3.000
 HYS  H3   C06  C01  119.20  3.000
 HYS  C05  C06  C01  120.74  3.000
 HYS  H5   C07  H4   107.18  3.000
 HYS  H5   C07  C08  109.38  3.000
 HYS  H4   C07  C08  109.30  3.000
 HYS  H5   C07  C05  109.22  3.000
 HYS  H4   C07  C05  110.53  3.000
 HYS  C08  C07  C05  111.15  3.000
 HYS  H7   C08  H6   106.19  3.000
 HYS  H7   C08  N09  108.43  3.000
 HYS  H6   C08  N09  112.85  3.000
 HYS  H7   C08  C07  109.15  3.000
 HYS  H6   C08  C07  109.13  3.000
 HYS  N09  C08  C07  110.94  3.000
 HYS  H8   N09  C10  108.71  3.000
 HYS  H8   N09  C08  108.59  3.000
 HYS  C10  N09  C08  112.40  3.000
 HYS  H11  C10  H10  105.96  3.000
 HYS  H11  C10  C11  108.85  3.000
 HYS  H10  C10  C11  108.86  3.000
 HYS  H11  C10  N09  108.52  3.000
 HYS  H10  C10  N09  112.66  3.000
 HYS  C11  C10  N09  111.77  3.000
 HYS  H12  C11  O25  105.83  3.000
 HYS  H12  C11  C12  107.92  3.000
 HYS  O25  C11  C12  112.30  3.000
 HYS  H12  C11  C10  108.65  3.000
 HYS  O25  C11  C10  112.87  3.000
 HYS  C12  C11  C10  109.05  3.000
 HYS  H14  C12  H13  107.71  3.000
 HYS  H14  C12  O13  110.33  3.000
 HYS  H13  C12  O13  110.82  3.000
 HYS  H14  C12  C11  110.36  3.000
 HYS  H13  C12  C11  109.22  3.000
 HYS  O13  C12  C11  108.40  3.000
 HYS  C14  O13  C12  118.69  3.000
 HYS  C19  C14  C15  119.24  3.000
 HYS  C15  C14  O13  116.36  3.000
 HYS  C19  C14  O13  124.40  3.000
 HYS  H15  C15  C16  120.13  3.000
 HYS  H15  C15  C14  119.59  3.000
 HYS  C16  C15  C14  120.28  3.000
 HYS  H16  C16  C17  119.97  3.000
 HYS  H16  C16  C15  119.43  3.000
 HYS  C17  C16  C15  120.60  3.000
 HYS  N20  C17  C18  120.12  3.000
 HYS  N20  C17  C16  120.77  3.000
 HYS  C18  C17  C16  119.09  3.000
 HYS  H17  C18  C19  119.23  3.000
 HYS  H17  C18  C17  120.03  3.000
 HYS  C19  C18  C17  120.73  3.000
 HYS  H18  C19  C18  118.43  3.000
 HYS  H18  C19  C14  121.50  3.000
 HYS  C18  C19  C14  120.05  3.000
 HYS  H19  N20  S21  111.68  3.000
 HYS  H19  N20  C17  114.89  3.000
 HYS  S21  N20  C17  119.62  3.000
 HYS  O24  S21  O23  119.66  3.000
 HYS  O23  S21  C22  108.90  3.000
 HYS  O24  S21  C22  108.05  3.000
 HYS  O23  S21  N20  105.72  3.000
 HYS  O24  S21  N20  107.27  3.000
 HYS  C22  S21  N20  106.52  3.000
 HYS  H22  C22  H21  110.05  3.000
 HYS  H22  C22  H20  109.70  3.000
 HYS  H21  C22  H20  110.46  3.000
 HYS  H22  C22  S21  107.87  3.000
 HYS  H21  C22  S21  109.27  3.000
 HYS  H20  C22  S21  109.44  3.000
 HYS  H23  O25  C11  108.57  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
 HYS  CONST_01  C04  C03  C02  C01     0.00   0.0  0
 HYS  CONST_02  C04  C05  C06  C01     0.00   0.0  0
 HYS  CONST_03  C05  C04  C03  C02     0.00   0.0  0
 HYS  CONST_04  C05  C06  C01  C02     0.00   0.0  0
 HYS  CONST_05  C06  C05  C04  C03     0.00   0.0  0
 HYS  CONST_06  C06  C01  C02  C03     0.00   0.0  0
 HYS  CONST_07  C17  C18  C19  C14     0.00   0.0  0
 HYS  CONST_08  C17  C16  C15  C14     0.00   0.0  0
 HYS  CONST_09  C18  C19  C14  C15     0.00   0.0  0
 HYS  CONST_10  C18  C17  C16  C15     0.00   0.0  0
 HYS  CONST_11  C19  C18  C17  C16     0.00   0.0  0
 HYS  CONST_12  C19  C14  C15  C16     0.00   0.0  0
 HYS  CONST_13  C07  C05  C06  C01   180.00   0.0  0
 HYS  CONST_14  C07  C05  C04  C03   180.00   0.0  0
 HYS  CONST_15  CL2  C01  C02  C03   180.00   0.0  0
 HYS  CONST_16  CL1  C02  C03  C04   180.00   0.0  0
 HYS  CONST_17  CL2  C01  C06  C05   180.00   0.0  0
 HYS  CONST_18  CL1  C02  C01  C06   180.00   0.0  0
 HYS  CONST_19  C18  C19  C14  O13   180.00   0.0  0
 HYS  CONST_20  C16  C15  C14  O13   180.00   0.0  0
 HYS  CONST_21  N20  C17  C16  C15   180.00   0.0  0
 HYS  CONST_22  N20  C17  C18  C19   180.00   0.0  0
 HYS  CONST_23  H1   C03  C02  C01   180.00   0.0  0
 HYS  CONST_24  H2   C04  C03  C02   180.00   0.0  0
 HYS  CONST_25  H3   C06  C01  C02   180.00   0.0  0
 HYS  CONST_26  H17  C18  C19  C14   180.00   0.0  0
 HYS  CONST_27  H16  C16  C15  C14   180.00   0.0  0
 HYS  CONST_28  H18  C19  C14  C15   180.00   0.0  0
 HYS  CONST_29  H15  C15  C16  C17   180.00   0.0  0
 HYS  Var_01    C08  C07  C05  C04    91.25  30.0  2
 HYS  Var_02    C19  C14  O13  C12    -2.99  30.0  2
 HYS  Var_03    N09  C08  C07  C05  -178.60  30.0  2
 HYS  Var_04    C22  S21  N20  C17    64.70  30.0  2
 HYS  Var_05    H13  C12  O13  C14    57.61  30.0  2
 HYS  Var_06    C10  N09  C08  C07   179.66  30.0  1
 HYS  Var_07    C11  C10  N09  C08   179.07  30.0  3
 HYS  Var_08    H20  C22  S21  N20   -58.36  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
 HYS  chir_01  C11  C10  C12  O25  negativ

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
 HYS  plan-1  C01  0.020
 HYS  plan-1  C02  0.020
 HYS  plan-1  C03  0.020
 HYS  plan-1  C04  0.020
 HYS  plan-1  C05  0.020
 HYS  plan-1  C06  0.020
 HYS  plan-1  C07  0.020
 HYS  plan-1  CL1  0.020
 HYS  plan-1  CL2  0.020
 HYS  plan-1  H1   0.020
 HYS  plan-1  H2   0.020
 HYS  plan-1  H3   0.020
 HYS  plan-2  O13  0.020
 HYS  plan-2  C14  0.020
 HYS  plan-2  C15  0.020
 HYS  plan-2  C16  0.020
 HYS  plan-2  C17  0.020
 HYS  plan-2  C18  0.020
 HYS  plan-2  C19  0.020
 HYS  plan-2  N20  0.020
 HYS  plan-2  H15  0.020
 HYS  plan-2  H16  0.020
 HYS  plan-2  H17  0.020
 HYS  plan-2  H18  0.020
 HYS  plan-3  C17  0.020
 HYS  plan-3  N20  0.020
 HYS  plan-3  S21  0.020
 HYS  plan-3  H19  0.020

