# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu May  7 00:50:26 2020
#   Inital geometry file: a 139 line input string
#   Ligand name: N-{4-[(2S)-3-{[2-(3,4-dichlorophenyl)ethyl](propyl)amino}-2-hydroxypropoxy]phenyl}methanesulfonamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCN(CCc1ccc(Cl)c(Cl)c1)C[C@H](O)COc2ccc(N[S](C)(=O)=O)cc2
#
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
 HYY  HYY  N-{4-[(2S)-3-{[2-(3,4-dichlorophenyl)ethyl](propyl)amino}-2-hydroxypropoxy]phenyl}methanesulfonamide  ligand  58  30  .  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_HYY
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
 HYY  C01  C   CR16  0  -0.307   6.1220  -0.5006  -0.7120
 HYY  C02  C   CR16  0  -0.199   7.0665   0.4113  -1.1510
 HYY  C03  C   CR6   0  -0.023   7.2173   1.6244  -0.4954
 HYY  C04  C   CR6   0   0.024   6.4151   1.9145   0.6015
 HYY  C05  C   CR16  0  -0.276   5.4673   0.9981   1.0325
 HYY  C06  C   CR6   0   0.141   5.3090  -0.2205   0.3836
 HYY  C07  C   CH2   0  -0.544   4.2549  -1.1922   0.8276
 HYY  C08  C   CH2   0  -0.261   3.0079  -1.0668  -0.0490
 HYY  N09  N   NT    0  -0.433   1.8905  -1.8645   0.4274
 HYY  C10  C   CH2   0  -0.314   2.1824  -3.2888   0.5268
 HYY  C11  C   CH2   0  -0.452   2.5820  -4.0076  -0.7638
 HYY  C12  C   CH3   0  -0.660   2.8451  -5.4857  -0.5095
 HYY  C13  C   CH2   0  -0.294   0.6726  -1.5365  -0.2918
 HYY  C14  C   CH1   0  -0.017  -0.6194  -1.8644   0.4567
 HYY  C15  C   CH2   0  -0.191  -1.7592  -1.0508  -0.1421
 HYY  O16  O   O2    0  -0.469  -2.9271  -1.3245   0.6064
 HYY  C17  C   CR6   0   0.395  -4.0946  -0.7838   0.2191
 HYY  C18  C   CR16  0  -0.383  -4.2534   0.0365  -0.8954
 HYY  C19  C   CR16  0  -0.258  -5.5096   0.5452  -1.2020
 HYY  C20  C   CR6   0   0.238  -6.6153   0.2340  -0.4250
 HYY  C21  C   CR16  0  -0.235  -6.4541  -0.5942   0.6833
 HYY  C22  C   CR16  0  -0.352  -5.2074  -1.0908   1.0068
 HYY  N23  N   NC1   0  -0.818  -7.9092   0.7195  -0.7582
 HYY  S24  S   S     0   1.317  -8.5145   2.0312   0.0630
 HYY  C25  C   CH3   0  -0.797  -7.4863   3.4160  -0.3671
 HYY  O26  O   OS    0  -0.668  -9.8470   2.2562  -0.4725
 HYY  O27  O   OS    0  -0.659  -8.3432   1.7658   1.4815
 HYY  O28  O   OH1   0  -0.653  -0.9451  -3.2369   0.4780
 HYY  CL1  CL  CL    0  -0.101   6.5875   3.4093   1.4430
 HYY  CL2  CL  CL    0  -0.102   8.3988   2.7512  -1.0480
 HYY  H1   H   HCR6  0   0.263   6.0243  -1.4462  -1.2311
 HYY  H2   H   HCR6  0   0.287   7.6921   0.1819  -2.0027
 HYY  H3   H   HCR6  0   0.279   4.8501   1.2377   1.8892
 HYY  H4   H   HCH2  0   0.256   4.6600  -2.2051   0.7787
 HYY  H5   H   HCH2  0   0.253   3.9805  -1.0045   1.8681
 HYY  H6   H   HCH2  0   0.243   2.6940  -0.0193  -0.0388
 HYY  H7   H   HCH2  0   0.201   3.2832  -1.2888  -1.0930
 HYY  H9   H   HCH2  0   0.228   2.9799  -3.4247   1.2626
 HYY  H10  H   HCH2  0   0.247   1.3124  -3.7870   0.9536
 HYY  H11  H   HCH2  0   0.218   1.7953  -3.9049  -1.5164
 HYY  H12  H   HCH2  0   0.217   3.4782  -3.5501  -1.1932
 HYY  H13  H   HCH3  0   0.230   3.1469  -6.0008  -1.4219
 HYY  H14  H   HCH3  0   0.218   3.6401  -5.6258   0.2257
 HYY  H15  H   HCH3  0   0.218   1.9533  -5.9874  -0.1292
 HYY  H16  H   HCH2  0   0.240   0.6825  -0.4550  -0.4517
 HYY  H17  H   HCH2  0   0.206   0.6274  -1.9795  -1.3010
 HYY  H18  H   HCH1  0   0.239  -0.4886  -1.5688   1.5022
 HYY  H19  H   HCH2  0   0.234  -1.5196   0.0175  -0.1017
 HYY  H20  H   HCH2  0   0.226  -1.9006  -1.3213  -1.1969
 HYY  H21  H   HCR6  0   0.284  -3.4201   0.2995  -1.5322
 HYY  H22  H   HCR6  0   0.271  -5.6197   1.1889  -2.0666
 HYY  H23  H   HCR6  0   0.267  -7.3101  -0.8606   1.2879
 HYY  H24  H   HCR6  0   0.268  -5.0870  -1.7352   1.8685
 HYY  H25  H   HNC1  0   0.418  -8.1026   0.7782  -1.7527
 HYY  H26  H   HCH3  0   0.295  -7.5447   3.5862  -1.4395
 HYY  H27  H   HCH3  0   0.309  -7.8583   4.2873   0.1695
 HYY  H28  H   HCH3  0   0.291  -6.4596   3.2126  -0.0706
 HYY  H29  H   HOH1  0   0.444  -0.9480  -3.5649  -0.4282

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
 HYY  C19  C18  aromatic  1.389  0.020  1.389
 HYY  C19  C20  aromatic  1.387  0.020  1.387
 HYY  C18  C17  aromatic  1.393  0.020  1.393
 HYY  O28  C14  single    1.411  0.020  1.411
 HYY  N23  C20  single    1.422  0.020  1.422
 HYY  N23  S24  single    1.662  0.020  1.662
 HYY  C20  C21  aromatic  1.393  0.020  1.393
 HYY  CL1  C04  single    1.724  0.020  1.724
 HYY  C17  O16  single    1.344  0.020  1.344
 HYY  C17  C22  aromatic  1.398  0.020  1.398
 HYY  O16  C15  single    1.414  0.020  1.414
 HYY  C04  C05  aromatic  1.387  0.020  1.387
 HYY  C04  C03  aromatic  1.389  0.020  1.389
 HYY  C05  C06  aromatic  1.390  0.020  1.390
 HYY  CL2  C03  single    1.724  0.020  1.724
 HYY  O26  S24  double    1.454  0.020  1.454
 HYY  C03  C02  aromatic  1.387  0.020  1.387
 HYY  O27  S24  double    1.453  0.020  1.453
 HYY  C06  C07  single    1.501  0.020  1.501
 HYY  C06  C01  aromatic  1.393  0.020  1.393
 HYY  C07  C08  single    1.529  0.020  1.529
 HYY  C02  C01  aromatic  1.384  0.020  1.384
 HYY  S24  C25  single    1.778  0.020  1.778
 HYY  C14  C15  single    1.523  0.020  1.523
 HYY  C14  C13  single    1.529  0.020  1.529
 HYY  C21  C22  aromatic  1.380  0.020  1.380
 HYY  N09  C08  single    1.453  0.020  1.453
 HYY  N09  C13  single    1.452  0.020  1.452
 HYY  N09  C10  single    1.457  0.020  1.457
 HYY  C11  C12  single    1.523  0.020  1.523
 HYY  C11  C10  single    1.530  0.020  1.530
 HYY  C01  H1   single    0.930  0.020  1.080
 HYY  C02  H2   single    0.930  0.020  1.080
 HYY  C05  H3   single    0.930  0.020  1.080
 HYY  C07  H4   single    0.970  0.020  1.090
 HYY  C07  H5   single    0.970  0.020  1.090
 HYY  C08  H6   single    0.970  0.020  1.090
 HYY  C08  H7   single    0.970  0.020  1.090
 HYY  C10  H9   single    0.970  0.020  1.090
 HYY  C10  H10  single    0.970  0.020  1.090
 HYY  C11  H11  single    0.970  0.020  1.090
 HYY  C11  H12  single    0.970  0.020  1.090
 HYY  C12  H13  single    0.970  0.020  1.090
 HYY  C12  H14  single    0.970  0.020  1.090
 HYY  C12  H15  single    0.970  0.020  1.090
 HYY  C13  H16  single    0.970  0.020  1.090
 HYY  C13  H17  single    0.970  0.020  1.090
 HYY  C14  H18  single    0.970  0.020  1.090
 HYY  C15  H19  single    0.970  0.020  1.090
 HYY  C15  H20  single    0.970  0.020  1.090
 HYY  C18  H21  single    0.930  0.020  1.080
 HYY  C19  H22  single    0.930  0.020  1.080
 HYY  C21  H23  single    0.930  0.020  1.080
 HYY  C22  H24  single    0.930  0.020  1.080
 HYY  N23  H25  single    0.890  0.020  1.040
 HYY  C25  H26  single    0.970  0.020  1.090
 HYY  C25  H27  single    0.970  0.020  1.090
 HYY  C25  H28  single    0.970  0.020  1.090
 HYY  O28  H29  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
 HYY  H1   C01  C06  119.99  3.000
 HYY  H1   C01  C02  118.99  3.000
 HYY  C06  C01  C02  121.02  3.000
 HYY  H2   C02  C03  119.66  3.000
 HYY  H2   C02  C01  120.31  3.000
 HYY  C03  C02  C01  120.03  3.000
 HYY  CL2  C03  C04  120.82  3.000
 HYY  CL2  C03  C02  119.65  3.000
 HYY  C04  C03  C02  119.53  3.000
 HYY  CL1  C04  C05  119.31  3.000
 HYY  C05  C04  C03  120.12  3.000
 HYY  CL1  C04  C03  120.57  3.000
 HYY  H3   C05  C06  119.91  3.000
 HYY  H3   C05  C04  119.29  3.000
 HYY  C06  C05  C04  120.81  3.000
 HYY  C07  C06  C05  120.64  3.000
 HYY  C07  C06  C01  120.83  3.000
 HYY  C05  C06  C01  118.50  3.000
 HYY  H5   C07  H4   107.18  3.000
 HYY  H5   C07  C08  109.09  3.000
 HYY  H4   C07  C08  110.67  3.000
 HYY  H5   C07  C06  110.30  3.000
 HYY  H4   C07  C06  109.07  3.000
 HYY  C08  C07  C06  110.49  3.000
 HYY  H7   C08  H6   105.87  3.000
 HYY  H7   C08  N09  113.07  3.000
 HYY  H6   C08  N09  107.58  3.000
 HYY  H7   C08  C07  108.83  3.000
 HYY  H6   C08  C07  107.90  3.000
 HYY  N09  C08  C07  113.21  3.000
 HYY  C13  N09  C10  115.00  3.000
 HYY  C10  N09  C08  113.88  3.000
 HYY  C13  N09  C08  111.02  3.000
 HYY  H10  C10  H9   105.18  3.000
 HYY  H10  C10  C11  108.91  3.000
 HYY  H9   C10  C11  108.58  3.000
 HYY  H10  C10  N09  108.28  3.000
 HYY  H9   C10  N09  108.27  3.000
 HYY  C11  C10  N09  116.99  3.000
 HYY  H12  C11  H11  106.26  3.000
 HYY  H12  C11  C12  109.26  3.000
 HYY  H11  C11  C12  109.29  3.000
 HYY  H12  C11  C10  110.40  3.000
 HYY  H11  C11  C10  110.39  3.000
 HYY  C12  C11  C10  111.11  3.000
 HYY  H15  C12  H14  107.53  3.000
 HYY  H15  C12  H13  107.49  3.000
 HYY  H14  C12  H13  107.54  3.000
 HYY  H15  C12  C11  111.29  3.000
 HYY  H14  C12  C11  111.27  3.000
 HYY  H13  C12  C11  111.51  3.000
 HYY  H17  C13  H16  105.30  3.000
 HYY  H17  C13  C14  109.10  3.000
 HYY  H16  C13  C14  106.95  3.000
 HYY  H17  C13  N09  113.38  3.000
 HYY  H16  C13  N09  106.75  3.000
 HYY  C14  C13  N09  114.70  3.000
 HYY  H18  C14  O28  106.02  3.000
 HYY  H18  C14  C15  108.71  3.000
 HYY  O28  C14  C15  110.66  3.000
 HYY  H18  C14  C13  107.99  3.000
 HYY  C15  C14  C13  108.99  3.000
 HYY  O28  C14  C13  114.28  3.000
 HYY  H20  C15  H19  107.69  3.000
 HYY  H20  C15  O16  110.76  3.000
 HYY  H19  C15  O16  110.48  3.000
 HYY  H20  C15  C14  110.02  3.000
 HYY  H19  C15  C14  110.04  3.000
 HYY  O16  C15  C14  107.85  3.000
 HYY  C17  O16  C15  119.15  3.000
 HYY  C22  C17  C18  119.31  3.000
 HYY  C22  C17  O16  116.16  3.000
 HYY  C18  C17  O16  124.53  3.000
 HYY  H21  C18  C19  118.54  3.000
 HYY  H21  C18  C17  121.77  3.000
 HYY  C19  C18  C17  119.69  3.000
 HYY  H22  C19  C20  119.95  3.000
 HYY  H22  C19  C18  119.04  3.000
 HYY  C20  C19  C18  121.00  3.000
 HYY  N23  C20  C21  119.66  3.000
 HYY  C21  C20  C19  119.14  3.000
 HYY  N23  C20  C19  121.18  3.000
 HYY  H23  C21  C22  119.68  3.000
 HYY  H23  C21  C20  119.99  3.000
 HYY  C22  C21  C20  120.33  3.000
 HYY  H24  C22  C21  120.07  3.000
 HYY  H24  C22  C17  119.39  3.000
 HYY  C21  C22  C17  120.53  3.000
 HYY  H25  N23  S24  111.67  3.000
 HYY  H25  N23  C20  115.01  3.000
 HYY  S24  N23  C20  119.03  3.000
 HYY  O27  S24  O26  119.73  3.000
 HYY  O27  S24  C25  108.07  3.000
 HYY  O26  S24  C25  108.69  3.000
 HYY  C25  S24  N23  106.54  3.000
 HYY  O27  S24  N23  107.18  3.000
 HYY  O26  S24  N23  105.91  3.000
 HYY  H28  C25  H27  109.74  3.000
 HYY  H28  C25  H26  110.41  3.000
 HYY  H27  C25  H26  110.02  3.000
 HYY  H28  C25  S24  109.53  3.000
 HYY  H27  C25  S24  107.85  3.000
 HYY  H26  C25  S24  109.24  3.000
 HYY  H29  O28  C14  108.52  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
 HYY  CONST_01  C04  C05  C06  C01     0.00   0.0  0
 HYY  CONST_02  C04  C03  C02  C01     0.00   0.0  0
 HYY  CONST_03  C05  C04  C03  C02     0.00   0.0  0
 HYY  CONST_04  C05  C06  C01  C02     0.00   0.0  0
 HYY  CONST_05  C06  C05  C04  C03     0.00   0.0  0
 HYY  CONST_06  C06  C01  C02  C03     0.00   0.0  0
 HYY  CONST_07  C20  C19  C18  C17     0.00   0.0  0
 HYY  CONST_08  C20  C21  C22  C17     0.00   0.0  0
 HYY  CONST_09  C21  C20  C19  C18     0.00   0.0  0
 HYY  CONST_10  C21  C22  C17  C18     0.00   0.0  0
 HYY  CONST_11  C22  C17  C18  C19     0.00   0.0  0
 HYY  CONST_12  C22  C21  C20  C19     0.00   0.0  0
 HYY  CONST_13  CL2  C03  C02  C01   180.00   0.0  0
 HYY  CONST_14  CL1  C04  C03  C02   180.00   0.0  0
 HYY  CONST_15  C07  C06  C01  C02   180.00   0.0  0
 HYY  CONST_16  C07  C06  C05  C04   180.00   0.0  0
 HYY  CONST_17  CL2  C03  C04  C05   180.00   0.0  0
 HYY  CONST_18  CL1  C04  C05  C06   180.00   0.0  0
 HYY  CONST_19  C19  C18  C17  O16   180.00   0.0  0
 HYY  CONST_20  C21  C22  C17  O16   180.00   0.0  0
 HYY  CONST_21  N23  C20  C19  C18   180.00   0.0  0
 HYY  CONST_22  N23  C20  C21  C22   180.00   0.0  0
 HYY  CONST_23  H3   C05  C06  C01   180.00   0.0  0
 HYY  CONST_24  H1   C01  C02  C03   180.00   0.0  0
 HYY  CONST_25  H2   C02  C03  C04   180.00   0.0  0
 HYY  CONST_26  H22  C19  C18  C17   180.00   0.0  0
 HYY  CONST_27  H23  C21  C22  C17   180.00   0.0  0
 HYY  CONST_28  H24  C22  C17  C18   180.00   0.0  0
 HYY  CONST_29  H21  C18  C19  C20   180.00   0.0  0
 HYY  Var_01    C08  C07  C06  C01   -80.13  30.0  2
 HYY  Var_02    C18  C17  O16  C15     0.58  30.0  2
 HYY  Var_03    N09  C08  C07  C06  -172.98  30.0  3
 HYY  Var_04    O26  S24  N23  C20  -178.46  30.0  3
 HYY  Var_05    H19  C15  O16  C17    63.73  30.0  3
 HYY  Var_06    C13  N09  C08  C07   170.04  30.0  2
 HYY  Var_07    C14  C13  N09  C08  -156.58  30.0  3
 HYY  Var_08    C11  C10  N09  C08   -60.35  30.0  3
 HYY  Var_09    C12  C11  C10  N09  -179.56  30.0  1
 HYY  Var_10    H13  C12  C11  C10  -179.03  30.0  3
 HYY  Var_11    H26  C25  S24  N23    61.05  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
 HYY  chir_01  C14  O28  C15  C13  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
 HYY  plan-1  C01  0.020
 HYY  plan-1  C02  0.020
 HYY  plan-1  C03  0.020
 HYY  plan-1  C04  0.020
 HYY  plan-1  C05  0.020
 HYY  plan-1  C06  0.020
 HYY  plan-1  C07  0.020
 HYY  plan-1  CL1  0.020
 HYY  plan-1  CL2  0.020
 HYY  plan-1  H1   0.020
 HYY  plan-1  H2   0.020
 HYY  plan-1  H3   0.020
 HYY  plan-2  O16  0.020
 HYY  plan-2  C17  0.020
 HYY  plan-2  C18  0.020
 HYY  plan-2  C19  0.020
 HYY  plan-2  C20  0.020
 HYY  plan-2  C21  0.020
 HYY  plan-2  C22  0.020
 HYY  plan-2  N23  0.020
 HYY  plan-2  H21  0.020
 HYY  plan-2  H22  0.020
 HYY  plan-2  H23  0.020
 HYY  plan-2  H24  0.020
 HYY  plan-3  C20  0.020
 HYY  plan-3  N23  0.020
 HYY  plan-3  S24  0.020
 HYY  plan-3  H25  0.020

