# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu May  7 09:31:47 2020
#   Inital geometry file: a 155 line input string
#   Ligand name: (2S)-4-{4-[4-(benzyloxy)-2-fluorophenyl]-2-oxopyridin-1(2H)-yl}-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@](CCN1C=CC(=CC1=O)c2ccc(OCc3ccccc3)cc2F)(C(=O)NO)[S](C)(=O)=O
#
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
 HUM  HUM  (2S)-4-{4-[4-(benzyloxy)-2-fluorophenyl]-2-oxopyridin-1(2H)-yl}-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide  ligand  59  34  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_HUM
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
 HUM  C10  C  CR6   0   0.592    1.4703   0.8765  -0.9167
 HUM  C12  C  CR6   0  -0.168   -2.1522   0.5055   0.1772
 HUM  C13  C  CR6   0   0.547   -3.0515   1.3199   0.8586
 HUM  C15  C  CR16  0  -0.499   -4.4137   1.1419   0.8175
 HUM  C16  C  CR6   0   0.406   -4.9379   0.0901   0.0628
 HUM  C01  C  CH3   0  -0.722    6.1476   0.2734   1.7479
 HUM  C02  C  CT    0  -0.414    5.6702  -0.3126   0.4200
 HUM  C03  C  CH2   0  -0.445    4.1431  -0.2553   0.2800
 HUM  C06  C  CR16  0   0.067    1.3200   0.9848   1.4826
 HUM  C07  C  CR16  0  -0.442   -0.0271   0.8513   1.4805
 HUM  C08  C  CR6   0   0.230   -0.6942   0.7131   0.2341
 HUM  C09  C  CR16  0  -0.517    0.0424   0.7315  -0.9150
 HUM  C18  C  CH2   0  -0.275   -6.8701  -1.1096  -0.6387
 HUM  C19  C  CR6   0   0.100   -8.3500  -1.0229  -0.4240
 HUM  C20  C  CR16  0  -0.286   -8.9163  -1.4906   0.7593
 HUM  C21  C  CR16  0  -0.242  -10.2834  -1.3910   0.9723
 HUM  C22  C  CR16  0  -0.261  -11.0994  -0.8214   0.0020
 HUM  C23  C  CR16  0  -0.241  -10.5425  -0.3531  -1.1801
 HUM  C24  C  CR16  0  -0.297   -9.1727  -0.4515  -1.3887
 HUM  C25  C  CR16  0  -0.383   -4.0729  -0.7474  -0.6399
 HUM  C26  C  CR16  0  -0.257   -2.7059  -0.5249  -0.5767
 HUM  C27  C  C     0   0.596    6.0952  -1.7676   0.1645
 HUM  F14  F  F     0  -0.303   -2.5735   2.3485   1.5739
 HUM  N05  N  NR6   0  -0.512    2.0502   1.0074   0.3400
 HUM  N29  N  NH1   0  -0.366    6.8699  -2.3161   1.1051
 HUM  O11  O  O     0  -0.515    2.1674   0.8940  -1.9307
 HUM  O17  O  O2    0  -0.462   -6.2732  -0.0300   0.0755
 HUM  O28  O  O     0  -0.460    5.7393  -2.3568  -0.8396
 HUM  O30  O  OH1   0  -0.534    7.1884  -3.6345   1.0262
 HUM  S31  S  S     0   1.217    6.5328   0.6609  -0.8880
 HUM  H1   H  HCR6  0   0.289   -5.0699   1.8121   1.3582
 HUM  H2   H  HCH3  0   0.291    5.8499   1.3127   1.8557
 HUM  H3   H  HCH3  0   0.283    5.6918  -0.2771   2.5716
 HUM  H4   H  HCH3  0   0.274    7.2311   0.2399   1.8600
 HUM  H5   H  HCH2  0   0.289    3.8429  -0.7030  -0.6663
 HUM  H6   H  HCH2  0   0.291    3.7430  -0.8995   1.0688
 HUM  H7   H  HCH2  0   0.279    3.7406   1.5737   1.3826
 HUM  H8   H  HCH2  0   0.276    3.8325   1.8176  -0.3470
 HUM  H9   H  HCR6  0   0.311    1.8796   1.0803   2.4023
 HUM  H10  H  HCR6  0   0.274   -0.5566   0.8182   2.4201
 HUM  H11  H  HCR6  0   0.271   -0.4346   0.6422  -1.8823
 HUM  H12  H  HCH2  0   0.248   -6.4806  -2.0634  -0.2687
 HUM  H13  H  HCH2  0   0.249   -6.6304  -1.0388  -1.7044
 HUM  H14  H  HCR6  0   0.255   -8.2870  -1.9439   1.5163
 HUM  H15  H  HCR6  0   0.259  -10.7134  -1.7625   1.8932
 HUM  H16  H  HCR6  0   0.259  -12.1666  -0.7472   0.1666
 HUM  H17  H  HCR6  0   0.259  -11.1726   0.0881  -1.9415
 HUM  H18  H  HCR6  0   0.256   -8.7420  -0.0842  -2.3124
 HUM  H19  H  HCR6  0   0.291   -4.4373  -1.5763  -1.2295
 HUM  H20  H  HCR6  0   0.275   -2.0453  -1.1901  -1.1178
 HUM  H21  H  HCH3  0   0.297    4.6721   0.6466  -2.3784
 HUM  H22  H  HCH3  0   0.315    6.2341   0.9729  -3.1666
 HUM  H23  H  HCH3  0   0.302    5.8050  -0.6970  -2.7056
 HUM  H24  H  HNH1  0   0.437    7.1028  -1.8772   1.9826
 HUM  H25  H  HOH1  0   0.482    8.0355  -3.6826   0.5625
 HUM  C04  C  CH2   0  -0.330    3.5015   1.1241   0.4210
 HUM  C32  C  CH3   0  -0.800    5.7165   0.3503  -2.4373
 HUM  O33  O  OS    0  -0.665    6.3583   2.0808  -0.5757
 HUM  O34  O  OS    0  -0.669    7.8997   0.1428  -0.9534

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
 HUM  O30  N29  single    1.359  0.020  1.359
 HUM  N29  C27  single    1.336  0.020  1.336
 HUM  O28  C27  double    1.217  0.020  1.217
 HUM  C27  C02  single    1.537  0.020  1.537
 HUM  O34  S31  double    1.463  0.020  1.463
 HUM  O33  S31  double    1.464  0.020  1.464
 HUM  C04  N05  single    1.458  0.020  1.458
 HUM  C04  C03  single    1.528  0.020  1.528
 HUM  C02  S31  single    1.845  0.020  1.845
 HUM  C02  C03  single    1.535  0.020  1.535
 HUM  C02  C01  single    1.528  0.020  1.528
 HUM  S31  C32  single    1.778  0.020  1.778
 HUM  N05  C06  single    1.356  0.020  1.356
 HUM  N05  C10  single    1.390  0.020  1.390
 HUM  C06  C07  double    1.354  0.020  1.354
 HUM  O11  C10  double    1.231  0.020  1.231
 HUM  C10  C09  single    1.435  0.020  1.435
 HUM  F14  C13  single    1.341  0.020  1.341
 HUM  C07  C08  single    1.420  0.020  1.420
 HUM  C09  C08  double    1.365  0.020  1.365
 HUM  C08  C12  single    1.474  0.020  1.474
 HUM  C13  C12  aromatic  1.391  0.020  1.391
 HUM  C13  C15  aromatic  1.374  0.020  1.374
 HUM  C12  C26  aromatic  1.392  0.020  1.392
 HUM  C15  C16  aromatic  1.397  0.020  1.397
 HUM  C26  C25  aromatic  1.386  0.020  1.386
 HUM  C16  C25  aromatic  1.394  0.020  1.394
 HUM  C16  O17  single    1.341  0.020  1.341
 HUM  C18  O17  single    1.425  0.020  1.425
 HUM  C18  C19  single    1.498  0.020  1.498
 HUM  C19  C24  aromatic  1.391  0.020  1.391
 HUM  C19  C20  aromatic  1.393  0.020  1.393
 HUM  C24  C23  aromatic  1.389  0.020  1.389
 HUM  C20  C21  aromatic  1.387  0.020  1.387
 HUM  C23  C22  aromatic  1.388  0.020  1.388
 HUM  C21  C22  aromatic  1.390  0.020  1.390
 HUM  C15  H1   single    0.930  0.020  1.080
 HUM  C01  H2   single    0.970  0.020  1.090
 HUM  C01  H3   single    0.970  0.020  1.090
 HUM  C01  H4   single    0.970  0.020  1.090
 HUM  C03  H5   single    0.970  0.020  1.090
 HUM  C03  H6   single    0.970  0.020  1.090
 HUM  C04  H7   single    0.970  0.020  1.090
 HUM  C04  H8   single    0.970  0.020  1.090
 HUM  C06  H9   single    0.930  0.020  1.080
 HUM  C07  H10  single    0.930  0.020  1.080
 HUM  C09  H11  single    0.930  0.020  1.080
 HUM  C18  H12  single    0.970  0.020  1.090
 HUM  C18  H13  single    0.970  0.020  1.090
 HUM  C20  H14  single    0.930  0.020  1.080
 HUM  C21  H15  single    0.930  0.020  1.080
 HUM  C22  H16  single    0.930  0.020  1.080
 HUM  C23  H17  single    0.930  0.020  1.080
 HUM  C24  H18  single    0.930  0.020  1.080
 HUM  C25  H19  single    0.930  0.020  1.080
 HUM  C26  H20  single    0.930  0.020  1.080
 HUM  C32  H21  single    0.970  0.020  1.090
 HUM  C32  H22  single    0.970  0.020  1.090
 HUM  C32  H23  single    0.970  0.020  1.090
 HUM  N29  H24  single    0.860  0.020  1.020
 HUM  O30  H25  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
 HUM  O11  C10  N05  120.48  3.000
 HUM  O11  C10  C09  124.47  3.000
 HUM  N05  C10  C09  115.05  3.000
 HUM  C26  C12  C08  121.25  3.000
 HUM  C26  C12  C13  116.21  3.000
 HUM  C08  C12  C13  122.55  3.000
 HUM  F14  C13  C15  117.95  3.000
 HUM  C15  C13  C12  123.37  3.000
 HUM  F14  C13  C12  118.68  3.000
 HUM  H1   C15  C16  120.57  3.000
 HUM  H1   C15  C13  120.36  3.000
 HUM  C16  C15  C13  119.06  3.000
 HUM  O17  C16  C25  124.68  3.000
 HUM  O17  C16  C15  115.86  3.000
 HUM  C25  C16  C15  119.47  3.000
 HUM  H4   C01  H3   108.80  3.000
 HUM  H4   C01  H2   106.96  3.000
 HUM  H3   C01  H2   107.06  3.000
 HUM  H4   C01  C02  112.85  3.000
 HUM  H3   C01  C02  109.40  3.000
 HUM  H2   C01  C02  111.57  3.000
 HUM  S31  C02  C27  104.62  3.000
 HUM  S31  C02  C03  112.39  3.000
 HUM  C27  C02  C03  107.18  3.000
 HUM  C03  C02  C01  112.08  3.000
 HUM  S31  C02  C01  105.53  3.000
 HUM  C27  C02  C01  114.91  3.000
 HUM  H6   C03  H5   106.47  3.000
 HUM  H6   C03  C04  108.15  3.000
 HUM  H5   C03  C04  109.61  3.000
 HUM  H6   C03  C02  106.02  3.000
 HUM  H5   C03  C02  109.77  3.000
 HUM  C04  C03  C02  116.31  3.000
 HUM  H9   C06  N05  115.90  3.000
 HUM  H9   C06  C07  121.68  3.000
 HUM  N05  C06  C07  122.42  3.000
 HUM  H10  C07  C08  122.05  3.000
 HUM  H10  C07  C06  119.34  3.000
 HUM  C08  C07  C06  118.57  3.000
 HUM  C09  C08  C07  118.94  3.000
 HUM  C09  C08  C12  120.22  3.000
 HUM  C07  C08  C12  120.81  3.000
 HUM  H11  C09  C08  120.89  3.000
 HUM  H11  C09  C10  116.48  3.000
 HUM  C08  C09  C10  122.63  3.000
 HUM  H13  C18  H12  107.92  3.000
 HUM  H13  C18  O17  110.31  3.000
 HUM  H12  C18  O17  109.97  3.000
 HUM  H13  C18  C19  110.62  3.000
 HUM  H12  C18  C19  110.70  3.000
 HUM  O17  C18  C19  107.33  3.000
 HUM  C24  C19  C20  119.13  3.000
 HUM  C20  C19  C18  120.27  3.000
 HUM  C24  C19  C18  120.59  3.000
 HUM  H14  C20  C21  119.67  3.000
 HUM  H14  C20  C19  119.86  3.000
 HUM  C21  C20  C19  120.47  3.000
 HUM  H15  C21  C22  120.11  3.000
 HUM  H15  C21  C20  119.84  3.000
 HUM  C22  C21  C20  120.05  3.000
 HUM  H16  C22  C23  120.13  3.000
 HUM  H16  C22  C21  120.05  3.000
 HUM  C23  C22  C21  119.82  3.000
 HUM  H17  C23  C24  119.82  3.000
 HUM  H17  C23  C22  120.20  3.000
 HUM  C24  C23  C22  119.98  3.000
 HUM  H18  C24  C23  119.74  3.000
 HUM  H18  C24  C19  119.71  3.000
 HUM  C23  C24  C19  120.55  3.000
 HUM  H19  C25  C26  118.72  3.000
 HUM  H19  C25  C16  121.78  3.000
 HUM  C26  C25  C16  119.50  3.000
 HUM  H20  C26  C25  118.70  3.000
 HUM  H20  C26  C12  118.89  3.000
 HUM  C25  C26  C12  122.40  3.000
 HUM  O28  C27  N29  123.46  3.000
 HUM  O28  C27  C02  120.96  3.000
 HUM  N29  C27  C02  115.58  3.000
 HUM  C06  N05  C04  119.36  3.000
 HUM  C06  N05  C10  122.37  3.000
 HUM  C04  N05  C10  118.22  3.000
 HUM  H24  N29  O30  114.75  3.000
 HUM  H24  N29  C27  124.59  3.000
 HUM  O30  N29  C27  119.56  3.000
 HUM  C18  O17  C16  118.69  3.000
 HUM  H25  O30  N29  106.35  3.000
 HUM  O34  S31  O33  117.66  3.000
 HUM  O33  S31  C32  107.49  3.000
 HUM  O34  S31  C32  109.15  3.000
 HUM  C32  S31  C02  108.12  3.000
 HUM  O33  S31  C02  107.74  3.000
 HUM  O34  S31  C02  106.36  3.000
 HUM  H8   C04  H7   107.10  3.000
 HUM  H8   C04  N05  108.36  3.000
 HUM  H7   C04  N05  107.51  3.000
 HUM  H8   C04  C03  112.53  3.000
 HUM  H7   C04  C03  111.24  3.000
 HUM  N05  C04  C03  109.91  3.000
 HUM  H23  C32  H22  110.33  3.000
 HUM  H23  C32  H21  110.79  3.000
 HUM  H22  C32  H21  109.68  3.000
 HUM  H23  C32  S31  110.28  3.000
 HUM  H22  C32  S31  105.38  3.000
 HUM  H21  C32  S31  110.25  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
 HUM  CONST_01  C16  C15  C13  C12     0.00   0.0  0
 HUM  CONST_02  C16  C25  C26  C12     0.00   0.0  0
 HUM  CONST_03  C25  C26  C12  C13     0.00   0.0  0
 HUM  CONST_04  C25  C16  C15  C13     0.00   0.0  0
 HUM  CONST_05  C26  C12  C13  C15     0.00   0.0  0
 HUM  CONST_06  C26  C25  C16  C15     0.00   0.0  0
 HUM  CONST_07  C22  C23  C24  C19     0.00   0.0  0
 HUM  CONST_08  C22  C21  C20  C19     0.00   0.0  0
 HUM  CONST_09  C23  C24  C19  C20     0.00   0.0  0
 HUM  CONST_10  C23  C22  C21  C20     0.00   0.0  0
 HUM  CONST_11  C24  C19  C20  C21     0.00   0.0  0
 HUM  CONST_12  C24  C23  C22  C21     0.00   0.0  0
 HUM  CONST_13  C08  C12  C13  C15   180.00   0.0  0
 HUM  CONST_14  C25  C26  C12  C08   180.00   0.0  0
 HUM  CONST_15  C09  C10  N05  C06     0.00   0.0  0
 HUM  CONST_16  O17  C16  C15  C13   180.00   0.0  0
 HUM  CONST_17  F14  C13  C15  C16   180.00   0.0  0
 HUM  CONST_18  F14  C13  C12  C08     0.00   0.0  0
 HUM  CONST_19  C23  C24  C19  C18   180.00   0.0  0
 HUM  CONST_20  C21  C20  C19  C18   180.00   0.0  0
 HUM  CONST_21  F14  C13  C12  C26   180.00   0.0  0
 HUM  CONST_22  O17  C16  C25  C26   180.00   0.0  0
 HUM  CONST_23  C09  C10  N05  C04   180.00   0.0  0
 HUM  CONST_24  O11  C10  N05  C06   180.00   0.0  0
 HUM  CONST_25  H1   C15  C13  C12   180.00   0.0  0
 HUM  CONST_26  H19  C25  C26  C12   180.00   0.0  0
 HUM  CONST_27  H20  C26  C12  C13   180.00   0.0  0
 HUM  CONST_28  H17  C23  C24  C19   180.00   0.0  0
 HUM  CONST_29  H15  C21  C20  C19   180.00   0.0  0
 HUM  CONST_30  H18  C24  C19  C20   180.00   0.0  0
 HUM  CONST_31  H16  C22  C21  C20   180.00   0.0  0
 HUM  CONST_32  H14  C20  C21  C22   180.00   0.0  0
 HUM  CONST_33  O11  C10  N05  C04     0.00   0.0  0
 HUM  CONST_34  O30  N29  C27  C02   180.00   0.0  0
 HUM  CONST_35  O30  N29  C27  O28     0.00   0.0  0
 HUM  CONST_36  H24  N29  C27  C02     0.00   0.0  0
 HUM  Var_01    C07  C08  C12  C13    50.68  30.0  2
 HUM  Var_02    C03  C04  N05  C10   -79.27  30.0  2
 HUM  Var_03    C19  C18  O17  C16   178.48  30.0  1
 HUM  Var_04    C25  C16  O17  C18     2.13  30.0  2
 HUM  Var_05    O17  C18  C19  C20   -79.43  30.0  2
 HUM  Var_06    N05  C04  C03  C02  -176.82  30.0  1
 HUM  Var_07    H21  C32  S31  C02    59.59  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
 HUM  chir_01  C02  S31  C03  C01  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
 HUM  plan-1  C12  0.020
 HUM  plan-1  C13  0.020
 HUM  plan-1  C15  0.020
 HUM  plan-1  C16  0.020
 HUM  plan-1  C08  0.020
 HUM  plan-1  C25  0.020
 HUM  plan-1  C26  0.020
 HUM  plan-1  F14  0.020
 HUM  plan-1  O17  0.020
 HUM  plan-1  H1   0.020
 HUM  plan-1  H19  0.020
 HUM  plan-1  H20  0.020
 HUM  plan-2  C18  0.020
 HUM  plan-2  C19  0.020
 HUM  plan-2  C20  0.020
 HUM  plan-2  C21  0.020
 HUM  plan-2  C22  0.020
 HUM  plan-2  C23  0.020
 HUM  plan-2  C24  0.020
 HUM  plan-2  H14  0.020
 HUM  plan-2  H15  0.020
 HUM  plan-2  H16  0.020
 HUM  plan-2  H17  0.020
 HUM  plan-2  H18  0.020
 HUM  plan-3  C10  0.020
 HUM  plan-3  C12  0.020
 HUM  plan-3  C06  0.020
 HUM  plan-3  C07  0.020
 HUM  plan-3  C08  0.020
 HUM  plan-3  C09  0.020
 HUM  plan-3  N05  0.020
 HUM  plan-3  O11  0.020
 HUM  plan-3  H9   0.020
 HUM  plan-3  H10  0.020
 HUM  plan-3  H11  0.020
 HUM  plan-3  C04  0.020
 HUM  plan-4  C02  0.020
 HUM  plan-4  C27  0.020
 HUM  plan-4  N29  0.020
 HUM  plan-4  O28  0.020
 HUM  plan-4  O30  0.020
 HUM  plan-4  H24  0.020

