# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Jun 10 11:14:05 2020
#   Inital geometry file: a 141 line input string
#   Ligand name: pentyl (3,5-dihydroxy-2-nonanoylphenyl)acetate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCCCCCC(=O)c1c(O)cc(O)cc1CC(=O)OCCCCC
#
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
 ZHN  ZHN  'pentyl (3,5-dihydroxy-2-nonanoylphenyl)acetate'  ligand  61  27  .  2021-08-25  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_ZHN
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
 ZHN  O28  O  O     0  -0.449  -3.6200  -0.1176  -0.8491
 ZHN  C20  C  C     0   0.622  -3.1491   0.2258   0.2049
 ZHN  O27  O  O2    0  -0.459  -3.0548   1.4849   0.6018
 ZHN  C22  C  CH2   0  -0.159  -3.4877   2.5165  -0.2951
 ZHN  C23  C  CH2   0  -0.463  -3.3708   3.8386   0.4325
 ZHN  C24  C  CH2   0  -0.420  -3.7254   5.0117  -0.4735
 ZHN  C25  C  CH2   0  -0.418  -3.6560   6.3516   0.2492
 ZHN  C26  C  CH3   0  -0.662  -3.9664   7.5303  -0.6620
 ZHN  C19  C  CH2   0  -0.712  -2.6622  -0.7218   1.2753
 ZHN  C4   C  CR6   0   0.175  -2.2416  -2.0484   0.7084
 ZHN  C3   C  CR16  0  -0.430  -3.1127  -3.1169   0.8181
 ZHN  C2   C  CR6   0   0.397  -2.7655  -4.3628   0.2968
 ZHN  O8   O  OH1   0  -0.624  -3.6545  -5.3586   0.4258
 ZHN  C5   C  CR6   0  -0.178  -0.9839  -2.2156   0.1096
 ZHN  C6   C  CR6   0   0.385  -0.6607  -3.4665  -0.4287
 ZHN  O7   O  OH1   0  -0.622   0.5092  -3.5814  -1.0782
 ZHN  C1   C  CR16  0  -0.523  -1.5432  -4.5367  -0.3373
 ZHN  C9   C  C     0   0.380  -0.0403  -1.0699   0.0014
 ZHN  O18  O  O     0  -0.399  -0.4262   0.0018  -0.4208
 ZHN  C10  C  CH2   0  -0.558   1.3577  -1.2249   0.5495
 ZHN  C11  C  CH2   0  -0.421   2.4212  -0.4461  -0.2143
 ZHN  C12  C  CH2   0  -0.416   3.7672  -0.4487   0.4985
 ZHN  C13  C  CH2   0  -0.412   4.8370   0.3247  -0.2616
 ZHN  C14  C  CH2   0  -0.412   6.1578   0.4278   0.4901
 ZHN  C15  C  CH2   0  -0.406   7.2203   1.2103  -0.2707
 ZHN  C16  C  CH2   0  -0.419   8.5252   1.3683   0.5001
 ZHN  C17  C  CH3   0  -0.663   9.5745   2.1554  -0.2725
 ZHN  H1   H  HCH2  0   0.228  -2.8575   2.5070  -1.1886
 ZHN  H2   H  HCH2  0   0.231  -4.5185   2.3345  -0.6084
 ZHN  H3   H  HCH2  0   0.229  -4.0310   3.8341   1.3050
 ZHN  H4   H  HCH2  0   0.229  -2.3496   3.9635   0.8043
 ZHN  H5   H  HCH2  0   0.215  -3.0451   5.0277  -1.3317
 ZHN  H6   H  HCH2  0   0.216  -4.7316   4.8732  -0.8834
 ZHN  H7   H  HCH2  0   0.214  -4.3552   6.3447   1.0907
 ZHN  H8   H  HCH2  0   0.213  -2.6595   6.4765   0.6837
 ZHN  H9   H  HCH3  0   0.217  -4.9643   7.4428  -1.0960
 ZHN  H10  H  HCH3  0   0.228  -3.9254   8.4758  -0.1201
 ZHN  H11  H  HCH3  0   0.217  -3.2538   7.5913  -1.4867
 ZHN  H12  H  HCH2  0   0.288  -1.8693  -0.2519   1.8583
 ZHN  H13  H  HCH2  0   0.312  -3.4934  -0.8721   1.9711
 ZHN  H14  H  HCR6  0   0.263  -4.0707  -2.9929   1.3079
 ZHN  H15  H  HOH1  0   0.479  -3.3184  -6.1714   0.0305
 ZHN  H16  H  HOH1  0   0.482   0.6401  -4.4843  -1.3906
 ZHN  H17  H  HCR6  0   0.289  -1.2798  -5.4963  -0.7707
 ZHN  H18  H  HCH2  0   0.270   1.2899  -0.8455   1.5784
 ZHN  H19  H  HCH2  0   0.259   1.6357  -2.2733   0.6453
 ZHN  H20  H  HCH2  0   0.224   2.5343  -0.8747  -1.2150
 ZHN  H21  H  HCH2  0   0.224   2.0922   0.5862  -0.3542
 ZHN  H22  H  HCH2  0   0.210   3.6434  -0.0121   1.4959
 ZHN  H23  H  HCH2  0   0.212   4.1035  -1.4787   0.6582
 ZHN  H24  H  HCH2  0   0.209   5.0072  -0.1482  -1.2352
 ZHN  H25  H  HCH2  0   0.207   4.4667   1.3332  -0.4779
 ZHN  H26  H  HCH2  0   0.206   5.9816   0.9053   1.4607
 ZHN  H27  H  HCH2  0   0.208   6.5346  -0.5767   0.7128
 ZHN  H28  H  HCH2  0   0.206   7.4224   0.7153  -1.2274
 ZHN  H29  H  HCH2  0   0.205   6.8283   2.2023  -0.5229
 ZHN  H30  H  HCH2  0   0.210   8.3211   1.8653   1.4537
 ZHN  H31  H  HCH2  0   0.210   8.9203   0.3795   0.7534
 ZHN  H32  H  HCH3  0   0.226  10.4966   2.2674   0.2990
 ZHN  H33  H  HCH3  0   0.216   9.8261   1.6590  -1.2116
 ZHN  H34  H  HCH3  0   0.216   9.2134   3.1560  -0.5179

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
 ZHN  C16  C17  single    1.522  0.020  1.522
 ZHN  C16  C15  single    1.524  0.020  1.524
 ZHN  C13  C14  single    1.523  0.020  1.523
 ZHN  C13  C12  single    1.523  0.020  1.523
 ZHN  C14  C15  single    1.523  0.020  1.523
 ZHN  C12  C11  single    1.523  0.020  1.523
 ZHN  C11  C10  single    1.523  0.020  1.523
 ZHN  C10  C9   single    1.510  0.020  1.510
 ZHN  C19  C4   single    1.503  0.020  1.503
 ZHN  C19  C20  single    1.510  0.020  1.510
 ZHN  C24  C25  single    1.524  0.020  1.524
 ZHN  C24  C23  single    1.524  0.020  1.524
 ZHN  C3   C4   aromatic  1.383  0.020  1.383
 ZHN  C3   C2   aromatic  1.395  0.020  1.395
 ZHN  C4   C5   aromatic  1.403  0.020  1.403
 ZHN  C22  O27  single    1.434  0.020  1.434
 ZHN  C22  C23  single    1.514  0.020  1.514
 ZHN  O8   C2   single    1.341  0.020  1.341
 ZHN  C2   C1   aromatic  1.388  0.020  1.388
 ZHN  C5   C9   single    1.488  0.020  1.488
 ZHN  C5   C6   aromatic  1.400  0.020  1.400
 ZHN  C25  C26  single    1.522  0.020  1.522
 ZHN  C9   O18  double    1.215  0.020  1.215
 ZHN  O27  C20  single    1.324  0.020  1.324
 ZHN  C1   C6   aromatic  1.390  0.020  1.390
 ZHN  C6   O7   single    1.343  0.020  1.343
 ZHN  C20  O28  double    1.204  0.020  1.204
 ZHN  C22  H1   single    0.970  0.020  1.090
 ZHN  C22  H2   single    0.970  0.020  1.090
 ZHN  C23  H3   single    0.970  0.020  1.090
 ZHN  C23  H4   single    0.970  0.020  1.090
 ZHN  C24  H5   single    0.970  0.020  1.090
 ZHN  C24  H6   single    0.970  0.020  1.090
 ZHN  C25  H7   single    0.970  0.020  1.090
 ZHN  C25  H8   single    0.970  0.020  1.090
 ZHN  C26  H9   single    0.970  0.020  1.090
 ZHN  C26  H10  single    0.970  0.020  1.090
 ZHN  C26  H11  single    0.970  0.020  1.090
 ZHN  C19  H12  single    0.970  0.020  1.090
 ZHN  C19  H13  single    0.970  0.020  1.090
 ZHN  C3   H14  single    0.930  0.020  1.080
 ZHN  O8   H15  single    0.850  0.020  0.980
 ZHN  O7   H16  single    0.850  0.020  0.980
 ZHN  C1   H17  single    0.930  0.020  1.080
 ZHN  C10  H18  single    0.970  0.020  1.090
 ZHN  C10  H19  single    0.970  0.020  1.090
 ZHN  C11  H20  single    0.970  0.020  1.090
 ZHN  C11  H21  single    0.970  0.020  1.090
 ZHN  C12  H22  single    0.970  0.020  1.090
 ZHN  C12  H23  single    0.970  0.020  1.090
 ZHN  C13  H24  single    0.970  0.020  1.090
 ZHN  C13  H25  single    0.970  0.020  1.090
 ZHN  C14  H26  single    0.970  0.020  1.090
 ZHN  C14  H27  single    0.970  0.020  1.090
 ZHN  C15  H28  single    0.970  0.020  1.090
 ZHN  C15  H29  single    0.970  0.020  1.090
 ZHN  C16  H30  single    0.970  0.020  1.090
 ZHN  C16  H31  single    0.970  0.020  1.090
 ZHN  C17  H32  single    0.970  0.020  1.090
 ZHN  C17  H33  single    0.970  0.020  1.090
 ZHN  C17  H34  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
 ZHN  C19  C20  O27  111.18  3.000
 ZHN  O27  C20  O28  124.16  3.000
 ZHN  C19  C20  O28  124.57  3.000
 ZHN  C22  O27  C20  118.38  3.000
 ZHN  H2   C22  H1   107.94  3.000
 ZHN  H2   C22  C23  110.87  3.000
 ZHN  H1   C22  C23  110.85  3.000
 ZHN  H2   C22  O27  110.14  3.000
 ZHN  H1   C22  O27  109.33  3.000
 ZHN  C23  C22  O27  107.73  3.000
 ZHN  H4   C23  H3   107.02  3.000
 ZHN  H4   C23  C24  109.36  3.000
 ZHN  H3   C23  C24  109.68  3.000
 ZHN  H4   C23  C22  109.58  3.000
 ZHN  H3   C23  C22  109.45  3.000
 ZHN  C24  C23  C22  111.63  3.000
 ZHN  H6   C24  H5   106.22  3.000
 ZHN  H6   C24  C25  109.30  3.000
 ZHN  H5   C24  C25  109.29  3.000
 ZHN  H6   C24  C23  109.81  3.000
 ZHN  H5   C24  C23  109.42  3.000
 ZHN  C25  C24  C23  112.60  3.000
 ZHN  H8   C25  H7   106.09  3.000
 ZHN  H8   C25  C26  109.58  3.000
 ZHN  H7   C25  C26  109.57  3.000
 ZHN  H8   C25  C24  109.28  3.000
 ZHN  H7   C25  C24  109.27  3.000
 ZHN  C26  C25  C24  112.82  3.000
 ZHN  H11  C26  H10  107.60  3.000
 ZHN  H11  C26  H9   107.51  3.000
 ZHN  H10  C26  H9   107.54  3.000
 ZHN  H11  C26  C25  111.25  3.000
 ZHN  H10  C26  C25  111.48  3.000
 ZHN  H9   C26  C25  111.25  3.000
 ZHN  H13  C19  H12  105.75  3.000
 ZHN  H13  C19  C4   109.34  3.000
 ZHN  H12  C19  C4   112.24  3.000
 ZHN  H13  C19  C20  106.98  3.000
 ZHN  H12  C19  C20  110.06  3.000
 ZHN  C4   C19  C20  112.13  3.000
 ZHN  C5   C4   C3   120.43  3.000
 ZHN  C5   C4   C19  121.14  3.000
 ZHN  C3   C4   C19  118.42  3.000
 ZHN  H14  C3   C2   119.45  3.000
 ZHN  H14  C3   C4   120.30  3.000
 ZHN  C2   C3   C4   120.25  3.000
 ZHN  C1   C2   O8   122.32  3.000
 ZHN  C1   C2   C3   120.14  3.000
 ZHN  O8   C2   C3   117.54  3.000
 ZHN  H15  O8   C2   110.82  3.000
 ZHN  C9   C5   C6   120.91  3.000
 ZHN  C6   C5   C4   118.53  3.000
 ZHN  C9   C5   C4   120.51  3.000
 ZHN  C1   C6   O7   121.26  3.000
 ZHN  O7   C6   C5   117.62  3.000
 ZHN  C1   C6   C5   121.08  3.000
 ZHN  H16  O7   C6   110.80  3.000
 ZHN  H17  C1   C6   120.02  3.000
 ZHN  H17  C1   C2   120.46  3.000
 ZHN  C6   C1   C2   119.51  3.000
 ZHN  C10  C9   O18  120.73  3.000
 ZHN  O18  C9   C5   120.20  3.000
 ZHN  C10  C9   C5   118.80  3.000
 ZHN  H19  C10  H18  105.42  3.000
 ZHN  H19  C10  C11  110.99  3.000
 ZHN  H18  C10  C11  109.63  3.000
 ZHN  H19  C10  C9   111.55  3.000
 ZHN  H18  C10  C9   104.32  3.000
 ZHN  C11  C10  C9   114.33  3.000
 ZHN  H21  C11  H20  106.51  3.000
 ZHN  H21  C11  C12  109.13  3.000
 ZHN  H20  C11  C12  109.62  3.000
 ZHN  H21  C11  C10  109.70  3.000
 ZHN  H20  C11  C10  109.29  3.000
 ZHN  C12  C11  C10  112.42  3.000
 ZHN  H23  C12  H22  106.05  3.000
 ZHN  H23  C12  C13  109.55  3.000
 ZHN  H22  C12  C13  109.35  3.000
 ZHN  H23  C12  C11  109.95  3.000
 ZHN  H22  C12  C11  108.99  3.000
 ZHN  C13  C12  C11  112.73  3.000
 ZHN  H25  C13  H24  105.92  3.000
 ZHN  H25  C13  C14  109.16  3.000
 ZHN  H24  C13  C14  109.46  3.000
 ZHN  H25  C13  C12  109.17  3.000
 ZHN  H24  C13  C12  109.47  3.000
 ZHN  C14  C13  C12  113.40  3.000
 ZHN  H27  C14  H26  105.94  3.000
 ZHN  H27  C14  C15  109.43  3.000
 ZHN  H26  C14  C15  109.32  3.000
 ZHN  H27  C14  C13  109.65  3.000
 ZHN  H26  C14  C13  109.10  3.000
 ZHN  C15  C14  C13  113.15  3.000
 ZHN  H29  C15  H28  105.89  3.000
 ZHN  H29  C15  C16  109.20  3.000
 ZHN  H28  C15  C16  109.30  3.000
 ZHN  H29  C15  C14  109.29  3.000
 ZHN  H28  C15  C14  109.44  3.000
 ZHN  C16  C15  C14  113.45  3.000
 ZHN  H31  C16  H30  106.01  3.000
 ZHN  H31  C16  C17  109.62  3.000
 ZHN  H30  C16  C17  109.63  3.000
 ZHN  H31  C16  C15  109.42  3.000
 ZHN  H30  C16  C15  109.16  3.000
 ZHN  C17  C16  C15  112.78  3.000
 ZHN  H34  C17  H33  107.44  3.000
 ZHN  H34  C17  H32  107.65  3.000
 ZHN  H33  C17  H32  107.62  3.000
 ZHN  H34  C17  C16  111.10  3.000
 ZHN  H33  C17  C16  111.12  3.000
 ZHN  H32  C17  C16  111.71  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
 ZHN  CONST_01  C1   C2   C3   C4      0.00   0.0  0
 ZHN  CONST_02  C1   C6   C5   C4      0.00   0.0  0
 ZHN  CONST_03  C6   C5   C4   C3      0.00   0.0  0
 ZHN  CONST_04  C6   C1   C2   C3      0.00   0.0  0
 ZHN  CONST_05  C5   C4   C3   C2      0.00   0.0  0
 ZHN  CONST_06  C5   C6   C1   C2      0.00   0.0  0
 ZHN  CONST_07  C2   C3   C4   C19   180.00   0.0  0
 ZHN  CONST_08  C6   C5   C4   C19   180.00   0.0  0
 ZHN  CONST_09  O8   C2   C3   C4    180.00   0.0  0
 ZHN  CONST_10  O7   C6   C5   C4    180.00   0.0  0
 ZHN  CONST_11  C9   C5   C4   C3    180.00   0.0  0
 ZHN  CONST_12  O7   C6   C1   C2    180.00   0.0  0
 ZHN  CONST_13  C6   C1   C2   O8    180.00   0.0  0
 ZHN  CONST_14  C9   C5   C6   C1    180.00   0.0  0
 ZHN  CONST_15  H17  C1   C2   C3    180.00   0.0  0
 ZHN  CONST_16  H14  C3   C4   C5    180.00   0.0  0
 ZHN  Var_01    C3   C4   C19  C20  -101.23  30.0  2
 ZHN  Var_02    C10  C9   C5   C4    125.92  30.0  2
 ZHN  Var_03    C4   C19  C20  O28    25.89  30.0  1
 ZHN  Var_04    C11  C10  C9   C5    147.60  30.0  2
 ZHN  Var_05    C23  C22  O27  C20   175.90  30.0  1
 ZHN  Var_06    C24  C23  C22  O27   176.33  30.0  3
 ZHN  Var_07    C19  C20  O27  C22  -179.49  30.0  3
 ZHN  Var_08    C25  C24  C23  C22   178.26  30.0  1
 ZHN  Var_09    C26  C25  C24  C23   178.19  30.0  3
 ZHN  Var_10    C12  C11  C10  C9    170.75  30.0  2
 ZHN  Var_11    C13  C12  C11  C10   179.82  30.0  2
 ZHN  Var_12    C14  C13  C12  C11   175.33  30.0  2
 ZHN  Var_13    C15  C14  C13  C12  -179.61  30.0  3
 ZHN  Var_14    C16  C15  C14  C13   177.55  30.0  3
 ZHN  Var_15    C17  C16  C15  C14  -179.85  30.0  1
 ZHN  Var_16    H9   C26  C25  C24    59.10  30.0  3
 ZHN  Var_17    H32  C17  C16  C15   179.37  30.0  3

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
 ZHN  plan-1  C19  0.020
 ZHN  plan-1  C4   0.020
 ZHN  plan-1  C3   0.020
 ZHN  plan-1  C2   0.020
 ZHN  plan-1  O8   0.020
 ZHN  plan-1  C5   0.020
 ZHN  plan-1  C6   0.020
 ZHN  plan-1  O7   0.020
 ZHN  plan-1  C1   0.020
 ZHN  plan-1  C9   0.020
 ZHN  plan-1  H14  0.020
 ZHN  plan-1  H17  0.020
 ZHN  plan-2  C5   0.020
 ZHN  plan-2  C9   0.020
 ZHN  plan-2  O18  0.020
 ZHN  plan-2  C10  0.020
 ZHN  plan-3  O28  0.020
 ZHN  plan-3  C20  0.020
 ZHN  plan-3  O27  0.020
 ZHN  plan-3  C19  0.020

