# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 29 05:46:55 2022
#   Inital geometry file: a 113 line input string
#   Ligand name: 5-[(2~{S},7~{R})-7-fluoranyl-2-methyl-undecyl]benzene-1,3-diol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCC[C@@H](F)CCCC[C@H](C)Cc1cc(O)cc(O)c1
#
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
 4ON  4ON  "5-[(2S,7R)-7-fluoranyl-2-methyl-undecyl]benzene-1,3-diol"  ligand  50  21  .  2022-09-22  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_4ON
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
 4ON  C10  C  CH2   0  -0.423  -5.4419   2.9681  23.8158
 4ON  C13  C  CH2   0  -0.492  -4.2916   5.1843  23.8143
 4ON  C15  C  CR16  0  -0.424  -2.5607   6.0898  22.2492
 4ON  C21  C  CR16  0  -0.480  -2.3894   6.6347  24.5873
 4ON  C01  C  CH3   0  -0.659  -5.7909   0.5631  14.7555
 4ON  C02  C  CH2   0  -0.418  -6.2386   1.2034  16.0620
 4ON  C04  C  CH2   0  -0.472  -5.8641   1.3773  18.5659
 4ON  C05  C  CH1   0   0.217  -5.1195   0.8703  19.7829
 4ON  C07  C  CH2   0  -0.476  -5.5740   1.5006  21.0827
 4ON  C08  C  CH2   0  -0.439  -4.8422   0.9647  22.3088
 4ON  C09  C  CH2   0  -0.440  -5.4266   1.4518  23.6327
 4ON  C11  C  CH1   0  -0.234  -4.0888   3.6685  23.6685
 4ON  C12  C  CH3   0  -0.656  -3.0635   3.1452  24.6672
 4ON  C14  C  CR6   0   0.169  -3.0534   5.9939  23.5459
 4ON  C16  C  CR6   0   0.389  -1.4062   6.8268  21.9982
 4ON  C18  C  CR16  0  -0.488  -0.7378   7.4700  23.0350
 4ON  C19  C  CR6   0   0.387  -1.2354   7.3705  24.3299
 4ON  F06  F  F     0  -0.396  -3.7469   1.1282  19.6130
 4ON  O17  O  OH1   0  -0.633  -0.9730   6.8925  20.7232
 4ON  O20  O  OH1   0  -0.632  -0.5559   8.0111  25.3020
 4ON  H1   H  HCH2  0   0.221  -6.1450   3.4131  23.1045
 4ON  H2   H  HCH2  0   0.218  -5.8441   3.1947  24.8095
 4ON  H3   H  HCH2  0   0.241  -5.0795   5.4958  23.1218
 4ON  H4   H  HCH2  0   0.233  -4.6616   5.3974  24.8217
 4ON  H5   H  HCR6  0   0.245  -3.0730   5.5987  21.4298
 4ON  H6   H  HCR6  0   0.255  -2.7733   6.5597  25.5996
 4ON  H7   H  HCH3  0   0.225  -6.3864   0.9147  13.9122
 4ON  H8   H  HCH3  0   0.215  -4.7460   0.7946  14.5418
 4ON  H9   H  HCH3  0   0.216  -5.8849  -0.5235  14.7964
 4ON  H10  H  HCH2  0   0.212  -6.1678   2.2923  15.9793
 4ON  H11  H  HCH2  0   0.211  -7.2956   0.9810  16.2366
 4ON  H12  H  HCH2  0   0.210  -5.4969  -0.3552  17.3439
 4ON  H13  H  HCH2  0   0.216  -4.3629   0.9524  17.0762
 4ON  H14  H  HCH2  0   0.224  -5.7644   2.4662  18.5034
 4ON  H15  H  HCH2  0   0.227  -6.9279   1.1754  18.7242
 4ON  H16  H  HCH1  0   0.193  -5.2198  -0.2195  19.8476
 4ON  H17  H  HCH2  0   0.230  -5.4661   2.5876  21.0088
 4ON  H18  H  HCH2  0   0.227  -6.6462   1.3055  21.1862
 4ON  H19  H  HCH2  0   0.223  -4.8819  -0.1292  22.2959
 4ON  H20  H  HCH2  0   0.222  -3.7825   1.2273  22.2521
 4ON  H21  H  HCH2  0   0.221  -6.4543   1.0859  23.7230
 4ON  H22  H  HCH2  0   0.223  -4.8742   0.9857  24.4528
 4ON  H23  H  HCH1  0   0.224  -3.7090   3.4852  22.6563
 4ON  H24  H  HCH3  0   0.230  -2.1102   3.6664  24.5754
 4ON  H25  H  HCH3  0   0.211  -3.4176   3.2795  25.6928
 4ON  H26  H  HCH3  0   0.231  -2.8656   2.0827  24.5219
 4ON  H27  H  HCR6  0   0.268   0.1601   8.0480  22.8438
 4ON  H28  H  HOH1  0   0.471  -0.1697   7.4222  20.6666
 4ON  H29  H  HOH1  0   0.472  -0.9840   7.8740  26.1547
 4ON  C03  C  CH2   0  -0.414  -5.4188   0.7342  17.2575

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
 4ON  C01  C02  single    1.522  0.020  1.522
 4ON  C02  C03  single    1.524  0.020  1.524
 4ON  C03  C04  single    1.524  0.020  1.524
 4ON  C04  C05  single    1.514  0.020  1.514
 4ON  F06  C05  single    1.407  0.020  1.407
 4ON  C05  C07  single    1.514  0.020  1.514
 4ON  C07  C08  single    1.525  0.020  1.525
 4ON  C08  C09  single    1.527  0.020  1.527
 4ON  C09  C10  single    1.527  0.020  1.527
 4ON  O17  C16  single    1.348  0.020  1.348
 4ON  C10  C11  single    1.531  0.020  1.531
 4ON  C15  C16  aromatic  1.393  0.020  1.393
 4ON  C15  C14  aromatic  1.390  0.020  1.390
 4ON  C16  C18  aromatic  1.391  0.020  1.391
 4ON  C13  C11  single    1.536  0.020  1.536
 4ON  C13  C14  single    1.504  0.020  1.504
 4ON  C11  C12  single    1.524  0.020  1.524
 4ON  C14  C21  aromatic  1.391  0.020  1.391
 4ON  C18  C19  aromatic  1.391  0.020  1.391
 4ON  C21  C19  aromatic  1.393  0.020  1.393
 4ON  C19  O20  single    1.348  0.020  1.348
 4ON  C10  H1   single    0.970  0.020  1.090
 4ON  C10  H2   single    0.970  0.020  1.090
 4ON  C13  H3   single    0.970  0.020  1.090
 4ON  C13  H4   single    0.970  0.020  1.090
 4ON  C15  H5   single    0.930  0.020  1.080
 4ON  C21  H6   single    0.930  0.020  1.080
 4ON  C01  H7   single    0.970  0.020  1.090
 4ON  C01  H8   single    0.970  0.020  1.090
 4ON  C01  H9   single    0.970  0.020  1.090
 4ON  C02  H10  single    0.970  0.020  1.090
 4ON  C02  H11  single    0.970  0.020  1.090
 4ON  C03  H12  single    0.970  0.020  1.090
 4ON  C03  H13  single    0.970  0.020  1.090
 4ON  C04  H14  single    0.970  0.020  1.090
 4ON  C04  H15  single    0.970  0.020  1.090
 4ON  C05  H16  single    0.970  0.020  1.090
 4ON  C07  H17  single    0.970  0.020  1.090
 4ON  C07  H18  single    0.970  0.020  1.090
 4ON  C08  H19  single    0.970  0.020  1.090
 4ON  C08  H20  single    0.970  0.020  1.090
 4ON  C09  H21  single    0.970  0.020  1.090
 4ON  C09  H22  single    0.970  0.020  1.090
 4ON  C11  H23  single    0.970  0.020  1.090
 4ON  C12  H24  single    0.970  0.020  1.090
 4ON  C12  H25  single    0.970  0.020  1.090
 4ON  C12  H26  single    0.970  0.020  1.090
 4ON  C18  H27  single    0.930  0.020  1.080
 4ON  O17  H28  single    0.850  0.020  0.980
 4ON  O20  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
 4ON  H2   C10  H1   105.63  3.000
 4ON  H2   C10  C11  108.49  3.000
 4ON  H1   C10  C11  108.62  3.000
 4ON  H2   C10  C09  108.52  3.000
 4ON  H1   C10  C09  109.40  3.000
 4ON  C11  C10  C09  115.71  3.000
 4ON  H4   C13  H3   106.48  3.000
 4ON  H4   C13  C14  109.76  3.000
 4ON  H3   C13  C14  109.07  3.000
 4ON  H4   C13  C11  108.92  3.000
 4ON  H3   C13  C11  108.42  3.000
 4ON  C14  C13  C11  113.94  3.000
 4ON  H5   C15  C16  119.69  3.000
 4ON  H5   C15  C14  120.41  3.000
 4ON  C16  C15  C14  119.89  3.000
 4ON  H6   C21  C19  120.13  3.000
 4ON  H6   C21  C14  119.84  3.000
 4ON  C19  C21  C14  120.03  3.000
 4ON  H9   C01  H8   107.51  3.000
 4ON  H9   C01  H7   107.64  3.000
 4ON  H8   C01  H7   107.64  3.000
 4ON  H9   C01  C02  111.18  3.000
 4ON  H8   C01  C02  111.12  3.000
 4ON  H7   C01  C02  111.56  3.000
 4ON  H11  C02  H10  106.06  3.000
 4ON  H11  C02  C03  109.39  3.000
 4ON  H10  C02  C03  109.33  3.000
 4ON  H11  C02  C01  109.61  3.000
 4ON  H10  C02  C01  109.55  3.000
 4ON  C03  C02  C01  112.69  3.000
 4ON  H15  C04  H14  106.27  3.000
 4ON  H15  C04  C05  107.46  3.000
 4ON  H14  C04  C05  109.51  3.000
 4ON  H15  C04  C03  109.29  3.000
 4ON  H14  C04  C03  110.11  3.000
 4ON  C05  C04  C03  113.89  3.000
 4ON  H16  C05  F06  106.18  3.000
 4ON  H16  C05  C07  109.61  3.000
 4ON  F06  C05  C07  108.67  3.000
 4ON  H16  C05  C04  109.59  3.000
 4ON  C07  C05  C04  113.76  3.000
 4ON  F06  C05  C04  108.75  3.000
 4ON  H18  C07  H17  106.25  3.000
 4ON  H18  C07  C08  109.35  3.000
 4ON  H17  C07  C08  110.84  3.000
 4ON  H18  C07  C05  107.51  3.000
 4ON  H17  C07  C05  109.01  3.000
 4ON  C08  C07  C05  113.57  3.000
 4ON  H20  C08  H19  105.93  3.000
 4ON  H20  C08  C09  109.84  3.000
 4ON  H19  C08  C09  108.37  3.000
 4ON  H20  C08  C07  109.82  3.000
 4ON  H19  C08  C07  108.92  3.000
 4ON  C09  C08  C07  113.67  3.000
 4ON  H22  C09  H21  105.67  3.000
 4ON  H22  C09  C08  108.73  3.000
 4ON  H21  C09  C08  108.92  3.000
 4ON  H22  C09  C10  109.78  3.000
 4ON  H21  C09  C10  108.21  3.000
 4ON  C08  C09  C10  115.12  3.000
 4ON  H23  C11  C12  108.33  3.000
 4ON  H23  C11  C13  107.35  3.000
 4ON  C12  C11  C13  111.43  3.000
 4ON  H23  C11  C10  108.57  3.000
 4ON  C12  C11  C10  112.00  3.000
 4ON  C13  C11  C10  109.01  3.000
 4ON  H26  C12  H25  107.66  3.000
 4ON  H26  C12  H24  107.21  3.000
 4ON  H25  C12  H24  107.66  3.000
 4ON  H26  C12  C11  111.67  3.000
 4ON  H25  C12  C11  110.77  3.000
 4ON  H24  C12  C11  111.65  3.000
 4ON  C21  C14  C15  119.81  3.000
 4ON  C21  C14  C13  120.49  3.000
 4ON  C15  C14  C13  119.70  3.000
 4ON  O17  C16  C18  121.86  3.000
 4ON  C18  C16  C15  120.58  3.000
 4ON  O17  C16  C15  117.56  3.000
 4ON  H27  C18  C19  119.89  3.000
 4ON  H27  C18  C16  120.84  3.000
 4ON  C19  C18  C16  119.27  3.000
 4ON  O20  C19  C18  117.20  3.000
 4ON  O20  C19  C21  122.38  3.000
 4ON  C18  C19  C21  120.42  3.000
 4ON  H28  O17  C16  110.49  3.000
 4ON  H29  O20  C19  110.27  3.000
 4ON  H13  C03  H12  106.29  3.000
 4ON  H13  C03  C04  109.89  3.000
 4ON  H12  C03  C04  109.33  3.000
 4ON  H13  C03  C02  109.15  3.000
 4ON  H12  C03  C02  109.25  3.000
 4ON  C04  C03  C02  112.73  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
 4ON  CONST_01  C19  C18  C16  C15     0.00   0.0  0
 4ON  CONST_02  C19  C21  C14  C15     0.00   0.0  0
 4ON  CONST_03  C16  C15  C14  C21     0.00   0.0  0
 4ON  CONST_04  C16  C18  C19  C21     0.00   0.0  0
 4ON  CONST_05  C18  C16  C15  C14     0.00   0.0  0
 4ON  CONST_06  C18  C19  C21  C14     0.00   0.0  0
 4ON  CONST_07  C16  C15  C14  C13   180.00   0.0  0
 4ON  CONST_08  C19  C21  C14  C13   180.00   0.0  0
 4ON  CONST_09  O17  C16  C15  C14   180.00   0.0  0
 4ON  CONST_10  O20  C19  C21  C14   180.00   0.0  0
 4ON  CONST_11  O20  C19  C18  C16   180.00   0.0  0
 4ON  CONST_12  O17  C16  C18  C19   180.00   0.0  0
 4ON  CONST_13  H27  C18  C16  C15   180.00   0.0  0
 4ON  CONST_14  H6   C21  C14  C15   180.00   0.0  0
 4ON  CONST_15  H5   C15  C14  C21   180.00   0.0  0
 4ON  CONST_16  H27  C18  C19  C21   180.00   0.0  0
 4ON  CONST_17  H5   C15  C16  C18   180.00   0.0  0
 4ON  CONST_18  H6   C21  C19  C18   180.00   0.0  0
 4ON  Var_01    C11  C13  C14  C15    70.26  30.0  2
 4ON  Var_02    C11  C13  C14  C21  -109.02  30.0  2
 4ON  Var_03    H3   C13  C14  C15   -51.02  30.0  2
 4ON  Var_04    H4   C13  C14  C15  -167.31  30.0  2
 4ON  Var_05    H3   C13  C14  C21   129.71  30.0  2
 4ON  Var_06    H4   C13  C14  C21    13.42  30.0  2
 4ON  Var_07    C07  C08  C09  C10   -58.96  30.0  1
 4ON  Var_08    C04  C03  C02  C01   179.86  30.0  3
 4ON  Var_09    C05  C04  C03  C02   176.69  30.0  3
 4ON  Var_10    C09  C08  C07  C05  -172.00  30.0  3
 4ON  Var_11    C11  C10  C09  C08   -55.69  30.0  3
 4ON  Var_12    H19  C08  C09  C10   179.80  30.0  1
 4ON  Var_13    H20  C08  C09  C10    64.52  30.0  1
 4ON  Var_14    H12  C03  C02  C01   -58.38  30.0  3
 4ON  Var_15    H13  C03  C02  C01    57.46  30.0  3
 4ON  Var_16    H14  C04  C03  C02   -59.87  30.0  3
 4ON  Var_17    H15  C04  C03  C02    56.51  30.0  3
 4ON  Var_18    H7   C01  C02  C03  -179.75  30.0  3
 4ON  Var_19    H8   C01  C02  C03   -59.62  30.0  3
 4ON  Var_20    H9   C01  C02  C03    60.09  30.0  3
 4ON  Var_21    H10  C02  C03  C04    57.79  30.0  1
 4ON  Var_22    H11  C02  C03  C04   -57.95  30.0  1
 4ON  Var_23    H12  C03  C04  C05    54.97  30.0  1
 4ON  Var_24    H13  C03  C04  C05   -61.32  30.0  1
 4ON  Var_25    H19  C08  C07  C05   -51.07  30.0  3
 4ON  Var_26    H20  C08  C07  C05    64.51  30.0  3
 4ON  Var_27    H21  C09  C08  C07    62.74  30.0  3
 4ON  Var_28    H22  C09  C08  C07   177.42  30.0  3
 4ON  Var_29    H1   C10  C09  C08    67.35  30.0  3
 4ON  Var_30    H2   C10  C09  C08  -177.86  30.0  3
 4ON  Var_31    H17  C07  C08  C09    64.89  30.0  1
 4ON  Var_32    H18  C07  C08  C09   -51.92  30.0  1
 4ON  Var_33    H21  C09  C10  C11  -177.77  30.0  2
 4ON  Var_34    H22  C09  C10  C11    67.37  30.0  2

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
 4ON  chir_01  C05  C04  F06  C07  negativ
 4ON  chir_02  C11  C10  C13  C12  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
 4ON  plan-1  C13  0.020
 4ON  plan-1  C15  0.020
 4ON  plan-1  C21  0.020
 4ON  plan-1  C14  0.020
 4ON  plan-1  C16  0.020
 4ON  plan-1  C18  0.020
 4ON  plan-1  C19  0.020
 4ON  plan-1  O17  0.020
 4ON  plan-1  O20  0.020
 4ON  plan-1  H5   0.020
 4ON  plan-1  H6   0.020
 4ON  plan-1  H27  0.020

