# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Jul 21 15:36:57 2021
#   Inital geometry file: a 146 line input string
#   Ligand name: docosanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCCCCCCCCCCCCCCCCCCC(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
 EO3  EO3  'docosanoic acid          '  ligand  68  24  .  2022-03-18  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_EO3
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
 EO3  C10   C  CH2   0  -0.409  -64.3242  31.6018  -10.6786
 EO3  C13   C  CH2   0  -0.430  -62.6679  28.4978  -12.4051
 EO3  C15   C  CH2   0  -0.426  -61.6518  26.2536  -11.6431
 EO3  C17   C  CH2   0  -0.423  -60.9639  26.0958  -14.1159
 EO3  C20   C  CH2   0  -0.426  -60.8094  25.5879  -17.9989
 EO3  C21   C  CH2   0  -0.584  -62.2042  25.9898  -18.4529
 EO3  C22   C  C     0   0.553  -62.5321  25.5552  -19.8541
 EO3  C01   C  CH3   0  -0.664  -65.1610  33.7187   -4.1542
 EO3  C02   C  CH2   0  -0.438  -65.5137  35.1358   -4.5865
 EO3  C03   C  CH2   0  -0.430  -66.9498  35.2822   -5.0936
 EO3  C04   C  CH2   0  -0.436  -67.2878  34.5594   -6.4038
 EO3  C05   C  CH2   0  -0.437  -67.0463  35.3722   -7.6769
 EO3  C06   C  CH2   0  -0.437  -65.5953  35.7370   -7.9875
 EO3  C07   C  CH2   0  -0.431  -64.6473  34.5482   -8.1362
 EO3  C08   C  CH2   0  -0.413  -64.9943  33.6258   -9.2979
 EO3  C09   C  CH2   0  -0.408  -64.0113  32.4734   -9.4693
 EO3  C11   C  CH2   0  -0.418  -63.3516  30.4435  -10.8683
 EO3  C12   C  CH2   0  -0.413  -63.6679  29.6126  -12.1067
 EO3  C14   C  CH2   0  -0.428  -62.6587  27.3738  -11.3753
 EO3  C16   C  CH2   0  -0.434  -61.8304  25.5387  -12.9890
 EO3  C18   C  CH2   0  -0.422  -61.3219  25.5293  -15.4839
 EO3  C19   C  CH2   0  -0.426  -60.4679  26.1100  -16.6056
 EO3  O23   O  O     0  -0.447  -61.8064  24.9160  -20.5750
 EO3  O1    O  OH1   0  -0.599  -63.7451  25.9574  -20.2267
 EO3  H101  H  HCH2  0   0.205  -64.3209  32.2245  -11.5803
 EO3  H102  H  HCH2  0   0.206  -65.3426  31.2071  -10.5895
 EO3  H132  H  HCH2  0   0.222  -62.9050  28.0837  -13.3893
 EO3  H131  H  HCH2  0   0.203  -61.6624  28.9260  -12.4909
 EO3  H152  H  HCH2  0   0.223  -61.7414  25.5277  -10.8309
 EO3  H151  H  HCH2  0   0.210  -60.6330  26.6506  -11.5727
 EO3  H172  H  HCH2  0   0.212  -59.9110  25.8901  -13.8949
 EO3  H171  H  HCH2  0   0.218  -61.0527  27.1853  -14.1526
 EO3  H201  H  HCH2  0   0.223  -60.7136  24.4986  -18.0143
 EO3  H202  H  HCH2  0   0.233  -60.0742  25.9717  -18.7098
 EO3  H212  H  HCH2  0   0.273  -62.3275  27.0766  -18.3949
 EO3  H211  H  HCH2  0   0.278  -62.9710  25.5763  -17.7910
 EO3  H012  H  HCH3  0   0.226  -64.1406  33.6655   -3.7725
 EO3  H013  H  HCH3  0   0.216  -65.8288  33.3704   -3.3635
 EO3  H011  H  HCH3  0   0.217  -65.2354  33.0091   -4.9796
 EO3  H022  H  HCH2  0   0.221  -64.8034  35.4707   -5.3455
 EO3  H021  H  HCH2  0   0.221  -65.3788  35.8088   -3.7352
 EO3  H032  H  HCH2  0   0.217  -67.1833  36.3458   -5.2099
 EO3  H031  H  HCH2  0   0.214  -67.6163  34.9176   -4.3053
 EO3  H041  H  HCH2  0   0.225  -68.3486  34.2951   -6.3878
 EO3  H042  H  HCH2  0   0.214  -66.7569  33.6038   -6.4604
 EO3  H051  H  HCH2  0   0.217  -67.6312  36.2959   -7.6141
 EO3  H052  H  HCH2  0   0.217  -67.4674  34.8203   -8.5223
 EO3  H062  H  HCH2  0   0.220  -65.2113  36.4087   -7.2153
 EO3  H061  H  HCH2  0   0.218  -65.5759  36.3185   -8.9154
 EO3  H071  H  HCH2  0   0.212  -64.6199  33.9695   -7.2067
 EO3  H072  H  HCH2  0   0.216  -63.6304  34.9284   -8.2774
 EO3  H082  H  HCH2  0   0.204  -65.0292  34.2128  -10.2229
 EO3  H081  H  HCH2  0   0.211  -66.0005  33.2164   -9.1634
 EO3  H092  H  HCH2  0   0.206  -64.0116  31.8577   -8.5631
 EO3  H091  H  HCH2  0   0.205  -62.9954  32.8731   -9.5636
 EO3  H112  H  HCH2  0   0.212  -63.3649  29.8129   -9.9739
 EO3  H111  H  HCH2  0   0.204  -62.3313  30.8358  -10.9475
 EO3  H121  H  HCH2  0   0.214  -63.7118  30.2812  -12.9727
 EO3  H122  H  HCH2  0   0.205  -64.6714  29.1825  -12.0099
 EO3  H142  H  HCH2  0   0.220  -62.4578  27.7855  -10.3818
 EO3  H141  H  HCH2  0   0.205  -63.6633  26.9378  -11.3242
 EO3  H161  H  HCH2  0   0.209  -62.8859  25.5843  -13.2828
 EO3  H162  H  HCH2  0   0.221  -61.6031  24.4748  -12.8744
 EO3  H181  H  HCH2  0   0.213  -62.3816  25.7299  -15.6731
 EO3  H182  H  HCH2  0   0.209  -61.2182  24.4383  -15.4761
 EO3  H191  H  HCH2  0   0.224  -59.4156  25.8901  -16.4015
 EO3  H192  H  HCH2  0   0.211  -60.5538  27.2025  -16.5960
 EO3  H1    H  HOH1  0   0.477  -63.9275  25.6618  -21.1312

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
 EO3  O23  C22   double  1.206  0.020  1.206
 EO3  C22  C21   single  1.503  0.020  1.503
 EO3  C21  C20   single  1.521  0.020  1.521
 EO3  C20  C19   single  1.527  0.020  1.527
 EO3  C19  C18   single  1.525  0.020  1.525
 EO3  C18  C17   single  1.523  0.020  1.523
 EO3  C17  C16   single  1.527  0.020  1.527
 EO3  C13  C12   single  1.527  0.020  1.527
 EO3  C13  C14   single  1.525  0.020  1.525
 EO3  C12  C11   single  1.525  0.020  1.525
 EO3  C16  C15   single  1.534  0.020  1.534
 EO3  C14  C15   single  1.530  0.020  1.530
 EO3  C11  C10   single  1.524  0.020  1.524
 EO3  C10  C09   single  1.523  0.020  1.523
 EO3  C09  C08   single  1.524  0.020  1.524
 EO3  C08  C07   single  1.523  0.020  1.523
 EO3  C07  C06   single  1.528  0.020  1.528
 EO3  C06  C05   single  1.528  0.020  1.528
 EO3  C05  C04   single  1.530  0.020  1.530
 EO3  C04  C03   single  1.534  0.020  1.534
 EO3  C03  C02   single  1.530  0.020  1.530
 EO3  C02  C01   single  1.523  0.020  1.523
 EO3  C22  O1    single  1.331  0.020  1.331
 EO3  C10  H101  single  0.970  0.020  1.090
 EO3  C10  H102  single  0.970  0.020  1.090
 EO3  C13  H132  single  0.970  0.020  1.090
 EO3  C13  H131  single  0.970  0.020  1.090
 EO3  C15  H152  single  0.970  0.020  1.090
 EO3  C15  H151  single  0.970  0.020  1.090
 EO3  C17  H172  single  0.970  0.020  1.090
 EO3  C17  H171  single  0.970  0.020  1.090
 EO3  C20  H201  single  0.970  0.020  1.090
 EO3  C20  H202  single  0.970  0.020  1.090
 EO3  C21  H212  single  0.970  0.020  1.090
 EO3  C21  H211  single  0.970  0.020  1.090
 EO3  C01  H012  single  0.970  0.020  1.090
 EO3  C01  H013  single  0.970  0.020  1.090
 EO3  C01  H011  single  0.970  0.020  1.090
 EO3  C02  H022  single  0.970  0.020  1.090
 EO3  C02  H021  single  0.970  0.020  1.090
 EO3  C03  H032  single  0.970  0.020  1.090
 EO3  C03  H031  single  0.970  0.020  1.090
 EO3  C04  H041  single  0.970  0.020  1.090
 EO3  C04  H042  single  0.970  0.020  1.090
 EO3  C05  H051  single  0.970  0.020  1.090
 EO3  C05  H052  single  0.970  0.020  1.090
 EO3  C06  H062  single  0.970  0.020  1.090
 EO3  C06  H061  single  0.970  0.020  1.090
 EO3  C07  H071  single  0.970  0.020  1.090
 EO3  C07  H072  single  0.970  0.020  1.090
 EO3  C08  H082  single  0.970  0.020  1.090
 EO3  C08  H081  single  0.970  0.020  1.090
 EO3  C09  H092  single  0.970  0.020  1.090
 EO3  C09  H091  single  0.970  0.020  1.090
 EO3  C11  H112  single  0.970  0.020  1.090
 EO3  C11  H111  single  0.970  0.020  1.090
 EO3  C12  H121  single  0.970  0.020  1.090
 EO3  C12  H122  single  0.970  0.020  1.090
 EO3  C14  H142  single  0.970  0.020  1.090
 EO3  C14  H141  single  0.970  0.020  1.090
 EO3  C16  H161  single  0.970  0.020  1.090
 EO3  C16  H162  single  0.970  0.020  1.090
 EO3  C18  H181  single  0.970  0.020  1.090
 EO3  C18  H182  single  0.970  0.020  1.090
 EO3  C19  H191  single  0.970  0.020  1.090
 EO3  C19  H192  single  0.970  0.020  1.090
 EO3  O1   H1    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
 EO3  H102  C10  H101  105.93  3.000
 EO3  H102  C10  C11   109.23  3.000
 EO3  H101  C10  C11   109.11  3.000
 EO3  H102  C10  C09   109.42  3.000
 EO3  H101  C10  C09   109.12  3.000
 EO3  C11   C10  C09   113.74  3.000
 EO3  H131  C13  H132  106.05  3.000
 EO3  H131  C13  C14   109.59  3.000
 EO3  H132  C13  C14   109.27  3.000
 EO3  H131  C13  C12   109.32  3.000
 EO3  H132  C13  C12   108.07  3.000
 EO3  C14   C13  C12   114.22  3.000
 EO3  H151  C15  H152  105.61  3.000
 EO3  H151  C15  C16   109.48  3.000
 EO3  H152  C15  C16   109.44  3.000
 EO3  H151  C15  C14   109.60  3.000
 EO3  H152  C15  C14   107.59  3.000
 EO3  C16   C15  C14   114.72  3.000
 EO3  H171  C17  H172  105.78  3.000
 EO3  H171  C17  C18   108.74  3.000
 EO3  H172  C17  C18   109.71  3.000
 EO3  H171  C17  C16   110.01  3.000
 EO3  H172  C17  C16   109.15  3.000
 EO3  C18   C17  C16   113.19  3.000
 EO3  H202  C20  H201  106.37  3.000
 EO3  H202  C20  C19   108.86  3.000
 EO3  H201  C20  C19   109.51  3.000
 EO3  H202  C20  C21   109.27  3.000
 EO3  H201  C20  C21   109.84  3.000
 EO3  C19   C20  C21   112.79  3.000
 EO3  H211  C21  H212  105.31  3.000
 EO3  H211  C21  C22   107.56  3.000
 EO3  H212  C21  C22   108.16  3.000
 EO3  H211  C21  C20   111.24  3.000
 EO3  H212  C21  C20   110.46  3.000
 EO3  C22   C21  C20   113.70  3.000
 EO3  O1    C22  O23   122.75  3.000
 EO3  O1    C22  C21   111.86  3.000
 EO3  O23   C22  C21   125.38  3.000
 EO3  H011  C01  H013  107.37  3.000
 EO3  H011  C01  H012  107.27  3.000
 EO3  H013  C01  H012  107.65  3.000
 EO3  H011  C01  C02   112.00  3.000
 EO3  H013  C01  C02   111.14  3.000
 EO3  H012  C01  C02   111.19  3.000
 EO3  H021  C02  H022  105.79  3.000
 EO3  H021  C02  C03   108.36  3.000
 EO3  H022  C02  C03   110.54  3.000
 EO3  H021  C02  C01   108.84  3.000
 EO3  H022  C02  C01   109.39  3.000
 EO3  C03   C02  C01   113.61  3.000
 EO3  H031  C03  H032  105.67  3.000
 EO3  H031  C03  C04   108.90  3.000
 EO3  H032  C03  C04   108.66  3.000
 EO3  H031  C03  C02   107.51  3.000
 EO3  H032  C03  C02   109.16  3.000
 EO3  C04   C03  C02   116.41  3.000
 EO3  H042  C04  H041  105.08  3.000
 EO3  H042  C04  C05   110.14  3.000
 EO3  H041  C04  C05   107.08  3.000
 EO3  H042  C04  C03   110.40  3.000
 EO3  H041  C04  C03   108.37  3.000
 EO3  C05   C04  C03   115.19  3.000
 EO3  H052  C05  H051  105.33  3.000
 EO3  H052  C05  C06   109.20  3.000
 EO3  H051  C05  C06   108.51  3.000
 EO3  H052  C05  C04   108.32  3.000
 EO3  H051  C05  C04   108.43  3.000
 EO3  C06   C05  C04   116.48  3.000
 EO3  H061  C06  H062  105.42  3.000
 EO3  H061  C06  C07   108.65  3.000
 EO3  H062  C06  C07   109.21  3.000
 EO3  H061  C06  C05   108.41  3.000
 EO3  H062  C06  C05   109.67  3.000
 EO3  C07   C06  C05   115.04  3.000
 EO3  H072  C07  H071  105.64  3.000
 EO3  H072  C07  C08   108.88  3.000
 EO3  H071  C07  C08   109.44  3.000
 EO3  H072  C07  C06   108.59  3.000
 EO3  H071  C07  C06   110.13  3.000
 EO3  C08   C07  C06   113.83  3.000
 EO3  H081  C08  H082  105.95  3.000
 EO3  H081  C08  C09   108.90  3.000
 EO3  H082  C08  C09   109.30  3.000
 EO3  H081  C08  C07   110.01  3.000
 EO3  H082  C08  C07   109.05  3.000
 EO3  C09   C08  C07   113.37  3.000
 EO3  H091  C09  H092  106.05  3.000
 EO3  H091  C09  C08   109.38  3.000
 EO3  H092  C09  C08   109.37  3.000
 EO3  H091  C09  C10   109.32  3.000
 EO3  H092  C09  C10   109.57  3.000
 EO3  C08   C09  C10   112.92  3.000
 EO3  H111  C11  H112  106.06  3.000
 EO3  H111  C11  C12   109.24  3.000
 EO3  H112  C11  C12   110.32  3.000
 EO3  H111  C11  C10   109.33  3.000
 EO3  H112  C11  C10   109.17  3.000
 EO3  C12   C11  C10   112.51  3.000
 EO3  H122  C12  H121  105.83  3.000
 EO3  H122  C12  C11   109.39  3.000
 EO3  H121  C12  C11   108.54  3.000
 EO3  H122  C12  C13   109.29  3.000
 EO3  H121  C12  C13   108.51  3.000
 EO3  C11   C12  C13   114.88  3.000
 EO3  H141  C14  H142  106.00  3.000
 EO3  H141  C14  C15   108.67  3.000
 EO3  H142  C14  C15   108.28  3.000
 EO3  H141  C14  C13   108.61  3.000
 EO3  H142  C14  C13   109.70  3.000
 EO3  C15   C14  C13   115.19  3.000
 EO3  H162  C16  H161  105.58  3.000
 EO3  H162  C16  C17   108.32  3.000
 EO3  H161  C16  C17   109.48  3.000
 EO3  H162  C16  C15   109.69  3.000
 EO3  H161  C16  C15   109.13  3.000
 EO3  C17   C16  C15   114.29  3.000
 EO3  H182  C18  H181  105.97  3.000
 EO3  H182  C18  C19   109.36  3.000
 EO3  H181  C18  C19   110.20  3.000
 EO3  H182  C18  C17   109.97  3.000
 EO3  H181  C18  C17   108.33  3.000
 EO3  C19   C18  C17   112.79  3.000
 EO3  H192  C19  H191  105.91  3.000
 EO3  H192  C19  C18   109.23  3.000
 EO3  H191  C19  C18   108.96  3.000
 EO3  H192  C19  C20   109.35  3.000
 EO3  H191  C19  C20   108.46  3.000
 EO3  C18   C19  C20   114.57  3.000
 EO3  H1    O1   C22   109.92  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
 EO3  CONST_01  H1    O1   C22  C21   180.00   0.0  0
 EO3  Var_01    C13   C12  C11  C10   175.80  30.0  1
 EO3  Var_02    C07   C08  C09  C10  -176.86  30.0  3
 EO3  Var_03    C16   C15  C14  C13   -58.65  30.0  3
 EO3  Var_04    C18   C17  C16  C15  -170.50  30.0  1
 EO3  Var_05    C12   C13  C14  C15  -179.25  30.0  1
 EO3  Var_06    C20   C19  C18  C17  -178.98  30.0  1
 EO3  Var_07    C14   C15  C16  C17    94.41  30.0  3
 EO3  Var_08    O23   C22  C21  C20     1.95  30.0  2
 EO3  Var_09    C18   C19  C20  C21    64.99  30.0  3
 EO3  Var_10    C19   C20  C21  C22   176.61  30.0  3
 EO3  Var_11    C04   C03  C02  C01   -66.82  30.0  1
 EO3  Var_12    C05   C04  C03  C02   -89.23  30.0  1
 EO3  Var_13    C06   C05  C04  C03    65.34  30.0  1
 EO3  Var_14    C07   C06  C05  C04    58.54  30.0  1
 EO3  Var_15    C08   C07  C06  C05    62.95  30.0  1
 EO3  Var_16    C09   C08  C07  C06   177.79  30.0  1
 EO3  Var_17    C11   C10  C09  C08   179.97  30.0  1
 EO3  Var_18    C12   C11  C10  C09  -178.44  30.0  2
 EO3  Var_19    C14   C13  C12  C11    67.19  30.0  1
 EO3  Var_20    C19   C18  C17  C16   178.98  30.0  1
 EO3  Var_21    H012  C01  C02  C03  -178.29  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
 EO3  plan-1  C21  0.020
 EO3  plan-1  C22  0.020
 EO3  plan-1  O23  0.020
 EO3  plan-1  O1   0.020
 EO3  plan-1  H1   0.020

