# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr 29 14:45:06 2020
#   Inital geometry file: a 146 line input string
#   Ligand name: (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC/C=C\C\C=C/C/C=C\C\C=C/C/C=C\C\C=C/CCC(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
 F22  F22  '(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid'  ligand  55  24  .  2021-08-09  2021-08-09  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_F22
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
 F22  C1    C  C      0   0.414   10.1619   0.9357   0.4263
 F22  O1    O  OC    -1  -0.632   11.1674   0.2407   0.6839
 F22  O2    O  O      0  -0.607    9.9746   2.1198   0.7674
 F22  C2    C  CH2    0  -0.581    9.0620   0.2420  -0.3979
 F22  C3    C  CH2    0  -0.480    7.8149   1.0778  -0.6692
 F22  C4    C  C1     0  -0.205    6.8561   0.3605  -1.5660
 F22  C5    C  C1     0  -0.215    5.6064  -0.0197  -1.3038
 F22  C6    C  CH2    0  -0.574    4.8282   0.2099  -0.0390
 F22  C7    C  C1     0  -0.204    3.7515   1.2323  -0.2636
 F22  C8    C  C1     0  -0.204    2.4362   1.0303  -0.3141
 F22  C9    C  CH2    0  -0.581    1.7006  -0.2662  -0.1266
 F22  C10   C  C1     0  -0.206    0.9268  -0.2513   1.1613
 F22  C11   C  C1     0  -0.203   -0.3901  -0.1186   1.3092
 F22  C12   C  CH2    0  -0.576   -1.4173   0.0148   0.2224
 F22  C13   C  C1     0  -0.200   -2.3045  -1.1954   0.1670
 F22  C14   C  C1     0  -0.209   -3.6109  -1.2515   0.4194
 F22  C15   C  CH2    0  -0.580   -4.5121  -0.1078   0.7900
 F22  C16   C  C1     0  -0.203   -5.3013   0.3396  -0.4070
 F22  C17   C  C1     0  -0.202   -6.6105   0.2138  -0.6157
 F22  C18   C  CH2    0  -0.579   -7.6381  -0.3742   0.3080
 F22  C19   C  C1     0  -0.210   -8.5698   0.6969   0.8022
 F22  C20   C  C1     0  -0.207   -9.8159   0.9305   0.3934
 F22  C21   C  CH2    0  -0.488  -10.5997   0.1682  -0.6290
 F22  C22   C  CH3    0  -0.659  -11.8778  -0.4291  -0.0443
 F22  H2C1  H  HCH2   0   0.223    9.5012  -0.0816  -1.3490
 F22  H2C2  H  HCH2   0   0.225    8.7775  -0.6848   0.1116
 F22  H3C1  H  HCH2   0   0.222    7.3439   1.3618   0.2728
 F22  H3C2  H  HCH2   0   0.224    8.1130   2.0133  -1.1515
 F22  H4    H  H      0   0.226    7.2513   0.1109  -2.5486
 F22  H5    H  H      0   0.232    5.0557  -0.5325  -2.0875
 F22  H6C1  H  HCH2   0   0.248    4.4026  -0.7368   0.3008
 F22  H6C2  H  HCH2   0   0.251    5.4847   0.5576   0.7614
 F22  H7    H  H      0   0.238    4.1134   2.2433  -0.4288
 F22  H8    H  H      0   0.238    1.7986   1.8915  -0.4928
 F22  H9C1  H  HCH2   0   0.253    1.0328  -0.4207  -0.9776
 F22  H9C2  H  HCH2   0   0.254    2.3938  -1.1100  -0.1189
 F22  H10   H  H      0   0.239    1.5327  -0.3312   2.0592
 F22  H11   H  H      0   0.239   -0.7899  -0.1195   2.3195
 F22  H121  H  HCH2   0   0.253   -2.0052   0.9196   0.3929
 F22  H122  H  HCH2   0   0.252   -0.9364   0.1442  -0.7501
 F22  H13   H  H      0   0.240   -1.8012  -2.1181  -0.1071
 F22  H14   H  H      0   0.239   -4.1067  -2.2120   0.3136
 F22  H15   H  HCH2   0   0.254   -5.1709  -0.4171   1.6034
 F22  H16   H  H      0   0.238   -4.7078   0.7961  -1.1944
 F22  H171  H  H      0   0.238   -7.0092   0.5956  -1.5515
 F22  H172  H  HCH2   0   0.253   -3.9309   0.7358   1.1695
 F22  H181  H  HCH2   0   0.253   -8.1901  -1.1530  -0.2236
 F22  H182  H  HCH2   0   0.252   -7.1623  -0.8594   1.1622
 F22  H19   H  H      0   0.236   -8.1453   1.3606   1.5499
 F22  H20   H  H      0   0.231  -10.3456   1.7633   0.8497
 F22  H211  H  HCH2   0   0.233  -10.8690   0.8478  -1.4438
 F22  H212  H  HCH2   0   0.232   -9.9946  -0.6197  -1.0799
 F22  H221  H  HCH3   0   0.230  -12.4682  -0.9244  -0.8157
 F22  H222  H  HCH3   0   0.223  -11.6511  -1.1647   0.7284
 F22  H223  H  HCH3   0   0.221  -12.5038   0.3427   0.4067

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
 F22  C1   O1    deloc   1.249  0.020  1.249
 F22  C1   O2    deloc   1.246  0.020  1.246
 F22  C1   C2    single  1.540  0.020  1.540
 F22  C2   C3    single  1.526  0.020  1.526
 F22  C3   C4    single  1.496  0.020  1.496
 F22  C4   C5    double  1.332  0.020  1.332
 F22  C5   C6    single  1.503  0.020  1.503
 F22  C6   C7    single  1.502  0.020  1.502
 F22  C7   C8    double  1.332  0.020  1.332
 F22  C8   C9    single  1.502  0.020  1.502
 F22  C9   C10   single  1.503  0.020  1.503
 F22  C10  C11   double  1.332  0.020  1.332
 F22  C11  C12   single  1.501  0.020  1.501
 F22  C12  C13   single  1.502  0.020  1.502
 F22  C13  C14   double  1.332  0.020  1.332
 F22  C14  C15   single  1.503  0.020  1.503
 F22  C15  C16   single  1.502  0.020  1.502
 F22  C16  C17   double  1.332  0.020  1.332
 F22  C17  C18   single  1.502  0.020  1.502
 F22  C18  C19   single  1.503  0.020  1.503
 F22  C19  C20   double  1.332  0.020  1.332
 F22  C20  C21   single  1.497  0.020  1.497
 F22  C21  C22   single  1.527  0.020  1.527
 F22  C2   H2C1  single  0.970  0.020  1.090
 F22  C2   H2C2  single  0.970  0.020  1.090
 F22  C3   H3C1  single  0.970  0.020  1.090
 F22  C3   H3C2  single  0.970  0.020  1.090
 F22  C4   H4    single  0.930  0.020  1.080
 F22  C5   H5    single  0.930  0.020  1.080
 F22  C6   H6C1  single  0.970  0.020  1.090
 F22  C6   H6C2  single  0.970  0.020  1.090
 F22  C7   H7    single  0.930  0.020  1.080
 F22  C8   H8    single  0.930  0.020  1.080
 F22  C9   H9C1  single  0.970  0.020  1.090
 F22  C9   H9C2  single  0.970  0.020  1.090
 F22  C10  H10   single  0.930  0.020  1.080
 F22  C11  H11   single  0.930  0.020  1.080
 F22  C12  H121  single  0.970  0.020  1.090
 F22  C12  H122  single  0.970  0.020  1.090
 F22  C13  H13   single  0.930  0.020  1.080
 F22  C14  H14   single  0.930  0.020  1.080
 F22  C15  H15   single  0.970  0.020  1.090
 F22  C16  H16   single  0.930  0.020  1.080
 F22  C17  H171  single  0.930  0.020  1.080
 F22  C15  H172  single  0.970  0.020  1.090
 F22  C18  H181  single  0.970  0.020  1.090
 F22  C18  H182  single  0.970  0.020  1.090
 F22  C19  H19   single  0.930  0.020  1.080
 F22  C20  H20   single  0.930  0.020  1.080
 F22  C21  H211  single  0.970  0.020  1.090
 F22  C21  H212  single  0.970  0.020  1.090
 F22  C22  H221  single  0.970  0.020  1.090
 F22  C22  H222  single  0.970  0.020  1.090
 F22  C22  H223  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
 F22  C2    C1   O2    117.86  3.000
 F22  C2    C1   O1    115.77  3.000
 F22  O2    C1   O1    126.37  3.000
 F22  H2C2  C2   H2C1  104.94  3.000
 F22  H2C2  C2   C3    109.51  3.000
 F22  H2C1  C2   C3    109.57  3.000
 F22  H2C2  C2   C1    108.53  3.000
 F22  H2C1  C2   C1    108.13  3.000
 F22  C3    C2   C1    115.62  3.000
 F22  H3C2  C3   H3C1  106.01  3.000
 F22  H3C2  C3   C4    108.69  3.000
 F22  H3C1  C3   C4    111.46  3.000
 F22  H3C2  C3   C2    108.91  3.000
 F22  H3C1  C3   C2    110.00  3.000
 F22  C4    C3   C2    111.58  3.000
 F22  H4    C4   C5    116.93  3.000
 F22  H4    C4   C3    114.75  3.000
 F22  C5    C4   C3    128.32  3.000
 F22  H5    C5   C6    114.63  3.000
 F22  H5    C5   C4    117.91  3.000
 F22  C6    C5   C4    127.43  3.000
 F22  H6C2  C6   H6C1  106.39  3.000
 F22  H6C2  C6   C7    108.90  3.000
 F22  H6C1  C6   C7    110.93  3.000
 F22  H6C2  C6   C5    110.75  3.000
 F22  H6C1  C6   C5    109.34  3.000
 F22  C7    C6   C5    110.45  3.000
 F22  H7    C7   C8    117.67  3.000
 F22  H7    C7   C6    114.67  3.000
 F22  C8    C7   C6    127.63  3.000
 F22  H8    C8   C9    114.66  3.000
 F22  H8    C8   C7    117.75  3.000
 F22  C9    C8   C7    127.57  3.000
 F22  H9C2  C9   H9C1  106.50  3.000
 F22  H9C2  C9   C10   109.18  3.000
 F22  H9C1  C9   C10   110.75  3.000
 F22  H9C2  C9   C8    110.91  3.000
 F22  H9C1  C9   C8    108.91  3.000
 F22  C10   C9   C8    110.52  3.000
 F22  H10   C10  C11   117.84  3.000
 F22  H10   C10  C9    114.87  3.000
 F22  C11   C10  C9    127.26  3.000
 F22  H11   C11  C12   114.92  3.000
 F22  H11   C11  C10   117.85  3.000
 F22  C12   C11  C10   127.23  3.000
 F22  H122  C12  H121  106.12  3.000
 F22  H122  C12  C13   108.83  3.000
 F22  H121  C12  C13   110.81  3.000
 F22  H122  C12  C11   110.71  3.000
 F22  H121  C12  C11   109.19  3.000
 F22  C13   C12  C11   111.06  3.000
 F22  H13   C13  C14   117.81  3.000
 F22  H13   C13  C12   114.84  3.000
 F22  C14   C13  C12   127.35  3.000
 F22  H14   C14  C15   115.04  3.000
 F22  H14   C14  C13   117.82  3.000
 F22  C15   C14  C13   127.09  3.000
 F22  H172  C15  H15   106.32  3.000
 F22  H172  C15  C16   109.05  3.000
 F22  H15   C15  C16   111.18  3.000
 F22  H172  C15  C14   110.75  3.000
 F22  H15   C15  C14   109.28  3.000
 F22  C16   C15  C14   110.20  3.000
 F22  H16   C16  C17   117.59  3.000
 F22  H16   C16  C15   114.56  3.000
 F22  C17   C16  C15   127.83  3.000
 F22  H171  C17  C18   114.60  3.000
 F22  H171  C17  C16   117.55  3.000
 F22  C18   C17  C16   127.83  3.000
 F22  H182  C18  H181  106.51  3.000
 F22  H182  C18  C19   109.24  3.000
 F22  H181  C18  C19   110.78  3.000
 F22  H182  C18  C17   110.92  3.000
 F22  H181  C18  C17   109.00  3.000
 F22  C19   C18  C17   110.32  3.000
 F22  H19   C19  C20   118.01  3.000
 F22  H19   C19  C18   114.80  3.000
 F22  C20   C19  C18   127.15  3.000
 F22  H20   C20  C21   114.94  3.000
 F22  H20   C20  C19   117.46  3.000
 F22  C21   C20  C19   127.60  3.000
 F22  H212  C21  H211  106.10  3.000
 F22  H212  C21  C22   109.88  3.000
 F22  H211  C21  C22   108.78  3.000
 F22  H212  C21  C20   111.07  3.000
 F22  H211  C21  C20   108.72  3.000
 F22  C22   C21  C20   112.08  3.000
 F22  H223  C22  H222  107.67  3.000
 F22  H223  C22  H221  107.64  3.000
 F22  H222  C22  H221  107.90  3.000
 F22  H223  C22  C21   111.20  3.000
 F22  H222  C22  C21   111.17  3.000
 F22  H221  C22  C21   111.09  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
 F22  Var_01  C6    C5   C4   C3     1.66   0.0  2
 F22  Var_02  C9    C8   C7   C6     1.56   0.0  2
 F22  Var_03  C12   C11  C10  C9     1.58   0.0  2
 F22  Var_04  C15   C14  C13  C12    1.49   0.0  2
 F22  Var_05  C18   C17  C16  C15    1.80   0.0  2
 F22  Var_06  C21   C20  C19  C18    1.56   0.0  2
 F22  Var_07  C4    C3   C2   C1   175.41  30.0  3
 F22  Var_08  C3    C2   C1   O1   177.96  30.0  3
 F22  Var_09  C5    C4   C3   C2   118.43  30.0  3
 F22  Var_10  C7    C6   C5   C4   108.53  30.0  3
 F22  Var_11  C8    C7   C6   C5   109.12  30.0  3
 F22  Var_12  C10   C9   C8   C7   110.58  30.0  3
 F22  Var_13  C11   C10  C9   C8   105.55  30.0  3
 F22  Var_14  C13   C12  C11  C10  112.35  30.0  3
 F22  Var_15  C14   C13  C12  C11  114.89  30.0  3
 F22  Var_16  C16   C15  C14  C13  101.06  30.0  3
 F22  Var_17  C17   C16  C15  C14  111.14  30.0  3
 F22  Var_18  C19   C18  C17  C16  112.00  30.0  3
 F22  Var_19  C20   C19  C18  C17  103.38  30.0  3
 F22  Var_20  C22   C21  C20  C19  120.03  30.0  3
 F22  Var_21  H221  C22  C21  C20  176.28  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
 F22  plan-1  C1    0.020
 F22  plan-1  O1    0.020
 F22  plan-1  O2    0.020
 F22  plan-1  C2    0.020
 F22  plan-2  C3    0.020
 F22  plan-2  C4    0.020
 F22  plan-2  C5    0.020
 F22  plan-2  C6    0.020
 F22  plan-2  H4    0.020
 F22  plan-2  H5    0.020
 F22  plan-3  C6    0.020
 F22  plan-3  C7    0.020
 F22  plan-3  C8    0.020
 F22  plan-3  C9    0.020
 F22  plan-3  H7    0.020
 F22  plan-3  H8    0.020
 F22  plan-4  C9    0.020
 F22  plan-4  C10   0.020
 F22  plan-4  C11   0.020
 F22  plan-4  C12   0.020
 F22  plan-4  H10   0.020
 F22  plan-4  H11   0.020
 F22  plan-5  C12   0.020
 F22  plan-5  C13   0.020
 F22  plan-5  C14   0.020
 F22  plan-5  C15   0.020
 F22  plan-5  H13   0.020
 F22  plan-5  H14   0.020
 F22  plan-6  C15   0.020
 F22  plan-6  C16   0.020
 F22  plan-6  C17   0.020
 F22  plan-6  C18   0.020
 F22  plan-6  H16   0.020
 F22  plan-6  H171  0.020
 F22  plan-7  C18   0.020
 F22  plan-7  C19   0.020
 F22  plan-7  C20   0.020
 F22  plan-7  C21   0.020
 F22  plan-7  H19   0.020
 F22  plan-7  H20   0.020

