# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 27 07:14:48 2020
#   Inital geometry file: a 159 line input string
#   Ligand name: (8E,12Z,15Z,18Z,21Z)-6-oxotetracosa-8,12,15,18,21-pentaenoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC\C=C/C/C=C\C\C=C/C\C=C/CC\C=C\CC(=O)CCCCC(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
 66B  66B  '(8E,12Z,15Z,18Z,21Z)-6-oxotetracosa-8,12,15,18,21-pentaenoic acid'  ligand  63  27  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_66B
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
 66B  O25  O  O     0  -0.446  -10.4143   1.7528   1.0205
 66B  C24  C  C     0   0.550   -9.4781   2.5128   1.0085
 66B  O26  O  OH1   0  -0.598   -9.6027   3.8175   1.2377
 66B  C23  C  CH2   0  -0.581   -8.0502   2.1286   0.7390
 66B  C22  C  CH2   0  -0.420   -7.8471   0.6433   0.4930
 66B  C21  C  CH2   0  -0.418   -6.3809   0.3173   0.2354
 66B  C20  C  CH2   0  -0.559   -6.1685  -1.1655  -0.0157
 66B  C19  C  C     0   0.408   -4.7381  -1.5705  -0.2627
 66B  O27  O  O     0  -0.400   -3.8440  -0.7645  -0.3774
 66B  C18  C  CH2   0  -0.633   -4.4880  -3.0616  -0.3527
 66B  C17  C  C1    0  -0.190   -3.1126  -3.4141  -0.8131
 66B  C16  C  C1    0  -0.209   -2.2248  -4.0834  -0.0856
 66B  C15  C  CH2   0  -0.484   -0.8398  -4.4280  -0.5307
 66B  C14  C  CH2   0  -0.488    0.2251  -3.7431   0.3370
 66B  C13  C  C1    0  -0.207    1.6110  -4.1625  -0.0393
 66B  C12  C  C1    0  -0.210    2.6089  -3.3841  -0.4549
 66B  C11  C  CH2   0  -0.579    2.5884  -1.8895  -0.6117
 66B  C10  C  C1    0  -0.201    3.3149  -1.2356   0.5282
 66B  C9   C  C1    0  -0.203    4.4696  -0.5744   0.4840
 66B  C8   C  CH2   0  -0.583    5.3152  -0.2866  -0.7238
 66B  C7   C  C1    0  -0.208    5.2379   1.1719  -1.0768
 66B  C6   C  C1    0  -0.199    6.1508   2.1108  -0.8347
 66B  C5   C  CH2   0  -0.577    7.4895   1.9361  -0.1777
 66B  C4   C  C1    0  -0.203    8.6047   2.2425  -1.1372
 66B  C3   C  C1    0  -0.215    9.4194   3.2962  -1.1138
 66B  C2   C  CH2   0  -0.491    9.4378   4.4097  -0.1132
 66B  C1   C  CH3   0  -0.656   10.6729   4.3522   0.7850
 66B  H1   H  HOH1  0   0.478  -10.5308   4.0375   1.4067
 66B  H2   H  HCH2  0   0.277   -7.6994   2.7118  -0.1188
 66B  H3   H  HCH2  0   0.276   -7.4416   2.4646   1.5846
 66B  H4   H  HCH2  0   0.229   -8.2020   0.0718   1.3546
 66B  H5   H  HCH2  0   0.229   -8.4496   0.3211  -0.3605
 66B  H6   H  HCH2  0   0.227   -6.0246   0.8933  -0.6226
 66B  H7   H  HCH2  0   0.226   -5.7806   0.6386   1.0914
 66B  H8   H  HCH2  0   0.263   -6.5510  -1.7632   0.8193
 66B  H9   H  HCH2  0   0.270   -6.7526  -1.4958  -0.8829
 66B  H10  H  HCH2  0   0.286   -4.6937  -3.4867   0.6360
 66B  H11  H  HCH2  0   0.273   -5.2482  -3.4918  -1.0144
 66B  H12  H  H     0   0.238   -2.8436  -3.0974  -1.8173
 66B  H14  H  H     0   0.234   -2.4955  -4.3967   0.9211
 66B  H16  H  HCH2  0   0.234   -0.6951  -5.5125  -0.4761
 66B  H17  H  HCH2  0   0.237   -0.6979  -4.1432  -1.5763
 66B  H18  H  HCH2  0   0.237    0.1023  -2.6609   0.2700
 66B  H19  H  HCH2  0   0.238    0.0476  -4.0081   1.3850
 66B  H20  H  H     0   0.234    1.8039  -5.2299   0.0361
 66B  H21  H  H     0   0.237    3.5625  -3.8547  -0.6761
 66B  H22  H  HCH2  0   0.253    3.0397  -1.6182  -1.5680
 66B  H23  H  HCH2  0   0.252    1.5615  -1.5176  -0.6378
 66B  H24  H  H     0   0.238    2.8343  -1.3480   1.4961
 66B  H25  H  H     0   0.238    4.8530  -0.1644   1.4141
 66B  H26  H  HCH2  0   0.254    6.3460  -0.5813  -0.5151
 66B  H27  H  HCH2  0   0.254    4.9900  -0.8810  -1.5805
 66B  H28  H  H     0   0.239    4.3096   1.4794  -1.5496
 66B  H29  H  H     0   0.239    5.9244   3.1273  -1.1439
 66B  H30  H  HCH2  0   0.252    7.5401   2.5900   0.6968
 66B  H31  H  HCH2  0   0.251    7.6082   0.9161   0.1946
 66B  H32  H  H     0   0.236    8.7278   1.5198  -1.9386
 66B  H33  H  H     0   0.232   10.1787   3.3596  -1.8890
 66B  H34  H  HCH2  0   0.234    9.4306   5.3642  -0.6479
 66B  H35  H  HCH2  0   0.231    8.5375   4.3988   0.5024
 66B  H36  H  HCH3  0   0.229   10.7014   5.2027   1.4669
 66B  H37  H  HCH3  0   0.223   10.6765   3.4398   1.3823
 66B  H38  H  HCH3  0   0.222   11.5925   4.3671   0.1978

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
 66B  C7   C6   double  1.332  0.020  1.332
 66B  C7   C8   single  1.503  0.020  1.503
 66B  C9   C10  double  1.331  0.020  1.331
 66B  C9   C8   single  1.502  0.020  1.502
 66B  C6   C5   single  1.501  0.020  1.501
 66B  C1   C2   single  1.528  0.020  1.528
 66B  C10  C11  single  1.502  0.020  1.502
 66B  C4   C3   double  1.332  0.020  1.332
 66B  C4   C5   single  1.503  0.020  1.503
 66B  C3   C2   single  1.497  0.020  1.497
 66B  C11  C12  single  1.503  0.020  1.503
 66B  C12  C13  double  1.332  0.020  1.332
 66B  C13  C14  single  1.496  0.020  1.496
 66B  C14  C15  single  1.535  0.020  1.535
 66B  C15  C16  single  1.495  0.020  1.495
 66B  C16  C17  double  1.329  0.020  1.329
 66B  C17  C18  single  1.493  0.020  1.493
 66B  O27  C19  double  1.209  0.020  1.209
 66B  C18  C19  single  1.515  0.020  1.515
 66B  C19  C20  single  1.507  0.020  1.507
 66B  C20  C21  single  1.519  0.020  1.519
 66B  C22  C21  single  1.524  0.020  1.524
 66B  C22  C23  single  1.519  0.020  1.519
 66B  C23  C24  single  1.503  0.020  1.503
 66B  C24  O25  double  1.206  0.020  1.206
 66B  C24  O26  single  1.330  0.020  1.330
 66B  O26  H1   single  0.850  0.020  0.980
 66B  C23  H2   single  0.970  0.020  1.090
 66B  C23  H3   single  0.970  0.020  1.090
 66B  C22  H4   single  0.970  0.020  1.090
 66B  C22  H5   single  0.970  0.020  1.090
 66B  C21  H6   single  0.970  0.020  1.090
 66B  C21  H7   single  0.970  0.020  1.090
 66B  C20  H8   single  0.970  0.020  1.090
 66B  C20  H9   single  0.970  0.020  1.090
 66B  C18  H10  single  0.970  0.020  1.090
 66B  C18  H11  single  0.970  0.020  1.090
 66B  C17  H12  single  0.930  0.020  1.080
 66B  C16  H14  single  0.930  0.020  1.080
 66B  C15  H16  single  0.970  0.020  1.090
 66B  C15  H17  single  0.970  0.020  1.090
 66B  C14  H18  single  0.970  0.020  1.090
 66B  C14  H19  single  0.970  0.020  1.090
 66B  C13  H20  single  0.930  0.020  1.080
 66B  C12  H21  single  0.930  0.020  1.080
 66B  C11  H22  single  0.970  0.020  1.090
 66B  C11  H23  single  0.970  0.020  1.090
 66B  C10  H24  single  0.930  0.020  1.080
 66B  C9   H25  single  0.930  0.020  1.080
 66B  C8   H26  single  0.970  0.020  1.090
 66B  C8   H27  single  0.970  0.020  1.090
 66B  C7   H28  single  0.930  0.020  1.080
 66B  C6   H29  single  0.930  0.020  1.080
 66B  C5   H30  single  0.970  0.020  1.090
 66B  C5   H31  single  0.970  0.020  1.090
 66B  C4   H32  single  0.930  0.020  1.080
 66B  C3   H33  single  0.930  0.020  1.080
 66B  C2   H34  single  0.970  0.020  1.090
 66B  C2   H35  single  0.970  0.020  1.090
 66B  C1   H36  single  0.970  0.020  1.090
 66B  C1   H37  single  0.970  0.020  1.090
 66B  C1   H38  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
 66B  C23  C24  O26  111.75  3.000
 66B  O26  C24  O25  122.93  3.000
 66B  C23  C24  O25  125.33  3.000
 66B  H1   O26  C24  110.03  3.000
 66B  H3   C23  H2   105.28  3.000
 66B  H3   C23  C22  110.54  3.000
 66B  H2   C23  C22  110.55  3.000
 66B  H3   C23  C24  108.13  3.000
 66B  H2   C23  C24  107.98  3.000
 66B  C22  C23  C24  113.95  3.000
 66B  H5   C22  H4   106.40  3.000
 66B  H5   C22  C21  109.58  3.000
 66B  H4   C22  C21  109.49  3.000
 66B  H5   C22  C23  109.93  3.000
 66B  H4   C22  C23  109.88  3.000
 66B  C21  C22  C23  111.42  3.000
 66B  H7   C21  H6   106.30  3.000
 66B  H7   C21  C20  109.84  3.000
 66B  H6   C21  C20  109.82  3.000
 66B  H7   C21  C22  109.44  3.000
 66B  H6   C21  C22  109.48  3.000
 66B  C20  C21  C22  111.80  3.000
 66B  H9   C20  H8   104.62  3.000
 66B  H9   C20  C19  107.16  3.000
 66B  H8   C20  C19  108.03  3.000
 66B  H9   C20  C21  110.51  3.000
 66B  H8   C20  C21  110.96  3.000
 66B  C19  C20  C21  114.97  3.000
 66B  C18  C19  O27  121.90  3.000
 66B  C18  C19  C20  115.53  3.000
 66B  O27  C19  C20  122.56  3.000
 66B  H11  C18  H10  105.21  3.000
 66B  H11  C18  C17  111.11  3.000
 66B  H10  C18  C17  111.08  3.000
 66B  H11  C18  C19  107.93  3.000
 66B  H10  C18  C19  107.30  3.000
 66B  C17  C18  C19  113.76  3.000
 66B  H12  C17  C16  119.17  3.000
 66B  H12  C17  C18  116.37  3.000
 66B  C16  C17  C18  124.45  3.000
 66B  H14  C16  C15  116.06  3.000
 66B  H14  C16  C17  119.03  3.000
 66B  C15  C16  C17  124.89  3.000
 66B  H17  C15  H16  106.77  3.000
 66B  H17  C15  C14  109.54  3.000
 66B  H16  C15  C14  108.78  3.000
 66B  H17  C15  C16  110.18  3.000
 66B  H16  C15  C16  109.61  3.000
 66B  C14  C15  C16  111.81  3.000
 66B  H19  C14  H18  106.28  3.000
 66B  H19  C14  C13  108.84  3.000
 66B  H18  C14  C13  111.52  3.000
 66B  H19  C14  C15  108.69  3.000
 66B  H18  C14  C15  109.25  3.000
 66B  C13  C14  C15  112.05  3.000
 66B  H20  C13  C12  117.55  3.000
 66B  H20  C13  C14  114.96  3.000
 66B  C12  C13  C14  127.49  3.000
 66B  H21  C12  C11  114.94  3.000
 66B  H21  C12  C13  117.91  3.000
 66B  C11  C12  C13  127.12  3.000
 66B  H23  C11  H22  106.44  3.000
 66B  H23  C11  C10  108.95  3.000
 66B  H22  C11  C10  110.90  3.000
 66B  H23  C11  C12  110.72  3.000
 66B  H22  C11  C12  109.44  3.000
 66B  C10  C11  C12  110.32  3.000
 66B  H24  C10  C9   117.68  3.000
 66B  H24  C10  C11  114.66  3.000
 66B  C9   C10  C11  127.64  3.000
 66B  H25  C9   C8   114.67  3.000
 66B  H25  C9   C10  117.72  3.000
 66B  C8   C9   C10  127.59  3.000
 66B  H27  C8   H26  106.51  3.000
 66B  H27  C8   C7   109.19  3.000
 66B  H26  C8   C7   110.82  3.000
 66B  H27  C8   C9   111.02  3.000
 66B  H26  C8   C9   109.01  3.000
 66B  C7   C8   C9   110.24  3.000
 66B  H28  C7   C6   117.73  3.000
 66B  H28  C7   C8   114.90  3.000
 66B  C6   C7   C8   127.33  3.000
 66B  H29  C6   C5   114.78  3.000
 66B  H29  C6   C7   117.72  3.000
 66B  C5   C6   C7   127.50  3.000
 66B  H31  C5   H30  106.31  3.000
 66B  H31  C5   C4   109.11  3.000
 66B  H30  C5   C4   110.76  3.000
 66B  H31  C5   C6   110.77  3.000
 66B  H30  C5   C6   108.77  3.000
 66B  C4   C5   C6   111.01  3.000
 66B  H32  C4   C3   118.03  3.000
 66B  H32  C4   C5   114.81  3.000
 66B  C3   C4   C5   127.15  3.000
 66B  H33  C3   C2   115.13  3.000
 66B  H33  C3   C4   117.44  3.000
 66B  C2   C3   C4   127.41  3.000
 66B  H35  C2   H34  106.21  3.000
 66B  H35  C2   C1   109.57  3.000
 66B  H34  C2   C1   108.99  3.000
 66B  H35  C2   C3   111.08  3.000
 66B  H34  C2   C3   108.79  3.000
 66B  C1   C2   C3   112.00  3.000
 66B  H38  C1   H37  107.66  3.000
 66B  H38  C1   H36  107.69  3.000
 66B  H37  C1   H36  108.06  3.000
 66B  H38  C1   C2   111.37  3.000
 66B  H37  C1   C2   110.86  3.000
 66B  H36  C1   C2   111.05  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
 66B  CONST_01  H1   O26  C24  O25     0.00   0.0  0
 66B  Var_01    C15  C16  C17  C18  -179.26   0.0  2
 66B  Var_02    C11  C12  C13  C14     1.67   0.0  2
 66B  Var_03    C8   C9   C10  C11     1.77   0.0  2
 66B  Var_04    C5   C6   C7   C8      1.42   0.0  2
 66B  Var_05    C2   C3   C4   C5      1.36   0.0  2
 66B  Var_06    C22  C23  C24  O25    -1.01  30.0  2
 66B  Var_07    C21  C22  C23  C24  -179.64  30.0  1
 66B  Var_08    C20  C21  C22  C23  -179.83  30.0  3
 66B  Var_09    C19  C20  C21  C22  -179.29  30.0  1
 66B  Var_10    O27  C19  C20  C21    -6.62  30.0  2
 66B  Var_11    C17  C18  C19  C20   170.69  30.0  1
 66B  Var_12    C16  C17  C18  C19   117.27  30.0  2
 66B  Var_13    C14  C15  C16  C17   116.16  30.0  2
 66B  Var_14    C13  C14  C15  C16   175.81  30.0  1
 66B  Var_15    C12  C13  C14  C15   120.72  30.0  1
 66B  Var_16    C10  C11  C12  C13   103.18  30.0  2
 66B  Var_17    C9   C10  C11  C12   111.60  30.0  1
 66B  Var_18    C7   C8   C9   C10   108.36  30.0  3
 66B  Var_19    C6   C7   C8   C9    102.78  30.0  2
 66B  Var_20    C4   C5   C6   C7    115.44  30.0  3
 66B  Var_21    C3   C4   C5   C6    109.18  30.0  1
 66B  Var_22    C1   C2   C3   C4    109.62  30.0  3
 66B  Var_23    H36  C1   C2   C3    176.59  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
 66B  plan-1  C20  0.020
 66B  plan-1  C19  0.020
 66B  plan-1  O27  0.020
 66B  plan-1  C18  0.020
 66B  plan-2  O25  0.020
 66B  plan-2  C24  0.020
 66B  plan-2  O26  0.020
 66B  plan-2  C23  0.020
 66B  plan-2  H1   0.020
 66B  plan-3  C8   0.020
 66B  plan-3  C7   0.020
 66B  plan-3  C6   0.020
 66B  plan-3  C5   0.020
 66B  plan-3  H28  0.020
 66B  plan-3  H29  0.020
 66B  plan-4  C11  0.020
 66B  plan-4  C10  0.020
 66B  plan-4  C9   0.020
 66B  plan-4  C8   0.020
 66B  plan-4  H24  0.020
 66B  plan-4  H25  0.020
 66B  plan-5  C5   0.020
 66B  plan-5  C4   0.020
 66B  plan-5  C3   0.020
 66B  plan-5  C2   0.020
 66B  plan-5  H32  0.020
 66B  plan-5  H33  0.020
 66B  plan-6  C14  0.020
 66B  plan-6  C13  0.020
 66B  plan-6  C12  0.020
 66B  plan-6  C11  0.020
 66B  plan-6  H20  0.020
 66B  plan-6  H21  0.020
 66B  plan-7  C18  0.020
 66B  plan-7  C17  0.020
 66B  plan-7  C16  0.020
 66B  plan-7  C15  0.020
 66B  plan-7  H12  0.020
 66B  plan-7  H14  0.020

