# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr 15 22:10:46 2020
#   Inital geometry file: a 154 line input string
#   Ligand name: 1-hydroxy-2-methyl-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]quinolin-4(1H)-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)=CCCC(/C)=C/CCC(/C)=C/CC1=C(C)N(O)c2ccccc2C1=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
 AUK  AUK  1-hydroxy-2-methyl-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]quinolin-4(1H)-one  ligand  61  28  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_AUK
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
 AUK  O27   O  O     0  -0.468  -3.2759   1.3950  -1.9105
 AUK  C7    C  CR6   0   0.441  -3.5926   0.8283  -0.8625
 AUK  C8    C  CR6   0  -0.179  -3.1539   1.2839   0.4378
 AUK  C9    C  CR6   0   0.312  -3.5249   0.6156   1.5744
 AUK  C28   C  CH3   0  -0.724  -3.0869   0.9932   2.9532
 AUK  N10   N  NR6   0  -0.321  -4.3427  -0.4722   1.4947
 AUK  O26   O  OH1   0  -0.518  -4.6265  -1.1496   2.6387
 AUK  C3    C  CR66  0   0.372  -4.8040  -1.0017   0.3176
 AUK  C4    C  CR16  0  -0.311  -5.6124  -2.1487   0.2956
 AUK  C5    C  CR16  0  -0.251  -6.0553  -2.6357  -0.9129
 AUK  C6    C  CR16  0  -0.255  -5.7122  -2.0068  -2.1148
 AUK  C1    C  CR16  0  -0.296  -4.9177  -0.8850  -2.0877
 AUK  C2    C  CR66  0  -0.131  -4.4471  -0.3616  -0.8760
 AUK  C11   C  CH2   0  -0.602  -2.2250   2.4709   0.4605
 AUK  C12   C  C1    0  -0.245  -0.7897   2.0345   0.3894
 AUK  C13   C  C     0   0.114   0.0973   2.2669  -0.5805
 AUK  C23   C  CH3   0  -0.729  -0.1765   3.0634  -1.8214
 AUK  C14   C  CH2   0  -0.484   1.4922   1.7081  -0.4734
 AUK  C15   C  CH2   0  -0.489   1.7143   0.4799  -1.3723
 AUK  C16   C  C1    0  -0.276   3.1335   0.0045  -1.3172
 AUK  C17   C  C     0   0.121   3.6299  -0.9839  -0.5679
 AUK  C24   C  CH3   0  -0.734   2.8057  -1.8327   0.3562
 AUK  C18   C  CH2   0  -0.483   5.1027  -1.2943  -0.5912
 AUK  C19   C  CH2   0  -0.494   5.8120  -0.9624   0.7314
 AUK  C20   C  C1    0  -0.256   7.2592  -1.3443   0.6960
 AUK  C21   C  C     0   0.081   8.3159  -0.5362   0.5776
 AUK  C22   C  CH3   0  -0.717   8.2374   0.9582   0.4699
 AUK  C25   C  CH3   0  -0.706   9.7121  -1.0870   0.5375
 AUK  H28   H  HCH3  0   0.268  -3.9380   1.2292   3.5934
 AUK  H28A  H  HCH3  0   0.273  -2.5359   0.1809   3.4271
 AUK  H28B  H  HCH3  0   0.263  -2.4411   1.8629   2.9331
 AUK  HO26  H  HOH1  0   0.491  -5.4595  -0.7897   2.9797
 AUK  H4    H  HCR6  0   0.279  -5.8853  -2.6522   1.2111
 AUK  H5    H  HCR6  0   0.268  -6.6779  -3.5206  -0.9263
 AUK  H6    H  HCR6  0   0.261  -6.0681  -2.4029  -3.0561
 AUK  H1    H  HCR6  0   0.261  -4.6430  -0.3874  -3.0081
 AUK  H11   H  HCH2  0   0.264  -2.4758   3.1275  -0.3707
 AUK  H11A  H  HCH2  0   0.255  -2.3757   3.0676   1.3627
 AUK  H12   H  H     0   0.221  -0.4538   1.4461   1.2419
 AUK  H23   H  HCH3  0   0.231   0.3895   3.9986  -1.8031
 AUK  H23A  H  HCH3  0   0.232   0.1539   2.5242  -2.7120
 AUK  H23B  H  HCH3  0   0.246  -1.2277   3.3020  -1.9581
 AUK  H14   H  HCH2  0   0.227   2.2215   2.4813  -0.7400
 AUK  H14A  H  HCH2  0   0.234   1.7045   1.4218   0.5596
 AUK  H15   H  HCH2  0   0.234   1.0150  -0.3028  -1.0699
 AUK  H15A  H  HCH2  0   0.233   1.4636   0.7331  -2.4063
 AUK  H16   H  H     0   0.220   3.8333   0.5672  -1.9315
 AUK  H24   H  HCH3  0   0.233   3.0389  -2.8913   0.2202
 AUK  H24A  H  HCH3  0   0.241   3.0181  -1.6002   1.4025
 AUK  H24B  H  HCH3  0   0.241   1.7345  -1.7058   0.2116
 AUK  H18   H  HCH2  0   0.225   5.2487  -2.3584  -0.8107
 AUK  H18A  H  HCH2  0   0.233   5.5889  -0.7392  -1.3972
 AUK  H19   H  HCH2  0   0.235   5.6789   0.0998   0.9458
 AUK  H19A  H  HCH2  0   0.236   5.3248  -1.5027   1.5482
 AUK  H20   H  H     0   0.220   7.4490  -2.4145   0.7451
 AUK  H22   H  HCH3  0   0.234   8.7710   1.4340   1.2967
 AUK  H22A  H  HCH3  0   0.234   8.7253   1.2983  -0.4470
 AUK  H22B  H  HCH3  0   0.238   7.2191   1.3412   0.4640
 AUK  H25   H  HCH3  0   0.235   9.7294  -2.1741   0.6155
 AUK  H25A  H  HCH3  0   0.230  10.2166  -0.8062  -0.3910
 AUK  H25B  H  HCH3  0   0.230  10.3172  -0.6803   1.3525

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
 AUK  O27  C7    double    1.233  0.020  1.233
 AUK  C7   C8    single    1.446  0.020  1.446
 AUK  C7   C2    single    1.465  0.020  1.465
 AUK  C8   C9    double    1.370  0.020  1.370
 AUK  C8   C11   single    1.507  0.020  1.507
 AUK  C9   C28   single    1.495  0.020  1.495
 AUK  C9   N10   single    1.363  0.020  1.363
 AUK  N10  O26   single    1.360  0.020  1.360
 AUK  N10  C3    single    1.371  0.020  1.371
 AUK  C3   C4    aromatic  1.403  0.020  1.403
 AUK  C3   C2    aromatic  1.401  0.020  1.401
 AUK  C4   C5    aromatic  1.376  0.020  1.376
 AUK  C5   C6    aromatic  1.399  0.020  1.399
 AUK  C6   C1    aromatic  1.375  0.020  1.375
 AUK  C1   C2    aromatic  1.401  0.020  1.401
 AUK  C11  C12   single    1.502  0.020  1.502
 AUK  C12  C13   double    1.335  0.020  1.335
 AUK  C13  C23   single    1.500  0.020  1.500
 AUK  C13  C14   single    1.506  0.020  1.506
 AUK  C14  C15   single    1.538  0.020  1.538
 AUK  C15  C16   single    1.498  0.020  1.498
 AUK  C16  C17   double    1.336  0.020  1.336
 AUK  C17  C24   single    1.501  0.020  1.501
 AUK  C17  C18   single    1.505  0.020  1.505
 AUK  C18  C19   single    1.537  0.020  1.537
 AUK  C19  C20   single    1.497  0.020  1.497
 AUK  C20  C21   double    1.336  0.020  1.336
 AUK  C21  C22   single    1.500  0.020  1.500
 AUK  C21  C25   single    1.501  0.020  1.501
 AUK  C28  H28   single    0.970  0.020  1.090
 AUK  C28  H28A  single    0.970  0.020  1.090
 AUK  C28  H28B  single    0.970  0.020  1.090
 AUK  O26  HO26  single    0.850  0.020  0.980
 AUK  C4   H4    single    0.930  0.020  1.080
 AUK  C5   H5    single    0.930  0.020  1.080
 AUK  C6   H6    single    0.930  0.020  1.080
 AUK  C1   H1    single    0.930  0.020  1.080
 AUK  C11  H11   single    0.970  0.020  1.090
 AUK  C11  H11A  single    0.970  0.020  1.090
 AUK  C12  H12   single    0.930  0.020  1.080
 AUK  C23  H23   single    0.970  0.020  1.090
 AUK  C23  H23A  single    0.970  0.020  1.090
 AUK  C23  H23B  single    0.970  0.020  1.090
 AUK  C14  H14   single    0.970  0.020  1.090
 AUK  C14  H14A  single    0.970  0.020  1.090
 AUK  C15  H15   single    0.970  0.020  1.090
 AUK  C15  H15A  single    0.970  0.020  1.090
 AUK  C16  H16   single    0.930  0.020  1.080
 AUK  C24  H24   single    0.970  0.020  1.090
 AUK  C24  H24A  single    0.970  0.020  1.090
 AUK  C24  H24B  single    0.970  0.020  1.090
 AUK  C18  H18   single    0.970  0.020  1.090
 AUK  C18  H18A  single    0.970  0.020  1.090
 AUK  C19  H19   single    0.970  0.020  1.090
 AUK  C19  H19A  single    0.970  0.020  1.090
 AUK  C20  H20   single    0.930  0.020  1.080
 AUK  C22  H22   single    0.970  0.020  1.090
 AUK  C22  H22A  single    0.970  0.020  1.090
 AUK  C22  H22B  single    0.970  0.020  1.090
 AUK  C25  H25   single    0.970  0.020  1.090
 AUK  C25  H25A  single    0.970  0.020  1.090
 AUK  C25  H25B  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
 AUK  C2    C7   C8    116.18  3.000
 AUK  C2    C7   O27   121.02  3.000
 AUK  C8    C7   O27   122.80  3.000
 AUK  C11   C8   C9    122.59  3.000
 AUK  C11   C8   C7    116.66  3.000
 AUK  C9    C8   C7    120.68  3.000
 AUK  N10   C9   C28   115.55  3.000
 AUK  N10   C9   C8    120.21  3.000
 AUK  C28   C9   C8    124.24  3.000
 AUK  H28B  C28  H28A  107.75  3.000
 AUK  H28B  C28  H28   107.60  3.000
 AUK  H28A  C28  H28   107.49  3.000
 AUK  H28B  C28  C9    111.11  3.000
 AUK  H28A  C28  C9    111.15  3.000
 AUK  H28   C28  C9    111.55  3.000
 AUK  C3    N10  O26   117.38  3.000
 AUK  C3    N10  C9    124.09  3.000
 AUK  O26   N10  C9    118.27  3.000
 AUK  HO26  O26  N10   106.88  3.000
 AUK  C2    C3   C4    120.46  3.000
 AUK  C2    C3   N10   118.00  3.000
 AUK  C4    C3   N10   121.54  3.000
 AUK  H4    C4   C5    119.88  3.000
 AUK  H4    C4   C3    120.89  3.000
 AUK  C5    C4   C3    119.23  3.000
 AUK  H5    C5   C6    119.87  3.000
 AUK  H5    C5   C4    119.04  3.000
 AUK  C6    C5   C4    121.09  3.000
 AUK  H6    C6   C1    120.40  3.000
 AUK  H6    C6   C5    120.16  3.000
 AUK  C1    C6   C5    119.44  3.000
 AUK  H1    C1   C2    118.60  3.000
 AUK  H1    C1   C6    120.35  3.000
 AUK  C2    C1   C6    121.05  3.000
 AUK  C1    C2   C3    118.73  3.000
 AUK  C1    C2   C7    120.48  3.000
 AUK  C3    C2   C7    120.79  3.000
 AUK  H11A  C11  H11   105.63  3.000
 AUK  H11A  C11  C12   109.25  3.000
 AUK  H11   C11  C12   111.06  3.000
 AUK  H11A  C11  C8    110.95  3.000
 AUK  H11   C11  C8    108.75  3.000
 AUK  C12   C11  C8    111.06  3.000
 AUK  H12   C12  C13   117.25  3.000
 AUK  H12   C12  C11   114.50  3.000
 AUK  C13   C12  C11   128.24  3.000
 AUK  C14   C13  C23   115.14  3.000
 AUK  C14   C13  C12   119.94  3.000
 AUK  C23   C13  C12   124.92  3.000
 AUK  H23B  C23  H23A  107.36  3.000
 AUK  H23B  C23  H23   108.36  3.000
 AUK  H23A  C23  H23   106.22  3.000
 AUK  H23B  C23  C13   113.41  3.000
 AUK  H23A  C23  C13   110.93  3.000
 AUK  H23   C23  C13   110.24  3.000
 AUK  H14A  C14  H14   106.59  3.000
 AUK  H14A  C14  C15   108.37  3.000
 AUK  H14   C14  C15   108.97  3.000
 AUK  H14A  C14  C13   110.14  3.000
 AUK  H14   C14  C13   109.71  3.000
 AUK  C15   C14  C13   112.85  3.000
 AUK  H15A  C15  H15   106.31  3.000
 AUK  H15A  C15  C16   109.00  3.000
 AUK  H15   C15  C16   111.66  3.000
 AUK  H15A  C15  C14   109.55  3.000
 AUK  H15   C15  C14   108.54  3.000
 AUK  C16   C15  C14   111.64  3.000
 AUK  H16   C16  C17   117.41  3.000
 AUK  H16   C16  C15   115.12  3.000
 AUK  C17   C16  C15   127.42  3.000
 AUK  C18   C17  C24   115.47  3.000
 AUK  C18   C17  C16   120.49  3.000
 AUK  C24   C17  C16   124.02  3.000
 AUK  H24B  C24  H24A  107.08  3.000
 AUK  H24B  C24  H24   107.85  3.000
 AUK  H24A  C24  H24   106.49  3.000
 AUK  H24B  C24  C17   113.12  3.000
 AUK  H24A  C24  C17   111.25  3.000
 AUK  H24   C24  C17   110.74  3.000
 AUK  H18A  C18  H18   106.62  3.000
 AUK  H18A  C18  C19   108.64  3.000
 AUK  H18   C18  C19   108.69  3.000
 AUK  H18A  C18  C17   110.00  3.000
 AUK  H18   C18  C17   109.49  3.000
 AUK  C19   C18  C17   113.18  3.000
 AUK  H19A  C19  H19   106.24  3.000
 AUK  H19A  C19  C20   108.79  3.000
 AUK  H19   C19  C20   111.76  3.000
 AUK  H19A  C19  C18   109.29  3.000
 AUK  H19   C19  C18   108.83  3.000
 AUK  C20   C19  C18   111.76  3.000
 AUK  H20   C20  C21   117.46  3.000
 AUK  H20   C20  C19   114.74  3.000
 AUK  C21   C20  C19   127.77  3.000
 AUK  C25   C21  C22   114.34  3.000
 AUK  C25   C21  C20   121.08  3.000
 AUK  C22   C21  C20   124.59  3.000
 AUK  H22B  C22  H22A  107.68  3.000
 AUK  H22B  C22  H22   107.93  3.000
 AUK  H22A  C22  H22   106.33  3.000
 AUK  H22B  C22  C21   113.58  3.000
 AUK  H22A  C22  C21   110.30  3.000
 AUK  H22   C22  C21   110.71  3.000
 AUK  H25B  C25  H25A  106.39  3.000
 AUK  H25B  C25  H25   107.98  3.000
 AUK  H25A  C25  H25   108.03  3.000
 AUK  H25B  C25  C21   111.00  3.000
 AUK  H25A  C25  C21   110.95  3.000
 AUK  H25   C25  C21   112.25  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
 AUK  CONST_01  C6   C5   C4   C3     0.00   0.0  0
 AUK  CONST_02  C6   C1   C2   C3     0.00   0.0  0
 AUK  CONST_03  C1   C2   C3   C4     0.00   0.0  0
 AUK  CONST_04  C1   C6   C5   C4     0.00   0.0  0
 AUK  CONST_05  C2   C3   C4   C5     0.00   0.0  0
 AUK  CONST_06  C2   C1   C6   C5     0.00   0.0  0
 AUK  CONST_07  H1   C1   C2   C7     0.00   0.0  0
 AUK  CONST_08  H4   C4   C3   N10    0.00   0.0  0
 AUK  CONST_09  H5   C5   C4   C3   180.00   0.0  0
 AUK  CONST_10  H6   C6   C5   C4   180.00   0.0  0
 AUK  Var_01    C12  C11  C8   C7   -89.63  30.0  3
 AUK  Var_02    H28  C28  C9   C8   120.15  30.0  3
 AUK  Var_03    C13  C12  C11  C8   115.30  30.0  3
 AUK  Var_04    C23  C13  C12  C11    1.30   0.0  2
 AUK  Var_05    C24  C17  C16  C15    1.45   0.0  2
 AUK  Var_06    C22  C21  C20  C19    0.73   0.0  2
 AUK  Var_07    C15  C14  C13  C12  103.60  30.0  3
 AUK  Var_08    C16  C15  C14  C13  176.05  30.0  3
 AUK  Var_09    C17  C16  C15  C14   97.20  30.0  3
 AUK  Var_10    C19  C18  C17  C16  111.83  30.0  3
 AUK  Var_11    C20  C19  C18  C17  177.24  30.0  3
 AUK  Var_12    C21  C20  C19  C18  105.20  30.0  3
 AUK  Var_13    H23  C23  C13  C12  111.56  30.0  3
 AUK  Var_14    H24  C24  C17  C16  132.97  30.0  3
 AUK  Var_15    H22  C22  C21  C20  119.72  30.0  3
 AUK  Var_16    H25  C25  C21  C20   -0.05  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
 AUK  plan-1  O27  0.020
 AUK  plan-1  C7   0.020
 AUK  plan-1  C8   0.020
 AUK  plan-1  C9   0.020
 AUK  plan-1  C28  0.020
 AUK  plan-1  N10  0.020
 AUK  plan-1  O26  0.020
 AUK  plan-1  C3   0.020
 AUK  plan-1  C4   0.020
 AUK  plan-1  C5   0.020
 AUK  plan-1  C6   0.020
 AUK  plan-1  C1   0.020
 AUK  plan-1  C2   0.020
 AUK  plan-1  C11  0.020
 AUK  plan-1  H4   0.020
 AUK  plan-1  H5   0.020
 AUK  plan-1  H6   0.020
 AUK  plan-1  H1   0.020
 AUK  plan-2  C11  0.020
 AUK  plan-2  C12  0.020
 AUK  plan-2  C13  0.020
 AUK  plan-2  C23  0.020
 AUK  plan-2  C14  0.020
 AUK  plan-2  H12  0.020
 AUK  plan-3  C15  0.020
 AUK  plan-3  C16  0.020
 AUK  plan-3  C17  0.020
 AUK  plan-3  C24  0.020
 AUK  plan-3  C18  0.020
 AUK  plan-3  H16  0.020
 AUK  plan-4  C19  0.020
 AUK  plan-4  C20  0.020
 AUK  plan-4  C21  0.020
 AUK  plan-4  C22  0.020
 AUK  plan-4  C25  0.020
 AUK  plan-4  H20  0.020

