# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Mar  9 09:44:11 2022
#   Inital geometry file: a 154 line input string
#   Ligand name: 3-[(2E,6E,9R)-9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-2-methylquinolin-4(1H)-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)=C[C@H](O)CC(/C)=C/CCC(/C)=C/CC1=C(C)Nc2ccccc2C1=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
 AUI  AUI  3-[(2E,6E,9R)-9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-2-methylquinolin-4(1H)-one  ligand  61  28  .  2022-03-11  2022-03-11
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_AUI
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
 AUI  O13  O  O     0  -0.472   3.5698  -1.2952  -1.7242
 AUI  C1   C  CR6   0   0.434   3.9191  -0.7628  -0.6679
 AUI  C4   C  CR66  0  -0.106   4.7468   0.4495  -0.6648
 AUI  C5   C  CR16  0  -0.300   5.1626   1.0448  -1.8642
 AUI  C6   C  CR16  0  -0.258   5.9320   2.1850  -1.8584
 AUI  C7   C  CR16  0  -0.256   6.3092   2.7631  -0.6386
 AUI  C8   C  CR16  0  -0.316   5.9172   2.2018   0.5537
 AUI  C9   C  CR66  0   0.370   5.1319   1.0396   0.5439
 AUI  N10  N  NR16  0  -0.750   4.7276   0.4679   1.7162
 AUI  C3   C  CR6   0   0.311   3.9625  -0.6466   1.7712
 AUI  C11  C  CH3   0  -0.753   3.6060  -1.1206   3.1456
 AUI  C2   C  CR6   0  -0.157   3.5536  -1.2804   0.6292
 AUI  C12  C  CH2   0  -0.583   2.6569  -2.4885   0.6770
 AUI  C14  C  C1    0  -0.252   1.2149  -2.0778   0.5830
 AUI  C15  C  C     0   0.118   0.3491  -2.3151  -0.4047
 AUI  C26  C  CH3   0  -0.720   0.6575  -3.1083  -1.6394
 AUI  C16  C  CH2   0  -0.483  -1.0439  -1.7470  -0.3328
 AUI  C17  C  CH2   0  -0.491  -1.2678  -0.5819  -1.3122
 AUI  C18  C  C1    0  -0.261  -2.6702  -0.0614  -1.2398
 AUI  C19  C  C     0   0.123  -3.1164   0.9702  -0.5175
 AUI  C27  C  CH3   0  -0.733  -2.2364   1.8398   0.3314
 AUI  C20  C  CH2   0  -0.540  -4.5901   1.2948  -0.5179
 AUI  C21  C  CH1   0  -0.001  -5.3766   0.6381   0.6261
 AUI  O28  O  OH1   0  -0.664  -4.8748   0.9867   1.9042
 AUI  C22  C  C1    0  -0.292  -6.8355   0.9772   0.5140
 AUI  C23  C  C     0   0.083  -7.8299   0.1828   0.1120
 AUI  C24  C  CH3   0  -0.705  -9.2394   0.6919   0.0249
 AUI  C25  C  CH3   0  -0.721  -7.6678  -1.2494  -0.3044
 AUI  H1   H  HCR6  0   0.258   4.8674   0.5902  -2.8005
 AUI  H2   H  HCR6  0   0.259   6.2433   2.6375  -2.7902
 AUI  H3   H  HCR6  0   0.267   6.9143   3.6601  -0.6312
 AUI  H4   H  HCR6  0   0.276   6.2050   2.6487   1.4975
 AUI  H5   H  HCH3  0   0.267   3.9808  -0.4466   3.9141
 AUI  H6   H  HCH3  0   0.271   2.5257  -1.1947   3.2657
 AUI  H7   H  HCH3  0   0.274   4.0233  -2.1095   3.3363
 AUI  H9   H  HCH2  0   0.258   2.9267  -3.1678  -0.1309
 AUI  H10  H  HCH2  0   0.250   2.8140  -3.0407   1.6070
 AUI  H11  H  H     0   0.220   0.8604  -1.4854   1.4250
 AUI  H12  H  HCH3  0   0.225  -0.0970  -3.8842  -1.7894
 AUI  H13  H  HCH3  0   0.235   0.6387  -2.4757  -2.5294
 AUI  H14  H  HCH3  0   0.241   1.6326  -3.5879  -1.6088
 AUI  H15  H  HCH2  0   0.224  -1.7784  -2.5326  -0.5435
 AUI  H16  H  HCH2  0   0.233  -1.2514  -1.3907   0.6794
 AUI  H17  H  HCH2  0   0.235  -0.5362   0.1998  -1.0951
 AUI  H18  H  HCH2  0   0.233  -1.0650  -0.9176  -2.3328
 AUI  H19  H  H     0   0.219  -3.4025  -0.6260  -1.8137
 AUI  H20  H  HCH3  0   0.230  -2.4517   2.8961   0.1553
 AUI  H21  H  HCH3  0   0.240  -2.4153   1.6572   1.3921
 AUI  H22  H  HCH3  0   0.235  -1.1752   1.6825   0.1461
 AUI  H23  H  HCH2  0   0.232  -4.7411   2.3807  -0.4796
 AUI  H24  H  HCH2  0   0.248  -5.0426   0.9549  -1.4528
 AUI  H25  H  HCH1  0   0.234  -5.2272  -0.4411   0.5491
 AUI  H26  H  HOH1  0   0.441  -4.9291   1.9438   2.0009
 AUI  H27  H  H     0   0.230  -7.0783   2.0086   0.7673
 AUI  H28  H  HCH3  0   0.233  -9.6314   0.5777  -0.9891
 AUI  H29  H  HCH3  0   0.234  -9.9016   0.1187   0.6787
 AUI  H30  H  HCH3  0   0.238  -9.3188   1.7431   0.3005
 AUI  H31  H  HCH3  0   0.237  -8.3632  -1.8887   0.2443
 AUI  H32  H  HCH3  0   0.240  -7.9118  -1.3653  -1.3632
 AUI  H33  H  HCH3  0   0.240  -6.6640  -1.6420  -0.1550
 AUI  H34  H  HNR6  0   0.418   5.0045   0.9060   2.5818

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
 AUI  C12  C14  single    1.502  0.020  1.502
 AUI  C12  C2   single    1.505  0.020  1.505
 AUI  C14  C15  double    1.335  0.020  1.335
 AUI  C11  C3   single    1.497  0.020  1.497
 AUI  C24  C23  single    1.501  0.020  1.501
 AUI  C27  C19  single    1.500  0.020  1.500
 AUI  C22  C21  single    1.502  0.020  1.502
 AUI  C22  C23  double    1.335  0.020  1.335
 AUI  C17  C16  single    1.538  0.020  1.538
 AUI  C17  C18  single    1.498  0.020  1.498
 AUI  C16  C15  single    1.506  0.020  1.506
 AUI  C2   C3   double    1.369  0.020  1.369
 AUI  C2   C1   single    1.444  0.020  1.444
 AUI  C21  C20  single    1.536  0.020  1.536
 AUI  C21  O28  single    1.417  0.020  1.417
 AUI  C23  C25  single    1.500  0.020  1.500
 AUI  C15  C26  single    1.500  0.020  1.500
 AUI  C19  C18  double    1.336  0.020  1.336
 AUI  C19  C20  single    1.509  0.020  1.509
 AUI  C3   N10  single    1.353  0.020  1.353
 AUI  O13  C1   double    1.233  0.020  1.233
 AUI  C1   C4   single    1.468  0.020  1.468
 AUI  N10  C9   single    1.366  0.020  1.366
 AUI  C4   C9   aromatic  1.399  0.020  1.399
 AUI  C4   C5   aromatic  1.402  0.020  1.402
 AUI  C9   C8   aromatic  1.403  0.020  1.403
 AUI  C5   C6   aromatic  1.376  0.020  1.376
 AUI  C8   C7   aromatic  1.375  0.020  1.375
 AUI  C6   C7   aromatic  1.402  0.020  1.402
 AUI  C5   H1   single    0.930  0.020  1.080
 AUI  C6   H2   single    0.930  0.020  1.080
 AUI  C7   H3   single    0.930  0.020  1.080
 AUI  C8   H4   single    0.930  0.020  1.080
 AUI  C11  H5   single    0.970  0.020  1.090
 AUI  C11  H6   single    0.970  0.020  1.090
 AUI  C11  H7   single    0.970  0.020  1.090
 AUI  C12  H9   single    0.970  0.020  1.090
 AUI  C12  H10  single    0.970  0.020  1.090
 AUI  C14  H11  single    0.930  0.020  1.080
 AUI  C26  H12  single    0.970  0.020  1.090
 AUI  C26  H13  single    0.970  0.020  1.090
 AUI  C26  H14  single    0.970  0.020  1.090
 AUI  C16  H15  single    0.970  0.020  1.090
 AUI  C16  H16  single    0.970  0.020  1.090
 AUI  C17  H17  single    0.970  0.020  1.090
 AUI  C17  H18  single    0.970  0.020  1.090
 AUI  C18  H19  single    0.930  0.020  1.080
 AUI  C27  H20  single    0.970  0.020  1.090
 AUI  C27  H21  single    0.970  0.020  1.090
 AUI  C27  H22  single    0.970  0.020  1.090
 AUI  C20  H23  single    0.970  0.020  1.090
 AUI  C20  H24  single    0.970  0.020  1.090
 AUI  C21  H25  single    0.970  0.020  1.090
 AUI  O28  H26  single    0.850  0.020  0.980
 AUI  C22  H27  single    0.930  0.020  1.080
 AUI  C24  H28  single    0.970  0.020  1.090
 AUI  C24  H29  single    0.970  0.020  1.090
 AUI  C24  H30  single    0.970  0.020  1.090
 AUI  C25  H31  single    0.970  0.020  1.090
 AUI  C25  H32  single    0.970  0.020  1.090
 AUI  C25  H33  single    0.970  0.020  1.090
 AUI  N10  H34  single    0.860  0.020  1.020

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
 AUI  C2   C1   C4   115.91  3.000
 AUI  C4   C1   O13  121.20  3.000
 AUI  C2   C1   O13  122.89  3.000
 AUI  C9   C4   C5   118.58  3.000
 AUI  C5   C4   C1   121.07  3.000
 AUI  C9   C4   C1   120.36  3.000
 AUI  H1   C5   C6   120.30  3.000
 AUI  H1   C5   C4   118.76  3.000
 AUI  C6   C5   C4   120.94  3.000
 AUI  H2   C6   C7   119.98  3.000
 AUI  H2   C6   C5   120.27  3.000
 AUI  C7   C6   C5   119.74  3.000
 AUI  H3   C7   C8   119.47  3.000
 AUI  H3   C7   C6   119.89  3.000
 AUI  C8   C7   C6   120.64  3.000
 AUI  H4   C8   C9   119.78  3.000
 AUI  H4   C8   C7   120.76  3.000
 AUI  C9   C8   C7   119.46  3.000
 AUI  N10  C9   C8   120.44  3.000
 AUI  C8   C9   C4   120.64  3.000
 AUI  N10  C9   C4   118.92  3.000
 AUI  H34  N10  C3   118.56  3.000
 AUI  H34  N10  C9   118.26  3.000
 AUI  C3   N10  C9   123.18  3.000
 AUI  C2   C3   C11  123.25  3.000
 AUI  C2   C3   N10  121.10  3.000
 AUI  C11  C3   N10  115.64  3.000
 AUI  H7   C11  H6   107.38  3.000
 AUI  H7   C11  H5   107.84  3.000
 AUI  H6   C11  H5   107.80  3.000
 AUI  H7   C11  C3   110.89  3.000
 AUI  H6   C11  C3   111.03  3.000
 AUI  H5   C11  C3   111.72  3.000
 AUI  C12  C2   C3   121.54  3.000
 AUI  C3   C2   C1   120.53  3.000
 AUI  C12  C2   C1   117.85  3.000
 AUI  H10  C12  H9   106.29  3.000
 AUI  H10  C12  C14  109.23  3.000
 AUI  H9   C12  C14  111.21  3.000
 AUI  H10  C12  C2   110.30  3.000
 AUI  H9   C12  C2   109.22  3.000
 AUI  C14  C12  C2   110.51  3.000
 AUI  H11  C14  C15  117.24  3.000
 AUI  H11  C14  C12  114.38  3.000
 AUI  C15  C14  C12  128.34  3.000
 AUI  C16  C15  C26  115.40  3.000
 AUI  C26  C15  C14  124.74  3.000
 AUI  C16  C15  C14  119.84  3.000
 AUI  H14  C26  H13  107.09  3.000
 AUI  H14  C26  H12  108.05  3.000
 AUI  H13  C26  H12  106.71  3.000
 AUI  H14  C26  C15  113.25  3.000
 AUI  H13  C26  C15  111.17  3.000
 AUI  H12  C26  C15  110.28  3.000
 AUI  H16  C16  H15  106.53  3.000
 AUI  H16  C16  C17  108.36  3.000
 AUI  H15  C16  C17  108.84  3.000
 AUI  H16  C16  C15  110.04  3.000
 AUI  H15  C16  C15  109.90  3.000
 AUI  C17  C16  C15  112.95  3.000
 AUI  H18  C17  H17  106.32  3.000
 AUI  H18  C17  C18  109.00  3.000
 AUI  H17  C17  C18  111.64  3.000
 AUI  H18  C17  C16  109.56  3.000
 AUI  H17  C17  C16  108.54  3.000
 AUI  C18  C17  C16  111.64  3.000
 AUI  H19  C18  C19  117.44  3.000
 AUI  H19  C18  C17  115.11  3.000
 AUI  C19  C18  C17  127.39  3.000
 AUI  C20  C19  C27  116.63  3.000
 AUI  C20  C19  C18  119.48  3.000
 AUI  C27  C19  C18  123.88  3.000
 AUI  H22  C27  H21  107.53  3.000
 AUI  H22  C27  H20  107.72  3.000
 AUI  H21  C27  H20  106.63  3.000
 AUI  H22  C27  C19  113.06  3.000
 AUI  H21  C27  C19  110.91  3.000
 AUI  H20  C27  C19  110.71  3.000
 AUI  H24  C20  H23  106.30  3.000
 AUI  H24  C20  C21  106.99  3.000
 AUI  H23  C20  C21  109.07  3.000
 AUI  H24  C20  C19  109.74  3.000
 AUI  H23  C20  C19  110.33  3.000
 AUI  C21  C20  C19  114.08  3.000
 AUI  H25  C21  C22  110.53  3.000
 AUI  H25  C21  O28  104.97  3.000
 AUI  C22  C21  O28  110.85  3.000
 AUI  H25  C21  C20  107.45  3.000
 AUI  O28  C21  C20  112.67  3.000
 AUI  C22  C21  C20  110.20  3.000
 AUI  H26  O28  C21  108.37  3.000
 AUI  H27  C22  C23  117.87  3.000
 AUI  H27  C22  C21  114.39  3.000
 AUI  C23  C22  C21  127.72  3.000
 AUI  C25  C23  C24  114.15  3.000
 AUI  C25  C23  C22  124.84  3.000
 AUI  C24  C23  C22  121.01  3.000
 AUI  H30  C24  H29  108.09  3.000
 AUI  H30  C24  H28  108.02  3.000
 AUI  H29  C24  H28  106.43  3.000
 AUI  H30  C24  C23  112.39  3.000
 AUI  H29  C24  C23  110.87  3.000
 AUI  H28  C24  C23  110.80  3.000
 AUI  H33  C25  H32  107.50  3.000
 AUI  H33  C25  H31  107.89  3.000
 AUI  H32  C25  H31  106.40  3.000
 AUI  H33  C25  C23  113.96  3.000
 AUI  H32  C25  C23  110.24  3.000
 AUI  H31  C25  C23  110.52  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
 AUI  CONST_01  C7   C8   C9   C4      0.00   0.0  0
 AUI  CONST_02  C7   C6   C5   C4      0.00   0.0  0
 AUI  CONST_03  C8   C9   C4   C5      0.00   0.0  0
 AUI  CONST_04  C8   C7   C6   C5      0.00   0.0  0
 AUI  CONST_05  C9   C4   C5   C6      0.00   0.0  0
 AUI  CONST_06  C9   C8   C7   C6      0.00   0.0  0
 AUI  CONST_07  H1   C5   C4   C1      0.00   0.0  0
 AUI  CONST_08  H4   C8   C9   C4    180.00   0.0  0
 AUI  CONST_09  H2   C6   C5   C4    180.00   0.0  0
 AUI  CONST_10  H3   C7   C6   C5    180.00   0.0  0
 AUI  Var_01    C14  C12  C2   C1    -84.81  30.0  3
 AUI  Var_02    H5   C11  C3   N10     3.25  30.0  3
 AUI  Var_03    C15  C14  C12  C2    113.10  30.0  3
 AUI  Var_04    C16  C15  C14  C12  -176.75   0.0  2
 AUI  Var_05    C27  C19  C18  C17     2.51   0.0  2
 AUI  Var_06    C24  C23  C22  C21  -178.47   0.0  2
 AUI  Var_07    C17  C16  C15  C14   107.25  30.0  2
 AUI  Var_08    C18  C17  C16  C15   178.63  30.0  1
 AUI  Var_09    C19  C18  C17  C16    95.07  30.0  3
 AUI  Var_10    C21  C20  C19  C18    93.09  30.0  3
 AUI  Var_11    H12  C26  C15  C14   128.35  30.0  3
 AUI  Var_12    H20  C27  C19  C18   132.86  30.0  3
 AUI  Var_13    H28  C24  C23  C22   122.10  30.0  3
 AUI  Var_14    H31  C25  C23  C22   127.80  30.0  3

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
 AUI  chir_01  C21  C22  C20  O28  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
 AUI  plan-1  O13  0.020
 AUI  plan-1  C1   0.020
 AUI  plan-1  C4   0.020
 AUI  plan-1  C5   0.020
 AUI  plan-1  C6   0.020
 AUI  plan-1  C7   0.020
 AUI  plan-1  C8   0.020
 AUI  plan-1  C9   0.020
 AUI  plan-1  N10  0.020
 AUI  plan-1  C3   0.020
 AUI  plan-1  C11  0.020
 AUI  plan-1  C2   0.020
 AUI  plan-1  C12  0.020
 AUI  plan-1  H1   0.020
 AUI  plan-1  H2   0.020
 AUI  plan-1  H3   0.020
 AUI  plan-1  H4   0.020
 AUI  plan-1  H34  0.020
 AUI  plan-2  C12  0.020
 AUI  plan-2  C14  0.020
 AUI  plan-2  C15  0.020
 AUI  plan-2  C26  0.020
 AUI  plan-2  C16  0.020
 AUI  plan-2  H11  0.020
 AUI  plan-3  C21  0.020
 AUI  plan-3  C22  0.020
 AUI  plan-3  C23  0.020
 AUI  plan-3  C24  0.020
 AUI  plan-3  C25  0.020
 AUI  plan-3  H27  0.020
 AUI  plan-4  C17  0.020
 AUI  plan-4  C18  0.020
 AUI  plan-4  C19  0.020
 AUI  plan-4  C27  0.020
 AUI  plan-4  C20  0.020
 AUI  plan-4  H19  0.020

