# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May  4 20:27:05 2020
#   Inital geometry file: a 134 line input string
#   Ligand name: (E)-3-[4-[(1R,3R)-3-methyl-2-(2-methylpropyl)-6-oxidanyl-3,4-dihydro-1H-isoquinolin-1-yl]phenyl]prop-2-enoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)CN1[C@H](C)Cc2cc(O)ccc2[C@H]1c3ccc(\C=C\C(O)=O)cc3
#
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
 GQD  GQD  '(E)-3-[4-[(1R,3R)-3-methyl-2-(2-methylpropyl)-6-oxidanyl-3,4-dihydro-1H-isoquinolin-1-yl]phenyl]prop-2-enoic acid'  ligand  53  27  .  2021-08-10  2021-08-10  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_GQD
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
 GQD  C1    C  CH3    0  -0.673   4.2362  -1.6318   0.7966
 GQD  C2    C  CH1    0  -0.126   3.2062  -1.6026  -0.3350
 GQD  C4    C  CH2    0  -0.482   3.4422  -0.4449  -1.2942
 GQD  C5    C  CR6    0   0.070   3.0968   0.8595  -0.6419
 GQD  C6    C  CR16   0  -0.399   3.7244   2.0363  -1.0393
 GQD  C7    C  CR6    0   0.350   3.4368   3.2437  -0.4165
 GQD  C8    C  CR16   0  -0.389   2.5209   3.2679   0.6336
 GQD  C9    C  CR16   0  -0.265   1.9010   2.0936   1.0227
 GQD  C10   C  CR6    0   0.060   2.1643   0.8807   0.3923
 GQD  C11   C  CH1    0  -0.148   1.4424  -0.3732   0.8557
 GQD  N13   N  NT     0  -0.442   1.8159  -1.5489   0.0917
 GQD  C14   C  CH2    0  -0.237   1.3163  -2.7683   0.6957
 GQD  C15   C  CH1    0  -0.273   1.2503  -3.9657  -0.2532
 GQD  C16   C  CH3    0  -0.651   0.5932  -5.1368   0.4697
 GQD  C17   C  CH3    0  -0.644   0.5051  -3.6226  -1.5365
 GQD  C18   C  CR6    0   0.110  -0.0527  -0.1395   0.7399
 GQD  C19   C  CR16   0  -0.307  -0.8244   0.1503   1.8557
 GQD  C20   C  CR16   0  -0.308  -2.1809   0.4231   1.7313
 GQD  C21   C  CR6    0   0.140  -2.8104   0.4064   0.4870
 GQD  C22   C  CR16   0  -0.312  -2.0259   0.0961  -0.6323
 GQD  C23   C  CR16   0  -0.245  -0.6771  -0.1711  -0.5076
 GQD  C24   C  C1     0  -0.251  -4.2400   0.7090   0.4091
 GQD  C25   C  C1     0  -0.441  -5.0012   0.7453  -0.6874
 GQD  C26   C  C      0   0.401  -6.4756   1.0764  -0.6606
 GQD  O27   O  OC    -1  -0.617  -7.0485   1.0566  -1.7703
 GQD  O28   O  O      0  -0.601  -6.9961   1.3391   0.4423
 GQD  O29   O  OH1    0  -0.637   4.0731   4.3508  -0.8545
 GQD  H11C  H  HCH3   0   0.224   4.2122  -0.7223   1.3995
 GQD  H12C  H  HCH3   0   0.233   4.0743  -2.4783   1.4652
 GQD  H13C  H  HCH3   0   0.231   5.2430  -1.7302   0.3880
 GQD  H2    H  HCH1   0   0.245   3.3221  -2.5223  -0.9125
 GQD  H41C  H  HCH2   0   0.240   4.4803  -0.4337  -1.6341
 GQD  H42C  H  HCH2   0   0.254   2.8240  -0.5951  -2.1846
 GQD  H6    H  HCR6   0   0.251   4.4558   2.0094  -1.8395
 GQD  H8    H  HCR6   0   0.266   2.2937   4.1962   1.1459
 GQD  H29   H  HOH1   0   0.473   3.8064   5.1167  -0.3346
 GQD  H9    H  HCR6   0   0.252   1.1912   2.1308   1.8406
 GQD  H11   H  HCH1   0   0.231   1.6683  -0.5043   1.9303
 GQD  H141  H  HCH2   0   0.203   1.8862  -3.0522   1.5966
 GQD  H142  H  HCH2   0   0.227   0.2964  -2.5733   1.0403
 GQD  H15   H  HCH1   0   0.219   2.2672  -4.2756  -0.5185
 GQD  H161  H  HCH3   0   0.228   0.5657  -6.0259  -0.1621
 GQD  H162  H  HCH3   0   0.224   1.1304  -5.3973   1.3838
 GQD  H163  H  HCH3   0   0.214  -0.4361  -4.8962   0.7472
 GQD  H171  H  HCH3   0   0.233   0.9918  -2.8110  -2.0778
 GQD  H172  H  HCH3   0   0.218   0.4500  -4.4880  -2.1992
 GQD  H173  H  HCH3   0   0.209  -0.5165  -3.3005  -1.3191
 GQD  H19   H  HCR6   0   0.247  -0.3654   0.1636   2.8380
 GQD  H23   H  HCR6   0   0.247  -0.0948  -0.4184  -1.3863
 GQD  H20   H  HCR6   0   0.249  -2.7611   0.6487   2.6186
 GQD  H22   H  HCR6   0   0.243  -2.4739   0.0634  -1.6176
 GQD  H24   H  H      0   0.234  -4.7183   0.9291   1.3595
 GQD  H25   H  H      0   0.225  -4.5760   0.5325  -1.6641

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
 GQD  C1   C2    single    1.530  0.020  1.530
 GQD  C2   C4    single    1.522  0.020  1.522
 GQD  C2   N13   single    1.455  0.020  1.455
 GQD  C4   C5    single    1.499  0.020  1.499
 GQD  C5   C6    aromatic  1.392  0.020  1.392
 GQD  C5   C10   aromatic  1.393  0.020  1.393
 GQD  C6   C7    aromatic  1.389  0.020  1.389
 GQD  C7   C8    aromatic  1.394  0.020  1.394
 GQD  C7   O29   single    1.350  0.020  1.350
 GQD  C8   C9    aromatic  1.384  0.020  1.384
 GQD  C9   C10   aromatic  1.392  0.020  1.392
 GQD  C10  C11   single    1.519  0.020  1.519
 GQD  C11  N13   single    1.451  0.020  1.451
 GQD  C11  C18   single    1.518  0.020  1.518
 GQD  N13  C14   single    1.450  0.020  1.450
 GQD  C14  C15   single    1.529  0.020  1.529
 GQD  C15  C16   single    1.525  0.020  1.525
 GQD  C15  C17   single    1.523  0.020  1.523
 GQD  C18  C19   aromatic  1.387  0.020  1.387
 GQD  C18  C23   aromatic  1.395  0.020  1.395
 GQD  C19  C20   aromatic  1.389  0.020  1.389
 GQD  C20  C21   aromatic  1.395  0.020  1.395
 GQD  C21  C22   aromatic  1.402  0.020  1.402
 GQD  C21  C24   single    1.463  0.020  1.463
 GQD  C22  C23   aromatic  1.381  0.020  1.381
 GQD  C24  C25   double    1.335  0.020  1.335
 GQD  C25  C26   single    1.511  0.020  1.511
 GQD  C26  O27   deloc     1.249  0.020  1.249
 GQD  C26  O28   deloc     1.248  0.020  1.248
 GQD  C1   H11C  single    0.970  0.020  1.090
 GQD  C1   H12C  single    0.970  0.020  1.090
 GQD  C1   H13C  single    0.970  0.020  1.090
 GQD  C2   H2    single    0.970  0.020  1.090
 GQD  C4   H41C  single    0.970  0.020  1.090
 GQD  C4   H42C  single    0.970  0.020  1.090
 GQD  C6   H6    single    0.930  0.020  1.080
 GQD  C8   H8    single    0.930  0.020  1.080
 GQD  O29  H29   single    0.850  0.020  0.980
 GQD  C9   H9    single    0.930  0.020  1.080
 GQD  C11  H11   single    0.970  0.020  1.090
 GQD  C14  H141  single    0.970  0.020  1.090
 GQD  C14  H142  single    0.970  0.020  1.090
 GQD  C15  H15   single    0.970  0.020  1.090
 GQD  C16  H161  single    0.970  0.020  1.090
 GQD  C16  H162  single    0.970  0.020  1.090
 GQD  C16  H163  single    0.970  0.020  1.090
 GQD  C17  H171  single    0.970  0.020  1.090
 GQD  C17  H172  single    0.970  0.020  1.090
 GQD  C17  H173  single    0.970  0.020  1.090
 GQD  C19  H19   single    0.930  0.020  1.080
 GQD  C23  H23   single    0.930  0.020  1.080
 GQD  C20  H20   single    0.930  0.020  1.080
 GQD  C22  H22   single    0.930  0.020  1.080
 GQD  C24  H24   single    0.930  0.020  1.080
 GQD  C25  H25   single    0.930  0.020  1.080

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
 GQD  H13C  C1   H12C  107.25  3.000
 GQD  H13C  C1   H11C  107.60  3.000
 GQD  H12C  C1   H11C  107.75  3.000
 GQD  H13C  C1   C2    110.23  3.000
 GQD  H12C  C1   C2    111.60  3.000
 GQD  H11C  C1   C2    112.19  3.000
 GQD  H2    C2   N13   106.70  3.000
 GQD  H2    C2   C4    106.91  3.000
 GQD  N13   C2   C4    107.75  3.000
 GQD  H2    C2   C1    107.67  3.000
 GQD  N13   C2   C1    115.27  3.000
 GQD  C4    C2   C1    112.10  3.000
 GQD  H42C  C4   H41C  106.56  3.000
 GQD  H42C  C4   C5    110.08  3.000
 GQD  H41C  C4   C5    110.21  3.000
 GQD  H42C  C4   C2    108.71  3.000
 GQD  H41C  C4   C2    110.57  3.000
 GQD  C5    C4   C2    110.61  3.000
 GQD  C10   C5   C6    120.07  3.000
 GQD  C10   C5   C4    119.39  3.000
 GQD  C6    C5   C4    120.52  3.000
 GQD  H6    C6   C7    119.49  3.000
 GQD  H6    C6   C5    119.60  3.000
 GQD  C7    C6   C5    120.92  3.000
 GQD  O29   C7   C8    122.68  3.000
 GQD  O29   C7   C6    118.03  3.000
 GQD  C8    C7   C6    119.29  3.000
 GQD  H8    C8   C9    119.99  3.000
 GQD  H8    C8   C7    120.57  3.000
 GQD  C9    C8   C7    119.44  3.000
 GQD  H9    C9   C10   119.72  3.000
 GQD  H9    C9   C8    118.46  3.000
 GQD  C10   C9   C8    121.82  3.000
 GQD  C11   C10  C9    119.41  3.000
 GQD  C11   C10  C5    122.15  3.000
 GQD  C9    C10  C5    118.44  3.000
 GQD  H11   C11  C18   107.08  3.000
 GQD  H11   C11  N13   111.29  3.000
 GQD  C18   C11  N13   109.77  3.000
 GQD  H11   C11  C10   107.28  3.000
 GQD  C18   C11  C10   108.52  3.000
 GQD  N13   C11  C10   112.69  3.000
 GQD  C14   N13  C11   111.93  3.000
 GQD  C14   N13  C2    114.86  3.000
 GQD  C11   N13  C2    115.48  3.000
 GQD  H142  C14  H141  105.68  3.000
 GQD  H142  C14  C15   107.14  3.000
 GQD  H141  C14  C15   109.12  3.000
 GQD  H142  C14  N13   107.61  3.000
 GQD  H141  C14  N13   112.26  3.000
 GQD  C15   C14  N13   114.52  3.000
 GQD  H15   C15  C17   108.28  3.000
 GQD  H15   C15  C16   107.30  3.000
 GQD  C17   C15  C16   111.20  3.000
 GQD  H15   C15  C14   109.37  3.000
 GQD  C17   C15  C14   111.57  3.000
 GQD  C16   C15  C14   109.01  3.000
 GQD  H163  C16  H162  107.66  3.000
 GQD  H163  C16  H161  107.63  3.000
 GQD  H162  C16  H161  107.63  3.000
 GQD  H163  C16  C15   110.92  3.000
 GQD  H162  C16  C15   111.59  3.000
 GQD  H161  C16  C15   111.23  3.000
 GQD  H173  C17  H172  107.89  3.000
 GQD  H173  C17  H171  107.26  3.000
 GQD  H172  C17  H171  108.14  3.000
 GQD  H173  C17  C15   110.86  3.000
 GQD  H172  C17  C15   110.96  3.000
 GQD  H171  C17  C15   111.57  3.000
 GQD  C23   C18  C19   118.35  3.000
 GQD  C23   C18  C11   120.37  3.000
 GQD  C19   C18  C11   121.25  3.000
 GQD  H19   C19  C20   119.47  3.000
 GQD  H19   C19  C18   119.72  3.000
 GQD  C20   C19  C18   120.81  3.000
 GQD  H20   C20  C21   119.43  3.000
 GQD  H20   C20  C19   119.35  3.000
 GQD  C21   C20  C19   121.22  3.000
 GQD  C24   C21  C22   123.38  3.000
 GQD  C24   C21  C20   119.08  3.000
 GQD  C22   C21  C20   117.55  3.000
 GQD  H22   C22  C23   118.72  3.000
 GQD  H22   C22  C21   120.11  3.000
 GQD  C23   C22  C21   121.17  3.000
 GQD  H23   C23  C22   119.75  3.000
 GQD  H23   C23  C18   119.35  3.000
 GQD  C22   C23  C18   120.90  3.000
 GQD  H24   C24  C25   117.51  3.000
 GQD  H24   C24  C21   115.17  3.000
 GQD  C25   C24  C21   127.31  3.000
 GQD  H25   C25  C26   116.15  3.000
 GQD  H25   C25  C24   120.66  3.000
 GQD  C26   C25  C24   123.19  3.000
 GQD  O28   C26  O27   126.68  3.000
 GQD  O28   C26  C25   117.96  3.000
 GQD  O27   C26  C25   115.36  3.000
 GQD  H29   O29  C7    110.27  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
 GQD  CONST_01  C8    C7   C6   C5      0.00   0.0  0
 GQD  CONST_02  C8    C9   C10  C5      0.00   0.0  0
 GQD  CONST_03  C9    C10  C5   C6      0.00   0.0  0
 GQD  CONST_04  C9    C8   C7   C6      0.00   0.0  0
 GQD  CONST_05  C10   C5   C6   C7      0.00   0.0  0
 GQD  CONST_06  C10   C9   C8   C7      0.00   0.0  0
 GQD  CONST_07  C21   C20  C19  C18     0.00   0.0  0
 GQD  CONST_08  C21   C22  C23  C18     0.00   0.0  0
 GQD  CONST_09  C22   C23  C18  C19     0.00   0.0  0
 GQD  CONST_10  C22   C21  C20  C19     0.00   0.0  0
 GQD  CONST_11  C23   C18  C19  C20     0.00   0.0  0
 GQD  CONST_12  C23   C22  C21  C20     0.00   0.0  0
 GQD  CONST_13  C20   C19  C18  C11   180.00   0.0  0
 GQD  CONST_14  C22   C23  C18  C11   180.00   0.0  0
 GQD  CONST_15  O29   C7   C6   C5    180.00   0.0  0
 GQD  CONST_16  O29   C7   C8   C9    180.00   0.0  0
 GQD  CONST_17  C24   C21  C20  C19   180.00   0.0  0
 GQD  CONST_18  C24   C21  C22  C23   180.00   0.0  0
 GQD  CONST_19  H6    C6   C5   C4      0.00   0.0  0
 GQD  CONST_20  H9    C9   C10  C5    180.00   0.0  0
 GQD  CONST_21  H8    C8   C7   C6    180.00   0.0  0
 GQD  CONST_22  H19   C19  C18  C11     0.00   0.0  0
 GQD  CONST_23  H23   C23  C18  C11     0.00   0.0  0
 GQD  CONST_24  H20   C20  C19  C18   180.00   0.0  0
 GQD  CONST_25  H22   C22  C23  C18   180.00   0.0  0
 GQD  Var_01    C6    C5   C4   C2    152.37  30.0  1
 GQD  Var_02    C15   C14  N13  C2    -65.38  30.0  3
 GQD  Var_03    C25   C24  C21  C20   179.69  30.0  2
 GQD  Var_04    C26   C25  C24  C21  -179.72   0.0  2
 GQD  Var_05    C16   C15  C14  N13  -174.88  30.0  3
 GQD  Var_06    O27   C26  C25  C24  -179.38  30.0  2
 GQD  Var_07    H161  C16  C15  C14  -177.59  30.0  3
 GQD  Var_08    H171  C17  C15  C14    60.25  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
 GQD  chir_01  C2   C1   C4   N13  positiv
 GQD  chir_02  C11  N13  C18  C10  positiv

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
 GQD  plan-1  C11  0.020
 GQD  plan-1  C18  0.020
 GQD  plan-1  C19  0.020
 GQD  plan-1  C20  0.020
 GQD  plan-1  C21  0.020
 GQD  plan-1  C22  0.020
 GQD  plan-1  C23  0.020
 GQD  plan-1  C24  0.020
 GQD  plan-1  H19  0.020
 GQD  plan-1  H23  0.020
 GQD  plan-1  H20  0.020
 GQD  plan-1  H22  0.020
 GQD  plan-2  C4   0.020
 GQD  plan-2  C5   0.020
 GQD  plan-2  C6   0.020
 GQD  plan-2  C7   0.020
 GQD  plan-2  C8   0.020
 GQD  plan-2  C9   0.020
 GQD  plan-2  C10  0.020
 GQD  plan-2  C11  0.020
 GQD  plan-2  O29  0.020
 GQD  plan-2  H6   0.020
 GQD  plan-2  H8   0.020
 GQD  plan-2  H9   0.020
 GQD  plan-3  C25  0.020
 GQD  plan-3  C26  0.020
 GQD  plan-3  O27  0.020
 GQD  plan-3  O28  0.020
 GQD  plan-4  C21  0.020
 GQD  plan-4  C24  0.020
 GQD  plan-4  C25  0.020
 GQD  plan-4  C26  0.020
 GQD  plan-4  H24  0.020
 GQD  plan-4  H25  0.020

