# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May  4 21:57:41 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  54  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   4.2384  -1.5925   0.7876
 GQD  C2    C  CH1   0  -0.126   3.2063  -1.5550  -0.3415
 GQD  C4    C  CH2   0  -0.483   3.4284  -0.3790  -1.2814
 GQD  C5    C  CR6   0   0.071   3.0666   0.9103  -0.6083
 GQD  C6    C  CR16  0  -0.447   3.6771   2.1032  -0.9910
 GQD  C7    C  CR6   0   0.356   3.3771   3.2963  -0.3489
 GQD  C8    C  CR16  0  -0.344   2.4659   3.2935   0.7067
 GQD  C9    C  CR16  0  -0.264   1.8640   2.1070   1.0797
 GQD  C10   C  CR6   0   0.057   2.1398   0.9056   0.4283
 GQD  C11   C  CH1   0  -0.149   1.4354  -0.3641   0.8743
 GQD  N13   N  NT    0  -0.443   1.8162  -1.5226   0.0895
 GQD  C14   C  CH2   0  -0.238   1.3302  -2.7566   0.6757
 GQD  C15   C  CH1   0  -0.274   1.2780  -3.9403  -0.2907
 GQD  C16   C  CH3   0  -0.651   0.6347  -5.1299   0.4144
 GQD  C17   C  CH3   0  -0.644   0.5300  -3.5868  -1.5695
 GQD  C18   C  CR6   0   0.116  -0.0619  -0.1426   0.7621
 GQD  C19   C  CR16  0  -0.307  -0.8372   0.1093   1.8850
 GQD  C20   C  CR16  0  -0.292  -2.1957   0.3670   1.7643
 GQD  C21   C  CR6   0   0.132  -2.8162   0.3708   0.5154
 GQD  C22   C  CR16  0  -0.301  -2.0302   0.1008  -0.6134
 GQD  C23   C  CR16  0  -0.242  -0.6799  -0.1518  -0.4900
 GQD  C24   C  C1    0  -0.211  -4.2434   0.6514   0.4443
 GQD  C25   C  C1    0  -0.424  -4.9988   0.6885  -0.6604
 GQD  C26   C  C     0   0.534  -6.4350   0.9871  -0.5747
 GQD  O27   O  OH1   0  -0.604  -7.0073   0.9705  -1.7758
 GQD  O28   O  O     0  -0.453  -7.0472   1.2202   0.4433
 GQD  O29   O  OH1   0  -0.636   3.9412   4.4734  -0.6916
 GQD  H11C  H  HCH3  0   0.225   4.2084  -0.6918   1.4033
 GQD  H12C  H  HCH3  0   0.234   4.0845  -2.4495   1.4446
 GQD  H13C  H  HCH3  0   0.232   5.2450  -1.6770   0.3754
 GQD  H2    H  HCH1  0   0.246   3.3301  -2.4633  -0.9350
 GQD  H41C  H  HCH2  0   0.241   4.4673  -0.3497  -1.6181
 GQD  H42C  H  HCH2  0   0.255   2.8145  -0.5211  -2.1760
 GQD  H6    H  HCR6  0   0.260   4.4049   2.0888  -1.7966
 GQD  H8    H  HCR6  0   0.258   2.2369   4.2144   1.2285
 GQD  H29   H  HOH1  0   0.473   4.5488   4.3515  -1.4296
 GQD  H9    H  HCR6  0   0.251   1.1586   2.1226   1.9021
 GQD  H11   H  HCH1  0   0.235   1.6638  -0.5094   1.9463
 GQD  H141  H  HCH2  0   0.205   1.9033  -3.0466   1.5725
 GQD  H142  H  HCH2  0   0.227   0.3080  -2.5785   1.0233
 GQD  H15   H  HCH1  0   0.220   2.2985  -4.2348  -0.5594
 GQD  H161  H  HCH3  0   0.228   0.6215  -6.0103  -0.2299
 GQD  H162  H  HCH3  0   0.224   1.1736  -5.3955   1.3260
 GQD  H163  H  HCH3  0   0.214  -0.3985  -4.9080   0.6928
 GQD  H171  H  HCH3  0   0.233   1.0091  -2.7634  -2.0996
 GQD  H172  H  HCH3  0   0.219   0.4837  -4.4434  -2.2442
 GQD  H173  H  HCH3  0   0.208  -0.4949  -3.2779  -1.3484
 GQD  H19   H  HCR6  0   0.254  -0.3802   0.1035   2.8678
 GQD  H23   H  HCR6  0   0.254  -0.0897  -0.3688  -1.3709
 GQD  H20   H  HCR6  0   0.259  -2.7831   0.5627   2.6536
 GQD  H22   H  HCR6  0   0.254  -2.4751   0.0888  -1.6003
 GQD  H24   H  H     0   0.268  -4.7244   0.8492   1.3977
 GQD  H25   H  H     0   0.280  -4.5899   0.5002  -1.6451
 GQD  H27   H  HOH1  0   0.480  -7.9525   1.1644  -1.6924

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    1.456  0.020  1.456
 GQD  C4   C5    single    1.499  0.020  1.499
 GQD  C5   C6    aromatic  1.394  0.020  1.394
 GQD  C5   C10   aromatic  1.391  0.020  1.391
 GQD  C6   C7    aromatic  1.388  0.020  1.388
 GQD  C7   C8    aromatic  1.395  0.020  1.395
 GQD  C7   O29   single    1.349  0.020  1.349
 GQD  C8   C9    aromatic  1.382  0.020  1.382
 GQD  C9   C10   aromatic  1.394  0.020  1.394
 GQD  C10  C11   single    1.519  0.020  1.519
 GQD  C11  N13   single    1.450  0.020  1.450
 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  1.388  0.020  1.388
 GQD  C18  C23   aromatic  1.396  0.020  1.396
 GQD  C19  C20   aromatic  1.388  0.020  1.388
 GQD  C20  C21   aromatic  1.395  0.020  1.395
 GQD  C21  C22   aromatic  1.402  0.020  1.402
 GQD  C21  C24   single    1.456  0.020  1.456
 GQD  C22  C23   aromatic  1.379  0.020  1.379
 GQD  C24  C25   double    1.339  0.020  1.339
 GQD  C25  C26   single    1.469  0.020  1.469
 GQD  C26  O27   single    1.331  0.020  1.331
 GQD  C26  O28   double    1.211  0.020  1.211
 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
 GQD  O27  H27   single    0.850  0.020  0.980

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  107.27  3.000
 GQD  H13C  C1   H11C  107.61  3.000
 GQD  H12C  C1   H11C  107.74  3.000
 GQD  H13C  C1   C2    110.21  3.000
 GQD  H12C  C1   C2    111.62  3.000
 GQD  H11C  C1   C2    112.18  3.000
 GQD  H2    C2   N13   106.72  3.000
 GQD  H2    C2   C4    106.89  3.000
 GQD  N13   C2   C4    107.76  3.000
 GQD  H2    C2   C1    107.70  3.000
 GQD  N13   C2   C1    115.23  3.000
 GQD  C4    C2   C1    112.10  3.000
 GQD  H42C  C4   H41C  106.56  3.000
 GQD  H42C  C4   C5    110.09  3.000
 GQD  H41C  C4   C5    110.18  3.000
 GQD  H42C  C4   C2    108.82  3.000
 GQD  H41C  C4   C2    110.48  3.000
 GQD  C5    C4   C2    110.62  3.000
 GQD  C10   C5   C6    119.97  3.000
 GQD  C10   C5   C4    119.53  3.000
 GQD  C6    C5   C4    120.49  3.000
 GQD  H6    C6   C7    119.98  3.000
 GQD  H6    C6   C5    119.08  3.000
 GQD  C7    C6   C5    120.94  3.000
 GQD  O29   C7   C8    117.85  3.000
 GQD  O29   C7   C6    122.82  3.000
 GQD  C8    C7   C6    119.33  3.000
 GQD  H8    C8   C9    120.53  3.000
 GQD  H8    C8   C7    120.08  3.000
 GQD  C9    C8   C7    119.39  3.000
 GQD  H9    C9   C10   119.72  3.000
 GQD  H9    C9   C8    118.43  3.000
 GQD  C10   C9   C8    121.85  3.000
 GQD  C11   C10  C9    119.43  3.000
 GQD  C11   C10  C5    122.06  3.000
 GQD  C9    C10  C5    118.51  3.000
 GQD  H11   C11  C18   107.14  3.000
 GQD  H11   C11  N13   111.44  3.000
 GQD  C18   C11  N13   109.61  3.000
 GQD  H11   C11  C10   107.38  3.000
 GQD  C18   C11  C10   108.29  3.000
 GQD  N13   C11  C10   112.77  3.000
 GQD  C14   N13  C11   111.90  3.000
 GQD  C14   N13  C2    114.89  3.000
 GQD  C11   N13  C2    115.38  3.000
 GQD  H142  C14  H141  105.66  3.000
 GQD  H142  C14  C15   107.16  3.000
 GQD  H141  C14  C15   109.15  3.000
 GQD  H142  C14  N13   107.64  3.000
 GQD  H141  C14  N13   112.22  3.000
 GQD  C15   C14  N13   114.50  3.000
 GQD  H15   C15  C17   108.30  3.000
 GQD  H15   C15  C16   107.25  3.000
 GQD  C17   C15  C16   111.23  3.000
 GQD  H15   C15  C14   109.35  3.000
 GQD  C17   C15  C14   111.58  3.000
 GQD  C16   C15  C14   109.02  3.000
 GQD  H163  C16  H162  107.65  3.000
 GQD  H163  C16  H161  107.63  3.000
 GQD  H162  C16  H161  107.62  3.000
 GQD  H163  C16  C15   110.99  3.000
 GQD  H162  C16  C15   111.57  3.000
 GQD  H161  C16  C15   111.19  3.000
 GQD  H173  C17  H172  107.88  3.000
 GQD  H173  C17  H171  107.28  3.000
 GQD  H172  C17  H171  108.11  3.000
 GQD  H173  C17  C15   110.87  3.000
 GQD  H172  C17  C15   110.96  3.000
 GQD  H171  C17  C15   111.57  3.000
 GQD  C23   C18  C19   118.66  3.000
 GQD  C23   C18  C11   120.13  3.000
 GQD  C19   C18  C11   121.19  3.000
 GQD  H19   C19  C20   119.51  3.000
 GQD  H19   C19  C18   119.81  3.000
 GQD  C20   C19  C18   120.68  3.000
 GQD  H20   C20  C21   119.56  3.000
 GQD  H20   C20  C19   119.52  3.000
 GQD  C21   C20  C19   120.92  3.000
 GQD  C24   C21  C22   123.18  3.000
 GQD  C24   C21  C20   118.70  3.000
 GQD  C22   C21  C20   118.11  3.000
 GQD  H22   C22  C23   118.81  3.000
 GQD  H22   C22  C21   120.38  3.000
 GQD  C23   C22  C21   120.81  3.000
 GQD  H23   C23  C22   119.85  3.000
 GQD  H23   C23  C18   119.33  3.000
 GQD  C22   C23  C18   120.82  3.000
 GQD  H24   C24  C25   118.00  3.000
 GQD  H24   C24  C21   115.23  3.000
 GQD  C25   C24  C21   126.77  3.000
 GQD  H25   C25  C26   117.22  3.000
 GQD  H25   C25  C24   122.18  3.000
 GQD  C26   C25  C24   120.60  3.000
 GQD  O28   C26  O27   122.95  3.000
 GQD  O28   C26  C25   125.62  3.000
 GQD  O27   C26  C25   111.43  3.000
 GQD  H27   O27  C26   109.85  3.000
 GQD  H29   O29  C7    110.35  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  CONST_26  H27   O27  C26  C25   180.00   0.0  0
 GQD  Var_01    C6    C5   C4   C2    152.65  30.0  1
 GQD  Var_02    C15   C14  N13  C2    -65.19  30.0  3
 GQD  Var_03    C25   C24  C21  C20  -179.59  30.0  2
 GQD  Var_04    C26   C25  C24  C21   179.99   0.0  2
 GQD  Var_05    C16   C15  C14  N13  -174.91  30.0  3
 GQD  Var_06    O27   C26  C25  C24  -179.69  30.0  2
 GQD  Var_07    H161  C16  C15  C14  -177.37  30.0  3
 GQD  Var_08    H171  C17  C15  C14    60.37  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-3  H27  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

