# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 28 19:20:31 2020
#   Inital geometry file: a 144 line input string
#   Ligand name: 15-(ethylamino)retinal
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCNC(=O)/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C
#
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
 ETR  ETR  '15-(ethylamino)retinal   '  ligand  57  24  .  2021-08-08  2021-08-08  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_ETR
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
 ETR  C1    C  CT    0  -0.123  29.8612  21.5827  45.0930
 ETR  C2    C  CH2   0  -0.422  29.2242  21.6074  43.6734
 ETR  C3    C  CH2   0  -0.437  29.5387  20.4049  42.7921
 ETR  C4    C  CH2   0  -0.495  30.9318  19.8630  43.0786
 ETR  C5    C  C     0   0.044  31.0145  19.4400  44.5210
 ETR  C6    C  C     0   0.124  30.4591  20.2230  45.4621
 ETR  C7    C  C1    0  -0.314  30.4768  19.8930  46.8920
 ETR  C8    C  C1    0  -0.266  31.5767  19.6076  47.6070
 ETR  C9    C  C     0   0.127  31.5976  19.2907  49.0264
 ETR  C10   C  C1    0  -0.309  32.7960  19.0298  49.6029
 ETR  C11   C  C1    0  -0.239  33.0391  18.7135  50.9847
 ETR  C12   C  C1    0  -0.296  34.2694  18.4446  51.4668
 ETR  C13   C  C     0   0.193  34.5763  18.1247  52.8525
 ETR  C14   C  C1    0  -0.482  35.8676  17.8585  53.1478
 ETR  C15   C  C     0   0.559  36.4562  17.5038  54.4563
 ETR  O     O  O     0  -0.504  35.8248  17.3397  55.4975
 ETR  N     N  NH1   0  -0.641  37.7963  17.3535  54.4112
 ETR  C16   C  CH3   0  -0.681  28.7996  22.0399  46.0993
 ETR  C17   C  CH3   0  -0.637  31.0203  22.5930  45.1505
 ETR  C18   C  CH3   0  -0.737  31.6631  18.1116  44.7659
 ETR  C19   C  CH3   0  -0.761  30.2941  19.2720  49.7647
 ETR  C20   C  CH3   0  -0.777  33.4417  18.1218  53.8319
 ETR  C21   C  CH2   0  -0.290  38.6012  17.0676  55.5782
 ETR  C22   C  CH3   0  -0.662  38.9414  18.3065  56.3949
 ETR  H21   H  HCH2  0   0.232  28.1397  21.7012  43.7673
 ETR  H22   H  HCH2  0   0.223  29.5578  22.5188  43.1700
 ETR  H31   H  HCH2  0   0.217  28.8182  19.6038  42.9772
 ETR  H32   H  HCH2  0   0.228  29.4367  20.6785  41.7395
 ETR  H41   H  HCH2  0   0.237  31.1543  19.0164  42.4253
 ETR  H42   H  HCH2  0   0.234  31.6861  20.6265  42.8531
 ETR  H7    H  H     0   0.254  29.5200  19.9257  47.4051
 ETR  H8    H  H     0   0.239  32.5419  19.6244  47.1083
 ETR  H10   H  H     0   0.241  33.6749  19.0624  48.9642
 ETR  H11   H  H     0   0.259  32.1938  18.6969  51.6621
 ETR  H12   H  H     0   0.244  35.1096  18.4594  50.7779
 ETR  H14   H  H     0   0.251  36.5760  17.9106  52.3269
 ETR  HN    H  HNH1  0   0.400  38.2804  17.5532  53.5516
 ETR  H161  H  HCH3  0   0.228  29.2110  22.1923  47.0987
 ETR  H162  H  HCH3  0   0.234  28.3774  22.9934  45.7757
 ETR  H163  H  HCH3  0   0.229  27.9766  21.3259  46.1746
 ETR  H171  H  HCH3  0   0.225  31.4895  22.5977  46.1365
 ETR  H172  H  HCH3  0   0.228  31.7926  22.3644  44.4142
 ETR  H173  H  HCH3  0   0.221  30.6583  23.6040  44.9462
 ETR  H181  H  HCH3  0   0.241  31.5315  17.7454  45.7811
 ETR  H182  H  HCH3  0   0.234  31.2587  17.3657  44.0768
 ETR  H183  H  HCH3  0   0.237  32.7376  18.1597  44.5678
 ETR  H191  H  HCH3  0   0.257  30.4047  19.0314  50.8185
 ETR  H192  H  HCH3  0   0.247  29.7955  20.2415  49.7003
 ETR  H193  H  HCH3  0   0.250  29.6140  18.5375  49.3295
 ETR  H201  H  HCH3  0   0.280  33.7703  17.9191  54.8429
 ETR  H202  H  HCH3  0   0.245  32.9296  19.0857  53.8188
 ETR  H203  H  HCH3  0   0.247  32.7009  17.3690  53.5539
 ETR  H211  H  HCH2  0   0.238  38.0779  16.3407  56.1997
 ETR  H212  H  HCH2  0   0.245  39.5150  16.5862  55.2307
 ETR  H221  H  HCH3  0   0.229  39.5656  18.0363  57.2474
 ETR  H222  H  HCH3  0   0.225  39.4883  19.0345  55.7951
 ETR  H223  H  HCH3  0   0.230  38.0404  18.7855  56.7769

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
 ETR  C1   C2    single  1.556  0.020  1.556
 ETR  C1   C6    single  1.530  0.020  1.530
 ETR  C1   C16   single  1.533  0.020  1.533
 ETR  C1   C17   single  1.539  0.020  1.539
 ETR  C2   C3    single  1.524  0.020  1.524
 ETR  C2   H21   single  0.970  0.020  1.090
 ETR  C2   H22   single  0.970  0.020  1.090
 ETR  C3   C4    single  1.522  0.020  1.522
 ETR  C3   H31   single  0.970  0.020  1.090
 ETR  C3   H32   single  0.970  0.020  1.090
 ETR  C4   C5    single  1.505  0.020  1.505
 ETR  C4   H41   single  0.970  0.020  1.090
 ETR  C4   H42   single  0.970  0.020  1.090
 ETR  C5   C6    double  1.344  0.020  1.344
 ETR  C5   C18   single  1.498  0.020  1.498
 ETR  C6   C7    single  1.468  0.020  1.468
 ETR  C7   C8    double  1.342  0.020  1.342
 ETR  C7   H7    single  0.930  0.020  1.080
 ETR  C8   C9    single  1.454  0.020  1.454
 ETR  C8   H8    single  0.930  0.020  1.080
 ETR  C9   C10   double  1.355  0.020  1.355
 ETR  C9   C19   single  1.498  0.020  1.498
 ETR  C10  C11   single  1.438  0.020  1.438
 ETR  C10  H10   single  0.930  0.020  1.080
 ETR  C11  C12   double  1.348  0.020  1.348
 ETR  C11  H11   single  0.930  0.020  1.080
 ETR  C12  C13   single  1.455  0.020  1.455
 ETR  C12  H12   single  0.930  0.020  1.080
 ETR  C13  C14   double  1.351  0.020  1.351
 ETR  C13  C20   single  1.499  0.020  1.499
 ETR  C14  C15   single  1.478  0.020  1.478
 ETR  C14  H14   single  0.930  0.020  1.080
 ETR  C15  O     double  1.229  0.020  1.229
 ETR  C15  N     single  1.349  0.020  1.349
 ETR  N    C21   single  1.446  0.020  1.446
 ETR  N    HN    single  0.860  0.020  1.020
 ETR  C16  H161  single  0.970  0.020  1.090
 ETR  C16  H162  single  0.970  0.020  1.090
 ETR  C16  H163  single  0.970  0.020  1.090
 ETR  C17  H171  single  0.970  0.020  1.090
 ETR  C17  H172  single  0.970  0.020  1.090
 ETR  C17  H173  single  0.970  0.020  1.090
 ETR  C18  H181  single  0.970  0.020  1.090
 ETR  C18  H182  single  0.970  0.020  1.090
 ETR  C18  H183  single  0.970  0.020  1.090
 ETR  C19  H191  single  0.970  0.020  1.090
 ETR  C19  H192  single  0.970  0.020  1.090
 ETR  C19  H193  single  0.970  0.020  1.090
 ETR  C20  H201  single  0.970  0.020  1.090
 ETR  C20  H202  single  0.970  0.020  1.090
 ETR  C20  H203  single  0.970  0.020  1.090
 ETR  C21  C22   single  1.522  0.020  1.522
 ETR  C21  H211  single  0.970  0.020  1.090
 ETR  C21  H212  single  0.970  0.020  1.090
 ETR  C22  H221  single  0.970  0.020  1.090
 ETR  C22  H222  single  0.970  0.020  1.090
 ETR  C22  H223  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
 ETR  C17   C1   C16   107.54  3.000
 ETR  C17   C1   C6    106.26  3.000
 ETR  C16   C1   C6    112.17  3.000
 ETR  C17   C1   C2    109.39  3.000
 ETR  C16   C1   C2    108.10  3.000
 ETR  C6    C1   C2    113.20  3.000
 ETR  H22   C2   H21   105.71  3.000
 ETR  H22   C2   C3    109.18  3.000
 ETR  H21   C2   C3    108.81  3.000
 ETR  H22   C2   C1    107.96  3.000
 ETR  H21   C2   C1    109.23  3.000
 ETR  C3    C2   C1    115.51  3.000
 ETR  H32   C3   H31   106.57  3.000
 ETR  H32   C3   C4    110.86  3.000
 ETR  H31   C3   C4    108.09  3.000
 ETR  H32   C3   C2    109.90  3.000
 ETR  H31   C3   C2    110.14  3.000
 ETR  C4    C3   C2    111.17  3.000
 ETR  H42   C4   H41   106.05  3.000
 ETR  H42   C4   C5    110.79  3.000
 ETR  H41   C4   C5    110.13  3.000
 ETR  H42   C4   C3    110.05  3.000
 ETR  H41   C4   C3    110.48  3.000
 ETR  C5    C4   C3    109.31  3.000
 ETR  C18   C5   C6    125.50  3.000
 ETR  C18   C5   C4    115.44  3.000
 ETR  C6    C5   C4    118.97  3.000
 ETR  C7    C6   C5    123.10  3.000
 ETR  C7    C6   C1    116.07  3.000
 ETR  C5    C6   C1    120.67  3.000
 ETR  H7    C7   C8    118.46  3.000
 ETR  H7    C7   C6    116.28  3.000
 ETR  C8    C7   C6    125.22  3.000
 ETR  H8    C8   C9    116.00  3.000
 ETR  H8    C8   C7    118.69  3.000
 ETR  C9    C8   C7    125.30  3.000
 ETR  C19   C9   C10   123.87  3.000
 ETR  C19   C9   C8    118.11  3.000
 ETR  C10   C9   C8    118.03  3.000
 ETR  H10   C10  C11   115.75  3.000
 ETR  H10   C10  C9    117.34  3.000
 ETR  C11   C10  C9    126.91  3.000
 ETR  H11   C11  C12   119.03  3.000
 ETR  H11   C11  C10   118.18  3.000
 ETR  C12   C11  C10   122.79  3.000
 ETR  H12   C12  C13   116.34  3.000
 ETR  H12   C12  C11   118.43  3.000
 ETR  C13   C12  C11   125.23  3.000
 ETR  C20   C13  C14   125.47  3.000
 ETR  C20   C13  C12   117.59  3.000
 ETR  C14   C13  C12   116.94  3.000
 ETR  H14   C14  C15   114.90  3.000
 ETR  H14   C14  C13   116.67  3.000
 ETR  C15   C14  C13   128.42  3.000
 ETR  N     C15  O     121.59  3.000
 ETR  N     C15  C14   113.12  3.000
 ETR  O     C15  C14   125.28  3.000
 ETR  HN    N    C21   117.43  3.000
 ETR  HN    N    C15   118.96  3.000
 ETR  C21   N    C15   123.22  3.000
 ETR  H163  C16  H162  107.45  3.000
 ETR  H163  C16  H161  108.19  3.000
 ETR  H162  C16  H161  107.16  3.000
 ETR  H163  C16  C1    111.86  3.000
 ETR  H162  C16  C1    109.50  3.000
 ETR  H161  C16  C1    112.45  3.000
 ETR  H173  C17  H172  107.58  3.000
 ETR  H173  C17  H171  107.88  3.000
 ETR  H172  C17  H171  107.82  3.000
 ETR  H173  C17  C1    110.54  3.000
 ETR  H172  C17  C1    111.74  3.000
 ETR  H171  C17  C1    111.12  3.000
 ETR  H183  C18  H182  106.22  3.000
 ETR  H183  C18  H181  107.62  3.000
 ETR  H182  C18  H181  108.30  3.000
 ETR  H183  C18  C5    110.90  3.000
 ETR  H182  C18  C5    109.99  3.000
 ETR  H181  C18  C5    113.51  3.000
 ETR  H193  C19  H192  106.83  3.000
 ETR  H193  C19  H191  107.52  3.000
 ETR  H192  C19  H191  107.48  3.000
 ETR  H193  C19  C9    110.73  3.000
 ETR  H192  C19  C9    110.92  3.000
 ETR  H191  C19  C9    113.09  3.000
 ETR  H203  C20  H202  106.70  3.000
 ETR  H203  C20  H201  108.34  3.000
 ETR  H202  C20  H201  108.61  3.000
 ETR  H203  C20  C13   110.40  3.000
 ETR  H202  C20  C13   110.22  3.000
 ETR  H201  C20  C13   112.39  3.000
 ETR  H212  C21  H211  106.84  3.000
 ETR  H212  C21  C22   110.07  3.000
 ETR  H211  C21  C22   110.13  3.000
 ETR  H212  C21  N     107.26  3.000
 ETR  H211  C21  N     108.94  3.000
 ETR  C22   C21  N     113.36  3.000
 ETR  H223  C22  H222  108.31  3.000
 ETR  H223  C22  H221  107.94  3.000
 ETR  H222  C22  H221  107.96  3.000
 ETR  H223  C22  C21   111.16  3.000
 ETR  H222  C22  C21   111.12  3.000
 ETR  H221  C22  C21   110.23  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
 ETR  CONST_01  C21   N    C15  C14   180.00   0.0  0
 ETR  CONST_02  C21   N    C15  O       0.00   0.0  0
 ETR  CONST_03  HN    N    C15  C14     0.00   0.0  0
 ETR  Var_01    C4    C3   C2   C1    -32.79  30.0  1
 ETR  Var_02    C4    C5   C6   C1     -5.40  30.0  1
 ETR  Var_03    C5    C6   C1   C2     33.25  30.0  1
 ETR  Var_04    C5    C4   C3   C2     59.96  30.0  1
 ETR  Var_05    C6    C1   C2   C3    -11.83  30.0  1
 ETR  Var_06    C6    C5   C4   C3    -41.96  30.0  1
 ETR  Var_07    C8    C7   C6   C1   -121.54  30.0  2
 ETR  Var_08    H161  C16  C1   C2   -171.45  30.0  3
 ETR  Var_09    H171  C17  C1   C2   -179.92  30.0  3
 ETR  Var_10    H181  C18  C5   C4   -168.45  30.0  3
 ETR  Var_11    C9    C8   C7   C6    179.48   0.0  2
 ETR  Var_12    C11   C10  C9   C8    179.18   0.0  2
 ETR  Var_13    C13   C12  C11  C10   179.72   0.0  2
 ETR  Var_14    C15   C14  C13  C12  -179.80   0.0  2
 ETR  Var_15    C10   C9   C8   C7   -179.76  30.0  2
 ETR  Var_16    C12   C11  C10  C9    178.82  30.0  2
 ETR  Var_17    C14   C13  C12  C11   178.79  30.0  2
 ETR  Var_18    O     C15  C14  C13     3.25  30.0  2
 ETR  Var_19    C22   C21  N    C15   -82.23  30.0  3
 ETR  Var_20    H191  C19  C9   C8   -179.71  30.0  3
 ETR  Var_21    H201  C20  C13  C12  -177.34  30.0  3
 ETR  Var_22    H221  C22  C21  N    -178.76  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
 ETR  plan-1  C14  0.020
 ETR  plan-1  C15  0.020
 ETR  plan-1  O    0.020
 ETR  plan-1  N    0.020
 ETR  plan-1  C21  0.020
 ETR  plan-1  HN   0.020
 ETR  plan-2  C6   0.020
 ETR  plan-2  C7   0.020
 ETR  plan-2  C8   0.020
 ETR  plan-2  C9   0.020
 ETR  plan-2  H7   0.020
 ETR  plan-2  H8   0.020
 ETR  plan-3  C8   0.020
 ETR  plan-3  C9   0.020
 ETR  plan-3  C10  0.020
 ETR  plan-3  C11  0.020
 ETR  plan-3  C19  0.020
 ETR  plan-3  H10  0.020
 ETR  plan-4  C10  0.020
 ETR  plan-4  C11  0.020
 ETR  plan-4  C12  0.020
 ETR  plan-4  C13  0.020
 ETR  plan-4  H11  0.020
 ETR  plan-4  H12  0.020
 ETR  plan-5  C12  0.020
 ETR  plan-5  C13  0.020
 ETR  plan-5  C14  0.020
 ETR  plan-5  C15  0.020
 ETR  plan-5  C20  0.020
 ETR  plan-5  H14  0.020

