# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 30 23:58:31 2020
#   Inital geometry file: a 160 line input string
#   Ligand name: 15-[(4-hydroxyphenyl)amino]retinal
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC1=C(\C=C\C(C)=C\C=C\C(C)=C\C(=O)Nc2ccc(O)cc2)C(C)(C)CCC1
#
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
 FEN  FEN  15-[(4-hydroxyphenyl)amino]retinal  ligand  62  29  .  2021-08-09  2021-08-09  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_FEN
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
 FEN  C1    C  CT    0  -0.158  29.7308  21.2136  45.2227
 FEN  C2    C  CH2   0  -0.413  30.0395  21.7742  43.8308
 FEN  C3    C  CH2   0  -0.448  30.1978  20.6801  42.7928
 FEN  C4    C  CH2   0  -0.468  31.3594  19.7791  43.1730
 FEN  C5    C  C     0   0.008  31.3921  19.4009  44.6307
 FEN  C6    C  C     0   0.127  30.6716  20.0545  45.5614
 FEN  C7    C  C1    0  -0.304  30.6793  19.6937  46.9846
 FEN  C8    C  C1    0  -0.267  31.7654  19.5319  47.7561
 FEN  C9    C  C     0   0.129  31.7475  19.2241  49.1770
 FEN  C10   C  C1    0  -0.310  32.9363  19.1150  49.8198
 FEN  C11   C  C1    0  -0.236  33.1382  18.8472  51.2174
 FEN  C12   C  C1    0  -0.297  34.3634  18.7509  51.7736
 FEN  C13   C  C     0   0.199  34.6287  18.5019  53.1812
 FEN  C14   C  C1    0  -0.501  35.9274  18.4392  53.5542
 FEN  C15   C  C     0   0.561  36.4791  18.2010  54.8995
 FEN  C16   C  CH3   0  -0.645  28.2755  20.7265  45.2799
 FEN  C17   C  CH3   0  -0.637  29.9091  22.3508  46.2371
 FEN  C18   C  CH3   0  -0.728  32.2905  18.2314  44.9147
 FEN  C19   C  CH3   0  -0.762  30.4190  19.0485  49.8469
 FEN  C20   C  CH3   0  -0.777  33.4490  18.3435  54.0920
 FEN  C1'   C  CR6   0   0.356  38.7236  18.1706  55.9936
 FEN  C2'   C  CR16  0  -0.342  40.0771  18.3966  55.7250
 FEN  C3'   C  CR16  0  -0.323  41.0375  18.2886  56.7121
 FEN  C4'   C  CR6   0   0.339  40.6690  17.9499  58.0118
 FEN  C5'   C  CR16  0  -0.370  39.3268  17.7212  58.2871
 FEN  C6'   C  CR16  0  -0.306  38.3602  17.8280  57.2956
 FEN  O     O  O     0  -0.480  35.8220  17.9361  55.8983
 FEN  N     N  NH1   0  -0.760  37.8373  18.3053  54.9198
 FEN  O4'   O  OH1   0  -0.636  41.6401  17.8619  58.9459
 FEN  H21   H  HCH2  0   0.225  29.2473  22.4737  43.5479
 FEN  H22   H  HCH2  0   0.220  30.9662  22.3581  43.8747
 FEN  H31   H  HCH2  0   0.221  29.2793  20.0913  42.7242
 FEN  H32   H  HCH2  0   0.232  30.3636  21.1095  41.8025
 FEN  H41   H  HCH2  0   0.233  31.3407  18.8656  42.5708
 FEN  H42   H  HCH2  0   0.233  32.3106  20.2649  42.9208
 FEN  H7    H  H     0   0.252  29.7001  19.6164  47.4512
 FEN  H8    H  H     0   0.243  32.7483  19.6641  47.3131
 FEN  H10   H  H     0   0.242  33.8389  19.2502  49.2299
 FEN  H11   H  H     0   0.259  32.2639  18.7305  51.8464
 FEN  H12   H  H     0   0.245  35.2328  18.8671  51.1323
 FEN  H14   H  H     0   0.256  36.6635  18.5842  52.7700
 FEN  H161  H  HCH3  0   0.229  28.0204  20.3249  46.2621
 FEN  H162  H  HCH3  0   0.226  27.5889  21.5527  45.0794
 FEN  H163  H  HCH3  0   0.230  28.0814  19.9443  44.5452
 FEN  H171  H  HCH3  0   0.226  29.6058  22.0620  47.2447
 FEN  H172  H  HCH3  0   0.225  30.9498  22.6778  46.2845
 FEN  H173  H  HCH3  0   0.225  29.3025  23.2110  45.9446
 FEN  H181  H  HCH3  0   0.246  32.1586  17.8119  45.9086
 FEN  H182  H  HCH3  0   0.233  32.1130  17.4386  44.1845
 FEN  H183  H  HCH3  0   0.237  33.3422  18.5140  44.8108
 FEN  H191  H  HCH3  0   0.257  30.5002  18.8690  50.9155
 FEN  H192  H  HCH3  0   0.247  29.7915  19.9314  49.7107
 FEN  H193  H  HCH3  0   0.251  29.8767  18.2059  49.4134
 FEN  H201  H  HCH3  0   0.280  33.7324  18.2420  55.1313
 FEN  H202  H  HCH3  0   0.247  32.7802  19.1999  53.9950
 FEN  H203  H  HCH3  0   0.251  32.8712  17.4618  53.8072
 FEN  H2'   H  HCR6  0   0.271  40.3880  18.6642  54.7216
 FEN  H3'   H  HCR6  0   0.267  42.0779  18.4694  56.4727
 FEN  H5'   H  HCR6  0   0.271  39.0150  17.4544  59.2906
 FEN  H6'   H  HCR6  0   0.283  37.3318  17.6411  57.5547
 FEN  HN    H  HNH1  0   0.415  38.2795  18.5411  54.0449
 FEN  HO4'  H  HOH1  0   0.473  41.2642  17.6146  59.7980

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
 FEN  C1   C2    single    1.532  0.020  1.532
 FEN  C1   C6    single    1.531  0.020  1.531
 FEN  C1   C16   single    1.536  0.020  1.536
 FEN  C1   C17   single    1.534  0.020  1.534
 FEN  C2   C3    single    1.516  0.020  1.516
 FEN  C2   H21   single    0.970  0.020  1.090
 FEN  C2   H22   single    0.970  0.020  1.090
 FEN  C3   C4    single    1.518  0.020  1.518
 FEN  C3   H31   single    0.970  0.020  1.090
 FEN  C3   H32   single    0.970  0.020  1.090
 FEN  C4   C5    single    1.506  0.020  1.506
 FEN  C4   H41   single    0.970  0.020  1.090
 FEN  C4   H42   single    0.970  0.020  1.090
 FEN  C5   C6    double    1.346  0.020  1.346
 FEN  C5   C18   single    1.502  0.020  1.502
 FEN  C6   C7    single    1.468  0.020  1.468
 FEN  C7   C8    double    1.342  0.020  1.342
 FEN  C7   H7    single    0.930  0.020  1.080
 FEN  C8   C9    single    1.454  0.020  1.454
 FEN  C8   H8    single    0.930  0.020  1.080
 FEN  C9   C10   double    1.356  0.020  1.356
 FEN  C9   C19   single    1.498  0.020  1.498
 FEN  C10  C11   single    1.437  0.020  1.437
 FEN  C10  H10   single    0.930  0.020  1.080
 FEN  C11  C12   double    1.349  0.020  1.349
 FEN  C11  H11   single    0.930  0.020  1.080
 FEN  C12  C13   single    1.454  0.020  1.454
 FEN  C12  H12   single    0.930  0.020  1.080
 FEN  C13  C14   double    1.353  0.020  1.353
 FEN  C13  C20   single    1.499  0.020  1.499
 FEN  C14  C15   single    1.473  0.020  1.473
 FEN  C14  H14   single    0.930  0.020  1.080
 FEN  C15  O     double    1.225  0.020  1.225
 FEN  C15  N     single    1.362  0.020  1.362
 FEN  C16  H161  single    0.970  0.020  1.090
 FEN  C16  H162  single    0.970  0.020  1.090
 FEN  C16  H163  single    0.970  0.020  1.090
 FEN  C17  H171  single    0.970  0.020  1.090
 FEN  C17  H172  single    0.970  0.020  1.090
 FEN  C17  H173  single    0.970  0.020  1.090
 FEN  C18  H181  single    0.970  0.020  1.090
 FEN  C18  H182  single    0.970  0.020  1.090
 FEN  C18  H183  single    0.970  0.020  1.090
 FEN  C19  H191  single    0.970  0.020  1.090
 FEN  C19  H192  single    0.970  0.020  1.090
 FEN  C19  H193  single    0.970  0.020  1.090
 FEN  C20  H201  single    0.970  0.020  1.090
 FEN  C20  H202  single    0.970  0.020  1.090
 FEN  C20  H203  single    0.970  0.020  1.090
 FEN  C1'  C2'   aromatic  1.398  0.020  1.398
 FEN  C1'  C6'   aromatic  1.394  0.020  1.394
 FEN  C1'  N     single    1.399  0.020  1.399
 FEN  C2'  C3'   aromatic  1.381  0.020  1.381
 FEN  C2'  H2'   single    0.930  0.020  1.080
 FEN  C3'  C4'   aromatic  1.393  0.020  1.393
 FEN  C3'  H3'   single    0.930  0.020  1.080
 FEN  C4'  C5'   aromatic  1.389  0.020  1.389
 FEN  C4'  O4'   single    1.350  0.020  1.350
 FEN  C5'  C6'   aromatic  1.389  0.020  1.389
 FEN  C5'  H5'   single    0.930  0.020  1.080
 FEN  C6'  H6'   single    0.930  0.020  1.080
 FEN  N    HN    single    0.860  0.020  1.020
 FEN  O4'  HO4'  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
 FEN  C17   C1   C16   108.70  3.000
 FEN  C17   C1   C6    110.09  3.000
 FEN  C16   C1   C6    109.51  3.000
 FEN  C17   C1   C2    107.82  3.000
 FEN  C16   C1   C2    109.93  3.000
 FEN  C6    C1   C2    110.75  3.000
 FEN  H22   C2   H21   106.38  3.000
 FEN  H22   C2   C3    108.88  3.000
 FEN  H21   C2   C3    111.09  3.000
 FEN  H22   C2   C1    109.20  3.000
 FEN  H21   C2   C1    108.84  3.000
 FEN  C3    C2   C1    112.26  3.000
 FEN  H32   C3   H31   106.41  3.000
 FEN  H32   C3   C4    110.13  3.000
 FEN  H31   C3   C4    109.81  3.000
 FEN  H32   C3   C2    110.66  3.000
 FEN  H31   C3   C2    110.12  3.000
 FEN  C4    C3   C2    109.67  3.000
 FEN  H42   C4   H41   104.95  3.000
 FEN  H42   C4   C5    108.34  3.000
 FEN  H41   C4   C5    108.86  3.000
 FEN  H42   C4   C3    110.05  3.000
 FEN  H41   C4   C3    110.15  3.000
 FEN  C5    C4   C3    114.07  3.000
 FEN  C18   C5   C6    124.57  3.000
 FEN  C18   C5   C4    113.05  3.000
 FEN  C6    C5   C4    122.38  3.000
 FEN  C7    C6   C5    123.23  3.000
 FEN  C7    C6   C1    113.81  3.000
 FEN  C5    C6   C1    122.93  3.000
 FEN  H7    C7   C8    118.26  3.000
 FEN  H7    C7   C6    115.38  3.000
 FEN  C8    C7   C6    126.23  3.000
 FEN  H8    C8   C9    115.82  3.000
 FEN  H8    C8   C7    118.89  3.000
 FEN  C9    C8   C7    125.27  3.000
 FEN  C19   C9   C10   123.78  3.000
 FEN  C19   C9   C8    118.21  3.000
 FEN  C10   C9   C8    118.00  3.000
 FEN  H10   C10  C11   115.75  3.000
 FEN  H10   C10  C9    117.44  3.000
 FEN  C11   C10  C9    126.81  3.000
 FEN  H11   C11  C12   119.07  3.000
 FEN  H11   C11  C10   118.12  3.000
 FEN  C12   C11  C10   122.80  3.000
 FEN  H12   C12  C13   116.35  3.000
 FEN  H12   C12  C11   118.40  3.000
 FEN  C13   C12  C11   125.25  3.000
 FEN  C20   C13  C14   125.68  3.000
 FEN  C20   C13  C12   117.57  3.000
 FEN  C14   C13  C12   116.75  3.000
 FEN  H14   C14  C15   115.30  3.000
 FEN  H14   C14  C13   116.48  3.000
 FEN  C15   C14  C13   128.23  3.000
 FEN  N     C15  O     122.64  3.000
 FEN  N     C15  C14   111.99  3.000
 FEN  O     C15  C14   125.36  3.000
 FEN  H163  C16  H162  107.87  3.000
 FEN  H163  C16  H161  107.50  3.000
 FEN  H162  C16  H161  107.25  3.000
 FEN  H163  C16  C1    111.78  3.000
 FEN  H162  C16  C1    110.41  3.000
 FEN  H161  C16  C1    111.82  3.000
 FEN  H173  C17  H172  107.76  3.000
 FEN  H173  C17  H171  107.53  3.000
 FEN  H172  C17  H171  107.71  3.000
 FEN  H173  C17  C1    110.00  3.000
 FEN  H172  C17  C1    111.19  3.000
 FEN  H171  C17  C1    112.46  3.000
 FEN  H183  C18  H182  106.27  3.000
 FEN  H183  C18  H181  107.66  3.000
 FEN  H182  C18  H181  108.14  3.000
 FEN  H183  C18  C5    110.86  3.000
 FEN  H182  C18  C5    109.97  3.000
 FEN  H181  C18  C5    113.64  3.000
 FEN  H193  C19  H192  106.80  3.000
 FEN  H193  C19  H191  107.47  3.000
 FEN  H192  C19  H191  107.41  3.000
 FEN  H193  C19  C9    110.69  3.000
 FEN  H192  C19  C9    111.04  3.000
 FEN  H191  C19  C9    113.13  3.000
 FEN  H203  C20  H202  106.64  3.000
 FEN  H203  C20  H201  108.26  3.000
 FEN  H202  C20  H201  108.64  3.000
 FEN  H203  C20  C13   110.08  3.000
 FEN  H202  C20  C13   110.21  3.000
 FEN  H201  C20  C13   112.80  3.000
 FEN  N     C1'  C6'   125.12  3.000
 FEN  N     C1'  C2'   116.76  3.000
 FEN  C6'   C1'  C2'   118.12  3.000
 FEN  H2'   C2'  C3'   118.77  3.000
 FEN  H2'   C2'  C1'   119.69  3.000
 FEN  C3'   C2'  C1'   121.54  3.000
 FEN  H3'   C3'  C4'   120.08  3.000
 FEN  H3'   C3'  C2'   119.80  3.000
 FEN  C4'   C3'  C2'   120.12  3.000
 FEN  O4'   C4'  C5'   123.17  3.000
 FEN  O4'   C4'  C3'   118.11  3.000
 FEN  C5'   C4'  C3'   118.73  3.000
 FEN  H5'   C5'  C6'   118.65  3.000
 FEN  H5'   C5'  C4'   120.13  3.000
 FEN  C6'   C5'  C4'   121.22  3.000
 FEN  H6'   C6'  C5'   118.66  3.000
 FEN  H6'   C6'  C1'   121.08  3.000
 FEN  C5'   C6'  C1'   120.27  3.000
 FEN  HN    N    C1'   114.25  3.000
 FEN  HN    N    C15   116.25  3.000
 FEN  C1'   N    C15   129.47  3.000
 FEN  HO4'  O4'  C4'   110.36  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
 FEN  CONST_01  C4'   C3'  C2'  C1'     0.00   0.0  0
 FEN  CONST_02  C4'   C5'  C6'  C1'     0.00   0.0  0
 FEN  CONST_03  C5'   C6'  C1'  C2'     0.00   0.0  0
 FEN  CONST_04  C5'   C4'  C3'  C2'     0.00   0.0  0
 FEN  CONST_05  C6'   C1'  C2'  C3'     0.00   0.0  0
 FEN  CONST_06  C6'   C5'  C4'  C3'     0.00   0.0  0
 FEN  CONST_07  O4'   C4'  C3'  C2'   180.00   0.0  0
 FEN  CONST_08  N     C1'  C2'  C3'   180.00   0.0  0
 FEN  CONST_09  N     C1'  C6'  C5'   180.00   0.0  0
 FEN  CONST_10  O4'   C4'  C5'  C6'   180.00   0.0  0
 FEN  CONST_11  H3'   C3'  C2'  C1'   180.00   0.0  0
 FEN  CONST_12  H5'   C5'  C6'  C1'   180.00   0.0  0
 FEN  CONST_13  H6'   C6'  C1'  C2'   180.00   0.0  0
 FEN  CONST_14  H2'   C2'  C3'  C4'   180.00   0.0  0
 FEN  CONST_15  C2'   C1'  N    C15   180.00   0.0  0
 FEN  CONST_16  C6'   C1'  N    C15     0.00   0.0  0
 FEN  CONST_17  HN    N    C1'  C2'     0.00   0.0  0
 FEN  CONST_18  C1'   N    C15  C14   180.00   0.0  0
 FEN  CONST_19  O     C15  N    C1'     0.00   0.0  0
 FEN  Var_01    C4    C3   C2   C1    -61.34  30.0  1
 FEN  Var_02    C4    C5   C6   C1      1.57  30.0  1
 FEN  Var_03    C5    C6   C1   C2    -16.95  30.0  1
 FEN  Var_04    C5    C4   C3   C2     44.22  30.0  1
 FEN  Var_05    C6    C1   C2   C3     46.72  30.0  1
 FEN  Var_06    C6    C5   C4   C3    -15.58  30.0  1
 FEN  Var_07    C8    C7   C6   C1   -130.29  30.0  2
 FEN  Var_08    H161  C16  C1   C2   -179.69  30.0  3
 FEN  Var_09    H171  C17  C1   C2    173.96  30.0  3
 FEN  Var_10    H181  C18  C5   C4   -167.28  30.0  3
 FEN  Var_11    C9    C8   C7   C6    177.51   0.0  2
 FEN  Var_12    C11   C10  C9   C8    178.57   0.0  2
 FEN  Var_13    C13   C12  C11  C10   179.05   0.0  2
 FEN  Var_14    C15   C14  C13  C12  -179.95   0.0  2
 FEN  Var_15    C10   C9   C8   C7   -178.86  30.0  2
 FEN  Var_16    C12   C11  C10  C9    179.78  30.0  2
 FEN  Var_17    C14   C13  C12  C11  -179.96  30.0  2
 FEN  Var_18    O     C15  C14  C13     4.80  30.0  2
 FEN  Var_19    H191  C19  C9   C8   -177.21  30.0  3
 FEN  Var_20    H201  C20  C13  C12  -175.32  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
 FEN  plan-1  C1'  0.020
 FEN  plan-1  C2'  0.020
 FEN  plan-1  C3'  0.020
 FEN  plan-1  C4'  0.020
 FEN  plan-1  C5'  0.020
 FEN  plan-1  C6'  0.020
 FEN  plan-1  N    0.020
 FEN  plan-1  O4'  0.020
 FEN  plan-1  H2'  0.020
 FEN  plan-1  H3'  0.020
 FEN  plan-1  H5'  0.020
 FEN  plan-1  H6'  0.020
 FEN  plan-2  C14  0.020
 FEN  plan-2  C15  0.020
 FEN  plan-2  C1'  0.020
 FEN  plan-2  O    0.020
 FEN  plan-2  N    0.020
 FEN  plan-2  HN   0.020
 FEN  plan-3  C6   0.020
 FEN  plan-3  C7   0.020
 FEN  plan-3  C8   0.020
 FEN  plan-3  C9   0.020
 FEN  plan-3  H7   0.020
 FEN  plan-3  H8   0.020
 FEN  plan-4  C8   0.020
 FEN  plan-4  C9   0.020
 FEN  plan-4  C10  0.020
 FEN  plan-4  C11  0.020
 FEN  plan-4  C19  0.020
 FEN  plan-4  H10  0.020
 FEN  plan-5  C10  0.020
 FEN  plan-5  C11  0.020
 FEN  plan-5  C12  0.020
 FEN  plan-5  C13  0.020
 FEN  plan-5  H11  0.020
 FEN  plan-5  H12  0.020
 FEN  plan-6  C12  0.020
 FEN  plan-6  C13  0.020
 FEN  plan-6  C14  0.020
 FEN  plan-6  C15  0.020
 FEN  plan-6  C20  0.020
 FEN  plan-6  H14  0.020

