# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Mar 22 19:41:41 2022
#   Inital geometry file: a 115 line input string
#   Ligand name: (2E,4E,6R)-7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H](\C=C(C)\C=C\C(=O)NO)C(=O)c1ccc(cc1)N(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
 TSN  TSN  (2E,4E,6R)-7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide  ligand  44  22  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_TSN
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
 TSN  O1    O  OH1   0  -0.542  -0.9377  -0.7197   8.2041
 TSN  O2    O  O     0  -0.480   0.9661  -0.6575   6.2831
 TSN  N1    N  NH1   0  -0.393  -1.2106  -0.5097   6.8869
 TSN  N2    N  NT    0  -0.496  -0.9777  -0.2995  -6.1862
 TSN  C1    C  CR6   0  -0.056   0.5699  -0.0834  -2.2868
 TSN  C2    C  CR16  0  -0.248   0.8985  -1.1381  -3.1498
 TSN  C3    C  CR16  0  -0.342   0.4001  -1.2176  -4.4283
 TSN  C4    C  CR6   0   0.406  -0.4733  -0.2252  -4.9328
 TSN  C5    C  CR16  0  -0.343  -0.7962   0.8441  -4.0685
 TSN  C6    C  CR16  0  -0.282  -0.2892   0.9004  -2.7885
 TSN  C7    C  C     0   0.397   1.1379  -0.0619  -0.9307
 TSN  C8    C  CH1   0  -0.493   0.8125   1.1115  -0.0097
 TSN  C9    C  C1    0  -0.194   0.8867   0.6903   1.4227
 TSN  C10   C  C     0   0.119  -0.1220   0.6083   2.3061
 TSN  C11   C  C1    0  -0.214   0.2156   0.1905   3.6604
 TSN  C12   C  C1    0  -0.437  -0.6510   0.0449   4.6700
 TSN  C13   C  C     0   0.534  -0.1926  -0.3924   6.0041
 TSN  C14   C  CH3   0  -0.643   1.8222   2.2401  -0.2797
 TSN  C15   C  CH3   0  -0.758  -1.5601   0.9028   2.0042
 TSN  C17   C  CH3   0  -0.540  -0.6262  -1.4068  -7.0475
 TSN  C16   C  CH3   0  -0.540  -1.8311   0.7538  -6.6896
 TSN  HO1   H  HOH1  0   0.478  -1.0684  -1.6644   8.3569
 TSN  HN1   H  HNH1  0   0.414  -2.1186  -0.1042   6.7086
 TSN  H21   H  HCR6  0   0.255   1.5643  -1.9196  -2.8072
 TSN  H31   H  HCR6  0   0.272   0.6958  -2.0553  -5.0439
 TSN  H51   H  HCR6  0   0.274  -1.4529   1.6383  -4.3937
 TSN  H61   H  HCR6  0   0.254  -0.5866   1.7433  -2.1786
 TSN  H8    H  HCH1  0   0.266  -0.1833   1.4900  -0.2359
 TSN  H9    H  H     0   0.253   1.8825   0.4431   1.7792
 TSN  H111  H  H     0   0.257   1.2643  -0.0190   3.8493
 TSN  H121  H  H     0   0.271  -1.7092   0.2383   4.5347
 TSN  H141  H  HCH3  0   0.236   2.8356   1.9222  -0.0320
 TSN  H142  H  HCH3  0   0.244   1.8095   2.5485  -1.3251
 TSN  H143  H  HCH3  0   0.251   1.5799   3.1102   0.3295
 TSN  H151  H  HCH3  0   0.255  -1.7285   1.1813   0.9675
 TSN  H152  H  HCH3  0   0.249  -2.1861   0.0329   2.2116
 TSN  H153  H  HCH3  0   0.248  -1.9313   1.7177   2.6288
 TSN  H171  H  HCH3  0   0.261  -1.1540  -1.3092  -7.9912
 TSN  H172  H  HCH3  0   0.240   0.4447  -1.4366  -7.2650
 TSN  H173  H  HCH3  0   0.242  -0.9080  -2.3670  -6.6092
 TSN  H161  H  HCH3  0   0.241  -1.3176   1.7184  -6.7160
 TSN  H162  H  HCH3  0   0.262  -2.1399   0.5136  -7.7024
 TSN  H163  H  HCH3  0   0.241  -2.7352   0.8694  -6.0872
 TSN  O3    O  O     0  -0.417   1.8872  -0.9419  -0.5450

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
 TSN  O1   N1    single    1.361  0.020  1.361
 TSN  O1   HO1   single    0.850  0.020  0.980
 TSN  O2   C13   double    1.221  0.020  1.221
 TSN  O3   C7    double    1.218  0.020  1.218
 TSN  N1   C13   single    1.353  0.020  1.353
 TSN  N1   HN1   single    0.890  0.020  1.040
 TSN  N2   C4    single    1.353  0.020  1.353
 TSN  N2   C17   single    1.446  0.020  1.446
 TSN  N2   C16   single    1.446  0.020  1.446
 TSN  C1   C2    aromatic  1.402  0.020  1.402
 TSN  C1   C6    aromatic  1.399  0.020  1.399
 TSN  C1   C7    single    1.470  0.020  1.470
 TSN  C2   C3    aromatic  1.374  0.020  1.374
 TSN  C2   H21   single    0.930  0.020  1.080
 TSN  C3   C4    aromatic  1.415  0.020  1.415
 TSN  C3   H31   single    0.930  0.020  1.080
 TSN  C4   C5    aromatic  1.412  0.020  1.412
 TSN  C5   C6    aromatic  1.378  0.020  1.378
 TSN  C5   H51   single    0.930  0.020  1.080
 TSN  C6   H61   single    0.930  0.020  1.080
 TSN  C7   C8    single    1.527  0.020  1.527
 TSN  C8   C9    single    1.495  0.020  1.495
 TSN  C8   C14   single    1.538  0.020  1.538
 TSN  C8   H8    single    0.970  0.020  1.090
 TSN  C9   C10   double    1.343  0.020  1.343
 TSN  C9   H9    single    0.930  0.020  1.080
 TSN  C10  C11   single    1.457  0.020  1.457
 TSN  C10  C15   single    1.499  0.020  1.499
 TSN  C11  C12   double    1.338  0.020  1.338
 TSN  C11  H111  single    0.930  0.020  1.080
 TSN  C12  C13   single    1.477  0.020  1.477
 TSN  C12  H121  single    0.930  0.020  1.080
 TSN  C14  H141  single    0.970  0.020  1.090
 TSN  C14  H142  single    0.970  0.020  1.090
 TSN  C14  H143  single    0.970  0.020  1.090
 TSN  C15  H151  single    0.970  0.020  1.090
 TSN  C15  H152  single    0.970  0.020  1.090
 TSN  C15  H153  single    0.970  0.020  1.090
 TSN  C17  H171  single    0.970  0.020  1.090
 TSN  C17  H172  single    0.970  0.020  1.090
 TSN  C17  H173  single    0.970  0.020  1.090
 TSN  C16  H161  single    0.970  0.020  1.090
 TSN  C16  H162  single    0.970  0.020  1.090
 TSN  C16  H163  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
 TSN  HO1   O1   N1    106.07  3.000
 TSN  HN1   N1   C13   121.76  3.000
 TSN  HN1   N1   O1    114.39  3.000
 TSN  C13   N1   O1    119.60  3.000
 TSN  C16   N2   C17   119.59  3.000
 TSN  C16   N2   C4    120.16  3.000
 TSN  C17   N2   C4    120.21  3.000
 TSN  C7    C1   C6    123.89  3.000
 TSN  C7    C1   C2    119.22  3.000
 TSN  C6    C1   C2    116.88  3.000
 TSN  H21   C2   C3    118.41  3.000
 TSN  H21   C2   C1    119.51  3.000
 TSN  C3    C2   C1    122.09  3.000
 TSN  H31   C3   C4    120.62  3.000
 TSN  H31   C3   C2    118.39  3.000
 TSN  C4    C3   C2    120.99  3.000
 TSN  C5    C4   C3    116.99  3.000
 TSN  C5    C4   N2    121.55  3.000
 TSN  C3    C4   N2    121.46  3.000
 TSN  H51   C5   C6    118.24  3.000
 TSN  H51   C5   C4    120.74  3.000
 TSN  C6    C5   C4    121.02  3.000
 TSN  H61   C6   C5    117.02  3.000
 TSN  H61   C6   C1    120.96  3.000
 TSN  C5    C6   C1    122.03  3.000
 TSN  C8    C7   C1    119.03  3.000
 TSN  C8    C7   O3    119.69  3.000
 TSN  C1    C7   O3    121.26  3.000
 TSN  H8    C8   C14   107.98  3.000
 TSN  H8    C8   C9    110.02  3.000
 TSN  C14   C8   C9    110.02  3.000
 TSN  H8    C8   C7    109.68  3.000
 TSN  C14   C8   C7    108.55  3.000
 TSN  C9    C8   C7    110.54  3.000
 TSN  H9    C9   C10   117.30  3.000
 TSN  H9    C9   C8    115.09  3.000
 TSN  C10   C9   C8    127.60  3.000
 TSN  C15   C10  C11   117.77  3.000
 TSN  C15   C10  C9    125.18  3.000
 TSN  C11   C10  C9    117.05  3.000
 TSN  H111  C11  C12   118.23  3.000
 TSN  H111  C11  C10   116.15  3.000
 TSN  C12   C11  C10   125.61  3.000
 TSN  H121  C12  C13   117.93  3.000
 TSN  H121  C12  C11   121.23  3.000
 TSN  C13   C12  C11   120.84  3.000
 TSN  C12   C13  N1    112.44  3.000
 TSN  C12   C13  O2    124.42  3.000
 TSN  N1    C13  O2    123.11  3.000
 TSN  H143  C14  H142  107.92  3.000
 TSN  H143  C14  H141  108.21  3.000
 TSN  H142  C14  H141  108.12  3.000
 TSN  H143  C14  C8    109.99  3.000
 TSN  H142  C14  C8    111.61  3.000
 TSN  H141  C14  C8    110.87  3.000
 TSN  H153  C15  H152  106.93  3.000
 TSN  H153  C15  H151  107.56  3.000
 TSN  H152  C15  H151  107.26  3.000
 TSN  H153  C15  C10   110.96  3.000
 TSN  H152  C15  C10   110.82  3.000
 TSN  H151  C15  C10   113.03  3.000
 TSN  H173  C17  H172  107.97  3.000
 TSN  H173  C17  H171  107.60  3.000
 TSN  H172  C17  H171  107.80  3.000
 TSN  H173  C17  N2    111.80  3.000
 TSN  H172  C17  N2    112.17  3.000
 TSN  H171  C17  N2    109.31  3.000
 TSN  H163  C16  H162  107.60  3.000
 TSN  H163  C16  H161  107.98  3.000
 TSN  H162  C16  H161  107.83  3.000
 TSN  H163  C16  N2    111.93  3.000
 TSN  H162  C16  N2    109.36  3.000
 TSN  H161  C16  N2    111.96  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
 TSN  CONST_01  C4    C3   C2   C1      0.00   0.0  0
 TSN  CONST_02  C4    C5   C6   C1      0.00   0.0  0
 TSN  CONST_03  C5    C6   C1   C2      0.00   0.0  0
 TSN  CONST_04  C5    C4   C3   C2      0.00   0.0  0
 TSN  CONST_05  C6    C1   C2   C3      0.00   0.0  0
 TSN  CONST_06  C6    C5   C4   C3      0.00   0.0  0
 TSN  CONST_07  C2    C3   C4   N2    180.00   0.0  0
 TSN  CONST_08  C6    C5   C4   N2    180.00   0.0  0
 TSN  CONST_09  C7    C1   C2   C3    180.00   0.0  0
 TSN  CONST_10  C7    C1   C6   C5    180.00   0.0  0
 TSN  CONST_11  H31   C3   C2   C1    180.00   0.0  0
 TSN  CONST_12  H51   C5   C6   C1    180.00   0.0  0
 TSN  CONST_13  H61   C6   C1   C2    180.00   0.0  0
 TSN  CONST_14  H21   C2   C3   C4    180.00   0.0  0
 TSN  CONST_15  C17   N2   C4   C3      0.00   0.0  0
 TSN  CONST_16  C16   N2   C4   C3    180.00   0.0  0
 TSN  CONST_17  C17   N2   C4   C5    180.00   0.0  0
 TSN  CONST_18  C16   N2   C4   C5      0.00   0.0  0
 TSN  CONST_19  O2    C13  N1   O1      0.00   0.0  0
 TSN  CONST_20  C12   C13  N1   O1    180.00   0.0  0
 TSN  CONST_21  HN1   N1   C13  O2    180.00   0.0  0
 TSN  Var_01    C2    C1   C7   O3      0.02  30.0  2
 TSN  Var_02    H171  C17  N2   C4    177.96  30.0  3
 TSN  Var_03    H161  C16  N2   C4     60.98  30.0  3
 TSN  Var_04    C11   C10  C9   C8   -178.93   0.0  2
 TSN  Var_05    C13   C12  C11  C10   179.69   0.0  2
 TSN  Var_06    C11   C12  C13  O2     -0.61  30.0  2
 TSN  Var_07    C12   C11  C10  C9   -179.63  30.0  2
 TSN  Var_08    H151  C15  C10  C9      1.09  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
 TSN  chir_01  C8  C7  C9  C14  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
 TSN  plan-1  N2    0.020
 TSN  plan-1  C1    0.020
 TSN  plan-1  C2    0.020
 TSN  plan-1  C3    0.020
 TSN  plan-1  C4    0.020
 TSN  plan-1  C5    0.020
 TSN  plan-1  C6    0.020
 TSN  plan-1  C7    0.020
 TSN  plan-1  H21   0.020
 TSN  plan-1  H31   0.020
 TSN  plan-1  H51   0.020
 TSN  plan-1  H61   0.020
 TSN  plan-2  O1    0.020
 TSN  plan-2  O2    0.020
 TSN  plan-2  N1    0.020
 TSN  plan-2  C12   0.020
 TSN  plan-2  C13   0.020
 TSN  plan-2  HN1   0.020
 TSN  plan-3  N2    0.020
 TSN  plan-3  C4    0.020
 TSN  plan-3  C17   0.020
 TSN  plan-3  C16   0.020
 TSN  plan-4  C1    0.020
 TSN  plan-4  C7    0.020
 TSN  plan-4  C8    0.020
 TSN  plan-4  O3    0.020
 TSN  plan-5  C8    0.020
 TSN  plan-5  C9    0.020
 TSN  plan-5  C10   0.020
 TSN  plan-5  C11   0.020
 TSN  plan-5  C15   0.020
 TSN  plan-5  H9    0.020
 TSN  plan-6  C10   0.020
 TSN  plan-6  C11   0.020
 TSN  plan-6  C12   0.020
 TSN  plan-6  C13   0.020
 TSN  plan-6  H111  0.020
 TSN  plan-6  H121  0.020

