Hydroarylation of unsaturated carbon-carbon bonds in cross-conjugated enynones under the action of superacid CF<sub>3</sub>SO<sub>3</sub>H or acidic zeolite HUSY. Reaction mechanism and DFT study on cationic intermediate species.
Aleksandrova, Maiia I.; Lozovskiy, Stanislav V.; Saulnier, Steve; Golovanov, Alexander A.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.; Organic & biomolecular chemistry 16 (2018) 7891–7902; doi:10.1039/c8ob01985a

data_7156477
_publ_section_title
;
 Hydroarylation of unsaturated carbon-carbon bonds in cross-conjugated
 enynones under the action of superacid CF<sub>3</sub>SO<sub>3</sub>H or
 acidic zeolite HUSY. Reaction mechanism and DFT study on cationic
 intermediate species.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7891
_journal_page_last               7902
_journal_paper_doi               10.1039/c8ob01985a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C23 H17 F O'
_chemical_formula_sum            'C23 H17 F O'
_chemical_formula_weight         328.36
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_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
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Olex2 1.2
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2018-06-05 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
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  1 omega  -93.00   -4.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
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  2 omega  -78.00  -50.00   1.0000   14.7100
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  3 omega  -87.00  -55.00   1.0000   14.7100
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  4 omega  -45.00   39.00   1.0000   14.7100
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  5 omega   63.00   89.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
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  6 omega   38.00   64.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
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  7 omega  -18.00    8.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
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  8 omega   10.00   89.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
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  9 omega   -5.00   39.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000   90.0000 44

 10 omega  -52.00    7.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000 -150.0000 59

 11 omega  -52.00  -27.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   77.0000    0.0000 25

 12 omega   18.00   44.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   77.0000    0.0000 26

 13 omega  -14.00   25.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   19.0000    0.0000 39

 14 omega  -46.00   46.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
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 15 omega   65.00   92.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000   30.0000 27

 16 omega  -25.00   65.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  -90.0000 90

 17 omega    3.00   28.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000   30.0000 25

 18 omega   -5.00   21.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000   60.0000 26

 19 omega   55.00   81.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000   60.0000 26

 20 omega   47.00   83.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -129.0000  162.2029 36
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
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_diffrn_orient_matrix_UB_12      0.0162310000
_diffrn_orient_matrix_UB_13      0.0598922000
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_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0219
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_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30881
_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.637
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
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_exptl_crystal_size_min          0.2
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_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3969
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0399
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+0.6189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_cod_depositor_comments
'Adding full bibliography for 7156474--7156479.cif.'
_cod_original_cell_volume        1732.22(7)
_cod_database_code               7156477
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C23 H17 F O'
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_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
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;
_shelx_res_checksum              82211
_olex2_submission_special_instructions 'No special instructions were received'