Tandem Cyclization of α-Cyano α-Alkynyl Aryl Ketones Induced by tert-Butyl Hydroperoxide and Tetrabutylammonium Iodide.
Wong, Ying-Chieh; Tseng, Chen-Tso; Kao, Tzu-Ting; Yeh, Yu-Cheng; Shia, Kak-Shan; Organic letters 14 (2012) 6024–6027; doi:10.1021/ol3028972

data_1508778
_publ_section_title
;
 Tandem Cyclization of \a-Cyano \a-Alkynyl Aryl Ketones Induced by
 tert-Butyl Hydroperoxide and Tetrabutylammonium Iodide.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6024
_journal_page_last               6027
_journal_paper_doi               10.1021/ol3028972
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C17 H18 Cl N O Si'
_chemical_formula_sum            'C17 H18 Cl N O Si'
_chemical_formula_weight         315.86
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.155(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.1290(12)
_cell_length_b                   10.1809(6)
_cell_length_c                   19.7805(10)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     3344.8(4)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18471
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.9428
_exptl_absorpt_correction_T_min  0.9028
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0763
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1229P)^2^+6.5070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2132
_refine_ls_wR_factor_ref         0.2286
_reflns_number_gt                4614
_reflns_number_total             5875
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3028972_si_002.cif
_cod_data_source_block           a14028
_cod_original_cell_volume        3344.8(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1508778