Iridium-Catalyzed [3 + 2] Annulation of Cyclic N-Sulfonyl Ketimines with 1,3-Dienes via C-H Activation
Takahiro Nishimura; Yusuke Ebe; Tamio Hayashi; Journal of the American Chemical Society 135 (2013) 2092–2095; doi:10.1021/ja311968d

data_4119339
_publ_section_title
;
 Iridium-Catalyzed [3 + 2] Annulation of Cyclic N-Sulfonyl Ketimines with
 1,3-Dienes via C-H Activation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2092
_journal_page_last               2095
_journal_paper_doi               10.1021/ja311968d
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C23 H19 N O2 S'
_chemical_formula_weight         373.45
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                70.5189(11)
_cell_angle_beta                 71.0817(10)
_cell_angle_gamma                69.3580(11)
_cell_formula_units_Z            2
_cell_length_a                   8.9432(2)
_cell_length_b                   9.9942(2)
_cell_length_c                   11.8822(2)
_cell_measurement_reflns_used    14132
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      3.27
_cell_volume                     910.89(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9603
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         4.06
_exptl_absorpt_coefficient_mu    1.719
_exptl_absorpt_correction_T_max  0.8469
_exptl_absorpt_correction_T_min  0.6265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;Higashi, T. (1995). 
 Program for Absorption Correction.
 Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1480
_reflns_number_gt                2828
_reflns_number_total             3234
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja311968d_si_002.cif
_cod_data_source_block           3ao
_cod_database_code               4119339