Enantioselective [3 + 2] annulation via C–H activation between cyclic N-acyl ketimines and 1,3-dienes catalyzed by iridium/chiral diene complexes
Nishimura, Takahiro; Nagamoto, Midori; Ebe, Yusuke; Hayashi, Tamio; Chemical Science 4 (2013) 4499–; doi:10.1039/c3sc52379a

data_1514628
_publ_section_title
;
 Enantioselective [3 + 2] annulation via C--H activation between cyclic
 N-acyl ketimines and 1,3-dienes catalyzed by iridium/chiral diene
 complexes
;
_journal_issue                   12
_journal_name_full               'Chemical Science'
_journal_page_first              4499
_journal_paper_doi               10.1039/c3sc52379a
_journal_volume                  4
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H23 N O3 S'
_chemical_formula_sum            'C26 H23 N O3 S'
_chemical_formula_weight         429.51
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 100.721(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6436(3)
_cell_length_b                   12.2137(4)
_cell_length_c                   10.5880(3)
_cell_measurement_temperature    93(2)
_cell_volume                     1098.27(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0753
_diffrn_reflns_av_sigmaI/netI    0.1016
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10421
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         4.25
_exptl_absorpt_coefficient_mu    1.531
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.5795
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3740
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0592
_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          0.1455
_refine_ls_wR_factor_ref         0.1877
_reflns_number_gt                2726
_reflns_number_total             3740
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc52379a.txt
_cod_data_source_block           30419yu
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1514628