Iridium-catalyzed asymmetric [3+2] annulation of aromatic ketimines with alkynes via C-H activation: unexpected inversion of the enantioselectivity induced by protic acids
Midori Nagamoto; Daisuke Yamauchi; Takahiro Nishimura; Chem.Commun. 52 (2016) 5876–; doi:

data_7119024
_publ_section_title
;
 Iridium-catalyzed asymmetric [3+2] annulation of aromatic ketimines with
 alkynes via C-H activation: unexpected inversion of the
 enantioselectivity induced by protic acids
;
_journal_name_full               Chem.Commun.
_journal_page_first              5876
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H21 Cl2 N O3, 0.1(C7 H8), 0.1(O) '
_chemical_formula_sum            'C61.4 H43.6 Cl4 N2 O6.2'
_chemical_formula_weight         1050.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           173
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      173
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-01-26 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   29.440(5)
_cell_length_b                   29.440(5)
_cell_length_c                   11.679(2)
_cell_measurement_reflns_used    4946
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      31.5
_cell_volume                     8766(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 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_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  0.0881
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            109145
_diffrn_reflns_theta_full        64.95
_diffrn_reflns_theta_max         64.95
_diffrn_reflns_theta_min         6.95
_exptl_absorpt_coefficient_mu    2.241
_exptl_absorpt_correction_T_max  0.9566
_exptl_absorpt_correction_T_min  0.5529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             3262
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.078(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     708
_refine_ls_number_reflns         9945
_refine_ls_number_restraints     447
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0962P)^2^+8.5270P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1842
_refine_ls_wR_factor_ref         0.1890
_reflns_number_gt                8542
_reflns_number_total             9945
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc01398h2.cif
_cod_data_source_block           50507ya
_cod_original_formula_sum        'C61.40 H43.60 Cl4 N2 O6.20'
_cod_database_code               7119024