Cyclic Ketimines as Superior Electrophiles for NHC-Catalyzed Homoenolate Additions with Broad Scope and Low Catalyst Loadings
Michael Rommel; Takeo Fukuzumi; Jeffrey W. Bode; Journal of the American Chemical Society 130 (2008) 17266–17267; doi:10.1021/ja807937m

data_4108904
_publ_section_title
;
 Cyclic Ketimines as Superior Electrophiles for NHC-Catalyzed Homoenolate
 Additions with Broad Scope and Low Catalyst Loadings
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17266
_journal_page_last               17267
_journal_paper_doi               10.1021/ja807937m
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C22 H17 N O3 S'
_chemical_formula_weight         375.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.505(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.6026(13)
_cell_length_b                   17.9592(13)
_cell_length_c                   12.9034(10)
_cell_measurement_temperature    143(1)
_cell_volume                     3648.5(5)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23317
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;  Shape and scale corrections using equivalent reflections.
   Shape function based on spherical harmonics.
   Highest even and odd order for spherical harmonics:  4  and  3
   Laue group:  mmm
   Friedel opposites are equivalent.
;
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         6411
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+1.4809P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1098
_reflns_number_gt                5197
_reflns_number_total             6411
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja807937m_si_003.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4108904