Nickel-Catalyzed Decarbonylative Alkylidenation of Phthalimides with Trimethylsilyl-Substituted Alkynes
Takahiro Shiba; Takuya Kurahashi; Seijiro Matsubara; Journal of the American Chemical Society 135 (2013) 13636–13639; doi:10.1021/ja4068172

data_4120798
_publ_section_title
;
 Nickel-Catalyzed Decarbonylative Alkylidenation of Phthalimides with
 Trimethylsilyl-Substituted Alkynes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13636
_journal_page_last               13639
_journal_paper_doi               10.1021/ja4068172
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C20 H28 N2 O Si2'
_chemical_formula_weight         368.62
_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                 91.826(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6834(17)
_cell_length_b                   16.116(3)
_cell_length_c                   14.179(2)
_cell_measurement_reflns_used    4952
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.59
_cell_measurement_theta_min      2.45
_cell_volume                     2211.6(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13134
_diffrn_reflns_theta_full        27.06
_diffrn_reflns_theta_max         27.06
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_correction_T_min  0.9832
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0922P)^2^+0.3009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1582
_reflns_number_gt                3858
_reflns_number_total             4823
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4068172_3ag.cif
_cod_data_source_block           3ag
_cod_original_cell_volume        2211.6(7)
_cod_original_formula_sum        'C16 H22.40 N1.60 O0.80 Si1.60'
_cod_database_code               4120798