Cobalt-Catalyzed Asymmetric Addition of Silylacetylenes to 1,1-Disubstituted Allenes
Takahiro Sawano; Keiyu Ou; Takahiro Nishimura; Tamio Hayashi; Journal of Organic Chemistry 78 (2013) 8986–8993; doi:10.1021/jo401604n

data_4028624
_publ_section_title
;
 Cobalt-Catalyzed Asymmetric Addition of Silylacetylenes to
 1,1-Disubstituted Allenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8986
_journal_page_last               8993
_journal_paper_doi               10.1021/jo401604n
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H18 Cl N3 O'
_chemical_formula_weight         339.81
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 97.666(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.8589(8)
_cell_length_b                   5.7629(2)
_cell_length_c                   17.1929(8)
_cell_measurement_reflns_used    2911
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      78.05
_cell_measurement_theta_min      5.19
_cell_volume                     1655.47(12)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1012
_diffrn_reflns_av_sigmaI/netI    0.1381
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8249
_diffrn_reflns_theta_full        62.99
_diffrn_reflns_theta_max         62.99
_diffrn_reflns_theta_min         5.19
_exptl_absorpt_coefficient_mu    2.122
_exptl_absorpt_correction_T_max  0.9013
_exptl_absorpt_correction_T_min  0.3625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;Higashi, T. (1995). 
 Program for Absorption Correction.
 Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2630
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.0734
_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^)+(0.0729P)^2^+0.2036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.2062
_reflns_number_gt                1378
_reflns_number_total             2630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401604n_si_002.cif
_cod_data_source_block           1013yu
_cod_original_cell_volume        1655.46(12)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4028624