Catalytically Asymmetric Synthesis of 1,3-Bis(silyl)propenes via Copper-Catalyzed Double Proto-Silylations of Polar Enynes
Meng, Fei-Fan; Xie, Jia-Hao; Xu, Yun-He; Loh, Teck-Peng; ACS Catalysis 8 (2018) 5306–; doi:10.1021/acscatal.8b00999

data_4515646
_publ_section_title
;
 Catalytically Asymmetric Synthesis of 1,3-Bis(silyl)propenes via
 Copper-Catalyzed Double Proto-Silylations of Polar Enynes
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              5306
_journal_paper_doi               10.1021/acscatal.8b00999
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C39 H38 Br N O Si2'
_chemical_formula_weight         672.79
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6879(10)
_cell_length_b                   9.8487(11)
_cell_length_c                   34.927(4)
_cell_measurement_reflns_used    7612
_cell_measurement_temperature    153
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.1
_cell_volume                     3332.5(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  'SHELXTL (Bruker, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXTL (Bruker, 2008)'
_diffrn_ambient_temperature      153
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            28905
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.148
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.338
_exptl_absorpt_correction_T_max  0.755
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bulk
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 2441 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.107(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         7612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0293P)^2^+1.5082P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0950
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                6737
_reflns_number_total             7612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b00999_si_002.cif
_cod_data_source_block           20171021zjl_s_0m_a_a
_cod_database_code               4515646
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.694
_shelx_estimated_absorpt_t_max   0.755
_shelx_res_checksum              55819
_shelx_hkl_checksum              54727