Unexpected stereoselective CuBr2-catalyzed cascade reaction of 2-ethynylanilines with silylynamides: facile and atom-economical access to N-vinylsilylindoles
Li, Zengzeng; Lu, Fei; Xu, Qingchun; Liu, Gang; Zhao, Ximei; Wang, Guanghui; Green Chemistry 26 (2024) 259–263; doi:10.1039/D3GC04244H

data_7247827
_publ_section_title
;
 Unexpected stereoselective CuBr2-catalyzed cascade reaction of
 2-ethynylanilines with silylynamides: facile and atom-economical access
 to N-vinylsilylindoles
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              259
_journal_page_last               263
_journal_paper_doi               10.1039/D3GC04244H
_journal_volume                  26
_journal_year                    2024
_chemical_formula_sum            'C29 H40 N2 O4 S Si'
_chemical_formula_weight         540.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-10-05 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.697(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2243(4)
_cell_length_b                   10.5039(3)
_cell_length_c                   23.3691(8)
_cell_measurement_reflns_used    4564
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1450
_cell_measurement_theta_min      3.7940
_cell_volume                     2999.34(17)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10887
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.245
_diffrn_reflns_theta_max         67.245
_diffrn_reflns_theta_min         3.617
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.618
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            WHITE
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5363
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0615
_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^)+(0.1039P)^2^+0.9565P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1674
_refine_ls_wR_factor_ref         0.1835
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4100
_reflns_number_total             5363
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc04244h2.cif
_cod_data_source_block           exp_13211
_cod_depositor_comments          'Adding full bibliography for 7247827.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7247827
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.817
_shelx_estimated_absorpt_t_max   0.829
_shelx_res_checksum              18018