Catalyst-controlled regiodivergent ring-opening C(sp3)–Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis
Takeda, Youhei; Shibuta, Kaoru; Aoki, Shohei; Tohnai, Norimitsu; Minakata, Satoshi; Chemical Science  (2019) –; doi:10.1039/C9SC02507C

data_1552177
_publ_section_title
;
 Catalyst-controlled regiodivergent ring-opening C(sp3)--Si bond-forming
 reactions of 2-arylaziridines with silylborane enabled by synergistic
 palladium/copper dual catalysis
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC02507C
_journal_year                    2019
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C23 H27 N O2 S Si'
_chemical_formula_sum            'C23 H27 N O2 S Si'
_chemical_formula_weight         409.62
_chemical_melting_point          373.8
_chemical_name_systematic
(S)-N-(2-(dimethyl(phenyl)silyl)-2-phenylethyl)-4-methylbenzenesulfonamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-09-12
_audit_creation_method           'by CrystalStructure 4.2.5'
_audit_update_record
;
2019-04-23 deposited with the CCDC.    2019-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.2700(12)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   9.63219(11)
_cell_length_b                   9.47828(9)
_cell_length_c                   12.72130(14)
_cell_measurement_reflns_used    10912
_cell_measurement_temperature    93
_cell_measurement_theta_max      74.19
_cell_measurement_theta_min      4.79
_cell_volume                     1114.90(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12316
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         74.398
_diffrn_reflns_theta_min         3.619
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.939
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             436.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.43
_refine_ls_abs_structure_details
;
 Flack x determined using 1943 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4387
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0617P)^2^+0.1773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0950
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                4325
_reflns_number_total             4387
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c9sc02507c2.cif
_cod_data_source_block           global
_cod_database_code               1552177
_shelx_res_checksum              1287