Divergent synthesis of polysubstituted cyclopropanes and β-silyoxy imidates via switchable additions of N-tert-butanesulfinylimidates to acylsilanes
Tang, Fan; Ma, Peng-Ju; Yao, Yun; Xu, Yan-Jun; Lu, Chong-Dao; Chemical Communications  (2019) –; doi:10.1039/C9CC00963A

data_7123143
_publ_section_title
;
 Divergent synthesis of polysubstituted cyclopropanes and \b-silyoxy
 imidates via switchable additions of N-tert-butanesulfinylimidates to
 acylsilanes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC00963A
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C22 H39 N O3 S Si'
_chemical_formula_sum            'C22 H39 N O3 S Si'
_chemical_formula_weight         425.70
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-01-21 deposited with the CCDC.    2019-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                108.471(14)
_cell_angle_beta                 90.746(16)
_cell_angle_gamma                107.794(15)
_cell_formula_units_Z            1
_cell_length_a                   7.182(8)
_cell_length_b                   9.354(10)
_cell_length_c                   10.768(11)
_cell_measurement_reflns_used    420
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.7120
_cell_measurement_theta_min      2.4289
_cell_volume                     648.5(12)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  bruker-CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0883
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3280
_diffrn_reflns_point_group_measured_fraction_full 0.602
_diffrn_reflns_point_group_measured_fraction_max 0.602
_diffrn_reflns_theta_full        25.008
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         2.429
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.8709
_exptl_absorpt_correction_T_min  0.7257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0641 before and 0.0415 after correction.
The Ratio of minimum to maximum transmission is 0.8333.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 270 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2752
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0703
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0123P)^2^+0.5712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1432
_reflns_Friedel_coverage         0.229
_reflns_Friedel_fraction_full    0.224
_reflns_Friedel_fraction_max     0.224
_reflns_number_gt                1518
_reflns_number_total             2752
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc00963a2.cif
_cod_data_source_block           5k
_cod_database_code               7123143
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.970
_shelx_res_checksum              43886