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_7123142
_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         'C25 H45 N O3 S Si'
_chemical_formula_sum            'C25 H45 N O3 S Si'
_chemical_formula_weight         467.78
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-21
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-01-21 deposited with the CCDC.    2019-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.809(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.328(5)
_cell_length_b                   12.879(6)
_cell_length_c                   10.995(5)
_cell_measurement_reflns_used    1104
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.297
_cell_measurement_theta_min      2.539
_cell_volume                     1452.2(12)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  bruker-CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0907
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8972
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         2.539
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0583 before and 0.0494 after correction.
The Ratio of minimum to maximum transmission is 0.9461.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.070
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.117
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 904 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         6082
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.0628
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0690P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1689
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.857
_reflns_Friedel_fraction_max     0.830
_reflns_number_gt                2905
_reflns_number_total             6082
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc00963a2.cif
_cod_data_source_block           3l
_cod_database_code               7123142
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C21)
\\sim Ueq, Uanis(C20A) \\sim Ueq, Uanis(C19A) \\sim Ueq, Uanis(C21A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C19A)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(1)
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(1)
4.a Riding coordinates:
 N1(H1), C19(H19A,H19B,H19C), C2(H2A,H2B,H2C), C20(H20A,H20B,H20C), C21(H21A,
 H21B,H21C), C20A(H20D,H20E,H20F), C19A(H19D,H19E,H19F), C21A(H21D,H21E,H21F)
4.b Ternary CH refined with riding coordinates:
 C10(H10)
4.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C17(H17), C16(H16)
4.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C8(H8A,H8B,
 H8C), C25(H25A,H25B,H25C), C9(H9A,H9B,H9C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C),
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              5651
_olex2_submission_special_instructions 'No special instructions were received'