Nucleophilic Addition to Silyl-Protected Five-Membered Ring Oxocarbenium Ions Governed by Stereoelectronic Effects
Vi Tuong Tran; K. A. Woerpel; Journal of Organic Chemistry 78 (2013) 6609–6621; doi:10.1021/jo400945j

data_4028407
_publ_section_title
;
 Nucleophilic Addition to Silyl-Protected Five-Membered Ring Oxocarbenium
 Ions Governed by Stereoelectronic Effects
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6609
_journal_page_last               6621
_journal_paper_doi               10.1021/jo400945j
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C26 H44 N4 O8 Si2'
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_symmetry_space_group_name_Hall  '-P 2ybc'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 100.870(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.418(6)
_cell_length_b                   7.6590(19)
_cell_length_c                   18.298(5)
_cell_measurement_reflns_used    5762
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.30
_cell_measurement_theta_min      2.27
_cell_volume                     3085.4(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1028
_diffrn_reflns_av_sigmaI/netI    0.2135
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31572
_diffrn_reflns_theta_full        21.99
_diffrn_reflns_theta_max         21.99
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       needle
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         3768
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_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1617
_refine_ls_R_factor_gt           0.0933
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2181
_refine_ls_wR_factor_ref         0.2357
_reflns_number_gt                1719
_reflns_number_total             3768
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400945j_si_004.cif
_cod_data_source_block           12kaw3h2
_cod_original_cell_volume        3085.4(13)
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4028407