Insertions of Silylenes into Vinyl Epoxides: Diastereoselective Synthesis of Functionalized, Optically Active trans-Dioxasilacyclooctenes
Michel Prévost; K. A. Woerpel; Journal of the American Chemical Society 131 (2009) 14182–14183; doi:10.1021/ja906204a

data_4105124
_publ_section_title
;
 Insertions of Silylenes into Vinyl Epoxides: Diastereoselective Synthesis
 of Functionalized, Optically Active trans-Dioxasilacyclooctenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14182
_journal_page_last               14183
_journal_paper_doi               10.1021/ja906204a
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C19 H36 O2 Si'
_chemical_formula_weight         324.57
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 101.8435(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9471(5)
_cell_length_b                   10.0500(4)
_cell_length_c                   14.9118(6)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      28.69
_cell_measurement_theta_min      2.33
_cell_volume                     1898.99(13)
_computing_cell_refinement       'Bruker SMART APEX2/SAINT'
_computing_data_collection       'Bruker SMART 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      103(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'phi and omega'
_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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21906
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_correction_T_min  0.9670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+0.6078P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0861
_reflns_number_gt                4118
_reflns_number_total             4515
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja906204a_si_002.cif
_cod_data_source_block           kaw129
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4105124