Diastereoselective Synthesis of Seven-Membered-Ring trans-Alkenes from Dienes and Aldehydes by Silylene Transfer
Margaret A. Greene; Michel Prévost; Joshua Tolopilo; K. A. Woerpel; Journal of the American Chemical Society 134 (2012) 12482–12484; doi:10.1021/ja305713v

data_4118441
_publ_section_title
;
 Diastereoselective Synthesis of Seven-Membered-Ring trans-Alkenes from
 Dienes and Aldehydes by Silylene Transfer
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12482
_journal_page_last               12484
_journal_paper_doi               10.1021/ja305713v
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C20 H32 O Si'
_chemical_formula_weight         316.55
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 99.6550(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6430(8)
_cell_length_b                   9.0342(5)
_cell_length_c                   14.9309(8)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.65
_cell_volume                     1947.20(18)
_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      143(2)
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21783
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         28.50
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9535
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_density_meas      ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0547P)^2^+0.4634P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                3999
_reflns_number_total             4619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja305713v_si_003.cif
_cod_data_source_block           kaw155
_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               4118441