Stereoselective Synthesis of 2,8-Dioxabicyclo[3.3.1]nonane Derivatives via a Sequential Michael Addition/Bicyclization Reaction
Guodong Yin; Tianbing Ren; Yin Rao; Yifan Zhou; Zhexian Li; Wenming Shu; Anxin Wu; Journal of Organic Chemistry 78 (2013) 3132–3141; doi:10.1021/jo400081q

data_4028095
_publ_section_title
;
 Stereoselective Synthesis of 2,8-Dioxabicyclo[3.3.1]nonane Derivatives
 via a Sequential Michael Addition/Bicyclization Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3132
_journal_page_last               3141
_journal_paper_doi               10.1021/jo400081q
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C21 H20 O3 S'
_chemical_formula_sum            'C21 H20 O3 S'
_chemical_formula_weight         352.43
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.883(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5257(18)
_cell_length_b                   9.4236(15)
_cell_length_c                   17.540(3)
_cell_measurement_reflns_used    7513
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      31.99
_cell_measurement_theta_min      2.44
_cell_volume                     1813.0(5)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12412
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_correction_T_min  0.9565
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0509
_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^)+(0.0961P)^2^+0.6564P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1650
_reflns_number_gt                3266
_reflns_number_total             3752
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400081q_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        1813.1(5)
_cod_database_code               4028095