Thia-Prins Bicyclization Approach for the Stereoselective Synthesis of Dithia- and Azathia-Bicycles
B. V. Subba Reddy; A. Venkateswarlu; Prashant Borkar; J. S. Yadav; M. Kanakaraju; A. C. Kunwar; B. Sridhar; Journal of Organic Chemistry 78 (2013) 6303–6308; doi:10.1021/jo400680w

data_4028339
_publ_contact_author_address
;Laboratory of x-ray Crystallography
CSIR-Indian Institute of Chemical Technology
Hyderabad- 500 007
India
;
_publ_contact_author_email       sshiya@yahoo.com
_publ_contact_author_name        B.Sridhar
_publ_section_title
;
 Thia-Prins Bicyclization Approach for the Stereoselective Synthesis of
 Dithia- and Azathia-Bicycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6303
_journal_page_last               6308
_journal_paper_doi               10.1021/jo400680w
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C17 H18 S2'
_chemical_formula_sum            'C17 H18 S2'
_chemical_formula_weight         286.43
_chemical_name_systematic
; 
(3aS*,4R*,7aS*)-4-(naphthalen-1-yl)hexahydro-2H-thieno[3,2-c]thiopyran
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.394(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.8483(16)
_cell_length_b                   10.6900(8)
_cell_length_c                   13.6039(11)
_cell_measurement_reflns_used    5167
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.47
_cell_volume                     2893.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       '\w scan'
_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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27182
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0514P)^2^+0.7155P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                4256
_reflns_number_total             5093
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo400680w_si_001.cif
_cod_data_source_block           ao63
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028339