Diastereoselective Synthesis of Substituted Tetrahydrothiopyrans via (3,5)-Thionium-Ene Cyclization Reaction
Somasekhar Bondalapati; Paramartha Gogoi; Kiran Indukuri; Anil K. Saikia; Journal of Organic Chemistry 77 (2012) 2508–2512; doi:10.1021/jo2023944

data_4027016
_publ_section_title
;
 Diastereoselective Synthesis of Substituted Tetrahydrothiopyrans via
 (3,5)-Thionium-Ene Cyclization Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2508
_journal_page_last               2512
_journal_paper_doi               10.1021/jo2023944
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         '2(C21 H23 S), C21 H24 S'
_chemical_formula_sum            'C21 H24 S'
_chemical_formula_weight         308.13
_chemical_name_systematic
; 
 ? 
;
_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                 97.836(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   9.953(3)
_cell_length_b                   22.576(5)
_cell_length_c                   23.586(6)
_cell_measurement_reflns_used    1113
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      13.56
_cell_measurement_theta_min      2.25
_cell_volume                     5250(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_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  0.1017
_diffrn_reflns_av_sigmaI/netI    0.1005
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            24274
_diffrn_reflns_theta_full        25.44
_diffrn_reflns_theta_max         25.44
_diffrn_reflns_theta_min         1.25
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       needle
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         9704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1370
_refine_ls_R_factor_gt           0.0775
_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^)+(0.1224P)^2^+3.0879P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2011
_refine_ls_wR_factor_ref         0.2468
_reflns_number_gt                8652
_reflns_number_total             9704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2023944_si_003.cif
_cod_data_source_block           s-1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4027016