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_4027015
_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_sum            'C15 H19 N O2 S'
_chemical_formula_weight         277.37
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.585(2)
_cell_angle_beta                 84.603(3)
_cell_angle_gamma                69.277(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4612(3)
_cell_length_b                   9.3954(3)
_cell_length_c                   11.6354(5)
_cell_measurement_reflns_used    3457
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.67
_cell_volume                     744.90(5)
_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  0.0677
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10495
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1256
_reflns_number_gt                2287
_reflns_number_total             3724
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2023944_si_002.cif
_cod_data_source_block           platon
_cod_original_formula_sum        'C15 H19 N1 O2 S'
_cod_database_code               4027015