Regioselective synthesis of tetrahydrothiochromen-5-ones via a one-pot three-component solvent-free domino protocol.
Chowdhury, Sushobhan; Nandi, Ganesh Chandra; Samai, Subhasis; Singh, Maya Shankar; Organic letters 13 (2011) 3762–3765; doi:10.1021/ol201458q

data_1502303
_publ_section_title
;
 Regioselective synthesis of tetrahydrothiochromen-5-ones via a one-pot
 three-component solvent-free domino protocol.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3762
_journal_page_last               3765
_journal_paper_doi               10.1021/ol201458q
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C23 H19 F O2 S2'
_chemical_formula_weight         410.52
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                90.857(10)
_cell_angle_beta                 99.261(10)
_cell_angle_gamma                113.392(13)
_cell_formula_units_Z            2
_cell_length_a                   9.2779(13)
_cell_length_b                   9.5225(13)
_cell_length_c                   12.6163(14)
_cell_measurement_temperature    293(2)
_cell_volume                     1005.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.834
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_sigmaI/netI    0.1277
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8537
_diffrn_reflns_theta_full        55.00
_diffrn_reflns_theta_max         25.31
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.290
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1922
_refine_ls_R_factor_gt           0.0853
_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^)+(0.1019P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1905
_refine_ls_wR_factor_ref         0.2663
_reflns_number_gt                1875
_reflns_number_total             4596
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201458q_si_003.cif
_cod_data_source_block           sr-66
_cod_original_cell_volume        1005.9(2)
_cod_original_formula_sum        C23H19F1O2S2
_cod_database_code               1502303