Regioselective Synthesis of Dihydrothiophenes and Thiophenes via the Rhodium-Catalyzed Transannulation of 1,2,3-Thiadiazoles with Alkenes.
Son, Jeong-Yu; Kim, Jonghye; Han, Sang Hoon; Kim, Sung Hong; Lee, Phil Ho; Organic letters 18 (2016) 5408–5411; doi:10.1021/acs.orglett.6b02805

data_1555876
_publ_section_title
;
 Regioselective Synthesis of Dihydrothiophenes and Thiophenes via the
 Rhodium-Catalyzed Transannulation of 1,2,3-Thiadiazoles with Alkenes.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5408
_journal_page_last               5411
_journal_paper_doi               10.1021/acs.orglett.6b02805
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C19 H17 Br O2 S'
_chemical_formula_weight         389.29
_chemical_name_common            SJY-005
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.8765(6)
_cell_length_b                   9.6372(4)
_cell_length_c                   24.3534(9)
_cell_measurement_reflns_used    113
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      18.8334
_cell_measurement_theta_min      3.1807
_cell_volume                     3491.5(2)
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_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_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            101803
_diffrn_reflns_theta_full        28.45
_diffrn_reflns_theta_max         28.45
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    2.481
_exptl_absorpt_correction_T_max  0.66
_exptl_absorpt_correction_T_min  0.43
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.485
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0406P)^2^+4.4447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1343
_reflns_number_gt                2840
_reflns_number_total             4391
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02805_si_003.cif
_cod_data_source_block           I
_cod_database_code               1555876