A Radical Cascade Cyclization To Prepare Dihydrothiophenes Induced by Thiyl Radicals as Sulfur Biradical Equivalents
Akio Kamimura; Koichiro Miyazaki; Yu Yamane; Ryuichiro Yo; Shingo Ishikawa; Hidemitsu Uno; Michinori Sumimoto; Journal of Organic Chemistry 78 (2013) 7816–7822; doi:10.1021/jo400975t

data_4028491
_publ_section_title
;
 A Radical Cascade Cyclization To Prepare Dihydrothiophenes Induced by
 Thiyl Radicals as Sulfur Biradical Equivalents
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7816
_journal_page_last               7822
_journal_paper_doi               10.1021/jo400975t
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C24 H27 N O4 S2'
_chemical_formula_sum            'C24 H27 N O4 S2'
_chemical_formula_weight         457.60
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_symmetry_cell_setting           orthorhombic
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_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.5849(5)
_cell_length_b                   10.9787(8)
_cell_length_c                   26.2197(16)
_cell_measurement_reflns_used    14750
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.01
_cell_volume                     2471.2(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
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_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             968.00
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.230
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2419 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_coef       0.0111(11)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     282
_refine_ls_number_reflns         5611
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.0677P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1143
_reflns_number_gt                3205
_reflns_number_total             5611
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo400975t_si_002.cif
_cod_data_source_block           KM05027-A
_cod_database_code               4028491