Three-Component Cascade Annulation of β-Ketothioamides Promoted by CF3CH2OH: A Regioselective Synthesis of Tetrasubstituted Thiophenes
Li-Rong Wen; Tao He; Ming-Chao Lan; Ming Li; Journal of Organic Chemistry 78 (2013) 10617–10628; doi:10.1021/jo401397d

data_4028694
_publ_section_title
;
 Three-Component Cascade Annulation of \b-Ketothioamides Promoted by
 CF3CH2OH: A Regioselective Synthesis of Tetrasubstituted Thiophenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10617
_journal_page_last               10628
_journal_paper_doi               10.1021/jo401397d
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C31 H26 Cl N O3 S'
_chemical_formula_sum            'C31 H26 Cl N O3 S'
_chemical_formula_weight         528.04
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 105.09(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.627(5)
_cell_length_b                   10.341(2)
_cell_length_c                   19.766(4)
_cell_measurement_reflns_used    16162
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.97
_cell_volume                     5254.9(19)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30879
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         0.79
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_correction_T_min  0.8946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       plate
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.283
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     735
_refine_ls_number_reflns         9247
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.279
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0856
_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^)+(0.0262P)^2^+6.8442P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1477
_reflns_number_gt                7930
_reflns_number_total             9247
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401397d_si_001.cif
_cod_data_source_block           a
_cod_original_cell_volume        5254.8(18)
_cod_database_code               4028694