π-Face-Selective Diels-Alder Reactions of 3,4-Di-tert-butylthiophene 1-Oxide and 1-Imide and Formation of 1,2-Thiazetidines
Takashi Otani; Jun Takayama; Yoshiaki Sugihara; Akihiko Ishii; Juzo Nakayama; Journal of the American Chemical Society 125 (2003) 8255–8263; doi:10.1021/ja029867i

data_4113872
_publ_contact_author_address
;
Department of Chemistry, Faculty of Science, Saitama University
Saitama, Saitama 338-8570, Japan
;
_publ_contact_author_email       nakaj@post.saitama-u.ac.jp
_publ_contact_author_fax         +81-48-858-3700
_publ_contact_author_name        'Dr. Juzo Nakayama'
_publ_contact_author_phone       +81-48-858-3390
_publ_section_title
;
 \p-Face-Selective Diels-Alder Reactions of 3,4-Di-tert-butylthiophene
 1-Oxide and 1-Imide and Formation of 1,2-Thiazetidines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8255
_journal_page_last               8263
_journal_paper_doi               10.1021/ja029867i
_journal_volume                  125
_journal_year                    2003
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C16 H22 O4 S '
_chemical_formula_sum            'C16 H22 O4 S'
_chemical_formula_weight         310.412
_space_group_IT_number           85
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-P 4a'
_symmetry_space_group_name_H-M   'P 4/n :2'
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   21.4715(12)
_cell_length_b                   21.4715(12)
_cell_length_c                   15.3680(11)
_cell_measurement_temperature    153
_cell_volume                     7085.0(8)
_computing_cell_refinement       'HKL Scalepack'
_computing_data_collection       'DIP Image plate'
_computing_data_reduction        'maXus (Mackay et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device       'DIP Image plate'
_diffrn_measurement_method       IP
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.114
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7634
_diffrn_reflns_theta_full        27.27
_diffrn_reflns_theta_max         27.27
_diffrn_reflns_theta_min         0.00
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       Cube
_refine_diff_density_max         1.711
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       0.0032(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         7374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.2258
_refine_ls_R_factor_gt           0.0991
_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^)+ (0.1000P)^2^+1.3000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2441
_refine_ls_wR_factor_ref         0.2741
_reflns_number_gt                2620
_reflns_number_total             7374
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja029867isi20021221_041534.cif
_cod_data_source_block           global
_cod_original_sg_symbol_H-M      'P 4/n '
_cod_original_formula_sum        'C16 H22 O4 S '
_cod_database_code               4113872