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_4113877
_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         'C22 H28 N4 O3 S '
_chemical_formula_sum            'C22 H28 N4 O3 S'
_chemical_formula_weight         428.555
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           maXus
_cell_angle_alpha                66.974(5)
_cell_angle_beta                 82.138(4)
_cell_angle_gamma                85.308(6)
_cell_formula_units_Z            2
_cell_length_a                   7.8070(7)
_cell_length_b                   10.9520(6)
_cell_length_c                   14.1090(11)
_cell_measurement_temperature    153
_cell_volume                     1099.27(15)
_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 0.845
_diffrn_measured_fraction_theta_max 0.845
_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  0.052
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4037
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         0.00
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.855
_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    1.295
_exptl_crystal_description       Cube
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0225(18)
_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   1.012
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0593
_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^)+(0.0080P)^2^+0.8000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1447
_reflns_number_gt                2247
_reflns_number_total             4037
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja029867isi20021221_041539.cif
_cod_data_source_block           global
_cod_original_cell_volume        1099.27(14)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C22 H28 N4 O3 S '
_cod_database_code               4113877