[5 + 2] Cycloaddition Reaction of 2-Vinylaziridines and Sulfonyl Isocyanates. Synthesis of Seven-Membered Cyclic Ureas
Eri Kanno; Kenichi Yamanoi; Shunsuke Koya; Isao Azumaya; Hyuma Masu; Ryu Yamasaki; Shinichi Saito; Journal of Organic Chemistry 77 (2012) 2142–2148; doi:10.1021/jo201959a

data_4026998
_publ_contact_author_address
;Department of Chemistry, 
Faculty of Science Tokyo University of Science
1-3 Kagurazaka,Shinjuku, Tokyo 162-8601, JAPAN
;
_publ_contact_author_email       ssaito@rs.kagu.tus.ac.jp
_publ_contact_author_fax         +81-3-3235-2214
_publ_contact_author_name        'Shinichi Saito'
_publ_contact_author_phone       +81-3-5228-8715
_publ_section_title
;
 [5 + 2] Cycloaddition Reaction of 2-Vinylaziridines and Sulfonyl
 Isocyanates. Synthesis of Seven-Membered Cyclic Ureas
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2142
_journal_page_last               2148
_journal_paper_doi               10.1021/jo201959a
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H20 N2 O3 S'
_chemical_formula_weight         356.43
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1338(9)
_cell_length_b                   10.1569(9)
_cell_length_c                   16.9149(15)
_cell_measurement_reflns_used    3162
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.73
_cell_measurement_theta_min      2.34
_cell_volume                     1741.0(3)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8680
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.25
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.9406
_exptl_absorpt_correction_T_min  0.9219
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+0.2028P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0762
_reflns_number_gt                3203
_reflns_number_total             3523
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201959a_si_001.cif
_cod_data_source_block           a0810021mas
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4026998