Unexpected multiple electrophilic addition reaction of (Z)-alk-2-en-4-ynoates with N,N-dibromo-p-toluenesulfonamide (TsNBr(2)): a highly diastereoselective synthesis of densely functionalized aziridines.
Shen, Ruwei; Huang, Xian; Organic letters 11 (2009) 5698–5701; doi:10.1021/ol902446h

data_1504308
_publ_section_title
;
 Unexpected multiple electrophilic addition reaction of
 (Z)-alk-2-en-4-ynoates with N,N-dibromo-p-toluenesulfonamide (TsNBr(2)):
 a highly diastereoselective synthesis of densely functionalized
 aziridines.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5698
_journal_page_last               5701
_journal_paper_doi               10.1021/ol902446h
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C20 H19 Br2 N O5 S'
_chemical_formula_weight         545.24
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.695(3)
_cell_angle_beta                 90.130(3)
_cell_angle_gamma                101.330(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1285(11)
_cell_length_b                   11.5022(19)
_cell_length_c                   13.676(2)
_cell_measurement_reflns_used    1656
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.203
_cell_measurement_theta_min      4.364
_cell_volume                     1086.3(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0774
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            5757
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    3.858
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3257
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.423
_exptl_crystal_size_min          0.207
_refine_diff_density_max         1.171
_refine_diff_density_min         -1.293
_refine_diff_density_rms         0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3992
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0855
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1531P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2308
_refine_ls_wR_factor_ref         0.2467
_reflns_number_gt                2480
_reflns_number_total             3992
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902446h_si_003.cif
_cod_data_source_block           cd28601
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1504308