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_1504309
_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            'C27 H27 Br3 N2 O6 S2'
_chemical_formula_weight         779.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.622(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7972(17)
_cell_length_b                   17.906(4)
_cell_length_c                   22.658(5)
_cell_measurement_reflns_used    1745
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      37.899
_cell_measurement_theta_min      4.894
_cell_volume                     3153.1(12)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1039
_diffrn_reflns_av_sigmaI/netI    0.1828
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16192
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    4.012
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4675
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5867
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.890
_refine_ls_R_factor_all          0.1455
_refine_ls_R_factor_gt           0.0701
_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^)+(0.0699P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1611
_refine_ls_wR_factor_ref         0.1756
_reflns_number_gt                2498
_reflns_number_total             5867
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902446h_si_004.cif
_cod_data_source_block           cd29268
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_cell_volume        3153.2(12)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1504309