Reaction of 2,3-Allenoates with TsNBr~2~ in the Presence of Base: A Facile Highly Stereoselective Synthesis of (1E,2E)-3-Bromo-4-oxo-N'-tosyl-2-alkenoxylimidic Acid Ethyl Esters
Ruwei Shen; Xian Huang; Journal of Organic Chemistry 72 (2007) 3961–3964; doi:10.1021/jo070239z

data_4022918
_publ_section_title
;
 Reaction of 2,3-Allenoates with TsNBr~2~ in the Presence of Base:
 A Facile Highly Stereoselective Synthesis of
 (1E,2E)-3-Bromo-4-oxo-N'-tosyl-2-alkenoxylimidic Acid Ethyl Esters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3961
_journal_page_last               3964
_journal_paper_doi               10.1021/jo070239z
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C24 H22 Br N O4 S'
_chemical_formula_weight         500.40
_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                 99.855(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8562(15)
_cell_length_b                   18.118(3)
_cell_length_c                   14.055(2)
_cell_measurement_reflns_used    2110
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.720
_cell_measurement_theta_min      5.074
_cell_volume                     2221.9(6)
_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  0.1488
_diffrn_reflns_av_sigmaI/netI    0.1259
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11977
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    1.975
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6575
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.506
_exptl_crystal_size_mid          0.478
_exptl_crystal_size_min          0.345
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.868
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.841
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.841
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0607
_refine_ls_shift/su_max          0.060
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                2220
_reflns_number_total             4351
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070239zsi20070205_123313.cif
_cod_data_source_block           cd26490
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022918