Metal-free halonium mediated acetate shifts of ynamides to access α-halo acrylamides/acrylimides.
Kramer, Søren; Friis, Stig D.; Xin, Zhuo; Odabachian, Yann; Skrydstrup, Troels; Organic letters 13 (2011) 1750–1753; doi:10.1021/ol200269h

data_1502073
_publ_section_title
;
 Metal-free halonium mediated acetate shifts of ynamides to access \a-halo
 acrylamides/acrylimides.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1750
_journal_page_last               1753
_journal_paper_doi               10.1021/ol200269h
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C27 H23 Br N2 O5 S'
_chemical_formula_weight         567.44
_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                 98.5892(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.71437(13)
_cell_length_b                   9.95279(11)
_cell_length_c                   19.7029(2)
_cell_measurement_reflns_used    25437
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      29.2031
_cell_measurement_theta_min      2.2932
_cell_volume                     2465.31(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET)
(compiled Aug 18 2010,17:42:00)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET)
(compiled Aug 18 2010,17:42:00)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET)
(compiled Aug 18 2010,17:42:00)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3590
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0920
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            58296
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.2031
_diffrn_reflns_theta_min         2.2932
_exptl_absorpt_coefficient_mu    1.794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET)
(compiled Aug 18 2010,17:42:00)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         2.273
_refine_diff_density_min         -1.544
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.531
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         6412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.531
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0538
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1942
_refine_ls_wR_factor_ref         0.2023
_reflns_number_gt                5465
_reflns_number_total             6412
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200269h_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               1502073