A General Process for the Haloamidation of Olefins. Scope and Mechanism
Ying-Yeung Yeung; Xuri Gao; E. J. Corey; Journal of the American Chemical Society 128 (2006) 9644–9645; doi:10.1021/ja063675w

data_4110798
_publ_section_title
;
 A General Process for the Haloamidation of Olefins. Scope and Mechanism
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9644
_journal_page_last               9645
_journal_paper_doi               10.1021/ja063675w
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C9 H12 Br N O3'
_chemical_formula_weight         262.11
_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   difmap
_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                   8.209(3)
_cell_length_b                   10.253(4)
_cell_length_c                   12.101(5)
_cell_measurement_reflns_used    930
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      3.60
_cell_volume                     1018.5(7)
_computing_cell_refinement       'SMART (BRUKER, V5.625, 2001)'
_computing_data_collection       'ASTRO (BRUKER, V5.007, 1997)'
_computing_data_reduction        'SAINT (BRUKER, V6.22, 2001)'
_computing_molecular_graphics    'SHELXTL (BRUKER, 2000, V6.1)'
_computing_publication_material  'XCIF (Sheldrick and BRUKER, 1997, V5.1)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       '\w, 0.3 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0135
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8325
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.017
_exptl_absorpt_correction_T_max  0.6032
_exptl_absorpt_correction_T_min  0.5005
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_description       chunk
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.495(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.549
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.549
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0164
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+1.4761P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0412
_refine_ls_wR_factor_ref         0.0415
_reflns_number_gt                2057
_reflns_number_total             2087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja063675wsi20060525_052836.cif
_cod_data_source_block           ejc120t
_cod_database_code               4110798