Low-Temperature Heck Reactions of Axially Chiral o-Iodoacrylanilides Occur with Chirality Transfer: Implications for Catalytic Asymmetric Heck Reactions
Andre J. B. Lapierre; Steven J. Geib; Dennis P. Curran; Journal of the American Chemical Society 129 (2007) 494–495; doi:10.1021/ja067790i

data_4108996
_publ_contact_author_address
;Department of Chemistry 
University of Pittsburgh
Pittsburgh, PA 15260
;
_publ_contact_author_email       curran@pitt.edu
_publ_contact_author_name        'Dennis P. Curran'
_publ_contact_author_phone       412-624-8240
_publ_section_title
;
 Low-Temperature Heck Reactions of Axially Chiral o-Iodoacrylanilides
 Occur with Chirality Transfer: Implications for Catalytic Asymmetric Heck
 Reactions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              494
_journal_page_last               495
_journal_paper_doi               10.1021/ja067790i
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H14 Br N O'
_chemical_formula_weight         280.16
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 100.891(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4400(15)
_cell_length_b                   7.1595(13)
_cell_length_c                   10.6031(18)
_cell_measurement_reflns_used    1938
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.48
_cell_measurement_theta_min      2.46
_cell_volume                     629.16(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Smart Apex 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  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0726
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6284
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    3.246
_exptl_absorpt_correction_T_max  0.6967
_exptl_absorpt_correction_T_min  0.4975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;Bruker (1997). SADABS. Bruker AXS Inc., Madison,
Wisconsin, USA.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       anti-prism
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.104
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3080
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0792P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1398
_reflns_number_gt                2141
_reflns_number_total             3080
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja067790irom20061031_015127.cif
_cod_data_source_block           5b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4108996