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_4108997
_publ_contact_author_address
;Department of Chemistry
University of Pittsburgh
Pittsburgh, PA 1526
USA
;
_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_formula_moiety         'C13 H15 Br I N O'
_chemical_formula_sum            'C13 H15 Br I N O'
_chemical_formula_weight         408.07
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5577(7)
_cell_length_b                   13.4492(13)
_cell_length_c                   16.1147(16)
_cell_measurement_temperature    100(2)
_cell_volume                     1421.2(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18553
_diffrn_reflns_theta_full        32.58
_diffrn_reflns_theta_max         32.58
_diffrn_reflns_theta_min         1.97
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    5.049
_exptl_absorpt_correction_T_max  0.3650
_exptl_absorpt_correction_T_min  0.2786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.907
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.006
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.018(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.858
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         5040
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.858
_refine_ls_R_factor_all          0.0156
_refine_ls_R_factor_gt           0.0148
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0233P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0372
_refine_ls_wR_factor_ref         0.0375
_reflns_number_gt                4880
_reflns_number_total             5040
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja067790irom20061031_015154.cif
_cod_data_source_block           4b
_cod_database_code               4108997