Intramolecular asymmetric Heck reactions: evidence for dynamic kinetic resolution effects.
McDermott, Michael C.; Stephenson, G. Richard; Hughes, David L.; Walkington, Andrew J.; Organic letters 8 (2006) 2917–2920; doi:10.1021/ol0606132

data_1505973
_publ_section_title
;
 Intramolecular asymmetric Heck reactions: evidence for dynamic kinetic
 resolution effects.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2917
_journal_page_last               2920
_journal_paper_doi               10.1021/ol0606132
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C12 H14 I N O'
_chemical_formula_structural     C6H4I,-(NMeCOCMe=CHMe)-2
_chemical_formula_sum            'C12 H14 I N O'
_chemical_formula_weight         315.14
_chemical_name_common            'Compound 5'
_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   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                   11.126(14)
_cell_length_b                   12.092(9)
_cell_length_c                   8.986(5)
_cell_measurement_temperature    140(1)
_cell_volume                     1208.9(19)
_computing_cell_refinement       'MSC/AFC Diffractometer Software (MSC, 1993)'
_computing_data_collection       'MSC/AFC Diffractometer Software (MSC, 1993)'
_computing_data_reduction        'MSC texSan/PROCESS (MSC, 1993)'
_computing_molecular_graphics    'ORTEP (Johnson, 1971)'
_computing_publication_material  'SHELXL (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS (Sheldrick, 1997)'
_diffrn_ambient_temperature      140(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Rigaku/MSC AFC7R diffractometer'
_diffrn_measurement_method       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.095
_diffrn_reflns_av_sigmaI/netI    0.0757
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2829
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 250
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.623
_exptl_absorpt_correction_type   'not applied'
_exptl_crystal_colour            'clear, colourless'
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_refine_diff_density_max         1.621
_refine_diff_density_min         -2.980
_refine_diff_density_rms         0.200
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0972P)^2^+0.8416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                2103
_reflns_number_total             2120
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ol0606132si20060313_042055.cif
_cod_data_source_block           richs1
_cod_original_sg_symbol_H-M      'P 212121  (no. 19)'
_cod_database_code               1505973