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_1505975
_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         'C16 H18 I N O2'
_chemical_formula_structural     IC6H4-N(COCMe=CHMe)2-2
_chemical_formula_sum            'C16 H18 I N O2'
_chemical_formula_weight         383.21
_chemical_name_common            'Compound 3'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 116.4280(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.2310(4)
_cell_length_b                   8.0976(3)
_cell_length_c                   15.6700(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1617.05(9)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'ORTEP (Johnson, 1971)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  'graphite or 10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_sigmaI/netI    0.0835
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18338
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    1.981
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       shard
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.0029(10)
_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   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.1869P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                3088
_reflns_number_total             3717
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ol0606132si20060313_042055.cif
_cod_data_source_block           richs8
_cod_original_sg_symbol_H-M      'P 21/c  (no. 14)'
_cod_database_code               1505975