Studies on the Heck Reaction with Alkenyl Phosphates: Can the 1,2-Migration Be Controlled? Scope and Limitations
Jean-Philippe Ebran; Anders L. Hansen; Thomas M. Gøgsig; Troels Skrydstrup; Journal of the American Chemical Society 129 (2007) 6931–6942; doi:10.1021/ja070321b

data_4109460
_publ_contact_author             'Overgaard, Jacob'
_publ_contact_author_email       jacobo@chem.au.dk
_publ_section_title
;
 Studies on the Heck Reaction with Alkenyl Phosphates: Can the
 1,2-Migration Be Controlled? Scope and Limitations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6931
_journal_page_last               6942
_journal_paper_doi               10.1021/ja070321b
_journal_volume                  129
_journal_year                    2007
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H22 N2 O3'
_chemical_formula_sum            'C18 H22 N2 O3'
_chemical_formula_weight         157.19
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-09-14T08:47:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                65.844(10)
_cell_angle_beta                 86.374(15)
_cell_angle_gamma                89.887(18)
_cell_formula_units_Z            4
_cell_length_a                   6.1433(19)
_cell_length_b                   16.535(7)
_cell_length_c                   18.466(8)
_cell_measurement_reflns_used    1023
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.45
_cell_measurement_theta_min      2.7
_cell_measurement_wavelength     0.71073
_cell_volume                     1707.5(12)
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2006)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2006)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.681
_diffrn_measured_fraction_theta_max 0.681
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       '\f-scans and \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0849
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3674
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         1.35
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0934
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1604P)^2^+5.0929P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2789
_refine_ls_wR_factor_ref         0.3042
_reflns_number_gt                2253
_reflns_number_total             3344
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja070321bsi20070116_082524.cif
_cod_data_source_block           06jo0036_01
_cod_original_cell_volume        1707.5(11)
_cod_database_code               4109460