On the Mechanism of the Palladium(II)-Catalyzed Decarboxylative Olefination of Arene Carboxylic Acids. Crystallographic Characterization of Non-Phosphine Palladium(II) Intermediates and Observation of Their Stepwise Transformation in Heck-like Processes
Daisuke Tanaka; Stuart P. Romeril; Andrew G. Myers; Journal of the American Chemical Society 127 (2005) 10323–10333; doi:10.1021/ja052099l

data_4111812
_publ_contact_author_address
;Harvard University
Department of Chemistry and Chemical Biology
12 Oxford St
Cambridge MA 02138
;
_publ_contact_author_email       Myers@chemistry.harvard.edu
_publ_contact_author_fax         617-496-4976
_publ_contact_author_name        'Andrew G. Myers'
_publ_contact_author_phone       617-495-5718
_publ_section_title
;
 On the Mechanism of the Palladium(II)-Catalyzed Decarboxylative
 Olefination of Arene Carboxylic Acids. Crystallographic Characterization
 of Non-Phosphine Palladium(II) Intermediates and Observation of Their
 Stepwise Transformation in Heck-like Processes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10323
_journal_page_last               10333
_journal_paper_doi               10.1021/ja052099l
_journal_volume                  127
_journal_year                    2005
_chemical_formula_moiety         'C20 H21 D6 F3 O6 Pd S'
_chemical_formula_sum            'C20 H21 D6 F3 O6 Pd S'
_chemical_formula_weight         564.91
_chemical_name_systematic
; 
 ? 
;
_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                   9.3554(12)
_cell_length_b                   14.1121(19)
_cell_length_c                   16.823(2)
_cell_measurement_temperature    193(2)
_cell_volume                     2221.0(5)
_computing_cell_refinement       'SMART (BRUKER, V5.625, 2001)'
_computing_data_collection       'ASTRO (BRUKER, V5.007, 1997)'
_computing_data_reduction        'SAINT (BRUKER, V6.22, 2001)'
_computing_molecular_graphics    'SHELXTL (BRUKER, 2000, V6.1)'
_computing_publication_material  'XCIF (Sheldrick and BRUKER, 1997, V5.1)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       '\w, 0.3 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15825
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_T_max  0.9251
_exptl_absorpt_correction_T_min  0.7973
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.082
_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   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0281P)^2^+0.1548P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0697
_reflns_number_gt                5108
_reflns_number_total             5281
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja052099lsi20050408_020553.cif
_cod_data_source_block           Compound_11
_cod_original_cell_volume        2221.1(5)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4111812