Assessment of the Intermediacy of Arylpalladium Carboxylate Complexes in the Direct Arylation of Benzene: Evidence for C-H Bond Cleavage by "Ligandless" Species
Yichen Tan; John F. Hartwig; Journal of the American Chemical Society 133 (2011) 3308–3311; doi:10.1021/ja1113936

data_4105761
_publ_section_title
;
 Assessment of the Intermediacy of Arylpalladium Carboxylate Complexes in
 the Direct Arylation of Benzene: Evidence for C-H Bond Cleavage by
 "Ligandless" Species
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3308
_journal_page_last               3311
_journal_paper_doi               10.1021/ja1113936
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C24 H43 O2 P Pd'
_chemical_formula_sum            'C24 H43 O2 P Pd'
_chemical_formula_weight         500.95
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_audit_update_record
; 
? 
;
_cell_angle_alpha                94.415(4)
_cell_angle_beta                 94.031(4)
_cell_angle_gamma                116.913(4)
_cell_formula_units_Z            4
_cell_length_a                   10.9975(8)
_cell_length_b                   12.0887(9)
_cell_length_c                   21.6801(14)
_cell_measurement_reflns_used    2163
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.16
_cell_measurement_theta_min      2.28
_cell_volume                     2544.5(3)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.0-1 (Bruker, 2004)'
_computing_data_reduction
; 
SAINT V7.23A, XPREP V2005/2, SADABS V2007/4, TWINABS V2007/5 
(Bruker, 2005 & 2007) 
;
_computing_molecular_graphics
; 
SHELXTL V6.12 (Bruker, 2005), CrystalMaker v2.1.3 (CrystalMaker, 1994)
;
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  ba85j_twin5
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18424
_diffrn_reflns_theta_full        26.47
_diffrn_reflns_theta_max         26.47
_diffrn_reflns_theta_min         0.95
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  0.8856
_exptl_absorpt_correction_T_min  0.8337
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_id                ba85j_twin5
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research). 
;
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.174
_refine_diff_density_max         0.928
_refine_diff_density_min         -0.756
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         18424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1227P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1778
_reflns_number_gt                14858
_reflns_number_total             18424
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1113936_si_002.cif
_cod_data_source_block           twin5
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4105761