Synthesis of 1,2- and 1,3-Dicarboxylic Acids via Pd(II)-Catalyzed Carboxylation of Aryl and Vinyl C-H Bonds
Ramesh Giri; Jin-Quan Yu; Journal of the American Chemical Society 130 (2008) 14082–14083; doi:10.1021/ja8063827

data_4108569
_publ_section_title
;
 Synthesis of 1,2- and 1,3-Dicarboxylic Acids via Pd(II)-Catalyzed
 Carboxylation of Aryl and Vinyl C-H Bonds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14082
_journal_page_last               14083
_journal_paper_doi               10.1021/ja8063827
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C104 H84 O8 P4 Pd4'
_chemical_formula_weight         2011.19
_chemical_name_systematic
; 
 ? 
;
_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                 97.371(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.651(9)
_cell_length_b                   15.403(6)
_cell_length_c                   27.484(11)
_cell_measurement_reflns_used    9850
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.41
_cell_measurement_theta_min      2.23
_cell_volume                     9930(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\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_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            108354
_diffrn_reflns_theta_full        24.47
_diffrn_reflns_theta_max         24.47
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_T_max  0.9366
_exptl_absorpt_correction_T_min  0.7434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       plate
_exptl_crystal_F_000             4064
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.08
_platon_squeeze_details
; 
 SQUEEZE (PLATON, A.Spek) was used to treat diffuse solvent 
 contributions.  Total electron count found = 554/unit cell.  Solvent is a 
 mix of hexane and CH2Cl2.  The intensive
 properties (density, F(000), etc.) do not reflect these contributions.  
;
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1081
_refine_ls_number_reflns         16348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0871
_reflns_number_gt                12671
_reflns_number_total             16348
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8063827_si_001.cif
_cod_data_source_block           yu10
_cod_original_cell_volume        9929(7)
_cod_database_code               4108569