Palladium-Catalyzed Coupling of Arene C-H Bonds with Methyl- and Arylboron Reagents Assisted by the Removable 2-Pyridylsulfinyl Group
José A. Romero-Revilla; Alfonso García-Rubia; Ramón Goméz Arrayás; M. Ángeles Fernández-Ibáñez; Juan C. Carretero; Journal of Organic Chemistry 76 (2011) 9525–9530; doi:10.1021/jo2018137

data_4026745
_publ_section_title
;
 Palladium-Catalyzed Coupling of Arene C-H Bonds with Methyl- and
 Arylboron Reagents Assisted by the Removable 2-Pyridylsulfinyl Group
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9525
_journal_page_last               9530
_journal_paper_doi               10.1021/jo2018137
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C26.5 H23 Cl N2 O6.5 Pd2 S2'
_chemical_formula_weight         785.84
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 105.9220(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.0429(6)
_cell_length_b                   19.2530(5)
_cell_length_c                   15.1462(4)
_cell_measurement_reflns_used    9346
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      2.80
_cell_volume                     6461.7(3)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            69707
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.366
_exptl_absorpt_correction_T_max  0.8869
_exptl_absorpt_correction_T_min  0.7624
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      0
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             3112
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.575
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.294
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         8004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.218
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0781P)^2^+7.8047P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1377
_reflns_number_gt                6695
_reflns_number_total             8004
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2018137_si_001.cif
_cod_data_source_block           datos_0m
_cod_original_formula_sum        'C26.50 H23 Cl N2 O6.50 Pd2 S2'
_cod_database_code               4026745