Palladium(II)-Catalyzed Direct Alkenylation and Arylation of Arenes: Removable 2-Pyridylsulfinyl Group Assisted C-H Bond Activation
Ming Yu; Zunjun Liang; Yongyong Wang; Yuhong Zhang; Journal of Organic Chemistry 76 (2011) 4987–4994; doi:10.1021/jo200666z

data_4026385
_publ_section_title
;
 Palladium(II)-Catalyzed Direct Alkenylation and Arylation of Arenes:
 Removable 2-Pyridylsulfinyl Group Assisted C-H Bond Activation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4987
_journal_page_last               4994
_journal_paper_doi               10.1021/jo200666z
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C21 H17 N O3 S'
_chemical_formula_sum            'C21 H17 N O3 S'
_chemical_formula_weight         363.42
_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                 99.668(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1178(2)
_cell_length_b                   23.1935(6)
_cell_length_c                   15.3254(5)
_cell_measurement_reflns_used    4390
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.9942
_cell_measurement_theta_min      2.9225
_cell_volume                     1793.28(10)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11635
_diffrn_reflns_theta_full        67.11
_diffrn_reflns_theta_max         67.11
_diffrn_reflns_theta_min         3.49
_exptl_absorpt_coefficient_mu    1.774
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0684P)^2^+0.3282P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                2339
_reflns_number_total             3080
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200666z_si_001.cif
_cod_data_source_block           101020_ym193_2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026385