Palladium-Catalyzed Aromatic C-H Halogenation with Hydrogen Halides by Means of Electrochemical Oxidation
Fumitoshi Kakiuchi; Takuya Kochi; Hitoshi Mutsutani; Noboru Kobayashi; Seiya Urano; Mitsuo Sato; Shigeru Nishiyama; Takamasa Tanabe; Journal of the American Chemical Society 131 (2009) 11310–11311; doi:10.1021/ja9049228

data_4104878
_publ_section_title
;
 Palladium-Catalyzed Aromatic C-H Halogenation with Hydrogen Halides by
 Means of Electrochemical Oxidation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11310
_journal_page_last               11311
_journal_paper_doi               10.1021/ja9049228
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C15 H10 Cl N'
_chemical_formula_weight         239.69
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.5764(18)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.182(4)
_cell_length_b                   15.809(9)
_cell_length_c                   8.773(5)
_cell_measurement_reflns_used    3515
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      3.4765
_cell_volume                     1131.2(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8473
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.9697
_exptl_absorpt_correction_T_min  0.8861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Jacobson, R. (1998). Private communication to the Rigaku Corporation'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0498P)^2^+0.3269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0865
_reflns_number_gt                2293
_reflns_number_total             2538
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9049228_si_002.cif
_cod_data_source_block           20
_cod_database_code               4104878