Palladium(II)-Catalyzed Direct Ortho Arylation of 4-Methyl-N-phenylpyridin-2-amines via C–H Activation/C–C Coupling and Synthetic Applications
Chu, Jean-Ho; Huang, Hao-Ping; Hsu, Wen-Ting; Chen, Shih-Tien; Wu, Ming-Jung; Organometallics 33 (2014) 1190–; doi:10.1021/om401195w

data_4082714
_publ_section_title
;
 Palladium(II)-Catalyzed Direct Ortho Arylation of
 4-Methyl-N-phenylpyridin-2-amines via C--H Activation/C--C Coupling and
 Synthetic Applications
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              1190
_journal_paper_doi               10.1021/om401195w
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C113 H114 Cl2 N16 O16 Pd8'
_chemical_formula_sum            'C113 H114 Cl2 N16 O16 Pd8'
_chemical_formula_weight         2874.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 108.510(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.023(3)
_cell_length_b                   24.029(4)
_cell_length_c                   16.748(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     5733.1(18)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0834
_diffrn_reflns_av_sigmaI/netI    0.1046
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            35951
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    1.341
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_correction_T_min  0.6228
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2868
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.476
_refine_diff_density_min         -0.958
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     707
_refine_ls_number_reflns         10138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+7.1948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1678
_reflns_number_gt                6299
_reflns_number_total             10138
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om401195w_si_001.cif
_cod_data_source_block           a14703
_cod_original_cell_volume        5733.0(16)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4082714