Palladium-Catalyzed Picolinamide-Directed Alkylation of Unactivated C(sp3)-H Bonds with Alkyl Iodides
Shu-Yu Zhang; Gang He; William A. Nack; Yingsheng Zhao; Qiong Li; Gong Chen; Journal of the American Chemical Society 135 (2013) 2124–2127; doi:10.1021/ja312277g

data_4119342
_publ_section_title
;
 Palladium-Catalyzed Picolinamide-Directed Alkylation of Unactivated
 C(sp3)-H Bonds with Alkyl Iodides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2124
_journal_page_last               2127
_journal_paper_doi               10.1021/ja312277g
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C34 H44 N4 O8 Pd2'
_chemical_formula_sum            'C34 H44 N4 O8 Pd2'
_chemical_formula_weight         849.53
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           167
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3 2"c'
_symmetry_space_group_name_H-M   'R -3 c :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   36.000(16)
_cell_length_b                   36.000(16)
_cell_length_c                   16.050(8)
_cell_measurement_reflns_used    7427
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.212
_cell_measurement_theta_min      2.260
_cell_volume                     18014(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0671
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            54610
_diffrn_reflns_theta_full        28.61
_diffrn_reflns_theta_max         28.61
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.947
_exptl_absorpt_correction_T_max  0.9367
_exptl_absorpt_correction_T_min  0.8480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       rod
_exptl_crystal_F_000             7776
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_platon_squeeze_details
;
;
_refine_diff_density_max         1.000
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         5083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0861
_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^)+(0.0808P)^2^+67.6815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1912
_refine_ls_wR_factor_ref         0.2106
_reflns_number_gt                3755
_reflns_number_total             5083
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja312277g_si_002.cif
_cod_data_source_block           suz2s
_cod_original_sg_symbol_H-M      'R -3 c'
_cod_database_code               4119342