Palladium-Catalyzed C-H Activation/Cross-Coupling of Pyridine N-Oxides with Nonactivated Secondary Alkyl Bromides
Bin Xiao; Zhao-Jing Liu; Lei Liu; Yao Fu; Journal of the American Chemical Society 135 (2013) 616–619; doi:10.1021/ja3113752

data_4119200
_publ_section_title
;
 Palladium-Catalyzed C-H Activation/Cross-Coupling of Pyridine N-Oxides
 with Nonactivated Secondary Alkyl Bromides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              616
_journal_page_last               619
_journal_paper_doi               10.1021/ja3113752
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C38 H54 Cl10 N2 O2 Si'
_chemical_formula_weight         953.42
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8079(13)
_cell_length_b                   11.3243(11)
_cell_length_c                   39.272(5)
_cell_measurement_reflns_used    4911
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      69.6840
_cell_measurement_theta_min      3.3733
_cell_volume                     4806.6(10)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Gemini S Ultra, Oxford Diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) x-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0630
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            16512
_diffrn_reflns_theta_full        65.09
_diffrn_reflns_theta_max         65.09
_diffrn_reflns_theta_min         4.06
_exptl_absorpt_coefficient_mu    5.807
_exptl_absorpt_correction_T_max  0.2662
_exptl_absorpt_correction_T_min  0.2290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       0.00146(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     484
_refine_ls_number_reflns         8120
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0605
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0898P)^2^+6.7816P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.2230
_reflns_number_gt                5135
_reflns_number_total             8120
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3113752_si_003.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        4806.6(9)
_cod_database_code               4119200