Palladium-assisted regioselective C-H cyanation of heteroarenes using isonitrile as cyanide source.
Xu, Shuguang; Huang, Xiaomei; Hong, Xiaohu; Xu, Bin; Organic letters 14 (2012) 4614–4617; doi:10.1021/ol302070t

data_1508629
_publ_section_title
;
 Palladium-assisted regioselective C-H cyanation of heteroarenes using
 isonitrile as cyanide source.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4614
_journal_page_last               4617
_journal_paper_doi               10.1021/ol302070t
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C15 H11 N3 O'
_chemical_formula_weight         249.27
_space_group_IT_number           14
_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                90.000(5)
_cell_angle_beta                 103.102(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   7.713(5)
_cell_length_b                   14.167(5)
_cell_length_c                   11.379(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1211.0(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7377
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.089
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.047(3)
_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   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0502P)^2^+0.1913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                2288
_reflns_number_total             2752
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302070t_si_002.cif
_cod_data_source_block           xsg119
_cod_database_code               1508629