Ir(III)-Catalyzed Mild C-H Amidation of Arenes and Alkenes: An Efficient Usage of Acyl Azides as the Nitrogen Source
Jaeyune Ryu; Jaesung Kwak; Kwangmin Shin; Donggun Lee; Sukbok Chang; Journal of the American Chemical Society 135 (2013) 12861–12868; doi:10.1021/ja406383h

data_4120388
_publ_section_title
;
 Ir(III)-Catalyzed Mild C-H Amidation of Arenes and Alkenes: An Efficient
 Usage of Acyl Azides as the Nitrogen Source
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12861
_journal_page_last               12868
_journal_paper_doi               10.1021/ja406383h
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C15 H19 N3 O4'
_chemical_formula_sum            'C15 H19 N3 O4'
_chemical_formula_weight         305.33
_space_group_IT_number           148
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-P 3*'
_symmetry_space_group_name_H-M   'R -3 :R'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                113.28
_cell_angle_beta                 113.28
_cell_angle_gamma                113.28
_cell_formula_units_Z            6
_cell_length_a                   15.5832(8)
_cell_length_b                   15.5832(8)
_cell_length_c                   15.5832(8)
_cell_measurement_reflns_used    3841
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      23.58
_cell_measurement_theta_min      2.45
_cell_volume                     2416.9(2)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0543
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15391
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             972
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0520
_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^)+(0.1073P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1836
_reflns_number_gt                1766
_reflns_number_total             3184
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja406383h_si_002.cif
_cod_data_source_block           No1
_cod_original_cell_volume        2417.2(2)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4120388