Indirect C-H Azidation of Heterocycles via Copper-Catalyzed Regioselective Fragmentation of Unsymmetrical λ3-Iodanes
Dmitrijs Lubriks; Igors Sokolovs; Edgars Suna; Journal of the American Chemical Society 134 (2012) 15436–15442; doi:10.1021/ja305574k

data_4118628
_publ_contact_author_name        Dmitry
_publ_section_title
;
 Indirect C-H Azidation of Heterocycles via Copper-Catalyzed
 Regioselective Fragmentation of Unsymmetrical \l3-Iodanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15436
_journal_page_last               15442
_journal_paper_doi               10.1021/ja305574k
_journal_volume                  134
_journal_year                    2012
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         '2(C21 H20 Br I N O2), 2(N3), 3(H2 O)'
_chemical_formula_sum            'C42 H46 Br2 I2 N8 O7'
_chemical_formula_weight         1188.465
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                92.675(2)
_cell_angle_beta                 94.9141(14)
_cell_angle_gamma                97.142(2)
_cell_formula_units_Z            1
_cell_length_a                   7.7822(3)
_cell_length_b                   12.3633(5)
_cell_length_c                   12.6194(6)
_cell_measurement_reflns_used    13304
_cell_measurement_temperature    193
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      0.9
_cell_volume                     1198.29(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.04514
_diffrn_orient_matrix_UB_12      0.12197
_diffrn_orient_matrix_UB_13      0.00138
_diffrn_orient_matrix_UB_21      0.00011
_diffrn_orient_matrix_UB_22      0.01035
_diffrn_orient_matrix_UB_23      0.08100
_diffrn_orient_matrix_UB_31      0.07185
_diffrn_orient_matrix_UB_32      0.03443
_diffrn_orient_matrix_UB_33      0.00016
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9109
_diffrn_reflns_theta_full        29.0
_diffrn_reflns_theta_max         29.0
_diffrn_reflns_theta_min         2.2
_exptl_absorpt_coefficient_mu    3.034
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_description       Needle
_exptl_crystal_F_000             586
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.402
_refine_diff_density_min         -1.390
_refine_diff_density_rms         0.413
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.438
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         6144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.438
_refine_ls_R_factor_all          0.1376
_refine_ls_R_factor_gt           0.0791
_refine_ls_shift/su_max          0.073
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1915
_refine_ls_wR_factor_ref         0.2510
_reflns_number_gt                4029
_reflns_number_total             6144
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja305574k_si_003.cif
_cod_data_source_block           Dmitry
_cod_depositor_comments          'Adding Fobs data.'
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C42 H46 Br2 I2 N8 O7 '
_cod_database_code               4118628
_cod_database_fobs_code          4118628