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_4118627
_publ_contact_author_name        D.Lubrik
_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         'C18 H16 Br I N O2, C4 H8 O, N3'
_chemical_formula_sum            'C22 H24 Br I N4 O3'
_chemical_formula_weight         599.25
_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_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                87.896(2)
_cell_angle_beta                 74.343(2)
_cell_angle_gamma                67.681(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1750(3)
_cell_length_b                   11.2802(4)
_cell_length_c                   11.3973(4)
_cell_measurement_reflns_used    20082
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      0.9
_cell_volume                     1162.05(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'
_computing_publication_material  'maXus(Mackay et al., 1999)'
_computing_structure_refinement  'maXus(Mackay et al., 1999)'
_computing_structure_solution
'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device       KappaCCD
_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      0.10104
_diffrn_orient_matrix_UB_12      -0.01741
_diffrn_orient_matrix_UB_13      -0.04137
_diffrn_orient_matrix_UB_21      -0.05809
_diffrn_orient_matrix_UB_22      -0.07570
_diffrn_orient_matrix_UB_23      -0.01133
_diffrn_orient_matrix_UB_31      -0.04848
_diffrn_orient_matrix_UB_32      0.03869
_diffrn_orient_matrix_UB_33      -0.06709
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8720
_diffrn_reflns_theta_full        28.5
_diffrn_reflns_theta_max         28.5
_diffrn_reflns_theta_min         1.8
_exptl_absorpt_coefficient_mu    3.128
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_description       Prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.92
_refine_diff_density_min         -1.93
_refine_diff_density_rms         0.42
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   2.245
_refine_ls_goodness_of_fit_gt    2.016
_refine_ls_goodness_of_fit_ref   1.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.078
_refine_ls_R_factor_gt           0.051
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef F^2^
_refine_ls_weighting_details     ' w = 1 / ( s^2^(Fo^2^) + 0.10000 * Fo^2^)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.194
_refine_ls_wR_factor_gt          0.137
_refine_ls_wR_factor_ref         0.125
_reflns_d_resolution_high        0.62
_reflns_d_resolution_low         2.34
_reflns_limit_h_max              13
_reflns_limit_h_min              0
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                4225
_reflns_number_total             5767
_reflns_threshold_expression     'I> 3.00 sigma(I)'
_cod_data_source_file            ja305574k_si_002.cif
_cod_data_source_block           DLG310
_cod_depositor_comments
;Adding Fobs data.

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom, diff' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C22 H24 Br I N4 O3 '
_cod_database_code               4118627
_cod_database_fobs_code          4118627