Regioselective Iodoazidation of Alkynes: Synthesis of α,α-Diazidoketones
Okamoto, Noriko; Sueda, Takuya; Minami, Hideki; Miwa, Yoshihisa; Yanada, Reiko; Organic Letters  (2015) 150226085504000–; doi:10.1021/acs.orglett.5b00395

data_1518767
_publ_section_title
;
 Regioselective Iodoazidation of Alkynes: Synthesis of
 \a,\a-Diazidoketones
;
_journal_name_full               'Organic Letters'
_journal_page_first              150226085504000
_journal_paper_doi               10.1021/acs.orglett.5b00395
_journal_year                    2015
_chemical_formula_moiety         'C16 H11 Br N6 O3'
_chemical_formula_sum            'C16 H11 Br N6 O3'
_chemical_formula_weight         415.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 111.672(15)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   17.554(5)
_cell_length_b                   6.4450(19)
_cell_length_c                   15.846(4)
_cell_measurement_reflns_used    14770
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      3.00
_cell_volume                     1666.0(8)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14632
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         5.424
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.652
_exptl_absorpt_correction_T_max  0.694
_exptl_absorpt_correction_T_min  0.363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.831
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2946
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.056
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
    Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
    1.2138    -0.4563    -0.7140
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0246
_reflns_number_gt                2757
_reflns_number_total             2946
_reflns_threshold_expression     F>2.0\s(F)
_cod_data_source_file            ol5b00395_si_002.cif
_cod_data_source_block           140806okamoto18
_cod_database_code               1518767