Synthesis of Polyhydroxylated 2H-Azirines and 2-Halo-2H-azirines from 3-Azido-2,3-dideoxyhexopyranoses by Alkoxyl Radical Fragmentation
Carmen R. Alonso-Cruz; Alan R. Kennedy; María S. Rodríguez; Ernesto Suárez; Journal of Organic Chemistry 73 (2008) 4116–4122; doi:10.1021/jo800182y

data_4023427
_publ_section_title
;
 Synthesis of Polyhydroxylated 2H-Azirines and 2-Halo-2H-azirines
 from 3-Azido-2,3-dideoxyhexopyranoses by Alkoxyl Radical Fragmentation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4116
_journal_page_last               4122
_journal_paper_doi               10.1021/jo800182y
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C13 H12 I N3 O4'
_chemical_formula_weight         401.16
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.115(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.427(2)
_cell_length_b                   41.337(19)
_cell_length_c                   8.158(4)
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.47
_cell_volume                     1492.9(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'fine-slice \w scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6911
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0976
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10658
_diffrn_reflns_theta_full        24.31
_diffrn_reflns_theta_max         24.31
_diffrn_reflns_theta_min         2.43
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.243
_refine_diff_density_min         -0.934
_refine_diff_density_rms         0.160
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         10658
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0675
_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^)+(0.0554P)^2^+7.8875P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1637
_refine_ls_wR_factor_ref         0.1718
_reflns_number_gt                9359
_reflns_number_total             10658
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo800182y-File002.cif
_cod_data_source_block           38d-Z
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023427