Ceric Ammonium Nitrate-Catalyzed Azidation of 1,2-Anhydro Sugars: Application in the Synthesis of Structurally Diverse Sugar-Derived Morpholine 1,2,3-Triazoles and 1,4-Oxazin-2-ones
Y. Suman Reddy; A. P. John Pal; Preeti Gupta; Alafia A. Ansari; Yashwant D. Vankar; Journal of Organic Chemistry 76 (2011) 5972–5984; doi:10.1021/jo200260w

data_4026464
_publ_contact_author_address
;Department of Chemistry 
Indian Institute of Technology 
Kanpur, Uttar Pradesh 
India, 208 016 
;
_publ_contact_author_email       vankar@iitk.ac.in
_publ_contact_author_name        'Dr. Y D Vankar'
_publ_contact_author_phone       +91-512-2597169
_publ_section_title
;
 Ceric Ammonium Nitrate-Catalyzed Azidation of 1,2-Anhydro Sugars:
 Application in the Synthesis of Structurally Diverse Sugar-Derived
 Morpholine 1,2,3-Triazoles and 1,4-Oxazin-2-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5972
_journal_page_last               5984
_journal_paper_doi               10.1021/jo200260w
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C9 H13 N3 O5'
_chemical_formula_sum            'C9 H13 N3 O5'
_chemical_formula_weight         243.22
_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                 94.640(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.545(3)
_cell_length_b                   8.428(4)
_cell_length_c                   9.345(4)
_cell_measurement_reflns_used    3369
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.2
_cell_volume                     513.8(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Diamond 3'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '\p and \w 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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3369
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker 2003)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       needle
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2128
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.202
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0830P)^2^+0.4817P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1901
_reflns_number_gt                1893
_reflns_number_total             2128
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200260w_si_002.cif
_cod_data_source_block           7junbm
_cod_original_sg_symbol_Hall     P2yb
_cod_database_code               4026464