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_4026465
_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_formula_moiety         'C7 H10 N O5 '
_chemical_formula_sum            'C7 H10 N O5 '
_chemical_formula_weight         189.17
_chemical_name_systematic
; 
 ? 
;
_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                 99.138(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.368(12)
_cell_length_b                   6.633(7)
_cell_length_c                   12.241(13)
_cell_measurement_reflns_used    1099
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      21.82
_cell_measurement_theta_min      2.80
_cell_volume                     831.1(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD are Detector'
_diffrn_measurement_method       'phi-omega 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  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0562
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4493
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.749
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2836
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.749
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.115
_refine_ls_shift/su_mean         0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1554P)^2^+0.1924P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1763
_reflns_number_gt                2083
_reflns_number_total             2836
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200260w_si_003.cif
_cod_data_source_block           31janb
_cod_original_cell_volume        831.2(16)
_cod_original_sg_symbol_Hall     'P 2yb   '
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4026465