I2 mediated synthesis of 5-substituted-3-methyl/benzyl-1,3,4-oxadiazol-2(3H)-ones via sequential condensation/oxidative cyclization and rearrangement.
Patel, Shyam Sunder; Chandna, Nisha; Kumar, Shreemoyee; Jain, Nidhi; Organic & biomolecular chemistry 14 (2016) 5683–5689; doi:10.1039/c5ob02667a

data_7154955
_publ_section_title
;
 I2 mediated synthesis of
 5-substituted-3-methyl/benzyl-1,3,4-oxadiazol-2(3H)-ones via sequential
 condensation/oxidative cyclization and rearrangement.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5683
_journal_page_last               5689
_journal_paper_doi               10.1039/c5ob02667a
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C8 H7 N3 O2'
_chemical_formula_sum            'C8 H7 N3 O2'
_chemical_formula_weight         177.17
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-08-27 deposited with the CCDC.
2016-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                72.891(4)
_cell_angle_beta                 85.142(4)
_cell_angle_gamma                74.695(4)
_cell_formula_units_Z            2
_cell_length_a                   5.7205(15)
_cell_length_b                   7.824(2)
_cell_length_c                   9.811(3)
_cell_measurement_temperature    298(2)
_cell_volume                     404.78(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
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_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3825
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
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_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             184.0
_exptl_crystal_recrystallization_method
'By slow evaporation CDCl3 solvent slow evaporation'
_exptl_crystal_size_max          0.53
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         1419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0983P)^2^+0.0077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1581
_reflns_number_gt                1071
_reflns_number_total             1419
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob02667a2.cif
_cod_data_source_block           oxam
_cod_depositor_comments          'Adding full bibliography for 7154955.cif.'
_cod_original_cell_volume        404.79(19)
_cod_database_code               7154955