I2-TBHP-catalyzed one-pot highly efficient synthesis of 4,3-fused 1,2,4-triazoles from N-tosylhydrazones and aromatic N-heterocycles via intermolecular formal 1,3-dipolar cycloaddition.
Inturi, Surendra Babu; Kalita, Biswajit; Ahamed, A. Jafar; Organic & biomolecular chemistry 14 (2016) 11061–11064; doi:10.1039/c6ob01926a

data_7155334
_publ_section_title
;
 I2-TBHP-catalyzed one-pot highly efficient synthesis of 4,3-fused
 1,2,4-triazoles from N-tosylhydrazones and aromatic N-heterocycles via
 intermolecular formal 1,3-dipolar cycloaddition.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              11061
_journal_page_last               11064
_journal_paper_doi               10.1039/c6ob01926a
_journal_volume                  14
_journal_year                    2016
_chemical_compound_source        'Synthesized compound'
_chemical_formula_moiety         C12H8FN3
_chemical_formula_sum            'C12 H8 F N3'
_chemical_formula_weight         213.21
_chemical_melting_point          435.15
_chemical_name_systematic
6-fluoro-3-phenyl-[1,2,4]triazolo[4,3-a]pyridine
_chemical_properties_physical    ', Heat-sensitive'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-06-25 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5842(10)
_cell_length_b                   10.527(3)
_cell_length_c                   14.581(3)
_cell_measurement_reflns_used    1803
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.76
_cell_measurement_theta_min      2.38
_cell_volume                     1010.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2534
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         3.40
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.031
_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   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0016P)^2^+0.5613P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0765
_reflns_number_gt                1088
_reflns_number_total             1422
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob01926a4.cif
_cod_data_source_block           ra-070
_cod_depositor_comments
'Adding full bibliography for 7155333--7155334.cif.'
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7155334
_solvent_exptl_crystal_recrystallization_method MeOH/DCM