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_7155333
_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         C12H10N4
_chemical_formula_sum            'C12 H10 N4'
_chemical_formula_weight         210.24
_chemical_melting_point          447.15
_chemical_name_systematic
6-methyl-3-(pyridin-2-yl)-[1,2,4]triazolo[4,3-a]pyridine
_chemical_properties_physical    ', Heat-sensitive'
_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
;
2016-06-25 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                73.705(8)
_cell_angle_beta                 83.998(8)
_cell_angle_gamma                68.210(8)
_cell_formula_units_Z            2
_cell_length_a                   7.5325(7)
_cell_length_b                   8.2606(7)
_cell_length_c                   9.0301(8)
_cell_measurement_reflns_used    2246
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.24
_cell_measurement_theta_min      3.74
_cell_volume                     500.78(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2839
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         3.74
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             220
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0320P)^2^+0.0573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1054
_reflns_number_gt                1440
_reflns_number_total             1792
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob01926a4.cif
_cod_data_source_block           bpk-069
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155333--7155334.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7155333
_solvent_exptl_crystal_recrystallization_method MeOH/DCM