A facile, practical and metal-free microwave-assisted protocol for mono- and bis-[1,2,4]triazolo[1,5-a]pyridines synthesis utilizing 1-amino-2-imino-pyridine derivatives as versatile precursors
Ibrahim, Hamada Mohamed; Behbehani, Haider; Ahmed Arafa, Wael Abdelgayed; RSC Advances 10 (2020) 15554–15572; doi:10.1039/D0RA02256J

data_7240365
_publ_section_title
;
 A facile, practical and metal-free microwave-assisted protocol for mono-
 and bis-[1,2,4]triazolo[1,5-a]pyridines synthesis utilizing
 1-amino-2-imino-pyridine derivatives as versatile precursors
;
_journal_issue                   26
_journal_name_full               'RSC Advances'
_journal_page_first              15554
_journal_page_last               15572
_journal_paper_doi               10.1039/D0RA02256J
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C12 H8 Cl N3'
_chemical_formula_sum            'C12 H8 Cl N3'
_chemical_formula_weight         229.67
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc24jtvc
_audit_update_record
;
2020-02-06 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.964(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   3.8851(9)
_cell_length_b                   19.350(4)
_cell_length_c                   14.116(3)
_cell_measurement_reflns_used    2415
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      3.09
_cell_volume                     1055.5(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0858
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5853
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             472.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.370
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1863
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0782
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1382P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2332
_reflns_number_gt                1153
_reflns_number_total             1863
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d0ra02256j1.cif
_cod_data_source_block           User-defined_CCDC3
_cod_depositor_comments
'Adding full bibliography for 7240361--7240366.cif.'
_cod_database_code               7240365