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_7240362
_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_sum            'C19 H12 Cl N5'
_chemical_formula_weight         345.79
_chemical_name_common            Hamada_GH180_18_11_18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc24jttb
_audit_update_record
;
2020-02-06 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                71.352(4)
_cell_angle_beta                 80.896(4)
_cell_angle_gamma                86.548(5)
_cell_formula_units_Z            4
_cell_length_a                   8.9886(8)
_cell_length_b                   12.8468(10)
_cell_length_c                   15.1372(12)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      66.1876
_cell_measurement_theta_min      4.9833
_cell_volume                     1635.2(2)
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_data_collection       'Bruker Instrument Service v2012.4.0.0'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22733
_diffrn_reflns_theta_full        66.47
_diffrn_reflns_theta_max         66.47
_diffrn_reflns_theta_min         5.48
_diffrn_source_type              'Incoatec Cu-ImS'
_exptl_absorpt_coefficient_mu    2.158
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.386
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.598
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.598
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0634P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1438
_reflns_number_gt                4527
_reflns_number_total             5570
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ra02256j1.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 7240361--7240366.cif.'
_cod_database_code               7240362