A one pot, multicomponent CuAAC reaction has been exploited for the safe generation of alkyl, benzyl or aryl linked polydentate pyridyl-1,2,3-triazole ligands from their corresponding halides, sodium azide and alkynes in excellent yields. The ligands have been fully characterised by elemental analysis, HR-ESMS, IR, (1)H and (13)C NMR and in two cases the structures were confirmed by X-ray crystallography. Additionally, we have examined the Ag(I) coordination chemistry of these ligands and found, using HR-ESMS, (1)H NMR, and X-ray crystallography, that both discrete and polymeric metallosupramolecular architectures can be formed.
In the structure of the title compound, C10H11BrN4, the plane of the substituted 1,2,3-triazole ring is tilted by 14.84 (10)° with respect to the mean plane of the pyridine ring. The pyridine and closest triazole N atoms adopt an anti arrangement which removes any lone pair–lone pair repulsions between the N atoms. This conformation is further stabilized by weak intermolecular C—H⋯N interactions. There are two molecules in the unit cell, which form a centrosymmetric head-to-tail dimer. The dimers are stabilized through π–π interactions [centroid–centroid distance = 3.733 (4) Å and mean interplanar distance = 3.806 (12) Å] between the substituted 1,2,3-triazole ring and the pyridine rings in adjacent molecules. Each dimer interacts with two neighbouring dimers above and below, forming a slipped stack of dimers through the crystal. The 3-bromopropyl chain sits over the pyridine ring of a neighbouring molecule and the triazole rings of nearby molecules are adjacent.
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