1421925-62-3Relevant academic research and scientific papers
The differing influence of halides upon supramolecular aggregation through C-X...π interactions in the crystal structures of (5-methyl-1-(4-X- arylamino)-1H-1,2,3-triazol-4-yl)methanol derivatives, X = H, F and Cl
Jordao, Alessandro K.,Ferreira, Vitor F.,Cunha, Anna C.,Wardell, James L.,Wardell, Solange M. S. V.,Tiekink, Edward R. T.
, p. 6534 - 6539,6 (2020/08/24)
The presence of localised C-X...π [or C-X...π(CC)] interactions are shown to be pivotal in the crystal structures of (5-methyl-1-(4-X-arylamino)-1H-1,2,3-triazol-4-yl)methanol derivatives, X = H (1), F (2) and Cl (3). In the absence of halide (1), molecules aggregate into supramolecular chains via alternating ten-membered {...HOC 2N}2 and 14-membered {...HN2C 3O}2 synthons. Molecules assemble into a three-dimensional architecture via edge-to-face C-H...π(arene) interactions occurring between the phenyl rings. In the presence of halide (i.e. F (2) and Cl (3) in the 4-position of the phenyl ring), two-dimensional arrays are formed by interconnected ten-membered {...HOC2N}2 (as seen in 1) and 24-membered {...HO...NC2OH...N 4H}2 hydrogen bonded synthons. The latter arrangement allows for the close approach of halide to the 1,2,3-triazole ring and the formation of C-X...π interactions which appear to be particularly significant in the case of Cl (3), as evidenced by systematic changes (i.e. elongation) in the geometric parameters within the five-membered ring. In this series of structures, the presence of C-X...π interactions is shown to moderate the supramolecular aggregation based on conventional hydrogen bonding. This journal is
