(2E)-1-[5-Methyl-1-(4-methyl-phen-yl)-1H-1,2,3-triazol-4-yl]-3-[4-(piperidin-1-yl)phen-yl]prop-2-en-1-one

Abstract

Two independent mol-ecules comprise the asymmetric unit of the title compound, C24H26N4O. The major difference between them is found in the relative orientation of the triazole-bound p-tolyl group which have the opposite sense of twist [N-N-C-C torsion angles = 55.8 (3) and -49.8 (3)°]. The chalcone residue is almost coplanar with the triazole ring [N-C-C-O and C-C-C-C torsion angles = -178.9 (2) and -178.5 (2)°, respectively; cf. 177.9 (3) and 168.5 (3)°, respectively, in the second mol-ecule]. The conformation about each C=C double bond is E and in each case the triazole methyl group is syn to the carbonyl O atom. In the crystal, mol-ecules aggregate into layers parallel to (-113). The first independent mol-ecule self-associates into a layer via C-H⋯O and C-H⋯π inter-actions. By contrast, layers comprising the second independent mol-ecule do not feature specific inter-actions between mol-ecules. The global crystal packing comprises alternating layers.

Fig. 1.

The molecular structure of (I) showing displacement ellipsoids at the 35% probability level.

Fig. 2.

Overlay diagram of the two independent molecules comprising the asymmetric unit of (I). The O1- (red image) and O2-containing (blue) molecules have been superimposed so that the five-membered rings are coincident.

Fig. 3.

A view of the supramolecular layer in (I) comprising O1-containing molecules only, and sustained by C—H···O and C—H···π interactions, shown as orange and purple dashed lines, respectively.

Fig. 4.

A view of the crystal packing in projection down the a axis, highlighting the alternating layers of O1- and O2-containing molecules. The C—H···O and C—H···π interactions are shown as orange and purple dashed lines, respectively.