Synthesis, crystal structure and Hirshfeld surface analysis of 5-cyclopropyl-N-(2-hydroxyethyl)-1-(4-methylphenyl)-1H-1 ,2,3-triazole-4-carboxamide

The title compound, C is H18N4O2, was obtained via a two-step synthesis (Dimroth reaction and amidation) for anticancer activity screening and was selected from a 1H-1,2,3-triazole-4-carboxamide library. The cyclopropyl ring is oriented almost perpendicular to the benzene ring [dihedral angle = 87.9 (1)degrees], while the dihedral angle between the mean plane of the cyclopropyl ring and that of the triazole ring is 55.6 (1)degrees. In the crystal, the molecules are linked by O-H center dot center dot center dot O and C-H center dot center dot center dot N interactions into infinite ribbons propagating in the [001] direction, which are interconnected by weak C-H center dot center dot center dot O interactions into layers. The intermolecular interactions were characterized via Hirshfeld surface analysis, which indicated that the largest fingerprint contact percentages are H center dot center dot center dot H (55.5%), N center dot center dot center dot H/H center dot center dot center dot N (15.4%), C center dot center dot center dot H/H center dot center dot center dot C (13.2%) and O center dot center dot center dot H/H center dot center dot center dot O (12.9%).

Automated summary

The title compound was synthesized through a two-step process and the crystal structure revealed intermolecular interactions involving hydrogen bonding and van der Waals forces, forming infinite ribbons and layers in the crystal lattice.