Synthesis, crystal structure and Hirshfeld surface analysis of 5-cyclo-propyl- N-(2-hy-droxy-eth-yl)-1-(4-methyl-phen-yl)-1 H-1,2,3-triazole-4-carboxamide

Acta Crystallogr E Crystallogr Commun. 2021 Sep 28;77(Pt 10):1043-1047. doi: 10.1107/S2056989021009774. eCollection 2021 Oct 1.

Abstract

The title compound, C15H18N4O2, was obtained via a two-step synthesis (Dimroth reaction and amidation) for anti-cancer activity screening and was selected from a 1H-1,2,3-triazole-4-carboxamide library. The cyclo-propyl ring is oriented almost perpendicular to the benzene ring [dihedral angle = 87.9 (1)°], while the dihedral angle between the mean plane of the cyclo-propyl ring and that of the triazole ring is 55.6 (1)°. In the crystal, the mol-ecules are linked by O-H⋯O and C-H⋯N inter-actions into infinite ribbons propagating in the [001] direction, which are inter-connected by weak C-H⋯O inter-actions into layers. The inter-molecular inter-actions were characterized via Hirshfeld surface analysis, which indicated that the largest fingerprint contact percentages are H⋯H (55.5%), N⋯H/H⋯N (15.4%), C⋯H/H⋯C (13.2%) and O⋯H/H⋯O (12.9%).

Keywords: 1,2,3-triazole; 1,2,3-triazole-4-carboxamide; Hirshfeld surface analysis; amide; crystal structure.

Grants and funding

This work was funded by Ministry of Education and Science of Ukraine grant 0121U107777.