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

Nazariy T Pokhodylo,Volodymyr Pavlyuk,Yurii Slyvka

doi:10.1107/s2056989021009774

Nazariy T Pokhodylo, Volodymyr Pavlyuk + Show 1 more

Open Access

https://doi.org/10.1107/s2056989021009774

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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%).

Highlights

The title compound, C15H18N4O2, 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 molecules are linked by O—HÁ Á ÁO and C—HÁ Á ÁN interactions into infinite ribbons propagating in the [001] direction, which are interconnected by weak C—HÁ Á ÁO interactions into layers
The intermolecular interactions were characterized via Hirshfeld surface analysis, which indicated that the largest fingerprint contact percentages are HÁ Á ÁH (55.5%), NÁ Á ÁH/HÁ Á ÁN (15.4%), CÁ Á ÁH/HÁ Á ÁC (13.2%) and OÁ Á ÁH/ HÁ Á ÁO (12.9%)

Summary

Chemical context

The 1,2,3-triazolyl-4-carboxamide motif is of great interest in drug discovery, especially in relation to anticancer and antimicrobial research. Given the practical interest of 1-aryl-1H-1,2,3-triazole-4carboxamides in anticancer and antimicrobial research, in the present paper, we report the molecular and crystal structure of the title compound C15H18N4O2, highlighting its molecular conformation and analysing the intermolecular interactions. A similar location of the cyclopropyl ring relative to the 1,2,3-triazole ring was observed in 5-cyclopropyl-1-(3methoxyphenyl)-1H-1,2,3-triazole-4-carboxylic acid (Pokhodylo et al, 2017), but in the structure of the related compound N-(4-chlorophenyl)-5-cyclopropyl-1-(4-methoxyphenyl)-1H1,2,3-triazole-4-carboxamide (Pokhodylo & Slyvka et al, 2020), the cyclopropyl ring is close to coplanar with the aryl substituent. The dihedral angle between the tolyl and 1,2,3-triazole rings in the title compound is 32.75 (7), which is comparable with the corresponding angle in 5-cyclopropyl-1-(3-methoxyphenyl)-1H-1,2,3-triazole-4-carboxylic acid [39.1 (2)] but lower than in the structure of 5-methyl-1-(4-nitrophenyl)-1H-1,2,3triazol-4-ylphosphonate [45.36 (6)] (Pokhodylo, Shykka, Goreshnik et al, 2020). In the triazoles unsubstituted at the 5-position, [1-(3-bromo- or 4-fluorophenyl)-1H1,2,3-triazol-4-yl]methyl methylphosphonate, these angle are 22.9 (3) and 15.7 (2), respectively (Pokhodylo, Shyyka et al, 2019)

Supramolecular features

Hirshfeld surface analysis

Database survey

Synthesis and crystallization

Findings

Refinement