Crystal structure and Hirshfeld surface analysis of 4-azido-2-(3,5-di-methyl-phen-yl)-5-(4-nitro-phen-yl)-2 H-1,2,3-triazole

Abel Maharramov; Namiq Q Shikhaliyev; Afaq Abdullayeva; Gulnar T Atakishiyeva; Ayten Niyazova; Victor N Khrustalev; Shahnaz I Gahramanova; Zeliha Atioğlu; Mehmet Akkurt; Ajaya Bhattarai

doi:10.1107/S2056989023007855

Crystal structure and Hirshfeld surface analysis of 4-azido-2-(3,5-di-methyl-phen-yl)-5-(4-nitro-phen-yl)-2 H-1,2,3-triazole

Acta Crystallogr E Crystallogr Commun. 2023 Sep 14;79(Pt 10):905-909. doi: 10.1107/S2056989023007855. eCollection 2023 Oct 1.

Authors

Affiliations

¹ Organic Chemistry Department, Baku State University, Z. Khalilov str. 23, AZ 1148 Baku, Azerbaijan.
² Department of Engineering and Applied Sciences, Azerbaijan State University of Economics, M. Mukhtarov 194, Baku AZ1001, Azerbaijan.
³ Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St. 6, Moscow, 117198, Russian Federation.
⁴ N. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation.
⁵ Institute of Catalysis and Inorganic Chemistry , 113 H. Javid Ave., AZ1143 Baku, Azerbaijan.
⁶ Department of Aircraft Electrics and Electronics, School of Applied Sciences, Cappadocia University, Mustafapaşa, 50420 Ürgüp, Nevşehir, Türkiye.
⁷ Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye.
⁸ Department of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal.

Abstract

In the title compound, C₁₆H₁₃N₇O₂, the 3,5-di-methyl-phenyl and 4-nitro-phenyl rings are inclined to the central 2H-1,2,3-triazole ring by 1.80 (7) and 1.79 (7)°, respectively, and to one another by 2.16 (7)°. In the crystal, the mol-ecules are linked by C-H⋯N hydrogen bonds and π-π stacking inter-actions [centroid-to-centroid distances = 3.7295 (9) and 3.7971 (9) Å], forming ribbons along the b-axis direction. These ribbons are connected to each other by weak van der Waals inter-actions and the stability of the crystal structure is ensured. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (31.5%), N⋯H/H⋯N (19.2%), O⋯H/H⋯O (14.5%), N⋯C/C⋯C (10.9%) and C⋯H/H⋯C (10.2%) contacts.

Keywords: 2H-1,2,3-triazole; Hirshfeld surface analysis; azido group; crystal structure; hydrogen bonds.

Grants and funding

This work was funded by the Science Development Foundation under the President of the Republic of Azerbaijan, grant No. EIF–BGM-4-RFTF-1/2017–21/13/4.