Crystal structure and Hirshfeld surface analysis of 4-{2,2-di-chloro-1-[(E)-(4-fluoro-phen-yl)diazen-yl]ethen-yl}- N, N-di-methyl-aniline

Kadriye Özkaraca; Mehmet Akkurt; Namiq Q Shikhaliyev; Ulviyya F Askerova; Gulnar T Suleymanova; Irada M Shikhaliyeva; Ajaya Bhattarai

doi:10.1107/S2056989020006106

Crystal structure and Hirshfeld surface analysis of 4-{2,2-di-chloro-1-[(E)-(4-fluoro-phen-yl)diazen-yl]ethen-yl}- N, N-di-methyl-aniline

Acta Crystallogr E Crystallogr Commun. 2020 May 6;76(Pt 6):811-815. doi: 10.1107/S2056989020006106. eCollection 2020 Jun 1.

Authors

Kadriye Özkaraca¹, Mehmet Akkurt², Namiq Q Shikhaliyev³, Ulviyya F Askerova³, Gulnar T Suleymanova³, Irada M Shikhaliyeva³, Ajaya Bhattarai⁴

Affiliations

¹ Institute of Natural and Applied Science, Erciyes University, 38039 Kayseri, Turkey.
² Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.
³ Organic Chemistry Department, Baku State University, Z. Khalilov str. 23, AZ 1148 Baku, Azerbaijan.
⁴ Department of Chemistry, M.M.A.M.C (Tribhuvan University), Biratnagar, Nepal.

Abstract

In the title compound, C₁₆H₁₄Cl₂FN₃, the dihedral angle between the two aromatic rings is 64.12 (14)°. The crystal structure is stabilized by a short Cl⋯H contact, C-Cl⋯π and van der Waals inter-actions. The Hirshfeld surface analysis and two-dimensional fingerprint plots show that H⋯H (33.3%), Cl⋯H/H⋯Cl (22.9%) and C⋯H/H⋯C (15.5%) inter-actions are the most important contributors towards the crystal packing.

Keywords: C—Cl⋯π interactions; Hirshfeld surface analysis; crystal structure; van der Waals interactions.

Grants and funding

This work was funded by Science Development Foundation Azerbaijan grant EIF– BGM-4-RFTF-1/2017–21/13/4. Russian Foundation for Basic Research grant 18–53-06006.