Crystal structure and Hirshfeld surface analysis of (E)-4-{2,2-di-chloro-1-[(3,5-di-methyl-phen-yl)diazen-yl]ethen-yl}- N, N-di-methyl-aniline

Kadriye Özkaraca; Mehmet Akkurt; Namiq Q Shikhaliyev; Ulviyya F Askerova; Gulnar T Suleymanova; Gunay Z Mammadova; Daniel M Shadrack

doi:10.1107/S2056989020009202

Crystal structure and Hirshfeld surface analysis of (E)-4-{2,2-di-chloro-1-[(3,5-di-methyl-phen-yl)diazen-yl]ethen-yl}- N, N-di-methyl-aniline

Acta Crystallogr E Crystallogr Commun. 2020 Jul 10;76(Pt 8):1251-1254. doi: 10.1107/S2056989020009202. eCollection 2020 Aug 1.

Authors

Kadriye Özkaraca¹, Mehmet Akkurt², Namiq Q Shikhaliyev³, Ulviyya F Askerova³, Gulnar T Suleymanova³, Gunay Z Mammadova³, Daniel M Shadrack^{4

5}

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 Health & Biomedical Sciences, School of Life Science and Bioengineering, The Nelson Mandela Africa Institute of Science and Technology, PO Box 447, Arusha, Tanzania.
⁵ Department of Chemistry, St. John's University of Tanzania, PO Box 47, Dodoma, Tanzania.

Abstract

In the title compound, C₁₈H₁₉Cl₂N₃, the planes of the benzene rings subtend a dihedral angle of 77.07 (10)°. In the crystal, mol-ecules are associated into inversion dimers via short Cl⋯Cl contacts [3.3763 (9) Å]. A Hirshfeld surface analysis indicates that the most important contact percentages for the different types of inter-actions are H⋯H (43.9%), Cl⋯H/H⋯Cl (22.9%), C⋯H/H⋯C (20.8%) and N⋯H/H⋯N (8.0%).

Keywords: Cl⋯Cl halogen bonds; Hirshfeld surface analysis; crystal structure.

Grants and funding

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