Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-di-chloro-1-(4-methyl-phen-yl)ethen-yl]-2-(4-meth-oxy-phen-yl)diazene

Namiq Q Shikhaliyev; Zeliha Atioğlu; Mehmet Akkurt; Ayten M Qacar; Rizvan K Askerov; Ajaya Bhattarai

doi:10.1107/S2056989021008756

Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-di-chloro-1-(4-methyl-phen-yl)ethen-yl]-2-(4-meth-oxy-phen-yl)diazene

Acta Crystallogr E Crystallogr Commun. 2021 Aug 27;77(Pt 9):965-970. doi: 10.1107/S2056989021008756. eCollection 2021 Sep 1.

Authors

Namiq Q Shikhaliyev¹, Zeliha Atioğlu², Mehmet Akkurt³, Ayten M Qacar¹, Rizvan K Askerov¹, Ajaya Bhattarai⁴

Affiliations

¹ Organic Chemistry Department, Baku State University, Z. Khalilov str. 23, AZ 1148 Baku, Azerbaijan.
² Department of Aircraft Electrics and Electronics, School of Applied Sciences, Cappadocia University, Mustafapaşa, 50420 Ürgüp, Nevşehir, Turkey.
³ Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.
⁴ Department of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal.

Abstract

The asymmetric unit of the title compound, C₁₆H₁₄Cl₂N₂O, comprises two similar mol-ecules, A and B, in which the dihedral angles between the two aromatic rings are 70.1 (3) and 73.2 (2)°, respectively. The crystal structure features short C-H⋯Cl and C-H⋯O contacts and C-H⋯π and van der Waals inter-actions. The title compound was refined as a two-component non-merohedral twin, BASF 0.1076 (5). The Hirshfeld surface analysis and two-dimensional fingerprint plots show that H⋯H (38.2% for mol-ecule A; 36.0% for mol-ecule B), Cl⋯H/H⋯Cl (24.6% for mol-ecule A; 26.7% for mol-ecule B) and C⋯H/H⋯C (20.0% for mol-ecule A; 20.2% for mol-ecule B) inter-actions are the most important contributors to the crystal packing.

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

Grants and funding

This work was funded by Science Development Foundation under the President of the Republic of Azerbaijan grant EIF-BGM-4- RFTF-1/2017–21/13/4).