Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-di-bromo-1-(4-nitro-phen-yl)ethen-yl]-2-(4-fluoro-phen-yl)diazene

Zeliha Atioğlu; Mehmet Akkurt; Namiq Q Shikhaliyev; Naila A Mammadova; Gulnara V Babayeva; Victor N Khrustalev; Ajaya Bhattarai

doi:10.1107/S2056989022004388

Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-di-bromo-1-(4-nitro-phen-yl)ethen-yl]-2-(4-fluoro-phen-yl)diazene

Acta Crystallogr E Crystallogr Commun. 2022 Apr 28;78(Pt 5):530-535. doi: 10.1107/S2056989022004388. eCollection 2022 May 1.

Authors

Zeliha Atioğlu¹, Mehmet Akkurt², Namiq Q Shikhaliyev³, Naila A Mammadova³, Gulnara V Babayeva^{3

4}, Victor N Khrustalev^{5

6}, Ajaya Bhattarai⁷

Affiliations

¹ Department of Aircraft Electrics and Electronics, School of Applied Sciences, Cappadocia University, Mustafapaşa, 50420 Ürgüp, Nevşehir, 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 Azerbaijan State Pedagogical University, Uzeyir Hajibeyli str., 68, Baku, Azerbaijan.
⁵ Peoples' Friendship University of Russia, 6 Miklukho-Maklaya, Moscow, Russian Federation.
⁶ N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Av., Moscow, Russian Federation.
⁷ Department of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal.

Abstract

In the title compound, C₁₄H₈Br₂FN₃O₂, the 4-fluoro-phenyl ring and the nitro-substituted phenyl ring form a dihedral angle of 64.37 (10)°. Mol-ecules in the crystal are connected by C-H⋯O and C-H⋯F hydrogen bonds into layers parallel to (011). The crystal packing is consolidated by C-Br⋯π and C-F⋯π inter-actions, as well as by π-π stacking inter-actions. According to a Hirshfeld surface analysis of the crystal structure, the most significant contributions to the crystal packing are from O⋯H/H⋯O (15.0%), H⋯H (14.3%), Br⋯H/H⋯Br (14.2%), C⋯H/H⋯C (10.1%), F⋯H/H⋯F (7.9%), Br⋯Br (7.2%) and Br⋯C/C⋯Br (5.8%) contacts.

Keywords: C—Br⋯π interactions; C—F⋯π interactions; C—H⋯F hydrogen bonds; C—H⋯O hydrogen bonds; Hirshfeld surface analysis; crystal structure; π–π stacking interactions.

Grants and funding

This work was performed under the support of the Science Development Foundation under the President of the Republic of Azerbaijan (grant No. EIF-BGM-4-RFTF-1/2017–21/13/4).