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

Mehmet Akkurt; Sema Öztürk Yıldırım; Namiq Q Shikhaliyev; Naila A Mammadova; Ayten A Niyazova; Victor N Khrustalev; Ajaya Bhattarai

doi:10.1107/S205698902200620X

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

Acta Crystallogr E Crystallogr Commun. 2022 Jun 16;78(Pt 7):732-736. doi: 10.1107/S205698902200620X. eCollection 2022 Jul 1.

Authors

Mehmet Akkurt¹, Sema Öztürk Yıldırım^{2

1}, Namiq Q Shikhaliyev³, Naila A Mammadova³, Ayten A Niyazova^{3

4}, Victor N Khrustalev^{5

6}, Ajaya Bhattarai⁷

Affiliations

¹ Department of Physics, Faculty of Science, Erciyes University, 38039 Kayseri, Turkey.
² Department of Physics, Faculty of Science, Eskisehir Technical University, Yunus Emre Campus 26470 Eskisehir, Turkey.
³ Organic Chemistry Department, Baku State University, Z. Khalilov str. 23, AZ 1148 Baku, Azerbaijan.
⁴ Azerbaijan State University of Economics (UNEC), Istiglaliyyat str., Baku, Azerbaijan.
⁵ Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St. 6, Moscow, 117198, Russian Federation.
⁶ N. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation.
⁷ Department of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal.

Abstract

The mol-ecule of the title compound, C₁₄H₈Br₃N₃O₂, consists of three almost planar groups: the central di-bromo-ethenyldiazene fragment and two attached aromatic rings. The mean planes of these rings form dihedral angles with the plane of the central fragment of 26.35 (15) and 72.57 (14)° for bromine- and nitro-substituted rings, respectively. In the crystal, C-H⋯Br inter-actions connect mol-ecules, generating zigzag C(8) chains along the [100] direction. These chains are linked by C-Br⋯π inter-actions into layers parallel to (001). van der Waals inter-actions between the layers aid in the cohesion of the crystal packing. The most substantial contributions to crystal packing, according to a Hirshfeld surface analysis, are from Br⋯H/H⋯Br (20.9%), C⋯H/H⋯C (15.2%), O⋯H/H⋯O (12.6%) and H⋯H (11.7%) contacts.

Keywords: C(8) chains; C—H⋯Br interactions; Hirshfeld surface analysis; crystal structure; non-covalent 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).