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

Abstract

In the title compound, C₁₄H₇Cl₄FN₂, the dihedral angle between the 4-fluoro-phenyl ring and the 2,4-di-chloro-phenyl ring is 46.03 (19)°. In the crystal, the mol-ecules are linked by C-H⋯N inter-actions along the a-axis direction, forming a C(6) chain. The mol-ecules are further connected by C-Cl⋯π inter-actions and face-to-face π-π stacking inter-actions, forming ribbons along the a-axis direction. Hirshfeld surface analysis indicates that the greatest contributions to the crystal packing are from Cl⋯H/H⋯Cl (35.1%), H⋯H (10.6%), C⋯C (9.7%), Cl⋯Cl (9.4%) and C⋯H/H⋯C (9.2%) inter-actions.

Keywords: C—Cl⋯π inter­actions; Hirshfeld surface analysis; crystal structure; face-to-face π–π stacking inter­actions; short inter HL⋯HL contact.