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. 2019 Jan 18;75(Pt 2):237-241.
doi: 10.1107/S2056989019000707. eCollection 2019 Feb 1.

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

Zeliha Atioğlu  1 , Mehmet Akkurt  2 , Namiq Q Shikhaliyev  3 , Gulnar T Suleymanova  3 , Khanim N Bagirova  3 , Flavien A A Toze  4
Affiliations

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

Zeliha Atioğlu et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

In the title compound, C14H8Cl2FN3O2, the 4-fluoro-phenyl ring and the nitro-substituted benzene ring form a dihedral angle of 63.29 (8)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds into chains running parallel to the c axis. The crystal packing is further stabilized by C-Cl⋯π, C-F⋯π and N-O⋯π inter-actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯O/O⋯H (15.5%), H⋯H (15.3%), Cl⋯H/H⋯Cl (13.8%), C⋯H/H⋯C (9.5%) and F⋯H/H⋯F (8.2%) inter-actions.

Keywords: 4-fluoro­phenyl ring; Hirshfeld surface analysis; crystal structure; hydrogen bonding; nitro-substituted benzene ring.

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Figures

Figure 1
Figure 1
The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
Figure 2
Figure 2
Crystal packing of the title compound, viewed down the a axis, showing the formation of chains parallel to the c axis through C—H⋯O hydrogen bonds (dashed lines).
Figure 3
Figure 3
View of the three-dimensional Hirshfeld surface of the title compound plotted over d norm in the range −0.1603 to 1.2420 a.u.
Figure 4
Figure 4
The full two-dimensional fingerprint plots for the title compound, showing (a) all inter­actions, and delineated into (b) O⋯H/H⋯O, (c) H⋯H, (d) Cl⋯H/H⋯Cl, (e) C⋯H/H⋯C, (f) F⋯H/H⋯F, (g) Cl⋯Cl, (h) N⋯H/H⋯N and (i) Cl⋯C/C⋯Cl inter­actions. The d i and d e values are the closest inter­nal and external distances (in Å) from given points on the Hirshfeld surface.
Figure 5
Figure 5
Hirshfeld surface representations with the function d norm plotted onto the surface for (a) all inter­actions, (b) O⋯H/H⋯O, (c) H⋯H, (d) Cl⋯H/H⋯Cl, (e) C⋯H/H⋯C, (f) F⋯H/H⋯F, (g) Cl⋯Cl, (h) N⋯H/H⋯N and (i) Cl⋯C/C⋯Cl inter­actions.
Figure 6
Figure 6
Hirshfeld surface of the title compound plotted over shape-index.
See this image and copyright information in PMC

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