Crystal structure and Hirshfeld surface analysis of 1,3-bis{2,2-dichloro-1-[(E)-phenyldiazenyl]ethenyl}benzene

In the crystal, molecules of the title compound are connected through C—H⋯π, C—Cl⋯π, Cl⋯Cl and Cl⋯H interactions, generating a three-dimensional network.


Structural commentary
The molecule of the title compound consists of three nearly planar fragments: the central benzene ring and the two attached 2,2-dichloro-1-[(E)-phenyldiazenyl]vinyl groups, Cl1-C8 and Cl3-C22 ( Fig. 1), the largest deviations from the least-squares planes of these side groups being 0.060 (1) and 0.083 (3) Å for Cl2 and C18, respectively. These groups are nearly perpendicular to the central benzene ring, subtending dihedral angles of 77.03 (9) and 81.42 (9) , respectively, with this ring. All bond dimensions within the molecule are typical of such type of compounds (Allen et al., 1987).

Hirshfeld surface analysis
The Hirshfeld surfaces and two-dimensional fingerprint plots were generated using Crystal Explorer 17.5 (Turner et al., 2017). Hirshfeld surfaces show intermolecular interactions by different hues and intensities to denote short and long Symmetry code: (i) x; Ày þ 3 2 ; z À 1 2 .

Figure 2
A fragment of the molecular packing showing the C-HÁ Á Á and C-ClÁ Á Á interactions.

Figure 3
A fragment of the molecular packing showing the ClÁ Á ÁCl and Cl-H interactions.

Figure 1
The title molecule with the labelling scheme and 30% probability ellipsoids.

Figure 4
View of the three-dimensional Hirshfeld surface of the title compound plotted over d norm in the range À0.0453 to 1.4337 a.u.