Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]-2-(4-fluorophenyl)diazene

The dihedral angle between the 4-fluorophenyl ring and the nitro-substituted benzene ring of the title compound is 63.29 (8)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into chains parallel to the c axis. The crystal packing is further stabilized by C—Cl⋯π, C—F⋯π and N—O⋯π interactions

Hirshfeld surfaces and fingerprint plots were generated for the title compound using CrystalExplorer (McKinnon et al., 2007) to quantify and visualize the intermolecular interactions and to explain the observed crystal packing. The Hirshfeld surface mapped over d norm using a standard surface resolution with a fixed colour scale of À0.1603 (red) to 1.2420 (blue) a.u. is shown in Fig. 3. The dark-red spots on the d norm surface arise as a result of short interatomic contacts (Table 2), while the other weaker intermolecular interactions appear as light-red spots. The red points, which represent closer contacts and negative d norm values on the surface, correspond to the C-HÁ Á ÁO interactions.
The percentage contributions of various contacts to the total Hirshfeld surface are shown in the two-dimensional fingerprint plots in Fig. 4 The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. Table 1 Hydrogen-bond geometry (Å , ).

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-HÁ Á ÁO hydrogen bonds (dashed lines).

Figure 3
View of the three-dimensional Hirshfeld surface of the title compound plotted over d norm in the range À0.1603 to 1.2420 a.u.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 4. C-bound H atoms were constrained to an ideal geometry with C-H = 0.93 Å and refined as riding with U iso (H) = 1.2U eq (C). Three outliers (100,110,200) were omitted in the last cycles of refinement.