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

Abstract

In the title compound, C₁₄H₈Br₂FN₃O₂, the nitro-substituted benzene ring and the 4-fluoro-phenyl ring form a dihedral angle of 65.73 (7)°. In the crystal, mol-ecules are linked into chains by C-H⋯O hydrogen bonds running parallel to the c-axis direction. The crystal packing is consolidated by C-F⋯π inter-actions and π-π stacking inter-actions, and short Br⋯O [2.9828 (13) Å] contacts are observed. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (17.4%), O⋯H/H⋯O (16.3%), Br⋯H/H⋯Br (15.5%), Br⋯C/C⋯Br (10.1%) and F⋯H/H⋯F (8.1%) contacts.

Keywords: C—F⋯π inter­action; Hirshfeld surface analysis; crystal structure; π–π stacking inter­action.

Figure 1

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Figure 2

View of the C—H⋯O, C—F⋯π and π–π stacking inter­actions in the title compound.

Figure 3

The three-dimensional Hirshfeld surface of the title compound plotted over d _norm in the range −0.24 to 1.44 a.u.

Figure 4

The full two-dimensional fingerprint plot (a) for the title compound and those delineated into (b) H⋯H (17.4%), (c) O⋯H/H⋯O (16.3%), (d) Br⋯H/H⋯Br (15.5%), (e) Br⋯C/C⋯Br (10.1%) and (f) F⋯H/H⋯F (8.1%) inter­actions.