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

Abstract

In the title compound, C14H8Br2FN3O2, the nitro-substituted benzene ring and the 4-fluorophenyl ring form a dihedral angle of 65.73 (7)°. In the crystal, molecules 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 interactions and π–π stacking interactions, 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

• crystal structure
• c—f...π interaction
• π–π stacking interaction
• hirshfeld surface analysis