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

Abstract

In the title compound, C14H8Br2FN3O2, the 4-fluorophenyl ring and the nitro-substituted phenyl ring form a dihedral angle of 64.37 (10)°. Molecules in the crystal are connected by C—H...O and C—H...F hydrogen bonds into layers parallel to (011). The crystal packing is consolidated by C—Br...π and C—F...π interactions, as well as by π–π stacking interactions. According to a Hirshfeld surface analysis of the crystal structure, the most significant contributions to the crystal packing are from O...H/H...O (15.0%), H...H (14.3%), Br...H/H...Br (14.2%), C...H/H...C (10.1%), F...H/H...F (7.9%), Br...Br (7.2%) and Br...C/C...Br (5.8%) contacts.

Keywords

• crystal structure
• c—h...o hydrogen bonds
• c—h...f hydrogen bonds
• c—br...π interactions
• c—f...π interactions
• π–π stacking interactions
• hirshfeld surface analysis