Crystal structure and Hirshfeld surface analysis of 2,6-diiodo-4-nitrotoluene and 2,4,6-tribromotoluene

Abstract

The title compounds, 2,6-diiodo-4-nitrotoluene (DINT, C7H5I2NO2) and 2,4,6-tribromotoluene (TBT, C7H5Br3,), are trisubstituted toluene molecules. Both molecules are planar, only the H atoms of the methyl group, and the nitro group in DINT, deviate significantly from the plane of the benzene ring. In the crystals of both compounds, molecules stack in columns up the shortest crystallographic axis, viz. the a axis in DINT and the b axis in TBT. In the crystal of DINT, molecules are linked via short N—O...I contacts, forming chains along [100]. In TBT, molecules are linked by C—H...Br hydrogen bonds, forming chains along [010]. Hirshfeld surface analysis was used to explore the intermolecular contacts in the crystals of both DINT and TBT.

Keywords

• x-ray diffraction
• crystal structure
• 2,6-diiodo-4-nitrotoluene
• 2,4,6-tribromotoluene
• hirshfeld surface