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

The title compounds, 2,6-di­iodo-4-nitro­toluene (DINT, C(7)H(5)I(2)NO(2)) and 2,4,6-tri­bromo­toluene (TBT, C(7)H(5)Br(3),), 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.