Abstract
The title compounds, 2,6-di-iodo-4-nitro-toluene (DINT, C7H5I2NO2) and 2,4,6-tri-bromo-toluene (TBT, C7H5Br3,), are tris-ubstituted toluene mol-ecules. Both mol-ecules 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, mol-ecules 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, mol-ecules are linked via short N-O⋯I contacts, forming chains along [100]. In TBT, mol-ecules are linked by C-H⋯Br hydrogen bonds, forming chains along [010]. Hirshfeld surface analysis was used to explore the inter-molecular contacts in the crystals of both DINT and TBT.
Highlights
The title compounds, 2,6-diiodo-4-nitrotoluene (DINT, C7H5I2NO2) and 2,4,6tribromotoluene (TBT, C7H5Br3,), are trisubstituted toluene molecules
In order to understand the methyl radical behaviour of benzene molecules substituted by halogens and methyl groups, we have studied a number of halogenomesitylenes, such as triiodomesitylene (TIM; Boudjada et al, 2001), trichloromesitylene (TCM; Tazi et al, 1995), tribromomesitylene (TBM; Boudjada et al, 1999) and dibromomesitylene (DBM; Hernandez et al, 2003)
This study has been extended to understand and identify the methyl-group behaviour of halogeno-toluene molecules, and we report on the crystal and molecular structures of the title compounds, 2,6-diiodo-4-nitrotoluene (DINT; systematic name: 1,3-diiodo-2-methyl-5-nitrobenzene) and 2,4,6-tribromotoluene (TBT; systematic name: 1,3,5-tribromo-2-methyl-benzene)
Summary
In order to understand the methyl radical behaviour of benzene molecules substituted by halogens and methyl groups, we have studied a number of halogenomesitylenes, such as triiodomesitylene (TIM; Boudjada et al, 2001), trichloromesitylene (TCM; Tazi et al, 1995), tribromomesitylene (TBM; Boudjada et al, 1999) and dibromomesitylene (DBM; Hernandez et al, 2003). In the solid state of these halogenomethyl-benzene (HMB) compounds, the steric hindrance between the methyl group and the halogen atoms results in small out-of -plane deformations of the heavy atoms. This study has been extended to understand and identify the methyl-group behaviour of halogeno-toluene molecules, and we report on the crystal and molecular structures of the title compounds, 2,6-diiodo-4-nitrotoluene (DINT; systematic name: 1,3-diiodo-2-methyl-5-nitrobenzene) and 2,4,6-tribromotoluene (TBT; systematic name: 1,3,5-tribromo-2-methyl-benzene). Hirshfeld surface analysis was used to explore the intermolecular contacts in the crystals of both compounds
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Schedule a callMore From: Acta crystallographica. Section E, Crystallographic communications
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