Dibromonitrotoluene

Abstract

The title compound, C7H5Br2NO2 (common name: dibromonitrotoluene; systematic name: 1,3-dibromo-2-methyl-5-nitrobenzene) crystallizes with two independent molecules (A and B) in the asymmetric unit. In molecule A, the Br atoms lie almost in the plane of the benzene ring, with deviations of 0.012 (1) and 0.009 (1) Å, while for the methyl C atom the deviation is 0.038 (4) Å. In molecule B, the opposite is observed; for the methyl C atom the deviation is 0.003 (4) Å, while the two Br atoms deviate by 0.032 (1) and 0.025 (1) Å. In the crystal, the B molecules are linked via C—H...Br hydrogen bonds, forming chains along [101]. The A molecules are also aligned along the same direction, and there is a short Br...O contact of 3.101 (4) Å involving the A and B molecules. The molecules stack in layers parallel to (101) and are linked by weak π–π interactions [intercentroid distances = 3.564 (3) Å between A molecules and 3.662 (3) Å between B molecules].

Keywords

• crystal structure
• halogen–mesitylene
• dibromonitrotoluene
• Br...O interactions