Supramolecular assemblies of single-substituted nitrobenzenes in their experimental and predicted crystal structures

Intermolecular interactions leading to particular molecular packing have been studied in the crystals of 30 single-substituted nitrobenzenes. The experimental and predicted crystal structures of ortho, meta and para isomers of nitrophenol, nitroaniline, nitrobenzoic acid, halogenonitrobenzenes, dinitrobenzene, nitrobenzaldehyde, cyano- and isocyanobenzene have been analyzed. The stacking and herringbone modes of molecular packing and the resulting interactions in the crystals exhibiting, or not exhibiting intermolecular hydrogen bondings, are discussed. The relevance of the intermolecular interactions between nitro groups is stressed.