The potential of intermolecular N⋯O interactions of nitro groups in crystal engineering, as revealed by structures of hexakis(4-nitrophenyl)benzene

Like other derivatives of hexaphenylbenzene, hexakis(4-nitrophenyl)benzene (1) crystallizes under a variety of conditions as layered structures in which significant quantities of guests are included in spaces between the layers or within them. In structures of nitroarene 1, multiple intermolecular N⋯O interactions of NO2 groups help to hold the layers together and determine how the molecular constituents are positioned. The behavior of nitroarene 1 confirms that N⋯O interactions can allow crystal engineers to position molecules with a useful degree of predictability, particularly when stronger interactions such as hydrogen bonds are absent, and when competition with other weak interactions is limited.