Weak Interactions in Crystal Engineering - Understanding the Recognition Properties of the Nitro Group

1,3,5-Trinitrobenzene and 1,3,5-triethynylbenzene cocrystallise to form a solid state structure in which the two components assemble to form segregated hydrogen-bonded tapes. This behaviour is rationalised, through the use of the Cambridge Structural Database and ab initio electronic structure calculations, in terms of the fundamental recognition properties of the nitro group. The recognition behaviour of the nitro group is a function of both the intrinsic electronic properties of the nitro group itself and the nature of the hydrogen bond donor with which it interacts.