Molecular complexes. Part X. The crystal and molecular structure of the 1 : 1 complex of 8-hydroxyquinoline and 1,3,5-trinitrobenzene

Abstract

The crystal structure of the 1 : 1 complex of 8-hydroxyquinoline and 1,3,5-trinitrobenzene has been determined by three-dimensional X-ray methods. It is a plane-to-plane π–π* electron donor–acceptor complex formed from dimeric 8-hydroxyquinoline molecules as electron donors and 1,3,5-trinitrobenzene molecules as acceptors. In the stacks of alternating donor and acceptor molecules, each 1,3,5-trinitrobenzene molecule is located in the position of maximum π–π* overlap with respect to one of its neighbouring 8-hydroxyquinoline molecules and somewhat shifted from that position with respect to the other.

The 8-hydroxyquinoline dimer is held together by a bifurcated hydrogen-bond system similar to that in the 8-hydroxyquinoline–chloranil complex.