A co-crystal of heterobicyclic isomers as a product of the cyclocondensation reaction of 3,4-diaminofurazan with diethyl-2-oxosuccinate

Abstract

Using single crystal XRD, it was proved that the cyclocondensation of 3,4-diaminofurazan with diethyl-2-oxosuccinate gives two products belonging to different heterocyclic systems, being structural isomers – derivatives of furazano[3,4-b]pyrazin-6-one (2) and furazano[3,4-b][1,4]diazepin-7-one (6). The simultaneous formation of compounds 2 and 6 in this reaction provokes also the generation of a third solid product, an unusual co-crystal (2)_0.40(6)_0.60. This is a rare example of co-crystallization of two isomers, the molecules of which occupy the same position in the crystal structure, despite the differences of the heterocyclic systems.