Crystal structure of a complex between lumiflavin and 2,6-diamino-9-ethylpurine: a flavin adenine dinucleotide model exhibiting charge-transfer interactions.

The x-ray structure of the deep red crystalline complex lumiflavin-2,6-diamino-9-ethylpurine has been determined. The flavin and adenine derivatives form hydrogen-bonded base pairs of the Watson-Crick type. The molecules in the crystal also associate via extensively overlapped flavin/adenine and flavin/flavin stacking interactions in which there are several contacts that are closer than van der Waals distances. This, together with the red color of the crystals, is indicative of the formation of a charge-transfer complex.