The crystal of [(R)-1-cyanoethyl]bis(dimethylglyoximato)(pyrrolidine)cobalt(III) (dimethylglyoximato=2,3-butanedione dioximato) revealed a gradual change of cell parameters keeping the single-crystal form when it was irradiated by X-rays. It contains one water molecule as solvent in the asymmetric unit. The reactive cyanoethyl group is hydrogen bonded to the water molecule. In spite of the restriction by the hydrogen bond, the ordered chiral cyanoethyl group is converted to disordered racemates without degradation of crystallinity
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Takenaka et al. (1993) studied this question.