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Crystallography shows that with the smaller xanthate-bound methyl groups in Zn(S 2 COMe) 2 (dafone) ( 1 ) and Cd(S 2 COMe) 2 (dafone) ( 3 ) anti-parallel C=O…C=O interactions link molecules into dimers. These are further associated via π—π interactions into a supramolecular chain, and in the case of  3  into a supramolecular two-dimensional array via C—H…S contacts. Increasing the size of the organic residue,  i.e.  to ethyl and isopropyl in Zn(S 2 COEt) 2 (dafone) ( 2 ), Cd(S 2 COEt) 2 (dafone) ( 4 ) and Cd(S 2 CO-iPr) 2 (dafone) ( 5 ), does not allow for the formation of this supramolecular architecture. Instead, supramolecular chains are sustained by C—H…S and C—H…π(chelate) interactions (the latter exclusively in the case of  5 ). The presence of recognisable/significant π—π and C—H…S and C—H…π(chelate) interactions is not consistent amongst the series yet only two crystal packing patterns are noted depending on the presence of the C=O…C=O interactions. This observation points to the importance of overall crystal packing considerations of binuclear species in  1  and  3 , and mononuclear species in  2 ,  4  and  5 .

Steric control over C=O...C=O interactions in M(S 2 COR) 2 (dafone) compounds: M = Zn and Cd; R = Me, Et and iPr; dafone = 4,5-diazafluoren-9-one-N,N′