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Keywords:

  • supramolecular interactions;
  • dimeric structure;
  • hydrogen bonding

Tris(N,N-dimethyldithiocarbamato-S,S′)antimony(III) has been isolated as a dimer in acetonitrile. Single-crystal X-ray analysis shows that the molecule possesses both Sb...S and C—H...S interactions, which results in a supramolecular association in the absence of hydrogen-bonding functionality on the R group. The co-existence in the title compound of such interactions is a unique character of known dimeric antimony(III) alkyl and/or aryl dithiocarbamate complexes. The literature reveals that the species where the alkyl and/or aryl dithiocarbamates carry the following groups: R = methyl (chloroform solvated), ethyl, n-propyl, pyrrolidine, morpholine, piperidine, azepane, benzyl, methylphenyl, are not capable of forming significant hydrogen-bonding interactions. However, either Sb...S or C—H...S intermolecular interactions dominate between two centrosymmetrically related molecules leading to a supramolecular aggregation. In the species where the R group carries hydrogen-bonding functionality, i.e. 2-hydroxylethyl, the C—H...S interactions are subverted by O—H...O hydrogen bonding. In addition, the title compound does not have steric hindrance or any hydrogen-bonding group but is stabilized with the co-existence of Sb...S and C—H...S interactions. Analysis of the secondary interactions of a series of analogues previously reported reveals that steric bulk is unnecessary for the mitigation of Sb...S interactions and for the establishment of C—H...S secondary bonding.