Four cycloalkanespiro-4′-imidazolidine-2′,5′-dithiones

Abstract

The crystal structures of four cyclo­alkane­spiro-4′-imidazolidine-2′,5′-dithiones, namely cyclo­pentane­spiro-4′-imidazolidine-2′,5′-dithione {systematic name: 1,3-diaza­spiro­[4.4]­nonane-2,4-dithione}, C7H10N2S2, cyclo­hexane­spiro-4′-imidazolidine-2′,5′-dithione {systematic name: 1,3-diaza­spiro­[4.5]decane-2,4-dithione}, C8H12N2S2, cyclo­heptane­spiro-4′-imidazolidine-2′,5′-dithione {systematic name: 1,3-diaza­spiro­[4.6]undecane-2,4-dithione}, C9H14N2S2, and cyclo­octane­spiro-4′-imidazolidine-2′,5′-dithione {systematic name: 1,3-di­aza­spiro­[4.7]dodecane-2,4-dithione}, C10H16N2S2, have been determined. The three-dimensional packing in all of the structures is based on closely similar chains, in which hydantoin moieties are linked through N—H⋯S hydrogen bonding. The size of the cyclo­alkane moiety influences the degree of its deformation. In the cyclo­octane compound, the cyclo­octane ring assumes both boat–chair and boat–boat conformations.