The crystal structures of 4,5-bis(bromomethyl)-1,3-dithiol-2-one, C(5)H(4)Br(2)OS(2), (I), and 4,5-bis[(dihydroxyphosphoryl)methyl]-1,3-dithiol-2-one, C(5)H(8)O(7)P(2)S(2), (II), occur with similar unit cells in the same monoclinic space group. Both molecules reside on a twofold symmetry axis coincident with the C=O bond, so that the substituents in the 4- and 5-positions project above and below the plane of the 1,3-dithiol-2-one ring. In both structures, the molecules align themselves in a head-to-tail fashion along the b axis, and these rows of molecules then stack, with alternating directionality, along the c axis. For (II), an extensive network of intermolecular hydrogen bonds occurs between molecules within the same stack and between adjacent stacks. Each -CH(2)P(O)(OH)(2) group participates in four hydrogen bonds, twice as donor and twice as acceptor.
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