Three salts from the reactions of cysteamine and cystamine withL-(+)-tartaric acid

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Reaction between cysteamine (systematic name: 2-aminoethanethiol, C2H7NS) and L-(+)-tartaric acid [systematic name: (2R,3R)-2,3-dihydroxybutanedioic acid, C4H6O6] results in a mixture of cysteamine tartrate(1-) monohydrate, C2H8NS(+)·C4H5O6(-)·H2O, (I), and cystamine bis[tartrate(1-)] dihydrate, C4H14N2S2(2+)·2C4H5O6(-)·2H2O, (III). Cystamine [systematic name: 2,2'-dithiobis(ethylamine), C4H12N2S2], reacts with L-(+)-tartaric acid to produce a mixture of cystamine tartrate(2-), C4H14N2S2(2+)·C4H4O6(2-), (II), and (III). In each crystal structure, the anions are linked by O-H···O hydrogen bonds that run parallel to the a axis. In addition, hydrogen bonding involving protonated amino groups in all three salts, and water molecules in (I) and (III), leads to extensive three-dimensional hydrogen-bonding networks. All three salts crystallize in the orthorhombic space group P2(1)2(1)2(1).