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

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, C₄H₁₄N₂S₂²⁺·2C₄H₅O₆^-·2H₂O, (III). Cystamine [systematic name: 2,2'-di­thio­bis­(ethyl­amine), C₄H₁₂N₂S₂], reacts with L-(+)-tartaric acid to produce a mixture of cystamine tartrate(2-), C₄H₁₄N₂S₂²⁺·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 P2₁2₁2₁.