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 bistartrate(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.