Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 5 (May 2013)


organic compounds



fg3289 scheme

Acta Cryst. (2013). C69, 534-537    [ doi:10.1107/S0108270113008846 ]

Hydrogen bonding in two ammonium salts of 5-sulfosalicylic acid: ammonium 3-carboxy-4-hydroxybenzenesulfonate monohydrate and triammonium 3-carboxy-4-hydroxybenzenesulfonate 3-carboxylato-4-hydroxybenzenesulfonate

G. Smith and U. D. Wermuth

Abstract: The structures of two ammonium salts of 3-carboxy-4-hydroxybenzenesulfonic acid (5-sulfosalicylic acid, 5-SSA) have been determined at 200 K. In the 1:1 hydrated salt, ammonium 3-carboxy-4-hydroxybenzenesulfonate monohydrate, NH4+·C7H5O6S-·H2O, (I), the 5-SSA- monoanions give two types of head-to-tail laterally linked cyclic hydrogen-bonding associations, both with graph-set R44(20). The first involves both carboxylic acid O-H...Owater and water O-H...Osulfonate hydrogen bonds at one end, and ammonium N-H...Osulfonate and N-H...Ocarboxy hydrogen bonds at the other. The second association is centrosymmetric, with end linkages through water O-H...Osulfonate hydrogen bonds. These conjoined units form stacks down c and are extended into a three-dimensional framework structure through N-H...O and water O-H...O hydrogen bonds to sulfonate O-atom acceptors. Anhydrous triammonium 3-carboxy-4-hydroxybenzenesulfonate 3-carboxylato-4-hydroxybenzenesulfonate, 3NH4+·C7H4O6S2-·C7H5O6S-, (II), is unusual, having both dianionic 5-SSA2- and monoanionic 5-SSA- species. These are linked by a carboxylic acid O-H...O hydrogen bond and, together with the three ammonium cations (two on general sites and the third comprising two independent half-cations lying on crystallographic twofold rotation axes), give a pseudo-centrosymmetric asymmetric unit. Cation-anion hydrogen bonding within this layered unit involves a cyclic R33(8) association which, together with extensive peripheral N-H...O hydrogen bonding involving both sulfonate and carboxy/carboxylate acceptors, gives a three-dimensional framework structure. This work further demonstrates the utility of the 5-SSA- monoanion for the generation of stable hydrogen-bonded crystalline materials, and provides the structure of a dianionic 5-SSA2- species of which there are only a few examples in the crystallographic literature.

Formula: NH4+·C7H5O6S-·H2O and 3NH4+·C7H4O6S2-·C7H5O6S-


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Chemical Markup Language (CML) file (4.1 kbytes)
[ doi:10.1107/S0108270113008846/fg3289Isup4.cml ]
Supplementary material


cmldisplay filedownload file

Chemical Markup Language (CML) file (7.7 kbytes)
[ doi:10.1107/S0108270113008846/fg3289IIsup5.cml ]
Supplementary material


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