Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 5 (May 2013)

organic compounds

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-

hkldisplay filedownload file

Structure factor file (CIF format) (95.7 kbytes)
[ doi:10.1107/S0108270113008846/fg3289Isup2.hkl ]
Contains datablock I

hkldisplay filedownload file

Structure factor file (CIF format) (186.5 kbytes)
[ doi:10.1107/S0108270113008846/fg3289IIsup3.hkl ]
Contains datablock II


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