Acta Crystallographica Section C

Crystal Structure Communications

Volume 61, Part 9 (September 2005)

organic compounds

ta1503 scheme

Acta Cryst. (2005). C61, o555-o558 [doi:10.1107/S010827010502439X]

Layered structures in proton-transfer compounds of 5-sulfosalicylic acid with the aromatic polyamines 2,6-diaminopyridine and 1,4-phenylenediamine

G. Smith, U. D. Wermuth and P. C. Healy

Abstract: The crystal structures of two proton-transfer compounds of 3-carboxy-4-hydroxybenzenesulfonic acid (5-sulfosalicylic acid) with the aromatic polyamines 2,6-diaminopyridine [namely 2,6-diaminopyridinium 3-carboxy-4-hydroxybenzenesulfonate monohydrate, C₅H₈N₃⁺·C₇H₅O₆S^-·H₂O, (I)] and 1,4-phenylenediamine [namely 1,4-phenylenediaminium 3-carboxylato-4-hydroxybenzenesulfonate, C₆H₁₀N₂²⁺·C₇H₄O₆S^2-, (II)] have been determined. Both compounds feature extensively hydrogen-bonded three-dimensional layered polymer structures having significant interlayer [pi] - [pi] interactions between the cation and anion species. In (I), the pyridine N atom of the Lewis base is protonated and forms a direct hydrogen-bonding interaction with the water molecule, which together with the two amine groups of the cation and the carboxylic acid group of the anion also give additional interactions with O-atom acceptors of the sulfonate group. In (II), a dianionic species results from deprotonation of both the sulfonic and the carboxylic acid groups, and all available O-atom acceptors interact with all dication donors, which lie about inversion centres.

Formula: C₅H₈N₃⁺·C₇H₅O₆S^-·H₂O and C₆H₁₀N₂²⁺·C₇H₄O₆S^2-


	Structure factor file (CIF format) (49.1 kbytes) Contains datablock I

	Structure factor file (CIF format) (86.1 kbytes) Contains datablock II

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