Acta Crystallographica Section C

Crystal Structure Communications

Volume 61, Part 2 (February 2005)

organic compounds

bm1595 scheme

Acta Cryst. (2005). C61, o105-o109 [doi:10.1107/S0108270104033451]

Hydrogen bonding in 1:1 proton-transfer compounds of 5-sulfosalicylic acid with 4-X-substituted anilines (X = F, Cl or Br)

G. Smith, U. D. Wermuth and J. M. White

Abstract: The crystal structures of three proton-transfer compounds of 5-sulfosalicylic acid (3-carboxy-4-hydroxybenzenesulfonic acid) with 4-X-substituted anilines (X = F, Cl and Br), namely 4-fluoroanilinium 5-sulfosalicylate (3-carboxy-4-hydroxybenzenesulfonate) monohydrate, C₆H₇FN⁺·C₇H₅O₆S^-·H₂O, (I), 4-chloroanilinium 5-sulfosalicylate hemihydrate, C₆H₇ClN⁺·C₇H₅O₆S^-·0.5H₂O, (II), and 4-bromoanilinium 5-sulfosalicylate monohydrate, C₆H₇BrN⁺·C₇H₅O₆S^-·H₂O, (III), have been determined. The asymmetric unit in (II) contains two formula units. All three compounds have three-dimensional hydrogen-bonded polymeric structures in which both the water molecule and the carboxylic acid group are involved in structure extension. With both (II) and (III), which are structurally similar, the common cyclic $R_{2}^{2}$ (8) dimeric carboxylic acid association is present, whereas in (I), an unusual cyclic $R_{3}^{3}$ (8) association involving all three hetero-species is found.

Formula: C₆H₇FN⁺/C₆H₇ClN⁺/C₆H₇BrN⁺·C₇H₅O₆S^-·xH₂O


	Structure factor file (CIF format) (113.6 kbytes) Contains datablock I

	Structure factor file (CIF format) (225.7 kbytes) Contains datablock II

	Structure factor file (CIF format) (134.2 kbytes) Contains datablock III

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