Acta Crystallographica Section C

Crystal Structure Communications

Volume 64, Part 9 (September 2008)

organic compounds

 

Two- and three-dimensional hydrogen-bonded structures in the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with the isomeric monoaminobenzoic acids

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

Abstract: The crystal structures of the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with the three isomeric monoaminobenzoic acids, namely the hydrate 2-carboxyanilinium 2-carboxy-4,5-dichlorobenzoate dihydrate, C₇H₈NO₂⁺·C₈H₃Cl₂O₄^-·2H₂O, (I), and the anhydrous salts 3-carboxyanilinium 2-carboxy-4,5-dichlorobenzoate, C₇H₈NO₂⁺·C₈H₃Cl₂O₄^-, (II), and 4-carboxyanilinium 2-carboxy-4,5-dichlorobenzoate, C₇H₈NO₂⁺·C₈H₃Cl₂O₄^-, (III), have been determined at 130 K. Compound (I) has a two-dimensional hydrogen-bonded sheet structure, while (II) and (III) are three-dimensional. All three compounds feature sheet substructures formed through anilinium N⁺-HO_carboxyl and anion carboxylic acid O-HO_carboxyl interactions and, in the case of (I), additionally linked through the donor and acceptor associations of the solvent water molecules. However, (II) and (III) have additional lateral extensions of these substructures though cyclic R²₂(8) associations involving the carboxylic acid groups of the cations. Also, (II) and (III) have cation-anion - aromatic ring interactions. This work provides further examples illustrating the regular formation of network substructures in the 1:1 proton-transfer salts of 4,5-dichlorophthalic acid with the bifunctional aromatic amines.

Formula: C₇H₈NO₂⁺·C₈H₃Cl₂O₄^-·2H₂O, C₇H₈NO₂⁺·C₈H₃Cl₂O₄^- and C₇H₈NO₂⁺·C₈H₃Cl₂O₄^-

	Structure factor file (CIF format) (153.3 kbytes) [ doi:10.1107/S0108270108027054/sf3087Isup2.hkl ] Contains datablock I
	Structure factor file (CIF format) (335.4 kbytes) [ doi:10.1107/S0108270108027054/sf3087IIsup3.hkl ] Contains datablock II
	Structure factor file (CIF format) (166.7 kbytes) [ doi:10.1107/S0108270108027054/sf3087IIIsup4.hkl ] Contains datablock III

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