Acta Crystallographica Section C

Crystal Structure Communications

Volume 64, Part 3 (March 2008)

organic compounds

 

One-dimensional hydrogen-bonded structures in the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with 8-hydroxyquinoline, 8-aminoquinoline and quinoline-2-carboxylic acid (quinaldic acid)

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

Abstract: The structures of the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with 8-hydroxyquinoline, 8-aminoquinoline and quinoline-2-carboxylic acid (quinaldic acid), namely anhydrous 8-hydroxyquinolinium 2-carboxy-4,5-dichlorobenzoate, C₉H₈NO⁺·C₈H₃Cl₂O₄^-, (I), 8-aminoquinolinium 2-carboxy-4,5-dichlorobenzoate, C₉H₉N₂⁺·C₈H₃Cl₂O₄^-, (II), and the adduct hydrate 2-carboxyquinolinium 2-carboxy-4,5-dichlorobenzoate quinolinium-2-carboxylate monohydrate, C₁₀H₈NO₂⁺·C₈H₃Cl₂O₄^-·C₁₀H₇NO₂·H₂O, (III), have been determined at 130 K. Compounds (I) and (II) are isomorphous and all three compounds have one-dimensional hydrogen-bonded chain structures, formed in (I) through O-HO_carboxyl extensions and in (II) through N⁺-HO_carboxyl extensions of cation-anion pairs. In (III), a hydrogen-bonded cyclic R₂²(10) pseudo-dimer unit comprising a protonated quinaldic acid cation and a zwitterionic quinaldic acid adduct molecule is found and is propagated through carboxylic acid O-HO_carboxyl and water O-HO_carboxyl interactions. In both (I) and (II), there are also cation-anion aromatic ring - associations. This work further illustrates the utility of both hydrogen phthalate anions and interactive-group-substituted quinoline cations in the formation of low-dimensional hydrogen-bonded structures.

Formula: C₉H₈NO⁺·C₈H₃Cl₂O₄^-, C₉H₉N₂⁺·C₈H₃Cl₂O₄^- and C₁₀H₈NO₂⁺·C₈H₃Cl₂O₄^-·C₁₀H₇NO₂·H₂O

	Structure factor file (CIF format) (120.6 kbytes) [ doi:10.1107/S0108270108004034/gd3186Isup2.hkl ] Contains datablock I
	Structure factor file (CIF format) (173.1 kbytes) [ doi:10.1107/S0108270108004034/gd3186IIsup3.hkl ] Contains datablock II
	Structure factor file (CIF format) (234.1 kbytes) [ doi:10.1107/S0108270108004034/gd3186IIIsup4.hkl ] Contains datablock III

To open or display or play some files, you may need to set your browser up to use the appropriate software. See the full list of file types for an explanation of the different file types and their related mime types and, where available links to sites from where the appropriate software may be obtained.

The download button will force most browsers to prompt for a file name to store the data on your hard disk.

Where possible, images are represented by thumbnails.

Copyright © International Union of Crystallography
IUCr Webmaster