Acta Crystallographica Section C

Crystal Structure Communications

Volume 65, Part 4 (April 2009)

organic compounds

Acta Cryst. (2009). C65, o123-o127 [ doi:10.1107/S0108270109005836 ]

The crucial role of C-HO and C=O interactions in the building of three-dimensional structures of dicarboxylic acid-biimidazole compounds

X.-L. Gao, L.-P. Lu and M.-L. Zhu

Abstract: The supramolecular architectures of three dicarboxylic acid-biimidazole compounds, namely, 2,2'-biimidazolium malonate, C₆H₈N₄²⁺·C₃H₂O₄^2-, (I), 2,2'-bi(1H-imidazole) succinic acid, C₆H₆N₄·C₄H₆O₄, (II), and 2,2'-biimidazolium 2,2'-iminiodiacetate chloride, C₆H₈N₄²⁺·C₄H₆NO₄^-·Cl^-, (III), are reported. The crystal structures are assembled by the same process, namely double conventional N-HO or O-HN hydrogen bonds link the dicarboxylates and biimidazoles to form tapes, which are stacked in parallel through lone-pair-aromatic interactions between carbonyl O atoms and biimidazole groups and are further linked via weak C-HO interactions. The C=O [pi] interactions involved in stacking the tapes in (II) and the C-HO interactions involved in linking the tapes in (II) and (III) demonstrate the crucial role of these interactions in the crystal packing. There is crystallographically imposed symmetry in all three structures. In (I), two independent malonate anions have their central C atoms on twofold axes and two biimidazolium dications each lie about independent inversion centres; in (II), the components lie about inversion centres, while in (III), the unique cation lies about an inversion centre and the iminiodiacetate and chloride anions lie across and on a mirror plane, respectively.

Formula: C₆H₈N₄²⁺·C₃H₂O₄^2-, C₆H₆N₄·C₄H₆O₄ and C₆H₈N₄²⁺·C₄H₆NO₄^-·Cl^-


	Structure factor file (CIF format) (90.6 kbytes) [ doi:10.1107/S0108270109005836/fg3076Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (52.3 kbytes) [ doi:10.1107/S0108270109005836/fg3076IIsup3.hkl ] Contains datablock II

	Structure factor file (CIF format) (57.3 kbytes) [ doi:10.1107/S0108270109005836/fg3076IIIsup4.hkl ] Contains datablock III

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