Acta Crystallographica Section B

Structural Science

Volume 58, Part 2 (April 2002)

research papers

Acta Cryst. (2002). B58, 272-288 [ doi:10.1107/S0108768101019632 ]

Chiral versus racemic building blocks in supramolecular chemistry: tartrate salts of organic diamines

D. M. M. Farrell, G. Ferguson, A. J. Lough and C. Glidewell

Abstract: In the 1:1 adducts C₁₂H₁₀N₂·C₄H₆O₆ formed between 1,2-bis(4'-pyridyl)ethene and racemic tartaric acid [(I), triclinic P $\bar 1$ , Z' = 1] and (2R,3R)-tartaric acid [(II), triclinic P1, Z' = 2], the ionic components are linked by hard hydrogen bonds into single sheets, which are further linked by C-HO hydrogen bonds. In the analogous adducts C₁₀H₁₈N₂·C₄H₆O₆ formed by 4,4'-bipyridyl with racemic tartaric acid [(III), triclinic P $\bar 1$ , Z' = 1] and the chiral acid [(IV), monoclinic P2₁, Z' = 1], the hard hydrogen bonds generate bilayers which are again linked by C-HO hydrogen bonds. Piperazine forms a 1:1 salt [{(C₄H₁₀N₂)H₂}²⁺]·[(C₄H₄O₆)^2-] with (2R,3R)-tartaric acid [(V), monoclinic P2₁] sheets, which are linked by the cations to form a pillared-layer framework. In each of the 1:2 salts formed by racemic tartaric acid with piperazine [(VI), monoclinic P2₁/n, Z' = 0.5] and 1,4-diazabicyclo[2.2.2]octane (DABCO) [(VII), monoclinic P2₁/n, Z' = 0.5], the cation lies across a centre of inversion, with the [{HN(CH₂CH₂)₃NH}²⁺] cation disordered over two sets of sites: in both (VI) and (VII) the anions form a three-dimensional framework encapsulating large voids which accommodate the cations. The salt formed between DABCO and (2R,3R)-tartaric acid [(VIII), orthorhombic P2₁2₁2₁, Z' = 1] has 3:4 stoichiometry and contains four different types of ion, [{HN(CH₂CH₂)₃NH}²⁺]₂·[N(CH₂CH₂)₃NH]⁺·3(C₄H₅O₆)^-·C₄H₄O₆^2-: the hard hydrogen bonds generate a three-dimensional framework.

Keywords: chiral; racemic; supramolecular chemistry; adducts; hydrogen bonds.


	Structure factor file (CIF format) (128.8 kbytes) Contains datablock I

	Structure factor file (CIF format) (61.3 kbytes) Contains datablock V

	Structure factor file (CIF format) (166.3 kbytes) Contains datablock II

	Structure factor file (CIF format) (149.6 kbytes) Contains datablock III

	Structure factor file (CIF format) (68.8 kbytes) Contains datablock IV

	Structure factor file (CIF format) (87.5 kbytes) Contains datablock VI

	Structure factor file (CIF format) (98.0 kbytes) Contains datablock VII

	Structure factor file (CIF format) (198.0 kbytes) Contains datablock VIII

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