Acta Crystallographica Section B

Structural Science

Volume 60, Part 1 (February 2004)

Acta Cryst. (2004). B60, 65-75 [doi:10.1107/S0108768103026739]

Adducts of 1,4,8,11-tetraazacyclotetradecane with carboxylic acids: hydrogen-bonded supramolecular structures in two or three dimensions

C. M. Zakaria, A. J. Lough, G. Ferguson and C. Glidewell

Abstract: Four solvated salt-type adducts derived from cyclam (1,4,8,11-tetraazacyclotetradecane) and carboxylic acids have been structurally characterized. In the salt derived from adamantane-1-carboxylic acid, 4,11-diaza-1,8-diazoniacyclotetradecane bis(adamantane-1-carboxylate) tetrahydrate, (1) (monoclinic, P2₁/c, Z' = 0.5), where the cation lies across a centre of inversion, the anions and the water molecules form chains of edge-fused (8) and (16) rings, which are linked into sheets by the cations. In the 4-aminobenzoate salt, 4,11-diaza-1,8-diazoniacyclotetradecane bis(4-aminobenzoate) monohydrate, (2) (monoclinic, C2/c, Z' = 0.5), where the cation lies across a centre of inversion and the water molecule lies across a twofold rotation axis, the cations and anions generate a three-dimensional framework, readily analysed in terms of two distinct two-dimensional substructures, viz. (10 $\overline 1$ ) sheets of (46) rings, and pairwise interwoven (100) sheets, reinforced by water molecules. The 3-hydroxybenzoate salt, 4,11-diaza-1,8-diazoniacyclotetradecane bis(3-hydroxybenzoate) dihydrate, (3) (monoclinic, Pc, Z' = 1), contains a three-dimensional framework constructed from anions and water molecules only, which encapsulates large voids and within which the cations are linked to the anion-water framework via N-HO hydrogen bonds. There are two independent cations in 4,11-diaza-1,8-diazoniacyclotetradecane 5-hydroxyisophthalate(2-) methanol solvate, (4) (monoclinic, P2₁/c, Z' = 1), both lying across centres of inversion but with entirely different configurations. The anions alone form simple chains, and these chains are linked by the two types of cation into a three-dimensional framework from which the methanol molecules are pendent. Comparisons are made with carboxylate complexes of the [Ni(cyclam)]²⁺ cation and with carboxylate salts derived from meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane.

Online 21 January 2004


	Structure factor file (CIF format) (182.3 kbytes) Contains datablock I

	Structure factor file (CIF format) (145.1 kbytes) Contains datablock 71

	Structure factor file (CIF format) (150.1 kbytes) Contains datablock 53

	Structure factor file (CIF format) (239.4 kbytes) Contains datablock 65

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