Acta Crystallographica Section B

Structural Science

Volume 56, Part 6 (December 2000)

Acta Cryst. (2000). B56, 1054-1062 [doi:10.1107/S0108768100008302]

Adducts of meso and racemic 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane with trigonally trisubstituted benzene carboxylic acids: supramolecular structures in one and two dimensions

C. J. Burchell, G. Ferguson, A. J. Lough and C. Glidewell

Abstract: The meso and racemic forms of 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C₁₆H₃₆N₄ (tet-a and tet-b, respectively), form adducts with trigonally trisubstituted benzene carboxylic acids; tet-a-3,5-dinitrobenzoic acid (1/2) (1), tet-a-5-hydroxyisophthalic acid-water (1/1/1) (3) and tet-b-5-hydroxyisophthalic acid-water (1/1/1) (4) are all salts, [C₁₆H₃₈N₄]²⁺·2[C₇H₃N₂O₆]^- (1) and [C₁₆H₃₈N₄]²⁺·[C₈H₄O₅]^2-·H₂O (3) and (4). The conformations of the [(tet-a)H₂]²⁺ and [(tet-b)H₂]²⁺ cations are entirely different: [(tet-a)H₂]²⁺ is precisely centrosymmetric in (1) and approximately so in (3), while [(tet-b)H₂]²⁺ has approximate C₂ symmetry in (4). In each salt the cation forms two intramolecular N-HN and four intermolecular N-HO hydrogen bonds. In (1) the supramolecular structure is one-dimensional, a C₂²(13)[R₂⁴(16)] chain of rings. Compounds (3) and (4) crystallize in space groups P2₁2₁2₁ and P2₁/c, respectively, but the supramolecular structures are very similar: in each, the anions and the water molecules form a C(7)[R₃³(13)] chain of rings, generated in (3) by a 2₁ axis and in (4) by a glide plane. These chains are linked, in both (3) and (4), by cations to form sheets. Adjacent meso cations in (3) are related by a 2₁ axis and adjacent chiral cations in (4) are related by a glide plane.

Online 1 December 2000


	Structure factor file (CIF format) (245.5 kbytes) Contains datablock 16

	Structure factor file (CIF format) (206.0 kbytes) Contains datablock 14

	Structure factor file (CIF format) (288.8 kbytes) Contains datablock 15

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