Acta Crystallographica Section C

Crystal Structure Communications

Volume 62, Part 6 (June 2006)

organic compounds

gd3017 scheme

Acta Cryst. (2006). C62, o339-o343 [ doi:10.1107/S010827010601420X ]

cis-(6RS,13RS)-3,3,10,10-Tetramethyl-6,13-diphenyl-1,8-dioxa-4,11-diazacyclotetradecane-2,5,9,12-tetraone and two of its precursors

A. Linden, B. Iliev and H. Heimgartner

Abstract: The title macrocycle, C₂₆H₃₀N₂O₆, (VI), was obtained by `direct amide cyclization' from the linear precursor 3-hydroxy-N-[1-methyl-1-(N-methyl-N-phenylcarbamoyl)ethyl]-2-phenylpropanamide, the N-methylanilide of rac-2-methyl-2-[(3-hydroxy-2-phenylpropanoyl)amino]propanoic acid, C₁₃H₁₇NO₄, (IV). The reaction proceeds via the intermediate rac-2-(2-hydroxy-1-phenylethyl)-4,4-dimethyl-1,3-oxazol-5(4H)-one, C₁₃H₁₅NO₃, (V), which was synthesized independently and whose structure was also established. Unlike all previously described analogues, the title macrocycle has the cis-diphenyl configuration. The 14-membered ring has a distorted rectangular diamond-based [3434] configuration and intermolecular N-HO hydrogen bonds link the molecules into a three-dimensional framework. The propanoic acid precursor forms a complex series of intermolecular hydrogen bonds, each of which involves pairwise association of molecules and which together result in the formation of extended two-dimensional sheets. The oxazole intermediate forms centrosymmetric hydrogen-bonded dimers in the solid state.

Formula: C₁₃H₁₇NO₄, C₁₃H₁₅NO₃ and C₂₆H₃₀N₂O₆


	Structure factor file (CIF format) (142.5 kbytes) [ doi:10.1107/S010827010601420X/gd3017IVsup2.hkl ] Contains datablock IV

	Structure factor file (CIF format) (168.1 kbytes) [ doi:10.1107/S010827010601420X/gd3017Vsup3.hkl ] Contains datablock V

	Structure factor file (CIF format) (109.2 kbytes) [ doi:10.1107/S010827010601420X/gd3017VIsup4.hkl ] Contains datablock VI

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