Acta Crystallographica Section C

Crystal Structure Communications

Volume 61, Part 5 (May 2005)

organic compounds

sk1828 scheme

Acta Cryst. (2005). C61, o306-o311 [doi:10.1107/S0108270105008498]

Supramolecular structures of five 5-(arylmethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones: isolated molecules, hydrogen-bonded chains and chains of fused hydrogen-bonded rings

M. C. Rezende, M. Dominguez, J. L. Wardell, J. M. S. Skakle, J. N. Low and C. Glidewell

Abstract: In each of the five title compounds, namely 5-benzylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C₁₃H₁₂N₂O₃, (I), 5-(3-methoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C₁₄H₁₄N₂O₄, (II), 5-(4-methoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C₁₄H₁₄N₂O₄, (III), 5-[4-(dimethylamino)benzylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C₁₅H₁₇N₃O₃, (IV), and 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C₂₁H₂₈N₂O₄, (V), which crystallizes with Z' = 2 in P $\overline{1}$ , there is a very wide C-C-C angle at the methine C atom linking the two rings, ranging from 137.1 (2)° in (I) to 139.14 (14)° in (III). There is evidence for intramolecular charge separation in (IV) and, to a lesser degree, in (III). The molecules of (I)-(III) are linked by pairs of C-HO hydrogen bonds into chains of edge-fused rings, with alternating R₂²(14) and R₂²(16) rings in (I), alternating R₂²(14) and R₄⁴(20) rings in (II), with two types of R₂²(16) rings alternating in (III). The molecules in (IV) are linked by a single C-HO hydrogen bond into simple C(8) chains, but there are no direction-specific intermolecular interactions in (V).

Formula: C₁₃H₁₂N₂O₃, C₁₄H₁₄N₂O₄, C₁₄H₁₄N₂O₄, C₁₅H₁₇N₃O₃ and C₂₁H₂₈N₂O₄


	Structure factor file (CIF format) (126.4 kbytes) Contains datablock I

	Structure factor file (CIF format) (139.7 kbytes) Contains datablock II

	Structure factor file (CIF format) (140.4 kbytes) Contains datablock III

	Structure factor file (CIF format) (150.8 kbytes) Contains datablock IV

	Structure factor file (CIF format) (433.1 kbytes) Contains datablock V

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