Acta Crystallographica Section C

Crystal Structure Communications

Volume 64, Part 3 (March 2008)

organic compounds

Acta Cryst. (2008). C64, o149-o154 [ doi:10.1107/S0108270108003557 ]

Four products from the cyanoacetylation of pyrimidines: hydrogen-bonded dimers, -stacked hydrogen-bonded chains and hydrogen-bonded chains of edge-fused rings

J. Trilleras, J. N. Low, J. Cobo, A. Marchal and C. Glidewell

Abstract: The molecules of 2-[6-amino-3-methyl-2-(methylsulfanyl)-4-oxo-3,4-dihydropyrimidin-5-ylcarbonyl]acetonitrile, C₉H₁₀N₄O₂S, (I), are linked in pairs by N-HO hydrogen bonds to form cyclic centrosymmetric R₂²(4) dimers. Similar dimers formed by 2-(6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-ylcarbonyl)acetonitrile, C₉H₁₀N₄O₃, (II), are reinforced by paired N-HN hydrogen bonds and linked into chains of rings by C-HO hydrogen bonds. The molecules of 2-cyano-N-[6-methoxy-2-(methylsulfanyl)pyrimidin-4-yl]acetamide, C₉H₁₀N₄O₂S, (III), are linked into simple C(6) chains by an N-HN hydrogen bond, and the chains are weakly linked into sheets by a [pi] - [pi] stacking interaction. A combination of one two-centre N-HN hydrogen bond and one three-centre C-H(N,O) hydrogen bond links the molecules of 2-cyano-N-[6-chloro-2-(methylsulfanyl)pyrimidin-4-yl]acetamide, C₈H₇ClN₄OS, (IV), into a chain of alternating edge-fused R₂¹(6) and R₁²(6) rings. The crystal structures reported in this study, and those of some related examples from the recent literature, show a wide variation in hydrogen-bonded aggregation consequent upon rather small changes in molecular constitution.

Formula: C₉H₁₀N₄O₂S, C₉H₁₀N₄O₃, C₉H₁₀N₄O₂S and C₈H₇ClN₄OS


	Structure factor file (CIF format) (117.2 kbytes) [ doi:10.1107/S0108270108003557/ga3078Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (106.9 kbytes) [ doi:10.1107/S0108270108003557/ga3078IIsup3.hkl ] Contains datablock II

	Structure factor file (CIF format) (123.2 kbytes) [ doi:10.1107/S0108270108003557/ga3078IIIsup4.hkl ] Contains datablock III

	Structure factor file (CIF format) (114.9 kbytes) [ doi:10.1107/S0108270108003557/ga3078IVsup5.hkl ] Contains datablock IV

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