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

Jorge Trilleras, John N. Low, Justo Cobo, Antonio Marchal, Christopher Glidewell

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The molecules of 2-[6-amino-3-methyl-2-(methylsulfanyl)-4oxo-3,4-dihydropyrimidin-5-ylcarbonyl]acetonitrile, C9H10N4-O2S, (I), are linked in pairs by N - H center dot center dot center dot O hydrogen bonds to form cyclic centrosymmetric R-2(2)(4) dimers. Similar dimers formed by 2-(6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin5-ylcarbonyl)acetonitrile, C9H10N4O3, (II), are reinforced by paired N - H center dot center dot center dot N hydrogen bonds and linked into chains of rings by C - H center dot center dot center dot O 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 - H center dot center dot center dot N hydrogen bond, and the chains are weakly linked into sheets by a pi-pi stacking interaction. A combination of one two-centre N - H center dot center dot center dot N hydrogen bond and one three-centre C - H center dot center dot center dot(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 R-2(1)(6) and R-1(2)(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.

Original languageEnglish
Number of pages6
JournalActa Crystallographica Section C-Crystal Structure Communications
Volume64
DOIs
Publication statusPublished - Mar 2008

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