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Four products from the cyanoacetylation of pyrimidines: hydrogen-bonded dimers, π-stacked hydrogen-bonded chains and hydrogen-bonded chains of edge-fused rings
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—H⋯O 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—H⋯N hydrogen bonds and linked into chains of rings by C—H⋯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⋯N hydrogen bond, and the chains are weakly linked into sheets by a π–π stacking interaction. A combination of one two-centre N—H⋯N 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.
Tópico:
Crystal structures of chemical compounds
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Información de la Fuente:
FuenteActa Crystallographica Section C Crystal Structure Communications