Acta Crystallographica Section C

Crystal Structure Communications

Volume 59, Part 8 (August 2003)

Acta Cryst. (2003). C59, o454-o460 [doi:10.1107/S0108270103013465]

Benzylation and nitrosation of 4-amino-2-(methylsulfanyl)pyrimidin-6(1H)-one: two P2₁/c polymorphs of 4-amino-1-benzyl-2-(methylsulfanyl)pyrimidin-6(1H)-one with Z' = 1 and 2, 4-amino-6-benzyloxy-2-(methylsulfanyl)pyrimidine and 4-amino-1-benzyl-2-(methylsulfanyl)-5-nitrosopyrimidin-6(1H)-one all give different hydrogen-bonded supramolecular structures

C. Glidewell, J. N. Low, A. Marchal and A. Quesada

Abstract: 4-Amino-1-benzyl-2-(methylsulfanyl)pyrimidin-6(1H)-one, C₁₂H₁₃N₃OS, crystallizes in two polymorphic forms, both having space group P2₁/c, with Z' = 1 for form (I) and Z' = 2 for form (II). In (I), the molecules are linked by a single N-HO hydrogen bond into simple C(6) chains, which are themselves linked into sheets by aromatic [bold pi] - interactions, while in (II), chains of edge-fused R₄²(8) and R₄⁴(24) rings are generated by four distinct N-HO hydrogen bonds. In 4-amino-1-benzyl-2-(methylsulfanyl)-5-nitrosopyrimidin-6(1H)-one, C₁₂H₁₂N₄O₂S, (III), where Z' = 2, two independent three-centre N-H(N,O) hydrogen bonds generate a C(5)C(6)[R₁²(5)] chain of rings. In 4-amino-6-benzyloxy-2-(methylsulfanyl)pyrimidine, C₁₂H₁₃N₃OS, (IV), which is isomeric with (I) and (II), a combination of N-HN and N-HO hydrogen bonds generates a sheet of alternating R₂²(8) and R₆⁶(28) rings.

Formula: Isomers of C₁₂H₁₃N₃OS, and C₁₂H₁₂N₄O₂S

Online 22 July 2003


	Structure factor file (CIF format) (127.7 kbytes) Contains datablock I

	Structure factor file (CIF format) (260.8 kbytes) Contains datablock II

	Structure factor file (CIF format) (216.4 kbytes) Contains datablock III

	Structure factor file (CIF format) (58.2 kbytes) Contains datablock IV

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