Acta Crystallographica Section C

Crystal Structure Communications

Volume 65, Part 3 (March 2009)

organic compounds

Acta Cryst. (2009). C65, o111-o114 [ doi:10.1107/S0108270109004181 ]

Different hydrogen-bonded structures in the isomeric solvates 2-amino-6-anilino-4-methoxy-5-[(E)-4-nitrobenzylideneamino]pyrimidine dimethyl sulfoxide solvate and 2-amino-6-[methyl(phenyl)amino]-5-[(E)-4-nitrobenzylideneamino]pyrimidin-4(3H)-one dimethyl sulfoxide solvate

R. Rodríguez, M. Nogueras, J. Cobo and C. Glidewell

Abstract: The title solvates, (I) and (II), both C₁₈H₁₆N₆O₃·C₂H₆OS, are isomeric. The conformations adopted by the 6-substituent are significantly different, with the 6-aminophenyl unit remote from the nitrophenyl ring in methoxypyrimidine (I) but adjacent to it in pyrimidinone (II). Pairs of pyrimidine molecules in (I) are linked by N-HN hydrogen bonds to form cyclic centrosymmetric dimers from which the dimethyl sulfoxide molecules are pendent, while in (II) a combination of three independent N-HO hydrogen bonds links the components into a chain containing both R₂²(8) and R₄²(8) rings, in which the dimethyl sulfoxide component acts as a double acceptor of hydrogen bonds. The significance of this study lies in its observation of different conformations for the pyrimidine components in (I) and (II), and different hydrogen-bonded structures, apparently dominated by the different roles adopted by the dimethyl sulfoxide components.

Formula: C₁₈H₁₆N₆O₃·C₂H₆OS


	Structure factor file (CIF format) (226.0 kbytes) [ doi:10.1107/S0108270109004181/sk3294Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (223.2 kbytes) [ doi:10.1107/S0108270109004181/sk3294IIsup3.hkl ] Contains datablock II

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