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

Acta Crystallogr C. 2009 Mar;65(Pt 3):o111-4. doi: 10.1107/S0108270109004181. Epub 2009 Feb 25.

Abstract

The title solvates, (I) and (II), both C(18)H(16)N(6)O(3).C(2)H(6)OS, 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-H...N hydrogen bonds to form cyclic centrosymmetric dimers from which the dimethyl sulfoxide molecules are pendent, while in (II) a combination of three independent N-H...O hydrogen bonds links the components into a chain containing both R(2)(2)(8) and R(4)(2)(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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Dimethyl Sulfoxide / chemistry*
  • Hydrogen Bonding
  • Molecular Structure
  • Pyrimidines / chemistry*

Substances

  • Pyrimidines
  • Dimethyl Sulfoxide