1. Trimethoprim–hydrogen malonate (1/1).
- Author
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Hemamalini, Madhukar, Muthiah, Packianathan Thomas, and Butcher, Ray J.
- Subjects
- *
PYRIMIDINES , *TRIMETHOPRIM , *HYDROGEN bonding , *ORGANIC compounds , *CRYSTALLOGRAPHY - Abstract
In the title compound, 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidinium hydrogen malonate, C14H19N4O3+·C3H3O4−, the trimethoprim molecule is protonated at one of the pyrimidine N atoms. The carboxylate group of the hydrogen malonate ion accepts a pair of N—H⋯O hydrogen bonds from an adjacent trimethoprim molecule, which is similar to the carboxylate–trimethoprim cation interaction present in the complex of dihydrofolate reductase with trimethoprim. An O atom of the carboxyl group forms an intramolecular O—H⋯O hydrogen bond with the carboxylate group, leading to a folded conformation for the hydrogen malonate ion. Each hydrogen malonate ion bridges two diaminopyrimidine cations, via N—H⋯O and C—H⋯N hydrogen bonds, leading to a supramolecular ribbon made up of alternating cations and anions. Two such inversion-related ribbons are cross-linked by (amino)N—H⋯O(methoxy) hydrogen bonds, (pyrimidine)C—H⋯O(methoxy) hydrogen bonds and π–π stacking involving the benzene planes. [ABSTRACT FROM AUTHOR]
- Published
- 2004
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