Acta Cryst. (2002). E58, o180-o182  [ doi:10.1107/S1600536802000909 ]

N-HN hydrogen bonds in trimethoprim salicylate methanol solvate [trimethoprim is 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine]

P. Panneerselvam, N. Stanley and P. T. Muthiah

Abstract: In the title compound, trimethoprim salicylate methanol solvate [3,4,5-trimethoxybenzyl)pyrimidin-1-ium salicylate methanol solvate], C₁₄H₁₉N₄O₃⁺·C₇H₅O₃^-·CH₄O, the trimethoprim molecule is protonated at N1. The carboxylate group of the salicylate ion interacts with the protonated pyrimidine moiety of trimethoprim through a pair of nearly parallel N-HO hydrogen bonds. This is reminiscent of the carboxylate-trimethoprim interaction observed in dihydrofolate reductase-trimethoprim complexes. The pyrimidine moieties of the trimethoprim cations are centrosymmetrically paired through a pair of N-HN hydrogen bonds involving the 4-amino group and the unsubstituted pyrimidine N atom. The pyrimidine plane makes a dihedral angle of 89.5  (4)° with the phenyl ring in the trimethoprim cation.

Online 25 January 2002

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