Acta Cryst. (2001). E57, o1206-o1208  [ doi:10.1107/S1600536801018001 ]

N-HO and O-HO hydrogen bonds in crystal engineering: trimethoprim hydrogen glutarate

J. J. Robert, S. B. Raj and P. T. Muthiah

Abstract: In the title compound, C₁₄H₁₉N₄O₃⁺·C₅H₇O₄^-, trimethoprim (TMP) is protonated. In the glutarate anion, one of the two carboxylic acid groups is deprotonated while the other exists as -COOH. The carboxyl group of the hydrogen glutarate ion makes a hydrogen-bonding pattern with N-H groups of the trimethoprim cation which is similar to the carboxylate group (of Asp-27 of DHFR)-trimethoprim cation interaction observed in trimethoprim-DHFR complexes. Two TMP cations and two hydrogen glutarate anions are arranged about an inversion center so that complementary DDAA arrays of quadruple hydrogen-bonding patterns are formed. The hydrogen glutarate ion bridges the 2-amino and 4-amino groups of TMP. There are also carboxyl-carboxylate hydrogen-bonding interactions involving a head-to-tail arrangement of hydrogen glutarate ions which leads to hydrogen-bonded supramolecular ribbons.

Online 24 November 2001

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