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.
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