1,3,7-Trimethyl-2,4-dioxo-1,2,3,4-tetrahydropteridine-6-carboxylic acid hemihydrate

• Published in: Acta crystallographica. Section E, Structure reports online Structure reports online, 2010-03, Vol.66 (3), p.o719-o720
• Main Authors: Faure, René, Illán-Cabeza, Nuria A., Jiménez-Pulido, Sonia B., Linares-Ordóñez, Fátima M., Moreno-Carretero, Miguel N.
• Format: Article
• Language: English
• ISSN: 1600-5368; 1600-5368
• DOI: 10.1107/S1600536810007166

In the title compound, C10H10N4O4·0.5H2O, the two rings of the pteridine system are nearly coplanar [dihedral angle = 4.25 (9)°]. The atoms of the carboxyl group are also coplanar with the pteridine unit [r.m.s. deviation from the mean plane of the pteridine skeleton = 0.092 (2) Å]. In the crystal, the presence of the water molecule of crystallization (O atom site symmetry 2) leads to a hydrogen-bonding pattern different from the one shown by many carboxylic acid compounds (dimers formed through O—H...O hydrogen bonds between neighbouring carboxyl groups): in the present structure, the water molecule, which lies on a binary axis, acts as a bridge between two molecules, forming a hydrogen-bonded dimer. In addition to the hydrogen bonds, there are π–π ring stacking interactions involving the pyrimidine and pyrazine rings [centroid–centroid distance = 3.689 (1)Å], and two different pyrazine rings [centroid–centroid distance = 3.470 (1)Å]. Finally, there is a C—O...π contact involving a carboxylate C—O and the pyrimidine ring with a short O...Cg distance of 2.738 (2) Å.