Hydrogen bonding patterns in 3,5-diamino-6-aryl triazines

Abstract

The crystal structure of two related 1,2,4-triazine derivatives, C 9H 7N 5Cl 2·H 2O ( 1) and C 12H 14N 5Cl 2 +·CH 3SO 3 −·H 2O ( 2) that have different biological effects, have been determined. Lamotrigine (Lamictal, 1) is a novel anticonvulsant and BWA256C ( 2) is a class 1 antiarrythmic drug. The dihedral angles between the least-squares planes of almost exactly planar phenyl and triazine rings are 76.42(6) and 76.08(6)°, for compounds 1 and 2, respectively. In 2, protonation takes place at the iminium nitrogen atom, thus suggesting the importance of resonance through the triazine ring. This resonance is also confirmed by the pattern of bond lengths and angles. Extensive networks of hydrogen bonds, in which all molecular species are involved, rule the crystal packing in both compounds. The analysis of hydrogen bond networks in other 3,5-diamino-6-aryl derivatives suggests that there is a strong influence of co-crystallizing solvent molecule on the nature of resulting hydrogen bond topology.