Crystals of bis(2-ethyl-3-hydroxy-6-methylpyridinium) succinate-succinic acid (1/1), C(8)H(12)NO(+)·0.5C(4)H(4)O(4)(2-)·0.5C(4)H(6)O(4), (I), and 2-ethyl-3-hydroxy-6-methylpyridinium hydrogen succinate, C(8)H(12)NO(+)·C(4)H(5)O(4)(-), (II), were obtained by reaction of 2-ethyl-6-methylpyridin-3-ol with succinic acid. The succinate anion and succinic acid molecule in (I) are located about centres of inversion. Intermolecular O-H···O, N-H···O and C-H···O hydrogen bonds are responsible for the formation of a three-dimensional network in the crystal structure of (I) and a two-dimensional network in the crystal structure of (II). Both structures are additionally stabilized by π-π interactions between symmetry-related pyridine rings, forming a rod-like cationic arrangement for (I) and cationic dimers for (II).
The title compounds, C(8)H(11)NO, (I), and 2C(8)H(12)NO(+)·C(4)H(4)O(4)(2-), (II), both crystallize in the monoclinic space group P2(1)/c. In the crystal structure of (I), intermolecular O-H···N hydrogen bonds combine the molecules into polymeric chains extending along the c axis. The chains are linked by C-H···π interactions between the methylene H atoms and the pyridine rings into polymeric layers parallel to the ac plane. In the crystal structure of (II), the succinate anion lies on an inversion centre. Its carboxylate groups interact with the 2-ethyl-3-hydroxy-6-methylpyridinium cations via intermolecular N-H···O hydrogen bonds with the pyridine ring H atoms and O-H···O hydrogen bonds with the hydroxy H atoms to form polymeric chains, which extend along the [101] direction and comprise R(4)(4)(18) hydrogen-bonded ring motifs. These chains are linked to form a three-dimensional network through nonclassical C-H···O hydrogen bonds between the pyridine ring H atoms and the hydroxy-group O atoms of neighbouring cations. π-π interactions between the pyridine rings and C-H···π interactions between the methylene H atoms of the succinate anion and the pyridine rings are also present in this network.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.