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  • Title: 2-Ethyl-6-methylpyridin-3-ol and its salt bis(2-ethyl-3-hydroxy-6-methylpyridinium) succinate.
    Author: Lyakhov AS, Ivashkevich LS, Survilo VL, Kipnis AM, Trukhachova TV.
    Journal: Acta Crystallogr C; 2012 Sep; 68(Pt 9):o365-8. PubMed ID: 22935506.
    Abstract:
    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.
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