(E)-2-[4-(Diethylamino)styryl]-1-methylquinolin-1-ium 4-chlorobenzenesulfonate monohydrate

Abstract

The asymmetric unit of the title hydrated salt, C22H25N2 +·C6H4ClO3S−·H2O, comprises two 2-[4-(di­ethyl­amino)­styr­yl]-1-methyl­quinolin-1-ium cations, two 4-chloro­benzene­sul­fon­ate anions and two solvent water mol­ecules. One ethyl group of both cations displays disorder over two positions in a 0.659 (2):0.341 (2) ratio in one mol­ecule and in a 0.501 (2):0.499 (2) ratio in the other. The sulfonate group of one anion is also disordered over two positions in a 0.893 (7):0.107 (7) ratio. The dihedral angle between the mean plane of the quinolinium ring system and that of benzene ring is 10.57 (18)° in one cation and 14.4 (2)° in the other. In the crystal, cations, anions and water mol­ecules are linked into chains along the [010] direction by O—H⋯Osulfonate hydrogen bonds, together with weak C—H⋯Osulfonate and C—H⋯Cl inter­actions. The cations are stacked by π–π inter­actions, with centroid–centroid distances in the range 3.675 (2)–4.162 (3) Å.

4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones: crystal structures and regiochemistry

“…The structures of several simple 2-styrylquinolines have been published, including those of the unsubstituted 2-styrylquinoline itself (Valle et al, 1986), and of several analogues carrying simple substituents in the phenyl ring (Kuz'mina et al, 2012). In addition, structures have been reported for a number of salts derived from 2-styrylquinolines (Kobkeatthawin et al, 2008(Kobkeatthawin et al, , 2009Chantrapromma et al, 2008Chantrapromma et al, , 2014Fun et al, 2013). For all of these compounds, the styryl group was introduced into a preformed quinoline nucleus.…”