(E)-4-[4-(Dimethylamino)styryl]-1-methylpyridinium 4-bromobenzenesulfonate

Abstract

In the title compound, C16H19N2 +·C6H4BrO3S−, the cation is nearly planar, with a dihedral angle of 3.19 (15)° between the pyridinium and the dimethylaminophenyl rings, and exists in the trans configuration. In the crystal packing, the cations and anions are linked into chains parallel to the c axis. These chains are stacked along the b axis. The crystal is stabilized by weak C—H⋯O and C—H⋯π inter­actions, and a π–π inter­action is also observed with a Cg⋯Cg distance of 3.5675 (19) Å.

(E)-1-Methyl-4-[2-(1-naphthyl)vinyl]pyridinium 4-bromobenzenesulfonate

“…The cation and anion are inclined to each other with interplanar angles of 85.0 (4)° and 71.5 (9)° respectively between the benzene ring and the pyridinium units of the major and minor disorder components. The bond lengths in (I) are in normal ranges (Allen et al, 1987) and comparable to those in related structures (Chanawanno et al, 2008;Chantrapromma et al, 2006Chantrapromma et al, , 2007Chantrapromma et al, , 2008Chantrapromma et al, , 2009).…”

“…Styryl pyridinium derivatives are considered to be good conjugated π-systems (Cheng et al, 1991a(Cheng et al, , 1991b. We have previously synthesized and reported the crystal structures of several pyridinium salts (Chanawanno et al, 2008;Chantrapromma et al, 2006Chantrapromma et al, , 2007Chantrapromma et al, , 2008Chantrapromma et al, , 2009 in order to study their NLO properties. The title compound (I) was synthesized by introducing a naphthalenyl group into the cation in order to increase the extent of π-conjugation in the system.…”

2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-bromobenzenesulfonate

“…The methyl group is co-planar with the attached N1/C1-C5 ring. The bond lengths in (I) are in normal ranges (Allen et al, 1987) and comparable with those in related structures (Chanawanno et al, 2008;Chantrapromma et al, 2006Chantrapromma et al, , 2007Chantrapromma et al, , 2009Jindawong et al, 2005).…”

“…For background to non-linear optical materials research, see: Coe et al (2003); Dittrich et al (2003); Ogawa et al (2008); Otero et al (2002); Weir et al (2003); Yang et al (2007). For related structures, see, for example: Chanawanno et al (2008); Chantrapromma et al (2006Chantrapromma et al ( , 2007Chantrapromma et al ( , 2008Chantrapromma et al ( , 2009; Jindawong et al (2005). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).…”

“…One strategy to enhance the hyperpolariability of the cations is by elongation of its π-conjugation system. Based on these studies, we have previously synthesized and reported the crystal structure of the pyridinium salts (Chanawanno et al, 2008;Chantrapromma et al, 2006Chantrapromma et al, , 2007Chantrapromma et al, , 2008Chantrapromma et al, , 2009Jindawong et al, 2005) in order to study for their NLO properties. We herein report the crystal structure of the title compound, (I), which is another pyridinium salt.…”