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

Abstract

In the title compound, C18H16N+·I−, the cation is disordered over two orientations related by a 180° rotation about its long axis with occupancies of 0.554 (7) and 0.446 (7). Both disorder components exist in an E configuration. The dihedral angle between the pyridinium ring and the naphthalene ring system is 4.7 (6)° in the major disorder component and 1.6 (8)° in the minor component. In the crystal structure, centrosymmetrically related cations are stacked along the a axis, with significant π–π inter­actions between the pyridinium ring and the naphthalene ring system [centroid-centroid distance = 3.442 (9) Å]. The iodide ions are located between adjacent columns of cations. The cations are linked to the iodide ions by C—H⋯I inter­actions. Weak C—H⋯π inter­actions involving the methyl group are also observed.

(E)-4-[2-(4-Ethoxyphenyl)ethenyl]-1-methylpyridinium 4-bromobenzenesulfonate methanol hemisolvate

“…The ethoxy group is co-planar with the attached benzene ring as indicated by the torsion angle C11A-O1-C15A-C16A = 178.8 (8)° for major component and C11B-O1-C15B-C16B = -175 (2)° for minor component. The bond lengths in (I) are in normal ranges (Allen et al, 1987) and comparable to those in related structures (Chantrapromma et al, 2006;Chantrapromma, Jansrisewangwong et al, 2009;Fun et al, 2009).…”

“…For background to non-linear optical materials research, see: ; Cheng, Tam, Stevenson et al (1991); Ogawa et al (2008); Ruanwas et al (2010); Yang et al (2007). For related structures, see: Chantrapromma et al (2006); ; Chantrapromma, Jansrisewangwong et al (2009); Fun et al (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).…”

1,1′-Dimethyl-4,4′-(2,4-di-1-naphthylcyclobutane-1,3-diyl)dipyridinium–(E)-1-methyl-4-[2-(1-naphthyl)vinyl]pyridinium–4-aminobenzenesulfonate–water (0.25/1.50/2/2)

“…The dihedral angle between the pyridinium and two aromatic C1A-C6A and C1A/C6A-C10A rings being 13 (2) and 14 (2)°, respectively, with the C10A-C11A-C12A-C13A torsion angle being -115 (3)°. Bond lengths are in normal ranges (Allen et al, 1987) and comparable with those in related structures (Chantrapromma et al, 2009;Fun et al, 2009). (Fig.2)…”

“…For background to non-linear optical materials, see: Williams (1984). For related structures, see: Chantrapromma et al (2009); Fun et al (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986).…”

“…So the X-ray structure determination is a very important procedure to find out whether the compound is NLO active. During the course of our NLO research, we have previously reported crystal structures of (E)-1-methyl-4-[2-(2-naphthyl)vinyl]pyridinium iodide (I) (Fun et al, 2009) and (E)-1-methyl-4-[2-(1-naphthyl)vinyl]pyridinium 4-bromobenzenesulfonate (II) (Chantrapromma et al, 2009). These compounds were prepared by extending conjugated π-system which is a popular strategy to design NLO materials.…”