Research Article: (E)-1-Methyl-4-[2-(1-naphth­yl)vin­yl]pyridinium 4-bromo­benzene­sulfonate1

Date Published: May 01, 2009

Publisher: International Union of Crystallography

Author(s): Suchada Chantrapromma, Kullapa Chanawanno, Hoong-Kun Fun.


In the title compound, C18H16N+·C6H4BrO3S−, the cation exists in the E configuration and the whole mol­ecule of the cation is disordered with a refined site-occupancy ratio of 0.733 (1):0.267 (1). The naphthalene system is not planar, the inter­planar angle between the two aromatic rings being 5.0 (5)° for the major component and 5.7 (10)° for the minor component. The cation is twisted with dihedral angles between the pyridinium ring and the two aromatic rings of the naphthalene system of 56.3 (5) and 51.4 (5)° (for the major component) and 52.2 (11) and 53.4 (11)° (for the minor component). The pyridinium ring and the benzene ring of the anion are inclined to each other at inter­planar angles of 85.0 (4) and 71.5 (9)° for the major and minor components, respectively. In the crystal packing, the cations and anions are alternately arranged with the cations stacked in an anti­parallel manner along the c axis and the anions linked together into chains along the same direction. The cations are linked to the anions into chains along [102] by weak C—H⋯O inter­actions. The crystal structure is further stabilized by C—H⋯π inter­actions and π–π contacts, with Cg⋯Cg distances of 3.502 (9) and 3.698 (6) Å. A short Br⋯O contact [3.029 (4) Å] is also present.

Partial Text

For bond-length data, see: Allen et al. (1987 ▶). For background to NLO materials research, see: Cheng et al. (1991a ▶; 1991b ▶); Dittrich et al. (2003 ▶); Ogawa et al. (2008 ▶); Weir et al. (2003 ▶); Yang et al. (2007 ▶). For related structures, see, Chanawanno et al. (2008 ▶) and Chantrapromma et al. (2006 ▶; 2007 ▶; 2008 ▶; 2009 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).




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