1-Methyl-2-[(E)-2-(2-thien­yl)ethen­yl]quinolinium iodideThis paper is dedicated to the late Her Royal Highness Princess Galyani Vadhana Krom Luang Naradhiwas Rajanagarindra for her patronage of science in Thailand.

Ruanwas, P.; Kobkeatthawin, T.; Chantrapromma, S.; Fun, H.-K.; Karalai, C.

doi:10.1107/S1600536808020734

Volume 64
Part 8
Pages o1453-o1454
August 2008

Received 1 July 2008
Accepted 4 July 2008
Online 9 July 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.023
wR = 0.060
Data-to-parameter ratio = 24.6
Details

1-Methyl-2-[(E)-2-(2-thienyl)ethenyl]quinolinium iodide¹

Pumsak Ruanwas,^a Thawanrat Kobkeatthawin,^a Suchada Chantrapromma,^a ^* Hoong-Kun Fun ^b ⁺ and Chatchanok Karalai ^a

^aCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: suchada.c@psu.ac.th

In the title compound, C₁₆H₁₄NS⁺·I^-, the cation has an E configuration about the C=C double bond of the ethylene unit. The dihedral angle between the thiophene ring and the quinolinium ring system is 11.67 (11)°. A weak C-HS intramolecular interaction involving the thiophene ring generates an S(5) ring motif. In the crystal structure, the iodide ion, located between the cations arranged in an antiparallel manner, forms weak C-HI interactions. The crystal structure is further stabilized by a [pi] - [pi] interaction between the thiophene and pyridine rings; the centroid-centroid distance is 3.6818 (13) Å.

Related literature

For bond lengths, see: Allen et al. (1987). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see, for example: Chantrapromma et al. (2006, 2008); Chantrapromma, Jindawong & Fun (2007); Chantrapromma, Jindawong, Fun & Patil (2007). For background literature on non-linear optical properties, see, for example: Chou et al. (1996); Dittrich et al. (2003); Drost et al. (1995); Morley (1991).

Experimental

Crystal data

C₁₆H₁₄NS⁺·I^-
M_r = 379.25
Triclinic, $[P \overline 1]$
a = 7.8243 (1) Å
b = 9.6906 (1) Å
c = 10.7633 (2) Å
= 97.521 (1)°
= 95.338 (1)°
= 112.758 (1)°
V = 736.82 (2) Å³
Z = 2
Mo K radiation
= 2.30 mm^-1
T = 100.0 (1) K
0.58 × 0.28 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.346, T_max = 0.725
17060 measured reflections
4261 independent reflections
4118 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.022
wR(F²) = 0.059
S = 1.10
4261 reflections
173 parameters
H-atom parameters constrained
_max = 1.50 e Å^-3
_min = -0.90 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C10-H10AS1	0.93	2.80	3.189 (2)	106
C11-H11AI1ⁱ	0.93	3.06	3.934 (2)	157
C16-H16BI1ⁱⁱ	0.96	3.06	3.962 (2)	156
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2311 ).

Acknowledgements

The Center for Innovation in Chemistry: Postgraduate Education and Research Program in Chemistry (PERCH-CIC), Commission on Higher Education, Ministry of Education and the Graduate School, Prince of Songkla University are gratefully acknowledged for providing financial support to PR. The authors thank the Prince of Songkla University for a research grant and also the Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, S1-S19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chantrapromma, S., Jindawong, B. & Fun, H.-K. (2006). Acta Cryst. E62, o4004-o4006.
Chantrapromma, S., Jindawong, B. & Fun, H.-K. (2007). Acta Cryst. E63, o2020-o2022.
Chantrapromma, S., Jindawong, B., Fun, H.-K. & Patil, P. S. (2007). Acta Cryst. E63, o2321-o2323.
Chantrapromma, S., Laksana, C., Ruanwas, P. & Fun, H.-K. (2008). Acta Cryst. E64, o574-o575.
Chou, S.-S. P., Sun, D.-J., Huang, J.-Y., Yang, P.-K. & Lin, H.-C. (1996). Tetrahedron, 37, 7279-7282.
Dittrich, Ph., Bartlome, R., Montemezzani, G. & Günter, P. (2003). Appl. Surf. Sci. 220, 88-95.
Drost, K. J., Jen, A. K.-J. & Rao, V. P. (1995). Chemtech, 25, 16-25.
Morley, J. O. (1991). J. Chem. Soc. Faraday Trans. 87, 3009-3013.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds

1-Methyl-2-[(E)-2-(2-thienyl)ethenyl]quinolinium iodide1