(IUCr) (E)-2-[4-(Dimethylamino)styryl]-1-methylquinolinium 4-methoxybenzenesulfonate monohydrate1

Volume 64
Part 3
Pages o642-o643
March 2008

Received 14 February 2008
Accepted 24 February 2008
Online 29 February 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.053
wR = 0.140
Data-to-parameter ratio = 19.9
Details

(E)-2-[4-(Dimethylamino)styryl]-1-methylquinolinium 4-methoxybenzenesulfonate monohydrate¹

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

^aDepartment 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, C₂₀H₂₁N₂⁺·C₇H₇O₄S^-·H₂O, the cation is nearly planar and exists in the E configuration. The cations and anions form individual chains along the b axis and are interconnected by weak C-HO interactions. The 4-methoxybenzensulfonate anions are linked to water molecules through O-HO hydrogen bonds, forming a three-dimensional network. The crystal structure is further stabilized by a C-H [pi] interaction involving the methoxyphenyl ring. The sulfonate anion is also involved in a weak intramolecular C-HO interaction which generates an S(5) ring motif.

Related literature

For bond lengths and angles, see: Allen (2002); Allen et al. (1987). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For background to NLO materials research, see: Chia et al., (1995); Otero et al., (2002). For related structures, see for example: Chantrapromma et al. (2006, 2007, 2007a,b); Jindawong et al. (2005); Dittrich et al. (2003); Nogi et al. (2000); Sato et al. (1999).

Experimental

Crystal data

C₂₀H₂₁N₂⁺·C₇H₇O₄S^-·H₂O
M_r = 494.60
Monoclinic, P 2₁ /c
a = 14.6064 (5) Å
b = 10.4253 (4) Å
c = 19.5025 (6) Å
= 126.737 (2)°
V = 2379.94 (16) Å³
Z = 4
Mo K radiation
= 0.18 mm^-1
T = 100.0 (1) K
0.58 × 0.27 × 0.19 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.904, T_max = 0.967
33983 measured reflections
6953 independent reflections
5445 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.139
S = 1.06
6953 reflections
350 parameters
H-atom parameters constrained
_max = 0.74 e Å^-3
_min = -0.42 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1W-H1WO2ⁱ	0.84	2.04	2.875 (3)	169
O1W-H2WO4ⁱⁱ	0.85	2.10	2.926 (2)	161
C7-H7AO3ⁱⁱⁱ	0.93	2.49	3.015 (3)	116
C8-H8AO3ⁱⁱⁱ	0.93	2.57	3.049 (3)	113
C20-H20AO4^iv	0.96	2.46	3.325 (2)	151
C23-H23AO1W^v	0.93	2.44	3.365 (2)	176
C26-H26AO4	0.93	2.56	2.921 (2)	104
C27-H27AO1W^vi	0.96	2.58	3.160 (3)	119
C27-H27AO1^vii	0.96	2.55	3.282 (2)	133
C16-H16ACg1^iv	0.93	2.81	3.6513 (19)	151
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) -x+1, -y+1, -z+1; (v) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (vi) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vii) -x+2, -y-1, -z+2. Cg1 is the centroid of the C21-C26 methoxyphenyl ring.

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: SJ2466 ).

Acknowledgements

The authors thank Prince of Songkla University for financial support. The authors also thank the Malaysian Government and Universiti Sains Malaysia for Scientific Advancement Grant Allocation (SAGA) No. 304/PFIZIK/653003/A118.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. 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. & Patil, P. S. (2007a). Anal. Sci. 23, x81-x82.
Chantrapromma, S., Jindawong, B., Fun, H.-K. & Patil, P. S. (2007b). Acta Cryst. E63, o2124-o2126.
Chantrapromma, S., Jindawong, B., Fun, H.-K., Patil, P. S. & Karalai, C. (2006). Acta Cryst. E62, o1802-o1804.
Chantrapromma, S., Jindawong, B., Fun, H.-K., Patil, P. S. & Karalai, C. (2007). Anal. Sci. 23, x27-x28.
Chia, W.-L., Chen, C.-N. & Sheu, H.-J. (1995). Mater. Res. Bull. 30, 1421-1430.
Dittrich, Ph., Bartlome, R., Montemezzani, G. & Günter, P. (2003). Appl. Surf. Sci. 220, 88-95.
Jindawong, B., Chantrapromma, S., Fun, H.-K. & Karalai, C. (2005). Acta Cryst. E61, o3237-o3239.
Nogi, K., Anwar, U., Tsuji, K., Duan, X.-M., Okada, S., Oikawa, H., Matsuda, H. & Nakanishi, H. (2000). Nonlinear Optics, 24, 35-40.
Otero, M., Herranz, M. A., Seoane, C., Martín, N., Garín, J., Orduna, J., Alcalá, R. & Villacampa, B. (2002). Tetrahedron, 58, 7463-7475.
Sato, N., Rikukawa, M., Sanui, K. & Ogata, N. (1999). Synth. Met. 101, 132-133.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds

(E)-2-[4-(Dimethylamino)styryl]-1-methylquinolinium 4-methoxybenzenesulfonate monohydrate1