2-[(E)-2-(1H-Indol-3-yl)ethen­yl]-1-methyl­pyridinium 4-bromo­benzene­sulfonateThis paper is dedicated to the late Her Royal Highness Princess Galyani Vadhana Krom Luang Naradhiwas Rajanagarindra for her patronage of Science in Thailand.

Chantrapromma, S.; Kobkeatthawin, T.; Fun, H.-K.

doi:10.1107/S1600536809011386

Volume 65
Part 5
Pages o950-o951
May 2009

Received 16 March 2009
Accepted 27 March 2009
Online 2 April 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.033
wR = 0.085
Data-to-parameter ratio = 39.6
Details

2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-bromobenzenesulfonate¹

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

^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, C₁₆H₁₅N₂⁺·C₆H₄BrO₃S^-, the cation exists in the E configuration and is essentially planar with a dihedral angle of 3.10 (5)° between the pyridinium ring and the indole ring system. The [pi] -conjugated planes of the cation and the anion are inclined to each other at a dihedral angle of 64.32 (4)°. In the crystal structure, the cations are stacked in an antiparallel manner along the a axis. The anions are linked into a chain along the a axis. The cations and the anions are linked into a three-dimensional network by N-HO and weak C-HO hydrogen bonds. The crystal structure is further stabilized by C-H [pi] interactions. A [pi] - [pi] interaction between the five-membered heterocyclic ring of the indole system and the pyridinium ring is also observed with a centroid-centroid distance of 3.5855 (7) Å.

Related literature

For bond-length data, see: Allen et al. (1987). 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. (2006, 2007, 2008, 2009); Jindawong et al. (2005). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₁₆H₁₅N₂⁺·C₆H₄BrO₃S^-
M_r = 471.36
Monoclinic, P 2₁ /c
a = 7.5188 (1) Å
b = 13.3659 (2) Å
c = 20.2670 (3) Å
= 98.850 (1)°
V = 2012.49 (5) Å³
Z = 4
Mo K radiation
= 2.17 mm^-1
T = 100 K
0.31 × 0.27 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.548, T_max = 0.706
67716 measured reflections
10581 independent reflections
8073 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.085
S = 1.03
10581 reflections
267 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 1.02 e Å^-3
_min = -0.66 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H1N2O2ⁱ	0.85 (2)	1.91 (2)	2.7593 (14)	175.2 (17)
C1-H1AO3ⁱⁱ	0.93	2.53	3.2067 (16)	130
C7-H7AO1	0.93	2.58	3.3095 (16)	136
C9-H9AO1	0.93	2.58	3.2426 (16)	128
C14-H14AO1ⁱⁱⁱ	0.93	2.56	3.2987 (16)	137
C16-H16CO1ⁱⁱⁱ	0.96	2.36	3.2739 (17)	158
C19-H19AO3^iv	0.93	2.51	3.2052 (16)	131
C21-H21AO2^v	0.93	2.28	3.1310 (15)	152
C4-H4ACg3	0.93	2.82	3.5579 (13)	137
C16-H16ACg3^vi	0.96	2.69	3.5731 (13)	154
C16-H16BCg1^vii	0.96	2.74	3.4836 (14)	135
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+2, -y+2, -z+1; (iv) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) x-1, y, z; (vi) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (vii) -x+1, -y+2, -z+1. Cg1 and Cg3 are the centroids of the N2/C8-C10/C15 and C10-C15 rings, respectively.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2401 ).

Acknowledgements

The authors thank Prince of Songkla University for financial support through the Crystal Materials Research Unit. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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