(S)-2-(Pyrrolidinium-2-ylmethyl­sulfan­yl)pyridinium dibromide

Zhang, S.; Wang, Y.; Xia, A.; Luo, S.

doi:10.1107/S1600536808008313

Volume 64
Part 6
Page o1142
June 2008

Received 6 March 2008
Accepted 27 March 2008
Online 24 May 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.013 Å
R = 0.037
wR = 0.108
Data-to-parameter ratio = 23.0
Details

(S)-2-(Pyrrolidinium-2-ylmethylsulfanyl)pyridinium dibromide

Shuai Zhang,^a Yifeng Wang,^a Aibao Xia ^a and Shuping Luo ^a ^*

^aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
Correspondence e-mail: shuaizhang867@gmail.com

In the title compound, C₁₀H₁₆N₂S²⁺·2Br^-, the pyrrolidine ring displays an envelope conformation, with the flap C atom lying 0.484 (5) Å out of the plane of the rest of the pyrrolidine ring. The thioether group connects the pyridine ring and the 2-methylpyrrolidine group. Both pyrrolidine NH bonds form hydrogen bonds to the bromide anions. These hydrogen bonds link the cations and anions in a helical chain along the c axis.

Related literature

For related literature, see: Ishii et al. (2004); Xu et al. (2007); Larson (1970).

Experimental

Crystal data

C₁₀H₁₆N₂S²⁺·2Br^-
M_r = 356.12
Trigonal, P 3₂
a = 8.9892 (9) Å
c = 15.4567 (14) Å
V = 1081.66 (18) Å³
Z = 3
Mo K radiation
= 5.76 mm^-1
T = 296 (1) K
0.35 × 0.30 × 0.23 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi,1995) T_min = 0.162, T_max = 0.266
10585 measured reflections
3169 independent reflections
1902 reflections with F² > 2.0(F²)
R_int = 0.061

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.108
S = 1.01
3169 reflections
138 parameters
H-atom parameters constrained
_max = 0.67 e Å^-3
_min = -0.53 e Å^-3
Absolute structure: Flack (1983), 1037 Friedel pairs
Flack parameter: 0.017 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H2Br1	0.86	2.45	3.278 (7)	163
N1-H3Br1ⁱ	0.86	2.43	3.271 (5)	165
Symmetry code: (i) $[-x+y, -x+1, z+{\script{1\over 3}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2087 ).

Acknowledgements

We thank Professor Jian-Ming Gu of Zhejiang University for his help.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Ishii, T., Fujioka, S., Sekiguchi, Y. & Kotsuki, H. (2004). J. Am. Chem. Soc. 126, 9558-9559.
Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291-294. Copenhagen: Munksgaard.
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Xu, D. Q., Luo, S. P., Wang, Y. F. & Xu, Z. Y. (2007). Chem. Commun. pp. 4393-4395.

organic compounds