1,1′-(Butane-1,4-di­yl)dipyridinium dibromide dihydrate

Wu, M.-Q.; Xiao, X.; Zhang, Y.-Q.; Xue, S.-F.; Zhu, Q.-J.

doi:10.1107/S1600536808000913

Volume 64
Part 2
Page o467
February 2008

Received 17 December 2007
Accepted 10 January 2008
Online 18 January 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.030
wR = 0.074
Data-to-parameter ratio = 18.7
Details

1,1'-(Butane-1,4-diyl)dipyridinium dibromide dihydrate

Ming-Qiang Wu,^a Xin Xiao,^a Yun-Qian Zhang,^a ^* Sai-Feng Xue ^a and Qian-Jiang Zhu ^b

^aKey Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, People's Republic of China, and ^bInstitute of Applied Chemistry, Guizhou University, Guiyang 550025, People's Republic of China
Correspondence e-mail: sci.yqzhang@gzu.edu.cn

The organic cation in the title compound, C₁₄H₁₈N₂²⁺·2Br^-·2H₂O, is situated on an inversion centre. The cations, anions and water molecules are linked via O-HBr, C-HBr and C-HO hydrogen bonds, and [pi] - [pi] stacking interactions between adjacent pyridine rings, with a centroid-centroid separation of 3.8518 (17) Å.

Related literature

For general background, see: Day et al. (2000, 2002); Freeman et al. (1981); Kim et al. (2000).

Experimental

Crystal data

C₁₄H₁₈N₂²⁺·2Br^-·2H₂O
M_r = 410.14
Monoclinic, P 2₁ /n
a = 11.0068 (13) Å
b = 7.1484 (8) Å
c = 12.0607 (13) Å
= 111.602 (7)°
V = 882.30 (18) Å³
Z = 2
Mo K radiation
= 4.60 mm^-1
T = 293 (2) K
0.21 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.393, T_max = 0.478
7189 measured reflections
1723 independent reflections
1483 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.030
wR(F²) = 0.074
S = 1.06
1723 reflections
92 parameters
3 restraints
H-atom parameters constrained
_max = 0.48 e Å^-3
_min = -0.45 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1W-H1WABr1	0.85	2.48	3.323 (2)	172
O1W-H1WBBr1ⁱ	0.85	2.53	3.375 (2)	175
C2-H2Br1ⁱⁱ	0.93	2.86	3.664 (3)	145
C5-H5O1Wⁱⁱⁱ	0.93	2.55	3.376 (3)	148
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x, y, z-1; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2085 ).

Acknowledgements

We acknowledge the support of the National Natural Science Foundation of China (No. 20662003) and the Foundation of the Governor of Guizhou Province, China.

References

Bruker (2005). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Day, A. I., Arnold, A. P. & Blanch, R. J. (2000). Patent No. WO/2000/068232.
Day, A. I., Blanch, R. J., Arnold, A. P., Lorenzo, S., Lewis, G. R. & Dance, I. (2002). Angew. Chem. Int. Ed. 41, 275-277.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Freeman, W. A., Mock, W. L. & Shih, N. Y. (1981). J. Am. Chem. Soc. 103, 7367-7368.
Kim, J., Jung, I.-S., Kim, S.-Y., Lee, E., Kang, J.-K., Sakamoto, S., Yamaguchi, K. & Kim, K. (2000). J. Am. Chem. Soc. 122, 540-541.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds