1,1′-Dimethyl-1,1′-(butane-1,4-di­yl)dipyrrolidinium dibromide methanol disolvate

Yang, Y.-L.; Wang, W.-J.; Li, W.-H.; Fan, R.-Q.

doi:10.1107/S1600536808000172

Volume 64
Part 2
Page o417
February 2008

Received 18 December 2007
Accepted 3 January 2008
Online 11 January 2008

Key indicators
Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.003 Å
R = 0.028
wR = 0.067
Data-to-parameter ratio = 20.2
Details

1,1'-Dimethyl-1,1'-(butane-1,4-diyl)dipyrrolidinium dibromide methanol disolvate

Yu-Lin Yang,^a ^* Wen-Jiu Wang,^a Wen-Hui Li ^b and Rui-Qing Fan ^a

^aDepartment of Applied Chemistry, Harbin Institute of Technology, Harbin 150001, People's Republic of China, and ^bCollege of Materials Science and Engineering, Harbin University of Science & Technology, Harbin 150040, People's Republic of China
Correspondence e-mail: yangyulin2000@163.com

In the title compound, C₁₄H₃₀N₂²⁺·2Br^-·2CH₃OH, two terminal C atoms of the butane chain are connected to two N atoms of the 1-methylpyrollidines, forming a linear diquaternary ammonium cation. The cation lies across a centre of inversion located between the two central C atoms of the butane chain. The asymmetric unit therefore comprises one half-cation, a bromide anion and a methanol solvent molecule. In the crystal structure, the bromide anions are linked to the methanol solvent molecules by O-HBr hydrogen bonds.

Related literature

For information on the use of organic amines in zeolite synthesis, see: Gramm et al. (2006); Hong et al. (2007). For a previous synthesis of the title compound, see: Hong et al. (2004).

Experimental

Crystal data

C₁₄H₃₀N₂²⁺·2Br^-·2CH₄O
M_r = 450.30
Monoclinic, P 2₁ /n
a = 6.4919 (7) Å
b = 12.4861 (13) Å
c = 12.9683 (13) Å
= 90.748 (2)°
V = 1051.10 (19) Å³
Z = 2
Mo K radiation
= 3.87 mm^-1
T = 193 (2) K
0.30 × 0.25 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.390, T_max = 0.457 (expected range = 0.337-0.396)
5618 measured reflections
2013 independent reflections
1681 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.067
S = 1.09
2013 reflections
102 parameters
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1Br1	0.82	2.43	3.2453 (18)	172

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2458 ).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (20671025 and 20771030), the Development Program for Outstanding Young Teachers in Harbin Institute of Technology (HITQNJS.2006.029), the Science Innovation Special Foundation of Harbin City in China (2005AFXXJ034), the Young Foundation of Heilongjiang Province in China (QC06C029), and the Heilongjiang Natural Science Foundation (B200603).

References

Bruker (2000). SMART (Version 5.625) and SAINT (Version 6.01) and SADABS (Version?). Bruker AXS Inc., Madison, Wisconsin, USA.
Gramm, F., Baerlocher, C., McCusker, L. B., Warrender, S. J., Wright, P. A., Han, B., Hong, S. B., Liu, Z., Ohsuna, T. & Terasaki, O. (2006). Nature (London), 444, 79-81.
Hong, S. B., Lear, E. G., Wright, P. A., Zhou, W. Z., Cox, P. A., Shin, C. H., Park, J. H. & Nam, I. S. (2004). J. Am. Chem. Soc. 126, 5817-5826.
Hong, S. B., Min, H. K., Shin, C. H., Cox, P. A., Warrender, S. J. & Wright, P. A. (2007). J. Am. Chem. Soc. 129, 10870-10885.
Sheldrick, G. M. (1997). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds