Guanidinium chloride–18-crown-6 (2/1)

Wei, B.

doi:10.1107/S1600536812016959

Volume 68
Part 5
Page o1490
May 2012

Received 29 March 2012
Accepted 18 April 2012
Online 21 April 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.008 Å
R = 0.074
wR = 0.220
Data-to-parameter ratio = 21.5
Details

Guanidinium chloride-18-crown-6 (2/1)

Bin Wei ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 211189, People's Republic of China
Correspondence e-mail: seuwei@126.com

In the crystal of the title compound, 2CH₆N₃⁺·2Cl^-·C₁₂H₂₄O₆, the 18-crown-6 molecule is located across an inversion center. The guanidinium cation links to the 18-crown-6 molecule and chloride anion via N-HO and N-HCl hydrogen bonds.

Related literature

For applications of crown ethers, see: Clark et al. 1998). For ferroelectric metal-organic 18-crown-6 clathrates, see: Fu et al. (2009, 2011); Ye et al. (2006); Zhang et al. (2008, 2010).

Experimental

Crystal data

2CH₆N₃⁺·2Cl^-·C₁₂H₂₂O₆
M_r = 453.37
Monoclinic, P 2₁ /n
a = 8.9685 (18) Å
b = 9.7305 (19) Å
c = 13.995 (3) Å
= 102.14 (3)°
V = 1194.0 (4) Å³
Z = 2
Mo K radiation
= 0.31 mm^-1
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.939, T_max = 0.940
12074 measured reflections
2732 independent reflections
1154 reflections with I > 2(I)
R_int = 0.130
2 standard reflections every 150 reflections intensity decay: ?

Refinement

R[F² > 2(F²)] = 0.074
wR(F²) = 0.220
S = 1.01
2732 reflections
127 parameters
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1	0.86	2.19	2.976 (5)	152
N1-H1BCl1	0.86	2.49	3.294 (4)	155
N2-H2AO1	0.86	2.36	3.102 (5)	145
N3-H3ACl1ⁱ	0.86	2.42	3.228 (4)	158
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5505 ).

Acknowledgements

The author is grateful to the starter fund of Southeast University for the purchase of the diffractometer.

References

Clark, D. L., Keogh, D. W. & Palmer, C. L. (1998). Angew. Chem. Int. Ed. 37, 164-169.
Fu, D.-W., Ge, J.-Z., Dai, J., Ye, H.-Y. & Qu, Z.-R. (2009). Inorg. Chem. Commun. 12, 994-997.
Fu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z. & Xiong, R.-G. (2011). J. Am. Chem. Soc. 133, 12780-12786.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Ye, Q., Song, Y.-M., Wang, G.-X., Chen, K. & Fu, D.-W. (2006). J. Am. Chem. Soc. 128, 6554-6555.
Zhang, W., Xiong, R.-G. & Huang, S.-P. D. (2008). J. Am. Chem. Soc. 130, 10468-10469.
Zhang, W., Ye, H.-Y., Cai, H.-L., Ge, J.-Z. & Xiong, R.-G. (2010). J. Am. Chem. Soc. 132, 7300-7302.

organic compounds