(1H-Benzimidazol-2-yl)methanaminium perchlorate–18-crown-6–water (1/1/1)

Sun, S.-W.

doi:10.1107/S1600536811050665

Volume 68
Part 1
Page o25
January 2012

Received 3 October 2011
Accepted 25 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R = 0.076
wR = 0.236
Data-to-parameter ratio = 17.4
Details

(1H-Benzimidazol-2-yl)methanaminium perchlorate-18-crown-6-water (1/1/1)

Su-Wen Sun ^a ^*

^aOrdered Matter Science Research Cente, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
Correspondence e-mail: sunsuwen_5127@163.com

The crystal structure of the title compound C₈H₁₀N₃⁺·ClO₄^-·C₁₂H₂₄O₆·H₂O, consists of an organic (1H-benzimidazol-2-yl)methanaminium cation, an inorganic ClO₄^- anion, one 18-crown-6 molecule and one water molecule. In the crystal, the cations and 18-crown-6 molecules are linked by N-HO hydrogen bonds. The crystal packing is stabilized by intermolecular O-HO, O-HN and O-HCl hydrogen bonds between anions and the water molecules. One 18-crown-6 C atom and a perchlorate O atom are disordered; both have an occupancy factor ratio of 0.60 (2) and 0.40 (2).

Related literature

The title compound was studied during efforts to obtain potential ferroelectric phase-transition materials. For general background to ferroelectric metal-organic frameworks, see: Fu et al. (2009); Ye et al. (2006); Zhang et al. (2008, 2010).

Experimental

Crystal data

C₈H₁₀N₃⁺·ClO₄^-·C₁₂H₂₄O₆·H₂O
M_r = 529.97
Monoclinic, P 2₁ /n
a = 11.703 (2) Å
b = 18.623 (4) Å
c = 12.477 (3) Å
= 106.06 (3)°
V = 2613.2 (9) Å³
Z = 4
Mo K radiation
= 0.21 mm^-1
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.161, T_max = 0.183
26941 measured reflections
5984 independent reflections
2947 reflections with I > 2(I)
R_int = 0.097

Refinement

R[F² > 2(F²)] = 0.076
wR(F²) = 0.236
S = 1.04
5984 reflections
343 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.49 e Å^-3
_min = -0.48 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2CO10	0.90	2.26	3.032 (6)	143
N2-H2CO9	0.90	2.45	3.318 (7)	162
N3-H3AO1	0.90	2.10	2.850 (4)	141
N3-H3AO2	0.90	2.31	2.940 (4)	127
N3-H3BO3	0.90	2.06	2.831 (4)	143
N3-H3BO4	0.90	2.24	2.965 (4)	137
N3-H3CO5	0.90	2.12	2.934 (4)	151
N3-H3CO6	0.90	2.39	2.964 (4)	122
O1W-H1WAN1	0.90 (7)	2.01 (7)	2.873 (5)	161 (6)
O1W-H1WBO7ⁱ	0.78 (6)	2.50 (6)	3.202 (6)	150 (6)
O1W-H1WBCl1ⁱ	0.78 (6)	2.98 (6)	3.758 (5)	173 (6)
Symmetry code: (i) -x, -y+2, -z+1.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2375 ).

Acknowledgements

The author are grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

References

Fu, D. W., Ge, J. Z., Dai, J., Ye, H. Y. & Qu, Z. R. (2009). Inorg. Chem. Commun. 12, 994-997.
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