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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 [sigma](C-C) = 0.007 Å
Disorder in main residue
R = 0.076
wR = 0.236
Data-to-parameter ratio = 17.4
Details
Open access

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

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-H...O hydrogen bonds. The crystal packing is stabilized by intermolecular O-H...O, O-H...N and O-H...Cl 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[Fu, D. W., Ge, J. Z., Dai, J., Ye, H. Y. & Qu, Z. R. (2009). Inorg. Chem. Commun. 12, 994-997.]); Ye et al. (2006[Ye, Q., Song, Y. M., Wang, G. X., Chen, K. & Fu, D. W. (2006). J. Am. Chem. Soc. 128, 6554-6555.]); Zhang et al. (2008[Zhang, W., Xiong, R. G. & Huang, S. P. D. (2008). J. Am. Chem. Soc. 130, 10468-10469.], 2010[Zhang, W., Ye, H. Y., Cai, H. L., Ge, J. Z. & Xiong, R. G. (2010). J. Am. Chem. Soc. 132, 7300-7302.]).

[Scheme 1]

Experimental

Crystal data
  • C8H10N3+·ClO4-·C12H24O6·H2O

  • Mr = 529.97

  • Monoclinic, P 21 /n

  • a = 11.703 (2) Å

  • b = 18.623 (4) Å

  • c = 12.477 (3) Å

  • [beta] = 106.06 (3)°

  • V = 2613.2 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.161, Tmax = 0.183

  • 26941 measured reflections

  • 5984 independent reflections

  • 2947 reflections with I > 2[sigma](I)

  • Rint = 0.097

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.48 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2C...O10 0.90 2.26 3.032 (6) 143
N2-H2C...O9 0.90 2.45 3.318 (7) 162
N3-H3A...O1 0.90 2.10 2.850 (4) 141
N3-H3A...O2 0.90 2.31 2.940 (4) 127
N3-H3B...O3 0.90 2.06 2.831 (4) 143
N3-H3B...O4 0.90 2.24 2.965 (4) 137
N3-H3C...O5 0.90 2.12 2.934 (4) 151
N3-H3C...O6 0.90 2.39 2.964 (4) 122
O1W-H1WA...N1 0.90 (7) 2.01 (7) 2.873 (5) 161 (6)
O1W-H1WB...O7i 0.78 (6) 2.50 (6) 3.202 (6) 150 (6)
O1W-H1WB...Cl1i 0.78 (6) 2.98 (6) 3.758 (5) 173 (6)
Symmetry code: (i) -x, -y+2, -z+1.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [ISI] [CSD] [CrossRef] [ChemPort]
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Ye, Q., Song, Y. M., Wang, G. X., Chen, K. & Fu, D. W. (2006). J. Am. Chem. Soc. 128, 6554-6555.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Zhang, W., Xiong, R. G. & Huang, S. P. D. (2008). J. Am. Chem. Soc. 130, 10468-10469.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Zhang, W., Ye, H. Y., Cai, H. L., Ge, J. Z. & Xiong, R. G. (2010). J. Am. Chem. Soc. 132, 7300-7302.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o25  [ doi:10.1107/S1600536811050665 ]

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