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Volume 69 
Part 11 
Page o1645  
November 2013  

Received 22 September 2013
Accepted 9 October 2013
Online 16 October 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.136
Data-to-parameter ratio = 13.6
Details
Open access

5,6-Dimethyl-1H-benzimidazol-3-ium nitrate

aKey Laboratory of Advanced Materials, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
Correspondence e-mail: qdplastics@163.com

The title salt, C9H11N2+·NO3-, features a planar cation (r.m.s. for 11 non-H atoms = 0.016 Å). In the crystal, N-H...O hydrogen bonds link nitrate and benzimidazole ions into a three-dimensional network.

Related literature

For background to benzimidazole, see: Roderick et al. (1972[Roderick, W. R., Nordeen, C. W., Von Esch, A. M. & Appell, R. N. J. (1972). J. Med. Chem. 15, 655-658.]). For related crystal structures, see: Lee & Scheidt (1986[Lee, Y. J. & Scheidt, W. R. (1986). Acta Cryst. C42, 1652-1654.]), Liu (2012[Liu, H.-L. (2012). Z. Kristallogr. New Cryst. Struct. 227, 339-340.]), Cui et al. (2009[Cui, Y., Gao, Q., Zhang, C.-Y. & Xie, Y.-B. (2009). Acta Cryst. E65, o1335.]).

[Scheme 1]

Experimental

Crystal data
  • C9H11N2+·NO3-

  • Mr = 209.21

  • Monoclinic, P 21 /c

  • a = 6.938 (4) Å

  • b = 14.694 (8) Å

  • c = 10.379 (6) Å

  • [beta] = 108.598 (9)°

  • V = 1002.8 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 K

  • 0.29 × 0.27 × 0.22 mm

Data collection
  • Rigaku R-AXIS Spider diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.970, Tmax = 0.977

  • 5401 measured reflections

  • 1973 independent reflections

  • 1617 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.136

  • S = 1.05

  • 1973 reflections

  • 145 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O1i 0.96 (3) 2.31 (3) 3.043 (3) 133.0 (15)
N2-H2...O3i 0.96 (3) 1.86 (3) 2.797 (3) 165 (2)
N1-H1...O1ii 0.90 (3) 2.60 (2) 3.191 (3) 123.8 (17)
N1-H1...O2ii 0.90 (3) 1.89 (2) 2.797 (3) 178 (2)
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x-1, y, z-1.

Data collection: RAPID-AUTO (Rigaku, 2004[Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: HG5349 ).


Acknowledgements

This work was supported by the NSF of Shandong Province (No. 2009ZRA02071) and the Scientific Development Plan of Universities in Shandong Province (No. J09LB53)

References

Cui, Y., Gao, Q., Zhang, C.-Y. & Xie, Y.-B. (2009). Acta Cryst. E65, o1335.  [CSD] [CrossRef] [IUCr Journals]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Lee, Y. J. & Scheidt, W. R. (1986). Acta Cryst. C42, 1652-1654.  [CSD] [CrossRef] [IUCr Journals]
Liu, H.-L. (2012). Z. Kristallogr. New Cryst. Struct. 227, 339-340.  [CSD] [CrossRef] [ChemPort]
Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Roderick, W. R., Nordeen, C. W., Von Esch, A. M. & Appell, R. N. J. (1972). J. Med. Chem. 15, 655-658.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1645  [ doi:10.1107/S1600536813027578 ]

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