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Volume 69 
Part 2 
Page o211  
February 2013  

Received 26 November 2012
Accepted 21 December 2012
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.047
wR = 0.083
Data-to-parameter ratio = 12.6
Details
Open access

2-(Carboxymethyl)imidazo[1,2-a]pyridin-1-ium chloride

aDepartment of Chemistry & Materials Engineering, Jiangsu Laboratory of Advanced Functional Materials, Changshu Institute of Technology, Changshu 215500, Jiangsu, People's Republic of China
Correspondence e-mail: ywy21wz@sina.com

In the crystal structure of the title salt, C9H9N2O2+·Cl-, the cations and anions are linked into chains parallel to [021] by O-H...Cl and N-H...Cl hydrogen bonds.

Related literature

For the diversity of structures and the applications of compounds with an imidazole moiety, see: Catalano & Etogo (2007[Catalano, V. J. & Etogo, A. O. (2007). Inorg. Chem. 46, 5608-5615.]); Feng et al. (2012[Feng, X., Wang, Y. F., Shi, Z. Q., Shang, J. J. & Wang, L. Y. (2012). Inorg. Chem. Commun. 22, 131-136.]); Keppler et al. (1987[Keppler, B. K., Wehe, D., Endres, H. & Rupp, W. (1987). Inorg. Chem. 26, 844-846.]); Poul et al. (2007[Poul, N. L., Campion, M., Douziech, B., Rondelez, Y., Clainche, L. L., Reinaud, O. & Mest, Y. L. (2007). J. Am. Chem. Soc. 129, 8801-8810.]); Saha et al. (2012[Saha, D., Das, S., Mardanya, S. & Baitalik, S. (2012). Dalton Trans. 41, 8886-8898.]); Samantaray et al. (2007[Samantaray, M. K., Katiyar, V., Pang, K., Nanavati, H. & Ghosh, P. (2007). J. Organomet. Chem. 692, 1672-1682.]); Takagaki et al. (2012[Takagaki, T., Bando, T. & Sugiyama, H. (2012). J. Am. Chem. Soc. 134, 13074-13081.]).

[Scheme 1]

Experimental

Crystal data
  • C9H9N2O2+·Cl-

  • Mr = 212.63

  • Monoclinic, P 21 /c

  • a = 5.4032 (8) Å

  • b = 14.722 (2) Å

  • c = 12.1055 (18) Å

  • [beta] = 96.182 (4)°

  • V = 957.3 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.37 mm-1

  • T = 293 K

  • 0.25 × 0.15 × 0.12 mm

Data collection
  • Rigaku Mercury diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.913, Tmax = 0.957

  • 7948 measured reflections

  • 1689 independent reflections

  • 1417 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.083

  • S = 1.02

  • 1689 reflections

  • 134 parameters

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...Cl1i 0.82 2.19 2.984 (2) 163
N2-H2A...Cl1ii 0.89 (3) 2.18 (3) 3.074 (2) 175 (3)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

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/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL/PC and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HP2052 ).


Acknowledgements

This work was supported by the Natural Science Fund of Jiangsu Province, China (No. 08KJB150001).

References

Catalano, V. J. & Etogo, A. O. (2007). Inorg. Chem. 46, 5608-5615.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Feng, X., Wang, Y. F., Shi, Z. Q., Shang, J. J. & Wang, L. Y. (2012). Inorg. Chem. Commun. 22, 131-136.  [ISI] [CrossRef] [ChemPort]
Keppler, B. K., Wehe, D., Endres, H. & Rupp, W. (1987). Inorg. Chem. 26, 844-846.  [CrossRef] [ChemPort] [ISI]
Poul, N. L., Campion, M., Douziech, B., Rondelez, Y., Clainche, L. L., Reinaud, O. & Mest, Y. L. (2007). J. Am. Chem. Soc. 129, 8801-8810.  [PubMed]
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Saha, D., Das, S., Mardanya, S. & Baitalik, S. (2012). Dalton Trans. 41, 8886-8898.  [CSD] [CrossRef] [ChemPort] [PubMed]
Samantaray, M. K., Katiyar, V., Pang, K., Nanavati, H. & Ghosh, P. (2007). J. Organomet. Chem. 692, 1672-1682.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Takagaki, T., Bando, T. & Sugiyama, H. (2012). J. Am. Chem. Soc. 134, 13074-13081.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o211  [ doi:10.1107/S1600536812051549 ]

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