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Volume 69 
Part 11 
Page o1611  
November 2013  

Received 23 September 2013
Accepted 1 October 2013
Online 5 October 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.054
wR = 0.178
Data-to-parameter ratio = 18.7
Details
Open access

1-(5,5-Di­meth­oxy­pent­yl)-3-methyl­imidazolium-2-carboxyl­ate

aIKFT, KIT-Campus Nord, Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany
Correspondence e-mail: olaf.walter@kit.edu

The title compound, C12H20N2O4, represents one example of a zwitterionic imidazolium salt with a carboxyl­ate group at the 2-position of the imidazolium ring. The dihedral angle between the heterocyclic ring and the carboxyl­ate group is 31.3 (1)°. The side chain linking the N atom of the ring and the methine C atom has a gauche-anti-anti conformation [torsion angles = -60.3 (2), -175.7 (2) and 178.7 (2)°, respectively]. In the crystal, mol­ecules are linked by short C-H...O hydrogen bonds involving the C-H groups in the aromatic ring to generate (001) sheets.

Related literature

For related zwitterionic structures, see: Gurau et al. (2011[Gurau, G., Rodriguez, H., Kelley, S. P., Janiczek, P., Kalb, R. S. & Rogers, R. D. (2011). Angew. Chem. Int. Ed. Engl. 50, 12024-12026.]); Holbrey et al. (2003[Holbrey, J. D., Reichert, W. M., Tkatchenko, I., Bouajila, E., Walter, O., Tommasi, I. & Rogers, R. D. (2003). Chem. Commun. pp. 28-29.]); Smiglak et al. (2007[Smiglak, M., Holbrey, J. D., Griffin, S. T., Reichert, W. M., Swatloski, R. P., Katritzky, A. R., Yang, H., Zhang, D., Kirichenko, K. & Rogers, R. D. (2007). Green Chem. 9, 90-98.]); Reichert et al. (2010[Reichert, W. M., Trulove, P. C. & De Long, H. C. (2010). Acta Cryst. E66, o591.]).

[Scheme 1]

Experimental

Crystal data
  • C12H20N2O4

  • Mr = 256.30

  • Triclinic, [P \overline 1]

  • a = 7.1943 (8) Å

  • b = 7.3259 (8) Å

  • c = 13.2263 (15) Å

  • [alpha] = 85.124 (2)°

  • [beta] = 85.542 (2)°

  • [gamma] = 72.938 (2)°

  • V = 662.98 (13) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 200 K

  • 0.3 × 0.15 × 0.15 mm

Data collection
  • Siemens SMART CCD 1000 diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.940, Tmax = 1.000

  • 8022 measured reflections

  • 3192 independent reflections

  • 1962 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.178

  • S = 1.03

  • 3192 reflections

  • 171 parameters

  • Only H-atom displacement parameters refined

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O2i 0.93 2.30 3.141 (2) 151
C4-H4...O1ii 0.93 2.30 3.127 (2) 148
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SAINT (Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013[Sheldrick, G. M. (2013). SHELXL2013. University of Göttingen, Germany.]); molecular graphics: XPMA (Zsolnai, 1996[Zsolnai, L. (1996). XPMA. University of Heidelberg, Germany.]) and ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7143 ).


Acknowledgements

The author gratefully acknowledges financial support for this work from the Karlsruhe Institute for Technology.

References

Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gurau, G., Rodriguez, H., Kelley, S. P., Janiczek, P., Kalb, R. S. & Rogers, R. D. (2011). Angew. Chem. Int. Ed. Engl. 50, 12024-12026.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Holbrey, J. D., Reichert, W. M., Tkatchenko, I., Bouajila, E., Walter, O., Tommasi, I. & Rogers, R. D. (2003). Chem. Commun. pp. 28-29.  [CSD] [CrossRef]
Reichert, W. M., Trulove, P. C. & De Long, H. C. (2010). Acta Cryst. E66, o591.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2013). SHELXL2013. University of Göttingen, Germany.
Smiglak, M., Holbrey, J. D., Griffin, S. T., Reichert, W. M., Swatloski, R. P., Katritzky, A. R., Yang, H., Zhang, D., Kirichenko, K. & Rogers, R. D. (2007). Green Chem. 9, 90-98.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zsolnai, L. (1996). XPMA. University of Heidelberg, Germany.


Acta Cryst (2013). E69, o1611  [ doi:10.1107/S1600536813027013 ]

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