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Volume 69 
Part 9 
Page o1400  
September 2013  

Received 19 July 2013
Accepted 1 August 2013
Online 10 August 2013

Key indicators
Single-crystal X-ray study
T = 180 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.121
Data-to-parameter ratio = 24.1
Details
Open access

Bis(triethylammonium) chloranilate

aDepartment of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, Japan
Correspondence e-mail: ishidah@cc.okayama-u.ac.jp

In the crystal structure of the title compound [systematic name: bis(triethylammonium) 2,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,4-diolate], 2C6H16N+·C6Cl2O42-, the chloranilate anion lies on an inversion center. The triethylammonium cations are linked on both sides of the anion via bifurcated N-H...(O,O) and weak C-H...O hydrogen bonds to give a centrosymmetric 2:1 aggregate. The 2:1 aggregates are further linked by C-H...O hydrogen bonds into a zigzag chain running along [01-1].

Related literature

For related structures, see: Dayananda et al. (2012[Dayananda, A. S., Butcher, R. J., Akkurt, M., Yathirajan, H. S. & Narayana, B. (2012). Acta Cryst. E68, o1037-o1038.]); Gotoh et al. (2009[Gotoh, K., Nagoshi, H. & Ishida, H. (2009). Acta Cryst. C65, o273-o277.], 2010[Gotoh, K., Maruyama, S. & Ishida, H. (2010). Acta Cryst. E66, o3255.]); Yang (2007[Yang, D.-J. (2007). Acta Cryst. E63, o2600.]).

[Scheme 1]

Experimental

Crystal data
  • 2C6H16N+·C6Cl2O42-

  • Mr = 411.37

  • Triclinic, [P \overline 1]

  • a = 7.7347 (5) Å

  • b = 8.5151 (8) Å

  • c = 9.3913 (7) Å

  • [alpha] = 64.388 (4)°

  • [beta] = 68.435 (3)°

  • [gamma] = 79.060 (5)°

  • V = 518.36 (7) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.34 mm-1

  • T = 180 K

  • 0.65 × 0.31 × 0.21 mm

Data collection
  • Rigaku R-AXIS RAPID II diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.858, Tmax = 0.932

  • 10264 measured reflections

  • 3012 independent reflections

  • 2561 reflections with I > 2[sigma](I)

  • Rint = 0.078

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.121

  • S = 1.06

  • 3012 reflections

  • 125 parameters

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

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1 0.867 (18) 1.942 (18) 2.7601 (15) 156.9 (15)
N1-H1...O2i 0.867 (18) 2.339 (17) 2.9377 (14) 126.4 (14)
C5-H5C...O1 0.98 2.57 3.2911 (19) 131
C9-H9B...O1ii 0.98 2.55 3.5315 (17) 177
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x+1, -y+1, -z+1.

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004[Rigaku/MSC (2004). PROCESS-AUTO and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). PROCESS-AUTO and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, 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: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). PROCESS-AUTO and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) 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: LH5635 ).


Acknowledgements

This work was supported by a Grant-in-Aid for Scientific Research (C) (No. 22550013) from the Japan Society for the Promotion of Science.

References

Dayananda, A. S., Butcher, R. J., Akkurt, M., Yathirajan, H. S. & Narayana, B. (2012). Acta Cryst. E68, o1037-o1038.  [CSD] [CrossRef] [ChemPort] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gotoh, K., Maruyama, S. & Ishida, H. (2010). Acta Cryst. E66, o3255.  [CSD] [CrossRef] [details]
Gotoh, K., Nagoshi, H. & Ishida, H. (2009). Acta Cryst. C65, o273-o277.  [CSD] [CrossRef] [ChemPort] [details]
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2004). PROCESS-AUTO and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Yang, D.-J. (2007). Acta Cryst. E63, o2600.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o1400  [ doi:10.1107/S1600536813021405 ]

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