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Volume 69 
Part 11 
Page o1606  
November 2013  

Received 30 September 2013
Accepted 30 September 2013
Online 2 October 2013

Key indicators
Single-crystal X-ray study
T = 98 K
Mean [sigma](C-C) = 0.002 Å
R = 0.050
wR = 0.124
Data-to-parameter ratio = 14.4
Details
Open access

4-[2-(Pyridin-1-ium-4-yl)eth­yl]pyridin-1-ium bis­(2,6-di­nitro­benzoate)

aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

The asymmetric unit of the title salt, C12H14N22+·2C7H3N2O6-, comprises half a 4-[2-(pyridin-1-ium-4-yl)eth­yl]pyridin-1-ium dication, being disposed about a centre of inversion, and a 2,6-di­nitro­benzoate anion, in a general position. In the anion, the carboxyl­ate group is inclined to the benzene ring [dihedral angle = 85.45 (9)°], whereas near-coplanar and twisted arrangements are found for the nitro groups [O-N-C-C torsion angles = 179.80 (14) and 20.2 (2)°]. In the crystal, three-component aggregates sustained by charge-assisted N+-H...O- hydrogen bonds are found and these are consolidated into a three-dimensional architecture by C-H...O and [pi]-[pi] [inter-centroid distances = 3.6796 (14) and 3.7064 (14) Å] inter­actions.

Related literature

For the 2:1 salts of 2,6-di­nitro­benzoate with isomeric n-({[(pyri­din-1-ium-n-ylmeth­yl)carbamo­yl]formamido}­meth­yl)pyridin-1-ium, n = 2, 3 and 4, and for the structure of 2,6-di­nitro­benzoic acid, see: Arman et al. (2013[Arman, H. D., Miller, T. & Tiekink, E. R. T. (2013). Z. Kristallogr. Cryst. Mat. 228, 295-303.]).

[Scheme 1]

Experimental

Crystal data
  • 0.5C12H14N22+·C7H3N2O6-

  • Mr = 304.24

  • Triclinic, [P \overline 1]

  • a = 6.6916 (12) Å

  • b = 8.3690 (17) Å

  • c = 12.358 (3) Å

  • [alpha] = 88.809 (12)°

  • [beta] = 76.322 (8)°

  • [gamma] = 72.193 (9)°

  • V = 639.2 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 98 K

  • 0.36 × 0.12 × 0.07 mm

Data collection
  • Rigaku AFC12/SATURN724 diffractometer

  • 4421 measured reflections

  • 2915 independent reflections

  • 2538 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.124

  • S = 1.07

  • 2915 reflections

  • 202 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3n...O1 0.90 (1) 1.64 (2) 2.5240 (19) 166 (2)
C8-H8...O6i 0.95 2.50 3.436 (2) 169
C11-H11...O2ii 0.95 2.52 3.377 (2) 150
C12-H12...O4iii 0.95 2.46 3.118 (2) 126
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y+1, z; (iii) -x+1, -y+1, -z.

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005[Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and 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: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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: HG5351 ).


Acknowledgements

We gratefully thank the Ministry of Higher Education (Malaysia) and the University of Malaya (UM) for funding structural studies through the High-Impact Research scheme (UM·C/HIR-MOHE/SC/03).

References

Arman, H. D., Miller, T. & Tiekink, E. R. T. (2013). Z. Kristallogr. Cryst. Mat. 228, 295-303.  [CSD] [CrossRef] [ChemPort]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1606  [ doi:10.1107/S1600536813026810 ]

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