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Volume 68 
Part 1 
Page o196  
January 2012  

Received 10 December 2011
Accepted 12 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.051
wR = 0.140
Data-to-parameter ratio = 16.6
Details
Open access

Acridin-10-ium 6-carboxypyridine-2-carboxylate

aSchool of Applied Chemical Engineering, The Research Institute of Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea
Correspondence e-mail: hakwang@chonnam.ac.kr

The title compound, C13H10N+·C7H4NO4-, consists of a protonated acridinium cation and a 6-carboxypyridine-2-carboxylate monoanion. The carboxylate group of the anion appears to be delocalized on the basis of the nearly equivalent C-O bond lengths. In the crystal, the anions are connected by strong O-H...O hydrogen bonds, forming chains along the b axis. The acridinium cations are linked to the anionic chains by strong N-H...O hydrogen bonds between the carboxylate group of the anion and the N-H group of the cation. Along the b axis, successive chains stack in opposite directions. Weak intermolecular C-H...O hydrogen bonds further stabilize the crystal structure.

Related literature

For related crystal structures of acridinium compounds with carboxylate, see: Shaameri et al. (2001[Shaameri, Z., Shan, N. & Jones, W. (2001). Acta Cryst. E57, o945-o946.]); Derikvand et al. (2009[Derikvand, Z., Aghabozorg, H. & Attar Gharamaleki, J. (2009). Acta Cryst. E65, o1173.]); Attar Gharamaleki et al. (2010[Attar Gharamaleki, J., Derikvand, Z. & Stoeckli-Evans, H. (2010). Acta Cryst. E66, o2231.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10N+·C7H4NO4-

  • Mr = 346.33

  • Monoclinic, C 2/c

  • a = 16.6817 (8) Å

  • b = 8.2872 (4) Å

  • c = 23.7289 (12) Å

  • [beta] = 105.582 (1)°

  • V = 3159.8 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 200 K

  • 0.29 × 0.18 × 0.17 mm

Data collection
  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.884, Tmax = 1.000

  • 11354 measured reflections

  • 3894 independent reflections

  • 2198 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.140

  • S = 1.06

  • 3894 reflections

  • 235 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Selected geometric parameters (Å, °)

O1-C19 1.314 (2)
O2-C19 1.206 (2)
O3-C20 1.255 (2)
O4-C20 1.246 (3)
O2-C19-O1 124.6 (2)
O4-C20-O3 125.0 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O3i 0.92 1.70 2.602 (2) 165
O1-H1O...O4ii 0.84 1.73 2.535 (2) 160
C7-H7...O1iii 0.95 2.37 3.132 (2) 137
C10-H10...O3iv 0.95 2.49 3.435 (3) 171
C12-H12...O4i 0.95 2.56 3.466 (3) 160
C17-H17...O2v 0.95 2.44 3.387 (3) 171
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x, y+1, z; (iii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [x, -y+1, z-{\script{1\over 2}}]; (v) x, y-1, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2350 ).


Acknowledgements

This work was supported by the Priority Research Centers Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2010-0029626).

References

Attar Gharamaleki, J., Derikvand, Z. & Stoeckli-Evans, H. (2010). Acta Cryst. E66, o2231.  [CSD] [CrossRef] [details]
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Derikvand, Z., Aghabozorg, H. & Attar Gharamaleki, J. (2009). Acta Cryst. E65, o1173.  [CSD] [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Shaameri, Z., Shan, N. & Jones, W. (2001). Acta Cryst. E57, o945-o946.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o196  [ doi:10.1107/S1600536811053578 ]

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