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

Ha, K.

doi:10.1107/S1600536811053578

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 (C-C) = 0.003 Å
R = 0.051
wR = 0.140
Data-to-parameter ratio = 16.6
Details

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

Kwang Ha ^a ^*

^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-HO hydrogen bonds, forming chains along the b axis. The acridinium cations are linked to the anionic chains by strong N-HO 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-HO hydrogen bonds further stabilize the crystal structure.

Related literature

For related crystal structures of acridinium compounds with carboxylate, see: Shaameri et al. (2001); Derikvand et al. (2009); Attar Gharamaleki et al. (2010).

Experimental

Crystal data

C₁₃H₁₀N⁺·C₇H₄NO₄^-
M_r = 346.33
Monoclinic, C 2/c
a = 16.6817 (8) Å
b = 8.2872 (4) Å
c = 23.7289 (12) Å
= 105.582 (1)°
V = 3159.8 (3) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.884, T_max = 1.000
11354 measured reflections
3894 independent reflections
2198 reflections with I > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.140
S = 1.06
3894 reflections
235 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_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-HA	D-H	HA	DA	D-HA
N1-H1NO3ⁱ	0.92	1.70	2.602 (2)	165
O1-H1OO4ⁱⁱ	0.84	1.73	2.535 (2)	160
C7-H7O1ⁱⁱⁱ	0.95	2.37	3.132 (2)	137
C10-H10O3^iv	0.95	2.49	3.435 (3)	171
C12-H12O4ⁱ	0.95	2.56	3.466 (3)	160
C17-H17O2^v	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); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); 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.
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Derikvand, Z., Aghabozorg, H. & Attar Gharamaleki, J. (2009). Acta Cryst. E65, o1173.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Shaameri, Z., Shan, N. & Jones, W. (2001). Acta Cryst. E57, o945-o946.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds