2-Carboxy­pyridinium hydrogen chloranilate

Gotoh, K.; Nagoshi, H.; Ishida, H.

doi:10.1107/S1600536809006412

Volume 65
Part 3
Page o614
March 2009

Received 20 February 2009
Accepted 21 February 2009
Online 28 February 2009

Key indicators
Single-crystal X-ray study
T = 103 K
Mean (C-C) = 0.004 Å
R = 0.045
wR = 0.144
Data-to-parameter ratio = 17.0
Details

2-Carboxypyridinium hydrogen chloranilate

Kazuma Gotoh,^a Hirokazu Nagoshi ^a and Hiroyuki Ishida ^a ^*

^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 salt, C₆H₆NO₂⁺·C₆HCl₂O₄^-, the pyridine ring and the mean plane of the hydrogen chloranilate anion form a dihedral angle of 77.40 (8)°. The ionic components are held together by N-HO and O-HO hydrogen bonds, forming a supramolecular ladder. C-HO interactions are also present.

Related literature

For the structures of related carboxypyridinium hydrogen chloranilates, see: Gotoh et al. (2006); Tabuchi et al. (2005); Ishida (2009).

Experimental

Crystal data

C₆H₆NO₂⁺·C₆HCl₂O₄^-
M_r = 332.10
Monoclinic, P 2₁ /c
a = 9.4166 (8) Å
b = 19.6900 (16) Å
c = 6.7089 (6) Å
= 99.043 (3)°
V = 1228.45 (18) Å³
Z = 4
Mo K radiation
= 0.56 mm^-1
T = 103 K
0.30 × 0.30 × 0.23 mm

Data collection

Rigaku R-AXIS RAPID-II diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.847, T_max = 0.880
9710 measured reflections
3433 independent reflections
2228 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.144
S = 1.10
3433 reflections
202 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.47 e Å^-3
_min = -0.92 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1	0.92 (4)	2.11 (3)	2.932 (2)	147 (3)
O2-H2O5ⁱ	0.79 (3)	2.05 (3)	2.746 (2)	148 (3)
O6-H6O4ⁱⁱ	0.90 (3)	1.63 (3)	2.528 (2)	177.1 (15)
C8-H8O4ⁱⁱⁱ	0.95	2.50	3.338 (3)	147
C9-H9O3^iv	0.95	2.33	3.227 (3)	156
C11-H11O1^v	0.95	2.46	3.374 (3)	162
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y, z+1; (iii) -x+1, -y+1, -z+1; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) -x, -y+1, -z.

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2376 ).

Acknowledgements

This work was supported by a Grant-in-Aid for Scientific Research (C) (No. 19550018) from the Japan Society for the Promotion of Science.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gotoh, K., Tabuchi, Y., Akashi, H. & Ishida, H. (2006). Acta Cryst. E62, o4420-o4421.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Ishida, H. (2009). Private communication (deposition numbers CCDC 720198 and CCDC 720199). CCDC, Cambridge, England.
Rigaku/MSC (2004). PROCESS-AUTO and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Tabuchi, Y., Takahashi, A., Gotoh, K., Akashi, H. & Ishida, H. (2005). Acta Cryst. E61, o4215-o4217.

organic compounds