4-Amino­pyridinium cis-2-carb­oxy­cyclo­hexane-1-carboxyl­ate

Smith, G.; Wermuth, U.D.

doi:10.1107/S1600536811039547

Volume 67
Part 10
Page o2794
October 2011

Received 19 September 2011
Accepted 26 September 2011
Online 30 September 2011

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R = 0.028
wR = 0.060
Data-to-parameter ratio = 9.1
Details

4-Aminopyridinium cis-2-carboxycyclohexane-1-carboxylate

Graham Smith ^a ^* and Urs D. Wermuth ^a

^aFaculty of Science and Technology, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
Correspondence e-mail: g.smith@qut.edu.au

In the structure of the title molecular salt, C₅H₇N₂⁺·C₈H₁₁O₄^-, the cis monoanions associate through short O-HO hydrogen bonds in the carboxylic acid groups [graph set C(7)], forming zigzag chains which extend along the c axis. These are interlinked through pyridinium and amine N-HO hydrogen bonds, giving a three-dimensional network structure.

Related literature

For the structure of racemic cis-cyclohexane-1,2-dicarboxylic acid, see: Benedetti et al. (1970). For the structure of the racemic ammonium and 2-aminopyridinium salts of cis-2-carboxycyclohexane-1-carboxylate, see: Smith & Wermuth (2011a,b). For graph-set analysis, see Etter et al. (1990).

Experimental

Crystal data

C₅H₇N₂⁺·C₈H₁₁O₄^-
M_r = 266.29
Orthorhombic, P n a 2₁
a = 12.1359 (3) Å
b = 9.8351 (3) Å
c = 11.1850 (3) Å
V = 1335.02 (6) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 200 K
0.30 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.948, T_max = 0.990
9670 measured reflections
1709 independent reflections
1448 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.028
wR(F²) = 0.060
S = 0.99
1709 reflections
188 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.15 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1A-H1AO12ⁱ	0.88 (2)	1.91 (2)	2.795 (2)	180 (3)
N41A-H41AO12ⁱⁱ	0.86 (2)	2.14 (2)	2.989 (2)	168 (2)
N41A-H42AO22	0.91 (2)	2.13 (2)	2.974 (2)	152.6 (18)
O21-H21O11ⁱⁱⁱ	0.95 (3)	1.59 (3)	2.5302 (17)	170 (3)
Symmetry codes: (i) x, y, z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2453 ).

Acknowledgements

The authors acknowledge financial support from the Australian Research Council, the Faculty of Science and Technology and the University Library, Queensland University of Technology.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Benedetti, E., Pedone, C. & Allegra, G. (1970). J. Phys. Chem. 74, 512-516.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G. & Wermuth, U. D. (2011a). Acta Cryst. E67, o174.
Smith, G. & Wermuth, U. D. (2011b). Acta Cryst. E67, o1900.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds