rac-2-Amino­pyridinium cis-2-carb­oxy­cyclo­hexane-1-carboxyl­ate

Smith, G.; Wermuth, U.D.

doi:10.1107/S1600536811025256

Volume 67
Part 8
Page o1900
August 2011

Received 24 June 2011
Accepted 27 June 2011
Online 2 July 2011

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R = 0.033
wR = 0.081
Data-to-parameter ratio = 14.1
Details

rac-2-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 compound, C₅H₇N₂⁺·C₈H₁₁O₄^-, the cis anions associate through head-to-tail carboxylic acid-carboxyl O-HO hydrogen bonds [graph set C(7)], forming chains which extend along c and are interlinked through the carboxyl groups, forming cyclic R₂²(8) associations with the pyridinium and an amine H-atom donor of the cation. Further amine-carboxyl N-HO interactions form enlarged centrosymmetric rings [graph set R₄⁴(18)] and extensions down b, giving a three-dimensional structure.

Related literature

For the structure of racemic cis-cyclohexane,1,2-dicarboxylic acid, see: Benedetti et al. (1970). For the structure of racemic ammonium cis-2-carboxycyclohexane-1-carboxylate, see: Smith & Wermuth (2011) and of brucinium (1R,2S-2-carboxycyclohexane-1-carboxylate dihydrate, see: Smith et al. (2011). For the structure of the adduct of cis-cyclohexane-1,2-dicarboxylic acid with 4,4'-bipyridine, see: Bhogala et al. (2005). For graph-set analysis, see: Etter et al. (1990).

Experimental

Crystal data

C₅H₇N₂⁺·C₈H₁₁O₄^-
M_r = 266.29
Monoclinic, P 2₁ /c
a = 12.4709 (5) Å
b = 10.4191 (5) Å
c = 10.6451 (5) Å
= 101.250 (4)°
V = 1356.60 (11) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 200 K
0.35 × 0.32 × 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 = 0.90, T_max = 0.98
9200 measured reflections
2658 independent reflections
1947 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.081
S = 0.99
2658 reflections
188 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.16 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1A-H1AO11	0.981 (15)	1.656 (15)	2.6223 (15)	167.7 (14)
N21A-H21AO12	0.911 (18)	2.044 (17)	2.9361 (16)	166.3 (14)
N21A-H22AO22ⁱ	0.873 (16)	2.105 (16)	2.9103 (17)	153.1 (14)
O21-H21O11ⁱⁱ	0.991 (19)	1.595 (19)	2.5806 (13)	172.9 (18)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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: WN2440 ).

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.
Bhogala, B. R., Basavogu, S. & Nangia, A. (2005). Cryst. Struct. Commun. 7, 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. (2011). Acta Cryst. E67, o174.
Smith, G., Wermuth, U. W. & Williams, M. L. (2011). Acta Cryst. E67. Submitted.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds