Cyclo­hexane-1,2-diammonium bis­(pyridine-2-carboxyl­ate)

Kim, N.-H.; Hwang, I.-C.; Ha, K.

doi:10.1107/S1600536809038689

Volume 65
Part 10
Page o2571
October 2009

Received 23 September 2009
Accepted 24 September 2009
Online 30 September 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.064
wR = 0.171
Data-to-parameter ratio = 16.3
Details

Cyclohexane-1,2-diammonium bis(pyridine-2-carboxylate)

Nam-Ho Kim,^a In-Chul Hwang ^b and Kwang Ha ^a ^*

^aSchool of Applied Chemical Engineering, The Research Institute of Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea, and ^bInstitute of Basic Sciences, Pohang University of Science and Technology, Pohang 790-784, Republic of Korea
Correspondence e-mail: hakwang@chonnam.ac.kr

In the dication of the title salt, C₆H₁₆N₂²⁺·2C₆H₄NO₂^-, the two ammonium groups are in the equatorial positions of the chair-shaped cyclohexyl ring. In the crystal, the cations and anions are linked by N-HO and N-HN hydrogen bonds, forming a layer network parallel to the ac plane. Weak [pi] - [pi] interactions between adjacent pyridine rings with a centroid-centroid distance of 3.589 (2) Å are also present.

Related literature

For the syntheses and structures of cyclohexane-1,2-diammonium compounds, see: Lin & Lii (1998); Lin & Wang (2000). For the crystal structures of pyridine-2-carboxylates, see: Kim & Ha (2009a,b,c).

Experimental

Crystal data

C₆H₁₆N₂²⁺·2C₆H₄NO₂^-
M_r = 360.41
Monoclinic, P 2₁ /n
a = 9.2942 (11) Å
b = 20.329 (2) Å
c = 10.2189 (11) Å
= 101.775 (3)°
V = 1890.1 (4) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: none
11005 measured reflections
3854 independent reflections
1741 reflections with I > 2(I)
R_int = 0.064

Refinement

R[F² > 2(F²)] = 0.064
wR(F²) = 0.171
S = 0.98
3854 reflections
237 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO3	0.86	1.89	2.749 (3)	175
N1-H1BO2	0.86	1.92	2.743 (3)	160
N1-H1CO3ⁱ	0.86	2.10	2.790 (3)	137
N1-H1CN4ⁱ	0.86	2.49	3.271 (4)	152
N2-H2AO1ⁱⁱ	0.86	2.09	2.828 (3)	144
N2-H2AN3ⁱⁱ	0.86	2.53	3.254 (4)	142
N2-H2BO1	0.86	2.02	2.807 (3)	152
N2-H2CO4ⁱⁱⁱ	0.86	1.88	2.734 (3)	171
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y+1, -z+2.

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: NG2649 ).

Acknowledgements

This work was supported by a Korea Research Foundation Grant funded by the Korean Government (MOEHRD) (KRF-2007-412-J02001).

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Kim, N.-H. & Ha, K. (2009a). Acta Cryst. E65, o1415.
Kim, N.-H. & Ha, K. (2009b). Acta Cryst. E65, o2151.
Kim, N.-H. & Ha, K. (2009c). Acta Cryst. E65, o2504.
Lin, H.-M. & Lii, K.-H. (1998). Inorg. Chem. 37, 4220-4222.
Lin, C.-H. & Wang, S.-L. (2000). Chem. Mater. 12, 3617-3623.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds