2,3-Diamino­pyridinium sorbate–sorbic acid (1/1)

Hemamalini, M.; Goh, J.H.; Fun, H.-K.

doi:10.1107/S1600536811053025

Volume 68
Part 1
Page o186
January 2012

Received 5 December 2011
Accepted 9 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.047
wR = 0.152
Data-to-parameter ratio = 22.4
Details

2,3-Diaminopyridinium sorbate-sorbic acid (1/1)

Madhukar Hemamalini,^a Jia Hao Goh ^a ⁺ and Hoong-Kun Fun ^a ^*⁺⁺

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title molecular salt-adduct, C₅H₈N₃⁺·C₆H₇O₂^-·C₆H₈O₂, the 2,3-diaminopyridinium cation is essentially planar, with a maximum deviation of 0.013 (2) Å, and is protanated at its pyridine N atom. The sorbate anion and sorbic acid molecules exist in extended conformations. In the crystal, the protonated N atom and one of the two amino-group H atoms are hydrogen bonded to the sorbate anion through a pair of N-HO hydrogen bonds, forming an R₁²(6) ring motif. The carboxyl groups of the sorbic acid molecules and the carboxylate groups of the sorbate anions are connected via O-HO hydrogen bonds. Furthermore, the ion pairs and neutral molecules are connected via intermolecular N-HO hydrogen bonds, forming sheets lying parallel to (100).

Related literature

For a different crystal structure arising from the same synthesis conditions, see: Hemamalini & Fun (2010). For background to aminopyridines, see: Peng et al. (2001); Leung et al. (2002); Banerjee & Murugavel (2004); Lautie & Belabbes (1996). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₅H₈N₃⁺·C₆H₇O₂^-·C₆H₈O₂
M_r = 333.38
Monoclinic, P 2₁ /c
a = 16.1636 (17) Å
b = 9.6538 (10) Å
c = 12.6887 (13) Å
= 112.844 (2)°
V = 1824.6 (3) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.47 × 0.25 × 0.06 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.960, T_max = 0.994
27805 measured reflections
5345 independent reflections
2898 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.152
S = 1.02
5345 reflections
239 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.30 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1A-H1AO1B	0.82	1.79	2.5252 (19)	148
N1-H1N1O1Aⁱ	0.89 (3)	2.06 (3)	2.887 (2)	153 (3)
N1-H1N1O2Aⁱ	0.89 (3)	2.31 (3)	3.094 (2)	147 (2)
N2-H1N2O1Aⁱ	0.83 (2)	2.30 (2)	3.054 (2)	152 (2)
N2-H1N2O2Bⁱ	0.83 (2)	2.59 (3)	3.136 (2)	125 (2)
N2-H2N2O2A	0.86 (2)	2.00 (3)	2.863 (2)	177 (2)
N3-H1N3O2A	0.84 (2)	2.19 (2)	3.010 (2)	166.1 (16)
N3-H2N3O2Bⁱⁱ	0.92 (3)	2.09 (3)	3.002 (2)	170 (2)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTLand PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6558 ).

Acknowledgements

MH, JHG and HKF thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

Banerjee, S. & Murugavel, R. (2004). Cryst. Growth Des. 4, 545-522.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o2369.
Lautie, A. & Belabbes, Y. (1996). Spectrochim. Acta Part A, 52, 1903-1914.
Leung, M.-K., Mandal, A.-B., Wang, C.-C., Peng, S.-M., Lu, H.-F. & Chou, P.-T. (2002). J. Am. Chem. Soc. 124, 4287-4297.
Peng, S.-H., Wang, C.-C., Lo, W.-C. & Peng, S.-M. (2001). J. Chin. Chem. Soc. 48, 987-996.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds