4-Amino­pyridinium hydrogen succinate

Fun, H.-K.; John, J.; Jebas, S.R.; Balasubramanian, T.

doi:10.1107/S1600536809006990

Volume 65
Part 4
Pages o765-o766
April 2009

Received 24 February 2009
Accepted 25 February 2009
Online 14 March 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.062
wR = 0.150
Data-to-parameter ratio = 14.7
Details

4-Aminopyridinium hydrogen succinate

Hoong-Kun Fun,^a ^* Jain John,^b Samuel Robinson Jebas ^a ⁺ and T Balasubramanian ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Physics, National Institute of Technology, Tiruchirappalli 620015, India
Correspondence e-mail: hkfun@usm.my

In the title salt, C₅H₇N₂⁺·C₄H₅O₄^-, the asymmetric unit comprises an aminopyridinium cation and a hydrogen succinate anion as protonation of the aromatic N atom of the 4-aminopyridine molecule has occurred. The crystal packing is stabilized by intermolecular O-HO and N-HO hydrogen bonds that lead to a two-dimensional array. Short C-HO contacts are also present.

Related literature

For the biological activity of 4-aminopyridine, see: Judge & Bever (2006); Schwid et al. (1997); Strupp et al. (2004). For the applications of succinic acid, see: Sauer et al. (2008); Song & Lee (2006); Zeikus et al. (1999). For related structures, see: Chao & Schempp (1977); Anderson et al. (2005); Bhattacharya et al. (1994); Karle et al. (2003); Gopalan et al. (2000); Leviel et al., (1981). For stability of the temperature controller, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₅H₇N₂⁺·C₄H₅O₄^-
M_r = 212.21
Monoclinic, P 2₁ /c
a = 6.5443 (3) Å
b = 22.2867 (11) Å
c = 7.1112 (4) Å
= 114.587 (4)°
V = 943.13 (8) Å³
Z = 4
Mo K radiation
= 0.12 mm^-1
T = 100 K
0.38 × 0.14 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.956, T_max = 0.991
7174 measured reflections
2176 independent reflections
1483 reflections with I > 2(I)
R_int = 0.066

Refinement

R[F² > 2(F²)] = 0.062
wR(F²) = 0.150
S = 1.06
2176 reflections
148 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.44 e Å^-3
_min = -0.46 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H1O3O2ⁱ	1.09	1.40	2.482 (2)	176
N1-H1N1O3ⁱⁱ	0.94 (3)	2.00 (3)	2.926 (3)	168 (3)
N2-H1N2O1ⁱⁱⁱ	0.90 (3)	2.59 (3)	3.115 (3)	118 (3)
N2-H1N2O2ⁱⁱⁱ	0.90 (3)	1.92 (3)	2.810 (3)	174 (3)
N1-H2N1O4	0.85 (3)	2.08 (3)	2.934 (3)	175 (2)
C1-H1AO4ⁱⁱ	0.93	2.54	3.440 (3)	164
C2-H2AO1ⁱⁱⁱ	0.93	2.39	3.041 (3)	127
C3-H3AO1^iv	0.93	2.31	3.222 (3)	166
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z; (iii) $[-x-1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2378 ).

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No.1001/PFIZIK/811012.

References

Anderson, F. P., Gallagher, J. F., Kenny, P. T. M. & Lough, A. J. (2005). Acta Cryst. E61, o1350-o1353.
Bhattacharya, S., Dastidar, P. & Guru Row, T. N. (1994). Chem. Mater. 6, 531-537.
Bruker (2005). APEX2, SAINT and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.
Chao, M. & Schempp, E. (1977). Acta Cryst. B33, 1557-1564.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Gopalan, R. S., Kumaradhas, P., Kulkarani, G. U. & Rao, C. N. R. (2000). J. Mol. Struct. 521, 97-106.
Judge, S. & Bever, C. (2006). Pharmacol. Ther. 111, 224-259.
Karle, I., Gilardi, R. D., Chandrashekhar Rao, Ch., Muraleedharan, K. M. & Ranganathan, S. (2003). J. Chem. Crystallogr. 33, 727-749.
Leviel, J.-L., Auvert, G. & Savariault, J.-M. (1981). Acta Cryst. B37, 2185-2189.
Sauer, M., Porro, D., Mattanovich, D. & Branduaradi, P. (2008). Trends Biotechnol. 26, 100-108.
Schwid, S. B., Petrie, M. D., McDermott, M. P., Tierney, D. S., Mason, D. H. & Goodman, A. D. (1997). Neurology, 48, 817-821.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Song, H. & Lee, S. Y. (2006). Enzyme Microb. Technol. 39, 352-361.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Strupp, M., Kalla, R., Dichgans, M., Fraitinger, T., Glasauer, S. & Brandt, T. (2004). Neurology, 62, 1623-1625.
Zeikus, J. G., Jain, M. K. & Elankovan, P. (1999). Appl. Microbiol. Biotechnol. 51, 545-552.

organic compounds