2-Amino-5-bromo­pyridinium hydrogen succinate

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

doi:10.1107/S1600536810006495

Volume 66
Part 3
Pages o689-o690
March 2010

Received 17 February 2010
Accepted 19 February 2010
Online 27 February 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.025
wR = 0.057
Data-to-parameter ratio = 16.5
Details

2-Amino-5-bromopyridinium hydrogen succinate

Madhukar Hemamalini ^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 compound, C₅H₆BrN₂⁺·C₄H₅O₄^-, the pyridine N atom of the 2-amino-5-bromopyridine molecule is protonated. The protonated N atom and the amino group are linked via N-HO hydrogen bonds to the carboxylate O atoms of the singly deprotonated succinate anion. The hydrogen succinate anions are linked via O-HO hydrogen bonds. A weak intermolecular C-HO hydrogen bond is also observed.

Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997); Katritzky et al. (1996). For related structures, see: Goubitz et al. (2001); Vaday & Foxman (1999). For applications of succinic acid, see: Sauer et al. (2008). For bond-length data, see: Allen et al. (1987). For details of hydrogen bonding, see: Jeffrey & Saenger (1991); Jeffrey (1997); Scheiner (1997). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₅H₆N₂Br⁺·C₄H₅O₄^-
M_r = 291.11
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.3275 (2) Å
b = 13.6226 (5) Å
c = 15.1687 (5) Å
V = 1100.86 (7) Å³
Z = 4
Mo K radiation
= 3.74 mm^-1
T = 296 K
0.80 × 0.15 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.155, T_max = 0.650
10042 measured reflections
2472 independent reflections
2138 reflections with I > 2s(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.025
wR(F²) = 0.057
S = 0.99
2472 reflections
150 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.21 e Å^-3
_min = -0.31 e Å^-3
Absolute structure: Flack (1983), 995 Friedel pairs
Flack parameter: 0.013 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1O2	0.85 (3)	1.88 (3)	2.720 (3)	171 (3)
N2-H2AO1	0.86	1.92	2.782 (3)	178
N2-H2BO1ⁱ	0.86	2.01	2.805 (3)	154
O4-H4O2ⁱⁱ	0.82	1.85	2.609 (2)	154
C1-H1O3ⁱⁱⁱ	0.93	2.43	3.280 (3)	152
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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: IS2526 ).

Acknowledgements

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
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.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Goubitz, K., Sonneveld, E. J. & Schenk, H. (2001). Z. Kristallogr. 216, 176-181.
Jeffrey, G. A. (1997). An Introduction to Hydrogen Bonding. New York: Oxford University Press.
Jeffrey, G. A. & Saenger, W. (1991). Hydrogen Bonding in Biological Structures. Berlin: Springer.
Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). Comprehensive Heterocyclic Chemistry II. Oxford: Pergamon Press.
Pozharski, A. F., Soldatenkov, A. T. & Katritzky, A. R. (1997). Heterocycles in Life and Society. New York: Wiley.
Sauer, M., Porro, D., Mattanovich, D. & Branduaradi, P. (2008). Trends Biotechnol. 26, 100-108.
Scheiner, S. (1997). Hydrogen Bonding. A Theoretical Perspective. New York: Oxford University Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Vaday, S. & Foxman, M. B. (1999). Cryst. Eng. 2, 145-151.

organic compounds