2-Amino-5-bromo­pyridinium 2-hy­droxy­benzoate

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

doi:10.1107/S1600536810029855

Volume 66
Part 8
Pages o2164-o2165
August 2010

Received 26 July 2010
Accepted 27 July 2010
Online 31 July 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.025
wR = 0.070
Data-to-parameter ratio = 19.9
Details

2-Amino-5-bromopyridinium 2-hydroxybenzoate

Ching Kheng Quah,^a ⁺ 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⁺·C₇H₅O₃^-, the 2-amino-5-bromopyridinium cation and 2-hydroxybenzoate anion are essentially planar with maximum deviations of 0.020 (1) and 0.018 (2) Å, respectively. The anion is stabilized by an intramolecular O-HO hydrogen bond, which generates an S(6) ring motif. In the crystal, the cations and anions are linked by N-HO hydrogen bonds into chains propagating along [010]. The chains contain R₂²(8) ring motifs. The structure is further stabilized by [pi] - [pi] stacking interactions [centroid-centroid distances = 3.4908 (10) and 3.5927 (10) Å] and also features short BrO contacts [2.9671 (13) Å].

Related literature

For details of non-covalent interactions, see: Remenar et al. (2003); Sokolov et al. (2006). For the importance of salicylic acid, see: Sticher et al. (1997); Rairdan & Delaney (2002); Nawrath & Métraux (1999); Wildermuth et al. (2001). For related structures, see: Quah et al. (2008, 2010a,b). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₅H₆BrN₂⁺·C₇H₅O₃^-
M_r = 311.14
Monoclinic, P 2₁ /c
a = 8.9498 (2) Å
b = 10.8673 (2) Å
c = 13.1277 (3) Å
= 108.704 (1)°
V = 1209.37 (4) Å³
Z = 4
Mo K radiation
= 3.40 mm^-1
T = 100 K
0.48 × 0.27 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.291, T_max = 0.572
13299 measured reflections
3559 independent reflections
2942 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.025
wR(F²) = 0.070
S = 1.12
3559 reflections
179 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.62 e Å^-3
_min = -0.48 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O1O2	0.89 (3)	1.66 (3)	2.500 (2)	157 (2)
N1-H1NO3	0.96 (2)	1.66 (2)	2.611 (2)	172 (2)
N2-H1N2O2	0.85 (3)	1.98 (2)	2.818 (2)	170 (2)
N2-H2N2O1ⁱ	0.82 (2)	2.14 (2)	2.917 (2)	160 (2)
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ .

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: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5140 ).

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). CKQ also thanks USM for the award of a USM fellowship and HM also thanks USM for the award of postdoctoral fellowship.

References

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Wildermuth, M. C., Dewdney, J., Wu, G. & Ausubel, F. M. (2001). Nature (London), 414, 562-565.

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