2-Amino-5-methyl­pyridinium 4-hydroxy­benzoate

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

doi:10.1107/S1600536810009396

Volume 66
Part 4
Pages o936-o937
April 2010

Received 4 March 2010
Accepted 12 March 2010
Online 27 March 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R = 0.039
wR = 0.137
Data-to-parameter ratio = 24.3
Details

2-Amino-5-methylpyridinium 4-hydroxybenzoate

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 salt, C₆H₉N₂⁺·C₇H₅O₃^-, the carboxylate mean plane of the 4-hydroxybenzoate anion is twisted by 13.07 (4)° from the attached ring. In the crystal structure, the ions are linked into a two-dimensional network by N-HO, O-HO and C-HO hydrogen bonds. Within this network, the N-HO hydrogen bonds generate R₂²(8) ring motifs. In addition, [pi] - [pi] interactions involving the pyridinium rings, with a centroid-centroid distance of 3.7599 (4) Å, are observed.

Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997); Katritzky et al. (1996). For related structures, see: Hemamalini & Fun (2010a,b,c). For 4-hydroxybenzoic acid, see: Vishweshwar et al. (2003). For details of hydrogen bonding, see: Jeffrey & Saenger (1991); Jeffrey (1997); Scheiner (1997); Aakeröy et al. (2002). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₆H₉N₂⁺·C₇H₅O₃^-
M_r = 246.26
Monoclinic, P 2₁ /c
a = 12.9562 (6) Å
b = 8.7876 (4) Å
c = 11.3276 (5) Å
= 108.397 (1)°
V = 1223.78 (10) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 100 K
0.39 × 0.33 × 0.27 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.963, T_max = 0.975
20102 measured reflections
5326 independent reflections
4662 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.137
S = 1.15
5326 reflections
219 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.60 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1O3	0.957 (17)	1.726 (17)	2.6738 (9)	170.4 (15)
N2-H1N2O3ⁱ	0.905 (14)	1.967 (14)	2.8443 (9)	162.9 (13)
N2-H2N2O2	0.922 (14)	1.876 (14)	2.7962 (9)	176.1 (13)
O1-H101O2ⁱⁱ	0.892 (18)	1.779 (18)	2.6635 (8)	170.7 (19)
C3-H3AO2ⁱⁱⁱ	1.016 (16)	2.476 (15)	3.1887 (9)	126.7 (10)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (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: 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: RZ2424 ).

Acknowledgements

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

References

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Vishweshwar, P., Nangia, A. & Lynch, V. M. (2003). CrystEngComm. 5, 164-168.

organic compounds