2-Amino-5-methyl­pyridinium 4-methyl­benzoate

Thanigaimani, K.; Farhadikoutenaei, A.; Arshad, S.; Razak, I.A.

doi:10.1107/S1600536812050374

Volume 69
Part 1
Pages o94-o95
January 2013

Received 4 December 2012
Accepted 11 December 2012
Online 15 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R = 0.043
wR = 0.125
Data-to-parameter ratio = 25.4
Details

2-Amino-5-methylpyridinium 4-methylbenzoate

Kaliyaperumal Thanigaimani,^a Abbas Farhadikoutenaei,^a,^b Suhana Arshad ^a and Ibrahim Abdul Razak ^a ^*⁺

^aSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Physics, Faculty of Science, University of Mazandaran, Babolsar, Iran
Correspondence e-mail: arazaki@usm.my

The 4-methylbenzoate anion of the title salt, C₆H₉N₂⁺·C₈H₇O₂^-, is nearly planar, with a dihedral angle of 6.26 (10)° between the benzene ring and the carboxylate group. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxylate O atoms of the anion via a pair of N-HO hydrogen bonds with an R₂²(8) ring motif, forming an approximately planar ion pair with a dihedral angle of 9.63 (4)° between the pyridinium and benzene rings. The ion pairs are further connected via N-HO and weak C-HO hydrogen bonds, forming a two-dimensional network parallel to the bc plane.

Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997); Katritzky et al. (1996). For related structures, see: Nahringbauer & Kvick (1977); Thanigaimani et al. (2012a,b,c). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₆H₉N₂⁺·C₈H₇O₂^-
M_r = 244.29
Monoclinic, P 2₁ /c
a = 9.6315 (5) Å
b = 10.8713 (6) Å
c = 12.1481 (7) Å
= 104.093 (1)°
V = 1233.71 (12) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.52 × 0.32 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.955, T_max = 0.987
18139 measured reflections
4493 independent reflections
3783 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.125
S = 1.03
4493 reflections
177 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.43 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H1N2O2ⁱ	0.920 (16)	1.832 (16)	2.7469 (11)	172.7 (15)
N2-H2N2O1ⁱⁱ	0.926 (16)	1.919 (17)	2.8424 (11)	175.4 (15)
N1-H1N1O1ⁱ	0.976 (18)	1.751 (18)	2.7224 (10)	173.1 (16)
C10-H10AO2ⁱⁱⁱ	0.95	2.34	3.1120 (11)	138
Symmetry codes: (i) x+1, y-1, z+1; (ii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (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: IS5229 ).

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and USM Short Term Grant No. 304/PFIZIK/6312078 to conduct this work. KT thanks The Academy of Sciences for the Developing World and USM for a TWAS-USM 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). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). In Comprehensive Heterocyclic Chemistry II. Oxford: Pergamon Press.
Nahringbauer, I. & Kvick, Å. (1977). Acta Cryst. B33, 2902-2905.
Pozharski, A. F., Soldatenkov, A. T. & Katritzky, A. R. (1997). In Heterocycles in Life and Society. New York: Wiley.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012a). Acta Cryst. E68, o3151-o3152.
Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012b). Acta Cryst. E68, o3195.
Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012c). Acta Cryst. E68, o3196-o3197.

organic compounds