2-Amino-6-methyl­pyridinium 3-chloro­benzoate

Thanigaimani, K.; Khalib, N.C.; Arshad, S.; Razak, I.A.

doi:10.1107/S1600536813002559

Volume 69
Part 3
Page o318
March 2013

Received 20 December 2012
Accepted 25 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R = 0.045
wR = 0.128
Data-to-parameter ratio = 13.4
Details

2-Amino-6-methylpyridinium 3-chlorobenzoate

Kaliyaperumal Thanigaimani,^a Nuridayanti Che Khalib,^a Suhana Arshad ^a and Ibrahim Abdul Razak ^a ^*⁺

^aSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: arazaki@usm.my

In the title salt, C₆H₉N₂⁺·C₇H₄ClO₂^-, the 3-chlorobenzoate anion shows a whole-molecule disorder over two positions with a refined occupancy ratio of 0.505 (4):0.495 (4). In the crystal, the cations and anions are linked via N-HO hydrogen bonds, forming a centrosymmetric 2 + 2 aggregate with R₂²(8) and R₄²(8) ring motifs. The crystal structure also features a [pi] - [pi] stacking interaction between the pyridinium rings with a centroid-centroid distance of 3.8339 (9) Å.

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 (2010); Thanigaimani et al. (2012); Draguta et al. (2012). 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⁺·C₇H₄ClO₂^-
M_r = 264.70
Monoclinic, C 2/c
a = 22.3118 (15) Å
b = 15.2053 (10) Å
c = 7.4166 (5) Å
= 100.924 (1)°
V = 2470.5 (3) Å³
Z = 8
Mo K radiation
= 0.30 mm^-1
T = 100 K
0.36 × 0.06 × 0.05 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.898, T_max = 0.985
24731 measured reflections
3575 independent reflections
2446 reflections with I > 2(I)
R_int = 0.053

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.128
S = 1.06
3575 reflections
267 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.29 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H2N2O1	0.94 (2)	1.69 (2)	2.614 (7)	168 (2)
N2-H1N2O2	0.86 (2)	1.98 (3)	2.832 (14)	170 (2)
N2-H1N1O2ⁱ	0.88 (2)	2.06 (2)	2.853 (11)	150 (2)
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

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: IS5234 ).

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.
Draguta, S., Khrustalev, V. N., Sandhu, B., Antipin, M. Y. & Timofeeva, T. V. (2012). Acta Cryst. E68, o3466.
Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o1843-o1844.
Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). In Comprehensive Heterocyclic Chemistry II. Oxford: Pergamon Press.
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. (2012). Acta Cryst. E68, o3195.

organic compounds