2-Amino-4-methyl­pyridinium 4-nitro­benzoate

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

doi:10.1107/S1600536810000693

Volume 66
Part 2
Page o335
February 2010

Received 4 January 2010
Accepted 6 January 2010
Online 13 January 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.047
wR = 0.124
Data-to-parameter ratio = 12.8
Details

2-Amino-4-methylpyridinium 4-nitrobenzoate

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⁺·C₇H₄NO₄^-, the nitro group of the 4-nitrobenzoate anion is twisted by 7.66 (10)° from the attached ring. In the crystal structure, the 2-amino-4-methylpyridinium cations and 4-nitrobenzoate anions are linked via a pair of N-HO hydrogen bonds to form a ribbon-like structure along the c axis. The ribbons are crosslinked into a three-dimensional framework by C-HO hydrogen bonds.

Related literature

For substituted pyridines, see: Pozharski et al. (1997); Katritzky et al. (1996). 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). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₆H₉N₂⁺·C₇H₄NO₄^-
M_r = 275.26
Monoclinic, P c
a = 10.5267 (2) Å
b = 5.0187 (1) Å
c = 12.2436 (3) Å
= 92.194 (1)°
V = 646.36 (2) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 100 K
0.49 × 0.28 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.949, T_max = 0.983
10644 measured reflections
2841 independent reflections
2390 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.124
S = 1.03
2841 reflections
222 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.44 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H1N2O1ⁱ	0.93 (3)	2.55 (3)	3.254 (2)	134 (3)
N2-H1N2O2ⁱ	0.93 (3)	1.78 (3)	2.688 (2)	167 (3)
N3-H1N3O2ⁱⁱ	0.85 (4)	2.04 (4)	2.875 (2)	170 (4)
N3-H2N3O1ⁱ	0.94 (3)	1.84 (3)	2.778 (2)	173 (3)
C3-H3AO4ⁱⁱⁱ	0.97 (2)	2.53 (2)	3.160 (2)	123 (2)
C6-H6AO1ⁱⁱ	1.00 (2)	2.46 (2)	3.116 (2)	123 (3)
C7-H7AO1ⁱⁱ	1.00 (3)	2.45 (3)	3.102 (2)	122 (2)
C9-H9AO3^iv	0.96 (3)	2.33 (3)	3.276 (3)	168 (3)
C13-H13CO4^v	0.96	2.55	3.335 (2)	139
Symmetry codes: (i) x, y-1, z+1; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[x, -y, z-{\script{1\over 2}}]$ ; (iv) x-1, y+1, z+1; (v) $[x-1, -y, z+{\script{1\over 2}}]$ .

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: CI5013 ).

Acknowledgements

MH and H-KF 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.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Jeffrey, G. A. (1997). An Introduction to Hydrogen Bonding. 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.
Scheiner, S. (1997). Hydrogen Bonding, A Theoretical Perspective. Oxford University Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds