2-Amino-5-methyl­pyridinium 2-amino­benzoate

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

doi:10.1107/S1600536812043243

Volume 68
Part 11
Pages o3196-o3197
November 2012

Received 3 October 2012
Accepted 17 October 2012
Online 24 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.101
Data-to-parameter ratio = 14.7
Details

2-Amino-5-methylpyridinium 2-aminobenzoate

Kaliyaperumal Thanigaimani,^a Abbas Farhadikoutenaei,^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 2-aminobenzoate anion of the title salt, C₆H₉N₂⁺·C₇H₆NO₂^-, an intramolecular N-HO hydrogen bond is observed. The dihedral angle between the ring and the CO₂ group is 8.41 (13)°. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxylate O atoms via a pair of N-HO hydrogen bonds, forming an R₂²(8) ring motif. The ion pairs are further connected via N-HO hydrogen bonds, resulting in a donor-donor-acceptor-acceptor (DDAA) array of quadruple hydrogen bonds. The crystal structure also features a weak N-HO hydrogen bond and a C-H [pi] interaction, resulting in a three-dimensional network.

Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997); Katritzky et al. (1996). For details of hydrogen bonding, see: Jeffrey (1997); Scheiner (1997). For related structures, see: Nahringbauer & Kvick (1977); Hemamalini & Fun (2010a,b); Bis & Zaworotko (2005); Thanigaimani et al. (2012). For hydrogen-bond motifs, see: Bernstein et al. (1995). For hydrogen-bonding patterns in organic salts, see: Baskar Raj et al. (2003). 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⁺·C₇H₆NO₂^-
M_r = 245.28
Monoclinic, P 2₁ /c
a = 9.2394 (8) Å
b = 13.9200 (11) Å
c = 12.1514 (8) Å
= 129.850 (4)°
V = 1199.82 (16) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.35 × 0.33 × 0.14 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.968, T_max = 0.987
11650 measured reflections
2707 independent reflections
2361 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.101
S = 1.07
2707 reflections
184 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.27 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7-C12 ring.

D-HA	D-H	HA	DA	D-HA
N3-H3O2	0.92 (2)	1.97 (2)	2.6734 (18)	131.8 (15)
N2-H1O1ⁱ	0.926 (18)	1.982 (18)	2.8561 (14)	157 (2)
N3-H2O1ⁱⁱ	0.897 (17)	2.159 (18)	3.0445 (14)	168.7 (14)
N1-H4O2ⁱⁱⁱ	0.959 (18)	1.723 (18)	2.6776 (13)	172.7 (17)
N2-H5O1ⁱⁱⁱ	0.933 (17)	1.899 (18)	2.8305 (14)	176.8 (16)
C1-H1ACg1	0.95	2.58	3.5094 (13)	165
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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: IS5202 ).

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and Fundamental Research Grant Scheme (FRGS) No. 203/PFIZIK/6711171 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.
Baskar Raj, S., Stanley, N., Muthiah, P. T., Bocelli, G., Olla', R. & Cantoni, A. (2003). Cryst. Growth Des. 3, 567-571.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bis, J. A. & Zaworotko, M. J. (2005). Cryst. Growth Des. 5, 1169-1179.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Hemamalini, M. & Fun, H.-K. (2010a). Acta Cryst. E66, o936-o937.
Hemamalini, M. & Fun, H.-K. (2010b). Acta Cryst. E66, o623-o624.
Jeffrey, G. A. (1997). In An Introduction of Hydrogen Bonding. Oxford University Press.
Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). In Comprehensive Heterocyclic Chemistry II. Oxford: Pergamon Press.
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Pozharski, A. F., Soldatenkov, A. T. & Katritzky, A. R. (1997). In Heterocycles in Life and Society. New York: Wiley.
Scheiner, S. (1997). In 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.
Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o3195.

organic compounds