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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 [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.101
Data-to-parameter ratio = 14.7
Details
Open access

2-Amino-5-methylpyridinium 2-aminobenzoate

In the 2-aminobenzoate anion of the title salt, C6H9N2+·C7H6NO2-, an intramolecular N-H...O 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-H...O hydrogen bonds, forming an R22(8) ring motif. The ion pairs are further connected via N-H...O hydrogen bonds, resulting in a donor-donor-acceptor-acceptor (DDAA) array of quadruple hydrogen bonds. The crystal structure also features a weak N-H...O 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[Pozharski, A. F., Soldatenkov, A. T. & Katritzky, A. R. (1997). In Heterocycles in Life and Society. New York: Wiley.]); Katritzky et al. (1996[Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). In Comprehensive Heterocyclic Chemistry II. Oxford: Pergamon Press.]). For details of hydrogen bonding, see: Jeffrey (1997[Jeffrey, G. A. (1997). In An Introduction of Hydrogen Bonding. Oxford University Press.]); Scheiner (1997[Scheiner, S. (1997). In Hydrogen Bonding. A Theoretical Perspective. Oxford University Press.]). For related structures, see: Nahringbauer & Kvick (1977[Nahringbauer, I. & Kvick, Å. (1977). Acta Cryst. B33, 2902-2905.]); Hemamalini & Fun (2010a[Hemamalini, M. & Fun, H.-K. (2010a). Acta Cryst. E66, o936-o937.],b[Hemamalini, M. & Fun, H.-K. (2010b). Acta Cryst. E66, o623-o624.]); Bis & Zaworotko (2005[Bis, J. A. & Zaworotko, M. J. (2005). Cryst. Growth Des. 5, 1169-1179.]); Thanigaimani et al. (2012[Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o3195.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For hydrogen-bonding patterns in organic salts, see: Baskar Raj et al. (2003[Baskar Raj, S., Stanley, N., Muthiah, P. T., Bocelli, G., Olla', R. & Cantoni, A. (2003). Cryst. Growth Des. 3, 567-571.]). For bond-length data, see: Allen et al. (1987[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.]). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C6H9N2+·C7H6NO2-

  • Mr = 245.28

  • Monoclinic, P 21 /c

  • a = 9.2394 (8) Å

  • b = 13.9200 (11) Å

  • c = 12.1514 (8) Å

  • [beta] = 129.850 (4)°

  • V = 1199.82 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.987

  • 11650 measured reflections

  • 2707 independent reflections

  • 2361 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7-C12 ring.

D-H...A D-H H...A D...A D-H...A
N3-H3...O2 0.92 (2) 1.97 (2) 2.6734 (18) 131.8 (15)
N2-H1...O1i 0.926 (18) 1.982 (18) 2.8561 (14) 157 (2)
N3-H2...O1ii 0.897 (17) 2.159 (18) 3.0445 (14) 168.7 (14)
N1-H4...O2iii 0.959 (18) 1.723 (18) 2.6776 (13) 172.7 (17)
N2-H5...O1iii 0.933 (17) 1.899 (18) 2.8305 (14) 176.8 (16)
C1-H1A...Cg1 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[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [CrossRef] [ChemPort] [ISI]
Bis, J. A. & Zaworotko, M. J. (2005). Cryst. Growth Des. 5, 1169-1179.  [CSD] [CrossRef] [ChemPort]
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Hemamalini, M. & Fun, H.-K. (2010a). Acta Cryst. E66, o936-o937.  [CrossRef] [details]
Hemamalini, M. & Fun, H.-K. (2010b). Acta Cryst. E66, o623-o624.  [CSD] [CrossRef] [details]
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.
Nahringbauer, I. & Kvick, Å. (1977). Acta Cryst. B33, 2902-2905.  [CrossRef] [details] [ISI]
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.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o3195.  [CrossRef] [details]


Acta Cryst (2012). E68, o3196-o3197   [ doi:10.1107/S1600536812043243 ]

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