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Volume 68 
Part 12 
Pages o3319-o3320  
December 2012  

Received 22 October 2012
Accepted 2 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.046
wR = 0.114
Data-to-parameter ratio = 18.2
Details
Open access

2-Amino-5-methylpyridinium trifluoroacetate

In the title salt, C6H9N2+·C2F3O2-, the F atoms of the anion are disordered over two sets of sites, with refined occupancies in a ratio of 0.505 (17):0.495 (17). In the crystal, cations and anions are linked via N-H...O hydrogen bonds, forming R22(8) ring motifs. The ionic units are linked into a two-dimensional network parallel to (100) by N-H...O and weak C-H...O hydrogen bonds. The crystal structure is further stabilized by weak C-H...F hydrogen bonds, 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 & Saenger (1991[Jeffrey, G. A. & Saenger, W. (1991). In Hydrogen Bonding in Biological Structures. Berlin: Springer.]); 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 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 standard 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 the 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.]). For a related structure, see: Rodrigues et al. (2001[Rodrigues, V. H., Paixão, J. A., Costa, M. M. R. R. & Matos Beja, A. (2001). Acta Cryst. C57, 417-420.]).

[Scheme 1]

Experimental

Crystal data
  • C6H9N2+·C2F3O2-

  • Mr = 222.17

  • Orthorhombic, P n a 21

  • a = 18.725 (4) Å

  • b = 4.6256 (10) Å

  • c = 11.319 (2) Å

  • V = 980.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.15 mm-1

  • T = 100 K

  • 0.54 × 0.29 × 0.11 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 = 0.926, Tmax = 0.985

  • 12012 measured reflections

  • 3216 independent reflections

  • 2627 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.114

  • S = 1.07

  • 3216 reflections

  • 177 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1368 Friedel pairs

  • Flack parameter: -0.1 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O2 0.98 (3) 1.75 (3) 2.7281 (19) 177 (2)
N2-H2N2...O1 0.95 (3) 1.92 (3) 2.865 (2) 173 (2)
N2-H1N2...O2i 0.86 (3) 1.99 (3) 2.8347 (18) 167 (3)
C3-H3A...F2ii 0.95 2.51 3.429 (6) 164
C5-H5A...O1iii 0.95 2.27 3.1910 (19) 162
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]; (iii) [-x+{\script{3\over 2}}, y+{\script{1\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: LH5549 ).


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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
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]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Jeffrey, G. A. (1997). In An Introduction of Hydrogen Bonding. Oxford University Press.
Jeffrey, G. A. & Saenger, W. (1991). In Hydrogen Bonding in Biological Structures. Berlin: Springer.
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.
Rodrigues, V. H., Paixão, J. A., Costa, M. M. R. R. & Matos Beja, A. (2001). Acta Cryst. C57, 417-420.  [CSD] [CrossRef] [ChemPort] [details]
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]


Acta Cryst (2012). E68, o3319-o3320   [ doi:10.1107/S1600536812045291 ]

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