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Volume 69 
Part 6 
Pages o841-o842  
June 2013  

Received 1 April 2013
Accepted 1 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.042
wR = 0.118
Data-to-parameter ratio = 11.1
Details
Open access

2-Amino-5-nitropyridinium trifluoroacetate

aPostgraduate and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India
Correspondence e-mail: guqmc@yahoo.com

The title salt, C5H6N3O2+·C2F3O2-, crystallizes with two cations and two anions in the asymmetric unit. In the crystal, the acetate and pyridine groups are linked by a pair of N-H...O hydrogen bonds, forming loops described by the graph-set motif R22(8). These loops are linked via N-H...O hydrogen bonds, forming chains along [001]. The chains are in turn linked by C-H...O and C-H...F hydrogen bonds, generating a three-dimensional supramolecular network. In both anions, the O and F atoms are disordered over two sites, with occupancy ratios of 0.852 (3):0.148 (3) and 0.851 (3):0.149 (3).

Related literature

For the biological properties of pyridine derivatives and compounds containing the imidazo[1,2-a]pyridine ring system, see: Trapani et al. (2003[Trapani, G., Latrofa, A., Franco, M., Carrieri, A., Cellamare, S., Serra, M., Sanna, E., Biggio, G. & Liso, G. (2003). Eur. J. Pharm. Sci. 18, 231-240.]); Gueiffier et al. (1998[Gueiffier, A., Mavel, S., Lhassani, M., Elhakmaoui, A., Snoeck, R., Andrei, G., Chavignon, O., Teulade, I. C., Witvrouw, M., Balzarini, J., De Clercq, E. & Chapat, J. P. (1998). J. Med. Chem. 41, 5108-5112.]); Rival et al. (1992[Rival, Y., Grassy, G. & Michel, G. (1992). Chem. Pharm. Bull. 40, 1170-1176.]); Rupert et al. (2003[Rupert, K. C., Henry, J. R., Dodd, J. H., Wadsworth, S. A., Cavender, D. E., Olini, G. C., Fahmy, B. & Siekierka, J. J. (2003). Bioorg. Med. Chem. Lett. 13, 347-350.]). For the crystal structure of a related compound, see: Hemamalini & Fun (2010[Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o781-o782.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C5H6N3O2+·C2F3O2-

  • Mr = 506.30

  • Monoclinic, P 21 /c

  • a = 19.1388 (7) Å

  • b = 10.7716 (4) Å

  • c = 10.0707 (3) Å

  • [beta] = 104.668 (2)°

  • V = 2008.47 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.17 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.25 mm

Data collection
  • Bruker APEXII Kappa CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.950, Tmax = 0.958

  • 18608 measured reflections

  • 4064 independent reflections

  • 3006 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.118

  • S = 1.06

  • 4064 reflections

  • 367 parameters

  • 25 restraints

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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O4'i 0.86 1.90 2.758 (12) 175
N2-H2A...O3'i 0.93 (2) 1.88 (2) 2.791 (4) 168 (2)
N2-H2B...O8ii 0.90 (2) 2.06 (2) 2.935 (7) 166 (2)
N4-H4A...O8iii 0.86 1.91 2.772 (7) 175
N5-H5A...O7iii 0.91 (2) 1.86 (2) 2.763 (9) 172 (2)
N5-H5B...O3'iv 0.87 (2) 1.97 (2) 2.801 (3) 160 (2)
C1-H1...O7v 0.93 2.36 3.140 (5) 141
C4-H4...O2iv 0.93 2.57 3.264 (3) 132
C8-H8...F1'vi 0.93 2.44 3.089 (3) 127
C8-H8...O4'vi 0.93 2.36 3.253 (7) 161
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+2, -y, -z+2; (iii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iv) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (v) -x+2, -y+1, -z+2; (vi) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2582 ).


Acknowledgements

The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection and computer facilities.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Gueiffier, A., Mavel, S., Lhassani, M., Elhakmaoui, A., Snoeck, R., Andrei, G., Chavignon, O., Teulade, I. C., Witvrouw, M., Balzarini, J., De Clercq, E. & Chapat, J. P. (1998). J. Med. Chem. 41, 5108-5112.  [ISI] [CrossRef] [ChemPort] [PubMed]
Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o781-o782.  [CrossRef] [ChemPort] [details]
Rival, Y., Grassy, G. & Michel, G. (1992). Chem. Pharm. Bull. 40, 1170-1176.  [CrossRef] [PubMed] [ChemPort]
Rupert, K. C., Henry, J. R., Dodd, J. H., Wadsworth, S. A., Cavender, D. E., Olini, G. C., Fahmy, B. & Siekierka, J. J. (2003). Bioorg. Med. Chem. Lett. 13, 347-350.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Trapani, G., Latrofa, A., Franco, M., Carrieri, A., Cellamare, S., Serra, M., Sanna, E., Biggio, G. & Liso, G. (2003). Eur. J. Pharm. Sci. 18, 231-240.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o841-o842   [ doi:10.1107/S1600536813011896 ]

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