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Volume 69 
Part 9 
Pages o1425-o1426  
September 2013  

Received 20 July 2013
Accepted 7 August 2013
Online 14 August 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.048
wR = 0.136
Data-to-parameter ratio = 9.0
Details
Open access

3-Amino-1H-pyrazol-2-ium trifluoroacetate

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
Correspondence e-mail: jjasinski@keene.edu

The asymmetric unit of the title salt, C3H6N3+·C2F3O2-, contains two independent 3-aminopyrazolium cations and two independent trifluoroacetate anions. The F atoms of both anions were refined as disordered over two sets of sites, with common occupancy ratios of 0.639 (12):0.361 (12). In the crystal, the cations and anions are linked via N-H...O hydrogen bonds, forming chains along [100] and [010].

Related literature

For biological properties of pyrazole derivatives, see: Hall et al. (2008[Hall, A., Billinton, A., Brown, S. H., Clayton, N. M., Chowdhury, A., Gerald, M. P., Goldsmith, G. P., Hayhow, T. G., Hurst, D. N., Kilford, I. R., Naylor, A. & Passingham, B. (2008). Bioorg. Med. Chem. Lett. 18, 3392-3399.]); Isloor et al. (2009[Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784-3787.]); Patel et al. (2010[Patel, C. K., Rami, C. S., Panigrahi, B. & Patel, C. N. (2010). J. Chem. Pharm. Res. 2, 73-78.]); Samshuddin et al. (2010[Samshuddin, S., Narayana, B., Yathirajan, H. S., Safwan, A. P. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1279-o1280.]). For the chemistry of aminopyrazoles, see: Giuseppe et al. (1991[Giuseppe, D., Salvatore, P. & Demetrio, R. (1991). Trends Heterocycl. Chem. 2, 97.]). For the medicinal activity of pyrazoles, see: Vinogradov et al. (1994[Vinogradov, V. M., Dalinger, I. L. & Shevelev, S. A. (1994). Khim. Farm. Zh. 28, 37-46.]). For related structures, see: Dobson & Gerkin (1998[Dobson, A. J. & Gerkin, R. E. (1998). Acta Cryst. C54, 253-256.]); Foces-Foces et al. (1996[Foces-Foces, C., Cativiela, C., Zurbano, M. M., Sobrados, I., Jagerovic, N. & Elguero, J. (1996). J. Chem. Crystallogr. 26, 579-584.]); Hemamalini & Fun (2010[Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o783-o784.]); Thanigaimani et al. (2012[Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o3319-o3320.]). For hydrogen-bond graph-set 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 lengths, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C3H6N3+·C2F3O2-

  • Mr = 197.13

  • Monoclinic, P 21 /n

  • a = 10.9292 (8) Å

  • b = 10.9332 (6) Å

  • c = 13.7002 (13) Å

  • [beta] = 107.939 (9)°

  • V = 1557.5 (2) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 1.58 mm-1

  • T = 173 K

  • 0.16 × 0.14 × 0.06 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.662, Tmax = 1.000

  • 9227 measured reflections

  • 3031 independent reflections

  • 2343 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.136

  • S = 1.05

  • 3031 reflections

  • 338 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1A-H1AA...O1Ai 0.85 (3) 2.28 (3) 2.936 (3) 134 (2)
N1A-H1AB...O2Aii 0.91 (3) 1.99 (3) 2.884 (3) 169 (3)
N2A-H2AA...O1Aii 0.94 (3) 1.85 (3) 2.778 (2) 171 (3)
N3A-H3AA...O2A 0.93 (3) 1.78 (3) 2.705 (2) 172 (3)
N1B-H1BA...O2Biii 0.84 (3) 2.18 (3) 2.962 (2) 153 (2)
N1B-H1BB...O2Biv 0.90 (3) 2.03 (3) 2.929 (3) 173 (2)
N2B-H2BA...O1Biv 0.95 (3) 1.81 (3) 2.756 (2) 174 (2)
N3B-H3BA...O1Bv 0.91 (3) 1.82 (3) 2.728 (2) 171 (2)
Symmetry codes: (i) x, y+1, z; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x+1, -y+1, -z+1; (iv) x, y-1, z; (v) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5637 ).


Acknowledgements

TSY thanks the University of Mysore for research facilities and is also grateful to the Principal, Maharani's Science College for Women, Mysore, for giving permission to do research. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
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]
Dobson, A. J. & Gerkin, R. E. (1998). Acta Cryst. C54, 253-256.  [CSD] [CrossRef] [details]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Foces-Foces, C., Cativiela, C., Zurbano, M. M., Sobrados, I., Jagerovic, N. & Elguero, J. (1996). J. Chem. Crystallogr. 26, 579-584.  [ChemPort]
Giuseppe, D., Salvatore, P. & Demetrio, R. (1991). Trends Heterocycl. Chem. 2, 97.
Hall, A., Billinton, A., Brown, S. H., Clayton, N. M., Chowdhury, A., Gerald, M. P., Goldsmith, G. P., Hayhow, T. G., Hurst, D. N., Kilford, I. R., Naylor, A. & Passingham, B. (2008). Bioorg. Med. Chem. Lett. 18, 3392-3399.  [CrossRef] [PubMed] [ChemPort]
Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o783-o784.  [CrossRef] [ChemPort] [details]
Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784-3787.  [ISI] [CrossRef] [PubMed] [ChemPort]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [ISI] [CrossRef] [ChemPort] [details]
Patel, C. K., Rami, C. S., Panigrahi, B. & Patel, C. N. (2010). J. Chem. Pharm. Res. 2, 73-78.  [ChemPort]
Samshuddin, S., Narayana, B., Yathirajan, H. S., Safwan, A. P. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1279-o1280.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o3319-o3320.  [CSD] [CrossRef] [ChemPort] [details]
Vinogradov, V. M., Dalinger, I. L. & Shevelev, S. A. (1994). Khim. Farm. Zh. 28, 37-46.  [ChemPort]


Acta Cryst (2013). E69, o1425-o1426   [ doi:10.1107/S1600536813022204 ]

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