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Volume 69 
Part 5 
Page o759  
May 2013  

Received 7 March 2013
Accepted 9 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 290 K
Mean [sigma](C-C) = 0.004 Å
R = 0.051
wR = 0.150
Data-to-parameter ratio = 14.0
Details
Open access

2-({1-[2-(Methylsulfanyl)phenyl]-1H-tetrazol-5-yl}sulfanyl)acetic acid

aInstituto de Física de São Carlos, Av. do Trab. Sãocarlense, 400, São Carlos, SP, Brazil
Correspondence e-mail: mafud@usp.br

In the title compound, C10H10N4O2S2, the tetrazole and benzene rings are almost normal to one another, with a dihedral angle between their planes of 84.33 (9)°. In the crystal, molecules are linked via pairs of bifurcated O-H...(N,N) hydrogen bonds, forming inversion dimers with graph-set motif R44(12). The dimers are linked by significant [pi]-[pi] interactions involving inversion-related tetrazole rings and inversion-related benzene rings, with centroid-centroid distances of 3.7376 (14) and 3.8444 (15) Å, respectively.

Related literature

For details of the ZINC database, see: Irwin et al. (2012[Irwin, J. J., Sterling, T., Mnosinger, M. M., Bolstad, E. S. & Coleman, R. G. (2012). J. Chem. Inf. Model. 52, 1757-1768.]). For information on the biological properties of tetrazoles, see: Kees et al. (1989[Kees, K. L., Cheeseman, R. S., Prozialeck, D. H. & Steiner, K. E. (1989). J. Med. Chem. 32, 11-13.]); Nolte et al. (1998[Nolte, R. T., Wisely, G. B., Westin, S., Cobb, J. E., Lambert, M. H., Kurokawa, R., Rosenfeldk, M. G., Willson, T. M., Glass, C. K. & Milburn, M. V. (1998). Nature, 395, 137-143.]); Mafud & Nascimento (2013[Mafud, A. C. & Nascimento, A. S. (2013). In preparation.]).

[Scheme 1]

Experimental

Crystal data
  • C10H10N4O2S2

  • Mr = 282.34

  • Triclinic, [P \overline 1]

  • a = 7.1500 (3) Å

  • b = 8.3770 (3) Å

  • c = 11.0890 (5) Å

  • [alpha] = 74.7480 (14)°

  • [beta] = 79.3090 (14)°

  • [gamma] = 86.286 (3)°

  • V = 629.58 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.42 mm-1

  • T = 290 K

  • 0.1 × 0.05 × 0.05 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer

  • Absorption correction: for a cylinder mounted on the [varphi] axis (Dwiggins, 1975[Dwiggins, C. W. (1975). Acta Cryst. A31, 146-148.]) Tmin = 0.861, Tmax = 0.862

  • 15888 measured reflections

  • 2335 independent reflections

  • 1879 reflections with I > 2[sigma](I)

  • Rint = 0.079

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.15

  • S = 1.04

  • 2335 reflections

  • 167 parameters

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

  • [Delta][rho]max = 0.50 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
O1-H1...N1i 0.81 (4) 2.15 (4) 2.952 (4) 176 (4)
O1-H1...N2i 0.81 (4) 2.51 (4) 3.232 (4) 149 (4)
Symmetry code: (i) -x+1, -y, -z.

Data collection: COLLECT (Nonius, 1999[Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2571 ).


Acknowledgements

We are grateful to the CAPES National Council for the Improvement of Higher Education and FAPESP São Paulo Research Foundation for supporting this study.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Dwiggins, C. W. (1975). Acta Cryst. A31, 146-148.  [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Irwin, J. J., Sterling, T., Mnosinger, M. M., Bolstad, E. S. & Coleman, R. G. (2012). J. Chem. Inf. Model. 52, 1757-1768.  [CrossRef] [ChemPort]
Kees, K. L., Cheeseman, R. S., Prozialeck, D. H. & Steiner, K. E. (1989). J. Med. Chem. 32, 11-13.  [CrossRef] [ChemPort] [PubMed] [ISI]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Mafud, A. C. & Nascimento, A. S. (2013). In preparation.
Nolte, R. T., Wisely, G. B., Westin, S., Cobb, J. E., Lambert, M. H., Kurokawa, R., Rosenfeldk, M. G., Willson, T. M., Glass, C. K. & Milburn, M. V. (1998). Nature, 395, 137-143.  [ISI] [ChemPort] [PubMed]
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o759  [ doi:10.1107/S160053681300980X ]

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