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Volume 69 
Part 7 
Pages o1083-o1084  
July 2013  

Received 19 April 2013
Accepted 29 May 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 290 K
Mean [sigma](C-C) = 0.004 Å
R = 0.041
wR = 0.114
Data-to-parameter ratio = 13.6
Details
Open access

4-{5-[(2-Bromobenzyl)sulfanyl]-1H-tetrazol-1-yl}benzoic 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, C15H11BrN4O2S, the tetrazole ring makes dihedral angles of 45.97 (10) and 75.41 (1)°, respectively, with the benzoyl and bromobenzene rings while the dihedral angle between the benzene rings is 73.77 (1)°. In the crystal, molecules are linked through O-H... N and C-H... O hydrogen bonds, giving infinite chains in both the [110] and [1-10] directions. These chains are further connected by C-Br...[pi] and C-O...[pi] interactions and also by [pi]-[pi] stacking between tetrazole rings [centroid-centroid distance = 3.312 (1) Å], generating a three-dimensional network.

Related literature

For details of the ZINC database, see: Irwin et al. (2012[Irwin, J. J., Sterling, T., Mysinger, M. M., Bolstad, E. S. & Coleman, R. G. (2012). J. Chem. Inf. Model. 52, 1757-1768.]). For 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 et al. (2013[Mafud, A. C., Mascarenhas, Y. P. & Nascimento, A. S. (2013). Acta Cryst. E69, o759.]).

[Scheme 1]

Experimental

Crystal data
  • C15H11BrN4O2S

  • Mr = 391.25

  • Monoclinic, P 21 /n

  • a = 7.4570 (5) Å

  • b = 8.3500 (5) Å

  • c = 25.3680 (14) Å

  • [beta] = 97.626 (3)°

  • V = 1565.59 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.77 mm-1

  • T = 290 K

  • 0.1 x 0.1 (radius) mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: for a cylinder mounted on the [varphi] axis (modified Dwiggins, 1975[Dwiggins, C. W. (1975). Acta Cryst. A31, 146-148.]) Tmin = 0.604, Tmax = 0.608

  • 24464 measured reflections

  • 2889 independent reflections

  • 2388 reflections with I > 2[sigma](I)

  • Rint = 0.069

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.114

  • S = 1.06

  • 2889 reflections

  • 213 parameters

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

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.47 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1-N4/C8 tetrazole ring and the C10-C15 benzene ring, respectively.

D-H...A D-H H...A D...A D-H...A
C9-H9B...O1i 0.97 2.41 3.351 (4) 163
O2-H1...N4ii 0.73 (4) 2.05 (4) 2.746 (3) 161 (5)
C1-O1...Cg1iii 1.21 (1) 3.62 (1) 4.534 (1) 133 (2)
C11-Br1...Cg2iv 1.90 (1) 3.58 (1) 4.895 (2) 124 (1)
Symmetry codes: (i) x+1, y-1, z; (ii) x-1, y+1, z; (iii) x, y+1, z; (iv) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: LR2105 ).


Acknowledgements

We are grateful to 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] [IUCr Journals]
Dwiggins, C. W. (1975). Acta Cryst. A31, 146-148.  [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Irwin, J. J., Sterling, T., Mysinger, 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] [Web of Science]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Mafud, A. C., Mascarenhas, Y. P. & Nascimento, A. S. (2013). Acta Cryst. E69, o759.  [CrossRef] [IUCr Journals]
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.  [Web of Science] [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] [IUCr Journals]


Acta Cryst (2013). E69, o1083-o1084   [ doi:10.1107/S1600536813014840 ]

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