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Volume 69 
Part 6 
Page o943  
June 2013  

Received 16 April 2013
Accepted 25 April 2013
Online 22 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
R = 0.069
wR = 0.175
Data-to-parameter ratio = 12.1
Details
Open access

N-(5-Nitro-1,3-thiazol-2-yl)-4-(trifluoromethyl)benzamide

aKey Laboratory of New Animal Drug Project, Gansu Province, Key Laboratory of Veterinary Pharmaceutical Development, Ministry of Agriculture, Lanzhou Institute of Animal Science and Veterinary Pharmaceutics of CAAS, Lanzhou 730050, People's Republic of China
Correspondence e-mail: lijy1971@163.com

There are two independent and conformationally dissimilar molecules (A and B) in the asymmetric unit of the title compound, C11H6F3N3O3S; the dihedral angles between the benzene and thiazole rings are 33.8 (2)° in A and 59.7 (2)° in B. The similarity of the C-N bond lengths in the amide group [1.379 (5) and 1.358 (5) Å for A, and 1.365 (5) and 1.363 (5) Å for B] indicates the presence of conjugation between the two rings. In the crystal, molecules are linked by N-H...N hydrogen bonds, forming chains extending along [010]; weak N-H...Oamide interactions are also present in the structure.

Related literature

For the antiparasitic activity of nitazoxanide, see: Fox & Saravolatz (2005[Fox, L. M. & Saravolatz, L. D. (2005). Clin. Infect. Dis. 40, 1173-1180.]) and for the antibacterial activity of thiazolides, see: Gargala et al. (2010[Gargala, G., Le Goff, L., Ballet, J. J., Favennec, L., Stachulski, A. V. & Rossignol, J. F. (2010). Antimicrob. Agents Chemother. 54, 1315-1318.]); Stachulski et al. (2011[Stachulski, A. V., Pidathala, C., Row, E. C., Sharma, R., Berry, N. G., Iqbal, M., Bentley, J., Allman, S. A., Edwards, G., Helm, A., Hellier, J., Korba, B. E., Semple, J. E. & Rossignol, J. F. (2011). J. Med. Chem. 54, 4119-4132.]). For the synthesis and antibacterial activity of the title compound, see: Ballard et al. (2011[Ballard, T. E., Wang, X., Olekhnovich, I., Koerner, T., Seymour, C., Salamoun, J., Warthan, M., Hoffman, P. S. & Macdonald, T. L. (2011). ChemMedChem, 6, 362-377.]).

[Scheme 1]

Experimental

Crystal data
  • C11H6F3N3O3S

  • Mr = 317.26

  • Monoclinic, P 21 /c

  • a = 12.362 (4) Å

  • b = 8.946 (3) Å

  • c = 23.261 (8) Å

  • [beta] = 100.762 (4)°

  • V = 2527.2 (15) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 296 K

  • 0.34 × 0.32 × 0.25 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.903, Tmax = 0.927

  • 11671 measured reflections

  • 4588 independent reflections

  • 3183 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.069

  • wR(F2) = 0.175

  • S = 1.06

  • 4588 reflections

  • 379 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.50 e Å-3

  • [Delta][rho]min = -0.48 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N5i 0.86 2.32 3.044 (5) 142
N1-H1...O3i 0.86 2.57 3.023 (5) 115
N4-H4...N2ii 0.86 2.18 2.939 (5) 147
N4-H4...O2 0.86 2.62 3.146 (5) 121
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2257 ).


Acknowledgements

This study was supported by the earmarked fund for China Agriculture Research System (cars-38) and the program funded by the Basic Scientific Research Funds in Central Agricultural Scientific Research Institutions (1610322013005).

References

Ballard, T. E., Wang, X., Olekhnovich, I., Koerner, T., Seymour, C., Salamoun, J., Warthan, M., Hoffman, P. S. & Macdonald, T. L. (2011). ChemMedChem, 6, 362-377.  [CrossRef] [ChemPort] [PubMed]
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Fox, L. M. & Saravolatz, L. D. (2005). Clin. Infect. Dis. 40, 1173-1180.  [ISI] [CrossRef] [PubMed] [ChemPort]
Gargala, G., Le Goff, L., Ballet, J. J., Favennec, L., Stachulski, A. V. & Rossignol, J. F. (2010). Antimicrob. Agents Chemother. 54, 1315-1318.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Stachulski, A. V., Pidathala, C., Row, E. C., Sharma, R., Berry, N. G., Iqbal, M., Bentley, J., Allman, S. A., Edwards, G., Helm, A., Hellier, J., Korba, B. E., Semple, J. E. & Rossignol, J. F. (2011). J. Med. Chem. 54, 4119-4132.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o943  [ doi:10.1107/S1600536813011264 ]

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