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Volume 68 
Part 11 
Page o3168  
November 2012  

Received 7 October 2012
Accepted 9 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.005 Å
R = 0.050
wR = 0.090
Data-to-parameter ratio = 15.5
Details
Open access

4-Bromo-2-[(E)-{[4-nitro-2-(trifluoromethyl)phenyl]imino}methyl]phenol

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland,cChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, and dAnalytical Sciences, Manchester Metropolitan University, Manchester, M1 5GD, England
Correspondence e-mail: akkurt@erciyes.edu.tr

Except two F atoms of the -CF3 group, the title compound, C14H8BrF3N2O3, has an almost planar conformation, the dihedral angle between the aromatic rings being 3.60 (16)°. The molecule adopts the enol-imine tautomeric form, with an intramolecular O-H...N hydrogen bond, which generates an S(6) ring motif. In the crystal, face-to-face [pi]-[pi] stacking [centroid-centroid distances = 3.669 (2) and 3.732 (2) Å] between the aromatic rings of the molecules, which lie in sheets parallel to (202), help to establish the packing.

Related literature

For the biological activity of fluorine-containing compounds, see: Blair et al. (2000[Blair, J. B., Kurrasch-Orbaugh, D., Marona-Lewicka, D., Cumbay, M. G., Watts, V. J., Barker, E. L. & Nichols, D. E. (2000). J. Med. Chem. 43, 4701-4710.]); Chawla et al. (2012[Chawla, P., Singh, R. & Saraf, S. K. (2012). Med. Chem. Res. 21, 3263-3271.]); Bella et al. (2004[Bella, S. D., Fragala, I., Leonardi, N. & Sortino, S. (2004). Inorg. Chim. Acta, 357, 3865-3870.]); Chandra & Kumar (2005[Chandra, S. & Kumar, U. (2005). Spectrochim. Acta Part A, 61, 219-224.]); Yang et al. (2000[Yang, Z.-Y., Yang, R.-D., Li, F.-S. & Yu, K.-B. (2000). Polyhedron, 19, 2599-2604.]). For the synthesis of a similar azomethine compound, see: Mohamed et al. (2012[Mohamed, S. K., Abdelhamid, A. A., Akkurt, M., Fanwick, P. E. & Maharramov, A. M. (2012). Acta Cryst. E68, o1618.]). For the graph-set analysis of hydrogen bonding, 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
  • C14H8BrF3N2O3

  • Mr = 389.12

  • Monoclinic, P 21 /n

  • a = 7.3596 (5) Å

  • b = 16.4625 (10) Å

  • c = 11.2599 (6) Å

  • [beta] = 94.955 (5)°

  • V = 1359.12 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.08 mm-1

  • T = 123 K

  • 0.20 × 0.18 × 0.18 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.546, Tmax = 0.575

  • 6329 measured reflections

  • 3149 independent reflections

  • 2165 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.090

  • S = 1.02

  • 3149 reflections

  • 203 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.51 e Å-3

  • [Delta][rho]min = -0.59 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H1O...N1 0.84 1.88 2.623 (4) 146

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5632 ).


Acknowledgements

Manchester Metropolitan University, Erciyes University and the University of Strathclyde are gratefully acknowledged for supporting this study.

References

Bella, S. D., Fragala, I., Leonardi, N. & Sortino, S. (2004). Inorg. Chim. Acta, 357, 3865-3870.  [ISI] [CSD] [CrossRef]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Blair, J. B., Kurrasch-Orbaugh, D., Marona-Lewicka, D., Cumbay, M. G., Watts, V. J., Barker, E. L. & Nichols, D. E. (2000). J. Med. Chem. 43, 4701-4710.  [ISI] [CrossRef] [PubMed] [ChemPort]
Chandra, S. & Kumar, U. (2005). Spectrochim. Acta Part A, 61, 219-224.
Chawla, P., Singh, R. & Saraf, S. K. (2012). Med. Chem. Res. 21, 3263-3271.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Mohamed, S. K., Abdelhamid, A. A., Akkurt, M., Fanwick, P. E. & Maharramov, A. M. (2012). Acta Cryst. E68, o1618.  [CSD] [CrossRef] [details]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yang, Z.-Y., Yang, R.-D., Li, F.-S. & Yu, K.-B. (2000). Polyhedron, 19, 2599-2604.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3168  [ doi:10.1107/S1600536812042262 ]

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