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Volume 69 
Part 1 
Page o107  
January 2013  

Received 12 December 2012
Accepted 13 December 2012
Online 19 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.025
wR = 0.059
Data-to-parameter ratio = 15.4
Details
Open access

4-Bromo-2-[(E)-(2-fluoro-5-nitrophenyl)iminomethyl]phenol

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,bChemistry Department, Faculty of Science, Minia University, El-Minia, Egypt,cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,dSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, England, and ePharmaceutical Chemistry Department, Faculty of Pharmacy, Al AzharUniversity, Egypt
Correspondence e-mail: akkurt@erciyes.edu.tr

The molecular conformation of the title compound, C13H8BrFN2O3, is essentially planar, with maximum deviations of 0.076 (1) and -0.080 (2) Å for the O atoms of the NO2 group. The molecular conformation is stabilized by an intramolecular O-H...N hydrogen bond, forming an S(6) ring motif. In the crystal, pairs of molecules are linked via two pairs of C-H...O hydrogen bonds, forming inversion dimers that enclose R22(7)R22(10)R22(7) ring motifs.

Related literature

For the synthesis and biological activity of azomethines, see: Przybylski et al. (2009[Przybylski, P., Huczynski, A., Pyta, K. & Bartl, B. (2009). Curr. Org. Chem. 13, 124-130.]); Kalaivani et al. (2012[Kalaivani, S., Priya, N. P. & Arunachalam, S. (2012). Int. J. Appl. Biol. Pharm. Technol. 3, 219-223.]); 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.]). For the synthesis of fluorinated azomethines, 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 hydrogen-bond 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
  • C13H8BrFN2O3

  • Mr = 339.11

  • Monoclinic, P 21 /n

  • a = 4.5082 (9) Å

  • b = 19.815 (4) Å

  • c = 13.853 (3) Å

  • [beta] = 95.484 (5)°

  • V = 1231.8 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.36 mm-1

  • T = 100 K

  • 0.24 × 0.04 × 0.03 mm

Data collection
  • Rigaku AFC12 (Right) diffractometer

  • Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012[Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.500, Tmax = 0.906

  • 8107 measured reflections

  • 2811 independent reflections

  • 2633 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.025

  • wR(F2) = 0.059

  • S = 1.05

  • 2811 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.54 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.84 1.86 2.601 (2) 146
C7-H7...O3i 0.95 2.45 3.399 (3) 173
C13-H13...O3i 0.95 2.48 3.430 (3) 173
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: CrystalClear-SM Expert (Rigaku, 2012[Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: XU5665 ).


Acknowledgements

The EPSRC National Crystallography Service is gratefully acknowledged for the X-ray diffraction data. AAA and SKM thank the Ministry of Higher Education of Egypt for financial support of this collaporative project. The authors are also thankful to Manchester Metropolitan University and Erciyes University for supporting this study.

References

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]
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]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kalaivani, S., Priya, N. P. & Arunachalam, S. (2012). Int. J. Appl. Biol. Pharm. Technol. 3, 219-223.  [ChemPort]
Mohamed, S. K., Abdelhamid, A. A., Akkurt, M., Fanwick, P. E. & Maharramov, A. M. (2012). Acta Cryst. E68, o1618.  [CSD] [CrossRef] [details]
Przybylski, P., Huczynski, A., Pyta, K. & Bartl, B. (2009). Curr. Org. Chem. 13, 124-130.  [CrossRef] [ChemPort]
Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o107  [ doi:10.1107/S1600536812050696 ]

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