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

Mohamed, S.K.; Akkurt, M.; Horton, P.N.; Abdelhamid, A.A.; Marzouk, A.A.

doi:10.1107/S1600536812050696

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 (C-C) = 0.003 Å
R = 0.025
wR = 0.059
Data-to-parameter ratio = 15.4
Details

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

Shaaban K. Mohamed,^a,^b Mehmet Akkurt,^c ^* Peter N. Horton,^d Antar A. Abdelhamid ^a,^b and Adel A. Marzouk ^e

^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-HN hydrogen bond, forming an S(6) ring motif. In the crystal, pairs of molecules are linked via two pairs of C-HO 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); Kalaivani et al. (2012); Blair et al. (2000). For the synthesis of fluorinated azomethines, see: Mohamed et al. (2012). For hydrogen-bond motifs, see: Bernstein et al. (1995). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₁₃H₈BrFN₂O₃
M_r = 339.11
Monoclinic, P 2₁ /n
a = 4.5082 (9) Å
b = 19.815 (4) Å
c = 13.853 (3) Å
= 95.484 (5)°
V = 1231.8 (4) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.500, T_max = 0.906
8107 measured reflections
2811 independent reflections
2633 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.025
wR(F²) = 0.059
S = 1.05
2811 reflections
182 parameters
H-atom parameters constrained
_max = 0.52 e Å^-3
_min = -0.54 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.84	1.86	2.601 (2)	146
C7-H7O3ⁱ	0.95	2.45	3.399 (3)	173
C13-H13O3ⁱ	0.95	2.48	3.430 (3)	173
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: CrystalClear-SM Expert (Rigaku, 2012); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

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

organic compounds