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

Akkurt, M.; Kennedy, A.R.; Mohamed, S.K.; Abdelhamid, A.A.; Miller, G.J.

doi:10.1107/S1600536812042262

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 (C-C) = 0.005 Å
R = 0.050
wR = 0.090
Data-to-parameter ratio = 15.5
Details

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

Mehmet Akkurt,^a ^* Alan R. Kennedy,^b Shaaban K. Mohamed,^c Antar A. Abdelhamid ^c and Gary J. Miller ^d

^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-HN 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); Chawla et al. (2012); Bella et al. (2004); Chandra & Kumar (2005); Yang et al. (2000). For the synthesis of a similar azomethine compound, see: Mohamed et al. (2012). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₄H₈BrF₃N₂O₃
M_r = 389.12
Monoclinic, P 2₁ /n
a = 7.3596 (5) Å
b = 16.4625 (10) Å
c = 11.2599 (6) Å
= 94.955 (5)°
V = 1359.12 (14) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.546, T_max = 0.575
6329 measured reflections
3149 independent reflections
2165 reflections with I > 2(I)
R_int = 0.043

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.090
S = 1.02
3149 reflections
203 parameters
1 restraint
H-atom parameters constrained
_max = 0.51 e Å^-3
_min = -0.59 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H1ON1	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

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.
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.
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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Mohamed, S. K., Abdelhamid, A. A., Akkurt, M., Fanwick, P. E. & Maharramov, A. M. (2012). Acta Cryst. E68, o1618.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yang, Z.-Y., Yang, R.-D., Li, F.-S. & Yu, K.-B. (2000). Polyhedron, 19, 2599-2604.

organic compounds