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Volume 69 
Part 4 
Page o535  
April 2013  

Received 25 February 2013
Accepted 11 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
R = 0.050
wR = 0.092
Data-to-parameter ratio = 13.7
Details
Open access

1-{(E)-[4-Bromo-2-(trifluoromethoxy)phenyl]iminomethyl}naphthalen-2-ol

aDepartment of Physics, Faculty of Arts & Science, Ondokuz Mayis University, TR-55139 Kurupelit-Samsun, Turkey,bDepartment of Chemistry, Faculty of Arts & Science, Ondokuz Mayis University, TR-55139 Kurupelit-Samsun, Turkey, and cDepartment of Medical Services and Techniques, Vocational School of Health Services, Giresun University, TR-28200 Giresun, Turkey
Correspondence e-mail: gokhan.alpaslan@giresun.edu.tr

The title compound, C18H11BrF3NO2, crystallizes in the phenol-imine tautomeric form, with a strong intramolecular O-H...N hydrogen bond. The dihedral angle between the naphthalene ring system and the benzene ring is 28.54 (10)°.

Related literature

For biological properties of Schiff bases, see: Layer (1963[Layer, R. W. (1963). Chem. Rev. 63, 489-510.]); Ingold (1969[Ingold, C. K. (1969). In Structure and Mechanism in Organic Chemistry, 2nd ed. Ithaca: Cornell University Press.]); Barton & Ollis (1979[Barton, D. & Ollis, W. D. (1979). In Comprehensive Organic Chemistry, Vol 2. Oxford: Pergamon.]). For Schiff base tautomerism, see: Hökelek et al. (2000[Hökelek, T., Kiliç, Z., Isiklan, M. & Toy, M. (2000). J. Mol. Struct. 523, 61-69.]); Tüfekçi et al. (2009[Tüfekçi, M., Bingöl Alpaslan, Y., Macit, M. & Erdönmez, A. (2009). Acta Cryst. E65, o2704.]). For related strucures, see: Bingöl Alpaslan et al. (2010[Bingöl Alpaslan, Y., Alpaslan, G., Agar, A. & Isik, S. (2010). Acta Cryst. E66, o510.]); Soydemir et al. (2011[Soydemir, E., Büyükgüngör, O., Albayrak, Ç. & Odabasoglu, M. (2011). Acta Cryst. E67, o599-o600.]).

[Scheme 1]

Experimental

Crystal data
  • C18H11BrF3NO2

  • Mr = 410.19

  • Monoclinic, P 21 /c

  • a = 4.5315 (3) Å

  • b = 16.3228 (7) Å

  • c = 21.7622 (12) Å

  • [beta] = 93.025 (4)°

  • V = 1607.44 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.60 mm-1

  • T = 296 K

  • 0.73 × 0.32 × 0.08 mm

Data collection
  • Stoe IPDS-II diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.176, Tmax = 0.772

  • 17993 measured reflections

  • 3160 independent reflections

  • 1932 reflections with I > 2[sigma](I)

  • Rint = 0.080

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

  • wR(F2) = 0.092

  • S = 1.02

  • 3160 reflections

  • 230 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.85 (5) 1.77 (6) 2.551 (5) 151 (5)

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); 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.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2500 ).


Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS-II diffractometer (purchased under grant No. F279 of the University Research Fund).

References

Barton, D. & Ollis, W. D. (1979). In Comprehensive Organic Chemistry, Vol 2. Oxford: Pergamon.
Bingöl Alpaslan, Y., Alpaslan, G., Agar, A. & Isik, S. (2010). Acta Cryst. E66, o510.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hökelek, T., Kiliç, Z., Isiklan, M. & Toy, M. (2000). J. Mol. Struct. 523, 61-69.  [ISI] [CrossRef] [ChemPort]
Ingold, C. K. (1969). In Structure and Mechanism in Organic Chemistry, 2nd ed. Ithaca: Cornell University Press.
Layer, R. W. (1963). Chem. Rev. 63, 489-510.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Soydemir, E., Büyükgüngör, O., Albayrak, Ç. & Odabasoglu, M. (2011). Acta Cryst. E67, o599-o600.  [CSD] [CrossRef] [details]
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Tüfekçi, M., Bingöl Alpaslan, Y., Macit, M. & Erdönmez, A. (2009). Acta Cryst. E65, o2704.  [CrossRef] [details]


Acta Cryst (2013). E69, o535  [ doi:10.1107/S160053681300679X ]

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