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Volume 70 
Part 1 
Page o91  
January 2014  

Received 22 November 2013
Accepted 17 December 2013
Online 24 December 2013

Key indicators
Single-crystal X-ray study
T = 130 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.099
Data-to-parameter ratio = 17.7
Details
Open access

1-(1-Benzo­furan-2-yl)ethanone O-(2,6-di­fluoro­benz­yl)oxime

aDepartment of Organic Chemistry, Ludwik Rydygier Collegium Medicum in Bydgoszcz, Nicolaus Copernicus University in Torun, ul. A. Jurasza 2, 85-089 Bydgoszcz, Poland, and bDepartment of Organic Chemistry, Poznan University of Medical Sciences, ul. Grunwaldzka 6, 60-780 Poznan, Poland
Correspondence e-mail: akgzella@ump.edu.pl

In the title compound, C17H13F2NO2, the 2,2-di­fluoro­benz­yloxy residue assumes an E configuration with respect to the benzo­furan system. The benzene ring makes a dihedral angle of 61.70 (4)° with the fused ring system (r.m.s. deviation = 0.008 Å). In the crystal, mol­ecules are connected by weak C-H...F hydrogen bonds into chains extending parallel to the b-axis direction.

Related literature

For background to anti­fungal agents, see: Benedetti & Bani (1999[Benedetti, M. S. & Bani, M. (1999). Drug Metab. Rev. 31, 665-717.]); Sheehan et al. (1999[Sheehan, D. J., Hitchcock, Ch. A. & Sibley, C. M. (1999). Clin. Microbiol. Rev. 12, 40-79.]). For the biological activity of oximes and their ethers, see: Attia et al. (2013[Attia, M. I., Zakaria, A. S., Almutairi, M. S. & Ghoneim, S. W. (2013). Molecules, 18, 12208-12221.]); De Luca (2006[De Luca, L. (2006). Curr. Med. Chem. 69, 21-28.]); Emami et al. (2004[Emami, S., Falahati, M., Banifetami, A. & Shafiee, A. (2004). Bioorg. Med. Chem. 12, 5881-5889.]); Karakurt et al. (2001[Karakurt, A., Dalkara, S., Özalp, M., Özbey, S., Kendi, E. & Stables, J. P. (2001). Eur. J. Med. Chem. 36, 421-433.]); Massolini et al. (1993[Massolini, G., Carmellino, M. L., Kitsos, M. & Baruffini, A. (1993). Il Farmaco, 48, 503-514.]); Mixich & Thiele (1985[Mixich, G. & Thiele, K. (1985). US Patent 4 550 175.]). For the synthesis of the title compound, see: Demirayak et al. (2002[Demirayak, S., Uçucu, Ü., Benkli, K., Gündogdu-Karaburun, N., Karaburun, A., Akar, D., Karabacak, M. & Kiraz, N. (2002). Il Farmaco, 57, 609-612.]).

[Scheme 1]

Experimental

Crystal data
  • C17H13F2NO2

  • Mr = 301.28

  • Monoclinic, P 21 /n

  • a = 7.36652 (17) Å

  • b = 17.0314 (4) Å

  • c = 11.2047 (2) Å

  • [beta] = 90.020 (2)°

  • V = 1405.76 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 130 K

  • 0.35 × 0.15 × 0.12 mm

Data collection
  • Agilent Xcalibur Atlas diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.992, Tmax = 1.000

  • 24335 measured reflections

  • 3548 independent reflections

  • 2887 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.099

  • S = 1.03

  • 3548 reflections

  • 200 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...F22i 0.93 2.54 3.3537 (16) 147
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). 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, 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: ZS2281 ).


References

Agilent (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Attia, M. I., Zakaria, A. S., Almutairi, M. S. & Ghoneim, S. W. (2013). Molecules, 18, 12208-12221.  [CrossRef] [PubMed]
Benedetti, M. S. & Bani, M. (1999). Drug Metab. Rev. 31, 665-717.  [CrossRef] [PubMed]
De Luca, L. (2006). Curr. Med. Chem. 69, 21-28.
Demirayak, S., Uçucu, Ü., Benkli, K., Gündogdu-Karaburun, N., Karaburun, A., Akar, D., Karabacak, M. & Kiraz, N. (2002). Il Farmaco, 57, 609-612.  [CrossRef] [PubMed] [ChemPort]
Emami, S., Falahati, M., Banifetami, A. & Shafiee, A. (2004). Bioorg. Med. Chem. 12, 5881-5889.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Karakurt, A., Dalkara, S., Özalp, M., Özbey, S., Kendi, E. & Stables, J. P. (2001). Eur. J. Med. Chem. 36, 421-433.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Massolini, G., Carmellino, M. L., Kitsos, M. & Baruffini, A. (1993). Il Farmaco, 48, 503-514.  [ChemPort] [PubMed]
Mixich, G. & Thiele, K. (1985). US Patent 4 550 175.
Sheehan, D. J., Hitchcock, Ch. A. & Sibley, C. M. (1999). Clin. Microbiol. Rev. 12, 40-79.  [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o91  [ doi:10.1107/S1600536813034090 ]

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