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Volume 68 
Part 11 
Page o3178  
November 2012  

Received 11 October 2012
Accepted 11 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 130 K
Mean [sigma](C-C) = 0.003 Å
R = 0.056
wR = 0.137
Data-to-parameter ratio = 17.8
Details
Open access

1-(1-Benzofuran-2-yl)ethanone O-(4-chlorobenzyl)oxime

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

In the title compound, C17H14ClNO2, the p-chlorobenzyloxy residue assumes an E conformation with respect to the benzofuran system. The carbo- and heterocyclic systems make a dihedral angle of 47.99 (4)°. In the crystal, there are no significant intermolecular interactions present.

Related literature

For the biological activity of free oximes and their ethers, see: Chern et al. (2004[Chern, J.-H., Lee, C.-C., Chang, C.-S., Lee, Y.-C., Tai, C. L., Lin, Y.-T., Shia, K.-S., Lee, C.-Y. & Shih, S.-R. (2004). Bioorg. Med. Chem. Lett. 14, 5051-5056.]); Emami et al. (2004[Emami, S., Falahati, M., Banifatemi, A., Amanlou, M. & Shafiee, A. (2004). Bioorg. Med. Chem. 12, 3971-3976.]); 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.]); Bhandari et al. (2009[Bhandari, K., Srinivas, N., Keshava, S. & Shukla, P. (2009). Eur. J. Med. Chem. 44, 437-447.]); Jindal et al. (2003[Jindal, D. P., Chattopadhaya, R., Guleria, S. & Gupta, R. (2003). Eur. J. Med. Chem. 38, 1025-1034.]); 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.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14ClNO2

  • Mr = 299.74

  • Triclinic, [P \overline 1]

  • a = 5.8842 (4) Å

  • b = 7.1173 (6) Å

  • c = 17.2313 (16) Å

  • [alpha] = 93.802 (7)°

  • [beta] = 97.998 (7)°

  • [gamma] = 95.363 (7)°

  • V = 709.19 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 130 K

  • 0.50 × 0.40 × 0.05 mm

Data collection
  • Agilent Xcalibur Atlas diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.783, Tmax = 1.000

  • 9366 measured reflections

  • 3407 independent reflections

  • 2817 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.137

  • S = 1.10

  • 3407 reflections

  • 191 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.77 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]), 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: BT6848 ).


References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Bhandari, K., Srinivas, N., Keshava, S. & Shukla, P. (2009). Eur. J. Med. Chem. 44, 437-447.  [ISI] [CrossRef] [PubMed] [ChemPort]
Chern, J.-H., Lee, C.-C., Chang, C.-S., Lee, Y.-C., Tai, C. L., Lin, Y.-T., Shia, K.-S., Lee, C.-Y. & Shih, S.-R. (2004). Bioorg. Med. Chem. Lett. 14, 5051-5056.  [CrossRef] [PubMed] [ChemPort]
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., Banifatemi, A., Amanlou, M. & Shafiee, A. (2004). Bioorg. Med. Chem. 12, 3971-3976.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Jindal, D. P., Chattopadhaya, R., Guleria, S. & Gupta, R. (2003). Eur. J. Med. Chem. 38, 1025-1034.  [ISI] [CrossRef] [PubMed] [ChemPort]
Karakurt, A., Dalkara, S., Özalp, M., Özbey, S., Kendi, E. & Stables, J. P. (2001). Eur. J. Med. Chem. 36, 421-433.  [ISI] [CrossRef] [PubMed] [ChemPort]
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 (2012). E68, o3178  [ doi:10.1107/S1600536812042675 ]

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