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

Kosmalski, T.; Gzella, A.K.

doi:10.1107/S1600536812042675

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 (C-C) = 0.003 Å
R = 0.056
wR = 0.137
Data-to-parameter ratio = 17.8
Details

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

Tomasz Kosmalski ^a and Andrzej K. Gzella ^b,^c ^*

^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); Emami et al. (2004); Demirayak et al. (2002); Bhandari et al. (2009); Jindal et al. (2003); Karakurt et al. (2001).

Experimental

Crystal data

C₁₇H₁₄ClNO₂
M_r = 299.74
Triclinic, $[P \overline 1]$
a = 5.8842 (4) Å
b = 7.1173 (6) Å
c = 17.2313 (16) Å
= 93.802 (7)°
= 97.998 (7)°
= 95.363 (7)°
V = 709.19 (10) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.783, T_max = 1.000
9366 measured reflections
3407 independent reflections
2817 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.137
S = 1.10
3407 reflections
191 parameters
H-atom parameters constrained
_max = 0.77 e Å^-3
_min = -0.31 e Å^-3

Data collection: CrysAlis PRO (Agilent, 2010); 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), PLATON (Spek, 2009).

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.
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.
Demirayak, S., Uçucu, Ü., Benkli, K., Gündogdu-Karaburun, N., Karaburun, A., Akar, D., Karabacak, M. & Kiraz, N. (2002). Il Farmaco, 57, 609-612.
Emami, S., Falahati, M., Banifatemi, A., Amanlou, M. & Shafiee, A. (2004). Bioorg. Med. Chem. 12, 3971-3976.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Jindal, D. P., Chattopadhaya, R., Guleria, S. & Gupta, R. (2003). Eur. J. Med. Chem. 38, 1025-1034.
Karakurt, A., Dalkara, S., Özalp, M., Özbey, S., Kendi, E. & Stables, J. P. (2001). Eur. J. Med. Chem. 36, 421-433.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds