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Volume 69 
Part 1 
Page o74  
January 2013  

Received 31 October 2012
Accepted 26 November 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.030
wR = 0.076
Data-to-parameter ratio = 12.2
Details
Open access

2-[(3-Oxo-1-benzofuran-6-yl)oxy]acetonitrile

aResearch Center for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg, 2006, South Africa
Correspondence e-mail: zhphasha@uj.ac.za

The molecule of the title compound, C11H8O3, is essentially planar [r.m.s. deviation = 0.025 (2) Å]. In the crystal, molecules are stacked along [110] but no short [pi]-[pi] contacts are observed. Weak C-H...O interactions link the molecules into chains along [101].

Related literature

For background to the development of hybrid drug candidates against tuberculosis, malaria and cancer, see: Morphy et al. (2004[Morphy, R., Kay, C. & Rankovic, Z. (2004). Drug Discov. Today, 9, 641-651.]). For the synthesis of the title compound, see: Hoogendoorn et al. (2011[Hoogendoorn, S., Blom, A. E. M., Willems, L. I., Van der Marel, G. A. & Overkleeft, H. S. (2011). Org. Lett. 13, 5656-5659.]).

[Scheme 1]

Experimental

Crystal data
  • C11H8O3

  • Mr = 188.17

  • Monoclinic, C 2/c

  • a = 16.8785 (5) Å

  • b = 5.4202 (2) Å

  • c = 19.6107 (6) Å

  • [beta] = 91.469 (2)°

  • V = 1793.49 (10) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.85 mm-1

  • T = 100 K

  • 0.19 × 0.15 × 0.11 mm

Data collection
  • Bruker APEX DUO 4K CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.855, Tmax = 0.912

  • 10685 measured reflections

  • 1545 independent reflections

  • 1451 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.076

  • S = 1.04

  • 1545 reflections

  • 127 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11...O1i 0.95 2.24 3.1676 (15) 165
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2008[Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: LD2084 ).


Acknowledgements

Support by the research funds of the University of Johannesburg is gratefully acknowledged.

References

Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hoogendoorn, S., Blom, A. E. M., Willems, L. I., Van der Marel, G. A. & Overkleeft, H. S. (2011). Org. Lett. 13, 5656-5659.  [ISI] [CrossRef] [ChemPort] [PubMed]
Morphy, R., Kay, C. & Rankovic, Z. (2004). Drug Discov. Today, 9, 641-651.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o74  [ doi:10.1107/S1600536812048441 ]

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