[Journal logo]

Volume 68 
Part 12 
Page o3379  
December 2012  

Received 28 October 2012
Accepted 5 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.082
Data-to-parameter ratio = 11.9
Details
Open access

2-(2-Hydroxypropan-2-yl)-6-(prop-2-ynyloxy)-1-benzofuran-3(2H)-one

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

In the title compound, C14H14O4, the prop-2-ynyloxy O-C-C[triple bond]C plane [maximum deviation = 0.0116 (12) Å] forms a dihedral angle of 78.44 (9)° with the benzofuran-3(2H)-one ring system. In the crystal, molecules are linked by O-H...O hydrogen bonds, forming a tape along the a-axis direction. C-H...O interactions are observed between the tapes.

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 details of 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
  • C14H14O4

  • Mr = 246.25

  • Triclinic, [P \overline 1]

  • a = 5.4199 (2) Å

  • b = 9.0785 (3) Å

  • c = 12.3555 (4) Å

  • [alpha] = 85.758 (2)°

  • [beta] = 80.455 (2)°

  • [gamma] = 81.829 (2)°

  • V = 592.65 (4) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.84 mm-1

  • T = 100 K

  • 0.39 × 0.11 × 0.11 mm

Data collection
  • Bruker APEX DUO 4K CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.736, Tmax = 0.913

  • 10266 measured reflections

  • 1983 independent reflections

  • 1888 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.082

  • S = 1.03

  • 1983 reflections

  • 166 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H...O4i 0.84 2.01 2.8328 (12) 167
C1-H1...O1ii 0.95 2.45 3.3283 (16) 154
C5-H5...O1iii 0.95 2.52 3.3809 (15) 152
Symmetry codes: (i) x+1, y, z; (ii) x, y, z-1; (iii) -x, -y+2, -z+1.

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


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5212 ).


Acknowledgements

Research funds of the University of Johannesburg is gratefully acknowledged.

References

Bruker (2008). SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [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 (2012). E68, o3379  [ doi:10.1107/S1600536812045606 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.