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

Kinfe, H.H.; Belay, Y.H.; Phasha, Z.H.

doi:10.1107/S1600536812045606

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 (C-C) = 0.002 Å
R = 0.032
wR = 0.082
Data-to-parameter ratio = 11.9
Details

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

Henok H. Kinfe,^a Yonas H. Belay ^a and Zanele H. Phasha ^a ^*

^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-HO hydrogen bonds, forming a tape along the a-axis direction. C-HO 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). For details of the synthesis of the title compound, see: Hoogendoorn et al. (2011).

Experimental

Crystal data

C₁₄H₁₄O₄
M_r = 246.25
Triclinic, $[P \overline 1]$
a = 5.4199 (2) Å
b = 9.0785 (3) Å
c = 12.3555 (4) Å
= 85.758 (2)°
= 80.455 (2)°
= 81.829 (2)°
V = 592.65 (4) Å³
Z = 2
Cu K radiation
= 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) T_min = 0.736, T_max = 0.913
10266 measured reflections
1983 independent reflections
1888 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.082
S = 1.03
1983 reflections
166 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-HO4ⁱ	0.84	2.01	2.8328 (12)	167
C1-H1O1ⁱⁱ	0.95	2.45	3.3283 (16)	154
C5-H5O1ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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).

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.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Hoogendoorn, S., Blom, A. E. M., Willems, L. I., Van der Marel, G. A. & Overkleeft, H. S. (2011). Org. Lett. 13, 5656-5659.
Morphy, R., Kay, C. & Rankovic, Z. (2004). Drug Discov. Today, 9, 641-651.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds