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

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

doi:10.1107/S1600536812048441

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 (C-C) = 0.002 Å
R = 0.030
wR = 0.076
Data-to-parameter ratio = 12.2
Details

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

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

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-HO 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). For the synthesis of the title compound, see: Hoogendoorn et al. (2011).

Experimental

Crystal data

C₁₁H₈O₃
M_r = 188.17
Monoclinic, C 2/c
a = 16.8785 (5) Å
b = 5.4202 (2) Å
c = 19.6107 (6) Å
= 91.469 (2)°
V = 1793.49 (10) Å³
Z = 8
Cu K radiation
= 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) T_min = 0.855, T_max = 0.912
10685 measured reflections
1545 independent reflections
1451 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.030
wR(F²) = 0.076
S = 1.04
1545 reflections
127 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11-H11O1ⁱ	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); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

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.
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