5-Meth­oxy-2-benzofuran-1(3H)-one

Paixão, D.A.; Guilardi, S.; Pereira, J.L.; Teixeira, R.R.; Arantes, J.F.

doi:10.1107/S1600536812044789

Volume 68
Part 12
Page o3288
December 2012

Received 16 October 2012
Accepted 29 October 2012
Online 7 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.049
wR = 0.147
Data-to-parameter ratio = 14.6
Details

5-Methoxy-2-benzofuran-1(3H)-one

Drielly A. Paixão,^a Silvana Guilardi,^a ^* Jorge L. Pereira,^b Róbson R. Teixeira ^b ^* and Júnior F. Arantes ^b

^aInstituto de Química-UFU, Uberlândia, MG, Brazil, and ^bDepartamento de Química-UFV, Viçosa, MG, Brazil
Correspondence e-mail: silvana@ufu.br, robsonr.teixeira@ufv.br

In the title compound, C₉H₈O₃, the molecular skeleton is almost planar, with an r.m.s. deviation of 0.010 (2) Å. In the crystal, weak C-HO hydrogen bonds connect the molecules into a two-dimensional network parallel to the ac plane.

Related literature

For the biological activity of isobenzofuran-1(3H)-one, see: Ma et al. (2012); Huang et al. (2012); Zhao et al. (2012); Arnone et al. (2002). For the synthesis, see: Zhang et al. (2009). For related structures, see: Sun et al. (2009); Mendenhall et al. (2003); Pereira et al. (2012).

Experimental

Crystal data

C₉H₈O₃
M_r = 164.15
Monoclinic, P 2₁ /c
a = 8.1819 (9) Å
b = 10.4285 (18) Å
c = 9.2965 (9) Å
= 99.962 (8)°
V = 781.26 (18) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 293 K
0.30 × 0.18 × 0.16 mm

Data collection

Enraf-Nonius KappaCCD diffractometer
14100 measured reflections
1587 independent reflections
1101 reflections with I > 2(I)
R_int = 0.049

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.147
S = 1.06
1587 reflections
109 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6O1ⁱ	0.93	2.54	3.419 (2)	157
C8-H8AO2ⁱⁱ	0.97	2.52	3.372 (2)	146
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; 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: ZS2239 ).

Acknowledgements

The authors thank Professor Dr Javier Ellena of the IFSC, USP, Brazil, for the X-ray data collection. This work was supported financially by CAPES, CNPq, FUNARBE and FAPEMIG. This work is also a collaboration research project of members of the Rede Mineira de Química (RQ - MG) also supported by FAPEMIG.

References

Arnone, A., Assante, G., Nasini, G., Strada, S. & Vercesi, A. (2002). J. Nat. Prod. 65, 48-50.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Huang, X.-Z., Zhu, Y., Guan, X.-L., Tian, K., Guo, J.-M., Wang, H.-B. & Fu, G.-M. (2012). Molecules, 17, 4219-4224.
Ma, F., Gao, Y., Qiao, H., Hu, X. & Chang, J. (2012). J. Thromb. Thrombolysis, 33, 64-73.
Mendenhall, G. D., Luck, R. L., Bohn, R. K. & Castejon, H. J. (2003). J. Mol. Struct. 645, 249-258.
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Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Pereira, J. L., Teixeira, R. R., Guilardi, S. & Paixão, D. A. (2012). Acta Cryst. E68, o2995.
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Zhang, Y.-H., Shi, B.-F. & Yu, J.-Q. (2009). Angew. Chem. Int. Ed. 48, 6097-6100.
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organic compounds