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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 [sigma](C-C) = 0.002 Å
R = 0.049
wR = 0.147
Data-to-parameter ratio = 14.6
Details
Open access

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

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-H...O 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[Ma, F., Gao, Y., Qiao, H., Hu, X. & Chang, J. (2012). J. Thromb. Thrombolysis, 33, 64-73.]); Huang et al. (2012[Huang, X.-Z., Zhu, Y., Guan, X.-L., Tian, K., Guo, J.-M., Wang, H.-B. & Fu, G.-M. (2012). Molecules, 17, 4219-4224.]); Zhao et al. (2012[Zhao, N., Ji, M.-X., Xu, L. & Ji, B.-S. (2012). Drug. Dev. Res. 73, 11-17.]); Arnone et al. (2002[Arnone, A., Assante, G., Nasini, G., Strada, S. & Vercesi, A. (2002). J. Nat. Prod. 65, 48-50.]). For the synthesis, see: Zhang et al. (2009[Zhang, Y.-H., Shi, B.-F. & Yu, J.-Q. (2009). Angew. Chem. Int. Ed. 48, 6097-6100.]). For related structures, see: Sun et al. (2009[Sun, M.-X., Li, X., Liu, W.-Y. & Xiao, K. (2009). Acta Cryst. E65, o2146.]); Mendenhall et al. (2003[Mendenhall, G. D., Luck, R. L., Bohn, R. K. & Castejon, H. J. (2003). J. Mol. Struct. 645, 249-258.]); Pereira et al. (2012[Pereira, J. L., Teixeira, R. R., Guilardi, S. & Paixão, D. A. (2012). Acta Cryst. E68, o2995.]).

[Scheme 1]

Experimental

Crystal data
  • C9H8O3

  • Mr = 164.15

  • Monoclinic, P 21 /c

  • a = 8.1819 (9) Å

  • b = 10.4285 (18) Å

  • c = 9.2965 (9) Å

  • [beta] = 99.962 (8)°

  • V = 781.26 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.147

  • S = 1.06

  • 1587 reflections

  • 109 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 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
C6-H6...O1i 0.93 2.54 3.419 (2) 157
C8-H8A...O2ii 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[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[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.]); data reduction: DENZO-SMN; 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: 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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Huang, X.-Z., Zhu, Y., Guan, X.-L., Tian, K., Guo, J.-M., Wang, H.-B. & Fu, G.-M. (2012). Molecules, 17, 4219-4224.  [CrossRef] [ChemPort] [PubMed]
Ma, F., Gao, Y., Qiao, H., Hu, X. & Chang, J. (2012). J. Thromb. Thrombolysis, 33, 64-73.  [ISI] [CrossRef] [PubMed]
Mendenhall, G. D., Luck, R. L., Bohn, R. K. & Castejon, H. J. (2003). J. Mol. Struct. 645, 249-258.  [CSD] [CrossRef]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
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.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sun, M.-X., Li, X., Liu, W.-Y. & Xiao, K. (2009). Acta Cryst. E65, o2146.  [CSD] [CrossRef] [details]
Zhang, Y.-H., Shi, B.-F. & Yu, J.-Q. (2009). Angew. Chem. Int. Ed. 48, 6097-6100.  [ISI] [CrossRef] [ChemPort]
Zhao, N., Ji, M.-X., Xu, L. & Ji, B.-S. (2012). Drug. Dev. Res. 73, 11-17.  [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3288  [ doi:10.1107/S1600536812044789 ]

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