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Volume 69 
Part 1 
Page o139  
January 2013  

Received 26 November 2012
Accepted 17 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.085
Data-to-parameter ratio = 9.1
Details
Open access

1-(2-Hydroxy-4,5-dimethoxyphenyl)ethanone

aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South Africa
Correspondence e-mail: joseph.michael@wits.ac.za

The molecular structure of the title compound, C10H12O4, contains an intramolecular hydrogen bond between the phenol and acetyl substituents. In the crystal, C-H...[pi] interactions act between the molecules in a cyclic manner to stabilize stacks of molecules along the b axis. Several C-H...O interactions are present between the stacks.

Related literature

For a review on lamellarin alkaloids, see: Fan et al. (2008[Fan, H., Peng, J., Hamann, M. T. & Hu, J.-F. (2008). Chem. Rev. 108, 264-287.]). The experimental procedure of Combes et al. (2002[Combes, S., Finet, J.-P. & Siri, D. (2002). J. Chem. Soc. Perkin Trans. 1, pp. 38-44.]) for a related Fries rearrangement was adapted for the synthesis of the title compound. For alternative syntheses of the title compound by Fries rearrangement, see: Ploypradith et al. (2003[Ploypradith, P., Jinaglueng, W., Pavaro, C. & Ruchirawal, S. (2003). Tetrahedron Lett. 44, 1363-1366.]); Nolan et al. (2009[Nolan, K. A., Doncaster, J. R., Dunstan, M. S., Scott, K. A., Frenkel, A. D., Siegel, D., Ross, D., Barnes, J., Levy, C., Leys, D., Whitehead, R. C., Stratford, I. J. & Bryce, R. A. (2009). J. Med. Chem. 52, 7142-7156.]).

[Scheme 1]

Experimental

Crystal data
  • C10H12O4

  • Mr = 196.20

  • Orthorhombic, P c a 21

  • a = 19.1740 (12) Å

  • b = 5.5026 (3) Å

  • c = 8.9956 (5) Å

  • V = 949.10 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 173 K

  • 0.41 × 0.32 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 4718 measured reflections

  • 1214 independent reflections

  • 1106 reflections with I > 2[sigma](I)

  • Rint = 0.032

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

  • wR(F2) = 0.085

  • S = 1.06

  • 1214 reflections

  • 134 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
O1-H1...O4 0.93 (3) 1.71 (3) 2.549 (2) 150 (2)
C8-H8C...O3i 0.98 2.40 3.365 (2) 168
C9-H9B...O3ii 0.98 2.57 3.513 (3) 162
C10-H10C...O2i 0.98 2.53 3.334 (3) 139
C8-H8B...Cg1iii 0.98 2.80 3.738 (3) 160
C9-H9A...Cg1iv 0.98 2.90 3.828 (3) 158
Symmetry codes: (i) [-x+1, -y, z-{\script{1\over 2}}]; (ii) [-x+1, -y+1, z+{\script{1\over 2}}]; (iii) x, y-1, z; (iv) x, y+1, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and SCHAKAL99 (Keller, 1999[Keller, E. (1999). SCHAKAL99. University of Freiberg, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2196 ).


Acknowledgements

This work was supported by the University of the Witwatersrand and the National Research Foundation, Pretoria (grant No. 78837).

References

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Combes, S., Finet, J.-P. & Siri, D. (2002). J. Chem. Soc. Perkin Trans. 1, pp. 38-44.
Fan, H., Peng, J., Hamann, M. T. & Hu, J.-F. (2008). Chem. Rev. 108, 264-287.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Keller, E. (1999). SCHAKAL99. University of Freiberg, Germany.
Nolan, K. A., Doncaster, J. R., Dunstan, M. S., Scott, K. A., Frenkel, A. D., Siegel, D., Ross, D., Barnes, J., Levy, C., Leys, D., Whitehead, R. C., Stratford, I. J. & Bryce, R. A. (2009). J. Med. Chem. 52, 7142-7156.  [CrossRef] [PubMed] [ChemPort]
Ploypradith, P., Jinaglueng, W., Pavaro, C. & Ruchirawal, S. (2003). Tetrahedron Lett. 44, 1363-1366.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o139  [ doi:10.1107/S1600536812051057 ]

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