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

Scalzullo, S.M.; Khorasani, S.; Michael, J.P.

doi:10.1107/S1600536812051057

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 (C-C) = 0.002 Å
R = 0.032
wR = 0.085
Data-to-parameter ratio = 9.1
Details

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

Stefania M. Scalzullo,^a Sanaz Khorasani ^a and Joseph P. Michael ^a ^*

^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-HO interactions are present between the stacks.

Related literature

For a review on lamellarin alkaloids, see: Fan et al. (2008). The experimental procedure of Combes et al. (2002) 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); Nolan et al. (2009).

Experimental

Crystal data

C₁₀H₁₂O₄
M_r = 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 radiation
= 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(I)
R_int = 0.032

Refinement

R[F² > 2(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
_max = 0.20 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
O1-H1O4	0.93 (3)	1.71 (3)	2.549 (2)	150 (2)
C8-H8CO3ⁱ	0.98	2.40	3.365 (2)	168
C9-H9BO3ⁱⁱ	0.98	2.57	3.513 (3)	162
C10-H10CO2ⁱ	0.98	2.53	3.334 (3)	139
C8-H8BCg1ⁱⁱⁱ	0.98	2.80	3.738 (3)	160
C9-H9ACg1^iv	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); cell refinement: SAINT (Bruker, 2005); 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, 2012) and SCHAKAL99 (Keller, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
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.
Ploypradith, P., Jinaglueng, W., Pavaro, C. & Ruchirawal, S. (2003). Tetrahedron Lett. 44, 1363-1366.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds