5-Hy­droxy-7-meth­oxy-2-methyl-4H-chromen-4-one from Dysoxylum macrocarpum (Meliaceae)

Najmuldeen, I.A.; Abdul Hadi, A.H.; Awang, K.; Mohamad, K.; Ng, S.W.

doi:10.1107/S1600536810025146

Volume 66
Part 8
Page o1883
August 2010

Received 24 June 2010
Accepted 26 June 2010
Online 3 July 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R = 0.035
wR = 0.108
Data-to-parameter ratio = 15.1
Details

5-Hydroxy-7-methoxy-2-methyl-4H-chromen-4-one from Dysoxylum macrocarpum (Meliaceae)

Ibrahim A. Najmuldeen,^a Abdul Hamid Abdul Hadi,^a Khalijah Awang,^a Khalit Mohamad ^b and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bDepartment of Pharmacy, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

Both independent molecules in the asymmetric unit of the title compound, C₁₁H₁₀O₄, are almost planar (r.m.s. deviations = 0.011 and 0.033 Å). In both molecules, the hydroxy group is intramolecularly hydrogen bonded to the ketonic O atom. The independent molecules are stacked alternately along the a axis, with the centroids of their chromene ring separated by distances of 4.490 (1) and 3.621 (1) Å.

Related literature

For studies on other Dysoxylum species, see: Ismail et al. (2009); Lakshmi et al. (2007); Mohamad et al. (1999); Mohanakumara et al. (2010); Senthil Nathan et al. (2008); Xie et al. (2008).

Experimental

Crystal data

C₁₁H₁₀O₄
M_r = 206.19
Monoclinic, P 2₁ /c
a = 7.7393 (3) Å
b = 14.5373 (6) Å
c = 16.8263 (7) Å
= 98.848 (1)°
V = 1870.57 (13) Å³
Z = 8
Mo K radiation
= 0.11 mm^-1
T = 100 K
0.35 × 0.35 × 0.02 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
17796 measured reflections
4285 independent reflections
3795 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.108
S = 1.02
4285 reflections
283 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.34 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3O2	0.85 (1)	1.83 (1)	2.618 (1)	154 (2)
O7-H7O6	0.85 (1)	1.79 (1)	2.595 (1)	156 (2)

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5120 ).

Acknowledgements

The authors thank the University of Malaya (PPP PS378/009B) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Ismail, I. F., Nagakura, Y., Hirasawa, Y., Hosoya, T., Mohd Lazim, M. I., Hj Lajis, N. & Morita, H. (2009). Tetrahedron Lett. 50, 4830-4832.
Lakshmi, V., Pandey, K., Kapil, A., Singh, N., Samant, M. & Dube, A. (2007). Phytomedicine, 14, 36-42.
Mohamad, K., Martin, M. T., Litaudon, M. C., Gaspard, C., Sevenet, T. & Pais, M. (1999). Phytochemistry, 52, 1461-1468.
Mohanakumara, P., Sreejayan, N., Priti, V., Ramesha, B. T., Ravikanth, G., Ganeshaiah, K. N., Vasudeva, R., Mohan, J., Santhoshkumar, T. R. & Shaanker, R. U. (2010). Fitoterapia, 81, 145-148.
Senthil Nathan, S., Hisham, A. & Jayakumar, G. (2008). Fitoterapia, 79, 106-111.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Xie, J.-B., Yang, S.-P. & Yue, J.-M. (2008). Phytochemistry, 69, 2993-2997.

organic compounds