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Volume 69 
Part 4 
Page o578  
April 2013  

Received 16 January 2013
Accepted 18 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 300 K
Mean [sigma](C-C) = 0.005 Å
R = 0.042
wR = 0.126
Data-to-parameter ratio = 7.6
Details
Open access

5,7-Dihydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one

aS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan
Correspondence e-mail: adizovshahobiddin@yahoo.com

The title compound, C18H16O8, was isolated from the plant Artemisia baldshuanica Krasch et Zarp. The molecule is approximately planar, with the exception of the terminal methyl groups, the C atoms of which devitate from their attached ring planes by 1.243 (5) and 1.168 (5) Å. The dihedral angle between the substituted benzopyran and benzene rings is 5.8 (1)°; this near planarity could be due to conjugation or a packing effect. Intramolecular O-H...O and C-H...O hydrogen bonds occur. In the crystal, molecules are connected by O-H...O hydrogen bonds involving the hydroxy and carbonyl groups, forming hydrogen-bonded chains along [001] and [1-10]. The chains are linked by C-H...O interactions.

Related literature

For the biological activity of flavonoids, see: Bodewes et al. (2011[Bodewes, T. C. F., Luttikhold, J., van Stijn, M. F. M., Visser, M., van Norren, K., Vermeulen, M. A. R. & van Leeuwen, P. A. M. (2011). Curr. Org. Chem. 15, 2616-2626.]); Veitch & Grayer (2011[Veitch, N. C. & Grayer, R. J. (2011). Nat. Prod. Rep. 28, 626-1695.]). For related structures, see: Martinez-Vazquez et al. (1993[Martinez-Vazquez, M., Vazquez Garcia, H. M., Toscano, R. A. & Perez, G. E. (1993). J. Nat. Prod. 56, 1410-1415.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16O8

  • Mr = 360.31

  • Monoclinic, P c

  • a = 11.5837 (6) Å

  • b = 4.4677 (3) Å

  • c = 15.5521 (8) Å

  • [beta] = 103.310 (6)°

  • V = 783.23 (8) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 1.04 mm-1

  • T = 300 K

  • 0.60 × 0.40 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.638, Tmax = 0.813

  • 2540 measured reflections

  • 1841 independent reflections

  • 1632 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.126

  • S = 1.07

  • 1841 reflections

  • 242 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2A...O3 0.82 2.38 2.762 (4) 109
O2-H2A...O5i 0.82 1.96 2.713 (4) 152
O4-H4A...O5 0.82 1.85 2.579 (4) 148
O6-H6A...O4ii 0.82 2.20 2.954 (3) 153
O6-H6A...O7 0.82 2.31 2.734 (4) 113
C3-H3A...O2iii 0.93 2.58 3.246 (5) 129
C12-H12B...O4iv 0.96 2.55 3.459 (6) 157
C12-H12C...O8 0.96 2.32 2.927 (6) 122
Symmetry codes: (i) [x, -y+1, z+{\script{1\over 2}}]; (ii) x+1, y-1, z; (iii) [x, -y+1, z-{\script{1\over 2}}]; (iv) x+1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZP2001 ).


Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant No. FA-F7-T185)

References

Bodewes, T. C. F., Luttikhold, J., van Stijn, M. F. M., Visser, M., van Norren, K., Vermeulen, M. A. R. & van Leeuwen, P. A. M. (2011). Curr. Org. Chem. 15, 2616-2626.  [ChemPort]
Martinez-Vazquez, M., Vazquez Garcia, H. M., Toscano, R. A. & Perez, G. E. (1993). J. Nat. Prod. 56, 1410-1415.  [ChemPort]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Veitch, N. C. & Grayer, R. J. (2011). Nat. Prod. Rep. 28, 626-1695.  [CrossRef]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o578  [ doi:10.1107/S1600536813007381 ]

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