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Volume 64 
Part 2 
Page o371  
February 2008  

Received 15 November 2007
Accepted 20 December 2007
Online 4 January 2008

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© International Union of Crystallography 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.133
Data-to-parameter ratio = 16.1
Details
Open access

2-Hydroxy-1,6,7,8-tetramethoxy-3-methylanthraquinone

Li-Cai Zhu,a Zhen-Gang Zhaoa and Shu-Juan Yua*

aCollege of Light Industry and Food Sciences, South China University of Technology, Guangzhou 510641, People's Republic of China
Correspondence e-mail: lfshjyu@scut.edu.cn

The title compound, C19H18O7, also known as chrysoobtusin, was isolated from Cassia tora L. (Leguminosae). The anthraquinone ring system is almost planar, the dihedral angle between the two benzene rings being 4.27 (4)°. The structure is stabilized by intra- and intermolecular O-H...O and C-H...O hydrogen bonds, and by weak [pi]-[pi] stacking interactions along the b axis, with a centroid-centroid distance between related benzene rings of 3.800 (4) Å.

Related literature

For related literature, see: Boonnak et al. (2005[Boonnak, N., Chantrapromma, S., Fun, H.-K., Anjum, S., Ali, S., Atta-ur-Rahman & Karalai, C. (2005). Acta Cryst. E61, o410-o412.]); Hao et al. (1995[Hao, N. J., Huang, M. P. & Lee, H. (1995). Mutat. Res. 328, 183-191.]); Jia et al. (2007[Jia, Z. B., Tao, F., Guo, L., Tao, G. L. & Ding, X. L. (2007). LWT Food Sci. Technol. 40, 1072-1077.]); Ng et al. (2005[Ng, S.-L., Razak, I. A., Fun, H.-K., Boonsri, S., Chantrapromma, S. & Prawat, U. (2005). Acta Cryst. E61, o3656-o3658.]); Patil et al. (2004[Patil, U. K., Saraf, S. & Dixit, V. K. (2004). J. Ethnopharmacol. 90, 249-252.]); Wu & Yen (2004[Wu, C. H. & Yen, G. C. (2004). Life Sci. 76, 85-101.]); Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C19H18O7

  • Mr = 358.33

  • Monoclinic, P 21 /n

  • a = 12.2960 (3) Å

  • b = 7.8545 (2) Å

  • c = 18.3361 (5) Å

  • [beta] = 106.581 (2)°

  • V = 1697.24 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 (2) K

  • 0.30 × 0.28 × 0.26 mm
Data collection

  • Bruker APEXII area-detector diffractometer

  • Absorption correction: none

  • 13295 measured reflections

  • 3871 independent reflections

  • 2527 reflections with I > 2[sigma](I)

  • Rint = 0.032
Refinement

  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.133

  • S = 1.02

  • 3871 reflections

  • 241 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C18-H18A...O4 0.96 2.53 3.074 (3) 116
C17-H17A...O4 0.96 2.60 3.046 (3) 109
C16-H16A...O1 0.96 2.50 3.049 (3) 116
O7-H7...O6 0.82 2.19 2.6482 (17) 116
O7-H7...O3i 0.82 2.02 2.7221 (16) 144
Symmetry code: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 (Version 7.23A), SAINT (Version 7.23A) and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 (Version 7.23A), SAINT (Version 7.23A) and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Bruker, 2004[Bruker (2004). APEX2 (Version 7.23A), SAINT (Version 7.23A) and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2185 ).

Acknowledgements

The authors acknowledge the Ministry of Science and Technology of China (fund No. 2006BAD27B03) for financial support, and South China University of Technology and South China Normal University for supporting this work.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Boonnak, N., Chantrapromma, S., Fun, H.-K., Anjum, S., Ali, S., Atta-ur-Rahman & Karalai, C. (2005). Acta Cryst. E61, o410-o412.  [details]
Bruker (2004). APEX2 (Version 7.23A), SAINT (Version 7.23A) and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.
Hao, N. J., Huang, M. P. & Lee, H. (1995). Mutat. Res. 328, 183-191.  [ChemPort] [PubMed]
Jia, Z. B., Tao, F., Guo, L., Tao, G. L. & Ding, X. L. (2007). LWT Food Sci. Technol. 40, 1072-1077.
Ng, S.-L., Razak, I. A., Fun, H.-K., Boonsri, S., Chantrapromma, S. & Prawat, U. (2005). Acta Cryst. E61, o3656-o3658.  [CrossRef] [details]
Patil, U. K., Saraf, S. & Dixit, V. K. (2004). J. Ethnopharmacol. 90, 249-252.  [CrossRef] [PubMed]
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Wu, C. H. & Yen, G. C. (2004). Life Sci. 76, 85-101.  [CrossRef] [PubMed] [ChemPort]

Acta Cryst (2008). E64, o371  [ doi:10.1107/S1600536807067864 ]