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Volume 69 
Part 8 
Page o1361  
August 2013  

Received 26 May 2013
Accepted 12 July 2013
Online 31 July 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.008 Å
R = 0.034
wR = 0.070
Data-to-parameter ratio = 12.3
Details
Open access

2,4-Dibromo-1,3-dihydroxy-9H-xanthen-9-one

aKey Laboratory for the Chemistry & Molecular Engineering of Medicinal Resources, Ministry of Education of China, School of Chemistry & Chemical Engineering, Guangxi Normal University, Guilin, 541004, People's Republic of China, and bDepartment of Pharmacy, Youjiang Medical University for Nationalities, Baise 533000, People's Republic of China
Correspondence e-mail: jiangkeq@163.com

The title compound, C13H6Br2O4, derived from xanthone, a fundamental structural framework of active ingredients in many medicinal plants, and was synthesized by bromination of 1,3-dihydroxyxanthen-9-one with N-bromosuccinimide. The molecular conformation is essentially planar, the dihedral angle between the benzene rings being 1.1 (4)°. This conformation is favorable for the formation of an intramolecular O-H...O hydrogen bond between a hydroxy group and the xanthone carbonyl group. In the crystal, molecules are associated into chains along the b-axis direction via C=O...H-O hydrogen bonds involving the other hydroxy group.

Related literature

For the pharmacological activity of xanthone derivatives, see: Cheng et al. (2011[Cheng, J.-H., Huang, A.-M., Hour, T.-C., Yang, S.-C., Pu, Y.-S. & Lin, C.-N. (2011). Eur. J. Med. Chem. 46, 1222-1231.]); Dao et al. (2012[Dao, T. T., Dang, T. T., Nguyen, P. H., Kim, E., Thuong, P. T. & Oh, W. K. (2012). Bioorg. Med. Chem. Lett. 22, 3688-3692.]); Sousa et al. (2009[Sousa, E., Paiva, A., Nazareth, N., Gales, L., Damas, A. M., Nascimento, M. S. J. & Pinto, M. (2009). Eur. J. Med. Chem. 44, 3830-3835.]); Szkaradek et al. (2013[Szkaradek, N., Gunia, A., Waszkielewicz, A. M., Antkiewicz-Michaluk, L., Cegla, M., Szneler, E. & Marona, H. (2013). Bioorg. Med. Chem. 21, 1190-1198.]). For the synthesis of the xanthone used as a starting material, see: Liu et al. (2006[Liu, Y., Zou, L., Ma, L., Chen, W.-H., Wang, B. & Xu, Z.-L. (2006). Bioorg. Med. Chem. 14, 5683-5690.]). For related xanthone structures, see: Corrêa et al. (2010[Corrêa, R. S., dos Santos, M. H., Nagem, T. J. & Ellena, J. (2010). Struct. Chem. 21, 555-563.]).

[Scheme 1]

Experimental

Crystal data
  • C13H6Br2O4

  • Mr = 386.00

  • Orthorhombic, P n a 21

  • a = 18.4489 (15) Å

  • b = 16.9049 (13) Å

  • c = 3.8564 (3) Å

  • V = 1202.72 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 6.75 mm-1

  • T = 298 K

  • 0.28 × 0.09 × 0.06 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.254, Tmax = 0.688

  • 6188 measured reflections

  • 2120 independent reflections

  • 1830 reflections with I > 2[sigma](I)

  • Rint = 0.076

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.070

  • S = 1.04

  • 2120 reflections

  • 172 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 881 Friedel pairs

  • Absolute structure parameter: -0.008 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4...O2 0.82 1.81 2.555 (7) 149
O3-H3...O2i 0.82 2.02 2.741 (7) 147
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT (Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2480 ).


Acknowledgements

This work was supported financially by grants from the National Natural Science Foundation of PRC (21002015) and the Natural Science Foundation of Guangxi (2010GXNSFB013013).

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cheng, J.-H., Huang, A.-M., Hour, T.-C., Yang, S.-C., Pu, Y.-S. & Lin, C.-N. (2011). Eur. J. Med. Chem. 46, 1222-1231.  [CrossRef] [ChemPort] [PubMed]
Corrêa, R. S., dos Santos, M. H., Nagem, T. J. & Ellena, J. (2010). Struct. Chem. 21, 555-563.
Dao, T. T., Dang, T. T., Nguyen, P. H., Kim, E., Thuong, P. T. & Oh, W. K. (2012). Bioorg. Med. Chem. Lett. 22, 3688-3692.  [CrossRef] [ChemPort] [PubMed]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Liu, Y., Zou, L., Ma, L., Chen, W.-H., Wang, B. & Xu, Z.-L. (2006). Bioorg. Med. Chem. 14, 5683-5690.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sousa, E., Paiva, A., Nazareth, N., Gales, L., Damas, A. M., Nascimento, M. S. J. & Pinto, M. (2009). Eur. J. Med. Chem. 44, 3830-3835.  [CrossRef] [PubMed] [ChemPort]
Szkaradek, N., Gunia, A., Waszkielewicz, A. M., Antkiewicz-Michaluk, L., Cegla, M., Szneler, E. & Marona, H. (2013). Bioorg. Med. Chem. 21, 1190-1198.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1361  [ doi:10.1107/S1600536813019296 ]

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