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Volume 69 
Part 6 
Page o834  
June 2013  

Received 28 March 2013
Accepted 27 April 2013
Online 4 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.033
wR = 0.087
Data-to-parameter ratio = 11.3
Details
Open access

2-Bromo-1,6,6-trimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione

aChemical Engineering & Pharmaceutics College, Henan University of Science and Technology, Luoyang, Henan 471003, People's Republic of China, and bCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang, Henan 471022, People's Republic of China
Correspondence e-mail: fancuiping08@163.com

In the title compound, C19H17BrO3, the ring skeleton is located on a crystallographic mirror plane; two C atoms of the cyclohexene ring are disordered over the two locations to satisfy the preferred ring conformation. In the crystal, C-H...O hydrogen bonds link the molecules into chains along the a axis. [pi]-[pi] stacking interactions between benzoquinone rings, with a centroid-centroid distance of 3.7225 (4) Å, are also observed, which connect the chains into a two-dimensional networkparallel to the ab plane.

Related literature

The title compound is a derivative of Tanshinone IIA, the major active component isolated from the Chinese herbal medicine danshen, which is used in the treatment of coronary heart disease (Chang et al., 1991[Chang, H. M., Chui, K. Y., Tan, F. W. L., Yang, Y., Zhong, Z. P., Lee, C. M., Sham, H. L. & Wang, H. N. C. (1991). J. Med. Chem. 34, 1675-1692.]; Wang et al., 2005[Wang, H., Gao, X. M. & Zhang, B. L. (2005). J. Ethnopharmacol. 99, 93-98.]), myocardial infarction and angina pectoris (Xue et al., 1999[Xue, M., Cui, Y., Wang, H. Q., Hu, H. Y. & Zhang, B. (1999). J. Pharm. Biomed. Anal. 21, 207-213.]) and has antitumour activity (Ryu et al., 1997[Ryu, S. Y., Lee, C. O. & Choi, A. U. (1997). Planta Med. 63, 339-342.]). For the structure of 1,6,6-trimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione, see: Liu & Gao (2007[Liu, X.-Q. & Gao, W.-Y. (2007). Acta Cryst. E63, o2831.]).

[Scheme 1]

Experimental

Crystal data
  • C19H17BrO3

  • Mr = 373.24

  • Monoclinic, P 21 /m

  • a = 9.6063 (12) Å

  • b = 7.0457 (9) Å

  • c = 11.9688 (15) Å

  • [beta] = 96.723 (1)°

  • V = 804.52 (18) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.57 mm-1

  • T = 296 K

  • 0.48 × 0.15 × 0.12 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.372, Tmax = 0.748

  • 6178 measured reflections

  • 1634 independent reflections

  • 1177 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.087

  • S = 1.02

  • 1634 reflections

  • 144 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...O2i 0.93 2.39 3.322 (4) 177
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Bruker, 2005[Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2449 ).


Acknowledgements

We are grateful for financial support from the Natural Science Foundation of Henan Province of China (092102310075).

References

Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chang, H. M., Chui, K. Y., Tan, F. W. L., Yang, Y., Zhong, Z. P., Lee, C. M., Sham, H. L. & Wang, H. N. C. (1991). J. Med. Chem. 34, 1675-1692.  [CrossRef] [PubMed] [ChemPort] [ISI]
Liu, X.-Q. & Gao, W.-Y. (2007). Acta Cryst. E63, o2831.  [CSD] [CrossRef] [details]
Ryu, S. Y., Lee, C. O. & Choi, A. U. (1997). Planta Med. 63, 339-342.  [CrossRef] [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wang, H., Gao, X. M. & Zhang, B. L. (2005). J. Ethnopharmacol. 99, 93-98.  [ISI] [CrossRef] [PubMed] [ChemPort]
Xue, M., Cui, Y., Wang, H. Q., Hu, H. Y. & Zhang, B. (1999). J. Pharm. Biomed. Anal. 21, 207-213.  [ISI] [CrossRef] [PubMed]


Acta Cryst (2013). E69, o834  [ doi:10.1107/S1600536813011483 ]

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