[Journal logo]

Volume 69 
Part 5 
Page o754  
May 2013  

Received 9 April 2013
Accepted 14 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
R = 0.077
wR = 0.229
Data-to-parameter ratio = 12.7
Details
Open access

3,4-Dihydro-1H-benzo[c]chromene-1,6(2H)-dione

aSchool of Chemistry and Chemical Engineering, Henan Normal University, Henan 453007, People's Republic of China
Correspondence e-mail: xuesen.fan@htu.cn

In the title compound, C13H10O3, the pyranone and benzene rings are almost coplanar, making a dihedral angle of 1.9 (1)°. The cyclohexenone ring adopts an envelope conformation, with a methylene C atom located at the flap and displaced by 0.639 (3) Å from the mean plane of the other five atoms. In the crystal, pairs of weak C-H...[pi] interactions occur between inversion-related molecules.

Related literature

For applications of benzo[c]chromen-6-ones, see: Schmidt et al. (2003[Schmidt, J. M., Tremblay, G. B., Pagé, M., Mercure, J., Feher, M., Dunn-Dufult, R., Peter, M. G. & Redden, P. R. (2003). J. Med. Chem. 46, 1289-1292.]); Pandey et al. (2004[Pandey, J., Jha, A. K. & Hajela, K. (2004). Bioorg. Med. Chem. 12, 2239-2249.]); Matsumoto & Hanawalt (2000[Matsumoto, A. & Hanawalt, P. C. (2000). Cancer Res. 60, 3921-3926.]); Sun et al. (2006[Sun, W., Cama, L. D., Birzin, E. T., Warrier, S., Locco, L., Mosley, R., Hammond, M. L. & Rohrer, S. P. (2006). Bioorg. Med. Chem. Lett. 16, 1468-1472.]). For the synthesis, see: Fan et al. (2012[Fan, X.-S., He, Y., Cui, L.-Y., Guo, S.-H., Wang, J.-J. & Zhang, X.-Y. (2012). Eur. J. Org. Chem. pp. 673-677.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10O3

  • Mr = 214.21

  • Monoclinic, P 21 /c

  • a = 8.234 (3) Å

  • b = 10.199 (3) Å

  • c = 11.927 (4) Å

  • [beta] = 97.439 (4)°

  • V = 993.1 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.47 × 0.41 × 0.31 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • 6998 measured reflections

  • 1843 independent reflections

  • 1517 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.077

  • wR(F2) = 0.229

  • S = 1.18

  • 1843 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1-C6 benzene ring.

D-H...A D-H H...A D...A D-H...A
C11-H11B...Cgi 0.97 2.91 3.723 (5) 142
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5693 ).


Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 21272058).

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Fan, X.-S., He, Y., Cui, L.-Y., Guo, S.-H., Wang, J.-J. & Zhang, X.-Y. (2012). Eur. J. Org. Chem. pp. 673-677.  [CrossRef]
Matsumoto, A. & Hanawalt, P. C. (2000). Cancer Res. 60, 3921-3926.  [ISI] [PubMed] [ChemPort]
Pandey, J., Jha, A. K. & Hajela, K. (2004). Bioorg. Med. Chem. 12, 2239-2249.  [CrossRef] [PubMed] [ChemPort]
Schmidt, J. M., Tremblay, G. B., Pagé, M., Mercure, J., Feher, M., Dunn-Dufult, R., Peter, M. G. & Redden, P. R. (2003). J. Med. Chem. 46, 1289-1292.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sun, W., Cama, L. D., Birzin, E. T., Warrier, S., Locco, L., Mosley, R., Hammond, M. L. & Rohrer, S. P. (2006). Bioorg. Med. Chem. Lett. 16, 1468-1472.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o754  [ doi:10.1107/S1600536813010210 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.