[Journal logo]

Volume 69 
Part 4 
Page o484  
April 2013  

Received 18 February 2013
Accepted 27 February 2013
Online 2 March 2013

Key indicators
Single-crystal X-ray study
T = 446 K
Mean [sigma](C-C) = 0.001 Å
R = 0.037
wR = 0.104
Data-to-parameter ratio = 17.9
Details
Open access

1-(5-Hydroxy-2,2,8,8-tetramethyl-2H,8H-pyrano[2,3-f]chromen-6-yl)-3-(4-methoxyphenyl)prop-2-en-1-one

aSchool of Chemistry and Physics, University of KwaZulu-Natal, Durban 4000, South Africa
Correspondence e-mail: koorbanally@ukzn.ac.za

In the biologically active title compound, C26H26O5, the pyran ring of the chromene unit adopts a half-chair conformation. The C=C double bond of the propenone unit exhibits a trans conformation and the carbonyl group is syn conformation to the double bond. The dihedral angle between the benzene ring and the benzopyranone moiety is 31.54 (4)°. The molecular structure is stabilized by an intramolecular C=O...H-O hydrogen bond.

Related literature

For related structures, see: Bhattacharyya et al. (1999[Bhattacharyya, K., Mazumdar, S. K., Bocelli, G., Cantoni, A., Ray, A. B., Neogi, P. & Mazumdar, G. (1999). Acta Cryst. C55, 215-217.]); Lee & Li (2007[Lee, Y. R. & Li, X. (2007). Bull. Korean Chem. Soc. 28, 1739-1745.]); Lin et al. (1992[Lin, Y.-L., Chen, Y.-L. & Kuo, Y.-H. (1992). Chem. Pharm. Bull. 40, 2295-2299.]); Narender et al. (2005[Narender, T., Khaliq, T., Shweta, Nishi, Goyal, N. & Gupta, S. (2005). Bioorg. Med. Chem. 13, 6543-6550.]); Liu et al. (2005[Liu, T., Xu, Z.-M. & Hu, Y.-Z. (2005). Acta Cryst. E61, o3389-o3390.]). For the biological activity of similar molecules, see: Nicolaou et al. (2000[Nicolaou, K. C., Pfefferkorn, J. A., Roecker, A. J., Cao, G.-Q., Barluenga, S. & Mitchell, H. J. (2000). J. Am. Chem. Soc. 122, 9939-9953.]); Dhar (1981[Dhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds, pp. 1-32. New York: John Wiley and Sons.]). For bond lengths and angles in related structures, see: Bhattacharyya et al. (1999[Bhattacharyya, K., Mazumdar, S. K., Bocelli, G., Cantoni, A., Ray, A. B., Neogi, P. & Mazumdar, G. (1999). Acta Cryst. C55, 215-217.]); Pawar et al. (2012[Pawar, S., Cheddie, A., Omondi, B. & Koorbanally, N. A. (2012). Acta Cryst. E68, o3048.]).

[Scheme 1]

Experimental

Crystal data
  • C26H26O5

  • Mr = 418.47

  • Monoclinic, P 21 /c

  • a = 9.6422 (2) Å

  • b = 12.0871 (3) Å

  • c = 18.4517 (4) Å

  • [beta] = 99.228 (1)°

  • V = 2122.64 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 446 K

  • 0.37 × 0.33 × 0.21 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.981

  • 68753 measured reflections

  • 5126 independent reflections

  • 4677 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.104

  • S = 1.01

  • 5126 reflections

  • 286 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3A...O2 0.82 1.72 2.4523 (10) 148

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2099 ).


Acknowledgements

SP thanks the College of Agriculture, Engineering and Science of the University of KwaZulu-Natal for a doctoral bursary.

References

Bhattacharyya, K., Mazumdar, S. K., Bocelli, G., Cantoni, A., Ray, A. B., Neogi, P. & Mazumdar, G. (1999). Acta Cryst. C55, 215-217.  [CSD] [CrossRef] [details]
Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds, pp. 1-32. New York: John Wiley and Sons.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Lee, Y. R. & Li, X. (2007). Bull. Korean Chem. Soc. 28, 1739-1745.  [ChemPort]
Lin, Y.-L., Chen, Y.-L. & Kuo, Y.-H. (1992). Chem. Pharm. Bull. 40, 2295-2299.  [CrossRef] [ChemPort]
Liu, T., Xu, Z.-M. & Hu, Y.-Z. (2005). Acta Cryst. E61, o3389-o3390.  [CSD] [CrossRef] [details]
Narender, T., Khaliq, T., Shweta, Nishi, Goyal, N. & Gupta, S. (2005). Bioorg. Med. Chem. 13, 6543-6550.  [CrossRef] [PubMed] [ChemPort]
Nicolaou, K. C., Pfefferkorn, J. A., Roecker, A. J., Cao, G.-Q., Barluenga, S. & Mitchell, H. J. (2000). J. Am. Chem. Soc. 122, 9939-9953.  [ISI] [CrossRef] [ChemPort]
Pawar, S., Cheddie, A., Omondi, B. & Koorbanally, N. A. (2012). Acta Cryst. E68, o3048.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o484  [ doi:10.1107/S1600536813005734 ]

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.