Received 19 February 2011
In the title compound, [Cr(C16H16O2)(CO)3], the Cr0 atom of the Cr(CO)3 unit is coordinated to the phenyl ring of the flavan ligand in an 6 mode, with a normal arene-to-metal distance. The Cr(CO)3 unit exhibits a three-legged piano-stool conformation, while the dihydropyran ring displays a distorted envelope configuration. The phenyl ring is twisted away from the fused ring system by 25.5 (2)°. The methoxy group is almost coplanar with the phenyl ring [CMe-O-Car-Car torsion angle = 8.46 (2)°]. The crystal packing is stabilized by intermolecular C-HO interactions.
For similar structures, see: van Tonder et al. (2010a,b) and for other related structures, see: van Tonder et al. (2009a,b). For the synthesis of the title compound, see: Müller et al. (1999) and for the sythesis of 7-methoxyflavan-4-one, see: Sato et al. (2006). For standard bond lengths, see: Allen et al. (1987). For the importance of flavonoids in biological investigations, see: Rice-Evans & Packer (2003). For the use of tricarbonyl(arene)chromium complexes in regioselective organic synthesis, see: Muschalek et al. (2007).
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenberg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HP2002 ).
The University of the Free State and Sasol Ltd are gratefully acknowledged for financial support and Johannes van Tonder for the NMR data and help with the synthesis of the title compound. Special thanks are due to Prof Andreas Roodt.
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