Abstract
In the title compound, C26H24O5, the pyran ring has a flattened-boat con-formation, with the 1,4-related ether O and methine C atoms lying 0.1205 (18) and 0.271 (2) Å, respectively, above the least-squares plane involving the doubly bonded C atoms (r.m.s deviation = 0.0208 Å). An envelope conformation is found for the cyclo-hexene ring, with the flap atom being the middle methyl-ene C atom, lying 0.616 (2) Å out of the plane defined by the remaining atoms (r.m.s. deviation = 0.0173 Å). The fused four-ring system is approximately planar, with the dihedral angle between the least-squares planes through the cyclo-hexene and naphthyl rings being 10.78 (7)°. The tris-ubstituted benzene ring occupies a position almost perpendicular to the pyran ring [dihedral angle = 83.97 (4)°]. The most prominent feature of the packing is the formation of zigzag supra-molecular chains mediated by aryl-C-H⋯O(meth-oxy) inter-actions; chains are connected into a three-dimensional architecture by methyl-ene- and methyl-C-H⋯π inter-actions. The prevalence of C-H⋯O and C-H⋯π inter-actions is confirmed by an analysis of the Hirshfeld surface. A comparison with related structures suggests that the mol-ecular conformation of the title compound is relatively robust with respect to varying substitution patterns at the methine C atom of the pyran ring.
Highlights
In the title compound, C26H24O5, the pyran ring has a flattened-boat conformation, with the 1,4-related ether O and methine C atoms lying 0.1205 (18) and 0.271 (2) A, respectively, above the least-squares plane involving the doubly bonded C atoms (r.m.s deviation = 0.0208 A )
An envelope conformation is found for the cyclohexene ring, with the flap atom being the middle methylene C atom, lying 0.616 (2) Aout of the plane defined by the remaining atoms (r.m.s. deviation = 0.0173 A )
The most prominent feature of the packing is the formation of zigzag supramolecular chains mediated by aryl-C—HÁ Á ÁO(methO(methoxy) interactions; chains are connected into a three-dimensional architecture by methylene- and methyl-C—HÁ Á Á interactions
Summary
Xanthenes and benzoxanthenes are important bioactive compounds that possess a wide range of biological and therapeutic properties, such as analgesic (Hafez et al, 2008), antiviral and antibacterial and anti-inflammatory activities (Poupelin et al, 1978; Hideo & Teruomi, 1981; Asano et al, 1996; Matsumoto et al, 2005; Pinto et al, 2005; Woo et al, 2007; Pouli & Marakos, 2009) Some of these compounds have been used in photodynamic therapy (Ion, 1997). Various methods for the synthesis of tetrahydrobenzo[a]xanthen-11-ones have been reported (Knight & Stephens, 1989) These usually involve a three-component condensation of dimedone with an aromatic aldehyde and 2-naphthol. Symmetry codes: (i) Àx þ 12; y À 12; z; (ii) x À 12; Ày þ 12; Àz; (iii) Àx; Ày þ 1; Àz; (iv) x À 32; y; Àz À 12
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