12-(3,4,5-Tri-meth-oxy-phen-yl)-2,3,4,12-tetra-hydro-1H-5-oxa-tetra-phen-1-one: crystal structure and Hirshfeld surface analysis

Acta Crystallogr E Crystallogr Commun. 2016 May 13;72(Pt 6):809-14. doi: 10.1107/S2056989016007775. eCollection 2016 Jun 1.

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.

Keywords: Hirshfeld surface; conformation; crystal structure; xanthene.