12-(3,4,5-Trimethoxyphenyl)-2,3,4,12-tetrahydro-1H-5-oxatetraphen-1-one: crystal structure and Hirshfeld surface analysis

Jotani, Mukesh M. and Iniyavan, P. and Vijayakumar, V. and Sarveswari, S. and Tan, Yee Seng * and Tiekink, Edward R. T. * (2016) 12-(3,4,5-Trimethoxyphenyl)-2,3,4,12-tetrahydro-1H-5-oxatetraphen-1-one: crystal structure and Hirshfeld surface analysis. Acta Crystallographica Section E Crystallographic Communications, 72 (6). pp. 809-814. ISSN 2056-9890

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Official URL: http://dx.doi.org/10.1107/S2056989016007775


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) 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 cyclo­hexene ring, with the flap atom being the middle methyl­ene 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 cyclo­hexene and naphthyl rings being 10.78 (7)°. The tris­ubstituted 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 supra­molecular chains mediated by aryl-C-H...O(meth­oxy) inter­actions; chains are connected into a three-dimensional architecture by methyl­ene- and methyl-C-H...[pi] inter­actions. The prevalence of C-H...O and C-H...[pi] inter­actions is confirmed by an analysis of the Hirshfeld surface. A comparison with related structures suggests that the mol­ecular conformation of the title compound is relatively robust with respect to varying substitution patterns at the methine C atom of the pyran ring.

Item Type: Article
Additional Information: First author is with Department of Physics, Bhavan’s Sheth R. A. College of Science, Ahmedabad; 2nd, 3rd and 4th authors are with Centre for Organic and Medicinal Chemistry, VIT University, Vellore, Tamil Nadu; 5th and 6th authors are with Research Centre for Crystalline Materials, Faculty of Science and Technology, Sunway University
Uncontrolled Keywords: crystal structure; xanthene; conformation; Hirshfeld surface
Subjects: Q Science > QD Chemistry
Divisions: Others > Non Sunway Academics
Sunway University > School of Engineering and Technology [formerly School of Science and Technology until 2020] > Research Centre for Crystalline Materials moved to SMLS wef 2021
Depositing User: Ms. Molly Chuah
Related URLs:
Date Deposited: 31 Oct 2017 03:51
Last Modified: 07 Oct 2020 09:51
URI: http://eprints.sunway.edu.my/id/eprint/643

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