Partially reduced thiochromene based oxathiahelicenes: crystallographic, computational and Hirschfeld surface analyses?

CrystEngComm Pub Date: 2013-06-27 DOI: 10.1039/C3CE41078A

Abstract

An efficient and concise route for the construction of thiochromene based oxahelicenes in which heteroatoms are located on the outer helix through base-induced ring transformation of 4-sec.amino-2-oxo-2,5-dihydrothiochromeno[4,3-b]pyran-3-carbonitriles by thiochroman-4-one, 1-indanone and 2-indanone separately has been described. The X-ray studies for P and 4a show the formation of supramolecular structures through weak C–H?O and C–H?N intermolecular interactions. Supramolecular chains in 6a through C–H?N and π?π and in 7via C–H?π and π?π weak and intermolecular interactions have been observed. The detail analyses of Hirschfeld surface and fingerprint plots gave a comparative picture of the modes of non-covalent interactions in the newly synthesized compounds. The stabilization energies associated with these weak interactions have been estimated using DFT and AIM theory calculations.

Graphical abstract: Partially reduced thiochromene based oxathiahelicenes: crystallographic, computational and Hirschfeld surface analyses
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