An X-ray Crystallographic and Computational Study of Intermolecular Edge-to-Face Aromatic Interaction in Crystal Structure of exo [4+2]π Cycloadduct of Phencyclone and S-Allyl S-Methyl Dithiocarbonate

Phencyclone reacted with S-allyl S-methyl dithiocarbonate derived from the [3,3]-sigmatropic rearrangement of O-allyl S-methyl dithiocarbonate to give an 1:1 mixture of endo and exo [4+2]π cycloadducts. The single crystal X-ray analysis of the exo [4+2]π cycloadduct was performed. The molecules are linked together with the intermolecular edge-to-face interaction between the phenyl hydrogen atom and the phenanthrene ring. The PM3 calculation reproduced the structural feature of the molecular packing.