Crystal structure of ethyl 4-methylthio-3-phenyl-2-thioxo-2,3-dihydro-1,3-oxazole-5-carboxylate

Article abstract of DOI:10.1007/BF01665176

The title compound C13H13NO3S2 crystallizes in the triclinic space group P<*> (Z=2) with lattice constants a=8.382(2), b=10.042(2), c=10.134(2) Angstroem, α=119.35(1) deg, β=101.40(1) deg and γ=90.54(1) deg.The interplanar angle between the least squares planes of the 1,3-oxazoline ring and the phenyl ring amounts to 90.2 deg, thus hindering conjugation between the benzene and heterocyclic system.The observed bond parameters of the five-membered heterocycle suggest a significant contribution from a zwitterionic dipolar limiting structure <38.7(5)percent> to the description of this ring system.The particular contributions of the resonance structures were estimated by calculations using the HOSE model on the base of the observed bond lengths.KEY WORDS: Crystal structure, 1,3-oxazoline-2-thione, resonance structures.