6-Methyl-3-phenylthiochroman-4-one and 6-methoxy-3-phenylthiochroman-4-one : Configurational preference of the phenylthio group at the third position due to remote substitution
15 Aug 1997-Acta Crystallographica Section C-crystal Structure Communications (International Union of Crystallography)-Vol. 53, Iss: 8, pp 1073-1075
TL;DR: The pyran ring adopts a distorted sofa conformation in the title compounds, 6-methyl-3-phenylthiochroman-4-one (C 16 H 14 O 2 S), (I), and 6-methoxy-3,phenylthyiochroma-4,5,6,7,8,9,10,11,
Abstract: The pyran ring adopts a distorted sofa conformation in the title compounds, 6-methyl-3-phenylthiochroman-4-one (C 16 H 14 O 2 S), (I), and 6-methoxy-3-phenylthiochroman-4-one (C 16 H 14 O 3 S), (II). The S atom substituted at the third position is attached equatorially in (II) and axially in (I). High-resolution proton NMR studies could not provide a conclusive explanation for this feature.
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TL;DR: The crystal structures of CH3(C9H6O2)SO2C6H5 and CH3C8H8O2 )SO2−C6h5 have been determined by X-ray diffraction as discussed by the authors.
Abstract: The crystal structures of (i) CH3(C9H6O2)SO2C6H5 and (ii) CH3(C8H8O2)SO2−C6H5 have been determined by X-ray diffraction. (i) crystallizes in the monoclinic space groupP21/c with unit cell parametersa=8.814(1)A,b=10.310(1)A,c=15.841(4)A, β=98.17(1)o, andZ=4, and (ii) crystallizes in the orthorhombic space groupP212121 with unit cell parametersa=6.206(1)A,b=11.752(5)A,c=19.865(3)A, andZ=4. The pyran ring in both of them is in the distorted half-chair conformation with differeing degrees of distortion from the ideal.