[Arylméthylène thiocétones chirales. Structure du 3-(o-méthoxyphényl)méthylène thiocamphre]

Lamazouere, AM.;Elbatouti, N.;Sotiropoulos, J.;Dupont, L.;Germain, Gabriel
(1995) Zeitschrift fuer Kristallographie : international journal for structural, physical, and chemical aspects of crystalline materials — Vol. 210, n° 8, p. 597-601 (1995)

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  • Lamazouere, AM.
    Author
  • Elbatouti, N.
    Author
  • Sotiropoulos, J.
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  • Dupont, L.
    Author
  • Germain, GabrielUCLouvain
    Author
Abstract
Arylmethylene thiocamphors are easily obtained from corresponding (+)-arylmethylene camphors by reaction with Lawesson reagent or P4S10. Crystals of o-methoxyphenylmethylene thiocamphor C18H22OS belong to space-group P2(1)2(1)2(1) with a = 7.581(9) Angstrom, b = 12.884(7) Angstrom and c = 16.831(7) Angstrom, Z = 4, T = 293 K. The final R is 0.055 for 1300 unique reflections. The cohesion of the crystal is the result of van der Waals interactions. This compound and all arylmethylene thiocamphors adopt the E configuration, more stable from the stereochemical point of view. The conjugated S=C-C=C system is skewed in the sense of a left handed helix. Furthermore, the aromatic ring is twisted (-32 degrees). Exciton Circular Dichroism is consistent with this conformation.
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Lamazouere, AM., Elbatouti, N., Sotiropoulos, J., Dupont, L., & Germain, G. (1995). [Arylméthylène thiocétones chirales. Structure du 3-(o-méthoxyphényl)méthylène thiocamphre]. Zeitschrift fuer Kristallographie : international journal for structural, physical, and chemical aspects of crystalline materials, 210(8), 597-601. https://doi.org/10.1524/zkri.1995.210.8.597 (Original work published 1995)