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Structure of thiolactomycin.

Y Nawata¹, H Sasaki, H Oishi

¹Research Laboratories, Chugai Pharmaceutical Co. Ltd, Tokyo, Japan.

Acta Crystallographica. Section C, Crystal Structure Communications

|June 15, 1989

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This study details the crystal structure of a specific thiolactone, [4R,(2E,5E)]-3-Hydroxy-2,4,6-trimethyl-2,5,7-octatriene-4-thiolide. The absolute configuration was confirmed using the Bijvoet method, revealing a planar thiolactone ring.

Area of Science:

Crystallography
Organic Chemistry
Structural Chemistry

Background:

Thiolactones are sulfur-containing heterocyclic compounds with diverse chemical properties.
Understanding the precise three-dimensional structure of organic molecules is crucial for predicting their reactivity and function.

Purpose of the Study:

To determine the crystal structure and absolute configuration of [4R,(2E,5E)]-3-Hydroxy-2,4,6-trimethyl-2,5,7-octatriene-4-thiolide.
To analyze the geometric parameters of the thiolactone ring and its substituents.

Main Methods:

Single-crystal X-ray diffraction was employed to collect diffraction data.
The absolute configuration was established using the Bijvoet method.
Crystal structure refinement was performed using 1021 unique reflections.

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Main Results:

The crystal structure was solved in the hexagonal space group P6(5).
The thiolactone ring was found to be planar, with specific S-C bond distances and C-S-C angle reported.
The angle between the thiolactone and butadienyl groups was determined to be 101.7 degrees.

Conclusions:

The absolute configuration of the title compound was unambiguously determined.
The structural analysis provides insights into the planarity and conformation of the thiolactone moiety within this specific molecule.
This crystallographic data serves as a reference for related sulfur-containing organic compounds.