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Bostrycin.

Shao-Yuan Chen, Chao Huang, Chu-Long Zhang

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study reveals a potent plant toxin, C(16)H(16)O(8), whose crystal structure is an average of two tautomers. The compound features cyclohexene rings in a half-chair conformation and an extensive hydrogen-bonding network.

Area of Science:

* Phytochemistry and Plant Pathology
* Structural Chemistry and Crystallography

Background:

* The title compound, C(16)H(16)O(8), is identified as a potent, non-specific phytotoxin.
* Understanding the structural basis of its activity is crucial for agricultural and environmental science.

Purpose of the Study:

* To elucidate the crystal structure of the title compound.
* To characterize the tautomeric forms and conformational properties.
* To investigate the intermolecular interactions within the crystal lattice.

Main Methods:

* Single-crystal X-ray diffraction was employed to determine the crystal structure.
* Analysis of bond lengths, angles, and intermolecular contacts.
* Identification of tautomeric forms and conformational analysis of the cyclohexene rings.

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Main Results:

* The crystal structure represents an average of two tautomers: 5,6,7,9,10-penta-hydroxy-2-methoxy-7-methyl-1,4,5,6,7,8-hexahydroanthracene-1,4-dione and 1,4,5,6,7-pentahydroxy-2-methoxy-7-methyl-5,6,7,8,9,10-hexahydroanthracene-9,10-dione.
* Both tautomers exhibit cyclohexene rings in a half-chair conformation.
* An extensive O-H⋯O hydrogen-bonding network was observed, contributing to the crystal packing.

Conclusions:

* The crystal structure provides detailed insights into the molecular architecture of this potent phytotoxin.
* The identified tautomerism and conformational preferences are key structural features.
* The extensive hydrogen-bonding network likely influences the compound's stability and interactions.