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Alternariol.

David Siegel, Sergey Troyanov, Johannes Noack

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

The molecular structure of 3,7,9-trihydroxy-1-methyl-6H-benzo[c]chromen-6-one features a twisted benzene ring due to steric hindrance. Intramolecular and intermolecular hydrogen bonds stabilize the crystal structure into a 3D network.

Area of Science:

Organic Chemistry
Crystallography
Molecular Structure Analysis

Background:

Benzo[c]chromen-6-one derivatives are known for diverse biological activities.
Understanding the precise molecular geometry and intermolecular interactions is crucial for structure-activity relationship studies.

Purpose of the Study:

To elucidate the detailed molecular structure and crystal packing of 3,7,9-trihydroxy-1-methyl-6H-benzo[c]chromen-6-one.
To investigate the role of steric effects and hydrogen bonding in stabilizing the molecular and crystal structure.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
Analysis of bond lengths, bond angles, and intermolecular interactions (hydrogen bonds) was performed.

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Main Results:

The methyl group at position 1 is sterically hindered, causing a twist in the benzene ring system.
An intramolecular O-H⋯O hydrogen bond forms an S(6) ring, contributing to molecular stability.
Intermolecular O-H⋯O hydrogen bonds link molecules into a robust three-dimensional crystal network.

Conclusions:

The study provides a detailed structural characterization of the title compound.
Steric effects and hydrogen bonding play significant roles in the observed molecular conformation and crystal packing.