Methyl 9H-xanthene-9-carboxyl-ate

Area of Science:

• Organic Chemistry
• Crystallography
• Medicinal Chemistry

Background:

• Propantheline bromide is an anti-muscarinic drug.
• Xanthone derivatives possess diverse biological activities.
• Unintended synthesis can lead to discovery of novel compounds.

Purpose of the Study:

• To characterize the structure of an unintentionally synthesized xanthone derivative.
• To investigate the molecular conformation and packing of the novel compound.
• To understand the crystallization behavior of the byproduct.

Main Methods:

• Single-crystal X-ray diffraction was used for structural determination.
• Analysis of bond lengths, angles, and torsion angles.
• Investigation of intermolecular interactions, including C-H⋯π, π-π stacking, and C-H⋯O interactions.

Main Results:

• The title compound, C(15)H(12)O(3), was identified as a xanthone derivative.
• The xanthone unit exhibited a folded conformation with a dihedral angle of 24.81°.
• The ester substituent adopted a trans staggered conformation (torsion angle 178.4°).
• Molecules formed layered structures through weak C-H⋯π and π-π interactions, along with a C-H⋯O interaction.

Conclusions:

• The study successfully characterized a novel xanthone derivative obtained as a synthetic byproduct.
• The detailed structural analysis provides insights into the conformational preferences and solid-state packing of this xanthone.
• The findings contribute to the understanding of xanthone chemistry and crystallization phenomena.