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5-(Phenyl-diazen-yl)tropolone.

Tania N Hill¹, Moeketsi S Mangwaela, Gideon Steyl

¹Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa.

Acta Crystallographica. Section E, Structure Reports Online

|May 17, 2012

Summary

This study details the crystal structure of (E)-2-hydroxy-5-(phenyl-diazen-yl)cyclo-hepta-2,4,6-trien-1-one. Molecular interactions like hydrogen bonds and pi-pi stacking were analyzed, revealing a nearly planar structure.

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Area of Science:

Crystallography
Organic Chemistry
Molecular Structure

Background:

Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
Azo compounds, characterized by the -N=N- functional group, exhibit diverse applications in materials science and pharmaceuticals.
Tropolone derivatives are known for their unique chemical and biological activities.

Purpose of the Study:

To elucidate the crystal structure of (E)-2-hydroxy-5-(phenyl-diazen-yl)cyclo-hepta-2,4,6-trien-1-one.
To investigate the intermolecular interactions governing the solid-state packing of this compound.
To provide a detailed structural analysis for future research and applications.

Main Methods:

Single crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of bond lengths, bond angles, and dihedral angles provided insights into molecular geometry.
Identification and analysis of hydrogen bonding and π-π stacking interactions were performed.

Main Results:

The title compound, C(13)H(10)N(2)O(2), exhibits a nearly planar molecular geometry with a root-mean-square deviation of 0.036(2) Å.
A small dihedral angle of 1.57(8)° was observed between the phenyl and tropolone rings.
In the crystal lattice, molecules form inversion dimers via O-H⋯O hydrogen bonds, further linked by C-H⋯O hydrogen bonds and π-π stacking.

Conclusions:

The crystal structure reveals specific intermolecular forces that stabilize the solid-state arrangement.
The nearly planar conformation and observed interactions are key features of this azo-tropolone derivative.
This structural data serves as a foundation for understanding the compound's physical and chemical behavior.