5-(Phenyl-diazen-yl)tropolone.

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.