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N-(4-Meth-oxy-benz-yl)phthalimide: a triclinic polymorph.

Hiroki Takahashi¹

¹Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan.

Acta Crystallographica. Section E, Structure Reports Online

|August 21, 2012

Summary

This study describes a new triclinic polymorph of 2-(4-methoxy-benzyl)-isoindoline-1,3-dione, characterized by specific torsion angles and π-π interactions. The findings detail crystal structure and intermolecular forces.

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Area of Science:

Crystallography
Solid-state chemistry
Organic chemistry

Background:

Polymorphism is crucial in determining the physical and chemical properties of organic compounds.
Previous research documented a monoclinic form of 2-(4-methoxy-benzyl)-isoindoline-1,3-dione.
Understanding crystal structures aids in predicting material behavior and optimizing synthesis.

Purpose of the Study:

To characterize a novel triclinic polymorph of 2-(4-methoxy-benzyl)-isoindoline-1,3-dione.
To elucidate the crystal packing and intermolecular interactions of this new form.
To compare the structural features with the previously reported monoclinic polymorph.

Main Methods:

Synthesis of 2-(4-methoxy-benzyl)-isoindoline-1,3-dione via reaction of potassium phthalimide and 4-methoxy-benzyl chloride in dimethylformamide.
Crystal structure determination of both platelet-shaped (triclinic) and needle-shaped (monoclinic) polymorphs.
Analysis of torsion angles, π-π stacking interactions, and hydrogen bonding networks.

Main Results:

Identification and characterization of a triclinic polymorph of 2-(4-methoxy-benzyl)-isoindoline-1,3-dione.
Observed roof-shaped molecular conformation with specific N-C-C(ar)-C(ar) torsion angles (-82.66° and 95.28°).
Established offset face-face π-π interactions between phthalimide units and weak intermolecular C-H⋯O contacts forming infinite chain motifs.

Conclusions:

The study successfully identified and structurally characterized a new triclinic polymorph.
The distinct crystal packing, including π-π interactions and hydrogen bonds, differentiates it from the monoclinic form.
These findings contribute to the understanding of polymorphism in organic compounds and structure-property relationships.