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Polymorphic structures of 3-phenyl-1

Dabeen Hong¹, Kyounghoon Lee¹

¹Department of Chemical Education and Research Institute of Natural Sciences, Gyeongsang National University, Gyeongsangnam-do 52828, Republic of Korea.

Acta Crystallographica. Section E, Crystallographic Communications

|June 8, 2023

Summary

Polymorphic structures of 3-phenyl-1H-1,3-benzo-diazol-2(3H)-one exhibit distinct intermolecular interactions. Differences in dihedral angles influence hydrogen bonding and pi-pi stacking, impacting crystal packing.

Keywords:

benzimidazolone crystal structure hydrogen bond

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Area of Science:

Crystallography
Solid-state chemistry
Organic chemistry

Background:

Polymorphism is crucial in determining the physical and chemical properties of organic compounds.
Understanding crystal structures aids in predicting material behavior and optimizing synthesis.
3-phenyl-1H-1,3-benzo-diazol-2(3H)-one is a compound with potential applications in materials science.

Purpose of the Study:

To characterize and compare the polymorphic structures (I and II) of 3-phenyl-1H-1,3-benzo-diazol-2(3H)-one.
To investigate the influence of structural variations on intermolecular interactions.
To elucidate the relationship between crystal packing and molecular conformation.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the crystal structures.
Analysis of bond distances, angles, and torsion angles provided insights into molecular geometry.
Intermolecular interactions, including hydrogen bonding and pi-pi stacking, were quantified and compared.

Main Results:

Two distinct polymorphic forms (I and II) of 3-phenyl-1H-1,3-benzo-diazol-2(3H)-one were identified.
Negligible differences in bond parameters were observed, but significant variations in C-N-C-C torsion angles were found.
Form I exhibited stronger C=O⋯H-N hydrogen bonds, while Form II showed stronger pi-pi interactions with shorter inter-centroid distances.

Conclusions:

The polymorphic structures display distinct supramolecular interactions attributed to variations in dihedral angles.
Crystal packing is significantly influenced by the interplay between hydrogen bonding and pi-pi stacking.
These findings contribute to the understanding of polymorphism and its impact on the solid-state properties of organic molecules.