4-Acetyl-3-[2-(eth-oxy-carbon-yl)phen-yl]sydnone
David Grossie1, Leanna Harrison1, Kenneth Turnbull1
1Department of Chemistry, Wright State University, Dayton, OH 45435, USA.
Acta Crystallographica. Section E, Structure Reports Online
|January 24, 2014
Summary
Sydnones are mesoionic heterocyclic compounds. The study synthesized a novel sydnone derivative with an aromatic substituent, revealing insights into its structural stability and intermolecular interactions.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Sydnones are mesoionic five-membered heterocyclic compounds.
- Aromatic substituents at the N3 position enhance sydnone stability.
- Understanding the structural and bonding characteristics of sydnone derivatives is crucial.
Purpose of the Study:
- To synthesize and characterize a novel sydnone derivative with a 2-(ethoxy-carbonyl)phenyl substituent.
- To investigate the intra- and intermolecular interactions within the synthesized compound.
- To analyze the crystal structure and molecular geometry of the title compound.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Analysis of hydrogen bonding networks (intra- and intermolecular).
- Calculation of the inter-planar angle between the sydnone and phenyl rings.
Main Results:
- The crystal structure of 4-acetyl-3-[2-(ethoxy-carbonyl)phenyl]-1,2,3-oxadiazol-3-ium-5-olate (C13H12N2O5) was determined.
- Intra- and intermolecular hydrogen bonds were identified.
- A significant inter-planar angle of 71.94° between the sydnone and benzene rings was observed.
- π-ring⋯carbonyl interactions of 3.2038 Å were found between the sydnone ring and a symmetry-related carbonyl group.
Conclusions:
- The synthesized sydnone derivative exhibits a specific molecular conformation influenced by the bulky aromatic substituent.
- The presence of both hydrogen bonds and π-ring interactions contributes to the crystal packing and stability.
- This study provides valuable structural data for sydnone chemistry and supramolecular assembly.
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