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5-Cyano-1,3-phenyl-ene di-acetate.
Bahar Abbassi1, Michela Brumfield1, Lloyd M Jones1
1Department of Chemistry, Austin College, 900 North Grand, Sherman, TX 75090-4400, USA.
Summary
This study details the molecular structure of C11H9NO4, revealing significant twists in acetoxy groups and specific carbonyl positioning. Crystal analysis shows layered structures formed by C-H⋯O bonds and aromatic π-π interactions.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure Analysis
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Acet-oxy groups and aromatic rings are common functional groups in pharmaceuticals and materials science.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the molecule C11H9NO4.
- To analyze the conformational preferences of acet-oxy groups and the packing arrangement in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of intermolecular interactions, including hydrogen bonding and π-π stacking, was performed.
Main Results:
- The molecule C11H9NO4 exhibits significant twists of acet-oxy groups (67.89° and 53.30°) relative to the benzene ring plane.
- Carbonyl groups are positioned on the same side of the aromatic ring.
- Crystal packing is characterized by layered structures formed via weak C-H⋯O hydrogen bonds and π-π interactions between aromatic rings (inter-centroid distance of 3.767 Å).
Conclusions:
- The study provides detailed structural insights into C11H9NO4, highlighting its unique conformational features.
- The identified intermolecular interactions (hydrogen bonding and π-π stacking) are key to the observed crystal packing and may influence the molecule's bulk properties.