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Updated: May 11, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(E)-N-[(E)-3-(4-Nitro-phen-yl)allyl-idene]naphthalen-1-amine
Kee Dal Nam1, Joo Hwan Cha, Yong Seo Cho
1Chemical Kinomics Research Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea.
This study details the crystal structure of a C19H14N2O2 compound, revealing specific molecular geometry and intermolecular interactions. The research highlights the arrangement of nitro-phenyl and naphthalene rings and weak hydrogen bonds in its solid-state structure.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding the solid-state structure of organic molecules is crucial for predicting their physical and chemical properties.
- The specific arrangement of functional groups and aromatic systems influences molecular packing and intermolecular forces.
Purpose of the Study:
- To elucidate the detailed crystal structure of the organic compound C19H14N2O2.
- To analyze the dihedral angles between aromatic systems and the conformation of the imine group.
- To identify and characterize intermolecular interactions, such as hydrogen bonds, in the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
- Analysis of bond lengths, bond angles, torsion angles, and intermolecular contacts was performed.
Main Results:
- The dihedral angle between the 4-nitro-phenyl ring and the naphthalene ring system was determined to be 12.79(2)°.
- The imine group exhibited a C-C-N=C torsion angle of 41.0(2)°, with the C=N bond adopting an E conformation.
- Weak C-H⋯O hydrogen bonds were observed, leading to the formation of molecular layers parallel to the b axis.
Conclusions:
- The crystal structure of C19H14N2O2 is characterized by a specific spatial arrangement of its aromatic moieties and imine functional group.
- Intermolecular C-H⋯O hydrogen bonding plays a significant role in organizing the molecules into a layered supramolecular architecture.
- These findings contribute to the understanding of structure-property relationships in organic crystalline materials.
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