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Updated: Jun 1, 2026
06:46
Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(E)-3-(4-Decyl-oxyphen-yl)-1-(2-hydroxy-phen-yl)prop-2-en-1-one
Summary
This study details the crystal structure of a compound, C(25)H(32)O(3), highlighting its s-cis enone configuration and specific molecular interactions. The findings reveal how these interactions stabilize the crystal lattice through chain formation and stacking.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding the three-dimensional arrangement of atoms and molecules in crystalline solids is fundamental to materials science and drug design.
- The specific configuration of functional groups, such as enones and hydroxyl groups, dictates molecular interactions and bulk properties.
- Supramolecular chemistry explores the non-covalent interactions that govern the assembly of molecules into ordered structures.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(25)H(32)O(3).
- To characterize the specific molecular geometry, including the configuration of the enone group and the dihedral angle between benzene rings.
- To identify and analyze the intra- and inter-molecular interactions responsible for the compound's crystal packing.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the precise atomic coordinates and unit cell parameters.
- Analysis of the crystal structure involved identifying bond lengths, bond angles, dihedral angles, and intermolecular contacts.
- The Cambridge Crystallographic Data Centre (CCDC) database was utilized for structural analysis and comparison.
Main Results:
- The enone group within the C(25)H(32)O(3) molecule adopts an s-cis configuration.
- A significant dihedral angle of 8.84(7)° was measured between the two benzene rings.
- An intramolecular hydrogen bond between the keto and hydroxyl groups forms a stable six-membered ring (S(6) motif).
- Intermolecular interactions, including C-H⋯O and C-H⋯π bonds, facilitate the formation of supramolecular chains along the c-axis, which are further stacked along the b-axis, stabilizing the crystal structure.
Conclusions:
- The crystal structure of C(25)H(32)O(3) is characterized by an s-cis enone and specific benzene ring orientation.
- Intramolecular hydrogen bonding plays a crucial role in the molecule's conformation.
- A combination of intermolecular C-H⋯O and C-H⋯π interactions dictates the formation of a robust three-dimensional crystal lattice through chain assembly.
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