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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)-2-Eth-oxy-6-[(4-ethoxy-phen-yl)imino-meth-yl]phenol
Summary
This study details the crystal structure of C(17)H(19)NO(3), revealing three independent molecules adopting a phenol-imine tautomeric form. Intramolecular hydrogen bonds and C-H⋯π interactions influence their nearly parallel arrangement in the crystal lattice.
Area of Science:
- Crystallography
- Supramolecular Chemistry
- Organic Chemistry
Background:
- Understanding the solid-state behavior of organic molecules is crucial for predicting their physical and chemical properties.
- Tautomerism, particularly phenol-imine tautomerism, plays a significant role in the structural diversity and reactivity of organic compounds.
- Crystal engineering relies on identifying and characterizing intermolecular and intramolecular interactions to design materials with specific properties.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(17)H(19)NO(3).
- To investigate the tautomeric form and molecular arrangement in the solid state.
- To identify and analyze the types of interactions present in the crystal structure.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and dihedral angles provided insights into molecular geometry.
- Non-covalent interaction analysis, including hydrogen bonding and C-H⋯π interactions, was performed.
Main Results:
- The asymmetric unit contains three independent molecules of C(17)H(19)NO(3).
- All three molecules exist in the phenol-imine tautomeric form.
- Intramolecular O-H⋯N hydrogen bonds form S(6) ring motifs in each molecule.
- The dihedral angles between aromatic rings vary significantly (13.55(2)°, 21.24(2)°, and 46.26(1)°).
- C-H⋯π interactions were observed, contributing to the crystal packing.
Conclusions:
- The crystal structure of C(17)H(19)NO(3) reveals a complex arrangement of three independent phenol-imine tautomers.
- Intramolecular hydrogen bonding is a key feature dictating the conformation of individual molecules.
- The observed dihedral angles and C-H⋯π interactions provide insights into the supramolecular assembly and potential crystal engineering strategies.
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