(E)-2-[(2-Ethyl-phen-yl)iminiometh-yl]-6-hydroxy-phenolate

Area of Science:

• Crystallography
• Organic Chemistry
• Materials Science

Background:

• Understanding the solid-state structure of organic molecules is essential for predicting their physical and chemical properties.
• Zwitterionic compounds possess unique charge distributions influencing their intermolecular interactions and crystal packing.
• Aromatic interactions play a significant role in the self-assembly and stability of crystalline organic materials.

Purpose of the Study:

• To elucidate the crystal structure of the title compound, C(15)H(15)NO(2).
• To investigate the nature of intermolecular interactions, including hydrogen bonding and pi-pi stacking, within the crystal lattice.
• To characterize the molecular conformation and stereochemistry, specifically the E configuration around the C=N bond.

Main Methods:

• Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional molecular structure.
• Analysis of hydrogen bonding networks and non-covalent interactions was performed.
• Geometric parameters, including dihedral angles and bond lengths, were precisely measured.

Main Results:

• The compound crystallizes in a zwitterionic form with an E configuration about the C=N bond.
• A notable dihedral angle of 5.59(6)° was observed between the two aromatic rings.
• Intramolecular N-H⋯O hydrogen bonds formed an S(6) ring motif, while intermolecular O-H⋯O hydrogen bonds created R(2)(2)(10) dimers.
• Aromatic pi-pi interactions with a centroid-centroid distance of 3.4808(7) Å were identified between adjacent dimers.

Conclusions:

• The crystal structure provides detailed insights into the molecular organization and intermolecular forces governing the solid state of this zwitterionic compound.
• The observed hydrogen bonding and pi-pi interactions are key factors in the formation of the crystal lattice and dimer assembly.
• This structural characterization contributes to the broader understanding of structure-property relationships in organic crystalline materials.