(E)-4-Hy-droxy-2-{[(2-phenyl-eth-yl)iminium-yl]meth-yl}phenolate

Area of Science:

• Crystal Engineering
• Supramolecular Chemistry
• Organic Chemistry

Background:

• Schiff base compounds are versatile organic molecules with diverse applications.
• Understanding their solid-state structures is crucial for designing new materials.
• Zwitterionic forms and hydrogen bonding influence molecular packing and properties.

Purpose of the Study:

• To elucidate the crystal structure of the Schiff base compound C(15)H(15)NO(2).
• To investigate the nature of intra- and intermolecular interactions within the crystal lattice.
• To characterize the hydrogen bonding network and conformational preferences.

Main Methods:

• Single-crystal X-ray diffraction analysis was employed.
• Structural parameters, including bond lengths, angles, and hydrogen bonding, were determined.
• Analysis of intermolecular interactions such as hydrogen bonds and van der Waals forces.

Main Results:

• The compound C(15)H(15)NO(2) crystallizes as an iminium-phenolate zwitterion.
• A strong intramolecular hydrogen bond forms an S(6) ring motif involving the imine nitrogen and phenolate oxygen.
• The molecule exhibits an E conformation around the C=N bond.
• Intermolecular O-H⋯O hydrogen bonds link molecules into chains propagating along the [010] direction.
• C-H⋯O interactions are also present in the crystal structure.

Conclusions:

• The crystal structure reveals a stable zwitterionic form stabilized by intramolecular hydrogen bonding.
• The observed hydrogen bonding network dictates the supramolecular architecture in the solid state.
• These findings contribute to the understanding of structure-property relationships in Schiff base compounds.