2-Hydroxy-benzyl alcohol-phenanthroline (1/1)

Area of Science:

• Crystallography
• Supramolecular Chemistry
• Organic Chemistry

Background:

• Cocrystallization is a valuable technique for designing novel crystalline materials.
• Understanding intermolecular interactions is crucial for predicting crystal structures.
• Phenanthroline and 2-hydroxy-benzyl alcohol are common organic molecules with distinct hydrogen bonding capabilities.

Purpose of the Study:

• To investigate the crystal structure formed by cocrystallization of phenanthroline and 2-hydroxy-benzyl alcohol.
• To elucidate the nature of intermolecular interactions governing the crystal packing.
• To explore deviations from expected hydrogen bonding patterns in cocrystals.

Main Methods:

• Cocrystallization experiments were performed.
• Single-crystal X-ray diffraction was used to determine the crystal structure.
• Analysis of hydrogen bonding and π-π interactions was conducted.

Main Results:

• The title compound, C(12)H(8)N(2)·C(7)H(8)O(2), was successfully synthesized and characterized.
• An unexpected crystal packing arrangement was observed, deviating from simple dimer formation.
• One hydroxyl group formed a bifurcated hydrogen bond to both phenanthroline nitrogen atoms.
• The other hydroxyl group formed an O-H⋯O hydrogen bond with a symmetry-equivalent molecule.
• Stabilizing π-π interactions between phenanthroline ring systems were identified with a centroid-centroid distance of 3.570 Å.

Conclusions:

• The crystal structure is primarily stabilized by a combination of bifurcated and intermolecular hydrogen bonds, along with π-π stacking interactions.
• The study highlights the complexity of intermolecular interactions in cocrystal formation.
• This finding provides insights into crystal engineering strategies involving molecules with multiple hydrogen bond donors and acceptors.