2-[(E)-(4-Bromo-phenyl)imino-methyl]-4-chloro-phenol

Area of Science:

• Crystallography
• Chemical Physics

Background:

• Understanding molecular interactions and packing is crucial in crystal engineering.
• Halogenated organic compounds exhibit unique intermolecular forces influencing solid-state structures.

Purpose of the Study:

• To elucidate the crystal structure and intermolecular interactions of the title compound, C13H9BrClNO.
• To analyze the dihedral angle between substituted benzene rings and identify hydrogen bonding and halogen bonding networks.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Analysis of bond distances, angles, and non-covalent interactions (hydrogen bonds, halogen bonds, C-H interactions) was performed.

Main Results:

• The dihedral angle between the substituted benzene rings was determined to be 44.25(11)°.
• Strong intramolecular O-H⋯N hydrogen bonds forming S(6) rings were observed.
• Intermolecular contacts, including Cl⋯Cl [3.431(3) Å] and Br⋯Br [3.846(1) Å] interactions, were identified.
• Crystal packing is further influenced by C-H⋯O and C-H⋯π interactions.

Conclusions:

• The crystal structure of C13H9BrClNO is characterized by a significant dihedral angle and robust intramolecular hydrogen bonding.
• Intermolecular halogen-halogen contacts (Cl⋯Cl and Br⋯Br) play a key role in the crystal packing, alongside other non-covalent interactions.