2-[(4-Bromo-phen-yl)sulfan-yl]-2-meth-oxy-1-phenyl-ethan-1-one: crystal structure, Hirshfeld surface analysis and...

Area of Science:

• Organic Chemistry
• Crystallography
• Supramolecular Chemistry

Background:

• The synthesis and structural characterization of novel organic compounds are crucial for developing new materials and understanding molecular interactions.
• Chiral molecules with diverse functional groups present unique challenges and opportunities in chemical research.

Purpose of the Study:

• To elucidate the crystal structure and intermolecular interactions of a novel chiral compound containing bromo-phenyl, benzaldehyde, and methoxy moieties.
• To investigate the factors contributing to the self-assembly and stabilization of the molecular architecture in the solid state.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Hirshfeld surface analysis, non-covalent interaction (NCI) plots, and interaction energy calculations were used to probe weak intermolecular contacts.

Main Results:

• The compound crystallizes as a racemic mixture, featuring a chiral methine carbon atom bonded to (4-bromo-phenyl)sulfanyl, benzaldehyde, and methoxy groups.
• A significant twist was observed around the methine-C-C(carbonyl) bond (O-C-C-O torsion angle: -20.8°).
• The crystal packing is dominated by helical supramolecular chains formed through methyl- and methine-C-H⋯O(carbonyl) interactions, assembling into a 3D architecture stabilized by weaker H⋯H and C-H⋯C contacts.

Conclusions:

• The study successfully characterized a novel chiral molecule and its solid-state behavior.
• Intermolecular interactions, particularly C-H⋯O hydrogen bonds and weaker van der Waals forces, play a critical role in the formation of supramolecular structures.
• Hirshfeld surface analysis and computational methods provide valuable insights into the nature and contribution of weak interactions in crystal engineering.