Anisole at 100 K: the first crystal structure determination

Area of Science:

• Crystallography
• Solid-state chemistry
• Organic chemistry

Background:

• Anisole (methoxybenzene) is a fundamental feedstock chemical.
• It finds extensive applications within the pharmaceutical industry.

Purpose of the Study:

• To determine the precise crystal structure of anisole at 100 K.
• To elucidate the intermolecular interactions governing anisole's solid-state arrangement.

Main Methods:

• Single-crystal X-ray diffraction was employed.
• Crystals were grown from the melt.

Main Results:

• Anisole crystallizes in the P2(1)/c space group with Z'=2.
• Two unique, nearly planar anisole molecules occupy the asymmetric unit.
• The solid-state structure exhibits a herringbone packing motif.
• Intermolecular interactions are characterized by edge-to-face contacts, not face-to-face π-π stacking.

Conclusions:

• The study provides detailed structural insights into anisole at low temperatures.
• Understanding anisole's packing is crucial for its industrial applications.
• The observed packing highlights the importance of specific intermolecular forces in organic solids.