In situ cryocrystallization of diphenyl ether: C-H...pi mediated polymorphic forms

Area of Science:

• Solid-state chemistry
• Crystallography
• Supramolecular chemistry

Background:

• Diphenyl ether is a common organic compound with potential for diverse solid-state structures.
• Understanding crystal packing is crucial for predicting material properties.

Purpose of the Study:

• To investigate and characterize the polymorphic forms of diphenyl ether.
• To elucidate the intermolecular forces governing crystal packing.

Main Methods:

• In situ crystallization techniques were employed.
• Single-crystal X-ray diffraction was used to determine crystal structures.

Main Results:

• Two distinct crystal forms of diphenyl ether were identified: a monoclinic centrosymmetric form (P21/n) and an orthorhombic noncentrosymmetric form (P212121).
• Analysis revealed that weak inter- and intramolecular C-H...pi interactions are the primary drivers of molecular packing in both polymorphs.

Conclusions:

• Diphenyl ether exhibits polymorphism, influenced by subtle non-covalent interactions.
• The identified crystal structures provide insights into the role of C-H...pi interactions in controlling the solid-state arrangement of organic molecules.