Crystal structure of oxadiarg-yl

Area of Science:

• Agrochemical Science
• Crystallography
• Organic Chemistry

Background:

• The development of novel herbicides is critical for modern agriculture.
• Understanding the molecular structure and intermolecular interactions of herbicides informs their efficacy and environmental behavior.

Purpose of the Study:

• To elucidate the crystal structure of the oxadiazolone herbicide 5-tert-butyl-3-[2,4-di-chloro-5-(prop-2-yn-yloxy)phen-yl]-1,3,4-oxa-diazol-2(3H)-one.
• To analyze the intermolecular interactions governing the compound's solid-state packing.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Analysis of intermolecular interactions, including Cl⋯Cl contacts, C-H⋯O, C-H⋯N, C-H⋯Cl hydrogen bonds, and C-H⋯π interactions.

Main Results:

• The dihedral angle between the oxadiazolone and benzene rings was determined to be 65.84(6)°.
• Weak intermolecular Cl⋯Cl contacts [3.3600(7) Å] were observed, forming chains along the b-axis.
• A three-dimensional network was generated through C-H⋯O, C-H⋯N, and C-H⋯Cl hydrogen bonds, alongside weak C-H⋯π interactions.

Conclusions:

• The crystal structure reveals specific spatial arrangements and intermolecular forces influencing the herbicide's properties.
• The identified network of interactions provides insights into the compound's stability and potential mechanisms of action.