Crystal structure of flumioxazin.

Area of Science:

• Agricultural Chemistry
• Crystallography
• Organic Chemistry

Background:

• Dicarboximide herbicides are vital in modern agriculture.
• Understanding molecular structure is key to herbicide efficacy and design.
• Previous research has not fully elucidated the crystal structure of this specific compound.

Purpose of the Study:

• To characterize the molecular and crystal structure of the novel dicarboximide herbicide 2-[7-fluoro-3,4-di-hydro-3-oxo-4-(prop-2-yn-1-yl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetra-hydro-1H-iso-indole-1,3(2H)-dione (C19H15FN2O4).
• To investigate the intermolecular interactions governing crystal packing.
• To provide a foundation for future herbicide development.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Analysis of bond lengths, bond angles, and dihedral angles.
• Identification and analysis of intermolecular interactions, including hydrogen bonds and C-H···π interactions.

Main Results:

• The dihedral angle between the maleimide and benzene ring planes was determined to be 66.13(5)°.
• The crystal structure is stabilized by C-H⋯O and C-H⋯F hydrogen bonds.
• Weak C-H⋯π interactions contribute to the formation of 2D networks parallel to the (110) plane.

Conclusions:

• The detailed structural analysis provides critical insights into the solid-state behavior of this dicarboximide herbicide.
• The identified intermolecular interactions are fundamental to the compound's crystal lattice.
• This structural data can inform the design of new herbicides with improved properties.