Crystal structure of pymetrozine

Area of Science:

• Crystallography
• Chemical Crystallography
• Materials Science

Background:

• The compound 6-methyl-4-[(E)-(pyridin-3-yl-methyl-idene)amino]-4,5-di-hydro-1,2,4-triazin-3(2H)-one (C10H11N5O) is recognized for its application as an anti-feedant in pest control strategies.
• Understanding the precise molecular arrangement and intermolecular forces is crucial for optimizing its efficacy and developing new pest management solutions.

Purpose of the Study:

• To elucidate the crystal structure of the anti-feedant compound C10H11N5O.
• To analyze the molecular conformation, including dihedral angles between aromatic rings.
• To investigate the hydrogen bonding network and π-π interactions governing the crystal packing.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the crystal structure.
• Analysis of the asymmetric unit, including the identification of independent molecules (A and B).
• Calculation of dihedral angles between pyridinyl and triazinyl ring systems and characterization of hydrogen bonds (N-H⋯O, N-H⋯N, C-H⋯N, C-H⋯O) and π-π interactions.

Main Results:

• The asymmetric unit contains two independent molecules (A and B) with distinct dihedral angles (11.60(6)° and 18.06(4)°) between the pyridinyl and triazinyl ring planes.
• A comprehensive network of hydrogen bonds and weak π-π interactions (ring-centroid separations of 3.5456(9) Å and 3.9142(9) Å) was identified.
• These interactions effectively link the pyridinyl and triazinyl rings, resulting in a stable three-dimensional crystal network.

Conclusions:

• The detailed crystal structure provides fundamental insights into the solid-state behavior of this anti-feedant compound.
• The identified hydrogen bonding and π-π interactions are key to the compound's crystal packing and stability.
• This structural information can guide future research in designing more effective pest control agents.