Year: 2025
Type: article
Abstract: Metconazole is a systemic triazole fungicide that inhibits the ergosterol biosynthesis pathway. It is widely used in agriculture to control fungal infections, including rusts, fusarium and septoria diseases. The molecular structure is a three-ring system, namely, 5-(4-chlorobenzyl)-2,2-dimethyl-1-(1 H -1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol, C 17 H 22 ClN 3 O, consisting of a cyclopentan-1-ol with 1,2,4-triazol-1-ylmethyl, gem -dimethyl and 4-chlorobenzyl groups attached at the 1-, 2- and 5-positions of the cyclopentanol ring. It has two stereocentres (cyclopentanol positions 1 and 5) leading to four stereoisomers, with the (1 S ,5 R ) form being the most bioactive. Despite its agricultural significance, detailed crystallographic data remain scarce. This study reports the crystal structure and Hirshfeld surface analysis of racemic cis -metconazole [(1 S ,5 R )/(1 R ,5 S )], determined in the monoclinic space group P 2 1 / c with two independent molecules in the asymmetric unit ( Z ′ = 2). Both exhibit similar conformations, with minor differences in the cyclopentanol ring puckering and the torsion angles between the three rings. The crystal packing consists of 2 1 -screw-related hydrogen-bonded chains parallel to the b axis, with additional weak C—H...N and C—H...Cl contacts linking adjacent molecules. Hirshfeld surface analysis indicates that intermolecular interactions are dominated by contacts involving hydrogen (96.1 and 96.7% for the two molecules).
Language: English
Subfield: Inorganic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $500
Funder: National Science Foundation
OpenAlex ID: W4409268022