Crystal structure and Hirshfeld-surface analysis of the pesticide etoxazole

IF 0.5 Q4 CRYSTALLOGRAPHY
Chaluvarangaiah Sowbhagya , Thaluru M. Mohan Kumar , Hemmige S. Yathirajan , Sean Parkin
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引用次数: 0

Abstract

The crystal structure of the insecticide/acaricide etoxazole is presented along with a Hirshfeld surface analysis of inter­molecular inter­actions present in the crystal structure.
Etoxazole (C21H23F2NO2), systematic name 4-(4-tert-butyl-2-eth­oxy­phen­yl)-2-(2,6-di­fluoro­phen­yl)-4,5-di­hydro-1,3-oxazole, is a fluorinated insecticide and acaricide that inhibits chitin biosynthesis, disrupting insect development by preventing proper exoskeleton formation. Widely used in agriculture since 1998, it is readily absorbed by plant tissues and translocates within leaves. Metabolic studies have identified several oxidative degradation products, while toxicol­ogical assessments have examined potential effects, including oxidative stress. This study presents a detailed crystallographic and Hirshfeld surface analysis of etoxazole. The mol­ecule consists of a central di­hydro-oxazole ring flanked by 2,6-di­fluoro­phenyl and 4-tert-butyl-2-eth­oxy­phenyl groups, each twisted relative to the oxazole core. The di­hydro-oxazole ring is nearly planar, with the substituted phenyl rings forming dihedral angles of 44.20 (4)° and 47.87 (4)° with the mean plane of the di­hydro-oxazole. The eth­oxy group exhibits a dihedral angle of 15.04 (11)° to the tert-butyl­phenyl ring, while the tert-butyl group itself shows minor torsional disorder [major:minor occupancies are 0.760 (6):0.240 (6)]. The mol­ecular packing is dominated by van der Waals-type inter­actions, though weak C—H⋯F and C—H⋯O inter­actions lead to pleated layers parallel to the ab plane, which further stack along the c-axis direction. A Hirshfeld surface analysis confirms the prevalence of van der Waals inter­actions in crystal stabilization.
农药乙恶唑的晶体结构及赫氏表面分析。
乙恶唑(C21H23F2NO2),系统名称为4-(4-叔丁基-2-eth-氧-苯基)-2-(2,6-二氟-苯基)-4,5-二氢-1,3-恶唑,是一种含氟杀虫剂和杀螨剂,可抑制几丁质生物合成,通过阻止适当的外骨骼形成而破坏昆虫发育。自1998年以来广泛用于农业,它很容易被植物组织吸收并在叶片内转运。代谢研究已经确定了几种氧化降解产物,而毒理学评估已经检查了潜在的影响,包括氧化应激。本研究对乙恶唑进行了详细的晶体学和赫希菲尔德表面分析。该分子由一个中心的二氢恶唑环组成,两侧是2,6-二氟苯基和4-叔丁基-2-氧苯基,每个基团都相对于恶唑核扭曲。二氢恶唑环呈近平面结构,取代苯基环与二氢恶唑平均平面形成的二面角分别为44.20(4)°和47.87(4)°。eth-氧基与叔丁基苯基环呈15.04(11)°的二面角,而叔丁基本身表现出轻微的扭转紊乱[主要:次要占位为0.760(6):0.240(6)]。分子堆积由范德华式相互作用主导,尽管弱的C-H⋯F和C-H⋯O相互作用导致平行于ab平面的褶皱层,其进一步沿着c轴方向堆叠。Hirshfeld表面分析证实了范德华相互作用在晶体稳定中的普遍存在。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
CiteScore
1.90
自引率
0.00%
发文量
351
审稿时长
3 weeks
期刊介绍: Acta Crystallographica Section E: Crystallographic Communications is the IUCr''s open-access structural communications journal. It provides a fast, simple and easily accessible publication mechanism for crystal structure determinations of inorganic, metal-organic and organic compounds. The electronic submission, validation, refereeing and publication facilities of the journal ensure rapid and high-quality publication of fully validated structures. The primary article category is Research Communications; these are peer-reviewed articles describing one or more structure determinations with appropriate discussion of the science.
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