Crystal structure and Hirshfeld surface analysis of 1-[2-(2-chloroethoxy)ethyl]-2-methyl-4-nitro-1H-imidazole

IF 0.6 Q4 CRYSTALLOGRAPHY

Acta Crystallographica Section E: Crystallographic Communications Pub Date : 2025-07-01 DOI:10.1107/S2056989025005493

Thaluru M. Mohan Kumar , Papegowda Bhavya , Besagarahally L. Bhaskar , Holehundi J. Shankara Prasad , Hemmige S. Yathirajan , Sean Parkin

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Abstract

The crystal structure and a Hirshfeld surface analysis of 1-[2-(2-chloroethoxy)ethyl]-2-methyl-4-nitro-1H-imidazole are presented.

Imidazoles are a widely studied class of heterocyclic compounds with significant biological and pharmacological relevance, including applications as fungicides, herbicides, and therapeutic agents. The title compound, C₈H₁₂ClN₃O₃ (I), is a structural analogue and impurity of the anti-protozoal drug metronidazole, making it valuable for mechanistic and drug development studies. Here, we report its crystal structure and Hirshfeld surface analysis. Crystals of I are triclinic, space-group type P1, with two independent molecules (A and B) in the asymmetric unit, each exhibiting chloroethoxyethyl chain disorder over two conformations. Both molecules have essentially planar methyl-nitro-1H-imidazole cores, with conformational variation arising from the side chains. The structure lacks conventional hydrogen bonds but features several weak C—H⋯O, C—H⋯N, and C—H⋯Cl interactions, connecting molecules into dimers and layers parallel to the ac-plane. Hirshfeld surface analysis reveals that the molecular environments of A and B are similar and dominated by contacts involving hydrogen.

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1-[2-（2-氯-氧）- eth-yl]-2-甲基-4-硝基- 1h -咪唑的晶体结构和Hirshfeld表面分析。

咪唑是一类被广泛研究的杂环化合物，具有重要的生物学和药理学意义，包括杀菌剂、除草剂和治疗剂。标题化合物C8H12ClN3O3 (I)是抗原虫药物甲硝唑的结构类似物和杂质，在机理和药物开发研究中具有重要价值。本文报道了它的晶体结构和赫希菲尔德表面分析。I的晶体是三斜的，空间基型P1，在不对称单元中有两个独立的分子（A和B），每个分子在两个构象上都表现出氯-eth-氧-乙基链无序。两种分子本质上都具有平面甲基-硝基- 1h -咪唑核，侧链引起构象变化。该结构缺乏传统的氢键，但具有几个弱的C-H⋯O， C-H⋯N和C-H⋯Cl相互作用，将分子连接成二聚体和平行于ac平面的层。Hirshfeld表面分析表明，A和B的分子环境相似，以含氢接触为主。

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

Acta Crystallographica Section E: Crystallographic Communications Chemistry-Chemistry (all)

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.

Crystal structure and Hirshfeld surface analysis of 1-[2-(2-chloro­eth­oxy)eth­yl]-2-methyl-4-nitro-1H-imidazole

Abstract

Crystal structure and Hirshfeld surface analysis of 1-[2-(2-chloroethoxy)ethyl]-2-methyl-4-nitro-1H-imidazole