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1-[2-(2-氯乙氧基)乙基]-2-甲基-4-硝基-1-咪唑的晶体结构与 Hirshfeld 表面分析

Crystal structure and Hirshfeld surface analysis of 1-[2-(2-chloro-eth-oxy)eth-yl]-2-methyl-4-nitro-1-imidazole.

作者信息

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

机构信息

Department of Physical Sciences, Amrita School of Engineering, Amrita Vishwa Vidyapeetham, Bengaluru-560 035, India.

Department of Applied Sciences, New Horizon College of Engineering, Bengaluru-560 103, India.

出版信息

Acta Crystallogr E Crystallogr Commun. 2025 Jun 24;81(Pt 7):646-649. doi: 10.1107/S2056989025005493. eCollection 2025 Jul 1.

Abstract

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, CHClNO (), 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 are triclinic, space-group type 1, with two independent mol-ecules ( and ) in the asymmetric unit, each exhibiting chloro-eth-oxy-ethyl chain disorder over two conformations. Both mol-ecules have essentially planar methyl-nitro-1-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 inter-actions, connecting mol-ecules into dimers and layers parallel to the -plane. Hirshfeld surface analysis reveals that the mol-ecular environments of and are similar and dominated by contacts involving hydrogen.

摘要

咪唑是一类经过广泛研究的杂环化合物,具有重要的生物学和药理学意义,包括用作杀真菌剂、除草剂和治疗剂。标题化合物CHClNO( )是抗寄生虫药物甲硝唑的结构类似物和杂质,这使其在机理研究和药物开发研究中具有重要价值。在此,我们报道了其晶体结构和 Hirshfeld 表面分析。 的晶体为三斜晶系,空间群类型为1,不对称单元中有两个独立分子( 和 ),每个分子的氯乙氧基乙基链在两种构象上存在无序。两个分子都具有基本平面的甲基硝基 -1-咪唑核心,构象变化源于侧链。该结构缺乏传统氢键,但具有若干弱的C-H⋯O、C-H⋯N和C-H⋯Cl相互作用,将分子连接成平行于 平面的二聚体和层。Hirshfeld表面分析表明, 和 的分子环境相似,且以涉及氢的接触为主。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64ae/12230618/b444d167ac24/e-81-00646-fig1.jpg

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