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

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, C<sub>8</sub>H<sub>12</sub>ClN<sub>3</sub>O<sub>3</sub> (<b>I</b>), 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 <b>I</b> are triclinic, space-group type <i>P</i>1, with two independent mol-ecules (<i>A</i> and <i>B</i>) in the asymmetric unit, each exhibiting chloro-eth-oxy-ethyl chain disorder over two conformations. Both mol-ecules have essentially planar methyl-nitro-1<i>H</i>-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 <i>ac</i>-plane. Hirshfeld surface analysis reveals that the mol-ecular environments of <i>A</i> and <i>B</i> are similar and dominated by contacts involving hydrogen.

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Journal
Acta Crystallographica Section E Crystallographic Communications
Published
2025-06-24
DOI
https://doi.org/10.1107/s2056989025005493
Primary Topic
Crystal structures of chemical compounds
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article
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article

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

Sean Parkin, P. Bhavya, B.L. Bhaskar, Holehundi J. Shankara Prasad et al.
Acta Crystallographica Section E Crystallographic Communications
Crystal structures of chemical compounds
article

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

Sean Parkin, P. Bhavya, B.L. Bhaskar, Holehundi J. Shankara Prasad, H.S. Yathirajan, Thaluru M. Mohan Kumar
article en

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, C<sub>8</sub>H<sub>12</sub>ClN<sub>3</sub>O<sub>3</sub> (<b>I</b>), 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 <b>I</b> are triclinic, space-group type <i>P</i>1, with two independent mol-ecules (<i>A</i> and <i>B</i>) in the asymmetric unit, each exhibiting chloro-eth-oxy-ethyl chain disorder over two conformations. Both mol-ecules have essentially planar methyl-nitro-1<i>H</i>-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 <i>ac</i>-plane. Hirshfeld surface analysis reveals that the mol-ecular environments of <i>A</i> and <i>B</i> are similar and dominated by contacts involving hydrogen.

Acta Crystallographica Section E Crystallographic CommunicationsVol. 81(7)
University of Kentucky (US), University of Mysore (IN), Horizon College and Seminary (CA), Amrita Vishwa Vidyapeetham (IN)
Openalex Percentile: Top 88%
Crystal structures of chemical compounds
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Crystal structure and Hirshfeld surface analysis of 1-[2-(2-chloroethoxy)ethyl]-2-methyl-4-nitro-1<i>H</i>-imidazole — Sean Parkin, P. Bhavya, et al. · Acta Crystallographica Section E Crystallographic Communications (2025) | TGRS Research Map | TGRS