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.
Authors
- Sean Parkin (ORCID: https://orcid.org/0000-0001-5777-3918)
- P. Bhavya
- B.L. Bhaskar (ORCID: https://orcid.org/0000-0001-6733-0280)
- Holehundi J. Shankara Prasad
- H.S. Yathirajan (ORCID: https://orcid.org/0000-0001-9039-0273)
- Thaluru M. Mohan Kumar
Institutions
- University of Kentucky (US)
- University of Mysore (IN)
- Horizon College and Seminary (CA)
- Amrita Vishwa Vidyapeetham (IN)
Publication Details
- 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
- Type
- article
- Field-Weighted Citation Impact
- 0.00