Crystal structure and Hirshfeld surface analysis of 1-[2-(2-chloroethoxy)ethyl]-2-methyl-4-nitro-1H-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, C8H12ClN3O3 (I), is a structural analogue and impurity of the anti-protozoal drug m...
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International Union of Crystallography
2025-07-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
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| Online Access: | https://journals.iucr.org/paper?S2056989025005493 |
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| author | Thaluru M. Mohan Kumar Papegowda Bhavya Besagarahally L. Bhaskar Holehundi J. Shankara Prasad Hemmige S. Yathirajan Sean Parkin |
| author_facet | Thaluru M. Mohan Kumar Papegowda Bhavya Besagarahally L. Bhaskar Holehundi J. Shankara Prasad Hemmige S. Yathirajan Sean Parkin |
| author_sort | Thaluru M. Mohan Kumar |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-bef6550275f3407baa73f4e2ee61e8cb |
| institution | Kabale University |
| issn | 2056-9890 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj-art-bef6550275f3407baa73f4e2ee61e8cb2025-08-20T03:50:12ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902025-07-0181764664910.1107/S2056989025005493nx2027Crystal structure and Hirshfeld surface analysis of 1-[2-(2-chloroethoxy)ethyl]-2-methyl-4-nitro-1H-imidazoleThaluru M. Mohan Kumar0Papegowda Bhavya1Besagarahally L. Bhaskar2Holehundi J. Shankara Prasad3Hemmige S. Yathirajan4Sean Parkin5Department of Physical Sciences, Amrita School of Engineering, Amrita Vishwa Vidyapeetham, Bengaluru-560 035, IndiaDepartment of Applied Sciences, New Horizon College of Engineering, Bengaluru-560 103, IndiaDepartment of Physical Sciences, Amrita School of Engineering, Amrita Vishwa Vidyapeetham, Bengaluru-560 035, IndiaDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore-570 005, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, IndiaDepartment of Chemistry, University of Kentucky, Lexington, KY, 40506-0055, USAImidazoles 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.https://journals.iucr.org/paper?S2056989025005493crystal structuredisorderhirshfeld surfaceweak hydrogen bonds |
| spellingShingle | Thaluru M. Mohan Kumar Papegowda Bhavya Besagarahally L. Bhaskar Holehundi J. Shankara Prasad Hemmige S. Yathirajan Sean Parkin Crystal structure and Hirshfeld surface analysis of 1-[2-(2-chloroethoxy)ethyl]-2-methyl-4-nitro-1H-imidazole Acta Crystallographica Section E: Crystallographic Communications crystal structure disorder hirshfeld surface weak hydrogen bonds |
| title | Crystal structure and Hirshfeld surface analysis of 1-[2-(2-chloroethoxy)ethyl]-2-methyl-4-nitro-1H-imidazole |
| title_full | Crystal structure and Hirshfeld surface analysis of 1-[2-(2-chloroethoxy)ethyl]-2-methyl-4-nitro-1H-imidazole |
| title_fullStr | Crystal structure and Hirshfeld surface analysis of 1-[2-(2-chloroethoxy)ethyl]-2-methyl-4-nitro-1H-imidazole |
| title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of 1-[2-(2-chloroethoxy)ethyl]-2-methyl-4-nitro-1H-imidazole |
| title_short | Crystal structure and Hirshfeld surface analysis of 1-[2-(2-chloroethoxy)ethyl]-2-methyl-4-nitro-1H-imidazole |
| title_sort | crystal structure and hirshfeld surface analysis of 1 2 2 chloroethoxy ethyl 2 methyl 4 nitro 1h imidazole |
| topic | crystal structure disorder hirshfeld surface weak hydrogen bonds |
| url | https://journals.iucr.org/paper?S2056989025005493 |
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