Synthesis, crystal structure and Hirshfeld surface analysis of 5-methyl-1H-pyrazol-3-yl 4-nitrobenzenesulfonate at 90 K
This study presents the synthesis, crystal structure, and a Hirshfeld-surface analysis of the bioactive compound 5-methyl-1H-pyrazol-3-yl 4-nitrobenzenesulfonate(C10H9N3O5S), a pyrazole derivative with pharmacological potential. Pyrazoles are known for diverse bioactivities, and recent research emph...
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International Union of Crystallography
2024-12-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
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| Online Access: | https://journals.iucr.org/paper?S205698902401140X |
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| author | Vinaya Syida A. Yakuth Thaluru M. Mohan Kumar Besagarahally L. Bhaskar Thayamma R. Divakara Hemmige S. Yathirajan Yeriyur B. Basavaraju Sean Parkin |
| author_facet | Vinaya Syida A. Yakuth Thaluru M. Mohan Kumar Besagarahally L. Bhaskar Thayamma R. Divakara Hemmige S. Yathirajan Yeriyur B. Basavaraju Sean Parkin |
| author_sort | Vinaya |
| collection | DOAJ |
| description | This study presents the synthesis, crystal structure, and a Hirshfeld-surface analysis of the bioactive compound 5-methyl-1H-pyrazol-3-yl 4-nitrobenzenesulfonate(C10H9N3O5S), a pyrazole derivative with pharmacological potential. Pyrazoles are known for diverse bioactivities, and recent research emphasizes their role as a ‘privileged structure’ in drug design. Here, the asymmetric unit of the title compound contains two distinct molecules, A and B, exhibiting differences in conformation resulting from variation in key torsion angles. These distinctions influence the molecular orientation and intermolecular interactions, with strong N—H...N and N—H...O hydrogen bonds forming a centrosymmetric tetramer stabilized by π–π stacking. Hirshfeld surface analysis readily confirms differing intermolecular contacts for A and B, primarily involving hydrogen atoms and differences in their close contacts to nitrogen and oxygen. This study offers further insight into the molecular architecture and potential interactions of pyrazole-based drug candidates. |
| format | Article |
| id | doaj-art-5a85f311ff764fc5985d7edc49e15bef |
| institution | OA Journals |
| issn | 2056-9890 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj-art-5a85f311ff764fc5985d7edc49e15bef2025-08-20T02:19:08ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902024-12-0180121354135810.1107/S205698902401140Xnx2016Synthesis, crystal structure and Hirshfeld surface analysis of 5-methyl-1H-pyrazol-3-yl 4-nitrobenzenesulfonate at 90 KVinaya0Syida A. Yakuth1Thaluru M. Mohan Kumar2Besagarahally L. Bhaskar3Thayamma R. Divakara4Hemmige S. Yathirajan5Yeriyur B. Basavaraju6Sean Parkin7Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, IndiaDepartment of Physical Sciences, Amrita School of Engineering, Amrita Vishwa Vidyapeetham, Bengaluru-560 035, IndiaDepartment of Physical Sciences, Amrita School of Engineering, Amrita Vishwa Vidyapeetham, Bengaluru-560 035, IndiaDepartment of Chemistry, T. John Institute of Technology, Bengaluru-560 083, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, IndiaDepartment of Chemistry, University of Kentucky, Lexington, KY, 40506-0055, USAThis study presents the synthesis, crystal structure, and a Hirshfeld-surface analysis of the bioactive compound 5-methyl-1H-pyrazol-3-yl 4-nitrobenzenesulfonate(C10H9N3O5S), a pyrazole derivative with pharmacological potential. Pyrazoles are known for diverse bioactivities, and recent research emphasizes their role as a ‘privileged structure’ in drug design. Here, the asymmetric unit of the title compound contains two distinct molecules, A and B, exhibiting differences in conformation resulting from variation in key torsion angles. These distinctions influence the molecular orientation and intermolecular interactions, with strong N—H...N and N—H...O hydrogen bonds forming a centrosymmetric tetramer stabilized by π–π stacking. Hirshfeld surface analysis readily confirms differing intermolecular contacts for A and B, primarily involving hydrogen atoms and differences in their close contacts to nitrogen and oxygen. This study offers further insight into the molecular architecture and potential interactions of pyrazole-based drug candidates.https://journals.iucr.org/paper?S205698902401140Xsynthesiscrystal structurehirshfeld surfacehydrogen bondingπ–π stackingcentrosymmetric tetramer |
| spellingShingle | Vinaya Syida A. Yakuth Thaluru M. Mohan Kumar Besagarahally L. Bhaskar Thayamma R. Divakara Hemmige S. Yathirajan Yeriyur B. Basavaraju Sean Parkin Synthesis, crystal structure and Hirshfeld surface analysis of 5-methyl-1H-pyrazol-3-yl 4-nitrobenzenesulfonate at 90 K Acta Crystallographica Section E: Crystallographic Communications synthesis crystal structure hirshfeld surface hydrogen bonding π–π stacking centrosymmetric tetramer |
| title | Synthesis, crystal structure and Hirshfeld surface analysis of 5-methyl-1H-pyrazol-3-yl 4-nitrobenzenesulfonate at 90 K |
| title_full | Synthesis, crystal structure and Hirshfeld surface analysis of 5-methyl-1H-pyrazol-3-yl 4-nitrobenzenesulfonate at 90 K |
| title_fullStr | Synthesis, crystal structure and Hirshfeld surface analysis of 5-methyl-1H-pyrazol-3-yl 4-nitrobenzenesulfonate at 90 K |
| title_full_unstemmed | Synthesis, crystal structure and Hirshfeld surface analysis of 5-methyl-1H-pyrazol-3-yl 4-nitrobenzenesulfonate at 90 K |
| title_short | Synthesis, crystal structure and Hirshfeld surface analysis of 5-methyl-1H-pyrazol-3-yl 4-nitrobenzenesulfonate at 90 K |
| title_sort | synthesis crystal structure and hirshfeld surface analysis of 5 methyl 1h pyrazol 3 yl 4 nitrobenzenesulfonate at 90 k |
| topic | synthesis crystal structure hirshfeld surface hydrogen bonding π–π stacking centrosymmetric tetramer |
| url | https://journals.iucr.org/paper?S205698902401140X |
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