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N′-[(1E)-(5-Nitrofuran-2-yl)methylidene]thiophene-2-carbohydrazide: crystal structure and Hirshfeld surface analysis
In the title carbohydrazide, C(10)H(7)N(3)O(4)S, the dihedral angle between the terminal five-membered rings is 27.4 (2)°, with these lying to the same side of the plane through the central CN(2)C(=O) atoms (r.m.s. deviation = 0.0403 Å), leading to a curved molecule. The conformation about the C=N...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4992931/ https://www.ncbi.nlm.nih.gov/pubmed/27555956 http://dx.doi.org/10.1107/S2056989016009968 |
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author | Cardoso, Laura N. F. Nogueira, Thais C. M. Wardell, James L. Wardell, Solange M. S. V. de Souza, Marcus V. N. Jotani, Mukesh M. Tiekink, Edward R. T. |
author_facet | Cardoso, Laura N. F. Nogueira, Thais C. M. Wardell, James L. Wardell, Solange M. S. V. de Souza, Marcus V. N. Jotani, Mukesh M. Tiekink, Edward R. T. |
author_sort | Cardoso, Laura N. F. |
collection | PubMed |
description | In the title carbohydrazide, C(10)H(7)N(3)O(4)S, the dihedral angle between the terminal five-membered rings is 27.4 (2)°, with these lying to the same side of the plane through the central CN(2)C(=O) atoms (r.m.s. deviation = 0.0403 Å), leading to a curved molecule. The conformation about the C=N imine bond [1.281 (5) Å] is E, and the carbonyl O and amide H atoms are anti. In the crystal, N—H⋯O hydrogen bonds lead to supramolecular chains, generated by a 4(1) screw-axis along the c direction. A three-dimensional architecture is consolidated by thienyl-C—H⋯O(nitro) and furanyl-C—H⋯O(nitro) interactions, as well as π–π interactions between the thienyl and furanyl rings [inter-centroid distance = 3.515 (2) Å]. These, and other, weak intermolecular interactions, e.g. nitro-N—O⋯π(thienyl), have been investigated by Hirshfeld surface analysis, which confirms the dominance of the conventional N—H⋯O hydrogen bonding to the overall molecular packing. |
format | Online Article Text |
id | pubmed-4992931 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-49929312016-08-23 N′-[(1E)-(5-Nitrofuran-2-yl)methylidene]thiophene-2-carbohydrazide: crystal structure and Hirshfeld surface analysis Cardoso, Laura N. F. Nogueira, Thais C. M. Wardell, James L. Wardell, Solange M. S. V. de Souza, Marcus V. N. Jotani, Mukesh M. Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications In the title carbohydrazide, C(10)H(7)N(3)O(4)S, the dihedral angle between the terminal five-membered rings is 27.4 (2)°, with these lying to the same side of the plane through the central CN(2)C(=O) atoms (r.m.s. deviation = 0.0403 Å), leading to a curved molecule. The conformation about the C=N imine bond [1.281 (5) Å] is E, and the carbonyl O and amide H atoms are anti. In the crystal, N—H⋯O hydrogen bonds lead to supramolecular chains, generated by a 4(1) screw-axis along the c direction. A three-dimensional architecture is consolidated by thienyl-C—H⋯O(nitro) and furanyl-C—H⋯O(nitro) interactions, as well as π–π interactions between the thienyl and furanyl rings [inter-centroid distance = 3.515 (2) Å]. These, and other, weak intermolecular interactions, e.g. nitro-N—O⋯π(thienyl), have been investigated by Hirshfeld surface analysis, which confirms the dominance of the conventional N—H⋯O hydrogen bonding to the overall molecular packing. International Union of Crystallography 2016-06-24 /pmc/articles/PMC4992931/ /pubmed/27555956 http://dx.doi.org/10.1107/S2056989016009968 Text en © Cardoso et al. 2016 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Research Communications Cardoso, Laura N. F. Nogueira, Thais C. M. Wardell, James L. Wardell, Solange M. S. V. de Souza, Marcus V. N. Jotani, Mukesh M. Tiekink, Edward R. T. N′-[(1E)-(5-Nitrofuran-2-yl)methylidene]thiophene-2-carbohydrazide: crystal structure and Hirshfeld surface analysis |
title |
N′-[(1E)-(5-Nitrofuran-2-yl)methylidene]thiophene-2-carbohydrazide: crystal structure and Hirshfeld surface analysis |
title_full |
N′-[(1E)-(5-Nitrofuran-2-yl)methylidene]thiophene-2-carbohydrazide: crystal structure and Hirshfeld surface analysis |
title_fullStr |
N′-[(1E)-(5-Nitrofuran-2-yl)methylidene]thiophene-2-carbohydrazide: crystal structure and Hirshfeld surface analysis |
title_full_unstemmed |
N′-[(1E)-(5-Nitrofuran-2-yl)methylidene]thiophene-2-carbohydrazide: crystal structure and Hirshfeld surface analysis |
title_short |
N′-[(1E)-(5-Nitrofuran-2-yl)methylidene]thiophene-2-carbohydrazide: crystal structure and Hirshfeld surface analysis |
title_sort | n′-[(1e)-(5-nitrofuran-2-yl)methylidene]thiophene-2-carbohydrazide: crystal structure and hirshfeld surface analysis |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4992931/ https://www.ncbi.nlm.nih.gov/pubmed/27555956 http://dx.doi.org/10.1107/S2056989016009968 |
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