Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: 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.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2016
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
_version_ 1782449083873492992
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
work_keys_str_mv AT cardosolauranf n1e5nitrofuran2ylmethylidenethiophene2carbohydrazidecrystalstructureandhirshfeldsurfaceanalysis
AT nogueirathaiscm n1e5nitrofuran2ylmethylidenethiophene2carbohydrazidecrystalstructureandhirshfeldsurfaceanalysis
AT wardelljamesl n1e5nitrofuran2ylmethylidenethiophene2carbohydrazidecrystalstructureandhirshfeldsurfaceanalysis
AT wardellsolangemsv n1e5nitrofuran2ylmethylidenethiophene2carbohydrazidecrystalstructureandhirshfeldsurfaceanalysis
AT desouzamarcusvn n1e5nitrofuran2ylmethylidenethiophene2carbohydrazidecrystalstructureandhirshfeldsurfaceanalysis
AT jotanimukeshm n1e5nitrofuran2ylmethylidenethiophene2carbohydrazidecrystalstructureandhirshfeldsurfaceanalysis
AT tiekinkedwardrt n1e5nitrofuran2ylmethylidenethiophene2carbohydrazidecrystalstructureandhirshfeldsurfaceanalysis