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N′-[(1E,2E)-1-(2-Phenylhydrazin-1-ylidene)-1-(phenylsulfonyl)propan-2-ylidene]benzohydrazide
The configuration about each C=N bond in the title compound, C(22)H(20)N(4)O(3)S, is E. While to a first approximation the phenylhydrazin-1-ylidene and benzohydrazide residues are coplanar, in part due to the presence of an intramolecular N—H⋯N hydrogen bond, significant twists are evident in the...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3200681/ https://www.ncbi.nlm.nih.gov/pubmed/22058945 http://dx.doi.org/10.1107/S1600536811031953 |
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author | Abdel-Aziz, Hatem A. Ng, Seik Weng Tiekink, Edward R. T. |
author_facet | Abdel-Aziz, Hatem A. Ng, Seik Weng Tiekink, Edward R. T. |
author_sort | Abdel-Aziz, Hatem A. |
collection | PubMed |
description | The configuration about each C=N bond in the title compound, C(22)H(20)N(4)O(3)S, is E. While to a first approximation the phenylhydrazin-1-ylidene and benzohydrazide residues are coplanar, in part due to the presence of an intramolecular N—H⋯N hydrogen bond, significant twists are evident in the orientations of the hydrazine [N—N—C—C torsion angle = −170.74 (11)°] and benzoyl benzene [N—C—C—C = −21.72 (18)°] rings. The sulfonyl benzene ring occupies a position almost normal to the rest of the molecule [C—S—C—N = −92.28 (10)°]. Centrosymmetric aggregates mediated by pairs of hydrazide–sulfonyl N—H⋯O hydrogen bonds are the predominant packing motif in the crystal. These are connected into linear supramolecular chains via C—H⋯O interactions which are, in turn, linked into layers in the ac plane via C—H⋯π interactions. Connections between layers along the b-axis direction are of the π–π type and occur between centrosymmetrically related hydrazine-bound benzene rings [centroid–centroid separation = 3.7425 (9) Å]. |
format | Online Article Text |
id | pubmed-3200681 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32006812011-11-06 N′-[(1E,2E)-1-(2-Phenylhydrazin-1-ylidene)-1-(phenylsulfonyl)propan-2-ylidene]benzohydrazide Abdel-Aziz, Hatem A. Ng, Seik Weng Tiekink, Edward R. T. Acta Crystallogr Sect E Struct Rep Online Organic Papers The configuration about each C=N bond in the title compound, C(22)H(20)N(4)O(3)S, is E. While to a first approximation the phenylhydrazin-1-ylidene and benzohydrazide residues are coplanar, in part due to the presence of an intramolecular N—H⋯N hydrogen bond, significant twists are evident in the orientations of the hydrazine [N—N—C—C torsion angle = −170.74 (11)°] and benzoyl benzene [N—C—C—C = −21.72 (18)°] rings. The sulfonyl benzene ring occupies a position almost normal to the rest of the molecule [C—S—C—N = −92.28 (10)°]. Centrosymmetric aggregates mediated by pairs of hydrazide–sulfonyl N—H⋯O hydrogen bonds are the predominant packing motif in the crystal. These are connected into linear supramolecular chains via C—H⋯O interactions which are, in turn, linked into layers in the ac plane via C—H⋯π interactions. Connections between layers along the b-axis direction are of the π–π type and occur between centrosymmetrically related hydrazine-bound benzene rings [centroid–centroid separation = 3.7425 (9) Å]. International Union of Crystallography 2011-08-11 /pmc/articles/PMC3200681/ /pubmed/22058945 http://dx.doi.org/10.1107/S1600536811031953 Text en © Abdel-Aziz et al. 2011 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 | Organic Papers Abdel-Aziz, Hatem A. Ng, Seik Weng Tiekink, Edward R. T. N′-[(1E,2E)-1-(2-Phenylhydrazin-1-ylidene)-1-(phenylsulfonyl)propan-2-ylidene]benzohydrazide |
title |
N′-[(1E,2E)-1-(2-Phenylhydrazin-1-ylidene)-1-(phenylsulfonyl)propan-2-ylidene]benzohydrazide |
title_full |
N′-[(1E,2E)-1-(2-Phenylhydrazin-1-ylidene)-1-(phenylsulfonyl)propan-2-ylidene]benzohydrazide |
title_fullStr |
N′-[(1E,2E)-1-(2-Phenylhydrazin-1-ylidene)-1-(phenylsulfonyl)propan-2-ylidene]benzohydrazide |
title_full_unstemmed |
N′-[(1E,2E)-1-(2-Phenylhydrazin-1-ylidene)-1-(phenylsulfonyl)propan-2-ylidene]benzohydrazide |
title_short |
N′-[(1E,2E)-1-(2-Phenylhydrazin-1-ylidene)-1-(phenylsulfonyl)propan-2-ylidene]benzohydrazide |
title_sort | n′-[(1e,2e)-1-(2-phenylhydrazin-1-ylidene)-1-(phenylsulfonyl)propan-2-ylidene]benzohydrazide |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3200681/ https://www.ncbi.nlm.nih.gov/pubmed/22058945 http://dx.doi.org/10.1107/S1600536811031953 |
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