Crystal structures of three ortho-substituted N-acylhydrazone derivatives
To explore the effect of the nature of substitutions on the structural parameters and hydrogen-bond interactions in N-acylhydrazone derivatives, the crystal structures of three ortho-substituted N-acylhydrazone derivatives, namely (E)-N-{2-[2-(2-chlorobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenz...
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doaj-5bacf1aceb8947f0af301e61686a66972020-11-25T00:03:21ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902017-12-0173121946195110.1107/S2056989017016814rz5225Crystal structures of three ortho-substituted N-acylhydrazone derivativesH. Purandara0Sabine Foro1B. Thimme Gowda2Department of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, IndiaInstitute of Materials Science, Darmstadt University of Technology, Alarich-Weiss-Strasse 2, D-64287, Darmstadt, GermanyDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, IndiaTo explore the effect of the nature of substitutions on the structural parameters and hydrogen-bond interactions in N-acylhydrazone derivatives, the crystal structures of three ortho-substituted N-acylhydrazone derivatives, namely (E)-N-{2-[2-(2-chlorobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16ClN3O3S (I), (E)-N-{2-[2-(2-methylbenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C17H19N3O3S (II), and (E)-N-{2-[2-(2-nitrobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16N4O5S (III), have been determined. The structures of the three compounds display similar molecular conformations and hydrogen-bond patterns. The hydrazone part of the molecule, C—C—N—N=C, is almost planar in all the compounds, with the C—C—N—N and C—N—N=C torsion angles being 179.5 (3) and 177.1 (3)°, respectively, in (I), −179.4 (2) and −177.1 (3)° in (II) and −179.7 (2) and 173.4 (2)° in (III). The two phenyl rings on either side of the chain are approximately parallel to each other. In the crystal, the molecules are linked to each other via N—H...O hydrogen bonds, forming ribbons with R22(8) and R22(10) ring motifs. The introduction of electron-withdrawing groups (by a chloro or nitro group) to produce compounds (I) or (III) results in C—H...O hydrogen-bonding interactions involving the sulfonyl O atoms of adjacent ribbons, forming layers parallel to the ab plane in (I) or a three-dimensional network in (III). In (III), one O atom of the nitro group is disordered over two orientations with refined occupancy ratio of 0.836 (12):0.164 (12).http://scripts.iucr.org/cgi-bin/paper?S2056989017016814crystal structureN-acylhydrazonesring motifsconformationC—H...O interaction |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
H. Purandara Sabine Foro B. Thimme Gowda |
spellingShingle |
H. Purandara Sabine Foro B. Thimme Gowda Crystal structures of three ortho-substituted N-acylhydrazone derivatives Acta Crystallographica Section E: Crystallographic Communications crystal structure N-acylhydrazones ring motifs conformation C—H...O interaction |
author_facet |
H. Purandara Sabine Foro B. Thimme Gowda |
author_sort |
H. Purandara |
title |
Crystal structures of three ortho-substituted N-acylhydrazone derivatives |
title_short |
Crystal structures of three ortho-substituted N-acylhydrazone derivatives |
title_full |
Crystal structures of three ortho-substituted N-acylhydrazone derivatives |
title_fullStr |
Crystal structures of three ortho-substituted N-acylhydrazone derivatives |
title_full_unstemmed |
Crystal structures of three ortho-substituted N-acylhydrazone derivatives |
title_sort |
crystal structures of three ortho-substituted n-acylhydrazone derivatives |
publisher |
International Union of Crystallography |
series |
Acta Crystallographica Section E: Crystallographic Communications |
issn |
2056-9890 |
publishDate |
2017-12-01 |
description |
To explore the effect of the nature of substitutions on the structural parameters and hydrogen-bond interactions in N-acylhydrazone derivatives, the crystal structures of three ortho-substituted N-acylhydrazone derivatives, namely (E)-N-{2-[2-(2-chlorobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16ClN3O3S (I), (E)-N-{2-[2-(2-methylbenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C17H19N3O3S (II), and (E)-N-{2-[2-(2-nitrobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16N4O5S (III), have been determined. The structures of the three compounds display similar molecular conformations and hydrogen-bond patterns. The hydrazone part of the molecule, C—C—N—N=C, is almost planar in all the compounds, with the C—C—N—N and C—N—N=C torsion angles being 179.5 (3) and 177.1 (3)°, respectively, in (I), −179.4 (2) and −177.1 (3)° in (II) and −179.7 (2) and 173.4 (2)° in (III). The two phenyl rings on either side of the chain are approximately parallel to each other. In the crystal, the molecules are linked to each other via N—H...O hydrogen bonds, forming ribbons with R22(8) and R22(10) ring motifs. The introduction of electron-withdrawing groups (by a chloro or nitro group) to produce compounds (I) or (III) results in C—H...O hydrogen-bonding interactions involving the sulfonyl O atoms of adjacent ribbons, forming layers parallel to the ab plane in (I) or a three-dimensional network in (III). In (III), one O atom of the nitro group is disordered over two orientations with refined occupancy ratio of 0.836 (12):0.164 (12). |
topic |
crystal structure N-acylhydrazones ring motifs conformation C—H...O interaction |
url |
http://scripts.iucr.org/cgi-bin/paper?S2056989017016814 |
work_keys_str_mv |
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