Purandara, H. ; Foro, Sabine ; Thimme Gowda, B. (2018)
Comparison of the crystal structures and Hirshfeld surface analysis of five N-(4-methylbenzenesulfonyl)glycine hydrazone derivatives.
In: Acta Crystallographica Section C Structural Chemistry, 74 (11)
doi: 10.1107/S2053229618014420
Artikel, Bibliographie
Kurzbeschreibung (Abstract)
The crystal structures of N-(4-methylbenzenesulfonyl) glycine hydrazone and four derivatives with four different substituents have been investigated, namely, (E)-N-{2-[2-(benzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H17N3O3S, (I), (E)-N-{2-[2-(4-bromobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16BrN3O3S, (II), (E)-N-{2-[2-(4-chlorobenzylidene) hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16ClN3O3S, (III), (E)-N-(2-{2-[4-(dimethylamino)benzylidene]hydrazinyl}-2-oxoethyl)-4-methylbenzenesulfonamide, C18H22N4O3S, (IV), and (E)-N-{2-[2-(4-methoxybenzylidene) hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C17H19N3O4S, (V). The molecules in all five crystal structures show similar conformations and hydrogen-bonding patterns. The central part of the molecule, i.e. C-C-N-N=C, is almost linear in all the structures, with the C-C-N-N torsion angles ranging from -178.3 (1) to -180.0 (2)degrees and the C-N-N=C torsion angles ranging from -178.5 (4) to -179.8 (3)degrees. The conformation of the N-H and C=O bonds in the amide group of the hydrazone part is syn in all the compounds. In all the structures, sulfonamide and hydrazone dimers with R-2(2) (8) ring motifs are observed, which are further augmented by C-H center dot center dot center dot O interactions. A common feature of each of (I)-(V) is the formation of sulfonamide and hydrazone dimers with an R-2(2) (8) ring motif. Hirshfeld surface analyses gave fingerprint plots for H center dot center dot center dot H, O center dot center dot center dot H/H center dot center dot center dot O, N center dot center dot center dot H/H center dot center dot center dot N, C center dot center dot center dot H/H center dot center dot center dot C and other contacts. The H center dot center dot center dot H contacts show large surfaces, whereas the O center dot center dot center dot H plots show the presence of O center dot center dot center dot H/O center dot center dot center dot H contacts with the two characteristic long sharp spikes.
| Typ des Eintrags: | Artikel |
|---|---|
| Erschienen: | 2018 |
| Autor(en): | Purandara, H. ; Foro, Sabine ; Thimme Gowda, B. |
| Art des Eintrags: | Bibliographie |
| Titel: | Comparison of the crystal structures and Hirshfeld surface analysis of five N-(4-methylbenzenesulfonyl)glycine hydrazone derivatives |
| Sprache: | Englisch |
| Publikationsjahr: | November 2018 |
| Verlag: | International Union of Crystallography |
| Titel der Zeitschrift, Zeitung oder Schriftenreihe: | Acta Crystallographica Section C Structural Chemistry |
| Jahrgang/Volume einer Zeitschrift: | 74 |
| (Heft-)Nummer: | 11 |
| DOI: | 10.1107/S2053229618014420 |
| URL / URN: | https://doi.org/10.1107/S2053229618014420 |
| Kurzbeschreibung (Abstract): | The crystal structures of N-(4-methylbenzenesulfonyl) glycine hydrazone and four derivatives with four different substituents have been investigated, namely, (E)-N-{2-[2-(benzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H17N3O3S, (I), (E)-N-{2-[2-(4-bromobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16BrN3O3S, (II), (E)-N-{2-[2-(4-chlorobenzylidene) hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16ClN3O3S, (III), (E)-N-(2-{2-[4-(dimethylamino)benzylidene]hydrazinyl}-2-oxoethyl)-4-methylbenzenesulfonamide, C18H22N4O3S, (IV), and (E)-N-{2-[2-(4-methoxybenzylidene) hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C17H19N3O4S, (V). The molecules in all five crystal structures show similar conformations and hydrogen-bonding patterns. The central part of the molecule, i.e. C-C-N-N=C, is almost linear in all the structures, with the C-C-N-N torsion angles ranging from -178.3 (1) to -180.0 (2)degrees and the C-N-N=C torsion angles ranging from -178.5 (4) to -179.8 (3)degrees. The conformation of the N-H and C=O bonds in the amide group of the hydrazone part is syn in all the compounds. In all the structures, sulfonamide and hydrazone dimers with R-2(2) (8) ring motifs are observed, which are further augmented by C-H center dot center dot center dot O interactions. A common feature of each of (I)-(V) is the formation of sulfonamide and hydrazone dimers with an R-2(2) (8) ring motif. Hirshfeld surface analyses gave fingerprint plots for H center dot center dot center dot H, O center dot center dot center dot H/H center dot center dot center dot O, N center dot center dot center dot H/H center dot center dot center dot N, C center dot center dot center dot H/H center dot center dot center dot C and other contacts. The H center dot center dot center dot H contacts show large surfaces, whereas the O center dot center dot center dot H plots show the presence of O center dot center dot center dot H/O center dot center dot center dot H contacts with the two characteristic long sharp spikes. |
| Freie Schlagworte: | N-acylhydrazone derivatives, crystal structure, conformation, hydrogen-bond interaction, ring motif, Hirshfeld surface analysis |
| Zusätzliche Informationen: | HP thanks the Department of Science and Technology, Government of India, New Delhi, for a research fellowship under its INSPIRE Program. BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under a UGC-BSR one-time grant to faculty. |
| Fachbereich(e)/-gebiet(e): | 11 Fachbereich Material- und Geowissenschaften 11 Fachbereich Material- und Geowissenschaften > Materialwissenschaft 11 Fachbereich Material- und Geowissenschaften > Materialwissenschaft > Fachgebiet Strukturforschung |
| Hinterlegungsdatum: | 14 Sep 2020 05:33 |
| Letzte Änderung: | 14 Sep 2020 05:33 |
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