Cargando…
4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2H-1,3,4-thiadiazin-5-yl}-3-phenylsydnone
The title compound, C(18)H(13)ClN(6)O(2)S, exists in trans and cis configurations with respect to the acyclic C=N bonds [C=N = 1.2837 (15) and 1.3000 (14) Å, respectively]. The 3,6-dihydro-2H-1,3,4-thiadiazine ring adopts a half-boat conformation. The sydnone ring is approximately planar [maximum d...
Autores principales: | , , , |
---|---|
Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3089094/ https://www.ncbi.nlm.nih.gov/pubmed/21754481 http://dx.doi.org/10.1107/S1600536811013912 |
_version_ | 1782202976223363072 |
---|---|
author | Fun, Hoong-Kun Loh, Wan-Sin Nithinchandra, Kalluraya, Balakrishna |
author_facet | Fun, Hoong-Kun Loh, Wan-Sin Nithinchandra, Kalluraya, Balakrishna |
author_sort | Fun, Hoong-Kun |
collection | PubMed |
description | The title compound, C(18)H(13)ClN(6)O(2)S, exists in trans and cis configurations with respect to the acyclic C=N bonds [C=N = 1.2837 (15) and 1.3000 (14) Å, respectively]. The 3,6-dihydro-2H-1,3,4-thiadiazine ring adopts a half-boat conformation. The sydnone ring is approximately planar [maximum deviation = 0.002 (1) Å] and forms dihedral angles of 50.45 (7) and 61.21 (6)° with the aromatic rings. In the crystal, intermolecular N—H⋯N, C—H⋯Cl and C—H⋯S hydrogen bonds link the molecules into layers parallel to ab plane. The crystal packing is stabilized by C—H⋯π interactions and further consolidated by π–π interactions involving the phenyl rings [centroid–centroid distance = 3.6306 (7) Å]. |
format | Text |
id | pubmed-3089094 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-30890942011-07-13 4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2H-1,3,4-thiadiazin-5-yl}-3-phenylsydnone Fun, Hoong-Kun Loh, Wan-Sin Nithinchandra, Kalluraya, Balakrishna Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(18)H(13)ClN(6)O(2)S, exists in trans and cis configurations with respect to the acyclic C=N bonds [C=N = 1.2837 (15) and 1.3000 (14) Å, respectively]. The 3,6-dihydro-2H-1,3,4-thiadiazine ring adopts a half-boat conformation. The sydnone ring is approximately planar [maximum deviation = 0.002 (1) Å] and forms dihedral angles of 50.45 (7) and 61.21 (6)° with the aromatic rings. In the crystal, intermolecular N—H⋯N, C—H⋯Cl and C—H⋯S hydrogen bonds link the molecules into layers parallel to ab plane. The crystal packing is stabilized by C—H⋯π interactions and further consolidated by π–π interactions involving the phenyl rings [centroid–centroid distance = 3.6306 (7) Å]. International Union of Crystallography 2011-04-22 /pmc/articles/PMC3089094/ /pubmed/21754481 http://dx.doi.org/10.1107/S1600536811013912 Text en © Fun 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 Fun, Hoong-Kun Loh, Wan-Sin Nithinchandra, Kalluraya, Balakrishna 4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2H-1,3,4-thiadiazin-5-yl}-3-phenylsydnone |
title | 4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2H-1,3,4-thiadiazin-5-yl}-3-phenylsydnone |
title_full | 4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2H-1,3,4-thiadiazin-5-yl}-3-phenylsydnone |
title_fullStr | 4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2H-1,3,4-thiadiazin-5-yl}-3-phenylsydnone |
title_full_unstemmed | 4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2H-1,3,4-thiadiazin-5-yl}-3-phenylsydnone |
title_short | 4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2H-1,3,4-thiadiazin-5-yl}-3-phenylsydnone |
title_sort | 4-{2-[2-(4-chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2h-1,3,4-thiadiazin-5-yl}-3-phenylsydnone |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3089094/ https://www.ncbi.nlm.nih.gov/pubmed/21754481 http://dx.doi.org/10.1107/S1600536811013912 |
work_keys_str_mv | AT funhoongkun 4224chlorobenzylidenehydrazinylidene36dihydro2h134thiadiazin5yl3phenylsydnone AT lohwansin 4224chlorobenzylidenehydrazinylidene36dihydro2h134thiadiazin5yl3phenylsydnone AT nithinchandra 4224chlorobenzylidenehydrazinylidene36dihydro2h134thiadiazin5yl3phenylsydnone AT kallurayabalakrishna 4224chlorobenzylidenehydrazinylidene36dihydro2h134thiadiazin5yl3phenylsydnone |