4-{(Z)-2-[(E)-Benzyl­idenehydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate

The title compound, C(18)H(14)N(6)O(2)S, exists in trans and cis configurations with respect to the two acyclic C=N bonds [bond lengths = 1.2835 (9) and 1.3049 (9) Å]. The 3,6-dihydro-2H-1,3,4-thia­diazine ring adopts a half-boat conformation. The oxadiazol-3-ium ring makes dihedral angles of 53.70 ...

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Detalles Bibliográficos
Autores principales: Fun, Hoong-Kun, Quah, Ching Kheng, Nithinchandra, Kalluraya, Balakrishna
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3100016/
https://www.ncbi.nlm.nih.gov/pubmed/21754237
http://dx.doi.org/10.1107/S1600536811010609
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author Fun, Hoong-Kun
Quah, Ching Kheng
Nithinchandra,
Kalluraya, Balakrishna
author_facet Fun, Hoong-Kun
Quah, Ching Kheng
Nithinchandra,
Kalluraya, Balakrishna
author_sort Fun, Hoong-Kun
collection PubMed
description The title compound, C(18)H(14)N(6)O(2)S, exists in trans and cis configurations with respect to the two acyclic C=N bonds [bond lengths = 1.2835 (9) and 1.3049 (9) Å]. The 3,6-dihydro-2H-1,3,4-thia­diazine ring adopts a half-boat conformation. The oxadiazol-3-ium ring makes dihedral angles of 53.70 (4) and 60.26 (4)° with the two phenyl rings. In the crystal, mol­ecules are linked via pairs of inter­molecular N—H⋯N hydrogen bonds, generating R (2) (2)(8) ring motifs, and are further linked via inter­molecular C—H⋯O and C—H⋯S hydrogen bonds into a three-dimensional network. The short inter­molecular distance between the oxadiazol-3-ium rings [3.4154 (4) Å] indicates the existence of a π–π inter­action.
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spelling pubmed-31000162011-07-13 4-{(Z)-2-[(E)-Benzyl­idenehydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate Fun, Hoong-Kun Quah, Ching Kheng Nithinchandra, Kalluraya, Balakrishna Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(18)H(14)N(6)O(2)S, exists in trans and cis configurations with respect to the two acyclic C=N bonds [bond lengths = 1.2835 (9) and 1.3049 (9) Å]. The 3,6-dihydro-2H-1,3,4-thia­diazine ring adopts a half-boat conformation. The oxadiazol-3-ium ring makes dihedral angles of 53.70 (4) and 60.26 (4)° with the two phenyl rings. In the crystal, mol­ecules are linked via pairs of inter­molecular N—H⋯N hydrogen bonds, generating R (2) (2)(8) ring motifs, and are further linked via inter­molecular C—H⋯O and C—H⋯S hydrogen bonds into a three-dimensional network. The short inter­molecular distance between the oxadiazol-3-ium rings [3.4154 (4) Å] indicates the existence of a π–π inter­action. International Union of Crystallography 2011-03-26 /pmc/articles/PMC3100016/ /pubmed/21754237 http://dx.doi.org/10.1107/S1600536811010609 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
Quah, Ching Kheng
Nithinchandra,
Kalluraya, Balakrishna
4-{(Z)-2-[(E)-Benzyl­idenehydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate
title 4-{(Z)-2-[(E)-Benzyl­idenehydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate
title_full 4-{(Z)-2-[(E)-Benzyl­idenehydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate
title_fullStr 4-{(Z)-2-[(E)-Benzyl­idenehydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate
title_full_unstemmed 4-{(Z)-2-[(E)-Benzyl­idenehydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate
title_short 4-{(Z)-2-[(E)-Benzyl­idenehydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate
title_sort 4-{(z)-2-[(e)-benzyl­idenehydrazinyl­idene]-3,6-dihydro-2h-1,3,4-thia­diazin-5-yl}-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3100016/
https://www.ncbi.nlm.nih.gov/pubmed/21754237
http://dx.doi.org/10.1107/S1600536811010609
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AT kallurayabalakrishna 4z2ebenzylidenehydrazinylidene36dihydro2h134thiadiazin5yl3phenyl123oxadiazol3ium5olate

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