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(2Z)-N-(2-Chloro­benz­yl)-2-(2-oxo-2,3-dihydro-1H-indol-3-yl­idene)hydrazinecarbothio­amide

In the title compound, C(16)H(13)ClN(4)OS, the isatin ring system is oriented at dihedral angles of 10.60 (7) and 72.60 (3)° with respect to the thio­semicarbazide and 2-chloro­benzyl groups, respectively. The near planarity of the isatin and thio­semicarbazide groups [r.m.s. deviations of 0.0420 an...

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Autores principales: Pervez, Humayun, Khan, Nazia, Iqbal, Mohammad S., Yaqub, Muhammad, Tahir, M. Nawaz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3435743/
https://www.ncbi.nlm.nih.gov/pubmed/22969614
http://dx.doi.org/10.1107/S1600536812035076
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author Pervez, Humayun
Khan, Nazia
Iqbal, Mohammad S.
Yaqub, Muhammad
Tahir, M. Nawaz
author_facet Pervez, Humayun
Khan, Nazia
Iqbal, Mohammad S.
Yaqub, Muhammad
Tahir, M. Nawaz
author_sort Pervez, Humayun
collection PubMed
description In the title compound, C(16)H(13)ClN(4)OS, the isatin ring system is oriented at dihedral angles of 10.60 (7) and 72.60 (3)° with respect to the thio­semicarbazide and 2-chloro­benzyl groups, respectively. The near planarity of the isatin and thio­semicarbazide groups [r.m.s. deviations of 0.0420 and 0.0163 Å, respectively] is reinforced by intra­molecular N—H⋯O and N—H⋯N hydrogen bonds, which generate S(6) and S(5) rings, respectively. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R (2) (2)(8) loops. Aromatic π–π stacking inter­actions between the centroids of heterocyclic five-membered and benzene rings [distance = 3.6866 (11) Å] are also observed.
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spelling pubmed-34357432012-09-11 (2Z)-N-(2-Chloro­benz­yl)-2-(2-oxo-2,3-dihydro-1H-indol-3-yl­idene)hydrazinecarbothio­amide Pervez, Humayun Khan, Nazia Iqbal, Mohammad S. Yaqub, Muhammad Tahir, M. Nawaz Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(16)H(13)ClN(4)OS, the isatin ring system is oriented at dihedral angles of 10.60 (7) and 72.60 (3)° with respect to the thio­semicarbazide and 2-chloro­benzyl groups, respectively. The near planarity of the isatin and thio­semicarbazide groups [r.m.s. deviations of 0.0420 and 0.0163 Å, respectively] is reinforced by intra­molecular N—H⋯O and N—H⋯N hydrogen bonds, which generate S(6) and S(5) rings, respectively. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R (2) (2)(8) loops. Aromatic π–π stacking inter­actions between the centroids of heterocyclic five-membered and benzene rings [distance = 3.6866 (11) Å] are also observed. International Union of Crystallography 2012-08-23 /pmc/articles/PMC3435743/ /pubmed/22969614 http://dx.doi.org/10.1107/S1600536812035076 Text en © Pervez et al. 2012 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
Pervez, Humayun
Khan, Nazia
Iqbal, Mohammad S.
Yaqub, Muhammad
Tahir, M. Nawaz
(2Z)-N-(2-Chloro­benz­yl)-2-(2-oxo-2,3-dihydro-1H-indol-3-yl­idene)hydrazinecarbothio­amide
title (2Z)-N-(2-Chloro­benz­yl)-2-(2-oxo-2,3-dihydro-1H-indol-3-yl­idene)hydrazinecarbothio­amide
title_full (2Z)-N-(2-Chloro­benz­yl)-2-(2-oxo-2,3-dihydro-1H-indol-3-yl­idene)hydrazinecarbothio­amide
title_fullStr (2Z)-N-(2-Chloro­benz­yl)-2-(2-oxo-2,3-dihydro-1H-indol-3-yl­idene)hydrazinecarbothio­amide
title_full_unstemmed (2Z)-N-(2-Chloro­benz­yl)-2-(2-oxo-2,3-dihydro-1H-indol-3-yl­idene)hydrazinecarbothio­amide
title_short (2Z)-N-(2-Chloro­benz­yl)-2-(2-oxo-2,3-dihydro-1H-indol-3-yl­idene)hydrazinecarbothio­amide
title_sort (2z)-n-(2-chloro­benz­yl)-2-(2-oxo-2,3-dihydro-1h-indol-3-yl­idene)hydrazinecarbothio­amide
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3435743/
https://www.ncbi.nlm.nih.gov/pubmed/22969614
http://dx.doi.org/10.1107/S1600536812035076
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