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Crystal structure of 1-{(Z)-[(2E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-ethylthiourea
In the title thiosemicarbazone compound, C(18)H(18)ClN(3)S, the CN(3)S residue is almost planar (r.m.s. deviation = 0.0031 Å) and forms dihedral angles of 65.99 (7) and 34.60 (10)° with the phenyl and chlorobenzene rings, respectively; the dihedral angle between the aromatic rings is 85.13 (8)°. T...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4719972/ https://www.ncbi.nlm.nih.gov/pubmed/26870491 http://dx.doi.org/10.1107/S2056989015023531 |
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author | Tan, Ming Yueh Crouse, Karen A. Ravoof, Thahira Begum S. A. Tiekink, Edward R. T. |
author_facet | Tan, Ming Yueh Crouse, Karen A. Ravoof, Thahira Begum S. A. Tiekink, Edward R. T. |
author_sort | Tan, Ming Yueh |
collection | PubMed |
description | In the title thiosemicarbazone compound, C(18)H(18)ClN(3)S, the CN(3)S residue is almost planar (r.m.s. deviation = 0.0031 Å) and forms dihedral angles of 65.99 (7) and 34.60 (10)° with the phenyl and chlorobenzene rings, respectively; the dihedral angle between the aromatic rings is 85.13 (8)°. The conformation about the C=N bond is Z, and that about the C=C bonds is E. The imine N and ethyl N atoms are syn and are linked by an ethyl–imine N—H⋯N hydrogen bond. This H atom also forms an intermolecular hydrogen bond to the thione S atom, resulting in a supramolecular helical chain propagating along the b axis. The chains are consolidated into a three-dimensional architecture by phenyl-C—H⋯Cl contacts and weak π–π interactions between centrosymmetrically related chlorobenzene rings [inter-centroid distance = 3.9127 (15) Å]. |
format | Online Article Text |
id | pubmed-4719972 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-47199722016-02-11 Crystal structure of 1-{(Z)-[(2E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-ethylthiourea Tan, Ming Yueh Crouse, Karen A. Ravoof, Thahira Begum S. A. Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Data Reports In the title thiosemicarbazone compound, C(18)H(18)ClN(3)S, the CN(3)S residue is almost planar (r.m.s. deviation = 0.0031 Å) and forms dihedral angles of 65.99 (7) and 34.60 (10)° with the phenyl and chlorobenzene rings, respectively; the dihedral angle between the aromatic rings is 85.13 (8)°. The conformation about the C=N bond is Z, and that about the C=C bonds is E. The imine N and ethyl N atoms are syn and are linked by an ethyl–imine N—H⋯N hydrogen bond. This H atom also forms an intermolecular hydrogen bond to the thione S atom, resulting in a supramolecular helical chain propagating along the b axis. The chains are consolidated into a three-dimensional architecture by phenyl-C—H⋯Cl contacts and weak π–π interactions between centrosymmetrically related chlorobenzene rings [inter-centroid distance = 3.9127 (15) Å]. International Union of Crystallography 2015-12-12 /pmc/articles/PMC4719972/ /pubmed/26870491 http://dx.doi.org/10.1107/S2056989015023531 Text en © Tan et al. 2015 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 | Data Reports Tan, Ming Yueh Crouse, Karen A. Ravoof, Thahira Begum S. A. Tiekink, Edward R. T. Crystal structure of 1-{(Z)-[(2E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-ethylthiourea |
title | Crystal structure of 1-{(Z)-[(2E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-ethylthiourea |
title_full | Crystal structure of 1-{(Z)-[(2E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-ethylthiourea |
title_fullStr | Crystal structure of 1-{(Z)-[(2E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-ethylthiourea |
title_full_unstemmed | Crystal structure of 1-{(Z)-[(2E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-ethylthiourea |
title_short | Crystal structure of 1-{(Z)-[(2E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-ethylthiourea |
title_sort | crystal structure of 1-{(z)-[(2e)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-ethylthiourea |
topic | Data Reports |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4719972/ https://www.ncbi.nlm.nih.gov/pubmed/26870491 http://dx.doi.org/10.1107/S2056989015023531 |
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