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1-{(E)-[(2E)-3-(4-Methoxyphenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-phenylurea: crystal structure and Hirshfeld surface analysis
The title compound, C(23)H(21)N(3)O(2), is constructed about an almost planar disubstituted aminourea residue (r.m.s. deviation = 0.0201 Å), which features an intramolecular amine-N—H⋯N(imine) hydrogen bond. In the ‘all-trans’ chain connecting this to the terminal methoxybenzene residue, the con...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5683474/ https://www.ncbi.nlm.nih.gov/pubmed/29152334 http://dx.doi.org/10.1107/S2056989017014128 |
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author | Tan, Ming Yueh Crouse, Karen A. Ravoof, Thahira B. S. A. Jotani, Mukesh M. Tiekink, Edward R. T. |
author_facet | Tan, Ming Yueh Crouse, Karen A. Ravoof, Thahira B. S. A. Jotani, Mukesh M. Tiekink, Edward R. T. |
author_sort | Tan, Ming Yueh |
collection | PubMed |
description | The title compound, C(23)H(21)N(3)O(2), is constructed about an almost planar disubstituted aminourea residue (r.m.s. deviation = 0.0201 Å), which features an intramolecular amine-N—H⋯N(imine) hydrogen bond. In the ‘all-trans’ chain connecting this to the terminal methoxybenzene residue, the conformation about each of the imine and ethylene double bonds is E. In the crystal, amide-N—H⋯O(carbonyl) hydrogen bonds connect centrosymmetrically related molecules into dimeric aggregates, which also incorporate ethylene-C—H⋯O(amide) interactions. The dimers are linked by amine–phenyl-C—H⋯π(imine–phenyl) and methoxybenzene-C—H⋯π(amine–phenyl) interactions to generate a three-dimensional network. The importance of C—H⋯π interactions in the molecular packing is reflected in the relatively high contributions made by C⋯H/H⋯C contacts to the Hirshfeld surface, i.e. 31.6%. |
format | Online Article Text |
id | pubmed-5683474 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-56834742017-11-17 1-{(E)-[(2E)-3-(4-Methoxyphenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-phenylurea: crystal structure and Hirshfeld surface analysis Tan, Ming Yueh Crouse, Karen A. Ravoof, Thahira B. S. A. Jotani, Mukesh M. Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(23)H(21)N(3)O(2), is constructed about an almost planar disubstituted aminourea residue (r.m.s. deviation = 0.0201 Å), which features an intramolecular amine-N—H⋯N(imine) hydrogen bond. In the ‘all-trans’ chain connecting this to the terminal methoxybenzene residue, the conformation about each of the imine and ethylene double bonds is E. In the crystal, amide-N—H⋯O(carbonyl) hydrogen bonds connect centrosymmetrically related molecules into dimeric aggregates, which also incorporate ethylene-C—H⋯O(amide) interactions. The dimers are linked by amine–phenyl-C—H⋯π(imine–phenyl) and methoxybenzene-C—H⋯π(amine–phenyl) interactions to generate a three-dimensional network. The importance of C—H⋯π interactions in the molecular packing is reflected in the relatively high contributions made by C⋯H/H⋯C contacts to the Hirshfeld surface, i.e. 31.6%. International Union of Crystallography 2017-10-06 /pmc/articles/PMC5683474/ /pubmed/29152334 http://dx.doi.org/10.1107/S2056989017014128 Text en © Tan et al. 2017 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/ |
spellingShingle | Research Communications Tan, Ming Yueh Crouse, Karen A. Ravoof, Thahira B. S. A. Jotani, Mukesh M. Tiekink, Edward R. T. 1-{(E)-[(2E)-3-(4-Methoxyphenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-phenylurea: crystal structure and Hirshfeld surface analysis |
title | 1-{(E)-[(2E)-3-(4-Methoxyphenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-phenylurea: crystal structure and Hirshfeld surface analysis |
title_full | 1-{(E)-[(2E)-3-(4-Methoxyphenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-phenylurea: crystal structure and Hirshfeld surface analysis |
title_fullStr | 1-{(E)-[(2E)-3-(4-Methoxyphenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-phenylurea: crystal structure and Hirshfeld surface analysis |
title_full_unstemmed | 1-{(E)-[(2E)-3-(4-Methoxyphenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-phenylurea: crystal structure and Hirshfeld surface analysis |
title_short | 1-{(E)-[(2E)-3-(4-Methoxyphenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-phenylurea: crystal structure and Hirshfeld surface analysis |
title_sort | 1-{(e)-[(2e)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-phenylurea: crystal structure and hirshfeld surface analysis |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5683474/ https://www.ncbi.nlm.nih.gov/pubmed/29152334 http://dx.doi.org/10.1107/S2056989017014128 |
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