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3-{[(4Z)-1,2-Dimethyl-5-oxoimidazol-4-ylidene]methyl}-4-hydroxybenzonitrile
In the title compound, C(13)H(11)N(3)O(2), an intramolecular O—H⋯N hydrogen bond generates an S(7) ring. The dihedral angle between the mean plane of the benzene ring and the imidazolidinone ring is 3.05 (2)°. In the crystal, inversion-related molecules are linked by dual C—H⋯O(carbonyl) hydrogen...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3297918/ https://www.ncbi.nlm.nih.gov/pubmed/22412721 http://dx.doi.org/10.1107/S1600536812007532 |
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author | Tsai, Hsing-Yang Chang, Ming-Jen Fang, Tzu-Chien Luo, Ming-Hui Chen, Kew-Yu |
author_facet | Tsai, Hsing-Yang Chang, Ming-Jen Fang, Tzu-Chien Luo, Ming-Hui Chen, Kew-Yu |
author_sort | Tsai, Hsing-Yang |
collection | PubMed |
description | In the title compound, C(13)H(11)N(3)O(2), an intramolecular O—H⋯N hydrogen bond generates an S(7) ring. The dihedral angle between the mean plane of the benzene ring and the imidazolidinone ring is 3.05 (2)°. In the crystal, inversion-related molecules are linked by dual C—H⋯O(carbonyl) hydrogen bonds to form a dimer with an R (2) (2)(14) graph-set motif. A C—H⋯O(hydroxy) interaction links pairs of molecules into another type of cyclic dimer with an R (2) (2)(18) motif. The molecules are further linked by C—H⋯N interactions to form layers parallel to (001). Offset π–π stacking [3.3877 (8) Å] is observed in the crystal structure, with an interplanar spacing between the planes of neighboring benzene rings of 3.444 (1) Å. |
format | Online Article Text |
id | pubmed-3297918 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32979182012-03-12 3-{[(4Z)-1,2-Dimethyl-5-oxoimidazol-4-ylidene]methyl}-4-hydroxybenzonitrile Tsai, Hsing-Yang Chang, Ming-Jen Fang, Tzu-Chien Luo, Ming-Hui Chen, Kew-Yu Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(13)H(11)N(3)O(2), an intramolecular O—H⋯N hydrogen bond generates an S(7) ring. The dihedral angle between the mean plane of the benzene ring and the imidazolidinone ring is 3.05 (2)°. In the crystal, inversion-related molecules are linked by dual C—H⋯O(carbonyl) hydrogen bonds to form a dimer with an R (2) (2)(14) graph-set motif. A C—H⋯O(hydroxy) interaction links pairs of molecules into another type of cyclic dimer with an R (2) (2)(18) motif. The molecules are further linked by C—H⋯N interactions to form layers parallel to (001). Offset π–π stacking [3.3877 (8) Å] is observed in the crystal structure, with an interplanar spacing between the planes of neighboring benzene rings of 3.444 (1) Å. International Union of Crystallography 2012-02-29 /pmc/articles/PMC3297918/ /pubmed/22412721 http://dx.doi.org/10.1107/S1600536812007532 Text en © Tsai 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 Tsai, Hsing-Yang Chang, Ming-Jen Fang, Tzu-Chien Luo, Ming-Hui Chen, Kew-Yu 3-{[(4Z)-1,2-Dimethyl-5-oxoimidazol-4-ylidene]methyl}-4-hydroxybenzonitrile |
title | 3-{[(4Z)-1,2-Dimethyl-5-oxoimidazol-4-ylidene]methyl}-4-hydroxybenzonitrile |
title_full | 3-{[(4Z)-1,2-Dimethyl-5-oxoimidazol-4-ylidene]methyl}-4-hydroxybenzonitrile |
title_fullStr | 3-{[(4Z)-1,2-Dimethyl-5-oxoimidazol-4-ylidene]methyl}-4-hydroxybenzonitrile |
title_full_unstemmed | 3-{[(4Z)-1,2-Dimethyl-5-oxoimidazol-4-ylidene]methyl}-4-hydroxybenzonitrile |
title_short | 3-{[(4Z)-1,2-Dimethyl-5-oxoimidazol-4-ylidene]methyl}-4-hydroxybenzonitrile |
title_sort | 3-{[(4z)-1,2-dimethyl-5-oxoimidazol-4-ylidene]methyl}-4-hydroxybenzonitrile |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3297918/ https://www.ncbi.nlm.nih.gov/pubmed/22412721 http://dx.doi.org/10.1107/S1600536812007532 |
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