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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...

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Autores principales: Tsai, Hsing-Yang, Chang, Ming-Jen, Fang, Tzu-Chien, Luo, Ming-Hui, Chen, Kew-Yu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
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.
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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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