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Ethyl 2-[(3-chloro­phen­yl)hydrazono]-3-oxobutanoate

The mol­ecule of the title oxobutanoate derivative, C(12)H(13)ClN(2)O(3), adopts a keto–hydrazo tautomeric form and is roughly planar, the angle between the benzene ring and the mean plane through the hydrazone and aliphatic chain being 1.49 (6)°. This planarity is further aided by the formation of...

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Autores principales: Fun, Hoong-Kun, Padaki, Mahesh, Sowmya, Isloor, Arun M., Chantrapromma, Suchada
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969699/
https://www.ncbi.nlm.nih.gov/pubmed/21583177
http://dx.doi.org/10.1107/S160053680901784X
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author Fun, Hoong-Kun
Padaki, Mahesh
Sowmya,
Isloor, Arun M.
Chantrapromma, Suchada
author_facet Fun, Hoong-Kun
Padaki, Mahesh
Sowmya,
Isloor, Arun M.
Chantrapromma, Suchada
author_sort Fun, Hoong-Kun
collection PubMed
description The mol­ecule of the title oxobutanoate derivative, C(12)H(13)ClN(2)O(3), adopts a keto–hydrazo tautomeric form and is roughly planar, the angle between the benzene ring and the mean plane through the hydrazone and aliphatic chain being 1.49 (6)°. This planarity is further aided by the formation of an intra­molecular N—H⋯O hydrogen bond which generates an S(6) ring motif. The aromatic ring and aliphatic chain have a trans configuration with respect to the N—N bond. In the crystal packing, centrosymmetric R (2) (2)(16) dimers are formed through pairs of weak C—H⋯O(3-oxo) inter­actions. These dimers are linked together through weak C—H⋯O(carboxyl­ate C=O) inter­actions into ribbons along the b-axis direction. These ribbons are stacked along the a-axis direction. The crystal also exhibits Cl⋯Cl [3.4988 (6) Å] and C⋯O [3.167 (2)–3.335 (2) Å] short contacts.
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spelling pubmed-29696992010-12-30 Ethyl 2-[(3-chloro­phen­yl)hydrazono]-3-oxobutanoate Fun, Hoong-Kun Padaki, Mahesh Sowmya, Isloor, Arun M. Chantrapromma, Suchada Acta Crystallogr Sect E Struct Rep Online Organic Papers The mol­ecule of the title oxobutanoate derivative, C(12)H(13)ClN(2)O(3), adopts a keto–hydrazo tautomeric form and is roughly planar, the angle between the benzene ring and the mean plane through the hydrazone and aliphatic chain being 1.49 (6)°. This planarity is further aided by the formation of an intra­molecular N—H⋯O hydrogen bond which generates an S(6) ring motif. The aromatic ring and aliphatic chain have a trans configuration with respect to the N—N bond. In the crystal packing, centrosymmetric R (2) (2)(16) dimers are formed through pairs of weak C—H⋯O(3-oxo) inter­actions. These dimers are linked together through weak C—H⋯O(carboxyl­ate C=O) inter­actions into ribbons along the b-axis direction. These ribbons are stacked along the a-axis direction. The crystal also exhibits Cl⋯Cl [3.4988 (6) Å] and C⋯O [3.167 (2)–3.335 (2) Å] short contacts. International Union of Crystallography 2009-05-20 /pmc/articles/PMC2969699/ /pubmed/21583177 http://dx.doi.org/10.1107/S160053680901784X Text en © Fun et al. 2009 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
Fun, Hoong-Kun
Padaki, Mahesh
Sowmya,
Isloor, Arun M.
Chantrapromma, Suchada
Ethyl 2-[(3-chloro­phen­yl)hydrazono]-3-oxobutanoate
title Ethyl 2-[(3-chloro­phen­yl)hydrazono]-3-oxobutanoate
title_full Ethyl 2-[(3-chloro­phen­yl)hydrazono]-3-oxobutanoate
title_fullStr Ethyl 2-[(3-chloro­phen­yl)hydrazono]-3-oxobutanoate
title_full_unstemmed Ethyl 2-[(3-chloro­phen­yl)hydrazono]-3-oxobutanoate
title_short Ethyl 2-[(3-chloro­phen­yl)hydrazono]-3-oxobutanoate
title_sort ethyl 2-[(3-chloro­phen­yl)hydrazono]-3-oxobutanoate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969699/
https://www.ncbi.nlm.nih.gov/pubmed/21583177
http://dx.doi.org/10.1107/S160053680901784X
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