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Methyl 2-[(2-chloro­quinolin-3-yl)(hy­droxy)meth­yl]acrylate

There are two independent mol­ecules (A and B) in the asymmetric unit of the title compound, C(14)H(12)ClNO(3). The mean planes of the methyl ester unit (C(meth­yl)—O—C=O; r.m.s. deviation = 0.051 Å for mol­ecule A and 0.016 Å for mol­ecule B) and the chloro­quilonine ring system (r.m.s. deviation =...

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Autores principales: Anuradha, T., Srinivasan, J., Seshadri, P. R., Bakthadoss, M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3685122/
https://www.ncbi.nlm.nih.gov/pubmed/23795141
http://dx.doi.org/10.1107/S1600536813014050
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author Anuradha, T.
Srinivasan, J.
Seshadri, P. R.
Bakthadoss, M.
author_facet Anuradha, T.
Srinivasan, J.
Seshadri, P. R.
Bakthadoss, M.
author_sort Anuradha, T.
collection PubMed
description There are two independent mol­ecules (A and B) in the asymmetric unit of the title compound, C(14)H(12)ClNO(3). The mean planes of the methyl ester unit (C(meth­yl)—O—C=O; r.m.s. deviation = 0.051 Å for mol­ecule A and 0.016 Å for mol­ecule B) and the chloro­quilonine ring system (r.m.s. deviation = 0.023 Å for mol­ecule A and 0.014 Å for mol­ecule B) form dihedral angles of 63.5 (1)° in mol­ecule A and 78.1 (1)° in mol­ecule B. The main difference between the two independent mol­ecules is reflected in the (H)O—C—C=C(H(2)) torsion angle which is −109.7 (2)° in mol­ecule A and 10.6 (2)° in mol­ecule B. An intra­molecular O—H⋯O hydrogen bond is observed in mol­ecule A. In the crystal, mol­ecules A and B are linked into pairs via bifurcated O—H⋯(N,Cl) hydrogen bonds and a weak C—H⋯O hydrogen bond links pairs of mol­ecules into chains along [100].
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spelling pubmed-36851222013-06-21 Methyl 2-[(2-chloro­quinolin-3-yl)(hy­droxy)meth­yl]acrylate Anuradha, T. Srinivasan, J. Seshadri, P. R. Bakthadoss, M. Acta Crystallogr Sect E Struct Rep Online Organic Papers There are two independent mol­ecules (A and B) in the asymmetric unit of the title compound, C(14)H(12)ClNO(3). The mean planes of the methyl ester unit (C(meth­yl)—O—C=O; r.m.s. deviation = 0.051 Å for mol­ecule A and 0.016 Å for mol­ecule B) and the chloro­quilonine ring system (r.m.s. deviation = 0.023 Å for mol­ecule A and 0.014 Å for mol­ecule B) form dihedral angles of 63.5 (1)° in mol­ecule A and 78.1 (1)° in mol­ecule B. The main difference between the two independent mol­ecules is reflected in the (H)O—C—C=C(H(2)) torsion angle which is −109.7 (2)° in mol­ecule A and 10.6 (2)° in mol­ecule B. An intra­molecular O—H⋯O hydrogen bond is observed in mol­ecule A. In the crystal, mol­ecules A and B are linked into pairs via bifurcated O—H⋯(N,Cl) hydrogen bonds and a weak C—H⋯O hydrogen bond links pairs of mol­ecules into chains along [100]. International Union of Crystallography 2013-05-31 /pmc/articles/PMC3685122/ /pubmed/23795141 http://dx.doi.org/10.1107/S1600536813014050 Text en © Anuradha et al. 2013 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
Anuradha, T.
Srinivasan, J.
Seshadri, P. R.
Bakthadoss, M.
Methyl 2-[(2-chloro­quinolin-3-yl)(hy­droxy)meth­yl]acrylate
title Methyl 2-[(2-chloro­quinolin-3-yl)(hy­droxy)meth­yl]acrylate
title_full Methyl 2-[(2-chloro­quinolin-3-yl)(hy­droxy)meth­yl]acrylate
title_fullStr Methyl 2-[(2-chloro­quinolin-3-yl)(hy­droxy)meth­yl]acrylate
title_full_unstemmed Methyl 2-[(2-chloro­quinolin-3-yl)(hy­droxy)meth­yl]acrylate
title_short Methyl 2-[(2-chloro­quinolin-3-yl)(hy­droxy)meth­yl]acrylate
title_sort methyl 2-[(2-chloro­quinolin-3-yl)(hy­droxy)meth­yl]acrylate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3685122/
https://www.ncbi.nlm.nih.gov/pubmed/23795141
http://dx.doi.org/10.1107/S1600536813014050
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AT srinivasanj methyl22chloroquinolin3ylhydroxymethylacrylate
AT seshadripr methyl22chloroquinolin3ylhydroxymethylacrylate
AT bakthadossm methyl22chloroquinolin3ylhydroxymethylacrylate