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Ethyl 3-(9-chloro-10-oxo-9,10-di­hydro­anthracen-9-yl)-5-methyl­isoxazole-4-carboxyl­ate

The asymmetric unit of the title compound, C(21)H(16)ClNO(4), contains two independent mol­ecules (A and B), each adopting a conformation wherein the isoxazole ring is roughly orthogonal to the anthrone ring. The dihedral angle between the mean plane of the isoxazole (all atoms) and the mean plane o...

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Autores principales: Duncan, Nathan S., Beall, Howard D., Kearns, Alison K., Li, Chun, Natale, Nicholas R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998422/
https://www.ncbi.nlm.nih.gov/pubmed/24765016
http://dx.doi.org/10.1107/S1600536814003080
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author Duncan, Nathan S.
Beall, Howard D.
Kearns, Alison K.
Li, Chun
Natale, Nicholas R.
author_facet Duncan, Nathan S.
Beall, Howard D.
Kearns, Alison K.
Li, Chun
Natale, Nicholas R.
author_sort Duncan, Nathan S.
collection PubMed
description The asymmetric unit of the title compound, C(21)H(16)ClNO(4), contains two independent mol­ecules (A and B), each adopting a conformation wherein the isoxazole ring is roughly orthogonal to the anthrone ring. The dihedral angle between the mean plane of the isoxazole (all atoms) and the mean plane of the anthrone (all atoms) is 88.48 (3)° in one mol­ecule and 89.92 (4)° in the other. The ester is almost coplanar with the isoxazole ring, with mean-plane dihedral angles of 2.48 (15) and 8.62 (5)°. In both mol­ecules, the distance between the ester carbonyl O atom and the anthrone ketone C atom is about 3.3 Å. The anthrone ring is virtually planar (r.m.s. deviations of 0.070 and 0.065 Å) and adopts a shallow boat conformation in each mol­ecule, as evidenced by the sum of the six intra-B-ring torsion angles [41.43 (15) and 34.38 (15)° for molecules A and B, respectively]. The closest separation between the benzene moieties of anthrones A and B is 5.1162 (7) Å, with an angle of 57.98 (5)°, consistent with an edge-to-face π-stacking inter­action. In the crystal, weak C—H⋯O and C—H⋯N inter­actions link the mol­ecules, forming a three-dimensional network.
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spelling pubmed-39984222014-04-24 Ethyl 3-(9-chloro-10-oxo-9,10-di­hydro­anthracen-9-yl)-5-methyl­isoxazole-4-carboxyl­ate Duncan, Nathan S. Beall, Howard D. Kearns, Alison K. Li, Chun Natale, Nicholas R. Acta Crystallogr Sect E Struct Rep Online Organic Papers The asymmetric unit of the title compound, C(21)H(16)ClNO(4), contains two independent mol­ecules (A and B), each adopting a conformation wherein the isoxazole ring is roughly orthogonal to the anthrone ring. The dihedral angle between the mean plane of the isoxazole (all atoms) and the mean plane of the anthrone (all atoms) is 88.48 (3)° in one mol­ecule and 89.92 (4)° in the other. The ester is almost coplanar with the isoxazole ring, with mean-plane dihedral angles of 2.48 (15) and 8.62 (5)°. In both mol­ecules, the distance between the ester carbonyl O atom and the anthrone ketone C atom is about 3.3 Å. The anthrone ring is virtually planar (r.m.s. deviations of 0.070 and 0.065 Å) and adopts a shallow boat conformation in each mol­ecule, as evidenced by the sum of the six intra-B-ring torsion angles [41.43 (15) and 34.38 (15)° for molecules A and B, respectively]. The closest separation between the benzene moieties of anthrones A and B is 5.1162 (7) Å, with an angle of 57.98 (5)°, consistent with an edge-to-face π-stacking inter­action. In the crystal, weak C—H⋯O and C—H⋯N inter­actions link the mol­ecules, forming a three-dimensional network. International Union of Crystallography 2014-02-19 /pmc/articles/PMC3998422/ /pubmed/24765016 http://dx.doi.org/10.1107/S1600536814003080 Text en © Duncan et al. 2014 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
Duncan, Nathan S.
Beall, Howard D.
Kearns, Alison K.
Li, Chun
Natale, Nicholas R.
Ethyl 3-(9-chloro-10-oxo-9,10-di­hydro­anthracen-9-yl)-5-methyl­isoxazole-4-carboxyl­ate
title Ethyl 3-(9-chloro-10-oxo-9,10-di­hydro­anthracen-9-yl)-5-methyl­isoxazole-4-carboxyl­ate
title_full Ethyl 3-(9-chloro-10-oxo-9,10-di­hydro­anthracen-9-yl)-5-methyl­isoxazole-4-carboxyl­ate
title_fullStr Ethyl 3-(9-chloro-10-oxo-9,10-di­hydro­anthracen-9-yl)-5-methyl­isoxazole-4-carboxyl­ate
title_full_unstemmed Ethyl 3-(9-chloro-10-oxo-9,10-di­hydro­anthracen-9-yl)-5-methyl­isoxazole-4-carboxyl­ate
title_short Ethyl 3-(9-chloro-10-oxo-9,10-di­hydro­anthracen-9-yl)-5-methyl­isoxazole-4-carboxyl­ate
title_sort ethyl 3-(9-chloro-10-oxo-9,10-di­hydro­anthracen-9-yl)-5-methyl­isoxazole-4-carboxyl­ate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998422/
https://www.ncbi.nlm.nih.gov/pubmed/24765016
http://dx.doi.org/10.1107/S1600536814003080
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