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Crystal structure of 3-(3,4,5-tri­meth­oxy­phen­yl)-1,2,3,4-tetra­hydro­cyclo­penta[b]indole-2-carb­oxy­lic acid

In the title compound, C(21)H(21)NO(5), obtained from a Morita–Baylis–Hillman adduct, the hydrogenated five-membered ring adopts a shallow envelope conformation, with the C atom bearing the carb­oxy­lic acid substituent deviating by 0.237 (1) Å from the mean plane of the other four atoms (r.m.s. dev...

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Autores principales: Fernandes, Daniara, Simoni, Deborah de Alencar, Rodrigues, Manoel T., Santos, Marilia S., Coelho, Fernando
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4459319/
https://www.ncbi.nlm.nih.gov/pubmed/26090185
http://dx.doi.org/10.1107/S2056989015008786
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author Fernandes, Daniara
Simoni, Deborah de Alencar
Rodrigues, Manoel T.
Santos, Marilia S.
Coelho, Fernando
author_facet Fernandes, Daniara
Simoni, Deborah de Alencar
Rodrigues, Manoel T.
Santos, Marilia S.
Coelho, Fernando
author_sort Fernandes, Daniara
collection PubMed
description In the title compound, C(21)H(21)NO(5), obtained from a Morita–Baylis–Hillman adduct, the hydrogenated five-membered ring adopts a shallow envelope conformation, with the C atom bearing the carb­oxy­lic acid substituent deviating by 0.237 (1) Å from the mean plane of the other four atoms (r.m.s. deviation = 0.007 Å). The dihedral angle between the fused ring system (all atoms; r.m.s. deviation = 0.057 Å) and the pendant trimeth­oxy benzene ring is 66.65 (3)°. The C atoms of the meta-meth­oxy groups lie close to the plane of the benzene ring [deviations = 0.052 (1) and −0.083 (1) Å], whereas the C atom of the para-meth­oxy group is significantly displaced [deviation = −1.289 (1) Å]. In the crystal, carb­oxy­lic acid inversion dimers generate R (2) (2)(8) loops. The dimers are connected by N—H⋯O hydrogen bonds, forming [011] chains. A C—H⋯O inter­action is also observed.
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spelling pubmed-44593192015-06-18 Crystal structure of 3-(3,4,5-tri­meth­oxy­phen­yl)-1,2,3,4-tetra­hydro­cyclo­penta[b]indole-2-carb­oxy­lic acid Fernandes, Daniara Simoni, Deborah de Alencar Rodrigues, Manoel T. Santos, Marilia S. Coelho, Fernando Acta Crystallogr E Crystallogr Commun Data Reports In the title compound, C(21)H(21)NO(5), obtained from a Morita–Baylis–Hillman adduct, the hydrogenated five-membered ring adopts a shallow envelope conformation, with the C atom bearing the carb­oxy­lic acid substituent deviating by 0.237 (1) Å from the mean plane of the other four atoms (r.m.s. deviation = 0.007 Å). The dihedral angle between the fused ring system (all atoms; r.m.s. deviation = 0.057 Å) and the pendant trimeth­oxy benzene ring is 66.65 (3)°. The C atoms of the meta-meth­oxy groups lie close to the plane of the benzene ring [deviations = 0.052 (1) and −0.083 (1) Å], whereas the C atom of the para-meth­oxy group is significantly displaced [deviation = −1.289 (1) Å]. In the crystal, carb­oxy­lic acid inversion dimers generate R (2) (2)(8) loops. The dimers are connected by N—H⋯O hydrogen bonds, forming [011] chains. A C—H⋯O inter­action is also observed. International Union of Crystallography 2015-05-13 /pmc/articles/PMC4459319/ /pubmed/26090185 http://dx.doi.org/10.1107/S2056989015008786 Text en © C. Fernandes et al. 2015 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 Data Reports
Fernandes, Daniara
Simoni, Deborah de Alencar
Rodrigues, Manoel T.
Santos, Marilia S.
Coelho, Fernando
Crystal structure of 3-(3,4,5-tri­meth­oxy­phen­yl)-1,2,3,4-tetra­hydro­cyclo­penta[b]indole-2-carb­oxy­lic acid
title Crystal structure of 3-(3,4,5-tri­meth­oxy­phen­yl)-1,2,3,4-tetra­hydro­cyclo­penta[b]indole-2-carb­oxy­lic acid
title_full Crystal structure of 3-(3,4,5-tri­meth­oxy­phen­yl)-1,2,3,4-tetra­hydro­cyclo­penta[b]indole-2-carb­oxy­lic acid
title_fullStr Crystal structure of 3-(3,4,5-tri­meth­oxy­phen­yl)-1,2,3,4-tetra­hydro­cyclo­penta[b]indole-2-carb­oxy­lic acid
title_full_unstemmed Crystal structure of 3-(3,4,5-tri­meth­oxy­phen­yl)-1,2,3,4-tetra­hydro­cyclo­penta[b]indole-2-carb­oxy­lic acid
title_short Crystal structure of 3-(3,4,5-tri­meth­oxy­phen­yl)-1,2,3,4-tetra­hydro­cyclo­penta[b]indole-2-carb­oxy­lic acid
title_sort crystal structure of 3-(3,4,5-tri­meth­oxy­phen­yl)-1,2,3,4-tetra­hydro­cyclo­penta[b]indole-2-carb­oxy­lic acid
topic Data Reports
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4459319/
https://www.ncbi.nlm.nih.gov/pubmed/26090185
http://dx.doi.org/10.1107/S2056989015008786
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