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Ethyl 4-hydr­oxy-9-tosyl-9H-carbazole-3-carboxyl­ate

In the title compound, C(22)H(19)NO(5)S, the carbazole skeleton is nearly planar [maximum deviation = 0.043 (1) Å] with the pyrrole ring oriented at dihedral angles of 2.32 (6) and 1.77 (6)° with respect to the adjacent benzene rings. The dihedral angle between the benzene ring of the tosyl group an...

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Autores principales: Hökelek, Tuncer, Dal, Hakan, Tercan, Barış, Gülle, Sibel, Ergün, Yavuz
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969395/
https://www.ncbi.nlm.nih.gov/pubmed/21582808
http://dx.doi.org/10.1107/S1600536809021035
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author Hökelek, Tuncer
Dal, Hakan
Tercan, Barış
Gülle, Sibel
Ergün, Yavuz
author_facet Hökelek, Tuncer
Dal, Hakan
Tercan, Barış
Gülle, Sibel
Ergün, Yavuz
author_sort Hökelek, Tuncer
collection PubMed
description In the title compound, C(22)H(19)NO(5)S, the carbazole skeleton is nearly planar [maximum deviation = 0.043 (1) Å] with the pyrrole ring oriented at dihedral angles of 2.32 (6) and 1.77 (6)° with respect to the adjacent benzene rings. The dihedral angle between the benzene ring of the tosyl group and the carbazole skeleton is 82.25 (5)°. Intra­molecular O—H⋯O hydrogen bonding results in the formation of a planar six-membered ring, which is oriented at a dihedral angle of 3.06 (4)° with respect to the adjacent carbazole skeleton. In the crystal structure, weak inter­molecular C—H⋯O inter­actions link the mol­ecules into infinite chains and π–π contacts between the benzene rings and between the pyrrole and benzene rings [centroid–centroid distances = 3.374 (1) and 3.730 (1) Å, respectively] may further stabilize the structure. A weak C—H⋯π inter­action is also present.
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spelling pubmed-29693952010-12-30 Ethyl 4-hydr­oxy-9-tosyl-9H-carbazole-3-carboxyl­ate Hökelek, Tuncer Dal, Hakan Tercan, Barış Gülle, Sibel Ergün, Yavuz Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(22)H(19)NO(5)S, the carbazole skeleton is nearly planar [maximum deviation = 0.043 (1) Å] with the pyrrole ring oriented at dihedral angles of 2.32 (6) and 1.77 (6)° with respect to the adjacent benzene rings. The dihedral angle between the benzene ring of the tosyl group and the carbazole skeleton is 82.25 (5)°. Intra­molecular O—H⋯O hydrogen bonding results in the formation of a planar six-membered ring, which is oriented at a dihedral angle of 3.06 (4)° with respect to the adjacent carbazole skeleton. In the crystal structure, weak inter­molecular C—H⋯O inter­actions link the mol­ecules into infinite chains and π–π contacts between the benzene rings and between the pyrrole and benzene rings [centroid–centroid distances = 3.374 (1) and 3.730 (1) Å, respectively] may further stabilize the structure. A weak C—H⋯π inter­action is also present. International Union of Crystallography 2009-06-06 /pmc/articles/PMC2969395/ /pubmed/21582808 http://dx.doi.org/10.1107/S1600536809021035 Text en © Hökelek 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
Hökelek, Tuncer
Dal, Hakan
Tercan, Barış
Gülle, Sibel
Ergün, Yavuz
Ethyl 4-hydr­oxy-9-tosyl-9H-carbazole-3-carboxyl­ate
title Ethyl 4-hydr­oxy-9-tosyl-9H-carbazole-3-carboxyl­ate
title_full Ethyl 4-hydr­oxy-9-tosyl-9H-carbazole-3-carboxyl­ate
title_fullStr Ethyl 4-hydr­oxy-9-tosyl-9H-carbazole-3-carboxyl­ate
title_full_unstemmed Ethyl 4-hydr­oxy-9-tosyl-9H-carbazole-3-carboxyl­ate
title_short Ethyl 4-hydr­oxy-9-tosyl-9H-carbazole-3-carboxyl­ate
title_sort ethyl 4-hydr­oxy-9-tosyl-9h-carbazole-3-carboxyl­ate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969395/
https://www.ncbi.nlm.nih.gov/pubmed/21582808
http://dx.doi.org/10.1107/S1600536809021035
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AT dalhakan ethyl4hydroxy9tosyl9hcarbazole3carboxylate
AT tercanbarıs ethyl4hydroxy9tosyl9hcarbazole3carboxylate
AT gullesibel ethyl4hydroxy9tosyl9hcarbazole3carboxylate
AT ergunyavuz ethyl4hydroxy9tosyl9hcarbazole3carboxylate