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Ethyl 2-[5-(4-fluoro­phen­yl)pyridin-3-yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate

In the title compound, C(28)H(27)FN(4)O(3)·H(2)O, the benzimidazole ring system is essentially planar with a maximum deviation of 0.028 (1) Å. It makes dihedral angles of 47.59 (5) and 60.31 (5)°, respectively, with the pyridine and benzene rings, which make a dihedral angle of 22.58 (6)° with each...

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Autores principales: Yeong, Keng Yoon, Ali, Mohamed Ashraf, Choon, Tan Soo, Rosli, Mohd Mustaqim, Razak, Ibrahim Abdul
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3772454/
https://www.ncbi.nlm.nih.gov/pubmed/24046597
http://dx.doi.org/10.1107/S1600536813014177
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author Yeong, Keng Yoon
Ali, Mohamed Ashraf
Choon, Tan Soo
Rosli, Mohd Mustaqim
Razak, Ibrahim Abdul
author_facet Yeong, Keng Yoon
Ali, Mohamed Ashraf
Choon, Tan Soo
Rosli, Mohd Mustaqim
Razak, Ibrahim Abdul
author_sort Yeong, Keng Yoon
collection PubMed
description In the title compound, C(28)H(27)FN(4)O(3)·H(2)O, the benzimidazole ring system is essentially planar with a maximum deviation of 0.028 (1) Å. It makes dihedral angles of 47.59 (5) and 60.31 (5)°, respectively, with the pyridine and benzene rings, which make a dihedral angle of 22.58 (6)° with each other. The pyrrolidine ring shows an envelope conformation with one of the methyl­ene C atoms as the flap. In the crystal, the components are connected into a tape along the b-axis direction through O—H⋯O and O—H⋯N hydrogen bonds and a π–π inter­action between the pyridine and benzene rings [centroid–centroid distance of 3.685 (8) Å]. The tapes are further linked into layers parallel to the ab plane by C—H⋯O and C—H⋯F inter­actions.
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spelling pubmed-37724542013-09-17 Ethyl 2-[5-(4-fluoro­phen­yl)pyridin-3-yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate Yeong, Keng Yoon Ali, Mohamed Ashraf Choon, Tan Soo Rosli, Mohd Mustaqim Razak, Ibrahim Abdul Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(28)H(27)FN(4)O(3)·H(2)O, the benzimidazole ring system is essentially planar with a maximum deviation of 0.028 (1) Å. It makes dihedral angles of 47.59 (5) and 60.31 (5)°, respectively, with the pyridine and benzene rings, which make a dihedral angle of 22.58 (6)° with each other. The pyrrolidine ring shows an envelope conformation with one of the methyl­ene C atoms as the flap. In the crystal, the components are connected into a tape along the b-axis direction through O—H⋯O and O—H⋯N hydrogen bonds and a π–π inter­action between the pyridine and benzene rings [centroid–centroid distance of 3.685 (8) Å]. The tapes are further linked into layers parallel to the ab plane by C—H⋯O and C—H⋯F inter­actions. International Union of Crystallography 2013-06-08 /pmc/articles/PMC3772454/ /pubmed/24046597 http://dx.doi.org/10.1107/S1600536813014177 Text en © Yeong 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
Yeong, Keng Yoon
Ali, Mohamed Ashraf
Choon, Tan Soo
Rosli, Mohd Mustaqim
Razak, Ibrahim Abdul
Ethyl 2-[5-(4-fluoro­phen­yl)pyridin-3-yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate
title Ethyl 2-[5-(4-fluoro­phen­yl)pyridin-3-yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate
title_full Ethyl 2-[5-(4-fluoro­phen­yl)pyridin-3-yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate
title_fullStr Ethyl 2-[5-(4-fluoro­phen­yl)pyridin-3-yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate
title_full_unstemmed Ethyl 2-[5-(4-fluoro­phen­yl)pyridin-3-yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate
title_short Ethyl 2-[5-(4-fluoro­phen­yl)pyridin-3-yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate
title_sort ethyl 2-[5-(4-fluoro­phen­yl)pyridin-3-yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1h-benzimidazole-5-carboxyl­ate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3772454/
https://www.ncbi.nlm.nih.gov/pubmed/24046597
http://dx.doi.org/10.1107/S1600536813014177
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