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Crystal structure of azilsartan methyl ester ethyl acetate hemisolvate

The title compound, C(26)H(22)N(4)O(5) (systematic name: methyl 2-eth­oxy-1-{4-[2-(5-oxo-4,5-di­hydro-1,2,4-oxa­diazol-3-yl)phenyl]benz­yl}-1H-1,3-benzo­diazole-7-carboxyl­ate ethyl acetate hemisolvate), was obtained via cyclization of methyl (Z)-2-eth­oxy-1-{(2′-(N′-hy­droxy­carbamimido­yl)-[1,1′-b...

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Autores principales: Li, Zhengyi, Liu, Rong, Zhu, Meilan, Chen, Liang, Sun, Xiaoqiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4384622/
https://www.ncbi.nlm.nih.gov/pubmed/25878884
http://dx.doi.org/10.1107/S2056989014028023
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author Li, Zhengyi
Liu, Rong
Zhu, Meilan
Chen, Liang
Sun, Xiaoqiang
author_facet Li, Zhengyi
Liu, Rong
Zhu, Meilan
Chen, Liang
Sun, Xiaoqiang
author_sort Li, Zhengyi
collection PubMed
description The title compound, C(26)H(22)N(4)O(5) (systematic name: methyl 2-eth­oxy-1-{4-[2-(5-oxo-4,5-di­hydro-1,2,4-oxa­diazol-3-yl)phenyl]benz­yl}-1H-1,3-benzo­diazole-7-carboxyl­ate ethyl acetate hemisolvate), was obtained via cyclization of methyl (Z)-2-eth­oxy-1-{(2′-(N′-hy­droxy­carbamimido­yl)-[1,1′-biphen­yl]-4-yl)meth­yl}-1H-benzo[d]imidazole-7-carboxyl­ate with diphen­yl carbonate. There are two independent mol­ecules (A and B) with different conformations and an ethyl acetate solvent mol­ecule in the asymmetric unit. In mol­ecule A, the dihedral angle between the benzene ring and its attached oxa­diazole ring is 59.36 (17); the dihedral angle between the benzene rings is 43.89 (15) and that between the benzene ring and its attached imidazole ring system is 80.06 (11)°. The corres­ponding dihedral angles in mol­ecule B are 58.45 (18), 50.73 (16) and 85.37 (10)°, respectively. The C—O—C—C(m) (m = meth­yl) torsion angles for the eth­oxy side chains attached to the imidazole rings in mol­ecules A and B are 93.9 (3) and −174.6 (3)°, respectively. In the crystal, the components are linked by N—H⋯N and C—H⋯O hydrogen bonds, generating a three-dimensional network. Aromatic π–π stacking inter­actions [shortest centroid–centroid separation = 3.536 (3)Å] are also observed.
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spelling pubmed-43846222015-04-15 Crystal structure of azilsartan methyl ester ethyl acetate hemisolvate Li, Zhengyi Liu, Rong Zhu, Meilan Chen, Liang Sun, Xiaoqiang Acta Crystallogr E Crystallogr Commun Data Reports The title compound, C(26)H(22)N(4)O(5) (systematic name: methyl 2-eth­oxy-1-{4-[2-(5-oxo-4,5-di­hydro-1,2,4-oxa­diazol-3-yl)phenyl]benz­yl}-1H-1,3-benzo­diazole-7-carboxyl­ate ethyl acetate hemisolvate), was obtained via cyclization of methyl (Z)-2-eth­oxy-1-{(2′-(N′-hy­droxy­carbamimido­yl)-[1,1′-biphen­yl]-4-yl)meth­yl}-1H-benzo[d]imidazole-7-carboxyl­ate with diphen­yl carbonate. There are two independent mol­ecules (A and B) with different conformations and an ethyl acetate solvent mol­ecule in the asymmetric unit. In mol­ecule A, the dihedral angle between the benzene ring and its attached oxa­diazole ring is 59.36 (17); the dihedral angle between the benzene rings is 43.89 (15) and that between the benzene ring and its attached imidazole ring system is 80.06 (11)°. The corres­ponding dihedral angles in mol­ecule B are 58.45 (18), 50.73 (16) and 85.37 (10)°, respectively. The C—O—C—C(m) (m = meth­yl) torsion angles for the eth­oxy side chains attached to the imidazole rings in mol­ecules A and B are 93.9 (3) and −174.6 (3)°, respectively. In the crystal, the components are linked by N—H⋯N and C—H⋯O hydrogen bonds, generating a three-dimensional network. Aromatic π–π stacking inter­actions [shortest centroid–centroid separation = 3.536 (3)Å] are also observed. International Union of Crystallography 2015-01-03 /pmc/articles/PMC4384622/ /pubmed/25878884 http://dx.doi.org/10.1107/S2056989014028023 Text en © Li 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
Li, Zhengyi
Liu, Rong
Zhu, Meilan
Chen, Liang
Sun, Xiaoqiang
Crystal structure of azilsartan methyl ester ethyl acetate hemisolvate
title Crystal structure of azilsartan methyl ester ethyl acetate hemisolvate
title_full Crystal structure of azilsartan methyl ester ethyl acetate hemisolvate
title_fullStr Crystal structure of azilsartan methyl ester ethyl acetate hemisolvate
title_full_unstemmed Crystal structure of azilsartan methyl ester ethyl acetate hemisolvate
title_short Crystal structure of azilsartan methyl ester ethyl acetate hemisolvate
title_sort crystal structure of azilsartan methyl ester ethyl acetate hemisolvate
topic Data Reports
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4384622/
https://www.ncbi.nlm.nih.gov/pubmed/25878884
http://dx.doi.org/10.1107/S2056989014028023
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