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Bis(2-{[3-methyl-4-(2,2,2-trifluoro­eth­oxy)-2-pyrid­yl]methyl­sulfan­yl}-1H,3H (+)-benzimidazolium) 2,5-dichloro-3,6-dioxocyclo­hexa-1,4-diene-1,4-diolate

The title salt, 2C(16)H(15)F(3)N(3)OS(+)·C(6)Cl(2)O(4) (2−), is composed of two independent cations of a lansoprazole {systematic name 2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole} inter­mediate and a dianion of chloranilic acid. In the cations of the lanso...

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Autores principales: Hakim Al-arique, Q. N. M., Jasinski, Jerry P., Butcher, Ray J., Yathirajan, H. S., Narayana, B.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979375/
https://www.ncbi.nlm.nih.gov/pubmed/21579567
http://dx.doi.org/10.1107/S1600536810019665
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author Hakim Al-arique, Q. N. M.
Jasinski, Jerry P.
Butcher, Ray J.
Yathirajan, H. S.
Narayana, B.
author_facet Hakim Al-arique, Q. N. M.
Jasinski, Jerry P.
Butcher, Ray J.
Yathirajan, H. S.
Narayana, B.
author_sort Hakim Al-arique, Q. N. M.
collection PubMed
description The title salt, 2C(16)H(15)F(3)N(3)OS(+)·C(6)Cl(2)O(4) (2−), is composed of two independent cations of a lansoprazole {systematic name 2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole} inter­mediate and a dianion of chloranilic acid. In the cations of the lansoprazole inter­mediate, the dihedral angles between the least-squares planes of the pyridine and benzimidazole rings are 11.1 (6) and 13.1 (5)°, respectively. The dihedral angles between the mean plane of the benzene ring in the chloranilic acid dianion and the pryidine and benzimidazole rings of the two lansoprazole inter­mediate groups are 71.8 (1)/80.5 (7) and 74.2 (4)/74.8 (6)°. In addition to ionic bond inter­actions, the lansoprazole inter­mediate and chloranilic ions are connected by strong N—H⋯O hydrogen bonds, which produce a set of extended O—H⋯O—H⋯O—H chains along the b axis in the (011) plane. In addition, weak C—H⋯O, C—H⋯F, N—H⋯Cl and π–π [centroid–centroid distances = 3.5631 (15), 3.8187 (13), 3.7434 (17) and 3.842 (2) Å] inter­molecular inter­actions are observed, which contribute to crystal packing stability.
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spelling pubmed-29793752010-12-30 Bis(2-{[3-methyl-4-(2,2,2-trifluoro­eth­oxy)-2-pyrid­yl]methyl­sulfan­yl}-1H,3H (+)-benzimidazolium) 2,5-dichloro-3,6-dioxocyclo­hexa-1,4-diene-1,4-diolate Hakim Al-arique, Q. N. M. Jasinski, Jerry P. Butcher, Ray J. Yathirajan, H. S. Narayana, B. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title salt, 2C(16)H(15)F(3)N(3)OS(+)·C(6)Cl(2)O(4) (2−), is composed of two independent cations of a lansoprazole {systematic name 2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole} inter­mediate and a dianion of chloranilic acid. In the cations of the lansoprazole inter­mediate, the dihedral angles between the least-squares planes of the pyridine and benzimidazole rings are 11.1 (6) and 13.1 (5)°, respectively. The dihedral angles between the mean plane of the benzene ring in the chloranilic acid dianion and the pryidine and benzimidazole rings of the two lansoprazole inter­mediate groups are 71.8 (1)/80.5 (7) and 74.2 (4)/74.8 (6)°. In addition to ionic bond inter­actions, the lansoprazole inter­mediate and chloranilic ions are connected by strong N—H⋯O hydrogen bonds, which produce a set of extended O—H⋯O—H⋯O—H chains along the b axis in the (011) plane. In addition, weak C—H⋯O, C—H⋯F, N—H⋯Cl and π–π [centroid–centroid distances = 3.5631 (15), 3.8187 (13), 3.7434 (17) and 3.842 (2) Å] inter­molecular inter­actions are observed, which contribute to crystal packing stability. International Union of Crystallography 2010-05-29 /pmc/articles/PMC2979375/ /pubmed/21579567 http://dx.doi.org/10.1107/S1600536810019665 Text en © Hakim Al-arique et al. 2010 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
Hakim Al-arique, Q. N. M.
Jasinski, Jerry P.
Butcher, Ray J.
Yathirajan, H. S.
Narayana, B.
Bis(2-{[3-methyl-4-(2,2,2-trifluoro­eth­oxy)-2-pyrid­yl]methyl­sulfan­yl}-1H,3H (+)-benzimidazolium) 2,5-dichloro-3,6-dioxocyclo­hexa-1,4-diene-1,4-diolate
title Bis(2-{[3-methyl-4-(2,2,2-trifluoro­eth­oxy)-2-pyrid­yl]methyl­sulfan­yl}-1H,3H (+)-benzimidazolium) 2,5-dichloro-3,6-dioxocyclo­hexa-1,4-diene-1,4-diolate
title_full Bis(2-{[3-methyl-4-(2,2,2-trifluoro­eth­oxy)-2-pyrid­yl]methyl­sulfan­yl}-1H,3H (+)-benzimidazolium) 2,5-dichloro-3,6-dioxocyclo­hexa-1,4-diene-1,4-diolate
title_fullStr Bis(2-{[3-methyl-4-(2,2,2-trifluoro­eth­oxy)-2-pyrid­yl]methyl­sulfan­yl}-1H,3H (+)-benzimidazolium) 2,5-dichloro-3,6-dioxocyclo­hexa-1,4-diene-1,4-diolate
title_full_unstemmed Bis(2-{[3-methyl-4-(2,2,2-trifluoro­eth­oxy)-2-pyrid­yl]methyl­sulfan­yl}-1H,3H (+)-benzimidazolium) 2,5-dichloro-3,6-dioxocyclo­hexa-1,4-diene-1,4-diolate
title_short Bis(2-{[3-methyl-4-(2,2,2-trifluoro­eth­oxy)-2-pyrid­yl]methyl­sulfan­yl}-1H,3H (+)-benzimidazolium) 2,5-dichloro-3,6-dioxocyclo­hexa-1,4-diene-1,4-diolate
title_sort bis(2-{[3-methyl-4-(2,2,2-trifluoro­eth­oxy)-2-pyrid­yl]methyl­sulfan­yl}-1h,3h (+)-benzimidazolium) 2,5-dichloro-3,6-dioxocyclo­hexa-1,4-diene-1,4-diolate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979375/
https://www.ncbi.nlm.nih.gov/pubmed/21579567
http://dx.doi.org/10.1107/S1600536810019665
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