Cargando…
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...
Autores principales: | , , , , |
---|---|
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 |
_version_ | 1782191397669961728 |
---|---|
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. |
format | Text |
id | pubmed-2979375 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT hakimalariqueqnm bis23methyl4222trifluoroethoxy2pyridylmethylsulfanyl1h3hbenzimidazolium25dichloro36dioxocyclohexa14diene14diolate AT jasinskijerryp bis23methyl4222trifluoroethoxy2pyridylmethylsulfanyl1h3hbenzimidazolium25dichloro36dioxocyclohexa14diene14diolate AT butcherrayj bis23methyl4222trifluoroethoxy2pyridylmethylsulfanyl1h3hbenzimidazolium25dichloro36dioxocyclohexa14diene14diolate AT yathirajanhs bis23methyl4222trifluoroethoxy2pyridylmethylsulfanyl1h3hbenzimidazolium25dichloro36dioxocyclohexa14diene14diolate AT narayanab bis23methyl4222trifluoroethoxy2pyridylmethylsulfanyl1h3hbenzimidazolium25dichloro36dioxocyclohexa14diene14diolate |