6-Chloro-1-(3,5-dimethyl­phenyl­sulfon­yl)-1H-benzimidazol-2(3H)-one

The title compound, C(15)H(13)ClN(2)O(3)S, is one of a series of N (1)-benzyl-1,3-dihydro-2H-benzimidazol-2-one derivatives, a new class of non-nucleoside HIV-1 reverse transcriptase inhibitors. The dihedral angle between the two pharmacophoric groups, the dimethyl­benzene ring and the benzimidazolo...

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Detalles Bibliográficos
Autores principales: Meneghetti, Fiorella, Bombieri, Gabriella, Logoteta, Patrizia, De Luca, Laura
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968072/
https://www.ncbi.nlm.nih.gov/pubmed/21581616
http://dx.doi.org/10.1107/S1600536808042694
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author Meneghetti, Fiorella
Bombieri, Gabriella
Logoteta, Patrizia
De Luca, Laura
author_facet Meneghetti, Fiorella
Bombieri, Gabriella
Logoteta, Patrizia
De Luca, Laura
author_sort Meneghetti, Fiorella
collection PubMed
description The title compound, C(15)H(13)ClN(2)O(3)S, is one of a series of N (1)-benzyl-1,3-dihydro-2H-benzimidazol-2-one derivatives, a new class of non-nucleoside HIV-1 reverse transcriptase inhibitors. The dihedral angle between the two pharmacophoric groups, the dimethyl­benzene ring and the benzimidazolone ring system, is 88 (1)°, giving a butterfly-like conformation to the mol­ecule. The mol­ecular packing is characterized by a bifurcated N—H⋯(O,O) hydrogen bond and short Cl⋯O contacts of 3.122 (2) Å. In addition, π–π stacking of the benzimidazolone rings is also present, with inter­planar separations of 3.95 (1) Å.
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spelling pubmed-29680722010-12-30 6-Chloro-1-(3,5-dimethyl­phenyl­sulfon­yl)-1H-benzimidazol-2(3H)-one Meneghetti, Fiorella Bombieri, Gabriella Logoteta, Patrizia De Luca, Laura Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(15)H(13)ClN(2)O(3)S, is one of a series of N (1)-benzyl-1,3-dihydro-2H-benzimidazol-2-one derivatives, a new class of non-nucleoside HIV-1 reverse transcriptase inhibitors. The dihedral angle between the two pharmacophoric groups, the dimethyl­benzene ring and the benzimidazolone ring system, is 88 (1)°, giving a butterfly-like conformation to the mol­ecule. The mol­ecular packing is characterized by a bifurcated N—H⋯(O,O) hydrogen bond and short Cl⋯O contacts of 3.122 (2) Å. In addition, π–π stacking of the benzimidazolone rings is also present, with inter­planar separations of 3.95 (1) Å. International Union of Crystallography 2008-12-20 /pmc/articles/PMC2968072/ /pubmed/21581616 http://dx.doi.org/10.1107/S1600536808042694 Text en © Meneghetti 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
Meneghetti, Fiorella
Bombieri, Gabriella
Logoteta, Patrizia
De Luca, Laura
6-Chloro-1-(3,5-dimethyl­phenyl­sulfon­yl)-1H-benzimidazol-2(3H)-one
title 6-Chloro-1-(3,5-dimethyl­phenyl­sulfon­yl)-1H-benzimidazol-2(3H)-one
title_full 6-Chloro-1-(3,5-dimethyl­phenyl­sulfon­yl)-1H-benzimidazol-2(3H)-one
title_fullStr 6-Chloro-1-(3,5-dimethyl­phenyl­sulfon­yl)-1H-benzimidazol-2(3H)-one
title_full_unstemmed 6-Chloro-1-(3,5-dimethyl­phenyl­sulfon­yl)-1H-benzimidazol-2(3H)-one
title_short 6-Chloro-1-(3,5-dimethyl­phenyl­sulfon­yl)-1H-benzimidazol-2(3H)-one
title_sort 6-chloro-1-(3,5-dimethyl­phenyl­sulfon­yl)-1h-benzimidazol-2(3h)-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968072/
https://www.ncbi.nlm.nih.gov/pubmed/21581616
http://dx.doi.org/10.1107/S1600536808042694
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