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3-(Dimethylamino)-5,6,7,8,9,10-hexahydro- 12,13-dimethoxy-4H-spiro[benzo-1-thia-2,5-diazacyclododecene-4,1'-cyclobutan]-6-one 1,1-Dioxide Dichloromethane Solvate (1/1) at 173K


Linden, Anthony; Mihova, Tonya R; Heimgartner, Heinz (1998). 3-(Dimethylamino)-5,6,7,8,9,10-hexahydro- 12,13-dimethoxy-4H-spiro[benzo-1-thia-2,5-diazacyclododecene-4,1'-cyclobutan]-6-one 1,1-Dioxide Dichloromethane Solvate (1/1) at 173K. Acta Crystallographica. Section C: Crystal Structure Communications, 54(11):1659-1662.

Abstract

The 12-membered ring in the title compound, C20H29N3O5S.CH2Cl2, has conformational disorder with the two C atoms adjacent to the fused benzene ring each occupying two sites. The major conformer is present in 74.3(8)% of the molecules. The formal N2=C bond in the 12-membered ring and the adjacent C-N bond of the dimethylamino substituent have almost identical lengths, indicative of the electron donor character of the dimethylamino group. The amide group has the trans conformation and forms an intramolecular hydrogen bond with one of the sulfonyl O atoms. The solvent molecule forms C-H...O hydrogen bonds with the organic substrate. This novel heterocycle has been formed by a ring enlargement reaction of the corresponding nine-membered 1,2-benzothiazonin-3-one 1,1-dioxide and 2-(dimethylamino)-1-azaspiro[2.3]hex-1-ene.

Abstract

The 12-membered ring in the title compound, C20H29N3O5S.CH2Cl2, has conformational disorder with the two C atoms adjacent to the fused benzene ring each occupying two sites. The major conformer is present in 74.3(8)% of the molecules. The formal N2=C bond in the 12-membered ring and the adjacent C-N bond of the dimethylamino substituent have almost identical lengths, indicative of the electron donor character of the dimethylamino group. The amide group has the trans conformation and forms an intramolecular hydrogen bond with one of the sulfonyl O atoms. The solvent molecule forms C-H...O hydrogen bonds with the organic substrate. This novel heterocycle has been formed by a ring enlargement reaction of the corresponding nine-membered 1,2-benzothiazonin-3-one 1,1-dioxide and 2-(dimethylamino)-1-azaspiro[2.3]hex-1-ene.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1998
Deposited On:12 Nov 2013 14:16
Last Modified:07 Dec 2017 23:34
Publisher:Wiley-Blackwell
ISSN:0108-2701
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1107/S0108270198008476

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