Buthalital and methitural – 5,5-substituted derivatives of 2-thiobarbituric acid forming the same type of hydrogen-bonded chain

Buthalital and methitural – 5,5-substituted derivatives of 2-thiobarbituric acid forming the same type of hydrogen-bonded chain

The molecule of buthalital, (I) [systematic name: 5-(2-methylpropyl)-5-(prop-2-en-1-yl)-2-sulfanylidene-1,3-diazinane-4,6-dione], C11H16N2O2S, exhibits a planar pyrimidine ring, whereas the pyrimidine ring of methitural, (II) [systematic name: 5-(1-methylbutyl)-5-[2-(methylsulfanyl)ethyl]-2-sulfanyl...

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Main Authors: Thomas Gelbrich, Ulrich J. Griesser
Format: Article
Language:English
Published: International Union of Crystallography 2017-12-01
Series:Acta Crystallographica Section E: Crystallographic Communications
Subjects:
crystal structure
hydrogen bonding
barbiturates
pharmaceuticals
Online Access:http://scripts.iucr.org/cgi-bin/paper?S205698901701653X
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spelling doaj-13915a91ea8f4ca7a8f539fbdf5ef4b92020-11-24T22:37:31ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902017-12-0173121908191210.1107/S205698901701653Xdx2002Buthalital and methitural – 5,5-substituted derivatives of 2-thiobarbituric acid forming the same type of hydrogen-bonded chainThomas Gelbrich0Ulrich J. Griesser1University of Innsbruck, Institute of Pharmacy, Innrain 52, 6020 Innsbruck, AustriaUniversity of Innsbruck, Institute of Pharmacy, Innrain 52, 6020 Innsbruck, AustriaThe molecule of buthalital, (I) [systematic name: 5-(2-methylpropyl)-5-(prop-2-en-1-yl)-2-sulfanylidene-1,3-diazinane-4,6-dione], C11H16N2O2S, exhibits a planar pyrimidine ring, whereas the pyrimidine ring of methitural, (II) [systematic name: 5-(1-methylbutyl)-5-[2-(methylsulfanyl)ethyl]-2-sulfanylidene-1,3-diazinane-4,6-dione], C12H20N2O2S2, is slightly puckered. (I) and (II) contain the same hydrogen-bonded chain structure in which each molecule is connected, via four N—H...O=C hydrogen bonds, to two other molecules, resulting in a hydrogen-bonded chain displaying a sequence of R22(8) rings. The same type of N—H...O=C hydrogen-bonded chain has previously been found in several 5,5-disubstituted derivatives of barbituric acid which are chemically closely related to (I) and (II).http://scripts.iucr.org/cgi-bin/paper?S205698901701653Xcrystal structurehydrogen bondingbarbituratespharmaceuticals
collection DOAJ
language English
format Article
sources DOAJ
author Thomas Gelbrich
Ulrich J. Griesser
spellingShingle Thomas Gelbrich
Ulrich J. Griesser
Buthalital and methitural – 5,5-substituted derivatives of 2-thiobarbituric acid forming the same type of hydrogen-bonded chain
Acta Crystallographica Section E: Crystallographic Communications
crystal structure
hydrogen bonding
barbiturates
pharmaceuticals
author_facet Thomas Gelbrich
Ulrich J. Griesser
author_sort Thomas Gelbrich
title Buthalital and methitural – 5,5-substituted derivatives of 2-thiobarbituric acid forming the same type of hydrogen-bonded chain
title_short Buthalital and methitural – 5,5-substituted derivatives of 2-thiobarbituric acid forming the same type of hydrogen-bonded chain
title_full Buthalital and methitural – 5,5-substituted derivatives of 2-thiobarbituric acid forming the same type of hydrogen-bonded chain
title_fullStr Buthalital and methitural – 5,5-substituted derivatives of 2-thiobarbituric acid forming the same type of hydrogen-bonded chain
title_full_unstemmed Buthalital and methitural – 5,5-substituted derivatives of 2-thiobarbituric acid forming the same type of hydrogen-bonded chain
title_sort buthalital and methitural – 5,5-substituted derivatives of 2-thiobarbituric acid forming the same type of hydrogen-bonded chain
publisher International Union of Crystallography
series Acta Crystallographica Section E: Crystallographic Communications
issn 2056-9890
publishDate 2017-12-01
description The molecule of buthalital, (I) [systematic name: 5-(2-methylpropyl)-5-(prop-2-en-1-yl)-2-sulfanylidene-1,3-diazinane-4,6-dione], C11H16N2O2S, exhibits a planar pyrimidine ring, whereas the pyrimidine ring of methitural, (II) [systematic name: 5-(1-methylbutyl)-5-[2-(methylsulfanyl)ethyl]-2-sulfanylidene-1,3-diazinane-4,6-dione], C12H20N2O2S2, is slightly puckered. (I) and (II) contain the same hydrogen-bonded chain structure in which each molecule is connected, via four N—H...O=C hydrogen bonds, to two other molecules, resulting in a hydrogen-bonded chain displaying a sequence of R22(8) rings. The same type of N—H...O=C hydrogen-bonded chain has previously been found in several 5,5-disubstituted derivatives of barbituric acid which are chemically closely related to (I) and (II).
topic crystal structure
hydrogen bonding
barbiturates
pharmaceuticals
url http://scripts.iucr.org/cgi-bin/paper?S205698901701653X
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AT ulrichjgriesser buthalitalandmethitural55substitutedderivativesof2thiobarbituricacidformingthesametypeofhydrogenbondedchain
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