Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates: a robust (8) supramolecular motif (even when disordered)
Identifieur interne : 002122 ( Ncbi/Merge ); précédent : 002121; suivant : 002123Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates: a robust (8) supramolecular motif (even when disordered)
Auteurs : Mohammed A. E. Shaibah [Inde] ; Belakavadi K. Sagar [Inde] ; Hemmige S. Yathirajan [Inde] ; David B. Cordes ; Alexandra M. Z. Slawin ; William T. A. HarrisonSource :
- Acta Crystallographica Section E: Crystallographic Communications [ 2056-9890 ] ; 2019.
Abstract
The syntheses and structures of five molecular salts of protonated 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (C11H19N2S+) with different deprotonated carboxylic acids (4-methylbenzoic acid, 4-bromobenzoic acid, 3,5-dinitrobenzoic acid, fumaric acid and succinic acid) are reported·In every case, the cation protonation occurs at the N atom of the thiazole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methylene groups are disordered over two sets of sites). The C—N bond lengths of the nominal –NH+=C—NH2 fragment of the cation are indistinguishable, indicating a significant contribution of the –NH—C=N+H2 resonance form to the structure.
Url:
DOI: 10.1107/S2056989018018224
PubMed: 30800445
PubMed Central: 6362640
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(8) supramolecular motif (even when disordered)</title>
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<front><div type="abstract" xml:lang="en"><p>The syntheses and structures of five molecular salts of protonated 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
) with different deprotonated carboxylic acids (4-methylbenzoic acid, 4-bromobenzoic acid, 3,5-dinitrobenzoic acid, fumaric acid and succinic acid) are reported·In every case, the cation protonation occurs at the N atom of the thiazole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methylene groups are disordered over two sets of sites). The C—N bond lengths of the nominal –NH<sup>+</sup>
=C—NH<sub>2</sub>
fragment of the cation are indistinguishable, indicating a significant contribution of the –NH—C=N<sup>+</sup>
H<sub>2</sub>
resonance form to the structure.</p>
</div>
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(8) supramolecular motif (even when disordered)</title>
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(8) supramolecular motif (even when disordered)</title>
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<front><div type="abstract" xml:lang="en"><p>The syntheses and structures of five molecular salts of protonated 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
) with different deprotonated carboxylic acids (4-methylbenzoic acid, 4-bromobenzoic acid, 3,5-dinitrobenzoic acid, fumaric acid and succinic acid) are reported·In every case, the cation protonation occurs at the N atom of the thiazole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methylene groups are disordered over two sets of sites). The C—N bond lengths of the nominal –NH<sup>+</sup>
=C—NH<sub>2</sub>
fragment of the cation are indistinguishable, indicating a significant contribution of the –NH—C=N<sup>+</sup>
H<sub>2</sub>
resonance form to the structure.</p>
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</author>
<author><name sortKey="Harrison, William T A" sort="Harrison, William T A" uniqKey="Harrison W" first="William T A" last="Harrison">William T A. Harrison</name>
<affiliation wicri:level="2"><nlm:affiliation>Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland.</nlm:affiliation>
<country>Royaume-Uni</country>
<placeName><region type="country">Écosse</region>
</placeName>
<wicri:cityArea>Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE</wicri:cityArea>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PubMed</idno>
<date when="2019">2019</date>
<idno type="RBID">pubmed:30800445</idno>
<idno type="pmid">30800445</idno>
<idno type="doi">10.1107/S2056989018018224</idno>
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<sourceDesc><biblStruct><analytic><title xml:lang="en">Hydrogen-bonded mol-ecular salts of reduced benzo-thia-zole derivatives with carboxyl-ates: a robust (8) supra-molecular motif (even when disordered).</title>
<author><name sortKey="Shaibah, Mohammed A E" sort="Shaibah, Mohammed A E" uniqKey="Shaibah M" first="Mohammed A E" last="Shaibah">Mohammed A E. Shaibah</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India.</nlm:affiliation>
<country xml:lang="fr">Inde</country>
<wicri:regionArea>Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006</wicri:regionArea>
<wicri:noRegion>Mysuru 570 006</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Sagar, Belakavadi K" sort="Sagar, Belakavadi K" uniqKey="Sagar B" first="Belakavadi K" last="Sagar">Belakavadi K. Sagar</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India.</nlm:affiliation>
<country xml:lang="fr">Inde</country>
<wicri:regionArea>Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006</wicri:regionArea>
<wicri:noRegion>Mysuru 570 006</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Yathirajan, Hemmige S" sort="Yathirajan, Hemmige S" uniqKey="Yathirajan H" first="Hemmige S" last="Yathirajan">Hemmige S. Yathirajan</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India.</nlm:affiliation>
<country xml:lang="fr">Inde</country>
<wicri:regionArea>Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006</wicri:regionArea>
<wicri:noRegion>Mysuru 570 006</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Cordes, David B" sort="Cordes, David B" uniqKey="Cordes D" first="David B" last="Cordes">David B. Cordes</name>
<affiliation wicri:level="2"><nlm:affiliation>School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.</nlm:affiliation>
<country>Royaume-Uni</country>
<placeName><region type="country">Écosse</region>
</placeName>
<wicri:cityArea>School of Chemistry, University of St Andrews, Fife KY16 9ST</wicri:cityArea>
</affiliation>
</author>
<author><name sortKey="Slawin, Alexandra M Z" sort="Slawin, Alexandra M Z" uniqKey="Slawin A" first="Alexandra M Z" last="Slawin">Alexandra M Z. Slawin</name>
<affiliation wicri:level="2"><nlm:affiliation>School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.</nlm:affiliation>
<country>Royaume-Uni</country>
<placeName><region type="country">Écosse</region>
</placeName>
<wicri:cityArea>School of Chemistry, University of St Andrews, Fife KY16 9ST</wicri:cityArea>
</affiliation>
</author>
<author><name sortKey="Harrison, William T A" sort="Harrison, William T A" uniqKey="Harrison W" first="William T A" last="Harrison">William T A. Harrison</name>
<affiliation wicri:level="2"><nlm:affiliation>Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland.</nlm:affiliation>
<country>Royaume-Uni</country>
<placeName><region type="country">Écosse</region>
</placeName>
<wicri:cityArea>Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE</wicri:cityArea>
</affiliation>
</author>
</analytic>
<series><title level="j">Acta crystallographica. Section E, Crystallographic communications</title>
<idno type="ISSN">2056-9890</idno>
<imprint><date when="2019" type="published">2019</date>
</imprint>
</series>
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<front><div type="abstract" xml:lang="en">The syntheses and structures of five mol-ecular salts of protonated 4,4,7,7-tetra-methyl-3a,5,6,7a-tetra-hydro-benzo-thia-zol-2-yl-amine (C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
) with different deprotonated carb-oxy-lic acids (4-methyl-benzoic acid, 4-bromo-benzoic acid, 3,5-di-nitro-benzoic acid, fumaric acid and succinic acid) are reported, namely 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 4-methyl-benzoate, C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>8</sub>
H<sub>7</sub>
O<sub>2</sub>
<sup>-</sup>
, (I), 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 4-bromo-benzoate, C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>7</sub>
H<sub>4</sub>
BrO<sub>2</sub>
<sup>-</sup>
, (II), 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 3,5-di-nitro-benzoate, C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>7</sub>
H<sub>3</sub>
N<sub>2</sub>
O<sub>6</sub>
<sup>-</sup>
, (III), bis-(2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium) fumarate, 2C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>4</sub>
H<sub>2</sub>
O<sub>4</sub>
<sup>2-</sup>
,(IV), and the 1:1 co-crystal of bis-(2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium) succinate and 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium hydrogen succin-ate 4,4,7,7-tetra-methyl-3a,5,6,7a-tetra-hydro-benzo-thia-zol-2-yl-amine, 1.5C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·0.5C<sub>4</sub>
H<sub>4</sub>
O<sub>4</sub>
<sup>2-</sup>
·0.5C<sub>4</sub>
H<sub>5</sub>
O<sub>4</sub>
<sup>-</sup>
. 0.5C<sub>11</sub>
H<sub>18</sub>
N<sub>2</sub>
S, (V). In every case, the cation protonation occurs at the N atom of the thia-zole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methyl-ene groups are disordered over two sets of sites). The C-N bond lengths of the nominal -NH<sup>+</sup>
=C-NH<sub>2</sub>
fragment of the cation are indistinguishable, indicating a significant contribution of the -NH-C=N<sup>+</sup>
H<sub>2</sub>
resonance form to the structure. The packing for (I)-(V) features a robust local <i>R</i>
<sub>2</sub>
<sup>2</sup>
(8) loop motif in which the cation forms two near-linear N-H⋯O hydrogen bonds from the N<sup>+</sup>
-H group and <i>syn</i>
H atom of the amine group to the carboxyl-ate group of an adjacent anion [(V) shows disorder of one of these bonds over N-H⋯O and N⋯H-O contributors but the same <i>R</i>
<sub>2</sub>
<sup>2</sup>
(8) loop results for both disorder components]. The <i>anti</i>
H atom of the -NH<sub>2</sub>
group also forms an N-H⋯O hydrogen bond, which results in [001] chains in (I) and (II), isolated centrosymmetric tetra-mers in (III) and [100] chains in (IV) and (V). Hirshfeld fingerprint plots and contact percentages for the different types of contacts of the cations are discussed.</div>
</front>
</TEI>
</pubmed>
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