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dc.contributor.authorShaibah, Mohammed A. E.
dc.contributor.authorSagar, Belakavadi K.
dc.contributor.authorYathirajan, Hemmige S.
dc.contributor.authorCordes, David B.
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorHarrison, William T. A.
dc.date.accessioned2019-02-14T15:30:04Z
dc.date.available2019-02-14T15:30:04Z
dc.date.issued2019-02-01
dc.identifier.citationShaibah , M A E , Sagar , B K , Yathirajan , H S , Cordes , D B , Slawin , A M Z & Harrison , W T A 2019 , ' Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates : a robust R_{2}^{2}(8) supramolecular motif (even when disordered) ' , Acta Crystallographica Section E , vol. 75 , no. 2 , pp. 167-174 . https://doi.org/10.1107/S2056989018018224en
dc.identifier.issn2056-9890
dc.identifier.otherPURE: 257744368
dc.identifier.otherPURE UUID: 771cfdb6-0b95-4cdc-b0ff-c15c1c5d12a4
dc.identifier.otherRIS: urn:695BFC309A00A4735BE6AE10CDD82285
dc.identifier.otherScopus: 85061157335
dc.identifier.otherORCID: /0000-0002-5366-9168/work/54181493
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861528
dc.identifier.otherWOS: 000457717300015
dc.identifier.urihttp://hdl.handle.net/10023/17069
dc.descriptionHSY thanks UGC for the award of a UGC–BSR Faculty Fellowship for three years. BKS thanks the UGC for the award of a Rajeev Gandhi fellowship.en
dc.description.abstractThe syntheses and structures of five mol­ecular salts of protonated 4,4,7,7-tetra­methyl-3a,5,6,7a-tetra­hydro­benzo­thia­zol-2-yl­amine (C11H 19N 2S +) with different deprotonated carb­oxy­lic acids (4-methyl­benzoic acid, 4-bromo­benzoic acid, 3,5-di­nitro­benzoic acid, fumaric acid and succinic acid) are reported, namely 2-amino-4,4,7,7-tetra­methyl-4,5,6,7-tetra­hydro-1,3-benzo­thia­zol-3-ium 4-methyl­benzoate, C11H 19N 2S +·C 8H 7O 2 −, (I), 2-amino-4,4,7,7-tetra­methyl-4,5,6,7-tetra­hydro-1,3-benzo­thia­zol-3-ium 4-bromo­benzoate, C11H 19N 2S +·C 7H 4BrO 2 −, (II), 2-amino-4,4,7,7-tetra­methyl-4,5,6,7-tetra­hydro-1,3-benzo­thia­zol-3-ium 3,5-di­nitro­benzoate, C11H 19N 2S +·C 7H 3N 2O 6 −, (III), bis­(2-amino-4,4,7,7-tetra­methyl-4,5,6,7-tetra­hydro-1,3-benzo­thia­zol-3-ium) fumarate, 2C11H 19N 2S +·C 4H 2O 4 2−,(IV), and the 1:1 co-crystal of bis­(2-amino-4,4,7,7-tetra­methyl-4,5,6,7-tetra­hydro-1,3-benzo­thia­zol-3-ium) succinate and 2-amino-4,4,7,7-tetra­methyl-4,5,6,7-tetra­hydro-1,3-benzo­thia­zol-3-ium hydrogen succin­ate 4,4,7,7-tetra­methyl-3a,5,6,7a-tetra­hydro­benzo­thia­zol-2-yl­amine, 1.5C11H 19N 2S +·0.5C 4H 4O 4 2−·0.5C 4H 5O 4 −. 0.5C11H 18N 2S, (V). 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—NH 2 fragment of the cation are indistinguishable, indicating a significant contribution of the –NH—C=N+H 2 resonance form to the structure. The packing for (I)–(V) features a robust local R 2 2(8) loop motif in which the cation forms two near-linear N—H⋯O hydrogen bonds from the N+—H group and syn H atom of the amine group to the carboxyl­ate 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 R 2 2(8) loop results for both disorder components]. The anti H atom of the –NH2 group also forms an N—H⋯O hydrogen bond, which results in [001] chains in (I) and (II), isolated centrosymmetric tetra­mers 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.
dc.format.extent8
dc.language.isoeng
dc.relation.ispartofActa Crystallographica Section Een
dc.rightsCopyright © 2019 The Author(s). This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.en
dc.subjectBenzothiazoleen
dc.subjectHydrogen bonden
dc.subjectMolecular salten
dc.subjectCrystal structureen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleHydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates : a robust R_{2}^{2}(8) supramolecular motif (even when disordered)en
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.identifier.doihttps://doi.org/10.1107/S2056989018018224
dc.description.statusPeer revieweden


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