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π–π stacking motifs in dialkylbis{5-[(E)-2-aryldiazen-1-yl]-2-hydroxybenzoato}tin(IV) complexes


Linden, Anthony; Basu Baul, Tushar S (2016). π–π stacking motifs in dialkylbis{5-[(E)-2-aryldiazen-1-yl]-2-hydroxybenzoato}tin(IV) complexes. Acta Crystallographica. Section C: Structural Chemistry, 72(4):313-325.

Abstract

The diorganotin(IV) complexes of 5-[(E)-2-aryl­diazen-1-yl]-2-hy­droxy­benzoic acid are of inter­est because of their structural diversity in the crystalline state and their inter­esting biological activity. The structures of di­methyl­bis­{2-hy­droxy-5-[(E)-2-(4-methyl­phen­yl)diazen-1-yl]­benzoato}tin(IV), [Sn(CH3)2(C14H11N2O3)2], and di-n-butyl­bis­{2-hy­droxy-5-[(E)-2-(4-methyl­phen­yl)diazen-1-yl]­ben­zo­ato}tin(IV) benzene hemisolvate, [Sn(C4H9)2(C14H11N2O3)2]·0.5C6H6, exhibit the usual skew-trapezoidal bipyramidal coordination geometry observed for related complexes of this class. Each structure has two independent mol­ecules of the SnIV complex in the asymmetric unit. In the di­methyl­tin structure, inter­molecular O-H...O hydrogen bonds and a very weak Sn...O inter­action link the independent mol­ecules into dimers. The planar carboxyl­ate ligands lend themselves to [pi]-[pi] stacking inter­actions and the diversity of supra­molecular structural motifs formed by these inter­actions has been examined in detail for these two structures and four closely related analogues. While there are some recurring basic motifs amongst the observed stacking arrangements, such as dimers and step-like chains, variations through longi­tudinal slipping and inversion of the direction of the overlay add complexity. The [pi]-[pi] stacking motifs in the two title complexes are combinations of some of those observed in the other structures and are the most complex of the structures examined.

Abstract

The diorganotin(IV) complexes of 5-[(E)-2-aryl­diazen-1-yl]-2-hy­droxy­benzoic acid are of inter­est because of their structural diversity in the crystalline state and their inter­esting biological activity. The structures of di­methyl­bis­{2-hy­droxy-5-[(E)-2-(4-methyl­phen­yl)diazen-1-yl]­benzoato}tin(IV), [Sn(CH3)2(C14H11N2O3)2], and di-n-butyl­bis­{2-hy­droxy-5-[(E)-2-(4-methyl­phen­yl)diazen-1-yl]­ben­zo­ato}tin(IV) benzene hemisolvate, [Sn(C4H9)2(C14H11N2O3)2]·0.5C6H6, exhibit the usual skew-trapezoidal bipyramidal coordination geometry observed for related complexes of this class. Each structure has two independent mol­ecules of the SnIV complex in the asymmetric unit. In the di­methyl­tin structure, inter­molecular O-H...O hydrogen bonds and a very weak Sn...O inter­action link the independent mol­ecules into dimers. The planar carboxyl­ate ligands lend themselves to [pi]-[pi] stacking inter­actions and the diversity of supra­molecular structural motifs formed by these inter­actions has been examined in detail for these two structures and four closely related analogues. While there are some recurring basic motifs amongst the observed stacking arrangements, such as dimers and step-like chains, variations through longi­tudinal slipping and inversion of the direction of the overlay add complexity. The [pi]-[pi] stacking motifs in the two title complexes are combinations of some of those observed in the other structures and are the most complex of the structures examined.

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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
Uncontrolled Keywords:diorganotin carboxylate complexes; dibutyltin complexes; dimethyltin complexes; tin(IV); [pi]-[pi] stacking; biological activity; 5-[(E)- 2-aryldiazen-1-yl]-2-hydroxybenzoic acids; crystal structure.
Language:English
Date:2016
Deposited On:27 Apr 2016 17:03
Last Modified:28 Apr 2016 07:54
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:2053-2296
Funders:Indo Swiss Joint Research Programme
Publisher DOI:https://doi.org/10.1107/S2053229616004435

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