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Intra- and intermolecular Se...X(X= Se, O) interactions in selenium-containing heterocycles: 3-benzoylimino-5-(morpholin-4-yl)-1,2,4-diselenazole


Linden, Anthony; Zhou, Yuehui; Heimgartner, Heinz (2014). Intra- and intermolecular Se...X(X= Se, O) interactions in selenium-containing heterocycles: 3-benzoylimino-5-(morpholin-4-yl)-1,2,4-diselenazole. Acta Crystallographica. Section C, 70(5):482-487.

Abstract

In the selenium-containing heterocyclic title compound \{sys­tematic name: N-[5-(morpholin-4-yl)-3H-1,2,4-diselen­azol-3-yl­idene]benzamide}, C13H13N3O2Se2, the five-membered 1,2,4-diselenazole ring and the amide group form a planar unit, but the phenyl ring plane is twisted by 22.12 (19)° relative to this plane. The five consecutive N-C bond lengths are all of similar lengths [1.316 (6)-1.358 (6) Å], indicating substantial delocalization along these bonds. The Se...O distance of 2.302 (3) Å, combined with a longer than usual amide C=O bond of 2.252 (5) Å, suggest a significant inter­action between the amide O atom and its adjacent Se atom. An analysis of related structures containing an Se-Se...X unit (X = Se, S, O) shows a strong correlation between the Se-Se bond length and the strength of the Se...X inter­action. When X = O, the strength of the Se...O inter­action also correlates with the carbonyl C=O bond length. Weak inter­molecular Se...Se, Se...O, C-H...O, C-H...[pi] and [pi]-[pi] inter­actions each serve to link the mol­ecules into ribbons or chains, with the C-H...O motif being a double helix, while the combination of all inter­actions generates the overall three-dimensional supra­molecular framework.

In the selenium-containing heterocyclic title compound \{sys­tematic name: N-[5-(morpholin-4-yl)-3H-1,2,4-diselen­azol-3-yl­idene]benzamide}, C13H13N3O2Se2, the five-membered 1,2,4-diselenazole ring and the amide group form a planar unit, but the phenyl ring plane is twisted by 22.12 (19)° relative to this plane. The five consecutive N-C bond lengths are all of similar lengths [1.316 (6)-1.358 (6) Å], indicating substantial delocalization along these bonds. The Se...O distance of 2.302 (3) Å, combined with a longer than usual amide C=O bond of 2.252 (5) Å, suggest a significant inter­action between the amide O atom and its adjacent Se atom. An analysis of related structures containing an Se-Se...X unit (X = Se, S, O) shows a strong correlation between the Se-Se bond length and the strength of the Se...X inter­action. When X = O, the strength of the Se...O inter­action also correlates with the carbonyl C=O bond length. Weak inter­molecular Se...Se, Se...O, C-H...O, C-H...[pi] and [pi]-[pi] inter­actions each serve to link the mol­ecules into ribbons or chains, with the C-H...O motif being a double helix, while the combination of all inter­actions generates the overall three-dimensional supra­molecular framework.

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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:crystal structure selenium-containing heterocycles 1,2,4-diselenazoles double helix supramolecular framework intermolecular interactions hydrogen bonding Se...X (X = Se, O) interactions
Language:English
Date:2014
Deposited On:16 May 2014 15:36
Last Modified:05 Apr 2016 17:51
Publisher:Wiley-Blackwell
ISSN:2053-2296
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1107/S2053229614008237
Permanent URL: https://doi.org/10.5167/uzh-95694

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