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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
Author(s) -
Linden Anthony,
Zhou Yuehui,
Heimgartner Heinz
Publication year - 2014
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229614008237
Subject(s) - chemistry , intermolecular force , crystallography , amide , ring (chemistry) , bond length , delocalized electron , molecule , hydrogen bond , atom (system on chip) , stereochemistry , supramolecular chemistry , selenium , crystal structure , organic chemistry , computer science , embedded system
In the selenium‐containing heterocyclic title compound {systematic name: N ‐[5‐(morpholin‐4‐yl)‐3 H ‐1,2,4‐diselenazol‐3‐ylidene]benzamide}, C 13 H 13 N 3 O 2 Se 2 , 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...π and π–π 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.