Structural and theoretical study on the 1:2 addition complex of 1,2,4,5-bis{8′,11′-dithia[4.3.3]propella(3′,4′)}benzene with I2

Paweł Szlachcic , Tomasz Seidler , Katarzyna Stadnicka

Abstract

The crystal structure of the title compound, C22H26S4·2I2, contains two centrosymmetric molecules of 1,2,4,5-bis{8′,11′-dithia[4.3.3]propella(3′,4′)}benzene, and four I2 molecules in the unit cell of space group P21/c. The cyclohexene rings adopt boat conformation, whereas tetrahydrothiophene rings have envelope conformation. The iodine molecules are linked to one type of the sulphur atoms of the propellane molecule by a charge-transfer bond, with S⋯I distance of 2.7844(12) and I–I = 2.8153(5) Å. The second type of symmetrically independent sulphur atoms are engaged in a weak interaction of C–H⋯S type with the H⋯S distance of 3.09(1) Å. The geometry optimisation of the crystal structure at the B3LYP level with MIDI! basis set gave good agreement with the experimental data (S⋯I distance of 2.754 and I–I = 2.923 Å). NBO analysis for the complex showed that the S⋯I interaction is due to charge transfer from the lone pair on the sulphur to the vacant σ* orbital of the I2 acceptor.
Author Paweł Szlachcic (FoAaE / DoChaP)
Paweł Szlachcic,,
- Department of Chemistry and Physics
, Tomasz Seidler
Tomasz Seidler,,
-
, Katarzyna Stadnicka
Katarzyna Stadnicka,,
-
Journal seriesJournal of Molecular Structure, ISSN 0022-2860, (A 20 pkt)
Issue year2013
Vol1033
No6
Pages162-170
Publication size in sheets0.5
Keywords in EnglishPropellanes, CT complexes, Crystal structures, DFT calculations
ASJC Classification1604 Inorganic Chemistry; 1605 Organic Chemistry; 1607 Spectroscopy; 1602 Analytical Chemistry
DOIDOI:10.1016/j.molstruc.2012.07.052
URL http://www.sciencedirect.com/science/article/pii/S002228601200734X
Internal identifierWRE/2013/4
Languageen angielski
Score (nominal)20
Score sourcejournalList
Publication indicators WoS Citations = 4; Scopus SNIP (Source Normalised Impact per Paper): 2013 = 0.843; WoS Impact Factor: 2013 = 1.599 (2) - 2013=1.585 (5)
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FinansowanieGrant No. MNiSW/IBM_PC_HSZ1/UJ/083/2009
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