Transannular S···N interactions in 10-ethynyl-10H-phenothiazine 5-oxide and 5,5-dioxide

Transannular S···N interactions in 10-ethynyl-10H-phenothiazine 5-oxide and 5,5-dioxide

The title compounds, C14H9NOS, (1), and C14H9NO2S, (2), are oxidation products of the parent compound 10-ethynyl-10H-phenothiazine. They differ with respect to transannular interactions, the intramolecular S···N contact being shorter in (2). Intermolecular Csp-H···O hydrogen bonds were detected in b...

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Veröffentlicht in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2013-12, Vol.69 (Pt 12), p.1553
Hauptverfasser: Umezono, Satoru, Ikeda, Satoshi, Okuno, Tsunehisa
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container_issue Pt 12
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container_title Acta crystallographica. Section C, Crystal structure communications
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creator Umezono, Satoru
Ikeda, Satoshi
Okuno, Tsunehisa
description The title compounds, C14H9NOS, (1), and C14H9NO2S, (2), are oxidation products of the parent compound 10-ethynyl-10H-phenothiazine. They differ with respect to transannular interactions, the intramolecular S···N contact being shorter in (2). Intermolecular Csp-H···O hydrogen bonds were detected in both crystals, and (1) was found to form stronger hydrogen bonds. These results are in agreement with the lower acidity of Csp-H in (2), caused by an increase in π-electron density due to the transannular S···N interaction.
doi_str_mv 10.1107/S0108270113031661
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title Transannular S···N interactions in 10-ethynyl-10H-phenothiazine 5-oxide and 5,5-dioxide
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