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.
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Umezono et al. (2013) studied this question.
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