Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 12 (December 2013)


organic compounds



Acta Cryst. (2013). C69, 1553-1556    [ doi:10.1107/S0108270113031661 ]

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

S. Umezono, S. Ikeda and T. Okuno

Abstract: 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 [pi]-electron density due to the transannular S...N inter­action.

CCDC references: 972879 and 972880

Formula: C14H9NOS and C14H9NO2S

Keywords: crystal structure; oxidation products; 10-ethynyl-10H-pheno­thia­zine; transannular S...N inter­actions; intra­molecular S...N contact.


hkldisplay filedownload file

Structure factor file (CIF format) (123.6 kbytes)
[ doi:10.1107/S0108270113031661/eg31411sup2.hkl ]
Contains datablock 1


hkldisplay filedownload file

Structure factor file (CIF format) (68.0 kbytes)
[ doi:10.1107/S0108270113031661/eg31412sup3.hkl ]
Contains datablock 2


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