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The absence of nitrone form in re-determined crystal structure of 2-hydroxyimino-3-methyl-4-nitro-2,5-dihydrothiophene 1,1-dioxide

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Abstract

Crystal and molecular structures of 2-hydroxyimino-3-methyl-4-nitro-2,5-dihydrothiophene-1,1-dioxide C5H6N2O5S (I) have been re-determined by single crystal X-ray diffraction analysis. The structure of I (space group P212121, a = 6.124(1) Å, b = 9.205(2) Å, c = 14.884(3) Å, Z = 4) was solved by the direct method and refined anisotropically in the full-matrix approximation to R = 0.064 using all 1756 measured independent reflections (automated diffractometer CAD-4, λCuK α, anomalous scattering taken into account). This study proves that the compound I contains a disordered group H-O-N=C, but not the isomeric nitrone group O←N(H)=C, as it has been concluded by the workers who pioneered single crystal X-ray diffraction study of I and erroneously took the second low-occupied oxygen position of the disordered hydroxyimine group for H at N atom.

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka

    A. N. Chekhlov

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  1. A. N. Chekhlov
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Original Russian Text Copyright © 2005 A. N. Chekhlov

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Translated from Zhurnal Strukturnoi Khimii, Vol. 46, No. 2, pp.383–387, March–April, 2005.

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Chekhlov, A.N. The absence of nitrone form in re-determined crystal structure of 2-hydroxyimino-3-methyl-4-nitro-2,5-dihydrothiophene 1,1-dioxide. J Struct Chem 46, 376–380 (2005). https://doi.org/10.1007/s10947-006-0057-6

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  • DOI: https://doi.org/10.1007/s10947-006-0057-6

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