Abstract
Two polymorphic crystal forms of the title compound, C12H13NO2S (systematic name: 6-methyl-N-phenyl-2,3-di-hydro-1,4-oxathiine-5-carboxamide), were isolated from a truncated, (12 solvent), polymorph screen on pure lyophillized material. Crystals of form 1 were obtained from all solvents included in the screen with the exception of methanol. As isolated from aceto-nitrile the crystals are triclinic, space group P with Z' = 2. Crystals of form 2, which were isolated from methanol only are monoclinic, space group I2/a with Z' = 1. The crystal packing in both structures is dominated by the formation of infinite -NH⋯O hydrogen-bonded chains through the carboxamide core.
Highlights
6-Methyl-N-phenyl-2,3-dihydro-1,4-oxathiine-5-carboxamide, (Carboxine or Carboxin) 1, is a systemic fungicide from the oxathiin class of agents
The phenyl ring defined by atoms C1–C6 and the carboxamide core defined by atoms C6, N1, C7, O1 and C8 are almost planar
It is interesting to note that the carboxamide core for Molecule A is significantly less planar than that of Molecule B with atom N1A displaced from the mean plane by À0.0481 (6) A
Summary
6-Methyl-N-phenyl-2,3-dihydro-1,4-oxathiine-5-carboxamide, (Carboxine or Carboxin) 1, is a systemic fungicide from the oxathiin class of agents. This class of agents was discovered in 1964 (von Schmeling & Kulka, 1966) and was notable in that they were among the first fungicides that were known to exhibit translocation i.e. the ability to move from the leaves to other tissues in the plant. This unique property has made them effective for protection against rusts and smuts.
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