Abstract
The title compound, C22H33NO12·CHCl3, was obtained as a product of a double aza-Michael addition of hydroxyl-amine on a Chiron with a known absolute configuration. The enanti-opure compound crystallized as a chloro-form solvate, in space group P1, and diffraction data were collected at room temperature with Ag Kα radiation. The Flack parameter refined to x = -0.01 (16); however, the Flack and Watkin 2AD plot clearly shows that differences between Friedel opposites (the D component of the plot) do not carry any reliable information about resonant scattering of Cl atoms, and are rather dominated by random and systematic errors. The RD factor calculated using 1941 acentric Friedel pairs is RD = 0.995. On the other hand, the 2A component of the plot, related to average intensities of Friedel pairs, shows that data are of good quality (RA = 0.069). This example illustrates that while using Ag Kα radiation (λ = 0.56083 Å), scatterers heavier than Cl should be present in a chiral crystal in order to determine confidently the absolute structure of the crystal.
Highlights
The title compound, C22H33NO12ÁCHCl3, was obtained as a product of a double aza-Michael addition of hydroxylamine on a Chiron with a known absolute configuration
The enantiopure compound crystallized as a chloroform solvate, in space group P1, and diffraction data were collected at room temperature with Ag K radiation
The Flack parameter refined to x = À0.01 (16); the Flack and Watkin 2AD plot clearly shows that differences between Friedel opposites do not carry any reliable information about resonant scattering of Cl atoms, and are rather dominated by random and systematic errors
Summary
Isolates (Perez-Bautista et al, 2016). In a work aimed at the synthesis of 1-deoxynojirimycin (DNJ), an azasugar alkaloid presenting -glucosidase inhibitor properties, the title compound was obtained (Amaro Hernandez, 2019). A double aza-Michael addition was observed, followed by a transesterification in ethanol, affording a disubstituted isoxazolidinone, which was characterized by X-ray diffraction. This compound is closely related to other isoxazolidinone derivatives obtained through an Amadori rearrangement, which were studied for their potential antioxidant properties, and their application as flood flavouring agents (Hodge, 1955; Mills & Hodge, 1976; Mills, 1979). The chloroform lattice molecule does not interact with the organic molecule For this Cl-containing crystal, intensities were collected at room temperature using Ag K radiation.
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