F. Makaev, F. Shepel, S. Malinovskii
Nov 1, 2005
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Journal
Journal of Structural Chemistry
Abstract
The crystal and molecular structure of (±)-2S-2-(2-chlorophenyl)-3-acetyl-1,3-oxazolidine was determined by X-ray diffraction analysis. Orthorhombic crystal with unit cell parameters a = 6.7419(8) Å, b = 10.3797(12) Å, c = 14.9233(18) Å; space group P212121, Z = 4, ρ calc = 1.436 g/cm3, composition C11H12ClNO2. The deviation of the chlorine atom from the mean square plane of the phenyl cycle is −0.010(5) Å. The five-membered oxazolidine cycle has an envelope conformation, which is typical for this class of compounds; the cycle is rotated at the C-C bond with respect to the phenyl fragment (the dihedral angle is 79.7(1)°). The spatial structure of the C2 chiral center lying in the plane of the 2-chlorophenyl fragment may be described as a distorted tetrahedron with an S configuration of the sp3 hybridized carbon atom. Analysis of torsion angles and deviation of the nitrogen atom from the surrounding three-angle plane by −0.017(3) Å allows one to speak about a tendency toward a pyramidal structure for the trisubstituted nitrogen atom. The 3D crystal structure is formed by intermolecular hydrogen bonds of C-H...O type and a strong intermolecular contact of 3.164(3) Å between the chlorine atom and the carbonyl oxygen of the acyl group.