Crystal structure of 2-oxo-1,2-di-phenyl-ethyl diiso-propyl-carbamate

Acta Crystallogr E Crystallogr Commun. 2021 Oct 13;77(Pt 11):1091-1094. doi: 10.1107/S2056989021010367. eCollection 2021 Nov 1.

Abstract

The title compound, C21H25NO3, crystallized as a racemic twin in the Sohnke space group P21. In the mol-ecular structure of the title compound, both enanti-omers show a highly similar conformation with the urethane function and the benzoyl group showing an almost perpendicular arrangement [the dihedral angle is 72.46 (8)° in the S-enanti-omer and 76.21 (8)° in the R-enanti-omer]. In the crystal structure, mol-ecules of both enanti-omers show infinite helical arrangements parallel to the b axis formed by weak C-H⋯O hydrogen bonds between the phenyl ring of the benzoyl group and the carbamate carbonyl group. In case of the R-enanti-omer, this helix is additionally stabilized by a bifurcated hydrogen bond between the carbonyl function of the benzoyl group towards both phenyl groups of the mol-ecule.

Keywords: C—H⋯O hydrogen bonds; carbamates; crystal structure; urethanes.

Grants and funding

This work was funded by the Open Access Fund of the University of Koblenz-Landau; Lohmann GmbH and Co. KG.