Crystal structure of (2S,4R)-ethyl 4-nitro-methyl-1-[(S)-1-phenyl-eth-yl]-6-sulfanyl-idene-piperidine-2-carboxyl-ate.

Araceli Zárate,Angel Mendoza,David Aparicio,Angel Palillero

doi:10.1107/s2056989014026711

Abstract

In the title compound, C17H22N2O4S, a thiopiperidine derivative, the piperidine ring has an envelope conformation with the methylene C atom opposite to the C=S bond as the flap. The nitromethyl substituent is equatorial while the ethoxycarbonyl group is axial. The mean planes of the nitromethyl group, the carboxy group and phenyl ring are inclined to the mean plane through the five planar atoms of the piperidine ring [maximum deviation = 0.070 (4) Å] by 56.8 (2), 83.8 (5) and 87.1 (2)°, respectively. There is an intramolecular C—H⋯O hydrogen bond involving an H atom of the ethoxycarbonyl group and a nitro O atom. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming chains along [100]. The chains are linked by further C—H⋯O hydrogen bonds, forming corrugated layers lying parallel to (001).

Highlights

In the title compound, C17H22N2O4S, a thiopiperidine derivative, the piperidine ring has an envelope conformation with the methylene C atom opposite to the C S bond as the flap
The mean planes of the nitromethyl group, the carboxy group and phenyl ring are inclined to the mean plane through the five planar atoms of the piperidine ring [maximum deviation = 0.070 (4) Å] by
The corresponding nitro compounds can be transformed into a wide range of synthetically valuable products such as amines (Poupart et al, 1999), ketones (Pinnick et al, 1990), carboxylic acids, nitrile oxides and other functionalities (Mukaiyama et al, 1960)

Summary

Introduction

C17H22N2O4S, a thiopiperidine derivative, the piperidine ring has an envelope conformation with the methylene C atom opposite to the C S bond as the flap. There is an intramolecular C—H O hydrogen bond involving an H Molecules are linked by C—H O hydrogen bonds, forming chains along [100].

Results

Conclusion