Abstract
The structure of the title compound, C14H15ClN2O4, prepared by reaction of a methacryloyl dimer with nitro-aniline, was determined to establish the relative substituent orientation on the cyclo-penta-none ring. In agreement with an earlier proposed reaction mechanism, the amide group and the methyl group adjacent to the chloro substituent adopt equatorial positions and relative cis orientation, whereas the Cl substituent itself and the methyl group adjacent to the amide have axial orientations relative to the mean plane of the five-membered ring. The conformation of the mol-ecule is stabilized by one classical N-H⋯O (2.18 Å) and one non-classical C-H⋯O (2.23 Å) hydrogen bond, each possessing an S(6) graph-set motif. The crystal packing is defined by several non-classical intra-molecular hydrogen bonds, as well as by partial stacking of the aromatic rings.
Highlights
The structure of the title compound, C14H15ClN2O4, prepared by reaction of a methacryloyl dimer with nitroaniline, was determined to establish the relative substituent orientation on the cyclopentanone ring
The crystal packing is defined by several nonclassical intramolecular hydrogen bonds, as well as by partial stacking of the aromatic rings
The crystal packing is governed by several short contacts, which may be classified as non-classical hydrogen bonds, and by partial stacking of the aromatic rings
Summary
The title compound, cis-3-chloro-1,3-dimethyl-N-(4-nitrophenyl)-2-oxocyclopentane-1-carboxamide, (1), was prepared in the course of study of the formation and reactivity of methacryloyl chloride dimers (2), (3) and (4) (Warneke et al., 2014). The scheme below shows the reactivity of methacryloyl dimers and the synthesis of the title compound (1) Compounds (3) and (4) show similar 1H and 13C NMR spectra, making the direct assignment of the relative orientation of the cyclopentanone substituents almost impossible. The crystal structure of (1), as well as the crystal structure of another aromatic amide, cis-3-chloro-N-(3,5-dichlorophenyl)-1,3-dimethyl-2-oxocyclopentanecarboxamide, Acta Cryst. Solved and reported earlier (Warneke et al, 2014), were crucial for the determination of the substituent orientation of the cyclopentanone ring after the isolation and derivatization of (4). For the X-ray structures of related trans-3-chloro-N(3,5-dichlorophenyl)-1,3-dimethyl-2-oxocyclopentanecarboxamide with cis orientation of two methyl groups, see Fischer et al (1985)
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
