(1S,3'S,3a'R,6'S)-6'-(2-Chloro-phen-yl)-3'-[(2R,3S)-1-(4-meth-oxy-phen-yl)-4-oxo-3-phenyl-azetidin-2-yl]-2-oxo-3',3'a,4',6'-tetra-hydro-2H,2'H-spiro-[ace-naphthyl-ene-1,1'-pyrrolo-[1,2-c][1,3]thia-zole]-2',2'-dicarbo-nitrile

Abstract

The mol-ecular conformation of the title compound, C41H29ClN4O3S, is stabilized by intra-molecular C-H⋯O and C-H⋯Cl hydrogen bonds. The thia-zole ring adopts an envelope conformation with the N atom as the flap, while the pyrrolidine ring has a twisted conformation on the N-C bond involving the spiro C atom. The β la-ctam ring makes dihedral angles of 39.74 (15) and 16.21 (16)° with the mean planes of the thia-zole and pyrrolidine rings, respectively. The thia-zole ring mean plane makes dihedral angles of 23.79 (13) and 70.88 (13) ° with the pyrrolidine and cyclo-pentane rings, respectively, while the pyrrolidine ring makes a dihedral angle of 85.63 (13)° with the cyclo-pentane ring. The O atom attached to the β la-ctam ring deviates from its mean plane by 0.040 (2) Å, while the O atom attached to the cyclo-pentane ring deviates from its mean plane by 0.132 (2) Å. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming chains along [010], and C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.6928 (17) Å].

Fig. 1.

The molecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Fig. 2.

The crystal packing of the title compound viewed along the a axis, showing the hydrogen bonds as dashed lines [see Table 1 for details; H-atoms not involved in hydrogen bonds have been excluded for clarity].