1-[3-(Morpholin-4-yl)propyl]-4-(3-nitrophenyl)spiro[azetidine-3,9′-xanthen]-2-one

The β-lactam (azetidin-2-one) ring of the title compound, C28H27N3O5, is nearly planar [maximum deviation = 0.010 (1) Å] and makes dihedral angles of 75.77 (5), 52.78 (9) and 88.72 (5)°, respectively, with the benzene ring, the least-squares plane formed by the four C atoms of the morpholine ring, which adopts a chair conformation, and the xanthene ring system. In the crystal, C—H⋯O hydrogen-bond contacts connect neighbouring molecules into infinite zigzag chains running parallel to the b axis.


Comment
2-Azetidinones, commonly known as β-lactams, occupy a central place among medicinally important compounds due to their unique structure and their antibacterial activities (Arumugam et al., 2011;Jarrahpour et al., 2010;Singh, 2003;Singh et al., 2011Singh et al., , 2014. β-Lactams have shown many interesting biological properties, such as acting as cholesterol absorption inhibitors, and applications as antimicrobial, antifungal, antitubercular, anticancer, anti HIV and antiparkinsonian agents (Mehta et al. 2010). Moreover the morpholine moiety is present in many heterocyclic compounds with hypocholesterolemic and hypolipidemic activity (Chrysselis et al. 2000).
The bond lengths and angles in (I) are comparable with similar compounds that we have reported previously (Akkurt et al., 2008a,b;Çelik et al., 2009a,b;Yalçın et al., 2009).
In the crystal, molecules are linked by C-H···O hydrogen contacts (Table 1) into infinite zigzag chains running parallel to [010]. Fig. 2 shows a view down the a axis of the crystal packing of (I).

Figure 1
The title molecule (I) with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.

Figure 2
Hydrogen bonding and molecular packing of (I) viewed along the a axis. Only H atoms involved in H bonding are shown.   Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.