11-Hydroxy-9-[1-(4-methylphenyl)-4-oxo-3-phenylazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.01,8.02,6.012,17]octadeca-12,14,16-triene-8-carbonitrile

In the title compound, C33H29N3O5, the four-membered ring of the β-lactam fragment is essentially planar (r.m.s. deviation = 0.0122 Å), with the carbonyl O atom displaced from this ring by 0.856 (9) Å. The mean planes of the methoxyphenyl and phenyl rings are inclined at dihedral angles 85.10 (7) and 21.56 (14)°, respectively, with respect to the mean plane of the four-membered ring. The pyrrolidine rings adopt envelope conformations with C atoms lying 0.535 (4) and 0.519 (4) Å out of the planes formed by the remaining ring atoms. The furan ring also adopts an envelope conformation with a C atom 0.560 (3) Å out of the plane formed by the remaining ring atoms. The nine-membered indene ring is almost planar (r.m.s. deviation = 0.0240 Å), with the carbonyl O atom displaced by 0.145 (3) Å from this ring. The molecular structure is stabilized by a strong intramolecular O—H⋯N hydrogen bond and the crystal structure is consolidated by C—H⋯O hydrogen bonds.

In the title compound, C 33 H 29 N 3 O 5 , the four-membered ring of the -lactam fragment is essentially planar (r.m.s. deviation = 0.0122 Å ), with the carbonyl O atom displaced from this ring by 0.856 (9) Å . The mean planes of the methoxyphenyl and phenyl rings are inclined at dihedral angles 85.10 (7) and 21.56 (14) , respectively, with respect to the mean plane of the four-membered ring. The pyrrolidine rings adopt envelope conformations with C atoms lying 0.535 (4) and 0.519 (4) Å out of the planes formed by the remaining ring atoms. The furan ring also adopts an envelope conformation with a C atom 0.560 (3) Å out of the plane formed by the remaining ring atoms. The nine-membered indene ring is almost planar (r.m.s. deviation = 0.0240 Å ), with the carbonyl O atom displaced by 0.145 (3) Å from this ring. The molecular structure is stabilized by a strong intramolecular O-HÁ Á ÁN hydrogen bond and the crystal structure is consolidated by C-HÁ Á ÁO hydrogen bonds.
The molecular structure of the title compound is stabilized by a strong intramolecular hydrogen bond O4-H4A···N2 (Table 1). The crystal structure is consolidated by intermolecular C-H···O hydrogen bonds (Tab. 1 & Fig. 2).
The organic layer was separated and dried over sodium sulfate. After filteration and evaporation of the organic solvent was carried out under reduced pressure. The product was separated by column chromatography using hexane and ethyl acetate (4:6) as an eluent to give a colorless solid. The product was dissolved in chloroform (3 ml) and heated for two minutes. The resulting solution was subjected to crystallization by slow evaporation of the solvent resulting in single crystals suitable for X-ray crystallographic studies.

Refinement
All H atoms bonded to C-atoms were positioned geometrically and refined using a riding model, with C-H = 0.93, 0.96, 0.97 and 0.98 Å, for aryl, methyl, methylene and methine H-atoms, respectively. The U iso (H) were allowed at 1.5U eq (C methyl) or 1.2U eq (C non-methyl). The hydroxy H-atom was located from a difference map and was alloewed to refine freely. An absolute structure was not established due to insufficient anomalous dispersion effects. Therefore, 2699 Friedel pairs of reflections were merged.

Figure 1
The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.   Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) 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.