Crystal structure of 2-[(3S,4S)-4-(anthracen-9-yl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]-2-aza-2H-phenalene-1,3-dione unknown solvate

The central β-lactam ring of the title compound, C36H24N2O4, is almost planar (r.m.s. deviation = 0.003 Å) and makes dihedral angles of 17.17 (19), 89.76 (17) and 78.44 (17)° with the benzene ring, the anthracene ring (r.m.s. deviation = 0.003 Å) and the 1H-benzo[de]isoquinoline-1,3(2H)-dione moiety, which is nearly planar [maximum deviation = 0.098 (2) Å], respectively. The molecular structure is stabilized by an intramolecular C—H⋯N hydrogen bond. In the crystal, molecules are linked via C—H⋯π and π–π stacking interactions [centroid–centroid distances = 3.5270 (19) and 3.779 (2) Å], forming a three-dimensional structure. A region of disordered electron density, probably disordered solvent molecules, was treated with the SQUEEZE procedure in PLATON [Spek (2015 ▸). Acta Cryst. C71, 9–18], which indicated a solvent cavity of 322 Å3 containing approximately 91 electrons. Their formula mass and unit-cell characteristics were not taken into account during the refinement.

In the crystal, molecules are connected by C-H···π and π-π stacking interactions forming a three-dimensional structure; see

S3. Refinement
H atoms attached to C atoms were positioned geometrically (C-H = 0.93 -0.98 Å), and refined using a riding model with U iso (H) = 1.5U eq (C) for methyl H atoms and = 1.2U eq (C) fro other H atoms. The crystal was of poor quality and did not diffract significantly at high 2θ angles, probably due to the presence of the disordered solvent molecules. 23 reflections were omitted owing to bad disagreement. A region of disordered electron density, most probably disordered solvent molecules, occupying voids of ca 322 Å 3 for an electron count of 91, was removed with the SQUEEZE procedure in PLATON [Spek (2015). Acta Cryst. C71,[9][10][11][12][13][14][15][16][17][18] following unsuccessful attempts to model it as plausible solvent molecules. Their formula mass and unit-cell characteristics were not taken into account during refinement.

Figure 1
Perspective view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
View along a-axis of the crystal packing of the title compound.

2-[(3S,4S)-4-(Anthracen-9-yl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]-2-aza-2H-phenalene-1,3-dione
Crystal data 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.