4,4-Dimethyl-2-[3-nitro-2-phenyl-1-(phenylsulfanyl)propyl]-4,5-dihydro-1,3-oxazole

In the title compound, C20H22N2O3S, the oxazoline ring is planar (r.m.s. deviation = 0.045 Å) and forms dihedral angles of 47.24 (8) and 10.11 (8)° with the S- and C-bound phenyl rings, respectively. The nitro group lies to the same side of the molecule as the oxazoline ring but is orientated so as not to interact with the ring. Linear supramolecular chains along [010] are formed via C—H⋯O and C—H⋯S contacts. Chains are consolidated into a three-dimensional architecture by C—H⋯π and van der Waals interactions.

In the title compound, C 20 H 22 N 2 O 3 S, the oxazoline ring is planar (r.m.s. deviation = 0.045 Å ) and forms dihedral angles of 47.24 (8) and 10.11 (8) with the S-and C-bound phenyl rings, respectively. The nitro group lies to the same side of the molecule as the oxazoline ring but is orientated so as not to interact with the ring. Linear supramolecular chains along [010] are formed via C-HÁ Á ÁO and C-HÁ Á ÁS contacts. Chains are consolidated into a three-dimensional architecture by C-HÁ Á Á and van der Waals interactions.

Related literature
For background on the biological activities of Rolipram, see: de Visser et al. (2008). For the synthesis of the title compound, see Villar (2008) Table 1 Hydrogen-bond geometry (Å , ).
In (I), Fig. 1, the oxazoline ring is planar (r.m.s. deviation = 0.045 Å) with the maximum deviations being 0.036 (2) Å for the C3 atom and -0.038 (2) Å for the C4 atom. The five-membered ring and the S-bound phenyl ring (C7-C12) are proximate and make a dihedral angle of 47.24 (8)°. The dihedral angles formed by these rings and the C-bound phenyl ring (C15-C20) are 10.11 (8) and 57.13 (8)°, respectively. The nitro group lies to the same side of the molecule as the oxazoline ring but is orientated away from the ring.
Chains are consolidated in the three-dimensional packing by C-H···π and van der Waals interactions, Fig. 3 and Table 1.

Experimental
The detailed synthesis of the title compound is described in a Ph.D. thesis (Villar, 2008

Figure 1
The molecular structure of compound (I) showing atom labelling scheme and displacement ellipsoids at the 50% probability level (arbitrary spheres for the H atoms).  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 > 2σ(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.