(4Z)-4-Benzylidene-2-phenyl-1,3-oxazol-5(4H)-one

Abstract

In the title compound, C17H13NO2, the benzene ring is twisted slightly out of the plane of the oxazole ring to which it is attached [dihedral angle = 7.98 (8)°]. Similarly, there is a twist [dihedral angle = 5.50 (8)°] between the oxazole and phenyl rings that are linked via the C=C bond [1.348 (2) Å]; the conformation about the latter is Z. In the crystal, the presence of C—H⋯O, C—H⋯π and π–π inter­actions [centroid–centroid distance = 3.5259 (9) Å] link the mol­ecules into a three-dimensional architecture.

Dihydrooxazolones and dihydroimidazolones derived from acylglycines: syntheses, molecular structures and supramolecular assembly

“…1), in a reaction which involves both the condensation of the aldehyde unit with the methylene group of the glycine and an intramolecular dehydration to form the oxazolone ring. This compound has been reported previously as an orthorhombic polymorph, in the space group Pbca, following crystallization from ethanol (Asiri et al, 2012). We have now found a second polymorph, in the space group P1, resulting from crystallization from a mixture of acetone and toluene.…”

“…We have now found a second polymorph, in the space group P1, resulting from crystallization from a mixture of acetone and toluene. However, it is necessary to note here that in the original report (Asiri et al, 2012), compound (I) was named, incorrectly, as the 2-phenyl, rather than the 2-(4-methylphenyl) derivative, and that the Experimental section of that report refers, rather surprisingly, to 4methoxybenzoylglycine rather than to 4-methylbenzoylglycine.…”

“…Preparation of compound (I). Compound (I) was prepared as described previously (Asiri et al, 2012) but recrystallized from a mixture of acetone and toluene (1:1 v/v), rather than from ethanol as used previously, to give the triclinic polymorph instead of the original orthorhombic polymorph (see Scheme 1).…”

“…Data for the orthorhombic polymorph of compound (I) are taken from Asiri et al (2012), but with the atom-numbering modified to match the systematic numbering used for the triclinic polymorph. Notes: 'Dihedral 1' represents the dihedral angle between the oxazolone ring and the ring linked to it at atom C2.…”

Spectroscopic, Structural and Density Functional Theory (DFT) Studies of Two Oxazol-5-one Derivatives

“…deviation of -0.006(2) Å for 1 and 0.004(1) Å for 2. Phenyl rings are twisted slightly out of these planes, with the dihedral angles between two rings being 12.80(2)⁰ and 6.41 (2) [20][21][22][23] The molecules adopt a Z conformation about these olefinic bonds with C5 cis to N1. C2=O2 bond distances are also shown to have a typical double bond character with lengths of 1.196(1) Å and 1.201(1) Å, respectively.…”