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

Abdullah M Asiri; Hassan M Faidallah; Tariq R Sobahi; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536812011579

. 2012 Mar 24;68(Pt 4):o1154. doi: 10.1107/S1600536812011579

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

Abdullah M Asiri ^a,^b,^‡, Hassan M Faidallah ^a, Tariq R Sobahi ^a, Seik Weng Ng ^c,^a, Edward R T Tiekink ^c,^*

PMCID: PMC3344097 PMID: 22606100

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.

Related literature

For background to the biological activity of oxazolone derivatives, see: Fidanza & Dernoeden (1996 ▶); Khan et al. (2006 ▶); Puig et al. (2000 ▶) For the synthesis, see: Mariappan et al. (2011 ▶).

Experimental

Crystal data

C₁₇H₁₃NO₂
M _r = 263.28
Orthorhombic,
a = 12.0827 (6) Å
b = 7.7848 (3) Å
c = 27.6527 (16) Å
V = 2601.1 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.974, T _max = 0.983
7121 measured reflections
2990 independent reflections
2206 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.109
S = 1.03
2990 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011579/hb6681sup1.cif

e-68-o1154-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011579/hb6681Isup2.hkl

e-68-o1154-Isup2.hkl^{(146.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812011579/hb6681Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O2ⁱ	0.95	2.56	3.463 (2)	158
C6—H6⋯Cg1ⁱⁱ	0.95	2.93	3.8311 (17)	158
C9—H9⋯Cg1ⁱⁱⁱ	0.95	2.92	3.6532 (17)	135

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors are grateful to the Center of Excellence for Advanced Materials Research and the Chemistry Department at King Abdulaziz University for providing the research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

supplementary crystallographic information

Comment

Several oxazolone derivatives (Fidanza & Dernoeden, 1996) have proved effective as insecticides, herbicides and fungicides that control brown patch (Rhizoctonia solani (Kühn)). Oxazol-5-ones are known to inhibit the activity of the tyrosinase enzyme with a maximum inhibition by the derivative which bears a cinnamoyl residue at the C-4 position (Khan et al., 2006). Further, some 3,4-diaryloxazolones show inhibition of cyclooxygenase-2 (COX-2) and in vivo anti-inflammatory activity making them excellent candidates for the treatment of arthritis and hyperalgesia (Puig et al., 2000). In this connection, the title compound, 4(Z)-2-phenyl-4-(phenylmethylidene)-4,5-dihydro-1,3-oxazol-5-one (I), was synthesized and characterized by X-ray crystallography.

In (I), Fig. 1, the oxazole ring is planar with a r.m.s. deviation for the fitted atoms of 0.007 Å. The pendent benzene ring is slightly twisted out of this plane and forms a dihedral angle of 7.98 (8)°; the N1—C1—C11—C12 torsion angle = -171.85 (15)°. The conformation about the C3═C4 bond [1.348 (2) Å] is Z. There is a slight twist in this region of the molecule so that the dihedral angle between the oxazol and phenyl rings is 5.50 (8)°; the C4—C5—C10—C9 torsion angle = 177.79 (14)°. The r.m.s. deviation of the 20 non-hydrogen atoms comprising (I) = 0.131 Å with the maximum deviations being 0.258 (1) Å for the C16 atom and -0.224 (2) Å for the C13 atom.

The crystal packing is sustained by C—H···O and C—H···π interactions, Table 1, as well as π—π interactions occurring between the oxazole and benzene rings [ring centroid···ring centroid distance = 3.5259 (9) Å for symmetry operation 1 - x, 1 - y, 1 - z]. Globally, molecules assemble into undulating layers that stack along the b axis, Fig. 2.

Experimental

4-Methoxybenzoylglycine was prepared in accord with the literature procedure (Mariappan et al., 2011). A mixture of 4-methoxybenzoylglycine (2.1 g, 0.01 mmol), benzaldehyde (1.1 g, 0.02 mmol), anhydrous sodium acetate (0.8 g, 0.01 mmol) and acetic anhydride (4.0 g, 0.04 mmol) was refluxed for 1 h on a water bath with occasional stirring. The resulting mixture was left in a refrigerator overnight. The solid thus obtained was filtered, washed with cold water, dried in an hot-air oven at 333 K and recrystallized from ethanol as yellow polyhedra. Yield: 84%. M.pt: 470–471 K.