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

Abdullah Mohamed Asiri; Mehmet Akkurt; Islam Ullah Khan; Muhammad N Arshad

doi:10.1107/S1600536809010216

. 2009 Mar 25;65(Pt 4):o842. doi: 10.1107/S1600536809010216

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

Abdullah Mohamed Asiri ^a, Mehmet Akkurt ^b,^*, Islam Ullah Khan ^c, Muhammad N Arshad ^a

PMCID: PMC2968875 PMID: 21582561

Abstract

The title molecule, C₁₇H₁₃NO₃, adopts a Z configuration about the central olefinic bond. The 2-phenyl ring is almost coplanar with the plane of the oxazolone ring system, making a dihedral angle of 2.03 (11)°. The crystal structure is stabilized by π–π interactions between the oxazolone ring and phenyl ring of a neighbouring molecule [centroid–centroid distance = 3.550 (3)Å], and by two weak intermolecular C—H⋯π interactions. In addition, the crystal structure exhibits one weak intramolecular C—H⋯N hydrogen bond.

Related literature

For general background to azalactones and their biological and pharmaceutical properties, see: Cannella et al. (1996 ▶); Cavelier & Verducci (1995 ▶); Gelmi et al. (1997 ▶); Gonzalez-Martinez, Puchades, Maquieira, Ferrer, Marco & Barcelo (1999 ▶); Gottwald & Seebach (1999 ▶); Mesaik et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₇H₁₃NO₃
M _r = 279.28
Triclinic,
a = 8.8073 (6) Å
b = 9.6140 (6) Å
c = 9.8272 (6) Å
α = 66.503 (4)°
β = 67.248 (4)°
γ = 71.734 (4)°
V = 691.14 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.28 × 0.08 × 0.05 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: none
14582 measured reflections
3457 independent reflections
1464 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.133
S = 0.93
3457 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010216/lx2096sup1.cif

e-65-0o842-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010216/lx2096Isup2.hkl

e-65-0o842-Isup2.hkl^{(169.5KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯N1	0.93	2.43	3.087 (3)	127
C17—H17A⋯Cg3ⁱ	0.96	2.81	3.682 (3)	151
C17—H17C⋯Cg2ⁱⁱ	0.96	2.96	3.832 (3)	151

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Symmetry codes: (i) Inline graphic ; (ii) . Cg2 is the centroid of the C1–C6 benzene ring and Cg3 is the centroid of the C11—C16 phenyl ring.

Acknowledgments

AMA acknowledges the Chemistry Department, Faculty of Science, King Abdul-Aziz University, for providing the laboratories and facilities.

supplementary crystallographic information

Comment

Azalactones are a class of important heterocyclic compounds and exhibit a variety of biological and pharmaceutical properties (Mesaik et al., 2004) They are also useful precursors for the synthesis of amino acids (Gottwald & Seebach, 1999), peptides (Cavelier & Verducci, 1995), heterocycles (Cannella et al., 1996), biosensors (Gonzalez-Martinez et al., 1999), and antitumoror antimicrobial compounds (Gelmi et al., 1997). Here we report the crystal structure of the title compound, 4-(2-methoxybenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one (Fig. 1).

The title molecule (Fig. 1) possesses normal geometric parameters (Allen et al., 1987) and adopts a Z configuration about the central olefinic bond. The C11–C16 phenyl ring makes a dihedral angle of 2.03 (11) ° with the plane of the oxazolone ring system. The molecular packing (Fig. 2) is stabilized by intermolecular π—π interactions between the oxazolone ring and phenyl ring of neighbouring molecules, with a Cg1···Cg3ⁱⁱⁱ distance of 3.550 (3) Å (Cg1 and Cg3 are the centroids of the O1/C10/N1/C8/C9 oxazolone ring and the C11—C16 phenyl ring; symmetry code as in Fig, 2). The crystal packing is further stabilized by two intermolecular C—H···π interactions; one between the H atom of methoxy group and the phenyl ring of a neighbouring molecule, a second between the H atom of methoxy group and the methoxyphenyl ring of an adjacent molecule, respectively (Fig. 2 and Table 1; Cg2 is the centroid of the C1–C6 benzene ring, symmetry code as in Fig, 2). Additionally, there is one intramolecular C—H···N hydrogen bond between a benzene—H atom and the N atom of oxazolone ring (Table 1 and Fig. 2).

Experimental

Anhydrous sodium acetate (2.1 g, 25.3 mmol) was added to a solution of 2-methoxybenzaldehyde (3.5 g, 25.7 mmol) and hippuric acid (7.7 g, 31.1 mmol) in acetic anhydride (2.1 g, 20.6 mmol). The reaction mixture was heated to 353 K and stirred under reflux conditions for the appropriate time 2 h. The reaction mixture was cooled to room temperature and ethanol (10 ml) was added. The mixture was stirred for 10 min until a yellow solid precipitated. The mixture was allowed to stand overnight, and then it was cooled in an ice bath. The crude azalactones were obtained after filtration and washing with hot water. Recrystallization from acetone/water afforded the pure azalactones as yellow crystals. [Yield (5.79 g, 91%), m.p. 440–441 K]. IR (cm^-1) 1769 (C═O),1648 (C═C).