2-Phenyl-4-(3,4,5-trimethoxy­benzyl­idene)-1,3-oxazol-5(4H)-one

Yi-Feng Sun; Yi-Ping Cui

doi:10.1107/S1600536808005746

. 2008 Mar 7;64(Pt 4):o678. doi: 10.1107/S1600536808005746

2-Phenyl-4-(3,4,5-trimethoxybenzylidene)-1,3-oxazol-5(4H)-one

Yi-Feng Sun ^a,^b,^*, Yi-Ping Cui ^a

PMCID: PMC2960957 PMID: 21202071

Abstract

The title compound, C₁₉H₁₇NO₅, was synthesized as part of a continuing project involving the structures of oxazolone derivatives. The molecule adopts a Z configuration about the central olefinic bond. The 2-phenyl ring is slightly twisted out of the plane of the oxazolone ring system by 11.2 (2)°. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For background literature, see: Aaglawe et al. (2003 ▶); Grassi et al. (2004 ▶); Khan et al. (2006 ▶); Song et al. (2001 ▶). For related structures, see: Sun et al. (2007 ▶); Imhof & Garms (2005 ▶); Song et al. (2004 ▶); Vasuki et al. (2001 ▶).

Experimental

Crystal data

C₁₉H₁₇NO₅
M _r = 339.34
Triclinic,
a = 7.3897 (5) Å
b = 8.1532 (6) Å
c = 14.0023 (9) Å
α = 86.917 (5)°
β = 83.306 (4)°
γ = 82.471 (5)°
V = 830.02 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 (2) K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.985, T _max = 0.990
4665 measured reflections
2904 independent reflections
2056 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.121
S = 1.04
2904 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005746/pk2085sup1.cif

e-64-0o678-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005746/pk2085Isup2.hkl

e-64-0o678-Isup2.hkl^{(142.5KB, 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
C16—H16⋯O1ⁱ	0.93	2.59	3.503 (2)	168
C6—H6⋯O3ⁱⁱ	0.93	2.62	3.420 (2)	144

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

Acknowledgments

This project was supported by the Jiangsu Planned Projects for Postdoctoral Research Funds (grant No. 0701001B).

supplementary crystallographic information

Comment

The development of highly efficient nonlinear optical crystals is extremely important for laser spectroscopy and laser processing. Oxazolone derivatives are highly versatile intermediates used for the synthesis of several biologically active organic molecules, such as amino acids, peptides, antimicrobial or antitumor compounds, immunomodulators, heterocyclic precursors for biosensor coupling, and photosensitive composition devices for proteins (Aaglawe et al., 2003; Grassi et al., 2004; Khan et al., 2006). It has been reported (Song et al., 2001) that some oxazolone derivatives exhibit promising nonlinear optical properties. The second-harmonic generation (SHG) value of the title compound is 1.821, as compared with urea powder. In this contribution, we report the crystal structure of the title compound.

The molecule possesses normal geometric parameters and adopts a Z configuration about the central olefinic bond (Fig. 1). The C11–C16 phenyl ring and the oxazolone ring are almost coplanar. However, the C4–C9 phenyl ring is slightly twisted out of the plane of the oxazolone ring system by 11.2 (2) °. Comparison with 2,6-dimethoxy-4- (5-oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidenemethyl)-phenyl acetate (Sun et al., 2007) suggests that the presence of the 4-methoxy group leads to this deviation from coplanarity. Also, while O3, O4, O5, C17 and C19 are approximately coplanar with their attached benzene ring, C18 deviate from their mother benzene ring (Fig. 1). The crystal structure is stabilized by the weak intermolecular C—H···O hydrogen bonds (Table 1).

Similar structures have been observed in the related oxazolone analogues reported by Sun et al. (2007), Imhof & Garms (2005), Song et al. (2004), and by Vasuki et al. (2001).

Experimental

The title compound was synthesized from 3,4,5-trimethoxybenzaldehyde and hippuric acid as reported by Song et al. (2001). A mixture of hippuric acid (2.2 mmol), 3,4,5-trimethoxybenzaldehyde (2 mmol), sodium acetate (3 mmol) in acetic anhydride (8 ml) was refluxed for 5 hr. It was then cooled and ethanol (10 ml) was added to it. The resulting mixture was left over night at room temp. The solid thus obtained was filtered, dried and crystallized from ethanol to yield the title compound in 73% yield. A single-crystal suitable for an X-ray structural analysis was obtained by slowly evaporating from ethanol at room temperature.