2,6-Dimethoxy-4-(5-oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidenemethyl)phenyl acetate

Abstract

Key indicators: single-crystal X-ray study; T = 273 K; mean (C-C) = 0.003 Å; R factor = 0.040; wR factor = 0.117; data-to-parameter ratio = 12.8.The title compound, C 20 H 17 NO 6 , was synthesized by the reaction of syringaldehyde with hippuric acid. The molecule adopts a Z configuration about the central olefinic bond. The two benzene rings and the oxazolone ring are almost coplanar. The crystal structure is stabilized by weak intermolecular C-HÁ Á ÁO hydrogen bonds. Experimental Crystal dataC 20 H 17 NO 6 M r = 367.35 Triclinic, P1 a = 8.8400 (13) Å b = 10.4431 (15) Å c = 10.9693 (16) Å = 111.074 (6) = 96.544 (6) = 102.119 (6) V = 903.7 (2) Å 3 Z = 2 Mo K radiation = 0.10 mm À1 T = 273 (2) K 0.15 Â 0.12 Â 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 10391 measured reflections 3176 independent reflections 2244 reflections with I > 2(I) R int = 0.028

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

“…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).…”

“…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). T = 273 (2) K 0.15 Â 0.12 Â 0.10 mm…”

“…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-2phenyl-4,5-dihydro-1,3-oxazol-4-ylidenemethyl)-phenyl acetate (Sun et al, 2007) suggests that the presence of the 4methoxy 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.…”

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

“…These angle values and the exocyclic angles of C3 and C5 (Table 2) are in accordance with the repulsive intramolecular interactions between the N1 and H10 atoms, similar to the oxazol-5-one derivatives reported previously. [25][26][27] Bond lengths, angles and torsion angles of 1 and 2 are comparable with the similar compounds, especially for the oxazol-5-one rings, O1-C2-O2 exocyclic bond angles and N1/C3/C4/C5 torsion angles. Except the torsion angles, the bond parameters are comparable with the other oxazol-5-one derivatives.…”

4-{[(4Z)-5-Oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidene]methyl}phenyl acetate

“…For background to the biological activity of 1,3-oxazole and imidazoles, see: Williams & Fu (2010); Khbnadidah et al (2003). For related structures, see: Sun et al (2007); Jotani & Baldaniya (2008).…”