4-[(3-Meth­oxy­anilino)methyl­idene]-2-phenyl-1,3-oxazol-5(4H)-one

Wan-Yun Huang; Ye Zhang; Kun Hu; Qing-Mei Lin; Xian-Xian Liu

doi:10.1107/S1600536812008276

. 2012 Mar 10;68(Pt 4):o1008. doi: 10.1107/S1600536812008276

4-[(3-Methoxyanilino)methylidene]-2-phenyl-1,3-oxazol-5(4H)-one

Wan-Yun Huang ^a, Ye Zhang ^a, Kun Hu ^b, Qing-Mei Lin ^b, Xian-Xian Liu ^a,^*

PMCID: PMC3343974 PMID: 22589883

Abstract

In the title compound, C₁₇H₁₄N₂O₃, the oxazolone ring is essentially planar [maximum deviation = 0.004 (1) Å] and is oriented with respect to the phenyl and benzene rings at 10.06 (9) and 5.63 (8)°, respectively; the dihedral angle between the phenyl ring and the benzene ring is 15.69 (8)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into chains running along the a axis. Neighbouring chains are interconnected by π–π stacking, the centroid–centroid distance being 3.6201 (9) Å.

Related literature

For background to the oxazolones, see: Fisk et al. (2007 ▶); Mosey et al. (2008 ▶); Hewlett et al. (2009 ▶). For the bioactivities of 4-(aminomethylene)-2-phenyl-4H-oxazol-5-one derivatives, see: Tandon et al. (2004 ▶); John et al. (2008 ▶). For the synthesis, see: Matos et al. (2003 ▶). For related structures, see: Romeiro et al. (2010 ▶); Vasuki et al. (2002 ▶).

Experimental

Crystal data

C₁₇H₁₄N₂O₃
M _r = 294.30
Triclinic,
a = 6.6085 (5) Å
b = 7.1887 (5) Å
c = 15.3659 (10) Å
α = 98.629 (5)°
β = 94.096 (5)°
γ = 108.715 (6)°
V = 677.96 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 150 K
0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova (single source at offset) Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.975, T _max = 0.985
5557 measured reflections
2759 independent reflections
2317 reflections with I > 2σ(I)
R _int = 0.023
Standard reflections: 0

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.118
S = 1.02
2759 reflections
204 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.29 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: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008276/xu5464sup1.cif

e-68-o1008-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008276/xu5464Isup2.hkl

e-68-o1008-Isup2.hkl^{(135.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812008276/xu5464Isup3.cml

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
N2—H2A⋯O1ⁱ	0.92 (2)	2.26 (2)	3.0110 (18)	138.1 (17)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Science Foundation of Guilin Normal College (grant No. 2008), Guilin Scientific Research and Technological Development Projects (grant No. 20110106-2) and Guangxi University Scientific Research Projects (grant No. 200103YB159).

supplementary crystallographic information

Comment

Oxazolones are heterocyclic compounds which serve as a very important role in the synthesis of amino acids, peptides and natural product (Fisk et al., 2007; Mosey et al., 2008; Hewlett et al., 2009). Among them, 4- (aminomethylene)-2-phenyl-4H-oxazol-5-one derivatives show a range of interesting and medicinally relevant bioactivities (Tandon et al., 2004; John et al., 2008). Recently, Romeiro reported the crystal structure of the 4-[(Dimethylamino)methylidene]-2- (4-nitrophenyl)-1,3-oxazol-5(4H)-one (Romeiro et al., 2010). Herein, we wish to report the synthesis and crystal structure of 4-[(3-Methoxy-phenylamino)-methylene]-2- phenyl-4H-oxazol-5-one. The molecule with the Z-configuration (Fig. 1) of the title compound is planar with the maximum deviations from the least-squares plane through all non-hydrogen atoms being 0.292 Å for atom C4 and -0.237 Å for atom C1; the r.m.s. = 0.089 Å. The sequence of C7—N1, N1—C9, C9—C10, C10—N2, and N2—C11 bond distances of 1.2917 (19), 1.407 (2), 1.372 (2), 1.337 (2), and 1.4201 (19) Å, respectively, indicate substantial delocalization of π-electron density over these atoms. The geometric parameters match closely those related structure (Romeiro et al., 2010; Vasuki et al., 2002). The crystal packing is dominated by N—H···O and π-π interactions. An intermolecular N(2)—H(2 A)···O(1) (Symmetry code: x + 1, y, z) hydrogen bond (Table 1) link the molecule into a one-dimensional chain along the a axis (Fig. 2). And the neighbouring chains are interconnected by π-π stacking interactions occurring between oxazolin-5-one and the 3-methoxy-phenyl ring with a centroid-centroid distance of 3.62 Å, which lead to form a two-dimensional network (Fig. 3).

Experimental

A mixture of 4-ethoxymethylene-2-phenyl-4H-oxazol-5-one (Matos et al., 2003) (0.01 mol) and 3-methoxy-phenylamine (0.01 mol) in THF (25 ml) was stirred at room temperature for 4 h. The solvent was then evaporated under reduced pressure and the residue was crystallized from ethyl acetate to give orange crystals suitable for X-ray analysis (yield 82%).