Acta Cryst. (2009). E65, o842 [ doi:10.1107/S1600536809010216 ]
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 ![[pi]](/logos/entities/pi_rmgif.gif)
- 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
interactions. In addition, the crystal structure exhibits one weak intramolecular C-HN hydrogen bond.
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).
All H atoms were positioned geometrically with C—H = 0.93 and 0.96 Å and refined using a riding approximation model with Uiso(H) = 1.2 or 1.5Ueq(C).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).
![[Figure 1]](./lx2096fig1thm.gif)
| Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius. |
![[Figure 2]](./lx2096fig2thm.gif)
| Fig. 2. π—π, C—H···π and C—H···N interactions (dotted lines) in the title compound. Cg denotes the ring centroids. [Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y, -z; (iii) -x+1, -y+1, -z+1]. |
| C17H13NO3 | Z = 2 |
| Mr = 279.28 | F(000) = 292 |
| Triclinic, P1 | Dx = 1.342 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.8073 (6) Å | Cell parameters from 1969 reflections |
| b = 9.6140 (6) Å | θ = 2.4–22.4° |
| c = 9.8272 (6) Å | µ = 0.09 mm−1 |
| α = 66.503 (4)° | T = 296 K |
| β = 67.248 (4)° | Prism, yellow |
| γ = 71.734 (4)° | 0.28 × 0.08 × 0.05 mm |
| V = 691.14 (8) Å3 |
| Bruker Kappa APEXII CCD diffractometer | 1464 reflections with I > 2σ(I) |
| Radiation source: sealed tube | Rint = 0.048 |
| graphite | θmax = 28.5°, θmin = 2.4° |
| Detector resolution: 10.0 pixels mm-1 | h = −11→11 |
| φ and ω scans | k = −12→12 |
| 14582 measured reflections | l = −13→13 |
| 3457 independent reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
| wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0583P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 0.93 | (Δ/σ)max = 0.001 |
| 3457 reflections | Δρmax = 0.16 e Å−3 |
| 192 parameters | Δρmin = −0.13 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.008 (3) |
| C17H13NO3 | γ = 71.734 (4)° |
| Mr = 279.28 | V = 691.14 (8) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 8.8073 (6) Å | Mo Kα radiation |
| b = 9.6140 (6) Å | µ = 0.09 mm−1 |
| c = 9.8272 (6) Å | T = 296 K |
| α = 66.503 (4)° | 0.28 × 0.08 × 0.05 mm |
| β = 67.248 (4)° |
| Bruker Kappa APEXII CCD diffractometer | 1464 reflections with I > 2σ(I) |
| 14582 measured reflections | Rint = 0.048 |
| 3457 independent reflections | θmax = 28.5° |
| R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
| wR(F2) = 0.133 | Δρmax = 0.16 e Å−3 |
| S = 0.93 | Δρmin = −0.13 e Å−3 |
| 3457 reflections | Absolute structure: ? |
| 192 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.25166 (15) | 0.44719 (14) | 0.39300 (14) | 0.0569 (5) | |
| O2 | 0.21889 (18) | 0.24891 (17) | 0.34504 (18) | 0.0822 (6) | |
| O3 | 0.71016 (18) | 0.05676 (17) | −0.02406 (16) | 0.0758 (6) | |
| N1 | 0.51111 (18) | 0.48138 (17) | 0.23057 (16) | 0.0496 (6) | |
| C1 | 0.7332 (2) | 0.2733 (2) | 0.0149 (2) | 0.0506 (7) | |
| C2 | 0.8036 (2) | 0.1640 (2) | −0.0653 (2) | 0.0585 (8) | |
| C3 | 0.9578 (3) | 0.1700 (3) | −0.1783 (2) | 0.0728 (9) | |
| C4 | 1.0418 (3) | 0.2832 (3) | −0.2108 (3) | 0.0812 (9) | |
| C5 | 0.9784 (3) | 0.3890 (3) | −0.1317 (2) | 0.0741 (9) | |
| C6 | 0.8245 (3) | 0.3836 (2) | −0.0200 (2) | 0.0613 (8) | |
| C7 | 0.5675 (2) | 0.2690 (2) | 0.1242 (2) | 0.0534 (7) | |
| C8 | 0.4736 (2) | 0.3592 (2) | 0.2139 (2) | 0.0494 (7) | |
| C9 | 0.3054 (3) | 0.3362 (2) | 0.3179 (2) | 0.0570 (8) | |
| C10 | 0.3815 (2) | 0.5263 (2) | 0.3330 (2) | 0.0469 (6) | |
| C11 | 0.3562 (2) | 0.6487 (2) | 0.3944 (2) | 0.0496 (7) | |
| C12 | 0.2070 (3) | 0.6867 (2) | 0.5026 (2) | 0.0623 (8) | |
| C13 | 0.1867 (3) | 0.8024 (3) | 0.5607 (3) | 0.0762 (9) | |
| C14 | 0.3129 (4) | 0.8808 (3) | 0.5107 (3) | 0.0779 (10) | |
| C15 | 0.4617 (3) | 0.8459 (3) | 0.4015 (3) | 0.0760 (10) | |
| C16 | 0.4826 (3) | 0.7300 (2) | 0.3435 (2) | 0.0627 (8) | |
| C17 | 0.7702 (3) | −0.0552 (3) | −0.1038 (3) | 0.0876 (10) | |
| H3 | 1.00400 | 0.09810 | −0.23150 | 0.0870* | |
| H4 | 1.14440 | 0.28850 | −0.28830 | 0.0970* | |
| H5 | 1.03870 | 0.46320 | −0.15340 | 0.0890* | |
| H6 | 0.78080 | 0.45550 | 0.03320 | 0.0740* | |
| H7 | 0.51770 | 0.19180 | 0.13430 | 0.0640* | |
| H12 | 0.12020 | 0.63380 | 0.53610 | 0.0750* | |
| H13 | 0.08670 | 0.82700 | 0.63400 | 0.0910* | |
| H14 | 0.29880 | 0.95860 | 0.55060 | 0.0940* | |
| H15 | 0.54730 | 0.90020 | 0.36740 | 0.0910* | |
| H16 | 0.58250 | 0.70640 | 0.26970 | 0.0750* | |
| H17A | 0.78080 | −0.00370 | −0.21230 | 0.1310* | |
| H17B | 0.69250 | −0.12400 | −0.06060 | 0.1310* | |
| H17C | 0.87760 | −0.11310 | −0.09190 | 0.1310* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0465 (8) | 0.0591 (8) | 0.0597 (8) | −0.0112 (7) | −0.0015 (6) | −0.0266 (7) |
| O2 | 0.0612 (10) | 0.0754 (11) | 0.1086 (12) | −0.0262 (9) | 0.0020 (8) | −0.0443 (9) |
| O3 | 0.0732 (10) | 0.0836 (11) | 0.0839 (10) | −0.0087 (9) | −0.0127 (8) | −0.0548 (9) |
| N1 | 0.0455 (10) | 0.0547 (10) | 0.0470 (9) | −0.0084 (8) | −0.0074 (8) | −0.0216 (8) |
| C1 | 0.0443 (12) | 0.0614 (13) | 0.0448 (10) | −0.0030 (10) | −0.0130 (9) | −0.0211 (10) |
| C2 | 0.0491 (13) | 0.0736 (15) | 0.0529 (12) | 0.0025 (11) | −0.0192 (10) | −0.0271 (11) |
| C3 | 0.0546 (14) | 0.1005 (19) | 0.0614 (13) | 0.0044 (14) | −0.0130 (11) | −0.0424 (13) |
| C4 | 0.0519 (14) | 0.116 (2) | 0.0599 (14) | −0.0092 (15) | −0.0056 (11) | −0.0282 (15) |
| C5 | 0.0538 (14) | 0.0970 (18) | 0.0667 (14) | −0.0201 (13) | −0.0109 (12) | −0.0236 (13) |
| C6 | 0.0533 (13) | 0.0743 (15) | 0.0558 (12) | −0.0103 (12) | −0.0134 (10) | −0.0243 (11) |
| C7 | 0.0508 (12) | 0.0569 (13) | 0.0542 (11) | −0.0078 (10) | −0.0138 (10) | −0.0230 (10) |
| C8 | 0.0442 (12) | 0.0517 (12) | 0.0486 (11) | −0.0064 (10) | −0.0102 (9) | −0.0179 (10) |
| C9 | 0.0504 (13) | 0.0538 (13) | 0.0639 (13) | −0.0091 (11) | −0.0088 (10) | −0.0244 (11) |
| C10 | 0.0417 (11) | 0.0501 (12) | 0.0449 (10) | −0.0090 (10) | −0.0112 (9) | −0.0126 (9) |
| C11 | 0.0476 (12) | 0.0492 (12) | 0.0504 (11) | −0.0018 (10) | −0.0184 (9) | −0.0162 (10) |
| C12 | 0.0587 (14) | 0.0646 (14) | 0.0605 (12) | −0.0086 (11) | −0.0091 (10) | −0.0275 (11) |
| C13 | 0.0818 (18) | 0.0753 (16) | 0.0744 (15) | −0.0038 (14) | −0.0150 (13) | −0.0430 (13) |
| C14 | 0.100 (2) | 0.0622 (15) | 0.0858 (17) | 0.0001 (15) | −0.0409 (15) | −0.0367 (13) |
| C15 | 0.0810 (18) | 0.0670 (15) | 0.0942 (18) | −0.0148 (13) | −0.0392 (15) | −0.0266 (14) |
| C16 | 0.0569 (14) | 0.0641 (14) | 0.0705 (13) | −0.0072 (11) | −0.0207 (11) | −0.0264 (12) |
| C17 | 0.107 (2) | 0.0841 (17) | 0.0864 (16) | 0.0101 (15) | −0.0377 (15) | −0.0545 (15) |
| O1—C9 | 1.396 (2) | C11—C16 | 1.380 (3) |
| O1—C10 | 1.378 (2) | C12—C13 | 1.378 (3) |
| O2—C9 | 1.192 (3) | C13—C14 | 1.361 (5) |
| O3—C2 | 1.358 (3) | C14—C15 | 1.380 (4) |
| O3—C17 | 1.431 (3) | C15—C16 | 1.377 (3) |
| N1—C8 | 1.398 (3) | C3—H3 | 0.9300 |
| N1—C10 | 1.285 (2) | C4—H4 | 0.9300 |
| C1—C2 | 1.409 (3) | C5—H5 | 0.9300 |
| C1—C6 | 1.386 (3) | C6—H6 | 0.9300 |
| C1—C7 | 1.441 (3) | C7—H7 | 0.9300 |
| C2—C3 | 1.383 (3) | C12—H12 | 0.9300 |
| C3—C4 | 1.371 (4) | C13—H13 | 0.9300 |
| C4—C5 | 1.375 (4) | C14—H14 | 0.9300 |
| C5—C6 | 1.376 (3) | C15—H15 | 0.9300 |
| C7—C8 | 1.345 (3) | C16—H16 | 0.9300 |
| C8—C9 | 1.464 (3) | C17—H17A | 0.9600 |
| C10—C11 | 1.448 (3) | C17—H17B | 0.9600 |
| C11—C12 | 1.385 (3) | C17—H17C | 0.9600 |
| O1···N1 | 2.260 (2) | C4···H17Cvii | 3.0100 |
| O2···C14i | 3.236 (3) | C5···H17Cvii | 2.9800 |
| O2···C12ii | 3.411 (3) | C8···H6 | 2.8100 |
| O1···H4iii | 2.8000 | C14···H17Aiv | 3.0300 |
| O1···H12 | 2.4500 | C15···H17Aiv | 3.0200 |
| O2···H7 | 2.7000 | C16···H4viii | 3.0700 |
| O2···H14i | 2.7800 | C17···H3 | 2.5300 |
| O2···H12ii | 2.7900 | H3···C17 | 2.5300 |
| O2···H13ii | 2.9200 | H3···H17A | 2.3700 |
| O3···H7 | 2.2700 | H3···H17C | 2.2900 |
| N1···O1 | 2.260 (2) | H4···O1ix | 2.8000 |
| N1···C6 | 3.087 (3) | H4···C16viii | 3.0700 |
| N1···H6 | 2.4300 | H4···H16viii | 2.5000 |
| N1···H16 | 2.6300 | H6···N1 | 2.4300 |
| C1···C10iv | 3.553 (3) | H6···C8 | 2.8100 |
| C2···C10iv | 3.532 (3) | H7···O2 | 2.7000 |
| C5···C9iv | 3.481 (4) | H7···O3 | 2.2700 |
| C6···N1 | 3.087 (3) | H7···H17Bx | 2.5600 |
| C6···C9iv | 3.392 (3) | H12···O1 | 2.4500 |
| C6···C8iv | 3.561 (3) | H12···O2ii | 2.7900 |
| C8···C14v | 3.524 (4) | H13···O2ii | 2.9200 |
| C8···C6iv | 3.561 (3) | H14···O2vi | 2.7800 |
| C9···C5iv | 3.481 (4) | H16···N1 | 2.6300 |
| C9···C6iv | 3.392 (3) | H16···H4viii | 2.5000 |
| C10···C16v | 3.530 (3) | H17A···C3 | 2.7900 |
| C10···C2iv | 3.532 (3) | H17A···H3 | 2.3700 |
| C10···C1iv | 3.553 (3) | H17A···C14iv | 3.0300 |
| C12···O2ii | 3.411 (3) | H17A···C15iv | 3.0200 |
| C14···C8v | 3.524 (4) | H17B···H7x | 2.5600 |
| C14···O2vi | 3.236 (3) | H17C···C3 | 2.7400 |
| C16···C10v | 3.530 (3) | H17C···H3 | 2.2900 |
| C3···H17A | 2.7900 | H17C···C4vii | 3.0100 |
| C3···H17C | 2.7400 | H17C···C5vii | 2.9800 |
| C9—O1—C10 | 105.44 (16) | C14—C15—C16 | 119.5 (3) |
| C2—O3—C17 | 119.06 (18) | C11—C16—C15 | 120.4 (2) |
| C8—N1—C10 | 105.35 (16) | C2—C3—H3 | 120.00 |
| C2—C1—C6 | 118.16 (17) | C4—C3—H3 | 120.00 |
| C2—C1—C7 | 118.56 (17) | C3—C4—H4 | 119.00 |
| C6—C1—C7 | 123.23 (18) | C5—C4—H4 | 119.00 |
| O3—C2—C1 | 115.60 (17) | C4—C5—H5 | 120.00 |
| O3—C2—C3 | 123.94 (19) | C6—C5—H5 | 120.00 |
| C1—C2—C3 | 120.5 (2) | C1—C6—H6 | 119.00 |
| C2—C3—C4 | 119.2 (2) | C5—C6—H6 | 119.00 |
| C3—C4—C5 | 121.7 (3) | C1—C7—H7 | 115.00 |
| C4—C5—C6 | 119.1 (3) | C8—C7—H7 | 115.00 |
| C1—C6—C5 | 121.38 (19) | C11—C12—H12 | 120.00 |
| C1—C7—C8 | 130.09 (18) | C13—C12—H12 | 120.00 |
| N1—C8—C7 | 129.85 (18) | C12—C13—H13 | 120.00 |
| N1—C8—C9 | 108.50 (16) | C14—C13—H13 | 120.00 |
| C7—C8—C9 | 121.64 (18) | C13—C14—H14 | 120.00 |
| O1—C9—O2 | 121.5 (2) | C15—C14—H14 | 120.00 |
| O1—C9—C8 | 104.65 (18) | C14—C15—H15 | 120.00 |
| O2—C9—C8 | 133.90 (18) | C16—C15—H15 | 120.00 |
| O1—C10—N1 | 116.07 (17) | C11—C16—H16 | 120.00 |
| O1—C10—C11 | 116.07 (16) | C15—C16—H16 | 120.00 |
| N1—C10—C11 | 127.85 (18) | O3—C17—H17A | 110.00 |
| C10—C11—C12 | 121.32 (19) | O3—C17—H17B | 109.00 |
| C10—C11—C16 | 119.45 (17) | O3—C17—H17C | 109.00 |
| C12—C11—C16 | 119.23 (18) | H17A—C17—H17B | 109.00 |
| C11—C12—C13 | 120.2 (2) | H17A—C17—H17C | 109.00 |
| C12—C13—C14 | 120.0 (3) | H17B—C17—H17C | 109.00 |
| C13—C14—C15 | 120.6 (3) | ||
| C10—O1—C9—O2 | −179.7 (2) | C3—C4—C5—C6 | −1.8 (4) |
| C10—O1—C9—C8 | 0.43 (19) | C4—C5—C6—C1 | 0.5 (4) |
| C9—O1—C10—N1 | −0.3 (2) | C1—C7—C8—N1 | −2.0 (3) |
| C9—O1—C10—C11 | −179.54 (16) | C1—C7—C8—C9 | 179.55 (19) |
| C17—O3—C2—C1 | 177.88 (19) | N1—C8—C9—O1 | −0.5 (2) |
| C17—O3—C2—C3 | −1.9 (3) | N1—C8—C9—O2 | 179.7 (2) |
| C10—N1—C8—C7 | −178.4 (2) | C7—C8—C9—O1 | 178.32 (17) |
| C10—N1—C8—C9 | 0.3 (2) | C7—C8—C9—O2 | −1.5 (4) |
| C8—N1—C10—O1 | 0.0 (2) | O1—C10—C11—C12 | −2.4 (3) |
| C8—N1—C10—C11 | 179.13 (18) | O1—C10—C11—C16 | 178.04 (17) |
| C6—C1—C2—O3 | 178.68 (18) | N1—C10—C11—C12 | 178.42 (19) |
| C6—C1—C2—C3 | −1.6 (3) | N1—C10—C11—C16 | −1.1 (3) |
| C7—C1—C2—O3 | −3.8 (3) | C10—C11—C12—C13 | 179.2 (2) |
| C7—C1—C2—C3 | 175.91 (19) | C16—C11—C12—C13 | −1.2 (3) |
| C2—C1—C6—C5 | 1.2 (3) | C10—C11—C16—C15 | −179.4 (2) |
| C7—C1—C6—C5 | −176.2 (2) | C12—C11—C16—C15 | 1.1 (3) |
| C2—C1—C7—C8 | −179.85 (19) | C11—C12—C13—C14 | 0.6 (4) |
| C6—C1—C7—C8 | −2.5 (3) | C12—C13—C14—C15 | 0.2 (4) |
| O3—C2—C3—C4 | −180.0 (2) | C13—C14—C15—C16 | −0.4 (4) |
| C1—C2—C3—C4 | 0.3 (3) | C14—C15—C16—C11 | −0.3 (4) |
| C2—C3—C4—C5 | 1.4 (4) |
| Symmetry codes: (i) x, y−1, z; (ii) −x, −y+1, −z+1; (iii) x−1, y, z+1; (iv) −x+1, −y+1, −z; (v) −x+1, −y+1, −z+1; (vi) x, y+1, z; (vii) −x+2, −y, −z; (viii) −x+2, −y+1, −z; (ix) x+1, y, z−1; (x) −x+1, −y, −z. |
| 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···Cg3iv | 0.96 | 2.81 | 3.682 (3) | 151 |
| C17—H17C···Cg2vii | 0.96 | 2.96 | 3.832 (3) | 151 |
| Symmetry codes: (iv) −x+1, −y+1, −z; (vii) −x+2, −y, −z. |
| 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 |
| Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y, −z. |
AMA acknowledges the Chemistry Department, Faculty of Science, King Abdul-Aziz University, for providing the laboratories and facilities.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cannella, R., Clerici, F., Gelmi, M. L., Penso, M. & &Pocar, D. (1996). J. Org. Chem. 61,1854-1856.
Cavelier, F. & Verducci, J. (1995). Tetrahedron Lett. 36, 4425-4428.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Gelmi, M. L., Clerici, F. & Melis, A. (1997). Tetrahedron, 53, 1843-1854.
Gonzalez-Martinez, M. A., Puchades, R., Maquieira, A., Ferrer, I., Marco, M. P. & Barcelo, D. (1999). Anal. Chim. Acta, 386, 201-210.
Gottwald, K. & Seebach, D. (1999). Tetrahedron, 55 , 723-738.
Mesaik, M. A., Rahat, S., Khan, M. K., Ullah, Z., Choudhary, M. I., Murad, S., Ismail, Z. & Atta-ur-Rahman, A. A. (2004). Bioorg. Med. Chem. 12, 2049-2057.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
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).