Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051458/hg2317sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051458/hg2317Isup2.hkl |
CCDC reference: 667433
The title compound was synthesized from syringaldehyde and hippuric acid as reported (Song et al., 2001). A mixture of hippuric acid (2.2 mmol), syringaldehyde (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 it. The resulting mixture was left over night at room temp. The solid thus obtained was filtered, dried and crystallized from ethanol to get title compound (I) in 67% yield. A single-crystal suitable for an X-ray structural analysis was obtained by slowly evaporating from ethanol at room temperature.
All H atoms were initially located in a difference Fourier map. The methyl H atoms were then constrained to an ideal geometry with C—H distances of 0.96 Å and Uiso(H) = 1.5Ueq(C). All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances 0.93 Å and Uiso(H) = 1.2Ueq(C).
The title compound, (I), was prepared as part of our systematic search for organic functional materials with nonlinear optical properties (Sun & Cui, 2007). Oxazolones 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 biosensors coupling, and photosensitive composition devices for proteins (Aaglawe et al., 2003; Grassi et al., 2004; Khan et al., 2006). Moreover, some of them are reported to exhibit promising nonlinear optical properties (Song et al., 2001).
The molecule of compound (I) possesses normal geometric parameters and adopts a Z configuration about the central olefinic bond (Fig. 1). The two phenyl rings and the oxazolone ring are almost coplanar which allows conjugation (Table 1). Also, while O4, O5, O6, C17 and C18 are approximately coplanar with their attached benzene ring, O3,C19 and C20 deviate from their mother benzene ring on the same side (Fig. 1;Table 1). The title compound shows a weak intermolecular hydrogen bond between the C8 and O1 atoms (C8—H8···O1i: C8—H8 = 0.93 Å, H8···O1 = 2.56 Å, C8···O1 = 3.483 (2) Å and C8—H8···O1 = 172 °; symmetry code: (i) 3 - x, 1 - y, 1 - z), which contribute to the crystal structure stabilization.
Similar structures have been observed in the related oxazolone analogues reported by Imhof & Garms (2005), Song et al. (2004), and Vasuki et al. (2001).
For background literature, see: Aaglawe et al. (2003); Grassi et al. (2004); Khan et al. (2006); Song et al. (2001); Sun & Cui (2007). For related structures, see: Imhof & Garms (2005); Song et al. (2004); Vasuki et al. (2001).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radii. |
C20H17NO6 | Z = 2 |
Mr = 367.35 | F(000) = 384 |
Triclinic, P1 | Dx = 1.350 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8400 (13) Å | Cell parameters from 2426 reflections |
b = 10.4431 (15) Å | θ = 2.0–28.2° |
c = 10.9693 (16) Å | µ = 0.10 mm−1 |
α = 111.074 (6)° | T = 273 K |
β = 96.544 (6)° | Block, red |
γ = 102.119 (6)° | 0.15 × 0.12 × 0.10 mm |
V = 903.7 (2) Å3 |
Bruker SMART CCD area-detector diffractometer | 3176 independent reflections |
Radiation source: fine-focus sealed tube | 2244 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.985, Tmax = 0.990 | k = −12→12 |
10391 measured reflections | l = −13→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0571P)2 + 0.1424P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.009 |
3176 reflections | Δρmax = 0.17 e Å−3 |
248 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997) |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.005 (2) |
C20H17NO6 | γ = 102.119 (6)° |
Mr = 367.35 | V = 903.7 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.8400 (13) Å | Mo Kα radiation |
b = 10.4431 (15) Å | µ = 0.10 mm−1 |
c = 10.9693 (16) Å | T = 273 K |
α = 111.074 (6)° | 0.15 × 0.12 × 0.10 mm |
β = 96.544 (6)° |
Bruker SMART CCD area-detector diffractometer | 3176 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2244 reflections with I > 2σ(I) |
Tmin = 0.985, Tmax = 0.990 | Rint = 0.028 |
10391 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.17 e Å−3 |
3176 reflections | Δρmin = −0.16 e Å−3 |
248 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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 | 1.19578 (16) | 0.71134 (16) | 0.39534 (16) | 0.0721 (4) | |
O2 | 1.22759 (14) | 0.50852 (13) | 0.41266 (13) | 0.0552 (4) | |
O3 | 0.2048 (2) | 0.1945 (2) | −0.11379 (17) | 0.0945 (6) | |
O4 | 0.41331 (15) | 0.10522 (14) | 0.14667 (14) | 0.0628 (4) | |
O5 | 0.30933 (16) | 0.51339 (15) | 0.12013 (15) | 0.0665 (4) | |
O6 | 0.21087 (14) | 0.24950 (15) | 0.10383 (13) | 0.0595 (4) | |
N1 | 0.97910 (17) | 0.36389 (15) | 0.32873 (14) | 0.0478 (4) | |
C1 | 1.1388 (2) | 0.5898 (2) | 0.3770 (2) | 0.0535 (5) | |
C2 | 0.9783 (2) | 0.49460 (19) | 0.32069 (18) | 0.0478 (4) | |
C3 | 1.1222 (2) | 0.37709 (19) | 0.37993 (17) | 0.0466 (4) | |
C4 | 1.1841 (2) | 0.2698 (2) | 0.40751 (18) | 0.0478 (4) | |
C5 | 1.0819 (2) | 0.1380 (2) | 0.3802 (2) | 0.0633 (6) | |
H5 | 0.9751 | 0.1192 | 0.3446 | 0.076* | |
C6 | 1.1380 (3) | 0.0351 (2) | 0.4056 (2) | 0.0733 (6) | |
H6 | 1.0691 | −0.0533 | 0.3870 | 0.088* | |
C7 | 1.2958 (3) | 0.0623 (3) | 0.4584 (2) | 0.0708 (6) | |
H7 | 1.3334 | −0.0074 | 0.4759 | 0.085* | |
C8 | 1.3972 (3) | 0.1921 (2) | 0.4852 (2) | 0.0675 (6) | |
H8 | 1.5039 | 0.2102 | 0.5206 | 0.081* | |
C9 | 1.3425 (2) | 0.2959 (2) | 0.4601 (2) | 0.0582 (5) | |
H9 | 1.4123 | 0.3839 | 0.4785 | 0.070* | |
C10 | 0.8562 (2) | 0.5342 (2) | 0.27495 (18) | 0.0501 (5) | |
H10 | 0.8808 | 0.6257 | 0.2760 | 0.060* | |
C11 | 0.6911 (2) | 0.45420 (19) | 0.22406 (17) | 0.0456 (4) | |
C12 | 0.5844 (2) | 0.5246 (2) | 0.19266 (18) | 0.0498 (5) | |
H12 | 0.6204 | 0.6180 | 0.2003 | 0.060* | |
C13 | 0.4248 (2) | 0.4545 (2) | 0.15007 (18) | 0.0492 (5) | |
C14 | 0.3728 (2) | 0.3144 (2) | 0.13583 (17) | 0.0477 (5) | |
C15 | 0.4782 (2) | 0.24279 (19) | 0.16484 (17) | 0.0463 (4) | |
C16 | 0.6370 (2) | 0.31274 (19) | 0.20929 (17) | 0.0471 (4) | |
H16 | 0.7083 | 0.2657 | 0.2295 | 0.057* | |
C17 | 0.3567 (3) | 0.6575 (2) | 0.1335 (2) | 0.0708 (6) | |
H17A | 0.4077 | 0.7177 | 0.2245 | 0.106* | |
H17B | 0.2653 | 0.6860 | 0.1091 | 0.106* | |
H17C | 0.4289 | 0.6661 | 0.0761 | 0.106* | |
C18 | 0.5178 (3) | 0.0298 (2) | 0.1789 (3) | 0.0806 (7) | |
H18A | 0.5953 | 0.0248 | 0.1240 | 0.121* | |
H18B | 0.4585 | −0.0649 | 0.1633 | 0.121* | |
H18C | 0.5699 | 0.0787 | 0.2712 | 0.121* | |
C19 | 0.1360 (3) | 0.2004 (2) | −0.0251 (2) | 0.0656 (6) | |
C20 | −0.0388 (3) | 0.1572 (3) | −0.0365 (3) | 0.0983 (9) | |
H20A | −0.0876 | 0.2090 | −0.0784 | 0.147* | |
H20B | −0.0617 | 0.1782 | 0.0510 | 0.147* | |
H20C | −0.0795 | 0.0568 | −0.0893 | 0.147* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0513 (9) | 0.0497 (9) | 0.1113 (12) | 0.0051 (7) | 0.0100 (8) | 0.0341 (9) |
O2 | 0.0404 (7) | 0.0478 (8) | 0.0725 (9) | 0.0068 (6) | 0.0058 (6) | 0.0228 (7) |
O3 | 0.0773 (12) | 0.1121 (15) | 0.0666 (11) | 0.0024 (10) | 0.0038 (9) | 0.0201 (10) |
O4 | 0.0527 (8) | 0.0467 (8) | 0.0885 (10) | 0.0078 (6) | 0.0092 (7) | 0.0311 (7) |
O5 | 0.0562 (9) | 0.0639 (10) | 0.0866 (10) | 0.0272 (7) | 0.0063 (7) | 0.0343 (8) |
O6 | 0.0398 (7) | 0.0714 (10) | 0.0679 (9) | 0.0109 (6) | 0.0088 (6) | 0.0312 (8) |
N1 | 0.0415 (9) | 0.0440 (9) | 0.0555 (9) | 0.0101 (7) | 0.0086 (7) | 0.0182 (7) |
C1 | 0.0457 (11) | 0.0460 (12) | 0.0691 (13) | 0.0107 (9) | 0.0137 (9) | 0.0234 (10) |
C2 | 0.0435 (10) | 0.0440 (11) | 0.0535 (11) | 0.0100 (8) | 0.0117 (8) | 0.0170 (9) |
C3 | 0.0408 (10) | 0.0441 (11) | 0.0505 (10) | 0.0070 (8) | 0.0102 (8) | 0.0158 (9) |
C4 | 0.0444 (10) | 0.0474 (11) | 0.0492 (10) | 0.0127 (9) | 0.0106 (8) | 0.0159 (9) |
C5 | 0.0484 (12) | 0.0573 (13) | 0.0830 (15) | 0.0108 (10) | 0.0088 (10) | 0.0296 (11) |
C6 | 0.0676 (15) | 0.0547 (14) | 0.1002 (17) | 0.0125 (11) | 0.0155 (13) | 0.0364 (13) |
C7 | 0.0712 (15) | 0.0650 (15) | 0.0851 (16) | 0.0272 (12) | 0.0111 (12) | 0.0363 (13) |
C8 | 0.0564 (12) | 0.0656 (15) | 0.0743 (14) | 0.0208 (11) | −0.0014 (10) | 0.0224 (12) |
C9 | 0.0491 (11) | 0.0518 (12) | 0.0651 (12) | 0.0097 (9) | 0.0032 (9) | 0.0180 (10) |
C10 | 0.0481 (11) | 0.0444 (11) | 0.0571 (11) | 0.0103 (9) | 0.0110 (9) | 0.0206 (9) |
C11 | 0.0461 (10) | 0.0428 (11) | 0.0475 (10) | 0.0129 (8) | 0.0089 (8) | 0.0170 (8) |
C12 | 0.0531 (12) | 0.0436 (11) | 0.0537 (11) | 0.0151 (9) | 0.0089 (9) | 0.0199 (9) |
C13 | 0.0467 (11) | 0.0537 (12) | 0.0526 (11) | 0.0223 (9) | 0.0100 (8) | 0.0225 (9) |
C14 | 0.0395 (10) | 0.0520 (12) | 0.0512 (11) | 0.0119 (9) | 0.0095 (8) | 0.0203 (9) |
C15 | 0.0462 (10) | 0.0414 (11) | 0.0507 (10) | 0.0104 (9) | 0.0097 (8) | 0.0184 (9) |
C16 | 0.0428 (10) | 0.0461 (11) | 0.0554 (11) | 0.0146 (8) | 0.0074 (8) | 0.0229 (9) |
C17 | 0.0811 (16) | 0.0657 (15) | 0.0844 (15) | 0.0400 (12) | 0.0169 (12) | 0.0399 (12) |
C18 | 0.0790 (16) | 0.0514 (14) | 0.119 (2) | 0.0195 (12) | 0.0154 (14) | 0.0435 (14) |
C19 | 0.0554 (13) | 0.0597 (14) | 0.0735 (15) | 0.0134 (11) | 0.0024 (12) | 0.0216 (12) |
C20 | 0.0475 (13) | 0.108 (2) | 0.120 (2) | 0.0167 (13) | −0.0055 (13) | 0.0317 (18) |
O1—C1 | 1.196 (2) | C8—C9 | 1.375 (3) |
O2—C3 | 1.383 (2) | C8—H8 | 0.9300 |
O2—C1 | 1.392 (2) | C9—H9 | 0.9300 |
O3—C19 | 1.195 (3) | C10—C11 | 1.451 (3) |
O4—C15 | 1.362 (2) | C10—H10 | 0.9300 |
O4—C18 | 1.424 (2) | C11—C12 | 1.395 (2) |
O5—C13 | 1.364 (2) | C11—C16 | 1.397 (2) |
O5—C17 | 1.423 (2) | C12—C13 | 1.384 (3) |
O6—C19 | 1.350 (3) | C12—H12 | 0.9300 |
O6—C14 | 1.392 (2) | C13—C14 | 1.383 (3) |
N1—C3 | 1.282 (2) | C14—C15 | 1.388 (2) |
N1—C2 | 1.401 (2) | C15—C16 | 1.378 (2) |
C1—C2 | 1.466 (3) | C16—H16 | 0.9300 |
C2—C10 | 1.343 (3) | C17—H17A | 0.9600 |
C3—C4 | 1.452 (2) | C17—H17B | 0.9600 |
C4—C9 | 1.382 (3) | C17—H17C | 0.9600 |
C4—C5 | 1.386 (3) | C18—H18A | 0.9600 |
C5—C6 | 1.373 (3) | C18—H18B | 0.9600 |
C5—H5 | 0.9300 | C18—H18C | 0.9600 |
C6—C7 | 1.376 (3) | C19—C20 | 1.494 (3) |
C6—H6 | 0.9300 | C20—H20A | 0.9600 |
C7—C8 | 1.368 (3) | C20—H20B | 0.9600 |
C7—H7 | 0.9300 | C20—H20C | 0.9600 |
C3—O2—C1 | 105.38 (14) | C16—C11—C10 | 122.31 (15) |
C15—O4—C18 | 117.16 (15) | C13—C12—C11 | 119.58 (17) |
C13—O5—C17 | 117.50 (16) | C13—C12—H12 | 120.2 |
C19—O6—C14 | 117.78 (15) | C11—C12—H12 | 120.2 |
C3—N1—C2 | 105.86 (15) | O5—C13—C14 | 115.29 (16) |
O1—C1—O2 | 121.92 (17) | O5—C13—C12 | 124.87 (17) |
O1—C1—C2 | 133.03 (18) | C14—C13—C12 | 119.84 (15) |
O2—C1—C2 | 105.04 (16) | C13—C14—C15 | 121.01 (16) |
C10—C2—N1 | 128.66 (17) | C13—C14—O6 | 119.01 (15) |
C10—C2—C1 | 123.40 (17) | C15—C14—O6 | 119.71 (16) |
N1—C2—C1 | 107.90 (15) | O4—C15—C16 | 124.84 (15) |
N1—C3—O2 | 115.79 (15) | O4—C15—C14 | 115.76 (16) |
N1—C3—C4 | 127.05 (17) | C16—C15—C14 | 119.40 (16) |
O2—C3—C4 | 117.16 (15) | C15—C16—C11 | 120.15 (16) |
C9—C4—C5 | 119.23 (18) | C15—C16—H16 | 119.9 |
C9—C4—C3 | 121.59 (17) | C11—C16—H16 | 119.9 |
C5—C4—C3 | 119.19 (17) | O5—C17—H17A | 109.5 |
C6—C5—C4 | 120.1 (2) | O5—C17—H17B | 109.5 |
C6—C5—H5 | 119.9 | H17A—C17—H17B | 109.5 |
C4—C5—H5 | 119.9 | O5—C17—H17C | 109.5 |
C5—C6—C7 | 120.2 (2) | H17A—C17—H17C | 109.5 |
C5—C6—H6 | 119.9 | H17B—C17—H17C | 109.5 |
C7—C6—H6 | 119.9 | O4—C18—H18A | 109.5 |
C8—C7—C6 | 119.8 (2) | O4—C18—H18B | 109.5 |
C8—C7—H7 | 120.1 | H18A—C18—H18B | 109.5 |
C6—C7—H7 | 120.1 | O4—C18—H18C | 109.5 |
C7—C8—C9 | 120.5 (2) | H18A—C18—H18C | 109.5 |
C7—C8—H8 | 119.7 | H18B—C18—H18C | 109.5 |
C9—C8—H8 | 119.7 | O3—C19—O6 | 122.9 (2) |
C8—C9—C4 | 120.1 (2) | O3—C19—C20 | 127.1 (2) |
C8—C9—H9 | 120.0 | O6—C19—C20 | 110.0 (2) |
C4—C9—H9 | 120.0 | C19—C20—H20A | 109.5 |
C2—C10—C11 | 129.06 (17) | C19—C20—H20B | 109.5 |
C2—C10—H10 | 115.5 | H20A—C20—H20B | 109.5 |
C11—C10—H10 | 115.5 | C19—C20—H20C | 109.5 |
C12—C11—C16 | 120.00 (16) | H20A—C20—H20C | 109.5 |
C12—C11—C10 | 117.67 (16) | H20B—C20—H20C | 109.5 |
C3—O2—C1—O1 | 178.48 (18) | C2—C10—C11—C12 | 174.82 (18) |
C3—O2—C1—C2 | −0.84 (18) | C2—C10—C11—C16 | −3.6 (3) |
C3—N1—C2—C10 | −179.47 (19) | C16—C11—C12—C13 | 1.6 (3) |
C3—N1—C2—C1 | −1.48 (19) | C10—C11—C12—C13 | −176.85 (16) |
O1—C1—C2—C10 | 0.3 (4) | C17—O5—C13—C14 | 179.82 (16) |
O2—C1—C2—C10 | 179.56 (17) | C17—O5—C13—C12 | 0.1 (3) |
O1—C1—C2—N1 | −177.8 (2) | C11—C12—C13—O5 | 178.12 (16) |
O2—C1—C2—N1 | 1.44 (19) | C11—C12—C13—C14 | −1.6 (3) |
C2—N1—C3—O2 | 1.0 (2) | O5—C13—C14—C15 | −179.13 (16) |
C2—N1—C3—C4 | −179.38 (17) | C12—C13—C14—C15 | 0.6 (3) |
C1—O2—C3—N1 | −0.1 (2) | O5—C13—C14—O6 | −5.1 (2) |
C1—O2—C3—C4 | −179.73 (15) | C12—C13—C14—O6 | 174.63 (15) |
N1—C3—C4—C9 | 178.29 (18) | C19—O6—C14—C13 | 79.7 (2) |
O2—C3—C4—C9 | −2.1 (3) | C19—O6—C14—C15 | −106.2 (2) |
N1—C3—C4—C5 | −1.6 (3) | C18—O4—C15—C16 | 1.4 (3) |
O2—C3—C4—C5 | 178.04 (17) | C18—O4—C15—C14 | −178.39 (18) |
C9—C4—C5—C6 | 0.2 (3) | C13—C14—C15—O4 | −179.81 (16) |
C3—C4—C5—C6 | −179.96 (19) | O6—C14—C15—O4 | 6.2 (2) |
C4—C5—C6—C7 | 0.1 (3) | C13—C14—C15—C16 | 0.4 (3) |
C5—C6—C7—C8 | −0.3 (4) | O6—C14—C15—C16 | −173.58 (15) |
C6—C7—C8—C9 | 0.2 (3) | O4—C15—C16—C11 | 179.81 (16) |
C7—C8—C9—C4 | 0.1 (3) | C14—C15—C16—C11 | −0.4 (3) |
C5—C4—C9—C8 | −0.3 (3) | C12—C11—C16—C15 | −0.6 (3) |
C3—C4—C9—C8 | 179.89 (18) | C10—C11—C16—C15 | 177.78 (17) |
N1—C2—C10—C11 | 1.5 (3) | C14—O6—C19—O3 | 9.4 (3) |
C1—C2—C10—C11 | −176.21 (17) | C14—O6—C19—C20 | −170.48 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.93 | 2.56 | 3.483 (2) | 172 |
Symmetry code: (i) −x+3, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C20H17NO6 |
Mr | 367.35 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 273 |
a, b, c (Å) | 8.8400 (13), 10.4431 (15), 10.9693 (16) |
α, β, γ (°) | 111.074 (6), 96.544 (6), 102.119 (6) |
V (Å3) | 903.7 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.15 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.985, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10391, 3176, 2244 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.117, 1.02 |
No. of reflections | 3176 |
No. of parameters | 248 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.16 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.93 | 2.56 | 3.483 (2) | 172 |
Symmetry code: (i) −x+3, −y+1, −z+1. |
The title compound, (I), was prepared as part of our systematic search for organic functional materials with nonlinear optical properties (Sun & Cui, 2007). Oxazolones 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 biosensors coupling, and photosensitive composition devices for proteins (Aaglawe et al., 2003; Grassi et al., 2004; Khan et al., 2006). Moreover, some of them are reported to exhibit promising nonlinear optical properties (Song et al., 2001).
The molecule of compound (I) possesses normal geometric parameters and adopts a Z configuration about the central olefinic bond (Fig. 1). The two phenyl rings and the oxazolone ring are almost coplanar which allows conjugation (Table 1). Also, while O4, O5, O6, C17 and C18 are approximately coplanar with their attached benzene ring, O3,C19 and C20 deviate from their mother benzene ring on the same side (Fig. 1;Table 1). The title compound shows a weak intermolecular hydrogen bond between the C8 and O1 atoms (C8—H8···O1i: C8—H8 = 0.93 Å, H8···O1 = 2.56 Å, C8···O1 = 3.483 (2) Å and C8—H8···O1 = 172 °; symmetry code: (i) 3 - x, 1 - y, 1 - z), which contribute to the crystal structure stabilization.
Similar structures have been observed in the related oxazolone analogues reported by Imhof & Garms (2005), Song et al. (2004), and Vasuki et al. (2001).