Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803008134/su6021sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803008134/su6021Isup2.hkl |
CCDC reference: 214623
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.049
- wR factor = 0.108
- Data-to-parameter ratio = 13.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
A mixture of 2,6-dichlorobenzonitrile oxide (2 mmol) and 3-(4-chlorobenzylidene)dihydrofuran-2-one in dry chloroform (30 ml) was heated under reflux for 4 d. After evaporation of the solvent, the residue was separated by column chromatography (silica gel, petroleum ether/ethyl acetat e= 8:1) to give the title compound, (I). M.p. 464–465 K; IR (KBr): 1784 (C═O), 1600, 1581 (C═N, C═C) cm−1; 1.92 (1H, m), 2.44 (1H, m), 4.26 (1H, m), 4.51 (1H, m), 5.73 (1H, s), 7.17–7.33 (7H, m). 20 mg of (I) were dissolved in 15 ml chloroform, and colourless single crystals, suitable for X-ray analysis, were obtained by slow evaporation at room temperature over 15 d.
Data collection: SMART (Bruker, 1997); cell refinement: SMART; 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.
Fig. 1. The molecular structure of (I), with displacement ellipsoids at the 30% probability level. | |
Fig. 2. The crystal structure of (I), viewed down the a axis. |
C18H12Cl3NO3 | F(000) = 1616 |
Mr = 396.64 | Dx = 1.509 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.600 (6) Å | Cell parameters from 699 reflections |
b = 20.177 (9) Å | θ = 3.5–23.3° |
c = 14.202 (6) Å | µ = 0.54 mm−1 |
β = 104.768 (8)° | T = 293 K |
V = 3491 (3) Å3 | Plate, colourless |
Z = 8 | 0.20 × 0.10 × 0.06 mm |
Bruker SMART CCD area-detector diffractometer | 3078 independent reflections |
Radiation source: fine-focus sealed tube | 1702 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −14→14 |
Tmin = 0.870, Tmax = 1.000 | k = −24→21 |
8872 measured reflections | l = −11→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.049 | w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.108 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.34 e Å−3 |
3078 reflections | Δρmin = −0.21 e Å−3 |
226 parameters |
C18H12Cl3NO3 | V = 3491 (3) Å3 |
Mr = 396.64 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 12.600 (6) Å | µ = 0.54 mm−1 |
b = 20.177 (9) Å | T = 293 K |
c = 14.202 (6) Å | 0.20 × 0.10 × 0.06 mm |
β = 104.768 (8)° |
Bruker SMART CCD area-detector diffractometer | 3078 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 1702 reflections with I > 2σ(I) |
Tmin = 0.870, Tmax = 1.000 | Rint = 0.051 |
8872 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.34 e Å−3 |
3078 reflections | Δρmin = −0.21 e Å−3 |
226 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 | ||
Cl1 | 0.45260 (11) | 0.81182 (7) | 0.10115 (10) | 0.1227 (6) | |
Cl2 | 0.29602 (8) | 1.06152 (5) | 0.03211 (8) | 0.0728 (3) | |
Cl3 | 0.14847 (11) | 0.72810 (6) | 0.37502 (8) | 0.1041 (5) | |
N1 | 0.2605 (2) | 0.88569 (14) | −0.0668 (2) | 0.0563 (8) | |
O1 | 0.14935 (18) | 0.86562 (11) | −0.10339 (15) | 0.0555 (6) | |
O2 | 0.0619 (2) | 1.01248 (12) | −0.10202 (17) | 0.0648 (7) | |
O3 | −0.06824 (18) | 0.93826 (12) | −0.16235 (16) | 0.0581 (6) | |
C1 | 0.0289 (3) | 0.95672 (19) | −0.1037 (2) | 0.0462 (8) | |
C2 | 0.0836 (2) | 0.89728 (15) | −0.0444 (2) | 0.0419 (8) | |
C3 | −0.0145 (3) | 0.85400 (17) | −0.0456 (2) | 0.0538 (9) | |
H3A | −0.0481 | 0.8658 | 0.0064 | 0.065* | |
H3B | 0.0055 | 0.8075 | −0.0399 | 0.065* | |
C4 | −0.0904 (3) | 0.86942 (18) | −0.1452 (2) | 0.0587 (10) | |
H4A | −0.0742 | 0.8411 | −0.1949 | 0.070* | |
H4B | −0.1667 | 0.8633 | −0.1447 | 0.070* | |
C5 | 0.1672 (2) | 0.91561 (15) | 0.0506 (2) | 0.0414 (8) | |
H5 | 0.1538 | 0.9610 | 0.0694 | 0.050* | |
C6 | 0.2717 (3) | 0.91360 (16) | 0.0158 (2) | 0.0449 (8) | |
C7 | 0.1693 (3) | 0.86894 (16) | 0.1344 (2) | 0.0440 (8) | |
C8 | 0.1894 (3) | 0.80186 (18) | 0.1277 (3) | 0.0649 (11) | |
H8 | 0.2068 | 0.7858 | 0.0721 | 0.078* | |
C9 | 0.1842 (3) | 0.75841 (18) | 0.2008 (3) | 0.0692 (11) | |
H9 | 0.1971 | 0.7134 | 0.1948 | 0.083* | |
C10 | 0.1594 (3) | 0.78275 (19) | 0.2830 (3) | 0.0604 (10) | |
C11 | 0.1409 (3) | 0.84868 (18) | 0.2926 (2) | 0.0524 (9) | |
H11 | 0.1251 | 0.8645 | 0.3490 | 0.063* | |
C12 | 0.1458 (2) | 0.89165 (17) | 0.2187 (2) | 0.0439 (8) | |
H12 | 0.1330 | 0.9366 | 0.2255 | 0.053* | |
C13 | 0.3805 (3) | 0.9388 (2) | 0.0696 (2) | 0.0513 (9) | |
C14 | 0.4688 (3) | 0.8968 (2) | 0.1099 (3) | 0.0713 (12) | |
C15 | 0.5703 (4) | 0.9211 (3) | 0.1568 (3) | 0.0883 (15) | |
H15 | 0.6278 | 0.8921 | 0.1827 | 0.106* | |
C16 | 0.5864 (3) | 0.9879 (3) | 0.1653 (3) | 0.0863 (16) | |
H16 | 0.6553 | 1.0042 | 0.1970 | 0.104* | |
C17 | 0.5026 (4) | 1.0315 (2) | 0.1280 (3) | 0.0737 (12) | |
H17 | 0.5140 | 1.0770 | 0.1341 | 0.088* | |
C18 | 0.4008 (3) | 1.0063 (2) | 0.0810 (2) | 0.0563 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1022 (10) | 0.0931 (10) | 0.1468 (12) | 0.0528 (8) | −0.0158 (8) | −0.0250 (8) |
Cl2 | 0.0707 (7) | 0.0551 (6) | 0.0981 (8) | −0.0038 (5) | 0.0315 (6) | −0.0086 (5) |
Cl3 | 0.1364 (11) | 0.0943 (9) | 0.0910 (8) | 0.0350 (8) | 0.0463 (8) | 0.0486 (7) |
N1 | 0.0512 (18) | 0.066 (2) | 0.0516 (18) | 0.0095 (16) | 0.0124 (15) | −0.0151 (15) |
O1 | 0.0538 (15) | 0.0623 (16) | 0.0485 (14) | 0.0077 (12) | 0.0096 (12) | −0.0180 (12) |
O2 | 0.0679 (17) | 0.0467 (16) | 0.0717 (17) | −0.0028 (14) | 0.0031 (13) | 0.0116 (13) |
O3 | 0.0493 (15) | 0.0626 (17) | 0.0558 (15) | −0.0004 (13) | 0.0014 (12) | 0.0039 (12) |
C1 | 0.047 (2) | 0.052 (2) | 0.042 (2) | 0.0052 (18) | 0.0147 (17) | 0.0012 (17) |
C2 | 0.048 (2) | 0.0401 (19) | 0.0398 (18) | 0.0058 (16) | 0.0154 (16) | −0.0045 (15) |
C3 | 0.065 (2) | 0.046 (2) | 0.052 (2) | −0.0057 (18) | 0.0168 (19) | −0.0027 (17) |
C4 | 0.057 (2) | 0.062 (3) | 0.057 (2) | −0.0092 (19) | 0.0143 (19) | −0.0094 (19) |
C5 | 0.0479 (19) | 0.0379 (19) | 0.0394 (18) | 0.0082 (15) | 0.0128 (15) | −0.0035 (14) |
C6 | 0.047 (2) | 0.045 (2) | 0.044 (2) | 0.0100 (16) | 0.0124 (17) | −0.0049 (16) |
C7 | 0.0452 (19) | 0.046 (2) | 0.0386 (18) | 0.0070 (16) | 0.0075 (15) | −0.0036 (16) |
C8 | 0.096 (3) | 0.052 (2) | 0.048 (2) | 0.027 (2) | 0.019 (2) | 0.0008 (18) |
C9 | 0.103 (3) | 0.042 (2) | 0.060 (3) | 0.025 (2) | 0.017 (2) | 0.0072 (19) |
C10 | 0.061 (2) | 0.066 (3) | 0.053 (2) | 0.015 (2) | 0.0112 (19) | 0.018 (2) |
C11 | 0.051 (2) | 0.065 (3) | 0.043 (2) | 0.0158 (19) | 0.0139 (17) | 0.0040 (18) |
C12 | 0.0416 (19) | 0.046 (2) | 0.0434 (19) | 0.0098 (16) | 0.0087 (16) | −0.0022 (16) |
C13 | 0.044 (2) | 0.071 (3) | 0.0411 (19) | 0.0069 (19) | 0.0153 (17) | −0.0109 (18) |
C14 | 0.055 (3) | 0.098 (3) | 0.058 (2) | 0.017 (2) | 0.009 (2) | −0.019 (2) |
C15 | 0.054 (3) | 0.140 (5) | 0.069 (3) | 0.020 (3) | 0.011 (2) | −0.013 (3) |
C16 | 0.047 (3) | 0.160 (5) | 0.051 (3) | −0.017 (3) | 0.012 (2) | −0.017 (3) |
C17 | 0.064 (3) | 0.104 (4) | 0.060 (3) | −0.025 (3) | 0.027 (2) | −0.021 (2) |
C18 | 0.049 (2) | 0.081 (3) | 0.045 (2) | −0.006 (2) | 0.0217 (18) | −0.0122 (19) |
Cl1—C14 | 1.728 (5) | C6—C13 | 1.479 (4) |
Cl2—C18 | 1.731 (4) | C7—C12 | 1.383 (4) |
Cl3—C10 | 1.742 (4) | C7—C8 | 1.384 (4) |
N1—C6 | 1.276 (4) | C8—C9 | 1.373 (5) |
N1—O1 | 1.423 (3) | C8—H8 | 0.9300 |
O1—C2 | 1.466 (3) | C9—C10 | 1.374 (5) |
O2—C1 | 1.197 (4) | C9—H9 | 0.9300 |
O3—C1 | 1.345 (4) | C10—C11 | 1.363 (5) |
O3—C4 | 1.450 (4) | C11—C12 | 1.374 (4) |
C1—C2 | 1.526 (4) | C11—H11 | 0.9300 |
C2—C3 | 1.511 (4) | C12—H12 | 0.9300 |
C2—C5 | 1.531 (4) | C13—C18 | 1.389 (5) |
C3—C4 | 1.524 (4) | C13—C14 | 1.399 (5) |
C3—H3A | 0.9700 | C14—C15 | 1.373 (5) |
C3—H3B | 0.9700 | C15—C16 | 1.365 (6) |
C4—H4A | 0.9700 | C15—H15 | 0.9300 |
C4—H4B | 0.9700 | C16—C17 | 1.373 (6) |
C5—C7 | 1.513 (4) | C16—H16 | 0.9300 |
C5—C6 | 1.520 (4) | C17—C18 | 1.383 (5) |
C5—H5 | 0.9800 | C17—H17 | 0.9300 |
C6—N1—O1 | 109.2 (2) | C8—C7—C5 | 121.4 (3) |
N1—O1—C2 | 108.3 (2) | C9—C8—C7 | 121.8 (3) |
C1—O3—C4 | 110.2 (3) | C9—C8—H8 | 119.1 |
O2—C1—O3 | 121.9 (3) | C7—C8—H8 | 119.1 |
O2—C1—C2 | 128.4 (3) | C8—C9—C10 | 118.6 (3) |
O3—C1—C2 | 109.6 (3) | C8—C9—H9 | 120.7 |
O1—C2—C3 | 108.8 (3) | C10—C9—H9 | 120.7 |
O1—C2—C1 | 105.6 (2) | C11—C10—C9 | 121.0 (3) |
C3—C2—C1 | 101.2 (3) | C11—C10—Cl3 | 119.7 (3) |
O1—C2—C5 | 104.3 (2) | C9—C10—Cl3 | 119.3 (3) |
C3—C2—C5 | 121.8 (3) | C10—C11—C12 | 119.9 (3) |
C1—C2—C5 | 114.2 (3) | C10—C11—H11 | 120.1 |
C2—C3—C4 | 102.2 (3) | C12—C11—H11 | 120.1 |
C2—C3—H3A | 111.3 | C11—C12—C7 | 120.9 (3) |
C4—C3—H3A | 111.3 | C11—C12—H12 | 119.6 |
C2—C3—H3B | 111.3 | C7—C12—H12 | 119.6 |
C4—C3—H3B | 111.3 | C18—C13—C14 | 116.3 (3) |
H3A—C3—H3B | 109.2 | C18—C13—C6 | 121.0 (3) |
O3—C4—C3 | 104.4 (3) | C14—C13—C6 | 122.6 (4) |
O3—C4—H4A | 110.9 | C15—C14—C13 | 121.9 (4) |
C3—C4—H4A | 110.9 | C15—C14—Cl1 | 117.9 (4) |
O3—C4—H4B | 110.9 | C13—C14—Cl1 | 120.3 (3) |
C3—C4—H4B | 110.9 | C16—C15—C14 | 119.6 (4) |
H4A—C4—H4B | 108.9 | C16—C15—H15 | 120.2 |
C7—C5—C6 | 113.4 (3) | C14—C15—H15 | 120.2 |
C7—C5—C2 | 114.4 (3) | C15—C16—C17 | 121.1 (4) |
C6—C5—C2 | 99.5 (2) | C15—C16—H16 | 119.5 |
C7—C5—H5 | 109.7 | C17—C16—H16 | 119.5 |
C6—C5—H5 | 109.7 | C16—C17—C18 | 118.6 (4) |
C2—C5—H5 | 109.7 | C16—C17—H17 | 120.7 |
N1—C6—C13 | 119.8 (3) | C18—C17—H17 | 120.7 |
N1—C6—C5 | 114.2 (3) | C17—C18—C13 | 122.5 (4) |
C13—C6—C5 | 126.0 (3) | C17—C18—Cl2 | 118.4 (3) |
C12—C7—C8 | 117.8 (3) | C13—C18—Cl2 | 119.1 (3) |
C12—C7—C5 | 120.7 (3) | ||
C6—N1—O1—C2 | 12.6 (3) | C6—C5—C7—C8 | −55.5 (4) |
C4—O3—C1—O2 | −176.5 (3) | C2—C5—C7—C8 | 57.6 (4) |
C4—O3—C1—C2 | 3.2 (3) | C12—C7—C8—C9 | 1.3 (5) |
N1—O1—C2—C3 | −152.1 (2) | C5—C7—C8—C9 | −175.5 (3) |
N1—O1—C2—C1 | 99.9 (3) | C7—C8—C9—C10 | −0.7 (6) |
N1—O1—C2—C5 | −20.7 (3) | C8—C9—C10—C11 | −0.4 (6) |
O2—C1—C2—O1 | −90.8 (4) | C8—C9—C10—Cl3 | 178.1 (3) |
O3—C1—C2—O1 | 89.5 (3) | C9—C10—C11—C12 | 0.8 (6) |
O2—C1—C2—C3 | 155.9 (3) | Cl3—C10—C11—C12 | −177.8 (2) |
O3—C1—C2—C3 | −23.8 (3) | C10—C11—C12—C7 | −0.1 (5) |
O2—C1—C2—C5 | 23.2 (5) | C8—C7—C12—C11 | −0.9 (5) |
O3—C1—C2—C5 | −156.5 (2) | C5—C7—C12—C11 | 175.9 (3) |
O1—C2—C3—C4 | −77.7 (3) | N1—C6—C13—C18 | 110.3 (4) |
C1—C2—C3—C4 | 33.2 (3) | C5—C6—C13—C18 | −71.6 (4) |
C5—C2—C3—C4 | 161.1 (3) | N1—C6—C13—C14 | −68.3 (4) |
C1—O3—C4—C3 | 18.8 (3) | C5—C6—C13—C14 | 109.8 (4) |
C2—C3—C4—O3 | −32.7 (3) | C18—C13—C14—C15 | −0.9 (5) |
O1—C2—C5—C7 | −101.6 (3) | C6—C13—C14—C15 | 177.8 (3) |
C3—C2—C5—C7 | 21.7 (4) | C18—C13—C14—Cl1 | 179.3 (3) |
C1—C2—C5—C7 | 143.7 (3) | C6—C13—C14—Cl1 | −2.0 (5) |
O1—C2—C5—C6 | 19.6 (3) | C13—C14—C15—C16 | 0.3 (6) |
C3—C2—C5—C6 | 142.9 (3) | Cl1—C14—C15—C16 | −179.9 (3) |
C1—C2—C5—C6 | −95.1 (3) | C14—C15—C16—C17 | 0.2 (6) |
O1—N1—C6—C13 | 179.7 (3) | C15—C16—C17—C18 | −0.1 (6) |
O1—N1—C6—C5 | 1.4 (4) | C16—C17—C18—C13 | −0.5 (5) |
C7—C5—C6—N1 | 108.2 (3) | C16—C17—C18—Cl2 | −178.9 (3) |
C2—C5—C6—N1 | −13.7 (4) | C14—C13—C18—C17 | 1.0 (5) |
C7—C5—C6—C13 | −70.0 (4) | C6—C13—C18—C17 | −177.7 (3) |
C2—C5—C6—C13 | 168.1 (3) | C14—C13—C18—Cl2 | 179.3 (2) |
C6—C5—C7—C12 | 127.7 (3) | C6—C13—C18—Cl2 | 0.6 (4) |
C2—C5—C7—C12 | −119.1 (3) |
Experimental details
Crystal data | |
Chemical formula | C18H12Cl3NO3 |
Mr | 396.64 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.600 (6), 20.177 (9), 14.202 (6) |
β (°) | 104.768 (8) |
V (Å3) | 3491 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.54 |
Crystal size (mm) | 0.20 × 0.10 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.870, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8872, 3078, 1702 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.108, 1.01 |
No. of reflections | 3078 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.21 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
Cl3—C10 | 1.742 (4) | O1—C2 | 1.466 (3) |
N1—C6 | 1.276 (4) | O2—C1 | 1.197 (4) |
N1—O1 | 1.423 (3) | O3—C1 | 1.345 (4) |
C6—N1—O1 | 109.2 (2) | O2—C1—O3 | 121.9 (3) |
N1—O1—C2 | 108.3 (2) | O1—C2—C5 | 104.3 (2) |
C1—O3—C4 | 110.2 (3) | ||
C6—N1—O1—C2 | 12.6 (3) | O3—C1—C2—O1 | 89.5 (3) |
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Spiro-compounds represent an important class of naturally occurring substances characterized by highly pronounced biological properties (Kobayashi et al., 1991; James et al., 1991). 1,3-Dipolar cycloaddition reactions are important processes for the construction of spiro-compounds (Caramella & Grunanger, 1984). The molecular structure of the title compound, (I), is illustrated in Fig. 1.
There exists a spiro ring in (I), which consists of an isoxazoline ring and a dihydrofuran-2-one ring. The isoxazoline ring (O1/N1/C6/C5/C2) has an envelope conformation. Atoms O1/N1/C6/C5 form an almost perfect plane [mean deviation from this plane of 0.0053 (3) Å]. Spiro-atom C2 lies 0.3309 (3) Å from this plane and forms the flap of the envelope. The dihedral angle between plane C5/C2/O1 and mean plane O1/N1/C6/C5 is 21.1 (4)°. This is similar to the conformation found for isoxazoline rings in the literaure (Li, Feng & Gu, 2003; Li, Feng, Zhuang & Hu, 2003). The O1—N1, C6—N1 and O1—C2 bond l engths are 1.423 (3), 1.276 (4) and 1.466 (3) Å, respectively, and the angles O1—N1—C6 and C2—O1—N1 are 109.2 (2) and 108.3 (2)°, respectively. These values compare with the values of 1.425 (4), 1.268 (4) and 1.440 (4) Å, and 109.0 (3) and 110.5 (2)° reported in the literature (Li, Feng, Zhuang & Hu, 2003). The torsion angle C6—N1—O1—C2 is 12.6 (3)°. The dihedral angle between plane O1/N1/C6/C5 and the phenyl ring (C7–C12) is 99.2 (4)°, and that between plane O1/N1/C6/C5 and phenyl ring (C13–C18) is 109.9 (4)°. The dihedral angle between phenyl rings C7–C12 and C13–C18 is 95.1 (4)°. The dihydrofuran-2-one ring (C1–C4/O3) has an envelope conformation; atoms C1/C2/O3/C4 lie in a plane, with the mean deviation from this plane being 0.0132 (3) Å. Atom C3 lies 0.5384 (4) Å from this plane and forms the flap of the envelope. The dihedral angle between planes C2/C3/C4 and C2/C1/O3/C4 is 34.4 (4)°. The O2—C1, O3—C4 and O3—C1 bond lengths are 1.197 (4), 1.450 (4) and 1.345 (4) Å, respectively, and bond angles O2—C1—O3, C1—O3—C4 and C1—C2—C3 are 121.9 (3), 110.2 (3) and 101.2 (3)°, respectively. These values compare well with those of 1.197 (2), 1.443 (2) and 1.342 (2) Å, and 121.2 (18), 110.9 (15) and 102.48 (15)° reported in the literature (Guzei et al., 2002).