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In the title compound, C
24H
18ClNO
2, the phenyl ring and the tetralone moiety are approximately orthogonal to the isoxazoline ring. The isoxazoline ring adopts an envelope conformation, while the cyclohexenone ring of the tetralone moiety has an intermediate sofa/half-chair conformation. In this structure, one C—H
N intermolecular and two C—H
O intramolecular hydrogen bonds occur; the H
A distances are 2.60, and 2.35 and 2.57 Å, respectively. The molecules are held together by an intermolecular C—H
N hydrogen bond, forming a one-dimensional chain along the [100] direction.
Supporting information
CCDC reference: 169935
To a well stirred solution of 2-arylidine-1-tetralone (3 mmol) in CHCl3 (10 ml) p-chlorobenzhydroxyiminoyl chloride was added (3 mmol), followed by
3.3 mmol of triethylamine. The reaction was monitored via thin-layer
chromatography until the starting material had disappeared, and was then
quenched with water, extracted with CHCl3, dried with anhydrous MgSO4,
column chromatographed using hexane/ethyl acetate (4:1) and recrystallized
from hexane/ethyl acetate (3:1).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97, PARST (Nardelli, 1983b, 1995) and PLATON (Spek, 1999).
3-(
p-Chlorophenyl)-4-phenyl-4,5-dihydroisoxazole-5-spiro-2'-
1',2',3',4'-tetrahydronaphthalen-1'-one
top
Crystal data top
C24H18ClNO2 | Z = 2 |
Mr = 387.84 | F(000) = 404 |
Triclinic, P1 | Dx = 1.299 Mg m−3 |
a = 9.2559 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.9527 (9) Å | Cell parameters from 2150 reflections |
c = 11.6466 (10) Å | θ = 2.9–25.0° |
α = 62.867 (2)° | µ = 0.21 mm−1 |
β = 71.010 (2)° | T = 293 K |
γ = 78.653 (2)° | Rectangular, colourless |
V = 991.93 (15) Å3 | 0.42 × 0.16 × 0.14 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 2158 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
Detector resolution: 8.33 pixels mm-1 | h = −10→10 |
ω scans | k = −11→13 |
5316 measured reflections | l = −10→13 |
3387 independent reflections | |
Refinement top
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)] = 0.065 | H-atom parameters constrained |
wR(F2) = 0.191 | w = 1/[σ2(Fo2) + (0.0861P)2 + 0.4816P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3387 reflections | Δρmax = 0.38 e Å−3 |
254 parameters | Δρmin = −0.46 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.020 (5) |
Crystal data top
C24H18ClNO2 | γ = 78.653 (2)° |
Mr = 387.84 | V = 991.93 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.2559 (8) Å | Mo Kα radiation |
b = 10.9527 (9) Å | µ = 0.21 mm−1 |
c = 11.6466 (10) Å | T = 293 K |
α = 62.867 (2)° | 0.42 × 0.16 × 0.14 mm |
β = 71.010 (2)° | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 2158 reflections with I > 2σ(I) |
5316 measured reflections | Rint = 0.027 |
3387 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.191 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.38 e Å−3 |
3387 reflections | Δρmin = −0.46 e Å−3 |
254 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.6903 (2) | 0.73628 (14) | 0.03835 (16) | 0.1317 (7) | |
O1 | 0.3169 (2) | 1.2410 (2) | 0.3998 (2) | 0.0503 (6) | |
O2 | 0.3142 (3) | 1.4644 (3) | 0.1147 (2) | 0.0682 (8) | |
N1 | 0.3461 (3) | 1.1339 (3) | 0.3586 (3) | 0.0463 (7) | |
C1 | 0.4198 (3) | 1.3501 (3) | 0.3026 (3) | 0.0415 (7) | |
C2 | 0.4678 (3) | 1.1544 (3) | 0.2614 (3) | 0.0398 (7) | |
C3 | 0.5436 (3) | 1.2848 (3) | 0.2192 (3) | 0.0380 (7) | |
H3 | 0.5529 | 1.3426 | 0.1238 | 0.046* | |
C4 | 0.4717 (4) | 1.4044 (4) | 0.3807 (4) | 0.0638 (10) | |
H4A | 0.5309 | 1.3322 | 0.4365 | 0.077* | |
H4B | 0.5376 | 1.4796 | 0.3184 | 0.077* | |
C5 | 0.3408 (4) | 1.4532 (4) | 0.4663 (4) | 0.0665 (11) | |
H5A | 0.2880 | 1.3742 | 0.5400 | 0.080* | |
H5B | 0.3800 | 1.4981 | 0.5043 | 0.080* | |
C6 | 0.2306 (4) | 1.5484 (4) | 0.3968 (4) | 0.0687 (11) | |
C7 | 0.1357 (6) | 1.6373 (5) | 0.4475 (6) | 0.0998 (17) | |
H7 | 0.1428 | 1.6361 | 0.5258 | 0.120* | |
C8 | 0.0321 (7) | 1.7264 (6) | 0.3841 (8) | 0.121 (2) | |
H8 | −0.0312 | 1.7847 | 0.4202 | 0.145* | |
C9 | 0.0198 (6) | 1.7316 (5) | 0.2672 (7) | 0.115 (2) | |
H9 | −0.0502 | 1.7941 | 0.2240 | 0.138* | |
C10 | 0.1108 (4) | 1.6443 (4) | 0.2149 (5) | 0.0795 (13) | |
H10 | 0.1014 | 1.6463 | 0.1369 | 0.095* | |
C11 | 0.2175 (4) | 1.5523 (3) | 0.2786 (4) | 0.0569 (9) | |
C12 | 0.3167 (3) | 1.4598 (3) | 0.2206 (3) | 0.0458 (8) | |
C13 | 0.5241 (4) | 1.0531 (3) | 0.2050 (3) | 0.0486 (8) | |
C14 | 0.4494 (5) | 0.9323 (4) | 0.2608 (4) | 0.0753 (12) | |
H14 | 0.3632 | 0.9164 | 0.3335 | 0.090* | |
C15 | 0.5023 (6) | 0.8359 (4) | 0.2089 (5) | 0.0936 (15) | |
H15 | 0.4517 | 0.7554 | 0.2465 | 0.112* | |
C16 | 0.6280 (6) | 0.8587 (4) | 0.1030 (5) | 0.0795 (12) | |
C17 | 0.7043 (5) | 0.9766 (5) | 0.0459 (5) | 0.0815 (12) | |
H17 | 0.7907 | 0.9913 | −0.0265 | 0.098* | |
C18 | 0.6512 (4) | 1.0734 (4) | 0.0975 (4) | 0.0682 (10) | |
H18 | 0.7024 | 1.1537 | 0.0589 | 0.082* | |
C19 | 0.7000 (3) | 1.2567 (3) | 0.2436 (3) | 0.0400 (7) | |
C20 | 0.8095 (3) | 1.3540 (3) | 0.1633 (3) | 0.0501 (8) | |
H20 | 0.7869 | 1.4342 | 0.0934 | 0.060* | |
C21 | 0.9513 (4) | 1.3322 (4) | 0.1867 (4) | 0.0672 (10) | |
H21 | 1.0236 | 1.3979 | 0.1326 | 0.081* | |
C22 | 0.9862 (4) | 1.2138 (4) | 0.2894 (4) | 0.0701 (11) | |
H22 | 1.0824 | 1.1987 | 0.3042 | 0.084* | |
C23 | 0.8785 (4) | 1.1183 (4) | 0.3700 (4) | 0.0705 (11) | |
H23 | 0.9014 | 1.0387 | 0.4403 | 0.085* | |
C24 | 0.7363 (4) | 1.1394 (3) | 0.3475 (3) | 0.0554 (9) | |
H24 | 0.6641 | 1.0739 | 0.4030 | 0.066* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.1915 (17) | 0.0886 (9) | 0.1280 (12) | 0.0311 (10) | −0.0373 (11) | −0.0759 (9) |
O1 | 0.0518 (13) | 0.0495 (13) | 0.0433 (12) | −0.0087 (10) | −0.0041 (10) | −0.0181 (10) |
O2 | 0.0668 (16) | 0.0817 (18) | 0.0579 (15) | 0.0166 (13) | −0.0316 (13) | −0.0294 (14) |
N1 | 0.0443 (15) | 0.0444 (14) | 0.0479 (15) | −0.0079 (11) | −0.0112 (13) | −0.0165 (12) |
C1 | 0.0389 (15) | 0.0493 (17) | 0.0408 (16) | −0.0078 (13) | −0.0106 (13) | −0.0208 (14) |
C2 | 0.0359 (15) | 0.0444 (17) | 0.0431 (16) | −0.0053 (13) | −0.0142 (13) | −0.0183 (14) |
C3 | 0.0347 (15) | 0.0419 (16) | 0.0363 (15) | −0.0056 (12) | −0.0116 (12) | −0.0130 (13) |
C4 | 0.055 (2) | 0.087 (3) | 0.074 (2) | −0.0053 (19) | −0.0220 (18) | −0.051 (2) |
C5 | 0.058 (2) | 0.100 (3) | 0.077 (3) | −0.006 (2) | −0.0195 (19) | −0.065 (2) |
C6 | 0.057 (2) | 0.070 (2) | 0.090 (3) | −0.0179 (19) | 0.005 (2) | −0.053 (2) |
C7 | 0.079 (3) | 0.103 (4) | 0.133 (4) | −0.018 (3) | 0.015 (3) | −0.087 (4) |
C8 | 0.087 (4) | 0.085 (4) | 0.169 (6) | −0.013 (3) | 0.038 (4) | −0.082 (4) |
C9 | 0.079 (3) | 0.069 (3) | 0.142 (5) | 0.018 (3) | 0.003 (4) | −0.031 (3) |
C10 | 0.061 (2) | 0.055 (2) | 0.092 (3) | 0.0094 (19) | −0.005 (2) | −0.021 (2) |
C11 | 0.0466 (19) | 0.0490 (19) | 0.069 (2) | −0.0086 (15) | −0.0032 (17) | −0.0263 (18) |
C12 | 0.0437 (17) | 0.0444 (17) | 0.0501 (19) | −0.0051 (14) | −0.0115 (15) | −0.0202 (15) |
C13 | 0.0497 (18) | 0.0474 (18) | 0.0513 (19) | −0.0038 (14) | −0.0162 (15) | −0.0210 (15) |
C14 | 0.088 (3) | 0.061 (2) | 0.074 (3) | −0.024 (2) | 0.001 (2) | −0.034 (2) |
C15 | 0.131 (4) | 0.057 (2) | 0.096 (3) | −0.022 (3) | −0.009 (3) | −0.043 (2) |
C16 | 0.104 (3) | 0.060 (2) | 0.083 (3) | 0.015 (2) | −0.029 (3) | −0.042 (2) |
C17 | 0.075 (3) | 0.088 (3) | 0.082 (3) | 0.000 (2) | −0.002 (2) | −0.051 (3) |
C18 | 0.064 (2) | 0.071 (2) | 0.072 (2) | −0.0125 (19) | −0.0010 (19) | −0.040 (2) |
C19 | 0.0337 (15) | 0.0453 (17) | 0.0395 (16) | −0.0060 (13) | −0.0092 (13) | −0.0155 (14) |
C20 | 0.0417 (17) | 0.0521 (18) | 0.0496 (18) | −0.0108 (15) | −0.0113 (14) | −0.0132 (15) |
C21 | 0.0438 (19) | 0.084 (3) | 0.070 (2) | −0.0222 (18) | −0.0118 (18) | −0.024 (2) |
C22 | 0.0384 (18) | 0.098 (3) | 0.078 (3) | −0.0026 (19) | −0.0254 (18) | −0.035 (2) |
C23 | 0.056 (2) | 0.071 (2) | 0.077 (3) | 0.0044 (19) | −0.038 (2) | −0.016 (2) |
C24 | 0.0482 (18) | 0.054 (2) | 0.055 (2) | −0.0109 (15) | −0.0212 (16) | −0.0079 (16) |
Geometric parameters (Å, º) top
Cl1—C16 | 1.741 (4) | C8—C9 | 1.379 (9) |
O1—N1 | 1.407 (3) | C9—C10 | 1.369 (7) |
O1—C1 | 1.459 (4) | C10—C11 | 1.394 (5) |
O2—C12 | 1.218 (4) | C11—C12 | 1.476 (5) |
N1—C2 | 1.281 (4) | C13—C18 | 1.375 (5) |
C1—C4 | 1.518 (4) | C13—C14 | 1.390 (5) |
C1—C3 | 1.535 (4) | C14—C15 | 1.381 (5) |
C1—C12 | 1.536 (4) | C15—C16 | 1.356 (6) |
C2—C13 | 1.466 (4) | C16—C17 | 1.371 (6) |
C2—C3 | 1.517 (4) | C17—C18 | 1.382 (5) |
C3—C19 | 1.511 (4) | C19—C24 | 1.380 (4) |
C4—C5 | 1.481 (5) | C19—C20 | 1.391 (4) |
C5—C6 | 1.461 (6) | C20—C21 | 1.380 (5) |
C6—C7 | 1.385 (6) | C21—C22 | 1.374 (5) |
C6—C11 | 1.402 (5) | C22—C23 | 1.369 (5) |
C7—C8 | 1.360 (9) | C23—C24 | 1.380 (5) |
| | | |
N1—O1—C1 | 108.8 (2) | C10—C11—C12 | 119.7 (4) |
C2—N1—O1 | 110.0 (2) | C6—C11—C12 | 120.3 (3) |
O1—C1—C4 | 107.3 (3) | O2—C12—C11 | 122.4 (3) |
O1—C1—C3 | 105.2 (2) | O2—C12—C1 | 120.1 (3) |
C4—C1—C3 | 117.2 (2) | C11—C12—C1 | 117.4 (3) |
O1—C1—C12 | 103.5 (2) | C18—C13—C14 | 118.3 (3) |
C4—C1—C12 | 110.1 (3) | C18—C13—C2 | 121.6 (3) |
C3—C1—C12 | 112.3 (2) | C14—C13—C2 | 120.1 (3) |
N1—C2—C13 | 119.7 (3) | C15—C14—C13 | 120.5 (4) |
N1—C2—C3 | 114.0 (3) | C16—C15—C14 | 119.9 (4) |
C13—C2—C3 | 126.3 (3) | C15—C16—C17 | 121.0 (4) |
C19—C3—C2 | 112.8 (2) | C15—C16—Cl1 | 118.8 (4) |
C19—C3—C1 | 116.2 (2) | C17—C16—Cl1 | 120.2 (4) |
C2—C3—C1 | 99.7 (2) | C16—C17—C18 | 119.1 (4) |
C5—C4—C1 | 112.0 (3) | C13—C18—C17 | 121.2 (4) |
C6—C5—C4 | 114.4 (3) | C24—C19—C20 | 118.4 (3) |
C7—C6—C11 | 118.4 (4) | C24—C19—C3 | 122.0 (3) |
C7—C6—C5 | 120.1 (4) | C20—C19—C3 | 119.6 (3) |
C11—C6—C5 | 121.4 (3) | C21—C20—C19 | 120.4 (3) |
C8—C7—C6 | 120.9 (6) | C22—C21—C20 | 120.3 (3) |
C7—C8—C9 | 120.9 (5) | C23—C22—C21 | 119.6 (3) |
C10—C9—C8 | 119.8 (5) | C22—C23—C24 | 120.4 (3) |
C9—C10—C11 | 120.0 (5) | C19—C24—C23 | 120.8 (3) |
C10—C11—C6 | 119.9 (4) | | |
| | | |
C1—O1—N1—C2 | 9.9 (3) | C10—C11—C12—C1 | −173.6 (3) |
N1—O1—C1—C4 | −140.5 (2) | C6—C11—C12—C1 | 6.7 (4) |
N1—O1—C1—C3 | −15.0 (3) | O1—C1—C12—O2 | −96.1 (3) |
N1—O1—C1—C12 | 103.0 (2) | C4—C1—C12—O2 | 149.5 (3) |
O1—N1—C2—C13 | 177.8 (2) | C3—C1—C12—O2 | 16.9 (4) |
O1—N1—C2—C3 | −0.1 (3) | O1—C1—C12—C11 | 80.9 (3) |
N1—C2—C3—C19 | 115.1 (3) | C4—C1—C12—C11 | −33.5 (4) |
C13—C2—C3—C19 | −62.7 (4) | C3—C1—C12—C11 | −166.1 (3) |
N1—C2—C3—C1 | −8.8 (3) | N1—C2—C13—C18 | 177.7 (3) |
C13—C2—C3—C1 | 173.4 (3) | C3—C2—C13—C18 | −4.7 (5) |
O1—C1—C3—C19 | −107.8 (3) | N1—C2—C13—C14 | −2.9 (5) |
C4—C1—C3—C19 | 11.2 (4) | C3—C2—C13—C14 | 174.8 (3) |
C12—C1—C3—C19 | 140.2 (3) | C18—C13—C14—C15 | 0.0 (6) |
O1—C1—C3—C2 | 13.6 (3) | C2—C13—C14—C15 | −179.5 (4) |
C4—C1—C3—C2 | 132.7 (3) | C13—C14—C15—C16 | 0.1 (7) |
C12—C1—C3—C2 | −98.3 (3) | C14—C15—C16—C17 | 0.0 (8) |
O1—C1—C4—C5 | −56.9 (4) | C14—C15—C16—Cl1 | −179.1 (4) |
C3—C1—C4—C5 | −174.8 (3) | C15—C16—C17—C18 | −0.2 (7) |
C12—C1—C4—C5 | 55.1 (4) | Cl1—C16—C17—C18 | 178.9 (3) |
C1—C4—C5—C6 | −50.7 (5) | C14—C13—C18—C17 | −0.2 (6) |
C4—C5—C6—C7 | −157.5 (4) | C2—C13—C18—C17 | 179.3 (4) |
C4—C5—C6—C11 | 22.8 (5) | C16—C17—C18—C13 | 0.3 (7) |
C11—C6—C7—C8 | −0.1 (6) | C2—C3—C19—C24 | −30.8 (4) |
C5—C6—C7—C8 | −179.8 (4) | C1—C3—C19—C24 | 83.4 (4) |
C6—C7—C8—C9 | −0.6 (8) | C2—C3—C19—C20 | 152.1 (3) |
C7—C8—C9—C10 | 1.2 (9) | C1—C3—C19—C20 | −93.6 (3) |
C8—C9—C10—C11 | −1.1 (7) | C24—C19—C20—C21 | 0.8 (5) |
C9—C10—C11—C6 | 0.5 (6) | C3—C19—C20—C21 | 177.9 (3) |
C9—C10—C11—C12 | −179.2 (4) | C19—C20—C21—C22 | 0.2 (6) |
C7—C6—C11—C10 | 0.1 (5) | C20—C21—C22—C23 | −1.0 (6) |
C5—C6—C11—C10 | 179.8 (3) | C21—C22—C23—C24 | 0.8 (7) |
C7—C6—C11—C12 | 179.8 (3) | C20—C19—C24—C23 | −0.9 (5) |
C5—C6—C11—C12 | −0.4 (5) | C3—C19—C24—C23 | −178.0 (3) |
C10—C11—C12—O2 | 3.4 (5) | C22—C23—C24—C19 | 0.1 (6) |
C6—C11—C12—O2 | −176.3 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···O1 | 0.97 | 2.57 | 2.831 (6) | 95 |
C3—H3···O2 | 0.98 | 2.35 | 2.777 (4) | 105 |
C22—H22···N1i | 0.93 | 2.60 | 3.531 (5) | 175 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data |
Chemical formula | C24H18ClNO2 |
Mr | 387.84 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.2559 (8), 10.9527 (9), 11.6466 (10) |
α, β, γ (°) | 62.867 (2), 71.010 (2), 78.653 (2) |
V (Å3) | 991.93 (15) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.42 × 0.16 × 0.14 |
|
Data collection |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5316, 3387, 2158 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.191, 1.03 |
No. of reflections | 3387 |
No. of parameters | 254 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.46 |
Selected geometric parameters (Å, º) topCl1—C16 | 1.741 (4) | O2—C12 | 1.218 (4) |
O1—N1 | 1.407 (3) | N1—C2 | 1.281 (4) |
O1—C1 | 1.459 (4) | | |
| | | |
N1—O1—C1 | 108.8 (2) | N1—C2—C13 | 119.7 (3) |
C2—N1—O1 | 110.0 (2) | N1—C2—C3 | 114.0 (3) |
O1—C1—C4 | 107.3 (3) | O2—C12—C11 | 122.4 (3) |
O1—C1—C3 | 105.2 (2) | O2—C12—C1 | 120.1 (3) |
O1—C1—C12 | 103.5 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···O1 | 0.97 | 2.57 | 2.831 (6) | 95 |
C3—H3···O2 | 0.98 | 2.35 | 2.777 (4) | 105 |
C22—H22···N1i | 0.93 | 2.60 | 3.531 (5) | 175 |
Symmetry code: (i) x+1, y, z. |
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Isoxazoline derivatives have been used in many natural-product syntheses and have also proved to be efficient precursors for many synthetic intermediates, including γ-amino alcohols, β-hydroxy ketones etc. (Kozikowski, 1984; Kanemasa & Tsuge, 1990). Spiro-isoxazoline compounds display interesting biological properties, such as herbicidal, plant-growth regulatory and antitumour activities (Howe & Shelton 1990; De Amici et al., 1990; Smietana et al., 1999). We report here the structure of 3-(p-chlorophenyl)-4-phenyl-4,5-dihydroisoxazole-5-spiro-2'- 1',2',3',4'-tetrahydronaphthalen-1'-one, (I).
The structure of (I) (Fig. 1) consists of an isoxazoline ring (A) connected to a p-chlorophenyl ring (B) at C2, a phenyl ring (C) at C3 and a tetralone moiety [D (cyclohexenone) and E (phenyl)] at C1. Rings A and B are approximately coplanar, forming a dihedral angle of 1.2 (1)°. Phenyl ring C and tetralone ring D are approximately orthogonal to ring A, forming dihedral angles of 77.5 (1) and 88.5 (1)°, respectively. There is a slight folding of rings D and E of the tetralone substituent, which form a dihedral angle of 4.9 (1)° with one another.
The bond lengths O1—N1 and N1═C2 and the angles N1—O1—C1 and O1—N1—C2 in ring A are comparable with the corresponding values of two other structures (Mackay et al., 1994; Pereira et al., 1993). Also, bond lengths Cl1—C16 and C12═O2 are in good agreement with the values found in the literature (Allen et al., 1987). Selected bond lengths and angles are given in Table 1.
The puckering (Cremer & Pople, 1975) and asymmetry parameters (Nardelli, 1983a) calculated for ring D are QT = 0.450 (4) Å, ΔCs(C4) = 0.052 (2) and ΔC2(C1—C4) = 0.060 (2), and for ring A are QT = 0.146 (4) Å and ΔCs(C1) = 0.003 (2), which correspond to an intermediate sofa/half-chair conformation for ring D and an envelope conformation for ring A.
The N atom of ring A is involved in a C—H···N intermolecular hydrogen bond. The O atom of ring A and the carbonyl O atom of ring D are involved in two C—H.·O intramolecular hydrogen bonds (Table 2). The sums of the corresponding van der Waals radii of these hydrogen bonds (Bondi, 1964) are rH + rN = 1.75 Å and rH + rO = 1.72 Å, respectively. The C3—H3···O2 and C5—H5A···O1 intramolecular interactions are a result of the configurations at C3 and C1, respectively, while the intermolecular C22—H22···N1i interaction joins the molecules in chains running along the [100] direction [symmetry code: (i) 1 + x, y, z].