4-(4-Chloro­phenyl)-3-(2,6-di­chloro­phenyl)-1,7-dioxa-2-aza­spiro­[4.4]­non-2-en-6-one

Li, X.-F.; Feng, Y.-Q.; Xu, M.

doi:10.1107/S1600536803008134

4-(4-Chlorophenyl)-3-(2,6-dichlorophenyl)-1,7-dioxa-2-azaspiro[4.4]non-2-en-6-one

The title compound, C₁₈H₁₂Cl₃NO₃, was synthesized by the intermolecular [3 + 2]-cycloaddition of 2,6-dichlorobenzonitrile oxide and 3-(4-chlorobenzylidene)dihydrofuran-2-one. A spiro junction in the molecule links an isoxazoline ring and a dihydrofuran-2-one ring. Both rings are non-planar, with envelope conformations.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803008134/su6021sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803008134/su6021Isup2.hkl Contains datablock I

CCDC reference: 214623

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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

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No syntax errors found

ADDSYM reports no extra symmetry

Comment top

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).

Experimental top

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.

Computing details top

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.

Figures top

	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.

4-[(2-Chloro-phenyl)-hydroxyimino-methyl] −1,5-dimethyl-2-phenyl-pyrazolidin-3-one top

Crystal data top

C₁₈H₁₂Cl₃NO₃	F(000) = 1616
M_r = 396.64	D_x = 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

Data collection top

Bruker SMART CCD area-detector diffractometer	3078 independent reflections
Radiation source: fine-focus sealed tube	1702 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −14→14
T_min = 0.870, T_max = 1.000	k = −24→21
8872 measured reflections	l = −11→16

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.049	w = 1/[σ²(F_o²) + (0.084P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.108	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.34 e Å⁻³
3078 reflections	Δρ_min = −0.21 e Å⁻³
226 parameters

Crystal data top

C₁₈H₁₂Cl₃NO₃	V = 3491 (3) Å³
M_r = 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)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3078 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	1702 reflections with I > 2σ(I)
T_min = 0.870, T_max = 1.000	R_int = 0.051
8872 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.01	Δρ_max = 0.34 e Å⁻³
3078 reflections	Δρ_min = −0.21 e Å⁻³
226 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	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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
M_r	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)
T_min, T_max	0.870, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8872, 3078, 1702
R_int	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
Δρ_max, Δρ_min (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.

Selected geometric parameters (Å, º) top

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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		CIF
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4-(4-Chloro­phenyl)-3-(2,6-di­chloro­phenyl)-1,7-dioxa-2-aza­spiro­[4.4]­non-2-en-6-one

Supporting information

Key indicators

checkCIF results

4-(4-Chlorophenyl)-3-(2,6-dichlorophenyl)-1,7-dioxa-2-azaspiro[4.4]non-2-en-6-one