3-(2,6-Di­chloro­phenyl)-8-ethyl-4-phenyl-1-oxa-6-thia-2,8-di­aza­spiro­[4.4]­non-2-ene-7,9-dione

In the title compound, C₁₉H₁₄Cl₂N₂O₃S, which was synthesized by the intermolecular [3 + 2]-cyclo­addition of 2,6-di­chloro­benzo­nitrile oxide and 5-benzyl­idene-3-ethyl-thia­zolidine-2,4-dione, there is a spiro connection between an isoxazoline ring and a thia­zolidine ring. The thia­zolidine ring is essentially planar, but the isoxazoline ring has a mean deviation from the plane of 0.0177 (3) Å. The dihedral angle between the mean planes of the rings is 88.5 (4)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.052
• wR factor = 0.110
• Data-to-parameter ratio = 13.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Bruker, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

3-(2,6-Dichlorophenyl)-8-ethyl-4-phenyl-1-oxa-6-thia-2,8-diazaspiro[4.4]non- 2-ene-7,9-dione

Crystal data

C19H14Cl2N2O3S	Dx = 1.469 Mg m^−3
Mr = 421.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 864 reflections
a = 10.0339 (9) Å	θ = 2.7–21.2°
b = 12.5618 (12) Å	µ = 0.47 mm^−1
c = 30.220 (3) Å	T = 293 K
V = 3809.1 (7) Å^3	Plate, colorless
Z = 8	0.26 × 0.24 × 0.16 mm
F(000) = 1728

Data collection

Bruker SMART CCD area-detector diffractometer	3335 independent reflections
Radiation source: fine-focus sealed tube	2148 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→11
Tmin = 0.825, Tmax = 0.927	k = −14→14
13516 measured reflections	l = −35→33

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.052	w = 1/[σ^2(Fo^2) + (0.084P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.110	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.36 e Å^−3
3335 reflections	Δρmin = −0.33 e Å^−3
245 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.12407 (10)	0.47626 (8)	0.46069 (3)	0.0582 (3)
Cl1	0.28598 (11)	0.33697 (8)	0.27374 (3)	0.0688 (3)
Cl2	−0.03391 (12)	0.67094 (8)	0.31535 (4)	0.0833 (4)
N1	0.3347 (3)	0.3573 (2)	0.47022 (9)	0.0514 (8)
N2	0.2437 (3)	0.5770 (3)	0.35317 (9)	0.0605 (9)
O1	0.2129 (3)	0.3869 (2)	0.53316 (9)	0.0770 (9)
O2	0.4271 (3)	0.3571 (3)	0.40150 (10)	0.1123 (14)
O3	0.2809 (3)	0.5541 (2)	0.39765 (8)	0.0750 (9)
C1	0.2306 (4)	0.4008 (3)	0.49435 (12)	0.0517 (9)
C2	0.3407 (4)	0.3839 (3)	0.42664 (13)	0.0613 (11)
C3	0.2243 (3)	0.4544 (3)	0.41168 (11)	0.0475 (9)
C4	0.1537 (3)	0.4089 (3)	0.37016 (10)	0.0393 (8)
H4	0.2056	0.3479	0.3596	0.047*
C5	0.1750 (3)	0.5004 (3)	0.33819 (10)	0.0406 (8)
C6	0.4353 (4)	0.2884 (3)	0.49189 (14)	0.0671 (11)
H6A	0.4712	0.2390	0.4703	0.081*
H6B	0.3927	0.2473	0.5151	0.081*
C7	0.5473 (4)	0.3527 (3)	0.51148 (15)	0.0803 (14)
H7A	0.5924	0.3908	0.4884	0.120*
H7B	0.6091	0.3059	0.5260	0.120*
H7C	0.5119	0.4024	0.5326	0.120*
C8	0.0103 (3)	0.3735 (3)	0.37547 (10)	0.0379 (8)
C9	−0.0200 (4)	0.2668 (3)	0.37114 (11)	0.0507 (9)
H9	0.0462	0.2183	0.3636	0.061*
C10	−0.1499 (4)	0.2321 (3)	0.37810 (13)	0.0650 (11)
H10	−0.1704	0.1603	0.3749	0.078*
C11	−0.2473 (4)	0.3023 (3)	0.38958 (12)	0.0561 (10)
H11	−0.3336	0.2782	0.3946	0.067*
C12	−0.2186 (4)	0.4074 (3)	0.39364 (11)	0.0527 (9)
H12	−0.2853	0.4554	0.4013	0.063*
C13	−0.0900 (3)	0.4432 (3)	0.38640 (11)	0.0476 (9)
H13	−0.0712	0.5155	0.3890	0.057*
C14	0.1258 (3)	0.5055 (2)	0.29201 (10)	0.0404 (8)
C15	0.1724 (3)	0.4356 (3)	0.25966 (11)	0.0461 (9)
C16	0.1335 (4)	0.4427 (3)	0.21599 (12)	0.0610 (11)
H16	0.1682	0.3960	0.1951	0.073*
C17	0.0437 (5)	0.5187 (4)	0.20362 (14)	0.0740 (12)
H17	0.0168	0.5232	0.1742	0.089*
C18	−0.0071 (4)	0.5883 (4)	0.23403 (14)	0.0692 (12)
H18	−0.0688	0.6395	0.2254	0.083*
C19	0.0340 (4)	0.5823 (3)	0.27798 (12)	0.0528 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0514 (6)	0.0792 (7)	0.0439 (5)	0.0127 (5)	0.0001 (4)	−0.0091 (5)
Cl1	0.0706 (7)	0.0682 (6)	0.0677 (6)	0.0179 (5)	0.0087 (5)	−0.0122 (5)
Cl2	0.0988 (9)	0.0611 (6)	0.0899 (8)	0.0282 (6)	0.0247 (7)	0.0090 (6)
N1	0.0463 (19)	0.0584 (19)	0.0496 (19)	0.0027 (15)	−0.0077 (15)	−0.0078 (15)
N2	0.071 (2)	0.065 (2)	0.0450 (18)	−0.0225 (18)	0.0013 (17)	−0.0045 (16)
O1	0.090 (2)	0.095 (2)	0.0465 (17)	0.0104 (18)	0.0014 (15)	0.0064 (15)
O2	0.0519 (19)	0.223 (4)	0.0622 (19)	0.047 (2)	0.0023 (16)	−0.019 (2)
O3	0.085 (2)	0.086 (2)	0.0537 (16)	−0.0430 (17)	−0.0141 (15)	−0.0014 (15)
C1	0.057 (3)	0.052 (2)	0.046 (2)	−0.0067 (19)	−0.003 (2)	−0.0066 (18)
C2	0.037 (2)	0.099 (3)	0.048 (2)	0.003 (2)	−0.0052 (19)	−0.017 (2)
C3	0.038 (2)	0.064 (2)	0.0411 (19)	−0.0045 (18)	−0.0005 (16)	−0.0032 (17)
C4	0.037 (2)	0.0444 (19)	0.0368 (18)	0.0020 (15)	0.0000 (15)	−0.0065 (15)
C5	0.0371 (19)	0.0421 (19)	0.0428 (19)	−0.0050 (16)	0.0054 (15)	−0.0047 (16)
C6	0.066 (3)	0.057 (2)	0.078 (3)	0.010 (2)	−0.018 (2)	−0.007 (2)
C7	0.073 (3)	0.074 (3)	0.094 (3)	0.005 (2)	−0.036 (3)	−0.008 (3)
C8	0.038 (2)	0.0426 (19)	0.0330 (17)	−0.0003 (16)	−0.0034 (15)	0.0010 (15)
C9	0.048 (2)	0.046 (2)	0.059 (2)	0.0033 (18)	0.0082 (18)	−0.0027 (18)
C10	0.067 (3)	0.048 (2)	0.080 (3)	−0.017 (2)	0.008 (2)	−0.003 (2)
C11	0.043 (2)	0.070 (3)	0.055 (2)	−0.011 (2)	0.0016 (19)	0.001 (2)
C12	0.040 (2)	0.062 (2)	0.056 (2)	0.0077 (19)	0.0003 (18)	0.0019 (19)
C13	0.048 (2)	0.039 (2)	0.056 (2)	−0.0026 (17)	−0.0036 (18)	0.0019 (17)
C14	0.039 (2)	0.0411 (19)	0.0411 (18)	−0.0093 (16)	0.0046 (16)	0.0017 (15)
C15	0.047 (2)	0.048 (2)	0.043 (2)	−0.0080 (17)	0.0026 (17)	0.0000 (17)
C16	0.078 (3)	0.060 (3)	0.045 (2)	−0.015 (2)	0.005 (2)	−0.0079 (19)
C17	0.088 (3)	0.082 (3)	0.051 (2)	−0.018 (3)	−0.008 (2)	0.011 (2)
C18	0.066 (3)	0.071 (3)	0.071 (3)	0.000 (2)	−0.012 (2)	0.027 (2)
C19	0.053 (2)	0.047 (2)	0.058 (2)	−0.0052 (19)	0.0085 (19)	0.0069 (19)

Geometric parameters (Å, º)

S1—C1	1.754 (4)	C7—H7B	0.960
S1—C3	1.811 (3)	C7—H7C	0.960
Cl1—C15	1.737 (4)	C8—C13	1.374 (4)
Cl2—C19	1.726 (4)	C8—C9	1.381 (4)
N1—C2	1.360 (5)	C9—C10	1.390 (5)
N1—C1	1.387 (4)	C9—H9	0.930
N1—C6	1.481 (4)	C10—C11	1.361 (5)
N2—C5	1.268 (4)	C10—H10	0.930
N2—O3	1.425 (4)	C11—C12	1.357 (5)
O1—C1	1.199 (4)	C11—H11	0.930
O2—C2	1.201 (4)	C12—C13	1.384 (5)
O3—C3	1.440 (4)	C12—H12	0.930
C2—C3	1.534 (5)	C13—H13	0.930
C3—C4	1.550 (4)	C14—C15	1.395 (4)
C4—C8	1.514 (4)	C14—C19	1.399 (5)
C4—C5	1.516 (4)	C15—C16	1.379 (5)
C4—H4	0.980	C16—C17	1.365 (6)
C5—C14	1.482 (4)	C16—H16	0.930
C6—C7	1.505 (5)	C17—C18	1.367 (6)
C6—H6A	0.970	C17—H17	0.930
C6—H6B	0.970	C18—C19	1.393 (5)
C7—H7A	0.960	C18—H18	0.930
C1—S1—C3	93.10 (17)	H7B—C7—H7C	109.5
C2—N1—C1	116.5 (3)	C13—C8—C9	118.7 (3)
C2—N1—C6	122.8 (3)	C13—C8—C4	122.3 (3)
C1—N1—C6	120.7 (3)	C9—C8—C4	119.0 (3)
C5—N2—O3	109.0 (3)	C8—C9—C10	119.8 (3)
N2—O3—C3	110.5 (2)	C8—C9—H9	120.1
O1—C1—N1	124.7 (4)	C10—C9—H9	120.1
O1—C1—S1	123.8 (3)	C11—C10—C9	120.6 (4)
N1—C1—S1	111.5 (3)	C11—C10—H10	119.7
O2—C2—N1	125.1 (4)	C9—C10—H10	119.7
O2—C2—C3	121.7 (4)	C12—C11—C10	120.0 (4)
N1—C2—C3	113.2 (3)	C12—C11—H11	120.0
O3—C3—C2	106.7 (3)	C10—C11—H11	120.0
O3—C3—C4	105.2 (3)	C11—C12—C13	120.0 (3)
C2—C3—C4	112.0 (3)	C11—C12—H12	120.0
O3—C3—S1	109.1 (2)	C13—C12—H12	120.0
C2—C3—S1	105.6 (2)	C8—C13—C12	120.9 (3)
C4—C3—S1	117.7 (2)	C8—C13—H13	119.5
C8—C4—C5	115.1 (3)	C12—C13—H13	119.5
C8—C4—C3	117.2 (3)	C15—C14—C19	116.2 (3)
C5—C4—C3	99.9 (3)	C15—C14—C5	121.4 (3)
C8—C4—H4	108.0	C19—C14—C5	122.4 (3)
C5—C4—H4	108.0	C16—C15—C14	122.4 (3)
C3—C4—H4	108.0	C16—C15—Cl1	117.8 (3)
N2—C5—C14	119.0 (3)	C14—C15—Cl1	119.8 (3)
N2—C5—C4	115.1 (3)	C17—C16—C15	119.6 (4)
C14—C5—C4	125.9 (3)	C17—C16—H16	120.2
N1—C6—C7	111.7 (3)	C15—C16—H16	120.2
N1—C6—H6A	109.3	C16—C17—C18	120.6 (4)
C7—C6—H6A	109.3	C16—C17—H17	119.7
N1—C6—H6B	109.3	C18—C17—H17	119.7
C7—C6—H6B	109.3	C17—C18—C19	119.7 (4)
H6A—C6—H6B	107.9	C17—C18—H18	120.1
C6—C7—H7A	109.5	C19—C18—H18	120.1
C6—C7—H7B	109.5	C18—C19—C14	121.4 (4)
H7A—C7—H7B	109.5	C18—C19—Cl2	118.2 (3)
C6—C7—H7C	109.5	C14—C19—Cl2	120.4 (3)
H7A—C7—H7C	109.5
C5—N2—O3—C3	−2.5 (4)	C3—C4—C5—C14	−178.3 (3)
C2—N1—C1—O1	−178.5 (4)	C2—N1—C6—C7	91.1 (4)
C6—N1—C1—O1	−0.3 (5)	C1—N1—C6—C7	−86.8 (4)
C2—N1—C1—S1	3.2 (4)	C5—C4—C8—C13	−53.7 (4)
C6—N1—C1—S1	−178.7 (3)	C3—C4—C8—C13	63.2 (4)
C3—S1—C1—O1	179.6 (3)	C5—C4—C8—C9	129.2 (3)
C3—S1—C1—N1	−2.0 (3)	C3—C4—C8—C9	−113.8 (3)
C1—N1—C2—O2	176.7 (4)	C13—C8—C9—C10	−0.4 (5)
C6—N1—C2—O2	−1.4 (6)	C4—C8—C9—C10	176.8 (3)
C1—N1—C2—C3	−2.9 (5)	C8—C9—C10—C11	−0.6 (6)
C6—N1—C2—C3	179.1 (3)	C9—C10—C11—C12	1.0 (6)
N2—O3—C3—C2	123.4 (3)	C10—C11—C12—C13	−0.4 (6)
N2—O3—C3—C4	4.3 (4)	C9—C8—C13—C12	1.0 (5)
N2—O3—C3—S1	−122.9 (3)	C4—C8—C13—C12	−176.0 (3)
O2—C2—C3—O3	−62.3 (5)	C11—C12—C13—C8	−0.6 (5)
N1—C2—C3—O3	117.3 (3)	N2—C5—C14—C15	113.2 (4)
O2—C2—C3—C4	52.4 (5)	C4—C5—C14—C15	−65.4 (4)
N1—C2—C3—C4	−128.1 (3)	N2—C5—C14—C19	−64.6 (4)
O2—C2—C3—S1	−178.4 (4)	C4—C5—C14—C19	116.8 (4)
N1—C2—C3—S1	1.2 (4)	C19—C14—C15—C16	1.6 (5)
C1—S1—C3—O3	−114.0 (2)	C5—C14—C15—C16	−176.4 (3)
C1—S1—C3—C2	0.5 (3)	C19—C14—C15—Cl1	−179.7 (2)
C1—S1—C3—C4	126.3 (3)	C5—C14—C15—Cl1	2.4 (4)
O3—C3—C4—C8	−129.1 (3)	C14—C15—C16—C17	−1.6 (6)
C2—C3—C4—C8	115.3 (3)	Cl1—C15—C16—C17	179.6 (3)
S1—C3—C4—C8	−7.4 (4)	C15—C16—C17—C18	0.5 (6)
O3—C3—C4—C5	−4.2 (3)	C16—C17—C18—C19	0.5 (6)
C2—C3—C4—C5	−119.7 (3)	C17—C18—C19—C14	−0.6 (6)
S1—C3—C4—C5	117.6 (3)	C17—C18—C19—Cl2	−179.4 (3)
O3—N2—C5—C14	−179.3 (3)	C15—C14—C19—C18	−0.4 (5)
O3—N2—C5—C4	−0.6 (4)	C5—C14—C19—C18	177.5 (3)
C8—C4—C5—N2	129.5 (3)	C15—C14—C19—Cl2	178.3 (2)
C3—C4—C5—N2	3.1 (4)	C5—C14—C19—Cl2	−3.8 (4)
C8—C4—C5—C14	−51.9 (4)