3-(2,4-Dichloro­phen­yl)-2-oxo-1-oxa­spiro­[4.5]dec-3-en-4-yl 4-chloro­benzoate

Zhou, Y.; Cheng, J.-L.; Zhu, G.-N.; Zhao, J.-H.

doi:10.1107/S1600536809044109

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o2992

doi:10.1107/S1600536809044109

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3-(2,4-Dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl 4-chlorobenzoate

Yong Zhou,^a Jing-Li Cheng,^a Guo-Nian Zhu ^a and Jin-Hao Zhao ^a ^*

^aCollege of Agriculture and Biotechnology, Zhejiang University, Hangzhou 310029, People's Republic of China
^*Correspondence e-mail: jinhaozhao@zju.edu.cn

(Received 15 October 2009; accepted 23 October 2009; online 4 November 2009)

In the title spirodiclofen derivative, C₂₂H₁₇Cl₃O₄, the cyclohexane ring adopts a chair conformation [four C atoms are planar with a mean deviation of 0.018 Å and the two C atoms at the flap positions deviate by 0.613 (4) and −0.668 (5) Å from the plane]. The dihedral angles between the furan ring and the two benzene rings are 55.78 (3) and 49.92 (3)°. Weak intermolecular C—H⋯Cl interactions are observed in the crystal structure.

Related literature

For the chemistry of tetronic acid, the central unit of the title compound, see: Fischer et al. (1993 ); Benson et al. (2000 ). For the pesticides Spirodiclofen, Spiromesifen and Spirotetramate, see: BAYER Aktiengesellschaft (1995 ). For the synthesis and structure of the intermediate compound for the preparation of spirodiclofen, see: Zhao et al. (2009 ). For the extinction correction, see: Larson (1970 ).

Experimental

Crystal data

C₂₂H₁₇Cl₃O₄
M_r = 451.73
Monoclinic, P 2₁ /n
a = 14.7979 (8) Å
b = 10.3483 (5) Å
c = 15.0702 (8) Å
β = 115.1875 (12)°
V = 2088.33 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 296 K
0.46 × 0.32 × 0.28 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.800, T_max = 0.878
19403 measured reflections
4756 independent reflections
3289 reflections with F² > 2σ(F²)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.131
S = 1.00
4756 reflections
263 parameters
All H-atom parameters refined
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H52⋯Cl1ⁱ	0.97	2.79	3.726 (3)	162
C16—H16⋯Cl3ⁱⁱ	0.93	2.82	3.595 (3)	141
Symmetry codes: (i) -x+1, -y, -z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SIR97 (Altomare et al., 1993 ); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996 ); molecular graphics: CRYSTALS; software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044109/si2216sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809044109/si2216Isup2.hkl

checkCIF report

Comment top

The chemistry of tetronic acid compounds has being receiving increasing attention in recent years (Fischer et al.,1993; Benson et al., 2000). Bayer company have developed three tetronic acids pesticide-Spirodiclofen, Spiromesifen and Spirotetramat. 4-hydroxyl-3-(2,4-dichlorophenyl)-1- oxaspiro[4,5]dec-3-en-2-one (Zhao et al., 2009) is the key intermediate in preparing highly efficient acaricide-Spirodiclofen (BAYER et al.,1995). We have been involved in the synthesis and potential bioactivity of substituted 4-hydroxyl-3-(2,4-dichlorophenyl) -1-oxaspiro[4,5]dec-3-en-2-one. In order to find new compounds which have good bioactivity, we have isolated the product, (I), of the condensation reaction of 4-chlorobenzoyl chloride and 4-hydroxyl-3- (2,4-dichlorophenyl)-1-oxaspiro[4,5]dec-3-en-2-one as colorless crystals suitable for X-ray analysis. The molecular structure of (I) is shown in Fig. 1. The molecule contains three six membered rings and one five membered rings. The dihedral angles between the ring (C11—C16) and ring (C17—C22), ring (C11—C16) and furan ring, ring (C17—C22) and furan ring, are 67.84 (3), 55.78 (3), and 49.92 (3) °, respectively. The cyclohexane ring displays chair conformation with C1 and C7 atoms at the flap position 0.613 (4) and -0.668 (5) Å out of the mean plane formed by the other four atoms. As expected, C2—C3, C4—O1 and C10—O4 are typically double bonds with bond distances of 1.319 (3), 1.199 (3) and 1.190 (3) Å. The bond distance of C3—C4 is 1.487 (3) Å, suggesting that carbonyl group on C7 has formed a conjugate system with double bond on C2 and C3. It is worth notice that in the title compound there exist two weak intermolecular C—H···Cl contacts (Table 1).

Related literature top

For the chemistry of tetronic acid, the central unit of the title compound, see: Fischer et al. (1993); Benson et al. (2000). For the pesticides Spirodiclofen, Spiromesifen and Spirotetramate, see: BAYER Aktiengesellschaft (1995). For the synthesis and structure of the intermediate compound for the preparation of spirodiclofen, see: Zhao et al. (2009). For the extinction correction, see: Larson (1970).

Experimental top

4-hydroxyl-3-(2,4-dichlorophenyl)-1-oxaspiro[4,5]dec-3-en-2-one (3.12 g, 10 mmol), 4-dimethylaminopyridine (0.58 g, 1eq.), triethylamine (1.31 g, 1.3eq.) and chloroform (100 ml) were added to a 250 ml round flask. Then the mixture was stirred and cooled to 273–278 K. Within 30 min 4-chlorobenzoyl chloride (1.5eq.) was added dropwise to the solution. The mixture was stirred at room temperature for 3 h and then 1% aqueous HCl was added. The organic layer was washed to neutral with water and dried over Na₂SO₄. After filtered and concentrated, the organic residue was purified by silica gel column chromatography, eluted with ethyl acetate-petroleum(1:30,v/v) to give a white solid (yield 85%, 3.96 g), which was then recrystallized from ethyl acetate/ethanol (1:1,v/v) to give colourless blocks.

The 1H NMR, EI-MS data testified the title compound's structure. 1H-NMR (500MHz, CDCl3, δ ppm):7.969-7.942 (2H, m, -CO-Ph-H4), 7.492-7.465 (2H, m, -CO-Ph-H4), 7.455-7.301 (3H, m, Cl2-Ph-H3), 1.876-1.802 (10H, m, cyclohexane-H10); EI-MS (70eV, m/z) (relative intensity %): 452 (M+2, 5), 450 (M+, 5),141 (33) ,139 (100). So we are sure that our chemical formula of the compound is correctly presented.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: CRYSTALS (Watkin et al., 1996); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Molecular packing arrangement in the unit cell.

3-(2,4-Dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl 4-chlorobenzoate top

Crystal data top

C₂₂H₁₇Cl₃O₄	F(000) = 928.00
M_r = 451.73	D_x = 1.437 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 13096 reflections
a = 14.7979 (8) Å	θ = 3.0–27.4°
b = 10.3483 (5) Å	µ = 0.46 mm⁻¹
c = 15.0702 (8) Å	T = 296 K
β = 115.1875 (12)°	Chunk, colorless
V = 2088.33 (19) Å³	0.46 × 0.32 × 0.28 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	3289 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.029
ω scans	θ_max = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −19→19
T_min = 0.800, T_max = 0.878	k = −13→12
19403 measured reflections	l = −19→19
4756 independent reflections

Refinement top

Refinement on F²	w = 1/[0.0005F_o² + 3σ(F_o²)]/(4F_o²)
R[F² > 2σ(F²)] = 0.050	(Δ/σ)_max < 0.001
wR(F²) = 0.131	Δρ_max = 0.54 e Å⁻³
S = 1.00	Δρ_min = −0.43 e Å⁻³
4756 reflections	Extinction correction: Larson (1970), equation 22
263 parameters	Extinction coefficient: 127 (22)
All H-atom parameters refined

Crystal data top

C₂₂H₁₇Cl₃O₄	V = 2088.33 (19) Å³
M_r = 451.73	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.7979 (8) Å	µ = 0.46 mm⁻¹
b = 10.3483 (5) Å	T = 296 K
c = 15.0702 (8) Å	0.46 × 0.32 × 0.28 mm
β = 115.1875 (12)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4756 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3289 reflections with F² > 2σ(F²)
T_min = 0.800, T_max = 0.878	R_int = 0.029
19403 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	263 parameters
wR(F²) = 0.131	All H-atom parameters refined
S = 1.00	Δρ_max = 0.54 e Å⁻³
4756 reflections	Δρ_min = −0.43 e Å⁻³

Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.59797 (8)	−0.25919 (9)	0.12627 (8)	0.0964 (3)
Cl2	0.43688 (6)	0.27225 (6)	0.35188 (6)	0.0706 (2)
Cl3	0.74849 (6)	0.44566 (10)	0.67014 (5)	0.0783 (2)
O1	0.41594 (14)	0.74637 (17)	0.27583 (14)	0.0635 (6)
O2	0.32741 (12)	0.64354 (18)	0.13360 (12)	0.0526 (5)
O3	0.43940 (12)	0.33403 (16)	0.14982 (12)	0.0499 (5)
O4	0.60304 (16)	0.3775 (2)	0.2079 (2)	0.0823 (8)
C1	0.32759 (19)	0.5153 (2)	0.09125 (19)	0.0475 (7)
C2	0.41627 (18)	0.4558 (2)	0.17081 (19)	0.0426 (7)
C3	0.45501 (19)	0.5243 (2)	0.25228 (19)	0.0441 (7)
C4	0.4012 (2)	0.6500 (2)	0.2275 (2)	0.0495 (8)
C5	0.3374 (2)	0.5343 (2)	−0.00451 (19)	0.0545 (8)
C6	0.2448 (2)	0.5961 (3)	−0.0843 (2)	0.0693 (10)
C7	0.1506 (2)	0.5212 (3)	−0.0994 (2)	0.0712 (10)
C8	0.1395 (2)	0.5091 (3)	−0.0036 (2)	0.0653 (9)
C9	0.23153 (18)	0.4468 (2)	0.0752 (2)	0.0523 (8)
C10	0.5376 (2)	0.3002 (3)	0.1748 (2)	0.0548 (9)
C11	0.54804 (19)	0.1611 (2)	0.15495 (19)	0.0452 (7)
C12	0.6420 (2)	0.1213 (2)	0.1683 (2)	0.0553 (8)
C13	0.6566 (2)	−0.0088 (3)	0.1565 (2)	0.0628 (10)
C14	0.5783 (2)	−0.0928 (2)	0.1331 (2)	0.0552 (8)
C15	0.4847 (2)	−0.0556 (2)	0.1182 (2)	0.0620 (9)
C16	0.4699 (2)	0.0755 (2)	0.1285 (2)	0.0586 (9)
C17	0.53097 (19)	0.5005 (2)	0.35283 (19)	0.0454 (7)
C18	0.52788 (19)	0.3912 (2)	0.4051 (2)	0.0482 (8)
C19	0.5946 (2)	0.3713 (2)	0.5033 (2)	0.0528 (8)
C20	0.6659 (2)	0.4649 (2)	0.5479 (2)	0.0530 (8)
C21	0.6719 (2)	0.5728 (3)	0.4985 (2)	0.0620 (9)
C22	0.6042 (2)	0.5900 (3)	0.4017 (2)	0.0620 (9)
H12	0.6941	0.1801	0.1847	0.066*
H13	0.7188	−0.0386	0.1644	0.075*
H15	0.4330	−0.1150	0.1019	0.074*
H16	0.4067	0.1052	0.1174	0.070*
H19	0.5908	0.2979	0.5372	0.063*
H21	0.7210	0.6344	0.5297	0.074*
H22	0.6084	0.6641	0.3687	0.074*
H51	0.3944	0.5896	0.0079	0.065*
H52	0.3481	0.4507	−0.0276	0.065*
H61	0.2386	0.6841	−0.0654	0.083*
H62	0.2521	0.5969	−0.1454	0.083*
H71	0.1544	0.4355	−0.1236	0.085*
H72	0.0929	0.5662	−0.1472	0.085*
H81	0.0816	0.4562	−0.0146	0.078*
H82	0.1306	0.5944	0.0181	0.078*
H91	0.2245	0.4475	0.1363	0.063*
H92	0.2356	0.3583	0.0561	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1031 (7)	0.0598 (5)	0.1127 (7)	0.0265 (5)	0.0329 (6)	−0.0117 (5)
Cl2	0.0826 (5)	0.0506 (4)	0.0693 (5)	−0.0178 (4)	0.0235 (4)	0.0017 (3)
Cl3	0.0571 (4)	0.1195 (8)	0.0503 (4)	0.0126 (5)	0.0151 (3)	0.0049 (4)
O1	0.0807 (14)	0.0348 (11)	0.0636 (12)	0.0022 (9)	0.0196 (10)	−0.0103 (9)
O2	0.0553 (11)	0.0493 (11)	0.0461 (10)	0.0078 (9)	0.0148 (9)	−0.0039 (9)
O3	0.0434 (10)	0.0383 (10)	0.0612 (11)	0.0034 (8)	0.0158 (8)	−0.0091 (8)
O4	0.0564 (12)	0.0581 (14)	0.138 (2)	−0.0125 (11)	0.0469 (13)	−0.0256 (14)
C1	0.0482 (15)	0.0472 (16)	0.0453 (15)	0.0039 (12)	0.0182 (12)	−0.0063 (13)
C2	0.0475 (14)	0.0247 (13)	0.0544 (16)	0.0009 (11)	0.0206 (13)	−0.0045 (12)
C3	0.0459 (14)	0.0333 (14)	0.0511 (15)	−0.0006 (11)	0.0187 (12)	0.0004 (12)
C4	0.0531 (16)	0.0442 (17)	0.0501 (16)	−0.0031 (13)	0.0208 (14)	−0.0017 (14)
C5	0.0606 (17)	0.0535 (18)	0.0522 (16)	0.0033 (14)	0.0268 (14)	−0.0028 (14)
C6	0.075 (2)	0.081 (2)	0.0465 (16)	0.0048 (18)	0.0204 (15)	0.0007 (16)
C7	0.073 (2)	0.061 (2)	0.0576 (19)	0.0062 (17)	0.0067 (17)	−0.0070 (16)
C8	0.0466 (16)	0.066 (2)	0.075 (2)	0.0016 (14)	0.0172 (15)	−0.0164 (17)
C9	0.0508 (16)	0.0480 (17)	0.0576 (16)	−0.0013 (13)	0.0225 (14)	−0.0034 (14)
C10	0.0412 (15)	0.072 (2)	0.0535 (17)	−0.0007 (15)	0.0229 (13)	−0.0034 (15)
C11	0.0472 (15)	0.0394 (15)	0.0482 (15)	0.0087 (12)	0.0196 (13)	0.0017 (12)
C12	0.0523 (16)	0.0440 (17)	0.0713 (19)	0.0035 (14)	0.0279 (15)	−0.0033 (15)
C13	0.0522 (17)	0.074 (2)	0.0634 (19)	0.0174 (17)	0.0254 (15)	0.0025 (17)
C14	0.071 (2)	0.0293 (14)	0.0596 (18)	0.0143 (14)	0.0227 (16)	−0.0001 (13)
C15	0.0619 (19)	0.0420 (17)	0.077 (2)	0.0028 (15)	0.0241 (16)	−0.0074 (15)
C16	0.0395 (15)	0.072 (2)	0.0635 (18)	0.0048 (15)	0.0213 (14)	−0.0003 (16)
C17	0.0463 (15)	0.0402 (15)	0.0479 (15)	0.0015 (12)	0.0184 (13)	0.0011 (13)
C18	0.0489 (15)	0.0411 (16)	0.0537 (16)	0.0019 (12)	0.0209 (13)	−0.0061 (13)
C19	0.0581 (16)	0.0458 (17)	0.0562 (17)	0.0120 (14)	0.0259 (14)	0.0052 (14)
C20	0.0487 (16)	0.0595 (19)	0.0495 (16)	0.0098 (14)	0.0197 (13)	0.0009 (15)
C21	0.0494 (17)	0.068 (2)	0.0589 (18)	−0.0103 (15)	0.0138 (15)	−0.0052 (16)
C22	0.0545 (17)	0.074 (2)	0.0522 (17)	−0.0163 (15)	0.0176 (15)	−0.0006 (16)

Geometric parameters (Å, º) top

Cl1—C14	1.757 (2)	C15—C16	1.393 (4)
Cl2—C18	1.747 (2)	C17—C18	1.390 (3)
Cl3—C20	1.736 (2)	C17—C22	1.377 (3)
O1—C4	1.199 (3)	C18—C19	1.402 (3)
O2—C1	1.473 (3)	C19—C20	1.378 (3)
O2—C4	1.373 (2)	C20—C21	1.366 (4)
O3—C2	1.377 (3)	C21—C22	1.386 (3)
O3—C10	1.382 (3)	C5—H51	0.970
O4—C10	1.190 (3)	C5—H52	0.970
C1—C2	1.483 (3)	C6—H61	0.970
C1—C5	1.523 (4)	C6—H62	0.970
C1—C9	1.513 (3)	C7—H71	0.970
C2—C3	1.319 (3)	C7—H72	0.970
C3—C4	1.487 (3)	C8—H81	0.970
C3—C17	1.473 (3)	C8—H82	0.970
C5—C6	1.527 (3)	C9—H91	0.970
C6—C7	1.524 (4)	C9—H92	0.970
C7—C8	1.526 (5)	C12—H12	0.930
C8—C9	1.517 (3)	C13—H13	0.930
C10—C11	1.492 (4)	C15—H15	0.930
C11—C12	1.380 (4)	C16—H16	0.930
C11—C16	1.374 (3)	C19—H19	0.930
C12—C13	1.386 (4)	C21—H21	0.930
C13—C14	1.369 (4)	C22—H22	0.930
C14—C15	1.361 (4)

C1—O2—C4	110.07 (18)	Cl3—C20—C21	119.5 (2)
C2—O3—C10	120.29 (19)	C19—C20—C21	121.6 (2)
O2—C1—C2	100.83 (17)	C20—C21—C22	119.5 (2)
O2—C1—C5	108.2 (2)	C17—C22—C21	121.9 (2)
O2—C1—C9	108.5 (2)	C1—C5—H51	108.7
C2—C1—C5	114.3 (2)	C1—C5—H52	108.7
C2—C1—C9	112.5 (2)	C6—C5—H51	108.7
C5—C1—C9	111.7 (2)	C6—C5—H52	108.7
O3—C2—C1	114.5 (2)	H51—C5—H52	109.5
O3—C2—C3	130.8 (2)	C5—C6—H61	109.0
C1—C2—C3	114.5 (2)	C5—C6—H62	109.0
C2—C3—C4	105.2 (2)	C7—C6—H61	109.0
C2—C3—C17	135.0 (2)	C7—C6—H62	109.0
C4—C3—C17	119.8 (2)	H61—C6—H62	109.5
O1—C4—O2	121.7 (2)	C6—C7—H71	109.1
O1—C4—C3	129.5 (2)	C6—C7—H72	109.1
O2—C4—C3	108.8 (2)	C8—C7—H71	109.1
C1—C5—C6	112.7 (2)	C8—C7—H72	109.1
C5—C6—C7	111.2 (2)	H71—C7—H72	109.5
C6—C7—C8	111.2 (2)	C7—C8—H81	109.2
C7—C8—C9	110.7 (2)	C7—C8—H82	109.2
C1—C9—C8	113.3 (2)	C9—C8—H81	109.2
O3—C10—O4	121.2 (2)	C9—C8—H82	109.2
O3—C10—C11	112.1 (2)	H81—C8—H82	109.5
O4—C10—C11	126.7 (2)	C1—C9—H91	108.5
C10—C11—C12	116.3 (2)	C1—C9—H92	108.5
C10—C11—C16	122.3 (2)	C8—C9—H91	108.5
C12—C11—C16	121.4 (2)	C8—C9—H92	108.5
C11—C12—C13	118.2 (2)	H91—C9—H92	109.5
C12—C13—C14	119.3 (3)	C11—C12—H12	120.9
Cl1—C14—C13	119.7 (2)	C13—C12—H12	120.9
Cl1—C14—C15	116.7 (2)	C12—C13—H13	120.4
C13—C14—C15	123.6 (2)	C14—C13—H13	120.4
C14—C15—C16	117.0 (2)	C14—C15—H15	121.5
C11—C16—C15	120.5 (2)	C16—C15—H15	121.5
C3—C17—C18	121.6 (2)	C11—C16—H16	119.8
C3—C17—C22	121.3 (2)	C15—C16—H16	119.8
C18—C17—C22	116.9 (2)	C18—C19—H19	121.3
Cl2—C18—C17	121.20 (17)	C20—C19—H19	121.3
Cl2—C18—C19	116.1 (2)	C20—C21—H21	120.2
C17—C18—C19	122.6 (2)	C22—C21—H21	120.2
C18—C19—C20	117.4 (2)	C17—C22—H22	119.1
Cl3—C20—C19	119.0 (2)	C21—C22—H22	119.1

C1—O2—C4—O1	178.8 (3)	C17—C3—C4—O2	−173.4 (2)
C1—O2—C4—C3	0.2 (3)	C1—C5—C6—C7	−53.4 (3)
C4—O2—C1—C2	−4.5 (3)	C5—C6—C7—C8	55.8 (3)
C4—O2—C1—C5	−124.7 (2)	C6—C7—C8—C9	−56.1 (3)
C4—O2—C1—C9	113.9 (2)	C7—C8—C9—C1	54.5 (3)
C2—O3—C10—O4	−5.7 (4)	O3—C10—C11—C12	173.7 (2)
C2—O3—C10—C11	174.4 (2)	O3—C10—C11—C16	−8.8 (4)
C10—O3—C2—C1	137.8 (2)	O4—C10—C11—C12	−6.2 (5)
C10—O3—C2—C3	−48.0 (4)	O4—C10—C11—C16	171.4 (3)
O2—C1—C2—O3	−176.7 (2)	C10—C11—C12—C13	176.1 (2)
O2—C1—C2—C3	8.1 (3)	C10—C11—C16—C15	−174.9 (2)
O2—C1—C5—C6	−68.4 (2)	C12—C11—C16—C15	2.6 (4)
O2—C1—C9—C8	67.4 (3)	C16—C11—C12—C13	−1.5 (4)
C2—C1—C5—C6	−179.8 (2)	C11—C12—C13—C14	−0.5 (4)
C5—C1—C2—O3	−60.9 (3)	C12—C13—C14—Cl1	−175.6 (2)
C5—C1—C2—C3	124.0 (2)	C12—C13—C14—C15	1.5 (4)
C2—C1—C9—C8	178.0 (2)	Cl1—C14—C15—C16	176.8 (2)
C9—C1—C2—O3	67.9 (3)	C13—C14—C15—C16	−0.4 (4)
C9—C1—C2—C3	−107.2 (3)	C14—C15—C16—C11	−1.6 (4)
C5—C1—C9—C8	−51.8 (3)	C3—C17—C18—Cl2	3.1 (4)
C9—C1—C5—C6	51.0 (3)	C3—C17—C18—C19	−174.9 (3)
O3—C2—C3—C4	177.6 (3)	C3—C17—C22—C21	175.5 (3)
O3—C2—C3—C17	−4.5 (6)	C18—C17—C22—C21	−0.2 (4)
C1—C2—C3—C4	−8.2 (3)	C22—C17—C18—Cl2	178.7 (2)
C1—C2—C3—C17	169.7 (3)	C22—C17—C18—C19	0.8 (4)
C2—C3—C4—O1	−173.7 (3)	Cl2—C18—C19—C20	−178.7 (2)
C2—C3—C4—O2	4.9 (3)	C17—C18—C19—C20	−0.6 (4)
C2—C3—C17—C18	−50.1 (5)	C18—C19—C20—Cl3	178.8 (2)
C2—C3—C17—C22	134.5 (3)	C18—C19—C20—C21	−0.1 (4)
C4—C3—C17—C18	127.6 (3)	Cl3—C20—C21—C22	−178.2 (2)
C4—C3—C17—C22	−47.9 (4)	C19—C20—C21—C22	0.7 (5)
C17—C3—C4—O1	8.0 (5)	C20—C21—C22—C17	−0.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H52···Cl1ⁱ	0.97	2.79	3.726 (3)	162
C16—H16···Cl3ⁱⁱ	0.93	2.82	3.595 (3)	141

Symmetry codes: (i) −x+1, −y, −z; (ii) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇Cl₃O₄
M_r	451.73
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	14.7979 (8), 10.3483 (5), 15.0702 (8)
β (°)	115.1875 (12)
V (Å³)	2088.33 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.46 × 0.32 × 0.28

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.800, 0.878
No. of measured, independent and observed [F² > 2σ(F²)] reflections	19403, 4756, 3289
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.131, 1.00
No. of reflections	4756
No. of parameters	263
No. of restraints	?
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.43

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SIR97 (Altomare et al., 1993), CRYSTALS (Watkin et al., 1996), CrystalStructure and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H52···Cl1ⁱ	0.97	2.79	3.726 (3)	162
C16—H16···Cl3ⁱⁱ	0.93	2.82	3.595 (3)	141

Symmetry codes: (i) −x+1, −y, −z; (ii) x−1/2, −y+1/2, z−1/2.

Acknowledgements

The authors thank the National Natural Science Foundation of China (No. 30700532) and the Science and Technology Project of Zhejiang Province (No. 2009C21044) for financial support.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
BAYER Aktiengesellschaft (1995). WO patent No. 9 504 719A1. Google Scholar
Benson, D. A., Lipman, D. J., Ostell, J., Rapp, B. A., Wheeler, D. L. & Genbank, N. (2000). Acids Res. 28, 15–18. Web of Science CrossRef CAS Google Scholar
Fischer, R. M., Bretschneider, T. S. & Kruger, B.-W. (1993). US Patent No. 5 262 383. Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291–294. Copenhagen: Munksgaard. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watkin, D. J., Prout, C. K., Carruthers, J. R. & Betteridge, P. W. (1996). CRYSTALS. Chemical Crystallography Laboratory, Oxford, England. Google Scholar
Zhao, J. H., Zhou, Y., Xu, X. H., Cheng, J. L. & Zhu, G. N. (2009). Chin. J. Struct. Chem. 28, 837–840. CAS Google Scholar

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Volume 65| Part 12| December 2009| Page o2992

doi:10.1107/S1600536809044109

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-(2,4-Di­chloro­phen­yl)-2-oxo-1-oxa­spiro­[4.5]dec-3-en-4-yl 4-chloro­benzoate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-(2,4-Dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl 4-chlorobenzoate