4-Benz­yloxy-3-(2,4-dichloro­phen­yl)-1-oxaspiro­[4.5]dec-3-en-2-one

Xu, L.; Su, Q.; Huang, J.; Sun, S.

doi:10.1107/S1600536809008356

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o845

doi:10.1107/S1600536809008356

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4-Benzyloxy-3-(2,4-dichlorophenyl)-1-oxaspiro[4.5]dec-3-en-2-one

Liang-zhong Xu,^a ^* Qun-qun Su,^a Jin Huang ^a and Shan-qi Sun ^a

^aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: qknhs@yahoo.com.cn

(Received 5 March 2009; accepted 7 March 2009; online 25 March 2009)

In the title compound, C₂₂H₂₀Cl₂O₃, the cyclohexyl ring adopts a chair conformation. The furanyl ring plane makes dihedral angles of 70.10 (2) and 86.12 (3)° with the 2,4-dichlorophenyl ring and aromatic ring of the benzyl group, respectively. The crystal structure features weak intermolecular C—H⋯O and C—H⋯Cl hydrogen bonds.

Related literature

For similar compounds, see: Bretschneider et al. (2003 ). For the synthesis, see: Yu et al. (1994 ); Song et al. (2008 ).

Experimental

Crystal data

C₂₂H₂₀Cl₂O₃
M_r = 403.28
Triclinic, $[P \overline 1]$
a = 7.2624 (15) Å
b = 12.117 (2) Å
c = 12.679 (3) Å
α = 63.30 (2)°
β = 87.67 (3)°
γ = 73.32 (1)°
V = 949.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 113 K
0.18 × 0.16 × 0.10 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.938, T_max = 0.965
7095 measured reflections
3328 independent reflections
2376 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.078
S = 1.03
3328 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2ⁱ	0.97	2.54	3.477 (2)	162
C2—H2B⋯Cl1ⁱⁱ	0.97	2.69	3.5051 (19)	142
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+2.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809008356/ng2556sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809008356/ng2556Isup2.hkl

checkCIF report

Comment top

The title compound (I) was prepared as part of a project in search for new compounds with biological activity (Bretschneider et al., 2003). We report here the crystal structure of (I).

In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously (Bretschneider et al., 2003). The cyclohexane ring (C1—C6) adopts a chair conformation. The furan ring (O1/C1/C7/C8/C9) plane forms dihedral angles of 71.10 (2)° and 86.12 (3)° with the benzene ring (C10—C15) and the benzyl plane (C16—C22) respectively. In addition to van der Waals forces, the structure is stabilized by weak C—H···O and C—H···Cl hydrogen bonds.

Related literature top

For similar compounds, see: Bretschneider et al. (2003). For the synthesis, see: Yu et al. (1994); Song et al. (2008). [Please revise scheme to show ring carbonyl group]

Experimental top

3-(2,4-Dichlorophenyl)-2,4-dioxo-1-oxaspiro[4.5]decane 3.13 g (10.0 mmol), was suspended in a solution of sodium carbonate 0.54 g (5.1 mmol) in 20 ml of water in a flask equipped with stirrer, water separator and reflux condenser. Toluene (40 ml) was added after 0.5 h, the mixture was heated to dehydration to distil the toluene solvent. Then 1-(chloromethyl)benzene 1.39 g (11.0 mmol) and N,N-dimethylformamide(DMF) solvent (20 ml) were added while maintaining the temperature at 373 K for 4 h. Upon cooling at room temperature water (20 ml) was added. The mixture was extracted with CH₂Cl₂ (15 ml) and the organic layer was washed with water and dried over sodium sulfate. The excess CH₂Cl₂ was removedon a water vacuum pump to obtain the oily product. Crystallized from methanol to afford the title compound 2.95 g (80% yield) (Yu et al., 1994; Song et al., 2008). Single crystals suitable for X-ray diffraction were obtained by recrystallization from the mixture of acetone and methanol at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound (I), with displacement ellipsoids drawn at the 40% probability level.

4-Benzyloxy-3-(2,4-dichlorophenyl)-1-oxaspiro[4.5]dec-3-en-2-one top

Crystal data top

C₂₂H₂₀Cl₂O₃	Z = 2
M_r = 403.28	F(000) = 420
Triclinic, P1	D_x = 1.410 Mg m⁻³
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2624 (15) Å	Cell parameters from 2983 reflections
b = 12.117 (2) Å	θ = 2.0–27.9°
c = 12.679 (3) Å	µ = 0.36 mm⁻¹
α = 63.30 (2)°	T = 113 K
β = 87.67 (3)°	Block, colorless
γ = 73.32 (1)°	0.18 × 0.16 × 0.10 mm
V = 949.8 (3) Å³

Data collection top

Rigaku Saturn diffractometer	3328 independent reflections
Radiation source: rotating anode	2376 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.039
ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −8→8
T_min = 0.938, T_max = 0.965	k = −14→10
7095 measured reflections	l = −15→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.03P)²] where P = (F_o² + 2F_c²)/3
3328 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₂H₂₀Cl₂O₃	γ = 73.32 (1)°
M_r = 403.28	V = 949.8 (3) Å³
Triclinic, P1	Z = 2
a = 7.2624 (15) Å	Mo Kα radiation
b = 12.117 (2) Å	µ = 0.36 mm⁻¹
c = 12.679 (3) Å	T = 113 K
α = 63.30 (2)°	0.18 × 0.16 × 0.10 mm
β = 87.67 (3)°

Data collection top

Rigaku Saturn diffractometer	3328 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2376 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.965	R_int = 0.039
7095 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
3328 reflections	Δρ_min = −0.22 e Å⁻³
244 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	0.74501 (6)	0.33929 (4)	1.10256 (4)	0.02229 (14)
Cl2	1.16128 (7)	−0.12117 (5)	1.44683 (4)	0.02817 (15)
O1	0.65050 (16)	0.34607 (11)	0.77085 (11)	0.0161 (3)
O2	0.93505 (17)	0.29879 (11)	0.86875 (11)	0.0195 (3)
O3	0.37612 (16)	0.16179 (11)	0.97360 (11)	0.0159 (3)
C1	0.4713 (2)	0.31322 (16)	0.79970 (16)	0.0139 (4)
C2	0.3139 (3)	0.43289 (16)	0.79041 (17)	0.0181 (4)
H2A	0.1982	0.4093	0.8194	0.022*
H2B	0.3566	0.4644	0.8402	0.022*
C3	0.2661 (3)	0.54029 (17)	0.66320 (18)	0.0236 (5)
H3A	0.3781	0.5699	0.6365	0.028*
H3B	0.1616	0.6130	0.6600	0.028*
C4	0.2071 (3)	0.49221 (18)	0.58136 (19)	0.0313 (5)
H4A	0.0885	0.4698	0.6038	0.038*
H4B	0.1827	0.5608	0.5003	0.038*
C5	0.3647 (3)	0.37423 (18)	0.58838 (17)	0.0295 (5)
H5A	0.4781	0.3995	0.5568	0.035*
H5B	0.3201	0.3423	0.5396	0.035*
C6	0.4199 (3)	0.26580 (16)	0.71537 (16)	0.0199 (4)
H6A	0.3128	0.2307	0.7424	0.024*
H6B	0.5296	0.1967	0.7168	0.024*
C7	0.5194 (2)	0.21147 (15)	0.92748 (16)	0.0131 (4)
C8	0.6971 (2)	0.19522 (15)	0.96996 (16)	0.0135 (4)
C9	0.7788 (3)	0.28199 (16)	0.87102 (17)	0.0156 (4)
C10	0.8070 (2)	0.11567 (16)	1.08853 (16)	0.0129 (4)
C11	0.8439 (2)	0.17346 (16)	1.15576 (16)	0.0149 (4)
C12	0.9524 (2)	0.10299 (16)	1.26515 (16)	0.0172 (4)
H12	0.9773	0.1439	1.3075	0.021*
C13	1.0228 (2)	−0.02970 (17)	1.30966 (16)	0.0174 (4)
C14	0.9885 (2)	−0.09177 (16)	1.24730 (17)	0.0176 (4)
H14	1.0361	−0.1814	1.2790	0.021*
C15	0.8826 (2)	−0.01880 (16)	1.13717 (16)	0.0160 (4)
H15	0.8612	−0.0603	1.0945	0.019*
C16	0.3825 (3)	0.08932 (16)	1.10127 (16)	0.0162 (4)
H16A	0.5050	0.0213	1.1312	0.019*
H16B	0.2807	0.0483	1.1194	0.019*
C17	0.3590 (2)	0.17132 (17)	1.16439 (17)	0.0168 (4)
C18	0.2414 (3)	0.29913 (17)	1.11236 (18)	0.0202 (4)
H18	0.1803	0.3361	1.0361	0.024*
C19	0.2147 (3)	0.37185 (19)	1.17361 (19)	0.0278 (5)
H19	0.1380	0.4579	1.1378	0.033*
C20	0.3018 (3)	0.3168 (2)	1.2875 (2)	0.0347 (6)
H20	0.2826	0.3653	1.3289	0.042*
C21	0.4176 (3)	0.1892 (2)	1.3404 (2)	0.0344 (6)
H21	0.4759	0.1520	1.4175	0.041*
C22	0.4468 (3)	0.11721 (19)	1.27877 (18)	0.0248 (5)
H22	0.5260	0.0318	1.3143	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0253 (3)	0.0150 (2)	0.0274 (3)	−0.00301 (19)	−0.0009 (2)	−0.0119 (2)
Cl2	0.0312 (3)	0.0302 (3)	0.0146 (3)	−0.0031 (2)	−0.0051 (2)	−0.0062 (2)
O1	0.0157 (7)	0.0161 (6)	0.0147 (7)	−0.0071 (5)	0.0021 (5)	−0.0042 (6)
O2	0.0140 (7)	0.0208 (7)	0.0240 (8)	−0.0086 (6)	0.0042 (6)	−0.0087 (6)
O3	0.0160 (7)	0.0181 (6)	0.0130 (8)	−0.0081 (5)	0.0023 (6)	−0.0049 (6)
C1	0.0143 (9)	0.0136 (9)	0.0138 (10)	−0.0076 (7)	0.0019 (8)	−0.0042 (8)
C2	0.0171 (10)	0.0167 (9)	0.0189 (11)	−0.0040 (8)	0.0009 (8)	−0.0075 (8)
C3	0.0210 (11)	0.0182 (10)	0.0227 (12)	−0.0021 (8)	−0.0022 (9)	−0.0039 (9)
C4	0.0354 (13)	0.0295 (12)	0.0186 (12)	−0.0115 (10)	−0.0100 (10)	−0.0001 (10)
C5	0.0476 (14)	0.0311 (11)	0.0138 (12)	−0.0214 (10)	−0.0007 (10)	−0.0077 (9)
C6	0.0280 (11)	0.0184 (10)	0.0169 (11)	−0.0105 (8)	0.0028 (9)	−0.0090 (9)
C7	0.0147 (9)	0.0117 (9)	0.0163 (11)	−0.0054 (7)	0.0050 (8)	−0.0087 (8)
C8	0.0141 (9)	0.0114 (9)	0.0160 (11)	−0.0030 (7)	0.0024 (8)	−0.0078 (8)
C9	0.0159 (10)	0.0128 (9)	0.0179 (11)	−0.0018 (8)	0.0011 (8)	−0.0082 (8)
C10	0.0080 (9)	0.0159 (9)	0.0154 (11)	−0.0037 (7)	0.0028 (7)	−0.0076 (8)
C11	0.0127 (9)	0.0136 (9)	0.0177 (11)	−0.0039 (7)	0.0027 (8)	−0.0068 (8)
C12	0.0178 (10)	0.0214 (10)	0.0162 (11)	−0.0090 (8)	0.0040 (8)	−0.0102 (9)
C13	0.0136 (9)	0.0225 (10)	0.0126 (11)	−0.0043 (8)	0.0012 (8)	−0.0058 (8)
C14	0.0183 (10)	0.0147 (9)	0.0168 (11)	−0.0041 (8)	0.0034 (8)	−0.0053 (8)
C15	0.0144 (10)	0.0182 (9)	0.0187 (11)	−0.0074 (8)	0.0047 (8)	−0.0101 (8)
C16	0.0166 (10)	0.0157 (9)	0.0140 (11)	−0.0091 (8)	0.0046 (8)	−0.0025 (8)
C17	0.0132 (9)	0.0230 (10)	0.0162 (11)	−0.0114 (8)	0.0073 (8)	−0.0075 (8)
C18	0.0197 (10)	0.0246 (10)	0.0174 (11)	−0.0094 (8)	0.0071 (8)	−0.0093 (9)
C19	0.0269 (11)	0.0285 (11)	0.0358 (14)	−0.0124 (9)	0.0150 (10)	−0.0199 (10)
C20	0.0326 (13)	0.0555 (15)	0.0384 (15)	−0.0225 (11)	0.0141 (11)	−0.0358 (13)
C21	0.0277 (12)	0.0596 (15)	0.0243 (13)	−0.0180 (11)	0.0051 (10)	−0.0236 (12)
C22	0.0195 (11)	0.0326 (11)	0.0194 (12)	−0.0082 (9)	0.0024 (9)	−0.0091 (10)

Geometric parameters (Å, º) top

Cl1—C11	1.7325 (18)	C8—C9	1.464 (3)
Cl2—C13	1.7420 (19)	C8—C10	1.477 (2)
O1—C9	1.371 (2)	C10—C15	1.396 (2)
O1—C1	1.454 (2)	C10—C11	1.397 (2)
O2—C9	1.206 (2)	C11—C12	1.383 (2)
O3—C7	1.335 (2)	C12—C13	1.379 (2)
O3—C16	1.449 (2)	C12—H12	0.9300
C1—C7	1.507 (3)	C13—C14	1.382 (2)
C1—C6	1.523 (2)	C14—C15	1.382 (2)
C1—C2	1.526 (2)	C14—H14	0.9300
C2—C3	1.522 (3)	C15—H15	0.9300
C2—H2A	0.9700	C16—C17	1.504 (2)
C2—H2B	0.9700	C16—H16A	0.9700
C3—C4	1.524 (3)	C16—H16B	0.9700
C3—H3A	0.9700	C17—C22	1.386 (3)
C3—H3B	0.9700	C17—C18	1.390 (2)
C4—C5	1.522 (3)	C18—C19	1.386 (3)
C4—H4A	0.9700	C18—H18	0.9300
C4—H4B	0.9700	C19—C20	1.377 (3)
C5—C6	1.526 (3)	C19—H19	0.9300
C5—H5A	0.9700	C20—C21	1.384 (3)
C5—H5B	0.9700	C20—H20	0.9300
C6—H6A	0.9700	C21—C22	1.382 (3)
C6—H6B	0.9700	C21—H21	0.9300
C7—C8	1.345 (2)	C22—H22	0.9300

C9—O1—C1	109.44 (14)	O2—C9—C8	129.10 (17)
C7—O3—C16	119.28 (14)	O1—C9—C8	110.02 (15)
O1—C1—C7	102.54 (14)	C15—C10—C11	117.08 (16)
O1—C1—C6	109.19 (15)	C15—C10—C8	122.16 (15)
C7—C1—C6	114.33 (14)	C11—C10—C8	120.74 (14)
O1—C1—C2	108.53 (13)	C12—C11—C10	122.57 (15)
C7—C1—C2	109.95 (15)	C12—C11—Cl1	118.35 (13)
C6—C1—C2	111.78 (14)	C10—C11—Cl1	119.05 (13)
C3—C2—C1	111.71 (16)	C13—C12—C11	118.09 (16)
C3—C2—H2A	109.3	C13—C12—H12	121.0
C1—C2—H2A	109.3	C11—C12—H12	121.0
C3—C2—H2B	109.3	C12—C13—C14	121.61 (16)
C1—C2—H2B	109.3	C12—C13—Cl2	119.22 (14)
H2A—C2—H2B	107.9	C14—C13—Cl2	119.17 (14)
C2—C3—C4	110.71 (16)	C13—C14—C15	119.12 (16)
C2—C3—H3A	109.5	C13—C14—H14	120.4
C4—C3—H3A	109.5	C15—C14—H14	120.4
C2—C3—H3B	109.5	C14—C15—C10	121.52 (16)
C4—C3—H3B	109.5	C14—C15—H15	119.2
H3A—C3—H3B	108.1	C10—C15—H15	119.2
C5—C4—C3	110.90 (16)	O3—C16—C17	113.48 (14)
C5—C4—H4A	109.5	O3—C16—H16A	108.9
C3—C4—H4A	109.5	C17—C16—H16A	108.9
C5—C4—H4B	109.5	O3—C16—H16B	108.9
C3—C4—H4B	109.5	C17—C16—H16B	108.9
H4A—C4—H4B	108.0	H16A—C16—H16B	107.7
C4—C5—C6	112.11 (18)	C22—C17—C18	119.09 (17)
C4—C5—H5A	109.2	C22—C17—C16	119.83 (16)
C6—C5—H5A	109.2	C18—C17—C16	120.98 (16)
C4—C5—H5B	109.2	C19—C18—C17	120.35 (19)
C6—C5—H5B	109.2	C19—C18—H18	119.8
H5A—C5—H5B	107.9	C17—C18—H18	119.8
C1—C6—C5	111.93 (15)	C20—C19—C18	120.03 (18)
C1—C6—H6A	109.2	C20—C19—H19	120.0
C5—C6—H6A	109.2	C18—C19—H19	120.0
C1—C6—H6B	109.2	C19—C20—C21	120.01 (19)
C5—C6—H6B	109.2	C19—C20—H20	120.0
H6A—C6—H6B	107.9	C21—C20—H20	120.0
O3—C7—C8	134.71 (17)	C22—C21—C20	120.0 (2)
O3—C7—C1	113.78 (15)	C22—C21—H21	120.0
C8—C7—C1	111.46 (17)	C20—C21—H21	120.0
C7—C8—C9	106.26 (16)	C21—C22—C17	120.49 (18)
C7—C8—C10	133.14 (17)	C21—C22—H22	119.8
C9—C8—C10	120.56 (15)	C17—C22—H22	119.8
O2—C9—O1	120.86 (17)

C9—O1—C1—C7	−5.26 (15)	C10—C8—C9—O1	−179.53 (13)
C9—O1—C1—C6	−126.89 (14)	C7—C8—C10—C15	71.9 (2)
C9—O1—C1—C2	111.04 (15)	C9—C8—C10—C15	−110.56 (19)
O1—C1—C2—C3	66.38 (18)	C7—C8—C10—C11	−109.8 (2)
C7—C1—C2—C3	177.80 (15)	C9—C8—C10—C11	67.8 (2)
C6—C1—C2—C3	−54.1 (2)	C15—C10—C11—C12	0.9 (3)
C1—C2—C3—C4	56.4 (2)	C8—C10—C11—C12	−177.49 (16)
C2—C3—C4—C5	−56.7 (2)	C15—C10—C11—Cl1	−177.30 (14)
C3—C4—C5—C6	55.2 (2)	C8—C10—C11—Cl1	4.3 (2)
O1—C1—C6—C5	−68.13 (19)	C10—C11—C12—C13	−1.4 (3)
C7—C1—C6—C5	177.68 (15)	Cl1—C11—C12—C13	176.86 (14)
C2—C1—C6—C5	52.0 (2)	C11—C12—C13—C14	0.6 (3)
C4—C5—C6—C1	−52.9 (2)	C11—C12—C13—Cl2	179.62 (13)
C16—O3—C7—C8	13.0 (3)	C12—C13—C14—C15	0.6 (3)
C16—O3—C7—C1	−164.16 (13)	Cl2—C13—C14—C15	−178.43 (14)
O1—C1—C7—O3	−177.66 (12)	C13—C14—C15—C10	−1.0 (3)
C6—C1—C7—O3	−59.62 (19)	C11—C10—C15—C14	0.3 (3)
C2—C1—C7—O3	67.05 (18)	C8—C10—C15—C14	178.71 (16)
O1—C1—C7—C8	4.54 (17)	C7—O3—C16—C17	67.88 (19)
C6—C1—C7—C8	122.59 (17)	O3—C16—C17—C22	−149.82 (16)
C2—C1—C7—C8	−110.74 (16)	O3—C16—C17—C18	33.8 (2)
O3—C7—C8—C9	−179.26 (16)	C22—C17—C18—C19	0.9 (3)
C1—C7—C8—C9	−2.11 (18)	C16—C17—C18—C19	177.25 (18)
O3—C7—C8—C10	−1.4 (3)	C17—C18—C19—C20	−1.3 (3)
C1—C7—C8—C10	175.71 (16)	C18—C19—C20—C21	0.7 (3)
C1—O1—C9—O2	−177.12 (14)	C19—C20—C21—C22	0.3 (3)
C1—O1—C9—C8	4.38 (16)	C20—C21—C22—C17	−0.7 (3)
C7—C8—C9—O2	−179.72 (16)	C18—C17—C22—C21	0.1 (3)
C10—C8—C9—O2	2.1 (3)	C16—C17—C22—C21	−176.28 (18)
C7—C8—C9—O1	−1.38 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2ⁱ	0.97	2.54	3.477 (2)	162
C2—H2B···Cl1ⁱⁱ	0.97	2.69	3.5051 (19)	142

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀Cl₂O₃
M_r	403.28
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	7.2624 (15), 12.117 (2), 12.679 (3)
α, β, γ (°)	63.30 (2), 87.67 (3), 73.32 (1)
V (Å³)	949.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.18 × 0.16 × 0.10

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.938, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	7095, 3328, 2376
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.078, 1.03
No. of reflections	3328
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.22

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2ⁱ	0.97	2.54	3.477 (2)	162.1
C2—H2B···Cl1ⁱⁱ	0.97	2.69	3.5051 (19)	142.1

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

References

Bretschneider, T., Benet-Buchholz, J., Fischer, R. & Nauen, R. (2003). Chimia, 57, 697–701. Web of Science CrossRef CAS Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Song, R. F. (2008). Fine Chem. 25, 708–709. Google Scholar
Yu, M. X. (1994). Pestic. Sci. 33, 14–15. Google Scholar

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Volume 65| Part 4| April 2009| Page o845

doi:10.1107/S1600536809008356

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