4-[(6-Chloro-2-pyrid­yl)meth­oxy]-3-(2,4-dichloro­phen­yl)-1-oxaspiro­[4.5]dec-3-en-2-one

Xu, L.; Huang, J.; Su, Q.; Guo, W.

doi:10.1107/S1600536809010101

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o846

doi:10.1107/S1600536809010101

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ADDENDA AND ERRATA

A correction has been published for this article. To view the correction, click here.

4-[(6-Chloro-2-pyridyl)methoxy]-3-(2,4-dichlorophenyl)-1-oxaspiro[4.5]dec-3-en-2-one

Liang-zhong Xu,^a ^* Jin Huang,^a Qun-qun Su ^a and Wei Guo ^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 3 March 2009; accepted 19 March 2009; online 25 March 2009)

In the title compound, C₂₁H₁₈Cl₃NO₃, the cyclohexane ring is in a chair conformation. The five-membered ring forms a dihedral angle of 69.89 (2)° with the benzene ring. The dihedral angle between the benzene and pyridine rings is 14.03 (7)°.

Related literature

For the biological activity of the title compound and a similar structure, see: Thomas et al. (2003 ). For its preparation, see: Lu et al. (2008 ); Sarcevic et al. (1973 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₁H₁₈Cl₃NO₃
M_r = 438.71
Monoclinic, P 2₁ /n
a = 7.2457 (14) Å
b = 13.108 (3) Å
c = 21.054 (4) Å
β = 95.77 (3)°
V = 1989.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 113 K
0.18 × 0.12 × 0.06 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.918, T_max = 0.972
14740 measured reflections
3519 independent reflections
3191 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.089
S = 1.08
3519 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.31 e Å⁻³

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010101/bx2196sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010101/bx2196Isup2.hkl

checkCIF report

Comment top

The goal of the synthesis of the title compound (I) is to obtain compounds with biological activity (Thomas et al., 2003). We report here the crystal structure of (I), Fig.1.The cyclohexane ring is a chair conformation [Puckering Amplitude (Q_T) = 0.5531 (18) Å, θ = 4.39 (19) °, ϕ = 142 (3) °] (Cremer & Pople, 1975).The five membered ring form a dihedral angle of 69.89 (2)° with the benzene ring. In the crystal structure, the molecular packing is stabilized by one intermolecular C—H···O hydrogen bond.

Related literature top

For the biological activity of the title compound, see: Thomas et al. (2003). For a similar structure, see: Thomas et al. (2003). For the preparation, see: Lu et al. (2008); Sarcevic et al. (1973). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

3-(2,4-Dichlorophenyl)-2,4-dioxo-1-oxaspiro[4.5]decane (6.26 g ;20.0 mmol), was suspended in a solution of sodium carbonate (1.08 g ;10.2 mmol) in 40 ml of water in a flask equipped with stirrer, water separator and reflux condenser. Toluene (80 ml) was added after 0.5 h, the mixture was heated to dehydration. Then 2-chloro-6-(chloromethyl)pyridine 3.56 g (22.0 mmol) and N,N-dimethylformamide(DMF) (40 ml) were added while maintaining the temperature at 100° C for 4 h. Upon cooling at room temperature. Then water (40 ml) was added. The mixture was extracted with CH₂Cl₂ (35 ml) and the organic layer was washed with water and dried over sodium sulfate. The excess CH₂Cl₂ was removed on a water vacuum pump to obtain the oil product which was crystallized from methanol to afford the title compound 7.89 g (90% yield) (Lu et al., 2008; Sarcevic et al., 1973). Single crystals suitable for X-ray measurement 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: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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-[(6-Chloro-2-pyridyl)methoxy]-3-(2,4-dichlorophenyl)-1-oxaspiro[4.5]dec-3-en-2-one top

Crystal data top

C₂₁H₁₈Cl₃NO₃	F(000) = 904
M_r = 438.71	D_x = 1.465 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5265 reflections
a = 7.2457 (14) Å	θ = 1.6–28.0°
b = 13.108 (3) Å	µ = 0.48 mm⁻¹
c = 21.054 (4) Å	T = 113 K
β = 95.77 (3)°	Platelet, colourless
V = 1989.5 (7) Å³	0.18 × 0.12 × 0.06 mm
Z = 4

Data collection top

Rigaku Saturn diffractometer	3519 independent reflections
Radiation source: rotating anode	3191 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.041
ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −8→8
T_min = 0.918, T_max = 0.972	k = −15→15
14740 measured reflections	l = −25→25

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.053P)²] where P = (F_o² + 2F_c²)/3
3519 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₁H₁₈Cl₃NO₃	V = 1989.5 (7) Å³
M_r = 438.71	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.2457 (14) Å	µ = 0.48 mm⁻¹
b = 13.108 (3) Å	T = 113 K
c = 21.054 (4) Å	0.18 × 0.12 × 0.06 mm
β = 95.77 (3)°

Data collection top

Rigaku Saturn diffractometer	3519 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3191 reflections with I > 2σ(I)
T_min = 0.918, T_max = 0.972	R_int = 0.041
14740 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.08	Δρ_max = 0.18 e Å⁻³
3519 reflections	Δρ_min = −0.31 e Å⁻³
253 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	−0.28480 (7)	−0.08999 (4)	0.06950 (2)	0.03906 (15)
Cl2	−0.06561 (6)	0.21586 (3)	0.228775 (19)	0.02533 (13)
Cl3	0.36534 (7)	0.22352 (4)	0.06907 (2)	0.03617 (15)
O1	0.00146 (14)	0.14206 (8)	0.42592 (5)	0.0204 (3)
O2	−0.26135 (15)	0.13568 (9)	0.35960 (5)	0.0248 (3)
O3	0.35068 (14)	0.00872 (8)	0.35405 (5)	0.0226 (3)
N1	0.4102 (2)	0.18419 (11)	0.19104 (7)	0.0264 (3)
C1	0.1925 (2)	0.10733 (12)	0.42562 (7)	0.0188 (3)
C2	0.3193 (2)	0.20111 (12)	0.42615 (8)	0.0239 (4)
H2A	0.4436	0.1795	0.4190	0.029*
H2B	0.2745	0.2464	0.3915	0.029*
C3	0.3264 (2)	0.25889 (13)	0.48925 (8)	0.0275 (4)
H3A	0.2050	0.2870	0.4944	0.033*
H3B	0.4135	0.3150	0.4889	0.033*
C4	0.3862 (3)	0.18769 (13)	0.54514 (8)	0.0292 (4)
H4A	0.5117	0.1641	0.5416	0.035*
H4B	0.3862	0.2251	0.5849	0.035*
C5	0.2574 (2)	0.09592 (13)	0.54645 (8)	0.0259 (4)
H5A	0.1351	0.1188	0.5551	0.031*
H5B	0.3042	0.0502	0.5806	0.031*
C6	0.2430 (2)	0.03854 (12)	0.48280 (7)	0.0211 (4)
H6A	0.3608	0.0058	0.4780	0.025*
H6B	0.1498	−0.0145	0.4835	0.025*
C7	0.1869 (2)	0.05012 (11)	0.36345 (7)	0.0182 (3)
C8	0.3726 (2)	−0.04708 (12)	0.29626 (8)	0.0251 (4)
H8A	0.2760	−0.0984	0.2901	0.030*
H8B	0.4911	−0.0822	0.3010	0.030*
C9	0.3640 (2)	0.01985 (12)	0.23785 (8)	0.0221 (4)
C10	0.3138 (2)	−0.02018 (13)	0.17760 (8)	0.0285 (4)
H10	0.2810	−0.0886	0.1730	0.034*
C11	0.3125 (2)	0.04149 (14)	0.12452 (8)	0.0293 (4)
H11	0.2799	0.0162	0.0837	0.035*
C12	0.3619 (2)	0.14262 (13)	0.13470 (8)	0.0254 (4)
C13	0.4111 (2)	0.12222 (13)	0.24178 (8)	0.0247 (4)
H13	0.4453	0.1496	0.2820	0.030*
C14	0.0183 (2)	0.05485 (11)	0.33042 (7)	0.0185 (3)
C15	−0.0991 (2)	0.11385 (12)	0.37036 (7)	0.0199 (4)
C16	−0.0574 (2)	0.01791 (12)	0.26666 (7)	0.0190 (3)
C17	−0.0880 (2)	−0.08572 (12)	0.25352 (8)	0.0233 (4)
H17	−0.0618	−0.1332	0.2860	0.028*
C18	−0.1565 (2)	−0.11919 (13)	0.19334 (8)	0.0263 (4)
H18	−0.1736	−0.1885	0.1853	0.032*
C19	−0.1993 (2)	−0.04852 (13)	0.14529 (8)	0.0253 (4)
C20	−0.1746 (2)	0.05474 (12)	0.15634 (8)	0.0229 (4)
H20	−0.2048	0.1020	0.1240	0.027*
C21	−0.1040 (2)	0.08598 (11)	0.21652 (8)	0.0185 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0450 (3)	0.0442 (3)	0.0269 (3)	−0.0021 (2)	−0.0017 (2)	−0.0110 (2)
Cl2	0.0338 (3)	0.0155 (2)	0.0269 (2)	0.00057 (16)	0.00361 (19)	0.00429 (15)
Cl3	0.0350 (3)	0.0439 (3)	0.0300 (3)	−0.0021 (2)	0.0051 (2)	0.00633 (19)
O1	0.0162 (6)	0.0236 (6)	0.0215 (6)	0.0040 (5)	0.0021 (5)	0.0022 (5)
O2	0.0166 (6)	0.0297 (6)	0.0280 (6)	0.0052 (5)	0.0021 (5)	0.0069 (5)
O3	0.0187 (6)	0.0257 (6)	0.0233 (6)	0.0067 (5)	0.0016 (5)	−0.0029 (5)
N1	0.0241 (8)	0.0266 (8)	0.0287 (8)	−0.0017 (6)	0.0034 (6)	−0.0031 (6)
C1	0.0152 (8)	0.0185 (8)	0.0226 (8)	0.0032 (6)	0.0020 (7)	0.0025 (6)
C2	0.0237 (9)	0.0211 (8)	0.0276 (9)	−0.0004 (7)	0.0062 (7)	0.0020 (7)
C3	0.0257 (10)	0.0208 (9)	0.0361 (10)	−0.0019 (7)	0.0043 (8)	−0.0039 (7)
C4	0.0313 (10)	0.0279 (9)	0.0277 (10)	−0.0004 (8)	−0.0006 (8)	−0.0068 (8)
C5	0.0262 (9)	0.0291 (9)	0.0221 (9)	0.0026 (7)	0.0002 (7)	0.0017 (7)
C6	0.0186 (8)	0.0201 (8)	0.0242 (9)	0.0013 (7)	−0.0005 (7)	0.0018 (7)
C7	0.0181 (8)	0.0148 (8)	0.0220 (8)	0.0015 (6)	0.0034 (7)	0.0037 (6)
C8	0.0233 (9)	0.0229 (9)	0.0292 (9)	0.0074 (7)	0.0027 (7)	−0.0058 (7)
C9	0.0156 (8)	0.0231 (9)	0.0279 (9)	0.0034 (7)	0.0038 (7)	−0.0053 (7)
C10	0.0291 (10)	0.0248 (9)	0.0326 (10)	−0.0035 (7)	0.0083 (8)	−0.0096 (8)
C11	0.0289 (10)	0.0354 (10)	0.0240 (9)	−0.0051 (8)	0.0050 (7)	−0.0105 (8)
C12	0.0168 (9)	0.0346 (10)	0.0255 (9)	−0.0004 (7)	0.0051 (7)	−0.0024 (7)
C13	0.0210 (9)	0.0291 (9)	0.0237 (9)	−0.0018 (7)	0.0009 (7)	−0.0071 (7)
C14	0.0182 (8)	0.0152 (8)	0.0221 (8)	0.0000 (6)	0.0020 (7)	0.0047 (6)
C15	0.0219 (9)	0.0170 (8)	0.0207 (8)	−0.0012 (7)	0.0019 (7)	0.0071 (6)
C16	0.0158 (8)	0.0186 (8)	0.0226 (8)	−0.0003 (6)	0.0022 (7)	0.0024 (6)
C17	0.0223 (9)	0.0184 (8)	0.0290 (9)	−0.0011 (7)	0.0019 (7)	0.0048 (7)
C18	0.0257 (10)	0.0199 (9)	0.0332 (10)	−0.0032 (7)	0.0031 (8)	−0.0023 (7)
C19	0.0220 (9)	0.0300 (9)	0.0237 (9)	−0.0023 (7)	0.0015 (7)	−0.0054 (7)
C20	0.0202 (9)	0.0267 (9)	0.0218 (8)	0.0022 (7)	0.0030 (7)	0.0039 (7)
C21	0.0175 (8)	0.0150 (8)	0.0234 (9)	0.0009 (6)	0.0041 (7)	−0.0003 (6)

Geometric parameters (Å, º) top

Cl1—C19	1.7398 (17)	C6—H6A	0.9700
Cl2—C21	1.7400 (16)	C6—H6B	0.9700
Cl3—C12	1.7440 (17)	C7—C14	1.345 (2)
O1—C15	1.366 (2)	C8—C9	1.507 (2)
O1—C1	1.4577 (18)	C8—H8A	0.9700
O2—C15	1.2090 (19)	C8—H8B	0.9700
O3—C7	1.3375 (18)	C9—C13	1.385 (2)
O3—C8	1.4421 (18)	C9—C10	1.387 (2)
N1—C12	1.320 (2)	C10—C11	1.378 (2)
N1—C13	1.342 (2)	C10—H10	0.9300
C1—C7	1.505 (2)	C11—C12	1.384 (2)
C1—C6	1.519 (2)	C11—H11	0.9300
C1—C2	1.534 (2)	C13—H13	0.9300
C2—C3	1.526 (2)	C14—C15	1.474 (2)
C2—H2A	0.9700	C14—C16	1.480 (2)
C2—H2B	0.9700	C16—C21	1.398 (2)
C3—C4	1.530 (2)	C16—C17	1.400 (2)
C3—H3A	0.9700	C17—C18	1.385 (2)
C3—H3B	0.9700	C17—H17	0.9300
C4—C5	1.524 (2)	C18—C19	1.384 (2)
C4—H4A	0.9700	C18—H18	0.9300
C4—H4B	0.9700	C19—C20	1.382 (2)
C5—C6	1.531 (2)	C20—C21	1.380 (2)
C5—H5A	0.9700	C20—H20	0.9300
C5—H5B	0.9700

C15—O1—C1	109.69 (12)	C9—C8—H8A	108.9
C7—O3—C8	120.36 (13)	O3—C8—H8B	108.9
C12—N1—C13	116.43 (15)	C9—C8—H8B	108.9
O1—C1—C7	102.52 (12)	H8A—C8—H8B	107.7
O1—C1—C6	109.58 (12)	C13—C9—C10	117.49 (15)
C7—C1—C6	112.12 (13)	C13—C9—C8	121.71 (15)
O1—C1—C2	108.54 (12)	C10—C9—C8	120.77 (15)
C7—C1—C2	111.66 (12)	C11—C10—C9	119.95 (16)
C6—C1—C2	111.93 (14)	C11—C10—H10	120.0
C3—C2—C1	111.83 (13)	C9—C10—H10	120.0
C3—C2—H2A	109.2	C10—C11—C12	117.11 (16)
C1—C2—H2A	109.2	C10—C11—H11	121.4
C3—C2—H2B	109.2	C12—C11—H11	121.4
C1—C2—H2B	109.2	N1—C12—C11	125.13 (16)
H2A—C2—H2B	107.9	N1—C12—Cl3	115.93 (13)
C2—C3—C4	110.44 (14)	C11—C12—Cl3	118.94 (13)
C2—C3—H3A	109.6	N1—C13—C9	123.89 (15)
C4—C3—H3A	109.6	N1—C13—H13	118.1
C2—C3—H3B	109.6	C9—C13—H13	118.1
C4—C3—H3B	109.6	C7—C14—C15	105.99 (14)
H3A—C3—H3B	108.1	C7—C14—C16	133.52 (14)
C5—C4—C3	111.65 (14)	C15—C14—C16	120.44 (14)
C5—C4—H4A	109.3	O2—C15—O1	121.42 (14)
C3—C4—H4A	109.3	O2—C15—C14	128.58 (15)
C5—C4—H4B	109.3	O1—C15—C14	109.99 (13)
C3—C4—H4B	109.3	C21—C16—C17	116.66 (15)
H4A—C4—H4B	108.0	C21—C16—C14	121.05 (14)
C4—C5—C6	111.10 (14)	C17—C16—C14	122.28 (14)
C4—C5—H5A	109.4	C18—C17—C16	121.58 (15)
C6—C5—H5A	109.4	C18—C17—H17	119.2
C4—C5—H5B	109.4	C16—C17—H17	119.2
C6—C5—H5B	109.4	C19—C18—C17	119.35 (15)
H5A—C5—H5B	108.0	C19—C18—H18	120.3
C1—C6—C5	113.06 (13)	C17—C18—H18	120.3
C1—C6—H6A	109.0	C20—C19—C18	121.13 (16)
C5—C6—H6A	109.0	C20—C19—Cl1	119.24 (13)
C1—C6—H6B	109.0	C18—C19—Cl1	119.63 (13)
C5—C6—H6B	109.0	C21—C20—C19	118.36 (15)
H6A—C6—H6B	107.8	C21—C20—H20	120.8
O3—C7—C14	135.67 (15)	C19—C20—H20	120.8
O3—C7—C1	112.59 (13)	C20—C21—C16	122.90 (14)
C14—C7—C1	111.73 (13)	C20—C21—Cl2	117.74 (12)
O3—C8—C9	113.22 (12)	C16—C21—Cl2	119.32 (12)
O3—C8—H8A	108.9

C15—O1—C1—C7	−2.79 (15)	C12—N1—C13—C9	−0.3 (2)
C15—O1—C1—C6	−122.03 (13)	C10—C9—C13—N1	0.2 (2)
C15—O1—C1—C2	115.46 (13)	C8—C9—C13—N1	178.20 (15)
O1—C1—C2—C3	68.12 (17)	O3—C7—C14—C15	179.93 (16)
C7—C1—C2—C3	−179.60 (13)	C1—C7—C14—C15	−1.50 (17)
C6—C1—C2—C3	−52.96 (18)	O3—C7—C14—C16	−2.6 (3)
C1—C2—C3—C4	55.70 (18)	C1—C7—C14—C16	175.99 (15)
C2—C3—C4—C5	−57.18 (19)	C1—O1—C15—O2	−179.05 (13)
C3—C4—C5—C6	55.15 (19)	C1—O1—C15—C14	2.09 (16)
O1—C1—C6—C5	−69.25 (17)	C7—C14—C15—O2	−179.10 (15)
C7—C1—C6—C5	177.61 (13)	C16—C14—C15—O2	3.0 (2)
C2—C1—C6—C5	51.22 (18)	C7—C14—C15—O1	−0.35 (16)
C4—C5—C6—C1	−52.32 (18)	C16—C14—C15—O1	−178.24 (13)
C8—O3—C7—C14	0.0 (3)	C7—C14—C16—C21	−109.1 (2)
C8—O3—C7—C1	−178.59 (12)	C15—C14—C16—C21	68.14 (19)
O1—C1—C7—O3	−178.43 (12)	C7—C14—C16—C17	71.7 (2)
C6—C1—C7—O3	−60.99 (17)	C15—C14—C16—C17	−111.08 (17)
C2—C1—C7—O3	65.55 (16)	C21—C16—C17—C18	1.7 (2)
O1—C1—C7—C14	2.66 (16)	C14—C16—C17—C18	−179.07 (15)
C6—C1—C7—C14	120.10 (15)	C16—C17—C18—C19	−1.3 (2)
C2—C1—C7—C14	−113.36 (15)	C17—C18—C19—C20	0.1 (3)
C7—O3—C8—C9	69.36 (18)	C17—C18—C19—Cl1	179.83 (12)
O3—C8—C9—C13	26.2 (2)	C18—C19—C20—C21	0.7 (2)
O3—C8—C9—C10	−155.88 (14)	Cl1—C19—C20—C21	−179.05 (12)
C13—C9—C10—C11	0.1 (2)	C19—C20—C21—C16	−0.3 (2)
C8—C9—C10—C11	−177.88 (16)	C19—C20—C21—Cl2	177.62 (12)
C9—C10—C11—C12	−0.3 (2)	C17—C16—C21—C20	−0.9 (2)
C13—N1—C12—C11	0.2 (2)	C14—C16—C21—C20	179.87 (14)
C13—N1—C12—Cl3	−178.92 (12)	C17—C16—C21—Cl2	−178.75 (12)
C10—C11—C12—N1	0.2 (3)	C14—C16—C21—Cl2	2.0 (2)
C10—C11—C12—Cl3	179.21 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3	0.93	2.53	2.864 (2)	102

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈Cl₃NO₃
M_r	438.71
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	7.2457 (14), 13.108 (3), 21.054 (4)
β (°)	95.77 (3)
V (Å³)	1989.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.18 × 0.12 × 0.06

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.918, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	14740, 3519, 3191
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.089, 1.08
No. of reflections	3519
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.31

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3	0.93	2.53	2.864 (2)	102

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Lu, Y., Tao, J. Z. & Zhang, Z. R. (2008). Chem. Intermed. 10, 25–28. Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sarcevic, N., Zsindely, J. & Schmid, H. (1973). Helv. Chim. Acta, 56, 1457–1476. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thomas, B., Jordi, B. B., Reiner, F. & Ralf, N. (2003). Chimia, 57, 697–701. Google Scholar

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Volume 65| Part 4| April 2009| Page o846

doi:10.1107/S1600536809010101

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

4-[(6-Chloro-2-pyrid­yl)meth­­oxy]-3-(2,4-di­chloro­phen­yl)-1-oxa­spiro­[4.5]dec-3-en-2-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

4-[(6-Chloro-2-pyridyl)methoxy]-3-(2,4-dichlorophenyl)-1-oxaspiro[4.5]dec-3-en-2-one