3-Mesityl-2-oxo-1-oxaspiro­[4.4]non-3-en-4-yl 4-chloro­benzoate

Ji, M.-H.; Xia, M.; Zhu, G.-N.; Zhao, J.-H.

doi:10.1107/S1600536809006503

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o705

doi:10.1107/S1600536809006503

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3-Mesityl-2-oxo-1-oxaspiro[4.4]non-3-en-4-yl 4-chlorobenzoate

Ming-Hua Ji,^a Min Xia,^a Guo-Nian Zhu ^b and Jin-Hao Zhao ^b ^*

^aInstitute of Science, Zhejiang Sci_tec University, Hangzhou 310032, People's Republic of China, and ^bCollege of Agriculture and Biotechnology, Zhejiang University, Hangzhou 310029, People's Republic of China
^*Correspondence e-mail: jinhaozhao@zju.edu.cn

(Received 7 February 2009; accepted 23 February 2009; online 6 March 2009)

The title compound, C₂₄H₂₃ClO₄, is a potent insecticide and miticide. The five-membered cyclopentane ring displays an envelope conformation with the atom at the flap position 0.611 (2) Å out of the mean plane formed by the other four atoms. The furan ring makes dihedral angles of 71.3 (2) and 81.9 (2)°, respectively, with the 2,4,6-trimethylphenyl and 4-chlorophenyl rings. The dihedral angle between the two benzene rings is 76.6 (1)°. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds, forming chains running along the c axis.

Related literature

For a related insecticide, see: Bayer, (1995 ). For a related methylbutyrate structure, see: Yu et al. (2009 ). For the extinction correction, see: Larson (1970 ).

Experimental

Crystal data

C₂₄H₂₃ClO₄
M_r = 410.90
Monoclinic, P 2₁ /c
a = 6.4880 (2) Å
b = 22.9397 (8) Å
c = 14.6305 (6) Å
β = 91.533 (1)°
V = 2176.72 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.62 × 0.48 × 0.34 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.867, T_max = 0.934
33470 measured reflections
4926 independent reflections
3235 reflections with F² > 2σ(F²)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.092
S = 1.00
4926 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H242⋯O2ⁱ	0.97	2.57	3.475 (2)	155
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SIR97 (Altomare et al., 1993 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006503/si2154sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006503/si2154Isup2.hkl

checkCIF report

Comment top

4-hydroxyl-3-(2,4,6-trimethylphenyl)-1-oxaspiro[4,4]non-3-en-2-one (HTPO) is a key intermediate of Spiromesifen, which is an efficient insecticide and miticide, developed by Bayer company (Bayer, 1995). As part of our continuing interest in the design and synthesis of the new insecticide and miticide, we have isolated the title compound (Fig. 1), by the condensation reaction of 4-chlorophenyl- acetylchloride and HTPO as colorless crystals. The molecule contains two six-membered rings and two five-membered rings. Atoms C1, C2, C12, C20, O1 and O2 are coplanar, the largest deviation being 0.011 (11) Å for O1. As expected, C2=C12, C1=O2 and C13=O4 are typical double bonds with bond distances of 1.317 (2), 1.202 (2) and 1.195 (3) Å suggests that C2, C12 and C13 atoms are sp² hybridized. The bond distance of C1—C2 is 1.475 (2) Å, suggesting that the carbonyl group on C1 has formed a conjugate system with double bond on C2 and C12. In the crystal, molecules are linked through weak intermolecular C—H···O hydrogen bonds (Table 1), forming chains running along the c axis (Fig. 2), in contrast to the related 3-mesityl-2-oxo-1-oxaspiro[4.4]non-3-en-4-yl 2-(chlorophenyl)-3-methyl- butyrate structure, where intermolecular C—H···Cl hydrogen bonds forming chains along the screw axis direction b (Yu et al. 2009).

Related literature top

For a related insecticide, see: Bayer, (1995). For a related methylbutyrate structure, see: Yu et al. (2009). For related literature, see: Larson (1970).

Experimental top

4-hydroxyl-3-(2,4,6-trimethylphenyl)-1-oxaspiro[4,4]non-3-en-2-one (0.272 g, 1 mmol) and triethylamine (0.152 g, 1.5 mmol) were dissolved in dry dichloromethane (15 ml) with stirring. 4-chlorophenylacetyl chloride (0.210 g, 1.2 mmol) was added dropwise to the mixture in a water bath. The mixture was stirred at 293–298 K for 5 h, and then 1% aqueous HCl was added. The organic layer was washed to neutral with water and dried via Na₂SO₄. After filtered and concentrated, the organic residue was purified by silica gel column chromatography, eluted with ethyl acetate-petroleum ether (1:3. v/v) to give a white solid (yield 81%, 0.334 g), which was then recrystallized from acetone/ethanol (1:2, v/v) to give colourless blocks.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

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. A packing diagram of the title compound, viewed along the a axis.

3-Mesityl-2-oxo-1-oxaspiro[4.4]non-3-en-4-yl 4-chlorobenzoate top

Crystal data top

C₂₄H₂₃ClO₄	F(000) = 864.00
M_r = 410.90	D_x = 1.254 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 20338 reflections
a = 6.4880 (2) Å	θ = 3.0–27.4°
b = 22.9397 (8) Å	µ = 0.20 mm⁻¹
c = 14.6305 (6) Å	T = 296 K
β = 91.533 (1)°	Block, colorless
V = 2176.72 (14) Å³	0.62 × 0.48 × 0.34 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	3235 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.030
ω scans	θ_max = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→7
T_min = 0.867, T_max = 0.934	k = −29→29
33470 measured reflections	l = −18→18
4926 independent reflections

Refinement top

Refinement on F²	w = 1/[0.0002F_o² + 1.45σ(F_o²)]/(4F_o²)
R[F² > 2σ(F²)] = 0.037	(Δ/σ)_max < 0.001
wR(F²) = 0.092	Δρ_max = 0.14 e Å⁻³
S = 1.00	Δρ_min = −0.17 e Å⁻³
4926 reflections	Extinction correction: Larson (1970), equation 22
263 parameters	Extinction coefficient: 695 (30)
H-atom parameters constrained

Crystal data top

C₂₄H₂₃ClO₄	V = 2176.72 (14) Å³
M_r = 410.90	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.4880 (2) Å	µ = 0.20 mm⁻¹
b = 22.9397 (8) Å	T = 296 K
c = 14.6305 (6) Å	0.62 × 0.48 × 0.34 mm
β = 91.533 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4926 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3235 reflections with F² > 2σ(F²)
T_min = 0.867, T_max = 0.934	R_int = 0.030
33470 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	263 parameters
wR(F²) = 0.092	H-atom parameters constrained
S = 1.00	Δρ_max = 0.14 e Å⁻³
4926 reflections	Δρ_min = −0.17 e Å⁻³

Special details top

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	0.25024 (8)	0.45321 (2)	−0.01486 (4)	0.0960 (2)
O1	0.83337 (16)	0.19253 (4)	0.49303 (8)	0.0589 (3)
O2	0.83728 (17)	0.23623 (5)	0.62950 (8)	0.0671 (3)
O3	0.64511 (14)	0.29954 (4)	0.33174 (6)	0.0563 (3)
O4	0.31480 (18)	0.29640 (6)	0.37120 (10)	0.0822 (5)
C1	0.7983 (2)	0.23874 (6)	0.54880 (12)	0.0531 (5)
C2	0.7122 (2)	0.28760 (6)	0.49455 (12)	0.0493 (4)
C3	0.6530 (2)	0.34424 (6)	0.53503 (11)	0.0517 (4)
C4	0.4814 (2)	0.34712 (6)	0.59006 (12)	0.0617 (5)
C5	0.4308 (3)	0.40037 (8)	0.62872 (12)	0.0815 (7)
C6	0.5482 (4)	0.45001 (8)	0.61565 (16)	0.0906 (8)
C7	0.7148 (3)	0.44552 (8)	0.56064 (17)	0.0903 (7)
C8	0.7716 (2)	0.39386 (6)	0.51955 (12)	0.0664 (5)
C9	0.3514 (2)	0.29404 (8)	0.60759 (14)	0.0839 (7)
C10	0.4933 (4)	0.50730 (9)	0.66180 (18)	0.1028 (11)
C11	0.9564 (2)	0.39222 (8)	0.45970 (17)	0.0990 (8)
C12	0.7031 (2)	0.26889 (6)	0.40947 (12)	0.0498 (4)
C13	0.4412 (2)	0.31350 (6)	0.31964 (12)	0.0546 (5)
C14	0.4018 (2)	0.34881 (6)	0.23706 (11)	0.0479 (4)
C15	0.5560 (2)	0.37213 (6)	0.18689 (12)	0.0557 (5)
C16	0.5109 (2)	0.40460 (6)	0.10976 (12)	0.0653 (5)
C17	0.3095 (2)	0.41340 (6)	0.08306 (12)	0.0599 (5)
C18	0.1545 (2)	0.38918 (8)	0.13064 (14)	0.0864 (7)
C19	0.1998 (2)	0.35689 (8)	0.20804 (14)	0.0813 (6)
C20	0.7718 (2)	0.20699 (6)	0.39878 (11)	0.0526 (4)
C21	0.6061 (2)	0.16400 (6)	0.36752 (12)	0.0650 (5)
C22	0.7311 (3)	0.10964 (6)	0.34622 (13)	0.0819 (6)
C23	0.9180 (3)	0.13309 (9)	0.29939 (14)	0.0926 (7)
C24	0.9516 (2)	0.19490 (6)	0.33625 (12)	0.0718 (6)
H5	0.3147	0.4028	0.6644	0.098*
H7	0.7933	0.4787	0.5504	0.108*
H15	0.6928	0.3660	0.2050	0.067*
H16	0.6166	0.4205	0.0760	0.078*
H18	0.0182	0.3944	0.1111	0.104*
H19	0.0936	0.3405	0.2409	0.098*
H91	0.2999	0.2786	0.5504	0.101*
H92	0.2377	0.3047	0.6448	0.101*
H93	0.4337	0.2650	0.6387	0.101*
H101	0.3526	0.5060	0.6804	0.123*
H102	0.5823	0.5131	0.7145	0.123*
H103	0.5104	0.5389	0.6196	0.123*
H111	1.0216	0.3547	0.4648	0.119*
H112	0.9133	0.3989	0.3973	0.119*
H113	1.0523	0.4220	0.4788	0.119*
H211	0.5096	0.1565	0.4156	0.078*
H212	0.5318	0.1781	0.3135	0.078*
H221	0.7709	0.0891	0.4019	0.098*
H222	0.6533	0.0836	0.3060	0.098*
H231	1.0375	0.1090	0.3136	0.111*
H232	0.8938	0.1340	0.2337	0.111*
H241	1.0814	0.1973	0.3705	0.086*
H242	0.9517	0.2227	0.2863	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1083 (4)	0.0976 (3)	0.0808 (4)	0.0141 (2)	−0.0245 (3)	0.0319 (3)
O1	0.0795 (7)	0.0537 (6)	0.0429 (7)	0.0070 (5)	−0.0072 (5)	0.0039 (5)
O2	0.0907 (8)	0.0672 (7)	0.0425 (8)	−0.0056 (5)	−0.0117 (6)	0.0056 (6)
O3	0.0610 (6)	0.0657 (6)	0.0422 (7)	0.0093 (5)	0.0000 (5)	0.0114 (5)
O4	0.0608 (7)	0.1034 (11)	0.0823 (11)	−0.0012 (7)	0.0019 (7)	0.0253 (9)
C1	0.0638 (10)	0.0529 (9)	0.0423 (11)	−0.0086 (7)	−0.0043 (8)	0.0043 (8)
C2	0.0584 (9)	0.0474 (8)	0.0419 (10)	−0.0054 (6)	−0.0011 (7)	0.0040 (7)
C3	0.0668 (10)	0.0462 (8)	0.0417 (10)	−0.0040 (7)	−0.0053 (8)	0.0022 (7)
C4	0.0803 (11)	0.0605 (10)	0.0442 (11)	0.0015 (8)	−0.0008 (9)	−0.0006 (8)
C5	0.1075 (15)	0.0836 (13)	0.0534 (13)	0.0250 (11)	0.0025 (11)	−0.0061 (11)
C6	0.152 (2)	0.0569 (12)	0.0618 (15)	0.0231 (13)	−0.0212 (14)	−0.0090 (10)
C7	0.1344 (19)	0.0487 (10)	0.0867 (17)	−0.0122 (11)	−0.0215 (14)	0.0013 (11)
C8	0.0826 (12)	0.0518 (10)	0.0642 (13)	−0.0084 (8)	−0.0087 (10)	0.0072 (9)
C9	0.0858 (13)	0.0926 (13)	0.0745 (15)	−0.0107 (10)	0.0220 (11)	0.0034 (11)
C10	0.132 (3)	0.0769 (14)	0.098 (2)	0.0380 (17)	−0.026 (2)	−0.0258 (14)
C11	0.0945 (15)	0.0814 (13)	0.121 (2)	−0.0267 (10)	0.0057 (14)	0.0203 (13)
C12	0.0559 (9)	0.0510 (8)	0.0424 (10)	−0.0014 (6)	−0.0027 (7)	0.0088 (8)
C13	0.0541 (9)	0.0598 (9)	0.0496 (11)	−0.0062 (7)	−0.0040 (8)	0.0024 (8)
C14	0.0525 (9)	0.0445 (8)	0.0464 (10)	−0.0003 (6)	−0.0049 (7)	−0.0009 (7)
C15	0.0525 (9)	0.0602 (9)	0.0544 (11)	0.0090 (7)	−0.0011 (8)	0.0079 (8)
C16	0.0638 (11)	0.0705 (10)	0.0619 (12)	0.0078 (8)	0.0060 (9)	0.0169 (9)
C17	0.0697 (11)	0.0565 (9)	0.0527 (11)	0.0068 (8)	−0.0113 (9)	0.0048 (8)
C18	0.0590 (11)	0.1087 (15)	0.0901 (16)	−0.0019 (10)	−0.0229 (11)	0.0293 (13)
C19	0.0559 (11)	0.1068 (14)	0.0806 (15)	−0.0106 (9)	−0.0092 (10)	0.0308 (12)
C20	0.0637 (9)	0.0546 (9)	0.0392 (10)	0.0039 (7)	−0.0034 (8)	0.0036 (7)
C21	0.0785 (11)	0.0597 (9)	0.0562 (12)	−0.0025 (8)	−0.0077 (9)	−0.0014 (8)
C22	0.1206 (16)	0.0589 (11)	0.0655 (14)	0.0083 (10)	−0.0084 (12)	−0.0098 (10)
C23	0.1229 (17)	0.0889 (13)	0.0664 (15)	0.0319 (12)	0.0108 (13)	−0.0087 (11)
C24	0.0745 (11)	0.0834 (12)	0.0579 (13)	0.0147 (9)	0.0083 (10)	0.0063 (10)

Geometric parameters (Å, º) top

Cl1—C17	1.7334 (17)	C20—C24	1.527 (2)
O1—C1	1.361 (2)	C21—C22	1.524 (2)
O1—C20	1.4633 (19)	C22—C23	1.508 (3)
O2—C1	1.202 (2)	C23—C24	1.530 (2)
O3—C12	1.3807 (19)	C5—H5	0.930
O3—C13	1.3681 (18)	C7—H7	0.930
O4—C13	1.195 (2)	C9—H91	0.960
C1—C2	1.475 (2)	C9—H92	0.960
C2—C3	1.483 (2)	C9—H93	0.960
C2—C12	1.317 (2)	C10—H101	0.960
C3—C4	1.393 (2)	C10—H102	0.960
C3—C8	1.396 (2)	C10—H103	0.960
C4—C5	1.389 (2)	C11—H111	0.960
C4—C9	1.507 (2)	C11—H112	0.960
C5—C6	1.386 (2)	C11—H113	0.960
C6—C7	1.369 (3)	C15—H15	0.930
C6—C10	1.524 (3)	C16—H16	0.930
C7—C8	1.383 (2)	C18—H18	0.930
C8—C11	1.504 (2)	C19—H19	0.930
C12—C20	1.4978 (19)	C21—H211	0.970
C13—C14	1.471 (2)	C21—H212	0.970
C14—C15	1.366 (2)	C22—H221	0.970
C14—C19	1.380 (2)	C22—H222	0.970
C15—C16	1.377 (2)	C23—H231	0.970
C16—C17	1.368 (2)	C23—H232	0.970
C17—C18	1.357 (2)	C24—H241	0.970
C18—C19	1.378 (2)	C24—H242	0.970
C20—C21	1.520 (2)

C1—O1—C20	110.04 (11)	C6—C5—H5	119.0
C12—O3—C13	117.84 (11)	C6—C7—H7	118.5
O1—C1—O2	121.16 (14)	C8—C7—H7	118.5
O1—C1—C2	109.66 (14)	C4—C9—H91	109.5
O2—C1—C2	129.18 (15)	C4—C9—H92	109.5
C1—C2—C3	123.33 (15)	C4—C9—H93	109.5
C1—C2—C12	105.54 (13)	H91—C9—H92	109.5
C3—C2—C12	131.13 (14)	H91—C9—H93	109.5
C2—C3—C4	119.47 (13)	H92—C9—H93	109.5
C2—C3—C8	119.99 (14)	C6—C10—H101	109.5
C4—C3—C8	120.52 (14)	C6—C10—H102	109.5
C3—C4—C5	118.58 (15)	C6—C10—H103	109.5
C3—C4—C9	121.32 (14)	H101—C10—H102	109.5
C5—C4—C9	120.11 (16)	H101—C10—H103	109.5
C4—C5—C6	121.98 (19)	H102—C10—H103	109.5
C5—C6—C7	117.69 (18)	C8—C11—H111	109.5
C5—C6—C10	120.8 (2)	C8—C11—H112	109.5
C7—C6—C10	121.5 (2)	C8—C11—H113	109.5
C6—C7—C8	122.96 (18)	H111—C11—H112	109.5
C3—C8—C7	118.25 (17)	H111—C11—H113	109.5
C3—C8—C11	121.71 (15)	H112—C11—H113	109.5
C7—C8—C11	120.04 (16)	C14—C15—H15	119.7
O3—C12—C2	128.10 (12)	C16—C15—H15	119.7
O3—C12—C20	118.17 (13)	C15—C16—H16	120.2
C2—C12—C20	113.69 (13)	C17—C16—H16	120.2
O3—C13—O4	121.26 (15)	C17—C18—H18	120.1
O3—C13—C14	112.40 (13)	C19—C18—H18	120.1
O4—C13—C14	126.30 (15)	C14—C19—H19	119.8
C13—C14—C15	122.92 (13)	C18—C19—H19	119.8
C13—C14—C19	117.99 (14)	C20—C21—H211	111.2
C15—C14—C19	119.05 (15)	C20—C21—H212	111.2
C14—C15—C16	120.62 (14)	C22—C21—H211	111.2
C15—C16—C17	119.63 (15)	C22—C21—H212	111.2
Cl1—C17—C16	120.17 (13)	H211—C21—H212	109.5
Cl1—C17—C18	119.25 (13)	C21—C22—H221	110.9
C16—C17—C18	120.53 (16)	C21—C22—H222	110.9
C17—C18—C19	119.79 (16)	C23—C22—H221	110.9
C14—C19—C18	120.34 (16)	C23—C22—H222	110.9
O1—C20—C12	101.01 (11)	H221—C22—H222	109.5
O1—C20—C21	108.02 (12)	C22—C23—H231	110.3
O1—C20—C24	109.27 (12)	C22—C23—H232	110.3
C12—C20—C21	115.86 (12)	C24—C23—H231	110.3
C12—C20—C24	117.98 (12)	C24—C23—H232	110.3
C21—C20—C24	104.32 (12)	H231—C23—H232	109.5
C20—C21—C22	102.49 (13)	C20—C24—H241	110.3
C21—C22—C23	103.88 (14)	C20—C24—H242	110.3
C22—C23—C24	106.19 (16)	C23—C24—H241	110.3
C20—C24—C23	106.01 (14)	C23—C24—H242	110.3
C4—C5—H5	119.0	H241—C24—H242	109.5

C1—O1—C20—C12	1.70 (14)	C5—C6—C7—C8	−1.2 (3)
C1—O1—C20—C21	−120.35 (12)	C10—C6—C7—C8	178.4 (2)
C1—O1—C20—C24	126.75 (12)	C6—C7—C8—C3	0.1 (2)
C20—O1—C1—O2	179.74 (14)	C6—C7—C8—C11	179.8 (2)
C20—O1—C1—C2	−0.57 (16)	O3—C12—C20—O1	175.69 (11)
C12—O3—C13—O4	−5.0 (2)	O3—C12—C20—C21	−67.91 (18)
C12—O3—C13—C14	176.84 (12)	O3—C12—C20—C24	56.74 (18)
C13—O3—C12—C2	−71.27 (19)	C2—C12—C20—O1	−2.47 (16)
C13—O3—C12—C20	110.86 (14)	C2—C12—C20—C21	113.92 (16)
O1—C1—C2—C3	178.86 (12)	C2—C12—C20—C24	−121.43 (16)
O1—C1—C2—C12	−1.01 (16)	O3—C13—C14—C15	−9.4 (2)
O2—C1—C2—C3	−1.5 (2)	O3—C13—C14—C19	168.51 (14)
O2—C1—C2—C12	178.65 (16)	O4—C13—C14—C15	172.61 (16)
C1—C2—C3—C4	−70.0 (2)	O4—C13—C14—C19	−9.5 (2)
C1—C2—C3—C8	108.53 (18)	C13—C14—C15—C16	179.61 (14)
C1—C2—C12—O3	−175.75 (13)	C13—C14—C19—C18	−179.44 (16)
C1—C2—C12—C20	2.20 (17)	C15—C14—C19—C18	−1.5 (2)
C3—C2—C12—O3	4.4 (2)	C19—C14—C15—C16	1.7 (2)
C3—C2—C12—C20	−177.65 (14)	C14—C15—C16—C17	−0.2 (2)
C12—C2—C3—C4	109.8 (2)	C15—C16—C17—Cl1	−178.99 (12)
C12—C2—C3—C8	−71.6 (2)	C15—C16—C17—C18	−1.7 (2)
C2—C3—C4—C5	178.81 (15)	Cl1—C17—C18—C19	179.29 (14)
C2—C3—C4—C9	−1.5 (2)	C16—C17—C18—C19	1.9 (2)
C2—C3—C8—C7	−178.18 (17)	C17—C18—C19—C14	−0.4 (2)
C2—C3—C8—C11	2.1 (2)	O1—C20—C21—C22	−78.01 (15)
C4—C3—C8—C7	0.4 (2)	O1—C20—C24—C23	94.02 (15)
C4—C3—C8—C11	−179.37 (17)	C12—C20—C21—C22	169.61 (14)
C8—C3—C4—C5	0.3 (2)	C12—C20—C24—C23	−151.47 (14)
C8—C3—C4—C9	179.99 (14)	C21—C20—C24—C23	−21.28 (17)
C3—C4—C5—C6	−1.4 (2)	C24—C20—C21—C22	38.17 (16)
C9—C4—C5—C6	178.88 (19)	C20—C21—C22—C23	−40.81 (18)
C4—C5—C6—C7	1.8 (3)	C21—C22—C23—C24	27.7 (2)
C4—C5—C6—C10	−177.7 (2)	C22—C23—C24—C20	−4.02 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C24—H242···O2ⁱ	0.97	2.57	3.475 (2)	155

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₃ClO₄
M_r	410.90
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	6.4880 (2), 22.9397 (8), 14.6305 (6)
β (°)	91.533 (1)
V (Å³)	2176.72 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.62 × 0.48 × 0.34

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.867, 0.934
No. of measured, independent and observed [F² > 2σ(F²)] reflections	33470, 4926, 3235
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.092, 1.00
No. of reflections	4926
No. of parameters	263
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.17

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1993), CRYSTALS (Betteridge et al., 2003), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C24—H242···O2ⁱ	0.97	2.57	3.475 (2)	155

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

The authors are grateful for support from the National Natural Science Foundation of China (No. 30700532) and the Science and Technology Project of Zhejiang Province (No. 2008C02007-3, 2008C21029). They also thank Professor Jian-Ming Gu for help with the analysis of the crystal data.

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
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Web of Science CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals 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 (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Yu, C.-M., Zhou, Y., Cheng, J.-L. & Zhao, J.-H. (2009). Acta Cryst. E65, o183. Web of Science CSD CrossRef IUCr Journals Google Scholar