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

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ISSN: 2056-9890

3-Mesityl-2-oxo-1-oxa­spiro­[4.4]non-3-en-4-yl 2-(4-chloro­phen­yl)-3-methyl­butyrate

aCollege of Chemical Engineering and Materials Science, Zhejiang University of Technology, 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 18 November 2008; accepted 17 December 2008; online 20 December 2008)

In the title compound, C28H31ClO4, the five-membered cyclo­pentyl ring displays an envelope conformation with the atom at the flap position 0.519 (3) Å out of the mean plane formed by the other four atoms. The furan ring makes dihedral angles of 72.9 (1) and 82.4 (1)°, respectively, with the trimethyl- and chloro­phenyl rings. The dihedral angle between the two benzene rings is 15.3 (1)°. In the crystal, mol­ecules are linked through inter­molecular C—H⋯Cl hydrogen bonds, forming a chain running along the b axis.

Related literature

For related compounds, see: Holmstead et al. (1978[Holmstead, R. L., Fullmer, D. G. & Ruzo, L. O. (1978). J. Agric. Food Chem. 26, 954-959.]); Bayer Aktiengesellschaft (1995[Bayer Aktiengesellschaft (1995). WO patent No. 9 504 719A1.]).

[Scheme 1]

Experimental

Crystal data
  • C28H31ClO4

  • Mr = 467.00

  • Monoclinic, P 21 /n

  • a = 13.9224 (11) Å

  • b = 14.2735 (12) Å

  • c = 14.3209 (11) Å

  • β = 113.9567 (17)°

  • V = 2600.7 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.18 mm−1

  • T = 296 (1) K

  • 0.40 × 0.37 × 0.27 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.927, Tmax = 0.953

  • 25138 measured reflections

  • 5906 independent reflections

  • 2647 reflections with F2 > 2σ(F2)

  • Rint = 0.054

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.101

  • S = 1.00

  • 5906 reflections

  • 299 parameters

  • H-atom parameters constrained

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.54 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C17—H173⋯Cl1i 0.96 2.80 3.624 (5) 144
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]) and Larson (1970[Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291-294. Copenhagen: Munksgaard.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: CrystalStructure.

Supporting information


Comment top

2-(4-Chlorophenyl)-3-methylbutanoyl chloride is an intermediate in the synthesis of fenvalerate, an excellent insecticide (Holmstead et al., 1978). 4-Hydroxyl-3-(2,4,6-trimethylphenyl)-1-oxaspiro[4,4]non-3-en-2-one is the key intermediate in preparing highly efficient acaricide-Spiromesifen developed by Bayer company (BAYER Aktiengesellschaft, 1995). As part of our continuing interest in the new acaricide design and synthesis, We have isolated the product, (I), of the condensation reaction of 2-(4-chlorophenyl)-3-methylbutanoyl chloride and 4-hydroxyl-3-(2,4,6-trimethylphenyl)-1-oxaspiro[4,4]non-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 two six-membered rings and two five-membered rings. The dihedral angles between the (C9—C14) and (C23—C28) rings, the (C9—C14) and furan rings, and the (C23—C28) and furan rings, are 15.3 (1), 72.9 (1) and 82.4 (1)°, respectively. The cyclopentyl ring displays an envelope conformation with C3 atom at the flap position 0.519 (3) Å out of the mean plane formed by the other four atoms. The title molecules are linked through intermolecular hydrogen bond of C17—H173···Cl1, forming chains running along the b axis. As expected, C1—C8, C7—O2 and C18—O4 are typically double bonds with bond distances of 1.327 (2), 1.207 (2) and 1.189 (3) Å. The bond distance of C7—C8 is 1.480 (2) Å, suggesting that carbonyl group on C7 has formed conjugate system with double bond on C8 and C1.

Related literature top

For related compounds, see: Holmstead et al. (1978); BAYER Aktiengesellschaft (1995).

Experimental top

4-Hydroxyl-3-(2,4,6-trimethylphenyl)-1-oxaspiro[4,4]non-3-en-2-one (2.72 g, 10 mmol), 4-dimethylaminopyridine (0.58 g), triethylamine (1.31 g) 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 2-(4-chlorophenyl)-3-methylbutanoyl chloride (3.47 g) 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 ether (1:30, v/v) to give a white solid (yield 79%, 3.69 g), which was then recrystallized from ethyl acetate/ethanol (1:1, v/v) to give colourless blocks.

Refinement top

The H atoms were geometrically placed (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The methyl group was allowed to rotate, but not to tip, to best fit the electron density.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002) and Larson (1970); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2002).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A packing diagram of the title compound, viewed along the c axis.
3-Mesityl-2-oxo-1-oxaspiro[4.4]non-3-en-4-yl 2-(4-chlorophenyl)-3-methylbutyrate top
Crystal data top
C28H31ClO4F(000) = 992.00
Mr = 467.00Dx = 1.193 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ynCell parameters from 11287 reflections
a = 13.9224 (11) Åθ = 3.0–27.4°
b = 14.2735 (12) ŵ = 0.18 mm1
c = 14.3209 (11) ÅT = 296 K
β = 113.9567 (17)°Chunk, colorless
V = 2600.7 (4) Å30.40 × 0.37 × 0.27 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2647 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.054
ω scansθmax = 27.4°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1815
Tmin = 0.927, Tmax = 0.953k = 1818
25138 measured reflectionsl = 1818
5906 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046 w = 1/[0.0001Fo2 + 1.12σ(Fo2)]/(4Fo2)
wR(F2) = 0.101(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.54 e Å3
5906 reflectionsΔρmin = 0.54 e Å3
299 parametersExtinction correction: Larson (1970)
0 restraintsExtinction coefficient: 275 (22)
Crystal data top
C28H31ClO4V = 2600.7 (4) Å3
Mr = 467.00Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.9224 (11) ŵ = 0.18 mm1
b = 14.2735 (12) ÅT = 296 K
c = 14.3209 (11) Å0.40 × 0.37 × 0.27 mm
β = 113.9567 (17)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5906 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
2647 reflections with F2 > 2σ(F2)
Tmin = 0.927, Tmax = 0.953Rint = 0.054
25138 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 1.00Δρmax = 0.54 e Å3
5906 reflectionsΔρmin = 0.54 e Å3
299 parameters
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
xyzUiso*/Ueq
Cl10.42195 (6)0.31031 (6)0.32057 (8)0.1664 (4)
O10.37536 (12)0.34277 (11)0.19058 (12)0.0873 (5)
O20.24190 (12)0.27677 (12)0.05869 (11)0.1041 (6)
O30.54613 (10)0.15522 (10)0.32535 (9)0.0693 (4)
O40.61227 (11)0.11705 (12)0.21110 (12)0.1006 (6)
C10.46853 (17)0.20939 (16)0.25544 (16)0.0639 (7)
C20.47353 (17)0.31237 (17)0.27165 (16)0.0718 (8)
C30.56481 (19)0.36173 (18)0.25885 (19)0.0962 (10)
C40.5705 (2)0.4562 (2)0.3081 (2)0.1294 (13)
C50.5354 (2)0.4401 (2)0.3925 (2)0.1513 (15)
C60.48043 (18)0.34765 (18)0.37461 (17)0.0897 (9)
C70.3242 (2)0.26762 (19)0.13206 (19)0.0806 (9)
C80.38420 (16)0.18106 (16)0.17554 (14)0.0657 (7)
C90.35376 (16)0.08583 (18)0.13376 (17)0.0695 (8)
C100.36238 (18)0.0607 (2)0.04329 (18)0.0876 (9)
C110.3357 (2)0.0294 (2)0.0068 (2)0.1081 (11)
C120.3023 (2)0.0946 (2)0.0562 (2)0.1111 (12)
C130.29461 (17)0.0683 (2)0.1455 (2)0.0964 (10)
C140.31929 (16)0.0202 (2)0.18571 (18)0.0738 (8)
C150.4000 (2)0.1298 (2)0.01408 (17)0.1207 (11)
C160.2754 (2)0.1933 (2)0.0138 (2)0.1759 (15)
C170.31119 (16)0.04449 (17)0.28478 (16)0.0943 (9)
C180.61283 (16)0.10648 (16)0.29364 (18)0.0713 (8)
C190.67873 (16)0.04038 (16)0.37635 (14)0.0688 (7)
C200.78659 (17)0.02336 (17)0.37580 (17)0.0836 (8)
C210.84596 (18)0.11507 (19)0.3864 (2)0.1194 (11)
C220.84973 (17)0.04342 (17)0.46174 (19)0.1202 (10)
C230.61429 (14)0.04848 (16)0.36195 (16)0.0640 (7)
C240.59659 (18)0.1081 (2)0.28109 (17)0.0914 (9)
C250.5382 (2)0.1883 (2)0.2682 (2)0.1062 (11)
C260.49659 (18)0.20939 (19)0.3369 (2)0.0921 (10)
C270.5106 (2)0.1518 (2)0.4159 (2)0.1004 (11)
C280.57019 (19)0.07207 (19)0.42889 (16)0.0817 (9)
H110.34080.04620.05380.130*
H130.27180.11230.17990.116*
H190.68890.06790.44240.083*
H200.77690.00560.31050.100*
H240.62480.09370.23410.110*
H250.52720.22780.21320.127*
H270.48020.16580.46130.120*
H280.58090.03320.48430.098*
H310.62980.32730.29320.115*
H320.55080.36860.18710.115*
H410.64200.47990.33520.155*
H420.52440.50050.25890.155*
H510.59580.43940.45770.182*
H520.48770.48960.39260.182*
H610.52010.30390.42830.108*
H620.41050.35520.37300.108*
H1510.44630.17430.03300.145*
H1520.34080.16200.06380.145*
H1530.43690.09700.04800.145*
H1610.33520.22040.00670.211*
H1620.21720.19110.05170.211*
H1630.25690.23070.05980.211*
H1710.27360.00410.30200.113*
H1720.38040.05020.33810.113*
H1730.27440.10280.27720.113*
H2110.91550.10220.39110.143*
H2120.85050.14710.44690.143*
H2130.80940.15370.32770.143*
H2210.81440.10280.45100.144*
H2220.85620.01770.52590.144*
H2230.91840.05190.46240.144*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1490 (7)0.0969 (6)0.2528 (10)0.0309 (5)0.0811 (7)0.0047 (6)
O10.0850 (11)0.0733 (12)0.0947 (10)0.0176 (10)0.0273 (9)0.0109 (9)
O20.0821 (10)0.1143 (15)0.0921 (11)0.0278 (10)0.0108 (9)0.0219 (9)
O30.0591 (8)0.0761 (11)0.0651 (8)0.0144 (8)0.0172 (7)0.0001 (7)
O40.0949 (11)0.1351 (16)0.0831 (10)0.0363 (10)0.0478 (9)0.0247 (10)
C10.0606 (14)0.0651 (17)0.0666 (13)0.0096 (13)0.0264 (11)0.0041 (12)
C20.0654 (15)0.0737 (19)0.0756 (15)0.0058 (13)0.0279 (12)0.0049 (13)
C30.0989 (19)0.083 (2)0.1177 (19)0.0086 (16)0.0549 (16)0.0063 (16)
C40.158 (2)0.103 (2)0.130 (2)0.038 (2)0.060 (2)0.015 (2)
C50.239 (3)0.108 (2)0.123 (2)0.038 (2)0.089 (2)0.021 (2)
C60.0990 (18)0.083 (2)0.0945 (17)0.0096 (16)0.0468 (14)0.0046 (14)
C70.0748 (17)0.085 (2)0.0815 (16)0.0142 (17)0.0315 (13)0.0117 (16)
C80.0597 (14)0.0692 (18)0.0674 (14)0.0103 (13)0.0250 (11)0.0072 (13)
C90.0558 (13)0.0770 (19)0.0643 (15)0.0092 (13)0.0128 (11)0.0016 (14)
C100.0793 (16)0.106 (2)0.0632 (16)0.0215 (16)0.0138 (12)0.0028 (17)
C110.101 (2)0.120 (2)0.0779 (19)0.018 (2)0.0097 (15)0.030 (2)
C120.0754 (18)0.095 (2)0.122 (2)0.0022 (18)0.0015 (18)0.035 (2)
C130.0639 (15)0.084 (2)0.118 (2)0.0059 (15)0.0132 (15)0.0046 (18)
C140.0520 (13)0.082 (2)0.0751 (15)0.0024 (13)0.0134 (11)0.0015 (15)
C150.144 (2)0.149 (2)0.0794 (16)0.029 (2)0.0556 (17)0.0108 (18)
C160.145 (2)0.126 (2)0.212 (3)0.025 (2)0.026 (2)0.079 (2)
C170.0816 (16)0.109 (2)0.0970 (17)0.0076 (15)0.0410 (13)0.0154 (15)
C180.0582 (14)0.0827 (18)0.0715 (15)0.0098 (13)0.0250 (12)0.0012 (14)
C190.0604 (13)0.0752 (17)0.0644 (12)0.0112 (13)0.0186 (10)0.0014 (11)
C200.0618 (14)0.0789 (18)0.1046 (17)0.0063 (14)0.0282 (13)0.0084 (14)
C210.0784 (17)0.106 (2)0.169 (2)0.0032 (17)0.0455 (17)0.0001 (19)
C220.0646 (15)0.108 (2)0.152 (2)0.0190 (16)0.0073 (15)0.0158 (19)
C230.0587 (13)0.0717 (17)0.0555 (12)0.0099 (12)0.0169 (11)0.0017 (13)
C240.0884 (18)0.111 (2)0.0807 (17)0.0201 (17)0.0403 (13)0.0232 (16)
C250.097 (2)0.111 (2)0.106 (2)0.0161 (18)0.0368 (17)0.0342 (18)
C260.0726 (16)0.072 (2)0.125 (2)0.0007 (14)0.0333 (16)0.0003 (18)
C270.114 (2)0.087 (2)0.119 (2)0.0104 (19)0.0669 (17)0.0220 (19)
C280.0943 (18)0.081 (2)0.0755 (15)0.0144 (16)0.0407 (14)0.0085 (14)
Geometric parameters (Å, º) top
Cl1—C261.736 (2)C26—C271.347 (4)
O1—C21.455 (2)C27—C281.376 (4)
O1—C71.370 (2)C3—H310.970
O2—C71.207 (2)C3—H320.970
O3—C11.374 (2)C4—H410.970
O3—C181.377 (3)C4—H420.970
O4—C181.189 (3)C5—H510.970
C1—C21.485 (3)C5—H520.970
C1—C81.327 (2)C6—H610.970
C2—C31.528 (3)C6—H620.970
C2—C61.524 (3)C11—H110.930
C3—C41.509 (3)C13—H130.930
C4—C51.495 (5)C15—H1510.960
C5—C61.495 (4)C15—H1520.960
C7—C81.480 (3)C15—H1530.960
C8—C91.476 (3)C16—H1610.960
C9—C101.396 (3)C16—H1620.960
C9—C141.397 (3)C16—H1630.960
C10—C111.382 (4)C17—H1710.960
C10—C151.507 (4)C17—H1720.960
C11—C121.360 (5)C17—H1730.960
C12—C131.377 (5)C19—H190.980
C12—C161.519 (4)C20—H200.980
C13—C141.374 (4)C21—H2110.960
C14—C171.508 (3)C21—H2120.960
C18—C191.501 (2)C21—H2130.960
C19—C201.524 (3)C22—H2210.960
C19—C231.519 (3)C22—H2220.960
C20—C211.523 (3)C22—H2230.960
C20—C221.522 (3)C24—H240.930
C23—C241.376 (3)C25—H250.930
C23—C281.374 (3)C27—H270.930
C24—C251.372 (4)C28—H280.930
C25—C261.364 (5)
C2—O1—C7109.97 (17)C5—C4—H41110.4
C1—O3—C18118.69 (17)C5—C4—H42110.4
O3—C1—C2118.02 (15)H41—C4—H42109.5
O3—C1—C8128.0 (2)C4—C5—H51109.8
C2—C1—C8113.91 (18)C4—C5—H52109.8
O1—C2—C1101.61 (15)C6—C5—H51109.8
O1—C2—C3108.93 (18)C6—C5—H52109.8
O1—C2—C6110.08 (19)H51—C5—H52109.5
C1—C2—C3115.2 (2)C2—C6—H61110.2
C1—C2—C6117.3 (2)C2—C6—H62110.2
C3—C2—C6103.59 (18)C5—C6—H61110.2
C2—C3—C4104.2 (2)C5—C6—H62110.2
C3—C4—C5105.6 (2)H61—C6—H62109.5
C4—C5—C6108.0 (2)C10—C11—H11118.8
C2—C6—C5106.5 (2)C12—C11—H11118.8
O1—C7—O2121.5 (2)C12—C13—H13118.7
O1—C7—C8109.38 (16)C14—C13—H13118.7
O2—C7—C8129.1 (2)C10—C15—H151109.5
C1—C8—C7105.02 (19)C10—C15—H152109.5
C1—C8—C9129.65 (19)C10—C15—H153109.5
C7—C8—C9125.32 (16)H151—C15—H152109.5
C8—C9—C10119.6 (2)H151—C15—H153109.5
C8—C9—C14120.4 (2)H152—C15—H153109.5
C10—C9—C14120.0 (2)C12—C16—H161109.5
C9—C10—C11118.6 (2)C12—C16—H162109.5
C9—C10—C15121.2 (2)C12—C16—H163109.5
C11—C10—C15120.2 (2)H161—C16—H162109.5
C10—C11—C12122.4 (3)H161—C16—H163109.5
C11—C12—C13118.0 (3)H162—C16—H163109.5
C11—C12—C16120.5 (3)C14—C17—H171109.5
C13—C12—C16121.6 (3)C14—C17—H172109.5
C12—C13—C14122.6 (3)C14—C17—H173109.5
C9—C14—C13118.4 (2)H171—C17—H172109.5
C9—C14—C17121.3 (2)H171—C17—H173109.5
C13—C14—C17120.3 (2)H172—C17—H173109.5
O3—C18—O4122.08 (18)C18—C19—H19108.2
O3—C18—C19109.6 (2)C20—C19—H19108.2
O4—C18—C19128.3 (2)C23—C19—H19108.2
C18—C19—C20112.6 (2)C19—C20—H20108.5
C18—C19—C23106.25 (15)C21—C20—H20108.5
C20—C19—C23113.27 (19)C22—C20—H20108.5
C19—C20—C21111.0 (2)C20—C21—H211109.5
C19—C20—C22110.0 (2)C20—C21—H212109.5
C21—C20—C22110.24 (16)C20—C21—H213109.5
C19—C23—C24121.7 (2)H211—C21—H212109.5
C19—C23—C28121.1 (2)H211—C21—H213109.5
C24—C23—C28117.2 (2)H212—C21—H213109.5
C23—C24—C25121.5 (2)C20—C22—H221109.5
C24—C25—C26119.3 (2)C20—C22—H222109.5
Cl1—C26—C25119.5 (2)C20—C22—H223109.5
Cl1—C26—C27119.6 (2)H221—C22—H222109.5
C25—C26—C27120.8 (2)H221—C22—H223109.5
C26—C27—C28119.5 (3)H222—C22—H223109.5
C23—C28—C27121.6 (2)C23—C24—H24119.2
C2—C3—H31110.8C25—C24—H24119.2
C2—C3—H32110.8C24—C25—H25120.4
C4—C3—H31110.8C26—C25—H25120.4
C4—C3—H32110.8C26—C27—H27120.3
H31—C3—H32109.5C28—C27—H27120.3
C3—C4—H41110.4C23—C28—H28119.2
C3—C4—H42110.4C27—C28—H28119.2
C2—O1—C7—O2178.3 (2)C8—C9—C10—C151.4 (3)
C2—O1—C7—C83.1 (3)C8—C9—C14—C13178.19 (18)
C7—O1—C2—C13.2 (2)C8—C9—C14—C170.5 (2)
C7—O1—C2—C3118.8 (2)C10—C9—C14—C130.0 (2)
C7—O1—C2—C6128.2 (2)C10—C9—C14—C17178.74 (18)
C1—O3—C18—O47.7 (2)C14—C9—C10—C110.3 (3)
C1—O3—C18—C19170.62 (17)C14—C9—C10—C15179.6 (2)
C18—O3—C1—C2115.3 (2)C9—C10—C11—C120.6 (3)
C18—O3—C1—C868.4 (3)C15—C10—C11—C12179.4 (2)
O3—C1—C2—O1174.4 (2)C10—C11—C12—C130.4 (4)
O3—C1—C2—C368.0 (2)C10—C11—C12—C16179.1 (2)
O3—C1—C2—C654.4 (3)C11—C12—C13—C140.0 (3)
O3—C1—C8—C7175.8 (2)C16—C12—C13—C14179.5 (2)
O3—C1—C8—C95.6 (4)C12—C13—C14—C90.2 (3)
C2—C1—C8—C70.6 (3)C12—C13—C14—C17178.9 (2)
C2—C1—C8—C9177.9 (2)O3—C18—C19—C20149.74 (17)
C8—C1—C2—O12.4 (3)O3—C18—C19—C2385.7 (2)
C8—C1—C2—C3115.2 (2)O4—C18—C19—C2032.0 (3)
C8—C1—C2—C6122.4 (2)O4—C18—C19—C2392.5 (2)
O1—C2—C3—C482.6 (2)C18—C19—C20—C2157.2 (2)
O1—C2—C6—C591.6 (2)C18—C19—C20—C22179.54 (18)
C1—C2—C3—C4164.07 (18)C18—C19—C23—C2471.0 (2)
C1—C2—C6—C5152.9 (2)C18—C19—C23—C28108.2 (2)
C3—C2—C6—C524.7 (2)C20—C19—C23—C2453.1 (2)
C6—C2—C3—C434.6 (2)C20—C19—C23—C28127.7 (2)
C2—C3—C4—C531.7 (2)C23—C19—C20—C21177.81 (18)
C3—C4—C5—C616.4 (2)C23—C19—C20—C2259.9 (2)
C4—C5—C6—C25.4 (2)C19—C23—C24—C25179.93 (19)
O1—C7—C8—C11.5 (3)C19—C23—C28—C27179.2 (2)
O1—C7—C8—C9179.8 (2)C24—C23—C28—C270.1 (2)
O2—C7—C8—C1180.0 (2)C28—C23—C24—C250.6 (3)
O2—C7—C8—C91.3 (5)C23—C24—C25—C260.1 (3)
C1—C8—C9—C10106.0 (3)C24—C25—C26—Cl1179.56 (19)
C1—C8—C9—C1472.2 (3)C24—C25—C26—C271.1 (3)
C7—C8—C9—C1072.4 (3)Cl1—C26—C27—C28179.72 (19)
C7—C8—C9—C14109.4 (2)C25—C26—C27—C281.9 (3)
C8—C9—C10—C11178.6 (2)C26—C27—C28—C231.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H173···Cl1i0.962.803.624 (5)144
Symmetry code: (i) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC28H31ClO4
Mr467.00
Crystal system, space groupMonoclinic, P21/n
Temperature (K)296
a, b, c (Å)13.9224 (11), 14.2735 (12), 14.3209 (11)
β (°) 113.9567 (17)
V3)2600.7 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.40 × 0.37 × 0.27
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.927, 0.953
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
25138, 5906, 2647
Rint0.054
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.101, 1.00
No. of reflections5906
No. of parameters299
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.54, 0.54

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002) and Larson (1970), SIR97 (Altomare et al., 1999), CRYSTALS (Betteridge et al., 2003), ORTEP-3 (Farrugia, 1997), CrystalStructure (Rigaku/MSC, 2002).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H173···Cl1i0.9602.8043.624 (5)144
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

Acknowledgements

The authors thank the Natural Science Foundation of Zhejiang Province, China, for financial support (2008 C21029)

References

First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationBayer Aktiengesellschaft (1995). WO patent No. 9 504 719A1.  Google Scholar
First citationBetteridge, 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
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationHolmstead, R. L., Fullmer, D. G. & Ruzo, L. O. (1978). J. Agric. Food Chem. 26, 954–959.  CrossRef CAS Web of Science Google Scholar
First citationLarson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291–294. Copenhagen: Munksgaard.  Google Scholar
First citationRigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar

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