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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o183.
Published online 2008 December 20. doi:  10.1107/S1600536808043043
PMCID: PMC2968092

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

Abstract

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 [triangle]); Bayer Aktiengesellschaft (1995 [triangle]).

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Object name is e-65-0o183-scheme1.jpg

Experimental

Crystal data

  • C28H31ClO4
  • M r = 467.00
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o183-efi1.jpg
  • 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 [triangle]) T min = 0.927, T max = 0.953
  • 25138 measured reflections
  • 5906 independent reflections
  • 2647 reflections with F 2 > 2σ(F 2)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks General, I. DOI: 10.1107/S1600536808043043/is2366sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043043/is2366Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

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 c axis.

Crystal data

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

Rigaku R-AXIS RAPID diffractometer2647 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 = −18→15
Tmin = 0.927, Tmax = 0.953k = −18→18
25138 measured reflectionsl = −18→18
5906 independent reflections

Refinement

Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046w = 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)

Special details

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)

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)
H110.3408−0.0462−0.05380.130*
H130.2718−0.11230.17990.116*
H190.68890.06790.44240.083*
H200.7769−0.00560.31050.100*
H240.6248−0.09370.23410.110*
H250.5272−0.22780.21320.127*
H270.4802−0.16580.46130.120*
H280.5809−0.03320.48430.098*
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*
H1520.34080.1620−0.06380.145*
H1530.43690.0970−0.04800.145*
H1610.3352−0.22040.00670.211*
H1620.2172−0.1911−0.05170.211*
H1630.2569−0.23070.05980.211*
H1710.2736−0.00410.30200.113*
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*
H2210.8144−0.10280.45100.144*
H2220.8562−0.01770.52590.144*
H2230.9184−0.05190.46240.144*

Atomic displacement parameters (Å2)

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, °)

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—O2−178.3 (2)C8—C9—C10—C15−1.4 (3)
C2—O1—C7—C83.1 (3)C8—C9—C14—C13−178.19 (18)
C7—O1—C2—C1−3.2 (2)C8—C9—C14—C170.5 (2)
C7—O1—C2—C3118.8 (2)C10—C9—C14—C130.0 (2)
C7—O1—C2—C6−128.2 (2)C10—C9—C14—C17178.74 (18)
C1—O3—C18—O47.7 (2)C14—C9—C10—C110.3 (3)
C1—O3—C18—C19−170.62 (17)C14—C9—C10—C15−179.6 (2)
C18—O3—C1—C2−115.3 (2)C9—C10—C11—C12−0.6 (3)
C18—O3—C1—C868.4 (3)C15—C10—C11—C12179.4 (2)
O3—C1—C2—O1−174.4 (2)C10—C11—C12—C130.4 (4)
O3—C1—C2—C368.0 (2)C10—C11—C12—C16−179.1 (2)
O3—C1—C2—C6−54.4 (3)C11—C12—C13—C14−0.0 (3)
O3—C1—C8—C7175.8 (2)C16—C12—C13—C14179.5 (2)
O3—C1—C8—C9−5.6 (4)C12—C13—C14—C9−0.2 (3)
C2—C1—C8—C7−0.6 (3)C12—C13—C14—C17−178.9 (2)
C2—C1—C8—C9177.9 (2)O3—C18—C19—C20−149.74 (17)
C8—C1—C2—O12.4 (3)O3—C18—C19—C2385.7 (2)
C8—C1—C2—C3−115.2 (2)O4—C18—C19—C2032.0 (3)
C8—C1—C2—C6122.4 (2)O4—C18—C19—C23−92.5 (2)
O1—C2—C3—C482.6 (2)C18—C19—C20—C2157.2 (2)
O1—C2—C6—C5−91.6 (2)C18—C19—C20—C22179.54 (18)
C1—C2—C3—C4−164.07 (18)C18—C19—C23—C2471.0 (2)
C1—C2—C6—C5152.9 (2)C18—C19—C23—C28−108.2 (2)
C3—C2—C6—C524.7 (2)C20—C19—C23—C24−53.1 (2)
C6—C2—C3—C4−34.6 (2)C20—C19—C23—C28127.7 (2)
C2—C3—C4—C531.7 (2)C23—C19—C20—C21177.81 (18)
C3—C4—C5—C6−16.4 (2)C23—C19—C20—C22−59.9 (2)
C4—C5—C6—C2−5.4 (2)C19—C23—C24—C25−179.93 (19)
O1—C7—C8—C1−1.5 (3)C19—C23—C28—C27179.2 (2)
O1—C7—C8—C9179.8 (2)C24—C23—C28—C27−0.1 (2)
O2—C7—C8—C1180.0 (2)C28—C23—C24—C25−0.6 (3)
O2—C7—C8—C91.3 (5)C23—C24—C25—C260.1 (3)
C1—C8—C9—C10−106.0 (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—C14−109.4 (2)C25—C26—C27—C28−1.9 (3)
C8—C9—C10—C11178.6 (2)C26—C27—C28—C231.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C17—H173···Cl1i0.962.803.624 (5)144

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2366).

References

  • 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.
  • Bayer Aktiengesellschaft (1995). WO patent No. 9 504 719A1.
  • Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst.36, 1487.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Holmstead, R. L., Fullmer, D. G. & Ruzo, L. O. (1978). J. Agric. Food Chem.26, 954–959.
  • Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291–294. Copenhagen: Munksgaard.
  • Rigaku (1998). PROCESS-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.

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