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

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ISSN: 2056-9890

7,7-Di­methyl-3,3,4a-tris­­(3-methyl­but-2-en­yl)-4a,5,6,7-tetra­hydro-2H-chromene-2,4(3H)-dione

aFakultät Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany, and bInstitut für Organische Chemie, Fakultät Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany
*Correspondence e-mail: hans.preut@udo.edu

(Received 22 June 2009; accepted 29 June 2009; online 4 July 2009)

The title compound, C26H38O3, was prepared by an intra­molecular Claisen-like cyclization of ethyl 2-acet­oxy-4,4-dimethyl-1-(3-methyl­but-2-en­yl)cyclo­hex-2-enecarboxyl­ate followed by dialkyl­ation. One of the methyl groups is disordered over two sets of sites in a 0.67:0.33 ratio.

Related literature

For further information, see: Ciochina & Grossman (2006[Ciochina, R. & Grossman, R. B. (2006). Chem. Rev. 106, 3963-3986.]).

[Scheme 1]

Experimental

Crystal data
  • C26H38O3

  • Mr = 398.56

  • Triclinic, [P \overline 1]

  • a = 9.534 (2) Å

  • b = 11.753 (3) Å

  • c = 11.994 (2) Å

  • α = 77.862 (13)°

  • β = 78.325 (12)°

  • γ = 66.427 (9)°

  • V = 1193.7 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 173 K

  • 0.50 × 0.27 × 0.04 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: none

  • 14072 measured reflections

  • 4134 independent reflections

  • 1323 reflections with I > 2σ(I)

  • Rint = 0.078

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.112

  • S = 1.02

  • 4134 reflections

  • 280 parameters

  • H-atom parameters constrained

  • Δρmax = 0.11 e Å−3

  • Δρmin = −0.10 e Å−3

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Related literature top

For further synthetic information, see: Ciochina & Grossman (2006).

Experimental top

Diethyl ether was dryed over sodium. All other solvents and reagents were commercially available and used as received. Flash-chromatography was performed on silicagel 60 (230–400 mesh) using head pressure by means of compressed air. Infrared spectra (IR) were recorded as a thin film between KBr-plates. The instrument used was a Bruker IFS 66 FT—IR spectrophotometer. GC—MS spectra were recorded on a Finnigan Polaris GCQ spectrometer. Proton (1H NMR, 500 MHz) and carbon (13C NMR, 125 MHz) nuclear magnetic resonance spectra were recorded in chloroform(d-1) and referenced to the solvent signal. The instrument used was a Bruker DRX 500. The multiplicities of the signals are given as s (singlet), d (doublet), t (triplet), and m (multiplet).

HMDS (780 µL, 3.425 mmol) was dissolved in diethylether (3 ml) at 273 K. Butyllithium (2.1 ml, 3.36 mmol, 1.6 M in hexane) was added at that temperature and the mixture was stirred for 15 minutes. After cooling to 195 K a suspension of CuI (360 mg, 1.89 mmol) and ethyl 2-acetoxy-4,4-dimethyl-1-(3-methylbut-2-enyl)cyclohex-2-enecarboxylate (580 mg, 1.88 mmol) in diethylether (3 ml) was added (Ciochina & Grossman, 2006). The mixture was stirred for 2 h. Isoprenylbromide (440 µl, 3.78 mmol) was added dropwise and the mixture was stirred for 5 days at room temperature. An aqueous Seignette salt-solution was added. Phases were separated and the aqueous layer was extracted with diethylether (3 x 10 ml). The combined organic layers were dried over Na2SO4 and concentrated in vacuum. The crude product was purified via column chromatography (20:1 i-hexane/ethyl acetate). The title compound was obtained in 30% yield (223 mg, 0.559 mmol) and crystallized by slow evaporation of a mixture of diethyether and i-hexane.

Rf: 0.57 (isohexan/ethyl acetate 10:1), mp: 325 K, 1H NMR (500 MHz, CDCl3): δ(p.p.m.) = 5.40 (s, 1H, CH), 5.01–4.96 (m, 2H, CH), 4.84 (m, 1H, CH–), 2.64–2.54 (m, 3H, CH2), 2.33–2.26 (m, 2H, CH2), 2.07–2.00 (m, 2H, CH2), 1.82–1.87 (m, 1H, CH2), 1.68 (s, 3H, CH3), 1.63 (s, 3H, CH3), 1.57/1.58 (2*s, 9H, CH3), 1.46–1.41 (m, 1H, CH2), 1.26–1.21 (m, 1H, CH2), 1.03 (s, 3H, CH3), 1.00 (s, 3H, CH3). 13C NMR (125 MHz, CDCl3): δ (p.p.m.) = 206.6, 169.7, 146.0, 137.1, 135.9, 135.6, 122.3, 117.5, 116.6, 61.5, 50.3, 37.4, 33.9, 32.4, 32.2, 29.7, 29.2, 26.2, 26.1, 26.0, 24.8, 18.2, 18.0. IR (film): ν (cm-1) = 2963 (m), 2917 (m), 1770 (s), 1717 (s), 1674 (m), 1449 (m), 1221 (m), 1113 (m), 1062 (m). MS (EI, 70 eV): m / z (%) = 398 (2) [M+], 370 (1) [C25H38O2+], 329 (28) [C21H29O3+], 315 (16) [C21H31O2+], 301 (1) [C25H38O2+], 262 (100) [C16H22O3+], 247 (69), 206 (77) [C13H18O2+], 191 (57) [C12H15O2+], 177 (7) [C12H17O+], 137 (10) [C9H13O+], 69 (74) [C5H9+]. HRMS (FAB+HR,C26H28O3) calc. [(M+H)+]: 399.2899; found: 399.2914.

Refinement top

H atoms were placed in calculated positions, with C—H = 0.95–0.99 Å and were refined as riding, with Uiso= 1.5Ueq for methyl and 1.2Ueq for others; the methyl groups were allowed to rotate but not to tip. One methyl group is disordered over two positions in a 0.67:0.33 ratio.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. : The molecular structure of (I) with displacement ellipsoids shown at the 30% probability level. Of the two disordered positions (C35 and C35') only one is shown.
7,7-Dimethyl-3,3,4a-tris(3-methylbut-2-enyl)-4a,5,6,7-tetrahydro-2H- chromene-2,4(3H)-dione top
Crystal data top
C26H38O3Z = 2
Mr = 398.56F(000) = 436
Triclinic, P1Dx = 1.109 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.534 (2) ÅCell parameters from 14072 reflections
b = 11.753 (3) Åθ = 3.1–25.0°
c = 11.994 (2) ŵ = 0.07 mm1
α = 77.862 (13)°T = 173 K
β = 78.325 (12)°Block, light yellow
γ = 66.427 (9)°0.50 × 0.27 × 0.04 mm
V = 1193.7 (5) Å3
Data collection top
Nonius KappaCCD
diffractometer
1323 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.078
Graphite monochromatorθmax = 25.0°, θmin = 3.1°
Detector resolution: 19 vertical, 18 horizontal pixels mm-1h = 1111
415 frames via ω–rotation (Δω = 2%) and two times 20 s per frame (four sets at different κ–angles) scansk = 1213
14072 measured reflectionsl = 1314
4134 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.02 w = {exp[6.80(sinθ/λ)2]}/[σ2(Fo2)]
4134 reflections(Δ/σ)max < 0.001
280 parametersΔρmax = 0.11 e Å3
0 restraintsΔρmin = 0.10 e Å3
Crystal data top
C26H38O3γ = 66.427 (9)°
Mr = 398.56V = 1193.7 (5) Å3
Triclinic, P1Z = 2
a = 9.534 (2) ÅMo Kα radiation
b = 11.753 (3) ŵ = 0.07 mm1
c = 11.994 (2) ÅT = 173 K
α = 77.862 (13)°0.50 × 0.27 × 0.04 mm
β = 78.325 (12)°
Data collection top
Nonius KappaCCD
diffractometer
1323 reflections with I > 2σ(I)
14072 measured reflectionsRint = 0.078
4134 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 1.02Δρmax = 0.11 e Å3
4134 reflectionsΔρmin = 0.10 e Å3
280 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
xyzUiso*/UeqOcc. (<1)
O10.4586 (2)0.12777 (19)0.11632 (17)0.0438 (6)
O20.2943 (3)0.5220 (2)0.00396 (18)0.0507 (6)
O30.1723 (2)0.3951 (2)0.08269 (17)0.0443 (6)
C10.4204 (4)0.3126 (3)0.0442 (2)0.0372 (8)
C20.3690 (4)0.2119 (3)0.0635 (2)0.0386 (8)
C30.2036 (3)0.2213 (3)0.0182 (3)0.0394 (8)
C40.1504 (4)0.2817 (3)0.0889 (3)0.0392 (8)
C60.2921 (4)0.4184 (3)0.0126 (3)0.0426 (9)
C70.1940 (4)0.0910 (3)0.0104 (3)0.0472 (9)
H7A0.20010.06040.06200.057*
H7B0.28310.03200.04980.057*
C80.0452 (4)0.0929 (3)0.0869 (3)0.0530 (10)
H8A0.04060.00850.09880.064*
H8B0.04380.15240.04760.064*
C90.0324 (4)0.1315 (3)0.2045 (3)0.0510 (9)
C100.0782 (4)0.2443 (3)0.1852 (3)0.0443 (8)
H10A0.05270.29090.24710.053*
C110.4951 (4)0.3655 (3)0.1577 (2)0.0455 (9)
H11A0.54020.42150.14050.055*
H11B0.58090.29490.19080.055*
C120.3886 (4)0.4374 (3)0.2471 (3)0.0474 (9)
H12A0.30950.51450.22980.057*
C130.3937 (4)0.4043 (3)0.3474 (3)0.0541 (10)
C140.5093 (4)0.2854 (3)0.3914 (3)0.0681 (12)
H14A0.57160.23190.33080.102*
H14B0.57690.30680.45850.102*
H14C0.45430.24040.41350.102*
C150.2786 (4)0.4871 (3)0.4286 (3)0.0691 (12)
H15A0.21060.56350.39580.104*
H15B0.21680.44200.44000.104*
H15C0.33380.50970.50270.104*
C210.5472 (3)0.2483 (3)0.0391 (2)0.0411 (8)
H21A0.64330.19690.00510.049*
H21B0.56850.31520.06240.049*
C220.5124 (3)0.1669 (3)0.1455 (3)0.0399 (8)
H22A0.51890.08680.13540.048*
C230.4738 (4)0.1926 (3)0.2516 (3)0.0417 (8)
C240.4434 (4)0.3177 (3)0.2852 (3)0.0564 (10)
H24A0.45660.37600.21610.085*
H24B0.51630.30710.33720.085*
H24C0.33760.35130.32420.085*
C250.4543 (4)0.0965 (3)0.3513 (3)0.0584 (10)
H25A0.47900.01710.32360.088*
H25B0.34730.12580.38880.088*
H25C0.52390.08390.40660.088*
C310.1015 (4)0.3067 (3)0.1133 (2)0.0476 (9)
H31A0.00820.32250.08280.057*
H31B0.11410.38850.13060.057*
C320.1389 (4)0.2524 (3)0.2233 (3)0.0529 (10)
H32A0.24070.19330.23900.064*
C330.0465 (4)0.2776 (3)0.2995 (3)0.0473 (9)
C340.0995 (4)0.2205 (3)0.4097 (3)0.0587 (10)
H34A0.20510.15840.40840.088*
H34B0.09700.28660.47540.088*
H34C0.03070.17950.41660.088*
C350.1086 (10)0.3876 (7)0.2954 (8)0.060 (2)0.67
H35A0.13380.41750.22070.091*0.67
H35B0.18900.36020.30590.091*0.67
H35C0.10250.45570.35690.091*0.67
C35'0.124 (2)0.3261 (15)0.273 (2)0.074 (6)0.33
H35D0.16030.25750.26580.111*0.33
H35E0.16920.39180.33520.111*0.33
H35F0.15500.36100.20050.111*0.33
C410.1364 (4)0.1687 (4)0.2621 (3)0.0694 (11)
H41A0.14620.19680.33570.104*
H41B0.16690.09610.27560.104*
H41C0.20350.23690.21170.104*
C420.1373 (4)0.0236 (3)0.2825 (3)0.0659 (11)
H42A0.24410.00210.24440.099*
H42B0.10390.04750.29740.099*
H42C0.13110.05150.35540.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0398 (14)0.0366 (14)0.0521 (14)0.0077 (11)0.0051 (11)0.0148 (11)
O20.0497 (15)0.0371 (15)0.0653 (16)0.0125 (12)0.0087 (12)0.0139 (12)
O30.0433 (15)0.0355 (14)0.0523 (14)0.0116 (12)0.0008 (12)0.0143 (11)
C10.038 (2)0.036 (2)0.0391 (18)0.0108 (17)0.0070 (16)0.0122 (16)
C20.044 (2)0.034 (2)0.0362 (19)0.0085 (18)0.0121 (16)0.0057 (16)
C30.035 (2)0.036 (2)0.0446 (19)0.0058 (17)0.0098 (16)0.0094 (16)
C40.037 (2)0.033 (2)0.048 (2)0.0101 (17)0.0093 (17)0.0093 (17)
C60.044 (2)0.037 (2)0.048 (2)0.0129 (18)0.0111 (18)0.0096 (17)
C70.040 (2)0.040 (2)0.064 (2)0.0118 (17)0.0118 (18)0.0128 (18)
C80.040 (2)0.047 (2)0.077 (3)0.0190 (18)0.0073 (19)0.015 (2)
C90.039 (2)0.053 (2)0.066 (2)0.0235 (19)0.0032 (19)0.010 (2)
C100.036 (2)0.046 (2)0.046 (2)0.0101 (17)0.0059 (17)0.0082 (17)
C110.049 (2)0.040 (2)0.047 (2)0.0147 (18)0.0057 (17)0.0087 (17)
C120.058 (2)0.036 (2)0.046 (2)0.0153 (18)0.0088 (18)0.0029 (17)
C130.073 (3)0.048 (2)0.046 (2)0.028 (2)0.0129 (19)0.0014 (18)
C140.092 (3)0.059 (3)0.053 (2)0.025 (2)0.008 (2)0.017 (2)
C150.093 (3)0.062 (3)0.054 (2)0.026 (2)0.031 (2)0.004 (2)
C210.036 (2)0.042 (2)0.046 (2)0.0108 (17)0.0068 (16)0.0115 (17)
C220.037 (2)0.035 (2)0.045 (2)0.0099 (16)0.0079 (16)0.0056 (17)
C230.039 (2)0.041 (2)0.043 (2)0.0098 (17)0.0073 (16)0.0086 (17)
C240.065 (3)0.054 (2)0.051 (2)0.019 (2)0.0064 (19)0.0158 (18)
C250.063 (3)0.058 (3)0.051 (2)0.019 (2)0.0108 (19)0.0045 (19)
C310.040 (2)0.048 (2)0.051 (2)0.0079 (17)0.0101 (17)0.0118 (18)
C320.036 (2)0.064 (3)0.053 (2)0.0066 (18)0.0073 (18)0.0204 (19)
C330.040 (2)0.054 (2)0.049 (2)0.0168 (18)0.0026 (17)0.0143 (18)
C340.058 (3)0.066 (3)0.052 (2)0.021 (2)0.0042 (19)0.016 (2)
C350.051 (5)0.072 (7)0.054 (4)0.009 (5)0.016 (3)0.018 (5)
C35'0.055 (10)0.060 (13)0.120 (17)0.015 (10)0.024 (9)0.043 (12)
C410.053 (3)0.076 (3)0.089 (3)0.034 (2)0.005 (2)0.025 (2)
C420.061 (3)0.060 (3)0.072 (3)0.024 (2)0.010 (2)0.006 (2)
Geometric parameters (Å, º) top
O1—C21.216 (3)C21—C221.491 (4)
O2—C61.207 (3)C21—H21A0.9900
O3—C61.361 (4)C21—H21B0.9900
O3—C41.413 (3)C22—C231.316 (4)
C1—C21.523 (4)C22—H22A0.9500
C1—C61.519 (4)C23—C251.499 (4)
C1—C111.534 (4)C23—C241.506 (4)
C1—C211.572 (4)C24—H24A0.9800
C2—C31.527 (4)C24—H24B0.9800
C3—C41.498 (4)C24—H24C0.9800
C3—C71.533 (4)C25—H25A0.9800
C3—C311.563 (4)C25—H25B0.9800
C4—C101.307 (4)C25—H25C0.9800
C7—C81.520 (4)C31—C321.502 (4)
C7—H7A0.9900C31—H31A0.9900
C7—H7B0.9900C31—H31B0.9900
C8—C91.539 (4)C32—C331.305 (4)
C8—H8A0.9900C32—H32A0.9500
C8—H8B0.9900C33—C351.526 (9)
C9—C101.514 (4)C33—C341.511 (4)
C9—C421.532 (4)C33—C35'1.48 (2)
C9—C411.541 (4)C34—H34A0.9800
C10—H10A0.9500C34—H34B0.9800
C11—C121.506 (4)C34—H34C0.9800
C11—H11A0.9900C35—H35A0.9800
C11—H11B0.9900C35—H35B0.9800
C12—C131.327 (4)C35—H35C0.9800
C12—H12A0.9500C35'—H35D0.9800
C13—C151.510 (4)C35'—H35E0.9800
C13—C141.513 (5)C35'—H35F0.9800
C14—H14A0.9800C41—H41A0.9800
C14—H14B0.9800C41—H41B0.9800
C14—H14C0.9800C41—H41C0.9800
C15—H15A0.9800C42—H42A0.9800
C15—H15B0.9800C42—H42B0.9800
C15—H15C0.9800C42—H42C0.9800
C6—O3—C4121.5 (3)H15B—C15—H15C109.5
C2—C1—C6113.8 (3)C22—C21—C1117.3 (3)
C2—C1—C11110.5 (2)C22—C21—H21A108.0
C6—C1—C11110.3 (3)C1—C21—H21A108.0
C2—C1—C21107.5 (2)C22—C21—H21B108.0
C6—C1—C21106.9 (2)C1—C21—H21B108.0
C11—C1—C21107.5 (2)H21A—C21—H21B107.2
O1—C2—C1119.7 (3)C23—C22—C21127.8 (3)
O1—C2—C3121.5 (3)C23—C22—H22A116.1
C1—C2—C3118.8 (3)C21—C22—H22A116.1
C4—C3—C2109.1 (2)C22—C23—C25121.5 (3)
C4—C3—C7108.7 (3)C22—C23—C24124.6 (3)
C2—C3—C7110.9 (2)C25—C23—C24113.9 (3)
C4—C3—C31109.3 (2)C23—C24—H24A109.5
C2—C3—C31106.9 (3)C23—C24—H24B109.5
C7—C3—C31111.7 (2)H24A—C24—H24B109.5
C10—C4—O3116.7 (3)C23—C24—H24C109.5
C10—C4—C3126.7 (3)H24A—C24—H24C109.5
O3—C4—C3116.5 (3)H24B—C24—H24C109.5
O2—C6—O3117.3 (3)C23—C25—H25A109.5
O2—C6—C1123.3 (3)C23—C25—H25B109.5
O3—C6—C1119.2 (3)H25A—C25—H25B109.5
C8—C7—C3111.9 (3)C23—C25—H25C109.5
C8—C7—H7A109.2H25A—C25—H25C109.5
C3—C7—H7A109.2H25B—C25—H25C109.5
C8—C7—H7B109.2C32—C31—C3114.1 (3)
C3—C7—H7B109.2C32—C31—H31A108.7
H7A—C7—H7B107.9C3—C31—H31A108.7
C7—C8—C9112.3 (2)C32—C31—H31B108.7
C7—C8—H8A109.2C3—C31—H31B108.7
C9—C8—H8A109.2H31A—C31—H31B107.6
C7—C8—H8B109.2C33—C32—C31127.0 (3)
C9—C8—H8B109.2C33—C32—H32A116.5
H8A—C8—H8B107.9C31—C32—H32A116.5
C10—C9—C42110.0 (3)C32—C33—C35121.1 (4)
C10—C9—C41108.8 (3)C32—C33—C34122.2 (3)
C42—C9—C41109.6 (3)C35—C33—C34115.4 (4)
C10—C9—C8108.4 (3)C32—C33—C35'123.6 (9)
C42—C9—C8110.9 (3)C34—C33—C35'111.2 (8)
C41—C9—C8109.1 (3)C33—C34—H34A109.5
C4—C10—C9124.3 (3)C33—C34—H34B109.5
C4—C10—H10A117.8H34A—C34—H34B109.5
C9—C10—H10A117.8C33—C34—H34C109.5
C12—C11—C1115.5 (3)H34A—C34—H34C109.5
C12—C11—H11A108.4H34B—C34—H34C109.5
C1—C11—H11A108.4C33—C35—H35A109.5
C12—C11—H11B108.4C33—C35—H35B109.5
C1—C11—H11B108.4C33—C35—H35C109.5
H11A—C11—H11B107.5C33—C35'—H35D109.5
C13—C12—C11126.8 (3)C33—C35'—H35E109.5
C13—C12—H12A116.6H35D—C35'—H35E109.5
C11—C12—H12A116.6C33—C35'—H35F109.5
C12—C13—C15120.6 (3)H35D—C35'—H35F109.5
C12—C13—C14125.2 (3)H35E—C35'—H35F109.5
C15—C13—C14114.2 (3)C9—C41—H41A109.5
C13—C14—H14A109.5C9—C41—H41B109.5
C13—C14—H14B109.5H41A—C41—H41B109.5
H14A—C14—H14B109.5C9—C41—H41C109.5
C13—C14—H14C109.5H41A—C41—H41C109.5
H14A—C14—H14C109.5H41B—C41—H41C109.5
H14B—C14—H14C109.5C9—C42—H42A109.5
C13—C15—H15A109.5C9—C42—H42B109.5
C13—C15—H15B109.5H42A—C42—H42B109.5
H15A—C15—H15B109.5C9—C42—H42C109.5
C13—C15—H15C109.5H42A—C42—H42C109.5
H15A—C15—H15C109.5H42B—C42—H42C109.5
C6—C1—C2—O1174.3 (3)C31—C3—C7—C877.5 (3)
C11—C1—C2—O149.6 (4)C3—C7—C8—C962.6 (4)
C21—C1—C2—O167.4 (3)C7—C8—C9—C1045.2 (4)
C6—C1—C2—C34.2 (4)C7—C8—C9—C4275.7 (4)
C11—C1—C2—C3128.9 (3)C7—C8—C9—C41163.6 (3)
C21—C1—C2—C3114.1 (3)O3—C4—C10—C9174.7 (3)
O1—C2—C3—C4149.8 (3)C3—C4—C10—C91.0 (5)
C1—C2—C3—C431.7 (4)C42—C9—C10—C4106.6 (4)
O1—C2—C3—C730.1 (4)C41—C9—C10—C4133.3 (3)
C1—C2—C3—C7151.5 (3)C8—C9—C10—C414.8 (4)
O1—C2—C3—C3192.0 (3)C2—C1—C11—C1266.1 (3)
C1—C2—C3—C3186.5 (3)C6—C1—C11—C1260.6 (3)
C6—O3—C4—C10153.2 (3)C21—C1—C11—C12176.8 (3)
C6—O3—C4—C330.6 (4)C1—C11—C12—C13113.0 (4)
C2—C3—C4—C10134.2 (3)C11—C12—C13—C15179.7 (3)
C7—C3—C4—C1013.0 (4)C11—C12—C13—C140.3 (6)
C31—C3—C4—C10109.2 (4)C2—C1—C21—C2248.5 (4)
C2—C3—C4—O350.1 (3)C6—C1—C21—C2274.2 (3)
C7—C3—C4—O3171.2 (2)C11—C1—C21—C22167.4 (3)
C31—C3—C4—O366.6 (3)C1—C21—C22—C23104.8 (4)
C4—O3—C6—O2173.1 (3)C21—C22—C23—C25175.1 (3)
C4—O3—C6—C110.8 (4)C21—C22—C23—C245.7 (5)
C2—C1—C6—O2156.6 (3)C4—C3—C31—C32177.0 (3)
C11—C1—C6—O231.8 (4)C2—C3—C31—C3264.9 (3)
C21—C1—C6—O284.8 (4)C7—C3—C31—C3256.6 (4)
C2—C1—C6—O327.5 (4)C3—C31—C32—C33155.0 (3)
C11—C1—C6—O3152.3 (2)C31—C32—C33—C3511.5 (7)
C21—C1—C6—O391.1 (3)C31—C32—C33—C34177.5 (3)
C4—C3—C7—C843.2 (3)C31—C32—C33—C35'24.0 (9)
C2—C3—C7—C8163.2 (2)

Experimental details

Crystal data
Chemical formulaC26H38O3
Mr398.56
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)9.534 (2), 11.753 (3), 11.994 (2)
α, β, γ (°)77.862 (13), 78.325 (12), 66.427 (9)
V3)1193.7 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.50 × 0.27 × 0.04
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
14072, 4134, 1323
Rint0.078
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.112, 1.02
No. of reflections4134
No. of parameters280
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.11, 0.10

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

 

References

First citationCiochina, R. & Grossman, R. B. (2006). Chem. Rev. 106, 3963–3986.  Web of Science CrossRef PubMed CAS Google Scholar
First citationNonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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