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

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ISSN: 2056-9890

(1SR,2RS,3SR,5SR,6RS)-6-[(Z)-1-Acet­­oxy-2-phenyl­ethen­yl]-3-eth­­oxy-2-phenyl­bi­cyclo­[3.1.0]hexan-1-yl acetate

aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China
*Correspondence e-mail: huwx66@163.com

(Received 10 December 2010; accepted 12 January 2011; online 29 January 2011)

The mol­ecule of the title compound, C26H28O5, is chiral with five stereogenic centres; however, the centrosymmetric triclinic group gives a racemic crystal. The fused ring system adopta boat conformation in which the cyclo­propane ring plane is roughly perpendicular to the styryl group plane, forming a dihedral angle of 74.78 (19)°. The dihedral angle between the two benzene rings is 77.24 (6)°.

Related literature

For related structures, see: Li et al. (2008[Li, G. T., Huang, X. G. & Zhang, L. M. (2008). J. Am. Chem. Soc. 130, 6944-6945.]); Zhang et al. (2008[Zhang, G. Z., Huang, X. G., Li, G. T. & Zhang, L. M. (2008). J. Am. Chem. Soc. 130, 1814-1815.]). For general backgound to the bicyclo­[3.1.0]hexane unit, see: Donaldson (2001[Donaldson, W. A. (2001). Tetrahedron, 57, 8589-8627.]); Ezzitouni & Marquez (1997[Ezzitouni, A. & Marquez, V. E. (1997). J. Chem. Soc. Perkin Trans. 1, pp. 1073-1078.]); Hanessian et al. (1995[Hanessian, S., Andreotti, D. & Gomtsyan, A. (1995). J. Am. Chem. Soc. 117, 10393-10394.]); Monn et al. (1997[Monn, J. A., Valli, M. J., Massey, S. M., Wright, R. A., Salhoff, C. R., Johnson, B. G., Howe, T., Alt, C. A., Rhodes, G. A., Robey, R. L., Griffey, K. R., Tizzano, J. P., Kallman, M. J., Helton, D. R. & Schoepp, D. D. (1997). J. Med. Chem. 40, 528-537.]).

[Scheme 1]

Experimental

Crystal data
  • C26H28O5

  • Mr = 420.48

  • Triclinic, [P \overline 1]

  • a = 5.8585 (14) Å

  • b = 12.368 (3) Å

  • c = 15.852 (4) Å

  • α = 73.170 (6)°

  • β = 88.967 (9)°

  • γ = 81.761 (7)°

  • V = 1087.7 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 103 K

  • 0.43 × 0.37 × 0.10 mm

Data collection
  • Rigaku AFC10/Saturn724+ diffractometer

  • 10211 measured reflections

  • 4888 independent reflections

  • 2841 reflections with I > 2σ(I)

  • Rint = 0.053

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.076

  • S = 0.94

  • 4888 reflections

  • 277 parameters

  • H-atom parameters constrained

  • Δρmax = 0.58 e Å−3

  • Δρmin = −0.32 e Å−3

Data collection: CrystalClear (Rigaku, 2008)[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]; cell refinement: CrystalClear[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]; data reduction: CrystalClear[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]; 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: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Small-ring compounds and their derivatives arouse considerable interest because their energy content relative to their acyclic counterparts often results in unexpected properties. Bicyclo[3.1.0]hexane, which contained a cyclopropane unit, is an important structural element in a wide range of naturally occurring compounds (Hanessian et al., 1995; Donaldson, 2001), and as a privileged unit in medicinal chemistry (Monn et al., 1997; Ezzitouni et al., 1997) since it possesses unique stereochemical and electronic properties in conjunction with high metabolic stability. In this paper, we will report the structure of the title compound, a new polysubstituted bicyclo[3.1.0]hexane compound, which was simply prepared from the gold catalysed reaction of vinyl ether with propargylic ester.

The title molecule (Fig.1), is mainly composed of two fused rings A (C1—C5—C6), and B (C1—C2—C3—C4—C5). The ring B has an envelope conformation, C3 and ring A lie to the same side of the plane defined by C1—C2—C4—C5. The ring A is roughly perpendicular to the styryl group and almost parallels the cyclopentane-attached benzene ring. The dihedral angle between ring A and the styryl group is 74.782 (99)°, while the dihedral angle data between two benzene rings is 77.235 (58)°.

Related literature top

For related structures, see: Li et al. (2008); Zhang et al. (2008). For general backgound to the bicyclo[3.1.0]hexane unit, see: Donaldson (2001); Ezzitouni & Marquez (1997); Hanessian et al. (1995); Monn et al. (1997).

Experimental top

Under an atmosphere of nitrogen, IprAuNTf2(12.92 mg, 0.0141 mmol) was added to a solution of 3-phenyl-1-propyn-3-yl acetate (98.46 mg, 0.565 mmol) and vinyl ethyl ether (0.8 ml) in 11 ml dry 1,2-dichloroethane. After stirring for 3 h, the solution was concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (diethyl ether:n-hexane = 1:20) to give the title compound as a white solid, which was then recrystallized from EtOAc and pentane (EtOAc:pentane = 1:9) to afford a colourless platee-like crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions(C—H=0.95 to 1.00 Å), respectively, and constrained to ride on their parent atoms with Uiso(H) set to 1.2–1.5 Uequiv(C).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing atom labeling scheme and displacement ellipsoids at the 50% probability level. Hydrogen atoms are omitted for clarity.
[Figure 2] Fig. 2. The three-dimensional structure of the title compound. The crystal packing is defined by van der Waals interactions.
(1SR,2RS,3SR,5SR,6RS)-6-[(Z)- 1-Acetoxy-2-phenylethenyl]-3-ethoxy-2-phenylbicyclo[3.1.0]hexan-1-yl acetate top
Crystal data top
C26H28O5Z = 2
Mr = 420.48F(000) = 448
Triclinic, P1Dx = 1.284 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.8585 (14) ÅCell parameters from 3076 reflections
b = 12.368 (3) Åθ = 3.3–27.5°
c = 15.852 (4) ŵ = 0.09 mm1
α = 73.170 (6)°T = 103 K
β = 88.967 (9)°Platelet, colourless
γ = 81.761 (7)°0.43 × 0.37 × 0.10 mm
V = 1087.7 (4) Å3
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
2841 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.053
Graphite monochromatorθmax = 27.5°, θmin = 3.4°
Detector resolution: 28.5714 pixels mm-1h = 77
ϕ and ω scansk = 1516
10211 measured reflectionsl = 2020
4888 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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0012P)2]
where P = (Fo2 + 2Fc2)/3
4888 reflections(Δ/σ)max < 0.001
277 parametersΔρmax = 0.58 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C26H28O5γ = 81.761 (7)°
Mr = 420.48V = 1087.7 (4) Å3
Triclinic, P1Z = 2
a = 5.8585 (14) ÅMo Kα radiation
b = 12.368 (3) ŵ = 0.09 mm1
c = 15.852 (4) ÅT = 103 K
α = 73.170 (6)°0.43 × 0.37 × 0.10 mm
β = 88.967 (9)°
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
2841 reflections with I > 2σ(I)
10211 measured reflectionsRint = 0.053
4888 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.076H-atom parameters constrained
S = 0.94Δρmax = 0.58 e Å3
4888 reflectionsΔρmin = 0.32 e Å3
277 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*/Ueq
O10.21125 (19)0.60902 (10)0.37934 (8)0.0188 (3)
O20.45865 (19)0.47059 (9)0.15005 (8)0.0165 (3)
O30.1062 (2)0.41550 (10)0.16972 (9)0.0256 (3)
O40.34585 (18)0.21945 (9)0.34813 (8)0.0171 (3)
O50.5217 (2)0.17190 (10)0.48169 (8)0.0232 (3)
C200.4622 (3)0.76441 (14)0.12130 (12)0.0190 (4)
H200.58580.74990.16290.023*
C190.4674 (3)0.84861 (14)0.04176 (12)0.0234 (5)
H190.59360.89070.02910.028*
C180.2871 (3)0.87087 (15)0.01919 (13)0.0273 (5)
H180.28790.92900.07360.033*
C170.1075 (3)0.80827 (15)0.00027 (13)0.0281 (5)
H170.01550.82250.04210.034*
C160.1049 (3)0.72458 (14)0.07945 (12)0.0227 (5)
H160.02100.68230.09180.027*
C150.2822 (3)0.70114 (14)0.14168 (12)0.0167 (4)
C20.2748 (3)0.60988 (13)0.22886 (11)0.0157 (4)
H20.11320.59280.23920.019*
C30.3613 (3)0.64292 (14)0.30821 (12)0.0172 (4)
H30.35760.72760.29170.021*
C40.6121 (3)0.58431 (14)0.32826 (12)0.0187 (4)
H4B0.72080.63880.30260.022*
H4A0.64220.55480.39270.022*
C50.6408 (3)0.48698 (14)0.28685 (11)0.0162 (4)
H50.79610.46070.26680.019*
C10.4341 (3)0.50053 (14)0.23016 (12)0.0151 (4)
C60.4684 (3)0.40331 (13)0.31560 (11)0.0159 (4)
H60.36710.41420.36480.019*
C70.5228 (3)0.28429 (14)0.31184 (12)0.0165 (4)
C80.7029 (3)0.23893 (14)0.27441 (11)0.0170 (4)
H80.80820.29000.24830.020*
C210.7645 (3)0.12233 (14)0.26717 (11)0.0170 (4)
C220.6235 (3)0.03660 (14)0.29030 (12)0.0223 (5)
H220.47410.05250.31200.027*
C230.6990 (3)0.07128 (15)0.28197 (13)0.0267 (5)
H230.60160.12870.29870.032*
C240.9144 (3)0.09582 (16)0.24957 (13)0.0270 (5)
H240.96520.16980.24380.032*
C251.0556 (3)0.01220 (15)0.22559 (13)0.0260 (5)
H251.20320.02820.20250.031*
C260.9818 (3)0.09516 (15)0.23522 (12)0.0213 (4)
H261.08180.15150.21970.026*
C110.2788 (3)0.42436 (14)0.12820 (13)0.0197 (4)
C120.3253 (3)0.38905 (16)0.04671 (13)0.0330 (5)
H12A0.22240.33450.04320.050*
H12B0.48610.35310.04820.050*
H12C0.29800.45630.00500.050*
C130.2398 (3)0.66215 (15)0.44723 (12)0.0233 (5)
H13B0.24720.74450.42050.028*
H13A0.38560.62680.48090.028*
C140.0379 (3)0.64685 (15)0.50811 (12)0.0252 (5)
H14B0.10540.68390.47470.038*
H14C0.05760.68150.55530.038*
H14A0.03060.56520.53380.038*
C90.3658 (3)0.16383 (15)0.43626 (13)0.0232 (3)
C100.1810 (3)0.09224 (14)0.46514 (12)0.0238 (5)
H10A0.22420.01900.45270.036*
H10B0.03680.13140.43320.036*
H10C0.15960.07890.52860.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0232 (7)0.0222 (7)0.0138 (7)0.0053 (5)0.0043 (6)0.0089 (5)
O20.0212 (7)0.0178 (7)0.0129 (7)0.0046 (5)0.0043 (5)0.0074 (5)
O30.0225 (8)0.0344 (8)0.0250 (9)0.0116 (6)0.0070 (6)0.0136 (6)
O40.0179 (7)0.0180 (7)0.0145 (7)0.0047 (5)0.0036 (5)0.0027 (5)
O50.0286 (7)0.0221 (6)0.0192 (7)0.0072 (5)0.0001 (5)0.0048 (5)
C200.0194 (11)0.0189 (10)0.0188 (11)0.0030 (8)0.0000 (8)0.0055 (8)
C190.0256 (11)0.0197 (10)0.0247 (12)0.0077 (8)0.0051 (9)0.0042 (8)
C180.0338 (12)0.0198 (10)0.0227 (12)0.0022 (9)0.0013 (10)0.0015 (8)
C170.0280 (12)0.0317 (12)0.0213 (13)0.0041 (10)0.0042 (9)0.0022 (9)
C160.0177 (10)0.0239 (10)0.0252 (12)0.0052 (8)0.0006 (9)0.0041 (9)
C150.0208 (10)0.0139 (9)0.0169 (11)0.0004 (8)0.0028 (8)0.0079 (8)
C20.0177 (10)0.0164 (9)0.0154 (11)0.0055 (8)0.0046 (8)0.0074 (8)
C30.0213 (11)0.0168 (9)0.0155 (11)0.0062 (8)0.0031 (8)0.0062 (8)
C40.0177 (10)0.0176 (10)0.0215 (11)0.0019 (8)0.0002 (8)0.0069 (8)
C50.0138 (10)0.0177 (10)0.0184 (11)0.0030 (8)0.0032 (8)0.0073 (8)
C10.0195 (10)0.0160 (9)0.0113 (10)0.0027 (8)0.0037 (8)0.0064 (7)
C60.0199 (10)0.0165 (9)0.0120 (10)0.0038 (8)0.0056 (8)0.0048 (7)
C70.0172 (10)0.0178 (10)0.0135 (10)0.0050 (8)0.0002 (8)0.0019 (8)
C80.0166 (10)0.0173 (9)0.0170 (11)0.0050 (8)0.0017 (8)0.0035 (8)
C210.0186 (10)0.0169 (10)0.0147 (11)0.0017 (8)0.0016 (8)0.0040 (8)
C220.0187 (11)0.0208 (10)0.0288 (13)0.0017 (8)0.0017 (9)0.0099 (9)
C230.0288 (12)0.0196 (10)0.0340 (13)0.0059 (9)0.0003 (10)0.0104 (9)
C240.0286 (12)0.0195 (10)0.0351 (14)0.0035 (9)0.0056 (10)0.0143 (9)
C250.0194 (11)0.0274 (11)0.0326 (13)0.0034 (9)0.0017 (9)0.0139 (9)
C260.0209 (11)0.0208 (10)0.0223 (12)0.0031 (8)0.0003 (9)0.0065 (8)
C110.0254 (12)0.0168 (10)0.0185 (11)0.0076 (8)0.0024 (9)0.0056 (8)
C120.0468 (14)0.0389 (13)0.0250 (13)0.0217 (11)0.0146 (10)0.0207 (10)
C130.0324 (12)0.0245 (11)0.0157 (11)0.0038 (9)0.0010 (9)0.0104 (8)
C140.0306 (12)0.0274 (11)0.0188 (12)0.0013 (9)0.0018 (9)0.0114 (9)
C90.0286 (7)0.0221 (6)0.0192 (7)0.0072 (5)0.0001 (5)0.0048 (5)
C100.0272 (11)0.0192 (10)0.0232 (12)0.0074 (8)0.0055 (9)0.0014 (8)
Geometric parameters (Å, º) top
O1—C31.420 (2)C1—C61.523 (2)
O1—C131.4372 (19)C6—C71.479 (2)
O2—C111.363 (2)C6—H61.0000
O2—C11.4215 (19)C7—C81.334 (2)
O3—C111.198 (2)C8—C211.473 (2)
O4—C91.366 (2)C8—H80.9500
O4—C71.414 (2)C21—C261.394 (2)
O5—C91.2057 (18)C21—C221.398 (2)
C20—C151.381 (2)C22—C231.387 (2)
C20—C191.387 (2)C22—H220.9500
C20—H200.9500C23—C241.381 (3)
C19—C181.387 (2)C23—H230.9500
C19—H190.9500C24—C251.380 (2)
C18—C171.373 (2)C24—H240.9500
C18—H180.9500C25—C261.387 (2)
C17—C161.384 (2)C25—H250.9500
C17—H170.9500C26—H260.9500
C16—C151.386 (2)C11—C121.488 (2)
C16—H160.9500C12—H12A0.9800
C15—C21.515 (2)C12—H12B0.9800
C2—C11.524 (2)C12—H12C0.9800
C2—C31.545 (2)C13—C141.511 (3)
C2—H21.0000C13—H13B0.9900
C3—C41.538 (2)C13—H13A0.9900
C3—H31.0000C14—H14B0.9800
C4—C51.518 (2)C14—H14C0.9800
C4—H4B0.9900C14—H14A0.9800
C4—H4A0.9900C9—C101.479 (2)
C5—C11.482 (2)C10—H10A0.9800
C5—C61.519 (2)C10—H10B0.9800
C5—H51.0000C10—H10C0.9800
C3—O1—C13112.11 (13)C1—C6—H6115.3
C11—O2—C1114.87 (14)C8—C7—O4120.48 (15)
C9—O4—C7116.41 (12)C8—C7—C6127.71 (17)
C15—C20—C19121.78 (16)O4—C7—C6111.64 (15)
C15—C20—H20119.1C7—C8—C21130.31 (17)
C19—C20—H20119.1C7—C8—H8114.8
C20—C19—C18119.51 (18)C21—C8—H8114.8
C20—C19—H19120.2C26—C21—C22117.45 (16)
C18—C19—H19120.2C26—C21—C8117.21 (16)
C17—C18—C19119.49 (18)C22—C21—C8125.33 (17)
C17—C18—H18120.3C23—C22—C21120.89 (18)
C19—C18—H18120.3C23—C22—H22119.6
C18—C17—C16120.24 (17)C21—C22—H22119.6
C18—C17—H17119.9C24—C23—C22120.54 (18)
C16—C17—H17119.9C24—C23—H23119.7
C17—C16—C15121.40 (18)C22—C23—H23119.7
C17—C16—H16119.3C25—C24—C23119.54 (17)
C15—C16—H16119.3C25—C24—H24120.2
C20—C15—C16117.56 (17)C23—C24—H24120.2
C20—C15—C2121.91 (15)C24—C25—C26119.97 (19)
C16—C15—C2120.53 (16)C24—C25—H25120.0
C15—C2—C1111.54 (15)C26—C25—H25120.0
C15—C2—C3113.55 (14)C25—C26—C21121.60 (17)
C1—C2—C3103.93 (12)C25—C26—H26119.2
C15—C2—H2109.2C21—C26—H26119.2
C1—C2—H2109.2O3—C11—O2123.27 (17)
C3—C2—H2109.2O3—C11—C12125.48 (17)
O1—C3—C4113.68 (14)O2—C11—C12111.24 (16)
O1—C3—C2108.36 (13)C11—C12—H12A109.5
C4—C3—C2106.92 (14)C11—C12—H12B109.5
O1—C3—H3109.3H12A—C12—H12B109.5
C4—C3—H3109.3C11—C12—H12C109.5
C2—C3—H3109.3H12A—C12—H12C109.5
C5—C4—C3106.17 (13)H12B—C12—H12C109.5
C5—C4—H4B110.5O1—C13—C14108.95 (14)
C3—C4—H4B110.5O1—C13—H13B109.9
C5—C4—H4A110.5C14—C13—H13B109.9
C3—C4—H4A110.5O1—C13—H13A109.9
H4B—C4—H4A108.7C14—C13—H13A109.9
C1—C5—C4107.90 (14)H13B—C13—H13A108.3
C1—C5—C660.96 (10)C13—C14—H14B109.5
C4—C5—C6115.09 (16)C13—C14—H14C109.5
C1—C5—H5119.6H14B—C14—H14C109.5
C4—C5—H5119.6C13—C14—H14A109.5
C6—C5—H5119.6H14B—C14—H14A109.5
O2—C1—C5119.36 (14)H14C—C14—H14A109.5
O2—C1—C6117.08 (14)O5—C9—O4122.20 (18)
C5—C1—C660.72 (10)O5—C9—C10126.33 (18)
O2—C1—C2117.65 (13)O4—C9—C10111.43 (14)
C5—C1—C2110.21 (14)C9—C10—H10A109.5
C6—C1—C2119.07 (15)C9—C10—H10B109.5
C7—C6—C5121.31 (16)H10A—C10—H10B109.5
C7—C6—C1119.45 (15)C9—C10—H10C109.5
C5—C6—C158.32 (11)H10A—C10—H10C109.5
C7—C6—H6115.3H10B—C10—H10C109.5
C5—C6—H6115.3
C15—C20—C19—C180.3 (3)C15—C2—C1—C6173.81 (14)
C20—C19—C18—C170.8 (3)C3—C2—C1—C651.09 (19)
C19—C18—C17—C160.8 (3)C1—C5—C6—C7107.50 (18)
C18—C17—C16—C150.4 (3)C4—C5—C6—C7155.14 (15)
C19—C20—C15—C160.0 (3)C4—C5—C6—C197.36 (16)
C19—C20—C15—C2179.41 (17)O2—C1—C6—C70.5 (2)
C17—C16—C15—C200.0 (3)C5—C1—C6—C7110.66 (18)
C17—C16—C15—C2179.45 (17)C2—C1—C6—C7151.20 (15)
C20—C15—C2—C177.7 (2)O2—C1—C6—C5110.16 (16)
C16—C15—C2—C1102.84 (19)C2—C1—C6—C598.13 (17)
C20—C15—C2—C339.3 (2)C9—O4—C7—C894.3 (2)
C16—C15—C2—C3140.13 (17)C9—O4—C7—C690.12 (17)
C13—O1—C3—C476.72 (17)C5—C6—C7—C89.5 (3)
C13—O1—C3—C2164.57 (12)C1—C6—C7—C859.3 (2)
C15—C2—C3—O1137.72 (15)C5—C6—C7—O4175.32 (14)
C1—C2—C3—O1100.89 (15)C1—C6—C7—O4115.93 (17)
C15—C2—C3—C499.37 (17)O4—C7—C8—C214.1 (3)
C1—C2—C3—C422.01 (18)C6—C7—C8—C21178.87 (15)
O1—C3—C4—C599.09 (17)C7—C8—C21—C26170.96 (17)
C2—C3—C4—C520.44 (18)C7—C8—C21—C228.6 (3)
C3—C4—C5—C110.56 (19)C26—C21—C22—C230.3 (3)
C3—C4—C5—C655.11 (19)C8—C21—C22—C23179.20 (16)
C11—O2—C1—C5144.83 (15)C21—C22—C23—C240.8 (3)
C11—O2—C1—C674.86 (18)C22—C23—C24—C250.2 (3)
C11—O2—C1—C277.26 (18)C23—C24—C25—C260.9 (3)
C4—C5—C1—O2144.23 (15)C24—C25—C26—C211.3 (3)
C6—C5—C1—O2106.47 (17)C22—C21—C26—C250.7 (3)
C4—C5—C1—C6109.30 (17)C8—C21—C26—C25179.71 (16)
C4—C5—C1—C23.5 (2)C1—O2—C11—O34.4 (2)
C6—C5—C1—C2112.78 (17)C1—O2—C11—C12176.47 (14)
C15—C2—C1—O234.6 (2)C3—O1—C13—C14165.68 (14)
C3—C2—C1—O2157.36 (14)C7—O4—C9—O52.2 (3)
C15—C2—C1—C5106.86 (16)C7—O4—C9—C10175.71 (14)
C3—C2—C1—C515.86 (19)

Experimental details

Crystal data
Chemical formulaC26H28O5
Mr420.48
Crystal system, space groupTriclinic, P1
Temperature (K)103
a, b, c (Å)5.8585 (14), 12.368 (3), 15.852 (4)
α, β, γ (°)73.170 (6), 88.967 (9), 81.761 (7)
V3)1087.7 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.43 × 0.37 × 0.10
Data collection
DiffractometerRigaku AFC10/Saturn724+
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10211, 4888, 2841
Rint0.053
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.076, 0.94
No. of reflections4888
No. of parameters277
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.58, 0.32

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), publCIF (Westrip, 2010).

 

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20872095). Special thanks are given to Dr Huang Xiaogen and Dr Chen Zili for their generous help.

References

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