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

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ISSN: 2056-9890

Bis(2,2-di­methyl-2,3-di­hydro-1-benzo­furan-7-yl) carbonate

aCollege of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, People's Republic of China, and bHunan Research Institute of Chemical Industry, Changsha 410007, People's Republic of China
*Correspondence e-mail: axhu0731@yahoo.com.cn

(Received 24 December 2010; accepted 5 January 2011; online 12 January 2011)

The title compound, C21H22O5, crystallizes with three mol­ecules in the asymmetric unit. In one mol­ecule, two methyl groups are disordered over two positions with a site occupation factor of 0.72 (2) for the major occupancy site. The benzene rings make dihedral angles of 35.3 (6), 29.7 (6) and 40.6 (7)° in the three molecules.

Related literature

The compound was obtained as a by-product during the derivatization of the commercially available carbofuran (systematic name 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl methyl­carbamate), a popular carbamate insecticide. For background to insecticides, see: Tomlin (1994[Tomlin, C. (1994). The Pesticide Manual. A World Compendium, 10th ed., pp. 152-153. Bath: The British Crop Protection Council, The Bath Press.]). For related structures, see: Xu et al. (2005[Xu, L.-Z., Yu, G.-P. & Yang, S.-H. (2005). Acta Cryst. E61, o1924-o1926.]); Li et al. (2009[Li, W.-S., Li, L. & Li, J.-S. (2009). Acta Cryst. E65, o2928.]).

[Scheme 1]

Experimental

Crystal data
  • C21H22O5

  • Mr = 354.39

  • Orthorhombic, P n a 21

  • a = 16.6409 (6) Å

  • b = 23.2581 (9) Å

  • c = 14.5045 (6) Å

  • V = 5613.8 (4) Å3

  • Z = 12

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 173 K

  • 0.46 × 0.44 × 0.42 mm

Data collection
  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.960, Tmax = 0.964

  • 27906 measured reflections

  • 6368 independent reflections

  • 4923 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.109

  • S = 1.06

  • 6368 reflections

  • 732 parameters

  • 32 restraints

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2003[Bruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Bis(2,2-dimethyldihydrobenzofuran-7-yl)carbonate(I), C21H22O5, was obtained as a by-product during the attempted preparation of the derivatives of the commercial Carbofuran (Xu et al., 2005; Li et al., 2009), which is a popular carbamate insecticide (Tomlin, 1994). In the molecule of the title compound, all bond lengths and angles are within normal ranges. In the crystal, the dihedral angles between the phenyl rings of C1—C6 and C12—C17, C22—C27 and C33—C38, C43—C48 and C54—C59 are 35.3 (6)°, 29.7 (6)°, 40.6 (7)°. The crystal packing is stabilized by π···π interactions.

Related literature top

The compound was obtained as a by-product during the derivatization of the commercially available carbofuran (systematic name 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl methylcarbamate), a popular carbamate insecticide. For background to insecticides, see: Tomlin (1994). For related structures, see: Xu et al. (2005); Li et al. (2009).

Experimental top

0.05 mol of bis(trichloromethyl)carbonate was dissolved in 200 mL toluene at room temperature, then the solution was cooled to 263.15 K, 1.0 mL triethylamine was added. After half an hour, the solution of 0.10 mol 2,2-dimethy-2,3-dihydrobenzofuran-7-ol in 100 mL toluene was added dropwise to give bis(2,2-dimethyldihydrobenzofuran-7-yl) carbonate as an amber solid of 14.3 g, yielded 80.5%. The solid was purified by recrystallization from saturated ethanol solution, giving the title compound as a colourless crystalline solid. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of five days. The identity of the title compound was confirmed by NMR and MS spectroscopy.

Refinement top

Methyl H atoms were placed in calculated positions, with C—H=0.96 Å, and torsion angles were refined, with Uiso(H)=1.5Ueq(C). Other H atoms were placed in geometrically idealized positions and refined as riding model, with N—H distance of 0.86 Å, C—H distances of 0.98Å (C3—H3), 0.93Å (aromatic H atoms) and 0.97Å (methylene H atoms). The constraint Uiso(H)=1.2Ueq(carrier) was applied. The the components of the anisotropic displacement parameters in the direction of the bond are restrained to be equal within an effective standard deviation 0.005, and C28, C29 are restrained with effective standard deviation 0.005 to have the same Uij components. The Uij values of the C62, C62B, C63, C63B atoms are refined to behave approximately isotropic within the effective standard deviation 0.005.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Perspective view of one the the three molecules of the title compound showing 30% probability displacement ellipsoids.
Bis(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl) carbonate top
Crystal data top
C21H22O5Dx = 1.258 Mg m3
Mr = 354.39Melting point: 361.45 K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 9606 reflections
a = 16.6409 (6) Åθ = 2.1–26.0°
b = 23.2581 (9) ŵ = 0.09 mm1
c = 14.5045 (6) ÅT = 173 K
V = 5613.8 (4) Å3Block, colourless
Z = 120.46 × 0.44 × 0.42 mm
F(000) = 2256
Data collection top
Bruker SMART 1000 CCD
diffractometer
6368 independent reflections
Radiation source: fine-focus sealed tube4923 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scansθmax = 27.1°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1621
Tmin = 0.960, Tmax = 0.964k = 2729
27906 measured reflectionsl = 1718
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0497P)2 + 1.3774P]
where P = (Fo2 + 2Fc2)/3
6368 reflections(Δ/σ)max < 0.001
732 parametersΔρmax = 0.23 e Å3
32 restraintsΔρmin = 0.21 e Å3
Crystal data top
C21H22O5V = 5613.8 (4) Å3
Mr = 354.39Z = 12
Orthorhombic, Pna21Mo Kα radiation
a = 16.6409 (6) ŵ = 0.09 mm1
b = 23.2581 (9) ÅT = 173 K
c = 14.5045 (6) Å0.46 × 0.44 × 0.42 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
6368 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
4923 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.964Rint = 0.030
27906 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04232 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 1.06Δρmax = 0.23 e Å3
6368 reflectionsΔρmin = 0.21 e Å3
732 parameters
Special details top

Experimental. 1H NMR in CDCl3 (300 MHz), delta: 1.50(s,12H,4CH3), 3.05(s,4H,2CH2), 6.78–7.27(m,6H,2C6H3)

LC-MS: 372.2(M+18)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)
C10.72869 (16)0.64804 (12)0.2593 (2)0.0317 (6)
C20.77503 (17)0.67717 (12)0.1957 (2)0.0339 (6)
C30.81873 (17)0.64739 (13)0.1300 (2)0.0367 (7)
C40.81567 (17)0.58778 (13)0.1275 (2)0.0383 (7)
H40.84470.56700.08200.046*
C50.76969 (18)0.55890 (13)0.1924 (2)0.0403 (7)
H50.76790.51810.19160.048*
C60.72644 (17)0.58870 (13)0.2582 (2)0.0375 (7)
H60.69530.56840.30240.045*
C70.8595 (2)0.69120 (15)0.0700 (3)0.0518 (9)
H7A0.83450.69290.00820.062*
H7B0.91750.68260.06320.062*
C80.84633 (17)0.74798 (13)0.1235 (2)0.0363 (7)
C90.8164 (2)0.79648 (16)0.0643 (2)0.0551 (9)
H9A0.76840.78410.03070.083*
H9B0.85840.80750.02030.083*
H9C0.80310.82950.10340.083*
C100.9177 (2)0.76493 (18)0.1789 (2)0.0547 (9)
H10A0.90400.79790.21790.082*
H10B0.96180.77550.13740.082*
H10C0.93440.73260.21780.082*
C110.63004 (16)0.71444 (13)0.2967 (2)0.0320 (6)
C120.55604 (16)0.79348 (12)0.34947 (19)0.0310 (6)
C130.48895 (16)0.79984 (12)0.40412 (19)0.0303 (6)
C140.43827 (17)0.84686 (12)0.3926 (2)0.0349 (7)
C150.45287 (19)0.88649 (13)0.3243 (2)0.0405 (7)
H150.41760.91810.31540.049*
C160.52035 (19)0.87953 (14)0.2683 (2)0.0424 (7)
H160.53070.90640.22040.051*
C170.57225 (18)0.83401 (13)0.2820 (2)0.0370 (7)
H170.61910.83050.24500.044*
C180.37437 (19)0.84320 (14)0.4653 (2)0.0440 (8)
H18A0.32030.84900.43850.053*
H18B0.38340.87200.51450.053*
C190.38424 (18)0.78166 (14)0.5022 (2)0.0379 (7)
C200.3244 (2)0.74160 (16)0.4557 (3)0.0544 (9)
H20A0.32990.74480.38860.082*
H20B0.26970.75230.47380.082*
H20C0.33510.70190.47470.082*
C210.3823 (3)0.77725 (19)0.6050 (2)0.0622 (10)
H21A0.39370.73760.62350.093*
H21B0.32900.78840.62750.093*
H21C0.42290.80290.63140.093*
C220.50518 (17)0.52554 (13)0.3246 (2)0.0355 (6)
C230.45542 (19)0.49810 (13)0.3866 (2)0.0397 (7)
C240.4071 (2)0.52908 (15)0.4452 (2)0.0495 (9)
C250.4077 (2)0.58836 (15)0.4427 (3)0.0513 (9)
H250.37460.60990.48350.062*
C260.4570 (2)0.61611 (14)0.3803 (3)0.0476 (8)
H260.45790.65690.37820.057*
C270.50489 (19)0.58482 (14)0.3211 (2)0.0424 (7)
H270.53790.60420.27750.051*
C280.3563 (3)0.48691 (17)0.4983 (3)0.0785 (13)
H28A0.29920.48920.47920.094*
H28B0.36000.49390.56550.094*
C290.3931 (2)0.42830 (16)0.4725 (3)0.0560 (9)
C300.4447 (3)0.40512 (19)0.5482 (3)0.0719 (12)
H30A0.47580.37230.52520.108*
H30B0.41060.39260.59960.108*
H30C0.48150.43520.56960.108*
C310.3326 (3)0.3848 (2)0.4381 (3)0.0740 (12)
H31A0.30200.40140.38680.111*
H31B0.29580.37450.48820.111*
H31C0.36080.35030.41680.111*
C320.60410 (16)0.45748 (14)0.2938 (2)0.0380 (7)
C330.67945 (18)0.37786 (13)0.2413 (2)0.0378 (7)
C340.74682 (17)0.37333 (12)0.1865 (2)0.0343 (6)
C350.79846 (19)0.32660 (13)0.1949 (2)0.0399 (7)
C360.7833 (2)0.28498 (15)0.2601 (2)0.0494 (8)
H360.81870.25330.26710.059*
C370.7160 (2)0.28993 (16)0.3153 (3)0.0552 (9)
H370.70550.26150.36070.066*
C380.6636 (2)0.33572 (15)0.3053 (2)0.0486 (8)
H380.61680.33810.34260.058*
C390.8623 (2)0.33340 (14)0.1226 (3)0.0484 (8)
H39A0.85310.30710.07010.058*
H39B0.91650.32620.14850.058*
C400.85265 (18)0.39687 (15)0.0932 (2)0.0421 (8)
C410.90819 (19)0.43531 (15)0.1465 (3)0.0496 (9)
H41A0.89830.47550.12940.074*
H41B0.96400.42520.13240.074*
H41C0.89850.43040.21270.074*
C420.8569 (2)0.40710 (19)0.0094 (2)0.0607 (10)
H42A0.81830.38200.04080.091*
H42B0.91130.39860.03150.091*
H42C0.84380.44730.02270.091*
C430.0015 (2)0.33792 (15)0.3517 (3)0.0486 (8)
C440.05123 (19)0.36897 (14)0.4055 (2)0.0417 (7)
C450.0936 (2)0.34370 (15)0.4767 (3)0.0500 (9)
C460.0841 (2)0.28554 (18)0.4923 (3)0.0697 (14)
H460.11260.26730.54090.084*
C470.0327 (3)0.25404 (18)0.4367 (4)0.0792 (15)
H470.02660.21390.44690.095*
C480.0094 (2)0.28026 (17)0.3668 (3)0.0665 (12)
H480.04410.25810.32890.080*
C490.1459 (3)0.38968 (18)0.5191 (3)0.0648 (11)
H49A0.13910.39110.58680.078*
H49B0.20330.38310.50460.078*
C500.11503 (19)0.44496 (15)0.4736 (2)0.0431 (7)
C510.0575 (2)0.47812 (19)0.5336 (3)0.0668 (11)
H51A0.01550.45220.55630.100*
H51B0.08670.49460.58600.100*
H51C0.03300.50910.49750.100*
C520.1806 (2)0.4841 (2)0.4376 (4)0.0790 (14)
H52A0.15630.51710.40620.118*
H52B0.21360.49760.48920.118*
H52C0.21440.46280.39400.118*
C530.10357 (19)0.39918 (16)0.3031 (3)0.0469 (8)
C540.19407 (19)0.46089 (16)0.2276 (2)0.0481 (8)
C550.2647 (2)0.44617 (16)0.1850 (2)0.0471 (8)
C560.3256 (2)0.48610 (18)0.1742 (3)0.0543 (9)
C570.3172 (3)0.54066 (18)0.2108 (3)0.0647 (11)
H570.35890.56830.20440.078*
C580.2467 (3)0.55435 (18)0.2571 (3)0.0679 (11)
H580.24070.59130.28400.081*
C590.1853 (2)0.51498 (18)0.2643 (3)0.0616 (10)
H590.13680.52520.29470.074*
C600.3903 (2)0.4579 (2)0.1167 (4)0.0740 (12)
H60A0.44380.46210.14580.089*
H60B0.39210.47450.05390.089*
C610.3646 (2)0.39495 (18)0.1140 (3)0.0551 (10)
C620.3733 (10)0.3503 (10)0.0322 (12)0.053 (5)0.28 (2)
H62A0.34700.36560.02310.080*0.28 (2)
H62B0.34790.31390.04970.080*0.28 (2)
H62C0.43040.34380.01930.080*0.28 (2)
C630.4118 (10)0.3650 (7)0.1904 (12)0.035 (4)0.28 (2)
H63A0.43430.39390.23220.052*0.28 (2)
H63B0.45550.34250.16310.052*0.28 (2)
H63C0.37590.33940.22480.052*0.28 (2)
C62B0.3559 (5)0.3804 (6)0.0136 (5)0.069 (2)0.72 (2)
H62D0.32470.41050.01730.104*0.72 (2)
H62E0.32810.34350.00730.104*0.72 (2)
H62F0.40930.37780.01470.104*0.72 (2)
C63B0.4127 (7)0.3545 (6)0.1693 (11)0.109 (4)0.72 (2)
H63D0.41920.36970.23190.163*0.72 (2)
H63E0.46570.34960.14080.163*0.72 (2)
H63F0.38530.31720.17200.163*0.72 (2)
O10.78087 (13)0.73538 (9)0.19029 (16)0.0444 (5)
O20.68790 (11)0.67934 (8)0.32817 (13)0.0346 (4)
O30.60238 (12)0.71474 (10)0.22166 (15)0.0428 (5)
O40.60936 (11)0.74815 (9)0.36804 (14)0.0357 (5)
O50.46542 (12)0.76326 (9)0.47200 (14)0.0372 (5)
O60.44698 (14)0.44023 (9)0.39277 (18)0.0533 (6)
O70.54932 (12)0.49397 (9)0.25984 (15)0.0398 (5)
O80.62912 (14)0.45562 (11)0.37023 (18)0.0556 (7)
O90.62560 (12)0.42365 (10)0.22312 (15)0.0411 (5)
O100.76908 (12)0.41200 (9)0.12079 (15)0.0395 (5)
O110.06665 (14)0.42617 (9)0.39410 (15)0.0472 (6)
O120.04291 (14)0.36401 (11)0.27900 (16)0.0506 (6)
O130.12750 (16)0.40829 (13)0.37863 (18)0.0665 (8)
O140.12937 (14)0.42191 (12)0.22380 (17)0.0538 (6)
O150.28074 (13)0.39351 (12)0.1484 (2)0.0617 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0255 (13)0.0375 (16)0.0320 (14)0.0011 (12)0.0016 (12)0.0040 (13)
C20.0291 (14)0.0344 (15)0.0382 (16)0.0030 (12)0.0014 (12)0.0035 (13)
C30.0312 (15)0.0416 (17)0.0375 (16)0.0018 (12)0.0024 (13)0.0056 (14)
C40.0339 (15)0.0412 (17)0.0398 (17)0.0045 (13)0.0004 (13)0.0089 (14)
C50.0371 (16)0.0335 (16)0.0502 (19)0.0011 (13)0.0031 (15)0.0057 (14)
C60.0284 (14)0.0409 (17)0.0433 (16)0.0037 (13)0.0004 (13)0.0045 (14)
C70.052 (2)0.050 (2)0.054 (2)0.0026 (16)0.0206 (17)0.0017 (17)
C80.0320 (15)0.0419 (17)0.0351 (16)0.0023 (13)0.0054 (13)0.0048 (13)
C90.057 (2)0.066 (2)0.042 (2)0.0163 (18)0.0035 (17)0.0103 (18)
C100.0382 (18)0.086 (3)0.0402 (19)0.0060 (17)0.0047 (15)0.0029 (18)
C110.0245 (13)0.0387 (16)0.0328 (15)0.0030 (12)0.0024 (12)0.0002 (12)
C120.0285 (14)0.0366 (15)0.0279 (14)0.0007 (12)0.0036 (11)0.0036 (12)
C130.0326 (15)0.0322 (15)0.0263 (13)0.0043 (11)0.0014 (12)0.0028 (12)
C140.0349 (15)0.0372 (16)0.0327 (15)0.0006 (12)0.0038 (12)0.0053 (13)
C150.0441 (17)0.0346 (16)0.0427 (18)0.0029 (13)0.0062 (14)0.0003 (14)
C160.0485 (18)0.0437 (18)0.0349 (16)0.0089 (14)0.0015 (15)0.0072 (14)
C170.0347 (15)0.0453 (18)0.0308 (16)0.0064 (13)0.0006 (13)0.0027 (13)
C180.0412 (17)0.0404 (17)0.050 (2)0.0054 (14)0.0057 (15)0.0005 (15)
C190.0356 (16)0.0409 (17)0.0373 (17)0.0045 (13)0.0071 (13)0.0019 (13)
C200.0396 (18)0.047 (2)0.076 (3)0.0026 (15)0.0025 (18)0.0062 (18)
C210.070 (2)0.077 (3)0.040 (2)0.021 (2)0.0151 (18)0.0024 (18)
C220.0280 (14)0.0436 (17)0.0350 (16)0.0030 (13)0.0001 (12)0.0049 (13)
C230.0397 (17)0.0391 (17)0.0402 (17)0.0094 (13)0.0037 (14)0.0011 (14)
C240.056 (2)0.045 (2)0.048 (2)0.0147 (16)0.0200 (17)0.0056 (15)
C250.060 (2)0.0437 (19)0.050 (2)0.0167 (16)0.0109 (17)0.0023 (15)
C260.0496 (19)0.0375 (17)0.056 (2)0.0040 (15)0.0028 (17)0.0037 (16)
C270.0334 (15)0.0461 (18)0.0478 (19)0.0041 (14)0.0007 (14)0.0004 (15)
C280.095 (3)0.055 (2)0.085 (3)0.025 (2)0.054 (2)0.016 (2)
C290.064 (2)0.0441 (18)0.060 (2)0.0113 (16)0.0285 (19)0.0100 (17)
C300.104 (3)0.064 (3)0.047 (2)0.013 (2)0.004 (2)0.0098 (19)
C310.054 (2)0.098 (3)0.070 (3)0.004 (2)0.016 (2)0.010 (2)
C320.0223 (13)0.0500 (19)0.0416 (18)0.0038 (13)0.0041 (13)0.0125 (14)
C330.0365 (16)0.0415 (17)0.0356 (17)0.0006 (13)0.0046 (13)0.0066 (13)
C340.0359 (15)0.0378 (16)0.0293 (15)0.0016 (12)0.0004 (12)0.0029 (13)
C350.0413 (17)0.0375 (16)0.0409 (17)0.0008 (13)0.0014 (14)0.0037 (14)
C360.060 (2)0.0440 (18)0.0442 (18)0.0050 (16)0.0014 (17)0.0016 (16)
C370.074 (3)0.050 (2)0.0415 (19)0.0058 (18)0.0062 (18)0.0059 (16)
C380.054 (2)0.048 (2)0.0435 (19)0.0087 (16)0.0151 (16)0.0030 (15)
C390.0439 (18)0.0465 (19)0.055 (2)0.0133 (15)0.0085 (16)0.0051 (17)
C400.0341 (16)0.053 (2)0.0394 (17)0.0124 (14)0.0111 (14)0.0040 (14)
C410.0372 (17)0.052 (2)0.060 (2)0.0065 (15)0.0063 (16)0.0094 (17)
C420.059 (2)0.080 (3)0.042 (2)0.025 (2)0.0153 (18)0.0029 (18)
C430.0464 (18)0.0462 (19)0.053 (2)0.0001 (16)0.0135 (17)0.0018 (16)
C440.0447 (18)0.0428 (18)0.0376 (17)0.0077 (14)0.0052 (14)0.0041 (14)
C450.0479 (19)0.055 (2)0.0468 (19)0.0177 (16)0.0089 (16)0.0155 (17)
C460.053 (2)0.068 (3)0.088 (3)0.026 (2)0.027 (2)0.043 (2)
C470.058 (2)0.048 (2)0.132 (5)0.001 (2)0.034 (3)0.021 (3)
C480.050 (2)0.052 (2)0.097 (3)0.0035 (18)0.020 (2)0.001 (2)
C490.069 (2)0.076 (3)0.050 (2)0.027 (2)0.015 (2)0.0076 (19)
C500.0385 (17)0.057 (2)0.0342 (16)0.0065 (15)0.0076 (14)0.0002 (15)
C510.073 (3)0.083 (3)0.044 (2)0.028 (2)0.011 (2)0.017 (2)
C520.047 (2)0.107 (4)0.084 (3)0.010 (2)0.011 (2)0.025 (3)
C530.0340 (17)0.061 (2)0.046 (2)0.0074 (15)0.0052 (16)0.0036 (17)
C540.0423 (18)0.070 (2)0.0320 (16)0.0017 (17)0.0059 (14)0.0007 (16)
C550.0445 (18)0.064 (2)0.0333 (16)0.0038 (16)0.0061 (15)0.0047 (16)
C560.0462 (19)0.070 (2)0.046 (2)0.0087 (18)0.0104 (17)0.0001 (18)
C570.068 (3)0.060 (2)0.067 (3)0.005 (2)0.024 (2)0.002 (2)
C580.076 (3)0.058 (2)0.070 (3)0.014 (2)0.020 (2)0.003 (2)
C590.061 (2)0.075 (3)0.049 (2)0.022 (2)0.0134 (19)0.004 (2)
C600.052 (2)0.090 (3)0.079 (3)0.023 (2)0.008 (2)0.010 (3)
C610.0402 (18)0.083 (3)0.042 (2)0.0155 (17)0.0100 (16)0.0219 (19)
C620.053 (6)0.061 (7)0.046 (6)0.004 (4)0.006 (4)0.016 (4)
C630.028 (5)0.033 (5)0.043 (5)0.010 (4)0.007 (4)0.016 (4)
C62B0.065 (3)0.090 (5)0.053 (3)0.017 (3)0.007 (3)0.014 (3)
C63B0.092 (5)0.120 (6)0.114 (6)0.002 (4)0.007 (4)0.008 (4)
O10.0434 (12)0.0377 (12)0.0521 (14)0.0032 (9)0.0185 (11)0.0066 (10)
O20.0298 (10)0.0430 (12)0.0310 (10)0.0040 (9)0.0036 (9)0.0001 (9)
O30.0373 (11)0.0540 (13)0.0371 (12)0.0072 (10)0.0085 (10)0.0111 (10)
O40.0310 (10)0.0451 (12)0.0311 (11)0.0045 (9)0.0020 (9)0.0036 (9)
O50.0360 (11)0.0422 (12)0.0335 (11)0.0050 (9)0.0058 (9)0.0032 (9)
O60.0556 (14)0.0377 (12)0.0667 (17)0.0113 (10)0.0289 (13)0.0022 (12)
O70.0325 (11)0.0500 (13)0.0368 (11)0.0023 (9)0.0072 (9)0.0049 (10)
O80.0452 (13)0.0713 (17)0.0502 (15)0.0167 (12)0.0141 (11)0.0236 (13)
O90.0382 (11)0.0488 (13)0.0364 (11)0.0039 (10)0.0084 (9)0.0042 (10)
O100.0349 (11)0.0450 (12)0.0387 (11)0.0100 (9)0.0098 (9)0.0033 (10)
O110.0611 (14)0.0405 (12)0.0399 (13)0.0074 (11)0.0163 (11)0.0020 (10)
O120.0430 (13)0.0650 (15)0.0439 (14)0.0032 (11)0.0005 (11)0.0105 (12)
O130.0603 (16)0.099 (2)0.0406 (14)0.0197 (15)0.0164 (13)0.0104 (14)
O140.0416 (13)0.0870 (19)0.0329 (12)0.0041 (12)0.0019 (10)0.0061 (12)
O150.0396 (13)0.0787 (18)0.0669 (17)0.0182 (12)0.0151 (12)0.0296 (14)
Geometric parameters (Å, º) top
C1—C21.380 (4)C34—O101.362 (4)
C1—C61.381 (4)C34—C351.391 (4)
C1—O21.410 (3)C35—C361.377 (5)
C2—O11.360 (4)C35—C391.501 (5)
C2—C31.385 (4)C36—C371.381 (5)
C3—C41.388 (4)C36—H360.9500
C3—C71.502 (5)C37—C381.384 (5)
C4—C51.387 (4)C37—H370.9500
C4—H40.9500C38—H380.9500
C5—C61.381 (4)C39—C401.545 (5)
C5—H50.9500C39—H39A0.9900
C6—H60.9500C39—H39B0.9900
C7—C81.547 (5)C40—O101.489 (3)
C7—H7A0.9900C40—C411.501 (5)
C7—H7B0.9900C40—C421.509 (5)
C8—O11.487 (4)C41—H41A0.9800
C8—C101.487 (4)C41—H41B0.9800
C8—C91.502 (4)C41—H41C0.9800
C9—H9A0.9800C42—H42A0.9800
C9—H9B0.9800C42—H42B0.9800
C9—H9C0.9800C42—H42C0.9800
C10—H10A0.9800C43—C481.365 (5)
C10—H10B0.9800C43—C441.378 (5)
C10—H10C0.9800C43—O121.398 (4)
C11—O31.182 (4)C44—O111.365 (4)
C11—O21.342 (3)C44—C451.382 (5)
C11—O41.343 (4)C45—C461.381 (5)
C12—C131.377 (4)C45—C491.510 (6)
C12—C171.386 (4)C46—C471.385 (7)
C12—O41.404 (3)C46—H460.9500
C13—O51.359 (3)C47—C481.375 (7)
C13—C141.391 (4)C47—H470.9500
C14—C151.375 (4)C48—H480.9500
C14—C181.500 (4)C49—C501.534 (5)
C15—C161.395 (5)C49—H49A0.9900
C15—H150.9500C49—H49B0.9900
C16—C171.380 (4)C50—O111.473 (4)
C16—H160.9500C50—C511.506 (5)
C17—H170.9500C50—C521.514 (5)
C18—C191.537 (4)C51—H51A0.9800
C18—H18A0.9900C51—H51B0.9800
C18—H18B0.9900C51—H51C0.9800
C19—O51.483 (4)C52—H52A0.9800
C19—C211.495 (5)C52—H52B0.9800
C19—C201.521 (5)C52—H52C0.9800
C20—H20A0.9800C53—O131.185 (4)
C20—H20B0.9800C53—O141.336 (4)
C20—H20C0.9800C53—O121.346 (4)
C21—H21A0.9800C54—C551.371 (5)
C21—H21B0.9800C54—C591.374 (5)
C21—H21C0.9800C54—O141.409 (4)
C22—C231.379 (4)C55—O151.361 (4)
C22—C271.380 (4)C55—C561.384 (5)
C22—O71.401 (3)C56—C571.382 (6)
C23—O61.356 (4)C56—C601.512 (6)
C23—C241.374 (4)C57—C581.389 (6)
C24—C251.379 (5)C57—H570.9500
C24—C281.507 (5)C58—C591.375 (6)
C25—C261.381 (5)C58—H580.9500
C25—H250.9500C59—H590.9500
C26—C271.380 (5)C60—C611.525 (6)
C26—H260.9500C60—H60A0.9900
C27—H270.9500C60—H60B0.9900
C28—C291.540 (5)C61—C63B1.474 (13)
C28—H28A0.9900C61—O151.482 (4)
C28—H28B0.9900C61—C62B1.501 (7)
C29—O61.490 (4)C61—C631.527 (19)
C29—C301.495 (6)C61—C621.584 (15)
C29—C311.512 (6)C62—H62A0.9800
C30—H30A0.9800C62—H62B0.9800
C30—H30B0.9800C62—H62C0.9800
C30—H30C0.9800C63—H63A0.9800
C31—H31A0.9800C63—H63B0.9800
C31—H31B0.9800C63—H63C0.9800
C31—H31C0.9800C62B—H62D0.9800
C32—O81.184 (4)C62B—H62E0.9800
C32—O71.340 (4)C62B—H62F0.9800
C32—O91.341 (4)C63B—H63D0.9800
C33—C381.375 (4)C63B—H63E0.9800
C33—C341.378 (4)C63B—H63F0.9800
C33—O91.417 (4)
C2—C1—C6119.8 (3)C38—C37—H37119.5
C2—C1—O2119.3 (2)C33—C38—C37119.9 (3)
C6—C1—O2120.8 (3)C33—C38—H38120.1
O1—C2—C1124.6 (3)C37—C38—H38120.1
O1—C2—C3114.9 (3)C35—C39—C40102.7 (2)
C1—C2—C3120.6 (3)C35—C39—H39A111.2
C2—C3—C4119.9 (3)C40—C39—H39A111.2
C2—C3—C7107.3 (3)C35—C39—H39B111.2
C4—C3—C7132.8 (3)C40—C39—H39B111.2
C5—C4—C3119.1 (3)H39A—C39—H39B109.1
C5—C4—H4120.4O10—C40—C41107.2 (3)
C3—C4—H4120.4O10—C40—C42105.8 (3)
C6—C5—C4120.9 (3)C41—C40—C42112.7 (3)
C6—C5—H5119.6O10—C40—C39104.4 (2)
C4—C5—H5119.6C41—C40—C39111.2 (3)
C1—C6—C5119.7 (3)C42—C40—C39114.7 (3)
C1—C6—H6120.1C40—C41—H41A109.5
C5—C6—H6120.1C40—C41—H41B109.5
C3—C7—C8103.0 (3)H41A—C41—H41B109.5
C3—C7—H7A111.2C40—C41—H41C109.5
C8—C7—H7A111.2H41A—C41—H41C109.5
C3—C7—H7B111.2H41B—C41—H41C109.5
C8—C7—H7B111.2C40—C42—H42A109.5
H7A—C7—H7B109.1C40—C42—H42B109.5
O1—C8—C10106.6 (3)H42A—C42—H42B109.5
O1—C8—C9106.1 (2)C40—C42—H42C109.5
C10—C8—C9112.0 (3)H42A—C42—H42C109.5
O1—C8—C7105.2 (2)H42B—C42—H42C109.5
C10—C8—C7112.6 (3)C48—C43—C44119.0 (4)
C9—C8—C7113.7 (3)C48—C43—O12120.0 (4)
C8—C9—H9A109.5C44—C43—O12120.9 (3)
C8—C9—H9B109.5O11—C44—C43124.2 (3)
H9A—C9—H9B109.5O11—C44—C45114.1 (3)
C8—C9—H9C109.5C43—C44—C45121.7 (3)
H9A—C9—H9C109.5C46—C45—C44118.8 (4)
H9B—C9—H9C109.5C46—C45—C49133.9 (4)
C8—C10—H10A109.5C44—C45—C49107.3 (3)
C8—C10—H10B109.5C45—C46—C47119.6 (4)
H10A—C10—H10B109.5C45—C46—H46120.2
C8—C10—H10C109.5C47—C46—H46120.2
H10A—C10—H10C109.5C48—C47—C46120.6 (4)
H10B—C10—H10C109.5C48—C47—H47119.7
O3—C11—O2126.6 (3)C46—C47—H47119.7
O3—C11—O4127.3 (3)C43—C48—C47120.3 (4)
O2—C11—O4106.1 (2)C43—C48—H48119.8
C13—C12—C17119.4 (3)C47—C48—H48119.8
C13—C12—O4118.8 (3)C45—C49—C50103.0 (3)
C17—C12—O4121.6 (2)C45—C49—H49A111.2
O5—C13—C12125.7 (3)C50—C49—H49A111.2
O5—C13—C14113.8 (2)C45—C49—H49B111.2
C12—C13—C14120.5 (3)C50—C49—H49B111.2
C15—C14—C13120.4 (3)H49A—C49—H49B109.1
C15—C14—C18132.1 (3)O11—C50—C51104.9 (3)
C13—C14—C18107.5 (3)O11—C50—C52107.6 (3)
C14—C15—C16118.9 (3)C51—C50—C52110.5 (4)
C14—C15—H15120.5O11—C50—C49105.7 (3)
C16—C15—H15120.5C51—C50—C49113.2 (3)
C17—C16—C15120.6 (3)C52—C50—C49114.2 (3)
C17—C16—H16119.7C50—C51—H51A109.5
C15—C16—H16119.7C50—C51—H51B109.5
C16—C17—C12120.1 (3)H51A—C51—H51B109.5
C16—C17—H17120.0C50—C51—H51C109.5
C12—C17—H17120.0H51A—C51—H51C109.5
C14—C18—C19102.8 (2)H51B—C51—H51C109.5
C14—C18—H18A111.2C50—C52—H52A109.5
C19—C18—H18A111.2C50—C52—H52B109.5
C14—C18—H18B111.2H52A—C52—H52B109.5
C19—C18—H18B111.2C50—C52—H52C109.5
H18A—C18—H18B109.1H52A—C52—H52C109.5
O5—C19—C21107.2 (3)H52B—C52—H52C109.5
O5—C19—C20106.7 (2)O13—C53—O14128.1 (3)
C21—C19—C20112.7 (3)O13—C53—O12126.9 (3)
O5—C19—C18105.2 (2)O14—C53—O12104.9 (3)
C21—C19—C18114.2 (3)C55—C54—C59119.6 (3)
C20—C19—C18110.2 (3)C55—C54—O14118.5 (3)
C19—C20—H20A109.5C59—C54—O14121.6 (3)
C19—C20—H20B109.5O15—C55—C54124.6 (3)
H20A—C20—H20B109.5O15—C55—C56114.6 (3)
C19—C20—H20C109.5C54—C55—C56120.8 (3)
H20A—C20—H20C109.5C57—C56—C55119.9 (4)
H20B—C20—H20C109.5C57—C56—C60133.1 (4)
C19—C21—H21A109.5C55—C56—C60107.0 (3)
C19—C21—H21B109.5C56—C57—C58118.8 (4)
H21A—C21—H21B109.5C56—C57—H57120.6
C19—C21—H21C109.5C58—C57—H57120.6
H21A—C21—H21C109.5C59—C58—C57120.7 (4)
H21B—C21—H21C109.5C59—C58—H58119.6
C23—C22—C27119.0 (3)C57—C58—H58119.6
C23—C22—O7120.6 (3)C54—C59—C58120.1 (4)
C27—C22—O7120.0 (3)C54—C59—H59119.9
O6—C23—C24114.8 (3)C58—C59—H59119.9
O6—C23—C22124.4 (3)C56—C60—C61103.4 (3)
C24—C23—C22120.8 (3)C56—C60—H60A111.1
C23—C24—C25120.2 (3)C61—C60—H60A111.1
C23—C24—C28107.7 (3)C56—C60—H60B111.1
C25—C24—C28131.9 (3)C61—C60—H60B111.1
C24—C25—C26119.2 (3)H60A—C60—H60B109.1
C24—C25—H25120.4C63B—C61—O15108.3 (6)
C26—C25—H25120.4C63B—C61—C62B115.9 (6)
C27—C26—C25120.3 (3)O15—C61—C62B103.4 (4)
C27—C26—H26119.8C63B—C61—C60116.5 (6)
C25—C26—H26119.8O15—C61—C60106.1 (3)
C22—C27—C26120.4 (3)C62B—C61—C60105.5 (6)
C22—C27—H27119.8O15—C61—C63103.3 (7)
C26—C27—H27119.8C62B—C61—C63130.6 (8)
C24—C28—C29103.2 (3)C60—C61—C63105.9 (6)
C24—C28—H28A111.1C63B—C61—C6286.5 (8)
C29—C28—H28A111.1O15—C61—C62108.9 (6)
C24—C28—H28B111.1C60—C61—C62128.5 (9)
C29—C28—H28B111.1C63—C61—C62101.4 (11)
H28A—C28—H28B109.1C61—C62—H62A109.5
O6—C29—C30107.0 (3)C61—C62—H62B109.5
O6—C29—C31105.6 (3)H62A—C62—H62B109.5
C30—C29—C31112.6 (3)C61—C62—H62C109.5
O6—C29—C28105.3 (3)H62A—C62—H62C109.5
C30—C29—C28111.7 (4)H62B—C62—H62C109.5
C31—C29—C28114.1 (4)C61—C63—H63A109.5
C29—C30—H30A109.5C61—C63—H63B109.5
C29—C30—H30B109.5H63A—C63—H63B109.5
H30A—C30—H30B109.5C61—C63—H63C109.5
C29—C30—H30C109.5H63A—C63—H63C109.5
H30A—C30—H30C109.5H63B—C63—H63C109.5
H30B—C30—H30C109.5C61—C62B—H62D109.5
C29—C31—H31A109.5C61—C62B—H62E109.5
C29—C31—H31B109.5H62D—C62B—H62E109.5
H31A—C31—H31B109.5C61—C62B—H62F109.5
C29—C31—H31C109.5H62D—C62B—H62F109.5
H31A—C31—H31C109.5H62E—C62B—H62F109.5
H31B—C31—H31C109.5C61—C63B—H63D109.5
O8—C32—O7127.3 (3)C61—C63B—H63E109.5
O8—C32—O9126.9 (3)H63D—C63B—H63E109.5
O7—C32—O9105.8 (3)C61—C63B—H63F109.5
C38—C33—C34119.4 (3)H63D—C63B—H63F109.5
C38—C33—O9122.7 (3)H63E—C63B—H63F109.5
C34—C33—O9117.7 (3)C2—O1—C8106.6 (2)
O10—C34—C33125.1 (3)C11—O2—C1114.8 (2)
O10—C34—C35114.2 (3)C11—O4—C12116.9 (2)
C33—C34—C35120.8 (3)C13—O5—C19107.2 (2)
C36—C35—C34119.8 (3)C23—O6—C29107.4 (2)
C36—C35—C39133.1 (3)C32—O7—C22116.2 (2)
C34—C35—C39107.1 (3)C32—O9—C33117.8 (2)
C35—C36—C37119.2 (3)C34—O10—C40106.6 (2)
C35—C36—H36120.4C44—O11—C50107.3 (2)
C37—C36—H36120.4C53—O12—C43116.0 (3)
C36—C37—C38121.0 (3)C53—O14—C54117.8 (3)
C36—C37—H37119.5C55—O15—C61107.2 (3)
C6—C1—C2—O1179.3 (3)C45—C46—C47—C480.7 (6)
O2—C1—C2—O14.3 (4)C44—C43—C48—C472.1 (6)
C6—C1—C2—C30.7 (4)O12—C43—C48—C47178.4 (3)
O2—C1—C2—C3177.0 (2)C46—C47—C48—C430.4 (6)
O1—C2—C3—C4178.4 (3)C46—C45—C49—C50173.2 (4)
C1—C2—C3—C40.4 (4)C44—C45—C49—C5010.0 (4)
O1—C2—C3—C70.9 (4)C45—C49—C50—O1115.1 (4)
C1—C2—C3—C7177.9 (3)C45—C49—C50—C5199.2 (4)
C2—C3—C4—C51.1 (4)C45—C49—C50—C52133.2 (4)
C7—C3—C4—C5177.9 (3)C59—C54—C55—O15178.3 (3)
C3—C4—C5—C60.8 (5)O14—C54—C55—O158.3 (5)
C2—C1—C6—C50.9 (4)C59—C54—C55—C563.5 (5)
O2—C1—C6—C5177.2 (3)O14—C54—C55—C56169.9 (3)
C4—C5—C6—C10.2 (5)O15—C55—C56—C57178.2 (3)
C2—C3—C7—C811.0 (3)C54—C55—C56—C573.3 (5)
C4—C3—C7—C8171.8 (3)O15—C55—C56—C604.2 (4)
C3—C7—C8—O116.6 (3)C54—C55—C56—C60174.3 (3)
C3—C7—C8—C1099.1 (3)C55—C56—C57—C580.7 (6)
C3—C7—C8—C9132.3 (3)C60—C56—C57—C58176.2 (4)
C17—C12—C13—O5179.3 (3)C56—C57—C58—C591.8 (6)
O4—C12—C13—O55.1 (4)C55—C54—C59—C581.0 (6)
C17—C12—C13—C140.8 (4)O14—C54—C59—C58172.2 (3)
O4—C12—C13—C14174.8 (2)C57—C58—C59—C541.7 (6)
O5—C13—C14—C15177.7 (3)C57—C56—C60—C61172.2 (4)
C12—C13—C14—C152.4 (4)C55—C56—C60—C6110.7 (4)
O5—C13—C14—C183.2 (3)C56—C60—C61—C63B107.4 (7)
C12—C13—C14—C18176.7 (3)C56—C60—C61—O1513.2 (4)
C13—C14—C15—C161.6 (4)C56—C60—C61—C62B122.5 (5)
C18—C14—C15—C16177.3 (3)C56—C60—C61—C6396.2 (7)
C14—C15—C16—C170.8 (5)C56—C60—C61—C62144.6 (10)
C15—C16—C17—C122.4 (5)C1—C2—O1—C8170.9 (3)
C13—C12—C17—C161.6 (4)C3—C2—O1—C810.3 (3)
O4—C12—C17—C16177.0 (3)C10—C8—O1—C2103.1 (3)
C15—C14—C18—C19167.9 (3)C9—C8—O1—C2137.4 (3)
C13—C14—C18—C1913.1 (3)C7—C8—O1—C216.6 (3)
C14—C18—C19—O517.8 (3)O3—C11—O2—C112.7 (4)
C14—C18—C19—C21135.0 (3)O4—C11—O2—C1168.3 (2)
C14—C18—C19—C2096.9 (3)C2—C1—O2—C1165.4 (3)
C27—C22—C23—O6176.0 (3)C6—C1—O2—C11118.3 (3)
O7—C22—C23—O62.4 (5)O3—C11—O4—C128.4 (4)
C27—C22—C23—C241.1 (5)O2—C11—O4—C12172.7 (2)
O7—C22—C23—C24174.7 (3)C13—C12—O4—C11129.4 (3)
O6—C23—C24—C25177.3 (3)C17—C12—O4—C1155.2 (4)
C22—C23—C24—C250.1 (5)C12—C13—O5—C19171.2 (3)
O6—C23—C24—C281.6 (5)C14—C13—O5—C198.8 (3)
C22—C23—C24—C28175.8 (3)C21—C19—O5—C13138.6 (3)
C23—C24—C25—C260.4 (6)C20—C19—O5—C13100.4 (3)
C28—C24—C25—C26174.1 (4)C18—C19—O5—C1316.7 (3)
C24—C25—C26—C270.1 (5)C24—C23—O6—C297.1 (4)
C23—C22—C27—C261.7 (5)C22—C23—O6—C29175.6 (3)
O7—C22—C27—C26175.3 (3)C30—C29—O6—C23106.6 (3)
C25—C26—C27—C221.2 (5)C31—C29—O6—C23133.3 (3)
C23—C24—C28—C299.1 (5)C28—C29—O6—C2312.4 (4)
C25—C24—C28—C29175.9 (4)O8—C32—O7—C2213.8 (5)
C24—C28—C29—O612.7 (5)O9—C32—O7—C22166.8 (2)
C24—C28—C29—C30103.0 (4)C23—C22—O7—C3263.1 (4)
C24—C28—C29—C31128.0 (4)C27—C22—O7—C32123.4 (3)
C38—C33—C34—O10179.9 (3)O8—C32—O9—C335.0 (5)
O9—C33—C34—O105.4 (4)O7—C32—O9—C33175.6 (2)
C38—C33—C34—C350.4 (5)C38—C33—O9—C3257.3 (4)
O9—C33—C34—C35174.1 (3)C34—C33—O9—C32128.3 (3)
O10—C34—C35—C36178.9 (3)C33—C34—O10—C40168.4 (3)
C33—C34—C35—C361.5 (5)C35—C34—O10—C4012.0 (3)
O10—C34—C35—C392.6 (4)C41—C40—O10—C3497.2 (3)
C33—C34—C35—C39177.1 (3)C42—C40—O10—C34142.3 (3)
C34—C35—C36—C371.1 (5)C39—C40—O10—C3420.9 (3)
C39—C35—C36—C37177.0 (4)C43—C44—O11—C50170.8 (3)
C35—C36—C37—C380.5 (5)C45—C44—O11—C509.4 (4)
C34—C33—C38—C371.2 (5)C51—C50—O11—C44104.7 (3)
O9—C33—C38—C37175.4 (3)C52—C50—O11—C44137.7 (3)
C36—C37—C38—C331.6 (5)C49—C50—O11—C4415.2 (3)
C36—C35—C39—C40166.5 (4)O13—C53—O12—C433.5 (5)
C34—C35—C39—C4015.2 (3)O14—C53—O12—C43175.4 (3)
C35—C39—C40—O1021.6 (3)C48—C43—O12—C53109.8 (4)
C35—C39—C40—C4193.7 (3)C44—C43—O12—C5373.9 (4)
C35—C39—C40—C42136.8 (3)O13—C53—O14—C541.4 (6)
C48—C43—C44—O11177.1 (3)O12—C53—O14—C54179.6 (3)
O12—C43—C44—O110.8 (5)C55—C54—O14—C53116.1 (4)
C48—C43—C44—C452.8 (5)C59—C54—O14—C5370.7 (4)
O12—C43—C44—C45179.0 (3)C54—C55—O15—C61177.0 (3)
O11—C44—C45—C46178.1 (3)C56—C55—O15—C614.6 (4)
C43—C44—C45—C461.7 (5)C63B—C61—O15—C55114.5 (7)
O11—C44—C45—C490.8 (4)C62B—C61—O15—C55122.1 (6)
C43—C44—C45—C49179.0 (3)C60—C61—O15—C5511.3 (4)
C44—C45—C46—C470.0 (5)C63—C61—O15—C5599.9 (7)
C49—C45—C46—C47176.4 (4)C62—C61—O15—C55152.9 (11)

Experimental details

Crystal data
Chemical formulaC21H22O5
Mr354.39
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)173
a, b, c (Å)16.6409 (6), 23.2581 (9), 14.5045 (6)
V3)5613.8 (4)
Z12
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.46 × 0.44 × 0.42
Data collection
DiffractometerBruker SMART 1000 CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.960, 0.964
No. of measured, independent and
observed [I > 2σ(I)] reflections
27906, 6368, 4923
Rint0.030
(sin θ/λ)max1)0.640
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.109, 1.06
No. of reflections6368
No. of parameters732
No. of restraints32
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.21

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by the Central University Basic Scientific Research Fund of Hunan University.

References

First citationBruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLi, W.-S., Li, L. & Li, J.-S. (2009). Acta Cryst. E65, o2928.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTomlin, C. (1994). The Pesticide Manual. A World Compendium, 10th ed., pp. 152–153. Bath: The British Crop Protection Council, The Bath Press.  Google Scholar
First citationXu, L.-Z., Yu, G.-P. & Yang, S.-H. (2005). Acta Cryst. E61, o1924–o1926.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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