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

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ISSN: 2056-9890

2,2-Di­methyl-5-tri­phenyl­methyl-1,3-dioxane

aDepartment of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou Hunan 425100, People's Republic of China
*Correspondence e-mail: zm_zmcm@sina.com

(Received 30 November 2008; accepted 5 January 2009; online 14 January 2009)

The title compound, C25H26O2, crystallizes with two crystallographically independent mol­ecules in the asymmetric unit. The differences between the two mol­ecules are marginal. The three benzene rings of each mol­ecule are in a propeller orientation and the 1,3-dioxane ring adopts a chair conformation.

Related literature

For the synthesis of the compound, see: Whilt & Finnerty (1961[Whilt, J. W. & Finnerty, J. L. (1961). J. Org. Chem. 26, 2173-2177.]); Yuan et al. (2007[Yuan, X. Y., Zhang, M. & Yuan, L. (2007). Chin. J. Org. Chem. 27, 1600-1604.]); Wang et al. (1995[Wang, G. W., Yuan, X. Y., Liu, Y. C., Lei, X. G. & Guo, Q. X. (1995). J. Am. Oil Chem. Soc. 72, 83-87.]). For applications of this class of compounds, see: Wang, Yuan, Liu et al. (1996[Wang, G. W., Yuan, X. Y., Liu, Y. C., Guo, Q. X. & Lei, X. G. (1996). Indian J. Chem. Sect. B, 35, 583-585.]); Wang, Yuan, Lei & Liu (1996[Wang, G. W., Yuan, X. Y., Lei, X. G. & Liu, Y. C. (1996). Chin. J. Appl. Chem. 11, 114-115.]); Yuan et al. (2005[Yuan, X. Y., Yang, N. F., Luo, H. A. & Liu, Y. J. (2005). Chin. J. Org. Chem. 25, 1049-1052.]). For related crystal structures, see: Chuprunov et al. (1981[Chuprunov, E. V., Tarkhova, T. N., Korallova, T. Y., Simonov, M. A. & Belov, W. V. (1981). Zh. Strukt. Khim. 22, 191-192.]); Yuan et al. (2008[Yuan, X.-Y., Zhang, M. & Ng, S. W. (2008). Acta Cryst. E64, o1314.]).

[Scheme 1]

Experimental

Crystal data
  • C25H26O2

  • Mr = 358.47

  • Triclinic, [P \overline 1]

  • a = 10.7252 (18) Å

  • b = 11.6933 (19) Å

  • c = 15.840 (3) Å

  • α = 89.574 (3)°

  • β = 88.906 (3)°

  • γ = 86.427 (3)°

  • V = 1982.3 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 298 (2) K

  • 0.45 × 0.38 × 0.29 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.967, Tmax = 0.979

  • 16710 measured reflections

  • 8543 independent reflections

  • 5142 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.193

  • S = 1.07

  • 8543 reflections

  • 491 parameters

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound was synthesized to be use as a intermediate in surface activating reagent syntheses. The compound belongs to a class of 1,3-dioxane derivatives that have application in fine chemical medicine such as biology pharmacy (Wang, Yuan, Liu et al., 1996) and cosmetic industry (Wang, Yuan, Lei & Liu, 1996; Yuan et al., 2005).

The title compound (Fig. 1) crystallizes with two crystallographically independent molecules per asymmetric unit. Differences between the two molecules are marginal. The three benzene rings of each molecule are in a propeller orientation and the 1,3-dioxane ring adopts a chair conformation. The structure is similar to that reported (Chuprunov et al., 1981; Yuan et al., 2008).

Related literature top

For the synthesis of the compound, see: Whilt et al. (1961); Yuan et al. (2007); Wang et al. (1995). For applications of this class of compounds, see: Wang, Yuan, Liu et al. (1996); Wang, Yuan, Lei & Liu (1996); Yuan et al. (2005). For related crystal structures, see: Chuprunov et al. (1981); Yuan et al. (2008).

Experimental top

A mixture of 0.24 g (5.0 mmol) of 2,2-bis(hydroxymethyl)-1,3-propanediol, 0.10 g of phosphotungstic acid supported on actived carbon and 10 ml of acetone were added to a round bottom flask of 50 ml and heated under microwave irradiation condition for 3 min, then 5 ml benzene was added to this mixture. Then, this solution was heated, filtrated, and washed by using hot benzene. After benzene was evaporated and the sample was cooled. The resultant solid was recrystallized from anhydrous ethanol to give 1.1 g (58%) of white solid.

Refinement top

H atoms were placed in calculated positions (C—H 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 Ueq(C) or 1.5 Ueq(Cmethyl).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 30% probability level. H-atoms have been excluded for clarity.
[Figure 2] Fig. 2. A view of the packing of the title compound.
2,2-Dimethyl-5-triphenylmethyl-1,3-dioxane top
Crystal data top
C25H26O2Z = 4
Mr = 358.47F(000) = 768
Triclinic, P1Dx = 1.201 Mg m3
a = 10.7252 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.6933 (19) ÅCell parameters from 5597 reflections
c = 15.840 (3) Åθ = 2.2–27.0°
α = 89.574 (3)°µ = 0.07 mm1
β = 88.906 (3)°T = 298 K
γ = 86.427 (3)°Prism, colorless
V = 1982.3 (6) Å30.45 × 0.38 × 0.29 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
8543 independent reflections
Radiation source: fine-focus sealed tube5142 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ϕ and ω scansθmax = 27.2°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.967, Tmax = 0.979k = 1414
16710 measured reflectionsl = 2020
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.1105P)2]
where P = (Fo2 + 2Fc2)/3
8543 reflections(Δ/σ)max < 0.001
491 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C25H26O2γ = 86.427 (3)°
Mr = 358.47V = 1982.3 (6) Å3
Triclinic, P1Z = 4
a = 10.7252 (18) ÅMo Kα radiation
b = 11.6933 (19) ŵ = 0.07 mm1
c = 15.840 (3) ÅT = 298 K
α = 89.574 (3)°0.45 × 0.38 × 0.29 mm
β = 88.906 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
8543 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5142 reflections with I > 2σ(I)
Tmin = 0.967, Tmax = 0.979Rint = 0.028
16710 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.193H-atom parameters constrained
S = 1.07Δρmax = 0.20 e Å3
8543 reflectionsΔρmin = 0.24 e Å3
491 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
O10.35990 (12)0.60731 (12)0.01269 (8)0.0549 (4)
O20.14384 (12)0.63492 (12)0.01747 (9)0.0563 (4)
C10.23664 (16)0.38835 (15)0.17018 (10)0.0397 (4)
C200.24344 (15)0.49994 (15)0.11561 (10)0.0409 (4)
H200.25020.56340.15500.049*
C20.11404 (16)0.39031 (15)0.22318 (10)0.0411 (4)
C140.34210 (17)0.37887 (16)0.23626 (11)0.0447 (4)
C80.24895 (18)0.28587 (15)0.10870 (11)0.0445 (4)
C220.35745 (17)0.49994 (17)0.05630 (12)0.0494 (5)
H22A0.43300.48680.08860.059*
H22B0.35430.43850.01580.059*
C90.1479 (2)0.25685 (17)0.06129 (12)0.0541 (5)
H90.07010.29480.07050.065*
C210.12987 (17)0.53031 (17)0.06175 (12)0.0510 (5)
H21A0.11960.46940.02170.061*
H21B0.05550.53740.09760.061*
C50.1020 (2)0.39266 (19)0.32589 (12)0.0564 (5)
H50.17440.39360.35920.068*
C30.06172 (19)0.49044 (17)0.25835 (12)0.0532 (5)
H30.09950.55880.24810.064*
C130.3626 (2)0.22658 (18)0.09322 (12)0.0576 (5)
H130.43190.24400.12400.069*
C150.3606 (2)0.27827 (19)0.28297 (13)0.0598 (5)
H150.30950.21820.27400.072*
C70.0561 (2)0.29087 (17)0.24326 (12)0.0559 (5)
H70.08970.22130.22230.067*
C110.2745 (3)0.1148 (2)0.01380 (14)0.0774 (8)
H110.28310.05810.05470.093*
C60.0505 (2)0.29260 (19)0.29377 (13)0.0628 (6)
H60.08760.22440.30590.075*
C100.1616 (3)0.1723 (2)0.00074 (13)0.0687 (7)
H100.09300.15430.03050.082*
C40.0455 (2)0.49138 (19)0.30843 (13)0.0605 (6)
H40.07930.56030.33040.073*
C120.3750 (3)0.1417 (2)0.03269 (14)0.0727 (7)
H120.45210.10250.02350.087*
C160.4528 (2)0.2656 (2)0.34232 (14)0.0753 (7)
H160.46390.19700.37220.090*
C190.4159 (2)0.4675 (2)0.25485 (13)0.0666 (6)
H190.40300.53740.22710.080*
C180.5097 (3)0.4537 (3)0.31478 (16)0.0946 (10)
H180.56000.51380.32550.113*
C170.5278 (2)0.3528 (3)0.35755 (15)0.0896 (9)
H170.59090.34340.39690.107*
O30.83700 (13)1.13075 (11)0.47955 (8)0.0561 (4)
C260.77111 (16)0.88371 (15)0.33012 (11)0.0409 (4)
C390.88286 (16)0.89755 (15)0.26818 (11)0.0414 (4)
O40.62945 (13)1.09080 (13)0.49852 (9)0.0633 (4)
C270.65934 (17)0.86683 (15)0.27145 (11)0.0426 (4)
C450.74962 (16)0.99479 (16)0.38537 (11)0.0442 (4)
H450.72371.05810.34740.053*
C400.88986 (19)0.99737 (17)0.22169 (12)0.0516 (5)
H400.82851.05620.22970.062*
C330.79058 (18)0.78071 (16)0.39142 (11)0.0466 (5)
C470.86490 (18)1.02937 (16)0.43135 (12)0.0493 (5)
H47A0.89420.96750.46860.059*
H47B0.93111.04270.39050.059*
C460.64654 (18)0.98545 (19)0.45268 (13)0.0571 (5)
H46A0.56900.96900.42600.069*
H46B0.66900.92310.49130.069*
C290.5612 (2)0.7445 (2)0.17364 (13)0.0642 (6)
H290.56180.67530.14500.077*
C280.6577 (2)0.76446 (17)0.22676 (12)0.0535 (5)
H280.72280.70890.23290.064*
C380.9023 (2)0.75861 (18)0.43297 (12)0.0561 (5)
H380.96960.80230.41960.067*
C440.9728 (2)0.81094 (18)0.25085 (13)0.0578 (5)
H440.96910.74110.27890.069*
C410.9853 (2)1.01248 (18)0.16365 (13)0.0593 (6)
H410.98771.08100.13370.071*
C431.0682 (2)0.8258 (2)0.19260 (14)0.0672 (6)
H431.12760.76600.18230.081*
C421.0762 (2)0.92683 (19)0.15016 (13)0.0608 (6)
H421.14240.93750.11270.073*
C320.5633 (2)0.94808 (19)0.25808 (12)0.0587 (5)
H320.56311.01820.28540.070*
C340.6930 (2)0.71336 (18)0.41398 (12)0.0578 (5)
H340.61640.72630.38800.069*
C310.4666 (2)0.9269 (2)0.20438 (14)0.0721 (7)
H310.40210.98270.19680.087*
C300.4647 (2)0.8250 (2)0.16248 (14)0.0706 (7)
H300.39920.81080.12720.085*
C360.8190 (3)0.6071 (2)0.51405 (15)0.0844 (8)
H360.82890.54910.55430.101*
C370.9166 (3)0.6740 (2)0.49340 (14)0.0753 (7)
H370.99250.66180.52050.090*
C350.7070 (3)0.6273 (2)0.47431 (14)0.0750 (7)
H350.64030.58300.48790.090*
C480.73853 (19)1.12060 (19)0.54019 (13)0.0584 (6)
C230.25244 (18)0.63539 (18)0.03605 (12)0.0533 (5)
C490.7751 (2)1.0359 (2)0.60968 (14)0.0728 (7)
H49A0.70591.02950.64840.109*
H49B0.84511.06220.63930.109*
H49C0.79750.96230.58540.109*
C250.2614 (2)0.7575 (2)0.06423 (17)0.0828 (8)
H25A0.27010.80510.01580.124*
H25B0.18710.78250.09370.124*
H25C0.33280.76300.10120.124*
C240.2427 (3)0.5554 (2)0.11037 (13)0.0809 (7)
H24A0.31680.55730.14520.121*
H24B0.17120.57960.14300.121*
H24C0.23390.47880.09000.121*
C500.7094 (2)1.2394 (2)0.57462 (16)0.0812 (8)
H50A0.68781.29110.52910.122*
H50B0.78141.26470.60250.122*
H50C0.64051.23820.61420.122*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0381 (7)0.0684 (9)0.0581 (8)0.0039 (6)0.0018 (6)0.0164 (7)
O20.0422 (7)0.0641 (9)0.0604 (8)0.0094 (6)0.0038 (6)0.0162 (7)
C10.0353 (9)0.0450 (10)0.0387 (9)0.0001 (7)0.0037 (7)0.0040 (8)
C200.0343 (9)0.0477 (10)0.0406 (9)0.0013 (8)0.0018 (7)0.0016 (8)
C20.0416 (10)0.0458 (10)0.0359 (9)0.0038 (8)0.0026 (7)0.0009 (8)
C140.0411 (10)0.0529 (11)0.0393 (9)0.0041 (8)0.0032 (8)0.0050 (8)
C80.0523 (11)0.0433 (10)0.0379 (9)0.0034 (8)0.0014 (8)0.0046 (8)
C220.0365 (10)0.0613 (12)0.0495 (11)0.0033 (9)0.0013 (8)0.0096 (9)
C90.0586 (13)0.0565 (12)0.0487 (11)0.0149 (10)0.0026 (9)0.0047 (9)
C210.0358 (10)0.0626 (12)0.0543 (11)0.0014 (9)0.0027 (8)0.0132 (10)
C50.0534 (12)0.0716 (14)0.0438 (11)0.0036 (10)0.0080 (9)0.0051 (10)
C30.0599 (13)0.0456 (11)0.0541 (11)0.0063 (9)0.0131 (10)0.0037 (9)
C130.0608 (13)0.0610 (13)0.0500 (11)0.0058 (10)0.0011 (10)0.0096 (10)
C150.0651 (14)0.0601 (13)0.0528 (12)0.0116 (10)0.0109 (10)0.0023 (10)
C70.0630 (13)0.0496 (12)0.0552 (12)0.0065 (10)0.0076 (10)0.0024 (9)
C110.122 (2)0.0614 (15)0.0502 (13)0.0180 (15)0.0145 (14)0.0183 (11)
C60.0662 (14)0.0636 (14)0.0600 (13)0.0201 (11)0.0101 (11)0.0029 (11)
C100.0908 (19)0.0685 (15)0.0502 (12)0.0308 (14)0.0022 (12)0.0122 (11)
C40.0671 (14)0.0585 (13)0.0541 (12)0.0065 (11)0.0136 (10)0.0037 (10)
C120.0911 (18)0.0627 (14)0.0613 (14)0.0150 (13)0.0144 (13)0.0119 (12)
C160.0769 (17)0.0918 (18)0.0531 (13)0.0291 (15)0.0106 (12)0.0094 (13)
C190.0656 (14)0.0833 (16)0.0538 (12)0.0241 (12)0.0184 (11)0.0088 (11)
C180.0801 (18)0.144 (3)0.0663 (16)0.0493 (18)0.0329 (14)0.0151 (17)
C170.0605 (16)0.156 (3)0.0525 (14)0.0076 (17)0.0195 (12)0.0122 (17)
O30.0539 (8)0.0572 (8)0.0582 (8)0.0094 (6)0.0013 (7)0.0184 (7)
C260.0394 (10)0.0427 (10)0.0406 (9)0.0018 (8)0.0012 (7)0.0035 (8)
C390.0398 (10)0.0427 (10)0.0420 (9)0.0046 (8)0.0009 (8)0.0058 (8)
O40.0431 (8)0.0839 (10)0.0627 (9)0.0004 (7)0.0009 (6)0.0299 (8)
C270.0412 (10)0.0491 (10)0.0383 (9)0.0082 (8)0.0007 (8)0.0000 (8)
C450.0398 (10)0.0494 (11)0.0433 (10)0.0008 (8)0.0002 (8)0.0076 (8)
C400.0551 (12)0.0476 (11)0.0519 (11)0.0030 (9)0.0043 (9)0.0021 (9)
C330.0514 (11)0.0475 (11)0.0405 (10)0.0005 (9)0.0007 (8)0.0029 (8)
C470.0423 (10)0.0527 (11)0.0534 (11)0.0062 (8)0.0038 (9)0.0145 (9)
C460.0407 (11)0.0751 (14)0.0565 (12)0.0095 (10)0.0034 (9)0.0248 (10)
C290.0742 (16)0.0693 (14)0.0521 (12)0.0245 (12)0.0074 (11)0.0092 (11)
C280.0598 (13)0.0521 (12)0.0498 (11)0.0116 (10)0.0029 (9)0.0037 (9)
C380.0605 (13)0.0566 (12)0.0508 (11)0.0013 (10)0.0087 (10)0.0056 (10)
C440.0615 (13)0.0482 (11)0.0626 (13)0.0028 (10)0.0121 (10)0.0009 (10)
C410.0722 (15)0.0529 (12)0.0541 (12)0.0156 (11)0.0066 (11)0.0014 (10)
C430.0620 (14)0.0647 (14)0.0723 (15)0.0099 (11)0.0193 (12)0.0033 (12)
C420.0550 (13)0.0701 (15)0.0578 (12)0.0125 (11)0.0150 (10)0.0062 (11)
C320.0546 (12)0.0692 (14)0.0518 (11)0.0035 (11)0.0092 (10)0.0106 (10)
C340.0614 (13)0.0649 (13)0.0477 (11)0.0104 (11)0.0058 (10)0.0008 (10)
C310.0536 (13)0.106 (2)0.0555 (13)0.0057 (13)0.0110 (10)0.0004 (13)
C300.0582 (14)0.105 (2)0.0509 (12)0.0175 (14)0.0097 (10)0.0061 (13)
C360.131 (3)0.0755 (17)0.0456 (13)0.0012 (17)0.0040 (15)0.0143 (12)
C370.0946 (19)0.0752 (16)0.0547 (13)0.0118 (14)0.0221 (13)0.0005 (12)
C350.099 (2)0.0758 (16)0.0509 (13)0.0183 (14)0.0130 (13)0.0066 (12)
C480.0465 (11)0.0760 (15)0.0531 (12)0.0049 (10)0.0003 (9)0.0229 (11)
C230.0398 (11)0.0672 (13)0.0519 (11)0.0037 (9)0.0009 (9)0.0150 (10)
C490.0682 (15)0.0963 (18)0.0542 (13)0.0077 (13)0.0022 (11)0.0114 (13)
C250.0684 (16)0.0839 (18)0.0941 (18)0.0031 (13)0.0052 (14)0.0387 (15)
C240.0796 (17)0.114 (2)0.0469 (12)0.0107 (15)0.0044 (12)0.0026 (13)
C500.0734 (17)0.0898 (18)0.0798 (16)0.0063 (13)0.0030 (13)0.0411 (14)
Geometric parameters (Å, º) top
O1—C231.420 (2)O4—C481.417 (2)
O1—C221.430 (2)O4—C461.435 (2)
O2—C211.420 (2)C27—C321.376 (3)
O2—C231.428 (2)C27—C281.396 (3)
C1—C21.546 (2)C45—C471.524 (2)
C1—C81.547 (2)C45—C461.529 (3)
C1—C141.554 (2)C45—H450.9800
C1—C201.565 (2)C40—C411.381 (3)
C20—C211.523 (2)C40—H400.9300
C20—C221.528 (2)C33—C381.388 (3)
C20—H200.9800C33—C341.388 (3)
C2—C31.383 (3)C47—H47A0.9700
C2—C71.384 (3)C47—H47B0.9700
C14—C191.379 (3)C46—H46A0.9700
C14—C151.391 (3)C46—H46B0.9700
C8—C131.383 (3)C29—C301.368 (3)
C8—C91.391 (3)C29—C281.378 (3)
C22—H22A0.9700C29—H290.9300
C22—H22B0.9700C28—H280.9300
C9—C101.382 (3)C38—C371.375 (3)
C9—H90.9300C38—H380.9300
C21—H21A0.9700C44—C431.383 (3)
C21—H21B0.9700C44—H440.9300
C5—C61.360 (3)C41—C421.369 (3)
C5—C41.361 (3)C41—H410.9300
C5—H50.9300C43—C421.361 (3)
C3—C41.384 (3)C43—H430.9300
C3—H30.9300C42—H420.9300
C13—C121.384 (3)C32—C311.389 (3)
C13—H130.9300C32—H320.9300
C15—C161.378 (3)C34—C351.386 (3)
C15—H150.9300C34—H340.9300
C7—C61.383 (3)C31—C301.369 (3)
C7—H70.9300C31—H310.9300
C11—C101.364 (4)C30—H300.9300
C11—C121.370 (4)C36—C351.374 (4)
C11—H110.9300C36—C371.377 (4)
C6—H60.9300C36—H360.9300
C10—H100.9300C37—H370.9300
C4—H40.9300C35—H350.9300
C12—H120.9300C48—C501.509 (3)
C16—C171.363 (4)C48—C491.516 (3)
C16—H160.9300C23—C251.501 (3)
C19—C181.398 (3)C23—C241.518 (3)
C19—H190.9300C49—H49A0.9600
C18—C171.362 (4)C49—H49B0.9600
C18—H180.9300C49—H49C0.9600
C17—H170.9300C25—H25A0.9600
O3—C481.424 (2)C25—H25B0.9600
O3—C471.428 (2)C25—H25C0.9600
C26—C331.548 (3)C24—H24A0.9600
C26—C391.550 (2)C24—H24B0.9600
C26—C271.554 (2)C24—H24C0.9600
C26—C451.574 (2)C50—H50A0.9600
C39—C441.379 (3)C50—H50B0.9600
C39—C401.381 (2)C50—H50C0.9600
C23—O1—C22114.18 (14)C46—C45—H45107.5
C21—O2—C23114.44 (14)C26—C45—H45107.5
C2—C1—C8112.14 (14)C39—C40—C41122.00 (19)
C2—C1—C14104.69 (13)C39—C40—H40119.0
C8—C1—C14110.69 (14)C41—C40—H40119.0
C2—C1—C20111.03 (14)C38—C33—C34116.75 (18)
C8—C1—C20107.10 (13)C38—C33—C26121.56 (17)
C14—C1—C20111.27 (14)C34—C33—C26121.36 (18)
C21—C20—C22106.52 (14)O3—C47—C45110.77 (15)
C21—C20—C1115.43 (14)O3—C47—H47A109.5
C22—C20—C1113.94 (14)C45—C47—H47A109.5
C21—C20—H20106.8O3—C47—H47B109.5
C22—C20—H20106.8C45—C47—H47B109.5
C1—C20—H20106.8H47A—C47—H47B108.1
C3—C2—C7116.45 (17)O4—C46—C45109.95 (16)
C3—C2—C1121.60 (16)O4—C46—H46A109.7
C7—C2—C1121.77 (16)C45—C46—H46A109.7
C19—C14—C15117.11 (18)O4—C46—H46B109.7
C19—C14—C1123.60 (18)C45—C46—H46B109.7
C15—C14—C1119.21 (17)H46A—C46—H46B108.2
C13—C8—C9117.53 (17)C30—C29—C28120.9 (2)
C13—C8—C1121.48 (17)C30—C29—H29119.5
C9—C8—C1120.75 (17)C28—C29—H29119.5
O1—C22—C20110.11 (15)C29—C28—C27121.1 (2)
O1—C22—H22A109.6C29—C28—H28119.5
C20—C22—H22A109.6C27—C28—H28119.5
O1—C22—H22B109.6C37—C38—C33121.9 (2)
C20—C22—H22B109.6C37—C38—H38119.0
H22A—C22—H22B108.2C33—C38—H38119.0
C10—C9—C8120.9 (2)C39—C44—C43121.4 (2)
C10—C9—H9119.6C39—C44—H44119.3
C8—C9—H9119.6C43—C44—H44119.3
O2—C21—C20110.71 (15)C42—C41—C40120.2 (2)
O2—C21—H21A109.5C42—C41—H41119.9
C20—C21—H21A109.5C40—C41—H41119.9
O2—C21—H21B109.5C42—C43—C44120.9 (2)
C20—C21—H21B109.5C42—C43—H43119.6
H21A—C21—H21B108.1C44—C43—H43119.6
C6—C5—C4118.78 (19)C43—C42—C41118.82 (19)
C6—C5—H5120.6C43—C42—H42120.6
C4—C5—H5120.6C41—C42—H42120.6
C2—C3—C4121.57 (18)C27—C32—C31120.9 (2)
C2—C3—H3119.2C27—C32—H32119.5
C4—C3—H3119.2C31—C32—H32119.5
C8—C13—C12121.1 (2)C35—C34—C33121.6 (2)
C8—C13—H13119.5C35—C34—H34119.2
C12—C13—H13119.5C33—C34—H34119.2
C16—C15—C14121.5 (2)C30—C31—C32121.0 (2)
C16—C15—H15119.3C30—C31—H31119.5
C14—C15—H15119.3C32—C31—H31119.5
C6—C7—C2121.51 (19)C29—C30—C31118.6 (2)
C6—C7—H7119.2C29—C30—H30120.7
C2—C7—H7119.2C31—C30—H30120.7
C10—C11—C12119.2 (2)C35—C36—C37119.0 (2)
C10—C11—H11120.4C35—C36—H36120.5
C12—C11—H11120.4C37—C36—H36120.5
C5—C6—C7120.88 (19)C38—C37—C36120.4 (2)
C5—C6—H6119.6C38—C37—H37119.8
C7—C6—H6119.6C36—C37—H37119.8
C11—C10—C9120.8 (2)C36—C35—C34120.3 (2)
C11—C10—H10119.6C36—C35—H35119.9
C9—C10—H10119.6C34—C35—H35119.9
C5—C4—C3120.77 (19)O4—C48—O3109.22 (15)
C5—C4—H4119.6O4—C48—C50106.01 (17)
C3—C4—H4119.6O3—C48—C50106.01 (18)
C11—C12—C13120.6 (2)O4—C48—C49111.97 (19)
C11—C12—H12119.7O3—C48—C49111.75 (18)
C13—C12—H12119.7C50—C48—C49111.56 (18)
C17—C16—C15120.5 (2)O1—C23—O2109.10 (15)
C17—C16—H16119.8O1—C23—C25106.39 (17)
C15—C16—H16119.8O2—C23—C25105.74 (17)
C14—C19—C18121.0 (2)O1—C23—C24112.28 (17)
C14—C19—H19119.5O2—C23—C24111.23 (18)
C18—C19—H19119.5C25—C23—C24111.78 (19)
C17—C18—C19120.2 (2)C48—C49—H49A109.5
C17—C18—H18119.9C48—C49—H49B109.5
C19—C18—H18119.9H49A—C49—H49B109.5
C18—C17—C16119.6 (2)C48—C49—H49C109.5
C18—C17—H17120.2H49A—C49—H49C109.5
C16—C17—H17120.2H49B—C49—H49C109.5
C48—O3—C47113.78 (14)C23—C25—H25A109.5
C33—C26—C39113.51 (14)C23—C25—H25B109.5
C33—C26—C27110.61 (14)H25A—C25—H25B109.5
C39—C26—C27103.98 (13)C23—C25—H25C109.5
C33—C26—C45107.38 (14)H25A—C25—H25C109.5
C39—C26—C45109.49 (13)H25B—C25—H25C109.5
C27—C26—C45111.94 (14)C23—C24—H24A109.5
C44—C39—C40116.61 (17)C23—C24—H24B109.5
C44—C39—C26123.42 (17)H24A—C24—H24B109.5
C40—C39—C26119.74 (16)C23—C24—H24C109.5
C48—O4—C46113.22 (15)H24A—C24—H24C109.5
C32—C27—C28117.37 (18)H24B—C24—H24C109.5
C32—C27—C26124.24 (16)C48—C50—H50A109.5
C28—C27—C26118.35 (17)C48—C50—H50B109.5
C47—C45—C46106.41 (14)H50A—C50—H50B109.5
C47—C45—C26114.60 (14)C48—C50—H50C109.5
C46—C45—C26113.10 (15)H50A—C50—H50C109.5
C47—C45—H45107.5H50B—C50—H50C109.5
C2—C1—C20—C2151.71 (19)C33—C26—C27—C32130.26 (19)
C8—C1—C20—C2171.02 (19)C39—C26—C27—C32107.5 (2)
C14—C1—C20—C21167.89 (14)C45—C26—C27—C3210.6 (2)
C2—C1—C20—C22175.46 (14)C33—C26—C27—C2852.2 (2)
C8—C1—C20—C2252.73 (19)C39—C26—C27—C2870.04 (19)
C14—C1—C20—C2268.36 (18)C45—C26—C27—C28171.86 (15)
C8—C1—C2—C3156.43 (17)C33—C26—C45—C4769.82 (19)
C14—C1—C2—C383.5 (2)C39—C26—C45—C4753.8 (2)
C20—C1—C2—C336.7 (2)C27—C26—C45—C47168.60 (15)
C8—C1—C2—C728.6 (2)C33—C26—C45—C4652.4 (2)
C14—C1—C2—C791.5 (2)C39—C26—C45—C46176.05 (16)
C20—C1—C2—C7148.34 (17)C27—C26—C45—C4669.19 (19)
C2—C1—C14—C19108.4 (2)C44—C39—C40—C413.1 (3)
C8—C1—C14—C19130.6 (2)C26—C39—C40—C41177.85 (17)
C20—C1—C14—C1911.6 (2)C39—C26—C33—C3845.1 (2)
C2—C1—C14—C1568.2 (2)C27—C26—C33—C38161.54 (16)
C8—C1—C14—C1552.8 (2)C45—C26—C33—C3876.1 (2)
C20—C1—C14—C15171.80 (16)C39—C26—C33—C34141.63 (17)
C2—C1—C8—C13141.65 (18)C27—C26—C33—C3425.2 (2)
C14—C1—C8—C1325.1 (2)C45—C26—C33—C3497.21 (19)
C20—C1—C8—C1396.32 (19)C48—O3—C47—C4557.8 (2)
C2—C1—C8—C944.2 (2)C46—C45—C47—O354.4 (2)
C14—C1—C8—C9160.70 (16)C26—C45—C47—O3179.86 (14)
C20—C1—C8—C977.8 (2)C48—O4—C46—C4559.9 (2)
C23—O1—C22—C2058.7 (2)C47—C45—C46—O455.2 (2)
C21—C20—C22—O154.90 (19)C26—C45—C46—O4178.10 (15)
C1—C20—C22—O1176.66 (14)C30—C29—C28—C270.7 (3)
C13—C8—C9—C100.4 (3)C32—C27—C28—C292.2 (3)
C1—C8—C9—C10173.99 (17)C26—C27—C28—C29179.92 (17)
C23—O2—C21—C2057.8 (2)C34—C33—C38—C370.2 (3)
C22—C20—C21—O254.6 (2)C26—C33—C38—C37173.79 (18)
C1—C20—C21—O2177.79 (14)C40—C39—C44—C432.9 (3)
C7—C2—C3—C42.3 (3)C26—C39—C44—C43177.44 (19)
C1—C2—C3—C4177.53 (18)C39—C40—C41—C420.5 (3)
C9—C8—C13—C120.1 (3)C39—C44—C43—C420.2 (4)
C1—C8—C13—C12174.26 (18)C44—C43—C42—C412.5 (3)
C19—C14—C15—C163.2 (3)C40—C41—C42—C432.3 (3)
C1—C14—C15—C16180.00 (18)C28—C27—C32—C312.2 (3)
C3—C2—C7—C61.9 (3)C26—C27—C32—C31179.79 (18)
C1—C2—C7—C6177.14 (18)C38—C33—C34—C350.8 (3)
C4—C5—C6—C70.9 (3)C26—C33—C34—C35174.35 (18)
C2—C7—C6—C50.3 (3)C27—C32—C31—C300.7 (3)
C12—C11—C10—C90.2 (4)C28—C29—C30—C310.8 (3)
C8—C9—C10—C110.3 (3)C32—C31—C30—C290.8 (4)
C6—C5—C4—C30.5 (3)C33—C38—C37—C360.6 (3)
C2—C3—C4—C51.1 (3)C35—C36—C37—C380.9 (4)
C10—C11—C12—C130.5 (4)C37—C36—C35—C340.4 (4)
C8—C13—C12—C110.4 (3)C33—C34—C35—C360.5 (3)
C14—C15—C16—C170.9 (3)C46—O4—C48—O358.7 (2)
C15—C14—C19—C183.5 (3)C46—O4—C48—C50172.54 (18)
C1—C14—C19—C18179.8 (2)C46—O4—C48—C4965.6 (2)
C14—C19—C18—C171.7 (4)C47—O3—C48—O457.6 (2)
C19—C18—C17—C160.8 (4)C47—O3—C48—C50171.43 (17)
C15—C16—C17—C181.2 (4)C47—O3—C48—C4966.8 (2)
C33—C26—C39—C4418.5 (2)C22—O1—C23—O256.8 (2)
C27—C26—C39—C44101.8 (2)C22—O1—C23—C25170.43 (16)
C45—C26—C39—C44138.43 (18)C22—O1—C23—C2467.0 (2)
C33—C26—C39—C40167.18 (16)C21—O2—C23—O156.3 (2)
C27—C26—C39—C4072.56 (19)C21—O2—C23—C25170.34 (17)
C45—C26—C39—C4047.2 (2)C21—O2—C23—C2468.1 (2)

Experimental details

Crystal data
Chemical formulaC25H26O2
Mr358.47
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)10.7252 (18), 11.6933 (19), 15.840 (3)
α, β, γ (°)89.574 (3), 88.906 (3), 86.427 (3)
V3)1982.3 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.45 × 0.38 × 0.29
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.967, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
16710, 8543, 5142
Rint0.028
(sin θ/λ)max1)0.642
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.193, 1.07
No. of reflections8543
No. of parameters491
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.24

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was financially supported by the Key Scientific Research Project of the Hunan Provincial Education Department (No. 08 A023) and the Key Subject Construction Project of Hunan Province (No. 2006–180).

References

First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChuprunov, E. V., Tarkhova, T. N., Korallova, T. Y., Simonov, M. A. & Belov, W. V. (1981). Zh. Strukt. Khim. 22, 191–192.  CAS
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWang, G. W., Yuan, X. Y., Lei, X. G. & Liu, Y. C. (1996). Chin. J. Appl. Chem. 11, 114–115.
First citationWang, G. W., Yuan, X. Y., Liu, Y. C., Guo, Q. X. & Lei, X. G. (1996). Indian J. Chem. Sect. B, 35, 583–585.
First citationWang, G. W., Yuan, X. Y., Liu, Y. C., Lei, X. G. & Guo, Q. X. (1995). J. Am. Oil Chem. Soc. 72, 83–87.  CrossRef CAS Web of Science
First citationWhilt, J. W. & Finnerty, J. L. (1961). J. Org. Chem. 26, 2173–2177.
First citationYuan, X. Y., Yang, N. F., Luo, H. A. & Liu, Y. J. (2005). Chin. J. Org. Chem. 25, 1049–1052.  CAS
First citationYuan, X.-Y., Zhang, M. & Ng, S. W. (2008). Acta Cryst. E64, o1314.  Web of Science CSD CrossRef IUCr Journals
First citationYuan, X. Y., Zhang, M. & Yuan, L. (2007). Chin. J. Org. Chem. 27, 1600–1604.  CAS

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