PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o304.
Published online 2009 January 14. doi:  10.1107/S1600536809000294
PMCID: PMC2968387

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

Abstract

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 [triangle]); Yuan et al. (2007 [triangle]); Wang et al. (1995 [triangle]). For applications of this class of compounds, see: Wang, Yuan, Liu et al. (1996 [triangle]); Wang, Yuan, Lei & Liu (1996 [triangle]); Yuan et al. (2005 [triangle]). For related crystal structures, see: Chuprunov et al. (1981 [triangle]); Yuan et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o304-scheme1.jpg

Experimental

Crystal data

  • C25H26O2
  • M r = 358.47
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o304-efi1.jpg
  • 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 [triangle]) T min = 0.967, T max = 0.979
  • 16710 measured reflections
  • 8543 independent reflections
  • 5142 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 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 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000294/bt2825sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000294/bt2825Isup2.hkl

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

Acknowledgments

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).

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

Fig. 1.
The molecular structure of the title compound, showing displacement ellipsoids at the 30% probability level. H-atoms have been excluded for clarity.
Fig. 2.
A view of the packing of the title compound.

Crystal data

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

Bruker SMART CCD area-detector diffractometer8543 independent reflections
Radiation source: fine-focus sealed tube5142 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] and ω scansθmax = 27.2°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.967, Tmax = 0.979k = −14→14
16710 measured reflectionsl = −20→20

Refinement

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 = 1.07w = 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

Special details

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)

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*
C5−0.1020 (2)0.39266 (19)0.32589 (12)0.0564 (5)
H5−0.17440.39360.35920.068*
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)
H110.28310.0581−0.05470.093*
C6−0.0505 (2)0.29260 (19)0.29377 (13)0.0628 (6)
H6−0.08760.22440.30590.075*
C100.1616 (3)0.1723 (2)0.00074 (13)0.0687 (7)
H100.09300.1543−0.03050.082*
C4−0.0455 (2)0.49138 (19)0.30843 (13)0.0605 (6)
H4−0.07930.56030.33040.073*
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)
H25A0.27010.8051−0.01580.124*
H25B0.18710.7825−0.09370.124*
H25C0.33280.7630−0.10120.124*
C240.2427 (3)0.5554 (2)−0.11037 (13)0.0809 (7)
H24A0.31680.5573−0.14520.121*
H24B0.17120.5796−0.14300.121*
H24C0.23390.4788−0.09000.121*
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)

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, °)

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—C21−51.71 (19)C33—C26—C27—C32130.26 (19)
C8—C1—C20—C2171.02 (19)C39—C26—C27—C32−107.5 (2)
C14—C1—C20—C21−167.89 (14)C45—C26—C27—C3210.6 (2)
C2—C1—C20—C22−175.46 (14)C33—C26—C27—C28−52.2 (2)
C8—C1—C20—C22−52.73 (19)C39—C26—C27—C2870.04 (19)
C14—C1—C20—C2268.36 (18)C45—C26—C27—C28−171.86 (15)
C8—C1—C2—C3−156.43 (17)C33—C26—C45—C4769.82 (19)
C14—C1—C2—C383.5 (2)C39—C26—C45—C47−53.8 (2)
C20—C1—C2—C3−36.7 (2)C27—C26—C45—C47−168.60 (15)
C8—C1—C2—C728.6 (2)C33—C26—C45—C46−52.4 (2)
C14—C1—C2—C7−91.5 (2)C39—C26—C45—C46−176.05 (16)
C20—C1—C2—C7148.34 (17)C27—C26—C45—C4669.19 (19)
C2—C1—C14—C19−108.4 (2)C44—C39—C40—C41−3.1 (3)
C8—C1—C14—C19130.6 (2)C26—C39—C40—C41−177.85 (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—C15−52.8 (2)C45—C26—C33—C38−76.1 (2)
C20—C1—C14—C15−171.80 (16)C39—C26—C33—C34−141.63 (17)
C2—C1—C8—C13−141.65 (18)C27—C26—C33—C34−25.2 (2)
C14—C1—C8—C13−25.1 (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—O3−54.4 (2)
C14—C1—C8—C9160.70 (16)C26—C45—C47—O3179.86 (14)
C20—C1—C8—C9−77.8 (2)C48—O4—C46—C45−59.9 (2)
C23—O1—C22—C20−58.7 (2)C47—C45—C46—O455.2 (2)
C21—C20—C22—O154.90 (19)C26—C45—C46—O4−178.10 (15)
C1—C20—C22—O1−176.66 (14)C30—C29—C28—C270.7 (3)
C13—C8—C9—C10−0.4 (3)C32—C27—C28—C29−2.2 (3)
C1—C8—C9—C10173.99 (17)C26—C27—C28—C29−179.92 (17)
C23—O2—C21—C2057.8 (2)C34—C33—C38—C370.2 (3)
C22—C20—C21—O2−54.6 (2)C26—C33—C38—C37173.79 (18)
C1—C20—C21—O2177.79 (14)C40—C39—C44—C432.9 (3)
C7—C2—C3—C4−2.3 (3)C26—C39—C44—C43177.44 (19)
C1—C2—C3—C4−177.53 (18)C39—C40—C41—C420.5 (3)
C9—C8—C13—C120.1 (3)C39—C44—C43—C42−0.2 (4)
C1—C8—C13—C12−174.26 (18)C44—C43—C42—C41−2.5 (3)
C19—C14—C15—C16−3.2 (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—C35−0.8 (3)
C4—C5—C6—C7−0.9 (3)C26—C33—C34—C35−174.35 (18)
C2—C7—C6—C5−0.3 (3)C27—C32—C31—C30−0.7 (3)
C12—C11—C10—C90.2 (4)C28—C29—C30—C310.8 (3)
C8—C9—C10—C110.3 (3)C32—C31—C30—C29−0.8 (4)
C6—C5—C4—C30.5 (3)C33—C38—C37—C360.6 (3)
C2—C3—C4—C51.1 (3)C35—C36—C37—C38−0.9 (4)
C10—C11—C12—C13−0.5 (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—C18−179.8 (2)C46—O4—C48—C49−65.6 (2)
C14—C19—C18—C17−1.7 (4)C47—O3—C48—O4−57.6 (2)
C19—C18—C17—C16−0.8 (4)C47—O3—C48—C50−171.43 (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—C44−101.8 (2)C22—O1—C23—C25170.43 (16)
C45—C26—C39—C44138.43 (18)C22—O1—C23—C24−67.0 (2)
C33—C26—C39—C40−167.18 (16)C21—O2—C23—O1−56.3 (2)
C27—C26—C39—C4072.56 (19)C21—O2—C23—C25−170.34 (17)
C45—C26—C39—C40−47.2 (2)C21—O2—C23—C2468.1 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2825).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chuprunov, E. V., Tarkhova, T. N., Korallova, T. Y., Simonov, M. A. & Belov, W. V. (1981). Zh. Strukt. Khim.22, 191–192.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, G. W., Yuan, X. Y., Lei, X. G. & Liu, Y. C. (1996). Chin. J. Appl. Chem.11, 114–115.
  • 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, G. W., Yuan, X. Y., Liu, Y. C., Lei, X. G. & Guo, Q. X. (1995). J. Am. Oil Chem. Soc.72, 83–87.
  • Whilt, J. W. & Finnerty, J. L. (1961). J. Org. Chem.26, 2173–2177.
  • Yuan, X. Y., Yang, N. F., Luo, H. A. & Liu, Y. J. (2005). Chin. J. Org. Chem.25, 1049–1052.
  • Yuan, X.-Y., Zhang, M. & Ng, S. W. (2008). Acta Cryst. E64, o1314. [PMC free article] [PubMed]
  • Yuan, X. Y., Zhang, M. & Yuan, L. (2007). Chin. J. Org. Chem.27, 1600–1604.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography