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Acta Cryst. (2008). E64, o588    [ doi:10.1107/S1600536808003644 ]

2,6-Di-tert-butyl-4-(methoxymethyl)phenol

T. Zeng and J.-F. Sun

Abstract top

The title compound, C16H26O2, was easily obtained in high yield when 4-bromomethyl-2,6-di-tert-butylphenol was reacted with methanol. There are two independent molecules in the asymmetric unit. The methoxy group in each of the independent molecules was found to be disordered, with site-occupation factors of 0.8728 (18)/0.1272 (18) and 0.8781 (17)/0.1219 (17).

Comment top

Hindered phenol antioxidants are widely used in polymers and lubricants. It could protect polymers by increasing both their process stability and long-term stability against oxidative degradation (Yamazaki & Seguchi, 1997). In former papers, we have reported the reaction of 4-bromomethyl-20,6-di-tet-butyl-phenol with amines (Zeng et al., 2005) and it was showed that the 4-bromomethyl-2,6-di-tet-butyl-phenol was highly reactive. The title compound, C16H26O2,(1),has been easily synthesied when we tried to dissolve the 4-bromomethyl-2,6-di-tert-butyl-phenol in methanol. It was found that there are two independent molecules in the asymmetric units. The phenolic hydroxyl are hindered by the adjacent tert-butyl groups. And both of the methoxyl groups in the two molecules were found disordered with with site occupation fators 0.8728 (18)/0.1272 (18) and 0.8781 (17)/0.1219 (17).

Related literature top

For related literature, see: Rieker et al. (1968); Yamazaki & Seguchi (1997); Zeng et al. (2005).

Experimental top

The 4-bromomethyl-2,6-di-tert-butyl-phenol (7.15 g) was synthesized from 2,6-di-tert-butyl-4-methylphenol (5.5 g, 0.025 mol) and equivalent NBS (Rieker et al., 1968) in a yield of 96%. Then 40 ml me thanol was added and stirred for 5 min the produt (5.85 g, 0.023 mol) was obtained in a yield of 97.3%. Suitable crystals were obtained by slow evaporation of a mixture of ethyl acetate and ethanol.

Refinement top

The H atoms of O—H were initially located in a difference Fourier Map and restrained on their parent atoms with O—H restrained 0.82 Å. In absence of significant anomalous dispersion effects, Friedel-pair reflections were merged prior to refinement. All H other atoms were positioned geometrically and refined using a riding model, in the range of 0.93–0.97 Å, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (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 two independent molecules in the structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
2,6-di-tert-butyl-4-(methoxymethyl)phenol top
Crystal data top
C16H26O2F000 = 1104
Mr = 250.37Dx = 1.080 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
a = 14.240 (3) ÅCell parameters from 2933 reflections
b = 18.012 (3) Åθ = 2.8–25.4º
c = 13.677 (3) ŵ = 0.07 mm−1
β = 118.603 (3)ºT = 294 (2) K
V = 3079.7 (10) Å3Block, colourless
Z = 80.26 × 0.24 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		5428 independent reflections
Radiation source: fine-focus sealed tube2928 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.046
T = 294(2) Kθmax = 25.0º
φ and ω scansθmin = 1.6º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)		h = −13→16
Tmin = 0.982, Tmax = 0.986k = −20→21
15799 measured reflectionsl = −16→10
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.189  w = 1/[σ2(Fo2) + (0.0751P)2 + 1.0963P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.002
5428 reflectionsΔρmax = 0.31 e Å−3
378 parametersΔρmin = −0.26 e Å−3
108 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0102 (7)
Crystal data top
C16H26O2V = 3079.7 (10) Å3
Mr = 250.37Z = 8
Monoclinic, P21/cMo Kα
a = 14.240 (3) ŵ = 0.07 mm−1
b = 18.012 (3) ÅT = 294 (2) K
c = 13.677 (3) Å0.26 × 0.24 × 0.20 mm
β = 118.603 (3)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		5428 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)		2928 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.986Rint = 0.046
15799 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.060108 restraints
wR(F2) = 0.189H-atom parameters constrained
S = 1.04Δρmax = 0.31 e Å−3
5428 reflectionsΔρmin = −0.26 e Å−3
378 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.29438 (11)0.73376 (8)0.66027 (11)0.0698 (5)
H10.25500.77000.63670.105*
O30.20663 (10)0.25936 (8)0.37111 (12)0.0701 (4)
H30.23810.21960.38210.105*
C10.35866 (12)0.74063 (10)0.77320 (14)0.0425 (5)
C20.39601 (12)0.67334 (9)0.83200 (14)0.0410 (5)
C30.46179 (12)0.67844 (10)0.94611 (14)0.0448 (5)
H3A0.48690.63490.98710.054*
C40.49145 (12)0.74549 (10)1.00116 (14)0.0453 (5)
C50.45463 (13)0.80952 (10)0.94014 (15)0.0501 (5)
H50.47560.85480.97710.060*
C60.38758 (12)0.80988 (10)0.82580 (15)0.0450 (5)
C70.34673 (15)0.88356 (11)0.76197 (18)0.0626 (6)
C80.22446 (17)0.88849 (13)0.7136 (2)0.0880 (9)
H8A0.19950.93530.67630.132*
H8B0.20670.88450.77280.132*
H8C0.19100.84880.66140.132*
C90.3953 (2)0.95088 (12)0.8398 (2)0.0973 (10)
H9A0.47140.95130.86840.146*
H9B0.37960.94740.90060.146*
H9C0.36510.99580.79900.146*
C100.37776 (19)0.89054 (13)0.6695 (2)0.0911 (8)
H10A0.34790.93540.62820.137*
H10B0.35060.84860.62050.137*
H10C0.45430.89200.70200.137*
C110.36507 (14)0.59799 (10)0.77160 (16)0.0528 (6)
C120.40573 (18)0.59247 (12)0.68675 (19)0.0808 (8)
H12A0.37080.62920.62980.121*
H12B0.39040.54390.65370.121*
H12C0.48160.60080.72340.121*
C130.41538 (18)0.53359 (11)0.8551 (2)0.0815 (9)
H13A0.39710.48720.81570.122*
H13B0.38860.53430.90760.122*
H13C0.49170.53920.89400.122*
C140.24411 (16)0.58545 (12)0.7145 (2)0.0785 (8)
H14A0.20890.62300.65880.118*
H14B0.21970.58810.76880.118*
H14C0.22770.53740.68000.118*
C170.14067 (12)0.25795 (10)0.41872 (14)0.0428 (5)
C180.11153 (12)0.19114 (9)0.44964 (14)0.0424 (5)
C190.04478 (13)0.19708 (10)0.49784 (14)0.0473 (5)
H190.02430.15390.52000.057*
C200.00815 (12)0.26412 (10)0.51383 (14)0.0463 (5)
C210.03681 (13)0.32793 (10)0.47987 (14)0.0469 (5)
H210.01070.37310.48940.056*
C220.10338 (13)0.32747 (10)0.43179 (14)0.0435 (5)
C230.13593 (15)0.40024 (10)0.39658 (16)0.0565 (6)
C240.25658 (16)0.41172 (13)0.4620 (2)0.0821 (8)
H24A0.27480.45830.44120.123*
H24B0.29200.37210.44560.123*
H24C0.27890.41200.54020.123*
C250.0990 (2)0.39898 (13)0.27121 (18)0.0843 (8)
H25A0.11680.44530.24950.126*
H25B0.02300.39160.23080.126*
H25C0.13420.35920.25490.126*
C260.08391 (18)0.46798 (11)0.4192 (2)0.0839 (8)
H26A0.10460.47000.49710.126*
H26B0.00750.46390.37660.126*
H26C0.10710.51240.39820.126*
C270.15203 (15)0.11556 (11)0.43482 (17)0.0591 (6)
C280.12020 (19)0.10122 (12)0.3133 (2)0.0873 (8)
H28A0.04370.10210.26960.131*
H28B0.14650.05350.30640.131*
H28C0.15030.13900.28720.131*
C290.10241 (17)0.05158 (11)0.4707 (2)0.0827 (8)
H29A0.12470.05590.54870.124*
H29B0.12600.00480.45660.124*
H29C0.02580.05440.42900.124*
C300.27315 (16)0.11003 (13)0.5082 (2)0.0907 (9)
H30A0.30740.14870.48850.136*
H30B0.29740.06260.49730.136*
H30C0.29070.11530.58490.136*
C150.55793 (15)0.75095 (12)1.12630 (15)0.0648 (6)0.8728 (18)
H15A0.59550.79801.14590.078*0.8728 (18)
H15B0.51140.74921.15980.078*0.8728 (18)
O20.63105 (11)0.69353 (9)1.16775 (11)0.0614 (5)0.8728 (18)
C160.6887 (2)0.69504 (18)1.28628 (18)0.0875 (10)0.8728 (18)
H16A0.73900.65481.31270.131*0.8728 (18)
H16B0.63970.69011.31550.131*0.8728 (18)
H16C0.72640.74131.31060.131*0.8728 (18)
C15'0.5580 (8)0.7510 (7)1.1264 (5)0.0648 (6)0.1272 (18)
H15C0.51020.76401.15570.078*0.1272 (18)
H15D0.58560.70181.15410.078*0.1272 (18)
O2'0.6430 (6)0.7997 (6)1.1711 (6)0.105 (6)0.1272 (18)
C16'0.6844 (13)0.7853 (10)1.2889 (7)0.073 (5)0.1272 (18)
H16D0.74630.81561.33100.110*0.1272 (18)
H16E0.70370.73391.30400.110*0.1272 (18)
H16F0.63060.79691.30970.110*0.1272 (18)
C31−0.0573 (9)0.2684 (4)0.5737 (4)0.0646 (6)0.8781 (17)
H31A−0.00980.26630.65330.078*0.8781 (17)
H31B−0.09480.31540.55680.078*0.8781 (17)
O4−0.13064 (10)0.21107 (9)0.54314 (11)0.0608 (5)0.8781 (17)
C32−0.18536 (18)0.21175 (19)0.6076 (2)0.0943 (11)0.8781 (17)
H32A−0.23580.17160.58450.141*0.8781 (17)
H32B−0.22260.25800.59660.141*0.8781 (17)
H32C−0.13450.20610.68500.141*0.8781 (17)
C31'−0.0573 (9)0.2684 (4)0.5737 (4)0.0646 (6)0.1219 (17)
H31C−0.08390.21900.57520.078*0.1219 (17)
H31D−0.01060.28310.65010.078*0.1219 (17)
O4'−0.1426 (5)0.3164 (5)0.5280 (6)0.071 (3)0.1219 (17)
C32'−0.1973 (8)0.3038 (9)0.5923 (9)0.060 (4)0.1219 (17)
H32D−0.25710.33710.56760.089*0.1219 (17)
H32E−0.14890.31250.66970.089*0.1219 (17)
H32F−0.22240.25350.58230.089*0.1219 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0750 (9)0.0690 (9)0.0423 (8)0.0148 (7)0.0095 (7)0.0070 (7)
O30.0796 (7)0.0652 (9)0.0971 (8)0.0051 (7)0.0677 (6)0.0076 (7)
C10.0349 (8)0.0530 (10)0.0384 (9)0.0040 (8)0.0167 (7)0.0026 (8)
C20.0342 (8)0.0445 (10)0.0426 (9)0.0019 (7)0.0171 (7)0.0041 (8)
C30.0345 (8)0.0532 (10)0.0451 (9)0.0028 (8)0.0178 (7)0.0099 (8)
C40.0330 (8)0.0600 (11)0.0424 (9)−0.0013 (8)0.0177 (7)−0.0034 (9)
C50.0427 (8)0.0513 (11)0.0595 (10)−0.0009 (8)0.0272 (8)−0.0114 (9)
C60.0379 (8)0.0463 (10)0.0548 (10)0.0044 (8)0.0255 (7)0.0010 (8)
C70.0625 (11)0.0460 (11)0.0771 (13)0.0114 (9)0.0318 (10)0.0058 (10)
C80.0754 (13)0.0737 (15)0.1056 (18)0.0319 (12)0.0358 (13)0.0151 (13)
C90.1047 (17)0.0478 (13)0.126 (2)0.0059 (13)0.0441 (15)−0.0020 (14)
C100.1118 (16)0.0688 (14)0.1058 (16)0.0121 (13)0.0626 (13)0.0317 (13)
C110.0470 (9)0.0475 (11)0.0550 (11)−0.0020 (8)0.0172 (8)0.0005 (9)
C120.0961 (14)0.0655 (14)0.0892 (15)−0.0035 (12)0.0511 (12)−0.0236 (12)
C130.0829 (15)0.0466 (12)0.0873 (17)−0.0029 (11)0.0184 (13)0.0079 (12)
C140.0588 (12)0.0702 (14)0.0853 (16)−0.0185 (11)0.0174 (12)−0.0097 (12)
C170.0356 (7)0.0538 (11)0.0412 (9)−0.0024 (8)0.0201 (7)0.0017 (8)
C180.0352 (8)0.0455 (10)0.0433 (9)0.0007 (8)0.0163 (7)0.0050 (8)
C190.0380 (8)0.0542 (11)0.0494 (10)−0.0012 (8)0.0206 (7)0.0113 (9)
C200.0346 (8)0.0618 (11)0.0409 (9)0.0026 (8)0.0167 (7)0.0020 (9)
C210.0399 (8)0.0511 (10)0.0457 (10)0.0012 (8)0.0172 (7)−0.0046 (9)
C220.0393 (8)0.0464 (10)0.0408 (9)−0.0026 (8)0.0158 (7)0.0003 (8)
C230.0612 (10)0.0472 (11)0.0587 (11)−0.0110 (9)0.0269 (9)−0.0012 (9)
C240.0755 (12)0.0713 (14)0.0990 (16)−0.0283 (11)0.0415 (12)−0.0053 (13)
C250.1207 (16)0.0698 (14)0.0628 (13)−0.0133 (13)0.0443 (12)0.0119 (11)
C260.1037 (15)0.0477 (12)0.1044 (17)−0.0043 (12)0.0532 (13)−0.0026 (12)
C270.0565 (9)0.0487 (11)0.0801 (12)0.0080 (9)0.0392 (9)0.0096 (10)
C280.1188 (16)0.0573 (13)0.0998 (16)0.0070 (13)0.0637 (13)−0.0119 (12)
C290.0912 (13)0.0477 (12)0.1248 (17)0.0076 (11)0.0643 (12)0.0154 (12)
C300.0632 (12)0.0791 (15)0.133 (2)0.0299 (11)0.0492 (12)0.0286 (14)
C150.0585 (10)0.0878 (15)0.0508 (10)0.0038 (10)0.0283 (8)−0.0017 (10)
O20.0523 (8)0.0869 (11)0.0372 (8)0.0066 (8)0.0153 (6)0.0022 (8)
C160.0718 (16)0.142 (3)0.0366 (13)0.0054 (17)0.0159 (12)0.0100 (15)
C15'0.0585 (10)0.0878 (15)0.0508 (10)0.0038 (10)0.0283 (8)−0.0017 (10)
O2'0.043 (6)0.204 (15)0.049 (7)0.037 (8)0.006 (5)−0.019 (8)
C16'0.069 (6)0.087 (7)0.061 (6)−0.005 (6)0.029 (5)−0.002 (6)
C310.0554 (9)0.0890 (14)0.0601 (10)−0.0009 (10)0.0362 (8)0.0004 (10)
O40.0464 (7)0.0904 (11)0.0556 (8)−0.0017 (8)0.0326 (6)0.0079 (8)
C320.0657 (12)0.163 (3)0.0771 (15)−0.0018 (17)0.0522 (11)0.0131 (17)
C31'0.0554 (9)0.0890 (14)0.0601 (10)−0.0009 (10)0.0362 (8)0.0004 (10)
O4'0.065 (4)0.091 (4)0.065 (4)0.001 (3)0.038 (3)−0.001 (4)
C32'0.061 (6)0.073 (7)0.066 (6)0.012 (5)0.048 (4)0.001 (5)
Geometric parameters (Å, °) top
O1—C11.373 (2)C21—H210.9300
O1—H10.8200C22—C231.542 (3)
O3—C171.376 (2)C23—C241.524 (3)
O3—H30.8200C23—C261.534 (3)
C1—C61.400 (2)C23—C251.534 (3)
C1—C21.410 (2)C24—H24A0.9600
C2—C31.386 (2)C24—H24B0.9600
C2—C111.539 (2)C24—H24C0.9600
C3—C41.378 (2)C25—H25A0.9600
C3—H3A0.9300C25—H25B0.9600
C4—C51.372 (2)C25—H25C0.9600
C4—C151.511 (2)C26—H26A0.9600
C5—C61.388 (2)C26—H26B0.9600
C5—H50.9300C26—H26C0.9600
C6—C71.541 (3)C27—C281.521 (3)
C7—C101.531 (4)C27—C301.528 (3)
C7—C81.541 (3)C27—C291.549 (3)
C7—C91.542 (3)C28—H28A0.9600
C8—H8A0.9600C28—H28B0.9600
C8—H8B0.9600C28—H28C0.9600
C8—H8C0.9600C29—H29A0.9600
C9—H9A0.9600C29—H29B0.9600
C9—H9B0.9600C29—H29C0.9600
C9—H9C0.9600C30—H30A0.9600
C10—H10A0.9600C30—H30B0.9600
C10—H10B0.9600C30—H30C0.9600
C10—H10C0.9600C15—O21.382 (2)
C11—C121.528 (3)C15—H15A0.9700
C11—C141.530 (3)C15—H15B0.9700
C11—C131.543 (3)O2—C161.424 (3)
C12—H12A0.9600C16—H16A0.9600
C12—H12B0.9600C16—H16B0.9600
C12—H12C0.9600C16—H16C0.9600
C13—H13A0.9600O2'—C16'1.449 (8)
C13—H13B0.9600C16'—H16D0.9600
C13—H13C0.9600C16'—H16E0.9600
C14—H14A0.9600C16'—H16F0.9600
C14—H14B0.9600C31—O41.383 (2)
C14—H14C0.9600C31—H31A0.9700
C17—C181.403 (2)C31—H31B0.9700
C17—C221.404 (2)O4—C321.429 (3)
C18—C191.396 (3)C32—H32A0.9600
C18—C271.529 (3)C32—H32B0.9600
C19—C201.374 (3)C32—H32C0.9600
C19—H190.9300O4'—C32'1.445 (9)
C20—C211.373 (3)C32'—H32D0.9600
C20—C311.507 (3)C32'—H32E0.9600
C21—C221.389 (3)C32'—H32F0.9600
C1—O1—H1109.5C24—C23—C26106.94 (17)
C17—O3—H3109.5C24—C23—C25110.1 (2)
O1—C1—C6122.15 (15)C26—C23—C25107.30 (17)
O1—C1—C2115.50 (15)C24—C23—C22110.80 (15)
C6—C1—C2122.33 (15)C26—C23—C22111.50 (19)
C3—C2—C1116.88 (16)C25—C23—C22110.07 (15)
C3—C2—C11121.88 (15)C23—C24—H24A109.5
C1—C2—C11121.24 (15)C23—C24—H24B109.5
C4—C3—C2122.57 (16)H24A—C24—H24B109.5
C4—C3—H3A118.7C23—C24—H24C109.5
C2—C3—H3A118.7H24A—C24—H24C109.5
C5—C4—C3118.45 (15)H24B—C24—H24C109.5
C5—C4—C15118.95 (17)C23—C25—H25A109.5
C3—C4—C15122.52 (17)C23—C25—H25B109.5
C4—C5—C6123.06 (17)H25A—C25—H25B109.5
C4—C5—H5118.5C23—C25—H25C109.5
C6—C5—H5118.5H25A—C25—H25C109.5
C5—C6—C1116.70 (16)H25B—C25—H25C109.5
C5—C6—C7120.77 (16)C23—C26—H26A109.5
C1—C6—C7122.53 (16)C23—C26—H26B109.5
C10—C7—C8110.73 (19)H26A—C26—H26B109.5
C10—C7—C6111.01 (18)C23—C26—H26C109.5
C8—C7—C6109.59 (17)H26A—C26—H26C109.5
C10—C7—C9107.1 (2)H26B—C26—H26C109.5
C8—C7—C9107.01 (19)C28—C27—C30111.0 (2)
C6—C7—C9111.29 (17)C28—C27—C18111.22 (16)
C7—C8—H8A109.5C30—C27—C18110.47 (16)
C7—C8—H8B109.5C28—C27—C29106.11 (18)
H8A—C8—H8B109.5C30—C27—C29106.62 (17)
C7—C8—H8C109.5C18—C27—C29111.22 (18)
H8A—C8—H8C109.5C27—C28—H28A109.5
H8B—C8—H8C109.5C27—C28—H28B109.5
C7—C9—H9A109.5H28A—C28—H28B109.5
C7—C9—H9B109.5C27—C28—H28C109.5
H9A—C9—H9B109.5H28A—C28—H28C109.5
C7—C9—H9C109.5H28B—C28—H28C109.5
H9A—C9—H9C109.5C27—C29—H29A109.5
H9B—C9—H9C109.5C27—C29—H29B109.5
C7—C10—H10A109.5H29A—C29—H29B109.5
C7—C10—H10B109.5C27—C29—H29C109.5
H10A—C10—H10B109.5H29A—C29—H29C109.5
C7—C10—H10C109.5H29B—C29—H29C109.5
H10A—C10—H10C109.5C27—C30—H30A109.5
H10B—C10—H10C109.5C27—C30—H30B109.5
C12—C11—C14110.25 (18)H30A—C30—H30B109.5
C12—C11—C2110.47 (17)C27—C30—H30C109.5
C14—C11—C2111.54 (16)H30A—C30—H30C109.5
C12—C11—C13107.62 (18)H30B—C30—H30C109.5
C14—C11—C13106.10 (17)O2—C15—C4110.88 (17)
C2—C11—C13110.70 (15)O2—C15—H15A109.5
C11—C12—H12A109.5C4—C15—H15A109.5
C11—C12—H12B109.5O2—C15—H15B109.5
H12A—C12—H12B109.5C4—C15—H15B109.5
C11—C12—H12C109.5H15A—C15—H15B108.1
H12A—C12—H12C109.5C15—O2—C16111.31 (19)
H12B—C12—H12C109.5O2—C16—H16A109.5
C11—C13—H13A109.5O2—C16—H16B109.5
C11—C13—H13B109.5H16A—C16—H16B109.5
H13A—C13—H13B109.5O2—C16—H16C109.5
C11—C13—H13C109.5H16A—C16—H16C109.5
H13A—C13—H13C109.5H16B—C16—H16C109.5
H13B—C13—H13C109.5O2'—C16'—H16D109.5
C11—C14—H14A109.5O2'—C16'—H16E109.5
C11—C14—H14B109.5H16D—C16'—H16E109.5
H14A—C14—H14B109.5O2'—C16'—H16F109.5
C11—C14—H14C109.5H16D—C16'—H16F109.5
H14A—C14—H14C109.5H16E—C16'—H16F109.5
H14B—C14—H14C109.5O4—C31—C20111.93 (17)
O3—C17—C18121.74 (16)O4—C31—H31A109.2
O3—C17—C22115.43 (16)C20—C31—H31A109.2
C18—C17—C22122.82 (18)O4—C31—H31B109.2
C19—C18—C17116.31 (16)C20—C31—H31B109.2
C19—C18—C27121.06 (17)H31A—C31—H31B107.9
C17—C18—C27122.61 (18)C31—O4—C32111.38 (19)
C20—C19—C18122.59 (17)O4—C32—H32A109.5
C20—C19—H19118.7O4—C32—H32B109.5
C18—C19—H19118.7H32A—C32—H32B109.5
C21—C20—C19119.02 (18)O4—C32—H32C109.5
C21—C20—C31120.16 (18)H32A—C32—H32C109.5
C19—C20—C31120.73 (18)H32B—C32—H32C109.5
C20—C21—C22122.41 (17)O4'—C32'—H32D109.5
C20—C21—H21118.8O4'—C32'—H32E109.5
C22—C21—H21118.8H32D—C32'—H32E109.5
C21—C22—C17116.82 (17)O4'—C32'—H32F109.5
C21—C22—C23121.21 (17)H32D—C32'—H32F109.5
C17—C22—C23121.97 (18)H32E—C32'—H32F109.5
O1—C1—C2—C3179.52 (16)C22—C17—C18—C27179.76 (15)
C6—C1—C2—C31.3 (3)C17—C18—C19—C200.5 (2)
O1—C1—C2—C11−0.3 (3)C27—C18—C19—C20179.07 (15)
C6—C1—C2—C11−178.52 (18)C18—C19—C20—C210.9 (2)
C1—C2—C3—C4−0.8 (3)C18—C19—C20—C31−175.59 (15)
C11—C2—C3—C4179.05 (18)C19—C20—C21—C22−1.3 (2)
C2—C3—C4—C5−0.3 (3)C31—C20—C21—C22175.23 (15)
C2—C3—C4—C15176.40 (18)C20—C21—C22—C170.2 (2)
C3—C4—C5—C61.0 (3)C20—C21—C22—C23−178.79 (15)
C15—C4—C5—C6−175.84 (18)O3—C17—C22—C21−179.85 (14)
C4—C5—C6—C1−0.5 (3)C18—C17—C22—C211.4 (2)
C4—C5—C6—C7178.64 (19)O3—C17—C22—C23−0.9 (2)
O1—C1—C6—C5−178.78 (17)C18—C17—C22—C23−179.64 (15)
C2—C1—C6—C5−0.7 (3)C21—C22—C23—C24117.6 (2)
O1—C1—C6—C72.1 (3)C17—C22—C23—C24−61.3 (2)
C2—C1—C6—C7−179.83 (18)C21—C22—C23—C26−1.4 (2)
C5—C6—C7—C10122.6 (2)C17—C22—C23—C26179.73 (15)
C1—C6—C7—C10−58.3 (2)C21—C22—C23—C25−120.32 (19)
C5—C6—C7—C8−114.8 (2)C17—C22—C23—C2560.8 (2)
C1—C6—C7—C864.4 (3)C19—C18—C27—C28122.42 (19)
C5—C6—C7—C93.4 (3)C17—C18—C27—C28−59.2 (2)
C1—C6—C7—C9−177.5 (2)C19—C18—C27—C30−113.8 (2)
C3—C2—C11—C12−118.3 (2)C17—C18—C27—C3064.6 (2)
C1—C2—C11—C1261.5 (2)C19—C18—C27—C294.4 (2)
C3—C2—C11—C14118.7 (2)C17—C18—C27—C29−177.19 (16)
C1—C2—C11—C14−61.5 (3)C5—C4—C15—O2−148.81 (18)
C3—C2—C11—C130.8 (3)C3—C4—C15—O234.4 (3)
C1—C2—C11—C13−179.37 (19)C4—C15—O2—C16−175.74 (19)
O3—C17—C18—C19179.58 (14)C21—C20—C31—O4142.81 (16)
C22—C17—C18—C19−1.7 (2)C19—C20—C31—O4−40.7 (2)
O3—C17—C18—C271.1 (2)C20—C31—O4—C32174.72 (17)
Acknowledgements top

The authors greatefully acknowledge financial support from the Start Foundation for Doctors (HY071314) of Yantai University.

references
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