19-Benzo-yloxy-13,16-seco-ent-beyeran 13,16-lactone.

The title compound, C(27)H(34)O(5), a beyerane-type diterpenoid prepared by peroxidation and benzoyl-ation of isosteviol, contains a fused six-membered ring system. The O atoms of the benzoic ester and the lactone are disordered with occupancy ratios of 0.6 (4):0.4 (4) and 0.6 (2):0.4 (2), respectively. Three cyclo-hexane rings have chair conformations, whereas the remaining lactone ring adopts a half-chair conformation.

Related literature

For the pharmaceutical activity of isosteviol, see: Liu et al. (2001 ▶); Braguini et al. (2003 ▶); Mizushina et al. (2005 ▶); Wong et al. (2004) ▶; Xu et al. (2007 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the synthesis of isosteviol derivatives via peroxidation and esterification, see: Chou et al. (2008 ▶); Wu et al. (2009 ▶); Chen (2010 ▶).

Experimental

Crystal data

C27H34O5

M = 438.54

Orthorhombic,

a = 7.7425 (16) Å

b = 11.871 (2) Å

c = 25.306 (5) Å

V = 2325.8 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.48 × 0.46 × 0.43 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.960, T max = 0.964

12234 measured reflections

2362 independent reflections

1500 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.154

S = 1.03

2362 reflections

310 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051561/rn2071sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051561/rn2071Isup2.hkl

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

C27H34O5	F(000) = 944
Mr = 438.54	Dx = 1.252 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2537 reflections
a = 7.7425 (16) Å	θ = 2.4–20.3°
b = 11.871 (2) Å	µ = 0.09 mm−1
c = 25.306 (5) Å	T = 298 K
V = 2325.8 (8) Å3	Prism, colourless
Z = 4	0.48 × 0.46 × 0.43 mm

Bruker SMART CCD area-detector diffractometer	2362 independent reflections
Radiation source: fine-focus sealed tube	1500 reflections with I > 2σ(I)
graphite	Rint = 0.064
phi and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −5→9
Tmin = 0.960, Tmax = 0.964	k = −14→14
12234 measured reflections	l = −28→30

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.154	w = 1/[σ2(Fo2) + (0.0594P)2 + 1.2539P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
2362 reflections	Δρmax = 0.18 e Å−3
310 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (3)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.918 (17)	0.286 (9)	0.376 (4)	0.067 (15)	0.6 (4)
O1'	0.87 (2)	0.259 (13)	0.388 (6)	0.07 (2)	0.4 (4)
O2	0.6430 (6)	0.2441 (3)	0.34276 (13)	0.0755 (11)
O3	0.5237 (5)	0.1873 (3)	0.05672 (13)	0.0754 (11)
O4	0.319 (14)	0.287 (9)	0.0949 (8)	0.087 (15)	0.6 (2)
O4'	0.388 (18)	0.324 (8)	0.0979 (18)	0.083 (18)	0.4 (2)
O5	0.8077 (6)	0.4534 (3)	0.37365 (15)	0.0865 (12)
C1	0.7924 (8)	0.2203 (4)	0.34546 (19)	0.0627 (13)
C2	0.8863 (7)	0.1252 (4)	0.31854 (18)	0.0609 (13)
C3	1.0812 (7)	0.1462 (4)	0.3150 (2)	0.0688 (15)
H3A	1.1236	0.1678	0.3496	0.083*
H3B	1.1379	0.0763	0.3052	0.083*
C4	1.1302 (7)	0.2357 (4)	0.2759 (2)	0.0733 (15)
H4A	1.2551	0.2410	0.2740	0.088*
H4B	1.0863	0.3078	0.2879	0.088*
C5	1.0590 (6)	0.2109 (5)	0.22116 (19)	0.0660 (14)
H5A	1.1146	0.1437	0.2075	0.079*
H5B	1.0879	0.2729	0.1978	0.079*
C6	0.8618 (6)	0.1932 (4)	0.22027 (17)	0.0515 (11)
C7	0.8138 (6)	0.1451 (4)	0.16440 (16)	0.0504 (11)
H7	0.8949	0.0828	0.1589	0.061*
C8	0.6345 (6)	0.0916 (4)	0.15766 (16)	0.0507 (11)
C9	0.5994 (7)	0.0101 (4)	0.20318 (16)	0.0582 (13)
H9A	0.6739	−0.0551	0.1995	0.070*
H9B	0.4808	−0.0157	0.2011	0.070*
C10	0.6299 (7)	0.0636 (4)	0.25735 (17)	0.0585 (13)
H10A	0.5532	0.1275	0.2619	0.070*
H10B	0.6049	0.0092	0.2849	0.070*
C11	0.8170 (7)	0.1023 (4)	0.26179 (17)	0.0533 (12)
H11	0.8832	0.0365	0.2502	0.064*
C12	0.8501 (7)	0.2262 (4)	0.11891 (16)	0.0631 (13)
H12A	0.7699	0.2888	0.1206	0.076*
H12B	0.9662	0.2560	0.1224	0.076*
C13	0.8323 (7)	0.1673 (4)	0.06560 (19)	0.0689 (15)
H13A	0.8412	0.2232	0.0378	0.083*
H13B	0.9274	0.1149	0.0613	0.083*
C14	0.6646 (7)	0.1041 (4)	0.05918 (18)	0.0647 (13)
C15	0.6338 (7)	0.0269 (4)	0.10523 (17)	0.0596 (12)
H15A	0.7231	−0.0304	0.1060	0.072*
H15B	0.5234	−0.0105	0.1009	0.072*
C16	0.4840 (7)	0.1744 (4)	0.15308 (18)	0.0590 (13)
H16A	0.3798	0.1352	0.1638	0.071*
H16B	0.5033	0.2343	0.1785	0.071*
C17	0.4497 (8)	0.2280 (5)	0.1007 (2)	0.0706 (15)
C18	0.8566 (9)	0.0239 (4)	0.35505 (19)	0.0830 (18)
H18A	0.9122	−0.0413	0.3405	0.124*
H18B	0.7349	0.0100	0.3582	0.124*
H18C	0.9040	0.0397	0.3893	0.124*
C19	0.6557 (9)	0.0447 (5)	0.00632 (19)	0.0854 (18)
H19A	0.6759	0.0980	−0.0215	0.128*
H19B	0.5434	0.0116	0.0020	0.128*
H19C	0.7420	−0.0133	0.0050	0.128*
C20	0.8505 (8)	0.3784 (5)	0.4017 (2)	0.0704 (14)
C21	0.8676 (7)	0.3817 (4)	0.45931 (19)	0.0642 (13)
C22	0.9247 (8)	0.2913 (5)	0.4883 (2)	0.0811 (17)
H22	0.9533	0.2242	0.4714	0.097*
C23	0.9396 (9)	0.3002 (6)	0.5427 (3)	0.0920 (19)
H23	0.9784	0.2391	0.5624	0.110*
C24	0.8976 (8)	0.3980 (6)	0.5672 (2)	0.0895 (19)
H24	0.9076	0.4035	0.6037	0.107*
C25	0.8411 (9)	0.4880 (6)	0.5388 (2)	0.0886 (18)
H25	0.8135	0.5547	0.5561	0.106*
C26	0.8243 (7)	0.4813 (5)	0.4848 (2)	0.0743 (15)
H26	0.7844	0.5428	0.4656	0.089*
C27	0.7749 (7)	0.3072 (3)	0.23161 (18)	0.0611 (13)
H27A	0.8062	0.3602	0.2046	0.092*
H27B	0.8125	0.3348	0.2654	0.092*
H27C	0.6518	0.2978	0.2319	0.092*

	U11	U22	U33	U12	U13	U23
O1	0.07 (2)	0.064 (16)	0.067 (14)	0.010 (18)	−0.005 (16)	−0.014 (14)
O1'	0.07 (3)	0.06 (2)	0.07 (2)	0.01 (3)	0.00 (2)	−0.01 (2)
O2	0.075 (3)	0.083 (2)	0.069 (2)	0.005 (2)	0.016 (2)	−0.0057 (19)
O3	0.084 (3)	0.085 (2)	0.058 (2)	0.016 (2)	0.005 (2)	0.0064 (19)
O4	0.08 (2)	0.08 (2)	0.097 (6)	0.03 (2)	−0.006 (8)	0.007 (8)
O4'	0.08 (3)	0.08 (2)	0.091 (9)	0.03 (2)	0.004 (12)	0.011 (10)
O5	0.098 (3)	0.083 (3)	0.078 (2)	0.014 (3)	−0.003 (2)	0.007 (2)
C1	0.071 (4)	0.059 (3)	0.057 (3)	0.007 (3)	−0.001 (3)	−0.002 (3)
C2	0.071 (3)	0.053 (3)	0.059 (3)	0.007 (3)	−0.001 (3)	−0.003 (2)
C3	0.069 (4)	0.065 (3)	0.072 (3)	0.014 (3)	−0.011 (3)	−0.013 (3)
C4	0.063 (3)	0.074 (3)	0.084 (4)	−0.001 (3)	−0.001 (3)	−0.017 (3)
C5	0.059 (3)	0.066 (3)	0.073 (3)	−0.008 (3)	0.009 (3)	−0.003 (3)
C6	0.052 (3)	0.047 (3)	0.055 (3)	0.000 (2)	0.008 (2)	−0.002 (2)
C7	0.054 (3)	0.048 (2)	0.049 (2)	0.002 (2)	0.010 (2)	−0.002 (2)
C8	0.053 (3)	0.047 (2)	0.051 (3)	0.001 (2)	0.009 (2)	0.002 (2)
C9	0.063 (3)	0.051 (3)	0.061 (3)	−0.011 (2)	0.006 (2)	0.005 (2)
C10	0.065 (3)	0.055 (3)	0.056 (3)	−0.006 (3)	0.008 (3)	0.012 (2)
C11	0.059 (3)	0.046 (2)	0.055 (3)	0.003 (2)	0.003 (2)	0.000 (2)
C12	0.070 (3)	0.063 (3)	0.056 (3)	−0.008 (3)	0.014 (3)	0.001 (2)
C13	0.075 (4)	0.078 (3)	0.054 (3)	−0.002 (3)	0.016 (3)	−0.001 (3)
C14	0.067 (3)	0.073 (3)	0.054 (3)	0.005 (3)	0.011 (3)	−0.003 (3)
C15	0.061 (3)	0.059 (3)	0.059 (3)	0.005 (3)	0.007 (3)	−0.009 (2)
C16	0.060 (3)	0.064 (3)	0.053 (3)	0.007 (3)	0.009 (2)	0.001 (2)
C17	0.076 (4)	0.073 (4)	0.063 (3)	0.017 (3)	0.007 (3)	0.004 (3)
C18	0.116 (5)	0.065 (3)	0.068 (3)	0.011 (4)	−0.011 (4)	0.011 (3)
C19	0.088 (4)	0.107 (4)	0.061 (3)	0.001 (4)	0.008 (3)	−0.019 (3)
C20	0.071 (4)	0.071 (4)	0.069 (3)	0.011 (3)	−0.004 (3)	−0.015 (3)
C21	0.061 (3)	0.067 (3)	0.065 (3)	0.003 (3)	−0.002 (3)	−0.014 (3)
C22	0.085 (4)	0.080 (4)	0.079 (4)	0.005 (4)	−0.011 (3)	−0.012 (3)
C23	0.091 (5)	0.098 (5)	0.087 (4)	−0.002 (4)	−0.010 (4)	0.004 (4)
C24	0.077 (4)	0.116 (5)	0.076 (4)	−0.001 (4)	0.000 (4)	−0.014 (4)
C25	0.082 (4)	0.096 (4)	0.088 (4)	0.004 (4)	0.003 (4)	−0.031 (4)
C26	0.069 (4)	0.077 (3)	0.076 (4)	0.005 (3)	−0.001 (3)	−0.018 (3)
C27	0.077 (3)	0.045 (3)	0.062 (3)	0.003 (3)	0.007 (3)	0.002 (2)

O1—C20	1.38 (2)	C10—H10B	0.9700
O1—C1	1.47 (9)	C11—H11	0.9800
O1'—C1	1.31 (4)	C12—C13	1.526 (6)
O1'—C20	1.47 (10)	C12—H12A	0.9700
O2—C1	1.193 (6)	C12—H12B	0.9700
O3—C17	1.341 (6)	C13—C14	1.509 (7)
O3—C14	1.473 (6)	C13—H13A	0.9700
O4—C17	1.24 (3)	C13—H13B	0.9700
O4'—C17	1.24 (4)	C14—C15	1.501 (6)
O5—C20	1.185 (6)	C14—C19	1.514 (6)
C1—C2	1.505 (7)	C15—H15A	0.9700
C2—C3	1.532 (8)	C15—H15B	0.9700
C2—C18	1.534 (6)	C16—C17	1.495 (7)
C2—C11	1.557 (6)	C16—H16A	0.9700
C3—C4	1.501 (7)	C16—H16B	0.9700
C3—H3A	0.9700	C18—H18A	0.9600
C3—H3B	0.9700	C18—H18B	0.9600
C4—C5	1.519 (7)	C18—H18C	0.9600
C4—H4A	0.9700	C19—H19A	0.9600
C4—H4B	0.9700	C19—H19B	0.9600
C5—C6	1.541 (6)	C19—H19C	0.9600
C5—H5A	0.9700	C20—C21	1.465 (7)
C5—H5B	0.9700	C21—C22	1.373 (7)
C6—C27	1.538 (6)	C21—C26	1.389 (7)
C6—C11	1.546 (6)	C22—C23	1.386 (8)
C6—C7	1.569 (6)	C22—H22	0.9300
C7—C12	1.526 (6)	C23—C24	1.355 (9)
C7—C8	1.537 (7)	C23—H23	0.9300
C7—H7	0.9800	C24—C25	1.359 (8)
C8—C9	1.528 (6)	C24—H24	0.9300
C8—C16	1.529 (6)	C25—C26	1.375 (7)
C8—C15	1.533 (6)	C25—H25	0.9300
C9—C10	1.529 (6)	C26—H26	0.9300
C9—H9A	0.9700	C27—H27A	0.9600
C9—H9B	0.9700	C27—H27B	0.9600
C10—C11	1.524 (7)	C27—H27C	0.9600
C10—H10A	0.9700
C20—O1—C1	115 (6)	H12A—C12—H12B	108.0
C1—O1'—C20	119 (6)	C14—C13—C12	113.6 (4)
C17—O3—C14	121.5 (4)	C14—C13—H13A	108.8
O2—C1—O1'	113 (6)	C12—C13—H13A	108.8
O2—C1—O1	123 (2)	C14—C13—H13B	108.8
O1'—C1—O1	23 (6)	C12—C13—H13B	108.8
O2—C1—C2	128.4 (5)	H13A—C13—H13B	107.7
O1'—C1—C2	115 (3)	O3—C14—C15	109.0 (4)
O1—C1—C2	108 (2)	O3—C14—C13	108.0 (4)
C1—C2—C3	112.4 (4)	C15—C14—C13	110.9 (4)
C1—C2—C18	104.0 (4)	O3—C14—C19	104.0 (4)
C3—C2—C18	108.1 (5)	C15—C14—C19	113.2 (4)
C1—C2—C11	112.4 (4)	C13—C14—C19	111.5 (5)
C3—C2—C11	108.3 (4)	C14—C15—C8	111.5 (4)
C18—C2—C11	111.5 (4)	C14—C15—H15A	109.3
C4—C3—C2	113.8 (5)	C8—C15—H15A	109.3
C4—C3—H3A	108.8	C14—C15—H15B	109.3
C2—C3—H3A	108.8	C8—C15—H15B	109.3
C4—C3—H3B	108.8	H15A—C15—H15B	108.0
C2—C3—H3B	108.8	C17—C16—C8	118.5 (4)
H3A—C3—H3B	107.7	C17—C16—H16A	107.7
C3—C4—C5	111.8 (4)	C8—C16—H16A	107.7
C3—C4—H4A	109.3	C17—C16—H16B	107.7
C5—C4—H4A	109.3	C8—C16—H16B	107.7
C3—C4—H4B	109.3	H16A—C16—H16B	107.1
C5—C4—H4B	109.3	O4—C17—O4'	32.7 (15)
H4A—C4—H4B	107.9	O4—C17—O3	117.0 (11)
C4—C5—C6	113.5 (4)	O4'—C17—O3	116.7 (14)
C4—C5—H5A	108.9	O4—C17—C16	119 (2)
C6—C5—H5A	108.9	O4'—C17—C16	121 (2)
C4—C5—H5B	108.9	O3—C17—C16	120.4 (5)
C6—C5—H5B	108.9	C2—C18—H18A	109.5
H5A—C5—H5B	107.7	C2—C18—H18B	109.5
C27—C6—C5	108.1 (4)	H18A—C18—H18B	109.5
C27—C6—C11	112.9 (4)	C2—C18—H18C	109.5
C5—C6—C11	107.9 (4)	H18A—C18—H18C	109.5
C27—C6—C7	112.6 (4)	H18B—C18—H18C	109.5
C5—C6—C7	107.3 (4)	C14—C19—H19A	109.5
C11—C6—C7	107.8 (3)	C14—C19—H19B	109.5
C12—C7—C8	110.1 (4)	H19A—C19—H19B	109.5
C12—C7—C6	114.0 (4)	C14—C19—H19C	109.5
C8—C7—C6	117.7 (4)	H19A—C19—H19C	109.5
C12—C7—H7	104.5	H19B—C19—H19C	109.5
C8—C7—H7	104.5	O5—C20—O1	115 (5)
C6—C7—H7	104.5	O5—C20—C21	127.0 (5)
C9—C8—C16	109.2 (4)	O1—C20—C21	117 (4)
C9—C8—C15	109.6 (3)	O5—C20—O1'	128 (4)
C16—C8—C15	104.7 (4)	O1—C20—O1'	24 (2)
C9—C8—C7	109.8 (4)	C21—C20—O1'	105 (6)
C16—C8—C7	115.5 (4)	C22—C21—C26	119.7 (5)
C15—C8—C7	107.8 (4)	C22—C21—C20	122.7 (5)
C8—C9—C10	112.7 (4)	C26—C21—C20	117.6 (5)
C8—C9—H9A	109.1	C21—C22—C23	119.8 (6)
C10—C9—H9A	109.1	C21—C22—H22	120.1
C8—C9—H9B	109.1	C23—C22—H22	120.1
C10—C9—H9B	109.1	C24—C23—C22	120.0 (6)
H9A—C9—H9B	107.8	C24—C23—H23	120.0
C11—C10—C9	109.7 (4)	C22—C23—H23	120.0
C11—C10—H10A	109.7	C23—C24—C25	120.6 (6)
C9—C10—H10A	109.7	C23—C24—H24	119.7
C11—C10—H10B	109.7	C25—C24—H24	119.7
C9—C10—H10B	109.7	C24—C25—C26	120.6 (6)
H10A—C10—H10B	108.2	C24—C25—H25	119.7
C10—C11—C6	112.0 (4)	C26—C25—H25	119.7
C10—C11—C2	116.6 (4)	C25—C26—C21	119.2 (6)
C6—C11—C2	115.3 (4)	C25—C26—H26	120.4
C10—C11—H11	103.6	C21—C26—H26	120.4
C6—C11—H11	103.6	C6—C27—H27A	109.5
C2—C11—H11	103.6	C6—C27—H27B	109.5
C13—C12—C7	111.2 (4)	H27A—C27—H27B	109.5
C13—C12—H12A	109.4	C6—C27—H27C	109.5
C7—C12—H12A	109.4	H27A—C27—H27C	109.5
C13—C12—H12B	109.4	H27B—C27—H27C	109.5
C7—C12—H12B	109.4
C20—O1'—C1—O2	−51 (23)	C18—C2—C11—C10	53.1 (6)
C20—O1'—C1—O1	68 (18)	C1—C2—C11—C6	71.1 (6)
C20—O1'—C1—C2	148 (12)	C3—C2—C11—C6	−53.7 (6)
C20—O1—C1—O2	0(15)	C18—C2—C11—C6	−172.5 (4)
C20—O1—C1—O1'	−73 (11)	C8—C7—C12—C13	−55.7 (5)
C20—O1—C1—C2	178 (8)	C6—C7—C12—C13	169.6 (4)
O2—C1—C2—C3	159.0 (5)	C7—C12—C13—C14	51.1 (6)
O1'—C1—C2—C3	−44 (13)	C17—O3—C14—C15	34.9 (6)
O1—C1—C2—C3	−19 (7)	C17—O3—C14—C13	−85.6 (6)
O2—C1—C2—C18	−84.3 (7)	C17—O3—C14—C19	155.9 (5)
O1'—C1—C2—C18	73 (13)	C12—C13—C14—O3	68.0 (5)
O1—C1—C2—C18	97 (7)	C12—C13—C14—C15	−51.3 (6)
O2—C1—C2—C11	36.5 (7)	C12—C13—C14—C19	−178.4 (4)
O1'—C1—C2—C11	−166 (13)	O3—C14—C15—C8	−61.8 (5)
O1—C1—C2—C11	−142 (7)	C13—C14—C15—C8	56.8 (5)
C1—C2—C3—C4	−71.8 (6)	C19—C14—C15—C8	−177.0 (5)
C18—C2—C3—C4	174.0 (4)	C9—C8—C15—C14	178.9 (4)
C11—C2—C3—C4	53.0 (5)	C16—C8—C15—C14	61.9 (5)
C2—C3—C4—C5	−55.2 (6)	C7—C8—C15—C14	−61.6 (5)
C3—C4—C5—C6	55.2 (6)	C9—C8—C16—C17	−154.6 (4)
C4—C5—C6—C27	69.4 (5)	C15—C8—C16—C17	−37.3 (6)
C4—C5—C6—C11	−53.0 (5)	C7—C8—C16—C17	81.1 (5)
C4—C5—C6—C7	−168.9 (4)	C14—O3—C17—O4	−171 (7)
C27—C6—C7—C12	54.5 (5)	C14—O3—C17—O4'	152 (9)
C5—C6—C7—C12	−64.3 (5)	C14—O3—C17—C16	−11.8 (8)
C11—C6—C7—C12	179.7 (4)	C8—C16—C17—O4	173 (7)
C27—C6—C7—C8	−76.6 (5)	C8—C16—C17—O4'	−149 (9)
C5—C6—C7—C8	164.5 (4)	C8—C16—C17—O3	13.9 (8)
C11—C6—C7—C8	48.5 (5)	C1—O1—C20—O5	−70 (13)
C12—C7—C8—C9	179.7 (4)	C1—O1—C20—C21	121 (7)
C6—C7—C8—C9	−47.4 (5)	C1—O1—C20—O1'	58 (11)
C12—C7—C8—C16	−56.3 (5)	C1—O1'—C20—O5	−18 (26)
C6—C7—C8—C16	76.6 (5)	C1—O1'—C20—O1	−83 (19)
C12—C7—C8—C15	60.4 (4)	C1—O1'—C20—C21	152 (17)
C6—C7—C8—C15	−166.7 (4)	O5—C20—C21—C22	−177.4 (6)
C16—C8—C9—C10	−76.2 (5)	O1—C20—C21—C22	−9(8)
C15—C8—C9—C10	169.7 (4)	O1'—C20—C21—C22	12 (9)
C7—C8—C9—C10	51.4 (5)	O5—C20—C21—C26	2.3 (10)
C8—C9—C10—C11	−60.0 (5)	O1—C20—C21—C26	170 (8)
C9—C10—C11—C6	61.9 (5)	O1'—C20—C21—C26	−168 (9)
C9—C10—C11—C2	−162.2 (4)	C26—C21—C22—C23	−0.4 (9)
C27—C6—C11—C10	70.7 (5)	C20—C21—C22—C23	179.4 (6)
C5—C6—C11—C10	−169.9 (4)	C21—C22—C23—C24	0.1 (10)
C7—C6—C11—C10	−54.3 (5)	C22—C23—C24—C25	−0.1 (10)
C27—C6—C11—C2	−65.8 (6)	C23—C24—C25—C26	0.4 (10)
C5—C6—C11—C2	53.6 (5)	C24—C25—C26—C21	−0.7 (10)
C7—C6—C11—C2	169.2 (4)	C22—C21—C26—C25	0.6 (9)
C1—C2—C11—C10	−63.3 (6)	C20—C21—C26—C25	−179.1 (6)
C3—C2—C11—C10	171.9 (4)