A dimeric sesquiterpene, gochnatiolide A.

THE TITLE COMPOUND [SYSTEMATIC NAME: 5'a-hydroxy-1',3,6,8'-tetrakis(methylene)-3a,4,5,5',5'a,6,6',6a,7,7',7'a,8',9a,9b,10'a,10'b-hexadecahydrospiro[azuleno[4,5-b]furan-9(2H),3'-[3H]benz[1,8]azuleno[4,5-b]furan]-2,2',8,9'(1'H,3H,4'H)-tetrone acetone 0.92-solvate], C(30)H(30)O(7)·0.92C(3)H(6)O, is a dimeric sequiterpene formed by a cyclohexane system connecting two monomeric sesquiterpene lactone units of dehydro-zaluzanin C. It was isolated from Ainsliaea henryi.

Related literature

For similar compounds and background information, see: Chinese Materia Medica (2007 ▶); Bohlmann & Zdero (1979 ▶); Bohlmann et al. (1981 ▶, 1982 ▶, 1983 ▶, 1984 ▶, 1986 ▶). For the pharmacological activity of a related compound, see: Wu et al. (2008 ▶).

Experimental

Crystal data

C30H30O7·0.92C3H6O

M = 555.94

Orthorhombic,

a = 8.709 (4) Å

b = 12.652 (6) Å

c = 25.890 (12) Å

V = 2853 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 294 K

0.15 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.986, T max = 0.993

11789 measured reflections

2864 independent reflections

1873 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.119

S = 0.93

2864 reflections

401 parameters

128 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809042743/pk2191sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042743/pk2191Isup2.hkl

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

C30H30O7·0.92C3H6O	F(000) = 1182
Mr = 555.94	Dx = 1.294 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1001 reflections
a = 8.709 (4) Å	θ = 2.5–24.3°
b = 12.652 (6) Å	µ = 0.09 mm−1
c = 25.890 (12) Å	T = 294 K
V = 2853 (2) Å3	Block, colourless
Z = 4	0.15 × 0.10 × 0.08 mm

Bruker SMART APEX CCD area-detector diffractometer	2864 independent reflections
Radiation source: sealed tube	1873 reflections with I > 2σ(I)
graphite	Rint = 0.078
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→10
Tmin = 0.986, Tmax = 0.993	k = −15→14
11789 measured reflections	l = −30→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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0673P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max < 0.001
2864 reflections	Δρmax = 0.32 e Å−3
401 parameters	Δρmin = −0.12 e Å−3
128 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.0034 (11)
Primary atom site location: structure-invariant direct methods

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 >2σ(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	0.4589 (3)	0.8430 (3)	0.72146 (11)	0.0859 (10)
O3	−0.0138 (4)	0.9219 (3)	0.95361 (11)	0.1010 (12)
O4	0.0768 (3)	0.8957 (2)	0.87468 (10)	0.0704 (8)
O5	0.3123 (4)	0.6000 (3)	0.68984 (12)	0.0936 (10)
O6	0.0973 (3)	0.9794 (2)	0.61271 (10)	0.0648 (8)
O7	0.0044 (4)	1.1419 (3)	0.60213 (13)	0.0963 (11)
C2	0.1914 (4)	0.8169 (3)	0.70590 (13)	0.0511 (9)
C3	0.3257 (5)	0.8549 (3)	0.73401 (15)	0.0609 (10)
C4	0.2677 (5)	0.9100 (3)	0.78106 (14)	0.0609 (11)
C5	0.0944 (4)	0.9005 (3)	0.78111 (13)	0.0523 (9)
H5	0.0503	0.9716	0.7791	0.063*
C6	0.0263 (4)	0.8446 (3)	0.82731 (13)	0.0510 (9)
H6	0.0602	0.7707	0.8274	0.061*
C7	−0.1479 (5)	0.8484 (4)	0.82852 (14)	0.0612 (10)
H7	−0.1816	0.9131	0.8111	0.073*
C11	−0.1797 (5)	0.8596 (4)	0.88515 (15)	0.0695 (12)
C12	−0.0371 (5)	0.8938 (4)	0.91013 (17)	0.0737 (12)
C13	−0.3092 (7)	0.8448 (5)	0.91028 (19)	0.0967 (16)
H13A	−0.3133	0.8562	0.9457	0.116*
H13B	−0.3965	0.8230	0.8926	0.116*
C8	−0.2239 (6)	0.7527 (4)	0.80139 (18)	0.0570 (14)	0.808 (5)
H8A	−0.2150	0.6919	0.8240	0.068*	0.808 (5)
H8B	−0.3325	0.7677	0.7974	0.068*	0.808 (5)
C9	−0.1589 (6)	0.7225 (4)	0.74833 (17)	0.0584 (13)	0.808 (5)
H9A	−0.2389	0.6861	0.7292	0.070*	0.808 (5)
H9B	−0.0761	0.6724	0.7537	0.070*	0.808 (5)
C10	−0.0979 (5)	0.8128 (4)	0.71442 (17)	0.0512 (11)	0.808 (5)
O2	−0.1932 (4)	0.9031 (3)	0.71949 (13)	0.0660 (10)	0.808 (5)
H2	−0.2835	0.8847	0.7197	0.099*	0.808 (5)
C14	−0.0889 (5)	0.7804 (5)	0.65696 (19)	0.0609 (17)	0.808 (5)
H14A	−0.1830	0.7440	0.6478	0.073*	0.808 (5)
H14B	−0.0833	0.8440	0.6361	0.073*	0.808 (5)
C1	0.0602 (6)	0.8438 (4)	0.7319 (3)	0.0468 (15)	0.808 (5)
C8'	−0.263 (2)	0.7876 (19)	0.7957 (6)	0.062 (5)*	0.192 (5)
H8'1	−0.2629	0.7133	0.8049	0.075*	0.192 (5)
H8'2	−0.3661	0.8153	0.8008	0.075*	0.192 (5)
C9'	−0.214 (2)	0.8023 (17)	0.7405 (7)	0.060 (3)*	0.192 (5)
H9'1	−0.2103	0.8778	0.7340	0.073*	0.192 (5)
H9'2	−0.2944	0.7736	0.7188	0.073*	0.192 (5)
C10'	−0.0634 (19)	0.7563 (13)	0.7216 (7)	0.051 (3)*	0.192 (5)
O2'	−0.0418 (17)	0.6540 (11)	0.7438 (6)	0.070 (4)*	0.192 (5)
H2'	0.0503	0.6411	0.7456	0.106*	0.192 (5)
C14'	−0.102 (2)	0.754 (3)	0.6631 (7)	0.062 (4)*	0.192 (5)
H14C	−0.1885	0.7082	0.6555	0.074*	0.192 (5)
H14D	−0.1220	0.8243	0.6495	0.074*	0.192 (5)
C1'	0.081 (3)	0.817 (2)	0.7323 (14)	0.045 (4)*	0.192 (5)
C15	0.3579 (6)	0.9603 (4)	0.81350 (18)	0.0902 (17)
H15A	0.4632	0.9626	0.8076	0.108*
H15B	0.3165	0.9935	0.8423	0.108*
C21	0.3861 (4)	0.7640 (3)	0.58050 (14)	0.0600 (10)
H21	0.4744	0.8079	0.5709	0.072*
C22	0.4426 (5)	0.6809 (4)	0.61919 (16)	0.0775 (13)
H22A	0.4597	0.6139	0.6019	0.093*
H22B	0.5383	0.7034	0.6349	0.093*
C23	0.3214 (5)	0.6699 (4)	0.65901 (15)	0.0693 (11)
C24	0.2052 (4)	0.7607 (3)	0.65507 (13)	0.0519 (9)
C25	0.2759 (4)	0.8337 (3)	0.61335 (13)	0.0511 (9)
H25	0.3408	0.8844	0.6318	0.061*
C26	0.1675 (4)	0.8979 (3)	0.58093 (12)	0.0509 (9)
H26	0.0862	0.8510	0.5682	0.061*
C27	0.2387 (5)	0.9549 (3)	0.53460 (13)	0.0558 (10)
H27	0.3469	0.9696	0.5422	0.067*
C28	0.2292 (5)	0.8915 (3)	0.48538 (14)	0.0612 (10)
H28A	0.2586	0.9365	0.4567	0.073*
H28B	0.1232	0.8706	0.4800	0.073*
C29	0.3292 (5)	0.7929 (4)	0.48453 (14)	0.0665 (11)
H29A	0.3035	0.7524	0.4539	0.080*
H29B	0.4355	0.8149	0.4812	0.080*
C30	0.3170 (4)	0.7206 (4)	0.53086 (14)	0.0585 (10)
C31	0.1522 (5)	1.0569 (3)	0.53462 (16)	0.0658 (11)
C32	0.0762 (5)	1.0678 (4)	0.58487 (18)	0.0683 (12)
C33	0.1407 (7)	1.1302 (4)	0.49896 (19)	0.0936 (16)
H33A	0.0833	1.1908	0.5053	0.112*
H33B	0.1899	1.1215	0.4674	0.112*
C34	0.2586 (5)	0.6260 (4)	0.5270 (2)	0.0837 (14)
H34A	0.2233	0.6017	0.4953	0.100*
H34B	0.2522	0.5829	0.5561	0.100*
C35	0.0480 (5)	0.7089 (3)	0.64304 (13)	0.0637 (11)
H35A	0.0434	0.6920	0.6065	0.076*
H35B	0.0397	0.6433	0.6622	0.076*
O8	0.3631 (7)	0.4623 (4)	0.8854 (2)	0.146 (2)	0.919 (7)
C40	0.3646 (10)	0.6279 (6)	0.9215 (3)	0.133 (3)	0.919 (7)
H40A	0.3417	0.5887	0.9523	0.199*	0.919 (7)
H40B	0.2852	0.6791	0.9155	0.199*	0.919 (7)
H40C	0.4612	0.6634	0.9255	0.199*	0.919 (7)
C41	0.3730 (8)	0.5566 (5)	0.8781 (3)	0.104 (2)	0.919 (7)
C42	0.3737 (11)	0.6047 (7)	0.8249 (3)	0.153 (3)	0.919 (7)
H42A	0.4679	0.5870	0.8077	0.230*	0.919 (7)
H42B	0.3649	0.6801	0.8276	0.230*	0.919 (7)
H42C	0.2886	0.5775	0.8054	0.230*	0.919 (7)

	U11	U22	U33	U12	U13	U23
O1	0.0530 (19)	0.142 (3)	0.0630 (18)	−0.0116 (19)	−0.0036 (14)	−0.0044 (19)
O3	0.105 (3)	0.149 (3)	0.0488 (18)	−0.008 (2)	0.0050 (17)	−0.024 (2)
O4	0.0734 (18)	0.090 (2)	0.0480 (15)	−0.0099 (17)	−0.0003 (14)	−0.0065 (15)
O5	0.120 (3)	0.088 (2)	0.072 (2)	0.024 (2)	0.009 (2)	0.0258 (19)
O6	0.0758 (18)	0.0645 (17)	0.0542 (16)	0.0076 (15)	0.0078 (14)	−0.0041 (15)
O7	0.114 (3)	0.071 (2)	0.104 (2)	0.021 (2)	0.007 (2)	−0.0157 (19)
C2	0.055 (2)	0.057 (2)	0.041 (2)	−0.0060 (19)	−0.0039 (18)	0.0063 (17)
C3	0.052 (2)	0.083 (3)	0.048 (2)	−0.016 (2)	−0.006 (2)	0.008 (2)
C4	0.069 (3)	0.070 (3)	0.044 (2)	−0.024 (2)	−0.0062 (19)	0.000 (2)
C5	0.058 (2)	0.051 (2)	0.048 (2)	−0.0062 (18)	−0.0026 (18)	−0.0016 (18)
C6	0.061 (2)	0.049 (2)	0.043 (2)	−0.0018 (18)	−0.0023 (18)	−0.0045 (17)
C7	0.059 (2)	0.076 (3)	0.049 (2)	0.006 (2)	0.0055 (19)	0.002 (2)
C11	0.068 (3)	0.088 (3)	0.053 (2)	0.003 (3)	0.012 (2)	−0.003 (2)
C12	0.078 (3)	0.088 (3)	0.055 (3)	0.006 (3)	0.010 (2)	−0.006 (2)
C13	0.091 (4)	0.128 (4)	0.071 (3)	−0.009 (3)	0.017 (3)	−0.014 (3)
C8	0.044 (3)	0.074 (3)	0.053 (3)	−0.002 (2)	0.002 (2)	0.002 (2)
C9	0.059 (3)	0.065 (3)	0.051 (2)	−0.013 (2)	0.004 (2)	−0.004 (2)
C10	0.047 (2)	0.056 (2)	0.051 (2)	−0.003 (2)	−0.0003 (19)	0.000 (2)
O2	0.060 (2)	0.076 (2)	0.062 (2)	0.0098 (19)	−0.0026 (18)	−0.0013 (19)
C14	0.051 (3)	0.084 (4)	0.048 (3)	−0.024 (3)	0.003 (2)	−0.002 (3)
C1	0.049 (3)	0.047 (3)	0.044 (2)	−0.003 (3)	−0.004 (2)	0.005 (3)
C15	0.085 (3)	0.119 (4)	0.067 (3)	−0.038 (3)	0.000 (3)	−0.014 (3)
C21	0.049 (2)	0.078 (3)	0.053 (2)	0.008 (2)	0.0035 (18)	0.002 (2)
C22	0.065 (3)	0.106 (4)	0.061 (3)	0.016 (3)	0.000 (2)	0.014 (2)
C23	0.082 (3)	0.077 (3)	0.048 (2)	0.012 (3)	−0.005 (2)	0.008 (2)
C24	0.059 (2)	0.062 (2)	0.0348 (18)	−0.0041 (19)	−0.0005 (17)	0.0052 (17)
C25	0.052 (2)	0.060 (2)	0.041 (2)	−0.0039 (18)	−0.0013 (17)	0.0007 (18)
C26	0.052 (2)	0.058 (2)	0.0423 (19)	−0.006 (2)	−0.0009 (17)	−0.0030 (18)
C27	0.059 (2)	0.064 (2)	0.044 (2)	−0.0039 (19)	−0.0001 (18)	0.0052 (19)
C28	0.066 (3)	0.078 (3)	0.039 (2)	−0.008 (2)	−0.0010 (18)	0.000 (2)
C29	0.068 (3)	0.089 (3)	0.042 (2)	−0.002 (3)	0.002 (2)	−0.007 (2)
C30	0.052 (2)	0.070 (3)	0.053 (2)	0.009 (2)	0.0046 (19)	−0.006 (2)
C31	0.074 (3)	0.067 (3)	0.056 (3)	−0.007 (2)	−0.010 (2)	0.008 (2)
C32	0.067 (3)	0.062 (3)	0.076 (3)	0.001 (2)	−0.007 (2)	−0.007 (2)
C33	0.122 (4)	0.074 (3)	0.084 (3)	0.009 (3)	−0.005 (3)	0.017 (3)
C34	0.085 (3)	0.083 (3)	0.083 (3)	0.010 (3)	0.007 (3)	−0.014 (3)
C35	0.081 (3)	0.067 (3)	0.043 (2)	−0.018 (2)	−0.010 (2)	0.0013 (19)
O8	0.191 (6)	0.105 (4)	0.143 (4)	0.033 (4)	−0.016 (4)	−0.010 (3)
C40	0.156 (7)	0.126 (6)	0.117 (5)	−0.007 (5)	−0.026 (5)	−0.016 (5)
C41	0.131 (6)	0.074 (4)	0.106 (5)	0.024 (4)	−0.027 (4)	−0.022 (4)
C42	0.208 (9)	0.138 (7)	0.114 (5)	−0.043 (7)	0.002 (6)	−0.016 (5)

O1—C3	1.214 (5)	C10'—C1'	1.499 (10)
O3—C12	1.198 (5)	C10'—C14'	1.554 (17)
O4—C12	1.351 (5)	O2'—H2'	0.8200
O4—C6	1.454 (4)	C14'—C35	1.518 (11)
O5—C23	1.193 (5)	C14'—H14C	0.9700
O6—C32	1.344 (5)	C14'—H14D	0.9700
O6—C26	1.454 (4)	C15—H15A	0.9300
O7—C32	1.212 (5)	C15—H15B	0.9300
C2—C1'	1.18 (3)	C21—C30	1.522 (5)
C2—C1	1.370 (8)	C21—C22	1.533 (6)
C2—C3	1.459 (5)	C21—C25	1.556 (5)
C2—C24	1.500 (5)	C21—H21	0.9800
C3—C4	1.492 (6)	C22—C23	1.482 (6)
C4—C15	1.315 (5)	C22—H22A	0.9700
C4—C5	1.514 (5)	C22—H22B	0.9700
C5—C1	1.491 (8)	C23—C24	1.535 (6)
C5—C6	1.511 (5)	C24—C25	1.548 (5)
C5—C1'	1.65 (3)	C24—C35	1.549 (5)
C5—H5	0.9800	C25—C26	1.502 (5)
C6—C7	1.518 (5)	C25—H25	0.9800
C6—H6	0.9800	C26—C27	1.531 (5)
C7—C11	1.499 (5)	C26—H26	0.9800
C7—C8'	1.525 (11)	C27—C31	1.494 (6)
C7—C8	1.548 (6)	C27—C28	1.509 (5)
C7—H7	0.9800	C27—H27	0.9800
C11—C13	1.315 (6)	C28—C29	1.522 (6)
C11—C12	1.465 (7)	C28—H28A	0.9700
C13—H13A	0.9300	C28—H28B	0.9700
C13—H13B	0.9300	C29—C30	1.512 (5)
C8—C9	1.534 (6)	C29—H29A	0.9700
C8—H8A	0.9700	C29—H29B	0.9700
C8—H8B	0.9700	C30—C34	1.304 (6)
C9—C10	1.536 (6)	C31—C33	1.312 (6)
C9—H9A	0.9700	C31—C32	1.466 (6)
C9—H9B	0.9700	C33—H33A	0.9300
C10—O2	1.418 (6)	C33—H33B	0.9300
C10—C1	1.502 (6)	C34—H34A	0.9300
C10—C14	1.545 (6)	C34—H34B	0.9300
O2—H2	0.8200	C35—H35A	0.9700
C14—C35	1.539 (6)	C35—H35B	0.9700
C14—H14A	0.9700	O8—C41	1.211 (7)
C14—H14B	0.9700	C40—C41	1.441 (8)
C8'—C9'	1.505 (17)	C40—H40A	0.9600
C8'—H8'1	0.9700	C40—H40B	0.9600
C8'—H8'2	0.9700	C40—H40C	0.9600
C9'—C10'	1.513 (16)	C41—C42	1.507 (9)
C9'—H9'1	0.9700	C42—H42A	0.9600
C9'—H9'2	0.9700	C42—H42B	0.9600
C10'—O2'	1.427 (15)	C42—H42C	0.9600
C12—O4—C6	110.1 (3)	H14C—C14'—H14D	109.7
C32—O6—C26	110.2 (3)	C2—C1'—C10'	125 (2)
C1'—C2—C3	111.3 (13)	C2—C1'—C5	112.8 (12)
C1—C2—C3	109.9 (4)	C10'—C1'—C5	122 (2)
C1'—C2—C24	125.1 (13)	C4—C15—H15A	120.0
C1—C2—C24	128.1 (4)	C4—C15—H15B	120.0
C3—C2—C24	121.9 (3)	H15A—C15—H15B	120.0
O1—C3—C2	126.3 (4)	C30—C21—C22	115.5 (4)
O1—C3—C4	126.9 (4)	C30—C21—C25	114.9 (3)
C2—C3—C4	106.8 (3)	C22—C21—C25	103.3 (3)
C15—C4—C3	123.0 (4)	C30—C21—H21	107.6
C15—C4—C5	129.3 (4)	C22—C21—H21	107.6
C3—C4—C5	107.6 (3)	C25—C21—H21	107.6
C1—C5—C6	111.9 (3)	C23—C22—C21	106.9 (3)
C1—C5—C4	103.7 (4)	C23—C22—H22A	110.3
C6—C5—C4	115.4 (3)	C21—C22—H22A	110.3
C6—C5—C1'	106.2 (11)	C23—C22—H22B	110.3
C4—C5—C1'	97.0 (8)	C21—C22—H22B	110.3
C1—C5—H5	108.5	H22A—C22—H22B	108.6
C6—C5—H5	108.5	O5—C23—C22	125.6 (4)
C4—C5—H5	108.5	O5—C23—C24	123.7 (4)
C1'—C5—H5	121.2	C22—C23—C24	110.7 (4)
O4—C6—C5	109.9 (3)	C2—C24—C23	110.4 (3)
O4—C6—C7	105.7 (3)	C2—C24—C25	111.2 (3)
C5—C6—C7	113.2 (3)	C23—C24—C25	103.3 (3)
O4—C6—H6	109.3	C2—C24—C35	107.8 (3)
C5—C6—H6	109.3	C23—C24—C35	106.2 (3)
C7—C6—H6	109.3	C25—C24—C35	117.6 (3)
C11—C7—C6	102.0 (3)	C26—C25—C24	117.6 (3)
C11—C7—C8'	118.1 (8)	C26—C25—C21	112.9 (3)
C6—C7—C8'	129.2 (10)	C24—C25—C21	106.8 (3)
C11—C7—C8	116.0 (4)	C26—C25—H25	106.3
C6—C7—C8	113.1 (4)	C24—C25—H25	106.3
C11—C7—H7	108.4	C21—C25—H25	106.3
C6—C7—H7	108.4	O6—C26—C25	109.4 (3)
C8'—C7—H7	88.1	O6—C26—C27	106.2 (3)
C8—C7—H7	108.4	C25—C26—C27	116.0 (3)
C13—C11—C12	123.4 (4)	O6—C26—H26	108.4
C13—C11—C7	129.0 (4)	C25—C26—H26	108.4
C12—C11—C7	107.6 (4)	C27—C26—H26	108.4
O3—C12—O4	120.6 (4)	C31—C27—C28	115.6 (3)
O3—C12—C11	130.2 (4)	C31—C27—C26	101.7 (3)
O4—C12—C11	109.1 (4)	C28—C27—C26	112.9 (3)
C11—C13—H13A	120.0	C31—C27—H27	108.8
C11—C13—H13B	120.0	C28—C27—H27	108.8
H13A—C13—H13B	120.0	C26—C27—H27	108.8
C9—C8—C7	116.3 (4)	C27—C28—C29	114.6 (3)
C9—C8—H8A	108.2	C27—C28—H28A	108.6
C7—C8—H8A	108.2	C29—C28—H28A	108.6
C9—C8—H8B	108.2	C27—C28—H28B	108.6
C7—C8—H8B	108.2	C29—C28—H28B	108.6
H8A—C8—H8B	107.4	H28A—C28—H28B	107.6
C8—C9—C10	117.0 (4)	C30—C29—C28	116.4 (3)
C8—C9—H9A	108.1	C30—C29—H29A	108.2
C10—C9—H9A	108.1	C28—C29—H29A	108.2
C8—C9—H9B	108.1	C30—C29—H29B	108.2
C10—C9—H9B	108.1	C28—C29—H29B	108.2
H9A—C9—H9B	107.3	H29A—C29—H29B	107.3
O2—C10—C1	107.3 (4)	C34—C30—C29	121.5 (4)
O2—C10—C9	110.1 (4)	C34—C30—C21	123.4 (4)
C1—C10—C9	109.8 (4)	C29—C30—C21	115.0 (4)
O2—C10—C14	109.4 (4)	C33—C31—C32	121.5 (4)
C1—C10—C14	108.3 (4)	C33—C31—C27	130.4 (4)
C9—C10—C14	111.8 (4)	C32—C31—C27	108.0 (3)
C35—C14—C10	114.8 (4)	O7—C32—O6	121.1 (4)
C35—C14—H14A	108.6	O7—C32—C31	129.3 (4)
C10—C14—H14A	108.6	O6—C32—C31	109.6 (4)
C35—C14—H14B	108.6	C31—C33—H33A	120.0
C10—C14—H14B	108.6	C31—C33—H33B	120.0
H14A—C14—H14B	107.5	H33A—C33—H33B	120.0
C2—C1—C5	111.9 (4)	C30—C34—H34A	120.0
C2—C1—C10	123.4 (5)	C30—C34—H34B	120.0
C5—C1—C10	124.5 (5)	H34A—C34—H34B	120.0
C9'—C8'—C7	106.1 (13)	C14'—C35—C24	122.2 (12)
C9'—C8'—H8'1	110.5	C14—C35—C24	112.9 (4)
C7—C8'—H8'1	110.5	C14'—C35—H35A	112.3
C9'—C8'—H8'2	110.5	C14—C35—H35A	109.0
C7—C8'—H8'2	110.5	C24—C35—H35A	109.0
H8'1—C8'—H8'2	108.7	C14'—C35—H35B	94.8
C8'—C9'—C10'	120.5 (16)	C14—C35—H35B	109.0
C8'—C9'—H9'1	107.2	C24—C35—H35B	109.0
C10'—C9'—H9'1	107.2	H35A—C35—H35B	107.8
C8'—C9'—H9'2	107.2	C41—C40—H40A	109.5
C10'—C9'—H9'2	107.2	C41—C40—H40B	109.5
H9'1—C9'—H9'2	106.8	H40A—C40—H40B	109.5
O2'—C10'—C1'	106.4 (15)	C41—C40—H40C	109.5
O2'—C10'—C9'	109.5 (14)	H40A—C40—H40C	109.5
C1'—C10'—C9'	117.9 (17)	H40B—C40—H40C	109.5
O2'—C10'—C14'	113.8 (16)	O8—C41—C40	119.4 (7)
C1'—C10'—C14'	111.8 (18)	O8—C41—C42	122.7 (6)
C9'—C10'—C14'	97.7 (11)	C40—C41—C42	117.4 (6)
C10'—O2'—H2'	109.5	C41—C42—H42A	109.5
C35—C14'—C10'	98.8 (11)	C41—C42—H42B	109.5
C35—C14'—H14C	112.0	H42A—C42—H42B	109.5
C10'—C14'—H14C	112.0	C41—C42—H42C	109.5
C35—C14'—H14D	112.0	H42A—C42—H42C	109.5
C10'—C14'—H14D	112.0	H42B—C42—H42C	109.5