Arborinol methyl ether from Areca catechu L.

The title compound isolated from Areca catechu L. (common name: arborinol methyl ether; a member of the arborane family) was established as 3α-methoxyarbor-9(11)-ene, C(31)H(52)O. Rings A/B/C/D assume a chair conformation, while ring E has an envelope conformation. The absolute configuration was determined to be (3R,5R,8S,10S,13R,14S,17S,18S, 21S) by analysis of Bijvoet pairs based on resonant scattering of light atoms, yielding a Hooft parameter y of -0.03 (3).

Related literature

For the biological activity of Areca catechu L. compounds, see: Dar et al. (1997 ▶); Hocart & Fankhauser (1996 ▶); Iwamoto et al. (1988 ▶); Kusumoto et al. (1995 ▶); Norton (1998 ▶); Lee & Choi (1999 ▶); Ohmoto & Natori (1969 ▶); Chan et al. (2008 ▶); Pithayanukul et al. (2009 ▶); Zhang et al. (2010 ▶). For related structures, see: Corrêa et al. (2009 ▶); Khera et al. (2003 ▶); Takahashi & Iitaka (1972 ▶). Analysis of the absolute configuration was performed by using likelihood methods (Hooft et al., 2008 ▶) using PLATON (Spek, 2009 ▶).

Experimental

Crystal data

C31H52O

M = 440.73

Triclinic,

a = 6.2684 (2) Å

b = 7.1162 (3) Å

c = 16.0814 (5) Å

α = 96.812 (3)°

β = 91.079 (3)°

γ = 114.397 (4)°

V = 646.86 (4) Å3

Z = 1

Cu Kα radiation

μ = 0.48 mm−1

T = 120 K

0.60 × 0.50 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.658, T max = 1.0

10247 measured reflections

4415 independent reflections

4408 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.04

4415 reflections

298 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1952 Friedel pairs

Flack parameter: 0.02 (22)

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810030758/si2282sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030758/si2282Isup2.hkl

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

C31H52O	Z = 1
Mr = 440.73	F(000) = 246
Triclinic, P1	Dx = 1.131 Mg m−3
Hall symbol: P 1	Cu Kα radiation, λ = 1.5418 Å
a = 6.2684 (2) Å	Cell parameters from 11404 reflections
b = 7.1162 (3) Å	θ = 2.8–69.9°
c = 16.0814 (5) Å	µ = 0.48 mm−1
α = 96.812 (3)°	T = 120 K
β = 91.079 (3)°	Block, colourless
γ = 114.397 (4)°	0.60 × 0.50 × 0.40 mm
V = 646.86 (4) Å3

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4415 independent reflections
Radiation source: fine-focus sealed tube	4408 reflections with I > 2σ(I)
graphite	Rint = 0.011
Detector resolution: 16.0356 pixels mm-1	θmax = 70.1°, θmin = 2.8°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −8→8
Tmin = 0.658, Tmax = 1.0	l = −19→19
10247 measured reflections

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0685P)2 + 0.1188P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
4415 reflections	Δρmax = 0.27 e Å−3
298 parameters	Δρmin = −0.18 e Å−3
3 restraints	Absolute structure: Flack (1983), 1952 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (22)

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
C1	0.5138 (3)	−0.3358 (2)	0.40741 (9)	0.0184 (3)
H1B	0.5050	−0.4577	0.4335	0.022*
H1A	0.3552	−0.3370	0.4057	0.022*
C2	0.5864 (3)	−0.3558 (2)	0.31749 (9)	0.0198 (3)
H2B	0.7412	−0.3622	0.3188	0.024*
H2A	0.4706	−0.4871	0.2852	0.024*
C3	0.6011 (3)	−0.1728 (2)	0.27380 (9)	0.0192 (3)
H3	0.6561	−0.1893	0.2165	0.023*
C4	0.7721 (3)	0.0390 (2)	0.32172 (8)	0.0179 (3)
C5	0.7148 (2)	0.0538 (2)	0.41576 (8)	0.0152 (3)
H5	0.5571	0.0575	0.4149	0.018*
C6	0.8804 (3)	0.2588 (2)	0.46836 (9)	0.0197 (3)
H6B	1.0362	0.2578	0.4785	0.024*
H6A	0.9012	0.3767	0.4374	0.024*
C7	0.7799 (3)	0.2871 (2)	0.55207 (9)	0.0200 (3)
H7A	0.6303	0.2993	0.5415	0.024*
H7B	0.8907	0.4186	0.5857	0.024*
C8	0.7348 (2)	0.1057 (2)	0.60306 (8)	0.0153 (3)
H8	0.8920	0.1098	0.6188	0.018*
C9	0.5957 (2)	−0.1040 (2)	0.54887 (8)	0.0150 (3)
C10	0.6864 (2)	−0.1349 (2)	0.46198 (8)	0.0154 (3)
C11	0.4202 (3)	−0.2573 (2)	0.57888 (9)	0.0197 (3)
H11	0.3307	−0.3797	0.5410	0.024*
C12	0.3540 (3)	−0.2501 (2)	0.66850 (9)	0.0199 (3)
H12B	0.3205	−0.3859	0.6878	0.024*
H12A	0.2094	−0.2262	0.6713	0.024*
C13	0.5521 (2)	−0.0759 (2)	0.72699 (8)	0.0154 (3)
C14	0.6215 (2)	0.1294 (2)	0.68650 (8)	0.0145 (3)
C15	0.7946 (3)	0.3152 (2)	0.74854 (8)	0.0179 (3)
H15B	0.9407	0.2963	0.7576	0.021*
H15A	0.8356	0.4446	0.7231	0.021*
C16	0.6969 (3)	0.3411 (2)	0.83427 (9)	0.0191 (3)
H16B	0.8175	0.4612	0.8710	0.023*
H16A	0.5581	0.3716	0.8261	0.023*
C17	0.6263 (2)	0.1459 (2)	0.87773 (8)	0.0173 (3)
C18	0.4636 (2)	−0.0441 (2)	0.81386 (8)	0.0166 (3)
H18	0.3244	−0.0145	0.8016	0.020*
C19	0.3707 (3)	−0.2239 (2)	0.86612 (10)	0.0259 (3)
H19B	0.4854	−0.2846	0.8728	0.031*
H19A	0.2198	−0.3348	0.8404	0.031*
C20	0.3376 (3)	−0.1160 (3)	0.95141 (10)	0.0285 (4)
H20B	0.4129	−0.1513	0.9982	0.034*
H20A	0.1684	−0.1626	0.9600	0.034*
C21	0.4542 (3)	0.1223 (2)	0.94855 (9)	0.0192 (3)
H21	0.3286	0.1607	0.9274	0.023*
C22	0.5449 (3)	0.2481 (3)	1.03637 (9)	0.0248 (3)
H22	0.6626	0.2042	1.0605	0.030*
C23	0.7374 (3)	0.2111 (2)	0.28168 (9)	0.0264 (3)
H23A	0.7427	0.1863	0.2206	0.040*
H23C	0.8627	0.3469	0.3041	0.040*
H23B	0.5848	0.2097	0.2947	0.040*
C24	1.0260 (3)	0.0673 (2)	0.30911 (10)	0.0243 (3)
H24C	1.0491	−0.0499	0.3275	0.036*
H24B	1.1358	0.1977	0.3423	0.036*
H24A	1.0547	0.0721	0.2495	0.036*
C25	0.9183 (3)	−0.1575 (2)	0.47981 (9)	0.0200 (3)
H25C	0.8942	−0.2552	0.5205	0.030*
H25B	1.0420	−0.0212	0.5027	0.030*
H25A	0.9650	−0.2102	0.4274	0.030*
C26	0.7569 (3)	−0.1429 (2)	0.73227 (9)	0.0205 (3)
H26C	0.7243	−0.2442	0.7719	0.031*
H26B	0.9031	−0.0205	0.7516	0.031*
H26A	0.7732	−0.2064	0.6766	0.031*
C27	0.4046 (3)	0.1723 (2)	0.66699 (9)	0.0192 (3)
H27B	0.4565	0.3150	0.6540	0.029*
H27C	0.3109	0.1553	0.7159	0.029*
H27A	0.3091	0.0738	0.6187	0.029*
C28	0.8488 (3)	0.1317 (3)	0.91300 (10)	0.0259 (3)
H28B	0.8048	−0.0020	0.9342	0.039*
H28C	0.9271	0.2459	0.9589	0.039*
H28A	0.9557	0.1421	0.8683	0.039*
C29	0.3424 (3)	0.1982 (3)	1.09390 (10)	0.0299 (4)
H29A	0.2243	0.2392	1.0712	0.045*
H29C	0.4025	0.2751	1.1502	0.045*
H29B	0.2708	0.0483	1.0971	0.045*
C30	0.6642 (4)	0.4834 (3)	1.03546 (11)	0.0385 (4)
H30B	0.8099	0.5187	1.0070	0.058*
H30C	0.7004	0.5551	1.0933	0.058*
H30A	0.5587	0.5273	1.0055	0.058*
C31	0.2276 (3)	−0.3154 (3)	0.19751 (10)	0.0283 (4)
H31B	0.3059	−0.2873	0.1453	0.043*
H31A	0.0790	−0.3013	0.1929	0.043*
H31C	0.1965	−0.4573	0.2075	0.043*
O1	0.37357 (19)	−0.17199 (17)	0.26493 (7)	0.0247 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0232 (8)	0.0137 (7)	0.0171 (7)	0.0071 (6)	0.0013 (6)	0.0005 (5)
C2	0.0255 (8)	0.0165 (7)	0.0180 (7)	0.0104 (6)	0.0000 (6)	−0.0020 (5)
C3	0.0238 (8)	0.0222 (7)	0.0143 (6)	0.0132 (6)	0.0022 (5)	−0.0010 (5)
C4	0.0239 (8)	0.0176 (7)	0.0139 (6)	0.0100 (6)	0.0027 (5)	0.0027 (5)
C5	0.0163 (7)	0.0152 (6)	0.0149 (6)	0.0074 (6)	0.0032 (5)	0.0016 (5)
C6	0.0249 (8)	0.0139 (7)	0.0173 (7)	0.0047 (6)	0.0042 (6)	0.0031 (5)
C7	0.0280 (8)	0.0116 (6)	0.0167 (6)	0.0048 (6)	0.0048 (6)	0.0012 (5)
C8	0.0167 (7)	0.0137 (6)	0.0143 (6)	0.0053 (5)	0.0009 (5)	0.0023 (5)
C9	0.0170 (7)	0.0135 (6)	0.0149 (6)	0.0071 (6)	0.0000 (5)	0.0010 (5)
C10	0.0156 (7)	0.0140 (6)	0.0167 (6)	0.0066 (6)	0.0008 (5)	0.0011 (5)
C11	0.0210 (7)	0.0151 (7)	0.0174 (6)	0.0031 (6)	0.0015 (6)	−0.0021 (5)
C12	0.0193 (7)	0.0153 (6)	0.0196 (7)	0.0019 (6)	0.0041 (6)	0.0010 (5)
C13	0.0143 (7)	0.0143 (6)	0.0166 (6)	0.0048 (6)	0.0019 (5)	0.0025 (5)
C14	0.0141 (7)	0.0129 (6)	0.0151 (6)	0.0043 (5)	0.0013 (5)	0.0013 (5)
C15	0.0179 (7)	0.0147 (7)	0.0164 (7)	0.0028 (6)	0.0030 (5)	0.0001 (5)
C16	0.0183 (7)	0.0186 (7)	0.0163 (6)	0.0047 (6)	0.0012 (5)	−0.0019 (5)
C17	0.0151 (7)	0.0225 (7)	0.0139 (6)	0.0082 (6)	0.0002 (5)	0.0000 (5)
C18	0.0151 (7)	0.0181 (7)	0.0165 (7)	0.0067 (6)	0.0022 (5)	0.0023 (5)
C19	0.0324 (9)	0.0232 (7)	0.0217 (7)	0.0101 (7)	0.0095 (6)	0.0054 (6)
C20	0.0356 (9)	0.0290 (8)	0.0215 (7)	0.0128 (7)	0.0106 (7)	0.0067 (6)
C21	0.0181 (7)	0.0262 (8)	0.0145 (6)	0.0106 (6)	0.0008 (5)	0.0021 (5)
C22	0.0242 (8)	0.0374 (9)	0.0151 (6)	0.0163 (7)	−0.0018 (6)	−0.0004 (6)
C23	0.0421 (10)	0.0224 (7)	0.0180 (7)	0.0163 (7)	0.0038 (6)	0.0044 (6)
C24	0.0250 (8)	0.0253 (7)	0.0216 (7)	0.0095 (6)	0.0091 (6)	0.0026 (6)
C25	0.0231 (7)	0.0236 (7)	0.0179 (6)	0.0146 (6)	0.0004 (5)	0.0024 (5)
C26	0.0258 (8)	0.0215 (7)	0.0191 (6)	0.0139 (6)	0.0050 (6)	0.0056 (5)
C27	0.0205 (7)	0.0231 (7)	0.0173 (6)	0.0120 (6)	0.0024 (5)	0.0034 (5)
C28	0.0208 (8)	0.0415 (9)	0.0191 (7)	0.0172 (7)	−0.0007 (6)	0.0021 (6)
C29	0.0354 (9)	0.0415 (9)	0.0166 (7)	0.0205 (8)	0.0048 (6)	0.0015 (6)
C30	0.0439 (11)	0.0391 (10)	0.0198 (8)	0.0078 (8)	0.0042 (7)	−0.0077 (7)
C31	0.0282 (9)	0.0290 (8)	0.0236 (7)	0.0094 (7)	−0.0047 (6)	−0.0015 (6)
O1	0.0263 (6)	0.0291 (6)	0.0206 (5)	0.0161 (5)	−0.0056 (4)	−0.0052 (4)

C1—C2	1.5324 (19)	C7—H7A	0.9900
C1—C10	1.5405 (18)	C7—H7B	0.9900
C2—C3	1.522 (2)	C8—H8	1.0000
C3—O1	1.4333 (17)	C11—H11	0.9500
C3—C4	1.541 (2)	C12—H12B	0.9900
C4—C23	1.5374 (19)	C12—H12A	0.9900
C4—C24	1.540 (2)	C15—H15B	0.9900
C4—C5	1.5625 (18)	C15—H15A	0.9900
C5—C6	1.5310 (18)	C16—H16B	0.9900
C5—C10	1.5596 (18)	C16—H16A	0.9900
C6—C7	1.5238 (19)	C18—H18	1.0000
C7—C8	1.5420 (18)	C19—H19B	0.9900
C8—C9	1.5276 (17)	C19—H19A	0.9900
C8—C14	1.5540 (18)	C20—H20B	0.9900
C9—C11	1.337 (2)	C20—H20A	0.9900
C9—C10	1.5441 (18)	C21—H21	1.0000
C10—C25	1.5518 (18)	C22—H22	1.0000
C11—C12	1.5081 (19)	C23—H23A	0.9800
C12—C13	1.5398 (19)	C23—H23C	0.9800
C13—C18	1.5389 (18)	C23—H23B	0.9800
C13—C26	1.5475 (18)	C24—H24C	0.9800
C13—C14	1.5681 (17)	C24—H24B	0.9800
C14—C15	1.5433 (18)	C24—H24A	0.9800
C14—C27	1.5459 (18)	C25—H25C	0.9800
C15—C16	1.5408 (18)	C25—H25B	0.9800
C16—C17	1.532 (2)	C25—H25A	0.9800
C17—C28	1.5416 (19)	C26—H26C	0.9800
C17—C18	1.5542 (18)	C26—H26B	0.9800
C17—C21	1.559 (2)	C26—H26A	0.9800
C18—C19	1.530 (2)	C27—H27B	0.9800
C19—C20	1.551 (2)	C27—H27C	0.9800
C20—C21	1.552 (2)	C27—H27A	0.9800
C21—C22	1.5389 (18)	C28—H28B	0.9800
C22—C30	1.528 (3)	C28—H28C	0.9800
C22—C29	1.531 (2)	C28—H28A	0.9800
C31—O1	1.4081 (17)	C29—H29A	0.9800
C1—H1B	0.9900	C29—H29C	0.9800
C1—H1A	0.9900	C29—H29B	0.9800
C2—H2B	0.9900	C30—H30B	0.9800
C2—H2A	0.9900	C30—H30C	0.9800
C3—H3	1.0000	C30—H30A	0.9800
C5—H5	1.0000	C31—H31B	0.9800
C6—H6B	0.9900	C31—H31A	0.9800
C6—H6A	0.9900	C31—H31C	0.9800
C2—C1—C10	112.49 (11)	C9—C11—H11	117.6
C3—C2—C1	111.47 (11)	C12—C11—H11	117.6
O1—C3—C2	110.02 (12)	C11—C12—H12B	109.4
O1—C3—C4	108.37 (10)	C13—C12—H12B	109.4
C2—C3—C4	112.71 (11)	C11—C12—H12A	109.4
C23—C4—C24	107.02 (13)	C13—C12—H12A	109.4
C23—C4—C3	107.93 (11)	H12B—C12—H12A	108.0
C24—C4—C3	108.99 (11)	C16—C15—H15B	108.8
C23—C4—C5	109.08 (11)	C14—C15—H15B	108.8
C24—C4—C5	113.95 (11)	C16—C15—H15A	108.8
C3—C4—C5	109.68 (11)	C14—C15—H15A	108.8
C6—C5—C10	110.54 (10)	H15B—C15—H15A	107.7
C6—C5—C4	113.02 (11)	C17—C16—H16B	109.2
C10—C5—C4	116.75 (10)	C15—C16—H16B	109.2
C7—C6—C5	110.12 (12)	C17—C16—H16A	109.2
C6—C7—C8	112.85 (11)	C15—C16—H16A	109.2
C9—C8—C7	110.87 (10)	H16B—C16—H16A	107.9
C9—C8—C14	112.63 (11)	C19—C18—H18	104.2
C7—C8—C14	112.86 (10)	C13—C18—H18	104.2
C11—C9—C8	121.21 (12)	C17—C18—H18	104.2
C11—C9—C10	122.38 (11)	C18—C19—H19B	111.3
C8—C9—C10	116.10 (11)	C20—C19—H19B	111.3
C1—C10—C9	111.82 (11)	C18—C19—H19A	111.3
C1—C10—C25	108.20 (11)	C20—C19—H19A	111.3
C9—C10—C25	105.67 (10)	H19B—C19—H19A	109.2
C1—C10—C5	108.28 (10)	C19—C20—H20B	110.3
C9—C10—C5	108.41 (10)	C21—C20—H20B	110.3
C25—C10—C5	114.52 (11)	C19—C20—H20A	110.3
C9—C11—C12	124.77 (12)	C21—C20—H20A	110.3
C11—C12—C13	111.37 (12)	H20B—C20—H20A	108.5
C18—C13—C12	110.26 (11)	C22—C21—H21	106.7
C18—C13—C26	111.86 (11)	C20—C21—H21	106.7
C12—C13—C26	106.74 (11)	C17—C21—H21	106.7
C18—C13—C14	108.59 (10)	C30—C22—H22	108.1
C12—C13—C14	107.04 (10)	C29—C22—H22	108.1
C26—C13—C14	112.23 (11)	C21—C22—H22	108.1
C15—C14—C27	107.89 (10)	C4—C23—H23A	109.5
C15—C14—C8	111.00 (11)	C4—C23—H23C	109.5
C27—C14—C8	108.65 (10)	H23A—C23—H23C	109.5
C15—C14—C13	109.22 (10)	C4—C23—H23B	109.5
C27—C14—C13	111.49 (11)	H23A—C23—H23B	109.5
C8—C14—C13	108.61 (10)	H23C—C23—H23B	109.5
C16—C15—C14	113.60 (11)	C4—C24—H24C	109.5
C17—C16—C15	112.21 (11)	C4—C24—H24B	109.5
C16—C17—C28	109.54 (13)	H24C—C24—H24B	109.5
C16—C17—C18	107.77 (10)	C4—C24—H24A	109.5
C28—C17—C18	115.07 (11)	H24C—C24—H24A	109.5
C16—C17—C21	116.94 (11)	H24B—C24—H24A	109.5
C28—C17—C21	109.01 (11)	C10—C25—H25C	109.5
C18—C17—C21	98.36 (11)	C10—C25—H25B	109.5
C19—C18—C13	120.14 (11)	H25C—C25—H25B	109.5
C19—C18—C17	104.13 (11)	C10—C25—H25A	109.5
C13—C18—C17	117.98 (11)	H25C—C25—H25A	109.5
C18—C19—C20	102.56 (12)	H25B—C25—H25A	109.5
C19—C20—C21	107.16 (12)	C13—C26—H26C	109.5
C22—C21—C20	112.19 (12)	C13—C26—H26B	109.5
C22—C21—C17	120.19 (12)	H26C—C26—H26B	109.5
C20—C21—C17	103.53 (11)	C13—C26—H26A	109.5
C30—C22—C29	109.14 (13)	H26C—C26—H26A	109.5
C30—C22—C21	113.42 (13)	H26B—C26—H26A	109.5
C29—C22—C21	109.97 (13)	C14—C27—H27B	109.5
C31—O1—C3	113.55 (11)	C14—C27—H27C	109.5
C2—C1—H1B	109.1	H27B—C27—H27C	109.5
C10—C1—H1B	109.1	C14—C27—H27A	109.5
C2—C1—H1A	109.1	H27B—C27—H27A	109.5
C10—C1—H1A	109.1	H27C—C27—H27A	109.5
H1B—C1—H1A	107.8	C17—C28—H28B	109.5
C3—C2—H2B	109.3	C17—C28—H28C	109.5
C1—C2—H2B	109.3	H28B—C28—H28C	109.5
C3—C2—H2A	109.3	C17—C28—H28A	109.5
C1—C2—H2A	109.3	H28B—C28—H28A	109.5
H2B—C2—H2A	108.0	H28C—C28—H28A	109.5
O1—C3—H3	108.6	C22—C29—H29A	109.5
C2—C3—H3	108.6	C22—C29—H29C	109.5
C4—C3—H3	108.6	H29A—C29—H29C	109.5
C6—C5—H5	105.1	C22—C29—H29B	109.5
C10—C5—H5	105.1	H29A—C29—H29B	109.5
C4—C5—H5	105.1	H29C—C29—H29B	109.5
C7—C6—H6B	109.6	C22—C30—H30B	109.5
C5—C6—H6B	109.6	C22—C30—H30C	109.5
C7—C6—H6A	109.6	H30B—C30—H30C	109.5
C5—C6—H6A	109.6	C22—C30—H30A	109.5
H6B—C6—H6A	108.2	H30B—C30—H30A	109.5
C6—C7—H7A	109.0	H30C—C30—H30A	109.5
C8—C7—H7A	109.0	O1—C31—H31B	109.5
C6—C7—H7B	109.0	O1—C31—H31A	109.5
C8—C7—H7B	109.0	H31B—C31—H31A	109.5
H7A—C7—H7B	107.8	O1—C31—H31C	109.5
C9—C8—H8	106.7	H31B—C31—H31C	109.5
C7—C8—H8	106.7	H31A—C31—H31C	109.5
C14—C8—H8	106.7
C10—C1—C2—C3	−59.20 (15)	C7—C8—C14—C27	50.92 (14)
C1—C2—C3—O1	−63.96 (15)	C9—C8—C14—C13	45.87 (13)
C1—C2—C3—C4	57.11 (16)	C7—C8—C14—C13	172.36 (11)
O1—C3—C4—C23	−47.33 (15)	C18—C13—C14—C15	53.03 (13)
C2—C3—C4—C23	−169.34 (12)	C12—C13—C14—C15	172.05 (11)
O1—C3—C4—C24	−163.22 (11)	C26—C13—C14—C15	−71.16 (13)
C2—C3—C4—C24	74.77 (15)	C18—C13—C14—C27	−66.11 (13)
O1—C3—C4—C5	71.40 (13)	C12—C13—C14—C27	52.92 (13)
C2—C3—C4—C5	−50.61 (14)	C26—C13—C14—C27	169.71 (11)
C23—C4—C5—C6	−63.07 (15)	C18—C13—C14—C8	174.21 (10)
C24—C4—C5—C6	56.44 (15)	C12—C13—C14—C8	−66.76 (12)
C3—C4—C5—C6	178.92 (11)	C26—C13—C14—C8	50.03 (13)
C23—C4—C5—C10	167.06 (12)	C27—C14—C15—C16	63.76 (14)
C24—C4—C5—C10	−73.43 (15)	C8—C14—C15—C16	−177.30 (10)
C3—C4—C5—C10	49.05 (15)	C13—C14—C15—C16	−57.58 (14)
C10—C5—C6—C7	−61.27 (14)	C14—C15—C16—C17	57.96 (15)
C4—C5—C6—C7	165.77 (11)	C15—C16—C17—C28	74.67 (14)
C5—C6—C7—C8	57.48 (15)	C15—C16—C17—C18	−51.19 (14)
C6—C7—C8—C9	−49.90 (16)	C15—C16—C17—C21	−160.71 (12)
C6—C7—C8—C14	−177.32 (11)	C12—C13—C18—C19	59.69 (16)
C7—C8—C9—C11	−137.79 (14)	C26—C13—C18—C19	−58.92 (17)
C14—C8—C9—C11	−10.25 (17)	C14—C13—C18—C19	176.68 (12)
C7—C8—C9—C10	48.41 (15)	C12—C13—C18—C17	−171.39 (11)
C14—C8—C9—C10	175.96 (10)	C26—C13—C18—C17	69.99 (15)
C2—C1—C10—C9	173.16 (10)	C14—C13—C18—C17	−54.41 (14)
C2—C1—C10—C25	−70.88 (14)	C16—C17—C18—C19	−171.12 (12)
C2—C1—C10—C5	53.79 (14)	C28—C17—C18—C19	66.36 (15)
C11—C9—C10—C1	15.03 (17)	C21—C17—C18—C19	−49.26 (12)
C8—C9—C10—C1	−171.26 (11)	C16—C17—C18—C13	52.82 (14)
C11—C9—C10—C25	−102.47 (15)	C28—C17—C18—C13	−69.71 (16)
C8—C9—C10—C25	71.24 (13)	C21—C17—C18—C13	174.68 (11)
C11—C9—C10—C5	134.32 (14)	C13—C18—C19—C20	171.98 (12)
C8—C9—C10—C5	−51.97 (14)	C17—C18—C19—C20	37.10 (15)
C6—C5—C10—C1	178.59 (11)	C18—C19—C20—C21	−10.02 (17)
C4—C5—C10—C1	−50.38 (14)	C19—C20—C21—C22	−151.34 (13)
C6—C5—C10—C9	57.09 (14)	C19—C20—C21—C17	−20.29 (16)
C4—C5—C10—C9	−171.88 (11)	C16—C17—C21—C22	−77.55 (16)
C6—C5—C10—C25	−60.60 (14)	C28—C17—C21—C22	47.34 (17)
C4—C5—C10—C25	70.43 (15)	C18—C17—C21—C22	167.58 (12)
C8—C9—C11—C12	−5.5 (2)	C16—C17—C21—C20	156.35 (12)
C10—C9—C11—C12	167.90 (13)	C28—C17—C21—C20	−78.77 (15)
C9—C11—C12—C13	−16.42 (19)	C18—C17—C21—C20	41.47 (13)
C11—C12—C13—C18	169.17 (11)	C20—C21—C22—C30	179.12 (14)
C11—C12—C13—C26	−69.12 (14)	C17—C21—C22—C30	57.15 (18)
C11—C12—C13—C14	51.23 (14)	C20—C21—C22—C29	−58.36 (16)
C9—C8—C14—C15	165.96 (10)	C17—C21—C22—C29	179.67 (13)
C7—C8—C14—C15	−67.56 (14)	C2—C3—O1—C31	−79.35 (14)
C9—C8—C14—C27	−75.56 (13)	C4—C3—O1—C31	157.01 (12)