6,7-cis-7,8-trans-3,3-Di­methyl-7-(5,5-di­methyl-3-oxo-1-cyclo­hexenyl)-6,8-di­phenyl-1,2,3,4,5,6,7,8-octa­hydro­naphthalen-1-one

An X-ray diffraction study has established the structure of the title compound, C₃₂H₃₆O₂, obtained from benz­aldehyde and isophorone under Claisen-Schmidt conditions.

Key indicators

• Single-crystal X-ray study
• T = 170 K
• Mean [sigma](C-C) = 0.004 Å
• H-atom completeness 100%
• R factor = 0.047
• wR factor = 0.139
• Data-to-parameter ratio = 14.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSMU_01  Alert C The ratio of given/expected absorption coefficient lies
          outside the range 0.99 <> 1.01
          Calculated value of mu =     0.072
          Value of mu given      =     0.073

PLAT_030  Alert C Refined Extinction parameter within range ....       3.00 Sigma

General Notes



FORMU_01  There is a discrepancy between the atom counts in the
          _chemical_formula_sum and the formula from the _atom_site* data.
          Atom count from _chemical_formula_sum:C32 H36 O2
          Atom count from the _atom_site data:  C32 H35.88600 O2.114

CELLZ_01
         From the CIF: _cell_formula_units_Z    4
         From the CIF: _chemical_formula_sum  C32 H36 O2
         TEST: Compare cell contents of formula and atom_site data

         atom    Z*formula  cif sites diff
         C        128.00    128.00    0.00
         H        144.00    143.54    0.46
         O          8.00      8.46   -0.46
          Difference between formula and atom_site contents detected.
          WARNING: H atoms missing from atom site list. Is this intentional?


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

S1. Comment

Two possible structures, including (Ia) without stereochemistry, were proposed for the high-melting condensation products formed in up to 59% yield from mixtures of isophorone, aromatic aldehydes, sodium hydroxide, and ethanol (Kabas, 1966). From its ¹H, HSQC, and HMBC NMR spectra, the benzaldehyde product was determined to have the constitution (Ia), but the stereochemistry remained in doubt. An X-ray study has firmly established structure (Ia), including the stereochemistry. The torsion angle between HC7 and HC8 is close to 90°, showing why coupling between these protons is not observed in the NMR spectra (given as supporting information). Compound (Ia) was proposed to be formed by a sequence involving two Michael additions, but a Diels–Alder reaction of benzylideneisophorone with itself to give (II) followed by base-catalysed double-bond isomerization to (Ia) seems more likely; precedent is found in the Diels–Alder reaction of benzylideneisophorone with maleic anhydride (Kabas, 1966). Difference maps revealed a small peak at a C–O distance [1.41 (2) Å] from C7, suggesting that 10% of the sample had air-oxidized to the alcohol (Ib).

S2. Experimental

Crystals suitable for structural determination were grown by slow evaporation from a deutero-chloroform solution of the compound.

S3. Refinement

Hydrogen atoms were added at idealized positions, constrained to ride on the atom to which they were bonded and given displacement parameters equal to 1.2 or 1.5 times U_iso of that bonded atom. Residual electron density (> 0.5 e^- per ų) was discovered in later difference maps, located approximately 1.4 Å from C7'and 0.4 Å from H7'A. As the distance was nearly an ideal alcoholic C–O bond length, the residual density was assigned to an oxygen atom, O3B. The neighboring proton (H7'A) and O3B were modeled as two parts of a disordered group, with the relative occupancies of the two parts allowed to refine. The final occupancies of the two parts were 88.566 (7)% for the proton and 11.434 (7)% for O3B. No protons were modeled for O3B. The resultant difference map was greatly improved.

Computing details

Data collection: SMART (Bruker, 1997a); cell refinement: SMART; data reduction: SAINT (Bruker, 1997a); program(s) used to solve structure: SHELXTL (Bruker, 1997b); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. Displacement ellipsoid plot rendered with 50% probability ellipsoids (Bruker, 1997).

(I)

Crystal data

C32H36O2	F(000) = 976
Mr = 452.61	Dx = 1.193 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.2381 (9) Å	Cell parameters from 4886 reflections
b = 21.8866 (15) Å	θ = 2.4–22.4°
c = 10.3089 (7) Å	µ = 0.07 mm^−1
β = 113.690 (1)°	T = 170 K
V = 2528.6 (3) Å^3	Block, colorless
Z = 4	0.3 × 0.15 × 0.1 mm

Data collection

CCD area-detector diffractometer	2142 reflections with I > \2s(I)
Radiation source: fine-focus sealed tube	Rint = 0.099
Graphite monochromator	θmax = 25.1°, θmin = 1.8°
ψ and ω scans	h = −14→14
23714 measured reflections	k = −26→26
4484 independent reflections	l = −12→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.0575P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.94	(Δ/σ)max < 0.001
4484 reflections	Δρmax = 0.25 e Å^−3
313 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0024 (8)

Special details

Experimental. NMR shifts (δ) and coupling constants (J, in Hz) of (Ia) in CDCl3 at 600 MHz

# 13 C 1H # 13 C 1H 1 200.3 - 1' 198.0 - 2 126.0 5.68 2' 131.7 - 3 164.2 - 3' 155.8 - 4 46.7 1.42,1.89 4' 46.0 2.40,2.50 5 33.0 - 5' 33.5 - 6 51.0 2.04,2.11 6' 52.1 2.32,2.36 7 55.3 2.71 7' 33.2 2.54,2.78 8 43.9 4.17 8' 36.2 3.37 9 145.0 - 9' 141.8 - 10 128.2 7.20 10' 128.0 6.98 11 128.7 7.31 11' 128.6 7.22 12 126.7 7.22 12' 127.0 7.17 15 28.0 0.71 15' 27.9 1.12 16 28.5 0.86 16' 29.5 1.16

J_4,4 = 18.5 J_4',4' = 18.0 J_6,6 = 16.0 J_6',6' = 15.5 J_7,8 = 0 J_7',7' = 19.5 J_7,8' = 3.5 J_7',8' = 5.0,12.0

A parameter describing extinction was included and refined to a final value of x = 0.0024 (8).

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.36245 (17)	0.74468 (9)	0.8237 (2)	0.0321 (5)
C9'	0.3943 (2)	1.03903 (12)	0.7511 (3)	0.0228 (7)
C3'	0.2773 (2)	0.89476 (12)	0.8749 (3)	0.0222 (7)
C4'	0.2047 (2)	0.88207 (12)	0.9595 (3)	0.0255 (7)
H4'A	0.1368	0.9110	0.9294	0.031*
H4'B	0.2548	0.8902	1.0606	0.031*
C5'	0.1556 (2)	0.81676 (12)	0.9458 (3)	0.0255 (7)
C11'	0.5107 (3)	1.11842 (13)	0.7029 (3)	0.0335 (8)
H11'	0.5833	1.1313	0.6986	0.040*
C2'	0.3297 (2)	0.85019 (12)	0.8292 (3)	0.0221 (7)
C7'	0.2868 (3)	0.96076 (12)	0.8406 (3)	0.0260 (7)
H7'A	0.3015	0.9857	0.9261	0.031*	0.886 (7)
H7'B	0.2099	0.9740	0.7661	0.031*
O3	0.2961 (16)	0.9985 (8)	0.9559 (19)	0.045 (9)*	0.114 (7)
C14'	0.3014 (3)	1.08048 (12)	0.7167 (3)	0.0279 (7)
H14'	0.2287	1.0681	0.7214	0.034*
C16'	0.1088 (3)	0.80508 (13)	1.0600 (3)	0.0344 (8)
H116	0.0778	0.7633	1.0508	0.052*
H216	0.0448	0.8341	1.0490	0.052*
H316	0.1738	0.8103	1.1536	0.052*
C8'	0.3856 (2)	0.97276 (12)	0.7902 (3)	0.0232 (7)
H8'	0.4624	0.9630	0.8717	0.028*
C1'	0.3195 (2)	0.78592 (13)	0.8677 (3)	0.0243 (7)
C12'	0.4166 (3)	1.15853 (13)	0.6680 (3)	0.0324 (8)
H12'	0.4235	1.1990	0.6388	0.039*
C13'	0.3126 (3)	1.13940 (13)	0.6759 (3)	0.0326 (8)
H13'	0.2476	1.1670	0.6530	0.039*
C6'	0.2590 (2)	0.77349 (12)	0.9658 (3)	0.0287 (7)
H6'A	0.3187	0.7768	1.0647	0.034*
H6'B	0.2286	0.7310	0.9508	0.034*
C15'	0.0536 (3)	0.80706 (13)	0.8006 (3)	0.0329 (8)
H115	0.0240	0.7651	0.7937	0.049*
H215	0.0827	0.8143	0.7261	0.049*
H315	−0.0113	0.8357	0.7890	0.049*
C10'	0.5000 (3)	1.05912 (13)	0.7445 (3)	0.0302 (7)
H10'	0.5657	1.0319	0.7689	0.036*
C5	0.1482 (3)	1.00026 (13)	0.3157 (3)	0.0312 (8)
C10	0.5730 (3)	0.82195 (13)	0.7023 (3)	0.0306 (8)
H10A	0.5250	0.8195	0.6036	0.037*
C11	0.6916 (3)	0.80428 (13)	0.7532 (4)	0.0388 (8)
H11A	0.7244	0.7896	0.6897	0.047*
C15	0.1685 (3)	1.03352 (15)	0.1968 (3)	0.0446 (9)
H15A	0.0915	1.0466	0.1245	0.067*
H15B	0.2078	1.0059	0.1541	0.067*
H15C	0.2191	1.0694	0.2356	0.067*
C6	0.0726 (3)	0.94340 (13)	0.2578 (3)	0.0347 (8)
H6A	−0.0083	0.9562	0.1919	0.042*
H6B	0.1080	0.9195	0.2028	0.042*
C12	0.7617 (3)	0.80811 (14)	0.8955 (4)	0.0406 (9)
H12A	0.8428	0.7956	0.9307	0.049*
C16	0.0861 (3)	1.04352 (13)	0.3814 (3)	0.0395 (9)
H16A	0.0714	1.0221	0.4563	0.059*
H16B	0.0100	1.0571	0.3082	0.059*
H16C	0.1372	1.0791	0.4218	0.059*
C13	0.7150 (3)	0.82991 (14)	0.9869 (4)	0.0390 (9)
H13A	0.7642	0.8330	1.0851	0.047*
C1	0.0618 (3)	0.90298 (14)	0.3694 (3)	0.0327 (8)
C2	0.1644 (2)	0.90066 (13)	0.5062 (3)	0.0284 (7)
H2A	0.1613	0.8738	0.5771	0.034*
C7	0.3747 (2)	0.92708 (12)	0.6696 (3)	0.0227 (7)
H7A	0.4435	0.9354	0.6434	0.027*
C9	0.5233 (2)	0.84313 (12)	0.7937 (3)	0.0239 (7)
C8	0.3922 (2)	0.86107 (11)	0.7313 (3)	0.0208 (7)
H8A	0.3524	0.8334	0.6484	0.025*
C14	0.5957 (3)	0.84752 (13)	0.9367 (3)	0.0308 (8)
H14A	0.5639	0.8626	1.0007	0.037*
C3	0.2624 (2)	0.93474 (12)	0.5356 (3)	0.0228 (7)
C4	0.2692 (2)	0.97973 (13)	0.4287 (3)	0.0278 (7)
H4A	0.3164	0.9612	0.3803	0.033*
H4B	0.3129	1.0164	0.4799	0.033*
O0	−0.02593 (19)	0.87050 (10)	0.3461 (2)	0.0470 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0348 (13)	0.0235 (12)	0.0395 (13)	0.0032 (10)	0.0166 (11)	−0.0008 (10)
C9'	0.0243 (17)	0.0183 (16)	0.0221 (16)	−0.0038 (13)	0.0053 (13)	−0.0033 (13)
C3'	0.0208 (16)	0.0221 (16)	0.0202 (16)	−0.0003 (13)	0.0047 (13)	0.0002 (13)
C4'	0.0290 (17)	0.0205 (17)	0.0259 (17)	0.0018 (13)	0.0100 (14)	0.0001 (13)
C5'	0.0270 (17)	0.0201 (16)	0.0293 (18)	0.0024 (13)	0.0111 (15)	0.0033 (13)
C11'	0.0305 (19)	0.0321 (19)	0.038 (2)	−0.0044 (15)	0.0142 (16)	0.0052 (16)
C2'	0.0225 (16)	0.0216 (16)	0.0194 (16)	−0.0024 (13)	0.0056 (13)	0.0001 (13)
C7'	0.0334 (18)	0.0190 (16)	0.0256 (17)	−0.0017 (13)	0.0117 (14)	−0.0021 (13)
C14'	0.0296 (18)	0.0219 (17)	0.0312 (18)	−0.0015 (14)	0.0110 (15)	−0.0037 (14)
C16'	0.0373 (19)	0.0293 (18)	0.041 (2)	0.0029 (15)	0.0202 (17)	0.0032 (15)
C8'	0.0218 (16)	0.0204 (16)	0.0257 (17)	0.0010 (13)	0.0077 (14)	−0.0013 (13)
C1'	0.0215 (16)	0.0209 (17)	0.0246 (18)	0.0027 (13)	0.0030 (14)	−0.0013 (13)
C12'	0.039 (2)	0.0209 (17)	0.0354 (19)	−0.0047 (15)	0.0127 (16)	0.0011 (14)
C13'	0.0320 (19)	0.0234 (18)	0.042 (2)	0.0017 (14)	0.0140 (16)	−0.0032 (15)
C6'	0.0298 (18)	0.0221 (17)	0.0344 (19)	0.0013 (14)	0.0131 (15)	0.0034 (14)
C15'	0.0340 (19)	0.0279 (18)	0.0353 (19)	0.0000 (14)	0.0123 (16)	0.0003 (15)
C10'	0.0262 (18)	0.0273 (18)	0.0356 (19)	−0.0009 (14)	0.0107 (15)	0.0029 (15)
C5	0.0352 (19)	0.0284 (17)	0.0242 (18)	0.0029 (15)	0.0058 (15)	0.0017 (14)
C10	0.0301 (19)	0.0290 (18)	0.0355 (19)	0.0046 (15)	0.0160 (16)	−0.0004 (15)
C11	0.036 (2)	0.033 (2)	0.055 (2)	0.0050 (16)	0.0262 (19)	0.0036 (17)
C15	0.052 (2)	0.041 (2)	0.034 (2)	0.0020 (17)	0.0108 (17)	0.0108 (17)
C6	0.0350 (19)	0.037 (2)	0.0252 (18)	0.0028 (15)	0.0045 (15)	0.0011 (15)
C12	0.0264 (19)	0.033 (2)	0.061 (3)	0.0031 (15)	0.0154 (19)	0.0065 (18)
C16	0.040 (2)	0.0335 (19)	0.037 (2)	0.0122 (16)	0.0071 (16)	0.0037 (16)
C13	0.032 (2)	0.039 (2)	0.037 (2)	0.0006 (16)	0.0055 (17)	0.0035 (16)
C1	0.0290 (19)	0.0297 (18)	0.035 (2)	0.0009 (15)	0.0077 (16)	−0.0038 (15)
C2	0.0282 (18)	0.0258 (17)	0.0276 (18)	0.0030 (14)	0.0074 (15)	0.0053 (14)
C7	0.0233 (16)	0.0190 (15)	0.0252 (17)	0.0012 (13)	0.0090 (14)	0.0019 (13)
C9	0.0268 (17)	0.0165 (15)	0.0285 (18)	0.0026 (13)	0.0111 (15)	0.0030 (13)
C8	0.0246 (16)	0.0162 (15)	0.0212 (16)	0.0013 (12)	0.0086 (14)	0.0000 (12)
C14	0.0285 (18)	0.0331 (19)	0.0288 (18)	0.0002 (15)	0.0092 (15)	−0.0008 (15)
C3	0.0249 (17)	0.0197 (16)	0.0229 (16)	0.0046 (13)	0.0088 (14)	−0.0016 (13)
C4	0.0366 (19)	0.0250 (17)	0.0243 (17)	0.0024 (14)	0.0151 (15)	0.0034 (13)
O0	0.0306 (13)	0.0506 (15)	0.0501 (15)	−0.0087 (12)	0.0059 (12)	−0.0009 (12)

Geometric parameters (Å, º)

O1—C1'	1.220 (3)	C10'—H10'	0.9500
C9'—C14'	1.384 (4)	C5—C6	1.522 (4)
C9'—C10'	1.393 (4)	C5—C15	1.530 (4)
C9'—C8'	1.520 (4)	C5—C16	1.531 (4)
C3'—C2'	1.351 (4)	C5—C4	1.538 (4)
C3'—C4'	1.500 (4)	C10—C11	1.386 (4)
C3'—C7'	1.503 (4)	C10—C9	1.390 (4)
C4'—C5'	1.535 (3)	C10—H10A	0.9500
C4'—H4'A	0.9900	C11—C12	1.373 (4)
C4'—H4'B	0.9900	C11—H11A	0.9500
C5'—C16'	1.524 (4)	C15—H15A	0.9800
C5'—C6'	1.527 (4)	C15—H15B	0.9800
C5'—C15'	1.531 (4)	C15—H15C	0.9800
C11'—C12'	1.377 (4)	C6—C1	1.499 (4)
C11'—C10'	1.390 (4)	C6—H6A	0.9900
C11'—H11'	0.9500	C6—H6B	0.9900
C2'—C1'	1.480 (4)	C12—C13	1.370 (4)
C2'—C8	1.510 (3)	C12—H12A	0.9500
C7'—O3	1.414 (18)	C16—H16A	0.9800
C7'—C8'	1.518 (4)	C16—H16B	0.9800
C7'—H7'A	0.9900	C16—H16C	0.9800
C7'—H7'B	0.9900	C13—C14	1.392 (4)
C14'—C13'	1.380 (4)	C13—H13A	0.9500
C14'—H14'	0.9500	C1—O0	1.228 (3)
C16'—H116	0.9800	C1—C2	1.464 (4)
C16'—H216	0.9800	C2—C3	1.340 (4)
C16'—H316	0.9800	C2—H2A	0.9500
C8'—C7	1.558 (4)	C7—C3	1.516 (4)
C8'—H8'	1.0000	C7—C8	1.558 (3)
C1'—C6'	1.498 (4)	C7—H7A	1.0000
C12'—C13'	1.373 (4)	C9—C14	1.385 (4)
C12'—H12'	0.9500	C9—C8	1.522 (4)
C13'—H13'	0.9500	C8—H8A	1.0000
C6'—H6'A	0.9900	C14—H14A	0.9500
C6'—H6'B	0.9900	C3—C4	1.505 (4)
C15'—H115	0.9800	C4—H4A	0.9900
C15'—H215	0.9800	C4—H4B	0.9900
C15'—H315	0.9800
C14'—C9'—C10'	117.6 (3)	C11'—C10'—H10'	119.5
C14'—C9'—C8'	123.8 (2)	C9'—C10'—H10'	119.5
C10'—C9'—C8'	118.6 (2)	C6—C5—C15	110.1 (2)
C2'—C3'—C4'	122.9 (2)	C6—C5—C16	110.4 (3)
C2'—C3'—C7'	121.3 (3)	C15—C5—C16	109.2 (2)
C4'—C3'—C7'	115.8 (2)	C6—C5—C4	107.9 (2)
C3'—C4'—C5'	114.8 (2)	C15—C5—C4	109.2 (2)
C3'—C4'—H4'A	108.6	C16—C5—C4	110.1 (2)
C5'—C4'—H4'A	108.6	C11—C10—C9	120.9 (3)
C3'—C4'—H4'B	108.6	C11—C10—H10A	119.5
C5'—C4'—H4'B	108.6	C9—C10—H10A	119.5
H4'A—C4'—H4'B	107.5	C12—C11—C10	119.8 (3)
C16'—C5'—C6'	109.9 (2)	C12—C11—H11A	120.1
C16'—C5'—C15'	108.7 (2)	C10—C11—H11A	120.1
C6'—C5'—C15'	110.6 (2)	C5—C15—H15A	109.5
C16'—C5'—C4'	109.9 (2)	C5—C15—H15B	109.5
C6'—C5'—C4'	107.0 (2)	H15A—C15—H15B	109.5
C15'—C5'—C4'	110.8 (2)	C5—C15—H15C	109.5
C12'—C11'—C10'	120.2 (3)	H15A—C15—H15C	109.5
C12'—C11'—H11'	119.9	H15B—C15—H15C	109.5
C10'—C11'—H11'	119.9	C1—C6—C5	114.1 (2)
C3'—C2'—C1'	119.4 (2)	C1—C6—H6A	108.7
C3'—C2'—C8	123.9 (2)	C5—C6—H6A	108.7
C1'—C2'—C8	116.6 (2)	C1—C6—H6B	108.7
O3—C7'—C3'	110.5 (8)	C5—C6—H6B	108.7
O3—C7'—C8'	112.4 (8)	H6A—C6—H6B	107.6
C3'—C7'—C8'	113.3 (2)	C13—C12—C11	120.2 (3)
O3—C7'—H7'A	5.7	C13—C12—H12A	119.9
C3'—C7'—H7'A	108.9	C11—C12—H12A	119.9
C8'—C7'—H7'A	108.9	C5—C16—H16A	109.5
O3—C7'—H7'B	102.2	C5—C16—H16B	109.5
C3'—C7'—H7'B	108.9	H16A—C16—H16B	109.5
C8'—C7'—H7'B	108.9	C5—C16—H16C	109.5
H7'A—C7'—H7'B	107.7	H16A—C16—H16C	109.5
C13'—C14'—C9'	121.2 (3)	H16B—C16—H16C	109.5
C13'—C14'—H14'	119.4	C12—C13—C14	120.4 (3)
C9'—C14'—H14'	119.4	C12—C13—H13A	119.8
C5'—C16'—H116	109.5	C14—C13—H13A	119.8
C5'—C16'—H216	109.5	O0—C1—C2	120.8 (3)
H116—C16'—H216	109.5	O0—C1—C6	122.1 (3)
C5'—C16'—H316	109.5	C2—C1—C6	117.0 (3)
H116—C16'—H316	109.5	C3—C2—C1	122.8 (3)
H216—C16'—H316	109.5	C3—C2—H2A	118.6
C7'—C8'—C9'	113.9 (2)	C1—C2—H2A	118.6
C7'—C8'—C7	109.7 (2)	C3—C7—C8'	114.3 (2)
C9'—C8'—C7	113.2 (2)	C3—C7—C8	113.6 (2)
C7'—C8'—H8'	106.5	C8'—C7—C8	108.4 (2)
C9'—C8'—H8'	106.5	C3—C7—H7A	106.7
C7—C8'—H8'	106.5	C8'—C7—H7A	106.7
O1—C1'—C2'	120.6 (3)	C8—C7—H7A	106.7
O1—C1'—C6'	121.3 (2)	C14—C9—C10	118.5 (3)
C2'—C1'—C6'	118.1 (2)	C14—C9—C8	123.1 (3)
C13'—C12'—C11'	119.2 (3)	C10—C9—C8	118.3 (2)
C13'—C12'—H12'	120.4	C2'—C8—C9	114.1 (2)
C11'—C12'—H12'	120.4	C2'—C8—C7	113.3 (2)
C12'—C13'—C14'	120.7 (3)	C9—C8—C7	111.1 (2)
C12'—C13'—H13'	119.6	C2'—C8—H8A	105.8
C14'—C13'—H13'	119.6	C9—C8—H8A	105.8
C1'—C6'—C5'	113.8 (2)	C7—C8—H8A	105.8
C1'—C6'—H6'A	108.8	C9—C14—C13	120.2 (3)
C5'—C6'—H6'A	108.8	C9—C14—H14A	119.9
C1'—C6'—H6'B	108.8	C13—C14—H14A	119.9
C5'—C6'—H6'B	108.8	C2—C3—C4	120.4 (3)
H6'A—C6'—H6'B	107.7	C2—C3—C7	123.1 (3)
C5'—C15'—H115	109.5	C4—C3—C7	116.3 (2)
C5'—C15'—H215	109.5	C3—C4—C5	115.2 (2)
H115—C15'—H215	109.5	C3—C4—H4A	108.5
C5'—C15'—H315	109.5	C5—C4—H4A	108.5
H115—C15'—H315	109.5	C3—C4—H4B	108.5
H215—C15'—H315	109.5	C5—C4—H4B	108.5
C11'—C10'—C9'	121.0 (3)	H4A—C4—H4B	107.5
C2'—C3'—C4'—C5'	−21.3 (4)	C16—C5—C6—C1	−67.4 (3)
C7'—C3'—C4'—C5'	157.6 (2)	C4—C5—C6—C1	52.9 (3)
C3'—C4'—C5'—C16'	167.1 (2)	C10—C11—C12—C13	−0.7 (5)
C3'—C4'—C5'—C6'	47.9 (3)	C11—C12—C13—C14	0.9 (5)
C3'—C4'—C5'—C15'	−72.8 (3)	C5—C6—C1—O0	151.3 (3)
C4'—C3'—C2'—C1'	−2.2 (4)	C5—C6—C1—C2	−32.6 (4)
C7'—C3'—C2'—C1'	179.0 (2)	O0—C1—C2—C3	179.2 (3)
C4'—C3'—C2'—C8	173.4 (2)	C6—C1—C2—C3	3.1 (4)
C7'—C3'—C2'—C8	−5.4 (4)	C7'—C8'—C7—C3	65.0 (3)
C2'—C3'—C7'—O3	−143.5 (8)	C9'—C8'—C7—C3	−63.4 (3)
C4'—C3'—C7'—O3	37.6 (8)	C7'—C8'—C7—C8	−62.8 (3)
C2'—C3'—C7'—C8'	−16.3 (4)	C9'—C8'—C7—C8	168.8 (2)
C4'—C3'—C7'—C8'	164.8 (2)	C11—C10—C9—C14	1.4 (4)
C10'—C9'—C14'—C13'	0.7 (4)	C11—C10—C9—C8	−179.3 (3)
C8'—C9'—C14'—C13'	−177.1 (3)	C3'—C2'—C8—C9	120.0 (3)
O3—C7'—C8'—C9'	−55.5 (8)	C1'—C2'—C8—C9	−64.3 (3)
C3'—C7'—C8'—C9'	178.4 (2)	C3'—C2'—C8—C7	−8.5 (4)
O3—C7'—C8'—C7	176.5 (8)	C1'—C2'—C8—C7	167.2 (2)
C3'—C7'—C8'—C7	50.4 (3)	C14—C9—C8—C2'	−32.4 (4)
C14'—C9'—C8'—C7'	−21.1 (4)	C10—C9—C8—C2'	148.3 (2)
C10'—C9'—C8'—C7'	161.1 (2)	C14—C9—C8—C7	97.2 (3)
C14'—C9'—C8'—C7	105.1 (3)	C10—C9—C8—C7	−82.1 (3)
C10'—C9'—C8'—C7	−72.7 (3)	C3—C7—C8—C2'	−86.7 (3)
C3'—C2'—C1'—O1	177.4 (3)	C8'—C7—C8—C2'	41.5 (3)
C8—C2'—C1'—O1	1.5 (4)	C3—C7—C8—C9	143.3 (2)
C3'—C2'—C1'—C6'	−4.7 (4)	C8'—C7—C8—C9	−88.5 (3)
C8—C2'—C1'—C6'	179.4 (2)	C10—C9—C14—C13	−1.1 (4)
C10'—C11'—C12'—C13'	0.5 (5)	C8—C9—C14—C13	179.5 (3)
C11'—C12'—C13'—C14'	−0.7 (5)	C12—C13—C14—C9	0.0 (4)
C9'—C14'—C13'—C12'	0.1 (4)	C1—C2—C3—C4	2.5 (4)
O1—C1'—C6'—C5'	−147.1 (3)	C1—C2—C3—C7	−172.2 (3)
C2'—C1'—C6'—C5'	35.0 (3)	C8'—C7—C3—C2	−97.2 (3)
C16'—C5'—C6'—C1'	−173.9 (2)	C8—C7—C3—C2	27.9 (4)
C15'—C5'—C6'—C1'	66.1 (3)	C8'—C7—C3—C4	87.9 (3)
C4'—C5'—C6'—C1'	−54.6 (3)	C8—C7—C3—C4	−147.0 (2)
C12'—C11'—C10'—C9'	0.3 (4)	C2—C3—C4—C5	21.3 (4)
C14'—C9'—C10'—C11'	−0.9 (4)	C7—C3—C4—C5	−163.6 (2)
C8'—C9'—C10'—C11'	177.0 (3)	C6—C5—C4—C3	−47.5 (3)
C9—C10—C11—C12	−0.5 (4)	C15—C5—C4—C3	−167.1 (2)
C15—C5—C6—C1	172.0 (2)	C16—C5—C4—C3	73.0 (3)