Cinnamolid-3β-ol hemihydrate and 3β-hydroxycinnamolide acetate, two drimanolide-class sesquiterpene lactones from Warburgia ugandensis

3β-Hydr­oxy-7-drimen-12,11-olide hemihydrate, C₁₅H₂₂O₃·0.5H₂O, (I), has two sesquiterpene mol­ecules and one water mol­ecule in the asymmetric unit. The OH groups of both mol­ecules and both H atoms of the water mol­ecule are involved in near-linear inter­molecular hydrogen bonds, having O...O distances in the range 2.632 (3)–2.791 (2) Å. 3β-Acet­oxy-7-drimen-12,11-olide, C₁₇H₂₄O₄, (II), has its ring system in very nearly the same conformation as the two mol­ecules of (I).

S1. Comment

Plants of the genus Warburgia are of interest because of their use by herbalists in Kenya for the treatment of a number of parasitic diseases (Kokwaro, 1976). Isolation of drimanolide-class sesquiterpenes (I) and (II) from the stem bark of Warburgia ugandensis Sprague (Canellaceae) has been described by Kioy et al. (1990). The molecular structures of 3β-hydroxy-7-drimen-12,11-olide hemihydrate, (I), and 3β-acetoxy-7-drimen-12,11-olide, (II), were determined in order to ascertain unambiguously the relative stereochemistry of the 3-OH and 3-OAc groups, respectively, as well as to confirm the relative configurations of the other asymmetric centers.

One of the two independent molecules of (I) is shown in Fig. 1. The OH group at C3 is seen to be β-oriented, and the configurations at the other chiral centers are confirmed to be those reported by Kioy et al. (1990). The conformations of the two independent molecules are nearly identical, with maximum deviation in an endocyclic torsion angle of 2.5 (6)°, about the double bond C7═C8. The OH-carrying A ring has a chair conformation, the central B ring a half-chair conformation, and the lactone ring a C₂ half-chair conformation, with the axis passing through C12 and bisecting C9—C11. The most notable difference in the conformations of the two molecules involves the OH group, in which the O—H bond is roughly parallel to C10—C15 in the A molecule and roughly antiparallel in the B molecule, in accordance with the hydrogen-bonding scheme. The OH group of the A molecule donates a hydrogen bond to the water molecule, while the OH of the B molecule instead donates to the OH group of the A molecule. The lactone carbonyl atom O2 of the A molecule accepts a hydrogen bond (from water), but that of the B molecule is not involved in hydrogen bonding. The acceptor for the second hydrogen bond donated by water is the OH group of the B molecule.

Compound (II) is shown in Fig. 2, and the configurations at all the chiral centers are seen to be the same as those of (I). The conformation of the ring system also agrees well with that of (I): the largest individual difference between an endocyclic torsion angle in (II) and the corresponding average value in (I) is 4.1 (5)°, for C7—C8—C9—C10. The conformations of the ring system in both title compounds agree fairly well with those of two molecules also having the drimanolide skeleton, insulicolide A (Rahbaek et al., 1997) and iresin dibromobenzoate (Rossman & Lipscomb, 1958). The cell dimensions of (II) at room temperature (299 K), measured on a Nonius CAD-4 diffractometer using Cu Kα radiation, are a = 6.8885 (6), b = 7.9753 (8) and c = 14.411 (2) Å, and β = 101.613 (7)°.

S2. Experimental

Compounds (I) and (II) were isolated from the stem bark of Warburgia ugandensis Sprague (Canellaceae) collected in Eldoret, Uasin Gishu District, Kenya. [Please give brief details of preparative procedure, or an appropriate reference] Crystals were grown from a solution in acetone–hexane (Ratio?).

S3. Refinement

H atoms were placed in calculated positions, guided by difference maps, with C—H bond distances in the range 0.95–1.00 Å and with U_iso(H) = 1.2U_eq(C), or 1.5U_eq(C) for methyl H, and thereafter treated as riding. Coordinates for OH H atoms were refined. A torsional parameter was refined for each OH group and each methyl group. The absolute configuration could not be established from the X-ray data, but was assigned based on the configuration of insulicolide A (Rahbaek et al., 1997). Friedel pairs were averaged.

Computing details

For both compounds, data collection: COLLECT (Nonius, 1999); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. One of the two independent molecules (molecule A) in (I), showing the atom-numbering scheme and with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A view of the acetate, (II), showing the atom-numbering scheme and with displacement ellipsoids drawn at the 50% probability level.

(I) 3β-Hydroxy-7-drimen-12,11-olide hemihydrate

Crystal data

C15H22O3·0.5H2O	F(000) = 564
Mr = 259.33	Dx = 1.238 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4619 reflections
a = 12.875 (3) Å	θ = 2.5–32.0°
b = 6.153 (2) Å	µ = 0.09 mm^−1
c = 18.268 (4) Å	T = 120 K
β = 106.031 (16)°	Prism, colorless
V = 1390.9 (6) Å^3	0.42 × 0.35 × 0.20 mm
Z = 4

Data collection

Nonius KappaCCD area-detector (with Oxford Cryostream) diffractometer	3773 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
Graphite monochromator	θmax = 32.0°, θmin = 3.1°
ω scans with κ offsets	h = −19→19
17077 measured reflections	k = −8→9
5214 independent reflections	l = −27→26

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0505P)^2 + 0.0592P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.003
5214 reflections	Δρmax = 0.38 e Å^−3
353 parameters	Δρmin = −0.23 e Å^−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.007 (2)

Special details

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
O1A	0.53239 (11)	0.8344 (3)	1.01792 (8)	0.0299 (3)
O2A	0.37960 (12)	0.8405 (3)	0.92329 (10)	0.0392 (4)
O3A	1.01372 (13)	0.5682 (3)	0.83070 (10)	0.0361 (4)
H3OA	1.055 (2)	0.678 (6)	0.8468 (16)	0.054*
C1A	0.86114 (14)	0.7138 (4)	0.97246 (10)	0.0210 (4)
H1A1	0.8824	0.7966	1.0208	0.025*
H1A2	0.8478	0.5615	0.9849	0.025*
C2A	0.95405 (15)	0.7185 (4)	0.93584 (10)	0.0240 (4)
H2A1	0.9713	0.8709	0.9263	0.029*
H2A2	1.0191	0.6522	0.9708	0.029*
C3A	0.92312 (16)	0.5942 (4)	0.86133 (11)	0.0244 (4)
H3A	0.9013	0.4451	0.8731	0.029*
C4A	0.82503 (16)	0.6933 (4)	0.80198 (10)	0.0234 (4)
C5A	0.73066 (15)	0.7079 (3)	0.83992 (9)	0.0194 (4)
H5A	0.7119	0.5532	0.8472	0.023*
C6A	0.62630 (16)	0.8045 (4)	0.78670 (10)	0.0302 (5)
H6A1	0.6426	0.9493	0.7690	0.036*
H6A2	0.6013	0.7098	0.7414	0.036*
C7A	0.53695 (16)	0.8271 (4)	0.82450 (11)	0.0289 (5)
H7A	0.4669	0.8688	0.7949	0.035*
C8A	0.55391 (15)	0.7902 (3)	0.89770 (11)	0.0232 (4)
C9A	0.66147 (14)	0.7336 (3)	0.95175 (9)	0.0187 (4)
H9A	0.6657	0.5718	0.9570	0.022*
C10A	0.75600 (14)	0.8099 (3)	0.92124 (9)	0.0166 (4)
C11A	0.64940 (15)	0.8286 (4)	1.02673 (10)	0.0245 (4)
H11A	0.6864	0.7355	1.0704	0.029*
H11B	0.6805	0.9766	1.0352	0.029*
C12A	0.47787 (17)	0.8244 (4)	0.94392 (12)	0.0288 (5)
C13A	0.7910 (2)	0.5376 (4)	0.73353 (12)	0.0361 (6)
H13A	0.7321	0.6032	0.6938	0.054*
H13B	0.7665	0.3998	0.7499	0.054*
H13C	0.8528	0.5108	0.7133	0.054*
C14A	0.85720 (19)	0.9103 (4)	0.77220 (12)	0.0296 (5)
H14A	0.8874	1.0079	0.8152	0.044*
H14B	0.7932	0.9777	0.7377	0.044*
H14C	0.9114	0.8834	0.7447	0.044*
C15A	0.76189 (16)	1.0592 (4)	0.92026 (11)	0.0231 (4)
H15A	0.7790	1.1144	0.9726	0.035*
H15B	0.6921	1.1179	0.8908	0.035*
H15C	0.8183	1.1044	0.8968	0.035*
O1B	0.46672 (11)	0.6360 (3)	0.50293 (8)	0.0286 (4)
O2B	0.37074 (12)	0.5687 (4)	0.38312 (7)	0.0379 (4)
O3B	0.10653 (15)	0.2489 (3)	0.77540 (9)	0.0374 (4)
H3OB	0.072 (2)	0.334 (6)	0.7943 (15)	0.056*
C1B	0.33611 (17)	0.4662 (4)	0.70622 (10)	0.0244 (4)
H1B1	0.4152	0.4571	0.7290	0.029*
H1B2	0.3157	0.6218	0.7035	0.029*
C2B	0.27970 (17)	0.3486 (4)	0.75802 (10)	0.0284 (5)
H2B1	0.3049	0.1960	0.7649	0.034*
H2B2	0.2987	0.4194	0.8087	0.034*
C3B	0.15803 (17)	0.3530 (4)	0.72424 (11)	0.0275 (5)
H3B	0.1345	0.5085	0.7190	0.033*
C4B	0.11959 (17)	0.2460 (4)	0.64484 (12)	0.0251 (4)
C5B	0.18268 (15)	0.3543 (4)	0.59266 (10)	0.0210 (4)
H5B	0.1565	0.5080	0.5867	0.025*
C6B	0.15093 (16)	0.2614 (4)	0.51106 (11)	0.0291 (5)
H6B1	0.1602	0.1016	0.5138	0.035*
H6B2	0.0735	0.2920	0.4871	0.035*
C7B	0.21586 (16)	0.3525 (4)	0.46151 (10)	0.0282 (5)
H7B	0.1958	0.3193	0.4087	0.034*
C8B	0.30057 (16)	0.4783 (4)	0.49016 (10)	0.0232 (4)
C9B	0.34082 (15)	0.5409 (3)	0.57263 (10)	0.0203 (4)
H9B	0.3067	0.6828	0.5793	0.024*
C10B	0.30801 (15)	0.3729 (3)	0.62499 (10)	0.0190 (4)
C11B	0.46115 (16)	0.5840 (4)	0.58015 (10)	0.0261 (5)
H11C	0.4880	0.7071	0.6151	0.031*
H11D	0.5051	0.4537	0.5999	0.031*
C12B	0.37772 (17)	0.5612 (4)	0.45014 (11)	0.0270 (4)
C13B	−0.00170 (16)	0.2957 (4)	0.61230 (13)	0.0352 (5)
H13D	−0.0408	0.2464	0.6483	0.053*
H13E	−0.0296	0.2198	0.5637	0.053*
H13F	−0.0119	0.4526	0.6043	0.053*
C14B	0.13066 (18)	−0.0031 (4)	0.65216 (13)	0.0293 (5)
H14D	0.2029	−0.0402	0.6843	0.044*
H14E	0.1201	−0.0673	0.6015	0.044*
H14F	0.0760	−0.0601	0.6753	0.044*
C15B	0.36673 (16)	0.1566 (3)	0.62423 (12)	0.0249 (4)
H15D	0.4443	0.1764	0.6478	0.037*
H15E	0.3549	0.1076	0.5715	0.037*
H15F	0.3385	0.0475	0.6528	0.037*
O1W	0.15716 (15)	0.8841 (4)	0.85921 (11)	0.0503 (5)
H1W	0.229 (3)	0.859 (7)	0.8750 (17)	0.076*
H2W	0.149 (3)	0.998 (7)	0.8288 (19)	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0251 (8)	0.0298 (8)	0.0410 (8)	0.0014 (7)	0.0194 (6)	−0.0033 (8)
O2A	0.0196 (7)	0.0308 (9)	0.0681 (10)	0.0000 (8)	0.0136 (7)	−0.0024 (9)
O3A	0.0326 (9)	0.0296 (9)	0.0571 (10)	−0.0033 (8)	0.0306 (8)	−0.0094 (9)
C1A	0.0169 (9)	0.0271 (11)	0.0188 (8)	0.0011 (8)	0.0045 (7)	0.0019 (8)
C2A	0.0177 (9)	0.0246 (11)	0.0299 (9)	0.0030 (9)	0.0072 (7)	0.0018 (9)
C3A	0.0233 (10)	0.0206 (10)	0.0354 (10)	−0.0004 (9)	0.0181 (8)	−0.0008 (9)
C4A	0.0293 (10)	0.0231 (11)	0.0200 (8)	−0.0035 (9)	0.0107 (7)	−0.0026 (8)
C5A	0.0202 (9)	0.0200 (10)	0.0185 (8)	−0.0038 (8)	0.0062 (7)	−0.0012 (8)
C6A	0.0266 (10)	0.0399 (14)	0.0203 (8)	−0.0032 (11)	−0.0002 (7)	0.0007 (10)
C7A	0.0189 (9)	0.0297 (12)	0.0327 (10)	−0.0032 (10)	−0.0017 (8)	−0.0001 (10)
C8A	0.0154 (8)	0.0201 (10)	0.0327 (9)	−0.0002 (8)	0.0044 (7)	−0.0016 (9)
C9A	0.0178 (8)	0.0183 (9)	0.0211 (8)	−0.0009 (8)	0.0076 (7)	−0.0019 (8)
C10A	0.0156 (8)	0.0157 (9)	0.0182 (8)	0.0000 (8)	0.0043 (6)	0.0005 (8)
C11A	0.0224 (9)	0.0263 (11)	0.0276 (9)	−0.0004 (9)	0.0117 (7)	−0.0027 (10)
C12A	0.0226 (10)	0.0184 (10)	0.0474 (12)	−0.0003 (9)	0.0130 (9)	−0.0004 (10)
C13A	0.0458 (14)	0.0381 (14)	0.0294 (10)	−0.0103 (12)	0.0190 (10)	−0.0108 (11)
C14A	0.0375 (12)	0.0284 (12)	0.0264 (9)	−0.0023 (10)	0.0148 (9)	0.0020 (9)
C15A	0.0220 (9)	0.0185 (10)	0.0284 (9)	0.0002 (9)	0.0064 (8)	−0.0006 (9)
O1B	0.0296 (8)	0.0350 (9)	0.0232 (6)	−0.0089 (7)	0.0105 (6)	−0.0003 (7)
O2B	0.0359 (8)	0.0586 (12)	0.0220 (7)	−0.0074 (9)	0.0126 (6)	0.0011 (8)
O3B	0.0558 (11)	0.0265 (9)	0.0441 (9)	0.0108 (8)	0.0374 (8)	0.0108 (8)
C1B	0.0311 (11)	0.0235 (11)	0.0190 (8)	−0.0013 (9)	0.0074 (8)	−0.0028 (8)
C2B	0.0376 (11)	0.0292 (11)	0.0216 (8)	0.0015 (10)	0.0134 (8)	0.0016 (10)
C3B	0.0396 (12)	0.0200 (10)	0.0304 (9)	0.0068 (10)	0.0224 (9)	0.0064 (10)
C4B	0.0243 (10)	0.0228 (10)	0.0321 (10)	0.0042 (9)	0.0142 (8)	0.0055 (9)
C5B	0.0224 (9)	0.0193 (9)	0.0223 (8)	0.0011 (8)	0.0080 (7)	0.0012 (8)
C6B	0.0246 (10)	0.0354 (13)	0.0267 (9)	−0.0073 (10)	0.0063 (8)	−0.0041 (10)
C7B	0.0271 (10)	0.0380 (13)	0.0199 (8)	−0.0022 (10)	0.0071 (7)	−0.0052 (10)
C8B	0.0259 (10)	0.0262 (11)	0.0188 (8)	0.0003 (9)	0.0082 (7)	−0.0001 (8)
C9B	0.0235 (9)	0.0191 (10)	0.0194 (8)	0.0001 (9)	0.0076 (7)	−0.0014 (8)
C10B	0.0225 (9)	0.0171 (9)	0.0177 (8)	0.0006 (8)	0.0063 (7)	−0.0016 (8)
C11B	0.0296 (10)	0.0311 (12)	0.0177 (8)	−0.0065 (10)	0.0065 (7)	−0.0019 (9)
C12B	0.0293 (10)	0.0299 (12)	0.0231 (9)	−0.0033 (10)	0.0096 (8)	−0.0025 (9)
C13B	0.0248 (11)	0.0367 (14)	0.0479 (12)	0.0037 (11)	0.0164 (9)	0.0105 (12)
C14B	0.0295 (11)	0.0208 (10)	0.0428 (12)	0.0005 (9)	0.0185 (10)	0.0007 (10)
C15B	0.0249 (10)	0.0206 (10)	0.0314 (10)	0.0026 (8)	0.0112 (8)	0.0007 (9)
O1W	0.0266 (8)	0.0432 (12)	0.0734 (13)	−0.0053 (9)	0.0007 (8)	0.0288 (10)

Geometric parameters (Å, º)

O1A—C12A	1.342 (3)	O1B—C11B	1.467 (2)
O1A—C11A	1.471 (2)	O2B—C12B	1.203 (2)
O2A—C12A	1.220 (2)	O3B—C3B	1.437 (2)
O3A—C3A	1.435 (2)	O3B—H3OB	0.82 (3)
O3A—H3OA	0.86 (3)	C1B—C2B	1.525 (3)
C1A—C2A	1.524 (3)	C1B—C10B	1.538 (2)
C1A—C10A	1.536 (2)	C1B—H1B1	0.9900
C1A—H1A1	0.9900	C1B—H1B2	0.9900
C1A—H1A2	0.9900	C2B—C3B	1.517 (3)
C2A—C3A	1.516 (3)	C2B—H2B1	0.9900
C2A—H2A1	0.9900	C2B—H2B2	0.9900
C2A—H2A2	0.9900	C3B—C4B	1.544 (3)
C3A—C4A	1.545 (3)	C3B—H3B	1.0000
C3A—H3A	1.0000	C4B—C13B	1.540 (3)
C4A—C13A	1.539 (3)	C4B—C14B	1.542 (3)
C4A—C14A	1.541 (3)	C4B—C5B	1.562 (3)
C4A—C5A	1.559 (3)	C5B—C6B	1.543 (3)
C5A—C6A	1.543 (3)	C5B—C10B	1.562 (3)
C5A—C10A	1.562 (2)	C5B—H5B	1.0000
C5A—H5A	1.0000	C6B—C7B	1.500 (3)
C6A—C7A	1.503 (3)	C6B—H6B1	0.9900
C6A—H6A1	0.9900	C6B—H6B2	0.9900
C6A—H6A2	0.9900	C7B—C8B	1.322 (3)
C7A—C8A	1.314 (3)	C7B—H7B	0.9500
C7A—H7A	0.9500	C8B—C12B	1.477 (3)
C8A—C12A	1.474 (3)	C8B—C9B	1.502 (3)
C8A—C9A	1.503 (3)	C9B—C11B	1.540 (3)
C9A—C11A	1.536 (3)	C9B—C10B	1.545 (3)
C9A—C10A	1.545 (3)	C9B—H9B	1.0000
C9A—H9A	1.0000	C10B—C15B	1.532 (3)
C10A—C15A	1.536 (3)	C11B—H11C	0.9900
C11A—H11A	0.9900	C11B—H11D	0.9900
C11A—H11B	0.9900	C13B—H13D	0.9800
C13A—H13A	0.9800	C13B—H13E	0.9800
C13A—H13B	0.9800	C13B—H13F	0.9800
C13A—H13C	0.9800	C14B—H14D	0.9800
C14A—H14A	0.9800	C14B—H14E	0.9800
C14A—H14B	0.9800	C14B—H14F	0.9800
C14A—H14C	0.9800	C15B—H15D	0.9800
C15A—H15A	0.9800	C15B—H15E	0.9800
C15A—H15B	0.9800	C15B—H15F	0.9800
C15A—H15C	0.9800	O1W—H1W	0.90 (3)
O1B—C12B	1.358 (2)	O1W—H2W	0.88 (4)
C12A—O1A—C11A	110.13 (15)	C3B—O3B—H3OB	113 (2)
C3A—O3A—H3OA	106 (2)	C2B—C1B—C10B	113.31 (18)
C2A—C1A—C10A	113.09 (15)	C2B—C1B—H1B1	108.9
C2A—C1A—H1A1	109.0	C10B—C1B—H1B1	108.9
C10A—C1A—H1A1	109.0	C2B—C1B—H1B2	108.9
C2A—C1A—H1A2	109.0	C10B—C1B—H1B2	108.9
C10A—C1A—H1A2	109.0	H1B1—C1B—H1B2	107.7
H1A1—C1A—H1A2	107.8	C3B—C2B—C1B	110.76 (16)
C3A—C2A—C1A	109.96 (16)	C3B—C2B—H2B1	109.5
C3A—C2A—H2A1	109.7	C1B—C2B—H2B1	109.5
C1A—C2A—H2A1	109.7	C3B—C2B—H2B2	109.5
C3A—C2A—H2A2	109.7	C1B—C2B—H2B2	109.5
C1A—C2A—H2A2	109.7	H2B1—C2B—H2B2	108.1
H2A1—C2A—H2A2	108.2	O3B—C3B—C2B	109.73 (16)
O3A—C3A—C2A	111.47 (17)	O3B—C3B—C4B	109.58 (18)
O3A—C3A—C4A	111.42 (16)	C2B—C3B—C4B	113.67 (16)
C2A—C3A—C4A	113.09 (17)	O3B—C3B—H3B	107.9
O3A—C3A—H3A	106.8	C2B—C3B—H3B	107.9
C2A—C3A—H3A	106.8	C4B—C3B—H3B	107.9
C4A—C3A—H3A	106.8	C13B—C4B—C14B	106.9 (2)
C13A—C4A—C14A	107.22 (16)	C13B—C4B—C3B	107.79 (17)
C13A—C4A—C3A	108.58 (19)	C14B—C4B—C3B	110.14 (18)
C14A—C4A—C3A	110.03 (17)	C13B—C4B—C5B	108.81 (16)
C13A—C4A—C5A	108.38 (17)	C14B—C4B—C5B	115.19 (19)
C14A—C4A—C5A	115.17 (18)	C3B—C4B—C5B	107.80 (17)
C3A—C4A—C5A	107.30 (15)	C6B—C5B—C10B	111.29 (15)
C6A—C5A—C4A	113.08 (15)	C6B—C5B—C4B	112.83 (17)
C6A—C5A—C10A	111.19 (16)	C10B—C5B—C4B	117.22 (15)
C4A—C5A—C10A	117.54 (15)	C6B—C5B—H5B	104.7
C6A—C5A—H5A	104.5	C10B—C5B—H5B	104.7
C4A—C5A—H5A	104.5	C4B—C5B—H5B	104.7
C10A—C5A—H5A	104.5	C7B—C6B—C5B	113.67 (17)
C7A—C6A—C5A	112.94 (16)	C7B—C6B—H6B1	108.8
C7A—C6A—H6A1	109.0	C5B—C6B—H6B1	108.8
C5A—C6A—H6A1	109.0	C7B—C6B—H6B2	108.8
C7A—C6A—H6A2	109.0	C5B—C6B—H6B2	108.8
C5A—C6A—H6A2	109.0	H6B1—C6B—H6B2	107.7
H6A1—C6A—H6A2	107.8	C8B—C7B—C6B	121.09 (17)
C8A—C7A—C6A	121.24 (18)	C8B—C7B—H7B	119.5
C8A—C7A—H7A	119.4	C6B—C7B—H7B	119.5
C6A—C7A—H7A	119.4	C7B—C8B—C12B	126.89 (18)
C7A—C8A—C12A	127.48 (18)	C7B—C8B—C9B	124.46 (18)
C7A—C8A—C9A	124.94 (18)	C12B—C8B—C9B	108.36 (17)
C12A—C8A—C9A	107.10 (16)	C8B—C9B—C11B	101.17 (15)
C8A—C9A—C11A	101.30 (16)	C8B—C9B—C10B	111.84 (16)
C8A—C9A—C10A	111.54 (15)	C11B—C9B—C10B	120.03 (16)
C11A—C9A—C10A	119.31 (16)	C8B—C9B—H9B	107.7
C8A—C9A—H9A	108.0	C11B—C9B—H9B	107.7
C11A—C9A—H9A	108.0	C10B—C9B—H9B	107.7
C10A—C9A—H9A	108.0	C15B—C10B—C1B	110.35 (16)
C1A—C10A—C15A	110.71 (16)	C15B—C10B—C9B	110.84 (16)
C1A—C10A—C9A	108.22 (15)	C1B—C10B—C9B	108.40 (16)
C15A—C10A—C9A	110.75 (16)	C15B—C10B—C5B	113.19 (16)
C1A—C10A—C5A	110.01 (15)	C1B—C10B—C5B	109.59 (15)
C15A—C10A—C5A	112.84 (16)	C9B—C10B—C5B	104.21 (14)
C9A—C10A—C5A	104.03 (14)	O1B—C11B—C9B	105.47 (14)
O1A—C11A—C9A	105.33 (15)	O1B—C11B—H11C	110.6
O1A—C11A—H11A	110.7	C9B—C11B—H11C	110.6
C9A—C11A—H11A	110.7	O1B—C11B—H11D	110.6
O1A—C11A—H11B	110.7	C9B—C11B—H11D	110.6
C9A—C11A—H11B	110.7	H11C—C11B—H11D	108.8
H11A—C11A—H11B	108.8	O2B—C12B—O1B	121.4 (2)
O2A—C12A—O1A	121.1 (2)	O2B—C12B—C8B	130.2 (2)
O2A—C12A—C8A	129.1 (2)	O1B—C12B—C8B	108.44 (15)
O1A—C12A—C8A	109.78 (16)	C4B—C13B—H13D	109.5
C4A—C13A—H13A	109.5	C4B—C13B—H13E	109.5
C4A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
H13A—C13A—H13B	109.5	C4B—C13B—H13F	109.5
C4A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13E—C13B—H13F	109.5
H13B—C13A—H13C	109.5	C4B—C14B—H14D	109.5
C4A—C14A—H14A	109.5	C4B—C14B—H14E	109.5
C4A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
H14A—C14A—H14B	109.5	C4B—C14B—H14F	109.5
C4A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14E—C14B—H14F	109.5
H14B—C14A—H14C	109.5	C10B—C15B—H15D	109.5
C10A—C15A—H15A	109.5	C10B—C15B—H15E	109.5
C10A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
H15A—C15A—H15B	109.5	C10B—C15B—H15F	109.5
C10A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15E—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H1W—O1W—H2W	105 (3)
C12B—O1B—C11B	110.67 (16)
C10A—C1A—C2A—C3A	−58.2 (2)	C10B—C1B—C2B—C3B	−57.0 (2)
C1A—C2A—C3A—O3A	−171.62 (17)	C1B—C2B—C3B—O3B	−177.73 (18)
C1A—C2A—C3A—C4A	61.9 (2)	C1B—C2B—C3B—C4B	59.2 (3)
O3A—C3A—C4A—C13A	61.4 (2)	O3B—C3B—C4B—C13B	66.1 (2)
C2A—C3A—C4A—C13A	−172.13 (17)	C2B—C3B—C4B—C13B	−170.73 (19)
O3A—C3A—C4A—C14A	−55.7 (2)	O3B—C3B—C4B—C14B	−50.2 (2)
C2A—C3A—C4A—C14A	70.8 (2)	C2B—C3B—C4B—C14B	73.0 (2)
O3A—C3A—C4A—C5A	178.32 (17)	O3B—C3B—C4B—C5B	−176.61 (16)
C2A—C3A—C4A—C5A	−55.2 (2)	C2B—C3B—C4B—C5B	−53.4 (2)
C13A—C4A—C5A—C6A	−62.8 (2)	C13B—C4B—C5B—C6B	−63.1 (2)
C14A—C4A—C5A—C6A	57.2 (2)	C14B—C4B—C5B—C6B	56.8 (2)
C3A—C4A—C5A—C6A	−179.89 (18)	C3B—C4B—C5B—C6B	−179.76 (18)
C13A—C4A—C5A—C10A	165.48 (18)	C13B—C4B—C5B—C10B	165.61 (18)
C14A—C4A—C5A—C10A	−74.5 (2)	C14B—C4B—C5B—C10B	−74.4 (2)
C3A—C4A—C5A—C10A	48.4 (2)	C3B—C4B—C5B—C10B	49.0 (2)
C4A—C5A—C6A—C7A	−177.59 (19)	C10B—C5B—C6B—C7B	−42.0 (3)
C10A—C5A—C6A—C7A	−42.8 (3)	C4B—C5B—C6B—C7B	−176.13 (18)
C5A—C6A—C7A—C8A	7.3 (3)	C5B—C6B—C7B—C8B	8.2 (3)
C6A—C7A—C8A—C12A	174.0 (2)	C6B—C7B—C8B—C12B	173.5 (2)
C6A—C7A—C8A—C9A	3.0 (4)	C6B—C7B—C8B—C9B	0.5 (4)
C7A—C8A—C9A—C11A	150.6 (2)	C7B—C8B—C9B—C11B	153.9 (2)
C12A—C8A—C9A—C11A	−21.9 (2)	C12B—C8B—C9B—C11B	−20.3 (2)
C7A—C8A—C9A—C10A	22.6 (3)	C7B—C8B—C9B—C10B	24.9 (3)
C12A—C8A—C9A—C10A	−149.91 (17)	C12B—C8B—C9B—C10B	−149.20 (18)
C2A—C1A—C10A—C15A	−75.9 (2)	C2B—C1B—C10B—C15B	−75.0 (2)
C2A—C1A—C10A—C9A	162.57 (17)	C2B—C1B—C10B—C9B	163.49 (17)
C2A—C1A—C10A—C5A	49.5 (2)	C2B—C1B—C10B—C5B	50.3 (2)
C8A—C9A—C10A—C1A	−170.75 (16)	C8B—C9B—C10B—C15B	67.7 (2)
C11A—C9A—C10A—C1A	71.7 (2)	C11B—C9B—C10B—C15B	−50.5 (2)
C8A—C9A—C10A—C15A	67.7 (2)	C8B—C9B—C10B—C1B	−171.07 (16)
C11A—C9A—C10A—C15A	−49.9 (2)	C11B—C9B—C10B—C1B	70.7 (2)
C8A—C9A—C10A—C5A	−53.8 (2)	C8B—C9B—C10B—C5B	−54.40 (19)
C11A—C9A—C10A—C5A	−171.37 (17)	C11B—C9B—C10B—C5B	−172.60 (17)
C6A—C5A—C10A—C1A	−179.03 (16)	C6B—C5B—C10B—C15B	−56.4 (2)
C4A—C5A—C10A—C1A	−46.5 (2)	C4B—C5B—C10B—C15B	75.5 (2)
C6A—C5A—C10A—C15A	−54.8 (2)	C6B—C5B—C10B—C1B	179.92 (19)
C4A—C5A—C10A—C15A	77.7 (2)	C4B—C5B—C10B—C1B	−48.1 (2)
C6A—C5A—C10A—C9A	65.3 (2)	C6B—C5B—C10B—C9B	64.1 (2)
C4A—C5A—C10A—C9A	−162.20 (17)	C4B—C5B—C10B—C9B	−163.94 (17)
C12A—O1A—C11A—C9A	−19.5 (2)	C12B—O1B—C11B—C9B	−20.1 (2)
C8A—C9A—C11A—O1A	24.7 (2)	C8B—C9B—C11B—O1B	23.8 (2)
C10A—C9A—C11A—O1A	147.45 (17)	C10B—C9B—C11B—O1B	147.30 (17)
C11A—O1A—C12A—O2A	−175.4 (2)	C11B—O1B—C12B—O2B	−172.9 (2)
C11A—O1A—C12A—C8A	5.3 (2)	C11B—O1B—C12B—C8B	7.1 (3)
C7A—C8A—C12A—O2A	20.0 (4)	C7B—C8B—C12B—O2B	15.3 (4)
C9A—C8A—C12A—O2A	−167.8 (2)	C9B—C8B—C12B—O2B	−170.7 (3)
C7A—C8A—C12A—O1A	−160.9 (2)	C7B—C8B—C12B—O1B	−164.7 (2)
C9A—C8A—C12A—O1A	11.4 (2)	C9B—C8B—C12B—O1B	9.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3A—H3OA···O1W^i	0.86 (3)	1.79 (3)	2.632 (3)	164 (3)
O3B—H3OB···O3A^ii	0.82 (3)	1.83 (4)	2.641 (2)	168 (3)
O1W—H1W···O2A	0.90 (3)	1.90 (3)	2.791 (2)	169 (3)
O1W—H2W···O3B^iii	0.88 (4)	1.83 (4)	2.694 (3)	166 (3)

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x, y+1, z.

(II) 3β-Acetoxy-7-drimen-12,11-olide

Crystal data

C17H24O4	F(000) = 316
Mr = 292.36	Dx = 1.285 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2218 reflections
a = 6.802 (3) Å	θ = 2.5–30.0°
b = 7.918 (4) Å	µ = 0.09 mm^−1
c = 14.302 (8) Å	T = 120 K
β = 101.22 (2)°	Prism, colorless
V = 755.6 (7) Å^3	0.33 × 0.18 × 0.15 mm
Z = 2

Data collection

Nonius KappaCCD area-detector (with Oxford Cryostream) diffractometer	1456 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
Graphite monochromator	θmax = 30.0°, θmin = 2.9°
ω scans with κ offsets	h = −9→9
8695 measured reflections	k = −11→11
2353 independent reflections	l = −20→20

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)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0473P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
2353 reflections	Δρmax = 0.22 e Å^−3
195 parameters	Δρmin = −0.20 e Å^−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (3)

Special details

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
O1	0.8176 (3)	0.4883 (3)	0.55905 (12)	0.0373 (5)
O2	0.9004 (3)	0.7238 (3)	0.64502 (13)	0.0466 (6)
O3	0.2946 (2)	0.7821 (3)	0.03214 (12)	0.0303 (5)
O4	−0.0282 (3)	0.7133 (3)	0.02549 (13)	0.0421 (6)
C1	0.5137 (4)	0.5137 (4)	0.24430 (18)	0.0291 (6)
H1A	0.5911	0.4071	0.2488	0.035*
H1B	0.3883	0.4910	0.2675	0.035*
C2	0.4608 (4)	0.5684 (4)	0.13965 (18)	0.0281 (6)
H2A	0.5848	0.5818	0.1138	0.034*
H2B	0.3767	0.4811	0.1017	0.034*
C3	0.3484 (4)	0.7340 (4)	0.13273 (17)	0.0272 (6)
H3	0.2227	0.7178	0.1581	0.033*
C4	0.4685 (4)	0.8808 (4)	0.18701 (18)	0.0277 (6)
C5	0.5321 (4)	0.8218 (4)	0.29222 (18)	0.0273 (6)
H5	0.4030	0.8075	0.3150	0.033*
C6	0.6462 (4)	0.9594 (4)	0.35766 (18)	0.0314 (7)
H6A	0.7580	1.0015	0.3290	0.038*
H6B	0.5544	1.0553	0.3609	0.038*
C7	0.7284 (4)	0.8995 (4)	0.45640 (19)	0.0307 (7)
H7	0.7873	0.9790	0.5033	0.037*
C8	0.7213 (4)	0.7382 (4)	0.48037 (18)	0.0298 (7)
C9	0.6281 (4)	0.6011 (4)	0.41395 (19)	0.0307 (7)
H9	0.4839	0.5919	0.4190	0.037*
C10	0.6365 (4)	0.6465 (4)	0.30899 (18)	0.0265 (6)
C11	0.7360 (4)	0.4441 (4)	0.45954 (19)	0.0327 (7)
H11A	0.6413	0.3483	0.4562	0.039*
H11B	0.8452	0.4117	0.4263	0.039*
C12	0.8213 (4)	0.6600 (4)	0.5705 (2)	0.0337 (7)
C13	0.3243 (4)	1.0323 (4)	0.1838 (2)	0.0392 (8)
H13A	0.2183	1.0040	0.2187	0.059*
H13B	0.2643	1.0581	0.1173	0.059*
H13C	0.3988	1.1309	0.2132	0.059*
C14	0.6407 (4)	0.9339 (4)	0.1383 (2)	0.0362 (7)
H14A	0.7388	0.9999	0.1830	0.054*
H14B	0.5877	1.0027	0.0821	0.054*
H14C	0.7057	0.8330	0.1187	0.054*
C15	0.8545 (3)	0.6492 (4)	0.29435 (18)	0.0310 (7)
H15A	0.9130	0.5362	0.3063	0.047*
H15B	0.9322	0.7300	0.3387	0.047*
H15C	0.8573	0.6829	0.2287	0.047*
C16	0.1016 (4)	0.7681 (4)	−0.01206 (18)	0.0278 (6)
C17	0.0738 (4)	0.8303 (4)	−0.11191 (18)	0.0316 (7)
H17A	−0.0402	0.7720	−0.1512	0.047*
H17B	0.1953	0.8077	−0.1371	0.047*
H17C	0.0480	0.9521	−0.1132	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0408 (11)	0.0408 (15)	0.0292 (11)	0.0011 (10)	0.0044 (8)	0.0066 (10)
O2	0.0573 (12)	0.0554 (15)	0.0253 (10)	−0.0093 (13)	0.0034 (9)	0.0001 (11)
O3	0.0265 (9)	0.0368 (13)	0.0257 (9)	−0.0003 (9)	0.0004 (7)	−0.0002 (8)
O4	0.0322 (10)	0.0568 (15)	0.0349 (12)	−0.0113 (11)	0.0003 (8)	0.0074 (11)
C1	0.0292 (13)	0.0250 (16)	0.0326 (15)	−0.0013 (12)	0.0048 (12)	−0.0010 (13)
C2	0.0299 (13)	0.0237 (17)	0.0280 (14)	−0.0027 (13)	−0.0007 (11)	−0.0022 (13)
C3	0.0267 (12)	0.0302 (17)	0.0241 (14)	−0.0004 (13)	0.0033 (10)	−0.0004 (13)
C4	0.0268 (12)	0.0263 (16)	0.0285 (15)	0.0013 (12)	0.0016 (11)	−0.0007 (13)
C5	0.0261 (12)	0.0241 (16)	0.0304 (15)	0.0042 (12)	0.0024 (11)	−0.0016 (13)
C6	0.0319 (13)	0.0263 (17)	0.0344 (15)	0.0033 (13)	0.0024 (12)	−0.0024 (13)
C7	0.0280 (14)	0.0361 (19)	0.0267 (14)	0.0001 (13)	0.0018 (11)	−0.0081 (14)
C8	0.0258 (13)	0.0349 (19)	0.0282 (15)	0.0021 (13)	0.0045 (11)	−0.0008 (14)
C9	0.0291 (12)	0.0287 (17)	0.0335 (15)	0.0016 (13)	0.0045 (11)	0.0007 (13)
C10	0.0282 (12)	0.0260 (16)	0.0239 (13)	0.0017 (12)	0.0015 (10)	0.0026 (12)
C11	0.0309 (14)	0.0364 (19)	0.0293 (15)	0.0038 (14)	0.0021 (12)	0.0019 (13)
C12	0.0314 (14)	0.043 (2)	0.0285 (15)	−0.0039 (14)	0.0095 (12)	−0.0001 (14)
C13	0.0440 (15)	0.0298 (18)	0.0390 (17)	0.0096 (14)	−0.0038 (13)	−0.0043 (14)
C14	0.0384 (14)	0.0350 (19)	0.0325 (14)	−0.0072 (13)	0.0000 (12)	0.0020 (13)
C15	0.0294 (12)	0.0306 (17)	0.0325 (14)	0.0012 (13)	0.0045 (11)	−0.0027 (14)
C16	0.0271 (13)	0.0242 (16)	0.0299 (14)	0.0004 (12)	0.0003 (11)	−0.0063 (12)
C17	0.0316 (13)	0.0296 (17)	0.0300 (15)	−0.0028 (13)	−0.0034 (11)	0.0010 (13)

Geometric parameters (Å, º)

O1—C12	1.369 (4)	C7—C8	1.326 (4)
O1—C11	1.466 (3)	C7—H7	0.9500
O2—C12	1.207 (3)	C8—C12	1.472 (4)
O3—C16	1.346 (3)	C8—C9	1.499 (4)
O3—C3	1.464 (3)	C9—C11	1.525 (4)
O4—C16	1.201 (3)	C9—C10	1.555 (4)
C1—C2	1.532 (3)	C9—H9	1.0000
C1—C10	1.536 (4)	C10—C15	1.537 (3)
C1—H1A	0.9900	C11—H11A	0.9900
C1—H1B	0.9900	C11—H11B	0.9900
C2—C3	1.511 (4)	C13—H13A	0.9800
C2—H2A	0.9900	C13—H13B	0.9800
C2—H2B	0.9900	C13—H13C	0.9800
C3—C4	1.540 (4)	C14—H14A	0.9800
C3—H3	1.0000	C14—H14B	0.9800
C4—C13	1.544 (4)	C14—H14C	0.9800
C4—C14	1.534 (4)	C15—H15A	0.9800
C4—C5	1.555 (4)	C15—H15B	0.9800
C5—C6	1.544 (4)	C15—H15C	0.9800
C5—C10	1.556 (4)	C16—C17	1.488 (4)
C5—H5	1.0000	C17—H17A	0.9800
C6—C7	1.492 (4)	C17—H17B	0.9800
C6—H6A	0.9900	C17—H17C	0.9800
C6—H6B	0.9900
C12—O1—C11	110.4 (2)	C11—C9—C10	119.8 (2)
C16—O3—C3	118.3 (2)	C8—C9—H9	107.9
C2—C1—C10	113.0 (2)	C11—C9—H9	107.9
C2—C1—H1A	109.0	C10—C9—H9	107.9
C10—C1—H1A	109.0	C1—C10—C15	110.7 (2)
C2—C1—H1B	109.0	C1—C10—C9	107.8 (2)
C10—C1—H1B	109.0	C15—C10—C9	110.6 (2)
H1A—C1—H1B	107.8	C1—C10—C5	109.84 (19)
C3—C2—C1	109.2 (2)	C15—C10—C5	113.0 (2)
C3—C2—H2A	109.8	C9—C10—C5	104.7 (2)
C1—C2—H2A	109.8	O1—C11—C9	106.3 (2)
C3—C2—H2B	109.8	O1—C11—H11A	110.5
C1—C2—H2B	109.8	C9—C11—H11A	110.5
H2A—C2—H2B	108.3	O1—C11—H11B	110.5
O3—C3—C2	108.4 (2)	C9—C11—H11B	110.5
O3—C3—C4	107.8 (2)	H11A—C11—H11B	108.7
C2—C3—C4	114.20 (19)	O2—C12—O1	121.1 (3)
O3—C3—H3	108.8	O2—C12—C8	130.3 (3)
C2—C3—H3	108.8	O1—C12—C8	108.6 (2)
C4—C3—H3	108.8	C4—C13—H13A	109.5
C14—C4—C3	110.8 (2)	C4—C13—H13B	109.5
C13—C4—C14	108.1 (2)	H13A—C13—H13B	109.5
C3—C4—C13	107.4 (2)	C4—C13—H13C	109.5
C14—C4—C5	115.4 (2)	H13A—C13—H13C	109.5
C3—C4—C5	106.3 (2)	H13B—C13—H13C	109.5
C13—C4—C5	108.6 (2)	C4—C14—H14A	109.5
C6—C5—C4	112.8 (2)	C4—C14—H14B	109.5
C6—C5—C10	112.05 (19)	H14A—C14—H14B	109.5
C4—C5—C10	116.8 (2)	C4—C14—H14C	109.5
C6—C5—H5	104.6	H14A—C14—H14C	109.5
C4—C5—H5	104.6	H14B—C14—H14C	109.5
C10—C5—H5	104.6	C10—C15—H15A	109.5
C7—C6—C5	113.6 (3)	C10—C15—H15B	109.5
C7—C6—H6A	108.8	H15A—C15—H15B	109.5
C5—C6—H6A	108.8	C10—C15—H15C	109.5
C7—C6—H6B	108.8	H15A—C15—H15C	109.5
C5—C6—H6B	108.8	H15B—C15—H15C	109.5
H6A—C6—H6B	107.7	O4—C16—O3	123.7 (2)
C8—C7—C6	121.7 (3)	O4—C16—C17	125.6 (2)
C8—C7—H7	119.1	O3—C16—C17	110.7 (2)
C6—C7—H7	119.1	C16—C17—H17A	109.5
C7—C8—C12	126.7 (3)	C16—C17—H17B	109.5
C7—C8—C9	124.4 (3)	H17A—C17—H17B	109.5
C12—C8—C9	108.5 (3)	C16—C17—H17C	109.5
C8—C9—C11	102.2 (2)	H17A—C17—H17C	109.5
C8—C9—C10	110.7 (2)	H17B—C17—H17C	109.5
C10—C1—C2—C3	−56.9 (3)	C2—C1—C10—C15	−74.8 (3)
C16—O3—C3—C2	107.0 (2)	C2—C1—C10—C9	164.1 (2)
C16—O3—C3—C4	−128.9 (2)	C2—C1—C10—C5	50.6 (3)
C1—C2—C3—O3	−178.54 (19)	C8—C9—C10—C1	−172.3 (2)
C1—C2—C3—C4	61.2 (3)	C11—C9—C10—C1	69.3 (3)
O3—C3—C4—C13	66.7 (3)	C8—C9—C10—C15	66.6 (3)
C2—C3—C4—C13	−172.7 (2)	C11—C9—C10—C15	−51.8 (3)
O3—C3—C4—C14	−51.1 (3)	C8—C9—C10—C5	−55.4 (3)
C2—C3—C4—C14	69.5 (3)	C11—C9—C10—C5	−173.8 (2)
O3—C3—C4—C5	−177.18 (19)	C6—C5—C10—C1	178.4 (2)
C2—C3—C4—C5	−56.6 (3)	C4—C5—C10—C1	−49.4 (3)
C14—C4—C5—C6	59.5 (3)	C6—C5—C10—C15	−57.5 (3)
C3—C4—C5—C6	−177.2 (2)	C4—C5—C10—C15	74.7 (3)
C13—C4—C5—C6	−61.9 (3)	C6—C5—C10—C9	62.9 (3)
C14—C4—C5—C10	−72.3 (3)	C4—C5—C10—C9	−164.9 (2)
C3—C4—C5—C10	50.9 (3)	C12—O1—C11—C9	−17.0 (3)
C13—C4—C5—C10	166.2 (2)	C8—C9—C11—O1	20.2 (3)
C4—C5—C6—C7	−173.6 (2)	C10—C9—C11—O1	142.9 (2)
C10—C5—C6—C7	−39.4 (3)	C11—O1—C12—O2	−173.0 (2)
C5—C6—C7—C8	7.1 (4)	C11—O1—C12—C8	6.0 (3)
C6—C7—C8—C12	170.7 (2)	C7—C8—C12—O2	13.2 (5)
C6—C7—C8—C9	−1.6 (4)	C9—C8—C12—O2	−173.5 (3)
C7—C8—C9—C11	156.4 (3)	C7—C8—C12—O1	−165.6 (3)
C12—C8—C9—C11	−17.1 (3)	C9—C8—C12—O1	7.6 (3)
C7—C8—C9—C10	27.8 (4)	C3—O3—C16—O4	−2.5 (4)
C12—C8—C9—C10	−145.7 (2)	C3—O3—C16—C17	177.2 (2)