1α,6,11β,15β-Tetra­acet­oxy-6,7-seco-7,20-olide-ent-kaur-16-ene

The title compound, C₂₈H₃₈O₁₀, is a natural ent-kaurane diterpenoid. It is a pure enanti­omer containing eight chiral centers and its absolute configuration is based on a related compound of known stereochemistry.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.038
• wR factor = 0.081
• Data-to-parameter ratio = 9.6

checkCIF/PLATON results

No syntax errors found



Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.790
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.95 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.10 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C7     -   C8      ..       6.41 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C23
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C27
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.99
           From the CIF: _reflns_number_total               3363
           Count of symmetry unique reflns         3363
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    = .          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   9 ALERT level G = General alerts; check

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: ORTEP-3 (Farrugia, 1997b); software used to prepare material for publication: SHELXTL.

1α,6,11β,15β-Tetraacetoxy-6,7-seco-7,20-olide-ent-kaur-16-ene

Crystal data

C28H38O10	Dx = 1.294 Mg m^−3
Mr = 534.58	Melting point: 487 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 31 reflections
a = 11.144 (2) Å	θ = 2.2–14.7°
b = 14.352 (2) Å	µ = 0.10 mm^−1
c = 17.151 (2) Å	T = 294 K
V = 2743.2 (7) Å^3	Block, colourless
Z = 4	0.65 × 0.35 × 0.27 mm
F(000) = 1144

Data collection

Siemens P4 diffractometer	Rint = 0.017
Radiation source: normal-focus sealed tube	θmax = 27.0°, θmin = 1.9°
Graphite monochromator	h = 0→14
ω scans	k = 0→18
3648 measured reflections	l = −1→21
3363 independent reflections	3 standard reflections every 97 reflections
1716 reflections with I > 2σ(I)	intensity decay: 2.1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.081	H-atom parameters constrained
S = 0.79	w = 1/[σ^2(Fo^2) + (0.038P)^2] where P = (Fo^2 + 2Fc^2)/3
3363 reflections	(Δ/σ)max < 0.001
349 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.12 e Å^−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	0.4815 (2)	0.20063 (14)	0.80841 (12)	0.0597 (6)
O2	0.4197 (3)	0.19593 (16)	0.92885 (13)	0.0775 (8)
O3	0.5462 (2)	0.37683 (15)	0.85187 (11)	0.0563 (6)
O4	0.5941 (2)	0.52204 (18)	0.88756 (14)	0.0837 (8)
O5	0.2341 (2)	0.32231 (15)	0.60528 (12)	0.0600 (6)
O6	0.2125 (3)	0.43922 (18)	0.52053 (16)	0.0957 (9)
O7	0.27261 (18)	0.50721 (13)	0.71704 (10)	0.0486 (5)
O8	0.2612 (2)	0.64692 (14)	0.77492 (13)	0.0694 (7)
O9	0.1857 (2)	0.19251 (15)	0.75918 (11)	0.0606 (6)
O10	0.0801 (3)	0.07003 (17)	0.80179 (15)	0.0890 (9)
C1	0.5410 (3)	0.4029 (2)	0.76947 (16)	0.0460 (8)
H1	0.5165	0.4684	0.7666	0.055*
C2	0.6627 (3)	0.3951 (2)	0.73331 (17)	0.0544 (9)
H2A	0.6862	0.3301	0.7298	0.065*
H2B	0.7214	0.4277	0.7649	0.065*
C3	0.6567 (3)	0.4378 (2)	0.65256 (18)	0.0624 (10)
H3A	0.7358	0.4353	0.6290	0.075*
H3B	0.6341	0.5029	0.6572	0.075*
C4	0.5671 (3)	0.3885 (2)	0.59883 (17)	0.0525 (8)
C5	0.4418 (3)	0.3761 (2)	0.64077 (15)	0.0458 (8)
H5	0.4053	0.4382	0.6406	0.055*
C6	0.3601 (3)	0.3156 (2)	0.58785 (17)	0.0575 (9)
H6A	0.3726	0.3340	0.5340	0.069*
H6B	0.3845	0.2510	0.5927	0.069*
C7	0.4062 (4)	0.2282 (2)	0.8647 (2)	0.0594 (10)
C8	0.3038 (3)	0.2933 (2)	0.84516 (16)	0.0475 (8)
C9	0.3195 (3)	0.35912 (18)	0.77162 (16)	0.0420 (7)
H9	0.2591	0.3381	0.7340	0.050*
C10	0.4435 (3)	0.34473 (18)	0.73016 (16)	0.0397 (7)
C11	0.2846 (3)	0.46020 (19)	0.79211 (15)	0.0447 (8)
H11	0.3490	0.4894	0.8224	0.054*
C12	0.1660 (3)	0.4689 (2)	0.83591 (18)	0.0597 (9)
H12A	0.1009	0.4728	0.7985	0.072*
H12B	0.1664	0.5261	0.8661	0.072*
C13	0.1430 (3)	0.3853 (2)	0.8915 (2)	0.0683 (10)
H13	0.0930	0.4031	0.9360	0.082*
C14	0.2648 (3)	0.3490 (2)	0.91734 (16)	0.0623 (10)
H14A	0.2580	0.3094	0.9629	0.075*
H14B	0.3200	0.3996	0.9283	0.075*
C15	0.1890 (3)	0.2349 (2)	0.83479 (17)	0.0553 (9)
H15	0.1855	0.1866	0.8751	0.066*
C16	0.0905 (4)	0.3042 (3)	0.8476 (2)	0.0677 (10)
C17	−0.0187 (4)	0.2974 (3)	0.8192 (3)	0.1166 (18)
H17A	−0.0395	0.2465	0.7885	0.140*
H17B	−0.0750	0.3434	0.8298	0.140*
C18	0.5480 (3)	0.4543 (2)	0.52889 (17)	0.0749 (11)
H18A	0.5097	0.5105	0.5463	0.112*
H18B	0.4982	0.4242	0.4908	0.112*
H18C	0.6242	0.4692	0.5060	0.112*
C19	0.6229 (3)	0.2977 (2)	0.56808 (19)	0.0736 (11)
H19A	0.6921	0.3121	0.5369	0.110*
H19B	0.5651	0.2650	0.5369	0.110*
H19C	0.6465	0.2592	0.6112	0.110*
C20	0.4659 (3)	0.23983 (19)	0.73156 (16)	0.0497 (8)
H20A	0.3988	0.2089	0.7065	0.060*
H20B	0.5371	0.2266	0.7010	0.060*
C21	0.5810 (3)	0.4415 (3)	0.9038 (2)	0.0644 (10)
C22	0.5990 (4)	0.3984 (3)	0.98173 (18)	0.1032 (15)
H22A	0.6824	0.4014	0.9955	0.155*
H22B	0.5737	0.3345	0.9802	0.155*
H22C	0.5525	0.4316	1.0198	0.155*
C23	0.1707 (4)	0.3882 (3)	0.5675 (2)	0.0680 (11)
C24	0.0438 (4)	0.3871 (3)	0.5937 (3)	0.1008 (14)
H24A	0.0307	0.4369	0.6301	0.151*
H24B	0.0266	0.3286	0.6185	0.151*
H24C	−0.0081	0.3950	0.5495	0.151*
C25	0.2624 (3)	0.6006 (2)	0.7163 (2)	0.0535 (9)
C26	0.2530 (3)	0.6360 (2)	0.63549 (18)	0.0700 (10)
H26A	0.2581	0.7028	0.6358	0.105*
H26B	0.1775	0.6173	0.6135	0.105*
H26C	0.3173	0.6109	0.6047	0.105*
C27	0.1261 (3)	0.1119 (2)	0.7496 (2)	0.0583 (9)
C28	0.1243 (3)	0.0857 (2)	0.66549 (18)	0.0750 (12)
H28A	0.1029	0.0212	0.6605	0.113*
H28B	0.2024	0.0956	0.6433	0.113*
H28C	0.0665	0.1234	0.6385	0.113*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0759 (16)	0.0500 (13)	0.0532 (13)	0.0083 (13)	0.0045 (13)	0.0110 (12)
O2	0.108 (2)	0.0738 (16)	0.0507 (14)	0.0019 (16)	−0.0030 (15)	0.0231 (13)
O3	0.0715 (16)	0.0584 (13)	0.0391 (12)	−0.0076 (13)	−0.0101 (11)	0.0024 (12)
O4	0.111 (2)	0.0725 (17)	0.0674 (17)	−0.0146 (17)	−0.0090 (16)	−0.0153 (14)
O5	0.0642 (17)	0.0684 (15)	0.0475 (13)	−0.0029 (13)	−0.0093 (12)	−0.0045 (12)
O6	0.120 (3)	0.0819 (18)	0.085 (2)	0.0045 (19)	−0.0167 (19)	0.0219 (17)
O7	0.0630 (14)	0.0406 (11)	0.0422 (11)	0.0063 (11)	0.0003 (11)	−0.0027 (10)
O8	0.0945 (19)	0.0467 (12)	0.0670 (15)	−0.0048 (14)	0.0050 (15)	−0.0109 (12)
O9	0.0743 (16)	0.0565 (13)	0.0510 (13)	−0.0206 (13)	0.0086 (12)	−0.0079 (11)
O10	0.116 (2)	0.0720 (17)	0.0790 (18)	−0.0389 (17)	0.0055 (19)	0.0101 (15)
C1	0.057 (2)	0.0460 (17)	0.0349 (17)	0.0003 (16)	0.0000 (17)	0.0031 (14)
C2	0.052 (2)	0.056 (2)	0.056 (2)	−0.0030 (17)	−0.0042 (18)	0.0013 (18)
C3	0.057 (2)	0.066 (2)	0.065 (2)	−0.005 (2)	0.0158 (19)	0.006 (2)
C4	0.060 (2)	0.056 (2)	0.0413 (17)	0.0077 (18)	0.0108 (18)	−0.0025 (18)
C5	0.057 (2)	0.0414 (16)	0.0390 (16)	0.0020 (17)	0.0004 (17)	−0.0045 (15)
C6	0.070 (3)	0.062 (2)	0.0409 (19)	0.0061 (19)	−0.0031 (18)	−0.0071 (17)
C7	0.087 (3)	0.046 (2)	0.045 (2)	−0.009 (2)	−0.001 (2)	0.0039 (18)
C8	0.063 (2)	0.0429 (17)	0.0360 (16)	−0.0017 (18)	0.0042 (16)	−0.0025 (15)
C9	0.055 (2)	0.0368 (16)	0.0342 (16)	−0.0027 (15)	0.0022 (15)	−0.0038 (14)
C10	0.0486 (19)	0.0354 (15)	0.0350 (16)	0.0021 (14)	−0.0010 (16)	−0.0007 (13)
C11	0.049 (2)	0.0437 (17)	0.0411 (17)	0.0042 (16)	−0.0007 (16)	−0.0042 (15)
C12	0.064 (2)	0.054 (2)	0.061 (2)	0.0043 (19)	0.0139 (19)	−0.0102 (18)
C13	0.078 (3)	0.068 (2)	0.059 (2)	0.004 (2)	0.031 (2)	−0.005 (2)
C14	0.096 (3)	0.0537 (19)	0.0373 (17)	−0.007 (2)	0.0123 (19)	−0.0033 (16)
C15	0.070 (2)	0.056 (2)	0.0406 (19)	−0.0115 (19)	0.0091 (18)	−0.0059 (16)
C16	0.059 (2)	0.064 (2)	0.081 (3)	−0.007 (2)	0.027 (2)	−0.007 (2)
C17	0.061 (3)	0.089 (3)	0.200 (5)	−0.006 (3)	0.018 (4)	−0.030 (4)
C18	0.090 (3)	0.085 (3)	0.0496 (19)	0.003 (2)	0.017 (2)	0.011 (2)
C19	0.082 (3)	0.076 (2)	0.063 (2)	0.015 (2)	0.016 (2)	−0.013 (2)
C20	0.064 (2)	0.0430 (17)	0.0426 (19)	0.0037 (17)	0.0064 (18)	0.0002 (15)
C21	0.072 (3)	0.075 (2)	0.046 (2)	−0.003 (2)	−0.007 (2)	−0.013 (2)
C22	0.143 (4)	0.123 (3)	0.044 (2)	−0.016 (3)	−0.031 (2)	0.001 (2)
C23	0.084 (3)	0.060 (2)	0.060 (2)	0.008 (2)	−0.027 (2)	−0.013 (2)
C24	0.082 (3)	0.101 (3)	0.120 (4)	0.021 (3)	−0.019 (3)	−0.026 (3)
C25	0.054 (2)	0.0389 (18)	0.068 (2)	0.0034 (16)	0.002 (2)	−0.0024 (18)
C26	0.093 (3)	0.0530 (19)	0.064 (2)	0.010 (2)	−0.011 (2)	0.0091 (18)
C27	0.052 (2)	0.056 (2)	0.067 (2)	−0.007 (2)	−0.0064 (19)	0.001 (2)
C28	0.087 (3)	0.073 (2)	0.065 (2)	−0.021 (2)	−0.006 (2)	−0.0097 (19)

Geometric parameters (Å, º)

O1—C7	1.339 (4)	C11—C12	1.525 (4)
O1—C20	1.444 (3)	C11—H11	0.9800
O2—C7	1.204 (3)	C12—C13	1.553 (4)
O3—C21	1.343 (4)	C12—H12A	0.9700
O3—C1	1.463 (3)	C12—H12B	0.9700
O4—C21	1.198 (4)	C13—C16	1.505 (5)
O5—C23	1.347 (4)	C13—C14	1.519 (5)
O5—C6	1.438 (4)	C13—H13	0.9800
O6—C23	1.184 (4)	C14—H14A	0.9700
O7—C25	1.345 (3)	C14—H14B	0.9700
O7—C11	1.460 (3)	C15—C16	1.497 (5)
O8—C25	1.205 (3)	C15—H15	0.9800
O9—C27	1.344 (4)	C16—C17	1.314 (5)
O9—C15	1.433 (3)	C17—H17A	0.9300
O10—C27	1.194 (4)	C17—H17B	0.9300
C1—C2	1.495 (4)	C18—H18A	0.9600
C1—C10	1.528 (4)	C18—H18B	0.9600
C1—H1	0.9800	C18—H18C	0.9600
C2—C3	1.516 (4)	C19—H19A	0.9600
C2—H2A	0.9700	C19—H19B	0.9600
C2—H2B	0.9700	C19—H19C	0.9600
C3—C4	1.532 (4)	C20—H20A	0.9700
C3—H3A	0.9700	C20—H20B	0.9700
C3—H3B	0.9700	C21—C22	1.486 (4)
C4—C19	1.538 (4)	C22—H22A	0.9600
C4—C18	1.541 (4)	C22—H22B	0.9600
C4—C5	1.580 (4)	C22—H22C	0.9600
C5—C6	1.552 (4)	C23—C24	1.484 (5)
C5—C10	1.598 (4)	C24—H24A	0.9600
C5—H5	0.9800	C24—H24B	0.9600
C6—H6A	0.9700	C24—H24C	0.9600
C6—H6B	0.9700	C25—C26	1.480 (4)
C7—C8	1.512 (5)	C26—H26A	0.9600
C8—C14	1.537 (4)	C26—H26B	0.9600
C8—C15	1.540 (4)	C26—H26C	0.9600
C8—C9	1.585 (4)	C27—C28	1.491 (4)
C9—C11	1.543 (4)	C28—H28A	0.9600
C9—C10	1.568 (4)	C28—H28B	0.9600
C9—H9	0.9800	C28—H28C	0.9600
C10—C20	1.526 (4)
C7—O1—C20	117.9 (2)	C14—C13—C12	107.2 (3)
C21—O3—C1	118.3 (2)	C16—C13—H13	111.7
C23—O5—C6	117.3 (3)	C14—C13—H13	111.7
C25—O7—C11	118.5 (2)	C12—C13—H13	111.7
C27—O9—C15	119.3 (2)	C13—C14—C8	101.3 (3)
O3—C1—C2	110.2 (3)	C13—C14—H14A	111.5
O3—C1—C10	108.3 (2)	C8—C14—H14A	111.5
C2—C1—C10	114.9 (2)	C13—C14—H14B	111.5
O3—C1—H1	107.7	C8—C14—H14B	111.5
C2—C1—H1	107.7	H14A—C14—H14B	109.3
C10—C1—H1	107.7	O9—C15—C16	113.3 (3)
C1—C2—C3	108.0 (3)	O9—C15—C8	110.9 (2)
C1—C2—H2A	110.1	C16—C15—C8	103.3 (3)
C3—C2—H2A	110.1	O9—C15—H15	109.7
C1—C2—H2B	110.1	C16—C15—H15	109.7
C3—C2—H2B	110.1	C8—C15—H15	109.7
H2A—C2—H2B	108.4	C17—C16—C15	125.1 (4)
C2—C3—C4	113.0 (3)	C17—C16—C13	127.1 (4)
C2—C3—H3A	109.0	C15—C16—C13	107.6 (3)
C4—C3—H3A	109.0	C16—C17—H17A	120.0
C2—C3—H3B	109.0	C16—C17—H17B	120.0
C4—C3—H3B	109.0	H17A—C17—H17B	120.0
H3A—C3—H3B	107.8	C4—C18—H18A	109.5
C3—C4—C19	109.5 (3)	C4—C18—H18B	109.5
C3—C4—C18	105.9 (3)	H18A—C18—H18B	109.5
C19—C4—C18	108.0 (3)	C4—C18—H18C	109.5
C3—C4—C5	110.7 (2)	H18A—C18—H18C	109.5
C19—C4—C5	114.7 (3)	H18B—C18—H18C	109.5
C18—C4—C5	107.5 (3)	C4—C19—H19A	109.5
C6—C5—C4	108.4 (2)	C4—C19—H19B	109.5
C6—C5—C10	114.2 (2)	H19A—C19—H19B	109.5
C4—C5—C10	117.3 (3)	C4—C19—H19C	109.5
C6—C5—H5	105.3	H19A—C19—H19C	109.5
C4—C5—H5	105.3	H19B—C19—H19C	109.5
C10—C5—H5	105.3	O1—C20—C10	114.7 (2)
O5—C6—C5	114.4 (3)	O1—C20—H20A	108.6
O5—C6—H6A	108.6	C10—C20—H20A	108.6
C5—C6—H6A	108.6	O1—C20—H20B	108.6
O5—C6—H6B	108.6	C10—C20—H20B	108.6
C5—C6—H6B	108.6	H20A—C20—H20B	107.6
H6A—C6—H6B	107.6	O4—C21—O3	123.2 (3)
O2—C7—O1	117.8 (3)	O4—C21—C22	126.4 (4)
O2—C7—C8	122.3 (3)	O3—C21—C22	110.4 (3)
O1—C7—C8	119.8 (3)	C21—C22—H22A	109.5
C7—C8—C14	110.9 (3)	C21—C22—H22B	109.5
C7—C8—C15	108.4 (2)	H22A—C22—H22B	109.5
C14—C8—C15	98.1 (3)	C21—C22—H22C	109.5
C7—C8—C9	117.5 (3)	H22A—C22—H22C	109.5
C14—C8—C9	111.2 (2)	H22B—C22—H22C	109.5
C15—C8—C9	108.9 (2)	O6—C23—O5	123.7 (4)
C11—C9—C10	116.7 (2)	O6—C23—C24	126.0 (4)
C11—C9—C8	110.6 (2)	O5—C23—C24	110.3 (4)
C10—C9—C8	112.3 (2)	C23—C24—H24A	109.5
C11—C9—H9	105.4	C23—C24—H24B	109.5
C10—C9—H9	105.4	H24A—C24—H24B	109.5
C8—C9—H9	105.4	C23—C24—H24C	109.5
C20—C10—C1	114.6 (2)	H24A—C24—H24C	109.5
C20—C10—C9	105.5 (2)	H24B—C24—H24C	109.5
C1—C10—C9	110.8 (2)	O8—C25—O7	122.9 (3)
C20—C10—C5	107.2 (2)	O8—C25—C26	126.2 (3)
C1—C10—C5	106.1 (2)	O7—C25—C26	110.9 (3)
C9—C10—C5	112.8 (2)	C25—C26—H26A	109.5
O7—C11—C12	108.5 (2)	C25—C26—H26B	109.5
O7—C11—C9	104.9 (2)	H26A—C26—H26B	109.5
C12—C11—C9	114.0 (2)	C25—C26—H26C	109.5
O7—C11—H11	109.7	H26A—C26—H26C	109.5
C12—C11—H11	109.7	H26B—C26—H26C	109.5
C9—C11—H11	109.7	O10—C27—O9	123.6 (3)
C11—C12—C13	112.4 (3)	O10—C27—C28	126.3 (3)
C11—C12—H12A	109.1	O9—C27—C28	110.0 (3)
C13—C12—H12A	109.1	C27—C28—H28A	109.5
C11—C12—H12B	109.1	C27—C28—H28B	109.5
C13—C12—H12B	109.1	H28A—C28—H28B	109.5
H12A—C12—H12B	107.8	C27—C28—H28C	109.5
C16—C13—C14	103.2 (3)	H28A—C28—H28C	109.5
C16—C13—C12	110.8 (3)	H28B—C28—H28C	109.5
C1—C2—C3—C4	−60.8 (3)	C8—C9—C11—C12	−47.1 (3)
C2—C3—C4—C5	49.3 (4)	C9—C11—C12—C13	33.9 (3)
C3—C4—C5—C10	−42.2 (4)	C11—C12—C13—C14	29.1 (4)
O1—C7—C8—C9	−25.5 (4)	C8—C13—C14—C15	−31.66 (18)
C7—C8—C9—C10	0.0 (3)	C13—C14—C15—C16	−7.7 (2)
C8—C9—C10—C20	40.0 (3)