Absolute configuration of di­acetyl­ated acrenol as its chloro­form solvate

The title compound, (15S)-15,16-diacetato-3β,20-epoxy-3α-hydroxy-9-epi-7-pimaren-19,6β-olide chloroform solvate, C₂₄H₃₂O₈·CHCl₃, formed from the di­acetyl­ation of acrenol, isolated from the tubers of Humirianthera ampla, crystallizes as a chloro­form solvate. The anomalous dispersion of the Cl atoms allows the absolute configuration to be determined. The structure is based on a pimarane skeleton and shows an identical conformation to the previously determined structures of icancinol and the acetyl­ated derivative of humirianthol.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.063
• wR factor = 0.161
• Data-to-parameter ratio = 7.3

checkCIF results

No syntax errors found

Structure: I
------------

ADDSYM reports no extra symmetry


 Alert Level A:



THETM_01  Alert A The value of sine(theta_max)/wavelength is less than 0.550
          Calculated sin(theta_max)/wavelength =    0.4826

Author response: The crystals diffracted poorly; the maximum theta readable from the ccd images was 20 deg.

 Alert Level C:



REFNR_01  Alert C Ratio of reflections to parameters is < 8 for a
          non-centrosymmetric structure, where ZMAX < 18
          sine(theta)/lambda                0.4826
          Proportion of unique data used    1.0000
          Ratio reflections to parameters   7.2590

RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.132

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           20.06
         From the CIF: _reflns_number_total               2410
         Count of symmetry unique reflns         1456
         Completeness (_total/calc)            165.52%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       954
         Fraction of Friedel pairs measured     0.655
         Are heavy atom types Z>Si present          yes
          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.


 1 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97.

3S,5R,6S,9S,10S,13R,15R,19R-3β,20-epoxy-3α-hydoroxy-15,16-diacetyl-7- pimaren-19,6β-olide1-(1-hydroxy-2,9-dimethyl-3-oxo-4,15- dioxapentacyclo[11.2.2^15,13.0^2,18.0^7,12]octadec-6-en-9-yl)- 2-methylcarbonyloxyethyl acetate

Crystal data

C24H32O8·CHCl3	F(000) = 1192
Mr = 567.86	Dx = 1.438 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8481 reflections
a = 8.0961 (8) Å	θ = 4.2–20.1°
b = 11.2954 (18) Å	µ = 0.40 mm^−1
c = 28.684 (4) Å	T = 100 K
V = 2623.1 (6) Å^3	Block, colourless
Z = 4	0.25 × 0.23 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer	2410 independent reflections
Radiation source: fine-focus sealed tube	1863 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.132
ψ scans and ω scans with κ offsets	θmax = 20.1°, θmin = 4.2°
Absorption correction: multi-scan The program Denzo-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The transmission factors in the experimental table are calculated from the 'size' command in the SHELXL-97 input file. Fox, G. C. & Holmes, K. C. (1966). Acta Cryst, 20, 886-891.	h = −7→7
Tmin = 0.907, Tmax = 0.925	k = −10→10
8481 measured reflections	l = −27→27

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.063	w = 1/[σ^2(Fo^2) + (0.0743P)^2 + 2.6838P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.161	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.20 e Å^−3
2410 reflections	Δρmin = −0.20 e Å^−3
332 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc2^λ3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0068 (19)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.17 (17)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The transmission factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fox, G. C. & Holmes, K. C. (1966). Acta Cryst, 20, 886–891.

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 2410 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
C1	0.7563 (11)	0.4113 (8)	0.7653 (4)	0.050 (3)
H1A	0.8477	0.4664	0.7727	0.060*
H1B	0.6867	0.4481	0.7409	0.060*
C2	0.6516 (11)	0.3885 (7)	0.8096 (3)	0.046 (3)
H2A	0.7019	0.4299	0.8366	0.055*
H2B	0.5387	0.4202	0.8051	0.055*
C3	0.6425 (12)	0.2560 (8)	0.8197 (4)	0.055 (3)
C4	0.5734 (13)	0.1887 (8)	0.7787 (3)	0.049 (3)
C5	0.6742 (11)	0.2180 (8)	0.7344 (3)	0.048 (3)
H5	0.6033	0.2642	0.7124	0.058*
C6	0.7190 (13)	0.0992 (9)	0.7118 (4)	0.055 (3)
H6	0.6311	0.0790	0.6887	0.066*
C7	0.8785 (13)	0.0970 (9)	0.6879 (3)	0.052 (3)
H7	0.9104	0.0248	0.6735	0.063*
C8	0.9808 (11)	0.1863 (9)	0.6845 (3)	0.051 (3)
C9	0.9442 (11)	0.3032 (8)	0.7067 (3)	0.044 (2)
H9	1.0512	0.3310	0.7202	0.053*
C10	0.8277 (11)	0.2923 (7)	0.7471 (3)	0.044 (3)
C11	0.9010 (10)	0.3928 (9)	0.6674 (3)	0.045 (3)
H11A	0.7982	0.3678	0.6516	0.054*
H11B	0.8820	0.4721	0.6812	0.054*
C12	1.0420 (12)	0.3996 (8)	0.6319 (3)	0.053 (3)
H12A	1.1393	0.4357	0.6473	0.064*
H12B	1.0081	0.4530	0.6063	0.064*
C13	1.0952 (12)	0.2781 (8)	0.6104 (3)	0.048 (3)
C14	1.1239 (11)	0.1868 (9)	0.6510 (3)	0.049 (3)
H14A	1.1383	0.1066	0.6378	0.058*
H14B	1.2264	0.2077	0.6680	0.058*
C15	1.2628 (11)	0.2956 (8)	0.5861 (3)	0.048 (3)
H15	1.3427	0.3333	0.6081	0.058*
C16	1.2568 (12)	0.3656 (9)	0.5410 (4)	0.059 (3)
H16A	1.2024	0.3182	0.5163	0.070*
H16B	1.1925	0.4392	0.5456	0.070*
C17	0.9616 (11)	0.2306 (9)	0.5773 (3)	0.062 (3)
H17A	0.9378	0.2899	0.5533	0.093*
H17B	0.8608	0.2137	0.5950	0.093*
H17C	1.0009	0.1577	0.5624	0.093*
C18	0.3845 (10)	0.2030 (8)	0.7726 (3)	0.052 (3)
H18A	0.3484	0.1588	0.7450	0.078*
H18B	0.3576	0.2870	0.7686	0.078*
H18C	0.3279	0.1722	0.8002	0.078*
C19	0.6109 (13)	0.0569 (10)	0.7861 (4)	0.057 (3)
C20	0.9152 (12)	0.2378 (8)	0.7885 (4)	0.054 (3)
H20A	0.9681	0.1631	0.7783	0.065*
H20B	1.0041	0.2922	0.7986	0.065*
C21	1.4688 (16)	0.1443 (10)	0.5901 (4)	0.061 (3)
C22	1.5278 (12)	0.0298 (9)	0.5709 (3)	0.056 (3)
H22A	1.6462	0.0213	0.5771	0.084*
H22B	1.5086	0.0279	0.5372	0.084*
H22C	1.4676	−0.0354	0.5857	0.084*
C23	1.4914 (15)	0.4847 (11)	0.5495 (4)	0.062 (3)
C24	1.6722 (13)	0.4973 (10)	0.5397 (4)	0.072 (3)
H24A	1.6952	0.5779	0.5289	0.108*
H24B	1.7046	0.4405	0.5155	0.108*
H24C	1.7350	0.4816	0.5682	0.108*
O25	0.5596 (8)	0.2413 (5)	0.8617 (2)	0.0560 (18)
H25A	0.5569	0.1690	0.8686	0.084*
O26	0.5678 (8)	−0.0069 (6)	0.8177 (3)	0.0543 (19)
O27	0.8112 (7)	0.2128 (5)	0.8279 (2)	0.0463 (16)
O28	0.7095 (8)	0.0124 (5)	0.7506 (3)	0.0524 (18)
O29	1.3247 (8)	0.1783 (6)	0.5719 (2)	0.0497 (17)
O30	1.5484 (9)	0.2028 (7)	0.6185 (3)	0.070 (2)
O31	1.4217 (9)	0.3936 (6)	0.5275 (2)	0.0534 (18)
O32	1.4172 (11)	0.5509 (7)	0.5739 (3)	0.077 (2)
C1S	0.9673 (12)	0.2592 (10)	0.9228 (4)	0.069 (3)
H1S	0.8853	0.2155	0.9032	0.082*
Cl1	0.9116 (4)	0.4096 (3)	0.92500 (11)	0.0863 (11)
Cl2	1.1635 (4)	0.2471 (3)	0.89705 (11)	0.0860 (11)
Cl3	0.9672 (3)	0.1985 (3)	0.97952 (10)	0.0768 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.055 (7)	0.020 (6)	0.076 (9)	0.011 (5)	−0.005 (6)	−0.005 (5)
C2	0.047 (6)	0.023 (6)	0.068 (8)	0.001 (4)	0.004 (5)	−0.002 (5)
C3	0.059 (7)	0.047 (8)	0.058 (8)	0.009 (6)	0.003 (6)	0.002 (6)
C4	0.075 (8)	0.026 (7)	0.046 (7)	−0.001 (6)	−0.005 (6)	0.002 (5)
C5	0.055 (6)	0.028 (6)	0.061 (7)	0.015 (5)	−0.009 (6)	−0.006 (5)
C6	0.062 (8)	0.040 (7)	0.062 (8)	0.004 (5)	−0.009 (6)	0.013 (6)
C7	0.068 (8)	0.041 (7)	0.047 (7)	−0.003 (6)	−0.006 (6)	−0.006 (5)
C8	0.038 (6)	0.059 (8)	0.056 (7)	−0.004 (6)	−0.010 (6)	0.011 (6)
C9	0.053 (6)	0.029 (6)	0.050 (6)	−0.006 (5)	0.010 (6)	−0.003 (6)
C10	0.050 (6)	0.026 (6)	0.055 (7)	−0.001 (5)	−0.024 (6)	0.001 (5)
C11	0.029 (6)	0.059 (7)	0.048 (6)	0.006 (5)	0.002 (5)	−0.008 (6)
C12	0.066 (7)	0.026 (6)	0.068 (8)	−0.001 (5)	−0.011 (6)	0.004 (5)
C13	0.063 (7)	0.031 (6)	0.052 (6)	0.000 (5)	−0.014 (6)	0.008 (5)
C14	0.038 (6)	0.043 (7)	0.065 (7)	−0.002 (5)	−0.010 (5)	−0.003 (6)
C15	0.056 (7)	0.041 (7)	0.048 (7)	0.002 (5)	−0.003 (5)	−0.005 (6)
C16	0.057 (8)	0.058 (8)	0.060 (8)	0.004 (5)	0.000 (6)	0.001 (6)
C17	0.078 (7)	0.056 (7)	0.051 (7)	0.007 (6)	−0.015 (6)	0.005 (6)
C18	0.046 (6)	0.037 (6)	0.074 (7)	−0.003 (5)	−0.015 (5)	−0.008 (5)
C19	0.056 (7)	0.051 (9)	0.064 (9)	−0.004 (6)	0.000 (7)	−0.014 (7)
C20	0.063 (6)	0.023 (6)	0.077 (8)	0.012 (5)	−0.018 (7)	0.001 (6)
C21	0.077 (9)	0.047 (8)	0.060 (9)	0.001 (7)	0.005 (8)	0.002 (7)
C22	0.057 (6)	0.050 (7)	0.061 (8)	0.000 (5)	0.010 (6)	0.001 (6)
C23	0.082 (10)	0.038 (8)	0.066 (9)	−0.004 (7)	0.000 (7)	0.008 (7)
C24	0.067 (8)	0.070 (8)	0.080 (9)	−0.003 (6)	−0.009 (7)	0.022 (7)
O25	0.073 (4)	0.042 (4)	0.053 (5)	−0.010 (4)	−0.002 (4)	0.001 (4)
O26	0.058 (4)	0.045 (5)	0.060 (5)	−0.005 (3)	−0.003 (4)	0.007 (4)
O27	0.045 (4)	0.041 (4)	0.052 (4)	0.003 (3)	0.010 (3)	0.005 (3)
O28	0.056 (4)	0.041 (4)	0.061 (5)	0.002 (3)	−0.002 (4)	0.002 (4)
O29	0.041 (4)	0.055 (5)	0.053 (4)	0.018 (4)	−0.001 (3)	−0.005 (4)
O30	0.069 (5)	0.064 (5)	0.078 (6)	0.010 (4)	−0.014 (4)	−0.013 (5)
O31	0.062 (5)	0.041 (4)	0.057 (5)	−0.001 (4)	−0.005 (4)	−0.001 (4)
O32	0.100 (6)	0.060 (6)	0.071 (6)	−0.013 (5)	−0.001 (5)	−0.007 (5)
C1S	0.063 (7)	0.084 (9)	0.058 (7)	0.011 (6)	−0.007 (6)	−0.007 (6)
Cl1	0.125 (3)	0.055 (2)	0.079 (2)	0.0194 (18)	−0.011 (2)	0.0021 (17)
Cl2	0.089 (2)	0.100 (3)	0.069 (2)	0.0051 (19)	0.0046 (17)	0.0012 (19)
Cl3	0.086 (2)	0.071 (2)	0.074 (2)	0.0042 (16)	−0.0038 (16)	0.0121 (16)

Geometric parameters (Å, º)

C1—C2	1.550 (12)	C14—H14A	0.9900
C1—C10	1.554 (12)	C14—H14B	0.9900
C1—H1A	0.9900	C15—O29	1.473 (10)
C1—H1B	0.9900	C15—C16	1.516 (13)
C2—C3	1.526 (12)	C15—H15	1.0000
C2—H2A	0.9900	C16—O31	1.426 (11)
C2—H2B	0.9900	C16—H16A	0.9900
C3—O25	1.390 (11)	C16—H16B	0.9900
C3—O27	1.469 (10)	C17—H17A	0.9800
C3—C4	1.507 (13)	C17—H17B	0.9800
C4—C19	1.534 (15)	C17—H17C	0.9800
C4—C5	1.547 (13)	C18—H18A	0.9800
C4—C18	1.548 (12)	C18—H18B	0.9800
C5—C6	1.533 (13)	C18—H18C	0.9800
C5—C10	1.543 (12)	C19—O26	1.210 (12)
C5—H5	1.0000	C19—O28	1.388 (12)
C6—C7	1.463 (13)	C20—O27	1.438 (11)
C6—O28	1.484 (11)	C20—H20A	0.9900
C6—H6	1.0000	C20—H20B	0.9900
C7—C8	1.309 (12)	C21—O30	1.233 (12)
C7—H7	0.9500	C21—O29	1.333 (13)
C8—C9	1.494 (13)	C21—C22	1.484 (14)
C8—C14	1.506 (12)	C22—H22A	0.9800
C9—C10	1.499 (12)	C22—H22B	0.9800
C9—C11	1.555 (12)	C22—H22C	0.9800
C9—H9	1.0000	C23—O32	1.188 (12)
C10—C20	1.514 (12)	C23—O31	1.333 (13)
C11—C12	1.531 (12)	C23—C24	1.497 (14)
C11—H11A	0.9900	C24—H24A	0.9800
C11—H11B	0.9900	C24—H24B	0.9800
C12—C13	1.566 (13)	C24—H24C	0.9800
C12—H12A	0.9900	O25—H25A	0.8400
C12—H12B	0.9900	C1S—Cl2	1.757 (10)
C13—C17	1.537 (12)	C1S—Cl1	1.759 (11)
C13—C15	1.539 (12)	C1S—Cl3	1.765 (10)
C13—C14	1.573 (12)	C1S—H1S	1.0000
C2—C1—C10	109.6 (7)	C15—C13—C14	106.8 (7)
C2—C1—H1A	109.7	C12—C13—C14	108.8 (8)
C10—C1—H1A	109.7	C8—C14—C13	111.2 (7)
C2—C1—H1B	109.7	C8—C14—H14A	109.4
C10—C1—H1B	109.7	C13—C14—H14A	109.4
H1A—C1—H1B	108.2	C8—C14—H14B	109.4
C3—C2—C1	110.1 (7)	C13—C14—H14B	109.4
C3—C2—H2A	109.6	H14A—C14—H14B	108.0
C1—C2—H2A	109.6	O29—C15—C16	104.2 (7)
C3—C2—H2B	109.6	O29—C15—C13	108.0 (7)
C1—C2—H2B	109.6	C16—C15—C13	115.1 (8)
H2A—C2—H2B	108.2	O29—C15—H15	109.8
O25—C3—O27	105.6 (8)	C16—C15—H15	109.8
O25—C3—C4	115.9 (8)	C13—C15—H15	109.8
O27—C3—C4	107.7 (8)	O31—C16—C15	108.5 (8)
O25—C3—C2	107.7 (8)	O31—C16—H16A	110.0
O27—C3—C2	108.1 (7)	C15—C16—H16A	110.0
C4—C3—C2	111.4 (8)	O31—C16—H16B	110.0
C3—C4—C19	107.9 (8)	C15—C16—H16B	110.0
C3—C4—C5	109.7 (8)	H16A—C16—H16B	108.4
C19—C4—C5	102.5 (8)	C13—C17—H17A	109.5
C3—C4—C18	113.8 (8)	C13—C17—H17B	109.5
C19—C4—C18	108.2 (8)	H17A—C17—H17B	109.5
C5—C4—C18	113.9 (8)	C13—C17—H17C	109.5
C6—C5—C10	112.7 (7)	H17A—C17—H17C	109.5
C6—C5—C4	106.5 (8)	H17B—C17—H17C	109.5
C10—C5—C4	110.3 (8)	C4—C18—H18A	109.5
C6—C5—H5	109.1	C4—C18—H18B	109.5
C10—C5—H5	109.1	H18A—C18—H18B	109.5
C4—C5—H5	109.1	C4—C18—H18C	109.5
C7—C6—O28	112.8 (8)	H18A—C18—H18C	109.5
C7—C6—C5	114.9 (8)	H18B—C18—H18C	109.5
O28—C6—C5	104.5 (8)	O26—C19—O28	120.0 (10)
C7—C6—H6	108.1	O26—C19—C4	128.6 (10)
O28—C6—H6	108.1	O28—C19—C4	111.4 (10)
C5—C6—H6	108.1	O27—C20—C10	115.1 (7)
C8—C7—C6	125.4 (9)	O27—C20—H20A	108.5
C8—C7—H7	117.3	C10—C20—H20A	108.5
C6—C7—H7	117.3	O27—C20—H20B	108.5
C7—C8—C9	121.6 (9)	C10—C20—H20B	108.5
C7—C8—C14	122.5 (10)	H20A—C20—H20B	107.5
C9—C8—C14	114.9 (8)	O30—C21—O29	124.1 (10)
C8—C9—C10	112.4 (7)	O30—C21—C22	123.0 (12)
C8—C9—C11	108.2 (8)	O29—C21—C22	112.9 (11)
C10—C9—C11	118.2 (7)	C21—C22—H22A	109.5
C8—C9—H9	105.7	C21—C22—H22B	109.5
C10—C9—H9	105.7	H22A—C22—H22B	109.5
C11—C9—H9	105.7	C21—C22—H22C	109.5
C9—C10—C20	110.2 (7)	H22A—C22—H22C	109.5
C9—C10—C5	111.6 (7)	H22B—C22—H22C	109.5
C20—C10—C5	109.9 (8)	O32—C23—O31	123.4 (11)
C9—C10—C1	115.1 (8)	O32—C23—C24	123.1 (12)
C20—C10—C1	105.2 (8)	O31—C23—C24	113.5 (12)
C5—C10—C1	104.5 (7)	C23—C24—H24A	109.5
C12—C11—C9	110.3 (7)	C23—C24—H24B	109.5
C12—C11—H11A	109.6	H24A—C24—H24B	109.5
C9—C11—H11A	109.6	C23—C24—H24C	109.5
C12—C11—H11B	109.6	H24A—C24—H24C	109.5
C9—C11—H11B	109.6	H24B—C24—H24C	109.5
H11A—C11—H11B	108.1	C3—O25—H25A	109.5
C11—C12—C13	115.0 (7)	C20—O27—C3	110.6 (7)
C11—C12—H12A	108.5	C19—O28—C6	109.9 (8)
C13—C12—H12A	108.5	C21—O29—C15	116.7 (8)
C11—C12—H12B	108.5	C23—O31—C16	116.0 (9)
C13—C12—H12B	108.5	Cl2—C1S—Cl1	108.8 (6)
H12A—C12—H12B	107.5	Cl2—C1S—Cl3	111.0 (5)
C17—C13—C15	112.7 (8)	Cl1—C1S—Cl3	110.0 (6)
C17—C13—C12	110.9 (7)	Cl2—C1S—H1S	109.0
C15—C13—C12	108.0 (7)	Cl1—C1S—H1S	109.0
C17—C13—C14	109.5 (8)	Cl3—C1S—H1S	109.0
C10—C1—C2—C3	−3.5 (10)	C2—C1—C10—C5	62.5 (9)
C1—C2—C3—O25	175.0 (7)	C8—C9—C11—C12	−56.3 (10)
C1—C2—C3—O27	61.3 (10)	C10—C9—C11—C12	174.6 (7)
C1—C2—C3—C4	−56.8 (10)	C9—C11—C12—C13	54.4 (10)
O25—C3—C4—C19	−71.3 (11)	C11—C12—C13—C17	70.5 (10)
O27—C3—C4—C19	46.7 (10)	C11—C12—C13—C15	−165.6 (7)
C2—C3—C4—C19	165.1 (8)	C11—C12—C13—C14	−49.9 (10)
O25—C3—C4—C5	177.7 (7)	C7—C8—C14—C13	110.2 (10)
O27—C3—C4—C5	−64.3 (9)	C9—C8—C14—C13	−58.3 (10)
C2—C3—C4—C5	54.2 (10)	C17—C13—C14—C8	−72.1 (10)
O25—C3—C4—C18	48.8 (11)	C15—C13—C14—C8	165.6 (8)
O27—C3—C4—C18	166.8 (7)	C12—C13—C14—C8	49.2 (10)
C2—C3—C4—C18	−74.8 (10)	C17—C13—C15—O29	−65.5 (9)
C3—C4—C5—C6	130.5 (8)	C12—C13—C15—O29	171.7 (7)
C19—C4—C5—C6	16.0 (9)	C14—C13—C15—O29	54.8 (9)
C18—C4—C5—C6	−100.6 (9)	C17—C13—C15—C16	50.5 (11)
C3—C4—C5—C10	7.9 (10)	C12—C13—C15—C16	−72.4 (10)
C19—C4—C5—C10	−106.6 (8)	C14—C13—C15—C16	170.7 (8)
C18—C4—C5—C10	136.8 (8)	O29—C15—C16—O31	−72.8 (9)
C10—C5—C6—C7	−25.9 (12)	C13—C15—C16—O31	169.1 (8)
C4—C5—C6—C7	−147.0 (8)	C3—C4—C19—O26	60.2 (14)
C10—C5—C6—O28	98.2 (9)	C5—C4—C19—O26	176.0 (10)
C4—C5—C6—O28	−22.8 (9)	C18—C4—C19—O26	−63.4 (14)
O28—C6—C7—C8	−119.7 (11)	C3—C4—C19—O28	−118.9 (9)
C5—C6—C7—C8	0.0 (15)	C5—C4—C19—O28	−3.1 (10)
C6—C7—C8—C9	1.3 (16)	C18—C4—C19—O28	117.5 (9)
C6—C7—C8—C14	−166.4 (9)	C9—C10—C20—O27	−174.4 (7)
C7—C8—C9—C10	24.3 (13)	C5—C10—C20—O27	−50.9 (10)
C14—C8—C9—C10	−167.1 (7)	C1—C10—C20—O27	61.0 (10)
C7—C8—C9—C11	−107.9 (10)	C10—C20—O27—C3	−4.6 (10)
C14—C8—C9—C11	60.6 (9)	O25—C3—O27—C20	−172.5 (7)
C8—C9—C10—C20	73.3 (9)	C4—C3—O27—C20	63.1 (9)
C11—C9—C10—C20	−159.6 (8)	C2—C3—O27—C20	−57.4 (10)
C8—C9—C10—C5	−49.2 (10)	O26—C19—O28—C6	169.1 (9)
C11—C9—C10—C5	77.9 (10)	C4—C19—O28—C6	−11.7 (11)
C8—C9—C10—C1	−168.0 (8)	C7—C6—O28—C19	147.0 (8)
C11—C9—C10—C1	−40.9 (11)	C5—C6—O28—C19	21.5 (10)
C6—C5—C10—C9	50.6 (10)	O30—C21—O29—C15	2.4 (14)
C4—C5—C10—C9	169.4 (7)	C22—C21—O29—C15	−175.3 (8)
C6—C5—C10—C20	−72.0 (10)	C16—C15—O29—C21	117.6 (9)
C4—C5—C10—C20	46.8 (9)	C13—C15—O29—C21	−119.5 (8)
C6—C5—C10—C1	175.5 (8)	O32—C23—O31—C16	−10.7 (15)
C4—C5—C10—C1	−65.6 (9)	C24—C23—O31—C16	170.4 (8)
C2—C1—C10—C9	−174.7 (7)	C15—C16—O31—C23	−79.6 (10)
C2—C1—C10—C20	−53.3 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O25—H25A···O32^i	0.84	2.13	2.840 (11)	142
O25—H25A···O26	0.84	2.47	3.075 (9)	130

Symmetry code: (i) −x+2, y−1/2, −z+3/2.