Absolute configuration of isoeichlerialactone.

The title seco-dammarane triterpenoid, C(27)H(42)O(4) (systematic name: 3-{(3S,3aR,5aR,6S,7S,9aR,9bR)-6,9a,9b-trimethyl-3-[(R)-2-methyl-5-oxotetra-hydro-furan-2-yl]-7-(prop-1-en-2-yl)dodeca-hydro-1H-cyclo-penta-[a]naphthalen-6-yl}propanoic acid), has been isolated for the first time from the seeds of Aglaia forbesii. The mol-ecule has three fused rings and all rings are in trans-fused. The two cyclo-hexane rings are in standard chair conformations and the cyclo-pentane ring adopts an envelope conformation. Its absolute configuration was determined by the refinement of the Flack parameter to 0.26 (17). In the crystal, mol-ecules are linked into chains along [010] by O-H⋯O hydrogen bonds.

Related literature

For details of ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For background to triterpenes and their biological activity, see: Engelmeier et al. (2000 ▶); Greger et al. (2001 ▶); Joycharat et al. (2008 ▶, 2010 ▶); Kim et al. (2006 ▶); Proksch et al. (2005 ▶). For a related structure, see: Singh & Aalbersberg (1992 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C27H42O4

M = 430.61

Monoclinic,

a = 11.8690 (4) Å

b = 7.0388 (3) Å

c = 14.1173 (5) Å

β = 94.962 (2)°

V = 1174.99 (8) Å3

Z = 2

Cu Kα radiation

μ = 0.63 mm−1

T = 100 K

0.56 × 0.14 × 0.06 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.720, T max = 0.962

29402 measured reflections

3253 independent reflections

3209 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.076

S = 1.05

3253 reflections

286 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1258 Friedel pairs

Flack parameter: 0.26 (17)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009499/rz2425sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009499/rz2425Isup2.hkl

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

C27H42O4	F(000) = 472
Mr = 430.61	Dx = 1.217 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 3253 reflections
a = 11.8690 (4) Å	θ = 3.1–63.5°
b = 7.0388 (3) Å	µ = 0.63 mm−1
c = 14.1173 (5) Å	T = 100 K
β = 94.962 (2)°	Needle, colourless
V = 1174.99 (8) Å3	0.56 × 0.14 × 0.06 mm
Z = 2

Bruker APEX DUO CCD area-detector diffractometer	3253 independent reflections
Radiation source: sealed tube	3209 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 63.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.720, Tmax = 0.962	k = −6→7
29402 measured reflections	l = −16→16

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.029	w = 1/[σ2(Fo2) + (0.0429P)2 + 0.3283P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.076	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.20 e Å−3
3253 reflections	Δρmin = −0.19 e Å−3
286 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0060 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1258 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.26 (17)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	1.02039 (9)	0.12899 (19)	0.98069 (8)	0.0230 (3)
O2	0.87449 (10)	−0.06457 (19)	0.94649 (9)	0.0269 (3)
H1O2	0.9144	−0.1370	0.9802	0.040*
O3	0.85383 (10)	0.17561 (19)	0.33396 (8)	0.0233 (3)
O4	0.92934 (11)	−0.0534 (2)	0.24954 (9)	0.0311 (3)
C1	0.73873 (13)	0.1943 (3)	0.85206 (11)	0.0165 (4)
H1A	0.7030	0.1786	0.9108	0.020*
H1B	0.7359	0.0721	0.8202	0.020*
C2	0.86329 (13)	0.2436 (3)	0.87797 (11)	0.0182 (4)
H2A	0.9005	0.2569	0.8198	0.022*
H2B	0.8674	0.3656	0.9101	0.022*
C3	0.92647 (13)	0.0998 (3)	0.94034 (11)	0.0181 (4)
C4	0.60276 (14)	0.5092 (3)	0.93919 (11)	0.0220 (4)
C5	0.65278 (13)	0.5261 (3)	0.84351 (11)	0.0180 (4)
H5A	0.7296	0.5754	0.8576	0.022*
C6	0.58968 (13)	0.6758 (3)	0.78086 (11)	0.0183 (4)
H6A	0.5825	0.7912	0.8174	0.022*
H6B	0.5142	0.6301	0.7612	0.022*
C7	0.65149 (14)	0.7207 (3)	0.69250 (11)	0.0190 (4)
H7A	0.7241	0.7776	0.7125	0.023*
H7B	0.6078	0.8131	0.6539	0.023*
C8	0.67072 (12)	0.5444 (3)	0.63145 (11)	0.0162 (4)
C9	0.72743 (13)	0.3854 (3)	0.69732 (11)	0.0150 (4)
H9A	0.8000	0.4401	0.7222	0.018*
C10	0.66594 (13)	0.3357 (3)	0.78849 (11)	0.0163 (4)
C11	0.75991 (13)	0.2106 (3)	0.64025 (11)	0.0178 (4)
H11A	0.6915	0.1505	0.6120	0.021*
H11B	0.7987	0.1198	0.6833	0.021*
C12	0.83640 (13)	0.2598 (3)	0.56117 (11)	0.0182 (4)
H12A	0.9090	0.3055	0.5890	0.022*
H12B	0.8492	0.1474	0.5238	0.022*
C13	0.77909 (13)	0.4124 (3)	0.49785 (11)	0.0164 (4)
H13A	0.7055	0.3611	0.4733	0.020*
C14	0.75490 (12)	0.5929 (3)	0.55434 (11)	0.0167 (4)
C15	0.71234 (13)	0.7261 (3)	0.47270 (11)	0.0195 (4)
H15A	0.7126	0.8574	0.4936	0.023*
H15B	0.6365	0.6920	0.4472	0.023*
C16	0.79861 (14)	0.6939 (3)	0.39867 (12)	0.0230 (4)
H16A	0.8625	0.7794	0.4101	0.028*
H16B	0.7638	0.7156	0.3349	0.028*
C17	0.83734 (13)	0.4841 (3)	0.41098 (11)	0.0185 (4)
H17A	0.9192	0.4831	0.4275	0.022*
C18	0.86642 (13)	0.6806 (3)	0.59992 (11)	0.0185 (4)
H18A	0.9253	0.6623	0.5583	0.028*
H18B	0.8872	0.6198	0.6598	0.028*
H18C	0.8558	0.8141	0.6099	0.028*
C19	0.55240 (13)	0.2318 (3)	0.76682 (11)	0.0184 (4)
H19A	0.5312	0.1710	0.8235	0.028*
H19B	0.5600	0.1379	0.7185	0.028*
H19C	0.4952	0.3218	0.7450	0.028*
C20	0.81270 (14)	0.3722 (3)	0.31846 (11)	0.0198 (4)
C21	0.88153 (15)	0.4451 (3)	0.23872 (12)	0.0256 (4)
H21A	0.8388	0.5371	0.1991	0.031*
H21B	0.9519	0.5027	0.2644	0.031*
C22	0.90316 (16)	0.2656 (3)	0.18336 (13)	0.0312 (5)
H22A	0.8455	0.2481	0.1311	0.037*
H22B	0.9767	0.2701	0.1583	0.037*
C23	0.89845 (14)	0.1082 (3)	0.25590 (12)	0.0246 (4)
C24	0.68744 (15)	0.3543 (3)	0.28607 (12)	0.0306 (5)
H24A	0.6503	0.2829	0.3322	0.046*
H24B	0.6786	0.2902	0.2259	0.046*
H24C	0.6544	0.4787	0.2797	0.046*
C25	0.67355 (16)	0.5249 (3)	1.02112 (12)	0.0328 (5)
H25A	0.6438	0.5250	1.0799	0.039*
H25B	0.7512	0.5354	1.0178	0.039*
C26	0.48110 (15)	0.4927 (3)	0.94372 (13)	0.0288 (5)
H26A	0.4654	0.4626	1.0076	0.043*
H26B	0.4522	0.3938	0.9016	0.043*
H26C	0.4455	0.6110	0.9250	0.043*
C27	0.55534 (13)	0.4831 (3)	0.58199 (11)	0.0198 (4)
H27A	0.4990	0.4881	0.6268	0.030*
H27B	0.5608	0.3557	0.5585	0.030*
H27C	0.5345	0.5673	0.5299	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0221 (6)	0.0222 (8)	0.0237 (6)	0.0001 (5)	−0.0039 (5)	−0.0002 (5)
O2	0.0239 (6)	0.0207 (8)	0.0348 (7)	−0.0002 (6)	−0.0052 (5)	0.0082 (6)
O3	0.0287 (6)	0.0248 (9)	0.0170 (6)	−0.0003 (5)	0.0044 (5)	−0.0021 (5)
O4	0.0385 (7)	0.0257 (10)	0.0308 (7)	−0.0002 (6)	0.0136 (5)	−0.0034 (6)
C1	0.0192 (8)	0.0153 (10)	0.0153 (7)	−0.0003 (7)	0.0036 (6)	−0.0009 (7)
C2	0.0209 (8)	0.0166 (11)	0.0172 (8)	0.0013 (7)	0.0019 (6)	0.0010 (7)
C3	0.0206 (8)	0.0183 (11)	0.0159 (8)	0.0003 (7)	0.0044 (6)	−0.0020 (7)
C4	0.0322 (9)	0.0147 (11)	0.0201 (8)	0.0067 (8)	0.0082 (7)	0.0009 (8)
C5	0.0178 (7)	0.0186 (11)	0.0176 (8)	−0.0009 (7)	0.0017 (6)	−0.0003 (7)
C6	0.0213 (8)	0.0156 (11)	0.0187 (8)	0.0005 (7)	0.0054 (6)	−0.0025 (7)
C7	0.0215 (8)	0.0166 (11)	0.0190 (8)	0.0019 (7)	0.0028 (6)	0.0036 (7)
C8	0.0172 (8)	0.0165 (11)	0.0150 (8)	0.0007 (7)	0.0024 (6)	0.0010 (7)
C9	0.0151 (7)	0.0138 (11)	0.0159 (7)	0.0004 (7)	0.0004 (6)	0.0006 (7)
C10	0.0161 (8)	0.0166 (11)	0.0161 (7)	0.0002 (7)	0.0015 (6)	0.0010 (7)
C11	0.0217 (8)	0.0154 (11)	0.0167 (8)	0.0007 (7)	0.0030 (6)	0.0007 (7)
C12	0.0210 (8)	0.0172 (11)	0.0169 (8)	0.0012 (7)	0.0040 (6)	−0.0022 (7)
C13	0.0165 (8)	0.0171 (11)	0.0157 (7)	−0.0001 (7)	0.0025 (6)	0.0005 (7)
C14	0.0164 (7)	0.0183 (11)	0.0156 (8)	−0.0003 (7)	0.0020 (6)	0.0016 (7)
C15	0.0226 (8)	0.0164 (11)	0.0198 (8)	0.0009 (7)	0.0028 (6)	0.0020 (7)
C16	0.0274 (9)	0.0225 (12)	0.0196 (8)	0.0005 (8)	0.0054 (7)	0.0049 (8)
C17	0.0167 (8)	0.0223 (12)	0.0165 (8)	−0.0003 (7)	0.0026 (6)	0.0011 (7)
C18	0.0206 (8)	0.0156 (11)	0.0197 (8)	−0.0020 (7)	0.0035 (6)	0.0001 (7)
C19	0.0187 (8)	0.0181 (11)	0.0187 (8)	−0.0004 (7)	0.0027 (6)	0.0003 (7)
C20	0.0225 (8)	0.0200 (12)	0.0168 (8)	0.0019 (7)	0.0018 (6)	0.0010 (7)
C21	0.0277 (9)	0.0305 (13)	0.0190 (8)	0.0014 (8)	0.0044 (7)	0.0027 (8)
C22	0.0354 (10)	0.0360 (14)	0.0237 (9)	−0.0007 (9)	0.0104 (7)	0.0009 (9)
C23	0.0261 (9)	0.0264 (14)	0.0219 (9)	−0.0034 (9)	0.0057 (7)	−0.0053 (8)
C24	0.0253 (9)	0.0462 (15)	0.0200 (8)	−0.0015 (9)	−0.0007 (7)	−0.0009 (9)
C25	0.0342 (10)	0.0465 (15)	0.0182 (8)	0.0131 (9)	0.0052 (7)	−0.0009 (9)
C26	0.0360 (10)	0.0268 (13)	0.0253 (9)	−0.0012 (9)	0.0122 (7)	−0.0018 (8)
C27	0.0169 (8)	0.0236 (12)	0.0190 (8)	0.0008 (7)	0.0015 (6)	0.0038 (7)

O1—C3	1.2246 (19)	C13—C14	1.540 (3)
O2—C3	1.318 (2)	C13—C17	1.544 (2)
O2—H1O2	0.8200	C13—H13A	0.9800
O3—C23	1.349 (2)	C14—C15	1.537 (2)
O3—C20	1.478 (2)	C14—C18	1.549 (2)
O4—C23	1.201 (3)	C15—C16	1.542 (2)
C1—C2	1.532 (2)	C15—H15A	0.9700
C1—C10	1.552 (2)	C15—H15B	0.9700
C1—H1A	0.9700	C16—C17	1.552 (3)
C1—H1B	0.9700	C16—H16A	0.9700
C2—C3	1.500 (2)	C16—H16B	0.9700
C2—H2A	0.9700	C17—C20	1.532 (2)
C2—H2B	0.9700	C17—H17A	0.9800
C4—C25	1.374 (3)	C18—H18A	0.9600
C4—C26	1.456 (2)	C18—H18B	0.9600
C4—C5	1.526 (2)	C18—H18C	0.9600
C5—C6	1.530 (2)	C19—H19A	0.9600
C5—C10	1.564 (3)	C19—H19B	0.9600
C5—H5A	0.9800	C19—H19C	0.9600
C6—C7	1.534 (2)	C20—C24	1.522 (2)
C6—H6A	0.9700	C20—C21	1.535 (2)
C6—H6B	0.9700	C21—C22	1.520 (3)
C7—C8	1.539 (3)	C21—H21A	0.9700
C7—H7A	0.9700	C21—H21B	0.9700
C7—H7B	0.9700	C22—C23	1.513 (3)
C8—C27	1.544 (2)	C22—H22A	0.9700
C8—C9	1.569 (2)	C22—H22B	0.9700
C8—C14	1.577 (2)	C24—H24A	0.9600
C9—C11	1.538 (2)	C24—H24B	0.9600
C9—C10	1.573 (2)	C24—H24C	0.9600
C9—H9A	0.9800	C25—H25A	0.9300
C10—C19	1.540 (2)	C25—H25B	0.9300
C11—C12	1.538 (2)	C26—H26A	0.9600
C11—H11A	0.9700	C26—H26B	0.9600
C11—H11B	0.9700	C26—H26C	0.9600
C12—C13	1.520 (2)	C27—H27A	0.9600
C12—H12A	0.9700	C27—H27B	0.9600
C12—H12B	0.9700	C27—H27C	0.9600
C3—O2—H1O2	109.5	C13—C14—C18	110.67 (13)
C23—O3—C20	110.86 (14)	C15—C14—C8	117.57 (12)
C2—C1—C10	118.06 (15)	C13—C14—C8	109.68 (14)
C2—C1—H1A	107.8	C18—C14—C8	111.65 (12)
C10—C1—H1A	107.8	C14—C15—C16	102.95 (13)
C2—C1—H1B	107.8	C14—C15—H15A	111.2
C10—C1—H1B	107.8	C16—C15—H15A	111.2
H1A—C1—H1B	107.1	C14—C15—H15B	111.2
C3—C2—C1	114.24 (15)	C16—C15—H15B	111.2
C3—C2—H2A	108.7	H15A—C15—H15B	109.1
C1—C2—H2A	108.7	C15—C16—C17	105.76 (14)
C3—C2—H2B	108.7	C15—C16—H16A	110.6
C1—C2—H2B	108.7	C17—C16—H16A	110.6
H2A—C2—H2B	107.6	C15—C16—H16B	110.6
O1—C3—O2	121.97 (16)	C17—C16—H16B	110.6
O1—C3—C2	123.28 (17)	H16A—C16—H16B	108.7
O2—C3—C2	114.73 (14)	C20—C17—C13	116.35 (15)
C25—C4—C26	120.40 (15)	C20—C17—C16	111.16 (14)
C25—C4—C5	118.84 (15)	C13—C17—C16	104.56 (13)
C26—C4—C5	120.56 (15)	C20—C17—H17A	108.2
C4—C5—C6	110.90 (13)	C13—C17—H17A	108.2
C4—C5—C10	115.86 (15)	C16—C17—H17A	108.2
C6—C5—C10	111.62 (12)	C14—C18—H18A	109.5
C4—C5—H5A	105.9	C14—C18—H18B	109.5
C6—C5—H5A	105.9	H18A—C18—H18B	109.5
C10—C5—H5A	105.9	C14—C18—H18C	109.5
C5—C6—C7	111.55 (13)	H18A—C18—H18C	109.5
C5—C6—H6A	109.3	H18B—C18—H18C	109.5
C7—C6—H6A	109.3	C10—C19—H19A	109.5
C5—C6—H6B	109.3	C10—C19—H19B	109.5
C7—C6—H6B	109.3	H19A—C19—H19B	109.5
H6A—C6—H6B	108.0	C10—C19—H19C	109.5
C6—C7—C8	113.22 (15)	H19A—C19—H19C	109.5
C6—C7—H7A	108.9	H19B—C19—H19C	109.5
C8—C7—H7A	108.9	O3—C20—C24	105.58 (15)
C6—C7—H7B	108.9	O3—C20—C17	108.60 (13)
C8—C7—H7B	108.9	C24—C20—C17	114.09 (14)
H7A—C7—H7B	107.7	O3—C20—C21	103.40 (14)
C7—C8—C27	108.07 (13)	C24—C20—C21	112.04 (13)
C7—C8—C9	108.67 (12)	C17—C20—C21	112.27 (15)
C27—C8—C9	112.73 (14)	C22—C21—C20	102.91 (16)
C7—C8—C14	110.24 (14)	C22—C21—H21A	111.2
C27—C8—C14	109.77 (12)	C20—C21—H21A	111.2
C9—C8—C14	107.36 (12)	C22—C21—H21B	111.2
C11—C9—C8	112.00 (12)	C20—C21—H21B	111.2
C11—C9—C10	113.94 (14)	H21A—C21—H21B	109.1
C8—C9—C10	115.97 (12)	C23—C22—C21	104.06 (14)
C11—C9—H9A	104.5	C23—C22—H22A	110.9
C8—C9—H9A	104.5	C21—C22—H22A	110.9
C10—C9—H9A	104.5	C23—C22—H22B	110.9
C19—C10—C1	104.15 (14)	C21—C22—H22B	110.9
C19—C10—C5	112.46 (13)	H22A—C22—H22B	109.0
C1—C10—C5	109.68 (12)	O4—C23—O3	122.54 (18)
C19—C10—C9	113.76 (12)	O4—C23—C22	127.84 (17)
C1—C10—C9	109.96 (12)	O3—C23—C22	109.62 (17)
C5—C10—C9	106.81 (13)	C20—C24—H24A	109.5
C9—C11—C12	112.96 (15)	C20—C24—H24B	109.5
C9—C11—H11A	109.0	H24A—C24—H24B	109.5
C12—C11—H11A	109.0	C20—C24—H24C	109.5
C9—C11—H11B	109.0	H24A—C24—H24C	109.5
C12—C11—H11B	109.0	H24B—C24—H24C	109.5
H11A—C11—H11B	107.8	C4—C25—H25A	120.0
C13—C12—C11	108.90 (13)	C4—C25—H25B	120.0
C13—C12—H12A	109.9	H25A—C25—H25B	120.0
C11—C12—H12A	109.9	C4—C26—H26A	109.5
C13—C12—H12B	109.9	C4—C26—H26B	109.5
C11—C12—H12B	109.9	H26A—C26—H26B	109.5
H12A—C12—H12B	108.3	C4—C26—H26C	109.5
C12—C13—C14	111.86 (12)	H26A—C26—H26C	109.5
C12—C13—C17	119.33 (13)	H26B—C26—H26C	109.5
C14—C13—C17	104.96 (14)	C8—C27—H27A	109.5
C12—C13—H13A	106.7	C8—C27—H27B	109.5
C14—C13—H13A	106.7	H27A—C27—H27B	109.5
C17—C13—H13A	106.7	C8—C27—H27C	109.5
C15—C14—C13	100.31 (12)	H27A—C27—H27C	109.5
C15—C14—C18	106.36 (14)	H27B—C27—H27C	109.5
C10—C1—C2—C3	179.42 (14)	C12—C13—C14—C18	61.31 (17)
C1—C2—C3—O1	−167.70 (14)	C17—C13—C14—C18	−69.49 (15)
C1—C2—C3—O2	14.2 (2)	C12—C13—C14—C8	−62.31 (16)
C25—C4—C5—C6	−127.01 (19)	C17—C13—C14—C8	166.89 (12)
C26—C4—C5—C6	47.9 (2)	C7—C8—C14—C15	−69.81 (18)
C25—C4—C5—C10	104.4 (2)	C27—C8—C14—C15	49.1 (2)
C26—C4—C5—C10	−80.6 (2)	C9—C8—C14—C15	171.98 (15)
C4—C5—C6—C7	169.65 (14)	C7—C8—C14—C13	176.54 (12)
C10—C5—C6—C7	−59.54 (18)	C27—C8—C14—C13	−64.53 (17)
C5—C6—C7—C8	57.01 (18)	C9—C8—C14—C13	58.33 (15)
C6—C7—C8—C27	71.31 (17)	C7—C8—C14—C18	53.50 (18)
C6—C7—C8—C9	−51.32 (17)	C27—C8—C14—C18	172.43 (15)
C6—C7—C8—C14	−168.72 (12)	C9—C8—C14—C18	−64.71 (17)
C7—C8—C9—C11	−174.60 (12)	C13—C14—C15—C16	−45.09 (16)
C27—C8—C9—C11	65.63 (16)	C18—C14—C15—C16	70.21 (16)
C14—C8—C9—C11	−55.38 (17)	C8—C14—C15—C16	−163.85 (15)
C7—C8—C9—C10	52.28 (18)	C14—C15—C16—C17	31.41 (17)
C27—C8—C9—C10	−67.49 (18)	C12—C13—C17—C20	87.32 (18)
C14—C8—C9—C10	171.50 (13)	C14—C13—C17—C20	−146.36 (14)
C2—C1—C10—C19	173.23 (14)	C12—C13—C17—C16	−149.67 (15)
C2—C1—C10—C5	−66.19 (17)	C14—C13—C17—C16	−23.35 (15)
C2—C1—C10—C9	50.98 (19)	C15—C16—C17—C20	121.33 (15)
C4—C5—C10—C19	58.99 (18)	C15—C16—C17—C13	−4.99 (17)
C6—C5—C10—C19	−69.22 (17)	C23—O3—C20—C24	94.59 (15)
C4—C5—C10—C1	−56.40 (17)	C23—O3—C20—C17	−142.66 (14)
C6—C5—C10—C1	175.39 (12)	C23—O3—C20—C21	−23.24 (16)
C4—C5—C10—C9	−175.53 (12)	C13—C17—C20—O3	−61.86 (17)
C6—C5—C10—C9	56.25 (15)	C16—C17—C20—O3	178.64 (13)
C11—C9—C10—C19	−62.02 (18)	C13—C17—C20—C24	55.6 (2)
C8—C9—C10—C19	70.2 (2)	C16—C17—C20—C24	−63.92 (19)
C11—C9—C10—C1	54.34 (17)	C13—C17—C20—C21	−175.56 (15)
C8—C9—C10—C1	−173.43 (13)	C16—C17—C20—C21	64.93 (18)
C11—C9—C10—C5	173.30 (12)	O3—C20—C21—C22	29.77 (16)
C8—C9—C10—C5	−54.48 (16)	C24—C20—C21—C22	−83.45 (19)
C8—C9—C11—C12	55.20 (17)	C17—C20—C21—C22	146.64 (15)
C10—C9—C11—C12	−170.68 (12)	C20—C21—C22—C23	−26.18 (17)
C9—C11—C12—C13	−54.70 (17)	C20—O3—C23—O4	−174.19 (16)
C11—C12—C13—C14	58.51 (17)	C20—O3—C23—C22	6.50 (18)
C11—C12—C13—C17	−178.51 (14)	C21—C22—C23—O4	−166.08 (19)
C12—C13—C14—C15	173.32 (12)	C21—C22—C23—O3	13.18 (18)
C17—C13—C14—C15	42.51 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1i	0.82	1.88	2.6541 (18)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1i	0.82	1.88	2.6541 (18)	156

Symmetry code: (i) .