Absolute configuration of methyl isoeichlerialactone.

The title compound, C(28)H(44)O(4)·0.56H(2)O, is a co-crystal of methyl isoeichlerialactone monohydrate as the major component and methyl isoeichlerialactone as the minor component in a 0.55778 (3):0.44222 (3) ratio. The conformations of both components are identical except for that of the -COOCH(3) group of the methyl propanoate side chain on the cyclo-hexane ring which is positionally disordered over two orientations. The mol-ecule of methyl isoeichlerialactone has three fused rings and all rings are trans-fused. The two cyclo-hexane rings are in standard chair conformations and the cyclo-pentane ring adopts an envelope conformation. In the crystal, weak C-H⋯O inter-actions link methyl isoeichlerialactone mol-ecules into screw chains along [010]. The crystal structure is further stabilized by O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions.

Related literature

For details of ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For previous studies on 3,4-secodammarane triterpenes in Aglaia see: Pointinger et al. (2008 ▶); Seger et al. (2008 ▶); Joycharat et al. (2010 ▶). For related structures, see: Fun et al. (2010 ▶); Joycharat et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C28H44O4·0.56H2O

M = 454.68

Orthorhombic,

a = 7.2246 (2) Å

b = 13.3872 (4) Å

c = 26.1898 (8) Å

V = 2533.00 (13) Å3

Z = 4

Cu Kα radiation

μ = 0.62 mm−1

T = 100 K

0.34 × 0.23 × 0.05 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.818, T max = 0.969

52930 measured reflections

3968 independent reflections

3522 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.099

S = 1.05

3968 reflections

327 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1634 Friedel pairs

Flack parameter: 0.0 (2)

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/S1600536810018295/sj5002sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018295/sj5002Isup2.hkl

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

C28H44O4·0.56H2O	F(000) = 998.1
Mr = 454.68	Dx = 1.192 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3968 reflections
a = 7.2246 (2) Å	θ = 3.4–63.0°
b = 13.3872 (4) Å	µ = 0.62 mm−1
c = 26.1898 (8) Å	T = 100 K
V = 2533.00 (13) Å3	Plate, colorless
Z = 4	0.34 × 0.23 × 0.05 mm

Bruker APEXII DUO CCD area-detector diffractometer	3968 independent reflections
Radiation source: sealed tube	3522 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 63.0°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→7
Tmin = 0.818, Tmax = 0.969	k = −15→15
52930 measured reflections	l = −29→30

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0559P)2 + 0.5383P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3968 reflections	Δρmax = 0.18 e Å−3
327 parameters	Δρmin = −0.19 e Å−3
0 restraints	Absolute structure: Flack (1983), 1634 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.0 (2)

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	Occ. (<1)
O1A	−0.273 (2)	−0.1142 (10)	0.8174 (8)	0.044 (3)	0.558 (3)
O2A	−0.1434 (13)	−0.2556 (6)	0.8441 (4)	0.050 (4)	0.558 (3)
O1B	−0.1464 (14)	−0.2552 (8)	0.8408 (5)	0.044 (4)	0.442 (3)
O2B	−0.286 (3)	−0.1069 (15)	0.8266 (10)	0.051 (5)	0.442 (3)
O3	0.0321 (2)	0.44352 (10)	0.80263 (5)	0.0326 (4)
O4	−0.1588 (2)	0.51204 (12)	0.74616 (6)	0.0430 (4)
C1	−0.0153 (3)	−0.07230 (15)	0.91294 (7)	0.0241 (4)
H1B	−0.0341	−0.1316	0.9336	0.029*
H1A	−0.1305	−0.0351	0.9133	0.029*
C2	0.0210 (3)	−0.10586 (17)	0.85799 (7)	0.0318 (5)
H2A	0.0452	−0.0482	0.8366	0.038*
H2B	0.1287	−0.1491	0.8569	0.038*
C3	−0.1439 (3)	−0.16044 (19)	0.83871 (8)	0.0349 (5)
C4	0.2820 (3)	−0.16680 (16)	0.97910 (8)	0.0302 (5)
C5	0.3125 (3)	−0.07180 (15)	0.94891 (8)	0.0259 (5)
H5A	0.3543	−0.0933	0.9151	0.031*
C6	0.4708 (3)	−0.00839 (15)	0.97075 (8)	0.0289 (5)
H6A	0.4339	0.0184	1.0036	0.035*
H6B	0.5786	−0.0504	0.9760	0.035*
C7	0.5214 (3)	0.07702 (15)	0.93534 (7)	0.0263 (5)
H7A	0.5692	0.0495	0.9037	0.032*
H7B	0.6196	0.1158	0.9510	0.032*
C8	0.3586 (3)	0.14722 (15)	0.92282 (7)	0.0221 (4)
C9	0.1912 (3)	0.08197 (14)	0.90423 (7)	0.0205 (4)
H9A	0.2350	0.0505	0.8727	0.025*
C10	0.1343 (3)	−0.00757 (15)	0.93938 (7)	0.0224 (4)
C11	0.0263 (3)	0.14707 (15)	0.88736 (7)	0.0247 (5)
H11A	−0.0693	0.1041	0.8734	0.030*
H11B	−0.0248	0.1803	0.9171	0.030*
C12	0.0774 (3)	0.22616 (15)	0.84740 (7)	0.0259 (5)
H12A	0.1084	0.1938	0.8154	0.031*
H12B	−0.0276	0.2698	0.8415	0.031*
C13	0.2412 (3)	0.28711 (15)	0.86592 (7)	0.0239 (5)
H13A	0.2034	0.3184	0.8981	0.029*
C14	0.4102 (3)	0.22061 (15)	0.87820 (7)	0.0224 (5)
C15	0.5590 (3)	0.30013 (15)	0.88955 (8)	0.0289 (5)
H15A	0.6820	0.2731	0.8840	0.035*
H15B	0.5498	0.3230	0.9246	0.035*
C16	0.5195 (3)	0.38659 (16)	0.85200 (8)	0.0337 (5)
H16A	0.6069	0.3853	0.8239	0.040*
H16B	0.5299	0.4505	0.8693	0.040*
C17	0.3182 (3)	0.37058 (15)	0.83198 (7)	0.0267 (5)
H17A	0.3272	0.3441	0.7972	0.032*
C18	0.4771 (3)	0.16521 (15)	0.82951 (7)	0.0270 (5)
H18A	0.5017	0.2129	0.8030	0.041*
H18B	0.3827	0.1197	0.8183	0.041*
H18C	0.5881	0.1287	0.8371	0.041*
C19	0.0426 (3)	0.02362 (15)	0.99005 (7)	0.0256 (5)
H19A	−0.0180	−0.0331	1.0050	0.038*
H19B	−0.0468	0.0752	0.9836	0.038*
H19C	0.1354	0.0482	1.0131	0.038*
C20	0.2067 (3)	0.46699 (16)	0.82936 (8)	0.0317 (5)
C21	0.2973 (4)	0.54557 (17)	0.79445 (9)	0.0412 (6)
H21A	0.3644	0.5949	0.8143	0.049*
H21B	0.3819	0.5144	0.7705	0.049*
C22	0.1347 (4)	0.59283 (19)	0.76687 (9)	0.0447 (6)
H22A	0.0959	0.6538	0.7838	0.054*
H22B	0.1663	0.6081	0.7317	0.054*
C23	−0.0139 (3)	0.51499 (17)	0.76943 (7)	0.0346 (5)
C24	0.1526 (4)	0.51003 (18)	0.88086 (8)	0.0483 (7)
H24A	0.0661	0.4661	0.8973	0.073*
H24B	0.0965	0.5744	0.8761	0.073*
H24C	0.2610	0.5169	0.9018	0.073*
C25	0.2746 (3)	−0.25788 (19)	0.95303 (10)	0.0453 (6)
H25A	0.2633	−0.3173	0.9712	0.054*
H25B	0.2809	−0.2590	0.9176	0.054*
C26	0.2721 (3)	−0.16537 (19)	1.03380 (9)	0.0429 (6)
H26A	0.2412	−0.2308	1.0461	0.064*
H26B	0.1789	−0.1187	1.0444	0.064*
H26C	0.3898	−0.1456	1.0475	0.064*
C27	0.3098 (3)	0.20673 (15)	0.97170 (7)	0.0264 (5)
H27A	0.1833	0.2283	0.9700	0.040*
H27B	0.3894	0.2640	0.9743	0.040*
H27C	0.3266	0.1648	1.0011	0.040*
C28A	−0.3009 (7)	−0.3076 (4)	0.82808 (17)	0.0485 (9)	0.558 (3)
H28A	−0.2859	−0.3774	0.8353	0.073*	0.558 (3)
H28B	−0.3175	−0.2984	0.7920	0.073*	0.558 (3)
H28C	−0.4074	−0.2826	0.8459	0.073*	0.558 (3)
C28B	−0.4627 (8)	−0.1624 (5)	0.8110 (2)	0.0485 (9)	0.442 (3)
H28D	−0.5465	−0.1166	0.7949	0.073*	0.442 (3)
H28E	−0.5202	−0.1905	0.8407	0.073*	0.442 (3)
H28F	−0.4319	−0.2149	0.7875	0.073*	0.442 (3)
O1W	0.3649 (5)	0.8328 (3)	0.78098 (12)	0.0633 (11)	0.558 (3)
H1W1	0.2851	0.8846	0.7596	0.095*	0.558 (3)
H2W1	0.4764	0.8450	0.7786	0.095*	0.558 (3)

	U11	U22	U33	U12	U13	U23
O1A	0.063 (6)	0.024 (4)	0.043 (5)	−0.004 (3)	−0.021 (4)	−0.002 (4)
O2A	0.080 (6)	0.034 (6)	0.036 (4)	−0.034 (3)	−0.006 (4)	0.010 (3)
O1B	0.039 (6)	0.035 (8)	0.056 (7)	0.020 (5)	−0.002 (4)	−0.017 (5)
O2B	0.028 (5)	0.069 (8)	0.057 (10)	−0.002 (4)	−0.010 (4)	−0.019 (4)
O3	0.0336 (9)	0.0289 (8)	0.0354 (8)	0.0033 (7)	−0.0003 (7)	0.0093 (7)
O4	0.0472 (11)	0.0473 (10)	0.0344 (8)	0.0120 (8)	−0.0045 (8)	0.0014 (8)
C1	0.0210 (11)	0.0223 (11)	0.0289 (10)	0.0008 (8)	0.0004 (9)	0.0052 (8)
C2	0.0377 (13)	0.0289 (12)	0.0289 (11)	−0.0039 (10)	−0.0012 (10)	−0.0018 (9)
C3	0.0434 (16)	0.0353 (16)	0.0261 (11)	0.0009 (12)	−0.0010 (11)	−0.0051 (12)
C4	0.0179 (11)	0.0294 (13)	0.0434 (12)	0.0039 (9)	−0.0001 (9)	0.0099 (10)
C5	0.0228 (11)	0.0259 (12)	0.0291 (10)	0.0037 (9)	0.0015 (9)	0.0032 (9)
C6	0.0218 (11)	0.0319 (13)	0.0330 (10)	0.0039 (9)	−0.0037 (9)	0.0065 (10)
C7	0.0187 (11)	0.0319 (12)	0.0284 (10)	−0.0018 (9)	−0.0027 (9)	0.0040 (9)
C8	0.0181 (11)	0.0244 (12)	0.0239 (9)	0.0008 (8)	0.0003 (8)	−0.0004 (8)
C9	0.0183 (11)	0.0216 (11)	0.0218 (9)	0.0015 (8)	−0.0003 (8)	−0.0003 (8)
C10	0.0209 (11)	0.0226 (12)	0.0238 (9)	0.0024 (8)	−0.0007 (8)	0.0002 (9)
C11	0.0194 (11)	0.0252 (12)	0.0294 (10)	−0.0009 (8)	−0.0025 (9)	0.0033 (9)
C12	0.0221 (11)	0.0267 (12)	0.0291 (10)	0.0011 (8)	−0.0032 (8)	0.0037 (9)
C13	0.0240 (11)	0.0238 (12)	0.0240 (10)	0.0019 (8)	0.0007 (8)	−0.0011 (9)
C14	0.0189 (11)	0.0226 (11)	0.0257 (10)	−0.0006 (8)	−0.0009 (8)	0.0001 (9)
C15	0.0241 (12)	0.0327 (12)	0.0299 (11)	−0.0021 (9)	−0.0001 (8)	0.0022 (9)
C16	0.0338 (13)	0.0300 (13)	0.0372 (12)	−0.0067 (10)	−0.0007 (10)	0.0047 (10)
C17	0.0293 (12)	0.0235 (11)	0.0274 (10)	−0.0012 (9)	0.0002 (9)	−0.0004 (9)
C18	0.0253 (12)	0.0285 (12)	0.0273 (10)	0.0020 (9)	0.0053 (9)	0.0031 (9)
C19	0.0230 (11)	0.0262 (11)	0.0277 (10)	−0.0001 (9)	0.0027 (9)	0.0011 (9)
C20	0.0390 (13)	0.0245 (12)	0.0316 (11)	−0.0026 (9)	−0.0025 (10)	0.0024 (9)
C21	0.0503 (15)	0.0284 (13)	0.0450 (13)	−0.0039 (11)	−0.0042 (12)	0.0064 (11)
C22	0.0555 (17)	0.0375 (15)	0.0410 (13)	0.0027 (11)	−0.0003 (12)	0.0145 (11)
C23	0.0438 (15)	0.0349 (14)	0.0252 (10)	0.0083 (11)	0.0036 (11)	0.0010 (10)
C24	0.078 (2)	0.0308 (14)	0.0359 (12)	0.0161 (13)	−0.0014 (12)	−0.0034 (11)
C25	0.0457 (15)	0.0310 (14)	0.0593 (15)	0.0032 (11)	−0.0005 (12)	0.0161 (12)
C26	0.0327 (14)	0.0439 (15)	0.0521 (14)	0.0036 (11)	−0.0031 (11)	0.0203 (13)
C27	0.0246 (12)	0.0276 (12)	0.0272 (10)	−0.0050 (9)	−0.0016 (9)	−0.0001 (9)
C28A	0.039 (2)	0.059 (2)	0.047 (2)	−0.0197 (18)	0.0002 (17)	−0.0083 (18)
C28B	0.039 (2)	0.059 (2)	0.047 (2)	−0.0197 (18)	0.0002 (17)	−0.0083 (18)
O1W	0.048 (2)	0.079 (3)	0.063 (2)	0.0069 (18)	0.0034 (18)	−0.0044 (19)

O1A—C3	1.253 (14)	C14—C15	1.542 (3)
O2A—C3	1.282 (9)	C14—C18	1.552 (3)
O2A—C28A	1.398 (11)	C15—C16	1.545 (3)
O1B—C3	1.270 (11)	C15—H15A	0.9700
O2B—C3	1.291 (19)	C15—H15B	0.9700
O2B—C28B	1.533 (19)	C16—C17	1.561 (3)
O3—C23	1.335 (3)	C16—H16A	0.9700
O3—C20	1.477 (3)	C16—H16B	0.9700
O4—C23	1.212 (3)	C17—C20	1.523 (3)
C1—C2	1.530 (3)	C17—H17A	0.9800
C1—C10	1.549 (3)	C18—H18A	0.9600
C1—H1B	0.9700	C18—H18B	0.9600
C1—H1A	0.9700	C18—H18C	0.9600
C2—C3	1.486 (3)	C19—H19A	0.9600
C2—H2A	0.9700	C19—H19B	0.9600
C2—H2B	0.9700	C19—H19C	0.9600
C4—C25	1.398 (3)	C20—C24	1.518 (3)
C4—C26	1.434 (3)	C20—C21	1.540 (3)
C4—C5	1.514 (3)	C21—C22	1.517 (3)
C5—C6	1.535 (3)	C21—H21A	0.9700
C5—C10	1.568 (3)	C21—H21B	0.9700
C5—H5A	0.9800	C22—C23	1.498 (3)
C6—C7	1.517 (3)	C22—H22A	0.9700
C6—H6A	0.9700	C22—H22B	0.9700
C6—H6B	0.9700	C24—H24A	0.9600
C7—C8	1.540 (3)	C24—H24B	0.9600
C7—H7A	0.9700	C24—H24C	0.9600
C7—H7B	0.9700	C25—H25A	0.9300
C8—C27	1.548 (3)	C25—H25B	0.9300
C8—C9	1.570 (3)	C26—H26A	0.9600
C8—C14	1.572 (3)	C26—H26B	0.9600
C9—C11	1.541 (3)	C26—H26C	0.9600
C9—C10	1.566 (3)	C27—H27A	0.9600
C9—H9A	0.9800	C27—H27B	0.9600
C10—C19	1.541 (3)	C27—H27C	0.9600
C11—C12	1.534 (3)	C28A—H28A	0.9600
C11—H11A	0.9700	C28A—H28B	0.9600
C11—H11B	0.9700	C28A—H28C	0.9600
C12—C13	1.517 (3)	C28B—H28D	0.9600
C12—H12A	0.9700	C28B—H28E	0.9600
C12—H12B	0.9700	C28B—H28F	0.9600
C13—C17	1.532 (3)	O1W—H1W1	1.0623
C13—C14	1.545 (3)	O1W—H2W1	0.8240
C13—H13A	0.9800
C3—O2A—C28A	117.3 (7)	C15—C14—C8	116.96 (15)
C3—O2B—C28B	117.3 (14)	C13—C14—C8	109.14 (15)
C23—O3—C20	111.64 (16)	C18—C14—C8	112.70 (16)
C2—C1—C10	117.72 (16)	C14—C15—C16	105.42 (16)
C2—C1—H1B	107.9	C14—C15—H15A	110.7
C10—C1—H1B	107.9	C16—C15—H15A	110.7
C2—C1—H1A	107.9	C14—C15—H15B	110.7
C10—C1—H1A	107.9	C16—C15—H15B	110.7
H1B—C1—H1A	107.2	H15A—C15—H15B	108.8
C3—C2—C1	109.05 (18)	C15—C16—C17	106.42 (17)
C3—C2—H2A	109.9	C15—C16—H16A	110.4
C1—C2—H2A	109.9	C17—C16—H16A	110.4
C3—C2—H2B	109.9	C15—C16—H16B	110.4
C1—C2—H2B	109.9	C17—C16—H16B	110.4
H2A—C2—H2B	108.3	H16A—C16—H16B	108.6
O1A—C3—O1B	120.2 (9)	C20—C17—C13	116.89 (17)
O1A—C3—O2A	122.9 (8)	C20—C17—C16	113.05 (18)
O1B—C3—O2B	123.7 (10)	C13—C17—C16	104.10 (16)
O2A—C3—O2B	125.6 (9)	C20—C17—H17A	107.4
O1A—C3—C2	120.4 (7)	C13—C17—H17A	107.4
O1B—C3—C2	119.2 (6)	C16—C17—H17A	107.4
O2A—C3—C2	116.7 (5)	C14—C18—H18A	109.5
O2B—C3—C2	116.6 (9)	C14—C18—H18B	109.5
C25—C4—C26	119.8 (2)	H18A—C18—H18B	109.5
C25—C4—C5	118.88 (19)	C14—C18—H18C	109.5
C26—C4—C5	121.2 (2)	H18A—C18—H18C	109.5
C4—C5—C6	112.25 (16)	H18B—C18—H18C	109.5
C4—C5—C10	115.08 (16)	C10—C19—H19A	109.5
C6—C5—C10	111.58 (16)	C10—C19—H19B	109.5
C4—C5—H5A	105.7	H19A—C19—H19B	109.5
C6—C5—H5A	105.7	C10—C19—H19C	109.5
C10—C5—H5A	105.7	H19A—C19—H19C	109.5
C7—C6—C5	111.62 (16)	H19B—C19—H19C	109.5
C7—C6—H6A	109.3	O3—C20—C24	106.38 (18)
C5—C6—H6A	109.3	O3—C20—C17	107.03 (16)
C7—C6—H6B	109.3	C24—C20—C17	114.70 (18)
C5—C6—H6B	109.3	O3—C20—C21	103.13 (16)
H6A—C6—H6B	108.0	C24—C20—C21	112.19 (19)
C6—C7—C8	113.96 (16)	C17—C20—C21	112.40 (18)
C6—C7—H7A	108.8	C22—C21—C20	103.79 (19)
C8—C7—H7A	108.8	C22—C21—H21A	111.0
C6—C7—H7B	108.8	C20—C21—H21A	111.0
C8—C7—H7B	108.8	C22—C21—H21B	111.0
H7A—C7—H7B	107.7	C20—C21—H21B	111.0
C7—C8—C27	108.17 (15)	H21A—C21—H21B	109.0
C7—C8—C9	108.34 (15)	C23—C22—C21	104.10 (18)
C27—C8—C9	111.55 (16)	C23—C22—H22A	110.9
C7—C8—C14	111.03 (16)	C21—C22—H22A	110.9
C27—C8—C14	110.31 (16)	C23—C22—H22B	110.9
C9—C8—C14	107.44 (14)	C21—C22—H22B	110.9
C11—C9—C10	113.48 (15)	H22A—C22—H22B	109.0
C11—C9—C8	111.72 (15)	O4—C23—O3	121.3 (2)
C10—C9—C8	116.48 (15)	O4—C23—C22	128.3 (2)
C11—C9—H9A	104.6	O3—C23—C22	110.47 (19)
C10—C9—H9A	104.6	C20—C24—H24A	109.5
C8—C9—H9A	104.6	C20—C24—H24B	109.5
C19—C10—C1	103.69 (15)	H24A—C24—H24B	109.5
C19—C10—C9	114.31 (16)	C20—C24—H24C	109.5
C1—C10—C9	110.40 (15)	H24A—C24—H24C	109.5
C19—C10—C5	111.38 (15)	H24B—C24—H24C	109.5
C1—C10—C5	109.72 (15)	C4—C25—H25A	120.0
C9—C10—C5	107.31 (15)	C4—C25—H25B	120.0
C12—C11—C9	113.57 (16)	H25A—C25—H25B	120.0
C12—C11—H11A	108.9	C4—C26—H26A	109.5
C9—C11—H11A	108.9	C4—C26—H26B	109.5
C12—C11—H11B	108.9	H26A—C26—H26B	109.5
C9—C11—H11B	108.9	C4—C26—H26C	109.5
H11A—C11—H11B	107.7	H26A—C26—H26C	109.5
C13—C12—C11	109.93 (16)	H26B—C26—H26C	109.5
C13—C12—H12A	109.7	C8—C27—H27A	109.5
C11—C12—H12A	109.7	C8—C27—H27B	109.5
C13—C12—H12B	109.7	H27A—C27—H27B	109.5
C11—C12—H12B	109.7	C8—C27—H27C	109.5
H12A—C12—H12B	108.2	H27A—C27—H27C	109.5
C12—C13—C17	119.33 (16)	H27B—C27—H27C	109.5
C12—C13—C14	111.90 (16)	O2B—C28B—H28D	109.5
C17—C13—C14	104.72 (15)	O2B—C28B—H28E	109.5
C12—C13—H13A	106.7	H28D—C28B—H28E	109.5
C17—C13—H13A	106.7	O2B—C28B—H28F	109.5
C14—C13—H13A	106.7	H28D—C28B—H28F	109.5
C15—C14—C13	101.14 (15)	H28E—C28B—H28F	109.5
C15—C14—C18	105.73 (16)	H1W1—O1W—H2W1	111.2
C13—C14—C18	110.52 (15)
C10—C1—C2—C3	−175.99 (17)	C9—C11—C12—C13	−52.3 (2)
C28A—O2A—C3—O1A	−4.2 (16)	C11—C12—C13—C17	179.56 (17)
C28A—O2A—C3—O1B	−52 (11)	C11—C12—C13—C14	56.9 (2)
C28A—O2A—C3—O2B	10.4 (19)	C12—C13—C14—C15	173.67 (15)
C28A—O2A—C3—C2	177.4 (5)	C17—C13—C14—C15	43.02 (18)
C28B—O2B—C3—O1A	74 (6)	C12—C13—C14—C18	62.0 (2)
C28B—O2B—C3—O1B	−4(3)	C17—C13—C14—C18	−68.62 (19)
C28B—O2B—C3—O2A	−8(3)	C12—C13—C14—C8	−62.44 (19)
C28B—O2B—C3—C2	−175.0 (12)	C17—C13—C14—C8	166.90 (15)
C1—C2—C3—O1A	88.7 (12)	C7—C8—C14—C15	−67.8 (2)
C1—C2—C3—O1B	−96.4 (6)	C27—C8—C14—C15	52.1 (2)
C1—C2—C3—O2A	−92.9 (5)	C9—C8—C14—C15	173.92 (16)
C1—C2—C3—O2B	75.3 (14)	C7—C8—C14—C13	178.27 (16)
C25—C4—C5—C6	−129.0 (2)	C27—C8—C14—C13	−61.8 (2)
C26—C4—C5—C6	47.1 (3)	C9—C8—C14—C13	59.96 (19)
C25—C4—C5—C10	101.9 (2)	C7—C8—C14—C18	55.1 (2)
C26—C4—C5—C10	−81.9 (2)	C27—C8—C14—C18	174.98 (16)
C4—C5—C6—C7	170.36 (17)	C9—C8—C14—C18	−63.2 (2)
C10—C5—C6—C7	−58.8 (2)	C13—C14—C15—C16	−36.41 (19)
C5—C6—C7—C8	57.2 (2)	C18—C14—C15—C16	78.84 (19)
C6—C7—C8—C27	69.8 (2)	C8—C14—C15—C16	−154.78 (17)
C6—C7—C8—C9	−51.2 (2)	C14—C15—C16—C17	17.0 (2)
C6—C7—C8—C14	−168.99 (16)	C12—C13—C17—C20	75.7 (2)
C7—C8—C9—C11	−176.10 (14)	C14—C13—C17—C20	−158.18 (17)
C27—C8—C9—C11	64.9 (2)	C12—C13—C17—C16	−158.89 (18)
C14—C8—C9—C11	−56.07 (19)	C14—C13—C17—C16	−32.73 (19)
C7—C8—C9—C10	51.2 (2)	C15—C16—C17—C20	137.46 (18)
C27—C8—C9—C10	−67.7 (2)	C15—C16—C17—C13	9.6 (2)
C14—C8—C9—C10	171.27 (15)	C23—O3—C20—C24	98.95 (19)
C2—C1—C10—C19	172.70 (17)	C23—O3—C20—C17	−138.00 (17)
C2—C1—C10—C9	49.8 (2)	C23—O3—C20—C21	−19.3 (2)
C2—C1—C10—C5	−68.2 (2)	C13—C17—C20—O3	−67.8 (2)
C11—C9—C10—C19	−61.2 (2)	C16—C17—C20—O3	171.40 (15)
C8—C9—C10—C19	70.7 (2)	C13—C17—C20—C24	50.0 (3)
C11—C9—C10—C1	55.2 (2)	C16—C17—C20—C24	−70.9 (3)
C8—C9—C10—C1	−172.91 (15)	C13—C17—C20—C21	179.70 (17)
C11—C9—C10—C5	174.77 (15)	C16—C17—C20—C21	58.9 (2)
C8—C9—C10—C5	−53.4 (2)	O3—C20—C21—C22	25.6 (2)
C4—C5—C10—C19	58.6 (2)	C24—C20—C21—C22	−88.4 (2)
C6—C5—C10—C19	−70.8 (2)	C17—C20—C21—C22	140.6 (2)
C4—C5—C10—C1	−55.6 (2)	C20—C21—C22—C23	−23.4 (2)
C6—C5—C10—C1	174.97 (15)	C20—O3—C23—O4	−175.35 (18)
C4—C5—C10—C9	−175.60 (16)	C20—O3—C23—C22	4.4 (2)
C6—C5—C10—C9	55.00 (19)	C21—C22—C23—O4	−167.6 (2)
C10—C9—C11—C12	−172.33 (16)	C21—C22—C23—O3	12.6 (2)
C8—C9—C11—C12	53.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O4i	1.06	1.94	2.912 (4)	151
C2—H2A···O4ii	0.97	2.45	3.305 (3)	146
C12—H12B···O3	0.97	2.58	3.154 (2)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O4i	1.06	1.94	2.912 (4)	151
C2—H2A⋯O4ii	0.97	2.45	3.305 (3)	146
C12—H12B⋯O3	0.97	2.58	3.154 (2)	118

Symmetry codes: (i) ; (ii) .