3β,11α-Dihy-droxy-12-ursen-3-yl palmitate.

In the title compound, C(46)H(80)O(3), a natural ursane-type triperpenoid, four of the five six-membered rings adopt chair conformations; the fifth, which has a C=C double bond, adopts an approximate half-boat conformation. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming chains along [010].

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For spectroscopic properties of the title compound, see: Kakuda et al. (2003 ▶).

Experimental

Crystal data

C46H80O3

M = 681.10

Monoclinic,

a = 11.389 (2) Å

b = 15.714 (3) Å

c = 11.766 (2) Å

β = 98.925 (3)°

V = 2080.3 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 93 K

0.60 × 0.50 × 0.30 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

16995 measured reflections

4832 independent reflections

4397 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.098

S = 1.00

4832 reflections

455 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811047106/bx2380sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047106/bx2380Isup2.hkl

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

C46H80O3	F(000) = 760
Mr = 681.10	Dx = 1.087 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 11.389 (2) Å	Cell parameters from 7345 reflections
b = 15.714 (3) Å	θ = 3.0–27.5°
c = 11.766 (2) Å	µ = 0.07 mm−1
β = 98.925 (3)°	T = 93 K
V = 2080.3 (7) Å3	Block, colourless
Z = 2	0.60 × 0.50 × 0.30 mm

Rigaku AFC10/Saturn724+ diffractometer	4397 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.032
graphite	θmax = 27.5°, θmin = 3.1°
Detector resolution: 28.5714 pixels mm-1	h = −14→14
phi and ω scans	k = −20→20
16995 measured reflections	l = −14→14
4832 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0286P)2 + 0.860P] where P = (Fo2 + 2Fc2)/3
4832 reflections	(Δ/σ)max < 0.001
455 parameters	Δρmax = 0.22 e Å−3
1 restraint	Δρmin = −0.15 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.7358 (2)	0.09757 (13)	0.56526 (16)	0.0423 (5)
O2	0.66023 (16)	0.51467 (12)	0.64282 (16)	0.0373 (4)
O3	0.48079 (18)	0.51257 (14)	0.53336 (17)	0.0469 (5)
C1	0.7086 (2)	0.27759 (15)	0.6092 (2)	0.0282 (5)
H1A	0.7494	0.2468	0.5531	0.034*
H1B	0.6248	0.2584	0.5980	0.034*
C2	0.7121 (2)	0.37373 (16)	0.5849 (2)	0.0321 (6)
H2A	0.7958	0.3925	0.5903	0.039*
H2B	0.6716	0.3853	0.5057	0.039*
C3	0.6522 (2)	0.42345 (17)	0.6692 (2)	0.0328 (6)
H3	0.5664	0.4069	0.6590	0.039*
C4	0.7061 (2)	0.41063 (16)	0.7958 (2)	0.0302 (5)
C5	0.7115 (2)	0.31251 (16)	0.8183 (2)	0.0263 (5)
H5	0.6264	0.2944	0.8085	0.032*
C6	0.7608 (2)	0.28945 (16)	0.9424 (2)	0.0298 (5)
H6A	0.7300	0.3299	0.9952	0.036*
H6B	0.8485	0.2940	0.9545	0.036*
C7	0.7248 (2)	0.19890 (16)	0.9696 (2)	0.0286 (5)
H7A	0.6374	0.1967	0.9651	0.034*
H7B	0.7605	0.1850	1.0496	0.034*
C8	0.76315 (19)	0.13074 (16)	0.8885 (2)	0.0245 (5)
C9	0.73602 (19)	0.15932 (16)	0.76015 (19)	0.0238 (5)
H9	0.6476	0.1558	0.7394	0.029*
C10	0.7685 (2)	0.25440 (16)	0.7329 (2)	0.0253 (5)
C11	0.7853 (2)	0.09126 (17)	0.6844 (2)	0.0288 (5)
H11	0.8727	0.1016	0.6903	0.035*
C12	0.7700 (2)	0.00159 (16)	0.7251 (2)	0.0274 (5)
H12	0.7920	−0.0427	0.6775	0.033*
C13	0.72899 (19)	−0.02268 (15)	0.8202 (2)	0.0241 (5)
C14	0.6930 (2)	0.04465 (16)	0.9029 (2)	0.0251 (5)
C15	0.7157 (2)	0.01434 (17)	1.0297 (2)	0.0307 (5)
H15A	0.7993	0.0270	1.0626	0.037*
H15B	0.6641	0.0473	1.0740	0.037*
C16	0.6926 (2)	−0.08099 (17)	1.0454 (2)	0.0318 (5)
H16A	0.6064	−0.0922	1.0249	0.038*
H16B	0.7164	−0.0962	1.1273	0.038*
C17	0.7605 (2)	−0.13792 (17)	0.9712 (2)	0.0293 (5)
C18	0.7145 (2)	−0.11755 (16)	0.8435 (2)	0.0268 (5)
H18	0.7681	−0.1483	0.7976	0.032*
C19	0.5867 (2)	−0.15270 (16)	0.8029 (2)	0.0288 (5)
H19	0.5315	−0.1230	0.8482	0.035*
C20	0.5810 (2)	−0.24905 (17)	0.8281 (2)	0.0320 (5)
H20	0.6385	−0.2786	0.7854	0.038*
C21	0.6193 (2)	−0.26572 (17)	0.9567 (2)	0.0350 (6)
H21A	0.5630	−0.2375	1.0008	0.042*
H21B	0.6170	−0.3276	0.9717	0.042*
C22	0.7438 (2)	−0.23238 (18)	0.9970 (2)	0.0351 (6)
H22A	0.8006	−0.2661	0.9596	0.042*
H22B	0.7638	−0.2414	1.0810	0.042*
C23	0.8264 (2)	0.45627 (17)	0.8259 (2)	0.0326 (6)
H23A	0.8791	0.4389	0.7716	0.039*
H23B	0.8628	0.4410	0.9042	0.039*
H23C	0.8142	0.5180	0.8209	0.039*
C24	0.6193 (2)	0.45184 (18)	0.8686 (3)	0.0413 (7)
H24A	0.6090	0.5122	0.8485	0.050*
H24B	0.6516	0.4465	0.9505	0.050*
H24C	0.5422	0.4229	0.8531	0.050*
C25	0.9039 (2)	0.26877 (17)	0.7378 (2)	0.0289 (5)
H25A	0.9380	0.2211	0.7003	0.035*
H25B	0.9420	0.2725	0.8182	0.035*
H25C	0.9172	0.3218	0.6979	0.035*
C26	0.8995 (2)	0.11656 (17)	0.9255 (2)	0.0294 (5)
H26A	0.9419	0.1698	0.9165	0.035*
H26B	0.9271	0.0725	0.8770	0.035*
H26C	0.9150	0.0985	1.0062	0.035*
C27	0.5556 (2)	0.05609 (17)	0.8704 (2)	0.0296 (5)
H27A	0.5349	0.0629	0.7869	0.036*
H27B	0.5304	0.1067	0.9090	0.036*
H27C	0.5152	0.0058	0.8949	0.036*
C28	0.8948 (2)	−0.11911 (19)	0.9984 (2)	0.0394 (6)
H28A	0.9383	−0.1596	0.9570	0.047*
H28B	0.9215	−0.1248	1.0813	0.047*
H28C	0.9101	−0.0610	0.9741	0.047*
C29	0.5451 (3)	−0.13413 (19)	0.6761 (2)	0.0426 (7)
H29A	0.5984	−0.1620	0.6298	0.051*
H29B	0.5458	−0.0725	0.6631	0.051*
H29C	0.4642	−0.1559	0.6537	0.051*
C30	0.4576 (2)	−0.28749 (19)	0.7892 (2)	0.0398 (6)
H30A	0.4577	−0.3473	0.8127	0.048*
H30B	0.4379	−0.2836	0.7053	0.048*
H30C	0.3985	−0.2561	0.8248	0.048*
C1'	0.5716 (2)	0.54980 (18)	0.5713 (2)	0.0350 (6)
C2'	0.5993 (3)	0.64035 (18)	0.5409 (2)	0.0390 (6)
H2'1	0.5272	0.6759	0.5379	0.047*
H2'2	0.6615	0.6639	0.6007	0.047*
C3'	0.6418 (3)	0.6424 (2)	0.4257 (3)	0.0492 (8)
H3'1	0.5834	0.6122	0.3687	0.059*
H3'2	0.7181	0.6113	0.4320	0.059*
C4'	0.6596 (3)	0.7331 (2)	0.3812 (3)	0.0549 (9)
H4'1	0.6651	0.7296	0.2982	0.066*
H4'2	0.5883	0.7672	0.3891	0.066*
C5'	0.7677 (3)	0.77948 (19)	0.4411 (2)	0.0403 (6)
H5'1	0.8392	0.7444	0.4376	0.048*
H5'2	0.7601	0.7874	0.5231	0.048*
C6'	0.7836 (3)	0.8663 (2)	0.3869 (3)	0.0511 (8)
H6'1	0.7864	0.8577	0.3040	0.061*
H6'2	0.7125	0.9012	0.3930	0.061*
C7'	0.8925 (2)	0.91628 (18)	0.4381 (2)	0.0369 (6)
H7'1	0.9642	0.8808	0.4367	0.044*
H7'2	0.8875	0.9296	0.5195	0.044*
C8'	0.9052 (3)	0.99922 (19)	0.3730 (3)	0.0407 (6)
H8'1	0.9087	0.9854	0.2915	0.049*
H8'2	0.8333	1.0342	0.3750	0.049*
C9'	1.0140 (3)	1.05190 (18)	0.4201 (3)	0.0413 (7)
H9'1	1.0856	1.0156	0.4244	0.050*
H9'2	1.0071	1.0704	0.4992	0.050*
C10'	1.0300 (2)	1.13012 (18)	0.3475 (3)	0.0414 (7)
H10A	1.0274	1.1123	0.2665	0.050*
H10B	1.1096	1.1547	0.3740	0.050*
C11'	0.9365 (3)	1.19878 (19)	0.3527 (3)	0.0424 (7)
H11A	0.9364	1.2146	0.4341	0.051*
H11B	0.8573	1.1750	0.3225	0.051*
C12'	0.9563 (2)	1.27902 (18)	0.2846 (2)	0.0382 (6)
H12A	1.0346	1.3038	0.3156	0.046*
H12B	0.9574	1.2635	0.2032	0.046*
C13'	0.8604 (2)	1.34523 (19)	0.2901 (3)	0.0396 (6)
H13A	0.8564	1.3576	0.3719	0.048*
H13B	0.7829	1.3208	0.2556	0.048*
C14'	0.8783 (2)	1.42849 (18)	0.2295 (2)	0.0357 (6)
H14A	0.9517	1.4562	0.2686	0.043*
H14B	0.8894	1.4162	0.1493	0.043*
C15'	0.7755 (3)	1.4889 (2)	0.2281 (3)	0.0464 (7)
H15C	0.7619	1.4983	0.3082	0.056*
H15D	0.7032	1.4618	0.1857	0.056*
C16'	0.7929 (3)	1.5745 (2)	0.1735 (3)	0.0502 (8)
H16'A	0.8613	1.6035	0.2178	0.060*
H16'B	0.7215	1.6093	0.1733	0.060*
H16'C	0.8072	1.5660	0.0943	0.060*
H1O	0.674 (3)	0.074 (3)	0.554 (3)	0.057 (11)*

	U11	U22	U33	U12	U13	U23
O1	0.0667 (14)	0.0380 (11)	0.0214 (10)	−0.0177 (11)	0.0045 (9)	−0.0005 (8)
O2	0.0324 (9)	0.0323 (10)	0.0443 (11)	−0.0016 (8)	−0.0027 (8)	0.0066 (9)
O3	0.0447 (11)	0.0427 (11)	0.0469 (12)	0.0035 (10)	−0.0134 (9)	−0.0033 (10)
C1	0.0303 (12)	0.0304 (13)	0.0224 (12)	−0.0072 (10)	−0.0010 (9)	0.0018 (10)
C2	0.0325 (12)	0.0337 (14)	0.0284 (13)	−0.0080 (11)	−0.0006 (10)	0.0063 (11)
C3	0.0245 (12)	0.0316 (13)	0.0411 (15)	−0.0042 (10)	0.0009 (10)	0.0036 (12)
C4	0.0253 (12)	0.0293 (13)	0.0364 (14)	−0.0021 (10)	0.0057 (10)	−0.0010 (11)
C5	0.0221 (11)	0.0303 (12)	0.0267 (13)	−0.0026 (9)	0.0039 (9)	0.0001 (10)
C6	0.0312 (12)	0.0323 (13)	0.0261 (13)	−0.0021 (10)	0.0054 (10)	−0.0045 (10)
C7	0.0304 (12)	0.0346 (14)	0.0208 (12)	−0.0002 (10)	0.0044 (9)	0.0002 (10)
C8	0.0205 (10)	0.0308 (12)	0.0219 (12)	−0.0010 (9)	0.0026 (8)	0.0005 (10)
C9	0.0204 (10)	0.0305 (12)	0.0196 (11)	−0.0041 (9)	0.0005 (8)	0.0008 (9)
C10	0.0224 (11)	0.0291 (12)	0.0242 (12)	−0.0053 (9)	0.0031 (9)	0.0001 (10)
C11	0.0304 (12)	0.0333 (13)	0.0231 (12)	−0.0075 (10)	0.0057 (10)	−0.0007 (10)
C12	0.0264 (11)	0.0304 (13)	0.0262 (12)	−0.0026 (10)	0.0067 (9)	−0.0030 (10)
C13	0.0199 (10)	0.0300 (12)	0.0214 (12)	0.0007 (9)	0.0003 (9)	0.0020 (9)
C14	0.0224 (11)	0.0310 (12)	0.0223 (12)	0.0010 (9)	0.0047 (9)	0.0019 (9)
C15	0.0321 (12)	0.0385 (14)	0.0218 (12)	0.0015 (11)	0.0053 (10)	0.0030 (11)
C16	0.0321 (12)	0.0404 (14)	0.0224 (12)	0.0015 (11)	0.0027 (10)	0.0089 (11)
C17	0.0235 (11)	0.0346 (13)	0.0285 (13)	0.0035 (10)	0.0000 (9)	0.0103 (11)
C18	0.0240 (11)	0.0299 (13)	0.0271 (13)	0.0036 (9)	0.0059 (9)	0.0046 (10)
C19	0.0283 (12)	0.0307 (13)	0.0271 (13)	0.0011 (10)	0.0031 (9)	0.0049 (10)
C20	0.0317 (13)	0.0320 (13)	0.0329 (14)	−0.0004 (10)	0.0071 (10)	0.0066 (11)
C21	0.0369 (14)	0.0334 (14)	0.0355 (15)	0.0008 (11)	0.0081 (11)	0.0118 (11)
C22	0.0320 (13)	0.0382 (15)	0.0341 (14)	0.0056 (11)	0.0024 (11)	0.0119 (12)
C23	0.0313 (13)	0.0309 (13)	0.0349 (14)	−0.0039 (10)	0.0028 (10)	−0.0002 (11)
C24	0.0387 (15)	0.0358 (15)	0.0519 (18)	0.0037 (12)	0.0152 (13)	0.0013 (13)
C25	0.0236 (11)	0.0329 (13)	0.0306 (13)	−0.0055 (10)	0.0052 (9)	0.0002 (10)
C26	0.0235 (11)	0.0376 (14)	0.0256 (12)	−0.0009 (10)	−0.0006 (9)	0.0008 (10)
C27	0.0217 (11)	0.0323 (13)	0.0357 (14)	0.0027 (10)	0.0072 (10)	0.0030 (11)
C28	0.0277 (13)	0.0424 (16)	0.0453 (16)	0.0058 (12)	−0.0034 (11)	0.0110 (13)
C29	0.0504 (16)	0.0360 (15)	0.0366 (15)	−0.0131 (13)	−0.0082 (12)	0.0079 (12)
C30	0.0389 (15)	0.0412 (16)	0.0398 (16)	−0.0052 (12)	0.0074 (12)	0.0088 (13)
C1'	0.0362 (13)	0.0364 (14)	0.0313 (14)	0.0044 (11)	0.0018 (11)	−0.0012 (11)
C2'	0.0428 (15)	0.0351 (15)	0.0373 (15)	0.0054 (12)	0.0005 (12)	0.0027 (12)
C3'	0.0579 (19)	0.0502 (19)	0.0373 (17)	−0.0116 (15)	0.0007 (13)	−0.0043 (14)
C4'	0.057 (2)	0.066 (2)	0.0379 (17)	−0.0130 (17)	−0.0059 (14)	0.0150 (16)
C5'	0.0404 (15)	0.0463 (17)	0.0338 (15)	0.0011 (12)	0.0046 (11)	0.0078 (13)
C6'	0.0489 (17)	0.054 (2)	0.0472 (18)	−0.0057 (15)	−0.0046 (14)	0.0187 (15)
C7'	0.0400 (14)	0.0384 (15)	0.0336 (14)	0.0072 (12)	0.0104 (11)	0.0007 (12)
C8'	0.0456 (15)	0.0388 (15)	0.0388 (15)	0.0046 (13)	0.0101 (12)	0.0040 (12)
C9'	0.0404 (15)	0.0389 (15)	0.0439 (17)	0.0098 (12)	0.0046 (12)	−0.0022 (13)
C10'	0.0367 (14)	0.0356 (15)	0.0534 (18)	0.0005 (12)	0.0115 (13)	−0.0058 (14)
C11'	0.0398 (15)	0.0373 (15)	0.0516 (18)	0.0040 (12)	0.0114 (13)	0.0041 (13)
C12'	0.0379 (14)	0.0349 (15)	0.0420 (16)	−0.0005 (11)	0.0075 (12)	−0.0010 (12)
C13'	0.0332 (14)	0.0396 (15)	0.0454 (16)	−0.0024 (12)	0.0042 (12)	0.0044 (13)
C14'	0.0322 (13)	0.0344 (14)	0.0399 (15)	−0.0026 (11)	0.0036 (11)	0.0013 (12)
C15'	0.0385 (15)	0.0436 (17)	0.0577 (19)	0.0051 (13)	0.0095 (14)	0.0114 (14)
C16'	0.0411 (16)	0.0417 (17)	0.068 (2)	0.0077 (13)	0.0100 (15)	0.0155 (16)

O1—C11	1.431 (3)	C24—H24B	0.9800
O1—H1O	0.79 (4)	C24—H24C	0.9800
O2—C1'	1.330 (3)	C25—H25A	0.9800
O2—C3	1.473 (3)	C25—H25B	0.9800
O3—C1'	1.211 (3)	C25—H25C	0.9800
C1—C2	1.539 (3)	C26—H26A	0.9800
C1—C10	1.552 (3)	C26—H26B	0.9800
C1—H1A	0.9900	C26—H26C	0.9800
C1—H1B	0.9900	C27—H27A	0.9800
C2—C3	1.507 (4)	C27—H27B	0.9800
C2—H2A	0.9900	C27—H27C	0.9800
C2—H2B	0.9900	C28—H28A	0.9800
C3—C4	1.533 (4)	C28—H28B	0.9800
C3—H3	1.0000	C28—H28C	0.9800
C4—C23	1.539 (3)	C29—H29A	0.9800
C4—C24	1.547 (4)	C29—H29B	0.9800
C4—C5	1.564 (3)	C29—H29C	0.9800
C5—C6	1.524 (3)	C30—H30A	0.9800
C5—C10	1.571 (3)	C30—H30B	0.9800
C5—H5	1.0000	C30—H30C	0.9800
C6—C7	1.528 (3)	C1'—C2'	1.513 (4)
C6—H6A	0.9900	C2'—C3'	1.508 (4)
C6—H6B	0.9900	C2'—H2'1	0.9900
C7—C8	1.542 (3)	C2'—H2'2	0.9900
C7—H7A	0.9900	C3'—C4'	1.542 (5)
C7—H7B	0.9900	C3'—H3'1	0.9900
C8—C9	1.559 (3)	C3'—H3'2	0.9900
C8—C26	1.562 (3)	C4'—C5'	1.508 (4)
C8—C14	1.594 (3)	C4'—H4'1	0.9900
C9—C11	1.552 (3)	C4'—H4'2	0.9900
C9—C10	1.584 (3)	C5'—C6'	1.528 (4)
C9—H9	1.0000	C5'—H5'1	0.9900
C10—C25	1.550 (3)	C5'—H5'2	0.9900
C11—C12	1.507 (4)	C6'—C7'	1.512 (4)
C11—H11	1.0000	C6'—H6'1	0.9900
C12—C13	1.333 (3)	C6'—H6'2	0.9900
C12—H12	0.9500	C7'—C8'	1.530 (4)
C13—C18	1.530 (3)	C7'—H7'1	0.9900
C13—C14	1.536 (3)	C7'—H7'2	0.9900
C14—C15	1.549 (3)	C8'—C9'	1.521 (4)
C14—C27	1.563 (3)	C8'—H8'1	0.9900
C15—C16	1.537 (4)	C8'—H8'2	0.9900
C15—H15A	0.9900	C9'—C10'	1.524 (4)
C15—H15B	0.9900	C9'—H9'1	0.9900
C16—C17	1.539 (4)	C9'—H9'2	0.9900
C16—H16A	0.9900	C10'—C11'	1.524 (4)
C16—H16B	0.9900	C10'—H10A	0.9900
C17—C22	1.533 (4)	C10'—H10B	0.9900
C17—C28	1.542 (3)	C11'—C12'	1.529 (4)
C17—C18	1.546 (3)	C11'—H11A	0.9900
C18—C19	1.561 (3)	C11'—H11B	0.9900
C18—H18	1.0000	C12'—C13'	1.517 (4)
C19—C29	1.522 (3)	C12'—H12A	0.9900
C19—C20	1.546 (4)	C12'—H12B	0.9900
C19—H19	1.0000	C13'—C14'	1.519 (4)
C20—C21	1.531 (4)	C13'—H13A	0.9900
C20—C30	1.533 (4)	C13'—H13B	0.9900
C20—H20	1.0000	C14'—C15'	1.505 (4)
C21—C22	1.517 (4)	C14'—H14A	0.9900
C21—H21A	0.9900	C14'—H14B	0.9900
C21—H21B	0.9900	C15'—C16'	1.517 (4)
C22—H22A	0.9900	C15'—H15C	0.9900
C22—H22B	0.9900	C15'—H15D	0.9900
C23—H23A	0.9800	C16'—H16'A	0.9800
C23—H23B	0.9800	C16'—H16'B	0.9800
C23—H23C	0.9800	C16'—H16'C	0.9800
C24—H24A	0.9800
C11—O1—H1O	110 (3)	C4—C24—H24B	109.5
C1'—O2—C3	118.1 (2)	H24A—C24—H24B	109.5
C2—C1—C10	112.6 (2)	C4—C24—H24C	109.5
C2—C1—H1A	109.1	H24A—C24—H24C	109.5
C10—C1—H1A	109.1	H24B—C24—H24C	109.5
C2—C1—H1B	109.1	C10—C25—H25A	109.5
C10—C1—H1B	109.1	C10—C25—H25B	109.5
H1A—C1—H1B	107.8	H25A—C25—H25B	109.5
C3—C2—C1	111.0 (2)	C10—C25—H25C	109.5
C3—C2—H2A	109.4	H25A—C25—H25C	109.5
C1—C2—H2A	109.4	H25B—C25—H25C	109.5
C3—C2—H2B	109.4	C8—C26—H26A	109.5
C1—C2—H2B	109.4	C8—C26—H26B	109.5
H2A—C2—H2B	108.0	H26A—C26—H26B	109.5
O2—C3—C2	108.4 (2)	C8—C26—H26C	109.5
O2—C3—C4	107.7 (2)	H26A—C26—H26C	109.5
C2—C3—C4	114.7 (2)	H26B—C26—H26C	109.5
O2—C3—H3	108.6	C14—C27—H27A	109.5
C2—C3—H3	108.6	C14—C27—H27B	109.5
C4—C3—H3	108.6	H27A—C27—H27B	109.5
C3—C4—C23	111.7 (2)	C14—C27—H27C	109.5
C3—C4—C24	106.8 (2)	H27A—C27—H27C	109.5
C23—C4—C24	107.5 (2)	H27B—C27—H27C	109.5
C3—C4—C5	107.1 (2)	C17—C28—H28A	109.5
C23—C4—C5	114.2 (2)	C17—C28—H28B	109.5
C24—C4—C5	109.3 (2)	H28A—C28—H28B	109.5
C6—C5—C4	113.3 (2)	C17—C28—H28C	109.5
C6—C5—C10	110.3 (2)	H28A—C28—H28C	109.5
C4—C5—C10	118.3 (2)	H28B—C28—H28C	109.5
C6—C5—H5	104.4	C19—C29—H29A	109.5
C4—C5—H5	104.4	C19—C29—H29B	109.5
C10—C5—H5	104.4	H29A—C29—H29B	109.5
C5—C6—C7	110.6 (2)	C19—C29—H29C	109.5
C5—C6—H6A	109.5	H29A—C29—H29C	109.5
C7—C6—H6A	109.5	H29B—C29—H29C	109.5
C5—C6—H6B	109.5	C20—C30—H30A	109.5
C7—C6—H6B	109.5	C20—C30—H30B	109.5
H6A—C6—H6B	108.1	H30A—C30—H30B	109.5
C6—C7—C8	113.97 (19)	C20—C30—H30C	109.5
C6—C7—H7A	108.8	H30A—C30—H30C	109.5
C8—C7—H7A	108.8	H30B—C30—H30C	109.5
C6—C7—H7B	108.8	O3—C1'—O2	123.6 (3)
C8—C7—H7B	108.8	O3—C1'—C2'	124.4 (3)
H7A—C7—H7B	107.7	O2—C1'—C2'	112.0 (2)
C7—C8—C9	111.5 (2)	C3'—C2'—C1'	109.9 (2)
C7—C8—C26	106.91 (19)	C3'—C2'—H2'1	109.7
C9—C8—C26	110.50 (18)	C1'—C2'—H2'1	109.7
C7—C8—C14	109.20 (18)	C3'—C2'—H2'2	109.7
C9—C8—C14	108.69 (18)	C1'—C2'—H2'2	109.7
C26—C8—C14	110.02 (19)	H2'1—C2'—H2'2	108.2
C11—C9—C8	108.81 (19)	C2'—C3'—C4'	113.7 (3)
C11—C9—C10	114.66 (18)	C2'—C3'—H3'1	108.8
C8—C9—C10	116.76 (18)	C4'—C3'—H3'1	108.8
C11—C9—H9	105.1	C2'—C3'—H3'2	108.8
C8—C9—H9	105.1	C4'—C3'—H3'2	108.8
C10—C9—H9	105.1	H3'1—C3'—H3'2	107.7
C25—C10—C1	106.87 (19)	C5'—C4'—C3'	115.4 (3)
C25—C10—C5	113.51 (19)	C5'—C4'—H4'1	108.4
C1—C10—C5	107.37 (19)	C3'—C4'—H4'1	108.4
C25—C10—C9	113.08 (19)	C5'—C4'—H4'2	108.4
C1—C10—C9	109.20 (18)	C3'—C4'—H4'2	108.4
C5—C10—C9	106.63 (18)	H4'1—C4'—H4'2	107.5
O1—C11—C12	109.2 (2)	C4'—C5'—C6'	112.2 (2)
O1—C11—C9	113.1 (2)	C4'—C5'—H5'1	109.2
C12—C11—C9	113.08 (19)	C6'—C5'—H5'1	109.2
O1—C11—H11	107.0	C4'—C5'—H5'2	109.2
C12—C11—H11	107.0	C6'—C5'—H5'2	109.2
C9—C11—H11	107.0	H5'1—C5'—H5'2	107.9
C13—C12—C11	127.4 (2)	C7'—C6'—C5'	116.1 (2)
C13—C12—H12	116.3	C7'—C6'—H6'1	108.3
C11—C12—H12	116.3	C5'—C6'—H6'1	108.3
C12—C13—C18	119.4 (2)	C7'—C6'—H6'2	108.3
C12—C13—C14	119.8 (2)	C5'—C6'—H6'2	108.3
C18—C13—C14	120.69 (19)	H6'1—C6'—H6'2	107.4
C13—C14—C15	112.2 (2)	C6'—C7'—C8'	112.2 (2)
C13—C14—C27	106.24 (19)	C6'—C7'—H7'1	109.2
C15—C14—C27	106.42 (19)	C8'—C7'—H7'1	109.2
C13—C14—C8	109.24 (18)	C6'—C7'—H7'2	109.2
C15—C14—C8	110.61 (19)	C8'—C7'—H7'2	109.2
C27—C14—C8	112.09 (19)	H7'1—C7'—H7'2	107.9
C16—C15—C14	114.1 (2)	C9'—C8'—C7'	114.6 (2)
C16—C15—H15A	108.7	C9'—C8'—H8'1	108.6
C14—C15—H15A	108.7	C7'—C8'—H8'1	108.6
C16—C15—H15B	108.7	C9'—C8'—H8'2	108.6
C14—C15—H15B	108.7	C7'—C8'—H8'2	108.6
H15A—C15—H15B	107.6	H8'1—C8'—H8'2	107.6
C15—C16—C17	112.8 (2)	C8'—C9'—C10'	113.4 (2)
C15—C16—H16A	109.0	C8'—C9'—H9'1	108.9
C17—C16—H16A	109.0	C10'—C9'—H9'1	108.9
C15—C16—H16B	109.0	C8'—C9'—H9'2	108.9
C17—C16—H16B	109.0	C10'—C9'—H9'2	108.9
H16A—C16—H16B	107.8	H9'1—C9'—H9'2	107.7
C22—C17—C16	111.3 (2)	C9'—C10'—C11'	113.8 (2)
C22—C17—C28	107.1 (2)	C9'—C10'—H10A	108.8
C16—C17—C28	109.9 (2)	C11'—C10'—H10A	108.8
C22—C17—C18	111.0 (2)	C9'—C10'—H10B	108.8
C16—C17—C18	107.82 (19)	C11'—C10'—H10B	108.8
C28—C17—C18	109.7 (2)	H10A—C10'—H10B	107.7
C13—C18—C17	110.3 (2)	C10'—C11'—C12'	113.7 (2)
C13—C18—C19	114.29 (19)	C10'—C11'—H11A	108.8
C17—C18—C19	112.55 (19)	C12'—C11'—H11A	108.8
C13—C18—H18	106.4	C10'—C11'—H11B	108.8
C17—C18—H18	106.4	C12'—C11'—H11B	108.8
C19—C18—H18	106.4	H11A—C11'—H11B	107.7
C29—C19—C20	111.1 (2)	C13'—C12'—C11'	112.2 (2)
C29—C19—C18	111.5 (2)	C13'—C12'—H12A	109.2
C20—C19—C18	110.7 (2)	C11'—C12'—H12A	109.2
C29—C19—H19	107.8	C13'—C12'—H12B	109.2
C20—C19—H19	107.8	C11'—C12'—H12B	109.2
C18—C19—H19	107.8	H12A—C12'—H12B	107.9
C21—C20—C30	109.6 (2)	C12'—C13'—C14'	114.9 (2)
C21—C20—C19	110.1 (2)	C12'—C13'—H13A	108.5
C30—C20—C19	113.1 (2)	C14'—C13'—H13A	108.5
C21—C20—H20	108.0	C12'—C13'—H13B	108.5
C30—C20—H20	108.0	C14'—C13'—H13B	108.5
C19—C20—H20	108.0	H13A—C13'—H13B	107.5
C22—C21—C20	111.0 (2)	C15'—C14'—C13'	112.8 (2)
C22—C21—H21A	109.4	C15'—C14'—H14A	109.0
C20—C21—H21A	109.4	C13'—C14'—H14A	109.0
C22—C21—H21B	109.4	C15'—C14'—H14B	109.0
C20—C21—H21B	109.4	C13'—C14'—H14B	109.0
H21A—C21—H21B	108.0	H14A—C14'—H14B	107.8
C21—C22—C17	114.3 (2)	C14'—C15'—C16'	114.3 (2)
C21—C22—H22A	108.7	C14'—C15'—H15C	108.7
C17—C22—H22A	108.7	C16'—C15'—H15C	108.7
C21—C22—H22B	108.7	C14'—C15'—H15D	108.7
C17—C22—H22B	108.7	C16'—C15'—H15D	108.7
H22A—C22—H22B	107.6	H15C—C15'—H15D	107.6
C4—C23—H23A	109.5	C15'—C16'—H16'A	109.5
C4—C23—H23B	109.5	C15'—C16'—H16'B	109.5
H23A—C23—H23B	109.5	H16'A—C16'—H16'B	109.5
C4—C23—H23C	109.5	C15'—C16'—H16'C	109.5
H23A—C23—H23C	109.5	H16'A—C16'—H16'C	109.5
H23B—C23—H23C	109.5	H16'B—C16'—H16'C	109.5
C4—C24—H24A	109.5
C10—C1—C2—C3	−58.1 (3)	C7—C8—C14—C13	178.74 (18)
C1'—O2—C3—C2	91.8 (3)	C9—C8—C14—C13	56.9 (2)
C1'—O2—C3—C4	−143.6 (2)	C26—C8—C14—C13	−64.2 (2)
C1—C2—C3—O2	179.05 (19)	C7—C8—C14—C15	−57.3 (2)
C1—C2—C3—C4	58.7 (3)	C9—C8—C14—C15	−179.17 (19)
O2—C3—C4—C23	−47.3 (3)	C26—C8—C14—C15	59.7 (2)
C2—C3—C4—C23	73.5 (3)	C7—C8—C14—C27	61.3 (2)
O2—C3—C4—C24	70.0 (2)	C9—C8—C14—C27	−60.6 (2)
C2—C3—C4—C24	−169.2 (2)	C26—C8—C14—C27	178.31 (19)
O2—C3—C4—C5	−173.05 (19)	C13—C14—C15—C16	−36.2 (3)
C2—C3—C4—C5	−52.2 (3)	C27—C14—C15—C16	79.6 (2)
C3—C4—C5—C6	−178.62 (19)	C8—C14—C15—C16	−158.42 (19)
C23—C4—C5—C6	57.2 (3)	C14—C15—C16—C17	53.3 (3)
C24—C4—C5—C6	−63.3 (3)	C15—C16—C17—C22	175.0 (2)
C3—C4—C5—C10	50.0 (3)	C15—C16—C17—C28	56.6 (3)
C23—C4—C5—C10	−74.2 (3)	C15—C16—C17—C18	−63.0 (3)
C24—C4—C5—C10	165.3 (2)	C12—C13—C18—C17	136.7 (2)
C4—C5—C6—C7	160.3 (2)	C14—C13—C18—C17	−45.3 (3)
C10—C5—C6—C7	−64.5 (2)	C12—C13—C18—C19	−95.3 (3)
C5—C6—C7—C8	56.4 (3)	C14—C13—C18—C19	82.7 (3)
C6—C7—C8—C9	−45.0 (3)	C22—C17—C18—C13	178.59 (19)
C6—C7—C8—C26	75.8 (2)	C16—C17—C18—C13	56.5 (2)
C6—C7—C8—C14	−165.16 (19)	C28—C17—C18—C13	−63.2 (3)
C7—C8—C9—C11	175.71 (19)	C22—C17—C18—C19	49.6 (3)
C26—C8—C9—C11	57.0 (2)	C16—C17—C18—C19	−72.5 (3)
C14—C8—C9—C11	−63.9 (2)	C28—C17—C18—C19	167.8 (2)
C7—C8—C9—C10	44.0 (2)	C13—C18—C19—C29	54.9 (3)
C26—C8—C9—C10	−74.8 (2)	C17—C18—C19—C29	−178.3 (2)
C14—C8—C9—C10	164.42 (17)	C13—C18—C19—C20	179.0 (2)
C2—C1—C10—C25	−70.0 (3)	C17—C18—C19—C20	−54.1 (3)
C2—C1—C10—C5	52.1 (3)	C29—C19—C20—C21	−178.1 (2)
C2—C1—C10—C9	167.35 (19)	C18—C19—C20—C21	57.5 (3)
C6—C5—C10—C25	−65.6 (3)	C29—C19—C20—C30	−55.2 (3)
C4—C5—C10—C25	67.2 (3)	C18—C19—C20—C30	−179.5 (2)
C6—C5—C10—C1	176.55 (19)	C30—C20—C21—C22	177.1 (2)
C4—C5—C10—C1	−50.7 (3)	C19—C20—C21—C22	−57.9 (3)
C6—C5—C10—C9	59.6 (2)	C20—C21—C22—C17	55.4 (3)
C4—C5—C10—C9	−167.66 (19)	C16—C17—C22—C21	69.4 (3)
C11—C9—C10—C25	−54.3 (3)	C28—C17—C22—C21	−170.5 (2)
C8—C9—C10—C25	74.7 (2)	C18—C17—C22—C21	−50.7 (3)
C11—C9—C10—C1	64.6 (2)	C3—O2—C1'—O3	5.6 (4)
C8—C9—C10—C1	−166.46 (19)	C3—O2—C1'—C2'	−172.8 (2)
C11—C9—C10—C5	−179.70 (19)	O3—C1'—C2'—C3'	−79.7 (3)
C8—C9—C10—C5	−50.7 (2)	O2—C1'—C2'—C3'	98.7 (3)
C8—C9—C11—O1	162.55 (19)	C1'—C2'—C3'—C4'	173.8 (3)
C10—C9—C11—O1	−64.6 (2)	C2'—C3'—C4'—C5'	73.9 (4)
C8—C9—C11—C12	37.8 (3)	C3'—C4'—C5'—C6'	176.2 (3)
C10—C9—C11—C12	170.67 (18)	C4'—C5'—C6'—C7'	−177.6 (3)
O1—C11—C12—C13	−132.5 (3)	C5'—C6'—C7'—C8'	176.1 (3)
C9—C11—C12—C13	−5.7 (3)	C6'—C7'—C8'—C9'	−179.5 (3)
C11—C12—C13—C18	177.1 (2)	C7'—C8'—C9'—C10'	175.0 (2)
C11—C12—C13—C14	−0.9 (4)	C8'—C9'—C10'—C11'	69.4 (3)
C12—C13—C14—C15	−147.9 (2)	C9'—C10'—C11'—C12'	177.2 (2)
C18—C13—C14—C15	34.1 (3)	C10'—C11'—C12'—C13'	179.0 (3)
C12—C13—C14—C27	96.2 (2)	C11'—C12'—C13'—C14'	176.9 (2)
C18—C13—C14—C27	−81.7 (2)	C12'—C13'—C14'—C15'	174.7 (3)
C12—C13—C14—C8	−24.9 (3)	C13'—C14'—C15'—C16'	177.1 (3)
C18—C13—C14—C8	157.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O3i	0.79 (4)	2.13 (4)	2.886 (3)	161 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O3i	0.79 (4)	2.13 (4)	2.886 (3)	161 (3)

Symmetry code: (i) .