Hoodigogenin A from Hoodia gordonii.

The title mol-ecule (systematic name: 12-O-β-tigloyl-3β,14β-dihydroxy-pregn-5-en-20-one), C(26)H(38)O(5), isolated from aerial parts of Hoodia gordonii, has its steroid A and C rings in chair conformations, its B ring in a half-chair conformation, and its five-membered ring in an envelope conformation. The OH group at the C/D ring junction forms an intra-molecular hydrogen bond with the keto substituent. The OH group on the A ring forms an inter-molecular hydrogen bond with the tiglate C=O group, propagating [010] chains in the crystal structure.

Related literature

For related literature, see: Allen (2002 ▶); Consumer Reports (2006 ▶); Etter (1990 ▶); MacLean & Luo (2004 ▶); Muller & Albers (2002 ▶); Nutrition Business Journal (2007 ▶); Pawar et al. (2007 ▶); Shin et al. (1990 ▶); Van Heerden et al. (1998 ▶).

Experimental

Crystal data

C26H38O5

M = 430.56

Orthorhombic,

a = 7.6523 (9) Å

b = 10.6885 (12) Å

c = 27.705 (3) Å

V = 2266.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.30 × 0.27 × 0.05 mm

Data collection

Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler) diffractometer

Absorption correction: none

9377 measured reflections

2677 independent reflections

2156 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.100

S = 1.02

2677 reflections

287 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022368/hb2752sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022368/hb2752Isup2.hkl

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

C26H38O5	F000 = 936
Mr = 430.56	Dx = 1.262 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2446 reflections
a = 7.6523 (9) Å	θ = 2.5–26.6º
b = 10.6885 (12) Å	µ = 0.09 mm−1
c = 27.705 (3) Å	T = 100 K
V = 2266.0 (4) Å3	Plate, colorless
Z = 4	0.30 × 0.27 × 0.05 mm

Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler) diffractometer	2156 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Monochromator: graphite	θmax = 26.7º
T = 100 K	θmin = 2.7º
ω and φ scans	h = −9→9
Absorption correction: none	k = −13→13
9377 measured reflections	l = −34→34
2677 independent reflections

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0516P)2 + 0.3846P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2677 reflections	Δρmax = 0.20 e Å−3
287 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.9957 (2)	0.46948 (17)	0.91649 (6)	0.0407 (5)
H10H	1.0621	0.4080	0.9120	0.061*
O2	0.3082 (2)	0.30783 (16)	0.67021 (6)	0.0341 (4)
H20H	0.2534	0.3094	0.6439	0.051*
O3	0.2237 (2)	0.30076 (18)	0.56873 (6)	0.0436 (5)
O4	0.7859 (2)	0.53134 (15)	0.59363 (6)	0.0305 (4)
O5	0.7923 (2)	0.74167 (16)	0.59427 (6)	0.0369 (4)
C1	0.9214 (3)	0.5459 (3)	0.78456 (8)	0.0302 (5)
H1A	1.0060	0.5598	0.7581	0.036*
H1B	0.8524	0.6236	0.7884	0.036*
C2	1.0228 (3)	0.5220 (3)	0.83123 (9)	0.0342 (6)
H2A	1.1021	0.4498	0.8266	0.041*
H2B	1.0951	0.5962	0.8389	0.041*
C3	0.9010 (4)	0.4954 (2)	0.87292 (8)	0.0338 (6)
H3	0.8282	0.5718	0.8785	0.041*
C4	0.7785 (3)	0.3879 (2)	0.86049 (9)	0.0329 (6)
H4A	0.8471	0.3095	0.8585	0.039*
H4B	0.6921	0.3780	0.8868	0.039*
C5	0.6821 (3)	0.4070 (2)	0.81332 (9)	0.0291 (5)
C6	0.5095 (3)	0.3951 (2)	0.81037 (9)	0.0329 (6)
H6	0.4469	0.3787	0.8393	0.039*
C7	0.4070 (3)	0.4058 (3)	0.76433 (9)	0.0349 (6)
H7A	0.3450	0.4871	0.7638	0.042*
H7B	0.3182	0.3385	0.7632	0.042*
C8	0.5244 (3)	0.3962 (2)	0.71992 (8)	0.0289 (5)
H8	0.5711	0.3089	0.7191	0.035*
C9	0.6822 (3)	0.4840 (2)	0.72681 (8)	0.0273 (5)
H9	0.6346	0.5680	0.7358	0.033*
C10	0.7967 (3)	0.4390 (2)	0.76984 (8)	0.0276 (5)
C11	0.7907 (3)	0.5023 (2)	0.68051 (8)	0.0292 (6)
H11A	0.8714	0.5738	0.6850	0.035*
H11B	0.8622	0.4266	0.6747	0.035*
C12	0.6770 (3)	0.5265 (2)	0.63685 (8)	0.0284 (5)
H12	0.6155	0.6084	0.6409	0.034*
C13	0.5413 (3)	0.4230 (2)	0.62780 (8)	0.0282 (5)
C14	0.4220 (3)	0.4154 (2)	0.67314 (9)	0.0283 (5)
C15	0.3094 (3)	0.5331 (2)	0.66889 (9)	0.0324 (6)
H15A	0.3745	0.6079	0.6798	0.039*
H15B	0.2013	0.5250	0.6883	0.039*
C16	0.2667 (3)	0.5414 (3)	0.61473 (9)	0.0361 (6)
H16A	0.2616	0.6299	0.6044	0.043*
H16B	0.1522	0.5019	0.6080	0.043*
C17	0.4140 (3)	0.4716 (2)	0.58736 (9)	0.0311 (5)
H17	0.4780	0.5329	0.5666	0.037*
C18	0.6315 (3)	0.2983 (2)	0.61696 (9)	0.0324 (6)
H18A	0.6999	0.2722	0.6451	0.049*
H18B	0.7093	0.3083	0.5891	0.049*
H18C	0.5431	0.2347	0.6097	0.049*
C19	0.9048 (3)	0.3220 (2)	0.75633 (9)	0.0306 (6)
H19A	0.9960	0.3454	0.7332	0.046*
H19B	0.8279	0.2592	0.7418	0.046*
H19C	0.9590	0.2873	0.7854	0.046*
C20	0.3456 (3)	0.3660 (2)	0.55563 (9)	0.0336 (6)
C21	0.4373 (4)	0.3454 (3)	0.50851 (9)	0.0427 (7)
H21A	0.5622	0.3317	0.5144	0.064*
H21B	0.4221	0.4191	0.4879	0.064*
H21C	0.3877	0.2719	0.4924	0.064*
C22	0.8251 (3)	0.6433 (2)	0.57417 (9)	0.0296 (5)
C23	0.9065 (3)	0.6338 (2)	0.52566 (9)	0.0301 (6)
C24	0.9321 (4)	0.7573 (3)	0.50011 (11)	0.0379 (6)
H24A	1.0187	0.8073	0.5176	0.057*
H24B	0.8209	0.8026	0.4990	0.057*
H24C	0.9735	0.7420	0.4672	0.057*
C25	0.9463 (3)	0.5220 (3)	0.50738 (9)	0.0344 (6)
H25	0.9221	0.4519	0.5274	0.041*
C26	1.0243 (4)	0.4940 (3)	0.45924 (9)	0.0412 (7)
H26A	1.0654	0.5719	0.4444	0.062*
H26B	0.9359	0.4553	0.4385	0.062*
H26C	1.1230	0.4364	0.4632	0.062*

	U11	U22	U33	U12	U13	U23
O1	0.0448 (11)	0.0395 (11)	0.0377 (10)	0.0083 (10)	−0.0043 (9)	−0.0037 (8)
O2	0.0286 (9)	0.0326 (9)	0.0412 (9)	−0.0092 (8)	−0.0009 (8)	0.0016 (8)
O3	0.0432 (10)	0.0413 (11)	0.0463 (10)	−0.0129 (10)	−0.0051 (10)	0.0009 (9)
O4	0.0285 (8)	0.0268 (9)	0.0363 (9)	0.0004 (8)	0.0056 (8)	0.0033 (8)
O5	0.0416 (10)	0.0273 (10)	0.0417 (10)	−0.0030 (9)	0.0086 (9)	−0.0013 (8)
C1	0.0268 (12)	0.0270 (13)	0.0369 (13)	−0.0032 (11)	0.0028 (11)	−0.0010 (11)
C2	0.0316 (12)	0.0317 (14)	0.0395 (14)	−0.0052 (12)	0.0004 (12)	−0.0019 (12)
C3	0.0355 (13)	0.0312 (15)	0.0346 (13)	0.0060 (12)	−0.0026 (12)	−0.0002 (11)
C4	0.0313 (12)	0.0314 (14)	0.0360 (13)	0.0003 (12)	0.0050 (11)	0.0008 (11)
C5	0.0279 (12)	0.0221 (13)	0.0371 (13)	0.0007 (10)	0.0024 (11)	0.0005 (10)
C6	0.0299 (13)	0.0333 (14)	0.0354 (13)	−0.0004 (12)	0.0046 (11)	0.0028 (12)
C7	0.0264 (13)	0.0380 (15)	0.0403 (15)	−0.0009 (12)	0.0048 (12)	0.0024 (12)
C8	0.0227 (11)	0.0254 (13)	0.0386 (13)	−0.0004 (11)	0.0007 (11)	0.0018 (11)
C9	0.0246 (11)	0.0237 (13)	0.0337 (13)	0.0011 (10)	0.0024 (10)	0.0006 (10)
C10	0.0239 (11)	0.0243 (13)	0.0345 (13)	−0.0002 (10)	0.0027 (10)	−0.0004 (10)
C11	0.0215 (11)	0.0298 (14)	0.0362 (13)	−0.0012 (10)	0.0008 (10)	0.0020 (10)
C12	0.0252 (12)	0.0263 (13)	0.0338 (13)	0.0008 (11)	0.0036 (11)	0.0018 (11)
C13	0.0227 (11)	0.0265 (13)	0.0354 (13)	0.0016 (10)	−0.0007 (10)	0.0025 (11)
C14	0.0200 (11)	0.0269 (13)	0.0381 (13)	−0.0023 (10)	0.0037 (11)	−0.0003 (11)
C15	0.0245 (12)	0.0305 (13)	0.0422 (13)	0.0005 (11)	0.0027 (12)	−0.0007 (12)
C16	0.0327 (13)	0.0323 (14)	0.0434 (15)	0.0060 (12)	0.0001 (12)	0.0011 (12)
C17	0.0277 (11)	0.0288 (13)	0.0369 (13)	0.0004 (11)	−0.0009 (11)	0.0029 (11)
C18	0.0340 (13)	0.0260 (13)	0.0372 (13)	0.0012 (11)	−0.0004 (12)	−0.0009 (11)
C19	0.0267 (12)	0.0280 (14)	0.0372 (13)	0.0000 (11)	0.0017 (11)	0.0006 (11)
C20	0.0333 (13)	0.0289 (14)	0.0388 (14)	0.0014 (12)	−0.0067 (12)	0.0057 (11)
C21	0.0473 (17)	0.0415 (17)	0.0393 (15)	0.0039 (14)	−0.0017 (14)	−0.0023 (13)
C22	0.0238 (12)	0.0273 (13)	0.0379 (13)	−0.0017 (11)	−0.0014 (11)	0.0030 (11)
C23	0.0238 (12)	0.0337 (14)	0.0327 (13)	−0.0027 (11)	−0.0010 (11)	0.0032 (11)
C24	0.0379 (14)	0.0369 (15)	0.0388 (13)	−0.0039 (13)	0.0075 (13)	0.0026 (11)
C25	0.0318 (13)	0.0343 (15)	0.0371 (13)	0.0018 (12)	0.0005 (12)	0.0025 (12)
C26	0.0426 (15)	0.0396 (17)	0.0415 (15)	0.0064 (13)	0.0018 (13)	−0.0021 (12)

O1—C3	1.435 (3)	C11—H11B	0.9900
O1—H10H	0.8400	C12—C13	1.538 (3)
O2—C14	1.445 (3)	C12—H12	1.0000
O2—H20H	0.8400	C13—C18	1.530 (3)
O3—C20	1.220 (3)	C13—C14	1.555 (3)
O4—C22	1.347 (3)	C13—C17	1.573 (3)
O4—C12	1.460 (3)	C14—C15	1.529 (3)
O5—C22	1.216 (3)	C15—C16	1.538 (3)
C1—C2	1.530 (3)	C15—H15A	0.9900
C1—C10	1.543 (3)	C15—H15B	0.9900
C1—H1A	0.9900	C16—C17	1.550 (3)
C1—H1B	0.9900	C16—H16A	0.9900
C2—C3	1.511 (3)	C16—H16B	0.9900
C2—H2A	0.9900	C17—C20	1.523 (4)
C2—H2B	0.9900	C17—H17	1.0000
C3—C4	1.523 (4)	C18—H18A	0.9800
C3—H3	1.0000	C18—H18B	0.9800
C4—C5	1.515 (3)	C18—H18C	0.9800
C4—H4A	0.9900	C19—H19A	0.9800
C4—H4B	0.9900	C19—H19B	0.9800
C5—C6	1.329 (3)	C19—H19C	0.9800
C5—C10	1.529 (3)	C20—C21	1.498 (4)
C6—C7	1.502 (3)	C21—H21A	0.9800
C6—H6	0.9500	C21—H21B	0.9800
C7—C8	1.527 (3)	C21—H21C	0.9800
C7—H7A	0.9900	C22—C23	1.485 (3)
C7—H7B	0.9900	C23—C25	1.333 (4)
C8—C14	1.528 (3)	C23—C24	1.511 (4)
C8—C9	1.542 (3)	C24—H24A	0.9800
C8—H8	1.0000	C24—H24B	0.9800
C9—C11	1.540 (3)	C24—H24C	0.9800
C9—C10	1.555 (3)	C25—C26	1.492 (4)
C9—H9	1.0000	C25—H25	0.9500
C10—C19	1.545 (3)	C26—H26A	0.9800
C11—C12	1.512 (3)	C26—H26B	0.9800
C11—H11A	0.9900	C26—H26C	0.9800
C3—O1—H10H	109.5	C12—C13—C14	107.59 (19)
C14—O2—H20H	109.5	C18—C13—C17	115.3 (2)
C22—O4—C12	119.14 (18)	C12—C13—C17	107.28 (19)
C2—C1—C10	114.4 (2)	C14—C13—C17	103.22 (18)
C2—C1—H1A	108.7	O2—C14—C8	104.46 (18)
C10—C1—H1A	108.7	O2—C14—C15	108.09 (18)
C2—C1—H1B	108.7	C8—C14—C15	117.7 (2)
C10—C1—H1B	108.7	O2—C14—C13	110.49 (19)
H1A—C1—H1B	107.6	C8—C14—C13	113.02 (17)
C3—C2—C1	111.38 (19)	C15—C14—C13	103.07 (19)
C3—C2—H2A	109.4	C14—C15—C16	104.0 (2)
C1—C2—H2A	109.4	C14—C15—H15A	111.0
C3—C2—H2B	109.4	C16—C15—H15A	111.0
C1—C2—H2B	109.4	C14—C15—H15B	111.0
H2A—C2—H2B	108.0	C16—C15—H15B	111.0
O1—C3—C2	111.6 (2)	H15A—C15—H15B	109.0
O1—C3—C4	110.8 (2)	C15—C16—C17	107.2 (2)
C2—C3—C4	110.4 (2)	C15—C16—H16A	110.3
O1—C3—H3	108.0	C17—C16—H16A	110.3
C2—C3—H3	108.0	C15—C16—H16B	110.3
C4—C3—H3	108.0	C17—C16—H16B	110.3
C5—C4—C3	113.1 (2)	H16A—C16—H16B	108.5
C5—C4—H4A	109.0	C20—C17—C16	112.9 (2)
C3—C4—H4A	109.0	C20—C17—C13	112.3 (2)
C5—C4—H4B	109.0	C16—C17—C13	105.12 (19)
C3—C4—H4B	109.0	C20—C17—H17	108.8
H4A—C4—H4B	107.8	C16—C17—H17	108.8
C6—C5—C4	121.6 (2)	C13—C17—H17	108.8
C6—C5—C10	122.9 (2)	C13—C18—H18A	109.5
C4—C5—C10	115.52 (19)	C13—C18—H18B	109.5
C5—C6—C7	124.3 (2)	H18A—C18—H18B	109.5
C5—C6—H6	117.8	C13—C18—H18C	109.5
C7—C6—H6	117.8	H18A—C18—H18C	109.5
C6—C7—C8	111.86 (19)	H18B—C18—H18C	109.5
C6—C7—H7A	109.2	C10—C19—H19A	109.5
C8—C7—H7A	109.2	C10—C19—H19B	109.5
C6—C7—H7B	109.2	H19A—C19—H19B	109.5
C8—C7—H7B	109.2	C10—C19—H19C	109.5
H7A—C7—H7B	107.9	H19A—C19—H19C	109.5
C7—C8—C14	111.91 (18)	H19B—C19—H19C	109.5
C7—C8—C9	108.7 (2)	O3—C20—C21	122.2 (2)
C14—C8—C9	115.15 (19)	O3—C20—C17	121.0 (2)
C7—C8—H8	106.9	C21—C20—C17	116.8 (2)
C14—C8—H8	106.9	C20—C21—H21A	109.5
C9—C8—H8	106.9	C20—C21—H21B	109.5
C11—C9—C8	113.34 (18)	H21A—C21—H21B	109.5
C11—C9—C10	111.96 (18)	C20—C21—H21C	109.5
C8—C9—C10	110.35 (19)	H21A—C21—H21C	109.5
C11—C9—H9	106.9	H21B—C21—H21C	109.5
C8—C9—H9	106.9	O5—C22—O4	122.6 (2)
C10—C9—H9	106.9	O5—C22—C23	124.1 (2)
C5—C10—C1	108.17 (19)	O4—C22—C23	113.2 (2)
C5—C10—C19	108.47 (19)	C25—C23—C22	120.1 (2)
C1—C10—C19	109.41 (19)	C25—C23—C24	125.1 (2)
C5—C10—C9	110.49 (19)	C22—C23—C24	114.7 (2)
C1—C10—C9	108.76 (19)	C23—C24—H24A	109.5
C19—C10—C9	111.48 (19)	C23—C24—H24B	109.5
C12—C11—C9	112.20 (18)	H24A—C24—H24B	109.5
C12—C11—H11A	109.2	C23—C24—H24C	109.5
C9—C11—H11A	109.2	H24A—C24—H24C	109.5
C12—C11—H11B	109.2	H24B—C24—H24C	109.5
C9—C11—H11B	109.2	C23—C25—C26	127.7 (2)
H11A—C11—H11B	107.9	C23—C25—H25	116.2
O4—C12—C11	109.50 (17)	C26—C25—H25	116.2
O4—C12—C13	106.10 (18)	C25—C26—H26A	109.5
C11—C12—C13	113.3 (2)	C25—C26—H26B	109.5
O4—C12—H12	109.3	H26A—C26—H26B	109.5
C11—C12—H12	109.3	C25—C26—H26C	109.5
C13—C12—H12	109.3	H26A—C26—H26C	109.5
C18—C13—C12	110.73 (19)	H26B—C26—H26C	109.5
C18—C13—C14	112.2 (2)
C10—C1—C2—C3	−56.4 (3)	O4—C12—C13—C17	−69.3 (2)
C1—C2—C3—O1	178.4 (2)	C11—C12—C13—C17	170.54 (19)
C1—C2—C3—C4	54.7 (3)	C7—C8—C14—O2	−67.2 (2)
O1—C3—C4—C5	−176.92 (19)	C9—C8—C14—O2	168.12 (18)
C2—C3—C4—C5	−52.8 (3)	C7—C8—C14—C15	52.7 (3)
C3—C4—C5—C6	−128.9 (3)	C9—C8—C14—C15	−72.1 (3)
C3—C4—C5—C10	51.8 (3)	C7—C8—C14—C13	172.7 (2)
C4—C5—C6—C7	−176.5 (2)	C9—C8—C14—C13	48.0 (3)
C10—C5—C6—C7	2.7 (4)	C18—C13—C14—O2	−49.4 (2)
C5—C6—C7—C8	15.6 (4)	C12—C13—C14—O2	−171.42 (18)
C6—C7—C8—C14	−176.4 (2)	C17—C13—C14—O2	75.3 (2)
C6—C7—C8—C9	−48.1 (3)	C18—C13—C14—C8	67.3 (3)
C7—C8—C9—C11	−168.6 (2)	C12—C13—C14—C8	−54.8 (2)
C14—C8—C9—C11	−42.2 (3)	C17—C13—C14—C8	−168.0 (2)
C7—C8—C9—C10	64.9 (2)	C18—C13—C14—C15	−164.7 (2)
C14—C8—C9—C10	−168.70 (19)	C12—C13—C14—C15	73.3 (2)
C6—C5—C10—C1	131.8 (3)	C17—C13—C14—C15	−39.9 (2)
C4—C5—C10—C1	−48.9 (3)	O2—C14—C15—C16	−76.7 (2)
C6—C5—C10—C19	−109.6 (3)	C8—C14—C15—C16	165.4 (2)
C4—C5—C10—C19	69.7 (3)	C13—C14—C15—C16	40.3 (2)
C6—C5—C10—C9	12.9 (3)	C14—C15—C16—C17	−25.1 (3)
C4—C5—C10—C9	−167.9 (2)	C15—C16—C17—C20	122.9 (2)
C2—C1—C10—C5	51.3 (3)	C15—C16—C17—C13	0.2 (3)
C2—C1—C10—C19	−66.7 (3)	C18—C13—C17—C20	23.8 (3)
C2—C1—C10—C9	171.30 (19)	C12—C13—C17—C20	147.6 (2)
C11—C9—C10—C5	−173.29 (19)	C14—C13—C17—C20	−98.9 (2)
C8—C9—C10—C5	−46.0 (2)	C18—C13—C17—C16	147.0 (2)
C11—C9—C10—C1	68.1 (2)	C12—C13—C17—C16	−89.2 (2)
C8—C9—C10—C1	−164.62 (18)	C14—C13—C17—C16	24.2 (2)
C11—C9—C10—C19	−52.6 (3)	C16—C17—C20—O3	−37.5 (3)
C8—C9—C10—C19	74.7 (2)	C13—C17—C20—O3	81.1 (3)
C8—C9—C11—C12	45.5 (3)	C16—C17—C20—C21	143.6 (2)
C10—C9—C11—C12	171.1 (2)	C13—C17—C20—C21	−97.7 (2)
C22—O4—C12—C11	−102.8 (2)	C12—O4—C22—O5	9.5 (3)
C22—O4—C12—C13	134.6 (2)	C12—O4—C22—C23	−168.83 (18)
C9—C11—C12—O4	−174.75 (19)	O5—C22—C23—C25	176.5 (3)
C9—C11—C12—C13	−56.5 (3)	O4—C22—C23—C25	−5.2 (3)
O4—C12—C13—C18	57.3 (2)	O5—C22—C23—C24	−5.4 (4)
C11—C12—C13—C18	−62.9 (2)	O4—C22—C23—C24	172.9 (2)
O4—C12—C13—C14	−179.76 (17)	C22—C23—C25—C26	178.5 (2)
C11—C12—C13—C14	60.1 (2)	C24—C23—C25—C26	0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H10H···O5i	0.84	2.11	2.941 (3)	173
O2—H20H···O3	0.84	2.10	2.886 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H10H⋯O5i	0.84	2.11	2.941 (3)	173
O2—H20H⋯O3	0.84	2.10	2.886 (2)	156

Symmetry code: (i) .