14,15-Didehydro-hellebrigenin.

The title compound, C(24)H(30)O(5), is the didehydro product of the steroid hellebrigenin (systematic name: 3β,5,14-trihy-droxy-19-oxo-5β-bufa-20,22-dienolide). It consists of three cyclo-hexane rings (A, B and C), a five-membered ring (D) and a six-membered lactone ring (E). The stereochemistry of the ring junctions are A/B cis, B/C trans and C/D cis. Cyclo-hexane rings A, B and C have normal chair conformations. The five-membered ring D with the C=C bond adopts an envelope conformation. Lactone ring E is essentially planar with a mean derivation of 0.006 (4) Å and is β-oriented at the C atom of ring D to which it is attached. There is an O-H⋯O hydrogen bond in the mol-ecule involving the hy-droxy groups. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into chains propagating along [010]. The chains are linked by C-H⋯O contacts into a three-dimensional network.

Related literature

For previous isolations of hellebrigenin, see: Urscheler et al. (1955 ▶); Yang et al. (2010 ▶); Zhao et al. (2010 ▶). For its inhibitory activity against adenosinetriphosphatase of the 3-acetate, 3,5-diacetate, 3-iodo­acetate and 3-bromo­acetate of hellebrigenin, see: Ruoho et al. (1968 ▶). For the treatment of hellebrigenin with sodium hydroxide, see: Kupchan et al. (1969 ▶). For the stereochemistry of bufalin and secohellebrigeninamide, see: Rohrer et al. (1982 ▶); Yuan et al. (2012 ▶).

Experimental

Crystal data

C24H30O5

M = 398.48

Monoclinic,

a = 10.7628 (4) Å

b = 6.6016 (2) Å

c = 14.6376 (5) Å

β = 94.224 (3)°

V = 1037.20 (6) Å3

Z = 2

Cu Kα radiation

μ = 0.71 mm−1

T = 291 K

0.40 × 0.26 × 0.23 mm

Data collection

Oxford Gemini S Ultra Sapphire CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.819, T max = 1.000

3100 measured reflections

2238 independent reflections

2042 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.115

S = 1.04

2238 reflections

266 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: XPREP (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018570/su2412sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018570/su2412Isup2.hkl

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

C24H30O5	F(000) = 428
Mr = 398.48	Dx = 1.276 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 10.7628 (4) Å	Cell parameters from 1435 reflections
b = 6.6016 (2) Å	θ = 3.0–62.5°
c = 14.6376 (5) Å	µ = 0.71 mm−1
β = 94.224 (3)°	T = 291 K
V = 1037.20 (6) Å3	Prism, colourless
Z = 2	0.40 × 0.26 × 0.23 mm

Oxford Gemini S Ultra Sapphire CCD diffractometer	2238 independent reflections
Radiation source: fine-focus sealed tube	2042 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scan	θmax = 62.6°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −6→12
Tmin = 0.819, Tmax = 1.000	k = −7→4
3100 measured reflections	l = −16→16

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0726P)2 + 0.1057P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2238 reflections	Δρmax = 0.24 e Å−3
266 parameters	Δρmin = −0.20 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0045 (12)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	0.40415 (18)	0.7669 (4)	1.06950 (14)	0.0564 (7)
O2	0.3968 (2)	0.9967 (4)	0.91061 (15)	0.0605 (8)
O3	0.1076 (3)	1.2425 (4)	0.8935 (2)	0.0882 (11)
O4	−0.6574 (2)	0.2486 (7)	0.5959 (2)	0.0998 (13)
O5	−0.4844 (3)	0.2651 (7)	0.69025 (19)	0.1009 (13)
C1	0.1594 (2)	0.8911 (5)	0.98577 (16)	0.0395 (8)
C2	0.1910 (3)	0.6866 (5)	1.02785 (18)	0.0438 (9)
C3	0.3250 (3)	0.6280 (5)	1.01530 (18)	0.0478 (9)
C4	0.3517 (3)	0.6385 (5)	0.91490 (19)	0.0475 (9)
C5	0.3174 (2)	0.8405 (5)	0.86880 (19)	0.0451 (9)
C6	0.3428 (3)	0.8346 (7)	0.7677 (2)	0.0609 (13)
C7	0.2526 (3)	0.6979 (6)	0.71152 (19)	0.0552 (10)
C8	0.1166 (2)	0.7489 (5)	0.72275 (17)	0.0435 (9)
C9	0.0893 (2)	0.7573 (5)	0.82503 (16)	0.0358 (8)
C10	0.1798 (2)	0.9001 (4)	0.88277 (16)	0.0376 (8)
C11	−0.0483 (2)	0.8023 (5)	0.83501 (19)	0.0438 (9)
C12	−0.1299 (2)	0.6349 (5)	0.79095 (17)	0.0427 (9)
C13	−0.1110 (2)	0.6065 (5)	0.68901 (16)	0.0390 (8)
C14	0.0279 (2)	0.6028 (5)	0.67349 (16)	0.0414 (8)
C15	0.0524 (3)	0.4602 (6)	0.61287 (19)	0.0544 (10)
C16	−0.0631 (3)	0.3465 (6)	0.5790 (2)	0.0597 (10)
C17	−0.1499 (3)	0.3905 (5)	0.65465 (18)	0.0439 (9)
C18	−0.1773 (3)	0.7733 (6)	0.6318 (2)	0.0599 (11)
C19	0.1572 (3)	1.1166 (5)	0.8511 (2)	0.0560 (11)
C20	−0.2876 (3)	0.3558 (5)	0.63458 (18)	0.0459 (9)
C21	−0.3594 (3)	0.3021 (8)	0.7029 (2)	0.0707 (13)
C22	−0.3499 (3)	0.3797 (7)	0.5489 (2)	0.0683 (13)
C23	−0.4722 (3)	0.3462 (7)	0.5348 (2)	0.0660 (13)
C24	−0.5468 (3)	0.2853 (7)	0.6046 (3)	0.0716 (13)
H1	0.47040	0.71120	1.08520	0.0850*
H1A	0.21060	0.99380	1.01750	0.0470*
H1B	0.07300	0.92230	0.99440	0.0470*
H2	0.40780	0.97540	0.96580	0.0910*
H2A	0.13570	0.58490	0.99960	0.0530*
H2B	0.17820	0.69050	1.09270	0.0530*
H3	0.34000	0.48970	1.03780	0.0570*
H4A	0.30580	0.53130	0.88210	0.0570*
H4B	0.43970	0.61350	0.90990	0.0570*
H6A	0.33670	0.97090	0.74300	0.0730*
H6B	0.42710	0.78710	0.76200	0.0730*
H7A	0.26790	0.55840	0.72980	0.0660*
H7B	0.26840	0.70970	0.64730	0.0660*
H8	0.10020	0.88370	0.69650	0.0520*
H9	0.10440	0.62050	0.84930	0.0430*
H11A	−0.06290	0.81300	0.89940	0.0530*
H11B	−0.07020	0.93080	0.80600	0.0530*
H12A	−0.21660	0.66700	0.79790	0.0510*
H12B	−0.11100	0.50860	0.82290	0.0510*
H15	0.13140	0.43410	0.59380	0.0650*
H16A	−0.04700	0.20260	0.57370	0.0720*
H16B	−0.09700	0.39790	0.52020	0.0720*
H17	−0.12410	0.29820	0.70490	0.0530*
H18A	−0.26480	0.76990	0.64050	0.0900*
H18B	−0.16490	0.75220	0.56830	0.0900*
H18C	−0.14390	0.90280	0.65080	0.0900*
H19	0.18410	1.15340	0.79450	0.0670*
H21	−0.32140	0.28980	0.76170	0.0850*
H22	−0.30540	0.42010	0.49990	0.0820*
H23	−0.50960	0.36410	0.47610	0.0790*

	U11	U22	U33	U12	U13	U23
O1	0.0446 (11)	0.0602 (15)	0.0613 (12)	0.0074 (11)	−0.0164 (9)	−0.0076 (12)
O2	0.0543 (12)	0.0632 (16)	0.0627 (12)	−0.0261 (12)	−0.0045 (10)	−0.0051 (12)
O3	0.116 (2)	0.0359 (15)	0.112 (2)	0.0128 (16)	0.0031 (17)	0.0009 (16)
O4	0.0522 (14)	0.124 (3)	0.120 (2)	−0.0018 (18)	−0.0148 (14)	−0.038 (2)
O5	0.0697 (16)	0.150 (3)	0.0816 (17)	−0.025 (2)	−0.0037 (13)	0.007 (2)
C1	0.0372 (13)	0.0389 (16)	0.0414 (13)	−0.0009 (12)	−0.0037 (10)	−0.0075 (13)
C2	0.0453 (15)	0.0443 (18)	0.0412 (13)	−0.0040 (13)	−0.0007 (11)	0.0019 (13)
C3	0.0476 (15)	0.0405 (18)	0.0535 (15)	0.0029 (14)	−0.0081 (12)	−0.0001 (14)
C4	0.0372 (14)	0.0475 (19)	0.0573 (15)	0.0057 (13)	0.0012 (11)	−0.0085 (15)
C5	0.0384 (14)	0.0475 (19)	0.0486 (14)	−0.0148 (14)	−0.0012 (11)	−0.0030 (14)
C6	0.0495 (16)	0.080 (3)	0.0543 (16)	−0.0202 (18)	0.0106 (13)	0.0022 (18)
C7	0.0486 (16)	0.075 (2)	0.0433 (14)	−0.0173 (16)	0.0113 (11)	−0.0056 (16)
C8	0.0496 (15)	0.0422 (18)	0.0382 (13)	−0.0053 (14)	0.0008 (11)	0.0031 (13)
C9	0.0392 (13)	0.0307 (15)	0.0370 (12)	−0.0043 (12)	−0.0011 (9)	−0.0034 (12)
C10	0.0413 (13)	0.0304 (15)	0.0404 (13)	−0.0012 (12)	−0.0026 (10)	−0.0007 (12)
C11	0.0411 (14)	0.0432 (18)	0.0458 (14)	0.0023 (13)	−0.0048 (11)	−0.0111 (13)
C12	0.0375 (13)	0.0494 (18)	0.0408 (13)	−0.0058 (13)	0.0007 (10)	−0.0094 (14)
C13	0.0458 (14)	0.0342 (16)	0.0361 (12)	−0.0023 (13)	−0.0039 (10)	−0.0006 (12)
C14	0.0467 (14)	0.0467 (18)	0.0306 (11)	−0.0092 (14)	0.0020 (10)	0.0004 (13)
C15	0.0555 (17)	0.061 (2)	0.0475 (15)	−0.0072 (17)	0.0087 (12)	−0.0118 (17)
C16	0.0653 (18)	0.062 (2)	0.0520 (15)	−0.0126 (18)	0.0053 (14)	−0.0218 (16)
C17	0.0509 (15)	0.0412 (17)	0.0388 (12)	−0.0044 (14)	−0.0010 (11)	−0.0025 (13)
C18	0.069 (2)	0.0444 (19)	0.0628 (18)	−0.0022 (17)	−0.0196 (14)	0.0090 (17)
C19	0.069 (2)	0.0352 (18)	0.0610 (17)	−0.0103 (17)	−0.0131 (15)	0.0044 (16)
C20	0.0526 (15)	0.0406 (17)	0.0431 (13)	−0.0074 (15)	−0.0064 (12)	−0.0031 (14)
C21	0.0501 (17)	0.106 (3)	0.0540 (17)	−0.021 (2)	−0.0095 (13)	0.010 (2)
C22	0.072 (2)	0.082 (3)	0.0487 (16)	−0.021 (2)	−0.0097 (15)	0.0023 (19)
C23	0.0618 (19)	0.079 (3)	0.0527 (16)	−0.0093 (19)	−0.0253 (15)	−0.0017 (18)
C24	0.0517 (18)	0.079 (3)	0.081 (2)	0.002 (2)	−0.0169 (16)	−0.020 (2)

O1—C3	1.448 (4)	C20—C22	1.387 (4)
O2—C5	1.446 (4)	C22—C23	1.336 (5)
O3—C19	1.187 (4)	C23—C24	1.404 (5)
O4—C24	1.212 (4)	C1—H1A	0.9700
O5—C21	1.367 (5)	C1—H1B	0.9700
O5—C24	1.384 (5)	C2—H2A	0.9700
O1—H1	0.8200	C2—H2B	0.9700
O2—H2	0.8200	C3—H3	0.9800
C1—C10	1.541 (3)	C4—H4A	0.9700
C1—C2	1.512 (4)	C4—H4B	0.9700
C2—C3	1.517 (5)	C6—H6A	0.9700
C3—C4	1.520 (4)	C6—H6B	0.9700
C4—C5	1.528 (5)	C7—H7A	0.9700
C5—C10	1.560 (3)	C7—H7B	0.9700
C5—C6	1.525 (4)	C8—H8	0.9800
C6—C7	1.522 (5)	C9—H9	0.9800
C7—C8	1.523 (4)	C11—H11A	0.9700
C8—C9	1.548 (3)	C11—H11B	0.9700
C8—C14	1.503 (4)	C12—H12A	0.9700
C9—C10	1.559 (4)	C12—H12B	0.9700
C9—C11	1.528 (3)	C15—H15	0.9300
C10—C19	1.517 (4)	C16—H16A	0.9700
C11—C12	1.525 (4)	C16—H16B	0.9700
C12—C13	1.532 (3)	C17—H17	0.9800
C13—C14	1.529 (3)	C18—H18A	0.9600
C13—C17	1.559 (5)	C18—H18B	0.9600
C13—C18	1.528 (5)	C18—H18C	0.9600
C14—C15	1.333 (4)	C19—H19	0.9300
C15—C16	1.505 (5)	C21—H21	0.9300
C16—C17	1.528 (4)	C22—H22	0.9300
C17—C20	1.507 (5)	C23—H23	0.9300
C20—C21	1.355 (4)
C21—O5—C24	120.8 (3)	C3—C2—H2A	109.00
C3—O1—H1	110.00	C3—C2—H2B	109.00
C5—O2—H2	109.00	H2A—C2—H2B	108.00
C2—C1—C10	112.9 (2)	O1—C3—H3	109.00
C1—C2—C3	111.4 (2)	C2—C3—H3	109.00
O1—C3—C2	107.4 (2)	C4—C3—H3	109.00
O1—C3—C4	110.8 (3)	C3—C4—H4A	109.00
C2—C3—C4	110.8 (2)	C3—C4—H4B	109.00
C3—C4—C5	114.2 (3)	C5—C4—H4A	109.00
O2—C5—C10	107.6 (2)	C5—C4—H4B	109.00
C4—C5—C6	110.6 (3)	H4A—C4—H4B	108.00
C4—C5—C10	111.3 (2)	C5—C6—H6A	109.00
C6—C5—C10	111.9 (2)	C5—C6—H6B	109.00
O2—C5—C6	106.6 (2)	C7—C6—H6A	109.00
O2—C5—C4	108.6 (2)	C7—C6—H6B	109.00
C5—C6—C7	112.8 (3)	H6A—C6—H6B	108.00
C6—C7—C8	113.0 (3)	C6—C7—H7A	109.00
C9—C8—C14	109.1 (2)	C6—C7—H7B	109.00
C7—C8—C9	111.4 (2)	C8—C7—H7A	109.00
C7—C8—C14	112.8 (3)	C8—C7—H7B	109.00
C8—C9—C10	113.0 (2)	H7A—C7—H7B	108.00
C8—C9—C11	110.72 (19)	C7—C8—H8	108.00
C10—C9—C11	113.7 (2)	C9—C8—H8	108.00
C1—C10—C5	108.88 (19)	C14—C8—H8	108.00
C5—C10—C9	109.7 (2)	C8—C9—H9	106.00
C5—C10—C19	109.3 (2)	C10—C9—H9	106.00
C9—C10—C19	108.9 (2)	C11—C9—H9	106.00
C1—C10—C9	112.3 (2)	C9—C11—H11A	110.00
C1—C10—C19	107.7 (2)	C9—C11—H11B	110.00
C9—C11—C12	110.5 (2)	C12—C11—H11A	110.00
C11—C12—C13	112.8 (2)	C12—C11—H11B	110.00
C12—C13—C17	112.0 (2)	H11A—C11—H11B	108.00
C12—C13—C14	110.37 (18)	C11—C12—H12A	109.00
C14—C13—C18	110.6 (2)	C11—C12—H12B	109.00
C17—C13—C18	112.3 (2)	C13—C12—H12A	109.00
C12—C13—C18	110.8 (2)	C13—C12—H12B	109.00
C14—C13—C17	100.4 (2)	H12A—C12—H12B	108.00
C13—C14—C15	110.7 (2)	C14—C15—H15	124.00
C8—C14—C13	120.8 (2)	C16—C15—H15	124.00
C8—C14—C15	128.5 (2)	C15—C16—H16A	112.00
C14—C15—C16	111.9 (3)	C15—C16—H16B	111.00
C15—C16—C17	101.6 (3)	C17—C16—H16A	112.00
C13—C17—C20	116.0 (3)	C17—C16—H16B	111.00
C16—C17—C20	118.3 (2)	H16A—C16—H16B	109.00
C13—C17—C16	104.1 (2)	C13—C17—H17	106.00
O3—C19—C10	124.6 (3)	C16—C17—H17	106.00
C17—C20—C22	124.2 (3)	C20—C17—H17	106.00
C17—C20—C21	120.1 (3)	C13—C18—H18A	109.00
C21—C20—C22	115.7 (3)	C13—C18—H18B	110.00
O5—C21—C20	123.8 (3)	C13—C18—H18C	109.00
C20—C22—C23	121.8 (3)	H18A—C18—H18B	109.00
C22—C23—C24	123.0 (3)	H18A—C18—H18C	109.00
O5—C24—C23	114.9 (3)	H18B—C18—H18C	110.00
O4—C24—O5	118.9 (4)	O3—C19—H19	118.00
O4—C24—C23	126.2 (4)	C10—C19—H19	118.00
C2—C1—H1A	109.00	O5—C21—H21	118.00
C2—C1—H1B	109.00	C20—C21—H21	118.00
C10—C1—H1A	109.00	C20—C22—H22	119.00
C10—C1—H1B	109.00	C23—C22—H22	119.00
H1A—C1—H1B	108.00	C22—C23—H23	118.00
C1—C2—H2A	109.00	C24—C23—H23	119.00
C1—C2—H2B	109.00
C24—O5—C21—C20	−1.4 (8)	C11—C9—C10—C1	58.1 (3)
C21—O5—C24—O4	179.1 (5)	C11—C9—C10—C5	179.4 (2)
C21—O5—C24—C23	−0.3 (7)	C11—C9—C10—C19	−61.1 (3)
C10—C1—C2—C3	57.9 (3)	C8—C9—C11—C12	61.7 (3)
C2—C1—C10—C5	−56.2 (3)	C10—C9—C11—C12	−169.8 (2)
C2—C1—C10—C9	65.5 (3)	C1—C10—C19—O3	−14.4 (4)
C2—C1—C10—C19	−174.6 (2)	C5—C10—C19—O3	−132.5 (3)
C1—C2—C3—O1	67.1 (3)	C9—C10—C19—O3	107.6 (3)
C1—C2—C3—C4	−54.0 (3)	C9—C11—C12—C13	−58.5 (3)
O1—C3—C4—C5	−66.2 (3)	C11—C12—C13—C14	46.1 (3)
C2—C3—C4—C5	52.8 (3)	C11—C12—C13—C17	157.0 (2)
C3—C4—C5—O2	65.4 (3)	C11—C12—C13—C18	−76.8 (3)
C3—C4—C5—C6	−177.9 (3)	C12—C13—C14—C8	−42.0 (4)
C3—C4—C5—C10	−52.9 (3)	C12—C13—C14—C15	138.7 (3)
O2—C5—C6—C7	−171.8 (3)	C17—C13—C14—C8	−160.3 (2)
C4—C5—C6—C7	70.3 (3)	C17—C13—C14—C15	20.4 (3)
C10—C5—C6—C7	−54.4 (4)	C18—C13—C14—C8	81.0 (3)
O2—C5—C10—C1	−66.4 (3)	C18—C13—C14—C15	−98.3 (3)
O2—C5—C10—C9	170.4 (2)	C12—C13—C17—C16	−148.9 (2)
O2—C5—C10—C19	51.1 (3)	C12—C13—C17—C20	79.3 (3)
C4—C5—C10—C1	52.5 (3)	C14—C13—C17—C16	−31.8 (3)
C4—C5—C10—C9	−70.7 (3)	C14—C13—C17—C20	−163.6 (2)
C4—C5—C10—C19	169.9 (2)	C18—C13—C17—C16	85.7 (3)
C6—C5—C10—C1	176.8 (3)	C18—C13—C17—C20	−46.1 (3)
C6—C5—C10—C9	53.6 (3)	C8—C14—C15—C16	−179.7 (3)
C6—C5—C10—C19	−65.8 (3)	C13—C14—C15—C16	−0.4 (4)
C5—C6—C7—C8	53.6 (4)	C14—C15—C16—C17	−20.3 (4)
C6—C7—C8—C9	−52.0 (4)	C15—C16—C17—C13	31.8 (3)
C6—C7—C8—C14	−175.2 (3)	C15—C16—C17—C20	162.3 (3)
C7—C8—C9—C10	52.9 (3)	C13—C17—C20—C21	−85.2 (4)
C7—C8—C9—C11	−178.3 (3)	C13—C17—C20—C22	93.2 (4)
C14—C8—C9—C10	178.1 (2)	C16—C17—C20—C21	149.9 (4)
C14—C8—C9—C11	−53.1 (3)	C16—C17—C20—C22	−31.7 (5)
C7—C8—C14—C13	169.8 (2)	C17—C20—C21—O5	−179.0 (4)
C7—C8—C14—C15	−10.9 (4)	C22—C20—C21—O5	2.4 (7)
C9—C8—C14—C13	45.4 (3)	C17—C20—C22—C23	179.8 (4)
C9—C8—C14—C15	−135.3 (3)	C21—C20—C22—C23	−1.8 (6)
C8—C9—C10—C1	−174.6 (2)	C20—C22—C23—C24	0.1 (7)
C8—C9—C10—C5	−53.4 (3)	C22—C23—C24—O4	−178.4 (5)
C8—C9—C10—C19	66.2 (3)	C22—C23—C24—O5	0.9 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	2.05	2.773 (3)	147
O1—H1···O2i	0.82	2.01	2.786 (3)	158
C9—H9···O3ii	0.98	2.58	3.545 (4)	169
C15—H15···O4iii	0.93	2.58	3.447 (4)	155
C22—H22···O4iv	0.93	2.60	3.233 (6)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	2.05	2.773 (3)	147
O1—H1⋯O2i	0.82	2.01	2.786 (3)	158
C9—H9⋯O3ii	0.98	2.58	3.545 (4)	169
C15—H15⋯O4iii	0.93	2.58	3.447 (4)	155
C22—H22⋯O4iv	0.93	2.60	3.233 (6)	126

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .