(22E,24R)-3β,5α,9α-Trihy-droxy-ergosta-7,22-dien-6-one monohydrate.

The title ergosterol compound, C(28)H(44)O(4)·H(2)O, is composed of four fused rings (three six-membered and one five-membered) and a side chain. It is a derivative of ergosterol and was isolated from a marine-derived halotolerant fungus, Cladosporium cladosporioides PXP-49. In the crystal, mol-ecules are assembled by classical O-H⋯O hydrogen bonds, forming a two-dimensional network, with base vectors [100] and [010]. The absolute configuration was assigned from the measured optical rotation and reference to the literature. An intra-molecular O-H⋯O hydrogen bond occurs.

Related literature

For general background to the cytotoxic activity of similar compounds, see: Valisolalao et al. (1983 ▶); Kawagishi et al. (1988 ▶); Takaishi et al. (1991 ▶); Ishizuka et al. (1997 ▶); Yaoita et al. (1998 ▶); Sun et al. (2006 ▶); Tang et al. (2007 ▶); Cui et al. (2010 ▶). For details of ring conformations and puckering parameters, see: Cremer & Pople (1975 ▶); Baginski et al. (1989 ▶); Gonzalez et al. (2002 ▶).

Experimental

Crystal data

C28H44O4·H2O

M = 462.65

Monoclinic,

a = 6.7605 (8) Å

b = 7.2626 (11) Å

c = 28.461 (2) Å

β = 96.083 (1)°

V = 1389.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 298 K

0.40 × 0.35 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.971, T max = 0.988

7040 measured reflections

2641 independent reflections

1557 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.108

S = 1.02

2641 reflections

304 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681101347X/su2267sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101347X/su2267Isup2.hkl

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

C28H44O4·H2O	F(000) = 508
Mr = 462.65	Dx = 1.106 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1224 reflections
a = 6.7605 (8) Å	θ = 2.9–18.6°
b = 7.2626 (11) Å	µ = 0.07 mm−1
c = 28.461 (2) Å	T = 298 K
β = 96.083 (1)°	Needle, colourless
V = 1389.5 (3) Å3	0.40 × 0.35 × 0.17 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2641 independent reflections
Radiation source: fine-focus sealed tube	1557 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
Tmin = 0.971, Tmax = 0.988	k = −8→8
7040 measured reflections	l = −22→33

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.036P)2] where P = (Fo2 + 2Fc2)/3
2641 reflections	(Δ/σ)max = 0.001
304 parameters	Δρmax = 0.14 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	0.8875 (4)	0.0054 (4)	0.52563 (10)	0.0738 (10)
H1	0.9909	0.0624	0.5235	0.111*
O2	0.4476 (4)	0.2358 (4)	0.60388 (9)	0.0554 (8)
H2	0.3863	0.2270	0.5775	0.083*
O3	0.5562 (4)	0.6238 (4)	0.55751 (10)	0.0686 (9)
O4	0.4840 (4)	0.2365 (4)	0.69723 (9)	0.0618 (8)
H4	0.4212	0.2108	0.6718	0.093*
O5	0.2328 (4)	0.1982 (4)	0.51822 (8)	0.0572 (8)
H5C	0.1825	0.3000	0.5082	0.069*
H5D	0.3038	0.1571	0.4976	0.069*
C1	0.8286 (7)	0.1178 (6)	0.65380 (14)	0.0609 (12)
H1A	0.9211	0.1058	0.6821	0.073*
H1B	0.7149	0.0399	0.6576	0.073*
C2	0.9293 (6)	0.0501 (6)	0.61159 (15)	0.0665 (13)
H2A	1.0513	0.1188	0.6097	0.080*
H2B	0.9640	−0.0787	0.6161	0.080*
C3	0.7952 (6)	0.0726 (6)	0.56552 (15)	0.0595 (12)
H3	0.6758	−0.0019	0.5680	0.071*
C4	0.7289 (6)	0.2714 (6)	0.55897 (13)	0.0515 (11)
H4A	0.6375	0.2816	0.5304	0.062*
H4B	0.8437	0.3478	0.5551	0.062*
C5	0.6271 (6)	0.3417 (5)	0.60092 (13)	0.0469 (11)
C6	0.5590 (6)	0.5400 (6)	0.59528 (15)	0.0506 (11)
C7	0.4882 (6)	0.6255 (6)	0.63688 (13)	0.0513 (11)
H7	0.4196	0.7364	0.6331	0.062*
C8	0.5173 (6)	0.5519 (5)	0.67999 (14)	0.0454 (10)
C9	0.6322 (6)	0.3742 (5)	0.69000 (14)	0.0481 (11)
C10	0.7588 (6)	0.3185 (5)	0.64904 (14)	0.0477 (11)
C11	0.7618 (7)	0.3829 (6)	0.73789 (14)	0.0615 (13)
H11A	0.8054	0.2592	0.7467	0.074*
H11B	0.8795	0.4554	0.7340	0.074*
C12	0.6586 (7)	0.4650 (6)	0.77811 (14)	0.0663 (13)
H12A	0.7531	0.4736	0.8061	0.080*
H12B	0.5519	0.3838	0.7852	0.080*
C13	0.5735 (6)	0.6555 (6)	0.76590 (13)	0.0510 (11)
C14	0.4259 (6)	0.6303 (6)	0.72149 (13)	0.0469 (10)
H14	0.3312	0.5369	0.7300	0.056*
C15	0.3080 (6)	0.8098 (6)	0.71665 (14)	0.0564 (12)
H15A	0.1746	0.7887	0.7014	0.068*
H15B	0.3738	0.8996	0.6984	0.068*
C16	0.3026 (7)	0.8755 (6)	0.76823 (15)	0.0661 (13)
H16A	0.1674	0.8727	0.7767	0.079*
H16B	0.3523	1.0005	0.7719	0.079*
C17	0.4362 (6)	0.7424 (6)	0.80017 (14)	0.0596 (12)
H17	0.3503	0.6441	0.8101	0.072*
C18	0.5296 (7)	0.8390 (7)	0.84525 (15)	0.0718 (14)
H18	0.6067	0.9439	0.8354	0.086*
C19	0.3696 (8)	0.9138 (8)	0.87252 (16)	0.0796 (15)
H19	0.2887	0.8264	0.8848	0.096*
C20	0.3289 (8)	1.0835 (8)	0.88128 (17)	0.0869 (16)
H20	0.4126	1.1709	0.8700	0.104*
C21	0.1657 (9)	1.1575 (9)	0.90707 (19)	0.1016 (19)
H21	0.1019	1.0547	0.9219	0.122*
C22	0.2406 (12)	1.2938 (10)	0.9449 (2)	0.131 (3)
H22	0.3067	1.3949	0.9299	0.157*
C23	0.0845 (14)	1.3730 (13)	0.9714 (3)	0.211 (4)
H23A	0.0014	1.2760	0.9811	0.316*
H23B	0.0052	1.4578	0.9516	0.316*
H23C	0.1454	1.4366	0.9988	0.316*
C24	0.9393 (6)	0.4470 (6)	0.64853 (14)	0.0608 (12)
H24A	1.0417	0.4093	0.6725	0.091*
H24B	0.9000	0.5711	0.6546	0.091*
H24C	0.9888	0.4409	0.6182	0.091*
C25	0.7358 (6)	0.7927 (6)	0.75607 (15)	0.0681 (14)
H25A	0.7981	0.7527	0.7291	0.102*
H25B	0.8335	0.7996	0.7831	0.102*
H25C	0.6775	0.9120	0.7499	0.102*
C26	0.6712 (9)	0.7170 (9)	0.87720 (17)	0.110 (2)
H26A	0.7094	0.7798	0.9064	0.165*
H26B	0.7876	0.6909	0.8617	0.165*
H26C	0.6055	0.6038	0.8835	0.165*
C27	0.0112 (11)	1.2509 (12)	0.8717 (2)	0.186 (4)
H27A	0.0681	1.3595	0.8593	0.280*
H27B	−0.1028	1.2843	0.8872	0.280*
H27C	−0.0285	1.1675	0.8462	0.280*
C28	0.3933 (12)	1.1993 (12)	0.9799 (2)	0.175 (3)
H28A	0.3376	1.0880	0.9910	0.262*
H28B	0.4293	1.2800	1.0061	0.262*
H28C	0.5095	1.1705	0.9646	0.262*

	U11	U22	U33	U12	U13	U23
O1	0.081 (2)	0.070 (2)	0.076 (2)	−0.0171 (19)	0.0347 (17)	−0.0278 (17)
O2	0.0557 (18)	0.0629 (19)	0.0479 (16)	−0.0209 (16)	0.0069 (13)	−0.0030 (14)
O3	0.092 (2)	0.068 (2)	0.0496 (18)	0.0010 (18)	0.0244 (17)	0.0116 (16)
O4	0.081 (2)	0.0486 (18)	0.0589 (18)	−0.0105 (17)	0.0215 (16)	0.0065 (14)
O5	0.0665 (19)	0.0589 (18)	0.0477 (16)	0.0020 (15)	0.0129 (14)	0.0026 (14)
C1	0.073 (3)	0.053 (3)	0.058 (3)	0.005 (3)	0.010 (2)	−0.002 (2)
C2	0.073 (3)	0.055 (3)	0.075 (3)	0.007 (3)	0.022 (3)	−0.002 (3)
C3	0.062 (3)	0.060 (3)	0.061 (3)	−0.005 (2)	0.023 (2)	−0.014 (2)
C4	0.053 (3)	0.056 (3)	0.048 (3)	−0.013 (2)	0.012 (2)	−0.007 (2)
C5	0.054 (3)	0.041 (3)	0.047 (3)	−0.011 (2)	0.011 (2)	−0.001 (2)
C6	0.056 (3)	0.047 (3)	0.049 (3)	−0.011 (2)	0.009 (2)	0.004 (2)
C7	0.062 (3)	0.048 (3)	0.046 (3)	0.000 (2)	0.013 (2)	0.001 (2)
C8	0.050 (3)	0.041 (3)	0.045 (3)	−0.010 (2)	0.006 (2)	−0.001 (2)
C9	0.055 (3)	0.042 (3)	0.048 (3)	0.001 (2)	0.009 (2)	0.005 (2)
C10	0.056 (3)	0.041 (2)	0.047 (3)	−0.004 (2)	0.010 (2)	−0.0045 (19)
C11	0.075 (3)	0.060 (3)	0.049 (3)	0.012 (3)	0.002 (2)	−0.003 (2)
C12	0.084 (3)	0.066 (3)	0.048 (3)	0.008 (3)	0.004 (2)	0.000 (2)
C13	0.058 (3)	0.054 (3)	0.042 (2)	−0.006 (2)	0.008 (2)	−0.004 (2)
C14	0.049 (2)	0.046 (3)	0.047 (2)	−0.009 (2)	0.009 (2)	−0.001 (2)
C15	0.060 (3)	0.054 (3)	0.056 (3)	−0.003 (2)	0.009 (2)	−0.007 (2)
C16	0.065 (3)	0.071 (3)	0.065 (3)	−0.008 (3)	0.016 (3)	−0.017 (3)
C17	0.066 (3)	0.061 (3)	0.054 (3)	−0.003 (3)	0.014 (2)	−0.007 (2)
C18	0.087 (4)	0.078 (3)	0.051 (3)	0.003 (3)	0.008 (3)	−0.012 (3)
C19	0.101 (4)	0.084 (4)	0.056 (3)	0.005 (4)	0.018 (3)	−0.014 (3)
C20	0.111 (4)	0.089 (4)	0.063 (3)	0.007 (4)	0.016 (3)	−0.018 (3)
C21	0.125 (5)	0.109 (5)	0.072 (4)	0.042 (4)	0.017 (4)	−0.019 (4)
C22	0.160 (7)	0.132 (6)	0.102 (5)	0.053 (5)	0.025 (5)	−0.033 (5)
C23	0.236 (10)	0.210 (10)	0.191 (9)	0.069 (9)	0.052 (7)	−0.078 (8)
C24	0.058 (3)	0.065 (3)	0.060 (3)	−0.008 (3)	0.007 (2)	−0.013 (2)
C25	0.059 (3)	0.082 (4)	0.064 (3)	−0.009 (3)	0.009 (2)	−0.020 (3)
C26	0.128 (5)	0.132 (5)	0.066 (3)	0.040 (5)	−0.008 (3)	−0.022 (4)
C27	0.166 (7)	0.252 (11)	0.135 (6)	0.113 (8)	−0.015 (5)	−0.017 (7)
C28	0.214 (9)	0.195 (9)	0.111 (5)	0.036 (8)	−0.004 (6)	−0.038 (6)

O1—C3	1.438 (4)	C14—H14	0.9800
O1—H1	0.8200	C15—C16	1.548 (5)
O2—C5	1.447 (4)	C15—H15A	0.9700
O2—H2	0.8200	C15—H15B	0.9700
O3—C6	1.234 (4)	C16—C17	1.550 (6)
O4—C9	1.446 (5)	C16—H16A	0.9700
O4—H4	0.8200	C16—H16B	0.9700
O5—H5C	0.8500	C17—C18	1.538 (5)
O5—H5D	0.8500	C17—H17	0.9800
C1—C2	1.524 (5)	C18—C19	1.498 (6)
C1—C10	1.533 (5)	C18—C26	1.531 (7)
C1—H1A	0.9700	C18—H18	0.9800
C1—H1B	0.9700	C19—C20	1.293 (6)
C2—C3	1.522 (6)	C19—H19	0.9300
C2—H2A	0.9700	C20—C21	1.489 (7)
C2—H2B	0.9700	C20—H20	0.9300
C3—C4	1.517 (6)	C21—C22	1.510 (8)
C3—H3	0.9800	C21—C27	1.531 (8)
C4—C5	1.528 (5)	C21—H21	0.9800
C4—H4A	0.9700	C22—C23	1.478 (9)
C4—H4B	0.9700	C22—C28	1.520 (9)
C5—C6	1.516 (6)	C22—H22	0.9800
C5—C10	1.561 (5)	C23—H23A	0.9600
C6—C7	1.461 (5)	C23—H23B	0.9600
C7—C8	1.334 (5)	C23—H23C	0.9600
C7—H7	0.9300	C24—H24A	0.9600
C8—C14	1.502 (5)	C24—H24B	0.9600
C8—C9	1.518 (5)	C24—H24C	0.9600
C9—C11	1.542 (5)	C25—H25A	0.9600
C9—C10	1.571 (5)	C25—H25B	0.9600
C10—C24	1.537 (5)	C25—H25C	0.9600
C11—C12	1.524 (5)	C26—H26A	0.9600
C11—H11A	0.9700	C26—H26B	0.9600
C11—H11B	0.9700	C26—H26C	0.9600
C12—C13	1.524 (6)	C27—H27A	0.9600
C12—H12A	0.9700	C27—H27B	0.9600
C12—H12B	0.9700	C27—H27C	0.9600
C13—C25	1.529 (6)	C28—H28A	0.9600
C13—C14	1.536 (5)	C28—H28B	0.9600
C13—C17	1.551 (5)	C28—H28C	0.9600
C14—C15	1.527 (5)
C3—O1—H1	109.5	C14—C15—C16	104.0 (3)
C5—O2—H2	109.5	C14—C15—H15A	111.0
C9—O4—H4	109.5	C16—C15—H15A	111.0
H5C—O5—H5D	108.0	C14—C15—H15B	111.0
C2—C1—C10	113.3 (4)	C16—C15—H15B	111.0
C2—C1—H1A	108.9	H15A—C15—H15B	109.0
C10—C1—H1A	108.9	C15—C16—C17	107.1 (3)
C2—C1—H1B	108.9	C15—C16—H16A	110.3
C10—C1—H1B	108.9	C17—C16—H16A	110.3
H1A—C1—H1B	107.7	C15—C16—H16B	110.3
C3—C2—C1	111.7 (4)	C17—C16—H16B	110.3
C3—C2—H2A	109.3	H16A—C16—H16B	108.6
C1—C2—H2A	109.3	C18—C17—C16	111.5 (4)
C3—C2—H2B	109.3	C18—C17—C13	119.3 (4)
C1—C2—H2B	109.3	C16—C17—C13	103.6 (3)
H2A—C2—H2B	107.9	C18—C17—H17	107.3
O1—C3—C4	111.9 (4)	C16—C17—H17	107.3
O1—C3—C2	112.0 (3)	C13—C17—H17	107.3
C4—C3—C2	110.4 (3)	C19—C18—C26	110.0 (4)
O1—C3—H3	107.4	C19—C18—C17	110.0 (4)
C4—C3—H3	107.4	C26—C18—C17	114.0 (4)
C2—C3—H3	107.4	C19—C18—H18	107.5
C3—C4—C5	111.9 (3)	C26—C18—H18	107.5
C3—C4—H4A	109.2	C17—C18—H18	107.5
C5—C4—H4A	109.2	C20—C19—C18	128.7 (6)
C3—C4—H4B	109.2	C20—C19—H19	115.6
C5—C4—H4B	109.2	C18—C19—H19	115.6
H4A—C4—H4B	107.9	C19—C20—C21	128.5 (6)
O2—C5—C6	105.3 (3)	C19—C20—H20	115.7
O2—C5—C4	108.5 (3)	C21—C20—H20	115.7
C6—C5—C4	113.1 (3)	C20—C21—C22	112.2 (5)
O2—C5—C10	107.2 (3)	C20—C21—C27	109.0 (5)
C6—C5—C10	109.5 (3)	C22—C21—C27	109.4 (6)
C4—C5—C10	112.8 (3)	C20—C21—H21	108.7
O3—C6—C7	121.4 (4)	C22—C21—H21	108.7
O3—C6—C5	122.5 (4)	C27—C21—H21	108.7
C7—C6—C5	116.1 (4)	C23—C22—C21	114.6 (7)
C8—C7—C6	123.1 (4)	C23—C22—C28	108.2 (7)
C8—C7—H7	118.4	C21—C22—C28	108.9 (6)
C6—C7—H7	118.4	C23—C22—H22	108.3
C7—C8—C14	122.6 (4)	C21—C22—H22	108.3
C7—C8—C9	122.4 (4)	C28—C22—H22	108.3
C14—C8—C9	114.8 (3)	C22—C23—H23A	109.5
O4—C9—C8	105.4 (3)	C22—C23—H23B	109.5
O4—C9—C11	103.9 (3)	H23A—C23—H23B	109.5
C8—C9—C11	111.3 (3)	C22—C23—H23C	109.5
O4—C9—C10	111.6 (3)	H23A—C23—H23C	109.5
C8—C9—C10	112.8 (3)	H23B—C23—H23C	109.5
C11—C9—C10	111.3 (3)	C10—C24—H24A	109.5
C1—C10—C24	109.9 (3)	C10—C24—H24B	109.5
C1—C10—C5	108.8 (3)	H24A—C24—H24B	109.5
C24—C10—C5	107.8 (3)	C10—C24—H24C	109.5
C1—C10—C9	111.5 (3)	H24A—C24—H24C	109.5
C24—C10—C9	110.2 (3)	H24B—C24—H24C	109.5
C5—C10—C9	108.6 (3)	C13—C25—H25A	109.5
C12—C11—C9	114.7 (4)	C13—C25—H25B	109.5
C12—C11—H11A	108.6	H25A—C25—H25B	109.5
C9—C11—H11A	108.6	C13—C25—H25C	109.5
C12—C11—H11B	108.6	H25A—C25—H25C	109.5
C9—C11—H11B	108.6	H25B—C25—H25C	109.5
H11A—C11—H11B	107.6	C18—C26—H26A	109.5
C11—C12—C13	112.1 (3)	C18—C26—H26B	109.5
C11—C12—H12A	109.2	H26A—C26—H26B	109.5
C13—C12—H12A	109.2	C18—C26—H26C	109.5
C11—C12—H12B	109.2	H26A—C26—H26C	109.5
C13—C12—H12B	109.2	H26B—C26—H26C	109.5
H12A—C12—H12B	107.9	C21—C27—H27A	109.5
C12—C13—C25	111.9 (4)	C21—C27—H27B	109.5
C12—C13—C14	106.0 (3)	H27A—C27—H27B	109.5
C25—C13—C14	110.1 (3)	C21—C27—H27C	109.5
C12—C13—C17	117.5 (3)	H27A—C27—H27C	109.5
C25—C13—C17	109.8 (3)	H27B—C27—H27C	109.5
C14—C13—C17	100.7 (3)	C22—C28—H28A	109.5
C8—C14—C15	120.5 (3)	C22—C28—H28B	109.5
C8—C14—C13	114.0 (3)	H28A—C28—H28B	109.5
C15—C14—C13	105.1 (3)	C22—C28—H28C	109.5
C8—C14—H14	105.3	H28A—C28—H28C	109.5
C15—C14—H14	105.3	H28B—C28—H28C	109.5
C13—C14—H14	105.3
C10—C1—C2—C3	−56.2 (5)	C8—C9—C10—C5	−45.5 (4)
C1—C2—C3—O1	−178.8 (3)	C11—C9—C10—C5	−171.4 (3)
C1—C2—C3—C4	55.8 (5)	O4—C9—C11—C12	−69.0 (4)
O1—C3—C4—C5	178.9 (3)	C8—C9—C11—C12	44.0 (5)
C2—C3—C4—C5	−55.6 (4)	C10—C9—C11—C12	170.8 (4)
C3—C4—C5—O2	−63.5 (4)	C9—C11—C12—C13	−54.7 (5)
C3—C4—C5—C6	−179.9 (3)	C11—C12—C13—C25	−61.0 (5)
C3—C4—C5—C10	55.2 (4)	C11—C12—C13—C14	59.0 (5)
O2—C5—C6—O3	−106.8 (4)	C11—C12—C13—C17	170.6 (4)
C4—C5—C6—O3	11.5 (5)	C7—C8—C14—C15	−5.1 (6)
C10—C5—C6—O3	138.2 (4)	C9—C8—C14—C15	179.3 (3)
O2—C5—C6—C7	70.7 (4)	C7—C8—C14—C13	−131.5 (4)
C4—C5—C6—C7	−170.9 (3)	C9—C8—C14—C13	53.0 (4)
C10—C5—C6—C7	−44.3 (5)	C12—C13—C14—C8	−58.9 (4)
O3—C6—C7—C8	−169.0 (4)	C25—C13—C14—C8	62.3 (5)
C5—C6—C7—C8	13.4 (6)	C17—C13—C14—C8	178.2 (3)
C6—C7—C8—C14	−173.5 (3)	C12—C13—C14—C15	167.1 (3)
C6—C7—C8—C9	1.7 (6)	C25—C13—C14—C15	−71.7 (4)
C7—C8—C9—O4	−106.3 (4)	C17—C13—C14—C15	44.1 (4)
C14—C8—C9—O4	69.2 (4)	C8—C14—C15—C16	−161.5 (3)
C7—C8—C9—C11	141.6 (4)	C13—C14—C15—C16	−31.2 (4)
C14—C8—C9—C11	−42.8 (4)	C14—C15—C16—C17	5.9 (4)
C7—C8—C9—C10	15.7 (5)	C15—C16—C17—C18	150.7 (4)
C14—C8—C9—C10	−168.7 (3)	C15—C16—C17—C13	21.1 (4)
C2—C1—C10—C24	−64.8 (4)	C12—C13—C17—C18	81.5 (5)
C2—C1—C10—C5	53.0 (5)	C25—C13—C17—C18	−47.9 (5)
C2—C1—C10—C9	172.7 (3)	C14—C13—C17—C18	−164.0 (4)
O2—C5—C10—C1	67.0 (4)	C12—C13—C17—C16	−153.8 (4)
C6—C5—C10—C1	−179.2 (3)	C25—C13—C17—C16	76.8 (4)
C4—C5—C10—C1	−52.4 (4)	C14—C13—C17—C16	−39.3 (4)
O2—C5—C10—C24	−173.8 (3)	C16—C17—C18—C19	58.6 (5)
C6—C5—C10—C24	−60.1 (4)	C13—C17—C18—C19	179.4 (4)
C4—C5—C10—C24	66.8 (4)	C16—C17—C18—C26	−177.3 (4)
O2—C5—C10—C9	−54.4 (4)	C13—C17—C18—C26	−56.5 (6)
C6—C5—C10—C9	59.3 (4)	C26—C18—C19—C20	119.0 (6)
C4—C5—C10—C9	−173.8 (3)	C17—C18—C19—C20	−114.6 (6)
O4—C9—C10—C1	−46.7 (4)	C18—C19—C20—C21	177.8 (5)
C8—C9—C10—C1	−165.2 (3)	C19—C20—C21—C22	130.0 (7)
C11—C9—C10—C1	68.8 (4)	C19—C20—C21—C27	−108.7 (8)
O4—C9—C10—C24	−169.1 (3)	C20—C21—C22—C23	179.5 (6)
C8—C9—C10—C24	72.4 (4)	C27—C21—C22—C23	58.5 (9)
C11—C9—C10—C24	−53.5 (4)	C20—C21—C22—C28	−59.1 (8)
O4—C9—C10—C5	73.0 (4)	C27—C21—C22—C28	179.8 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5i	0.82	1.93	2.749 (4)	180
O2—H2···O5	0.82	1.90	2.716 (4)	177
O4—H4···O2	0.82	1.97	2.642 (4)	139
O5—H5C···O1ii	0.85	1.81	2.642 (4)	165
O5—H5D···O3iii	0.85	1.93	2.761 (4)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5i	0.82	1.93	2.749 (4)	180
O2—H2⋯O5	0.82	1.90	2.716 (4)	177
O4—H4⋯O2	0.82	1.97	2.642 (4)	139
O5—H5C⋯O1ii	0.85	1.81	2.642 (4)	165
O5—H5D⋯O3iii	0.85	1.93	2.761 (4)	165

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