(2α,3α,5α,20S,22S)-2,3,5,14,20,20,24-Hepta­hydroxy­cholest-7-en-6-one monohydrate

The crystal structure of the title compound consists of discrete C₂₇H₄₄O₈ and H₂O mol­ecules, linked by hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.041
• wR factor = 0.064
• Data-to-parameter ratio = 9.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_213  Alert C Atom  O4     has ADP max/min Ratio ...........       3.20

PLAT_736  Alert C H...A   Calc     2.07(3), Rep   2.070(11) ....       2.73 s.u-Ratio
                     H9OB -O6      1.555   4.455

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.25
         From the CIF: _reflns_number_total               3185
         Count of symmetry unique reflns         3186
         Completeness (_total/calc)             99.97%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

S1. Comment

The title compound,, (I), has been isolated from Solanum nigrum L. (De Souza et al., 1970; Baltaev, 1995; Kissmer & Wichtl, 1987; Nishimoto et al., 1987). It was isolated from Solanaceae for the first time, its structure was established from the spectroscopic and chemical evidence, and confirmed by this X-ray diffraction study.

The title compound is a typical example of a sterone. Its main skeleton is composed of four rings. The A and C rings exist in chair conformations. Because of carbonyl and double-bond planarity, the B ring is in a distorted chair conformation. Ring D has a half-chair conformation. The Csp³—Csp³ bond lengths C1—C2, C2—C3, C5—C10, C9—C10, C9—C11, C13—C17, C20—C22, C22—C23, C24—C25, C25—C26 and C25—C27 show some significant deviations from standard values. The bond angles C7—C6—C5, C8—C7—C6, C7—C8—C9, C7—C8—C14, C14—C13—C17, C15—C14—C8 and C20—C17—C13 show significant deviations from the ideal tetrahedral value of 109.5°. These deviations are common in steroids as a result of the strain induced by ring junctions, side chains and unsaturated bonds. The C7—C8 bond length indicates double-bond nature. The title compound is a hydrate; the water molecule is involved in hydrogen bonding, as both donor and acceptor (Table 2).

S2. Experimental

The title compound was separated from a n-butanol fraction of Solanum nigrum L. by CHCl₃–CH₃OH–H₂O. Crystals were grown from methanol at room temperature by slowly evaporation of the solvent.

S3. Refinement

Atoms H9OA and H9OB were located by difference Fourier synthesis, the remaining H atoms were placed in geometrically calculated positions. All H atoms were included in the final refinement and allowed to ride on their parent atoms with U_iso(H)=1.2U_eq(parent). Friedel reflections were merged before the final refinement and only the relative stereochemistry is shown in the Scheme and Figures; the absolute configuration can not be determined reliably in this experiment.

Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Siemens, 1991); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The asymmetric unit of the title compound with atom labels, showing 50% probability displacement ellipsoids.
	Fig. 2. An illustration of the unit-cell packing of the title compound, viewed along the crystallographic a axis. H atoms are omitted for clarity. Hydrogen bonding is shown by dashed lines.

(2α,3α,5α,20S,22S)-2,3,5,14,20,20,24-Heptahydroxycholest-7-en-6-one monohydrate

Crystal data

C27H44O8·H2O	Dx = 1.248 Mg m^−3
Mr = 514.64	Melting point: 504 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 7.153 (1) Å	Cell parameters from 25 reflections
b = 10.290 (2) Å	θ = 2.9–15.0°
c = 37.220 (8) Å	µ = 0.09 mm^−1
V = 2739.6 (9) Å^3	T = 291 K
Z = 4	Prism, colourless
F(000) = 1120	0.36 × 0.30 × 0.24 mm

Data collection

Siemens P4 diffractometer	Rint = 0.019
Radiation source: normal-focus sealed tube	θmax = 26.3°, θmin = 2.1°
Graphite monochromator	h = 0→8
ω scans	k = 0→12
3426 measured reflections	l = −1→46
3185 independent reflections	3 standard reflections every 97 reflections
1635 reflections with I > 2σ(I)	intensity decay: 3.5%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.064	w = 1/[σ^2(Fo^2) + (0.0182P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.80	(Δ/σ)max < 0.001
3185 reflections	Δρmax = 0.17 e Å^−3
346 parameters	Δρmin = −0.17 e Å^−3
2 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0046 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.6536 (3)	0.4277 (3)	0.28174 (7)	0.0753 (11)
H1	0.7521	0.4176	0.2708	0.090*
O2	0.2587 (3)	0.4215 (3)	0.30614 (7)	0.0538 (8)
H2O	0.3367	0.4646	0.3170	0.065*
O3	0.0187 (3)	0.4542 (3)	0.25196 (7)	0.0493 (7)
H3O	0.0725	0.4735	0.2707	0.059*
O4	−0.1803 (3)	0.2792 (3)	0.21821 (7)	0.0849 (12)
O5	0.4460 (3)	0.0530 (2)	0.16004 (5)	0.0335 (6)
H5	0.3921	0.0182	0.1769	0.040*
O6	0.4750 (3)	0.16987 (19)	0.02590 (6)	0.0350 (6)
H6	0.3810	0.1274	0.0213	0.042*
O7	0.7219 (3)	−0.0198 (2)	0.00104 (5)	0.0378 (6)
H7	0.6427	−0.0120	−0.0147	0.045*
O8	0.9100 (3)	−0.4731 (2)	0.04515 (7)	0.0466 (7)
H8	0.8106	−0.4998	0.0370	0.056*
O9	0.0976 (4)	0.0705 (3)	−0.00769 (8)	0.0531 (8)
C1	0.4275 (5)	0.4755 (3)	0.23506 (9)	0.0459 (11)
H1A	0.5297	0.5095	0.2207	0.055*
H1B	0.3741	0.5472	0.2485	0.055*
C2	0.5032 (4)	0.3757 (4)	0.26104 (10)	0.0460 (11)
H2	0.5522	0.3028	0.2469	0.055*
C3	0.3513 (5)	0.3238 (4)	0.28517 (9)	0.0439 (11)
H3	0.4037	0.2576	0.3012	0.053*
C4	0.2036 (4)	0.2619 (3)	0.26101 (8)	0.0378 (10)
H4A	0.2589	0.1887	0.2485	0.045*
H4B	0.1027	0.2290	0.2759	0.045*
C5	0.1233 (4)	0.3563 (3)	0.23346 (9)	0.0351 (9)
C6	−0.0156 (5)	0.2832 (4)	0.21013 (10)	0.0456 (11)
C7	0.0562 (5)	0.2092 (4)	0.17967 (8)	0.0361 (10)
H7A	−0.0222	0.1504	0.1681	0.043*
C8	0.2313 (4)	0.2235 (3)	0.16795 (8)	0.0260 (8)
C9	0.3682 (4)	0.3156 (3)	0.18465 (8)	0.0296 (9)
H9	0.4483	0.2623	0.2001	0.036*
C10	0.2772 (5)	0.4188 (3)	0.20982 (9)	0.0356 (9)
C11	0.5003 (5)	0.3781 (3)	0.15648 (9)	0.0469 (11)
H11A	0.4318	0.4440	0.1433	0.056*
H11B	0.6024	0.4209	0.1689	0.056*
C12	0.5814 (4)	0.2796 (3)	0.12976 (8)	0.0354 (9)
H12A	0.6555	0.3251	0.1119	0.042*
H12B	0.6631	0.2199	0.1424	0.042*
C13	0.4273 (4)	0.2027 (3)	0.11091 (8)	0.0262 (8)
C14	0.3146 (4)	0.1319 (3)	0.14012 (8)	0.0235 (8)
C15	0.1874 (4)	0.0414 (3)	0.11942 (8)	0.0367 (9)
H15A	0.0759	0.0863	0.1113	0.044*
H15B	0.1510	−0.0327	0.1339	0.044*
C16	0.3109 (4)	−0.0009 (3)	0.08733 (9)	0.0389 (10)
H16A	0.3434	−0.0921	0.0895	0.047*
H16B	0.2443	0.0117	0.0649	0.047*
C17	0.4890 (4)	0.0836 (3)	0.08815 (8)	0.0252 (8)
H17	0.5779	0.0361	0.1033	0.030*
C18	0.2960 (5)	0.2947 (3)	0.09004 (8)	0.0415 (10)
H18A	0.2183	0.3412	0.1067	0.050*
H18B	0.2188	0.2447	0.0741	0.050*
H18C	0.3691	0.3553	0.0764	0.050*
C19	0.1888 (6)	0.5303 (3)	0.18797 (10)	0.0705 (14)
H19A	0.1230	0.5877	0.2039	0.085*
H19B	0.1030	0.4950	0.1707	0.085*
H19C	0.2853	0.5776	0.1757	0.085*
C20	0.5876 (5)	0.1006 (3)	0.05161 (8)	0.0272 (8)
C21	0.7649 (4)	0.1815 (3)	0.05492 (8)	0.0338 (9)
H21A	0.8318	0.1795	0.0326	0.041*
H21B	0.8423	0.1464	0.0736	0.041*
H21C	0.7325	0.2696	0.0607	0.041*
C22	0.6310 (5)	−0.0355 (3)	0.03529 (8)	0.0337 (9)
H22	0.5125	−0.0812	0.0315	0.040*
C23	0.7574 (5)	−0.1216 (3)	0.05791 (9)	0.0394 (10)
H23A	0.7036	−0.1308	0.0817	0.047*
H23B	0.8782	−0.0799	0.0605	0.047*
C24	0.7853 (5)	−0.2576 (3)	0.04143 (9)	0.0421 (10)
H24A	0.6642	−0.2909	0.0342	0.051*
H24B	0.8609	−0.2489	0.0199	0.051*
C25	0.8771 (5)	−0.3566 (3)	0.06596 (10)	0.0392 (10)
C26	1.0694 (5)	−0.3148 (3)	0.07772 (10)	0.0686 (14)
H26A	1.1289	−0.3847	0.0904	0.082*
H26B	1.0593	−0.2406	0.0932	0.082*
H26C	1.1426	−0.2923	0.0570	0.082*
C27	0.7571 (6)	−0.3909 (3)	0.09787 (10)	0.0730 (15)
H27A	0.6340	−0.4140	0.0898	0.088*
H27B	0.7491	−0.3175	0.1137	0.088*
H27C	0.8116	−0.4630	0.1104	0.088*
H9OA	−0.003 (3)	0.034 (3)	−0.0047 (10)	0.077 (17)*
H9OB	0.062 (6)	0.144 (2)	−0.0129 (12)	0.11 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0255 (14)	0.137 (3)	0.064 (2)	−0.013 (2)	0.0101 (14)	−0.068 (2)
O2	0.0316 (14)	0.081 (2)	0.0485 (17)	−0.0093 (17)	0.0125 (14)	−0.0367 (16)
O3	0.0382 (15)	0.0564 (18)	0.0532 (17)	0.0123 (15)	0.0097 (12)	−0.0194 (16)
O4	0.0195 (15)	0.161 (3)	0.074 (2)	−0.003 (2)	0.0062 (15)	−0.058 (2)
O5	0.0313 (13)	0.0401 (16)	0.0290 (14)	0.0089 (14)	0.0084 (11)	0.0108 (12)
O6	0.0368 (16)	0.0341 (15)	0.0341 (13)	0.0000 (13)	−0.0031 (13)	0.0042 (13)
O7	0.0425 (14)	0.0437 (15)	0.0271 (13)	−0.0007 (15)	0.0063 (12)	−0.0027 (14)
O8	0.0460 (16)	0.0291 (14)	0.0647 (18)	−0.0003 (14)	−0.0043 (16)	−0.0114 (14)
O9	0.0434 (19)	0.046 (2)	0.069 (2)	0.0059 (18)	0.0216 (17)	0.0117 (18)
C1	0.043 (2)	0.038 (2)	0.056 (3)	−0.015 (2)	0.027 (2)	−0.020 (2)
C2	0.0180 (19)	0.067 (3)	0.053 (3)	−0.009 (2)	0.004 (2)	−0.037 (2)
C3	0.034 (2)	0.058 (3)	0.040 (2)	0.000 (2)	0.004 (2)	−0.009 (2)
C4	0.032 (2)	0.046 (2)	0.036 (2)	−0.005 (2)	0.0106 (19)	−0.008 (2)
C5	0.0224 (19)	0.045 (2)	0.037 (2)	0.006 (2)	0.0051 (18)	−0.014 (2)
C6	0.023 (2)	0.066 (3)	0.048 (2)	0.002 (2)	0.0022 (19)	−0.008 (2)
C7	0.025 (2)	0.050 (2)	0.033 (2)	−0.003 (2)	0.0016 (17)	−0.013 (2)
C8	0.0197 (18)	0.032 (2)	0.0266 (19)	0.0029 (19)	−0.0011 (16)	0.0025 (17)
C9	0.023 (2)	0.037 (2)	0.0288 (19)	−0.0011 (19)	0.0023 (16)	−0.0043 (19)
C10	0.034 (2)	0.032 (2)	0.041 (2)	0.006 (2)	0.0053 (19)	−0.0004 (19)
C11	0.051 (3)	0.048 (2)	0.041 (2)	−0.022 (2)	0.020 (2)	−0.013 (2)
C12	0.036 (2)	0.039 (2)	0.032 (2)	−0.008 (2)	0.0119 (18)	−0.0015 (19)
C13	0.0230 (18)	0.0270 (19)	0.0285 (19)	−0.0025 (18)	−0.0040 (17)	0.0013 (17)
C14	0.0184 (17)	0.0257 (19)	0.0263 (19)	−0.0011 (17)	−0.0018 (16)	−0.0004 (16)
C15	0.031 (2)	0.038 (2)	0.041 (2)	−0.006 (2)	0.0061 (18)	−0.001 (2)
C16	0.043 (2)	0.034 (2)	0.039 (2)	−0.013 (2)	0.0061 (19)	−0.0075 (19)
C17	0.0250 (18)	0.0199 (19)	0.0306 (19)	−0.0032 (18)	0.0021 (16)	0.0005 (17)
C18	0.051 (2)	0.038 (2)	0.035 (2)	0.012 (2)	0.008 (2)	0.0102 (19)
C19	0.084 (3)	0.052 (3)	0.076 (3)	0.030 (3)	0.029 (3)	0.009 (3)
C20	0.030 (2)	0.027 (2)	0.0240 (19)	0.0004 (18)	−0.0030 (17)	0.0035 (17)
C21	0.034 (2)	0.035 (2)	0.033 (2)	−0.002 (2)	0.0043 (19)	0.0004 (19)
C22	0.036 (2)	0.034 (2)	0.031 (2)	−0.003 (2)	0.0070 (18)	−0.0001 (19)
C23	0.055 (3)	0.030 (2)	0.033 (2)	0.005 (2)	0.003 (2)	−0.0005 (18)
C24	0.054 (3)	0.035 (2)	0.038 (2)	0.005 (2)	0.000 (2)	−0.0052 (19)
C25	0.047 (3)	0.023 (2)	0.047 (2)	−0.003 (2)	0.001 (2)	−0.006 (2)
C26	0.069 (3)	0.041 (3)	0.097 (4)	0.003 (3)	−0.029 (3)	−0.011 (3)
C27	0.113 (4)	0.043 (3)	0.062 (3)	−0.006 (3)	0.029 (3)	0.004 (2)

Geometric parameters (Å, º)

O1—C2	1.427 (3)	C12—C13	1.527 (4)
O1—H1	0.820	C12—H12A	0.970
O2—C3	1.434 (4)	C12—H12B	0.970
O2—H2O	0.820	C13—C14	1.537 (4)
O3—C5	1.432 (4)	C13—C18	1.543 (4)
O3—H3O	0.820	C13—C17	1.554 (4)
O4—C6	1.217 (4)	C14—C15	1.513 (4)
O5—C14	1.446 (3)	C15—C16	1.548 (4)
O5—H5	0.820	C15—H15A	0.970
O6—C20	1.439 (3)	C15—H15B	0.970
O6—H6	0.820	C16—C17	1.543 (4)
O7—C22	1.440 (3)	C16—H16A	0.970
O7—H7	0.820	C16—H16B	0.970
O8—C25	1.446 (4)	C17—C20	1.542 (4)
O8—H8	0.820	C17—H17	0.980
O9—H9OA	0.822 (10)	C18—H18A	0.960
O9—H9OB	0.822 (10)	C18—H18B	0.960
C1—C2	1.511 (4)	C18—H18C	0.960
C1—C10	1.543 (4)	C19—H19A	0.960
C1—H1A	0.970	C19—H19B	0.960
C1—H1B	0.970	C19—H19C	0.960
C2—C3	1.507 (4)	C20—C21	1.522 (4)
C2—H2	0.980	C20—C22	1.558 (4)
C3—C4	1.526 (4)	C21—H21A	0.960
C3—H3	0.980	C21—H21B	0.960
C4—C5	1.525 (4)	C21—H21C	0.960
C4—H4A	0.970	C22—C23	1.520 (4)
C4—H4B	0.970	C22—H22	0.980
C5—C6	1.518 (4)	C23—C24	1.541 (4)
C5—C10	1.549 (4)	C23—H23A	0.970
C6—C7	1.459 (4)	C23—H23B	0.970
C7—C8	1.335 (4)	C24—C25	1.518 (4)
C7—H7A	0.930	C24—H24A	0.970
C8—C9	1.498 (4)	C24—H24B	0.970
C8—C14	1.522 (4)	C25—C26	1.507 (4)
C9—C11	1.551 (4)	C25—C27	1.508 (4)
C9—C10	1.558 (4)	C26—H26A	0.960
C9—H9	0.980	C26—H26B	0.960
C10—C19	1.542 (4)	C26—H26C	0.960
C11—C12	1.534 (4)	C27—H27A	0.960
C11—H11A	0.970	C27—H27B	0.960
C11—H11B	0.970	C27—H27C	0.960
C2—O1—H1	109.5	C15—C14—C13	104.3 (2)
C3—O2—H2O	109.5	C8—C14—C13	113.1 (3)
C5—O3—H3O	109.5	C14—C15—C16	102.9 (2)
C14—O5—H5	109.5	C14—C15—H15A	111.2
C20—O6—H6	109.5	C16—C15—H15A	111.2
C22—O7—H7	109.5	C14—C15—H15B	111.2
C25—O8—H8	109.5	C16—C15—H15B	111.2
H9OA—O9—H9OB	101 (4)	H15A—C15—H15B	109.1
C2—C1—C10	112.5 (3)	C17—C16—C15	107.3 (2)
C2—C1—H1A	109.1	C17—C16—H16A	110.3
C10—C1—H1A	109.1	C15—C16—H16A	110.3
C2—C1—H1B	109.1	C17—C16—H16B	110.3
C10—C1—H1B	109.1	C15—C16—H16B	110.3
H1A—C1—H1B	107.8	H16A—C16—H16B	108.5
O1—C2—C3	110.7 (3)	C20—C17—C16	115.1 (3)
O1—C2—C1	111.2 (3)	C20—C17—C13	121.4 (3)
C3—C2—C1	111.4 (3)	C16—C17—C13	102.8 (2)
O1—C2—H2	107.8	C20—C17—H17	105.4
C3—C2—H2	107.8	C16—C17—H17	105.4
C1—C2—H2	107.8	C13—C17—H17	105.4
O2—C3—C2	114.1 (3)	C13—C18—H18A	109.5
O2—C3—C4	107.1 (3)	C13—C18—H18B	109.5
C2—C3—C4	107.2 (3)	H18A—C18—H18B	109.5
O2—C3—H3	109.4	C13—C18—H18C	109.5
C2—C3—H3	109.4	H18A—C18—H18C	109.5
C4—C3—H3	109.4	H18B—C18—H18C	109.5
C5—C4—C3	113.0 (3)	C10—C19—H19A	109.5
C5—C4—H4A	109.0	C10—C19—H19B	109.5
C3—C4—H4A	109.0	H19A—C19—H19B	109.5
C5—C4—H4B	109.0	C10—C19—H19C	109.5
C3—C4—H4B	109.0	H19A—C19—H19C	109.5
H4A—C4—H4B	107.8	H19B—C19—H19C	109.5
O3—C5—C6	106.4 (3)	O6—C20—C21	104.4 (2)
O3—C5—C4	108.8 (3)	O6—C20—C17	112.7 (3)
C6—C5—C4	108.4 (3)	C21—C20—C17	111.8 (3)
O3—C5—C10	110.6 (3)	O6—C20—C22	107.3 (2)
C6—C5—C10	110.2 (3)	C21—C20—C22	110.9 (3)
C4—C5—C10	112.3 (3)	C17—C20—C22	109.5 (2)
O4—C6—C7	121.0 (4)	C20—C21—H21A	109.5
O4—C6—C5	120.6 (4)	C20—C21—H21B	109.5
C7—C6—C5	118.2 (3)	H21A—C21—H21B	109.5
C8—C7—C6	121.7 (3)	C20—C21—H21C	109.5
C8—C7—H7A	119.1	H21A—C21—H21C	109.5
C6—C7—H7A	119.1	H21B—C21—H21C	109.5
C7—C8—C9	123.2 (3)	O7—C22—C23	106.7 (3)
C7—C8—C14	121.4 (3)	O7—C22—C20	109.6 (3)
C9—C8—C14	114.7 (3)	C23—C22—C20	115.3 (3)
C8—C9—C11	112.3 (3)	O7—C22—H22	108.4
C8—C9—C10	114.0 (3)	C23—C22—H22	108.4
C11—C9—C10	112.2 (3)	C20—C22—H22	108.4
C8—C9—H9	105.8	C22—C23—C24	112.7 (3)
C11—C9—H9	105.8	C22—C23—H23A	109.1
C10—C9—H9	105.8	C24—C23—H23A	109.1
C19—C10—C1	109.0 (3)	C22—C23—H23B	109.1
C19—C10—C5	108.5 (3)	C24—C23—H23B	109.1
C1—C10—C5	107.9 (3)	H23A—C23—H23B	107.8
C19—C10—C9	111.2 (3)	C25—C24—C23	115.2 (3)
C1—C10—C9	109.4 (3)	C25—C24—H24A	108.5
C5—C10—C9	110.8 (3)	C23—C24—H24A	108.5
C12—C11—C9	113.2 (3)	C25—C24—H24B	108.5
C12—C11—H11A	108.9	C23—C24—H24B	108.5
C9—C11—H11A	108.9	H24A—C24—H24B	107.5
C12—C11—H11B	108.9	O8—C25—C26	104.1 (3)
C9—C11—H11B	108.9	O8—C25—C27	108.7 (3)
H11A—C11—H11B	107.7	C26—C25—C27	111.0 (3)
C13—C12—C11	111.5 (3)	O8—C25—C24	107.7 (3)
C13—C12—H12A	109.3	C26—C25—C24	112.2 (3)
C11—C12—H12A	109.3	C27—C25—C24	112.6 (3)
C13—C12—H12B	109.3	C25—C26—H26A	109.5
C11—C12—H12B	109.3	C25—C26—H26B	109.5
H12A—C12—H12B	108.0	H26A—C26—H26B	109.5
C12—C13—C14	107.4 (2)	C25—C26—H26C	109.5
C12—C13—C18	110.7 (3)	H26A—C26—H26C	109.5
C14—C13—C18	109.1 (3)	H26B—C26—H26C	109.5
C12—C13—C17	117.0 (3)	C25—C27—H27A	109.5
C14—C13—C17	99.2 (2)	C25—C27—H27B	109.5
C18—C13—C17	112.5 (3)	H27A—C27—H27B	109.5
O5—C14—C15	107.9 (3)	C25—C27—H27C	109.5
O5—C14—C8	104.7 (2)	H27A—C27—H27C	109.5
C15—C14—C8	119.5 (3)	H27B—C27—H27C	109.5
O5—C14—C13	106.7 (2)
C10—C1—C2—O1	174.7 (3)	C11—C12—C13—C18	59.7 (4)
C10—C1—C2—C3	−61.3 (4)	C11—C12—C13—C17	−169.7 (3)
O1—C2—C3—O2	65.6 (4)	C7—C8—C14—O5	−107.5 (3)
C1—C2—C3—O2	−58.7 (4)	C9—C8—C14—O5	63.8 (4)
O1—C2—C3—C4	−176.1 (3)	C7—C8—C14—C15	13.3 (5)
C1—C2—C3—C4	59.7 (4)	C9—C8—C14—C15	−175.4 (3)
O2—C3—C4—C5	65.2 (4)	C7—C8—C14—C13	136.7 (3)
C2—C3—C4—C5	−57.7 (4)	C9—C8—C14—C13	−52.1 (4)
C3—C4—C5—O3	−66.9 (3)	C12—C13—C14—O5	−56.8 (3)
C3—C4—C5—C6	177.8 (3)	C18—C13—C14—O5	−176.8 (2)
C3—C4—C5—C10	55.8 (4)	C17—C13—C14—O5	65.4 (3)
O3—C5—C6—O4	−25.7 (5)	C12—C13—C14—C15	−170.9 (2)
C4—C5—C6—O4	91.1 (5)	C18—C13—C14—C15	69.1 (3)
C10—C5—C6—O4	−145.6 (4)	C17—C13—C14—C15	−48.7 (3)
O3—C5—C6—C7	159.5 (3)	C12—C13—C14—C8	57.8 (3)
C4—C5—C6—C7	−83.7 (4)	C18—C13—C14—C8	−62.3 (3)
C10—C5—C6—C7	39.6 (5)	C17—C13—C14—C8	180.0 (2)
O4—C6—C7—C8	172.4 (4)	O5—C14—C15—C16	−77.4 (3)
C5—C6—C7—C8	−12.8 (6)	C8—C14—C15—C16	163.3 (3)
C6—C7—C8—C9	−0.1 (6)	C13—C14—C15—C16	35.8 (3)
C6—C7—C8—C14	170.4 (3)	C14—C15—C16—C17	−8.8 (3)
C7—C8—C9—C11	−144.5 (3)	C15—C16—C17—C20	−155.0 (3)
C14—C8—C9—C11	44.4 (4)	C15—C16—C17—C13	−20.8 (3)
C7—C8—C9—C10	−15.4 (5)	C12—C13—C17—C20	−73.2 (4)
C14—C8—C9—C10	173.5 (3)	C14—C13—C17—C20	171.8 (3)
C2—C1—C10—C19	172.3 (3)	C18—C13—C17—C20	56.6 (4)
C2—C1—C10—C5	54.7 (4)	C12—C13—C17—C16	156.4 (3)
C2—C1—C10—C9	−66.0 (4)	C14—C13—C17—C16	41.4 (3)
O3—C5—C10—C19	−47.8 (4)	C18—C13—C17—C16	−73.8 (3)
C6—C5—C10—C19	69.5 (4)	C16—C17—C20—O6	64.5 (4)
C4—C5—C10—C19	−169.5 (3)	C13—C17—C20—O6	−60.4 (4)
O3—C5—C10—C1	70.1 (3)	C16—C17—C20—C21	−178.2 (3)
C6—C5—C10—C1	−172.5 (3)	C13—C17—C20—C21	56.9 (4)
C4—C5—C10—C1	−51.6 (4)	C16—C17—C20—C22	−54.9 (3)
O3—C5—C10—C9	−170.1 (3)	C13—C17—C20—C22	−179.8 (3)
C6—C5—C10—C9	−52.8 (4)	O6—C20—C22—O7	56.9 (3)
C4—C5—C10—C9	68.2 (4)	C21—C20—C22—O7	−56.6 (3)
C8—C9—C10—C19	−79.0 (4)	C17—C20—C22—O7	179.6 (2)
C11—C9—C10—C19	50.2 (4)	O6—C20—C22—C23	177.2 (3)
C8—C9—C10—C1	160.6 (3)	C21—C20—C22—C23	63.8 (3)
C11—C9—C10—C1	−70.2 (4)	C17—C20—C22—C23	−60.1 (4)
C8—C9—C10—C5	41.8 (4)	O7—C22—C23—C24	−61.6 (4)
C11—C9—C10—C5	171.0 (3)	C20—C22—C23—C24	176.5 (3)
C8—C9—C11—C12	−46.1 (4)	C22—C23—C24—C25	−168.4 (3)
C10—C9—C11—C12	−176.1 (3)	C23—C24—C25—O8	−174.1 (3)
C9—C11—C12—C13	55.1 (4)	C23—C24—C25—C26	−60.0 (4)
C11—C12—C13—C14	−59.3 (4)	C23—C24—C25—C27	66.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^i	0.82	2.07	2.850 (3)	160
O2—H2O···O5^ii	0.82	1.99	2.807 (3)	172
O3—H3O···O2	0.82	1.95	2.669 (3)	146
O5—H5···O1^iii	0.82	1.83	2.620 (3)	162
O6—H6···O9	0.82	2.37	3.146 (4)	158
O7—H7···O8^iv	0.82	2.02	2.817 (3)	165
O8—H8···O9^v	0.82	2.01	2.819 (4)	168
O9—H9OB···O6^vi	0.82 (1)	2.07 (1)	2.892 (4)	180 (6)
O9—H9OA···O7^vii	0.82 (1)	2.05 (1)	2.862 (4)	168 (4)

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) x−1/2, −y−1/2, −z; (v) x+1/2, −y−1/2, −z; (vi) x−1/2, −y+1/2, −z; (vii) x−1, y, z.