The furan-osteroid viridiol.

The asymmetric unit of the title compound, C20H18O6 (systematic name: 1β,3β-dihy-droxy-2β-meth-oxyfuro[4',3',2':4,5,6]-18-norandrosta-8,11,13-triene-7,17-dione), a dihydro derivative of the fungal steroid viridin, contains two mol-ecules with similar conformations. The rings bearing the hy-droxy groups adopt boat conformations. The absolute structure was assigned based on the known chirality of a precursor compound. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, generating a three-dimensional network and weak C-H⋯O inter-actions consolidate the packing.

Related literature

For background to fungal metabolites, see: Brian & McGowan (1945 ▶); Moffatt et al. (1969 ▶); Jones & Hancock (1987 ▶); Hanson (1995 ▶); Cross et al. (1995 ▶); Przybyl (2002 ▶); Smith et al. (2009 ▶); Andersson et al. (2010 ▶); Queloz et al. (2011 ▶); Andersson (2012 ▶); Andersson et al. (2012 ▶, 2013 ▶). For related structures, see: Neidle et al. (1972 ▶); Lang et al. (2009 ▶). For other characterization methods, see: Brian et al. (1957 ▶); Aldridge et al. (1975 ▶); Blight & Grove (1986 ▶). For background to the assignment of the absolute structure of the title compound, see: MacMillan et al. (1972 ▶); Harrison (1990 ▶); Dewick (2002 ▶); Wipf & Kerekes (2003 ▶); Flack & Bernardinelli (2000 ▶).

Experimental

Crystal data

C20H18O6

M = 354.34

Orthorhombic,

a = 6.8285 (2) Å

b = 20.1939 (6) Å

c = 22.4344 (6) Å

V = 3093.57 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 93 K

0.3 × 0.25 × 0.2 mm

Data collection

Oxford Diffraction XcaliburIII Sapphire-3 CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.891, T max = 1.000

26916 measured reflections

4874 independent reflections

3294 reflections with I > 2σ(I)

R int = 0.085

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.089

S = 0.91

4874 reflections

485 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXD (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXL (Sheldrick, 2008 ▶); software used to prepare material for publication: DIAMOND (Brandenburg, 2001 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005606/hb7028sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005606/hb7028Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005606/hb7028Isup3.cml

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

C20H18O6	F(000) = 1488
Mr = 354.34	Dx = 1.522 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5568 reflections
a = 6.8285 (2) Å	θ = 2.9–32.3°
b = 20.1939 (6) Å	µ = 0.11 mm−1
c = 22.4344 (6) Å	T = 93 K
V = 3093.57 (15) Å3	Block, colourless
Z = 8	0.3 × 0.25 × 0.2 mm

Oxford Diffraction XcaliburIII Sapphire-3 CCD diffractometer	4874 independent reflections
Radiation source: fine-focus sealed tube	3294 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.085
Detector resolution: 16.5467 pixels mm-1	θmax = 29.6°, θmin = 3.1°
ω scans at different φ	h = −9→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −27→28
Tmin = 0.891, Tmax = 1.000	l = −31→27
26916 measured 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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.0383P)2] where P = (Fo2 + 2Fc2)/3
S = 0.91	(Δ/σ)max < 0.001
4874 reflections	Δρmax = 0.33 e Å−3
485 parameters	Δρmin = −0.25 e Å−3
0 restraints	Absolute structure: syn
Primary atom site location: structure-invariant direct methods

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
C1A	0.6537 (4)	0.27709 (14)	0.36272 (12)	0.0138 (6)
H1A	0.7696	0.2648	0.3378	0.017*
C2A	0.7233 (4)	0.33366 (13)	0.40850 (12)	0.0126 (6)
H2A	0.8510	0.3506	0.3928	0.015*
C3A	0.5943 (4)	0.39445 (13)	0.41746 (12)	0.0133 (6)
H3A	0.6728	0.4296	0.4379	0.016*
C4A	0.5392 (4)	0.41850 (13)	0.35652 (12)	0.0130 (6)
C5A	0.5063 (4)	0.37163 (12)	0.31066 (11)	0.0112 (5)
C6A	0.4956 (5)	0.40461 (12)	0.25876 (11)	0.0144 (6)
C7A	0.4926 (4)	0.37424 (13)	0.20055 (11)	0.0142 (6)
C8A	0.4930 (5)	0.29928 (12)	0.20388 (11)	0.0129 (6)
C9A	0.4948 (4)	0.26436 (12)	0.25865 (11)	0.0111 (6)
C10A	0.4855 (5)	0.29948 (12)	0.31901 (11)	0.0125 (6)
C11A	0.4926 (5)	0.19481 (13)	0.25915 (11)	0.0154 (6)
H11A	0.4941	0.1721	0.2962	0.019*
C12A	0.4883 (5)	0.15934 (13)	0.20748 (11)	0.0142 (6)
H12A	0.4869	0.1123	0.2082	0.017*
C13A	0.4860 (5)	0.19347 (13)	0.15357 (11)	0.0128 (6)
C14A	0.4907 (5)	0.26182 (13)	0.15062 (11)	0.0128 (6)
C15A	0.4908 (5)	0.28556 (13)	0.08641 (11)	0.0170 (6)
H15A	0.6103	0.3115	0.0776	0.020*
H15B	0.3744	0.3133	0.0781	0.020*
C16A	0.4857 (5)	0.22141 (13)	0.04961 (11)	0.0169 (6)
H16A	0.3696	0.2209	0.0232	0.020*
H16B	0.6048	0.2177	0.0247	0.020*
C17A	0.4762 (4)	0.16537 (14)	0.09340 (11)	0.0144 (6)
C18A	0.2815 (4)	0.28525 (15)	0.34602 (12)	0.0152 (6)
H18A	0.2704	0.3073	0.3848	0.023*
H18B	0.2650	0.2374	0.3512	0.023*
H18C	0.1798	0.3021	0.3192	0.023*
O19A	0.5889 (3)	0.21883 (10)	0.39170 (9)	0.0183 (5)
H19A	0.690 (5)	0.1979 (16)	0.4026 (14)	0.027*
O20A	0.4303 (3)	0.37778 (10)	0.45422 (9)	0.0175 (5)
H20A	0.360 (5)	0.4134 (16)	0.4665 (13)	0.026*
C21A	0.5428 (4)	0.47768 (14)	0.32940 (12)	0.0169 (7)
H21A	0.5620	0.5185	0.3495	0.020*
O22A	0.5152 (3)	0.47204 (8)	0.26879 (7)	0.0163 (4)
O23A	0.4968 (3)	0.40411 (9)	0.15318 (8)	0.0202 (5)
O24A	0.4658 (3)	0.10611 (9)	0.08101 (8)	0.0197 (5)
O25A	0.7644 (3)	0.30680 (10)	0.46491 (8)	0.0155 (5)
C26A	0.9470 (5)	0.27292 (15)	0.46869 (13)	0.0198 (7)
H26A	0.9599	0.2425	0.4349	0.030*
H26B	0.9525	0.2478	0.5060	0.030*
H26C	1.0542	0.3052	0.4678	0.030*
C1B	0.1585 (4)	0.56087 (14)	0.11712 (12)	0.0138 (6)
H1B	0.2773	0.5707	0.1416	0.017*
C2B	0.2209 (4)	0.50356 (13)	0.07249 (11)	0.0122 (6)
H2B	0.3410	0.4826	0.0897	0.015*
C3B	0.0753 (4)	0.44728 (14)	0.06042 (12)	0.0142 (6)
H3B	0.1451	0.4112	0.0385	0.017*
C4B	0.0186 (5)	0.42186 (13)	0.12046 (12)	0.0148 (6)
C5B	0.0000 (5)	0.46678 (12)	0.16840 (11)	0.0122 (6)
C6B	−0.0095 (5)	0.43195 (12)	0.21909 (12)	0.0153 (6)
C7B	0.0047 (5)	0.45916 (13)	0.27823 (12)	0.0147 (6)
C8B	0.0128 (5)	0.53407 (12)	0.27772 (11)	0.0131 (6)
C9B	0.0140 (4)	0.57193 (13)	0.22427 (11)	0.0124 (6)
C10B	−0.0063 (5)	0.54023 (12)	0.16285 (11)	0.0122 (6)
C11B	0.0197 (4)	0.64112 (12)	0.22764 (11)	0.0130 (6)
H11B	0.0221	0.6661	0.1917	0.016*
C12B	0.0220 (5)	0.67419 (13)	0.28128 (11)	0.0142 (6)
H12B	0.0244	0.7212	0.2827	0.017*
C13B	0.0207 (4)	0.63669 (13)	0.33360 (11)	0.0111 (6)
C14B	0.0183 (4)	0.56769 (12)	0.33227 (11)	0.0126 (6)
C15B	0.0213 (5)	0.53980 (13)	0.39498 (11)	0.0143 (6)
H15C	0.1383	0.5116	0.4011	0.017*
H15D	−0.0974	0.5130	0.4027	0.017*
C16B	0.0272 (5)	0.60024 (13)	0.43590 (11)	0.0152 (6)
H16C	−0.0855	0.5998	0.4636	0.018*
H16D	0.1496	0.6006	0.4596	0.018*
C17B	0.0180 (5)	0.66011 (13)	0.39581 (11)	0.0148 (6)
C18B	−0.2121 (5)	0.55864 (15)	0.13852 (13)	0.0175 (7)
H18D	−0.2304	0.5386	0.0991	0.026*
H18E	−0.2231	0.6069	0.1353	0.026*
H18F	−0.3128	0.5420	0.1658	0.026*
O19B	0.1100 (3)	0.62125 (10)	0.08747 (9)	0.0187 (5)
H19B	0.052 (5)	0.6121 (16)	0.0560 (14)	0.028*
O20B	−0.0878 (3)	0.46870 (10)	0.02504 (9)	0.0194 (5)
H20B	−0.090 (5)	0.4507 (15)	−0.0072 (14)	0.029*
C21B	0.0133 (5)	0.36090 (14)	0.14567 (12)	0.0180 (6)
H21B	0.0199	0.3206	0.1240	0.022*
O22B	−0.0029 (3)	0.36481 (8)	0.20658 (8)	0.0182 (4)
O23B	0.0138 (4)	0.42681 (9)	0.32411 (8)	0.0211 (5)
O24B	0.0124 (4)	0.71751 (9)	0.41237 (8)	0.0244 (5)
O25B	0.2759 (3)	0.53000 (9)	0.01613 (8)	0.0145 (4)
C26B	0.4663 (4)	0.55951 (14)	0.01558 (12)	0.0165 (6)
H26D	0.4740	0.5934	0.0468	0.025*
H26E	0.4899	0.5800	−0.0233	0.025*
H26F	0.5654	0.5254	0.0229	0.025*

	U11	U22	U33	U12	U13	U23
C1A	0.0182 (16)	0.0109 (15)	0.0122 (14)	0.0002 (12)	0.0016 (12)	0.0007 (12)
C2A	0.0151 (16)	0.0110 (14)	0.0118 (15)	0.0000 (12)	−0.0030 (12)	0.0008 (12)
C3A	0.0185 (16)	0.0079 (14)	0.0136 (14)	−0.0002 (12)	0.0016 (12)	−0.0013 (12)
C4A	0.0125 (16)	0.0121 (14)	0.0145 (14)	0.0004 (12)	−0.0001 (12)	−0.0001 (11)
C5A	0.0091 (14)	0.0125 (13)	0.0119 (13)	0.0005 (13)	0.0025 (13)	−0.0004 (10)
C6A	0.0152 (15)	0.0095 (14)	0.0185 (14)	0.0027 (14)	0.0001 (14)	0.0001 (11)
C7A	0.0112 (15)	0.0141 (13)	0.0174 (14)	−0.0001 (14)	−0.0007 (14)	0.0025 (12)
C8A	0.0134 (15)	0.0120 (13)	0.0134 (13)	0.0012 (14)	−0.0038 (13)	0.0007 (11)
C9A	0.0083 (14)	0.0108 (13)	0.0141 (13)	−0.0001 (13)	0.0005 (13)	−0.0004 (10)
C10A	0.0162 (16)	0.0113 (13)	0.0101 (12)	−0.0001 (14)	0.0004 (13)	0.0007 (10)
C11A	0.0211 (16)	0.0144 (14)	0.0108 (13)	−0.0001 (15)	0.0002 (14)	0.0033 (11)
C12A	0.0188 (16)	0.0085 (12)	0.0152 (14)	−0.0021 (14)	−0.0013 (14)	0.0011 (11)
C13A	0.0117 (15)	0.0142 (13)	0.0125 (13)	−0.0026 (14)	0.0023 (13)	−0.0013 (11)
C14A	0.0109 (15)	0.0159 (14)	0.0116 (13)	0.0009 (14)	0.0004 (13)	0.0017 (10)
C15A	0.0234 (17)	0.0141 (14)	0.0134 (13)	−0.0011 (15)	−0.0019 (14)	0.0036 (11)
C16A	0.0231 (17)	0.0176 (14)	0.0099 (13)	−0.0016 (15)	0.0023 (14)	0.0009 (11)
C17A	0.0124 (16)	0.0169 (14)	0.0139 (14)	0.0008 (14)	0.0010 (13)	−0.0039 (12)
C18A	0.0186 (16)	0.0125 (15)	0.0145 (15)	−0.0011 (13)	0.0036 (12)	−0.0005 (12)
O19A	0.0266 (14)	0.0097 (11)	0.0186 (11)	−0.0012 (10)	−0.0061 (9)	0.0043 (9)
O20A	0.0188 (12)	0.0145 (11)	0.0191 (11)	0.0039 (9)	0.0067 (9)	−0.0023 (9)
C21A	0.0189 (18)	0.0146 (15)	0.0172 (15)	0.0015 (13)	−0.0044 (13)	−0.0010 (12)
O22A	0.0256 (12)	0.0077 (9)	0.0156 (10)	−0.0006 (10)	−0.0014 (10)	0.0008 (7)
O23A	0.0269 (12)	0.0153 (10)	0.0185 (10)	−0.0001 (11)	−0.0040 (11)	0.0042 (8)
O24A	0.0285 (13)	0.0172 (11)	0.0134 (10)	−0.0004 (10)	0.0014 (9)	−0.0024 (8)
O25A	0.0172 (12)	0.0160 (11)	0.0133 (10)	0.0024 (9)	−0.0013 (8)	0.0035 (9)
C26A	0.0192 (18)	0.0183 (16)	0.0220 (16)	0.0018 (14)	−0.0027 (13)	0.0008 (13)
C1B	0.0179 (17)	0.0129 (16)	0.0106 (14)	0.0027 (13)	−0.0007 (12)	−0.0002 (12)
C2B	0.0188 (16)	0.0107 (14)	0.0070 (13)	0.0024 (12)	−0.0005 (12)	0.0002 (11)
C3B	0.0170 (17)	0.0102 (14)	0.0153 (15)	0.0035 (13)	−0.0002 (12)	−0.0018 (12)
C4B	0.0114 (15)	0.0133 (14)	0.0196 (15)	−0.0031 (14)	0.0018 (13)	−0.0041 (11)
C5B	0.0114 (15)	0.0102 (13)	0.0151 (14)	0.0002 (14)	−0.0001 (13)	−0.0042 (10)
C6B	0.0190 (16)	0.0067 (13)	0.0202 (14)	−0.0009 (14)	0.0039 (14)	−0.0019 (11)
C7B	0.0137 (15)	0.0125 (13)	0.0178 (14)	0.0023 (13)	0.0022 (14)	0.0019 (11)
C8B	0.0148 (15)	0.0104 (13)	0.0142 (13)	0.0035 (13)	−0.0013 (13)	0.0000 (11)
C9B	0.0123 (15)	0.0126 (14)	0.0124 (13)	−0.0020 (13)	0.0000 (13)	−0.0003 (10)
C10B	0.0155 (15)	0.0082 (13)	0.0131 (13)	0.0033 (14)	−0.0008 (13)	−0.0012 (10)
C11B	0.0161 (16)	0.0105 (13)	0.0125 (13)	0.0002 (13)	−0.0015 (13)	0.0032 (10)
C12B	0.0181 (17)	0.0073 (13)	0.0173 (14)	−0.0008 (13)	0.0001 (13)	−0.0024 (11)
C13B	0.0078 (14)	0.0156 (14)	0.0101 (13)	0.0014 (13)	−0.0008 (12)	−0.0015 (10)
C14B	0.0090 (15)	0.0132 (14)	0.0157 (14)	0.0013 (13)	−0.0007 (13)	0.0045 (11)
C15B	0.0186 (17)	0.0111 (13)	0.0132 (13)	0.0009 (14)	0.0009 (13)	0.0024 (10)
C16B	0.0173 (16)	0.0174 (14)	0.0109 (13)	0.0006 (14)	−0.0021 (12)	0.0025 (11)
C17B	0.0142 (16)	0.0133 (14)	0.0170 (14)	−0.0006 (14)	−0.0030 (13)	−0.0029 (11)
C18B	0.0209 (17)	0.0149 (16)	0.0167 (15)	0.0024 (14)	−0.0062 (13)	−0.0018 (13)
O19B	0.0324 (13)	0.0112 (11)	0.0125 (10)	0.0024 (9)	−0.0019 (10)	0.0015 (9)
O20B	0.0196 (12)	0.0227 (12)	0.0160 (11)	0.0050 (10)	−0.0058 (9)	−0.0068 (9)
C21B	0.0187 (16)	0.0165 (15)	0.0187 (15)	−0.0018 (15)	0.0013 (14)	−0.0054 (12)
O22B	0.0256 (12)	0.0097 (9)	0.0195 (10)	−0.0004 (10)	0.0039 (11)	−0.0013 (8)
O23B	0.0325 (13)	0.0138 (10)	0.0169 (10)	0.0022 (11)	0.0044 (11)	0.0042 (8)
O24B	0.0435 (14)	0.0147 (10)	0.0151 (10)	−0.0009 (12)	−0.0042 (11)	−0.0013 (8)
O25B	0.0178 (11)	0.0138 (10)	0.0118 (10)	0.0004 (9)	−0.0003 (8)	0.0019 (8)
C26B	0.0149 (17)	0.0177 (14)	0.0169 (14)	0.0017 (13)	−0.0008 (13)	−0.0007 (12)

C1A—O19A	1.415 (3)	C1B—O19B	1.428 (3)
C1A—C10A	1.576 (4)	C1B—C10B	1.579 (4)
C1A—C2A	1.608 (4)	C1B—C2B	1.589 (4)
C1A—H1A	1.0000	C1B—H1B	1.0000
C2A—O25A	1.405 (3)	C2B—O25B	1.423 (3)
C2A—C3A	1.524 (4)	C2B—C3B	1.534 (4)
C2A—H2A	1.0000	C2B—H2B	1.0000
C3A—O20A	1.431 (3)	C3B—O20B	1.434 (3)
C3A—C4A	1.499 (4)	C3B—C4B	1.492 (4)
C3A—H3A	1.0000	C3B—H3B	1.0000
C4A—C21A	1.341 (4)	C4B—C21B	1.355 (4)
C4A—C5A	1.416 (3)	C4B—C5B	1.413 (3)
C5A—C6A	1.343 (3)	C5B—C6B	1.339 (3)
C5A—C10A	1.476 (4)	C5B—C10B	1.489 (3)
C6A—O22A	1.386 (3)	C6B—O22B	1.385 (3)
C6A—C7A	1.443 (4)	C6B—C7B	1.439 (4)
C7A—O23A	1.222 (3)	C7B—O23B	1.221 (3)
C7A—C8A	1.516 (3)	C7B—C8B	1.514 (4)
C8A—C14A	1.414 (3)	C8B—C14B	1.400 (4)
C8A—C9A	1.417 (3)	C8B—C9B	1.422 (3)
C9A—C11A	1.405 (4)	C9B—C11B	1.400 (3)
C9A—C10A	1.530 (3)	C9B—C10B	1.526 (3)
C10A—C18A	1.546 (4)	C10B—C18B	1.553 (4)
C11A—C12A	1.363 (3)	C11B—C12B	1.377 (3)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.392 (3)	C12B—C13B	1.397 (3)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.382 (4)	C13B—C14B	1.394 (3)
C13A—C17A	1.466 (4)	C13B—C17B	1.474 (4)
C14A—C15A	1.518 (3)	C14B—C15B	1.515 (3)
C15A—C16A	1.537 (3)	C15B—C16B	1.528 (4)
C15A—H15A	0.9900	C15B—H15C	0.9900
C15A—H15B	0.9900	C15B—H15D	0.9900
C16A—C17A	1.500 (4)	C16B—C17B	1.508 (4)
C16A—H16A	0.9900	C16B—H16C	0.9900
C16A—H16B	0.9900	C16B—H16D	0.9900
C17A—O24A	1.231 (3)	C17B—O24B	1.218 (3)
C18A—H18A	0.9800	C18B—H18D	0.9800
C18A—H18B	0.9800	C18B—H18E	0.9800
C18A—H18C	0.9800	C18B—H18F	0.9800
O19A—H19A	0.84 (3)	O19B—H19B	0.83 (3)
O20A—H20A	0.91 (3)	O20B—H20B	0.81 (3)
C21A—O22A	1.377 (3)	C21B—O22B	1.373 (3)
C21A—H21A	0.9500	C21B—H21B	0.9500
O25A—C26A	1.425 (4)	O25B—C26B	1.430 (3)
C26A—H26A	0.9800	C26B—H26D	0.9800
C26A—H26B	0.9800	C26B—H26E	0.9800
C26A—H26C	0.9800	C26B—H26F	0.9800
O19A—C1A—C10A	107.2 (2)	O19B—C1B—C10B	111.3 (2)
O19A—C1A—C2A	112.9 (2)	O19B—C1B—C2B	113.0 (2)
C10A—C1A—C2A	114.1 (2)	C10B—C1B—C2B	114.1 (2)
O19A—C1A—H1A	107.4	O19B—C1B—H1B	105.9
C10A—C1A—H1A	107.4	C10B—C1B—H1B	105.9
C2A—C1A—H1A	107.4	C2B—C1B—H1B	105.9
O25A—C2A—C3A	107.9 (2)	O25B—C2B—C3B	107.0 (2)
O25A—C2A—C1A	111.1 (2)	O25B—C2B—C1B	110.9 (2)
C3A—C2A—C1A	119.0 (2)	C3B—C2B—C1B	118.5 (2)
O25A—C2A—H2A	106.0	O25B—C2B—H2B	106.6
C3A—C2A—H2A	106.0	C3B—C2B—H2B	106.6
C1A—C2A—H2A	106.0	C1B—C2B—H2B	106.6
O20A—C3A—C4A	113.9 (2)	O20B—C3B—C4B	113.7 (2)
O20A—C3A—C2A	109.8 (2)	O20B—C3B—C2B	112.2 (2)
C4A—C3A—C2A	106.6 (2)	C4B—C3B—C2B	105.3 (2)
O20A—C3A—H3A	108.8	O20B—C3B—H3B	108.5
C4A—C3A—H3A	108.8	C4B—C3B—H3B	108.5
C2A—C3A—H3A	108.8	C2B—C3B—H3B	108.5
C21A—C4A—C5A	105.6 (2)	C21B—C4B—C5B	105.3 (2)
C21A—C4A—C3A	134.3 (3)	C21B—C4B—C3B	134.1 (3)
C5A—C4A—C3A	119.1 (2)	C5B—C4B—C3B	119.3 (2)
C6A—C5A—C4A	107.9 (2)	C6B—C5B—C4B	108.3 (2)
C6A—C5A—C10A	126.5 (2)	C6B—C5B—C10B	126.4 (2)
C4A—C5A—C10A	125.7 (2)	C4B—C5B—C10B	125.3 (2)
C5A—C6A—O22A	109.9 (2)	C5B—C6B—O22B	109.9 (2)
C5A—C6A—C7A	125.1 (2)	C5B—C6B—C7B	125.4 (2)
O22A—C6A—C7A	124.4 (2)	O22B—C6B—C7B	123.9 (2)
O23A—C7A—C6A	125.2 (2)	O23B—C7B—C6B	125.2 (2)
O23A—C7A—C8A	122.4 (2)	O23B—C7B—C8B	122.6 (2)
C6A—C7A—C8A	112.3 (2)	C6B—C7B—C8B	112.1 (2)
C14A—C8A—C9A	117.8 (2)	C14B—C8B—C9B	118.4 (2)
C14A—C8A—C7A	119.5 (2)	C14B—C8B—C7B	118.6 (2)
C9A—C8A—C7A	122.7 (2)	C9B—C8B—C7B	123.0 (2)
C11A—C9A—C8A	120.3 (2)	C11B—C9B—C8B	119.4 (2)
C11A—C9A—C10A	117.1 (2)	C11B—C9B—C10B	118.0 (2)
C8A—C9A—C10A	122.5 (2)	C8B—C9B—C10B	122.4 (2)
C5A—C10A—C9A	110.0 (2)	C5B—C10B—C9B	109.9 (2)
C5A—C10A—C18A	108.7 (2)	C5B—C10B—C18B	107.1 (2)
C9A—C10A—C18A	107.3 (2)	C9B—C10B—C18B	107.4 (2)
C5A—C10A—C1A	107.0 (2)	C5B—C10B—C1B	107.3 (2)
C9A—C10A—C1A	112.8 (2)	C9B—C10B—C1B	114.3 (2)
C18A—C10A—C1A	111.1 (2)	C18B—C10B—C1B	110.7 (2)
C12A—C11A—C9A	121.3 (2)	C12B—C11B—C9B	122.1 (2)
C12A—C11A—H11A	119.4	C12B—C11B—H11B	118.9
C9A—C11A—H11A	119.4	C9B—C11B—H11B	118.9
C11A—C12A—C13A	118.6 (2)	C11B—C12B—C13B	118.1 (2)
C11A—C12A—H12A	120.7	C11B—C12B—H12B	120.9
C13A—C12A—H12A	120.7	C13B—C12B—H12B	120.9
C14A—C13A—C12A	122.4 (2)	C14B—C13B—C12B	121.6 (2)
C14A—C13A—C17A	110.1 (2)	C14B—C13B—C17B	109.9 (2)
C12A—C13A—C17A	127.5 (2)	C12B—C13B—C17B	128.4 (2)
C13A—C14A—C8A	119.6 (2)	C13B—C14B—C8B	120.2 (2)
C13A—C14A—C15A	111.1 (2)	C13B—C14B—C15B	110.6 (2)
C8A—C14A—C15A	129.3 (2)	C8B—C14B—C15B	129.2 (2)
C14A—C15A—C16A	104.1 (2)	C14B—C15B—C16B	105.2 (2)
C14A—C15A—H15A	110.9	C14B—C15B—H15C	110.7
C16A—C15A—H15A	110.9	C16B—C15B—H15C	110.7
C14A—C15A—H15B	110.9	C14B—C15B—H15D	110.7
C16A—C15A—H15B	110.9	C16B—C15B—H15D	110.7
H15A—C15A—H15B	109.0	H15C—C15B—H15D	108.8
C17A—C16A—C15A	106.6 (2)	C17B—C16B—C15B	106.3 (2)
C17A—C16A—H16A	110.4	C17B—C16B—H16C	110.5
C15A—C16A—H16A	110.4	C15B—C16B—H16C	110.5
C17A—C16A—H16B	110.4	C17B—C16B—H16D	110.5
C15A—C16A—H16B	110.4	C15B—C16B—H16D	110.5
H16A—C16A—H16B	108.6	H16C—C16B—H16D	108.7
O24A—C17A—C13A	125.9 (2)	O24B—C17B—C13B	126.5 (2)
O24A—C17A—C16A	126.0 (2)	O24B—C17B—C16B	125.6 (2)
C13A—C17A—C16A	108.0 (2)	C13B—C17B—C16B	107.9 (2)
C10A—C18A—H18A	109.5	C10B—C18B—H18D	109.5
C10A—C18A—H18B	109.5	C10B—C18B—H18E	109.5
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
C10A—C18A—H18C	109.5	C10B—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5
C1A—O19A—H19A	107 (2)	C1B—O19B—H19B	108 (2)
C3A—O20A—H20A	114 (2)	C3B—O20B—H20B	112 (2)
C4A—C21A—O22A	111.8 (2)	C4B—C21B—O22B	111.4 (2)
C4A—C21A—H21A	124.1	C4B—C21B—H21B	124.3
O22A—C21A—H21A	124.1	O22B—C21B—H21B	124.3
C21A—O22A—C6A	104.8 (2)	C21B—O22B—C6B	105.11 (19)
C2A—O25A—C26A	114.4 (2)	C2B—O25B—C26B	113.8 (2)
O25A—C26A—H26A	109.5	O25B—C26B—H26D	109.5
O25A—C26A—H26B	109.5	O25B—C26B—H26E	109.5
H26A—C26A—H26B	109.5	H26D—C26B—H26E	109.5
O25A—C26A—H26C	109.5	O25B—C26B—H26F	109.5
H26A—C26A—H26C	109.5	H26D—C26B—H26F	109.5
H26B—C26A—H26C	109.5	H26E—C26B—H26F	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O19A—H19A···O19Bi	0.85 (3)	2.08 (3)	2.886 (3)	160 (3)
O19B—H19B···O20Aii	0.83 (3)	2.30 (3)	3.002 (3)	143 (3)
O20A—H20A···O25Biii	0.91 (3)	1.85 (3)	2.717 (3)	160 (3)
O20B—H20B···O24Aiv	0.81 (3)	2.05 (3)	2.842 (3)	166 (3)
C2A—H2A···O23Bv	1.00	2.45	3.325 (3)	146
C2B—H2B···O23A	1.00	2.38	3.295 (3)	151
C11A—H11A···O19A	0.95	2.43	3.084 (3)	126
C11B—H11B···O19B	0.95	2.58	3.230 (3)	126
C18A—H18A···O20A	0.98	2.38	3.227 (3)	145
C18B—H18D···O20B	0.98	2.39	3.241 (4)	145
C21A—H21A···O24Avi	0.95	2.37	3.282 (3)	162
C21B—H21B···O24Bvii	0.95	2.25	3.180 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O19A—H19A⋯O19B i	0.85 (3)	2.08 (3)	2.886 (3)	160 (3)
O19B—H19B⋯O20A ii	0.83 (3)	2.30 (3)	3.002 (3)	143 (3)
O20A—H20A⋯O25B iii	0.91 (3)	1.85 (3)	2.717 (3)	160 (3)
O20B—H20B⋯O24A iv	0.81 (3)	2.05 (3)	2.842 (3)	166 (3)
C2A—H2A⋯O23B v	1.00	2.45	3.325 (3)	146
C2B—H2B⋯O23A	1.00	2.38	3.295 (3)	151
C11A—H11A⋯O19A	0.95	2.43	3.084 (3)	126
C11B—H11B⋯O19B	0.95	2.58	3.230 (3)	126
C18A—H18A⋯O20A	0.98	2.38	3.227 (3)	145
C18B—H18D⋯O20B	0.98	2.39	3.241 (4)	145
C21A—H21A⋯O24A vi	0.95	2.37	3.282 (3)	162
C21B—H21B⋯O24B vii	0.95	2.25	3.180 (3)	167

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .