Redetermination and absolute configuration of pruniflorone M monohydrate.

THE TITLE XANTHONE KNOWN AS PRUNIFLORONE M (SYSTEMATIC NAME: (2R)-5,10-dihy-droxy-2-hy-droxy-methyl-1,1-dimethyl-1H-furo[2,3-c]xanthen-6-one), crystallized in a monohydrate form, C(18)H(16)O(6)·H(2)O. It was isolated from the green fruits of Cratoxylum formosum ssp. pruniflorum. The structure of the title compound has been reported previously [Boonnak et al. (2010 ▶). Aust. J. Chem. 63, 1550-1556], but we report here the absolute configuration determined using Cu Kα radiation. There are two crystallograpically independent mol-ecules in the asymmetric unit, which differ slightly in the bond angles. The hy-droxy-methyl substituents at position 2 of the furan rings of both pruniflorone M mol-ecules adopt R configurations. In both mol-ecules, the three rings of the xanthone skeleton are approximately coplanar, with an r.m.s. deviation of 0.0124 (2) Å for one mol-ecule and 0.0289 (2) Å for the other, and the furan ring adopts an envelope conformation. In the crystal, mol-ecules of pruniflorone M and water are linked into a two-dimensional network by O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions. The crystal structure is further consolidated by π-π inter-actions with centroid-centroid distances in the range 3.5987 (13)-3.7498 (14) Å. Short C⋯C [3.378 (3) Å] and O⋯O [2.918 (3) Å] contacts are also observed.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶) and for ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For background to xanthones and their biological activity, see: Boonnak, Karalai et al. (2007 ▶); Boonnak et al. (2009 ▶, 2010 ▶); Hay et al. (2008 ▶); Marques et al. (2000 ▶); Molinar-Toribio et al. (2006 ▶); Phongpaichit et al. (1994 ▶); Yu et al. (2007 ▶). For related structures, see: Boonnak et al. (2006 ▶); Boonnak, Fun et al. (2007 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H16O6·H2O

M = 346.32

Orthorhombic,

a = 9.8887 (3) Å

b = 15.6028 (4) Å

c = 20.4857 (5) Å

V = 3160.77 (15) Å3

Z = 8

Cu Kα radiation

μ = 0.95 mm−1

T = 100 K

0.54 × 0.17 × 0.10 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.627, T max = 0.913

13449 measured reflections

4981 independent reflections

4753 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.120

S = 1.02

4981 reflections

456 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 2102 Friedel pairs

Flack parameter: 0.06 (19)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025177/sj5174sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025177/sj5174Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025177/sj5174Isup3.cml

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

C18H16O6·H2O	Dx = 1.456 Mg m−3
Mr = 346.32	Melting point = 508–510 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4981 reflections
a = 9.8887 (3) Å	θ = 5.3–63.5°
b = 15.6028 (4) Å	µ = 0.95 mm−1
c = 20.4857 (5) Å	T = 100 K
V = 3160.77 (15) Å3	Block, yellow
Z = 8	0.54 × 0.17 × 0.10 mm
F(000) = 1456

Bruker APEX DUO CCD area-detector diffractometer	4981 independent reflections
Radiation source: sealed tube	4753 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 63.5°, θmin = 5.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→11
Tmin = 0.627, Tmax = 0.913	k = −18→18
13449 measured reflections	l = −23→23

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0751P)2 + 0.9688P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4981 reflections	Δρmax = 0.56 e Å−3
456 parameters	Δρmin = −0.23 e Å−3
0 restraints	Absolute structure: Flack (1983), 2102 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (19)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1A	0.40973 (17)	0.43207 (10)	0.67334 (7)	0.0370 (4)
O2A	0.3650 (2)	0.44183 (12)	0.87235 (8)	0.0512 (5)
O3A	0.18470 (19)	0.55552 (12)	0.85896 (8)	0.0483 (4)
H3OA	0.2444	0.5118	0.8781	0.072*
O4A	0.58566 (19)	0.32867 (12)	0.61541 (8)	0.0484 (4)
H4OA	0.6449	0.2869	0.6019	0.062 (9)*
O5A	0.06909 (18)	0.63151 (11)	0.64104 (8)	0.0444 (4)
O6A	0.1454 (2)	0.74151 (11)	0.54195 (9)	0.0551 (5)
H6OA	0.0952	0.7697	0.5655	0.083*
C1A	0.2000 (2)	0.54898 (15)	0.79348 (11)	0.0357 (5)
C2A	0.1201 (2)	0.59682 (17)	0.75260 (11)	0.0381 (5)
H2A	0.0538	0.6334	0.7688	0.046*
C3A	0.1426 (2)	0.58815 (14)	0.68612 (11)	0.0353 (5)
C4A	0.2403 (2)	0.53548 (14)	0.65853 (11)	0.0339 (5)
C5A	0.5798 (2)	0.32706 (15)	0.68149 (11)	0.0378 (5)
C6A	0.6618 (3)	0.27595 (16)	0.71967 (13)	0.0426 (6)
H6A	0.7249	0.2404	0.6997	0.051*
C7A	0.6521 (3)	0.27649 (16)	0.78758 (13)	0.0460 (6)
H7A	0.7088	0.2418	0.8123	0.055*
C8A	0.5592 (3)	0.32806 (16)	0.81792 (12)	0.0428 (6)
H8A	0.5519	0.3275	0.8632	0.051*
C9A	0.4758 (3)	0.38129 (15)	0.78110 (11)	0.0375 (5)
C10A	0.3778 (2)	0.43875 (15)	0.81172 (11)	0.0374 (5)
C11A	0.2983 (2)	0.49098 (15)	0.76823 (11)	0.0341 (5)
C12A	0.3168 (2)	0.48597 (14)	0.70018 (11)	0.0336 (5)
C13A	0.4870 (2)	0.38085 (15)	0.71280 (11)	0.0345 (5)
C14A	0.2429 (2)	0.54925 (16)	0.58514 (11)	0.0376 (5)
C15A	0.1020 (3)	0.59373 (16)	0.57746 (11)	0.0409 (5)
H15A	0.0355	0.5485	0.5691	0.049*
C16A	0.0818 (3)	0.66176 (16)	0.52624 (12)	0.0476 (6)
H16A	0.1176	0.6411	0.4851	0.057*
H16B	−0.0144	0.6714	0.5205	0.057*
C17A	0.3638 (3)	0.6064 (2)	0.56656 (13)	0.0528 (7)
H17A	0.4466	0.5770	0.5764	0.079*
H17B	0.3598	0.6589	0.5910	0.079*
H17C	0.3604	0.6190	0.5207	0.079*
C18A	0.2474 (3)	0.46718 (18)	0.54526 (13)	0.0535 (7)
H18A	0.3326	0.4391	0.5520	0.080*
H18B	0.2370	0.4807	0.4998	0.080*
H18C	0.1754	0.4299	0.5588	0.080*
O1B	0.59342 (16)	0.57000 (10)	0.32981 (7)	0.0359 (4)
O2B	0.64340 (19)	0.55237 (12)	0.13115 (7)	0.0489 (4)
O3B	0.82577 (19)	0.44097 (12)	0.14837 (8)	0.0470 (4)
H3OB	0.7592	0.4841	0.1249	0.070*
O4B	0.42557 (18)	0.67981 (11)	0.38433 (7)	0.0433 (4)
H4OB	0.3510	0.7205	0.3997	0.065*
O5B	0.9092 (2)	0.35711 (12)	0.36836 (9)	0.0535 (5)
O6B	0.9636 (4)	0.2762 (3)	0.49615 (14)	0.1384 (16)
H6OB	0.9941	0.2549	0.4626	0.208*
C1B	0.8046 (2)	0.44754 (15)	0.21360 (11)	0.0356 (5)
C2B	0.8789 (3)	0.39760 (16)	0.25614 (11)	0.0395 (5)
H2B	0.9461	0.3606	0.2415	0.047*
C3B	0.8480 (3)	0.40551 (15)	0.32155 (11)	0.0386 (5)
C4B	0.7515 (2)	0.46058 (14)	0.34767 (11)	0.0353 (5)
C5B	0.4287 (2)	0.67673 (14)	0.31800 (11)	0.0348 (5)
C6B	0.3467 (3)	0.72657 (16)	0.27867 (13)	0.0444 (6)
H6B	0.2848	0.7640	0.2975	0.053*
C7B	0.3563 (3)	0.72109 (17)	0.21084 (13)	0.0496 (7)
H7B	0.2996	0.7545	0.1850	0.059*
C8B	0.4466 (3)	0.66814 (16)	0.18191 (12)	0.0437 (6)
H8B	0.4534	0.6663	0.1367	0.052*
C9B	0.5303 (2)	0.61584 (15)	0.22073 (11)	0.0348 (5)
C10B	0.6281 (2)	0.55735 (15)	0.19175 (10)	0.0359 (5)
C11B	0.7058 (2)	0.50642 (15)	0.23627 (11)	0.0336 (5)
C12B	0.6838 (2)	0.51255 (14)	0.30405 (11)	0.0313 (5)
C13B	0.5192 (2)	0.61998 (14)	0.28842 (11)	0.0328 (5)
C14B	0.7477 (2)	0.45210 (16)	0.42106 (11)	0.0396 (5)
C15B	0.8276 (3)	0.36851 (19)	0.42911 (13)	0.0539 (7)
H15B	0.7623	0.3214	0.4312	0.065*
C16B	0.9217 (3)	0.35831 (15)	0.48366 (10)	0.0792 (11)
H16C	0.8832	0.3818	0.5229	0.095*
H16D	1.0059	0.3875	0.4745	0.095*
C17B	0.8116 (3)	0.53045 (15)	0.45315 (10)	0.0629 (8)
H17D	0.9028	0.5369	0.4379	0.094*
H17E	0.8119	0.5231	0.4997	0.094*
H17F	0.7604	0.5806	0.4421	0.094*
C18B	0.6051 (3)	0.4398 (2)	0.44913 (14)	0.0662 (8)
H18D	0.5559	0.4927	0.4460	0.099*
H18E	0.6115	0.4230	0.4941	0.099*
H18F	0.5588	0.3961	0.4249	0.099*
O1WA	0.7567 (3)	0.21065 (14)	0.56948 (11)	0.0822 (8)
H1WA	0.7741	0.1639	0.5869	0.123*
H2WA	0.8243	0.2244	0.5407	0.123*
O1WB	0.2432 (2)	0.79095 (14)	0.42531 (11)	0.0745 (7)
H1WB	0.1943	0.7889	0.4620	0.112*
H2WB	0.2087	0.8328	0.4072	0.112*

	U11	U22	U33	U12	U13	U23
O1A	0.0379 (9)	0.0434 (8)	0.0296 (8)	0.0054 (8)	0.0003 (7)	0.0028 (7)
O2A	0.0608 (11)	0.0647 (11)	0.0282 (8)	0.0099 (10)	−0.0001 (8)	0.0017 (8)
O3A	0.0581 (11)	0.0559 (10)	0.0308 (8)	0.0056 (9)	0.0069 (8)	−0.0025 (8)
O4A	0.0507 (10)	0.0568 (10)	0.0378 (9)	0.0077 (9)	0.0027 (8)	0.0010 (8)
O5A	0.0495 (10)	0.0472 (9)	0.0366 (8)	0.0105 (8)	−0.0005 (7)	0.0036 (7)
O6A	0.0697 (13)	0.0465 (9)	0.0491 (10)	0.0035 (9)	0.0140 (9)	0.0032 (8)
C1A	0.0389 (12)	0.0386 (12)	0.0297 (11)	−0.0064 (10)	0.0026 (9)	−0.0022 (10)
C2A	0.0401 (13)	0.0396 (12)	0.0346 (12)	−0.0005 (11)	0.0056 (10)	−0.0039 (9)
C3A	0.0337 (12)	0.0364 (11)	0.0358 (12)	−0.0034 (10)	−0.0022 (10)	0.0030 (10)
C4A	0.0358 (12)	0.0363 (11)	0.0296 (12)	−0.0027 (10)	−0.0005 (9)	−0.0001 (9)
C5A	0.0377 (13)	0.0385 (11)	0.0371 (12)	−0.0047 (11)	0.0006 (10)	0.0021 (10)
C6A	0.0409 (14)	0.0387 (12)	0.0482 (14)	0.0029 (12)	−0.0041 (11)	−0.0003 (11)
C7A	0.0492 (15)	0.0405 (13)	0.0484 (14)	0.0062 (13)	−0.0079 (12)	0.0060 (11)
C8A	0.0475 (15)	0.0425 (12)	0.0385 (13)	−0.0009 (12)	−0.0093 (11)	0.0020 (11)
C9A	0.0388 (13)	0.0396 (13)	0.0341 (12)	−0.0045 (11)	−0.0034 (10)	0.0017 (10)
C10A	0.0368 (13)	0.0439 (12)	0.0314 (11)	−0.0035 (11)	−0.0024 (10)	0.0024 (10)
C11A	0.0351 (12)	0.0376 (11)	0.0297 (11)	−0.0067 (10)	0.0005 (9)	0.0001 (10)
C12A	0.0315 (12)	0.0353 (11)	0.0341 (12)	−0.0043 (10)	0.0012 (10)	−0.0033 (9)
C13A	0.0332 (12)	0.0358 (12)	0.0344 (11)	−0.0043 (10)	−0.0036 (9)	0.0013 (9)
C14A	0.0408 (13)	0.0441 (12)	0.0279 (11)	−0.0001 (11)	−0.0011 (9)	0.0020 (10)
C15A	0.0407 (13)	0.0451 (12)	0.0370 (12)	−0.0020 (11)	−0.0020 (10)	0.0000 (10)
C16A	0.0545 (15)	0.0507 (14)	0.0378 (13)	0.0056 (13)	−0.0074 (12)	0.0036 (11)
C17A	0.0467 (15)	0.0684 (17)	0.0435 (14)	−0.0061 (14)	0.0012 (12)	0.0105 (13)
C18A	0.0688 (19)	0.0559 (15)	0.0358 (13)	0.0049 (14)	−0.0066 (12)	−0.0031 (11)
O1B	0.0369 (9)	0.0433 (8)	0.0274 (7)	0.0066 (7)	0.0002 (6)	−0.0002 (7)
O2B	0.0573 (11)	0.0624 (11)	0.0269 (8)	0.0038 (10)	0.0001 (8)	−0.0015 (8)
O3B	0.0565 (11)	0.0537 (10)	0.0307 (8)	0.0019 (9)	0.0080 (8)	−0.0073 (8)
O4B	0.0482 (10)	0.0480 (9)	0.0339 (8)	0.0089 (8)	0.0033 (8)	−0.0014 (7)
O5B	0.0621 (12)	0.0578 (11)	0.0407 (9)	0.0249 (10)	−0.0030 (9)	0.0005 (8)
O6B	0.152 (3)	0.180 (3)	0.0829 (18)	0.119 (3)	0.0523 (19)	0.066 (2)
C1B	0.0375 (12)	0.0370 (11)	0.0323 (11)	−0.0074 (10)	0.0037 (10)	−0.0076 (9)
C2B	0.0393 (13)	0.0366 (11)	0.0426 (13)	0.0030 (11)	0.0017 (11)	−0.0058 (10)
C3B	0.0419 (13)	0.0361 (11)	0.0379 (12)	0.0043 (10)	−0.0042 (11)	−0.0019 (10)
C4B	0.0383 (12)	0.0343 (11)	0.0333 (12)	−0.0002 (10)	−0.0021 (9)	−0.0045 (9)
C5B	0.0361 (12)	0.0348 (11)	0.0336 (11)	−0.0027 (10)	−0.0001 (10)	−0.0009 (9)
C6B	0.0457 (14)	0.0386 (12)	0.0488 (14)	0.0061 (12)	−0.0013 (12)	−0.0004 (11)
C7B	0.0560 (17)	0.0451 (13)	0.0476 (15)	0.0068 (14)	−0.0128 (13)	0.0047 (12)
C8B	0.0521 (15)	0.0474 (13)	0.0315 (12)	−0.0016 (13)	−0.0073 (11)	0.0034 (11)
C9B	0.0359 (12)	0.0366 (12)	0.0320 (11)	−0.0040 (10)	−0.0048 (9)	0.0002 (9)
C10B	0.0375 (13)	0.0421 (12)	0.0280 (11)	−0.0084 (11)	0.0000 (9)	−0.0020 (10)
C11B	0.0328 (11)	0.0370 (11)	0.0310 (11)	−0.0046 (10)	−0.0012 (9)	−0.0028 (10)
C12B	0.0306 (12)	0.0325 (11)	0.0307 (11)	−0.0011 (9)	0.0015 (9)	−0.0022 (9)
C13B	0.0309 (12)	0.0319 (11)	0.0355 (12)	−0.0020 (10)	−0.0030 (9)	0.0024 (9)
C14B	0.0434 (14)	0.0447 (13)	0.0308 (12)	0.0000 (11)	−0.0027 (10)	0.0013 (10)
C15B	0.0582 (17)	0.0585 (15)	0.0449 (14)	0.0020 (14)	0.0059 (13)	0.0060 (12)
C16B	0.0600 (19)	0.128 (3)	0.0492 (17)	0.033 (2)	−0.0001 (14)	0.0274 (19)
C17B	0.093 (2)	0.0581 (16)	0.0370 (14)	−0.0074 (17)	−0.0121 (15)	−0.0035 (12)
C18B	0.0537 (17)	0.098 (2)	0.0468 (15)	0.0024 (17)	0.0042 (13)	0.0220 (16)
O1WA	0.117 (2)	0.0625 (12)	0.0666 (14)	0.0365 (14)	0.0257 (13)	0.0038 (11)
O1WB	0.0965 (18)	0.0644 (12)	0.0627 (14)	0.0328 (13)	0.0390 (12)	0.0206 (11)

O1A—C12A	1.361 (3)	O2B—C10B	1.253 (3)
O1A—C13A	1.370 (3)	O3B—C1B	1.356 (3)
O2A—C10A	1.249 (3)	O3B—H3OB	1.0564
O3A—C1A	1.354 (3)	O4B—C5B	1.360 (3)
O3A—H3OA	0.9841	O4B—H4OB	1.0223
O4A—C5A	1.355 (3)	O5B—C3B	1.363 (3)
O4A—H4OA	0.9200	O5B—C15B	1.494 (3)
O5A—C3A	1.356 (3)	O6B—C16B	1.371 (4)
O5A—C15A	1.466 (3)	O6B—H6OB	0.8200
O6A—C16A	1.431 (3)	C1B—C2B	1.381 (3)
O6A—H6OA	0.8200	C1B—C11B	1.419 (3)
C1A—C2A	1.372 (3)	C2B—C3B	1.380 (3)
C1A—C11A	1.425 (4)	C2B—H2B	0.9300
C2A—C3A	1.387 (3)	C3B—C4B	1.391 (3)
C2A—H2A	0.9300	C4B—C12B	1.380 (3)
C3A—C4A	1.389 (3)	C4B—C14B	1.510 (3)
C4A—C12A	1.377 (3)	C5B—C6B	1.382 (3)
C4A—C14A	1.519 (3)	C5B—C13B	1.397 (3)
C5A—C6A	1.380 (3)	C6B—C7B	1.395 (4)
C5A—C13A	1.399 (3)	C6B—H6B	0.9300
C6A—C7A	1.394 (4)	C7B—C8B	1.353 (4)
C6A—H6A	0.9300	C7B—H7B	0.9300
C7A—C8A	1.370 (4)	C8B—C9B	1.408 (3)
C7A—H7A	0.9300	C8B—H8B	0.9300
C8A—C9A	1.392 (3)	C9B—C13B	1.393 (3)
C8A—H8A	0.9300	C9B—C10B	1.457 (3)
C9A—C13A	1.404 (3)	C10B—C11B	1.433 (3)
C9A—C10A	1.462 (3)	C11B—C12B	1.409 (3)
C10A—C11A	1.441 (3)	C14B—C17B	1.525 (3)
C11A—C12A	1.408 (3)	C14B—C15B	1.534 (4)
C14A—C18A	1.520 (3)	C14B—C18B	1.535 (4)
C14A—C17A	1.539 (4)	C15B—C16B	1.463 (4)
C14A—C15A	1.565 (3)	C15B—H15B	0.9800
C15A—C16A	1.506 (3)	C16B—H16C	0.9633
C15A—H15A	0.9800	C16B—H16D	0.9669
C16A—H16A	0.9700	C17B—H17D	0.9600
C16A—H16B	0.9700	C17B—H17E	0.9600
C17A—H17A	0.9600	C17B—H17F	0.9600
C17A—H17B	0.9600	C18B—H18D	0.9600
C17A—H17C	0.9600	C18B—H18E	0.9600
C18A—H18A	0.9600	C18B—H18F	0.9600
C18A—H18B	0.9600	O1WA—H1WA	0.8300
C18A—H18C	0.9600	O1WA—H2WA	0.9169
O1B—C13B	1.366 (3)	O1WB—H1WB	0.8939
O1B—C12B	1.371 (3)	O1WB—H2WB	0.8249
C12A—O1A—C13A	119.90 (17)	C1B—O3B—H3OB	107.7
C1A—O3A—H3OA	106.0	C5B—O4B—H4OB	110.2
C5A—O4A—H4OA	108.4	C3B—O5B—C15B	106.26 (19)
C3A—O5A—C15A	106.59 (18)	C16B—O6B—H6OB	109.5
C16A—O6A—H6OA	109.5	O3B—C1B—C2B	119.8 (2)
O3A—C1A—C2A	119.9 (2)	O3B—C1B—C11B	118.5 (2)
O3A—C1A—C11A	118.9 (2)	C2B—C1B—C11B	121.7 (2)
C2A—C1A—C11A	121.1 (2)	C3B—C2B—C1B	116.4 (2)
C1A—C2A—C3A	117.0 (2)	C3B—C2B—H2B	121.8
C1A—C2A—H2A	121.5	C1B—C2B—H2B	121.8
C3A—C2A—H2A	121.5	O5B—C3B—C2B	122.4 (2)
O5A—C3A—C2A	122.3 (2)	O5B—C3B—C4B	112.1 (2)
O5A—C3A—C4A	113.02 (19)	C2B—C3B—C4B	125.5 (2)
C2A—C3A—C4A	124.7 (2)	C12B—C4B—C3B	116.5 (2)
C12A—C4A—C3A	117.5 (2)	C12B—C4B—C14B	133.2 (2)
C12A—C4A—C14A	133.1 (2)	C3B—C4B—C14B	110.2 (2)
C3A—C4A—C14A	109.32 (19)	O4B—C5B—C6B	123.3 (2)
O4A—C5A—C6A	123.5 (2)	O4B—C5B—C13B	118.1 (2)
O4A—C5A—C13A	118.3 (2)	C6B—C5B—C13B	118.6 (2)
C6A—C5A—C13A	118.2 (2)	C5B—C6B—C7B	120.4 (2)
C5A—C6A—C7A	121.4 (2)	C5B—C6B—H6B	119.8
C5A—C6A—H6A	119.3	C7B—C6B—H6B	119.8
C7A—C6A—H6A	119.3	C8B—C7B—C6B	121.2 (2)
C8A—C7A—C6A	120.2 (2)	C8B—C7B—H7B	119.4
C8A—C7A—H7A	119.9	C6B—C7B—H7B	119.4
C6A—C7A—H7A	119.9	C7B—C8B—C9B	119.6 (2)
C7A—C8A—C9A	120.1 (2)	C7B—C8B—H8B	120.2
C7A—C8A—H8A	119.9	C9B—C8B—H8B	120.2
C9A—C8A—H8A	119.9	C13B—C9B—C8B	119.3 (2)
C8A—C9A—C13A	119.4 (2)	C13B—C9B—C10B	119.1 (2)
C8A—C9A—C10A	121.7 (2)	C8B—C9B—C10B	121.6 (2)
C13A—C9A—C10A	118.9 (2)	O2B—C10B—C11B	122.1 (2)
O2A—C10A—C11A	122.5 (2)	O2B—C10B—C9B	121.5 (2)
O2A—C10A—C9A	121.1 (2)	C11B—C10B—C9B	116.38 (19)
C11A—C10A—C9A	116.32 (19)	C12B—C11B—C1B	118.2 (2)
C12A—C11A—C1A	118.9 (2)	C12B—C11B—C10B	120.4 (2)
C12A—C11A—C10A	120.6 (2)	C1B—C11B—C10B	121.3 (2)
C1A—C11A—C10A	120.4 (2)	O1B—C12B—C4B	116.81 (19)
O1A—C12A—C4A	117.8 (2)	O1B—C12B—C11B	121.63 (19)
O1A—C12A—C11A	121.5 (2)	C4B—C12B—C11B	121.6 (2)
C4A—C12A—C11A	120.7 (2)	O1B—C13B—C9B	123.3 (2)
O1A—C13A—C5A	116.4 (2)	O1B—C13B—C5B	115.90 (19)
O1A—C13A—C9A	122.8 (2)	C9B—C13B—C5B	120.8 (2)
C5A—C13A—C9A	120.8 (2)	C4B—C14B—C17B	110.42 (19)
C4A—C14A—C18A	114.4 (2)	C4B—C14B—C15B	99.73 (19)
C4A—C14A—C17A	109.87 (19)	C17B—C14B—C15B	115.0 (2)
C18A—C14A—C17A	109.4 (2)	C4B—C14B—C18B	114.0 (2)
C4A—C14A—C15A	98.47 (18)	C17B—C14B—C18B	108.6 (2)
C18A—C14A—C15A	110.2 (2)	C15B—C14B—C18B	109.1 (2)
C17A—C14A—C15A	114.2 (2)	C16B—C15B—O5B	106.2 (2)
O5A—C15A—C16A	107.8 (2)	C16B—C15B—C14B	120.1 (2)
O5A—C15A—C14A	106.66 (19)	O5B—C15B—C14B	106.9 (2)
C16A—C15A—C14A	120.1 (2)	C16B—C15B—H15B	107.7
O5A—C15A—H15A	107.2	O5B—C15B—H15B	107.7
C16A—C15A—H15A	107.2	C14B—C15B—H15B	107.7
C14A—C15A—H15A	107.2	O6B—C16B—C15B	115.9 (3)
O6A—C16A—C15A	113.4 (2)	O6B—C16B—H16C	108.7
O6A—C16A—H16A	108.9	C15B—C16B—H16C	110.2
C15A—C16A—H16A	108.9	O6B—C16B—H16D	102.5
O6A—C16A—H16B	108.9	C15B—C16B—H16D	110.3
C15A—C16A—H16B	108.9	H16C—C16B—H16D	108.9
H16A—C16A—H16B	107.7	C14B—C17B—H17D	109.5
C14A—C17A—H17A	109.5	C14B—C17B—H17E	109.5
C14A—C17A—H17B	109.5	H17D—C17B—H17E	109.5
H17A—C17A—H17B	109.5	C14B—C17B—H17F	109.5
C14A—C17A—H17C	109.5	H17D—C17B—H17F	109.5
H17A—C17A—H17C	109.5	H17E—C17B—H17F	109.5
H17B—C17A—H17C	109.5	C14B—C18B—H18D	109.5
C14A—C18A—H18A	109.5	C14B—C18B—H18E	109.5
C14A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
H18A—C18A—H18B	109.5	C14B—C18B—H18F	109.5
C14A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18E—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H1WA—O1WA—H2WA	109.3
C13B—O1B—C12B	118.98 (17)	H1WB—O1WB—H2WB	100.6
O3A—C1A—C2A—C3A	178.9 (2)	O3B—C1B—C2B—C3B	−177.6 (2)
C11A—C1A—C2A—C3A	−2.1 (3)	C11B—C1B—C2B—C3B	2.6 (4)
C15A—O5A—C3A—C2A	−168.9 (2)	C15B—O5B—C3B—C2B	−166.8 (3)
C15A—O5A—C3A—C4A	11.1 (3)	C15B—O5B—C3B—C4B	11.9 (3)
C1A—C2A—C3A—O5A	179.4 (2)	C1B—C2B—C3B—O5B	176.9 (2)
C1A—C2A—C3A—C4A	−0.6 (4)	C1B—C2B—C3B—C4B	−1.6 (4)
O5A—C3A—C4A—C12A	−177.4 (2)	O5B—C3B—C4B—C12B	179.9 (2)
C2A—C3A—C4A—C12A	2.6 (4)	C2B—C3B—C4B—C12B	−1.5 (4)
O5A—C3A—C4A—C14A	5.2 (3)	O5B—C3B—C4B—C14B	2.1 (3)
C2A—C3A—C4A—C14A	−174.8 (2)	C2B—C3B—C4B—C14B	−179.2 (2)
O4A—C5A—C6A—C7A	180.0 (2)	O4B—C5B—C6B—C7B	179.1 (2)
C13A—C5A—C6A—C7A	0.9 (4)	C13B—C5B—C6B—C7B	−1.1 (4)
C5A—C6A—C7A—C8A	0.4 (4)	C5B—C6B—C7B—C8B	−0.9 (4)
C6A—C7A—C8A—C9A	−1.1 (4)	C6B—C7B—C8B—C9B	1.7 (4)
C7A—C8A—C9A—C13A	0.6 (4)	C7B—C8B—C9B—C13B	−0.4 (4)
C7A—C8A—C9A—C10A	−178.5 (2)	C7B—C8B—C9B—C10B	179.5 (2)
C8A—C9A—C10A—O2A	−0.3 (4)	C13B—C9B—C10B—O2B	−178.8 (2)
C13A—C9A—C10A—O2A	−179.4 (2)	C8B—C9B—C10B—O2B	1.3 (4)
C8A—C9A—C10A—C11A	179.5 (2)	C13B—C9B—C10B—C11B	1.0 (3)
C13A—C9A—C10A—C11A	0.4 (3)	C8B—C9B—C10B—C11B	−179.0 (2)
O3A—C1A—C11A—C12A	−178.2 (2)	O3B—C1B—C11B—C12B	179.7 (2)
C2A—C1A—C11A—C12A	2.8 (3)	C2B—C1B—C11B—C12B	−0.5 (3)
O3A—C1A—C11A—C10A	1.4 (3)	O3B—C1B—C11B—C10B	0.9 (3)
C2A—C1A—C11A—C10A	−177.6 (2)	C2B—C1B—C11B—C10B	−179.3 (2)
O2A—C10A—C11A—C12A	179.4 (2)	O2B—C10B—C11B—C12B	−178.7 (2)
C9A—C10A—C11A—C12A	−0.4 (3)	C9B—C10B—C11B—C12B	1.5 (3)
O2A—C10A—C11A—C1A	−0.2 (4)	O2B—C10B—C11B—C1B	0.1 (4)
C9A—C10A—C11A—C1A	180.0 (2)	C9B—C10B—C11B—C1B	−179.7 (2)
C13A—O1A—C12A—C4A	−179.2 (2)	C13B—O1B—C12B—C4B	−176.88 (19)
C13A—O1A—C12A—C11A	0.4 (3)	C13B—O1B—C12B—C11B	2.7 (3)
C3A—C4A—C12A—O1A	177.84 (19)	C3B—C4B—C12B—O1B	−176.83 (19)
C14A—C4A—C12A—O1A	−5.5 (4)	C14B—C4B—C12B—O1B	0.3 (4)
C3A—C4A—C12A—C11A	−1.8 (3)	C3B—C4B—C12B—C11B	3.6 (3)
C14A—C4A—C12A—C11A	174.9 (2)	C14B—C4B—C12B—C11B	−179.2 (2)
C1A—C11A—C12A—O1A	179.6 (2)	C1B—C11B—C12B—O1B	177.8 (2)
C10A—C11A—C12A—O1A	0.0 (3)	C10B—C11B—C12B—O1B	−3.4 (3)
C1A—C11A—C12A—C4A	−0.8 (3)	C1B—C11B—C12B—C4B	−2.7 (3)
C10A—C11A—C12A—C4A	179.6 (2)	C10B—C11B—C12B—C4B	176.1 (2)
C12A—O1A—C13A—C5A	179.80 (19)	C12B—O1B—C13B—C9B	0.0 (3)
C12A—O1A—C13A—C9A	−0.4 (3)	C12B—O1B—C13B—C5B	179.70 (18)
O4A—C5A—C13A—O1A	−0.7 (3)	C8B—C9B—C13B—O1B	178.1 (2)
C6A—C5A—C13A—O1A	178.5 (2)	C10B—C9B—C13B—O1B	−1.8 (3)
O4A—C5A—C13A—C9A	179.5 (2)	C8B—C9B—C13B—C5B	−1.6 (3)
C6A—C5A—C13A—C9A	−1.4 (3)	C10B—C9B—C13B—C5B	178.5 (2)
C8A—C9A—C13A—O1A	−179.2 (2)	O4B—C5B—C13B—O1B	2.4 (3)
C10A—C9A—C13A—O1A	0.0 (3)	C6B—C5B—C13B—O1B	−177.4 (2)
C8A—C9A—C13A—C5A	0.6 (3)	O4B—C5B—C13B—C9B	−177.9 (2)
C10A—C9A—C13A—C5A	179.8 (2)	C6B—C5B—C13B—C9B	2.3 (3)
C12A—C4A—C14A—C18A	48.8 (4)	C12B—C4B—C14B—C17B	−70.3 (3)
C3A—C4A—C14A—C18A	−134.4 (2)	C3B—C4B—C14B—C17B	106.9 (2)
C12A—C4A—C14A—C17A	−74.8 (3)	C12B—C4B—C14B—C15B	168.3 (3)
C3A—C4A—C14A—C17A	102.1 (2)	C3B—C4B—C14B—C15B	−14.4 (3)
C12A—C4A—C14A—C15A	165.6 (3)	C12B—C4B—C14B—C18B	52.2 (4)
C3A—C4A—C14A—C15A	−17.5 (2)	C3B—C4B—C14B—C18B	−130.5 (3)
C3A—O5A—C15A—C16A	−152.6 (2)	C3B—O5B—C15B—C16B	−150.5 (2)
C3A—O5A—C15A—C14A	−22.4 (2)	C3B—O5B—C15B—C14B	−21.1 (3)
C4A—C14A—C15A—O5A	23.6 (2)	C4B—C14B—C15B—C16B	141.8 (2)
C18A—C14A—C15A—O5A	143.6 (2)	C17B—C14B—C15B—C16B	23.8 (3)
C17A—C14A—C15A—O5A	−92.7 (2)	C18B—C14B—C15B—C16B	−98.5 (3)
C4A—C14A—C15A—C16A	146.4 (2)	C4B—C14B—C15B—O5B	20.9 (3)
C18A—C14A—C15A—C16A	−93.5 (3)	C17B—C14B—C15B—O5B	−97.2 (3)
C17A—C14A—C15A—C16A	30.1 (3)	C18B—C14B—C15B—O5B	140.6 (2)
O5A—C15A—C16A—O6A	48.9 (3)	O5B—C15B—C16B—O6B	−73.8 (3)
C14A—C15A—C16A—O6A	−73.3 (3)	C14B—C15B—C16B—O6B	165.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3A—H3OA···O2A	0.98	1.62	2.530 (3)	152
O4A—H4OA···O1WA	0.92	1.75	2.672 (3)	175
O6A—H6OA···O4Bi	0.82	2.12	2.918 (3)	165
O3B—H3OB···O2B	1.06	1.57	2.529 (3)	148
O4B—H4OB···O1WB	1.02	1.62	2.639 (3)	175
O6B—H6OB···O4Aii	0.82	2.25	3.059 (4)	167
O1WA—H1WA···O3Aiii	0.83	2.06	2.889 (3)	173
O1WA—H2WA···O6B	0.92	1.84	2.737 (5)	165
O1WB—H1WB···O6A	0.89	1.86	2.691 (3)	153
O1WB—H2WB···O3Biv	0.82	2.06	2.868 (3)	164
C16B—H16C···O2Bv	0.96	2.46	3.389 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3A—H3OA⋯O2A	0.98	1.62	2.530 (3)	152
O4A—H4OA⋯O1WA	0.92	1.75	2.672 (3)	175
O6A—H6OA⋯O4Bi	0.82	2.12	2.918 (3)	165
O3B—H3OB⋯O2B	1.06	1.57	2.529 (3)	148
O4B—H4OB⋯O1WB	1.02	1.62	2.639 (3)	175
O6B—H6OB⋯O4Aii	0.82	2.25	3.059 (4)	167
O1WA—H1WA⋯O3Aiii	0.83	2.06	2.889 (3)	173
O1WA—H2WA⋯O6B	0.92	1.84	2.737 (5)	165
O1WB—H1WB⋯O6A	0.89	1.86	2.691 (3)	153
O1WB—H2WB⋯O3Biv	0.82	2.06	2.868 (3)	164
C16B—H16C⋯O2Bv	0.96	2.46	3.389 (3)	163

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