Swietenolide monohydrate.

The title compound, a natural b,d-seco-limonoid, C(27)H(34)O(8)·H(2)O, and known as Swietenolide monohydrate, has been isolated from S. macrophylla King. In the molecular structure, the four fused six-membered rings adopt twist-boat (ring A), approximate chair (ring B), envelope (ring C) and half-chair (ring D) conformations. The attached furan ring is essentially planar. O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions connect the mol-ecules into a two-dimensional network parallel to the (100) plane. C-H⋯π inter-actions are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For related structures, see, for example: Fowles et al. (2007 ▶); Solomon et al. (2003 ▶). For the bioactivities of Swietenolide, see, for example: Chan et al. (1976 ▶); Jean et al. (2000 ▶); Kipassa et al. (2008 ▶); Munoz et al. (2000 ▶); Soediro et al. (1990 ▶).

Experimental

Crystal data

C27H34O8·H2O

M = 504.56

Monoclinic,

a = 11.5897 (1) Å

b = 8.8972 (1) Å

c = 11.7397 (1) Å

β = 90.571 (1)°

V = 1210.49 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100.0 (1) K

0.51 × 0.26 × 0.15 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.949, T max = 0.985

29214 measured reflections

3748 independent reflections

3473 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.102

S = 1.06

3748 reflections

336 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.60 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017431/is2302sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017431/is2302Isup2.hkl

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

C27H34O8·H2O	F000 = 540
Mr = 504.56	Dx = 1.384 Mg m−3
Monoclinic, P21	Melting point = 494–495 K
Hall symbol: P 2yb	Mo Kα radiation λ = 0.71073 Å
a = 11.5897 (1) Å	Cell parameters from 3748 reflections
b = 8.8972 (1) Å	θ = 1.7–30.0º
c = 11.7397 (1) Å	µ = 0.10 mm−1
β = 90.571 (1)º	T = 100.0 (1) K
V = 1210.49 (2) Å3	Block, white
Z = 2	0.51 × 0.26 × 0.15 mm

Bruker SMART APEX2 CCD area-detector diffractometer	3748 independent reflections
Radiation source: fine-focus sealed tube	3473 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 1.7º
ω scans	h = −16→16
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −12→12
Tmin = 0.949, Tmax = 0.985	l = −16→16
29214 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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0598P)2 + 0.2523P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
3748 reflections	Δρmax = 0.60 e Å−3
336 parameters	Δρmin = −0.30 e Å−3
3 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.14701 (12)	0.92970 (17)	−0.07457 (11)	0.0202 (3)
O2	0.15836 (12)	0.51412 (17)	0.17362 (12)	0.0215 (3)
H2A	0.1147	0.4506	0.1998	0.032*
O3	0.59393 (12)	0.49859 (16)	0.32385 (11)	0.0178 (3)
O4	0.59920 (14)	0.30211 (18)	0.21195 (12)	0.0249 (3)
O5	0.05304 (14)	1.03697 (19)	0.33979 (13)	0.0281 (3)
H5A	0.0630	1.1155	0.3046	0.042*
O6	0.09281 (15)	0.89163 (19)	0.52750 (12)	0.0286 (3)
O7	0.23735 (14)	0.75766 (18)	0.45318 (12)	0.0254 (3)
O8	0.63962 (14)	0.8207 (2)	0.61555 (13)	0.0307 (4)
C1	0.09219 (16)	0.6289 (2)	0.11769 (16)	0.0174 (3)
H1A	0.0221	0.5819	0.0869	0.021*
C2	0.05482 (16)	0.7551 (2)	0.19977 (16)	0.0176 (3)
C3	0.16498 (16)	0.8467 (2)	0.22950 (15)	0.0157 (3)
H3A	0.2238	0.7719	0.2495	0.019*
C4	0.21274 (15)	0.9309 (2)	0.12163 (15)	0.0148 (3)
C5	0.16505 (15)	0.8578 (2)	0.01271 (16)	0.0168 (3)
C6	0.16287 (16)	0.6893 (2)	0.01549 (16)	0.0165 (3)
H6A	0.1268	0.6532	−0.0552	0.020*
C7	0.29236 (15)	0.6434 (2)	0.01551 (15)	0.0160 (3)
H7A	0.2981	0.5369	0.0322	0.019*
H7B	0.3227	0.6592	−0.0602	0.019*
C8	0.36654 (15)	0.7287 (2)	0.10020 (15)	0.0153 (3)
C9	0.34658 (16)	0.8973 (2)	0.10259 (16)	0.0162 (3)
H9A	0.3632	0.9326	0.0254	0.019*
C10	0.43068 (17)	0.9823 (2)	0.18131 (17)	0.0199 (4)
H10A	0.4973	1.0128	0.1376	0.024*
H10B	0.3932	1.0726	0.2086	0.024*
C11	0.47154 (16)	0.8905 (2)	0.28303 (16)	0.0189 (4)
H11A	0.4065	0.8699	0.3320	0.023*
H11B	0.5275	0.9485	0.3265	0.023*
C12	0.52646 (15)	0.7415 (2)	0.24632 (15)	0.0150 (3)
C13	0.44704 (16)	0.6598 (2)	0.16417 (15)	0.0152 (3)
C14	0.46133 (16)	0.4901 (2)	0.15927 (15)	0.0171 (3)
H14A	0.3891	0.4444	0.1820	0.021*
H14B	0.4744	0.4619	0.0806	0.021*
C15	0.55661 (17)	0.4233 (2)	0.23106 (16)	0.0188 (4)
C16	0.53698 (15)	0.6395 (2)	0.35230 (15)	0.0156 (3)
H16A	0.4589	0.6161	0.3783	0.019*
C17	0.60331 (16)	0.7034 (2)	0.45044 (16)	0.0173 (3)
C18	0.72511 (18)	0.7205 (3)	0.46494 (18)	0.0241 (4)
H18A	0.7817	0.6882	0.4150	0.029*
C19	0.74236 (19)	0.7921 (3)	0.56442 (19)	0.0246 (4)
H19A	0.8142	0.8184	0.5942	0.030*
C20	0.55640 (19)	0.7630 (3)	0.54466 (18)	0.0284 (5)
H20A	0.4778	0.7646	0.5596	0.034*
C21	−0.04291 (17)	0.8461 (3)	0.14183 (18)	0.0234 (4)
H21A	−0.1041	0.7793	0.1193	0.035*
H21B	−0.0134	0.8963	0.0759	0.035*
H21C	−0.0720	0.9192	0.1944	0.035*
C22	0.00204 (18)	0.6826 (2)	0.30642 (17)	0.0227 (4)
H22A	−0.0592	0.6160	0.2839	0.034*
H22B	−0.0280	0.7598	0.3550	0.034*
H22C	0.0605	0.6270	0.3468	0.034*
C23	0.15457 (18)	0.9491 (2)	0.33581 (15)	0.0196 (4)
H23A	0.2207	1.0177	0.3366	0.024*
C24	0.1553 (2)	0.8629 (2)	0.44867 (17)	0.0238 (4)
C25	0.2369 (2)	0.6683 (3)	0.55726 (19)	0.0297 (5)
H25A	0.2941	0.5906	0.5523	0.045*
H25B	0.1622	0.6236	0.5667	0.045*
H25C	0.2541	0.7318	0.6213	0.045*
C26	0.19021 (17)	1.0997 (2)	0.11612 (16)	0.0189 (4)
H26A	0.1087	1.1175	0.1091	0.028*
H26B	0.2287	1.1414	0.0513	0.028*
H26C	0.2190	1.1465	0.1844	0.028*
C27	0.64551 (17)	0.7674 (2)	0.19245 (17)	0.0207 (4)
H27A	0.6370	0.8298	0.1262	0.031*
H27B	0.6782	0.6725	0.1710	0.031*
H27C	0.6956	0.8161	0.2466	0.031*
O1W	0.01243 (14)	0.81352 (19)	0.74563 (13)	0.0267 (3)
H1W1	0.058 (2)	0.838 (4)	0.798 (2)	0.040*
H2W1	0.044 (2)	0.825 (4)	0.6819 (14)	0.040*

	U11	U22	U33	U12	U13	U23
O1	0.0206 (6)	0.0259 (7)	0.0140 (6)	0.0037 (6)	−0.0005 (5)	0.0029 (5)
O2	0.0224 (7)	0.0211 (7)	0.0212 (7)	0.0004 (6)	0.0047 (5)	0.0050 (6)
O3	0.0198 (6)	0.0185 (6)	0.0152 (6)	0.0036 (5)	0.0005 (5)	−0.0004 (5)
O4	0.0310 (8)	0.0233 (7)	0.0205 (7)	0.0089 (6)	−0.0003 (6)	−0.0039 (6)
O5	0.0347 (9)	0.0249 (8)	0.0249 (7)	0.0099 (7)	0.0088 (6)	0.0019 (6)
O6	0.0422 (9)	0.0274 (8)	0.0161 (7)	0.0006 (7)	0.0064 (6)	−0.0004 (6)
O7	0.0362 (8)	0.0245 (7)	0.0155 (6)	0.0021 (7)	0.0004 (6)	0.0027 (6)
O8	0.0296 (8)	0.0385 (9)	0.0238 (7)	0.0001 (7)	−0.0045 (6)	−0.0118 (7)
C1	0.0154 (8)	0.0208 (9)	0.0160 (8)	−0.0025 (7)	0.0013 (6)	0.0009 (7)
C2	0.0150 (8)	0.0217 (9)	0.0162 (8)	−0.0008 (7)	0.0025 (6)	0.0003 (7)
C3	0.0187 (8)	0.0174 (8)	0.0109 (7)	0.0001 (6)	0.0019 (6)	0.0009 (6)
C4	0.0157 (8)	0.0172 (8)	0.0115 (7)	0.0016 (6)	0.0018 (6)	0.0005 (6)
C5	0.0114 (7)	0.0223 (9)	0.0167 (8)	0.0011 (7)	0.0014 (6)	0.0006 (7)
C6	0.0151 (8)	0.0214 (9)	0.0130 (8)	−0.0011 (7)	−0.0002 (6)	−0.0002 (7)
C7	0.0157 (8)	0.0194 (8)	0.0129 (7)	−0.0005 (7)	0.0014 (6)	−0.0014 (6)
C8	0.0138 (8)	0.0175 (8)	0.0145 (8)	−0.0005 (6)	0.0028 (6)	−0.0004 (6)
C9	0.0158 (8)	0.0169 (8)	0.0160 (8)	−0.0009 (6)	0.0004 (6)	0.0012 (6)
C10	0.0183 (8)	0.0161 (8)	0.0252 (9)	−0.0013 (7)	−0.0041 (7)	0.0018 (7)
C11	0.0178 (8)	0.0177 (9)	0.0211 (9)	0.0002 (7)	−0.0033 (7)	−0.0019 (7)
C12	0.0130 (7)	0.0167 (8)	0.0154 (8)	−0.0001 (6)	0.0001 (6)	0.0007 (6)
C13	0.0145 (8)	0.0173 (8)	0.0138 (8)	−0.0003 (6)	0.0029 (6)	−0.0008 (6)
C14	0.0193 (8)	0.0180 (8)	0.0141 (8)	0.0024 (7)	0.0015 (6)	−0.0005 (6)
C15	0.0212 (9)	0.0210 (9)	0.0143 (8)	0.0024 (7)	0.0027 (6)	0.0004 (7)
C16	0.0146 (8)	0.0182 (8)	0.0141 (8)	0.0011 (6)	0.0014 (6)	−0.0007 (6)
C17	0.0161 (8)	0.0187 (8)	0.0170 (8)	0.0011 (7)	−0.0004 (6)	0.0006 (7)
C18	0.0179 (9)	0.0307 (11)	0.0237 (10)	0.0016 (8)	−0.0014 (7)	0.0001 (8)
C19	0.0223 (10)	0.0262 (10)	0.0253 (10)	−0.0013 (8)	−0.0072 (8)	0.0019 (8)
C20	0.0219 (9)	0.0410 (12)	0.0223 (10)	0.0003 (9)	0.0001 (7)	−0.0116 (9)
C21	0.0162 (8)	0.0321 (11)	0.0218 (9)	0.0018 (8)	0.0020 (7)	0.0011 (8)
C22	0.0249 (10)	0.0241 (10)	0.0193 (9)	−0.0040 (8)	0.0062 (8)	0.0008 (7)
C23	0.0273 (10)	0.0183 (8)	0.0134 (8)	0.0012 (7)	0.0041 (7)	0.0004 (7)
C24	0.0360 (11)	0.0195 (9)	0.0158 (9)	−0.0037 (8)	0.0003 (7)	−0.0007 (7)
C25	0.0349 (12)	0.0294 (11)	0.0248 (10)	0.0016 (9)	−0.0009 (9)	0.0061 (9)
C26	0.0221 (9)	0.0189 (8)	0.0156 (8)	0.0026 (7)	0.0019 (7)	0.0025 (7)
C27	0.0169 (8)	0.0252 (9)	0.0200 (9)	−0.0019 (7)	0.0031 (7)	0.0035 (8)
O1W	0.0309 (8)	0.0285 (8)	0.0209 (7)	−0.0014 (7)	0.0036 (6)	−0.0020 (6)

O1—C5	1.224 (2)	C11—C12	1.534 (3)
O2—C1	1.432 (2)	C11—H11A	0.9700
O2—H2A	0.8200	C11—H11B	0.9700
O3—C15	1.346 (2)	C12—C13	1.513 (3)
O3—C16	1.457 (2)	C12—C27	1.541 (3)
O4—C15	1.208 (2)	C12—C16	1.544 (3)
O5—C23	1.414 (2)	C13—C14	1.521 (3)
O5—H5A	0.8200	C14—C15	1.504 (3)
O6—C24	1.208 (3)	C14—H14A	0.9700
O7—C24	1.335 (3)	C14—H14B	0.9700
O7—C25	1.458 (3)	C16—C17	1.491 (3)
O8—C19	1.363 (3)	C16—H16A	0.9800
O8—C20	1.368 (3)	C17—C20	1.346 (3)
C1—C2	1.545 (3)	C17—C18	1.428 (3)
C1—C6	1.555 (3)	C18—C19	1.344 (3)
C1—H1A	0.9800	C18—H18A	0.9300
C2—C22	1.540 (3)	C19—H19A	0.9300
C2—C21	1.544 (3)	C20—H20A	0.9300
C2—C3	1.552 (3)	C21—H21A	0.9600
C3—C23	1.551 (3)	C21—H21B	0.9600
C3—C4	1.577 (2)	C21—H21C	0.9600
C3—H3A	0.9800	C22—H22A	0.9600
C4—C26	1.526 (3)	C22—H22B	0.9600
C4—C5	1.533 (3)	C22—H22C	0.9600
C4—C9	1.598 (2)	C23—C24	1.531 (3)
C5—C6	1.500 (3)	C23—H23A	0.9800
C6—C7	1.555 (3)	C25—H25A	0.9600
C6—H6A	0.9800	C25—H25B	0.9600
C7—C8	1.512 (3)	C25—H25C	0.9600
C7—H7A	0.9700	C26—H26A	0.9600
C7—H7B	0.9700	C26—H26B	0.9600
C8—C13	1.340 (3)	C26—H26C	0.9600
C8—C9	1.518 (3)	C27—H27A	0.9600
C9—C10	1.536 (3)	C27—H27B	0.9600
C9—H9A	0.9800	C27—H27C	0.9600
C10—C11	1.518 (3)	O1W—H1W1	0.834 (10)
C10—H10A	0.9700	O1W—H2W1	0.843 (10)
C10—H10B	0.9700
C1—O2—H2A	109.5	C8—C13—C12	123.60 (17)
C15—O3—C16	118.08 (15)	C8—C13—C14	120.57 (17)
C23—O5—H5A	109.5	C12—C13—C14	115.82 (16)
C24—O7—C25	114.02 (17)	C15—C14—C13	116.77 (17)
C19—O8—C20	106.00 (16)	C15—C14—H14A	108.1
O2—C1—C2	112.61 (15)	C13—C14—H14A	108.1
O2—C1—C6	108.45 (15)	C15—C14—H14B	108.1
C2—C1—C6	112.51 (16)	C13—C14—H14B	108.1
O2—C1—H1A	107.7	H14A—C14—H14B	107.3
C2—C1—H1A	107.7	O4—C15—O3	117.75 (18)
C6—C1—H1A	107.7	O4—C15—C14	123.19 (18)
C22—C2—C21	106.37 (16)	O3—C15—C14	119.02 (16)
C22—C2—C1	108.60 (16)	O3—C16—C17	105.89 (15)
C21—C2—C1	108.38 (15)	O3—C16—C12	110.70 (14)
C22—C2—C3	111.68 (15)	C17—C16—C12	115.75 (16)
C21—C2—C3	114.95 (17)	O3—C16—H16A	108.1
C1—C2—C3	106.68 (14)	C17—C16—H16A	108.1
C23—C3—C2	114.79 (15)	C12—C16—H16A	108.1
C23—C3—C4	113.45 (15)	C20—C17—C18	105.48 (18)
C2—C3—C4	111.33 (14)	C20—C17—C16	125.14 (18)
C23—C3—H3A	105.4	C18—C17—C16	129.34 (17)
C2—C3—H3A	105.4	C19—C18—C17	107.01 (19)
C4—C3—H3A	105.4	C19—C18—H18A	126.5
C26—C4—C5	108.80 (15)	C17—C18—H18A	126.5
C26—C4—C3	116.15 (15)	C18—C19—O8	110.39 (19)
C5—C4—C3	109.99 (15)	C18—C19—H19A	124.8
C26—C4—C9	110.15 (15)	O8—C19—H19A	124.8
C5—C4—C9	98.41 (13)	C17—C20—O8	111.09 (19)
C3—C4—C9	111.86 (14)	C17—C20—H20A	124.5
O1—C5—C6	122.52 (18)	O8—C20—H20A	124.5
O1—C5—C4	122.26 (17)	C2—C21—H21A	109.5
C6—C5—C4	114.33 (16)	C2—C21—H21B	109.5
C5—C6—C7	104.25 (15)	H21A—C21—H21B	109.5
C5—C6—C1	111.81 (16)	C2—C21—H21C	109.5
C7—C6—C1	115.12 (16)	H21A—C21—H21C	109.5
C5—C6—H6A	108.5	H21B—C21—H21C	109.5
C7—C6—H6A	108.5	C2—C22—H22A	109.5
C1—C6—H6A	108.5	C2—C22—H22B	109.5
C8—C7—C6	114.23 (15)	H22A—C22—H22B	109.5
C8—C7—H7A	108.7	C2—C22—H22C	109.5
C6—C7—H7A	108.7	H22A—C22—H22C	109.5
C8—C7—H7B	108.7	H22B—C22—H22C	109.5
C6—C7—H7B	108.7	O5—C23—C24	104.23 (15)
H7A—C7—H7B	107.6	O5—C23—C3	115.01 (16)
C13—C8—C7	121.79 (17)	C24—C23—C3	113.71 (16)
C13—C8—C9	123.16 (17)	O5—C23—H23A	107.9
C7—C8—C9	114.99 (16)	C24—C23—H23A	107.9
C8—C9—C10	113.69 (16)	C3—C23—H23A	107.9
C8—C9—C4	109.64 (15)	O6—C24—O7	123.39 (19)
C10—C9—C4	115.77 (15)	O6—C24—C23	124.0 (2)
C8—C9—H9A	105.6	O7—C24—C23	112.54 (17)
C10—C9—H9A	105.6	O7—C25—H25A	109.5
C4—C9—H9A	105.6	O7—C25—H25B	109.5
C11—C10—C9	113.56 (16)	H25A—C25—H25B	109.5
C11—C10—H10A	108.9	O7—C25—H25C	109.5
C9—C10—H10A	108.9	H25A—C25—H25C	109.5
C11—C10—H10B	108.9	H25B—C25—H25C	109.5
C9—C10—H10B	108.9	C4—C26—H26A	109.5
H10A—C10—H10B	107.7	C4—C26—H26B	109.5
C10—C11—C12	111.75 (16)	H26A—C26—H26B	109.5
C10—C11—H11A	109.3	C4—C26—H26C	109.5
C12—C11—H11A	109.3	H26A—C26—H26C	109.5
C10—C11—H11B	109.3	H26B—C26—H26C	109.5
C12—C11—H11B	109.3	C12—C27—H27A	109.5
H11A—C11—H11B	107.9	C12—C27—H27B	109.5
C13—C12—C11	110.05 (15)	H27A—C27—H27B	109.5
C13—C12—C27	110.61 (15)	C12—C27—H27C	109.5
C11—C12—C27	111.21 (16)	H27A—C27—H27C	109.5
C13—C12—C16	105.90 (15)	H27B—C27—H27C	109.5
C11—C12—C16	108.13 (14)	H1W1—O1W—H2W1	110 (3)
C27—C12—C16	110.78 (15)
O2—C1—C2—C22	−48.6 (2)	C10—C11—C12—C13	−50.7 (2)
C6—C1—C2—C22	−171.55 (16)	C10—C11—C12—C27	72.3 (2)
O2—C1—C2—C21	−163.78 (15)	C10—C11—C12—C16	−165.89 (15)
C6—C1—C2—C21	73.28 (19)	C7—C8—C13—C12	177.37 (16)
O2—C1—C2—C3	71.90 (18)	C9—C8—C13—C12	0.4 (3)
C6—C1—C2—C3	−51.0 (2)	C7—C8—C13—C14	−4.0 (3)
C22—C2—C3—C23	−44.9 (2)	C9—C8—C13—C14	178.97 (17)
C21—C2—C3—C23	76.4 (2)	C11—C12—C13—C8	23.8 (2)
C1—C2—C3—C23	−163.39 (15)	C27—C12—C13—C8	−99.5 (2)
C22—C2—C3—C4	−175.47 (16)	C16—C12—C13—C8	140.46 (17)
C21—C2—C3—C4	−54.2 (2)	C11—C12—C13—C14	−154.82 (15)
C1—C2—C3—C4	66.01 (19)	C27—C12—C13—C14	81.9 (2)
C23—C3—C4—C26	−26.9 (2)	C16—C12—C13—C14	−38.18 (19)
C2—C3—C4—C26	104.35 (19)	C8—C13—C14—C15	177.96 (16)
C23—C3—C4—C5	−151.03 (16)	C12—C13—C14—C15	−3.4 (2)
C2—C3—C4—C5	−19.7 (2)	C16—O3—C15—O4	−175.46 (16)
C23—C3—C4—C9	100.69 (18)	C16—O3—C15—C14	2.0 (2)
C2—C3—C4—C9	−128.02 (16)	C13—C14—C15—O4	−157.87 (18)
C26—C4—C5—O1	20.6 (2)	C13—C14—C15—O3	24.8 (2)
C3—C4—C5—O1	148.82 (17)	C15—O3—C16—C17	−174.57 (15)
C9—C4—C5—O1	−94.16 (19)	C15—O3—C16—C12	−48.4 (2)
C26—C4—C5—C6	−169.93 (15)	C13—C12—C16—O3	64.86 (17)
C3—C4—C5—C6	−41.7 (2)	C11—C12—C16—O3	−177.22 (14)
C9—C4—C5—C6	75.35 (17)	C27—C12—C16—O3	−55.1 (2)
O1—C5—C6—C7	101.4 (2)	C13—C12—C16—C17	−174.66 (15)
C4—C5—C6—C7	−68.06 (18)	C11—C12—C16—C17	−56.7 (2)
O1—C5—C6—C1	−133.60 (18)	C27—C12—C16—C17	65.4 (2)
C4—C5—C6—C1	56.9 (2)	O3—C16—C17—C20	−135.1 (2)
O2—C1—C6—C5	−132.57 (17)	C12—C16—C17—C20	101.9 (2)
C2—C1—C6—C5	−7.3 (2)	O3—C16—C17—C18	47.3 (3)
O2—C1—C6—C7	−13.8 (2)	C12—C16—C17—C18	−75.7 (3)
C2—C1—C6—C7	111.39 (18)	C20—C17—C18—C19	−1.6 (3)
C5—C6—C7—C8	47.4 (2)	C16—C17—C18—C19	176.3 (2)
C1—C6—C7—C8	−75.5 (2)	C17—C18—C19—O8	0.7 (3)
C6—C7—C8—C13	137.38 (17)	C20—O8—C19—C18	0.5 (3)
C6—C7—C8—C9	−45.4 (2)	C18—C17—C20—O8	2.0 (3)
C13—C8—C9—C10	2.5 (3)	C16—C17—C20—O8	−176.02 (19)
C7—C8—C9—C10	−174.69 (15)	C19—O8—C20—C17	−1.6 (3)
C13—C8—C9—C4	−128.88 (17)	C2—C3—C23—O5	−46.9 (2)
C7—C8—C9—C4	54.0 (2)	C4—C3—C23—O5	82.7 (2)
C26—C4—C9—C8	−176.16 (16)	C2—C3—C23—C24	73.2 (2)
C5—C4—C9—C8	−62.51 (17)	C4—C3—C23—C24	−157.22 (17)
C3—C4—C9—C8	53.1 (2)	C25—O7—C24—O6	6.5 (3)
C26—C4—C9—C10	53.6 (2)	C25—O7—C24—C23	−177.14 (18)
C5—C4—C9—C10	167.24 (15)	O5—C23—C24—O6	−12.4 (3)
C3—C4—C9—C10	−77.2 (2)	C3—C23—C24—O6	−138.4 (2)
C8—C9—C10—C11	−30.4 (2)	O5—C23—C24—O7	171.26 (17)
C4—C9—C10—C11	97.84 (19)	C3—C23—C24—O7	45.3 (2)
C9—C10—C11—C12	55.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1Wi	0.82	2.02	2.835 (2)	171
O5—H5A···O1Wii	0.82	2.05	2.760 (2)	144
O1W—H1W1···O1iii	0.84 (2)	1.98 (3)	2.809 (2)	169 (3)
O1W—H2W1···O6	0.842 (19)	1.994 (19)	2.821 (2)	167 (3)
C1—H1A···O1iv	0.98	2.39	3.325 (2)	160
C3—H3A···O2	0.98	2.57	3.032 (2)	109
C3—H3A···O7	0.98	2.40	2.861 (2)	108
C7—H7A···O2	0.97	2.34	2.690 (2)	100
C7—H7B···O4v	0.97	2.38	3.282 (2)	155
C21—H21B···O1	0.96	2.59	3.459 (2)	150
C21—H21C···O5	0.96	2.46	3.077 (3)	122
C27—H27B···O3	0.96	2.57	2.911 (2)	101
C23—H23A···Cg1vi	0.98	3.04	3.884 (2)	146
C25—H25A···Cg1vii	0.96	3.15	3.981 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1Wi	0.82	2.02	2.835 (2)	171
O5—H5A⋯O1Wii	0.82	2.05	2.760 (2)	144
O1W—H1W1⋯O1iii	0.84 (2)	1.98 (3)	2.809 (2)	169 (3)
O1W—H2W1⋯O6	0.842 (19)	1.994 (19)	2.821 (2)	167 (3)
C1—H1A⋯O1iv	0.98	2.38	3.325 (2)	160
C3—H3A⋯O2	0.98	2.57	3.032 (2)	109
C3—H3A⋯O7	0.98	2.40	2.861 (2)	108
C7—H7A⋯O2	0.97	2.34	2.690 (2)	100
C7—H7B⋯O4v	0.97	2.38	3.282 (2)	155
C21—H21B⋯O1	0.96	2.59	3.459 (2)	150
C21—H21C⋯O5	0.96	2.46	3.077 (3)	122
C27—H27B⋯O3	0.96	2.57	2.911 (2)	101
C23—H23A⋯Cg1vi	0.98	3.04	3.884 (2)	146
C25—H25A⋯Cg1vii	0.96	3.15	3.981 (3)	146

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) . Cg1 is the centroid of the C17–C20/O8 furan ring.