Xyloccensin L.

The title compound, C(32)H(40)O(10), also known as xyloccensin L [systematic name: (1R,4aR,4bS,5aR,6aR,9R,10S,10aS,10bR,2aR,13R)-1-(furan-3-yl)-6a-hy-droxy-10-(2-meth-oxy-2-oxoeth-yl)-9,10a,12a-trimethyl-3-oxododeca-hydro-1H,3H,5aH-6,9-methano-isochromeno[6,5-f]oxireno[g]chromen-13-yl (2E)-2-methyl-but-2-enoate], is a limonoid with a C1-C29 oxygen bridge: this is the first report of the X-ray crystal structure of such a limonoid. Two fused pyran rings and two cyclo-hexane rings adopt boat conformations, while another cyclo-hexane ring and the d-lactone ring are in half-chair conformations. The mol-ecular structure is stabilized by intra-molecular O-H⋯O hydrogen bonding.

Related literature

The title compound was isolated from seeds of an Indian mangrove, Xylocarpus moluccensis, collected in the mangrove wetlands of the Godavari estuary, Andhra Pradesh. For previous investigations of the seeds of Xylocarpus granatum and X. moluccensis, see: Kubo et al. (1976 ▶); Ng et al. (1979 ▶); Alvi et al. (1991 ▶); Kokpol et al. (1996 ▶); Mulholland et al. (2000 ▶). For our group’s work in this field, see: Wu et al. (2004a ▶,b ▶, 2005 ▶, 2008a ▶,b ▶).

Experimental

Crystal data

C32H40O10

M = 584.64

Orthorhombic,

a = 8.3859 (4) Å

b = 11.0454 (5) Å

c = 31.0799 (13) Å

V = 2878.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 110 K

0.46 × 0.44 × 0.25 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.956, T max = 0.976

14701 measured reflections

3569 independent reflections

3202 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.03

3569 reflections

386 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 .

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810028527/ez2224sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028527/ez2224Isup2.hkl

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

C32H40O10	F(000) = 1248
Mr = 584.64	Dx = 1.349 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7947 reflections
a = 8.3859 (4) Å	θ = 2.3–27.0°
b = 11.0454 (5) Å	µ = 0.10 mm−1
c = 31.0799 (13) Å	T = 110 K
V = 2878.8 (2) Å3	Block, colorless
Z = 4	0.46 × 0.44 × 0.25 mm

Bruker SMART 1000 CCD diffractometer	3569 independent reflections
Radiation source: fine-focus sealed tube	3202 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→8
Tmin = 0.956, Tmax = 0.976	k = −11→14
14701 measured reflections	l = −39→29

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0574P)2 + 0.880P] where P = (Fo2 + 2Fc2)/3
3569 reflections	(Δ/σ)max = 0.002
386 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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
C1	0.5981 (3)	0.5741 (2)	0.22231 (7)	0.0195 (4)
C2	0.7232 (3)	0.6275 (2)	0.19155 (7)	0.0182 (4)
H2	0.7917	0.6848	0.2082	0.022*
C3	0.6325 (3)	0.7006 (2)	0.15695 (7)	0.0189 (5)
H3	0.6422	0.7889	0.1635	0.023*
C4	0.4563 (3)	0.6652 (2)	0.15701 (7)	0.0179 (4)
C5	0.4478 (3)	0.5242 (2)	0.15534 (7)	0.0164 (4)
H5	0.5271	0.4973	0.1333	0.020*
C6	0.2853 (3)	0.4755 (2)	0.14117 (7)	0.0191 (4)
H6A	0.2777	0.3897	0.1501	0.023*
H6B	0.2015	0.5207	0.1568	0.023*
C7	0.2499 (3)	0.4829 (2)	0.09360 (7)	0.0200 (5)
C8	0.7803 (3)	0.4010 (2)	0.17338 (7)	0.0174 (4)
C9	0.6201 (3)	0.36277 (19)	0.19238 (7)	0.0172 (4)
H9	0.6436	0.3283	0.2214	0.021*
C10	0.5048 (3)	0.4712 (2)	0.19984 (7)	0.0169 (4)
C11	0.5487 (3)	0.2586 (2)	0.16552 (7)	0.0184 (4)
H11A	0.4458	0.2333	0.1783	0.022*
H11B	0.5280	0.2874	0.1359	0.022*
C12	0.6618 (3)	0.1505 (2)	0.16406 (8)	0.0212 (5)
H12A	0.6235	0.0933	0.1418	0.025*
H12B	0.6574	0.1084	0.1921	0.025*
C13	0.8391 (3)	0.1833 (2)	0.15411 (7)	0.0187 (5)
C14	0.8571 (3)	0.31658 (19)	0.14091 (7)	0.0170 (4)
H14	0.9738	0.3352	0.1406	0.020*
C15	0.7927 (3)	0.3404 (2)	0.09497 (7)	0.0187 (4)
H15A	0.6988	0.3943	0.0975	0.022*
H15B	0.8755	0.3853	0.0788	0.022*
C16	0.7446 (3)	0.2319 (2)	0.06835 (7)	0.0196 (5)
C17	0.8969 (3)	0.1031 (2)	0.11665 (7)	0.0198 (5)
H17	0.8806	0.0173	0.1259	0.024*
C18	0.9417 (3)	0.1573 (2)	0.19414 (7)	0.0252 (5)
H18A	1.0508	0.1857	0.1891	0.038*
H18B	0.9429	0.0700	0.1998	0.038*
H18C	0.8966	0.1997	0.2190	0.038*
C19	0.3680 (3)	0.4315 (2)	0.22968 (7)	0.0200 (5)
H19A	0.4090	0.4204	0.2589	0.030*
H19B	0.3230	0.3551	0.2193	0.030*
H19C	0.2848	0.4939	0.2298	0.030*
C20	1.0686 (3)	0.1145 (2)	0.10408 (8)	0.0229 (5)
C21	1.1915 (3)	0.0517 (3)	0.12110 (9)	0.0388 (7)
H21	1.1806	−0.0064	0.1435	0.047*
C22	1.1390 (3)	0.1892 (2)	0.07166 (9)	0.0291 (6)
H22	1.0848	0.2445	0.0534	0.035*
C23	1.2970 (3)	0.1660 (2)	0.07200 (10)	0.0352 (6)
H23	1.3731	0.2034	0.0536	0.042*
C28	0.3676 (3)	0.7303 (2)	0.12087 (7)	0.0227 (5)
H28A	0.2525	0.7192	0.1246	0.034*
H28B	0.4003	0.6966	0.0931	0.034*
H28C	0.3931	0.8168	0.1217	0.034*
C29	0.3932 (3)	0.7090 (2)	0.20030 (7)	0.0216 (5)
H29A	0.3890	0.7986	0.2004	0.026*
H29B	0.2834	0.6783	0.2046	0.026*
C30	0.8289 (3)	0.5291 (2)	0.17323 (7)	0.0186 (4)
H30	0.9032	0.5542	0.1497	0.022*
C31	0.3549 (4)	0.4634 (3)	0.02342 (7)	0.0309 (6)
H31A	0.2752	0.4020	0.0160	0.046*
H31B	0.4555	0.4450	0.0088	0.046*
H31C	0.3168	0.5433	0.0143	0.046*
C32	0.8270 (3)	0.7374 (2)	0.10287 (7)	0.0201 (5)
C33	0.8800 (3)	0.7130 (2)	0.05808 (7)	0.0217 (5)
C34	0.8116 (3)	0.6249 (2)	0.03490 (7)	0.0239 (5)
H34	0.7187	0.5880	0.0464	0.029*
C35	0.8694 (4)	0.5802 (3)	−0.00750 (8)	0.0334 (6)
H35A	0.9248	0.6458	−0.0226	0.050*
H35B	0.7784	0.5530	−0.0248	0.050*
H35C	0.9430	0.5124	−0.0030	0.050*
C36	1.0232 (3)	0.7845 (3)	0.04405 (8)	0.0308 (6)
H36A	1.1197	0.7488	0.0565	0.046*
H36B	1.0125	0.8684	0.0539	0.046*
H36C	1.0309	0.7831	0.0126	0.046*
O1	0.6661 (2)	0.53802 (16)	0.26154 (5)	0.0239 (4)
H1	0.7477	0.4960	0.2567	0.036*
O2	0.69261 (19)	0.67773 (14)	0.11384 (5)	0.0196 (3)
O3	0.8976 (2)	0.80205 (15)	0.12781 (5)	0.0266 (4)
O4	0.1193 (2)	0.50008 (15)	0.07891 (6)	0.0272 (4)
O5	0.3803 (2)	0.46342 (16)	0.06975 (5)	0.0231 (4)
O6	0.89406 (19)	0.44735 (15)	0.20546 (5)	0.0208 (3)
O7	0.6602 (2)	0.24246 (16)	0.03686 (5)	0.0278 (4)
O8	0.7975 (2)	0.12148 (15)	0.07864 (5)	0.0217 (3)
O9	1.3317 (2)	0.0814 (2)	0.10248 (7)	0.0412 (5)
O10	0.4921 (2)	0.66853 (14)	0.23485 (5)	0.0219 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0233 (11)	0.0216 (11)	0.0137 (9)	0.0018 (9)	−0.0003 (9)	−0.0023 (8)
C2	0.0207 (11)	0.0168 (10)	0.0172 (10)	−0.0010 (9)	−0.0009 (9)	−0.0035 (8)
C3	0.0237 (11)	0.0167 (10)	0.0163 (10)	−0.0004 (9)	0.0006 (9)	−0.0030 (8)
C4	0.0189 (11)	0.0180 (10)	0.0167 (10)	0.0014 (9)	0.0005 (9)	−0.0022 (8)
C5	0.0167 (10)	0.0174 (10)	0.0150 (10)	0.0016 (9)	0.0001 (8)	−0.0001 (8)
C6	0.0177 (11)	0.0216 (11)	0.0179 (10)	0.0006 (9)	0.0000 (9)	−0.0009 (9)
C7	0.0219 (11)	0.0136 (10)	0.0246 (11)	−0.0029 (9)	−0.0029 (9)	0.0004 (9)
C8	0.0186 (11)	0.0183 (10)	0.0152 (9)	0.0020 (9)	−0.0009 (9)	0.0005 (8)
C9	0.0182 (10)	0.0194 (10)	0.0140 (9)	0.0011 (9)	0.0016 (9)	0.0012 (8)
C10	0.0169 (10)	0.0191 (10)	0.0147 (10)	0.0015 (9)	0.0009 (8)	−0.0006 (8)
C11	0.0192 (10)	0.0170 (10)	0.0189 (10)	−0.0008 (9)	0.0026 (8)	0.0002 (8)
C12	0.0242 (12)	0.0157 (10)	0.0236 (11)	0.0002 (9)	0.0071 (9)	0.0024 (9)
C13	0.0218 (11)	0.0172 (10)	0.0172 (10)	0.0033 (9)	0.0030 (9)	0.0024 (8)
C14	0.0177 (10)	0.0163 (10)	0.0171 (10)	0.0018 (9)	0.0013 (8)	0.0008 (8)
C15	0.0216 (11)	0.0183 (10)	0.0162 (10)	0.0027 (9)	0.0031 (9)	0.0006 (8)
C16	0.0183 (11)	0.0245 (11)	0.0161 (10)	0.0004 (9)	0.0051 (9)	0.0001 (9)
C17	0.0241 (11)	0.0160 (10)	0.0193 (10)	0.0018 (9)	0.0013 (9)	0.0004 (8)
C18	0.0308 (13)	0.0244 (12)	0.0204 (11)	0.0066 (10)	0.0034 (10)	0.0038 (9)
C19	0.0219 (11)	0.0222 (11)	0.0160 (10)	0.0025 (10)	0.0052 (9)	0.0004 (8)
C20	0.0255 (12)	0.0209 (11)	0.0224 (11)	0.0031 (10)	0.0015 (9)	−0.0073 (9)
C21	0.0335 (15)	0.0531 (18)	0.0297 (13)	0.0206 (14)	0.0047 (12)	0.0016 (13)
C22	0.0263 (13)	0.0221 (12)	0.0388 (14)	0.0007 (10)	0.0089 (11)	0.0014 (10)
C23	0.0289 (14)	0.0248 (13)	0.0518 (17)	−0.0064 (12)	0.0125 (12)	−0.0126 (12)
C28	0.0245 (12)	0.0199 (11)	0.0237 (11)	0.0046 (10)	−0.0017 (9)	0.0000 (9)
C29	0.0251 (12)	0.0200 (11)	0.0198 (11)	0.0053 (10)	0.0014 (10)	−0.0025 (9)
C30	0.0179 (10)	0.0200 (10)	0.0178 (10)	0.0005 (9)	−0.0009 (9)	0.0001 (8)
C31	0.0377 (14)	0.0392 (14)	0.0160 (11)	−0.0076 (13)	−0.0023 (10)	−0.0010 (10)
C32	0.0224 (11)	0.0158 (10)	0.0220 (11)	0.0014 (9)	−0.0011 (9)	0.0047 (9)
C33	0.0217 (11)	0.0227 (11)	0.0206 (11)	0.0031 (10)	0.0000 (9)	0.0068 (9)
C34	0.0254 (12)	0.0260 (12)	0.0203 (10)	0.0061 (10)	−0.0013 (10)	0.0034 (9)
C35	0.0393 (15)	0.0390 (15)	0.0220 (12)	0.0101 (13)	−0.0014 (11)	−0.0037 (11)
C36	0.0282 (13)	0.0383 (14)	0.0260 (12)	−0.0044 (12)	0.0022 (11)	0.0097 (11)
O1	0.0276 (9)	0.0288 (9)	0.0153 (7)	0.0019 (8)	−0.0035 (7)	−0.0013 (7)
O2	0.0229 (8)	0.0194 (8)	0.0165 (7)	−0.0025 (7)	0.0030 (6)	−0.0014 (6)
O3	0.0325 (10)	0.0221 (8)	0.0251 (8)	−0.0089 (8)	−0.0013 (8)	−0.0023 (7)
O4	0.0222 (9)	0.0289 (9)	0.0306 (9)	−0.0016 (7)	−0.0080 (7)	0.0044 (7)
O5	0.0246 (8)	0.0280 (8)	0.0169 (7)	−0.0024 (8)	0.0000 (7)	−0.0037 (7)
O6	0.0211 (8)	0.0215 (8)	0.0199 (7)	0.0001 (7)	−0.0042 (7)	0.0008 (6)
O7	0.0291 (9)	0.0346 (9)	0.0197 (8)	0.0046 (8)	−0.0028 (7)	−0.0029 (7)
O8	0.0234 (8)	0.0201 (8)	0.0216 (8)	0.0005 (7)	0.0008 (7)	−0.0035 (6)
O9	0.0268 (10)	0.0582 (14)	0.0385 (11)	0.0118 (10)	−0.0020 (9)	−0.0137 (10)
O10	0.0281 (9)	0.0216 (8)	0.0160 (7)	0.0040 (7)	0.0015 (7)	−0.0048 (6)

C1—O1	1.404 (3)	C16—O8	1.336 (3)
C1—O10	1.424 (3)	C17—O8	1.460 (3)
C1—C2	1.537 (3)	C17—C20	1.498 (3)
C1—C10	1.546 (3)	C17—H17	1.0000
C2—C30	1.514 (3)	C18—H18A	0.9800
C2—C3	1.545 (3)	C18—H18B	0.9800
C2—H2	1.0000	C18—H18C	0.9800
C3—O2	1.454 (3)	C19—H19A	0.9800
C3—C4	1.529 (3)	C19—H19B	0.9800
C3—H3	1.0000	C19—H19C	0.9800
C4—C29	1.525 (3)	C20—C21	1.350 (4)
C4—C28	1.527 (3)	C20—C22	1.429 (4)
C4—C5	1.559 (3)	C21—O9	1.351 (4)
C5—C6	1.530 (3)	C21—H21	0.9500
C5—C10	1.576 (3)	C22—C23	1.350 (4)
C5—H5	1.0000	C22—H22	0.9500
C6—C7	1.510 (3)	C23—O9	1.362 (4)
C6—H6A	0.9900	C23—H23	0.9500
C6—H6B	0.9900	C28—H28A	0.9800
C7—O4	1.202 (3)	C28—H28B	0.9800
C7—O5	1.339 (3)	C28—H28C	0.9800
C8—O6	1.472 (3)	C29—O10	1.429 (3)
C8—C30	1.472 (3)	C29—H29A	0.9900
C8—C14	1.518 (3)	C29—H29B	0.9900
C8—C9	1.527 (3)	C30—O6	1.455 (3)
C9—C11	1.542 (3)	C30—H30	1.0000
C9—C10	1.557 (3)	C31—O5	1.455 (3)
C9—H9	1.0000	C31—H31A	0.9800
C10—C19	1.539 (3)	C31—H31B	0.9800
C11—C12	1.525 (3)	C31—H31C	0.9800
C11—H11A	0.9900	C32—O3	1.209 (3)
C11—H11B	0.9900	C32—O2	1.349 (3)
C12—C13	1.561 (3)	C32—C33	1.486 (3)
C12—H12A	0.9900	C33—C34	1.339 (3)
C12—H12B	0.9900	C33—C36	1.503 (3)
C13—C14	1.536 (3)	C34—C35	1.488 (3)
C13—C18	1.540 (3)	C34—H34	0.9500
C13—C17	1.541 (3)	C35—H35A	0.9800
C14—C15	1.549 (3)	C35—H35B	0.9800
C14—H14	1.0000	C35—H35C	0.9800
C15—C16	1.511 (3)	C36—H36A	0.9800
C15—H15A	0.9900	C36—H36B	0.9800
C15—H15B	0.9900	C36—H36C	0.9800
C16—O7	1.213 (3)	O1—H1	0.8400
O1—C1—O10	102.93 (16)	H15A—C15—H15B	107.2
O1—C1—C2	111.83 (19)	O7—C16—O8	118.3 (2)
O10—C1—C2	108.37 (18)	O7—C16—C15	121.4 (2)
O1—C1—C10	112.88 (18)	O8—C16—C15	120.26 (19)
O10—C1—C10	110.26 (18)	O8—C17—C20	109.06 (18)
C2—C1—C10	110.26 (17)	O8—C17—C13	110.62 (18)
C30—C2—C1	110.99 (18)	C20—C17—C13	116.84 (19)
C30—C2—C3	113.69 (18)	O8—C17—H17	106.6
C1—C2—C3	107.30 (18)	C20—C17—H17	106.6
C30—C2—H2	108.2	C13—C17—H17	106.6
C1—C2—H2	108.2	C13—C18—H18A	109.5
C3—C2—H2	108.2	C13—C18—H18B	109.5
O2—C3—C4	106.98 (17)	H18A—C18—H18B	109.5
O2—C3—C2	112.33 (18)	C13—C18—H18C	109.5
C4—C3—C2	109.95 (18)	H18A—C18—H18C	109.5
O2—C3—H3	109.2	H18B—C18—H18C	109.5
C4—C3—H3	109.2	C10—C19—H19A	109.5
C2—C3—H3	109.2	C10—C19—H19B	109.5
C29—C4—C28	109.30 (18)	H19A—C19—H19B	109.5
C29—C4—C3	104.77 (18)	C10—C19—H19C	109.5
C28—C4—C3	110.43 (19)	H19A—C19—H19C	109.5
C29—C4—C5	109.33 (18)	H19B—C19—H19C	109.5
C28—C4—C5	115.08 (18)	C21—C20—C22	105.0 (2)
C3—C4—C5	107.43 (18)	C21—C20—C17	126.1 (2)
C6—C5—C4	113.65 (19)	C22—C20—C17	129.0 (2)
C6—C5—C10	113.09 (18)	C20—C21—O9	111.8 (3)
C4—C5—C10	109.14 (18)	C20—C21—H21	124.1
C6—C5—H5	106.8	O9—C21—H21	124.1
C4—C5—H5	106.8	C23—C22—C20	106.9 (3)
C10—C5—H5	106.8	C23—C22—H22	126.6
C7—C6—C5	115.98 (19)	C20—C22—H22	126.6
C7—C6—H6A	108.3	C22—C23—O9	110.2 (3)
C5—C6—H6A	108.3	C22—C23—H23	124.9
C7—C6—H6B	108.3	O9—C23—H23	124.9
C5—C6—H6B	108.3	C4—C28—H28A	109.5
H6A—C6—H6B	107.4	C4—C28—H28B	109.5
O4—C7—O5	124.0 (2)	H28A—C28—H28B	109.5
O4—C7—C6	124.0 (2)	C4—C28—H28C	109.5
O5—C7—C6	111.90 (19)	H28A—C28—H28C	109.5
O6—C8—C30	59.23 (13)	H28B—C28—H28C	109.5
O6—C8—C14	112.87 (18)	O10—C29—C4	111.23 (18)
C30—C8—C14	118.07 (19)	O10—C29—H29A	109.4
O6—C8—C9	113.87 (17)	C4—C29—H29A	109.4
C30—C8—C9	120.70 (19)	O10—C29—H29B	109.4
C14—C8—C9	117.45 (18)	C4—C29—H29B	109.4
C8—C9—C11	109.77 (17)	H29A—C29—H29B	108.0
C8—C9—C10	113.02 (18)	O6—C30—C8	60.37 (14)
C11—C9—C10	114.46 (18)	O6—C30—C2	113.99 (18)
C8—C9—H9	106.3	C8—C30—C2	121.8 (2)
C11—C9—H9	106.3	O6—C30—H30	116.2
C10—C9—H9	106.3	C8—C30—H30	116.2
C19—C10—C1	108.32 (17)	C2—C30—H30	116.2
C19—C10—C9	109.48 (18)	O5—C31—H31A	109.5
C1—C10—C9	108.61 (17)	O5—C31—H31B	109.5
C19—C10—C5	114.11 (18)	H31A—C31—H31B	109.5
C1—C10—C5	106.07 (17)	O5—C31—H31C	109.5
C9—C10—C5	110.08 (17)	H31A—C31—H31C	109.5
C12—C11—C9	111.02 (19)	H31B—C31—H31C	109.5
C12—C11—H11A	109.4	O3—C32—O2	122.4 (2)
C9—C11—H11A	109.4	O3—C32—C33	124.2 (2)
C12—C11—H11B	109.4	O2—C32—C33	113.45 (19)
C9—C11—H11B	109.4	C34—C33—C32	120.5 (2)
H11A—C11—H11B	108.0	C34—C33—C36	124.6 (2)
C11—C12—C13	114.63 (18)	C32—C33—C36	114.5 (2)
C11—C12—H12A	108.6	C33—C34—C35	125.3 (2)
C13—C12—H12A	108.6	C33—C34—H34	117.3
C11—C12—H12B	108.6	C35—C34—H34	117.3
C13—C12—H12B	108.6	C34—C35—H35A	109.5
H12A—C12—H12B	107.6	C34—C35—H35B	109.5
C14—C13—C18	109.84 (19)	H35A—C35—H35B	109.5
C14—C13—C17	108.53 (17)	C34—C35—H35C	109.5
C18—C13—C17	109.13 (18)	H35A—C35—H35C	109.5
C14—C13—C12	111.65 (18)	H35B—C35—H35C	109.5
C18—C13—C12	109.20 (18)	C33—C36—H36A	109.5
C17—C13—C12	108.44 (19)	C33—C36—H36B	109.5
C8—C14—C13	111.67 (17)	H36A—C36—H36B	109.5
C8—C14—C15	111.12 (18)	C33—C36—H36C	109.5
C13—C14—C15	112.00 (18)	H36A—C36—H36C	109.5
C8—C14—H14	107.2	H36B—C36—H36C	109.5
C13—C14—H14	107.2	C1—O1—H1	109.5
C15—C14—H14	107.2	C32—O2—C3	115.97 (17)
C16—C15—C14	117.57 (18)	C7—O5—C31	115.3 (2)
C16—C15—H15A	107.9	C30—O6—C8	60.40 (13)
C14—C15—H15A	107.9	C16—O8—C17	120.65 (17)
C16—C15—H15B	107.9	C21—O9—C23	106.2 (2)
C14—C15—H15B	107.9	C1—O10—C29	112.70 (15)
O1—C1—C2—C30	73.3 (2)	C9—C8—C14—C15	85.2 (2)
O10—C1—C2—C30	−173.89 (17)	C18—C13—C14—C8	−69.2 (2)
C10—C1—C2—C30	−53.1 (2)	C17—C13—C14—C8	171.59 (18)
O1—C1—C2—C3	−161.90 (17)	C12—C13—C14—C8	52.1 (2)
O10—C1—C2—C3	−49.1 (2)	C18—C13—C14—C15	165.47 (18)
C10—C1—C2—C3	71.6 (2)	C17—C13—C14—C15	46.2 (2)
C30—C2—C3—O2	−12.4 (3)	C12—C13—C14—C15	−73.2 (2)
C1—C2—C3—O2	−135.55 (18)	C8—C14—C15—C16	−133.7 (2)
C30—C2—C3—C4	106.6 (2)	C13—C14—C15—C16	−8.0 (3)
C1—C2—C3—C4	−16.5 (2)	C14—C15—C16—O7	162.6 (2)
O2—C3—C4—C29	−171.39 (17)	C14—C15—C16—O8	−18.8 (3)
C2—C3—C4—C29	66.4 (2)	C14—C13—C17—O8	−62.9 (2)
O2—C3—C4—C28	−53.8 (2)	C18—C13—C17—O8	177.45 (18)
C2—C3—C4—C28	−176.06 (17)	C12—C13—C17—O8	58.6 (2)
O2—C3—C4—C5	72.4 (2)	C14—C13—C17—C20	62.7 (3)
C2—C3—C4—C5	−49.8 (2)	C18—C13—C17—C20	−57.0 (3)
C29—C4—C5—C6	85.0 (2)	C12—C13—C17—C20	−175.86 (19)
C28—C4—C5—C6	−38.5 (3)	O8—C17—C20—C21	−145.8 (2)
C3—C4—C5—C6	−161.87 (17)	C13—C17—C20—C21	87.9 (3)
C29—C4—C5—C10	−42.3 (2)	O8—C17—C20—C22	32.4 (3)
C28—C4—C5—C10	−165.69 (18)	C13—C17—C20—C22	−93.9 (3)
C3—C4—C5—C10	70.9 (2)	C22—C20—C21—O9	0.6 (3)
C4—C5—C6—C7	76.8 (2)	C17—C20—C21—O9	179.2 (2)
C10—C5—C6—C7	−158.06 (19)	C21—C20—C22—C23	−0.4 (3)
C5—C6—C7—O4	−146.4 (2)	C17—C20—C22—C23	−178.9 (2)
C5—C6—C7—O5	36.0 (3)	C20—C22—C23—O9	0.1 (3)
O6—C8—C9—C11	−149.39 (18)	C28—C4—C29—O10	−168.90 (19)
C30—C8—C9—C11	143.4 (2)	C3—C4—C29—O10	−50.6 (2)
C14—C8—C9—C11	−14.3 (3)	C5—C4—C29—O10	64.3 (2)
O6—C8—C9—C10	81.5 (2)	C14—C8—C30—O6	−101.3 (2)
C30—C8—C9—C10	14.3 (3)	C9—C8—C30—O6	101.2 (2)
C14—C8—C9—C10	−143.36 (19)	O6—C8—C30—C2	−101.4 (2)
O1—C1—C10—C19	61.0 (2)	C14—C8—C30—C2	157.3 (2)
O10—C1—C10—C19	−53.5 (2)	C9—C8—C30—C2	−0.2 (3)
C2—C1—C10—C19	−173.09 (18)	C1—C2—C30—O6	−49.4 (2)
O1—C1—C10—C9	−57.8 (2)	C3—C2—C30—O6	−170.44 (17)
O10—C1—C10—C9	−172.29 (16)	C1—C2—C30—C8	19.5 (3)
C2—C1—C10—C9	68.1 (2)	C3—C2—C30—C8	−101.6 (2)
O1—C1—C10—C5	−176.07 (18)	O3—C32—C33—C34	168.5 (2)
O10—C1—C10—C5	69.4 (2)	O2—C32—C33—C34	−10.0 (3)
C2—C1—C10—C5	−50.2 (2)	O3—C32—C33—C36	−5.3 (3)
C8—C9—C10—C19	−164.78 (18)	O2—C32—C33—C36	176.15 (19)
C11—C9—C10—C19	68.6 (2)	C32—C33—C34—C35	−170.6 (2)
C8—C9—C10—C1	−46.7 (2)	C36—C33—C34—C35	2.6 (4)
C11—C9—C10—C1	−173.34 (17)	O3—C32—O2—C3	3.1 (3)
C8—C9—C10—C5	69.0 (2)	C33—C32—O2—C3	−178.40 (18)
C11—C9—C10—C5	−57.6 (2)	C4—C3—O2—C32	159.42 (17)
C6—C5—C10—C19	−26.6 (3)	C2—C3—O2—C32	−79.9 (2)
C4—C5—C10—C19	101.0 (2)	O4—C7—O5—C31	−0.4 (3)
C6—C5—C10—C1	−145.73 (18)	C6—C7—O5—C31	177.3 (2)
C4—C5—C10—C1	−18.2 (2)	C2—C30—O6—C8	114.2 (2)
C6—C5—C10—C9	97.0 (2)	C14—C8—O6—C30	110.1 (2)
C4—C5—C10—C9	−135.48 (19)	C9—C8—O6—C30	−112.7 (2)
C8—C9—C11—C12	58.2 (2)	O7—C16—O8—C17	−178.86 (19)
C10—C9—C11—C12	−173.53 (17)	C15—C16—O8—C17	2.5 (3)
C9—C11—C12—C13	−46.5 (3)	C20—C17—O8—C16	−91.0 (2)
C11—C12—C13—C14	−8.9 (3)	C13—C17—O8—C16	38.8 (3)
C11—C12—C13—C18	112.8 (2)	C20—C21—O9—C23	−0.6 (3)
C11—C12—C13—C17	−128.4 (2)	C22—C23—O9—C21	0.3 (3)
O6—C8—C14—C13	94.9 (2)	O1—C1—O10—C29	−172.35 (18)
C30—C8—C14—C13	161.04 (19)	C2—C1—O10—C29	69.1 (2)
C9—C8—C14—C13	−40.7 (3)	C10—C1—O10—C29	−51.7 (2)
O6—C8—C14—C15	−139.27 (18)	C4—C29—O10—C1	−15.1 (3)
C30—C8—C14—C15	−73.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O6	0.84	2.08	2.774 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O6	0.84	2.08	2.774 (2)	139