Xyloccensin e.

The title compound (also known as phragmalin triacetate), C(35)H(42)O(14), is a phragmalin-type limonoid extracted from X. rumphii. The mol-ecule consists of eight rings with the orthoacetate group bridged at positions 1, 8 and 9. The two five-carbocyclic rings (A(1) and A(2)) and the dioxolane ring (G) adopt a distorted envelope conformation. The 1,3-dioxane ring (E) exists in a chair conformation. The six-carbocyclic rings (B and C) exhibit a twisted-boat conformation. The lactone ring has a half-chair conformation and the furan ring is planar (r.m.s. deviation = 0.002 Å). Rings A(1)/B, A(2)/B, B/C, C/D and C/G are all cis-fused. The two acet-oxy groups attached to ring B and the furan ring attached to the lactone ring are in equatorial positions. The porous crystal packing exhibits voids of 688 Å(3) and weak inter-molecular C-H⋯O inter-actions. The absolute configuration was assigned on the basis of literature data.

Related literature

For background to the structures of limonoids and their activities, see: Koul et al. (2004 ▶); Cui et al. (2005 ▶); Pudhom et al. (2009 ▶). For related structures and the assignment of the absolute configuration, see: Wu et al. (2004 ▶); Fan et al. (2007 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C35H42O14

M = 686.69

Hexagonal,

a = 17.7635 (5) Å

c = 19.6294 (6) Å

V = 5364.1 (3) Å3

Z = 6

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.40 × 0.40 × 0.30 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

28307 measured reflections

4183 independent reflections

3738 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.130

S = 1.10

4183 reflections

445 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.77 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016582/cv2715sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016582/cv2715Isup2.hkl

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

C35H42O14	F(000) = 2184
Mr = 686.69	Dx = 1.275 Mg m−3
Hexagonal, P61	Melting point: 168 K
Hall symbol: P 61	Mo Kα radiation, λ = 0.71073 Å
a = 17.7635 (5) Å	µ = 0.10 mm−1
c = 19.6294 (6) Å	T = 100 K
V = 5364.1 (3) Å3	Prism, colourless
Z = 6	0.40 × 0.40 × 0.30 mm

Bruker SMART APEXII CCD area-detector diffractometer	3738 reflections with I > 2σ(I)
Radiation source: Mo	Rint = 0.040
graphite	θmax = 27.5°, θmin = 2.5°
φ and ω scans	h = −23→22
28307 measured reflections	k = −22→21
4183 independent reflections	l = −22→24

Refinement on F2	1 restraint
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046	w = 1/[σ2(Fo2) + (0.085P)2 + 0.919P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.130	(Δ/σ)max = 0.029
S = 1.10	Δρmax = 0.77 e Å−3
4183 reflections	Δρmin = −0.27 e Å−3
445 parameters

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1'	1.16441 (19)	0.58265 (19)	0.76883 (15)	0.0217 (6)
C1	1.06376 (17)	0.61547 (17)	0.81972 (14)	0.0175 (5)
C2'	1.2166 (2)	0.5971 (2)	0.70457 (17)	0.0296 (7)
H2'1	1.1781	0.576	0.6661	0.044*
H2'2	1.2482	0.5665	0.7077	0.044*
H2'3	1.2567	0.6581	0.699	0.044*
C2	0.98030 (17)	0.52150 (17)	0.82913 (13)	0.0170 (5)
C3	0.91974 (17)	0.54361 (17)	0.87095 (14)	0.0170 (5)
H3	0.8741	0.5414	0.8416	0.02*
C4	0.98104 (17)	0.63768 (18)	0.89457 (15)	0.0189 (5)
C5	1.05140 (17)	0.63106 (18)	0.93977 (14)	0.0182 (5)
H5	1.0243	0.5723	0.959	0.022*
C6	1.08925 (19)	0.69610 (19)	0.99894 (15)	0.0237 (6)
H6A	1.1462	0.7048	1.0104	0.028*
H6B	1.0967	0.7515	0.9842	0.028*
C7	1.0333 (2)	0.6669 (2)	1.06132 (17)	0.0307 (7)
C8	1.09628 (18)	0.48402 (18)	0.85465 (14)	0.0186 (5)
C9	1.15837 (17)	0.57860 (18)	0.88338 (14)	0.0186 (5)
C10	1.11894 (17)	0.63904 (17)	0.88473 (14)	0.0169 (5)
C11	1.20720 (18)	0.57911 (19)	0.94751 (15)	0.0212 (6)
H11A	1.2226	0.6312	0.9737	0.025*
H11B	1.2605	0.5804	0.9347	0.025*
C12	1.15201 (19)	0.49887 (19)	0.99166 (15)	0.0220 (6)
H12A	1.0969	0.4954	1.0017	0.026*
H12B	1.1817	0.5046	1.0345	0.026*
C13	1.13502 (19)	0.41414 (19)	0.95545 (15)	0.0211 (6)
C14	1.13326 (18)	0.42580 (19)	0.87763 (15)	0.0201 (5)
H14	1.1948	0.4589	0.8648	0.024*
C15	1.0988 (2)	0.3398 (2)	0.83957 (15)	0.0247 (6)
H15A	1.0761	0.3454	0.7961	0.03*
H15B	1.1477	0.3314	0.83	0.03*
C16	1.0297 (2)	0.2590 (2)	0.87376 (17)	0.0309 (7)
C17	1.0464 (2)	0.33966 (19)	0.98038 (16)	0.0240 (6)
H17	1.0036	0.3588	0.9758	0.029*
C18	1.2087 (2)	0.3951 (2)	0.97206 (16)	0.0268 (6)
H18A	1.1967	0.3416	0.9508	0.04*
H18B	1.2124	0.3903	1.0205	0.04*
H18C	1.2628	0.4416	0.9552	0.04*
C19	1.19506 (18)	0.73425 (18)	0.88085 (16)	0.0230 (6)
H19A	1.2293	0.7481	0.9216	0.035*
H19B	1.1722	0.7728	0.8764	0.035*
H19C	1.2308	0.7407	0.8421	0.035*
C20	1.0459 (2)	0.3137 (2)	1.05295 (18)	0.0308 (7)
C21	1.0287 (3)	0.3468 (3)	1.10853 (19)	0.0436 (9)
H21	1.0145	0.3906	1.1076	0.052*
C22	1.0637 (3)	0.2486 (3)	1.0784 (2)	0.0523 (11)
H22	1.0777	0.2132	1.0528	0.063*
C23	1.0561 (3)	0.2487 (4)	1.1461 (3)	0.0651 (15)
H23	1.0645	0.2124	1.1754	0.078*
C24	0.79901 (18)	0.46072 (18)	0.94503 (15)	0.0212 (5)
C25	0.7784 (2)	0.4132 (2)	1.01126 (17)	0.0280 (6)
H25A	0.828	0.4098	1.0265	0.042*	0.5
H25B	0.73	0.3555	1.0053	0.042*	0.5
H25C	0.764	0.4436	1.0445	0.042*	0.5
H25D	0.72	0.3961	1.0244	0.042*	0.5
H25E	0.8181	0.4504	1.0456	0.042*	0.5
H25F	0.784	0.3624	1.0064	0.042*	0.5
C28	0.9336 (2)	0.6798 (2)	0.92673 (17)	0.0257 (6)
H28A	0.975	0.7379	0.9405	0.039*
H28B	0.9018	0.6467	0.9658	0.039*
H28C	0.8941	0.6814	0.8942	0.039*
C29	1.02450 (19)	0.67419 (18)	0.82469 (15)	0.0205 (5)
H29A	0.9828	0.6636	0.7888	0.025*
H29B	1.0681	0.7354	0.8265	0.025*
C30	1.00034 (17)	0.45462 (17)	0.86481 (14)	0.0171 (5)
H30	0.9871	0.4515	0.9136	0.021*
C31	0.87864 (19)	0.30753 (19)	0.86851 (19)	0.0278 (7)
C32	0.8275 (2)	0.2305 (2)	0.8248 (2)	0.0422 (9)
H32A	0.7737	0.1915	0.8469	0.063*
H32B	0.86	0.2014	0.8171	0.063*
H32C	0.8158	0.2487	0.7819	0.063*
C33	0.86812 (19)	0.43362 (19)	0.74661 (16)	0.0224 (6)
C34	0.8570 (2)	0.4182 (2)	0.67120 (18)	0.0360 (8)
H34A	0.8444	0.3601	0.6613	0.054*
H34B	0.9096	0.459	0.6484	0.054*
H34C	0.8099	0.4256	0.6556	0.054*
C35	1.0148 (3)	0.7155 (4)	1.1691 (2)	0.0732 (18)
H35A	1.0391	0.7675	1.196	0.11*	0.5
H35B	1.0208	0.6716	1.1929	0.11*	0.5
H35C	0.9543	0.6952	1.161	0.11*	0.5
H35D	0.9704	0.6554	1.1706	0.11*	0.5
H35E	0.9887	0.7513	1.1737	0.11*	0.5
H35F	1.0552	0.7277	1.2057	0.11*	0.5
O1	1.21889 (12)	0.61294 (13)	0.82626 (11)	0.0214 (4)
O2	1.10977 (13)	0.49352 (13)	0.78162 (10)	0.0208 (4)
O3	1.11411 (13)	0.62397 (13)	0.76107 (10)	0.0207 (4)
O4	0.88190 (12)	0.48674 (13)	0.92764 (10)	0.0184 (4)
O6	0.95079 (12)	0.49548 (12)	0.75992 (10)	0.0198 (4)
O7	0.94979 (13)	0.36999 (12)	0.83415 (11)	0.0215 (4)
O8	1.01541 (16)	0.25960 (14)	0.94147 (12)	0.0308 (5)
O9	0.9896 (2)	0.19177 (17)	0.84406 (16)	0.0500 (7)
O10	1.0349 (2)	0.3077 (2)	1.16646 (14)	0.0602 (10)
O11	0.75158 (15)	0.47641 (17)	0.91176 (13)	0.0351 (6)
O13	0.86291 (15)	0.31476 (14)	0.92703 (13)	0.0318 (5)
O14	0.81228 (14)	0.39672 (14)	0.78855 (12)	0.0266 (5)
O15	0.97453 (19)	0.59611 (19)	1.07362 (14)	0.0504 (8)
O16	1.05994 (17)	0.7337 (2)	1.10510 (14)	0.0500 (8)

	U11	U22	U33	U12	U13	U23
C1'	0.0198 (13)	0.0228 (14)	0.0195 (13)	0.0085 (11)	0.0022 (11)	0.0031 (11)
C1	0.0163 (12)	0.0178 (12)	0.0169 (12)	0.0073 (10)	0.0012 (10)	0.0031 (10)
C2'	0.0278 (16)	0.0324 (16)	0.0252 (16)	0.0126 (13)	0.0102 (13)	0.0070 (13)
C2	0.0157 (12)	0.0181 (12)	0.0145 (12)	0.0065 (10)	−0.0021 (9)	−0.0002 (10)
C3	0.0150 (12)	0.0178 (12)	0.0176 (12)	0.0077 (10)	0.0001 (10)	0.0019 (10)
C4	0.0143 (12)	0.0179 (13)	0.0226 (13)	0.0066 (10)	−0.0018 (10)	−0.0003 (10)
C5	0.0157 (12)	0.0185 (12)	0.0193 (13)	0.0076 (10)	−0.0009 (10)	0.0009 (10)
C6	0.0184 (13)	0.0243 (14)	0.0244 (14)	0.0077 (11)	−0.0026 (11)	−0.0056 (12)
C7	0.0228 (15)	0.0396 (18)	0.0222 (14)	0.0099 (14)	−0.0055 (12)	−0.0079 (13)
C8	0.0164 (12)	0.0224 (13)	0.0180 (13)	0.0104 (11)	0.0009 (10)	0.0022 (10)
C9	0.0124 (11)	0.0213 (13)	0.0205 (13)	0.0072 (10)	0.0016 (10)	0.0028 (10)
C10	0.0141 (12)	0.0165 (12)	0.0182 (12)	0.0063 (10)	0.0000 (9)	0.0013 (10)
C11	0.0182 (13)	0.0255 (14)	0.0193 (13)	0.0104 (11)	−0.0019 (10)	0.0008 (11)
C12	0.0206 (13)	0.0269 (14)	0.0194 (13)	0.0124 (11)	−0.0004 (11)	0.0013 (11)
C13	0.0216 (13)	0.0268 (14)	0.0184 (13)	0.0146 (12)	0.0034 (11)	0.0047 (11)
C14	0.0186 (13)	0.0263 (14)	0.0194 (13)	0.0142 (11)	0.0015 (10)	0.0018 (11)
C15	0.0297 (15)	0.0292 (15)	0.0214 (14)	0.0194 (13)	0.0013 (12)	0.0000 (11)
C16	0.0389 (18)	0.0290 (16)	0.0287 (16)	0.0200 (15)	0.0031 (14)	0.0008 (13)
C17	0.0251 (14)	0.0246 (14)	0.0230 (14)	0.0129 (12)	0.0006 (11)	0.0011 (11)
C18	0.0266 (15)	0.0343 (16)	0.0263 (15)	0.0204 (13)	−0.0008 (12)	0.0039 (13)
C19	0.0151 (12)	0.0179 (13)	0.0261 (14)	0.0008 (11)	0.0010 (11)	0.0021 (11)
C20	0.0243 (15)	0.0332 (17)	0.0287 (16)	0.0096 (13)	0.0038 (12)	0.0080 (13)
C21	0.0390 (19)	0.040 (2)	0.0275 (18)	0.0015 (16)	0.0070 (15)	0.0009 (15)
C22	0.064 (3)	0.062 (3)	0.042 (2)	0.040 (2)	0.010 (2)	0.024 (2)
C23	0.056 (3)	0.085 (4)	0.039 (2)	0.024 (3)	0.002 (2)	0.030 (2)
C24	0.0182 (13)	0.0213 (13)	0.0242 (14)	0.0099 (11)	0.0025 (11)	0.0020 (11)
C25	0.0231 (14)	0.0292 (16)	0.0284 (15)	0.0106 (13)	0.0066 (12)	0.0080 (12)
C28	0.0241 (14)	0.0270 (15)	0.0302 (16)	0.0159 (12)	−0.0019 (12)	−0.0015 (12)
C29	0.0213 (13)	0.0187 (13)	0.0214 (13)	0.0100 (11)	0.0000 (11)	0.0030 (11)
C30	0.0143 (12)	0.0154 (12)	0.0205 (13)	0.0066 (10)	−0.0010 (10)	0.0005 (10)
C31	0.0194 (14)	0.0179 (14)	0.0444 (19)	0.0079 (11)	0.0013 (13)	0.0037 (13)
C32	0.0288 (17)	0.0205 (15)	0.066 (3)	0.0035 (13)	0.0037 (17)	−0.0040 (16)
C33	0.0208 (13)	0.0195 (13)	0.0264 (14)	0.0097 (12)	−0.0066 (12)	−0.0034 (11)
C34	0.0328 (18)	0.0370 (18)	0.0273 (17)	0.0091 (15)	−0.0090 (14)	−0.0083 (13)
C35	0.039 (2)	0.111 (4)	0.036 (2)	0.012 (3)	0.0052 (18)	−0.035 (3)
O1	0.0151 (9)	0.0247 (10)	0.0207 (10)	0.0072 (8)	0.0027 (8)	0.0026 (8)
O2	0.0215 (10)	0.0227 (10)	0.0163 (9)	0.0095 (8)	0.0026 (7)	0.0038 (8)
O3	0.0208 (9)	0.0225 (10)	0.0171 (9)	0.0094 (8)	0.0036 (7)	0.0035 (8)
O4	0.0142 (9)	0.0197 (9)	0.0200 (10)	0.0075 (7)	0.0012 (7)	0.0045 (7)
O6	0.0195 (9)	0.0199 (9)	0.0175 (9)	0.0080 (8)	−0.0043 (7)	−0.0023 (7)
O7	0.0188 (9)	0.0160 (9)	0.0276 (10)	0.0072 (8)	−0.0006 (8)	−0.0003 (8)
O8	0.0372 (12)	0.0228 (10)	0.0284 (11)	0.0119 (10)	0.0035 (10)	0.0018 (9)
O9	0.0683 (19)	0.0263 (13)	0.0443 (15)	0.0154 (13)	0.0063 (14)	−0.0075 (11)
O10	0.0501 (17)	0.068 (2)	0.0228 (14)	0.0001 (16)	0.0038 (12)	0.0066 (14)
O11	0.0226 (11)	0.0506 (14)	0.0375 (13)	0.0225 (11)	0.0073 (10)	0.0155 (11)
O13	0.0267 (11)	0.0232 (11)	0.0425 (14)	0.0103 (9)	0.0095 (10)	0.0090 (10)
O14	0.0207 (10)	0.0248 (10)	0.0294 (11)	0.0078 (9)	−0.0025 (9)	−0.0004 (9)
O15	0.0473 (16)	0.0454 (16)	0.0280 (13)	0.0003 (13)	0.0066 (12)	0.0006 (11)
O16	0.0336 (13)	0.0577 (17)	0.0362 (15)	0.0059 (12)	0.0084 (11)	−0.0241 (13)

C1'—O2	1.405 (3)	C17—O8	1.458 (4)
C1'—O1	1.406 (4)	C17—C20	1.496 (4)
C1'—O3	1.420 (4)	C17—H17	0.98
C1'—C2'	1.509 (4)	C18—H18A	0.96
C1—O3	1.419 (3)	C18—H18B	0.96
C1—C29	1.520 (4)	C18—H18C	0.96
C1—C10	1.534 (4)	C19—H19A	0.96
C1—C2	1.595 (4)	C19—H19B	0.96
C2'—H2'1	0.96	C19—H19C	0.96
C2'—H2'2	0.96	C20—C21	1.346 (6)
C2'—H2'3	0.96	C20—C22	1.431 (5)
C2—O6	1.446 (3)	C21—O10	1.365 (5)
C2—C3	1.552 (4)	C21—H21	0.93
C2—C30	1.566 (4)	C22—C23	1.336 (7)
C3—O4	1.425 (3)	C22—H22	0.93
C3—C4	1.541 (4)	C23—O10	1.342 (8)
C3—H3	0.98	C23—H23	0.93
C4—C28	1.515 (4)	C24—O11	1.204 (4)
C4—C29	1.548 (4)	C24—O4	1.348 (3)
C4—C5	1.584 (4)	C24—C25	1.493 (4)
C5—C6	1.536 (4)	C25—H25A	0.96
C5—C10	1.567 (4)	C25—H25B	0.96
C5—H5	0.98	C25—H25C	0.96
C6—C7	1.497 (4)	C25—H25D	0.96
C6—H6A	0.97	C25—H25E	0.96
C6—H6B	0.97	C25—H25F	0.96
C7—O15	1.190 (4)	C28—H28A	0.96
C7—O16	1.345 (4)	C28—H28B	0.96
C8—O2	1.449 (3)	C28—H28C	0.96
C8—C30	1.525 (4)	C29—H29A	0.97
C8—C14	1.544 (4)	C29—H29B	0.97
C8—C9	1.582 (4)	C30—O7	1.442 (3)
C9—O1	1.459 (3)	C30—H30	0.98
C9—C11	1.526 (4)	C31—O13	1.204 (4)
C9—C10	1.548 (4)	C31—O7	1.372 (4)
C10—C19	1.552 (4)	C31—C32	1.481 (5)
C11—C12	1.532 (4)	C32—H32A	0.96
C11—H11A	0.97	C32—H32B	0.96
C11—H11B	0.97	C32—H32C	0.96
C12—C13	1.551 (4)	C33—O14	1.201 (4)
C12—H12A	0.97	C33—O6	1.348 (3)
C12—H12B	0.97	C33—C34	1.500 (5)
C13—C18	1.541 (4)	C34—H34A	0.96
C13—C14	1.544 (4)	C34—H34B	0.96
C13—C17	1.544 (4)	C34—H34C	0.96
C14—C15	1.527 (4)	C35—O16	1.437 (5)
C14—H14	0.98	C35—H35A	0.96
C15—C16	1.502 (5)	C35—H35B	0.96
C15—H15A	0.97	C35—H35C	0.96
C15—H15B	0.97	C35—H35D	0.96
C16—O9	1.193 (4)	C35—H35E	0.96
C16—O8	1.354 (4)	C35—H35F	0.96
O2—C1'—O1	104.1 (2)	C13—C18—H18C	109.5
O2—C1'—O3	110.0 (2)	H18A—C18—H18C	109.5
O1—C1'—O3	112.3 (2)	H18B—C18—H18C	109.5
O2—C1'—C2'	111.2 (2)	C10—C19—H19A	109.5
O1—C1'—C2'	111.0 (2)	C10—C19—H19B	109.5
O3—C1'—C2'	108.3 (2)	H19A—C19—H19B	109.5
O3—C1—C29	117.4 (2)	C10—C19—H19C	109.5
O3—C1—C10	111.3 (2)	H19A—C19—H19C	109.5
C29—C1—C10	102.1 (2)	H19B—C19—H19C	109.5
O3—C1—C2	114.3 (2)	C21—C20—C22	105.1 (4)
C29—C1—C2	101.9 (2)	C21—C20—C17	127.2 (3)
C10—C1—C2	108.8 (2)	C22—C20—C17	127.7 (3)
C1'—C2'—H2'1	109.5	C20—C21—O10	111.1 (4)
C1'—C2'—H2'2	109.5	C20—C21—H21	124.5
H2'1—C2'—H2'2	109.5	O10—C21—H21	124.5
C1'—C2'—H2'3	109.5	C23—C22—C20	106.5 (5)
H2'1—C2'—H2'3	109.5	C23—C22—H22	126.8
H2'2—C2'—H2'3	109.5	C20—C22—H22	126.8
O6—C2—C3	113.0 (2)	C22—C23—O10	111.4 (4)
O6—C2—C30	111.2 (2)	C22—C23—H23	124.3
C3—C2—C30	113.9 (2)	O10—C23—H23	124.3
O6—C2—C1	103.0 (2)	O11—C24—O4	123.7 (3)
C3—C2—C1	101.3 (2)	O11—C24—C25	127.0 (3)
C30—C2—C1	113.6 (2)	O4—C24—C25	109.3 (2)
O4—C3—C4	111.2 (2)	C24—C25—H25A	109.5
O4—C3—C2	112.0 (2)	C24—C25—H25B	109.5
C4—C3—C2	103.3 (2)	H25A—C25—H25B	109.5
O4—C3—H3	110.1	C24—C25—H25C	109.5
C4—C3—H3	110.1	H25A—C25—H25C	109.5
C2—C3—H3	110.1	H25B—C25—H25C	109.5
C28—C4—C3	113.3 (2)	C24—C25—H25D	109.5
C28—C4—C29	116.5 (2)	H25A—C25—H25D	141.1
C3—C4—C29	97.0 (2)	H25B—C25—H25D	56.3
C28—C4—C5	117.2 (2)	H25C—C25—H25D	56.3
C3—C4—C5	104.1 (2)	C24—C25—H25E	109.5
C29—C4—C5	106.3 (2)	H25A—C25—H25E	56.3
C6—C5—C10	115.2 (2)	H25B—C25—H25E	141.1
C6—C5—C4	115.6 (2)	H25C—C25—H25E	56.3
C10—C5—C4	101.8 (2)	H25D—C25—H25E	109.5
C6—C5—H5	107.9	C24—C25—H25F	109.5
C10—C5—H5	107.9	H25A—C25—H25F	56.3
C4—C5—H5	107.9	H25B—C25—H25F	56.3
C7—C6—C5	113.1 (2)	H25C—C25—H25F	141.1
C7—C6—H6A	109	H25D—C25—H25F	109.5
C5—C6—H6A	109	H25E—C25—H25F	109.5
C7—C6—H6B	109	C4—C28—H28A	109.5
C5—C6—H6B	109	C4—C28—H28B	109.5
H6A—C6—H6B	107.8	H28A—C28—H28B	109.5
O15—C7—O16	122.6 (3)	C4—C28—H28C	109.5
O15—C7—C6	127.7 (3)	H28A—C28—H28C	109.5
O16—C7—C6	109.7 (3)	H28B—C28—H28C	109.5
O2—C8—C30	105.1 (2)	C1—C29—C4	94.2 (2)
O2—C8—C14	105.4 (2)	C1—C29—H29A	112.9
C30—C8—C14	120.6 (2)	C4—C29—H29A	112.9
O2—C8—C9	104.0 (2)	C1—C29—H29B	112.9
C30—C8—C9	112.5 (2)	C4—C29—H29B	112.9
C14—C8—C9	107.6 (2)	H29A—C29—H29B	110.3
O1—C9—C11	109.5 (2)	O7—C30—C8	108.0 (2)
O1—C9—C10	102.6 (2)	O7—C30—C2	110.2 (2)
C11—C9—C10	115.8 (2)	C8—C30—C2	108.7 (2)
O1—C9—C8	98.4 (2)	O7—C30—H30	110
C11—C9—C8	113.1 (2)	C8—C30—H30	110
C10—C9—C8	115.2 (2)	C2—C30—H30	110
C1—C10—C9	104.2 (2)	O13—C31—O7	123.5 (3)
C1—C10—C19	110.3 (2)	O13—C31—C32	125.7 (3)
C9—C10—C19	107.8 (2)	O7—C31—C32	110.7 (3)
C1—C10—C5	101.1 (2)	C31—C32—H32A	109.5
C9—C10—C5	122.7 (2)	C31—C32—H32B	109.5
C19—C10—C5	110.0 (2)	H32A—C32—H32B	109.5
C9—C11—C12	111.3 (2)	C31—C32—H32C	109.5
C9—C11—H11A	109.4	H32A—C32—H32C	109.5
C12—C11—H11A	109.4	H32B—C32—H32C	109.5
C9—C11—H11B	109.4	O14—C33—O6	125.3 (3)
C12—C11—H11B	109.4	O14—C33—C34	125.4 (3)
H11A—C11—H11B	108	O6—C33—C34	109.3 (3)
C11—C12—C13	111.5 (2)	C33—C34—H34A	109.5
C11—C12—H12A	109.3	C33—C34—H34B	109.5
C13—C12—H12A	109.3	H34A—C34—H34B	109.5
C11—C12—H12B	109.3	C33—C34—H34C	109.5
C13—C12—H12B	109.3	H34A—C34—H34C	109.5
H12A—C12—H12B	108	H34B—C34—H34C	109.5
C18—C13—C14	108.4 (2)	O16—C35—H35A	109.5
C18—C13—C17	111.0 (2)	O16—C35—H35B	109.5
C14—C13—C17	110.4 (2)	H35A—C35—H35B	109.5
C18—C13—C12	109.9 (2)	O16—C35—H35C	109.5
C14—C13—C12	109.3 (2)	H35A—C35—H35C	109.5
C17—C13—C12	107.9 (2)	H35B—C35—H35C	109.5
C15—C14—C13	112.0 (2)	O16—C35—H35D	109.5
C15—C14—C8	115.8 (2)	H35A—C35—H35D	141.1
C13—C14—C8	115.0 (2)	H35B—C35—H35D	56.3
C15—C14—H14	104.1	H35C—C35—H35D	56.3
C13—C14—H14	104.1	O16—C35—H35E	109.5
C8—C14—H14	104.1	H35A—C35—H35E	56.3
C16—C15—C14	117.7 (3)	H35B—C35—H35E	141.1
C16—C15—H15A	107.9	H35C—C35—H35E	56.3
C14—C15—H15A	107.9	H35D—C35—H35E	109.5
C16—C15—H15B	107.9	O16—C35—H35F	109.5
C14—C15—H15B	107.9	H35A—C35—H35F	56.3
H15A—C15—H15B	107.2	H35B—C35—H35F	56.3
O9—C16—O8	117.8 (3)	H35C—C35—H35F	141.1
O9—C16—C15	122.1 (3)	H35D—C35—H35F	109.5
O8—C16—C15	119.9 (3)	H35E—C35—H35F	109.5
O8—C17—C20	104.9 (2)	C1'—O1—C9	103.5 (2)
O8—C17—C13	113.3 (2)	C1'—O2—C8	106.8 (2)
C20—C17—C13	114.4 (3)	C1'—O3—C1	112.6 (2)
O8—C17—H17	108	C24—O4—C3	119.2 (2)
C20—C17—H17	108	C33—O6—C2	121.0 (2)
C13—C17—H17	108	C31—O7—C30	118.7 (2)
C13—C18—H18A	109.5	C16—O8—C17	122.7 (3)
C13—C18—H18B	109.5	C23—O10—C21	106.0 (3)
H18A—C18—H18B	109.5	C7—O16—C35	116.7 (3)
O3—C1—C2—O6	−36.7 (3)	O2—C8—C14—C13	173.8 (2)
C29—C1—C2—O6	91.0 (2)	C30—C8—C14—C13	−67.7 (3)
C10—C1—C2—O6	−161.8 (2)	C9—C8—C14—C13	63.3 (3)
O3—C1—C2—C3	−153.8 (2)	C13—C14—C15—C16	33.8 (4)
C29—C1—C2—C3	−26.1 (2)	C8—C14—C15—C16	−100.8 (3)
C10—C1—C2—C3	81.1 (2)	C14—C15—C16—O9	168.1 (3)
O3—C1—C2—C30	83.7 (3)	C14—C15—C16—O8	−16.5 (4)
C29—C1—C2—C30	−148.7 (2)	C18—C13—C17—O8	−69.8 (3)
C10—C1—C2—C30	−41.4 (3)	C14—C13—C17—O8	50.4 (3)
O6—C2—C3—O4	117.4 (2)	C12—C13—C17—O8	169.7 (2)
C30—C2—C3—O4	−10.7 (3)	C18—C13—C17—C20	50.4 (4)
C1—C2—C3—O4	−133.1 (2)	C14—C13—C17—C20	170.6 (3)
O6—C2—C3—C4	−122.9 (2)	C12—C13—C17—C20	−70.1 (3)
C30—C2—C3—C4	109.0 (2)	O8—C17—C20—C21	−146.0 (3)
C1—C2—C3—C4	−13.4 (2)	C13—C17—C20—C21	89.2 (4)
O4—C3—C4—C28	−69.5 (3)	O8—C17—C20—C22	34.1 (5)
C2—C3—C4—C28	170.2 (2)	C13—C17—C20—C22	−90.7 (4)
O4—C3—C4—C29	167.7 (2)	C22—C20—C21—O10	0.4 (4)
C2—C3—C4—C29	47.4 (2)	C17—C20—C21—O10	−179.6 (3)
O4—C3—C4—C5	58.9 (3)	C21—C20—C22—C23	−0.3 (5)
C2—C3—C4—C5	−61.4 (2)	C17—C20—C22—C23	179.6 (4)
C28—C4—C5—C6	−22.4 (4)	C20—C22—C23—O10	0.2 (6)
C3—C4—C5—C6	−148.3 (2)	O3—C1—C29—C4	−179.6 (2)
C29—C4—C5—C6	109.9 (3)	C10—C1—C29—C4	−57.7 (2)
C28—C4—C5—C10	−148.0 (2)	C2—C1—C29—C4	54.7 (2)
C3—C4—C5—C10	86.1 (2)	C28—C4—C29—C1	177.0 (2)
C29—C4—C5—C10	−15.7 (3)	C3—C4—C29—C1	−62.7 (2)
C10—C5—C6—C7	−158.4 (3)	C5—C4—C29—C1	44.3 (2)
C4—C5—C6—C7	83.2 (3)	O2—C8—C30—O7	64.8 (3)
C5—C6—C7—O15	14.5 (5)	C14—C8—C30—O7	−53.9 (3)
C5—C6—C7—O16	−166.8 (3)	C9—C8—C30—O7	177.3 (2)
O2—C8—C9—O1	−22.2 (2)	O2—C8—C30—C2	−54.8 (3)
C30—C8—C9—O1	−135.4 (2)	C14—C8—C30—C2	−173.5 (2)
C14—C8—C9—O1	89.3 (2)	C9—C8—C30—C2	57.8 (3)
O2—C8—C9—C11	−137.7 (2)	O6—C2—C30—O7	−25.9 (3)
C30—C8—C9—C11	109.1 (3)	C3—C2—C30—O7	103.2 (2)
C14—C8—C9—C11	−26.2 (3)	C1—C2—C30—O7	−141.5 (2)
O2—C8—C9—C10	86.0 (3)	O6—C2—C30—C8	92.3 (3)
C30—C8—C9—C10	−27.2 (3)	C3—C2—C30—C8	−138.6 (2)
C14—C8—C9—C10	−162.5 (2)	C1—C2—C30—C8	−23.3 (3)
O3—C1—C10—C9	−55.7 (3)	O2—C1'—O1—C9	−49.3 (3)
C29—C1—C10—C9	178.3 (2)	O3—C1'—O1—C9	69.7 (3)
C2—C1—C10—C9	71.1 (3)	C2'—C1'—O1—C9	−169.0 (2)
O3—C1—C10—C19	59.7 (3)	C11—C9—O1—C1'	160.9 (2)
C29—C1—C10—C19	−66.3 (3)	C10—C9—O1—C1'	−75.6 (2)
C2—C1—C10—C19	−173.5 (2)	C8—C9—O1—C1'	42.6 (2)
O3—C1—C10—C5	176.1 (2)	O1—C1'—O2—C8	33.2 (3)
C29—C1—C10—C5	50.1 (2)	O3—C1'—O2—C8	−87.3 (3)
C2—C1—C10—C5	−57.0 (3)	C2'—C1'—O2—C8	152.8 (2)
O1—C9—C10—C1	68.8 (2)	C30—C8—O2—C1'	112.8 (2)
C11—C9—C10—C1	−172.0 (2)	C14—C8—O2—C1'	−118.8 (2)
C8—C9—C10—C1	−36.9 (3)	C9—C8—O2—C1'	−5.7 (3)
O1—C9—C10—C19	−48.3 (3)	O2—C1'—O3—C1	59.5 (3)
C11—C9—C10—C19	70.8 (3)	O1—C1'—O3—C1	−55.9 (3)
C8—C9—C10—C19	−154.0 (2)	C2'—C1'—O3—C1	−178.8 (2)
O1—C9—C10—C5	−177.6 (2)	C29—C1—O3—C1'	165.6 (2)
C11—C9—C10—C5	−58.5 (3)	C10—C1—O3—C1'	48.6 (3)
C8—C9—C10—C5	76.6 (3)	C2—C1—O3—C1'	−75.1 (3)
C6—C5—C10—C1	−145.5 (2)	O11—C24—O4—C3	6.9 (4)
C4—C5—C10—C1	−19.6 (2)	C25—C24—O4—C3	−171.5 (2)
C6—C5—C10—C9	99.4 (3)	C4—C3—O4—C24	102.6 (3)
C4—C5—C10—C9	−134.7 (2)	C2—C3—O4—C24	−142.4 (2)
C6—C5—C10—C19	−28.9 (3)	O14—C33—O6—C2	1.8 (4)
C4—C5—C10—C19	97.0 (2)	C34—C33—O6—C2	−178.2 (3)
O1—C9—C11—C12	−142.6 (2)	C3—C2—O6—C33	−50.3 (3)
C10—C9—C11—C12	102.2 (3)	C30—C2—O6—C33	79.2 (3)
C8—C9—C11—C12	−33.9 (3)	C1—C2—O6—C33	−158.8 (2)
C9—C11—C12—C13	66.1 (3)	O13—C31—O7—C30	−11.3 (4)
C11—C12—C13—C18	88.7 (3)	C32—C31—O7—C30	171.0 (3)
C11—C12—C13—C14	−30.1 (3)	C8—C30—O7—C31	137.3 (2)
C11—C12—C13—C17	−150.2 (2)	C2—C30—O7—C31	−104.1 (3)
C18—C13—C14—C15	71.8 (3)	O9—C16—O8—C17	−167.2 (3)
C17—C13—C14—C15	−49.9 (3)	C15—C16—O8—C17	17.2 (5)
C12—C13—C14—C15	−168.4 (2)	C20—C17—O8—C16	−160.4 (3)
C18—C13—C14—C8	−153.2 (2)	C13—C17—O8—C16	−35.0 (4)
C17—C13—C14—C8	85.1 (3)	C22—C23—O10—C21	0.0 (6)
C12—C13—C14—C8	−33.4 (3)	C20—C21—O10—C23	−0.3 (4)
O2—C8—C14—C15	−52.9 (3)	O15—C7—O16—C35	1.1 (6)
C30—C8—C14—C15	65.6 (3)	C6—C7—O16—C35	−177.7 (4)
C9—C8—C14—C15	−163.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O11i	0.97	2.41	3.326 (3)	157
C25—H25B···O1ii	0.96	2.34	3.294 (3)	176
C29—H29A···O10iii	0.97	2.51	3.348 (3)	145
C34—H34A···O11iv	0.96	2.62	3.293 (3)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O11i	0.97	2.41	3.326 (3)	157
C25—H25B⋯O1ii	0.96	2.34	3.294 (3)	176
C29—H29A⋯O10iii	0.97	2.51	3.348 (3)	145
C34—H34A⋯O11iv	0.96	2.62	3.293 (3)	127

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