14-De-oxyxyloccensin K from Chisocheton ceramicus (Meliaceae).

The title limonoid 14-de-oxyxyloccensin K, C(27)H(34)O(7), isolated from Chisocheton ceramicus (Meliaceae), features an oxygen linkage between carbon-3 and carbon-8 along with a tetra-hydro-furyl sub-unit. The six-membered rings adopt chair configurations and the tetra-hydro-furyl sub-unit has an envelope shape.

Related literature

For the synthesis of 14-de­oxyxyloccensin K from xyloccensin K, see: Kim et al. (2004 ▶). For the crystal structure of xyloccensin K, see: Kokpol et al. (1996 ▶). For a description of other xyloccensin limonoids, see: Wu et al. (2003 ▶).

Experimental

Crystal data

C27H34O7

M = 470.54

Orthorhombic,

a = 8.7174 (6) Å

b = 11.7401 (8) Å

c = 23.1106 (16) Å

V = 2365.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.25 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

22814 measured reflections

3083 independent reflections

2674 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.098

S = 1.03

3083 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002564X/bt5284sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002564X/bt5284Isup2.hkl

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

C27H34O7	F(000) = 1008
Mr = 470.54	Dx = 1.321 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5382 reflections
a = 8.7174 (6) Å	θ = 2.5–27.9°
b = 11.7401 (8) Å	µ = 0.10 mm−1
c = 23.1106 (16) Å	T = 100 K
V = 2365.2 (3) Å3	Triangular plate, colorless
Z = 4	0.25 × 0.15 × 0.05 mm

Bruker SMART APEX diffractometer	2674 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
graphite	θmax = 27.5°, θmin = 1.8°
ω scans	h = −11→10
22814 measured reflections	k = −15→15
3083 independent reflections	l = −29→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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0502P)2 + 0.7549P] where P = (Fo2 + 2Fc2)/3
3083 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.7791 (2)	0.99435 (15)	0.16955 (8)	0.0278 (4)
O2	0.34822 (19)	0.79390 (12)	0.19484 (7)	0.0208 (4)
O3	0.1819 (2)	0.65454 (13)	0.19079 (8)	0.0267 (4)
O4	0.20193 (19)	0.82792 (12)	0.31200 (6)	0.0177 (3)
O5	0.5624 (2)	1.06497 (15)	0.44621 (7)	0.0281 (4)
O6	0.4725 (2)	1.10625 (17)	0.53467 (8)	0.0333 (5)
O7	−0.0536 (2)	0.96552 (15)	0.46084 (8)	0.0306 (4)
C1	0.6616 (3)	0.9897 (2)	0.20877 (11)	0.0242 (5)
H1	0.6643	1.0232	0.2462	0.029*
C2	0.7301 (3)	0.9356 (2)	0.12191 (12)	0.0280 (6)
H2	0.7888	0.9241	0.0878	0.034*
C3	0.5866 (3)	0.8964 (2)	0.13033 (11)	0.0250 (5)
H3	0.5268	0.8537	0.1037	0.030*
C4	0.5416 (3)	0.93121 (19)	0.18712 (10)	0.0199 (5)
C5	0.3928 (3)	0.90631 (18)	0.21706 (10)	0.0181 (5)
H5	0.4153	0.8975	0.2592	0.022*
C6	0.2663 (3)	0.99724 (19)	0.21106 (10)	0.0174 (5)
C7	0.1137 (3)	0.94872 (18)	0.23416 (10)	0.0180 (5)
H7	0.0320	1.0060	0.2253	0.022*
C8	0.0746 (3)	0.84036 (19)	0.20019 (10)	0.0199 (5)
H8A	−0.0151	0.8033	0.2185	0.024*
H8B	0.0448	0.8621	0.1604	0.024*
C9	0.2029 (3)	0.75607 (19)	0.19700 (10)	0.0201 (5)
C10	0.2485 (3)	1.0343 (2)	0.14753 (11)	0.0237 (5)
H10A	0.3462	1.0648	0.1334	0.036*
H10B	0.1692	1.0932	0.1447	0.036*
H10C	0.2187	0.9685	0.1240	0.036*
C11	0.3102 (3)	1.10229 (18)	0.24743 (10)	0.0196 (5)
H11A	0.4114	1.1305	0.2343	0.024*
H11B	0.2341	1.1633	0.2403	0.024*
C12	0.3179 (3)	1.07930 (19)	0.31233 (10)	0.0204 (5)
H12A	0.3410	1.1513	0.3329	0.024*
H12B	0.4023	1.0251	0.3203	0.024*
C13	0.1678 (3)	1.03012 (18)	0.33536 (10)	0.0187 (5)
H13	0.0895	1.0914	0.3298	0.022*
C14	0.1096 (3)	0.92757 (18)	0.29983 (10)	0.0182 (5)
C15	−0.0487 (3)	0.8923 (2)	0.32228 (10)	0.0210 (5)
H15A	−0.0979	0.8353	0.2967	0.025*
H15B	−0.1176	0.9586	0.3271	0.025*
C16	−0.0026 (3)	0.8406 (2)	0.38075 (10)	0.0215 (5)
H16	−0.0819	0.7875	0.3966	0.026*
C17	0.1497 (3)	0.77978 (19)	0.36585 (10)	0.0196 (5)
H17	0.1292	0.6967	0.3602	0.024*
C18	0.2718 (3)	0.79431 (19)	0.41271 (10)	0.0204 (5)
C19	0.3077 (3)	0.92499 (19)	0.42077 (10)	0.0200 (5)
H19	0.3949	0.9428	0.3942	0.024*
C20	0.1715 (3)	1.00645 (19)	0.40270 (10)	0.0202 (5)
C21	0.0274 (3)	0.9414 (2)	0.41994 (10)	0.0221 (5)
C22	0.4198 (3)	0.7342 (2)	0.39397 (10)	0.0238 (5)
H22A	0.3997	0.6527	0.3888	0.036*
H22B	0.4985	0.7446	0.4238	0.036*
H22C	0.4559	0.7669	0.3574	0.036*
C23	0.2093 (3)	0.7351 (2)	0.46731 (10)	0.0269 (6)
H23A	0.1894	0.6547	0.4588	0.040*
H23B	0.1138	0.7721	0.4794	0.040*
H23C	0.2851	0.7408	0.4985	0.040*
C24	0.1745 (3)	1.1215 (2)	0.43403 (11)	0.0249 (5)
H24A	0.0877	1.1680	0.4211	0.037*
H24B	0.2707	1.1610	0.4252	0.037*
H24C	0.1671	1.1090	0.4759	0.037*
C25	0.3663 (3)	0.9470 (2)	0.48241 (10)	0.0245 (5)
H25A	0.2762	0.9555	0.5081	0.029*
H25B	0.4230	0.8785	0.4954	0.029*
C26	0.4692 (3)	1.0497 (2)	0.49100 (10)	0.0254 (5)
C27	0.6748 (3)	1.1553 (2)	0.45213 (12)	0.0317 (6)
H27A	0.7375	1.1592	0.4170	0.047*
H27B	0.7409	1.1395	0.4855	0.047*
H27C	0.6220	1.2281	0.4579	0.047*

	U11	U22	U33	U12	U13	U23
O1	0.0202 (9)	0.0236 (9)	0.0395 (10)	−0.0015 (8)	−0.0016 (8)	0.0028 (8)
O2	0.0216 (9)	0.0111 (7)	0.0297 (9)	−0.0028 (7)	−0.0001 (7)	−0.0013 (6)
O3	0.0285 (10)	0.0143 (8)	0.0372 (9)	−0.0041 (8)	−0.0022 (8)	−0.0015 (7)
O4	0.0210 (9)	0.0118 (7)	0.0202 (7)	0.0020 (6)	−0.0004 (7)	0.0014 (6)
O5	0.0338 (11)	0.0255 (9)	0.0250 (9)	−0.0024 (9)	−0.0002 (8)	−0.0053 (7)
O6	0.0369 (12)	0.0394 (11)	0.0235 (9)	−0.0049 (10)	−0.0029 (9)	−0.0100 (8)
O7	0.0355 (11)	0.0244 (9)	0.0319 (10)	0.0036 (8)	0.0113 (9)	−0.0022 (7)
C1	0.0217 (12)	0.0238 (12)	0.0272 (12)	−0.0006 (10)	−0.0013 (10)	0.0037 (10)
C2	0.0304 (15)	0.0207 (12)	0.0328 (13)	0.0014 (11)	0.0034 (11)	−0.0013 (10)
C3	0.0263 (14)	0.0197 (11)	0.0290 (13)	−0.0043 (10)	0.0019 (11)	−0.0025 (10)
C4	0.0211 (12)	0.0140 (10)	0.0248 (11)	−0.0005 (9)	−0.0033 (10)	0.0020 (9)
C5	0.0214 (12)	0.0101 (10)	0.0228 (11)	−0.0021 (9)	−0.0019 (9)	−0.0004 (8)
C6	0.0165 (11)	0.0131 (10)	0.0225 (11)	−0.0015 (9)	−0.0041 (9)	0.0019 (9)
C7	0.0180 (12)	0.0123 (10)	0.0237 (11)	−0.0006 (9)	−0.0036 (9)	0.0014 (8)
C8	0.0194 (12)	0.0173 (11)	0.0231 (12)	−0.0026 (9)	−0.0046 (9)	−0.0013 (9)
C9	0.0241 (13)	0.0169 (10)	0.0191 (11)	−0.0025 (9)	−0.0024 (10)	0.0014 (8)
C10	0.0268 (13)	0.0189 (11)	0.0255 (12)	−0.0012 (10)	−0.0043 (10)	0.0044 (9)
C11	0.0219 (13)	0.0097 (9)	0.0272 (11)	−0.0011 (9)	−0.0026 (10)	0.0025 (8)
C12	0.0237 (12)	0.0130 (10)	0.0246 (11)	−0.0029 (9)	−0.0017 (10)	−0.0029 (9)
C13	0.0217 (12)	0.0103 (9)	0.0241 (11)	0.0002 (9)	−0.0016 (9)	−0.0024 (8)
C14	0.0178 (11)	0.0114 (9)	0.0253 (12)	0.0010 (9)	−0.0014 (9)	−0.0005 (8)
C15	0.0207 (12)	0.0136 (10)	0.0286 (12)	−0.0022 (9)	0.0003 (10)	−0.0010 (9)
C16	0.0227 (13)	0.0149 (10)	0.0269 (12)	0.0005 (10)	0.0026 (10)	0.0002 (9)
C17	0.0237 (13)	0.0117 (10)	0.0234 (11)	0.0009 (9)	0.0030 (10)	0.0017 (8)
C18	0.0269 (13)	0.0148 (10)	0.0196 (11)	0.0034 (10)	−0.0006 (9)	−0.0005 (8)
C19	0.0237 (13)	0.0165 (10)	0.0198 (11)	0.0012 (10)	−0.0018 (10)	−0.0023 (9)
C20	0.0231 (13)	0.0159 (10)	0.0218 (11)	0.0018 (10)	−0.0005 (10)	−0.0026 (9)
C21	0.0278 (13)	0.0149 (11)	0.0236 (12)	0.0044 (10)	0.0000 (10)	0.0003 (9)
C22	0.0282 (14)	0.0195 (11)	0.0237 (12)	0.0063 (10)	−0.0016 (10)	−0.0007 (9)
C23	0.0343 (15)	0.0215 (12)	0.0248 (12)	0.0038 (11)	0.0024 (11)	0.0024 (10)
C24	0.0270 (14)	0.0171 (11)	0.0307 (13)	0.0028 (10)	−0.0005 (11)	−0.0055 (9)
C25	0.0306 (14)	0.0226 (12)	0.0203 (11)	0.0024 (11)	−0.0016 (10)	−0.0013 (9)
C26	0.0287 (14)	0.0279 (12)	0.0197 (11)	0.0055 (11)	−0.0058 (10)	−0.0020 (10)
C27	0.0345 (16)	0.0297 (13)	0.0308 (13)	−0.0056 (13)	−0.0013 (12)	−0.0045 (11)

O1—C2	1.368 (3)	C12—H12B	0.9900
O1—C1	1.369 (3)	C13—C14	1.543 (3)
O2—C9	1.343 (3)	C13—C20	1.581 (3)
O2—C5	1.468 (3)	C13—H13	1.0000
O3—C9	1.215 (3)	C14—C15	1.531 (3)
O4—C17	1.441 (3)	C15—C16	1.535 (3)
O4—C14	1.448 (3)	C15—H15A	0.9900
O5—C26	1.328 (3)	C15—H15B	0.9900
O5—C27	1.450 (3)	C16—C21	1.514 (3)
O6—C26	1.209 (3)	C16—C17	1.546 (3)
O7—C21	1.214 (3)	C16—H16	1.0000
C1—C4	1.348 (3)	C17—C18	1.528 (3)
C1—H1	0.9500	C17—H17	1.0000
C2—C3	1.347 (4)	C18—C22	1.533 (3)
C2—H2	0.9500	C18—C23	1.540 (3)
C3—C4	1.430 (3)	C18—C19	1.577 (3)
C3—H3	0.9500	C19—C25	1.535 (3)
C4—C5	1.499 (3)	C19—C20	1.580 (3)
C5—C6	1.541 (3)	C19—H19	1.0000
C5—H5	1.0000	C20—C21	1.523 (4)
C6—C10	1.539 (3)	C20—C24	1.533 (3)
C6—C11	1.541 (3)	C22—H22A	0.9800
C6—C7	1.543 (3)	C22—H22B	0.9800
C7—C8	1.533 (3)	C22—H22C	0.9800
C7—C14	1.538 (3)	C23—H23A	0.9800
C7—H7	1.0000	C23—H23B	0.9800
C8—C9	1.495 (3)	C23—H23C	0.9800
C8—H8A	0.9900	C24—H24A	0.9800
C8—H8B	0.9900	C24—H24B	0.9800
C10—H10A	0.9800	C24—H24C	0.9800
C10—H10B	0.9800	C25—C26	1.516 (4)
C10—H10C	0.9800	C25—H25A	0.9900
C11—C12	1.525 (3)	C25—H25B	0.9900
C11—H11A	0.9900	C27—H27A	0.9800
C11—H11B	0.9900	C27—H27B	0.9800
C12—C13	1.526 (3)	C27—H27C	0.9800
C12—H12A	0.9900
C2—O1—C1	106.2 (2)	C14—C15—C16	99.77 (19)
C9—O2—C5	122.25 (18)	C14—C15—H15A	111.8
C17—O4—C14	108.00 (17)	C16—C15—H15A	111.8
C26—O5—C27	116.02 (19)	C14—C15—H15B	111.8
C4—C1—O1	110.8 (2)	C16—C15—H15B	111.8
C4—C1—H1	124.6	H15A—C15—H15B	109.5
O1—C1—H1	124.6	C21—C16—C15	105.23 (19)
C3—C2—O1	110.3 (2)	C21—C16—C17	110.2 (2)
C3—C2—H2	124.9	C15—C16—C17	102.18 (18)
O1—C2—H2	124.9	C21—C16—H16	112.8
C2—C3—C4	106.8 (2)	C15—C16—H16	112.8
C2—C3—H3	126.6	C17—C16—H16	112.8
C4—C3—H3	126.6	O4—C17—C18	110.38 (19)
C1—C4—C3	105.9 (2)	O4—C17—C16	106.42 (18)
C1—C4—C5	126.9 (2)	C18—C17—C16	112.89 (19)
C3—C4—C5	127.3 (2)	O4—C17—H17	109.0
O2—C5—C4	104.05 (18)	C18—C17—H17	109.0
O2—C5—C6	113.69 (18)	C16—C17—H17	109.0
C4—C5—C6	116.28 (18)	C17—C18—C22	109.56 (19)
O2—C5—H5	107.5	C17—C18—C23	106.5 (2)
C4—C5—H5	107.5	C22—C18—C23	108.74 (19)
C6—C5—H5	107.5	C17—C18—C19	109.30 (18)
C10—C6—C11	108.62 (18)	C22—C18—C19	108.3 (2)
C10—C6—C5	110.7 (2)	C23—C18—C19	114.36 (19)
C11—C6—C5	109.13 (18)	C25—C19—C18	109.83 (19)
C10—C6—C7	110.34 (19)	C25—C19—C20	113.17 (19)
C11—C6—C7	108.73 (19)	C18—C19—C20	114.12 (19)
C5—C6—C7	109.28 (18)	C25—C19—H19	106.4
C8—C7—C14	111.49 (18)	C18—C19—H19	106.4
C8—C7—C6	108.70 (19)	C20—C19—H19	106.4
C14—C7—C6	114.90 (19)	C21—C20—C24	109.4 (2)
C8—C7—H7	107.1	C21—C20—C19	104.29 (18)
C14—C7—H7	107.1	C24—C20—C19	113.3 (2)
C6—C7—H7	107.1	C21—C20—C13	109.2 (2)
C9—C8—C7	114.10 (19)	C24—C20—C13	108.09 (18)
C9—C8—H8A	108.7	C19—C20—C13	112.45 (19)
C7—C8—H8A	108.7	O7—C21—C16	123.2 (2)
C9—C8—H8B	108.7	O7—C21—C20	124.5 (2)
C7—C8—H8B	108.7	C16—C21—C20	112.2 (2)
H8A—C8—H8B	107.6	C18—C22—H22A	109.5
O3—C9—O2	117.6 (2)	C18—C22—H22B	109.5
O3—C9—C8	122.8 (2)	H22A—C22—H22B	109.5
O2—C9—C8	119.23 (19)	C18—C22—H22C	109.5
C6—C10—H10A	109.5	H22A—C22—H22C	109.5
C6—C10—H10B	109.5	H22B—C22—H22C	109.5
H10A—C10—H10B	109.5	C18—C23—H23A	109.5
C6—C10—H10C	109.5	C18—C23—H23B	109.5
H10A—C10—H10C	109.5	H23A—C23—H23B	109.5
H10B—C10—H10C	109.5	C18—C23—H23C	109.5
C12—C11—C6	113.94 (18)	H23A—C23—H23C	109.5
C12—C11—H11A	108.8	H23B—C23—H23C	109.5
C6—C11—H11A	108.8	C20—C24—H24A	109.5
C12—C11—H11B	108.8	C20—C24—H24B	109.5
C6—C11—H11B	108.8	H24A—C24—H24B	109.5
H11A—C11—H11B	107.7	C20—C24—H24C	109.5
C11—C12—C13	111.8 (2)	H24A—C24—H24C	109.5
C11—C12—H12A	109.2	H24B—C24—H24C	109.5
C13—C12—H12A	109.2	C26—C25—C19	116.9 (2)
C11—C12—H12B	109.2	C26—C25—H25A	108.1
C13—C12—H12B	109.2	C19—C25—H25A	108.1
H12A—C12—H12B	107.9	C26—C25—H25B	108.1
C12—C13—C14	113.05 (19)	C19—C25—H25B	108.1
C12—C13—C20	113.1 (2)	H25A—C25—H25B	107.3
C14—C13—C20	113.16 (18)	O6—C26—O5	124.2 (3)
C12—C13—H13	105.5	O6—C26—C25	124.1 (2)
C14—C13—H13	105.5	O5—C26—C25	111.6 (2)
C20—C13—H13	105.5	O5—C27—H27A	109.5
O4—C14—C15	102.50 (17)	O5—C27—H27B	109.5
O4—C14—C7	108.01 (18)	H27A—C27—H27B	109.5
C15—C14—C7	113.50 (19)	O5—C27—H27C	109.5
O4—C14—C13	110.14 (18)	H27A—C27—H27C	109.5
C15—C14—C13	109.10 (19)	H27B—C27—H27C	109.5
C7—C14—C13	113.05 (18)
C2—O1—C1—C4	−0.5 (3)	O4—C14—C15—C16	45.6 (2)
C1—O1—C2—C3	0.7 (3)	C7—C14—C15—C16	161.85 (18)
O1—C2—C3—C4	−0.6 (3)	C13—C14—C15—C16	−71.1 (2)
O1—C1—C4—C3	0.1 (3)	C14—C15—C16—C21	77.3 (2)
O1—C1—C4—C5	179.1 (2)	C14—C15—C16—C17	−37.9 (2)
C2—C3—C4—C1	0.3 (3)	C14—O4—C17—C18	−111.5 (2)
C2—C3—C4—C5	−178.7 (2)	C14—O4—C17—C16	11.3 (2)
C9—O2—C5—C4	−159.5 (2)	C21—C16—C17—O4	−93.7 (2)
C9—O2—C5—C6	−32.0 (3)	C15—C16—C17—O4	17.8 (2)
C1—C4—C5—O2	−146.5 (2)	C21—C16—C17—C18	27.6 (3)
C3—C4—C5—O2	32.3 (3)	C15—C16—C17—C18	139.03 (19)
C1—C4—C5—C6	87.6 (3)	O4—C17—C18—C22	−59.7 (2)
C3—C4—C5—C6	−93.5 (3)	C16—C17—C18—C22	−178.62 (19)
O2—C5—C6—C10	−73.1 (2)	O4—C17—C18—C23	−177.11 (17)
C4—C5—C6—C10	47.7 (3)	C16—C17—C18—C23	63.9 (2)
O2—C5—C6—C11	167.36 (18)	O4—C17—C18—C19	58.9 (2)
C4—C5—C6—C11	−71.8 (2)	C16—C17—C18—C19	−60.1 (3)
O2—C5—C6—C7	48.6 (2)	C17—C18—C19—C25	153.7 (2)
C4—C5—C6—C7	169.41 (19)	C22—C18—C19—C25	−87.0 (2)
C10—C6—C7—C8	64.1 (2)	C23—C18—C19—C25	34.5 (3)
C11—C6—C7—C8	−176.87 (18)	C17—C18—C19—C20	25.4 (3)
C5—C6—C7—C8	−57.9 (2)	C22—C18—C19—C20	144.74 (19)
C10—C6—C7—C14	−170.21 (19)	C23—C18—C19—C20	−93.8 (2)
C11—C6—C7—C14	−51.2 (2)	C25—C19—C20—C21	−91.2 (2)
C5—C6—C7—C14	67.8 (2)	C18—C19—C20—C21	35.4 (2)
C14—C7—C8—C9	−77.0 (2)	C25—C19—C20—C24	27.7 (3)
C6—C7—C8—C9	50.6 (2)	C18—C19—C20—C24	154.2 (2)
C5—O2—C9—O3	−162.9 (2)	C25—C19—C20—C13	150.6 (2)
C5—O2—C9—C8	23.9 (3)	C18—C19—C20—C13	−82.8 (2)
C7—C8—C9—O3	153.6 (2)	C12—C13—C20—C21	−171.48 (18)
C7—C8—C9—O2	−33.5 (3)	C14—C13—C20—C21	−41.3 (3)
C10—C6—C11—C12	175.0 (2)	C12—C13—C20—C24	69.6 (3)
C5—C6—C11—C12	−64.2 (3)	C14—C13—C20—C24	−160.2 (2)
C7—C6—C11—C12	54.9 (3)	C12—C13—C20—C19	−56.2 (2)
C6—C11—C12—C13	−55.8 (3)	C14—C13—C20—C19	74.0 (3)
C11—C12—C13—C14	50.3 (2)	C15—C16—C21—O7	111.6 (3)
C11—C12—C13—C20	−179.43 (18)	C17—C16—C21—O7	−138.9 (2)
C17—O4—C14—C15	−36.1 (2)	C15—C16—C21—C20	−69.5 (2)
C17—O4—C14—C7	−156.17 (18)	C17—C16—C21—C20	39.9 (3)
C17—O4—C14—C13	79.9 (2)	C24—C20—C21—O7	−14.6 (3)
C8—C7—C14—O4	50.7 (2)	C19—C20—C21—O7	106.9 (3)
C6—C7—C14—O4	−73.6 (2)	C13—C20—C21—O7	−132.7 (2)
C8—C7—C14—C15	−62.3 (2)	C24—C20—C21—C16	166.6 (2)
C6—C7—C14—C15	173.51 (18)	C19—C20—C21—C16	−71.9 (2)
C8—C7—C14—C13	172.8 (2)	C13—C20—C21—C16	48.5 (2)
C6—C7—C14—C13	48.6 (3)	C18—C19—C25—C26	153.9 (2)
C12—C13—C14—O4	74.0 (2)	C20—C19—C25—C26	−77.3 (3)
C20—C13—C14—O4	−56.2 (3)	C27—O5—C26—O6	0.8 (4)
C12—C13—C14—C15	−174.24 (18)	C27—O5—C26—C25	−175.0 (2)
C20—C13—C14—C15	55.6 (3)	C19—C25—C26—O6	147.3 (3)
C12—C13—C14—C7	−46.9 (3)	C19—C25—C26—O5	−36.9 (3)
C20—C13—C14—C7	−177.13 (19)