Andirobin from X. moluccensis.

THE TITLE COMPOUND (SYSTEMATIC NAME: methyl 2-{(1R,2R)-2-[(1aS,4S,4aS,8aS)-4-(furan-3-yl)-4a-methyl-8-methyl-ene-2-oxoocta-hydro-oxireno[2,3-d]isochromen-7-yl]-2,6,6-trimethyl-5-oxocyclo-hex-3-en-1-yl}acetate), C(27)H(32)O(7), was isolated from X. moluccensis seeds from Thailand. The conformations of the six-membered rings are distorted half-chair, chair and half-chair for the isolated cyclo-hexane, fused cyclo-hexane and lactone rings, respectively. In addition, the lactone ring bears in an equatorial orientation an essentially planar furan ring (r.m.s. deviation = 0.004 Å), which forms an angle of 63.87 (13)° with the mean plane defined by the ten atoms of the two fused six-membered rings (r.m.s. deviation = 0.213 Å). The absolute configuration was fixed on the basis of literature data.

Related literature

For general background to limonoids and their activities, see: Alvi et al. (1991 ▶); Yu et al. (2007 ▶); Li et al. (2009 ▶). For related structures, see: Chanin et al. (2010 ▶); Pudhom et al. (2009 ▶, 2010 ▶). For the bioactivity of limonoids, see: Koul et al. (2004 ▶); Endo et al. (2002 ▶); Nakagawa et al. (2001 ▶); Ravangpai et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C27H32O7

M = 468.53

Orthorhombic,

a = 8.8125 (5) Å

b = 12.5907 (7) Å

c = 21.9393 (11) Å

V = 2434.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.48 × 0.40 × 0.36 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

13719 measured reflections

3132 independent reflections

2725 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.117

S = 1.11

5520 reflections

312 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.18 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 datablock(s) global, I. DOI: 10.1107/S1600536812027705/lr2061sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027705/lr2061Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027705/lr2061Isup3.cml

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

C27H32O7	Z = 4
Mr = 468.53	F(000) = 1000
Orthorhombic, P212121	Dx = 1.278 Mg m−3
Hall symbol: P 2ac 2ab	Mo Kα radiation, λ = 0.71073 Å
a = 8.8125 (5) Å	µ = 0.09 mm−1
b = 12.5907 (7) Å	T = 296 K
c = 21.9393 (11) Å	Prism, colourless
V = 2434.3 (2) Å3	0.48 × 0.40 × 0.36 mm

Bruker SMART APEXII CCD area-detector diffractometer	2725 reflections with I > 2σ(I)
Radiation source: Mo Kα	Rint = 0.020
Graphite monochromator	θmax = 27.5°, θmin = 1.9°
φ and ω scans	h = −11→7
13719 measured reflections	k = −15→15
3132 independent reflections	l = −28→19

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041	w = 1/[σ2(Fo2) + (0.0714P)2 + 0.1995P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.117	(Δ/σ)max = 0.014
S = 1.11	Δρmax = 0.68 e Å−3
5520 reflections	Δρmin = −0.18 e Å−3
312 parameters

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.

	x	y	z	Uiso*/Ueq
C1	0.8749 (3)	0.19440 (18)	0.08892 (10)	0.0410 (5)
H1	0.7868	0.1870	0.0660	0.049*
C2	0.9926 (3)	0.2397 (2)	0.06213 (12)	0.0504 (6)
H2	0.9842	0.2570	0.0211	0.060*
C3	1.1348 (3)	0.2640 (2)	0.09316 (12)	0.0487 (6)
C4	1.1303 (3)	0.25998 (19)	0.16248 (12)	0.0427 (5)
C5	1.0339 (2)	0.16189 (17)	0.18228 (10)	0.0344 (4)
H5	1.0890	0.1003	0.1664	0.041*
C6	1.0335 (3)	0.1469 (2)	0.25150 (11)	0.0417 (5)
H6A	1.0424	0.2159	0.2708	0.050*
H6B	0.9369	0.1166	0.2636	0.050*
C7	1.1586 (3)	0.07683 (19)	0.27427 (10)	0.0406 (5)
C8	0.6587 (2)	0.00557 (17)	0.15184 (10)	0.0352 (4)
C9	0.8277 (2)	0.03182 (16)	0.15559 (9)	0.0324 (4)
H9	0.8598	0.0073	0.1960	0.039*
C10	0.8716 (2)	0.15387 (17)	0.15342 (10)	0.0338 (4)
C11	0.9130 (2)	−0.04026 (19)	0.10972 (10)	0.0377 (5)
H11A	1.0170	−0.0156	0.1068	0.045*
H11B	0.9156	−0.1118	0.1261	0.045*
C12	0.8468 (2)	−0.04512 (19)	0.04580 (10)	0.0364 (4)
H12A	0.9024	−0.0975	0.0223	0.044*
H12B	0.8606	0.0233	0.0262	0.044*
C13	0.6761 (2)	−0.07398 (16)	0.04482 (9)	0.0321 (4)
C14	0.5934 (2)	−0.00153 (17)	0.08910 (10)	0.0338 (4)
C15	0.4320 (2)	0.0194 (2)	0.07674 (11)	0.0436 (5)
H15	0.3670	0.0315	0.1123	0.052*
C16	0.3595 (3)	−0.0313 (2)	0.02300 (11)	0.0466 (6)
C17	0.6142 (2)	−0.05036 (19)	−0.01938 (10)	0.0369 (5)
H17	0.6351	0.0243	−0.0288	0.044*
C18	0.6499 (3)	−0.18975 (18)	0.06402 (11)	0.0447 (5)
H18A	0.5447	−0.2074	0.0588	0.067*
H18B	0.6776	−0.1984	0.1060	0.067*
H18C	0.7109	−0.2358	0.0392	0.067*
C19	0.7500 (3)	0.21722 (19)	0.18871 (12)	0.0447 (6)
H19A	0.7865	0.2878	0.1964	0.067*
H19B	0.7291	0.1825	0.2267	0.067*
H19C	0.6587	0.2208	0.1649	0.067*
C20	0.6791 (3)	−0.11713 (19)	−0.06933 (10)	0.0394 (5)
C21	0.7912 (3)	−0.0869 (2)	−0.10764 (12)	0.0569 (7)
H21	0.8380	−0.0207	−0.1070	0.068*
C22	0.6448 (4)	−0.2222 (2)	−0.08653 (13)	0.0603 (7)
H22	0.5727	−0.2659	−0.0684	0.072*
C23	0.7334 (4)	−0.2479 (3)	−0.13315 (12)	0.0614 (8)
H23	0.7318	−0.3129	−0.1533	0.074*
C28	1.0646 (3)	0.3679 (2)	0.18309 (17)	0.0640 (8)
H28A	1.0457	0.3662	0.2262	0.096*
H28B	0.9713	0.3813	0.1618	0.096*
H28C	1.1360	0.4233	0.1741	0.096*
C29	1.2920 (3)	0.2503 (2)	0.18786 (14)	0.0534 (6)
H29A	1.3322	0.1816	0.1780	0.080*
H29B	1.2898	0.2590	0.2313	0.080*
H29C	1.3549	0.3043	0.1701	0.080*
C30	0.5775 (3)	−0.0189 (2)	0.20065 (11)	0.0503 (6)
H30A	0.4774	−0.0411	0.1963	0.060*
H30B	0.6205	−0.0139	0.2392	0.060*
C31	1.3128 (4)	0.0371 (3)	0.35953 (15)	0.0744 (9)
H31A	1.2729	−0.0330	0.3658	0.112*
H31B	1.3411	0.0674	0.3980	0.112*
H31C	1.4004	0.0333	0.3336	0.112*
O1	0.8261 (3)	−0.1661 (2)	−0.14718 (10)	0.0712 (6)
O2	0.44932 (17)	−0.06685 (16)	−0.02238 (8)	0.0484 (4)
O3	0.54407 (18)	0.09958 (13)	0.06392 (8)	0.0427 (4)
O4	0.22495 (19)	−0.0432 (2)	0.01901 (10)	0.0681 (6)
O5	1.2467 (2)	0.2941 (2)	0.06570 (11)	0.0795 (7)
O6	1.2129 (2)	0.00409 (15)	0.24700 (8)	0.0535 (4)
O7	1.1985 (2)	0.10284 (18)	0.33109 (8)	0.0591 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0448 (12)	0.0358 (11)	0.0423 (12)	0.0015 (10)	−0.0057 (10)	0.0053 (9)
C2	0.0575 (14)	0.0491 (14)	0.0446 (13)	−0.0022 (12)	0.0010 (11)	0.0135 (11)
C3	0.0472 (13)	0.0420 (12)	0.0571 (15)	−0.0019 (11)	0.0068 (12)	0.0113 (11)
C4	0.0369 (10)	0.0364 (11)	0.0549 (14)	−0.0032 (9)	0.0027 (10)	−0.0047 (10)
C5	0.0313 (9)	0.0342 (10)	0.0377 (11)	0.0007 (9)	0.0029 (9)	−0.0039 (9)
C6	0.0383 (11)	0.0486 (13)	0.0380 (11)	0.0017 (10)	0.0011 (10)	−0.0083 (10)
C7	0.0340 (10)	0.0505 (13)	0.0373 (11)	−0.0068 (10)	0.0002 (9)	−0.0020 (10)
C8	0.0333 (9)	0.0357 (10)	0.0368 (10)	0.0013 (9)	0.0054 (9)	−0.0015 (9)
C9	0.0317 (9)	0.0339 (10)	0.0316 (9)	0.0027 (8)	0.0000 (8)	0.0026 (8)
C10	0.0317 (9)	0.0330 (10)	0.0368 (10)	0.0028 (8)	0.0011 (9)	−0.0006 (8)
C11	0.0320 (9)	0.0398 (11)	0.0414 (11)	0.0074 (9)	−0.0018 (9)	−0.0077 (10)
C12	0.0293 (9)	0.0411 (11)	0.0386 (10)	0.0025 (9)	0.0041 (9)	−0.0052 (9)
C13	0.0306 (9)	0.0333 (10)	0.0325 (10)	−0.0015 (8)	0.0019 (8)	0.0001 (8)
C14	0.0295 (9)	0.0351 (10)	0.0367 (10)	0.0001 (8)	0.0056 (8)	0.0020 (9)
C15	0.0309 (10)	0.0559 (14)	0.0438 (12)	0.0045 (10)	0.0045 (9)	−0.0038 (11)
C16	0.0320 (10)	0.0609 (15)	0.0470 (13)	0.0008 (11)	0.0005 (10)	0.0015 (11)
C17	0.0299 (9)	0.0444 (11)	0.0365 (10)	−0.0002 (9)	0.0006 (8)	0.0017 (10)
C18	0.0554 (13)	0.0355 (11)	0.0433 (12)	−0.0041 (11)	0.0017 (11)	0.0028 (9)
C19	0.0380 (11)	0.0396 (12)	0.0565 (14)	0.0083 (10)	0.0023 (11)	−0.0089 (11)
C20	0.0365 (10)	0.0490 (12)	0.0327 (10)	−0.0007 (10)	−0.0034 (9)	0.0000 (10)
C21	0.0575 (15)	0.0646 (16)	0.0486 (14)	−0.0055 (14)	0.0143 (13)	−0.0092 (13)
C22	0.0700 (18)	0.0625 (16)	0.0485 (14)	−0.0169 (15)	0.0043 (14)	−0.0103 (13)
C23	0.079 (2)	0.0610 (17)	0.0440 (14)	0.0081 (16)	−0.0053 (14)	−0.0161 (13)
C28	0.0568 (16)	0.0386 (13)	0.097 (2)	−0.0021 (12)	0.0090 (16)	−0.0122 (14)
C29	0.0393 (11)	0.0538 (15)	0.0671 (16)	−0.0080 (12)	−0.0017 (12)	−0.0075 (13)
C30	0.0443 (12)	0.0640 (16)	0.0426 (12)	−0.0058 (12)	0.0092 (11)	0.0043 (12)
C31	0.0599 (16)	0.102 (3)	0.0610 (17)	0.0075 (19)	−0.0247 (15)	−0.0005 (18)
O1	0.0636 (12)	0.0953 (17)	0.0548 (11)	0.0116 (13)	0.0136 (10)	−0.0144 (11)
O2	0.0303 (7)	0.0707 (12)	0.0441 (9)	−0.0009 (8)	−0.0025 (7)	−0.0084 (8)
O3	0.0379 (7)	0.0408 (8)	0.0493 (9)	0.0077 (7)	−0.0028 (7)	0.0008 (7)
O4	0.0308 (8)	0.1065 (17)	0.0671 (12)	−0.0061 (10)	0.0017 (9)	−0.0101 (13)
O5	0.0559 (12)	0.110 (2)	0.0727 (13)	−0.0154 (12)	0.0136 (11)	0.0291 (14)
O6	0.0519 (10)	0.0581 (11)	0.0504 (10)	0.0105 (9)	−0.0017 (8)	−0.0012 (9)
O7	0.0537 (10)	0.0788 (13)	0.0450 (10)	0.0036 (10)	−0.0149 (8)	−0.0079 (9)

C1—C2	1.321 (3)	C14—C15	1.471 (3)
C1—C10	1.505 (3)	C15—O3	1.440 (3)
C1—H1	0.9300	C15—C16	1.485 (3)
C2—C3	1.459 (4)	C15—H15	0.9800
C2—H2	0.9300	C16—O4	1.198 (3)
C3—O5	1.215 (3)	C16—O2	1.348 (3)
C3—C4	1.522 (4)	C17—O2	1.469 (2)
C4—C29	1.534 (3)	C17—C20	1.495 (3)
C4—C28	1.545 (3)	C17—H17	0.9800
C4—C5	1.561 (3)	C18—H18A	0.9600
C5—C6	1.530 (3)	C18—H18B	0.9600
C5—C10	1.567 (3)	C18—H18C	0.9600
C5—H5	0.9800	C19—H19A	0.9600
C6—C7	1.498 (3)	C19—H19B	0.9600
C6—H6A	0.9700	C19—H19C	0.9600
C6—H6B	0.9700	C20—C21	1.351 (4)
C7—O6	1.194 (3)	C20—C22	1.408 (4)
C7—O7	1.336 (3)	C21—O1	1.358 (3)
C8—C30	1.324 (3)	C21—H21	0.9300
C8—C14	1.495 (3)	C22—C23	1.327 (4)
C8—C9	1.528 (3)	C22—H22	0.9300
C9—C11	1.550 (3)	C23—O1	1.350 (4)
C9—C10	1.585 (3)	C23—H23	0.9300
C9—H9	0.9800	C28—H28A	0.9600
C10—C19	1.545 (3)	C28—H28B	0.9600
C11—C12	1.520 (3)	C28—H28C	0.9600
C11—H11A	0.9700	C29—H29A	0.9600
C11—H11B	0.9700	C29—H29B	0.9600
C12—C13	1.547 (3)	C29—H29C	0.9600
C12—H12A	0.9700	C30—H30A	0.9300
C12—H12B	0.9700	C30—H30B	0.9300
C13—C14	1.519 (3)	C31—O7	1.445 (4)
C13—C18	1.535 (3)	C31—H31A	0.9600
C13—C17	1.540 (3)	C31—H31B	0.9600
C14—O3	1.454 (3)	C31—H31C	0.9600
C2—C1—C10	125.4 (2)	C15—C14—C13	116.97 (19)
C2—C1—H1	117.3	C8—C14—C13	116.10 (17)
C10—C1—H1	117.3	O3—C15—C14	59.93 (13)
C1—C2—C3	123.9 (2)	O3—C15—C16	116.2 (2)
C1—C2—H2	118.1	C14—C15—C16	119.0 (2)
C3—C2—H2	118.1	O3—C15—H15	116.5
O5—C3—C2	122.1 (2)	C14—C15—H15	116.5
O5—C3—C4	121.8 (3)	C16—C15—H15	116.5
C2—C3—C4	115.9 (2)	O4—C16—O2	119.0 (2)
C3—C4—C29	109.9 (2)	O4—C16—C15	122.5 (2)
C3—C4—C28	105.8 (2)	O2—C16—C15	118.41 (18)
C29—C4—C28	108.2 (2)	O2—C17—C20	105.46 (18)
C3—C4—C5	108.59 (19)	O2—C17—C13	111.37 (17)
C29—C4—C5	110.0 (2)	C20—C17—C13	115.22 (18)
C28—C4—C5	114.23 (19)	O2—C17—H17	108.2
C6—C5—C4	112.02 (19)	C20—C17—H17	108.2
C6—C5—C10	113.03 (17)	C13—C17—H17	108.2
C4—C5—C10	115.81 (18)	C13—C18—H18A	109.5
C6—C5—H5	104.9	C13—C18—H18B	109.5
C4—C5—H5	104.9	H18A—C18—H18B	109.5
C10—C5—H5	104.9	C13—C18—H18C	109.5
C7—C6—C5	113.70 (19)	H18A—C18—H18C	109.5
C7—C6—H6A	108.8	H18B—C18—H18C	109.5
C5—C6—H6A	108.8	C10—C19—H19A	109.5
C7—C6—H6B	108.8	C10—C19—H19B	109.5
C5—C6—H6B	108.8	H19A—C19—H19B	109.5
H6A—C6—H6B	107.7	C10—C19—H19C	109.5
O6—C7—O7	123.4 (2)	H19A—C19—H19C	109.5
O6—C7—C6	125.4 (2)	H19B—C19—H19C	109.5
O7—C7—C6	111.1 (2)	C21—C20—C22	104.8 (2)
C30—C8—C14	121.5 (2)	C21—C20—C17	125.2 (2)
C30—C8—C9	122.2 (2)	C22—C20—C17	130.0 (2)
C14—C8—C9	115.96 (17)	C20—C21—O1	110.9 (3)
C8—C9—C11	108.14 (17)	C20—C21—H21	124.6
C8—C9—C10	116.50 (17)	O1—C21—H21	124.6
C11—C9—C10	115.45 (17)	C23—C22—C20	108.0 (3)
C8—C9—H9	105.2	C23—C22—H22	126.0
C11—C9—H9	105.2	C20—C22—H22	126.0
C10—C9—H9	105.2	C22—C23—O1	110.2 (3)
C1—C10—C19	108.03 (19)	C22—C23—H23	124.9
C1—C10—C5	109.93 (18)	O1—C23—H23	124.9
C19—C10—C5	113.42 (18)	C4—C28—H28A	109.5
C1—C10—C9	111.20 (17)	C4—C28—H28B	109.5
C19—C10—C9	108.42 (17)	H28A—C28—H28B	109.5
C5—C10—C9	105.86 (16)	C4—C28—H28C	109.5
C12—C11—C9	115.89 (17)	H28A—C28—H28C	109.5
C12—C11—H11A	108.3	H28B—C28—H28C	109.5
C9—C11—H11A	108.3	C4—C29—H29A	109.5
C12—C11—H11B	108.3	C4—C29—H29B	109.5
C9—C11—H11B	108.3	H29A—C29—H29B	109.5
H11A—C11—H11B	107.4	C4—C29—H29C	109.5
C11—C12—C13	113.28 (18)	H29A—C29—H29C	109.5
C11—C12—H12A	108.9	H29B—C29—H29C	109.5
C13—C12—H12A	108.9	C8—C30—H30A	120.0
C11—C12—H12B	108.9	C8—C30—H30B	120.0
C13—C12—H12B	108.9	H30A—C30—H30B	120.0
H12A—C12—H12B	107.7	O7—C31—H31A	109.5
C14—C13—C18	108.80 (18)	O7—C31—H31B	109.5
C14—C13—C17	107.38 (17)	H31A—C31—H31B	109.5
C18—C13—C17	112.39 (18)	O7—C31—H31C	109.5
C14—C13—C12	108.47 (17)	H31A—C31—H31C	109.5
C18—C13—C12	111.46 (19)	H31B—C31—H31C	109.5
C17—C13—C12	108.19 (17)	C23—O1—C21	106.1 (2)
O3—C14—C15	58.98 (15)	C16—O2—C17	120.06 (18)
O3—C14—C8	114.37 (18)	C15—O3—C14	61.09 (14)
C15—C14—C8	122.08 (19)	C7—O7—C31	116.5 (2)
O3—C14—C13	115.22 (17)
C10—C1—C2—C3	−4.6 (4)	C9—C8—C14—C15	−153.4 (2)
C1—C2—C3—O5	171.1 (3)	C30—C8—C14—C13	−122.1 (2)
C1—C2—C3—C4	−14.6 (4)	C9—C8—C14—C13	52.1 (3)
O5—C3—C4—C29	−24.3 (4)	C18—C13—C14—O3	−151.59 (18)
C2—C3—C4—C29	161.4 (2)	C17—C13—C14—O3	−29.7 (2)
O5—C3—C4—C28	92.2 (3)	C12—C13—C14—O3	87.0 (2)
C2—C3—C4—C28	−82.1 (3)	C18—C13—C14—C15	−85.1 (2)
O5—C3—C4—C5	−144.7 (3)	C17—C13—C14—C15	36.8 (3)
C2—C3—C4—C5	41.0 (3)	C12—C13—C14—C15	153.5 (2)
C3—C4—C5—C6	175.64 (19)	C18—C13—C14—C8	70.8 (2)
C29—C4—C5—C6	55.3 (3)	C17—C13—C14—C8	−167.32 (18)
C28—C4—C5—C6	−66.5 (3)	C12—C13—C14—C8	−50.6 (2)
C3—C4—C5—C10	−52.7 (2)	C8—C14—C15—O3	101.0 (2)
C29—C4—C5—C10	−173.07 (19)	C13—C14—C15—O3	−104.6 (2)
C28—C4—C5—C10	65.1 (3)	O3—C14—C15—C16	105.2 (2)
C4—C5—C6—C7	−90.5 (2)	C8—C14—C15—C16	−153.8 (2)
C10—C5—C6—C7	136.50 (19)	C13—C14—C15—C16	0.6 (3)
C5—C6—C7—O6	−31.4 (3)	O3—C15—C16—O4	−132.8 (3)
C5—C6—C7—O7	151.5 (2)	C14—C15—C16—O4	158.6 (3)
C30—C8—C9—C11	127.1 (2)	O3—C15—C16—O2	48.4 (3)
C14—C8—C9—C11	−47.0 (2)	C14—C15—C16—O2	−20.2 (4)
C30—C8—C9—C10	−100.9 (3)	C14—C13—C17—O2	−58.0 (2)
C14—C8—C9—C10	84.9 (2)	C18—C13—C17—O2	61.6 (2)
C2—C1—C10—C19	118.2 (3)	C12—C13—C17—O2	−174.94 (18)
C2—C1—C10—C5	−6.1 (3)	C14—C13—C17—C20	−178.09 (18)
C2—C1—C10—C9	−123.0 (3)	C18—C13—C17—C20	−58.5 (3)
C6—C5—C10—C1	166.66 (19)	C12—C13—C17—C20	65.0 (2)
C4—C5—C10—C1	35.5 (2)	O2—C17—C20—C21	137.5 (3)
C6—C5—C10—C19	45.6 (3)	C13—C17—C20—C21	−99.2 (3)
C4—C5—C10—C19	−85.6 (2)	O2—C17—C20—C22	−44.4 (3)
C6—C5—C10—C9	−73.1 (2)	C13—C17—C20—C22	78.9 (3)
C4—C5—C10—C9	155.70 (18)	C22—C20—C21—O1	0.5 (3)
C8—C9—C10—C1	−81.7 (2)	C17—C20—C21—O1	179.0 (2)
C11—C9—C10—C1	46.8 (2)	C21—C20—C22—C23	−0.9 (3)
C8—C9—C10—C19	36.9 (3)	C17—C20—C22—C23	−179.3 (3)
C11—C9—C10—C19	165.38 (18)	C20—C22—C23—O1	0.9 (4)
C8—C9—C10—C5	158.90 (17)	C22—C23—O1—C21	−0.6 (4)
C11—C9—C10—C5	−72.6 (2)	C20—C21—O1—C23	0.0 (3)
C8—C9—C11—C12	48.3 (3)	O4—C16—O2—C17	178.2 (3)
C10—C9—C11—C12	−84.2 (2)	C15—C16—O2—C17	−3.0 (4)
C9—C11—C12—C13	−53.0 (3)	C20—C17—O2—C16	169.0 (2)
C11—C12—C13—C14	50.4 (2)	C13—C17—O2—C16	43.4 (3)
C11—C12—C13—C18	−69.3 (2)	C16—C15—O3—C14	−109.9 (2)
C11—C12—C13—C17	166.60 (19)	C8—C14—O3—C15	−114.1 (2)
C30—C8—C14—O3	99.9 (3)	C13—C14—O3—C15	107.6 (2)
C9—C8—C14—O3	−85.9 (2)	O6—C7—O7—C31	−0.4 (4)
C30—C8—C14—C15	32.5 (3)	C6—C7—O7—C31	176.7 (2)