X-ray crystal structures of diacetates of 6-s-cis and 6-s-trans astaxanthin and of 7,8-didehydroastaxanthin and 7,8,7′,8′-tetradehydroastaxanthin: comparison with free and protein-bound asta­xanthins

The crystal structures of the 6-s-cis [s-cis-(1)] and 6-s-trans [s-trans-(1)] conformers of the diacetates of astaxanthin (AXT) and those of (3S,3′S)-7,8-didehydroastaxanthin [(3S,3′S)-3,3′-dihydroxy-7,8-didehydro-β,β-carotene-4,4′-dione (2)] and (3S,3′S)-7,8,7′,8′-tetradehydroastaxanthin [(3S,3′S)-3,3′-dihydroxy-7,8,7′,8′-tetradehydro-β,β-carotene-4, 4′-dione (3)] are reported. The conformations of these four molecules vary in particular with the angle of twist of the end rings out of the plane of the polyene chain; for s-cis-(1), the end rings are twisted out of the plane of the polyene chain by an angle of −49.0 (5)°, and the conformation is therefore similar to that found for unesterified AXT as well as for the carotenoids, canthaxanthin and β,β-carotene. For s-trans-(1), the end rings are coplanar with the polyene chain and its conformation is much more similar to that of the protein-bound AXT in the blue protein, crustacyanin, which is found in the shell of lobsters, although s-trans-(1) shows much less bowing of the polyene chain. In (2) and (3) the end rings are also almost coplanar with the polyene chain with the end rings in (2) in the s-cis conformation, and in (3) in the s-trans conformation. Thus, an extensive ensemble of the possible β end-ring conformations has been determined. These structures are compared with one another as well as unbound, unesterified AXT and protein-bound AXT. Also, the effect of the end-ring conformations on the colour and UV–vis spectra of the crystals was established.

Computing details

For all compounds, data collection: Bruker SMART; cell refinement: Bruker SMART; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Bruker SHELXTL; PLATON (Spek,2003); software used to prepare material for publication: Bruker SHELXTL; PLATON (Spek,2003).

Figures

(s-cis-1)

Crystal data

C44H56O6·0.44(C4H8O2)	F(000) = 1556
Mr = 719.59	Dx = 1.153 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C2yc	Cell parameters from 4444 reflections
a = 12.9673 (15) Å	θ = 2.5–26.4°
b = 10.7883 (13) Å	µ = 0.08 mm^−1
c = 30.264 (4) Å	T = 100 K
β = 101.796 (1)°	Plate, orange
V = 4144.3 (8) Å^3	0.60 × 0.60 × 0.05 mm
Z = 4

Data collection

Bruker APEX CCD area detector diffractometer	2913 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.076
Graphite monochromator	θmax = 25.0°, θmin = 2.5°
phi and ω scans	h = −15→15
13064 measured reflections	k = −12→12
3632 independent reflections	l = −35→35

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.218	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0625P)^2 + 15.0678P] where P = (Fo^2 + 2Fc^2)/3
3632 reflections	(Δ/σ)max < 0.001
304 parameters	Δρmax = 0.54 e Å^−3
117 restraints	Δρmin = −0.28 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O3	0.8438 (2)	0.5392 (4)	0.76819 (10)	0.0500 (10)	0.743 (4)
O4	0.6749 (3)	0.6950 (6)	0.75060 (14)	0.0599 (13)	0.743 (4)
O21	0.7427 (3)	0.4588 (7)	0.81238 (14)	0.0756 (15)	0.743 (4)
C1	0.7275 (3)	0.4789 (4)	0.64577 (11)	0.0438 (9)	0.743 (4)
C2	0.8081 (4)	0.5029 (8)	0.68898 (18)	0.0405 (14)	0.743 (4)
H2A	0.8608	0.4352	0.6933	0.049*	0.743 (4)
H2B	0.8456	0.5812	0.6857	0.049*	0.743 (4)
C3	0.7618 (4)	0.5114 (5)	0.72946 (15)	0.0462 (11)	0.743 (4)
H3	0.7279	0.4307	0.7343	0.055*	0.743 (4)
C4	0.6796 (4)	0.6138 (6)	0.72271 (16)	0.0457 (13)	0.743 (4)
C21	0.8211 (5)	0.5079 (6)	0.80802 (18)	0.0496 (13)	0.743 (4)
C22	0.9124 (4)	0.5375 (5)	0.84551 (16)	0.0503 (13)	0.743 (4)
H22A	0.8883	0.5411	0.8741	0.075*	0.743 (4)
H22B	0.9423	0.6178	0.8397	0.075*	0.743 (4)
H22C	0.9663	0.4730	0.8472	0.075*	0.743 (4)
O3B	0.8679 (7)	0.7147 (9)	0.7386 (3)	0.046 (3)*	0.257 (4)
O4B	0.6627 (11)	0.7507 (12)	0.7393 (4)	0.051 (4)*	0.257 (4)
O21B	0.9789 (9)	0.7782 (11)	0.6958 (4)	0.058 (3)*	0.257 (4)
C1B	0.7275 (3)	0.4789 (4)	0.64577 (11)	0.0438 (9)	0.257 (4)
C2B	0.8039 (15)	0.5405 (15)	0.6861 (6)	0.038 (6)*	0.257 (4)
H2D	0.8011	0.4898	0.7131	0.046*	0.257 (4)
H2E	0.8758	0.5307	0.6802	0.046*	0.257 (4)
C3B	0.7942 (9)	0.6733 (11)	0.6995 (4)	0.038 (3)*	0.257 (4)
H3B	0.8021	0.7270	0.6735	0.046*	0.257 (4)
C4B	0.6841 (9)	0.6913 (14)	0.7080 (5)	0.038 (3)*	0.257 (4)
C21B	0.9549 (10)	0.7718 (14)	0.7303 (4)	0.039 (3)*	0.257 (4)
C22B	1.0088 (14)	0.8293 (18)	0.7739 (5)	0.055 (4)*	0.257 (4)
H22D	1.0709	0.7799	0.7872	0.083*	0.257 (4)
H22E	0.9602	0.8320	0.7947	0.083*	0.257 (4)
H22F	1.0308	0.9137	0.7682	0.083*	0.257 (4)
C5	0.5996 (3)	0.6111 (4)	0.67832 (13)	0.0465 (10)
C6	0.6200 (2)	0.5380 (3)	0.64475 (11)	0.0340 (8)
C7	0.5385 (2)	0.5087 (3)	0.60463 (10)	0.0285 (7)
H7	0.5563	0.5194	0.5759	0.034*
C8	0.4415 (2)	0.4683 (3)	0.60543 (11)	0.0310 (7)
H8	0.4235	0.4599	0.6342	0.037*
C9	0.3610 (2)	0.4362 (3)	0.56609 (10)	0.0279 (7)
C10	0.2652 (2)	0.3960 (3)	0.57222 (11)	0.0315 (7)
H10	0.2575	0.3832	0.6024	0.038*
C11	0.1752 (2)	0.3712 (3)	0.53719 (11)	0.0298 (7)
H11	0.1828	0.3822	0.5069	0.036*
C12	0.0804 (2)	0.3333 (3)	0.54402 (11)	0.0289 (7)
H12	0.0753	0.3136	0.5741	0.035*
C13	−0.0138 (2)	0.3203 (3)	0.50945 (10)	0.0278 (7)
C14	−0.1055 (2)	0.2856 (3)	0.52153 (11)	0.0291 (7)
H14	−0.1013	0.2693	0.5527	0.035*
C15	−0.2070 (2)	0.2707 (3)	0.49289 (11)	0.0293 (7)
H15	−0.2145	0.2914	0.4619	0.035*
C16	0.7122 (5)	0.3328 (5)	0.6457 (2)	0.0474 (13)	0.743 (4)
H16A	0.7788	0.2921	0.6439	0.071*	0.743 (4)
H16B	0.6577	0.3087	0.6197	0.071*	0.743 (4)
H16C	0.6907	0.3074	0.6736	0.071*	0.743 (4)
C17	0.7701 (4)	0.5087 (8)	0.60408 (16)	0.0474 (14)	0.743 (4)
H17A	0.8415	0.4750	0.6074	0.071*	0.743 (4)
H17B	0.7721	0.5988	0.6002	0.071*	0.743 (4)
H17C	0.7244	0.4717	0.5776	0.071*	0.743 (4)
C16B	0.723 (3)	0.3478 (19)	0.6298 (11)	0.112 (14)*	0.257 (4)
H16D	0.6493	0.3253	0.6173	0.168*	0.257 (4)
H16E	0.7512	0.2930	0.6552	0.168*	0.257 (4)
H16F	0.7643	0.3390	0.6064	0.168*	0.257 (4)
C17B	0.774 (2)	0.566 (2)	0.6114 (8)	0.074 (8)*	0.257 (4)
H17D	0.7871	0.6495	0.6243	0.110*	0.257 (4)
H17E	0.7238	0.5710	0.5826	0.110*	0.257 (4)
H17F	0.8409	0.5312	0.6065	0.110*	0.257 (4)
C18	0.4987 (3)	0.6817 (4)	0.67708 (13)	0.0500 (10)
H18A	0.4617	0.6924	0.6457	0.075*
H18B	0.5149	0.7632	0.6911	0.075*
H18C	0.4538	0.6354	0.6937	0.075*
C19	0.3862 (2)	0.4522 (3)	0.52046 (10)	0.0304 (7)
H19A	0.3309	0.4135	0.4977	0.046*
H19B	0.4540	0.4129	0.5199	0.046*
H19C	0.3902	0.5408	0.5138	0.046*
C20	−0.0072 (2)	0.3484 (3)	0.46176 (11)	0.0324 (7)
H20A	−0.0771	0.3397	0.4423	0.049*
H20B	0.0418	0.2904	0.4519	0.049*
H20C	0.0182	0.4334	0.4598	0.049*
O1S	0.5479 (16)	0.325 (2)	0.7471 (7)	0.152 (10)*	0.22
O2S	0.6797 (14)	0.4532 (16)	0.7699 (6)	0.106 (6)*	0.22
C1S	0.6170 (16)	0.3579 (19)	0.7746 (6)	0.104 (9)*	0.22
C2S	0.6516 (17)	0.3024 (19)	0.8190 (6)	0.071 (6)*	0.22
H2S1	0.6027	0.2361	0.8232	0.107*	0.22
H2S2	0.6528	0.3658	0.8423	0.107*	0.22
H2S3	0.7224	0.2679	0.8215	0.107*	0.22
C3S	0.746 (3)	0.512 (3)	0.8059 (13)	0.22 (4)*	0.22
H3S1	0.7149	0.5018	0.8329	0.260*	0.22
H3S2	0.7446	0.6021	0.7990	0.260*	0.22
C4S	0.859 (3)	0.475 (5)	0.8190 (16)	0.15 (2)*	0.22
H4S1	0.8983	0.5390	0.8387	0.231*	0.22
H4S2	0.8887	0.4668	0.7919	0.231*	0.22
H4S3	0.8646	0.3961	0.8351	0.231*	0.22

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0348 (17)	0.081 (3)	0.0312 (15)	0.0048 (17)	−0.0013 (13)	−0.0064 (16)
O4	0.045 (2)	0.091 (4)	0.040 (2)	0.005 (2)	−0.0026 (17)	−0.027 (2)
O21	0.052 (3)	0.131 (5)	0.043 (2)	−0.007 (2)	0.0074 (18)	0.002 (3)
C1	0.0272 (16)	0.069 (2)	0.0323 (17)	0.0071 (17)	−0.0002 (13)	−0.0107 (17)
C2	0.028 (3)	0.056 (4)	0.032 (2)	0.012 (2)	−0.0059 (16)	−0.003 (3)
C3	0.036 (2)	0.065 (3)	0.033 (2)	0.001 (2)	−0.0014 (17)	−0.002 (2)
C4	0.033 (2)	0.073 (4)	0.031 (2)	0.003 (2)	0.0056 (18)	−0.011 (2)
C21	0.043 (3)	0.070 (4)	0.032 (2)	0.007 (3)	0.000 (2)	−0.010 (2)
C22	0.061 (3)	0.052 (3)	0.031 (2)	0.003 (3)	−0.006 (2)	−0.006 (2)
C1B	0.0272 (16)	0.069 (2)	0.0323 (17)	0.0071 (17)	−0.0002 (13)	−0.0107 (17)
C5	0.0281 (17)	0.065 (3)	0.045 (2)	−0.0028 (17)	0.0043 (15)	−0.0190 (19)
C6	0.0266 (16)	0.0411 (19)	0.0332 (17)	−0.0021 (14)	0.0036 (13)	−0.0021 (14)
C7	0.0295 (16)	0.0248 (16)	0.0302 (16)	0.0030 (13)	0.0036 (13)	0.0012 (13)
C8	0.0295 (16)	0.0304 (17)	0.0317 (16)	0.0000 (14)	0.0028 (13)	0.0037 (13)
C9	0.0274 (16)	0.0207 (15)	0.0342 (17)	0.0020 (13)	0.0030 (13)	0.0012 (13)
C10	0.0325 (17)	0.0267 (16)	0.0342 (17)	−0.0005 (14)	0.0043 (13)	0.0015 (13)
C11	0.0313 (16)	0.0219 (16)	0.0353 (17)	0.0014 (13)	0.0048 (13)	−0.0016 (13)
C12	0.0285 (16)	0.0210 (15)	0.0363 (17)	0.0007 (13)	0.0044 (13)	−0.0025 (13)
C13	0.0277 (16)	0.0156 (14)	0.0388 (18)	0.0016 (12)	0.0038 (13)	−0.0069 (12)
C14	0.0301 (16)	0.0182 (14)	0.0379 (17)	0.0008 (13)	0.0044 (13)	−0.0041 (13)
C15	0.0299 (16)	0.0179 (14)	0.0386 (17)	0.0015 (12)	0.0036 (13)	−0.0049 (13)
C16	0.042 (3)	0.059 (3)	0.036 (3)	0.027 (2)	−0.007 (2)	−0.015 (2)
C17	0.023 (2)	0.088 (5)	0.030 (2)	0.009 (3)	0.0030 (18)	−0.012 (3)
C18	0.042 (2)	0.054 (2)	0.052 (2)	0.0042 (19)	0.0061 (17)	−0.0153 (19)
C19	0.0263 (16)	0.0255 (16)	0.0373 (17)	−0.0011 (13)	0.0016 (13)	−0.0039 (13)
C20	0.0287 (16)	0.0251 (16)	0.0410 (18)	−0.0017 (13)	0.0012 (13)	−0.0037 (14)

Geometric parameters (Å, º)

O3—C21	1.341 (7)	C11—C12	1.351 (4)
O3—C3	1.444 (5)	C11—H11	0.9500
O4—C4	1.227 (6)	C12—C13	1.443 (4)
O21—C21	1.178 (8)	C12—H12	0.9500
C1—C17	1.512 (6)	C13—C14	1.366 (4)
C1—C2	1.520 (6)	C13—C20	1.494 (4)
C1—C6	1.528 (5)	C14—C15	1.429 (4)
C1—C16	1.589 (7)	C14—H14	0.9500
C2—C3	1.473 (8)	C15—C15^ii	1.351 (6)
C2—H2A	0.9900	C15—H15	0.9500
C2—H2B	0.9900	C16—H16A	0.9800
C3—C4	1.520 (7)	C16—H16B	0.9800
C3—H3	1.0000	C16—H16C	0.9800
C4—C5	1.521 (6)	C17—H17A	0.9800
C21—C22	1.497 (7)	C17—H17B	0.9800
C22—H22A	0.9800	C17—H17C	0.9800
C22—H22B	0.9800	C16B—H16D	0.9800
C22—H22C	0.9800	C16B—H16E	0.9800
O3B—C21B	1.352 (14)	C16B—H16F	0.9800
O3B—C3B	1.432 (12)	C17B—H17D	0.9800
O4B—C4B	1.222 (14)	C17B—H17E	0.9800
O21B—C22B^i	1.05 (2)	C17B—H17F	0.9800
O21B—C21B	1.151 (14)	C18—H18A	0.9800
C2B—C3B	1.501 (15)	C18—H18B	0.9800
C2B—H2D	0.9900	C18—H18C	0.9800
C2B—H2E	0.9900	C19—H19A	0.9800
C3B—C4B	1.514 (14)	C19—H19B	0.9800
C3B—H3B	1.0000	C19—H19C	0.9800
C4B—C5	1.535 (13)	C20—H20A	0.9800
C21B—C22B^i	0.805 (19)	C20—H20B	0.9800
C21B—C22B	1.494 (15)	C20—H20C	0.9800
C21B—C21B^i	1.49 (2)	O1S—C1S	1.148 (14)
C22B—H22D	0.9800	O1S—O1S^iii	1.29 (5)
C22B—H22E	0.9800	O2S—C1S	1.337 (15)
C22B—H22F	0.9800	O2S—C3S	1.399 (19)
C5—C6	1.354 (5)	C1S—C2S	1.457 (13)
C5—C18	1.508 (5)	C2S—H2S1	0.9800
C6—C7	1.471 (4)	C2S—H2S2	0.9800
C7—C8	1.336 (4)	C2S—H2S3	0.9800
C7—H7	0.9500	C3S—C4S	1.489 (15)
C8—C9	1.456 (4)	C3S—H3S1	0.9900
C8—H8	0.9500	C3S—H3S2	0.9900
C9—C10	1.364 (4)	C4S—H4S1	0.9800
C9—C19	1.493 (4)	C4S—H4S2	0.9800
C10—C11	1.432 (4)	C4S—H4S3	0.9800
C10—H10	0.9500
C21—O3—C3	114.7 (4)	C9—C8—H8	117.2
C17—C1—C2	112.2 (4)	C10—C9—C8	119.0 (3)
C17—C1—C6	112.4 (3)	C10—C9—C19	122.7 (3)
C2—C1—C6	114.2 (4)	C8—C9—C19	118.2 (3)
C17—C1—C16	106.1 (5)	C9—C10—C11	125.8 (3)
C2—C1—C16	103.5 (4)	C9—C10—H10	117.1
C6—C1—C16	107.5 (3)	C11—C10—H10	117.1
C3—C2—C1	113.6 (4)	C12—C11—C10	124.9 (3)
C3—C2—H2A	108.8	C12—C11—H11	117.5
C1—C2—H2A	108.8	C10—C11—H11	117.5
C3—C2—H2B	108.8	C11—C12—C13	125.5 (3)
C1—C2—H2B	108.8	C11—C12—H12	117.3
H2A—C2—H2B	107.7	C13—C12—H12	117.3
O3—C3—C2	109.3 (4)	C14—C13—C12	119.1 (3)
O3—C3—C4	109.7 (4)	C14—C13—C20	122.6 (3)
C2—C3—C4	109.1 (5)	C12—C13—C20	118.2 (3)
O3—C3—H3	109.6	C13—C14—C15	127.8 (3)
C2—C3—H3	109.6	C13—C14—H14	116.1
C4—C3—H3	109.6	C15—C14—H14	116.1
O4—C4—C3	124.0 (5)	C15^ii—C15—C14	124.2 (4)
O4—C4—C5	120.0 (5)	C15^ii—C15—H15	117.9
C3—C4—C5	116.0 (4)	C14—C15—H15	117.9
O21—C21—O3	124.5 (5)	H16D—C16B—H16E	109.5
O21—C21—C22	125.3 (5)	H16D—C16B—H16F	109.5
O3—C21—C22	110.1 (5)	H16E—C16B—H16F	109.5
C21B—O3B—C3B	115.5 (9)	H17D—C17B—H17E	109.5
C22B^i—O21B—C21B	42.5 (11)	H17D—C17B—H17F	109.5
C3B—C2B—H2D	106.6	H17E—C17B—H17F	109.5
C3B—C2B—H2E	106.6	C5—C18—H18A	109.5
H2D—C2B—H2E	106.5	C5—C18—H18B	109.5
O3B—C3B—C2B	116.2 (11)	H18A—C18—H18B	109.5
O3B—C3B—C4B	108.2 (9)	C5—C18—H18C	109.5
C2B—C3B—C4B	107.6 (12)	H18A—C18—H18C	109.5
O3B—C3B—H3B	108.2	H18B—C18—H18C	109.5
C2B—C3B—H3B	108.2	C9—C19—H19A	109.5
C4B—C3B—H3B	108.2	C9—C19—H19B	109.5
O4B—C4B—C3B	124.8 (12)	H19A—C19—H19B	109.5
O4B—C4B—C5	120.0 (11)	C9—C19—H19C	109.5
C3B—C4B—C5	114.5 (9)	H19A—C19—H19C	109.5
C22B^i—C21B—O21B	62.2 (16)	H19B—C19—H19C	109.5
C22B^i—C21B—O3B	157 (2)	C13—C20—H20A	109.5
O21B—C21B—O3B	125.9 (12)	C13—C20—H20B	109.5
C22B^i—C21B—C22B	69 (2)	H20A—C20—H20B	109.5
O21B—C21B—C22B	127.6 (14)	C13—C20—H20C	109.5
O3B—C21B—C22B	106.5 (11)	H20A—C20—H20C	109.5
C22B^i—C21B—C21B^i	74.8 (16)	H20B—C20—H20C	109.5
O21B—C21B—C21B^i	114.2 (15)	C1S—O1S—O1S^iii	122 (3)
O3B—C21B—C21B^i	113.7 (12)	C1S—O2S—C3S	124.1 (19)
C22B—C21B—C21B^i	31.3 (8)	O1S—C1S—O2S	124.3 (13)
C21B—C22B—H22D	109.5	O1S—C1S—C2S	126.1 (14)
C21B—C22B—H22E	109.5	O2S—C1S—C2S	109.5 (11)
H22D—C22B—H22E	109.5	C1S—C2S—H2S1	109.5
C21B—C22B—H22F	109.5	C1S—C2S—H2S2	109.5
H22D—C22B—H22F	109.5	H2S1—C2S—H2S2	109.5
H22E—C22B—H22F	109.5	C1S—C2S—H2S3	109.5
C6—C5—C18	125.3 (3)	H2S1—C2S—H2S3	109.5
C6—C5—C4	118.1 (3)	H2S2—C2S—H2S3	109.5
C18—C5—C4	116.4 (3)	O2S—C3S—C4S	120 (3)
C6—C5—C4B	122.8 (5)	O2S—C3S—H3S1	107.3
C18—C5—C4B	104.0 (5)	C4S—C3S—H3S1	107.3
C4—C5—C4B	36.4 (6)	O2S—C3S—H3S2	107.3
C5—C6—C7	121.8 (3)	C4S—C3S—H3S2	107.3
C5—C6—C1	123.1 (3)	H3S1—C3S—H3S2	106.9
C7—C6—C1	115.2 (3)	C3S—C4S—H4S1	109.5
C8—C7—C6	125.1 (3)	C3S—C4S—H4S2	109.5
C8—C7—H7	117.5	H4S1—C4S—H4S2	109.5
C6—C7—H7	117.5	C3S—C4S—H4S3	109.5
C7—C8—C9	125.7 (3)	H4S1—C4S—H4S3	109.5
C7—C8—H8	117.2	H4S2—C4S—H4S3	109.5
C17—C1—C2—C3	162.7 (6)	C3B—C4B—C5—C18	−155.5 (10)
C6—C1—C2—C3	33.2 (8)	O4B—C4B—C5—C4	−82.3 (15)
C16—C1—C2—C3	−83.4 (7)	C3B—C4B—C5—C4	88.8 (13)
C21—O3—C3—C2	−158.0 (6)	C18—C5—C6—C7	−7.2 (6)
C21—O3—C3—C4	82.4 (6)	C4—C5—C6—C7	166.8 (4)
C1—C2—C3—O3	−177.7 (5)	C4B—C5—C6—C7	−151.0 (8)
C1—C2—C3—C4	−57.7 (7)	C18—C5—C6—C1	173.7 (4)
O3—C3—C4—O4	−11.8 (8)	C4—C5—C6—C1	−12.4 (6)
C2—C3—C4—O4	−131.6 (6)	C4B—C5—C6—C1	29.8 (9)
O3—C3—C4—C5	168.6 (4)	C17—C1—C6—C5	−126.0 (5)
C2—C3—C4—C5	48.9 (6)	C2—C1—C6—C5	3.4 (6)
C3—O3—C21—O21	1.8 (9)	C16—C1—C6—C5	117.6 (4)
C3—O3—C21—C22	178.4 (5)	C17—C1—C6—C7	54.8 (5)
C21B—O3B—C3B—C2B	95.3 (16)	C2—C1—C6—C7	−175.9 (4)
C21B—O3B—C3B—C4B	−143.5 (12)	C16—C1—C6—C7	−61.6 (4)
O3B—C3B—C4B—O4B	12 (2)	C5—C6—C7—C8	−49.1 (5)
C2B—C3B—C4B—O4B	138.1 (17)	C1—C6—C7—C8	130.2 (4)
O3B—C3B—C4B—C5	−158.8 (10)	C6—C7—C8—C9	−178.4 (3)
C2B—C3B—C4B—C5	−32.5 (16)	C7—C8—C9—C10	179.9 (3)
C22B^i—O21B—C21B—O3B	154 (3)	C7—C8—C9—C19	−1.8 (5)
C22B^i—O21B—C21B—C22B	−22.5 (18)	C8—C9—C10—C11	174.2 (3)
C22B^i—O21B—C21B—C21B^i	−55.7 (16)	C19—C9—C10—C11	−4.0 (5)
C3B—O3B—C21B—C22B^i	94 (5)	C9—C10—C11—C12	−178.8 (3)
C3B—O3B—C21B—O21B	−8 (2)	C10—C11—C12—C13	173.2 (3)
C3B—O3B—C21B—C22B	168.7 (11)	C11—C12—C13—C14	−177.5 (3)
C3B—O3B—C21B—C21B^i	−158.8 (9)	C11—C12—C13—C20	1.2 (4)
O4—C4—C5—C6	166.0 (5)	C12—C13—C14—C15	178.3 (3)
C3—C4—C5—C6	−14.4 (7)	C20—C13—C14—C15	−0.4 (5)
O4—C4—C5—C18	−19.5 (7)	C13—C14—C15—C15^ii	176.2 (4)
C3—C4—C5—C18	160.1 (4)	O1S^iii—O1S—C1S—O2S	−119 (2)
O4—C4—C5—C4B	58.0 (9)	O1S^iii—O1S—C1S—C2S	62 (2)
C3—C4—C5—C4B	−122.5 (9)	C3S—O2S—C1S—O1S	164 (3)
O4B—C4B—C5—C6	−176.4 (11)	C3S—O2S—C1S—C2S	−17 (3)
C3B—C4B—C5—C6	−5.3 (15)	C1S—O2S—C3S—C4S	96 (4)
O4B—C4B—C5—C18	33.4 (15)

Symmetry codes: (i) −x+2, y, −z+3/2; (ii) −x−1/2, −y+1/2, −z+1; (iii) −x+1, y, −z+3/2.

(s-trans-1)

Crystal data

C44H56O6	F(000) = 736
Mr = 680.89	Dx = 1.161 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 3456 reflections
a = 10.6598 (10) Å	θ = 2.3–26.2°
b = 10.1683 (10) Å	µ = 0.08 mm^−1
c = 18.2940 (18) Å	T = 100 K
β = 100.700 (2)°	Plate, red
V = 1948.4 (3) Å^3	0.60 × 0.60 × 0.10 mm
Z = 2

Data collection

Bruker APEX CCD area detector diffractometer	2506 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.072
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
phi and ω scans	h = −12→11
9816 measured reflections	k = −9→12
3425 independent reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.175	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0489P)^2 + 1.5414P] where P = (Fo^2 + 2Fc^2)/3
3425 reflections	(Δ/σ)max = 0.001
305 parameters	Δρmax = 0.39 e Å^−3
73 restraints	Δρmin = −0.21 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O4	0.86809 (19)	−0.07034 (18)	0.34294 (10)	0.0525 (5)
O3	1.0473 (3)	0.1135 (3)	0.35298 (15)	0.0504 (7)	0.788 (4)
O21	0.9139 (2)	0.2207 (3)	0.41407 (15)	0.0608 (8)	0.788 (4)
C1	0.9199 (5)	0.1090 (6)	0.1462 (3)	0.0412 (14)	0.788 (4)
C2	1.0123 (2)	0.1161 (2)	0.22110 (13)	0.0523 (10)	0.788 (4)
H2A	1.0743	0.0430	0.2235	0.063*	0.788 (4)
H2B	1.0608	0.1994	0.2230	0.063*	0.788 (4)
C3	0.9532 (2)	0.1091 (2)	0.28575 (13)	0.0574 (8)	0.788 (4)
H3	0.8959	0.1872	0.2852	0.069*	0.788 (4)
C16	1.0070 (5)	0.0802 (6)	0.0901 (3)	0.0500 (12)	0.788 (4)
H16A	0.9607	0.0982	0.0396	0.075*	0.788 (4)
H16B	1.0330	−0.0124	0.0939	0.075*	0.788 (4)
H16C	1.0829	0.1363	0.1009	0.075*	0.788 (4)
C17	0.8510 (7)	0.2415 (7)	0.1283 (3)	0.0490 (13)	0.788 (4)
H17A	0.7949	0.2364	0.0795	0.073*	0.788 (4)
H17B	0.9143	0.3112	0.1278	0.073*	0.788 (4)
H17C	0.8000	0.2612	0.1664	0.073*	0.788 (4)
C21	1.0126 (4)	0.1660 (4)	0.4135 (2)	0.0477 (9)	0.788 (4)
C22	1.1163 (10)	0.1437 (11)	0.4793 (3)	0.0541 (17)	0.788 (4)
H22A	1.1852	0.0927	0.4641	0.081*	0.788 (4)
H22B	1.0821	0.0952	0.5175	0.081*	0.788 (4)
H22C	1.1498	0.2286	0.4995	0.081*	0.788 (4)
O3B	0.9884 (16)	0.1680 (13)	0.3577 (6)	0.086 (4)	0.212 (4)
O21B	1.1647 (12)	0.0432 (13)	0.3953 (7)	0.092 (4)	0.212 (4)
C1B	0.8923 (19)	0.143 (2)	0.1490 (8)	0.033 (4)	0.212 (4)
C2B	0.9304 (11)	0.1951 (10)	0.2280 (5)	0.034 (2)	0.212 (4)
H2C	1.0084	0.2488	0.2299	0.041*	0.212 (4)
H2D	0.8620	0.2555	0.2371	0.041*	0.212 (4)
C3B	0.9532 (2)	0.1091 (2)	0.28575 (13)	0.0574 (8)	0.212 (4)
H3B	1.0366	0.0706	0.2789	0.069*	0.212 (4)
C16B	1.0126 (17)	0.103 (2)	0.1221 (8)	0.038 (4)	0.212 (4)
H16D	0.9920	0.0826	0.0689	0.056*	0.212 (4)
H16E	1.0494	0.0251	0.1496	0.056*	0.212 (4)
H16F	1.0743	0.1753	0.1305	0.056*	0.212 (4)
C17B	0.825 (2)	0.2538 (19)	0.0996 (10)	0.039 (4)	0.212 (4)
H17D	0.8135	0.2274	0.0472	0.059*	0.212 (4)
H17E	0.8769	0.3338	0.1073	0.059*	0.212 (4)
H17F	0.7413	0.2709	0.1126	0.059*	0.212 (4)
C21B	1.0830 (16)	0.1169 (16)	0.4087 (9)	0.067 (4)	0.212 (4)
C22B	1.084 (4)	0.171 (4)	0.4838 (13)	0.084 (15)	0.212 (4)
H22D	1.0070	0.1428	0.5013	0.125*	0.212 (4)
H22E	1.0867	0.2672	0.4818	0.125*	0.212 (4)
H22F	1.1597	0.1386	0.5180	0.125*	0.212 (4)
C4	0.8740 (2)	−0.0121 (3)	0.28521 (15)	0.0440 (6)
C5	0.8007 (2)	−0.0538 (2)	0.21228 (15)	0.0402 (6)
C6	0.8172 (2)	0.0049 (3)	0.14774 (15)	0.0431 (6)
C7	0.7383 (2)	−0.0415 (3)	0.07905 (15)	0.0476 (7)
H7	0.6825	−0.1119	0.0852	0.057*
C8	0.7310 (2)	−0.0012 (3)	0.00776 (15)	0.0425 (6)
H8	0.7853	0.0686	−0.0014	0.051*
C9	0.6457 (2)	−0.0577 (3)	−0.05540 (15)	0.0449 (7)
C10	0.6507 (2)	−0.0112 (3)	−0.12432 (15)	0.0442 (6)
H10	0.7107	0.0568	−0.1272	0.053*
C11	0.5747 (2)	−0.0542 (3)	−0.19332 (16)	0.0457 (7)
H11	0.5099	−0.1176	−0.1915	0.055*
C12	0.5898 (3)	−0.0100 (3)	−0.26051 (15)	0.0469 (7)
H12	0.6564	0.0516	−0.2617	0.056*
C13	0.5128 (3)	−0.0487 (3)	−0.33144 (16)	0.0481 (7)
C14	0.5442 (3)	0.0002 (3)	−0.39485 (16)	0.0500 (7)
H14	0.6155	0.0579	−0.3889	0.060*
C15	0.4814 (3)	−0.0260 (3)	−0.46986 (15)	0.0518 (7)
H15	0.4095	−0.0830	−0.4774	0.062*
C18	0.7081 (3)	−0.1646 (3)	0.21580 (16)	0.0498 (7)
H18A	0.6217	−0.1362	0.1934	0.075*
H18B	0.7103	−0.1891	0.2678	0.075*
H18C	0.7321	−0.2406	0.1885	0.075*
C19	0.5587 (3)	−0.1675 (3)	−0.04230 (16)	0.0545 (8)
H19A	0.5012	−0.1892	−0.0890	0.082*
H19B	0.5083	−0.1401	−0.0053	0.082*
H19C	0.6096	−0.2451	−0.0240	0.082*
C20	0.4038 (3)	−0.1426 (3)	−0.33138 (17)	0.0558 (8)
H20A	0.3506	−0.1457	−0.3812	0.084*
H20B	0.3522	−0.1128	−0.2955	0.084*
H20C	0.4376	−0.2306	−0.3175	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0581 (12)	0.0456 (11)	0.0557 (12)	0.0024 (9)	0.0156 (9)	0.0097 (9)
O3	0.0533 (17)	0.0532 (19)	0.0413 (16)	−0.0091 (13)	0.0001 (13)	0.0031 (13)
O21	0.0474 (16)	0.0661 (18)	0.0669 (18)	0.0059 (13)	0.0056 (13)	−0.0082 (14)
C1	0.036 (3)	0.042 (4)	0.045 (2)	−0.005 (2)	0.0062 (19)	−0.0026 (19)
C2	0.046 (2)	0.058 (2)	0.053 (2)	−0.0114 (18)	0.0091 (17)	−0.0015 (18)
C3	0.0627 (19)	0.0551 (18)	0.0530 (17)	−0.0119 (15)	0.0071 (14)	0.0016 (13)
C16	0.037 (2)	0.061 (3)	0.055 (3)	−0.0023 (19)	0.015 (2)	0.005 (3)
C17	0.054 (3)	0.042 (3)	0.050 (3)	−0.007 (2)	0.006 (3)	−0.002 (2)
C21	0.049 (3)	0.042 (2)	0.051 (3)	−0.0122 (19)	0.008 (2)	0.0009 (18)
C22	0.060 (3)	0.060 (5)	0.041 (3)	−0.008 (3)	0.004 (2)	−0.001 (2)
O3B	0.130 (10)	0.063 (8)	0.054 (4)	−0.021 (6)	−0.009 (7)	0.008 (5)
O21B	0.089 (9)	0.081 (9)	0.112 (10)	−0.021 (6)	0.033 (7)	−0.009 (7)
C1B	0.038 (8)	0.018 (8)	0.047 (4)	−0.002 (6)	0.021 (6)	−0.006 (5)
C2B	0.044 (6)	0.025 (5)	0.042 (4)	−0.018 (4)	0.030 (4)	−0.007 (3)
C3B	0.0627 (19)	0.0551 (18)	0.0530 (17)	−0.0119 (15)	0.0071 (14)	0.0016 (13)
C16B	0.041 (8)	0.047 (9)	0.027 (8)	0.007 (6)	0.014 (7)	0.003 (7)
C17B	0.045 (9)	0.015 (7)	0.056 (8)	0.000 (5)	0.008 (9)	−0.013 (7)
C21B	0.084 (11)	0.060 (10)	0.057 (8)	−0.026 (6)	0.010 (6)	−0.007 (7)
C22B	0.11 (3)	0.060 (19)	0.085 (19)	−0.04 (2)	0.037 (17)	−0.026 (12)
C4	0.0424 (15)	0.0401 (14)	0.0516 (16)	0.0070 (12)	0.0140 (12)	0.0044 (13)
C5	0.0333 (13)	0.0339 (13)	0.0556 (16)	0.0032 (10)	0.0142 (12)	−0.0004 (12)
C6	0.0367 (14)	0.0409 (15)	0.0518 (16)	−0.0025 (12)	0.0084 (12)	−0.0026 (12)
C7	0.0372 (15)	0.0450 (16)	0.0610 (18)	−0.0069 (12)	0.0107 (13)	−0.0034 (13)
C8	0.0324 (13)	0.0391 (14)	0.0550 (16)	0.0007 (11)	0.0055 (11)	−0.0043 (12)
C9	0.0356 (14)	0.0370 (14)	0.0604 (18)	0.0041 (11)	0.0043 (12)	−0.0065 (12)
C10	0.0340 (14)	0.0394 (14)	0.0569 (17)	0.0034 (11)	0.0026 (12)	−0.0085 (12)
C11	0.0361 (14)	0.0372 (14)	0.0605 (18)	0.0071 (11)	0.0001 (12)	−0.0095 (13)
C12	0.0398 (15)	0.0393 (14)	0.0574 (17)	0.0049 (12)	−0.0017 (13)	−0.0095 (13)
C13	0.0395 (15)	0.0396 (15)	0.0600 (18)	0.0091 (12)	−0.0043 (13)	−0.0095 (13)
C14	0.0457 (16)	0.0396 (15)	0.0589 (18)	0.0022 (12)	−0.0056 (13)	−0.0084 (13)
C15	0.0493 (17)	0.0392 (15)	0.0606 (18)	0.0042 (12)	−0.0061 (14)	−0.0091 (13)
C18	0.0458 (16)	0.0374 (15)	0.0673 (18)	−0.0012 (12)	0.0137 (14)	0.0024 (13)
C19	0.0437 (16)	0.0528 (17)	0.0647 (19)	−0.0057 (13)	0.0042 (14)	−0.0089 (14)
C20	0.0407 (16)	0.0518 (17)	0.070 (2)	0.0043 (13)	−0.0022 (14)	−0.0112 (15)

Geometric parameters (Å, º)

O4—C4	1.222 (3)	C17B—H17F	0.9800
O3—C21	1.342 (5)	C21B—C22B	1.477 (17)
O3—C3	1.437 (3)	C22B—H22D	0.9800
O21—C21	1.192 (4)	C22B—H22E	0.9800
C1—C6	1.526 (7)	C22B—H22F	0.9800
C1—C2	1.533 (5)	C4—C5	1.477 (4)
C1—C16	1.535 (6)	C5—C6	1.363 (4)
C1—C17	1.540 (6)	C5—C18	1.507 (3)
C2—C3	1.4413	C6—C7	1.455 (4)
C2—H2A	0.9900	C7—C8	1.356 (4)
C2—H2B	0.9900	C7—H7	0.9500
C3—C4	1.494 (4)	C8—C9	1.450 (4)
C3—H3	1.0000	C8—H8	0.9500
C16—H16A	0.9800	C9—C10	1.357 (4)
C16—H16B	0.9800	C9—C19	1.499 (4)
C16—H16C	0.9800	C10—C11	1.436 (4)
C17—H17A	0.9800	C10—H10	0.9500
C17—H17B	0.9800	C11—C12	1.346 (4)
C17—H17C	0.9800	C11—H11	0.9500
C21—C22	1.493 (8)	C12—C13	1.455 (4)
C22—H22A	0.9800	C12—H12	0.9500
C22—H22B	0.9800	C13—C14	1.360 (4)
C22—H22C	0.9800	C13—C20	1.505 (4)
O3B—C21B	1.344 (15)	C14—C15	1.436 (4)
O21B—C21B	1.208 (15)	C14—H14	0.9500
C1B—C16B	1.512 (15)	C15—C15^i	1.347 (6)
C1B—C2B	1.523 (15)	C15—H15	0.9500
C1B—C17B	1.538 (15)	C18—H18A	0.9800
C1B—C6	1.61 (2)	C18—H18B	0.9800
C2B—H2C	0.9900	C18—H18C	0.9800
C2B—H2D	0.9900	C19—H19A	0.9800
C16B—H16D	0.9800	C19—H19B	0.9800
C16B—H16E	0.9800	C19—H19C	0.9800
C16B—H16F	0.9800	C20—H20A	0.9800
C17B—H17D	0.9800	C20—H20B	0.9800
C17B—H17E	0.9800	C20—H20C	0.9800
C21—O3—C3	117.6 (3)	C6—C5—C4	121.7 (2)
C6—C1—C2	111.1 (4)	C6—C5—C18	123.7 (2)
C6—C1—C16	113.9 (4)	C4—C5—C18	114.6 (2)
C2—C1—C16	103.8 (4)	C5—C6—C7	117.3 (2)
C6—C1—C17	107.2 (4)	C5—C6—C1	121.8 (3)
C2—C1—C17	110.5 (4)	C7—C6—C1	120.7 (3)
C16—C1—C17	110.4 (5)	C5—C6—C1B	120.7 (6)
C3—C2—C1	115.1 (2)	C7—C6—C1B	120.0 (6)
C3—C2—H2A	108.5	C1—C6—C1B	16.6 (6)
C1—C2—H2A	108.5	C8—C7—C6	130.8 (3)
C3—C2—H2B	108.5	C8—C7—H7	114.6
C1—C2—H2B	108.5	C6—C7—H7	114.6
H2A—C2—H2B	107.5	C7—C8—C9	124.2 (3)
O3—C3—C2	111.02 (15)	C7—C8—H8	117.9
O3—C3—C4	109.6 (2)	C9—C8—H8	117.9
C2—C3—C4	111.57 (14)	C10—C9—C8	118.4 (3)
O3—C3—H3	108.2	C10—C9—C19	122.7 (2)
C2—C3—H3	108.2	C8—C9—C19	118.9 (2)
C4—C3—H3	108.2	C9—C10—C11	126.7 (3)
O21—C21—O3	124.9 (4)	C9—C10—H10	116.6
O21—C21—C22	125.9 (5)	C11—C10—H10	116.6
O3—C21—C22	109.2 (5)	C12—C11—C10	123.9 (3)
C16B—C1B—C2B	108.0 (13)	C12—C11—H11	118.0
C16B—C1B—C17B	109.7 (15)	C10—C11—H11	118.0
C2B—C1B—C17B	108.4 (13)	C11—C12—C13	125.5 (3)
C16B—C1B—C6	102.1 (13)	C11—C12—H12	117.2
C2B—C1B—C6	111.2 (12)	C13—C12—H12	117.2
C17B—C1B—C6	116.9 (15)	C14—C13—C12	118.3 (3)
C1B—C2B—H2C	107.5	C14—C13—C20	123.1 (2)
C1B—C2B—H2D	107.5	C12—C13—C20	118.6 (3)
H2C—C2B—H2D	107.0	C13—C14—C15	127.0 (3)
C1B—C16B—H16D	109.5	C13—C14—H14	116.5
C1B—C16B—H16E	109.5	C15—C14—H14	116.5
H16D—C16B—H16E	109.5	C15^i—C15—C14	123.6 (4)
C1B—C16B—H16F	109.5	C15^i—C15—H15	118.2
H16D—C16B—H16F	109.5	C14—C15—H15	118.2
H16E—C16B—H16F	109.5	C5—C18—H18A	109.5
C1B—C17B—H17D	109.5	C5—C18—H18B	109.5
C1B—C17B—H17E	109.5	H18A—C18—H18B	109.5
H17D—C17B—H17E	109.5	C5—C18—H18C	109.5
C1B—C17B—H17F	109.5	H18A—C18—H18C	109.5
H17D—C17B—H17F	109.5	H18B—C18—H18C	109.5
H17E—C17B—H17F	109.5	C9—C19—H19A	109.5
O21B—C21B—O3B	125.1 (16)	C9—C19—H19B	109.5
O21B—C21B—C22B	122.5 (19)	H19A—C19—H19B	109.5
O3B—C21B—C22B	112.2 (19)	C9—C19—H19C	109.5
C21B—C22B—H22D	109.5	H19A—C19—H19C	109.5
C21B—C22B—H22E	109.5	H19B—C19—H19C	109.5
H22D—C22B—H22E	109.5	C13—C20—H20A	109.5
C21B—C22B—H22F	109.5	C13—C20—H20B	109.5
H22D—C22B—H22F	109.5	H20A—C20—H20B	109.5
H22E—C22B—H22F	109.5	C13—C20—H20C	109.5
O4—C4—C5	122.6 (2)	H20A—C20—H20C	109.5
O4—C4—C3	120.9 (2)	H20B—C20—H20C	109.5
C5—C4—C3	116.5 (2)
C6—C1—C2—C3	−42.2 (4)	C17—C1—C6—C7	73.9 (5)
C16—C1—C2—C3	−165.0 (3)	C2—C1—C6—C1B	102 (2)
C17—C1—C2—C3	76.7 (4)	C16—C1—C6—C1B	−141 (2)
C21—O3—C3—C2	150.7 (3)	C17—C1—C6—C1B	−19 (2)
C21—O3—C3—C4	−85.6 (3)	C16B—C1B—C6—C5	111.8 (9)
C1—C2—C3—O3	178.7 (4)	C2B—C1B—C6—C5	−3.3 (14)
C1—C2—C3—C4	56.1 (3)	C17B—C1B—C6—C5	−128.5 (11)
C3—O3—C21—O21	−7.8 (6)	C16B—C1B—C6—C7	−84.3 (11)
C3—O3—C21—C22	171.8 (5)	C2B—C1B—C6—C7	160.6 (8)
O3—C3—C4—O4	20.4 (3)	C17B—C1B—C6—C7	35.4 (15)
C2—C3—C4—O4	143.8 (2)	C16B—C1B—C6—C1	12.9 (16)
O3—C3—C4—C5	−161.8 (2)	C2B—C1B—C6—C1	−102 (3)
C2—C3—C4—C5	−38.4 (2)	C17B—C1B—C6—C1	133 (3)
O4—C4—C5—C6	−173.9 (2)	C5—C6—C7—C8	178.3 (3)
C3—C4—C5—C6	8.4 (3)	C1—C6—C7—C8	−5.4 (5)
O4—C4—C5—C18	6.1 (4)	C1B—C6—C7—C8	13.9 (8)
C3—C4—C5—C18	−171.7 (2)	C6—C7—C8—C9	−179.6 (3)
C4—C5—C6—C7	−178.7 (2)	C7—C8—C9—C10	−177.9 (2)
C18—C5—C6—C7	1.4 (4)	C7—C8—C9—C19	0.3 (4)
C4—C5—C6—C1	5.1 (4)	C8—C9—C10—C11	179.9 (2)
C18—C5—C6—C1	−174.8 (3)	C19—C9—C10—C11	1.8 (4)
C4—C5—C6—C1B	−14.4 (8)	C9—C10—C11—C12	−175.5 (3)
C18—C5—C6—C1B	165.7 (8)	C10—C11—C12—C13	−178.4 (2)
C2—C1—C6—C5	10.9 (5)	C11—C12—C13—C14	−176.9 (3)
C16—C1—C6—C5	127.6 (4)	C11—C12—C13—C20	2.0 (4)
C17—C1—C6—C5	−110.0 (4)	C12—C13—C14—C15	179.7 (2)
C2—C1—C6—C7	−165.2 (3)	C20—C13—C14—C15	0.9 (4)
C16—C1—C6—C7	−48.5 (5)	C13—C14—C15—C15^i	−179.7 (3)

Symmetry code: (i) −x+1, −y, −z−1.

(2)

Crystal data

C40H50O4	Z = 1
Mr = 594.80	F(000) = 322
Triclinic, P1	Dx = 1.146 Mg m^−3
a = 7.7821 (4) Å	Synchrotron radiation, λ = 0.6709 Å
b = 9.9578 (5) Å	Cell parameters from 4494 reflections
c = 11.4162 (5) Å	θ = 3.3–30.5°
α = 88.126 (1)°	µ = 0.07 mm^−1
β = 78.329 (1)°	T = 100 K
γ = 84.340 (1)°	Plate, red
V = 862.08 (7) Å^3	0.2 × 0.2 × 0.02 mm

Data collection

Bruker APEXII CCD area detector diffractometer	3029 independent reflections
Radiation source: Station 9.8, SRS, Daresbury	2910 reflections with I > 2σ(I)
Silicon monochromator	Rint = 0.016
phi and ω scans	θmax = 23.8°, θmin = 2.6°
Absorption correction: multi-scan SADABS	h = −9→9
Tmin = 0.736, Tmax = 1.000	k = −11→11
6688 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0747P)^2 + 0.1591P] where P = (Fo^2 + 2Fc^2)/3
3029 reflections	(Δ/σ)max < 0.001
428 parameters	Δρmax = 0.17 e Å^−3
143 restraints	Δρmin = −0.16 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O3	1.5748 (4)	1.2999 (3)	0.0199 (3)	0.0704 (8)
H3	1.5429	1.3082	−0.0444	0.106*
O4	1.2814 (3)	1.2251 (3)	−0.0358 (2)	0.0555 (6)
O3B	−1.1944 (4)	−0.6539 (3)	1.3235 (2)	0.0728 (9)
H3B	−1.1476	−0.6619	1.3819	0.109*
O4B	−0.9174 (3)	−0.5515 (3)	1.3753 (2)	0.0544 (6)
C1	1.3989 (4)	1.0939 (3)	0.2911 (3)	0.0415 (7)
C2	1.4768 (4)	1.2122 (3)	0.2166 (3)	0.0447 (7)
H2A	1.4009	1.2943	0.2392	0.054*
H2B	1.5913	1.2235	0.2344	0.054*
C3	1.4970 (4)	1.1919 (3)	0.0851 (3)	0.0454 (7)
H3A	1.5740	1.1089	0.0632	0.054*
C4	1.3186 (4)	1.1752 (3)	0.0565 (3)	0.0419 (7)
C5	1.1975 (4)	1.0955 (3)	0.1406 (3)	0.0412 (7)
C6	1.2354 (4)	1.0563 (3)	0.2472 (3)	0.0419 (7)
C7	1.1177 (9)	0.9670 (6)	0.3138 (8)	0.0359 (13)	0.638 (17)
C8	1.0287 (4)	0.8948 (3)	0.3749 (3)	0.0420 (7)	0.638 (17)
C7A	1.1492 (16)	0.9770 (11)	0.3574 (15)	0.038 (2)	0.362 (17)
H7A	1.1929	0.9914	0.4255	0.046*	0.362 (17)
C8A	1.0287 (4)	0.8948 (3)	0.3749 (3)	0.0420 (7)	0.362 (17)
H8A	0.9793	0.8885	0.3078	0.050*	0.362 (17)
C9	0.9513 (4)	0.8107 (3)	0.4712 (3)	0.0384 (6)
C10	0.8070 (4)	0.7464 (3)	0.4648 (3)	0.0373 (6)
H10	0.7628	0.7582	0.3949	0.045*
C11	0.7176 (4)	0.6622 (3)	0.5568 (3)	0.0361 (6)
H11	0.7605	0.6497	0.6271	0.043*
C12	0.5747 (4)	0.5997 (3)	0.5474 (3)	0.0360 (6)
H12	0.5327	0.6131	0.4768	0.043*
C13	0.4822 (4)	0.5143 (3)	0.6376 (2)	0.0354 (6)
C14	0.3411 (4)	0.4553 (3)	0.6137 (3)	0.0363 (6)
H14	0.3102	0.4771	0.5404	0.044*
C15	0.2367 (4)	0.3640 (3)	0.6891 (3)	0.0359 (6)
H15	0.2675	0.3374	0.7615	0.043*
C15B	0.0952 (4)	0.3141 (3)	0.6604 (2)	0.0358 (6)
H15B	0.0629	0.3425	0.5888	0.043*
C14B	−0.0076 (4)	0.2199 (3)	0.7344 (2)	0.0346 (6)
H14B	0.0236	0.1969	0.8074	0.042*
C13B	−0.1448 (4)	0.1612 (3)	0.7094 (2)	0.0351 (6)
C12B	−0.2361 (4)	0.0702 (3)	0.7966 (2)	0.0350 (6)
H12B	−0.1930	0.0540	0.8665	0.042*
C11B	−0.3776 (4)	0.0068 (3)	0.7864 (3)	0.0363 (6)
H11B	−0.4200	0.0199	0.7159	0.044*
C10B	−0.4665 (4)	−0.0790 (3)	0.8764 (3)	0.0355 (6)
H10B	−0.4197	−0.0926	0.9450	0.043*
C9B	−0.6104 (4)	−0.1426 (3)	0.8733 (3)	0.0378 (6)
C7B	−0.8129 (8)	−0.3041 (6)	0.9895 (7)	0.0343 (13)	0.638 (17)
H7B	−0.8560	−0.3150	0.9205	0.041*	0.638 (17)
C8B	−0.6865 (4)	−0.2235 (3)	0.9741 (3)	0.0432 (7)	0.638 (17)
H8B	−0.6363	−0.2173	1.0409	0.052*	0.638 (17)
C7BB	−0.7805 (14)	−0.2885 (10)	1.0321 (13)	0.035 (2)	0.362 (17)
C8BB	−0.6865 (4)	−0.2235 (3)	0.9741 (3)	0.0432 (7)	0.362 (17)
C6B	−0.9018 (4)	−0.3816 (3)	1.0934 (3)	0.0428 (7)
C5B	−0.8453 (4)	−0.4276 (3)	1.1941 (3)	0.0441 (8)
C4B	−0.9459 (4)	−0.5222 (3)	1.2762 (3)	0.0408 (7)
C3B	−1.0860 (4)	−0.5869 (3)	1.2301 (3)	0.0450 (7)
H3B1	−1.0274	−0.6539	1.1705	0.054*
C2B	−1.1888 (4)	−0.4821 (3)	1.1699 (3)	0.0413 (6)
H2B1	−1.2436	−0.4130	1.2270	0.050*
H2B2	−1.2818	−0.5230	1.1429	0.050*
C1B	−1.0741 (4)	−0.4169 (3)	1.0632 (3)	0.0412 (7)
C16	1.5320 (5)	0.9694 (4)	0.2824 (4)	0.0579 (8)
H16A	1.5594	0.9375	0.2017	0.087*
H16B	1.4826	0.8999	0.3352	0.087*
H16C	1.6376	0.9927	0.3049	0.087*
C17	1.3463 (7)	1.1412 (5)	0.4208 (3)	0.0804 (13)
H17A	1.3042	1.0678	0.4717	0.121*	0.638 (17)
H17B	1.2549	1.2143	0.4268	0.121*	0.638 (17)
H17C	1.4469	1.1713	0.4454	0.121*	0.638 (17)
H17D	1.3665	1.2345	0.4242	0.121*	0.362 (17)
H17E	1.4158	1.0880	0.4691	0.121*	0.362 (17)
H17F	1.2237	1.1309	0.4505	0.121*	0.362 (17)
C18	1.0340 (5)	1.0653 (3)	0.0977 (4)	0.0604 (10)
H18A	1.0669	1.0070	0.0299	0.091*
H18B	0.9740	1.1481	0.0751	0.091*
H18C	0.9572	1.0217	0.1608	0.091*
C19	1.0397 (5)	0.7987 (4)	0.5771 (3)	0.0565 (9)
H19A	1.0045	0.7208	0.6243	0.085*
H19B	1.0059	0.8781	0.6249	0.085*
H19C	1.1653	0.7895	0.5497	0.085*
C20	0.5435 (4)	0.4920 (3)	0.7534 (3)	0.0413 (7)
H20A	0.4591	0.4452	0.8088	0.062*
H20B	0.5552	0.5775	0.7861	0.062*
H20C	0.6555	0.4391	0.7398	0.062*
C16B	−1.1812 (5)	−0.2881 (4)	1.0300 (3)	0.0575 (8)
H16D	−1.2922	−0.3106	1.0157	0.086*
H16E	−1.1167	−0.2478	0.9591	0.086*
H16F	−1.2014	−0.2254	1.0946	0.086*
C17B	−1.0380 (6)	−0.5118 (4)	0.9546 (3)	0.0620 (9)
H17H	−0.9745	−0.5946	0.9736	0.093*
H17I	−0.9693	−0.4690	0.8869	0.093*
H17J	−1.1479	−0.5309	0.9359	0.093*
C18B	−0.6797 (4)	−0.3914 (4)	1.2281 (4)	0.0625 (11)
H18D	−0.5816	−0.4119	1.1634	0.094*
H18E	−0.6609	−0.4423	1.2980	0.094*
H18F	−0.6906	−0.2967	1.2448	0.094*
C19B	−0.6997 (5)	−0.1330 (4)	0.7684 (3)	0.0557 (9)
H19D	−0.6286	−0.0885	0.7028	0.084*
H19E	−0.8127	−0.0824	0.7900	0.084*
H19F	−0.7151	−0.2221	0.7450	0.084*
C20B	−0.2094 (4)	0.1849 (3)	0.5930 (3)	0.0462 (8)
H20D	−0.1342	0.2422	0.5412	0.069*
H20E	−0.3278	0.2276	0.6093	0.069*
H20F	−0.2073	0.1001	0.5549	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0710 (17)	0.0839 (18)	0.0601 (16)	−0.0437 (14)	−0.0091 (13)	0.0292 (14)
O4	0.0581 (14)	0.0604 (14)	0.0492 (13)	−0.0059 (11)	−0.0149 (11)	0.0102 (11)
O3B	0.0741 (18)	0.099 (2)	0.0596 (16)	−0.0606 (16)	−0.0275 (13)	0.0407 (15)
O4B	0.0535 (13)	0.0651 (15)	0.0492 (13)	−0.0147 (11)	−0.0183 (10)	0.0070 (11)
C1	0.0471 (16)	0.0424 (15)	0.0322 (14)	−0.0059 (12)	−0.0010 (12)	0.0007 (12)
C2	0.0478 (16)	0.0425 (16)	0.0462 (16)	−0.0158 (13)	−0.0095 (13)	−0.0004 (12)
C3	0.0447 (15)	0.0520 (17)	0.0396 (15)	−0.0206 (13)	−0.0025 (12)	0.0058 (12)
C4	0.0444 (15)	0.0362 (15)	0.0436 (16)	−0.0049 (12)	−0.0045 (13)	−0.0023 (12)
C5	0.0370 (15)	0.0304 (14)	0.0549 (19)	−0.0080 (11)	−0.0033 (13)	−0.0031 (13)
C6	0.0360 (15)	0.0294 (13)	0.0528 (18)	−0.0056 (11)	0.0103 (12)	0.0000 (12)
C7	0.035 (2)	0.034 (2)	0.038 (3)	−0.0076 (17)	−0.004 (2)	−0.004 (2)
C8	0.0362 (13)	0.0377 (14)	0.0498 (17)	−0.0118 (11)	0.0019 (12)	−0.0036 (12)
C7A	0.036 (4)	0.039 (3)	0.038 (4)	−0.012 (3)	−0.001 (3)	0.000 (3)
C8A	0.0362 (13)	0.0377 (14)	0.0498 (17)	−0.0118 (11)	0.0019 (12)	−0.0036 (12)
C9	0.0364 (14)	0.0385 (15)	0.0405 (16)	−0.0107 (11)	−0.0045 (11)	−0.0005 (12)
C10	0.0406 (15)	0.0383 (15)	0.0346 (14)	−0.0098 (12)	−0.0094 (12)	0.0042 (12)
C11	0.0375 (14)	0.0362 (14)	0.0353 (14)	−0.0086 (12)	−0.0069 (11)	0.0036 (11)
C12	0.0381 (14)	0.0396 (15)	0.0319 (14)	−0.0093 (12)	−0.0084 (11)	0.0031 (11)
C13	0.0378 (15)	0.0354 (14)	0.0325 (14)	−0.0094 (11)	−0.0034 (11)	0.0015 (11)
C14	0.0373 (14)	0.0415 (14)	0.0310 (14)	−0.0120 (12)	−0.0060 (11)	0.0036 (11)
C15	0.0393 (15)	0.0385 (15)	0.0281 (13)	−0.0093 (12)	0.0003 (11)	0.0003 (11)
C15B	0.0393 (15)	0.0412 (15)	0.0254 (13)	−0.0098 (12)	0.0005 (11)	−0.0002 (11)
C14B	0.0415 (14)	0.0357 (14)	0.0245 (12)	−0.0095 (11)	0.0010 (10)	0.0006 (10)
C13B	0.0378 (14)	0.0373 (14)	0.0285 (14)	−0.0068 (12)	−0.0014 (11)	0.0000 (11)
C12B	0.0367 (14)	0.0381 (14)	0.0298 (14)	−0.0091 (11)	−0.0037 (11)	0.0043 (11)
C11B	0.0382 (14)	0.0391 (15)	0.0323 (14)	−0.0068 (12)	−0.0082 (11)	0.0019 (11)
C10B	0.0354 (14)	0.0362 (14)	0.0360 (14)	−0.0074 (11)	−0.0091 (11)	0.0051 (11)
C9B	0.0353 (14)	0.0399 (15)	0.0386 (15)	−0.0080 (11)	−0.0060 (11)	−0.0029 (11)
C7B	0.031 (2)	0.033 (2)	0.041 (3)	−0.0079 (16)	−0.008 (2)	−0.004 (2)
C8B	0.0364 (14)	0.0366 (14)	0.0535 (17)	−0.0098 (11)	0.0020 (12)	−0.0060 (12)
C7BB	0.030 (3)	0.035 (3)	0.042 (4)	−0.016 (3)	−0.006 (3)	−0.013 (3)
C8BB	0.0364 (14)	0.0366 (14)	0.0535 (17)	−0.0098 (11)	0.0020 (12)	−0.0060 (12)
C6B	0.0335 (14)	0.0310 (14)	0.0568 (18)	−0.0031 (11)	0.0077 (12)	0.0018 (12)
C5B	0.0319 (14)	0.0308 (14)	0.066 (2)	−0.0053 (11)	−0.0007 (14)	0.0009 (14)
C4B	0.0361 (14)	0.0395 (15)	0.0472 (17)	−0.0084 (11)	−0.0069 (12)	0.0005 (12)
C3B	0.0470 (16)	0.0497 (17)	0.0406 (15)	−0.0243 (13)	−0.0061 (12)	0.0090 (13)
C2B	0.0388 (14)	0.0498 (16)	0.0366 (14)	−0.0162 (12)	−0.0045 (11)	−0.0030 (11)
C1B	0.0448 (16)	0.0401 (16)	0.0348 (15)	−0.0019 (13)	−0.0004 (12)	0.0038 (12)
C16	0.0499 (18)	0.0511 (18)	0.070 (2)	−0.0031 (14)	−0.0077 (15)	0.0075 (15)
C17	0.108 (3)	0.085 (3)	0.0380 (19)	0.010 (2)	0.0008 (19)	−0.0062 (18)
C18	0.0474 (18)	0.0379 (17)	0.100 (3)	−0.0126 (14)	−0.0202 (19)	0.0035 (18)
C19	0.0477 (18)	0.076 (2)	0.0519 (19)	−0.0278 (17)	−0.0158 (15)	0.0071 (17)
C20	0.0475 (16)	0.0460 (16)	0.0332 (15)	−0.0195 (13)	−0.0084 (13)	0.0069 (12)
C16B	0.0566 (19)	0.0510 (19)	0.059 (2)	0.0059 (15)	−0.0048 (15)	0.0053 (15)
C17B	0.087 (3)	0.0543 (19)	0.0382 (17)	0.0064 (17)	−0.0023 (16)	−0.0032 (14)
C18B	0.0365 (16)	0.0468 (18)	0.107 (3)	−0.0140 (14)	−0.0201 (19)	0.0218 (19)
C19B	0.0489 (18)	0.077 (2)	0.0459 (18)	−0.0251 (17)	−0.0104 (15)	−0.0022 (17)
C20B	0.0503 (18)	0.0558 (19)	0.0350 (16)	−0.0208 (14)	−0.0082 (13)	0.0087 (14)

Geometric parameters (Å, º)

O3—C3	1.404 (4)	C7B—C8B	1.312 (8)
O3—H3	0.8200	C7B—C6B	1.481 (6)
O4—C4	1.225 (4)	C7B—H7B	0.9300
O3B—C3B	1.413 (3)	C8B—H8B	0.9300
O3B—H3B	0.8200	C7BB—C6B	1.450 (9)
O4B—C4B	1.217 (4)	C6B—C5B	1.362 (5)
C1—C16	1.527 (5)	C6B—C1B	1.525 (5)
C1—C17	1.532 (5)	C5B—C4B	1.473 (4)
C1—C2	1.532 (4)	C5B—C18B	1.498 (5)
C1—C6	1.541 (5)	C4B—C3B	1.508 (4)
C2—C3	1.496 (4)	C3B—C2B	1.487 (4)
C2—H2A	0.9700	C3B—H3B1	0.9800
C2—H2B	0.9700	C2B—C1B	1.525 (4)
C3—C4	1.515 (4)	C2B—H2B1	0.9700
C3—H3A	0.9800	C2B—H2B2	0.9700
C4—C5	1.473 (4)	C1B—C16B	1.539 (4)
C5—C6	1.347 (5)	C1B—C17B	1.547 (4)
C5—C18	1.512 (5)	C16—H16A	0.9600
C6—C7	1.429 (6)	C16—H16B	0.9600
C6—C7A	1.535 (12)	C16—H16C	0.9600
C7—C8	1.163 (6)	C17—H17A	0.9600
C8—C9	1.430 (4)	C17—H17B	0.9600
C7A—H7A	0.9300	C17—H17C	0.9600
C9—C10	1.362 (4)	C17—H17D	0.9600
C9—C19	1.504 (5)	C17—H17E	0.9600
C10—C11	1.433 (4)	C17—H17F	0.9600
C10—H10	0.9300	C18—H18A	0.9600
C11—C12	1.350 (4)	C18—H18B	0.9600
C11—H11	0.9300	C18—H18C	0.9600
C12—C13	1.437 (4)	C19—H19A	0.9600
C12—H12	0.9300	C19—H19B	0.9600
C13—C14	1.373 (4)	C19—H19C	0.9600
C13—C20	1.497 (4)	C20—H20A	0.9600
C14—C15	1.428 (4)	C20—H20B	0.9600
C14—H14	0.9300	C20—H20C	0.9600
C15—C15B	1.353 (3)	C16B—H16D	0.9600
C15—H15	0.9300	C16B—H16E	0.9600
C15B—C14B	1.434 (4)	C16B—H16F	0.9600
C15B—H15B	0.9300	C17B—H17H	0.9600
C14B—C13B	1.350 (4)	C17B—H17I	0.9600
C14B—H14B	0.9300	C17B—H17J	0.9600
C13B—C12B	1.448 (4)	C18B—H18D	0.9600
C13B—C20B	1.516 (4)	C18B—H18E	0.9600
C12B—C11B	1.348 (4)	C18B—H18F	0.9600
C12B—H12B	0.9300	C19B—H19D	0.9600
C11B—C10B	1.427 (4)	C19B—H19E	0.9600
C11B—H11B	0.9300	C19B—H19F	0.9600
C10B—C9B	1.346 (4)	C20B—H20D	0.9600
C10B—H10B	0.9300	C20B—H20E	0.9600
C9B—C8B	1.443 (4)	C20B—H20F	0.9600
C9B—C19B	1.498 (5)
C3—O3—H3	109.5	C5B—C4B—C3B	116.5 (3)
C3B—O3B—H3B	109.5	O3B—C3B—C2B	112.2 (3)
C16—C1—C17	110.0 (3)	O3B—C3B—C4B	110.8 (2)
C16—C1—C2	111.6 (3)	C2B—C3B—C4B	109.1 (2)
C17—C1—C2	106.7 (3)	O3B—C3B—H3B1	108.2
C16—C1—C6	108.5 (3)	C2B—C3B—H3B1	108.2
C17—C1—C6	110.0 (3)	C4B—C3B—H3B1	108.2
C2—C1—C6	110.0 (2)	C3B—C2B—C1B	112.2 (2)
C3—C2—C1	112.5 (2)	C3B—C2B—H2B1	109.2
C3—C2—H2A	109.1	C1B—C2B—H2B1	109.2
C1—C2—H2A	109.1	C3B—C2B—H2B2	109.2
C3—C2—H2B	109.1	C1B—C2B—H2B2	109.2
C1—C2—H2B	109.1	H2B1—C2B—H2B2	107.9
H2A—C2—H2B	107.8	C2B—C1B—C6B	111.4 (2)
O3—C3—C2	110.8 (2)	C2B—C1B—C16B	107.1 (2)
O3—C3—C4	111.3 (3)	C6B—C1B—C16B	110.1 (3)
C2—C3—C4	109.4 (2)	C2B—C1B—C17B	109.8 (3)
O3—C3—H3A	108.4	C6B—C1B—C17B	110.8 (3)
C2—C3—H3A	108.4	C16B—C1B—C17B	107.5 (3)
C4—C3—H3A	108.4	C1—C16—H16A	109.5
O4—C4—C5	122.5 (3)	C1—C16—H16B	109.5
O4—C4—C3	119.5 (3)	H16A—C16—H16B	109.5
C5—C4—C3	118.0 (3)	C1—C16—H16C	109.5
C6—C5—C4	120.1 (3)	H16A—C16—H16C	109.5
C6—C5—C18	124.8 (3)	H16B—C16—H16C	109.5
C4—C5—C18	115.1 (3)	C1—C17—H17A	109.5
C5—C6—C7	114.1 (5)	C1—C17—H17B	109.5
C5—C6—C1	123.7 (3)	H17A—C17—H17B	109.5
C7—C6—C1	121.9 (5)	C1—C17—H17C	109.5
C5—C6—C7A	136.8 (7)	H17A—C17—H17C	109.5
C7—C6—C7A	23.5 (4)	H17B—C17—H17C	109.5
C1—C6—C7A	99.4 (7)	C1—C17—H17D	109.5
C8—C7—C6	174.9 (9)	H17A—C17—H17D	141.1
C7—C8—C9	164.4 (6)	H17B—C17—H17D	56.3
C6—C7A—H7A	113.4	H17C—C17—H17D	56.3
C10—C9—C8	120.9 (3)	C1—C17—H17E	109.5
C10—C9—C19	123.3 (3)	H17A—C17—H17E	56.3
C8—C9—C19	115.7 (3)	H17B—C17—H17E	141.1
C9—C10—C11	125.4 (3)	H17C—C17—H17E	56.3
C9—C10—H10	117.3	H17D—C17—H17E	109.5
C11—C10—H10	117.3	C1—C17—H17F	109.5
C12—C11—C10	123.9 (3)	H17A—C17—H17F	56.3
C12—C11—H11	118.1	H17B—C17—H17F	56.3
C10—C11—H11	118.1	H17C—C17—H17F	141.1
C11—C12—C13	125.3 (3)	H17D—C17—H17F	109.5
C11—C12—H12	117.3	H17E—C17—H17F	109.5
C13—C12—H12	117.3	C5—C18—H18A	109.5
C14—C13—C12	118.5 (3)	C5—C18—H18B	109.5
C14—C13—C20	122.4 (3)	H18A—C18—H18B	109.5
C12—C13—C20	119.1 (2)	C5—C18—H18C	109.5
C13—C14—C15	127.1 (3)	H18A—C18—H18C	109.5
C13—C14—H14	116.4	H18B—C18—H18C	109.5
C15—C14—H14	116.4	C9—C19—H19A	109.5
C15B—C15—C14	123.3 (2)	C9—C19—H19B	109.5
C15B—C15—H15	118.4	H19A—C19—H19B	109.5
C14—C15—H15	118.4	C9—C19—H19C	109.5
C15—C15B—C14B	123.5 (2)	H19A—C19—H19C	109.5
C15—C15B—H15B	118.2	H19B—C19—H19C	109.5
C14B—C15B—H15B	118.2	C13—C20—H20A	109.5
C13B—C14B—C15B	126.9 (3)	C13—C20—H20B	109.5
C13B—C14B—H14B	116.5	H20A—C20—H20B	109.5
C15B—C14B—H14B	116.5	C13—C20—H20C	109.5
C14B—C13B—C12B	119.3 (3)	H20A—C20—H20C	109.5
C14B—C13B—C20B	123.2 (3)	H20B—C20—H20C	109.5
C12B—C13B—C20B	117.5 (2)	C1B—C16B—H16D	109.5
C11B—C12B—C13B	126.4 (3)	C1B—C16B—H16E	109.5
C11B—C12B—H12B	116.8	H16D—C16B—H16E	109.5
C13B—C12B—H12B	116.8	C1B—C16B—H16F	109.5
C12B—C11B—C10B	124.4 (3)	H16D—C16B—H16F	109.5
C12B—C11B—H11B	117.8	H16E—C16B—H16F	109.5
C10B—C11B—H11B	117.8	C1B—C17B—H17H	109.5
C9B—C10B—C11B	127.5 (3)	C1B—C17B—H17I	109.5
C9B—C10B—H10B	116.3	H17H—C17B—H17I	109.5
C11B—C10B—H10B	116.3	C1B—C17B—H17J	109.5
C10B—C9B—C8B	120.3 (3)	H17H—C17B—H17J	109.5
C10B—C9B—C19B	122.9 (3)	H17I—C17B—H17J	109.5
C8B—C9B—C19B	116.9 (3)	C5B—C18B—H18D	109.5
C8B—C7B—C6B	133.7 (8)	C5B—C18B—H18E	109.5
C8B—C7B—H7B	113.1	H18D—C18B—H18E	109.5
C6B—C7B—H7B	113.1	C5B—C18B—H18F	109.5
C7B—C8B—C9B	132.2 (5)	H18D—C18B—H18F	109.5
C7B—C8B—H8B	113.9	H18E—C18B—H18F	109.5
C9B—C8B—H8B	113.9	C9B—C19B—H19D	109.5
C5B—C6B—C7BB	108.1 (7)	C9B—C19B—H19E	109.5
C5B—C6B—C7B	130.4 (4)	H19D—C19B—H19E	109.5
C7BB—C6B—C7B	24.5 (4)	C9B—C19B—H19F	109.5
C5B—C6B—C1B	123.0 (3)	H19D—C19B—H19F	109.5
C7BB—C6B—C1B	128.7 (7)	H19E—C19B—H19F	109.5
C7B—C6B—C1B	106.4 (4)	C13B—C20B—H20D	109.5
C6B—C5B—C4B	120.3 (3)	C13B—C20B—H20E	109.5
C6B—C5B—C18B	124.2 (3)	H20D—C20B—H20E	109.5
C4B—C5B—C18B	115.5 (3)	C13B—C20B—H20F	109.5
O4B—C4B—C5B	123.3 (3)	H20D—C20B—H20F	109.5
O4B—C4B—C3B	120.2 (3)	H20E—C20B—H20F	109.5
C16—C1—C2—C3	72.6 (4)	C15—C15B—C14B—C13B	−176.7 (3)
C17—C1—C2—C3	−167.2 (3)	C15B—C14B—C13B—C12B	−178.6 (2)
C6—C1—C2—C3	−47.9 (3)	C15B—C14B—C13B—C20B	1.6 (5)
C1—C2—C3—O3	−177.7 (3)	C14B—C13B—C12B—C11B	178.1 (3)
C1—C2—C3—C4	59.2 (3)	C20B—C13B—C12B—C11B	−2.1 (4)
O3—C3—C4—O4	19.3 (4)	C13B—C12B—C11B—C10B	−178.1 (3)
C2—C3—C4—O4	142.1 (3)	C12B—C11B—C10B—C9B	178.2 (3)
O3—C3—C4—C5	−162.3 (3)	C11B—C10B—C9B—C8B	−178.4 (3)
C2—C3—C4—C5	−39.5 (4)	C11B—C10B—C9B—C19B	1.1 (5)
O4—C4—C5—C6	−172.2 (3)	C6B—C7B—C8B—C9B	−175.4 (4)
C3—C4—C5—C6	9.5 (4)	C10B—C9B—C8B—C7B	−172.6 (4)
O4—C4—C5—C18	7.1 (4)	C19B—C9B—C8B—C7B	7.8 (6)
C3—C4—C5—C18	−171.2 (3)	C8B—C7B—C6B—C5B	−23.8 (9)
C4—C5—C6—C7	−173.2 (3)	C8B—C7B—C6B—C7BB	3.7 (10)
C18—C5—C6—C7	7.5 (5)	C8B—C7B—C6B—C1B	161.8 (5)
C4—C5—C6—C1	2.1 (4)	C7BB—C6B—C5B—C4B	178.6 (5)
C18—C5—C6—C1	−177.1 (3)	C7B—C6B—C5B—C4B	−169.8 (4)
C4—C5—C6—C7A	179.2 (7)	C1B—C6B—C5B—C4B	3.7 (4)
C18—C5—C6—C7A	−0.1 (9)	C7BB—C6B—C5B—C18B	−3.1 (6)
C16—C1—C6—C5	−105.4 (3)	C7B—C6B—C5B—C18B	8.5 (6)
C17—C1—C6—C5	134.2 (3)	C1B—C6B—C5B—C18B	−178.0 (3)
C2—C1—C6—C5	16.9 (4)	C6B—C5B—C4B—O4B	−168.9 (3)
C16—C1—C6—C7	69.5 (4)	C18B—C5B—C4B—O4B	12.7 (5)
C17—C1—C6—C7	−50.8 (5)	C6B—C5B—C4B—C3B	13.0 (4)
C2—C1—C6—C7	−168.1 (4)	C18B—C5B—C4B—C3B	−165.4 (3)
C16—C1—C6—C7A	76.6 (5)	O4B—C4B—C3B—O3B	13.2 (4)
C17—C1—C6—C7A	−43.8 (6)	C5B—C4B—C3B—O3B	−168.7 (3)
C2—C1—C6—C7A	−161.1 (5)	O4B—C4B—C3B—C2B	137.2 (3)
C5—C6—C7—C8	−176 (6)	C5B—C4B—C3B—C2B	−44.7 (3)
C1—C6—C7—C8	9 (7)	O3B—C3B—C2B—C1B	−175.8 (3)
C7A—C6—C7—C8	−9 (5)	C4B—C3B—C2B—C1B	61.0 (3)
C6—C7—C8—C9	−3 (8)	C3B—C2B—C1B—C6B	−44.9 (3)
C7—C8—C9—C10	179.8 (14)	C3B—C2B—C1B—C16B	−165.3 (3)
C7—C8—C9—C19	−0.4 (17)	C3B—C2B—C1B—C17B	78.2 (3)
C8—C9—C10—C11	−178.8 (3)	C5B—C6B—C1B—C2B	12.1 (4)
C19—C9—C10—C11	1.4 (5)	C7BB—C6B—C1B—C2B	−161.6 (6)
C9—C10—C11—C12	−179.9 (3)	C7B—C6B—C1B—C2B	−173.0 (3)
C10—C11—C12—C13	179.8 (3)	C5B—C6B—C1B—C16B	130.7 (3)
C11—C12—C13—C14	−178.5 (3)	C7BB—C6B—C1B—C16B	−43.0 (7)
C11—C12—C13—C20	1.1 (5)	C7B—C6B—C1B—C16B	−54.4 (4)
C12—C13—C14—C15	177.6 (3)	C5B—C6B—C1B—C17B	−110.4 (3)
C20—C13—C14—C15	−2.0 (5)	C7BB—C6B—C1B—C17B	75.8 (6)
C13—C14—C15—C15B	177.4 (3)	C7B—C6B—C1B—C17B	64.5 (4)
C14—C15—C15B—C14B	178.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.82	2.25	2.669 (4)	112

(3)

Crystal data

C40H48O4	Z = 1
Mr = 592.78	F(000) = 320
Triclinic, P1	Dx = 1.148 Mg m^−3
Hall symbol: P1	Synchrotron radiation, λ = 0.67100 Å
a = 7.4769 (14) Å	Cell parameters from 979 reflections
b = 10.4729 (19) Å	θ = 2.3–24.0°
c = 11.633 (2) Å	µ = 0.07 mm^−1
α = 75.606 (2)°	T = 100 K
β = 85.901 (2)°	Plate, red
γ = 76.389 (2)°	0.04 × 0.03 × 0.01 mm
V = 857.5 (3) Å^3

Data collection

Bruker APEXII CCD area detector diffractometer	4002 independent reflections
Radiation source: Station 9.8, SRS, Daresbury	2799 reflections with I > 2σ(I)
Silicon monochromator	Rint = 0.062
phi and ω scans	θmax = 26.1°, θmin = 2.0°
Absorption correction: multi-scan SADABS	h = −9→9
Tmin = 0.749, Tmax = 1.000	k = −13→13
14633 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0581P)^2] where P = (Fo^2 + 2Fc^2)/3
4002 reflections	(Δ/σ)max = 0.003
409 parameters	Δρmax = 0.19 e Å^−3
3 restraints	Δρmin = −0.17 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O3	0.8989 (3)	1.2181 (2)	1.2004 (2)	0.0432 (5)
H3	0.9492	1.1765	1.2634	0.065*
O4	1.0608 (3)	0.9612 (2)	1.28650 (17)	0.0343 (5)
O3B	0.5316 (3)	−0.08464 (19)	−0.76918 (19)	0.0396 (5)
H3B	0.4859	−0.0538	−0.8351	0.059*
O4B	0.3773 (3)	0.1658 (2)	−0.87573 (17)	0.0367 (5)
C1	0.9374 (4)	1.0816 (3)	0.9257 (3)	0.0287 (6)
C2	0.9550 (4)	1.1761 (3)	1.0039 (3)	0.0312 (6)
H2A	1.0821	1.1833	1.0030	0.037*
H2B	0.8805	1.2657	0.9714	0.037*
C3	0.8949 (4)	1.1264 (3)	1.1297 (2)	0.0314 (6)
H3A	0.7682	1.1157	1.1291	0.038*
C4	1.0166 (4)	0.9893 (3)	1.1820 (2)	0.0271 (6)
C5	1.0676 (4)	0.8941 (3)	1.1061 (2)	0.0257 (6)
C6	1.0188 (4)	0.9345 (3)	0.9905 (2)	0.0249 (6)
C7	1.0400 (4)	0.8359 (3)	0.9220 (2)	0.0283 (6)
C8	1.0452 (4)	0.7499 (3)	0.8686 (2)	0.0273 (6)
C9	1.0483 (4)	0.6431 (3)	0.8133 (2)	0.0267 (6)
C10	0.9954 (4)	0.6728 (3)	0.6992 (2)	0.0261 (6)
H10	0.9680	0.7641	0.6604	0.031*
C11	0.9766 (4)	0.5803 (3)	0.6308 (2)	0.0273 (7)
H11	1.0066	0.4880	0.6656	0.033*
C12	0.9172 (4)	0.6216 (3)	0.5181 (2)	0.0266 (6)
H12	0.8927	0.7144	0.4855	0.032*
C13	0.8871 (4)	0.5396 (3)	0.4422 (2)	0.0256 (6)
C14	0.8166 (4)	0.6035 (3)	0.3333 (3)	0.0269 (6)
H14	0.7938	0.6974	0.3150	0.032*
C15	0.7729 (4)	0.5457 (3)	0.2434 (2)	0.0266 (6)
H15	0.7907	0.4521	0.2589	0.032*
C16	1.0449 (5)	1.1181 (3)	0.8109 (3)	0.0430 (8)
H16A	1.1727	1.1035	0.8283	0.064*
H16B	0.9987	1.2115	0.7725	0.064*
H16C	1.0311	1.0624	0.7594	0.064*
C17	0.7356 (4)	1.0966 (3)	0.8971 (3)	0.0386 (7)
H17D	0.7279	1.0357	0.8489	0.058*
H17E	0.6854	1.1879	0.8547	0.058*
H17F	0.6670	1.0754	0.9695	0.058*
C18	1.1667 (4)	0.7522 (3)	1.1629 (3)	0.0326 (7)
H18D	1.2130	0.7046	1.1024	0.049*
H18E	1.0831	0.7064	1.2141	0.049*
H18F	1.2673	0.7548	1.2084	0.049*
C19	1.1066 (4)	0.5018 (3)	0.8899 (3)	0.0306 (6)
H19D	1.0184	0.4875	0.9531	0.046*
H19E	1.2252	0.4905	0.9226	0.046*
H19F	1.1134	0.4375	0.8427	0.046*
C20	0.9321 (4)	0.3890 (3)	0.4876 (3)	0.0301 (6)
H20D	0.8526	0.3640	0.5538	0.045*
H20E	1.0579	0.3590	0.5125	0.045*
H20F	0.9147	0.3474	0.4257	0.045*
C1B	0.5262 (4)	0.0926 (3)	−0.5234 (2)	0.0288 (6)
C2B	0.5945 (4)	−0.0060 (3)	−0.6028 (3)	0.0295 (6)
H2B1	0.7085	0.0113	−0.6417	0.035*
H2B2	0.6209	−0.0977	−0.5536	0.035*
C3B	0.4587 (4)	0.0045 (3)	−0.6955 (3)	0.0311 (6)
H3B1	0.3480	−0.0210	−0.6554	0.037*
C4B	0.4043 (4)	0.1479 (3)	−0.7703 (2)	0.0273 (6)
C5B	0.3856 (4)	0.2597 (3)	−0.7118 (2)	0.0249 (6)
C6B	0.4485 (4)	0.2347 (3)	−0.6001 (2)	0.0256 (6)
C7B	0.4368 (4)	0.3432 (3)	−0.5458 (2)	0.0256 (6)
C8B	0.4343 (4)	0.4333 (3)	−0.4967 (2)	0.0265 (6)
C9B	0.4374 (4)	0.5392 (3)	−0.4410 (2)	0.0238 (6)
C10B	0.4945 (4)	0.5061 (3)	−0.3278 (2)	0.0269 (6)
H10B	0.5260	0.4141	−0.2919	0.032*
C11B	0.5123 (4)	0.5946 (3)	−0.2569 (2)	0.0250 (6)
H11B	0.4822	0.6873	−0.2897	0.030*
C12B	0.5711 (4)	0.5496 (3)	−0.1438 (2)	0.0264 (6)
H12B	0.5976	0.4563	−0.1137	0.032*
C13B	0.5977 (4)	0.6285 (3)	−0.0644 (2)	0.0251 (6)
C14B	0.6637 (4)	0.5635 (3)	0.0458 (2)	0.0261 (6)
H14B	0.6834	0.4696	0.0642	0.031*
C15B	0.7067 (4)	0.6205 (3)	0.1367 (3)	0.0279 (6)
H15B	0.6882	0.7141	0.1217	0.033*
C16B	0.6881 (4)	0.0925 (3)	−0.4508 (3)	0.0404 (8)
H16D	0.7357	0.0025	−0.4045	0.061*
H16E	0.6476	0.1523	−0.3988	0.061*
H16F	0.7828	0.1226	−0.5032	0.061*
C17B	0.3718 (5)	0.0509 (3)	−0.4387 (3)	0.0385 (7)
H17A	0.2700	0.0497	−0.4839	0.058*
H17B	0.3321	0.1147	−0.3902	0.058*
H17C	0.4166	−0.0376	−0.3889	0.058*
C18B	0.3024 (4)	0.3984 (3)	−0.7835 (3)	0.0327 (7)
H18A	0.3078	0.4641	−0.7399	0.049*
H18B	0.1764	0.4037	−0.7996	0.049*
H18C	0.3696	0.4164	−0.8569	0.049*
C19B	0.3774 (4)	0.6814 (3)	−0.5149 (3)	0.0284 (6)
H19A	0.3805	0.7443	−0.4679	0.043*
H19B	0.2544	0.6954	−0.5420	0.043*
H19C	0.4591	0.6954	−0.5820	0.043*
C20B	0.5514 (4)	0.7809 (3)	−0.1085 (3)	0.0295 (6)
H20A	0.5672	0.8214	−0.0455	0.044*
H20B	0.4260	0.8109	−0.1341	0.044*
H20C	0.6316	0.8072	−0.1739	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0563 (14)	0.0333 (11)	0.0446 (13)	−0.0041 (10)	−0.0034 (11)	−0.0226 (10)
O4	0.0356 (11)	0.0404 (12)	0.0290 (12)	−0.0049 (9)	−0.0041 (9)	−0.0144 (9)
O3B	0.0526 (14)	0.0269 (11)	0.0406 (12)	0.0010 (9)	−0.0039 (11)	−0.0186 (9)
O4B	0.0429 (12)	0.0388 (12)	0.0282 (12)	−0.0016 (10)	−0.0081 (9)	−0.0129 (9)
C1	0.0354 (16)	0.0227 (15)	0.0274 (14)	−0.0060 (12)	−0.0047 (12)	−0.0042 (11)
C2	0.0373 (16)	0.0185 (13)	0.0352 (15)	−0.0022 (11)	−0.0060 (13)	−0.0037 (11)
C3	0.0347 (16)	0.0273 (15)	0.0354 (16)	−0.0047 (12)	−0.0018 (12)	−0.0151 (12)
C4	0.0274 (14)	0.0280 (14)	0.0280 (15)	−0.0074 (11)	−0.0012 (12)	−0.0091 (12)
C5	0.0269 (15)	0.0223 (14)	0.0288 (15)	−0.0072 (11)	0.0003 (12)	−0.0066 (12)
C6	0.0278 (15)	0.0222 (14)	0.0248 (15)	−0.0033 (12)	−0.0003 (12)	−0.0082 (12)
C7	0.0285 (15)	0.0262 (15)	0.0275 (15)	−0.0027 (12)	−0.0022 (12)	−0.0041 (13)
C8	0.0295 (15)	0.0269 (15)	0.0251 (14)	−0.0029 (12)	−0.0004 (12)	−0.0085 (13)
C9	0.0256 (15)	0.0262 (15)	0.0295 (16)	−0.0048 (12)	−0.0008 (13)	−0.0096 (13)
C10	0.0267 (15)	0.0231 (14)	0.0288 (15)	−0.0040 (11)	0.0002 (12)	−0.0083 (12)
C11	0.0250 (15)	0.0242 (15)	0.0311 (17)	−0.0015 (12)	−0.0012 (13)	−0.0072 (13)
C12	0.0289 (15)	0.0227 (14)	0.0276 (15)	−0.0021 (12)	−0.0016 (12)	−0.0078 (12)
C13	0.0231 (14)	0.0261 (15)	0.0280 (15)	−0.0037 (12)	0.0005 (12)	−0.0090 (12)
C14	0.0290 (15)	0.0223 (14)	0.0292 (14)	−0.0020 (12)	−0.0008 (12)	−0.0092 (12)
C15	0.0258 (14)	0.0255 (15)	0.0268 (16)	−0.0021 (12)	0.0004 (12)	−0.0070 (12)
C16	0.057 (2)	0.0363 (17)	0.0328 (16)	−0.0123 (15)	0.0011 (15)	−0.0017 (14)
C17	0.0453 (18)	0.0245 (15)	0.0422 (17)	0.0012 (13)	−0.0135 (14)	−0.0060 (13)
C18	0.0421 (18)	0.0252 (14)	0.0276 (15)	−0.0023 (13)	−0.0094 (13)	−0.0036 (12)
C19	0.0371 (16)	0.0289 (15)	0.0277 (15)	−0.0068 (13)	−0.0013 (13)	−0.0106 (12)
C20	0.0354 (16)	0.0292 (15)	0.0256 (14)	−0.0044 (12)	−0.0046 (12)	−0.0076 (12)
C1B	0.0352 (16)	0.0201 (14)	0.0292 (15)	−0.0024 (12)	−0.0057 (12)	−0.0043 (12)
C2B	0.0305 (15)	0.0204 (13)	0.0345 (15)	−0.0015 (11)	−0.0037 (12)	−0.0040 (11)
C3B	0.0360 (15)	0.0227 (14)	0.0356 (16)	−0.0019 (12)	−0.0028 (12)	−0.0128 (12)
C4B	0.0238 (14)	0.0308 (15)	0.0280 (16)	−0.0045 (11)	−0.0018 (11)	−0.0094 (12)
C5B	0.0263 (15)	0.0230 (14)	0.0257 (15)	−0.0034 (11)	−0.0013 (12)	−0.0082 (11)
C6B	0.0252 (14)	0.0216 (14)	0.0292 (16)	−0.0030 (11)	0.0015 (12)	−0.0072 (12)
C7B	0.0288 (15)	0.0252 (15)	0.0218 (14)	−0.0040 (12)	−0.0053 (12)	−0.0046 (12)
C8B	0.0250 (15)	0.0255 (15)	0.0251 (14)	−0.0008 (11)	−0.0058 (12)	−0.0016 (12)
C9B	0.0250 (15)	0.0234 (14)	0.0243 (14)	−0.0043 (12)	0.0011 (12)	−0.0094 (12)
C10B	0.0252 (15)	0.0237 (14)	0.0313 (16)	−0.0023 (12)	−0.0011 (12)	−0.0087 (12)
C11B	0.0243 (15)	0.0235 (15)	0.0262 (15)	−0.0015 (12)	−0.0017 (12)	−0.0074 (12)
C12B	0.0267 (15)	0.0232 (14)	0.0278 (15)	−0.0018 (12)	−0.0020 (12)	−0.0065 (12)
C13B	0.0240 (15)	0.0252 (15)	0.0261 (15)	−0.0029 (12)	−0.0014 (12)	−0.0085 (12)
C14B	0.0277 (15)	0.0236 (14)	0.0277 (15)	−0.0014 (12)	−0.0010 (12)	−0.0112 (12)
C15B	0.0280 (15)	0.0263 (15)	0.0294 (16)	−0.0032 (12)	0.0006 (12)	−0.0098 (13)
C16B	0.0526 (19)	0.0250 (15)	0.0400 (18)	0.0036 (14)	−0.0214 (15)	−0.0070 (13)
C17B	0.0526 (19)	0.0239 (14)	0.0338 (16)	−0.0058 (13)	0.0061 (14)	−0.0016 (12)
C18B	0.0428 (17)	0.0235 (15)	0.0293 (15)	−0.0011 (13)	−0.0049 (13)	−0.0064 (12)
C19B	0.0333 (15)	0.0237 (14)	0.0289 (16)	−0.0054 (12)	−0.0039 (12)	−0.0074 (12)
C20B	0.0341 (16)	0.0265 (14)	0.0278 (15)	−0.0048 (12)	−0.0053 (12)	−0.0072 (12)

Geometric parameters (Å, º)

O3—C3	1.418 (3)	C20—H20D	0.9600
O3—H3	0.8200	C20—H20E	0.9600
O4—C4	1.228 (3)	C20—H20F	0.9600
O3B—C3B	1.412 (3)	C1B—C16B	1.524 (4)
O3B—H3B	0.8200	C1B—C2B	1.530 (4)
O4B—C4B	1.218 (3)	C1B—C17B	1.535 (4)
C1—C16	1.521 (4)	C1B—C6B	1.535 (4)
C1—C17	1.532 (4)	C2B—C3B	1.501 (4)
C1—C2	1.534 (4)	C2B—H2B1	0.9700
C1—C6	1.536 (4)	C2B—H2B2	0.9700
C2—C3	1.501 (4)	C3B—C4B	1.513 (4)
C2—H2A	0.9700	C3B—H3B1	0.9800
C2—H2B	0.9700	C4B—C5B	1.471 (4)
C3—C4	1.513 (4)	C5B—C6B	1.356 (4)
C3—H3A	0.9800	C5B—C18B	1.496 (4)
C4—C5	1.460 (4)	C6B—C7B	1.414 (4)
C5—C6	1.354 (4)	C7B—C8B	1.215 (4)
C5—C18	1.503 (4)	C8B—C9B	1.422 (4)
C6—C7	1.429 (4)	C9B—C10B	1.350 (4)
C7—C8	1.207 (4)	C9B—C19B	1.504 (4)
C8—C9	1.418 (4)	C10B—C11B	1.418 (4)
C9—C10	1.352 (4)	C10B—H10B	0.9300
C9—C19	1.507 (4)	C11B—C12B	1.351 (4)
C10—C11	1.434 (4)	C11B—H11B	0.9300
C10—H10	0.9300	C12B—C13B	1.434 (4)
C11—C12	1.347 (4)	C12B—H12B	0.9300
C11—H11	0.9300	C13B—C14B	1.360 (4)
C12—C13	1.437 (4)	C13B—C20B	1.513 (4)
C12—H12	0.9300	C14B—C15B	1.425 (4)
C13—C14	1.356 (4)	C14B—H14B	0.9300
C13—C20	1.496 (4)	C15B—H15B	0.9300
C14—C15	1.422 (4)	C16B—H16D	0.9600
C14—H14	0.9300	C16B—H16E	0.9600
C15—C15B	1.349 (3)	C16B—H16F	0.9600
C15—H15	0.9300	C17B—H17A	0.9600
C16—H16A	0.9600	C17B—H17B	0.9600
C16—H16B	0.9600	C17B—H17C	0.9600
C16—H16C	0.9600	C18B—H18A	0.9600
C17—H17D	0.9600	C18B—H18B	0.9600
C17—H17E	0.9600	C18B—H18C	0.9600
C17—H17F	0.9600	C19B—H19A	0.9600
C18—H18D	0.9600	C19B—H19B	0.9600
C18—H18E	0.9600	C19B—H19C	0.9600
C18—H18F	0.9600	C20B—H20A	0.9600
C19—H19D	0.9600	C20B—H20B	0.9600
C19—H19E	0.9600	C20B—H20C	0.9600
C19—H19F	0.9600
C3—O3—H3	109.5	H20E—C20—H20F	109.5
C3B—O3B—H3B	109.5	C16B—C1B—C2B	108.0 (2)
C16—C1—C17	109.4 (3)	C16B—C1B—C17B	109.1 (3)
C16—C1—C2	108.4 (2)	C2B—C1B—C17B	111.5 (2)
C17—C1—C2	111.0 (2)	C16B—C1B—C6B	110.9 (2)
C16—C1—C6	109.4 (2)	C2B—C1B—C6B	109.9 (2)
C17—C1—C6	109.4 (2)	C17B—C1B—C6B	107.5 (2)
C2—C1—C6	109.3 (2)	C3B—C2B—C1B	113.2 (2)
C3—C2—C1	112.0 (2)	C3B—C2B—H2B1	108.9
C3—C2—H2A	109.2	C1B—C2B—H2B1	108.9
C1—C2—H2A	109.2	C3B—C2B—H2B2	108.9
C3—C2—H2B	109.2	C1B—C2B—H2B2	108.9
C1—C2—H2B	109.2	H2B1—C2B—H2B2	107.8
H2A—C2—H2B	107.9	O3B—C3B—C2B	110.8 (2)
O3—C3—C2	112.2 (2)	O3B—C3B—C4B	109.8 (2)
O3—C3—C4	110.5 (2)	C2B—C3B—C4B	111.1 (2)
C2—C3—C4	109.1 (2)	O3B—C3B—H3B1	108.4
O3—C3—H3A	108.3	C2B—C3B—H3B1	108.4
C2—C3—H3A	108.3	C4B—C3B—H3B1	108.4
C4—C3—H3A	108.3	O4B—C4B—C5B	122.9 (3)
O4—C4—C5	123.2 (2)	O4B—C4B—C3B	118.9 (3)
O4—C4—C3	119.1 (2)	C5B—C4B—C3B	118.2 (2)
C5—C4—C3	117.6 (2)	C6B—C5B—C4B	119.9 (2)
C6—C5—C4	119.6 (2)	C6B—C5B—C18B	123.5 (3)
C6—C5—C18	123.0 (2)	C4B—C5B—C18B	116.5 (2)
C4—C5—C18	117.4 (2)	C5B—C6B—C7B	119.8 (2)
C5—C6—C7	119.3 (2)	C5B—C6B—C1B	124.1 (3)
C5—C6—C1	124.6 (2)	C7B—C6B—C1B	116.1 (2)
C7—C6—C1	116.1 (2)	C8B—C7B—C6B	177.0 (3)
C8—C7—C6	174.7 (3)	C7B—C8B—C9B	178.0 (3)
C7—C8—C9	176.1 (3)	C10B—C9B—C8B	118.5 (2)
C10—C9—C8	119.3 (3)	C10B—C9B—C19B	124.9 (3)
C10—C9—C19	124.6 (3)	C8B—C9B—C19B	116.6 (2)
C8—C9—C19	116.1 (2)	C9B—C10B—C11B	127.8 (3)
C9—C10—C11	127.7 (3)	C9B—C10B—H10B	116.1
C9—C10—H10	116.2	C11B—C10B—H10B	116.1
C11—C10—H10	116.2	C12B—C11B—C10B	122.6 (3)
C12—C11—C10	122.6 (3)	C12B—C11B—H11B	118.7
C12—C11—H11	118.7	C10B—C11B—H11B	118.7
C10—C11—H11	118.7	C11B—C12B—C13B	127.8 (3)
C11—C12—C13	127.8 (3)	C11B—C12B—H12B	116.1
C11—C12—H12	116.1	C13B—C12B—H12B	116.1
C13—C12—H12	116.1	C14B—C13B—C12B	118.9 (3)
C14—C13—C12	117.8 (3)	C14B—C13B—C20B	123.2 (3)
C14—C13—C20	123.5 (3)	C12B—C13B—C20B	117.9 (2)
C12—C13—C20	118.7 (2)	C13B—C14B—C15B	128.4 (3)
C13—C14—C15	128.5 (3)	C13B—C14B—H14B	115.8
C13—C14—H14	115.7	C15B—C14B—H14B	115.8
C15—C14—H14	115.7	C15—C15B—C14B	123.4 (2)
C15B—C15—C14	123.0 (2)	C15—C15B—H15B	118.3
C15B—C15—H15	118.5	C14B—C15B—H15B	118.3
C14—C15—H15	118.5	C1B—C16B—H16D	109.5
C1—C16—H16A	109.5	C1B—C16B—H16E	109.5
C1—C16—H16B	109.5	H16D—C16B—H16E	109.5
H16A—C16—H16B	109.5	C1B—C16B—H16F	109.5
C1—C16—H16C	109.5	H16D—C16B—H16F	109.5
H16A—C16—H16C	109.5	H16E—C16B—H16F	109.5
H16B—C16—H16C	109.5	C1B—C17B—H17A	109.5
C1—C17—H17D	109.5	C1B—C17B—H17B	109.5
C1—C17—H17E	109.5	H17A—C17B—H17B	109.5
H17D—C17—H17E	109.5	C1B—C17B—H17C	109.5
C1—C17—H17F	109.5	H17A—C17B—H17C	109.5
H17D—C17—H17F	109.5	H17B—C17B—H17C	109.5
H17E—C17—H17F	109.5	C5B—C18B—H18A	109.5
C5—C18—H18D	109.5	C5B—C18B—H18B	109.5
C5—C18—H18E	109.5	H18A—C18B—H18B	109.5
H18D—C18—H18E	109.5	C5B—C18B—H18C	109.5
C5—C18—H18F	109.5	H18A—C18B—H18C	109.5
H18D—C18—H18F	109.5	H18B—C18B—H18C	109.5
H18E—C18—H18F	109.5	C9B—C19B—H19A	109.5
C9—C19—H19D	109.5	C9B—C19B—H19B	109.5
C9—C19—H19E	109.5	H19A—C19B—H19B	109.5
H19D—C19—H19E	109.5	C9B—C19B—H19C	109.5
C9—C19—H19F	109.5	H19A—C19B—H19C	109.5
H19D—C19—H19F	109.5	H19B—C19B—H19C	109.5
H19E—C19—H19F	109.5	C13B—C20B—H20A	109.5
C13—C20—H20D	109.5	C13B—C20B—H20B	109.5
C13—C20—H20E	109.5	H20A—C20B—H20B	109.5
H20D—C20—H20E	109.5	C13B—C20B—H20C	109.5
C13—C20—H20F	109.5	H20A—C20B—H20C	109.5
H20D—C20—H20F	109.5	H20B—C20B—H20C	109.5
C16—C1—C2—C3	−165.6 (3)	C17B—C1B—C2B—C3B	71.3 (3)
C17—C1—C2—C3	74.2 (3)	C6B—C1B—C2B—C3B	−47.7 (3)
C6—C1—C2—C3	−46.5 (3)	C1B—C2B—C3B—O3B	177.6 (2)
C1—C2—C3—O3	−175.9 (2)	C1B—C2B—C3B—C4B	55.4 (3)
C1—C2—C3—C4	61.3 (3)	O3B—C3B—C4B—O4B	20.8 (4)
O3—C3—C4—O4	19.1 (4)	C2B—C3B—C4B—O4B	143.6 (3)
C2—C3—C4—O4	142.8 (3)	O3B—C3B—C4B—C5B	−159.5 (2)
O3—C3—C4—C5	−164.1 (2)	C2B—C3B—C4B—C5B	−36.7 (3)
C2—C3—C4—C5	−40.4 (3)	O4B—C4B—C5B—C6B	−168.2 (3)
O4—C4—C5—C6	−177.8 (3)	C3B—C4B—C5B—C6B	12.0 (4)
C3—C4—C5—C6	5.6 (4)	O4B—C4B—C5B—C18B	9.4 (4)
O4—C4—C5—C18	4.7 (4)	C3B—C4B—C5B—C18B	−170.3 (3)
C3—C4—C5—C18	−171.9 (3)	C4B—C5B—C6B—C7B	177.5 (2)
C4—C5—C6—C7	−169.1 (2)	C18B—C5B—C6B—C7B	0.0 (4)
C18—C5—C6—C7	8.2 (4)	C4B—C5B—C6B—C1B	−5.4 (4)
C4—C5—C6—C1	9.9 (4)	C18B—C5B—C6B—C1B	177.2 (3)
C18—C5—C6—C1	−172.7 (3)	C16B—C1B—C6B—C5B	142.3 (3)
C16—C1—C6—C5	129.2 (3)	C2B—C1B—C6B—C5B	23.0 (4)
C17—C1—C6—C5	−111.0 (3)	C17B—C1B—C6B—C5B	−98.6 (3)
C2—C1—C6—C5	10.7 (4)	C16B—C1B—C6B—C7B	−40.5 (3)
C16—C1—C6—C7	−51.7 (3)	C2B—C1B—C6B—C7B	−159.8 (2)
C17—C1—C6—C7	68.1 (3)	C17B—C1B—C6B—C7B	78.6 (3)
C2—C1—C6—C7	−170.2 (2)	C5B—C6B—C7B—C8B	−145 (5)
C5—C6—C7—C8	78 (3)	C1B—C6B—C7B—C8B	37 (5)
C1—C6—C7—C8	−101 (3)	C6B—C7B—C8B—C9B	58 (11)
C6—C7—C8—C9	−44 (7)	C7B—C8B—C9B—C10B	−98 (8)
C7—C8—C9—C10	148 (4)	C7B—C8B—C9B—C19B	82 (8)
C7—C8—C9—C19	−30 (5)	C8B—C9B—C10B—C11B	178.4 (3)
C8—C9—C10—C11	−175.2 (3)	C19B—C9B—C10B—C11B	−0.9 (5)
C19—C9—C10—C11	2.8 (5)	C9B—C10B—C11B—C12B	179.9 (3)
C9—C10—C11—C12	177.9 (3)	C10B—C11B—C12B—C13B	178.8 (3)
C10—C11—C12—C13	−177.8 (3)	C11B—C12B—C13B—C14B	−178.0 (3)
C11—C12—C13—C14	176.4 (3)	C11B—C12B—C13B—C20B	1.6 (4)
C11—C12—C13—C20	−2.7 (4)	C12B—C13B—C14B—C15B	177.5 (2)
C12—C13—C14—C15	−179.2 (3)	C20B—C13B—C14B—C15B	−2.1 (4)
C20—C13—C14—C15	−0.2 (5)	C14—C15—C15B—C14B	179.5 (3)
C13—C14—C15—C15B	−178.4 (3)	C13B—C14B—C15B—C15	−179.6 (3)
C16B—C1B—C2B—C3B	−168.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.82	2.17	2.648 (3)	117
O3B—H3B···O4B	0.82	2.19	2.629 (3)	114