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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768109004649/ry5026sup1.cif
Contains datablocks s-cis-1, s-trans-1, 2, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109004649/ry5026s-cis-1sup2.hkl
Contains datablock s-cis-1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109004649/ry5026s-trans-1sup3.hkl
Contains datablock s-trans-1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109004649/ry50262sup4.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109004649/ry50263sup5.hkl
Contains datablock 3

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768109004649/ry5026sup6.pdf
Crystals of s-cis and s-trans conformers of astaxanthin diacetate

CCDC references: 639543; 639544; 737461; 737462

Computing details top

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 top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
[Figure 12]
(s-cis-1) top
Crystal data top
C44H56O6·0.44(C4H8O2)F(000) = 1556
Mr = 719.59Dx = 1.153 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C2ycCell parameters from 4444 reflections
a = 12.9673 (15) Åθ = 2.5–26.4°
b = 10.7883 (13) ŵ = 0.08 mm1
c = 30.264 (4) ÅT = 100 K
β = 101.796 (1)°Plate, orange
V = 4144.3 (8) Å30.60 × 0.60 × 0.05 mm
Z = 4
Data collection top
Bruker APEX CCD area detector
diffractometer
2913 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.076
Graphite monochromatorθmax = 25.0°, θmin = 2.5°
phi and ω scansh = 1515
13064 measured reflectionsk = 1212
3632 independent reflectionsl = 3535
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.085Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.218H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0625P)2 + 15.0678P]
where P = (Fo2 + 2Fc2)/3
3632 reflections(Δ/σ)max < 0.001
304 parametersΔρmax = 0.54 e Å3
117 restraintsΔρmin = 0.28 e Å3
Crystal data top
C44H56O6·0.44(C4H8O2)V = 4144.3 (8) Å3
Mr = 719.59Z = 4
Monoclinic, C2/cMo Kα radiation
a = 12.9673 (15) ŵ = 0.08 mm1
b = 10.7883 (13) ÅT = 100 K
c = 30.264 (4) Å0.60 × 0.60 × 0.05 mm
β = 101.796 (1)°
Data collection top
Bruker APEX CCD area detector
diffractometer
2913 reflections with I > 2σ(I)
13064 measured reflectionsRint = 0.076
3632 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.085117 restraints
wR(F2) = 0.218H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0625P)2 + 15.0678P]
where P = (Fo2 + 2Fc2)/3
3632 reflectionsΔρmax = 0.54 e Å3
304 parametersΔρmin = 0.28 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O30.8438 (2)0.5392 (4)0.76819 (10)0.0500 (10)0.743 (4)
O40.6749 (3)0.6950 (6)0.75060 (14)0.0599 (13)0.743 (4)
O210.7427 (3)0.4588 (7)0.81238 (14)0.0756 (15)0.743 (4)
C10.7275 (3)0.4789 (4)0.64577 (11)0.0438 (9)0.743 (4)
C20.8081 (4)0.5029 (8)0.68898 (18)0.0405 (14)0.743 (4)
H2A0.86080.43520.69330.049*0.743 (4)
H2B0.84560.58120.68570.049*0.743 (4)
C30.7618 (4)0.5114 (5)0.72946 (15)0.0462 (11)0.743 (4)
H30.72790.43070.73430.055*0.743 (4)
C40.6796 (4)0.6138 (6)0.72271 (16)0.0457 (13)0.743 (4)
C210.8211 (5)0.5079 (6)0.80802 (18)0.0496 (13)0.743 (4)
C220.9124 (4)0.5375 (5)0.84551 (16)0.0503 (13)0.743 (4)
H22A0.88830.54110.87410.075*0.743 (4)
H22B0.94230.61780.83970.075*0.743 (4)
H22C0.96630.47300.84720.075*0.743 (4)
O3B0.8679 (7)0.7147 (9)0.7386 (3)0.046 (3)*0.257 (4)
O4B0.6627 (11)0.7507 (12)0.7393 (4)0.051 (4)*0.257 (4)
O21B0.9789 (9)0.7782 (11)0.6958 (4)0.058 (3)*0.257 (4)
C1B0.7275 (3)0.4789 (4)0.64577 (11)0.0438 (9)0.257 (4)
C2B0.8039 (15)0.5405 (15)0.6861 (6)0.038 (6)*0.257 (4)
H2D0.80110.48980.71310.046*0.257 (4)
H2E0.87580.53070.68020.046*0.257 (4)
C3B0.7942 (9)0.6733 (11)0.6995 (4)0.038 (3)*0.257 (4)
H3B0.80210.72700.67350.046*0.257 (4)
C4B0.6841 (9)0.6913 (14)0.7080 (5)0.038 (3)*0.257 (4)
C21B0.9549 (10)0.7718 (14)0.7303 (4)0.039 (3)*0.257 (4)
C22B1.0088 (14)0.8293 (18)0.7739 (5)0.055 (4)*0.257 (4)
H22D1.07090.77990.78720.083*0.257 (4)
H22E0.96020.83200.79470.083*0.257 (4)
H22F1.03080.91370.76820.083*0.257 (4)
C50.5996 (3)0.6111 (4)0.67832 (13)0.0465 (10)
C60.6200 (2)0.5380 (3)0.64475 (11)0.0340 (8)
C70.5385 (2)0.5087 (3)0.60463 (10)0.0285 (7)
H70.55630.51940.57590.034*
C80.4415 (2)0.4683 (3)0.60543 (11)0.0310 (7)
H80.42350.45990.63420.037*
C90.3610 (2)0.4362 (3)0.56609 (10)0.0279 (7)
C100.2652 (2)0.3960 (3)0.57222 (11)0.0315 (7)
H100.25750.38320.60240.038*
C110.1752 (2)0.3712 (3)0.53719 (11)0.0298 (7)
H110.18280.38220.50690.036*
C120.0804 (2)0.3333 (3)0.54402 (11)0.0289 (7)
H120.07530.31360.57410.035*
C130.0138 (2)0.3203 (3)0.50945 (10)0.0278 (7)
C140.1055 (2)0.2856 (3)0.52153 (11)0.0291 (7)
H140.10130.26930.55270.035*
C150.2070 (2)0.2707 (3)0.49289 (11)0.0293 (7)
H150.21450.29140.46190.035*
C160.7122 (5)0.3328 (5)0.6457 (2)0.0474 (13)0.743 (4)
H16A0.77880.29210.64390.071*0.743 (4)
H16B0.65770.30870.61970.071*0.743 (4)
H16C0.69070.30740.67360.071*0.743 (4)
C170.7701 (4)0.5087 (8)0.60408 (16)0.0474 (14)0.743 (4)
H17A0.84150.47500.60740.071*0.743 (4)
H17B0.77210.59880.60020.071*0.743 (4)
H17C0.72440.47170.57760.071*0.743 (4)
C16B0.723 (3)0.3478 (19)0.6298 (11)0.112 (14)*0.257 (4)
H16D0.64930.32530.61730.168*0.257 (4)
H16E0.75120.29300.65520.168*0.257 (4)
H16F0.76430.33900.60640.168*0.257 (4)
C17B0.774 (2)0.566 (2)0.6114 (8)0.074 (8)*0.257 (4)
H17D0.78710.64950.62430.110*0.257 (4)
H17E0.72380.57100.58260.110*0.257 (4)
H17F0.84090.53120.60650.110*0.257 (4)
C180.4987 (3)0.6817 (4)0.67708 (13)0.0500 (10)
H18A0.46170.69240.64570.075*
H18B0.51490.76320.69110.075*
H18C0.45380.63540.69370.075*
C190.3862 (2)0.4522 (3)0.52046 (10)0.0304 (7)
H19A0.33090.41350.49770.046*
H19B0.45400.41290.51990.046*
H19C0.39020.54080.51380.046*
C200.0072 (2)0.3484 (3)0.46176 (11)0.0324 (7)
H20A0.07710.33970.44230.049*
H20B0.04180.29040.45190.049*
H20C0.01820.43340.45980.049*
O1S0.5479 (16)0.325 (2)0.7471 (7)0.152 (10)*0.22
O2S0.6797 (14)0.4532 (16)0.7699 (6)0.106 (6)*0.22
C1S0.6170 (16)0.3579 (19)0.7746 (6)0.104 (9)*0.22
C2S0.6516 (17)0.3024 (19)0.8190 (6)0.071 (6)*0.22
H2S10.60270.23610.82320.107*0.22
H2S20.65280.36580.84230.107*0.22
H2S30.72240.26790.82150.107*0.22
C3S0.746 (3)0.512 (3)0.8059 (13)0.22 (4)*0.22
H3S10.71490.50180.83290.260*0.22
H3S20.74460.60210.79900.260*0.22
C4S0.859 (3)0.475 (5)0.8190 (16)0.15 (2)*0.22
H4S10.89830.53900.83870.231*0.22
H4S20.88870.46680.79190.231*0.22
H4S30.86460.39610.83510.231*0.22
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0348 (17)0.081 (3)0.0312 (15)0.0048 (17)0.0013 (13)0.0064 (16)
O40.045 (2)0.091 (4)0.040 (2)0.005 (2)0.0026 (17)0.027 (2)
O210.052 (3)0.131 (5)0.043 (2)0.007 (2)0.0074 (18)0.002 (3)
C10.0272 (16)0.069 (2)0.0323 (17)0.0071 (17)0.0002 (13)0.0107 (17)
C20.028 (3)0.056 (4)0.032 (2)0.012 (2)0.0059 (16)0.003 (3)
C30.036 (2)0.065 (3)0.033 (2)0.001 (2)0.0014 (17)0.002 (2)
C40.033 (2)0.073 (4)0.031 (2)0.003 (2)0.0056 (18)0.011 (2)
C210.043 (3)0.070 (4)0.032 (2)0.007 (3)0.000 (2)0.010 (2)
C220.061 (3)0.052 (3)0.031 (2)0.003 (3)0.006 (2)0.006 (2)
C1B0.0272 (16)0.069 (2)0.0323 (17)0.0071 (17)0.0002 (13)0.0107 (17)
C50.0281 (17)0.065 (3)0.045 (2)0.0028 (17)0.0043 (15)0.0190 (19)
C60.0266 (16)0.0411 (19)0.0332 (17)0.0021 (14)0.0036 (13)0.0021 (14)
C70.0295 (16)0.0248 (16)0.0302 (16)0.0030 (13)0.0036 (13)0.0012 (13)
C80.0295 (16)0.0304 (17)0.0317 (16)0.0000 (14)0.0028 (13)0.0037 (13)
C90.0274 (16)0.0207 (15)0.0342 (17)0.0020 (13)0.0030 (13)0.0012 (13)
C100.0325 (17)0.0267 (16)0.0342 (17)0.0005 (14)0.0043 (13)0.0015 (13)
C110.0313 (16)0.0219 (16)0.0353 (17)0.0014 (13)0.0048 (13)0.0016 (13)
C120.0285 (16)0.0210 (15)0.0363 (17)0.0007 (13)0.0044 (13)0.0025 (13)
C130.0277 (16)0.0156 (14)0.0388 (18)0.0016 (12)0.0038 (13)0.0069 (12)
C140.0301 (16)0.0182 (14)0.0379 (17)0.0008 (13)0.0044 (13)0.0041 (13)
C150.0299 (16)0.0179 (14)0.0386 (17)0.0015 (12)0.0036 (13)0.0049 (13)
C160.042 (3)0.059 (3)0.036 (3)0.027 (2)0.007 (2)0.015 (2)
C170.023 (2)0.088 (5)0.030 (2)0.009 (3)0.0030 (18)0.012 (3)
C180.042 (2)0.054 (2)0.052 (2)0.0042 (19)0.0061 (17)0.0153 (19)
C190.0263 (16)0.0255 (16)0.0373 (17)0.0011 (13)0.0016 (13)0.0039 (13)
C200.0287 (16)0.0251 (16)0.0410 (18)0.0017 (13)0.0012 (13)0.0037 (14)
Geometric parameters (Å, º) top
O3—C211.341 (7)C11—C121.351 (4)
O3—C31.444 (5)C11—H110.9500
O4—C41.227 (6)C12—C131.443 (4)
O21—C211.178 (8)C12—H120.9500
C1—C171.512 (6)C13—C141.366 (4)
C1—C21.520 (6)C13—C201.494 (4)
C1—C61.528 (5)C14—C151.429 (4)
C1—C161.589 (7)C14—H140.9500
C2—C31.473 (8)C15—C15ii1.351 (6)
C2—H2A0.9900C15—H150.9500
C2—H2B0.9900C16—H16A0.9800
C3—C41.520 (7)C16—H16B0.9800
C3—H31.0000C16—H16C0.9800
C4—C51.521 (6)C17—H17A0.9800
C21—C221.497 (7)C17—H17B0.9800
C22—H22A0.9800C17—H17C0.9800
C22—H22B0.9800C16B—H16D0.9800
C22—H22C0.9800C16B—H16E0.9800
O3B—C21B1.352 (14)C16B—H16F0.9800
O3B—C3B1.432 (12)C17B—H17D0.9800
O4B—C4B1.222 (14)C17B—H17E0.9800
O21B—C22Bi1.05 (2)C17B—H17F0.9800
O21B—C21B1.151 (14)C18—H18A0.9800
C2B—C3B1.501 (15)C18—H18B0.9800
C2B—H2D0.9900C18—H18C0.9800
C2B—H2E0.9900C19—H19A0.9800
C3B—C4B1.514 (14)C19—H19B0.9800
C3B—H3B1.0000C19—H19C0.9800
C4B—C51.535 (13)C20—H20A0.9800
C21B—C22Bi0.805 (19)C20—H20B0.9800
C21B—C22B1.494 (15)C20—H20C0.9800
C21B—C21Bi1.49 (2)O1S—C1S1.148 (14)
C22B—H22D0.9800O1S—O1Siii1.29 (5)
C22B—H22E0.9800O2S—C1S1.337 (15)
C22B—H22F0.9800O2S—C3S1.399 (19)
C5—C61.354 (5)C1S—C2S1.457 (13)
C5—C181.508 (5)C2S—H2S10.9800
C6—C71.471 (4)C2S—H2S20.9800
C7—C81.336 (4)C2S—H2S30.9800
C7—H70.9500C3S—C4S1.489 (15)
C8—C91.456 (4)C3S—H3S10.9900
C8—H80.9500C3S—H3S20.9900
C9—C101.364 (4)C4S—H4S10.9800
C9—C191.493 (4)C4S—H4S20.9800
C10—C111.432 (4)C4S—H4S30.9800
C10—H100.9500
C21—O3—C3114.7 (4)C9—C8—H8117.2
C17—C1—C2112.2 (4)C10—C9—C8119.0 (3)
C17—C1—C6112.4 (3)C10—C9—C19122.7 (3)
C2—C1—C6114.2 (4)C8—C9—C19118.2 (3)
C17—C1—C16106.1 (5)C9—C10—C11125.8 (3)
C2—C1—C16103.5 (4)C9—C10—H10117.1
C6—C1—C16107.5 (3)C11—C10—H10117.1
C3—C2—C1113.6 (4)C12—C11—C10124.9 (3)
C3—C2—H2A108.8C12—C11—H11117.5
C1—C2—H2A108.8C10—C11—H11117.5
C3—C2—H2B108.8C11—C12—C13125.5 (3)
C1—C2—H2B108.8C11—C12—H12117.3
H2A—C2—H2B107.7C13—C12—H12117.3
O3—C3—C2109.3 (4)C14—C13—C12119.1 (3)
O3—C3—C4109.7 (4)C14—C13—C20122.6 (3)
C2—C3—C4109.1 (5)C12—C13—C20118.2 (3)
O3—C3—H3109.6C13—C14—C15127.8 (3)
C2—C3—H3109.6C13—C14—H14116.1
C4—C3—H3109.6C15—C14—H14116.1
O4—C4—C3124.0 (5)C15ii—C15—C14124.2 (4)
O4—C4—C5120.0 (5)C15ii—C15—H15117.9
C3—C4—C5116.0 (4)C14—C15—H15117.9
O21—C21—O3124.5 (5)H16D—C16B—H16E109.5
O21—C21—C22125.3 (5)H16D—C16B—H16F109.5
O3—C21—C22110.1 (5)H16E—C16B—H16F109.5
C21B—O3B—C3B115.5 (9)H17D—C17B—H17E109.5
C22Bi—O21B—C21B42.5 (11)H17D—C17B—H17F109.5
C3B—C2B—H2D106.6H17E—C17B—H17F109.5
C3B—C2B—H2E106.6C5—C18—H18A109.5
H2D—C2B—H2E106.5C5—C18—H18B109.5
O3B—C3B—C2B116.2 (11)H18A—C18—H18B109.5
O3B—C3B—C4B108.2 (9)C5—C18—H18C109.5
C2B—C3B—C4B107.6 (12)H18A—C18—H18C109.5
O3B—C3B—H3B108.2H18B—C18—H18C109.5
C2B—C3B—H3B108.2C9—C19—H19A109.5
C4B—C3B—H3B108.2C9—C19—H19B109.5
O4B—C4B—C3B124.8 (12)H19A—C19—H19B109.5
O4B—C4B—C5120.0 (11)C9—C19—H19C109.5
C3B—C4B—C5114.5 (9)H19A—C19—H19C109.5
C22Bi—C21B—O21B62.2 (16)H19B—C19—H19C109.5
C22Bi—C21B—O3B157 (2)C13—C20—H20A109.5
O21B—C21B—O3B125.9 (12)C13—C20—H20B109.5
C22Bi—C21B—C22B69 (2)H20A—C20—H20B109.5
O21B—C21B—C22B127.6 (14)C13—C20—H20C109.5
O3B—C21B—C22B106.5 (11)H20A—C20—H20C109.5
C22Bi—C21B—C21Bi74.8 (16)H20B—C20—H20C109.5
O21B—C21B—C21Bi114.2 (15)C1S—O1S—O1Siii122 (3)
O3B—C21B—C21Bi113.7 (12)C1S—O2S—C3S124.1 (19)
C22B—C21B—C21Bi31.3 (8)O1S—C1S—O2S124.3 (13)
C21B—C22B—H22D109.5O1S—C1S—C2S126.1 (14)
C21B—C22B—H22E109.5O2S—C1S—C2S109.5 (11)
H22D—C22B—H22E109.5C1S—C2S—H2S1109.5
C21B—C22B—H22F109.5C1S—C2S—H2S2109.5
H22D—C22B—H22F109.5H2S1—C2S—H2S2109.5
H22E—C22B—H22F109.5C1S—C2S—H2S3109.5
C6—C5—C18125.3 (3)H2S1—C2S—H2S3109.5
C6—C5—C4118.1 (3)H2S2—C2S—H2S3109.5
C18—C5—C4116.4 (3)O2S—C3S—C4S120 (3)
C6—C5—C4B122.8 (5)O2S—C3S—H3S1107.3
C18—C5—C4B104.0 (5)C4S—C3S—H3S1107.3
C4—C5—C4B36.4 (6)O2S—C3S—H3S2107.3
C5—C6—C7121.8 (3)C4S—C3S—H3S2107.3
C5—C6—C1123.1 (3)H3S1—C3S—H3S2106.9
C7—C6—C1115.2 (3)C3S—C4S—H4S1109.5
C8—C7—C6125.1 (3)C3S—C4S—H4S2109.5
C8—C7—H7117.5H4S1—C4S—H4S2109.5
C6—C7—H7117.5C3S—C4S—H4S3109.5
C7—C8—C9125.7 (3)H4S1—C4S—H4S3109.5
C7—C8—H8117.2H4S2—C4S—H4S3109.5
C17—C1—C2—C3162.7 (6)C3B—C4B—C5—C18155.5 (10)
C6—C1—C2—C333.2 (8)O4B—C4B—C5—C482.3 (15)
C16—C1—C2—C383.4 (7)C3B—C4B—C5—C488.8 (13)
C21—O3—C3—C2158.0 (6)C18—C5—C6—C77.2 (6)
C21—O3—C3—C482.4 (6)C4—C5—C6—C7166.8 (4)
C1—C2—C3—O3177.7 (5)C4B—C5—C6—C7151.0 (8)
C1—C2—C3—C457.7 (7)C18—C5—C6—C1173.7 (4)
O3—C3—C4—O411.8 (8)C4—C5—C6—C112.4 (6)
C2—C3—C4—O4131.6 (6)C4B—C5—C6—C129.8 (9)
O3—C3—C4—C5168.6 (4)C17—C1—C6—C5126.0 (5)
C2—C3—C4—C548.9 (6)C2—C1—C6—C53.4 (6)
C3—O3—C21—O211.8 (9)C16—C1—C6—C5117.6 (4)
C3—O3—C21—C22178.4 (5)C17—C1—C6—C754.8 (5)
C21B—O3B—C3B—C2B95.3 (16)C2—C1—C6—C7175.9 (4)
C21B—O3B—C3B—C4B143.5 (12)C16—C1—C6—C761.6 (4)
O3B—C3B—C4B—O4B12 (2)C5—C6—C7—C849.1 (5)
C2B—C3B—C4B—O4B138.1 (17)C1—C6—C7—C8130.2 (4)
O3B—C3B—C4B—C5158.8 (10)C6—C7—C8—C9178.4 (3)
C2B—C3B—C4B—C532.5 (16)C7—C8—C9—C10179.9 (3)
C22Bi—O21B—C21B—O3B154 (3)C7—C8—C9—C191.8 (5)
C22Bi—O21B—C21B—C22B22.5 (18)C8—C9—C10—C11174.2 (3)
C22Bi—O21B—C21B—C21Bi55.7 (16)C19—C9—C10—C114.0 (5)
C3B—O3B—C21B—C22Bi94 (5)C9—C10—C11—C12178.8 (3)
C3B—O3B—C21B—O21B8 (2)C10—C11—C12—C13173.2 (3)
C3B—O3B—C21B—C22B168.7 (11)C11—C12—C13—C14177.5 (3)
C3B—O3B—C21B—C21Bi158.8 (9)C11—C12—C13—C201.2 (4)
O4—C4—C5—C6166.0 (5)C12—C13—C14—C15178.3 (3)
C3—C4—C5—C614.4 (7)C20—C13—C14—C150.4 (5)
O4—C4—C5—C1819.5 (7)C13—C14—C15—C15ii176.2 (4)
C3—C4—C5—C18160.1 (4)O1Siii—O1S—C1S—O2S119 (2)
O4—C4—C5—C4B58.0 (9)O1Siii—O1S—C1S—C2S62 (2)
C3—C4—C5—C4B122.5 (9)C3S—O2S—C1S—O1S164 (3)
O4B—C4B—C5—C6176.4 (11)C3S—O2S—C1S—C2S17 (3)
C3B—C4B—C5—C65.3 (15)C1S—O2S—C3S—C4S96 (4)
O4B—C4B—C5—C1833.4 (15)
Symmetry codes: (i) x+2, y, z+3/2; (ii) x1/2, y+1/2, z+1; (iii) x+1, y, z+3/2.
(s-trans-1) top
Crystal data top
C44H56O6F(000) = 736
Mr = 680.89Dx = 1.161 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 3456 reflections
a = 10.6598 (10) Åθ = 2.3–26.2°
b = 10.1683 (10) ŵ = 0.08 mm1
c = 18.2940 (18) ÅT = 100 K
β = 100.700 (2)°Plate, red
V = 1948.4 (3) Å30.60 × 0.60 × 0.10 mm
Z = 2
Data collection top
Bruker APEX CCD area detector
diffractometer
2506 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.072
Graphite monochromatorθmax = 25.0°, θmin = 1.9°
phi and ω scansh = 1211
9816 measured reflectionsk = 912
3425 independent reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0489P)2 + 1.5414P]
where P = (Fo2 + 2Fc2)/3
3425 reflections(Δ/σ)max = 0.001
305 parametersΔρmax = 0.39 e Å3
73 restraintsΔρmin = 0.21 e Å3
Crystal data top
C44H56O6V = 1948.4 (3) Å3
Mr = 680.89Z = 2
Monoclinic, P21/cMo Kα radiation
a = 10.6598 (10) ŵ = 0.08 mm1
b = 10.1683 (10) ÅT = 100 K
c = 18.2940 (18) Å0.60 × 0.60 × 0.10 mm
β = 100.700 (2)°
Data collection top
Bruker APEX CCD area detector
diffractometer
2506 reflections with I > 2σ(I)
9816 measured reflectionsRint = 0.072
3425 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06573 restraints
wR(F2) = 0.175H-atom parameters constrained
S = 1.08Δρmax = 0.39 e Å3
3425 reflectionsΔρmin = 0.21 e Å3
305 parameters
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O40.86809 (19)0.07034 (18)0.34294 (10)0.0525 (5)
O31.0473 (3)0.1135 (3)0.35298 (15)0.0504 (7)0.788 (4)
O210.9139 (2)0.2207 (3)0.41407 (15)0.0608 (8)0.788 (4)
C10.9199 (5)0.1090 (6)0.1462 (3)0.0412 (14)0.788 (4)
C21.0123 (2)0.1161 (2)0.22110 (13)0.0523 (10)0.788 (4)
H2A1.07430.04300.22350.063*0.788 (4)
H2B1.06080.19940.22300.063*0.788 (4)
C30.9532 (2)0.1091 (2)0.28575 (13)0.0574 (8)0.788 (4)
H30.89590.18720.28520.069*0.788 (4)
C161.0070 (5)0.0802 (6)0.0901 (3)0.0500 (12)0.788 (4)
H16A0.96070.09820.03960.075*0.788 (4)
H16B1.03300.01240.09390.075*0.788 (4)
H16C1.08290.13630.10090.075*0.788 (4)
C170.8510 (7)0.2415 (7)0.1283 (3)0.0490 (13)0.788 (4)
H17A0.79490.23640.07950.073*0.788 (4)
H17B0.91430.31120.12780.073*0.788 (4)
H17C0.80000.26120.16640.073*0.788 (4)
C211.0126 (4)0.1660 (4)0.4135 (2)0.0477 (9)0.788 (4)
C221.1163 (10)0.1437 (11)0.4793 (3)0.0541 (17)0.788 (4)
H22A1.18520.09270.46410.081*0.788 (4)
H22B1.08210.09520.51750.081*0.788 (4)
H22C1.14980.22860.49950.081*0.788 (4)
O3B0.9884 (16)0.1680 (13)0.3577 (6)0.086 (4)0.212 (4)
O21B1.1647 (12)0.0432 (13)0.3953 (7)0.092 (4)0.212 (4)
C1B0.8923 (19)0.143 (2)0.1490 (8)0.033 (4)0.212 (4)
C2B0.9304 (11)0.1951 (10)0.2280 (5)0.034 (2)0.212 (4)
H2C1.00840.24880.22990.041*0.212 (4)
H2D0.86200.25550.23710.041*0.212 (4)
C3B0.9532 (2)0.1091 (2)0.28575 (13)0.0574 (8)0.212 (4)
H3B1.03660.07060.27890.069*0.212 (4)
C16B1.0126 (17)0.103 (2)0.1221 (8)0.038 (4)0.212 (4)
H16D0.99200.08260.06890.056*0.212 (4)
H16E1.04940.02510.14960.056*0.212 (4)
H16F1.07430.17530.13050.056*0.212 (4)
C17B0.825 (2)0.2538 (19)0.0996 (10)0.039 (4)0.212 (4)
H17D0.81350.22740.04720.059*0.212 (4)
H17E0.87690.33380.10730.059*0.212 (4)
H17F0.74130.27090.11260.059*0.212 (4)
C21B1.0830 (16)0.1169 (16)0.4087 (9)0.067 (4)0.212 (4)
C22B1.084 (4)0.171 (4)0.4838 (13)0.084 (15)0.212 (4)
H22D1.00700.14280.50130.125*0.212 (4)
H22E1.08670.26720.48180.125*0.212 (4)
H22F1.15970.13860.51800.125*0.212 (4)
C40.8740 (2)0.0121 (3)0.28521 (15)0.0440 (6)
C50.8007 (2)0.0538 (2)0.21228 (15)0.0402 (6)
C60.8172 (2)0.0049 (3)0.14774 (15)0.0431 (6)
C70.7383 (2)0.0415 (3)0.07905 (15)0.0476 (7)
H70.68250.11190.08520.057*
C80.7310 (2)0.0012 (3)0.00776 (15)0.0425 (6)
H80.78530.06860.00140.051*
C90.6457 (2)0.0577 (3)0.05540 (15)0.0449 (7)
C100.6507 (2)0.0112 (3)0.12432 (15)0.0442 (6)
H100.71070.05680.12720.053*
C110.5747 (2)0.0542 (3)0.19332 (16)0.0457 (7)
H110.50990.11760.19150.055*
C120.5898 (3)0.0100 (3)0.26051 (15)0.0469 (7)
H120.65640.05160.26170.056*
C130.5128 (3)0.0487 (3)0.33144 (16)0.0481 (7)
C140.5442 (3)0.0002 (3)0.39485 (16)0.0500 (7)
H140.61550.05790.38890.060*
C150.4814 (3)0.0260 (3)0.46986 (15)0.0518 (7)
H150.40950.08300.47740.062*
C180.7081 (3)0.1646 (3)0.21580 (16)0.0498 (7)
H18A0.62170.13620.19340.075*
H18B0.71030.18910.26780.075*
H18C0.73210.24060.18850.075*
C190.5587 (3)0.1675 (3)0.04230 (16)0.0545 (8)
H19A0.50120.18920.08900.082*
H19B0.50830.14010.00530.082*
H19C0.60960.24510.02400.082*
C200.4038 (3)0.1426 (3)0.33138 (17)0.0558 (8)
H20A0.35060.14570.38120.084*
H20B0.35220.11280.29550.084*
H20C0.43760.23060.31750.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0581 (12)0.0456 (11)0.0557 (12)0.0024 (9)0.0156 (9)0.0097 (9)
O30.0533 (17)0.0532 (19)0.0413 (16)0.0091 (13)0.0001 (13)0.0031 (13)
O210.0474 (16)0.0661 (18)0.0669 (18)0.0059 (13)0.0056 (13)0.0082 (14)
C10.036 (3)0.042 (4)0.045 (2)0.005 (2)0.0062 (19)0.0026 (19)
C20.046 (2)0.058 (2)0.053 (2)0.0114 (18)0.0091 (17)0.0015 (18)
C30.0627 (19)0.0551 (18)0.0530 (17)0.0119 (15)0.0071 (14)0.0016 (13)
C160.037 (2)0.061 (3)0.055 (3)0.0023 (19)0.015 (2)0.005 (3)
C170.054 (3)0.042 (3)0.050 (3)0.007 (2)0.006 (3)0.002 (2)
C210.049 (3)0.042 (2)0.051 (3)0.0122 (19)0.008 (2)0.0009 (18)
C220.060 (3)0.060 (5)0.041 (3)0.008 (3)0.004 (2)0.001 (2)
O3B0.130 (10)0.063 (8)0.054 (4)0.021 (6)0.009 (7)0.008 (5)
O21B0.089 (9)0.081 (9)0.112 (10)0.021 (6)0.033 (7)0.009 (7)
C1B0.038 (8)0.018 (8)0.047 (4)0.002 (6)0.021 (6)0.006 (5)
C2B0.044 (6)0.025 (5)0.042 (4)0.018 (4)0.030 (4)0.007 (3)
C3B0.0627 (19)0.0551 (18)0.0530 (17)0.0119 (15)0.0071 (14)0.0016 (13)
C16B0.041 (8)0.047 (9)0.027 (8)0.007 (6)0.014 (7)0.003 (7)
C17B0.045 (9)0.015 (7)0.056 (8)0.000 (5)0.008 (9)0.013 (7)
C21B0.084 (11)0.060 (10)0.057 (8)0.026 (6)0.010 (6)0.007 (7)
C22B0.11 (3)0.060 (19)0.085 (19)0.04 (2)0.037 (17)0.026 (12)
C40.0424 (15)0.0401 (14)0.0516 (16)0.0070 (12)0.0140 (12)0.0044 (13)
C50.0333 (13)0.0339 (13)0.0556 (16)0.0032 (10)0.0142 (12)0.0004 (12)
C60.0367 (14)0.0409 (15)0.0518 (16)0.0025 (12)0.0084 (12)0.0026 (12)
C70.0372 (15)0.0450 (16)0.0610 (18)0.0069 (12)0.0107 (13)0.0034 (13)
C80.0324 (13)0.0391 (14)0.0550 (16)0.0007 (11)0.0055 (11)0.0043 (12)
C90.0356 (14)0.0370 (14)0.0604 (18)0.0041 (11)0.0043 (12)0.0065 (12)
C100.0340 (14)0.0394 (14)0.0569 (17)0.0034 (11)0.0026 (12)0.0085 (12)
C110.0361 (14)0.0372 (14)0.0605 (18)0.0071 (11)0.0001 (12)0.0095 (13)
C120.0398 (15)0.0393 (14)0.0574 (17)0.0049 (12)0.0017 (13)0.0095 (13)
C130.0395 (15)0.0396 (15)0.0600 (18)0.0091 (12)0.0043 (13)0.0095 (13)
C140.0457 (16)0.0396 (15)0.0589 (18)0.0022 (12)0.0056 (13)0.0084 (13)
C150.0493 (17)0.0392 (15)0.0606 (18)0.0042 (12)0.0061 (14)0.0091 (13)
C180.0458 (16)0.0374 (15)0.0673 (18)0.0012 (12)0.0137 (14)0.0024 (13)
C190.0437 (16)0.0528 (17)0.0647 (19)0.0057 (13)0.0042 (14)0.0089 (14)
C200.0407 (16)0.0518 (17)0.070 (2)0.0043 (13)0.0022 (14)0.0112 (15)
Geometric parameters (Å, º) top
O4—C41.222 (3)C17B—H17F0.9800
O3—C211.342 (5)C21B—C22B1.477 (17)
O3—C31.437 (3)C22B—H22D0.9800
O21—C211.192 (4)C22B—H22E0.9800
C1—C61.526 (7)C22B—H22F0.9800
C1—C21.533 (5)C4—C51.477 (4)
C1—C161.535 (6)C5—C61.363 (4)
C1—C171.540 (6)C5—C181.507 (3)
C2—C31.4413C6—C71.455 (4)
C2—H2A0.9900C7—C81.356 (4)
C2—H2B0.9900C7—H70.9500
C3—C41.494 (4)C8—C91.450 (4)
C3—H31.0000C8—H80.9500
C16—H16A0.9800C9—C101.357 (4)
C16—H16B0.9800C9—C191.499 (4)
C16—H16C0.9800C10—C111.436 (4)
C17—H17A0.9800C10—H100.9500
C17—H17B0.9800C11—C121.346 (4)
C17—H17C0.9800C11—H110.9500
C21—C221.493 (8)C12—C131.455 (4)
C22—H22A0.9800C12—H120.9500
C22—H22B0.9800C13—C141.360 (4)
C22—H22C0.9800C13—C201.505 (4)
O3B—C21B1.344 (15)C14—C151.436 (4)
O21B—C21B1.208 (15)C14—H140.9500
C1B—C16B1.512 (15)C15—C15i1.347 (6)
C1B—C2B1.523 (15)C15—H150.9500
C1B—C17B1.538 (15)C18—H18A0.9800
C1B—C61.61 (2)C18—H18B0.9800
C2B—H2C0.9900C18—H18C0.9800
C2B—H2D0.9900C19—H19A0.9800
C16B—H16D0.9800C19—H19B0.9800
C16B—H16E0.9800C19—H19C0.9800
C16B—H16F0.9800C20—H20A0.9800
C17B—H17D0.9800C20—H20B0.9800
C17B—H17E0.9800C20—H20C0.9800
C21—O3—C3117.6 (3)C6—C5—C4121.7 (2)
C6—C1—C2111.1 (4)C6—C5—C18123.7 (2)
C6—C1—C16113.9 (4)C4—C5—C18114.6 (2)
C2—C1—C16103.8 (4)C5—C6—C7117.3 (2)
C6—C1—C17107.2 (4)C5—C6—C1121.8 (3)
C2—C1—C17110.5 (4)C7—C6—C1120.7 (3)
C16—C1—C17110.4 (5)C5—C6—C1B120.7 (6)
C3—C2—C1115.1 (2)C7—C6—C1B120.0 (6)
C3—C2—H2A108.5C1—C6—C1B16.6 (6)
C1—C2—H2A108.5C8—C7—C6130.8 (3)
C3—C2—H2B108.5C8—C7—H7114.6
C1—C2—H2B108.5C6—C7—H7114.6
H2A—C2—H2B107.5C7—C8—C9124.2 (3)
O3—C3—C2111.02 (15)C7—C8—H8117.9
O3—C3—C4109.6 (2)C9—C8—H8117.9
C2—C3—C4111.57 (14)C10—C9—C8118.4 (3)
O3—C3—H3108.2C10—C9—C19122.7 (2)
C2—C3—H3108.2C8—C9—C19118.9 (2)
C4—C3—H3108.2C9—C10—C11126.7 (3)
O21—C21—O3124.9 (4)C9—C10—H10116.6
O21—C21—C22125.9 (5)C11—C10—H10116.6
O3—C21—C22109.2 (5)C12—C11—C10123.9 (3)
C16B—C1B—C2B108.0 (13)C12—C11—H11118.0
C16B—C1B—C17B109.7 (15)C10—C11—H11118.0
C2B—C1B—C17B108.4 (13)C11—C12—C13125.5 (3)
C16B—C1B—C6102.1 (13)C11—C12—H12117.2
C2B—C1B—C6111.2 (12)C13—C12—H12117.2
C17B—C1B—C6116.9 (15)C14—C13—C12118.3 (3)
C1B—C2B—H2C107.5C14—C13—C20123.1 (2)
C1B—C2B—H2D107.5C12—C13—C20118.6 (3)
H2C—C2B—H2D107.0C13—C14—C15127.0 (3)
C1B—C16B—H16D109.5C13—C14—H14116.5
C1B—C16B—H16E109.5C15—C14—H14116.5
H16D—C16B—H16E109.5C15i—C15—C14123.6 (4)
C1B—C16B—H16F109.5C15i—C15—H15118.2
H16D—C16B—H16F109.5C14—C15—H15118.2
H16E—C16B—H16F109.5C5—C18—H18A109.5
C1B—C17B—H17D109.5C5—C18—H18B109.5
C1B—C17B—H17E109.5H18A—C18—H18B109.5
H17D—C17B—H17E109.5C5—C18—H18C109.5
C1B—C17B—H17F109.5H18A—C18—H18C109.5
H17D—C17B—H17F109.5H18B—C18—H18C109.5
H17E—C17B—H17F109.5C9—C19—H19A109.5
O21B—C21B—O3B125.1 (16)C9—C19—H19B109.5
O21B—C21B—C22B122.5 (19)H19A—C19—H19B109.5
O3B—C21B—C22B112.2 (19)C9—C19—H19C109.5
C21B—C22B—H22D109.5H19A—C19—H19C109.5
C21B—C22B—H22E109.5H19B—C19—H19C109.5
H22D—C22B—H22E109.5C13—C20—H20A109.5
C21B—C22B—H22F109.5C13—C20—H20B109.5
H22D—C22B—H22F109.5H20A—C20—H20B109.5
H22E—C22B—H22F109.5C13—C20—H20C109.5
O4—C4—C5122.6 (2)H20A—C20—H20C109.5
O4—C4—C3120.9 (2)H20B—C20—H20C109.5
C5—C4—C3116.5 (2)
C6—C1—C2—C342.2 (4)C17—C1—C6—C773.9 (5)
C16—C1—C2—C3165.0 (3)C2—C1—C6—C1B102 (2)
C17—C1—C2—C376.7 (4)C16—C1—C6—C1B141 (2)
C21—O3—C3—C2150.7 (3)C17—C1—C6—C1B19 (2)
C21—O3—C3—C485.6 (3)C16B—C1B—C6—C5111.8 (9)
C1—C2—C3—O3178.7 (4)C2B—C1B—C6—C53.3 (14)
C1—C2—C3—C456.1 (3)C17B—C1B—C6—C5128.5 (11)
C3—O3—C21—O217.8 (6)C16B—C1B—C6—C784.3 (11)
C3—O3—C21—C22171.8 (5)C2B—C1B—C6—C7160.6 (8)
O3—C3—C4—O420.4 (3)C17B—C1B—C6—C735.4 (15)
C2—C3—C4—O4143.8 (2)C16B—C1B—C6—C112.9 (16)
O3—C3—C4—C5161.8 (2)C2B—C1B—C6—C1102 (3)
C2—C3—C4—C538.4 (2)C17B—C1B—C6—C1133 (3)
O4—C4—C5—C6173.9 (2)C5—C6—C7—C8178.3 (3)
C3—C4—C5—C68.4 (3)C1—C6—C7—C85.4 (5)
O4—C4—C5—C186.1 (4)C1B—C6—C7—C813.9 (8)
C3—C4—C5—C18171.7 (2)C6—C7—C8—C9179.6 (3)
C4—C5—C6—C7178.7 (2)C7—C8—C9—C10177.9 (2)
C18—C5—C6—C71.4 (4)C7—C8—C9—C190.3 (4)
C4—C5—C6—C15.1 (4)C8—C9—C10—C11179.9 (2)
C18—C5—C6—C1174.8 (3)C19—C9—C10—C111.8 (4)
C4—C5—C6—C1B14.4 (8)C9—C10—C11—C12175.5 (3)
C18—C5—C6—C1B165.7 (8)C10—C11—C12—C13178.4 (2)
C2—C1—C6—C510.9 (5)C11—C12—C13—C14176.9 (3)
C16—C1—C6—C5127.6 (4)C11—C12—C13—C202.0 (4)
C17—C1—C6—C5110.0 (4)C12—C13—C14—C15179.7 (2)
C2—C1—C6—C7165.2 (3)C20—C13—C14—C150.9 (4)
C16—C1—C6—C748.5 (5)C13—C14—C15—C15i179.7 (3)
Symmetry code: (i) x+1, y, z1.
(2) top
Crystal data top
C40H50O4Z = 1
Mr = 594.80F(000) = 322
Triclinic, P1Dx = 1.146 Mg m3
a = 7.7821 (4) ÅSynchrotron radiation, λ = 0.6709 Å
b = 9.9578 (5) ÅCell parameters from 4494 reflections
c = 11.4162 (5) Åθ = 3.3–30.5°
α = 88.126 (1)°µ = 0.07 mm1
β = 78.329 (1)°T = 100 K
γ = 84.340 (1)°Plate, red
V = 862.08 (7) Å30.2 × 0.2 × 0.02 mm
Data collection top
Bruker APEXII CCD area detector
diffractometer
3029 independent reflections
Radiation source: Station 9.8, SRS, Daresbury2910 reflections with I > 2σ(I)
Silicon monochromatorRint = 0.016
phi and ω scansθmax = 23.8°, θmin = 2.6°
Absorption correction: multi-scan
SADABS
h = 99
Tmin = 0.736, Tmax = 1.000k = 1111
6688 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0747P)2 + 0.1591P]
where P = (Fo2 + 2Fc2)/3
3029 reflections(Δ/σ)max < 0.001
428 parametersΔρmax = 0.17 e Å3
143 restraintsΔρmin = 0.16 e Å3
Crystal data top
C40H50O4γ = 84.340 (1)°
Mr = 594.80V = 862.08 (7) Å3
Triclinic, P1Z = 1
a = 7.7821 (4) ÅSynchrotron radiation, λ = 0.6709 Å
b = 9.9578 (5) ŵ = 0.07 mm1
c = 11.4162 (5) ÅT = 100 K
α = 88.126 (1)°0.2 × 0.2 × 0.02 mm
β = 78.329 (1)°
Data collection top
Bruker APEXII CCD area detector
diffractometer
3029 independent reflections
Absorption correction: multi-scan
SADABS
2910 reflections with I > 2σ(I)
Tmin = 0.736, Tmax = 1.000Rint = 0.016
6688 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046143 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.08Δρmax = 0.17 e Å3
3029 reflectionsΔρmin = 0.16 e Å3
428 parameters
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O31.5748 (4)1.2999 (3)0.0199 (3)0.0704 (8)
H31.54291.30820.04440.106*
O41.2814 (3)1.2251 (3)0.0358 (2)0.0555 (6)
O3B1.1944 (4)0.6539 (3)1.3235 (2)0.0728 (9)
H3B1.14760.66191.38190.109*
O4B0.9174 (3)0.5515 (3)1.3753 (2)0.0544 (6)
C11.3989 (4)1.0939 (3)0.2911 (3)0.0415 (7)
C21.4768 (4)1.2122 (3)0.2166 (3)0.0447 (7)
H2A1.40091.29430.23920.054*
H2B1.59131.22350.23440.054*
C31.4970 (4)1.1919 (3)0.0851 (3)0.0454 (7)
H3A1.57401.10890.06320.054*
C41.3186 (4)1.1752 (3)0.0565 (3)0.0419 (7)
C51.1975 (4)1.0955 (3)0.1406 (3)0.0412 (7)
C61.2354 (4)1.0563 (3)0.2472 (3)0.0419 (7)
C71.1177 (9)0.9670 (6)0.3138 (8)0.0359 (13)0.638 (17)
C81.0287 (4)0.8948 (3)0.3749 (3)0.0420 (7)0.638 (17)
C7A1.1492 (16)0.9770 (11)0.3574 (15)0.038 (2)0.362 (17)
H7A1.19290.99140.42550.046*0.362 (17)
C8A1.0287 (4)0.8948 (3)0.3749 (3)0.0420 (7)0.362 (17)
H8A0.97930.88850.30780.050*0.362 (17)
C90.9513 (4)0.8107 (3)0.4712 (3)0.0384 (6)
C100.8070 (4)0.7464 (3)0.4648 (3)0.0373 (6)
H100.76280.75820.39490.045*
C110.7176 (4)0.6622 (3)0.5568 (3)0.0361 (6)
H110.76050.64970.62710.043*
C120.5747 (4)0.5997 (3)0.5474 (3)0.0360 (6)
H120.53270.61310.47680.043*
C130.4822 (4)0.5143 (3)0.6376 (2)0.0354 (6)
C140.3411 (4)0.4553 (3)0.6137 (3)0.0363 (6)
H140.31020.47710.54040.044*
C150.2367 (4)0.3640 (3)0.6891 (3)0.0359 (6)
H150.26750.33740.76150.043*
C15B0.0952 (4)0.3141 (3)0.6604 (2)0.0358 (6)
H15B0.06290.34250.58880.043*
C14B0.0076 (4)0.2199 (3)0.7344 (2)0.0346 (6)
H14B0.02360.19690.80740.042*
C13B0.1448 (4)0.1612 (3)0.7094 (2)0.0351 (6)
C12B0.2361 (4)0.0702 (3)0.7966 (2)0.0350 (6)
H12B0.19300.05400.86650.042*
C11B0.3776 (4)0.0068 (3)0.7864 (3)0.0363 (6)
H11B0.42000.01990.71590.044*
C10B0.4665 (4)0.0790 (3)0.8764 (3)0.0355 (6)
H10B0.41970.09260.94500.043*
C9B0.6104 (4)0.1426 (3)0.8733 (3)0.0378 (6)
C7B0.8129 (8)0.3041 (6)0.9895 (7)0.0343 (13)0.638 (17)
H7B0.85600.31500.92050.041*0.638 (17)
C8B0.6865 (4)0.2235 (3)0.9741 (3)0.0432 (7)0.638 (17)
H8B0.63630.21731.04090.052*0.638 (17)
C7BB0.7805 (14)0.2885 (10)1.0321 (13)0.035 (2)0.362 (17)
C8BB0.6865 (4)0.2235 (3)0.9741 (3)0.0432 (7)0.362 (17)
C6B0.9018 (4)0.3816 (3)1.0934 (3)0.0428 (7)
C5B0.8453 (4)0.4276 (3)1.1941 (3)0.0441 (8)
C4B0.9459 (4)0.5222 (3)1.2762 (3)0.0408 (7)
C3B1.0860 (4)0.5869 (3)1.2301 (3)0.0450 (7)
H3B11.02740.65391.17050.054*
C2B1.1888 (4)0.4821 (3)1.1699 (3)0.0413 (6)
H2B11.24360.41301.22700.050*
H2B21.28180.52301.14290.050*
C1B1.0741 (4)0.4169 (3)1.0632 (3)0.0412 (7)
C161.5320 (5)0.9694 (4)0.2824 (4)0.0579 (8)
H16A1.55940.93750.20170.087*
H16B1.48260.89990.33520.087*
H16C1.63760.99270.30490.087*
C171.3463 (7)1.1412 (5)0.4208 (3)0.0804 (13)
H17A1.30421.06780.47170.121*0.638 (17)
H17B1.25491.21430.42680.121*0.638 (17)
H17C1.44691.17130.44540.121*0.638 (17)
H17D1.36651.23450.42420.121*0.362 (17)
H17E1.41581.08800.46910.121*0.362 (17)
H17F1.22371.13090.45050.121*0.362 (17)
C181.0340 (5)1.0653 (3)0.0977 (4)0.0604 (10)
H18A1.06691.00700.02990.091*
H18B0.97401.14810.07510.091*
H18C0.95721.02170.16080.091*
C191.0397 (5)0.7987 (4)0.5771 (3)0.0565 (9)
H19A1.00450.72080.62430.085*
H19B1.00590.87810.62490.085*
H19C1.16530.78950.54970.085*
C200.5435 (4)0.4920 (3)0.7534 (3)0.0413 (7)
H20A0.45910.44520.80880.062*
H20B0.55520.57750.78610.062*
H20C0.65550.43910.73980.062*
C16B1.1812 (5)0.2881 (4)1.0300 (3)0.0575 (8)
H16D1.29220.31061.01570.086*
H16E1.11670.24780.95910.086*
H16F1.20140.22541.09460.086*
C17B1.0380 (6)0.5118 (4)0.9546 (3)0.0620 (9)
H17H0.97450.59460.97360.093*
H17I0.96930.46900.88690.093*
H17J1.14790.53090.93590.093*
C18B0.6797 (4)0.3914 (4)1.2281 (4)0.0625 (11)
H18D0.58160.41191.16340.094*
H18E0.66090.44231.29800.094*
H18F0.69060.29671.24480.094*
C19B0.6997 (5)0.1330 (4)0.7684 (3)0.0557 (9)
H19D0.62860.08850.70280.084*
H19E0.81270.08240.79000.084*
H19F0.71510.22210.74500.084*
C20B0.2094 (4)0.1849 (3)0.5930 (3)0.0462 (8)
H20D0.13420.24220.54120.069*
H20E0.32780.22760.60930.069*
H20F0.20730.10010.55490.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0710 (17)0.0839 (18)0.0601 (16)0.0437 (14)0.0091 (13)0.0292 (14)
O40.0581 (14)0.0604 (14)0.0492 (13)0.0059 (11)0.0149 (11)0.0102 (11)
O3B0.0741 (18)0.099 (2)0.0596 (16)0.0606 (16)0.0275 (13)0.0407 (15)
O4B0.0535 (13)0.0651 (15)0.0492 (13)0.0147 (11)0.0183 (10)0.0070 (11)
C10.0471 (16)0.0424 (15)0.0322 (14)0.0059 (12)0.0010 (12)0.0007 (12)
C20.0478 (16)0.0425 (16)0.0462 (16)0.0158 (13)0.0095 (13)0.0004 (12)
C30.0447 (15)0.0520 (17)0.0396 (15)0.0206 (13)0.0025 (12)0.0058 (12)
C40.0444 (15)0.0362 (15)0.0436 (16)0.0049 (12)0.0045 (13)0.0023 (12)
C50.0370 (15)0.0304 (14)0.0549 (19)0.0080 (11)0.0033 (13)0.0031 (13)
C60.0360 (15)0.0294 (13)0.0528 (18)0.0056 (11)0.0103 (12)0.0000 (12)
C70.035 (2)0.034 (2)0.038 (3)0.0076 (17)0.004 (2)0.004 (2)
C80.0362 (13)0.0377 (14)0.0498 (17)0.0118 (11)0.0019 (12)0.0036 (12)
C7A0.036 (4)0.039 (3)0.038 (4)0.012 (3)0.001 (3)0.000 (3)
C8A0.0362 (13)0.0377 (14)0.0498 (17)0.0118 (11)0.0019 (12)0.0036 (12)
C90.0364 (14)0.0385 (15)0.0405 (16)0.0107 (11)0.0045 (11)0.0005 (12)
C100.0406 (15)0.0383 (15)0.0346 (14)0.0098 (12)0.0094 (12)0.0042 (12)
C110.0375 (14)0.0362 (14)0.0353 (14)0.0086 (12)0.0069 (11)0.0036 (11)
C120.0381 (14)0.0396 (15)0.0319 (14)0.0093 (12)0.0084 (11)0.0031 (11)
C130.0378 (15)0.0354 (14)0.0325 (14)0.0094 (11)0.0034 (11)0.0015 (11)
C140.0373 (14)0.0415 (14)0.0310 (14)0.0120 (12)0.0060 (11)0.0036 (11)
C150.0393 (15)0.0385 (15)0.0281 (13)0.0093 (12)0.0003 (11)0.0003 (11)
C15B0.0393 (15)0.0412 (15)0.0254 (13)0.0098 (12)0.0005 (11)0.0002 (11)
C14B0.0415 (14)0.0357 (14)0.0245 (12)0.0095 (11)0.0010 (10)0.0006 (10)
C13B0.0378 (14)0.0373 (14)0.0285 (14)0.0068 (12)0.0014 (11)0.0000 (11)
C12B0.0367 (14)0.0381 (14)0.0298 (14)0.0091 (11)0.0037 (11)0.0043 (11)
C11B0.0382 (14)0.0391 (15)0.0323 (14)0.0068 (12)0.0082 (11)0.0019 (11)
C10B0.0354 (14)0.0362 (14)0.0360 (14)0.0074 (11)0.0091 (11)0.0051 (11)
C9B0.0353 (14)0.0399 (15)0.0386 (15)0.0080 (11)0.0060 (11)0.0029 (11)
C7B0.031 (2)0.033 (2)0.041 (3)0.0079 (16)0.008 (2)0.004 (2)
C8B0.0364 (14)0.0366 (14)0.0535 (17)0.0098 (11)0.0020 (12)0.0060 (12)
C7BB0.030 (3)0.035 (3)0.042 (4)0.016 (3)0.006 (3)0.013 (3)
C8BB0.0364 (14)0.0366 (14)0.0535 (17)0.0098 (11)0.0020 (12)0.0060 (12)
C6B0.0335 (14)0.0310 (14)0.0568 (18)0.0031 (11)0.0077 (12)0.0018 (12)
C5B0.0319 (14)0.0308 (14)0.066 (2)0.0053 (11)0.0007 (14)0.0009 (14)
C4B0.0361 (14)0.0395 (15)0.0472 (17)0.0084 (11)0.0069 (12)0.0005 (12)
C3B0.0470 (16)0.0497 (17)0.0406 (15)0.0243 (13)0.0061 (12)0.0090 (13)
C2B0.0388 (14)0.0498 (16)0.0366 (14)0.0162 (12)0.0045 (11)0.0030 (11)
C1B0.0448 (16)0.0401 (16)0.0348 (15)0.0019 (13)0.0004 (12)0.0038 (12)
C160.0499 (18)0.0511 (18)0.070 (2)0.0031 (14)0.0077 (15)0.0075 (15)
C170.108 (3)0.085 (3)0.0380 (19)0.010 (2)0.0008 (19)0.0062 (18)
C180.0474 (18)0.0379 (17)0.100 (3)0.0126 (14)0.0202 (19)0.0035 (18)
C190.0477 (18)0.076 (2)0.0519 (19)0.0278 (17)0.0158 (15)0.0071 (17)
C200.0475 (16)0.0460 (16)0.0332 (15)0.0195 (13)0.0084 (13)0.0069 (12)
C16B0.0566 (19)0.0510 (19)0.059 (2)0.0059 (15)0.0048 (15)0.0053 (15)
C17B0.087 (3)0.0543 (19)0.0382 (17)0.0064 (17)0.0023 (16)0.0032 (14)
C18B0.0365 (16)0.0468 (18)0.107 (3)0.0140 (14)0.0201 (19)0.0218 (19)
C19B0.0489 (18)0.077 (2)0.0459 (18)0.0251 (17)0.0104 (15)0.0022 (17)
C20B0.0503 (18)0.0558 (19)0.0350 (16)0.0208 (14)0.0082 (13)0.0087 (14)
Geometric parameters (Å, º) top
O3—C31.404 (4)C7B—C8B1.312 (8)
O3—H30.8200C7B—C6B1.481 (6)
O4—C41.225 (4)C7B—H7B0.9300
O3B—C3B1.413 (3)C8B—H8B0.9300
O3B—H3B0.8200C7BB—C6B1.450 (9)
O4B—C4B1.217 (4)C6B—C5B1.362 (5)
C1—C161.527 (5)C6B—C1B1.525 (5)
C1—C171.532 (5)C5B—C4B1.473 (4)
C1—C21.532 (4)C5B—C18B1.498 (5)
C1—C61.541 (5)C4B—C3B1.508 (4)
C2—C31.496 (4)C3B—C2B1.487 (4)
C2—H2A0.9700C3B—H3B10.9800
C2—H2B0.9700C2B—C1B1.525 (4)
C3—C41.515 (4)C2B—H2B10.9700
C3—H3A0.9800C2B—H2B20.9700
C4—C51.473 (4)C1B—C16B1.539 (4)
C5—C61.347 (5)C1B—C17B1.547 (4)
C5—C181.512 (5)C16—H16A0.9600
C6—C71.429 (6)C16—H16B0.9600
C6—C7A1.535 (12)C16—H16C0.9600
C7—C81.163 (6)C17—H17A0.9600
C8—C91.430 (4)C17—H17B0.9600
C7A—H7A0.9300C17—H17C0.9600
C9—C101.362 (4)C17—H17D0.9600
C9—C191.504 (5)C17—H17E0.9600
C10—C111.433 (4)C17—H17F0.9600
C10—H100.9300C18—H18A0.9600
C11—C121.350 (4)C18—H18B0.9600
C11—H110.9300C18—H18C0.9600
C12—C131.437 (4)C19—H19A0.9600
C12—H120.9300C19—H19B0.9600
C13—C141.373 (4)C19—H19C0.9600
C13—C201.497 (4)C20—H20A0.9600
C14—C151.428 (4)C20—H20B0.9600
C14—H140.9300C20—H20C0.9600
C15—C15B1.353 (3)C16B—H16D0.9600
C15—H150.9300C16B—H16E0.9600
C15B—C14B1.434 (4)C16B—H16F0.9600
C15B—H15B0.9300C17B—H17H0.9600
C14B—C13B1.350 (4)C17B—H17I0.9600
C14B—H14B0.9300C17B—H17J0.9600
C13B—C12B1.448 (4)C18B—H18D0.9600
C13B—C20B1.516 (4)C18B—H18E0.9600
C12B—C11B1.348 (4)C18B—H18F0.9600
C12B—H12B0.9300C19B—H19D0.9600
C11B—C10B1.427 (4)C19B—H19E0.9600
C11B—H11B0.9300C19B—H19F0.9600
C10B—C9B1.346 (4)C20B—H20D0.9600
C10B—H10B0.9300C20B—H20E0.9600
C9B—C8B1.443 (4)C20B—H20F0.9600
C9B—C19B1.498 (5)
C3—O3—H3109.5C5B—C4B—C3B116.5 (3)
C3B—O3B—H3B109.5O3B—C3B—C2B112.2 (3)
C16—C1—C17110.0 (3)O3B—C3B—C4B110.8 (2)
C16—C1—C2111.6 (3)C2B—C3B—C4B109.1 (2)
C17—C1—C2106.7 (3)O3B—C3B—H3B1108.2
C16—C1—C6108.5 (3)C2B—C3B—H3B1108.2
C17—C1—C6110.0 (3)C4B—C3B—H3B1108.2
C2—C1—C6110.0 (2)C3B—C2B—C1B112.2 (2)
C3—C2—C1112.5 (2)C3B—C2B—H2B1109.2
C3—C2—H2A109.1C1B—C2B—H2B1109.2
C1—C2—H2A109.1C3B—C2B—H2B2109.2
C3—C2—H2B109.1C1B—C2B—H2B2109.2
C1—C2—H2B109.1H2B1—C2B—H2B2107.9
H2A—C2—H2B107.8C2B—C1B—C6B111.4 (2)
O3—C3—C2110.8 (2)C2B—C1B—C16B107.1 (2)
O3—C3—C4111.3 (3)C6B—C1B—C16B110.1 (3)
C2—C3—C4109.4 (2)C2B—C1B—C17B109.8 (3)
O3—C3—H3A108.4C6B—C1B—C17B110.8 (3)
C2—C3—H3A108.4C16B—C1B—C17B107.5 (3)
C4—C3—H3A108.4C1—C16—H16A109.5
O4—C4—C5122.5 (3)C1—C16—H16B109.5
O4—C4—C3119.5 (3)H16A—C16—H16B109.5
C5—C4—C3118.0 (3)C1—C16—H16C109.5
C6—C5—C4120.1 (3)H16A—C16—H16C109.5
C6—C5—C18124.8 (3)H16B—C16—H16C109.5
C4—C5—C18115.1 (3)C1—C17—H17A109.5
C5—C6—C7114.1 (5)C1—C17—H17B109.5
C5—C6—C1123.7 (3)H17A—C17—H17B109.5
C7—C6—C1121.9 (5)C1—C17—H17C109.5
C5—C6—C7A136.8 (7)H17A—C17—H17C109.5
C7—C6—C7A23.5 (4)H17B—C17—H17C109.5
C1—C6—C7A99.4 (7)C1—C17—H17D109.5
C8—C7—C6174.9 (9)H17A—C17—H17D141.1
C7—C8—C9164.4 (6)H17B—C17—H17D56.3
C6—C7A—H7A113.4H17C—C17—H17D56.3
C10—C9—C8120.9 (3)C1—C17—H17E109.5
C10—C9—C19123.3 (3)H17A—C17—H17E56.3
C8—C9—C19115.7 (3)H17B—C17—H17E141.1
C9—C10—C11125.4 (3)H17C—C17—H17E56.3
C9—C10—H10117.3H17D—C17—H17E109.5
C11—C10—H10117.3C1—C17—H17F109.5
C12—C11—C10123.9 (3)H17A—C17—H17F56.3
C12—C11—H11118.1H17B—C17—H17F56.3
C10—C11—H11118.1H17C—C17—H17F141.1
C11—C12—C13125.3 (3)H17D—C17—H17F109.5
C11—C12—H12117.3H17E—C17—H17F109.5
C13—C12—H12117.3C5—C18—H18A109.5
C14—C13—C12118.5 (3)C5—C18—H18B109.5
C14—C13—C20122.4 (3)H18A—C18—H18B109.5
C12—C13—C20119.1 (2)C5—C18—H18C109.5
C13—C14—C15127.1 (3)H18A—C18—H18C109.5
C13—C14—H14116.4H18B—C18—H18C109.5
C15—C14—H14116.4C9—C19—H19A109.5
C15B—C15—C14123.3 (2)C9—C19—H19B109.5
C15B—C15—H15118.4H19A—C19—H19B109.5
C14—C15—H15118.4C9—C19—H19C109.5
C15—C15B—C14B123.5 (2)H19A—C19—H19C109.5
C15—C15B—H15B118.2H19B—C19—H19C109.5
C14B—C15B—H15B118.2C13—C20—H20A109.5
C13B—C14B—C15B126.9 (3)C13—C20—H20B109.5
C13B—C14B—H14B116.5H20A—C20—H20B109.5
C15B—C14B—H14B116.5C13—C20—H20C109.5
C14B—C13B—C12B119.3 (3)H20A—C20—H20C109.5
C14B—C13B—C20B123.2 (3)H20B—C20—H20C109.5
C12B—C13B—C20B117.5 (2)C1B—C16B—H16D109.5
C11B—C12B—C13B126.4 (3)C1B—C16B—H16E109.5
C11B—C12B—H12B116.8H16D—C16B—H16E109.5
C13B—C12B—H12B116.8C1B—C16B—H16F109.5
C12B—C11B—C10B124.4 (3)H16D—C16B—H16F109.5
C12B—C11B—H11B117.8H16E—C16B—H16F109.5
C10B—C11B—H11B117.8C1B—C17B—H17H109.5
C9B—C10B—C11B127.5 (3)C1B—C17B—H17I109.5
C9B—C10B—H10B116.3H17H—C17B—H17I109.5
C11B—C10B—H10B116.3C1B—C17B—H17J109.5
C10B—C9B—C8B120.3 (3)H17H—C17B—H17J109.5
C10B—C9B—C19B122.9 (3)H17I—C17B—H17J109.5
C8B—C9B—C19B116.9 (3)C5B—C18B—H18D109.5
C8B—C7B—C6B133.7 (8)C5B—C18B—H18E109.5
C8B—C7B—H7B113.1H18D—C18B—H18E109.5
C6B—C7B—H7B113.1C5B—C18B—H18F109.5
C7B—C8B—C9B132.2 (5)H18D—C18B—H18F109.5
C7B—C8B—H8B113.9H18E—C18B—H18F109.5
C9B—C8B—H8B113.9C9B—C19B—H19D109.5
C5B—C6B—C7BB108.1 (7)C9B—C19B—H19E109.5
C5B—C6B—C7B130.4 (4)H19D—C19B—H19E109.5
C7BB—C6B—C7B24.5 (4)C9B—C19B—H19F109.5
C5B—C6B—C1B123.0 (3)H19D—C19B—H19F109.5
C7BB—C6B—C1B128.7 (7)H19E—C19B—H19F109.5
C7B—C6B—C1B106.4 (4)C13B—C20B—H20D109.5
C6B—C5B—C4B120.3 (3)C13B—C20B—H20E109.5
C6B—C5B—C18B124.2 (3)H20D—C20B—H20E109.5
C4B—C5B—C18B115.5 (3)C13B—C20B—H20F109.5
O4B—C4B—C5B123.3 (3)H20D—C20B—H20F109.5
O4B—C4B—C3B120.2 (3)H20E—C20B—H20F109.5
C16—C1—C2—C372.6 (4)C15—C15B—C14B—C13B176.7 (3)
C17—C1—C2—C3167.2 (3)C15B—C14B—C13B—C12B178.6 (2)
C6—C1—C2—C347.9 (3)C15B—C14B—C13B—C20B1.6 (5)
C1—C2—C3—O3177.7 (3)C14B—C13B—C12B—C11B178.1 (3)
C1—C2—C3—C459.2 (3)C20B—C13B—C12B—C11B2.1 (4)
O3—C3—C4—O419.3 (4)C13B—C12B—C11B—C10B178.1 (3)
C2—C3—C4—O4142.1 (3)C12B—C11B—C10B—C9B178.2 (3)
O3—C3—C4—C5162.3 (3)C11B—C10B—C9B—C8B178.4 (3)
C2—C3—C4—C539.5 (4)C11B—C10B—C9B—C19B1.1 (5)
O4—C4—C5—C6172.2 (3)C6B—C7B—C8B—C9B175.4 (4)
C3—C4—C5—C69.5 (4)C10B—C9B—C8B—C7B172.6 (4)
O4—C4—C5—C187.1 (4)C19B—C9B—C8B—C7B7.8 (6)
C3—C4—C5—C18171.2 (3)C8B—C7B—C6B—C5B23.8 (9)
C4—C5—C6—C7173.2 (3)C8B—C7B—C6B—C7BB3.7 (10)
C18—C5—C6—C77.5 (5)C8B—C7B—C6B—C1B161.8 (5)
C4—C5—C6—C12.1 (4)C7BB—C6B—C5B—C4B178.6 (5)
C18—C5—C6—C1177.1 (3)C7B—C6B—C5B—C4B169.8 (4)
C4—C5—C6—C7A179.2 (7)C1B—C6B—C5B—C4B3.7 (4)
C18—C5—C6—C7A0.1 (9)C7BB—C6B—C5B—C18B3.1 (6)
C16—C1—C6—C5105.4 (3)C7B—C6B—C5B—C18B8.5 (6)
C17—C1—C6—C5134.2 (3)C1B—C6B—C5B—C18B178.0 (3)
C2—C1—C6—C516.9 (4)C6B—C5B—C4B—O4B168.9 (3)
C16—C1—C6—C769.5 (4)C18B—C5B—C4B—O4B12.7 (5)
C17—C1—C6—C750.8 (5)C6B—C5B—C4B—C3B13.0 (4)
C2—C1—C6—C7168.1 (4)C18B—C5B—C4B—C3B165.4 (3)
C16—C1—C6—C7A76.6 (5)O4B—C4B—C3B—O3B13.2 (4)
C17—C1—C6—C7A43.8 (6)C5B—C4B—C3B—O3B168.7 (3)
C2—C1—C6—C7A161.1 (5)O4B—C4B—C3B—C2B137.2 (3)
C5—C6—C7—C8176 (6)C5B—C4B—C3B—C2B44.7 (3)
C1—C6—C7—C89 (7)O3B—C3B—C2B—C1B175.8 (3)
C7A—C6—C7—C89 (5)C4B—C3B—C2B—C1B61.0 (3)
C6—C7—C8—C93 (8)C3B—C2B—C1B—C6B44.9 (3)
C7—C8—C9—C10179.8 (14)C3B—C2B—C1B—C16B165.3 (3)
C7—C8—C9—C190.4 (17)C3B—C2B—C1B—C17B78.2 (3)
C8—C9—C10—C11178.8 (3)C5B—C6B—C1B—C2B12.1 (4)
C19—C9—C10—C111.4 (5)C7BB—C6B—C1B—C2B161.6 (6)
C9—C10—C11—C12179.9 (3)C7B—C6B—C1B—C2B173.0 (3)
C10—C11—C12—C13179.8 (3)C5B—C6B—C1B—C16B130.7 (3)
C11—C12—C13—C14178.5 (3)C7BB—C6B—C1B—C16B43.0 (7)
C11—C12—C13—C201.1 (5)C7B—C6B—C1B—C16B54.4 (4)
C12—C13—C14—C15177.6 (3)C5B—C6B—C1B—C17B110.4 (3)
C20—C13—C14—C152.0 (5)C7BB—C6B—C1B—C17B75.8 (6)
C13—C14—C15—C15B177.4 (3)C7B—C6B—C1B—C17B64.5 (4)
C14—C15—C15B—C14B178.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O40.822.252.669 (4)112
(3) top
Crystal data top
C40H48O4Z = 1
Mr = 592.78F(000) = 320
Triclinic, P1Dx = 1.148 Mg m3
Hall symbol: P1Synchrotron radiation, λ = 0.67100 Å
a = 7.4769 (14) ÅCell parameters from 979 reflections
b = 10.4729 (19) Åθ = 2.3–24.0°
c = 11.633 (2) ŵ = 0.07 mm1
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) Å3
Data collection top
Bruker APEXII CCD area detector
diffractometer
4002 independent reflections
Radiation source: Station 9.8, SRS, Daresbury2799 reflections with I > 2σ(I)
Silicon monochromatorRint = 0.062
phi and ω scansθmax = 26.1°, θmin = 2.0°
Absorption correction: multi-scan
SADABS
h = 99
Tmin = 0.749, Tmax = 1.000k = 1313
14633 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0581P)2]
where P = (Fo2 + 2Fc2)/3
4002 reflections(Δ/σ)max = 0.003
409 parametersΔρmax = 0.19 e Å3
3 restraintsΔρmin = 0.17 e Å3
Crystal data top
C40H48O4γ = 76.389 (2)°
Mr = 592.78V = 857.5 (3) Å3
Triclinic, P1Z = 1
a = 7.4769 (14) ÅSynchrotron radiation, λ = 0.67100 Å
b = 10.4729 (19) ŵ = 0.07 mm1
c = 11.633 (2) ÅT = 100 K
α = 75.606 (2)°0.04 × 0.03 × 0.01 mm
β = 85.901 (2)°
Data collection top
Bruker APEXII CCD area detector
diffractometer
4002 independent reflections
Absorption correction: multi-scan
SADABS
2799 reflections with I > 2σ(I)
Tmin = 0.749, Tmax = 1.000Rint = 0.062
14633 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0423 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 1.01Δρmax = 0.19 e Å3
4002 reflectionsΔρmin = 0.17 e Å3
409 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
O30.8989 (3)1.2181 (2)1.2004 (2)0.0432 (5)
H30.94921.17651.26340.065*
O41.0608 (3)0.9612 (2)1.28650 (17)0.0343 (5)
O3B0.5316 (3)0.08464 (19)0.76918 (19)0.0396 (5)
H3B0.48590.05380.83510.059*
O4B0.3773 (3)0.1658 (2)0.87573 (17)0.0367 (5)
C10.9374 (4)1.0816 (3)0.9257 (3)0.0287 (6)
C20.9550 (4)1.1761 (3)1.0039 (3)0.0312 (6)
H2A1.08211.18331.00300.037*
H2B0.88051.26570.97140.037*
C30.8949 (4)1.1264 (3)1.1297 (2)0.0314 (6)
H3A0.76821.11571.12910.038*
C41.0166 (4)0.9893 (3)1.1820 (2)0.0271 (6)
C51.0676 (4)0.8941 (3)1.1061 (2)0.0257 (6)
C61.0188 (4)0.9345 (3)0.9905 (2)0.0249 (6)
C71.0400 (4)0.8359 (3)0.9220 (2)0.0283 (6)
C81.0452 (4)0.7499 (3)0.8686 (2)0.0273 (6)
C91.0483 (4)0.6431 (3)0.8133 (2)0.0267 (6)
C100.9954 (4)0.6728 (3)0.6992 (2)0.0261 (6)
H100.96800.76410.66040.031*
C110.9766 (4)0.5803 (3)0.6308 (2)0.0273 (7)
H111.00660.48800.66560.033*
C120.9172 (4)0.6216 (3)0.5181 (2)0.0266 (6)
H120.89270.71440.48550.032*
C130.8871 (4)0.5396 (3)0.4422 (2)0.0256 (6)
C140.8166 (4)0.6035 (3)0.3333 (3)0.0269 (6)
H140.79380.69740.31500.032*
C150.7729 (4)0.5457 (3)0.2434 (2)0.0266 (6)
H150.79070.45210.25890.032*
C161.0449 (5)1.1181 (3)0.8109 (3)0.0430 (8)
H16A1.17271.10350.82830.064*
H16B0.99871.21150.77250.064*
H16C1.03111.06240.75940.064*
C170.7356 (4)1.0966 (3)0.8971 (3)0.0386 (7)
H17D0.72791.03570.84890.058*
H17E0.68541.18790.85470.058*
H17F0.66701.07540.96950.058*
C181.1667 (4)0.7522 (3)1.1629 (3)0.0326 (7)
H18D1.21300.70461.10240.049*
H18E1.08310.70641.21410.049*
H18F1.26730.75481.20840.049*
C191.1066 (4)0.5018 (3)0.8899 (3)0.0306 (6)
H19D1.01840.48750.95310.046*
H19E1.22520.49050.92260.046*
H19F1.11340.43750.84270.046*
C200.9321 (4)0.3890 (3)0.4876 (3)0.0301 (6)
H20D0.85260.36400.55380.045*
H20E1.05790.35900.51250.045*
H20F0.91470.34740.42570.045*
C1B0.5262 (4)0.0926 (3)0.5234 (2)0.0288 (6)
C2B0.5945 (4)0.0060 (3)0.6028 (3)0.0295 (6)
H2B10.70850.01130.64170.035*
H2B20.62090.09770.55360.035*
C3B0.4587 (4)0.0045 (3)0.6955 (3)0.0311 (6)
H3B10.34800.02100.65540.037*
C4B0.4043 (4)0.1479 (3)0.7703 (2)0.0273 (6)
C5B0.3856 (4)0.2597 (3)0.7118 (2)0.0249 (6)
C6B0.4485 (4)0.2347 (3)0.6001 (2)0.0256 (6)
C7B0.4368 (4)0.3432 (3)0.5458 (2)0.0256 (6)
C8B0.4343 (4)0.4333 (3)0.4967 (2)0.0265 (6)
C9B0.4374 (4)0.5392 (3)0.4410 (2)0.0238 (6)
C10B0.4945 (4)0.5061 (3)0.3278 (2)0.0269 (6)
H10B0.52600.41410.29190.032*
C11B0.5123 (4)0.5946 (3)0.2569 (2)0.0250 (6)
H11B0.48220.68730.28970.030*
C12B0.5711 (4)0.5496 (3)0.1438 (2)0.0264 (6)
H12B0.59760.45630.11370.032*
C13B0.5977 (4)0.6285 (3)0.0644 (2)0.0251 (6)
C14B0.6637 (4)0.5635 (3)0.0458 (2)0.0261 (6)
H14B0.68340.46960.06420.031*
C15B0.7067 (4)0.6205 (3)0.1367 (3)0.0279 (6)
H15B0.68820.71410.12170.033*
C16B0.6881 (4)0.0925 (3)0.4508 (3)0.0404 (8)
H16D0.73570.00250.40450.061*
H16E0.64760.15230.39880.061*
H16F0.78280.12260.50320.061*
C17B0.3718 (5)0.0509 (3)0.4387 (3)0.0385 (7)
H17A0.27000.04970.48390.058*
H17B0.33210.11470.39020.058*
H17C0.41660.03760.38890.058*
C18B0.3024 (4)0.3984 (3)0.7835 (3)0.0327 (7)
H18A0.30780.46410.73990.049*
H18B0.17640.40370.79960.049*
H18C0.36960.41640.85690.049*
C19B0.3774 (4)0.6814 (3)0.5149 (3)0.0284 (6)
H19A0.38050.74430.46790.043*
H19B0.25440.69540.54200.043*
H19C0.45910.69540.58200.043*
C20B0.5514 (4)0.7809 (3)0.1085 (3)0.0295 (6)
H20A0.56720.82140.04550.044*
H20B0.42600.81090.13410.044*
H20C0.63160.80720.17390.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0563 (14)0.0333 (11)0.0446 (13)0.0041 (10)0.0034 (11)0.0226 (10)
O40.0356 (11)0.0404 (12)0.0290 (12)0.0049 (9)0.0041 (9)0.0144 (9)
O3B0.0526 (14)0.0269 (11)0.0406 (12)0.0010 (9)0.0039 (11)0.0186 (9)
O4B0.0429 (12)0.0388 (12)0.0282 (12)0.0016 (10)0.0081 (9)0.0129 (9)
C10.0354 (16)0.0227 (15)0.0274 (14)0.0060 (12)0.0047 (12)0.0042 (11)
C20.0373 (16)0.0185 (13)0.0352 (15)0.0022 (11)0.0060 (13)0.0037 (11)
C30.0347 (16)0.0273 (15)0.0354 (16)0.0047 (12)0.0018 (12)0.0151 (12)
C40.0274 (14)0.0280 (14)0.0280 (15)0.0074 (11)0.0012 (12)0.0091 (12)
C50.0269 (15)0.0223 (14)0.0288 (15)0.0072 (11)0.0003 (12)0.0066 (12)
C60.0278 (15)0.0222 (14)0.0248 (15)0.0033 (12)0.0003 (12)0.0082 (12)
C70.0285 (15)0.0262 (15)0.0275 (15)0.0027 (12)0.0022 (12)0.0041 (13)
C80.0295 (15)0.0269 (15)0.0251 (14)0.0029 (12)0.0004 (12)0.0085 (13)
C90.0256 (15)0.0262 (15)0.0295 (16)0.0048 (12)0.0008 (13)0.0096 (13)
C100.0267 (15)0.0231 (14)0.0288 (15)0.0040 (11)0.0002 (12)0.0083 (12)
C110.0250 (15)0.0242 (15)0.0311 (17)0.0015 (12)0.0012 (13)0.0072 (13)
C120.0289 (15)0.0227 (14)0.0276 (15)0.0021 (12)0.0016 (12)0.0078 (12)
C130.0231 (14)0.0261 (15)0.0280 (15)0.0037 (12)0.0005 (12)0.0090 (12)
C140.0290 (15)0.0223 (14)0.0292 (14)0.0020 (12)0.0008 (12)0.0092 (12)
C150.0258 (14)0.0255 (15)0.0268 (16)0.0021 (12)0.0004 (12)0.0070 (12)
C160.057 (2)0.0363 (17)0.0328 (16)0.0123 (15)0.0011 (15)0.0017 (14)
C170.0453 (18)0.0245 (15)0.0422 (17)0.0012 (13)0.0135 (14)0.0060 (13)
C180.0421 (18)0.0252 (14)0.0276 (15)0.0023 (13)0.0094 (13)0.0036 (12)
C190.0371 (16)0.0289 (15)0.0277 (15)0.0068 (13)0.0013 (13)0.0106 (12)
C200.0354 (16)0.0292 (15)0.0256 (14)0.0044 (12)0.0046 (12)0.0076 (12)
C1B0.0352 (16)0.0201 (14)0.0292 (15)0.0024 (12)0.0057 (12)0.0043 (12)
C2B0.0305 (15)0.0204 (13)0.0345 (15)0.0015 (11)0.0037 (12)0.0040 (11)
C3B0.0360 (15)0.0227 (14)0.0356 (16)0.0019 (12)0.0028 (12)0.0128 (12)
C4B0.0238 (14)0.0308 (15)0.0280 (16)0.0045 (11)0.0018 (11)0.0094 (12)
C5B0.0263 (15)0.0230 (14)0.0257 (15)0.0034 (11)0.0013 (12)0.0082 (11)
C6B0.0252 (14)0.0216 (14)0.0292 (16)0.0030 (11)0.0015 (12)0.0072 (12)
C7B0.0288 (15)0.0252 (15)0.0218 (14)0.0040 (12)0.0053 (12)0.0046 (12)
C8B0.0250 (15)0.0255 (15)0.0251 (14)0.0008 (11)0.0058 (12)0.0016 (12)
C9B0.0250 (15)0.0234 (14)0.0243 (14)0.0043 (12)0.0011 (12)0.0094 (12)
C10B0.0252 (15)0.0237 (14)0.0313 (16)0.0023 (12)0.0011 (12)0.0087 (12)
C11B0.0243 (15)0.0235 (15)0.0262 (15)0.0015 (12)0.0017 (12)0.0074 (12)
C12B0.0267 (15)0.0232 (14)0.0278 (15)0.0018 (12)0.0020 (12)0.0065 (12)
C13B0.0240 (15)0.0252 (15)0.0261 (15)0.0029 (12)0.0014 (12)0.0085 (12)
C14B0.0277 (15)0.0236 (14)0.0277 (15)0.0014 (12)0.0010 (12)0.0112 (12)
C15B0.0280 (15)0.0263 (15)0.0294 (16)0.0032 (12)0.0006 (12)0.0098 (13)
C16B0.0526 (19)0.0250 (15)0.0400 (18)0.0036 (14)0.0214 (15)0.0070 (13)
C17B0.0526 (19)0.0239 (14)0.0338 (16)0.0058 (13)0.0061 (14)0.0016 (12)
C18B0.0428 (17)0.0235 (15)0.0293 (15)0.0011 (13)0.0049 (13)0.0064 (12)
C19B0.0333 (15)0.0237 (14)0.0289 (16)0.0054 (12)0.0039 (12)0.0074 (12)
C20B0.0341 (16)0.0265 (14)0.0278 (15)0.0048 (12)0.0053 (12)0.0072 (12)
Geometric parameters (Å, º) top
O3—C31.418 (3)C20—H20D0.9600
O3—H30.8200C20—H20E0.9600
O4—C41.228 (3)C20—H20F0.9600
O3B—C3B1.412 (3)C1B—C16B1.524 (4)
O3B—H3B0.8200C1B—C2B1.530 (4)
O4B—C4B1.218 (3)C1B—C17B1.535 (4)
C1—C161.521 (4)C1B—C6B1.535 (4)
C1—C171.532 (4)C2B—C3B1.501 (4)
C1—C21.534 (4)C2B—H2B10.9700
C1—C61.536 (4)C2B—H2B20.9700
C2—C31.501 (4)C3B—C4B1.513 (4)
C2—H2A0.9700C3B—H3B10.9800
C2—H2B0.9700C4B—C5B1.471 (4)
C3—C41.513 (4)C5B—C6B1.356 (4)
C3—H3A0.9800C5B—C18B1.496 (4)
C4—C51.460 (4)C6B—C7B1.414 (4)
C5—C61.354 (4)C7B—C8B1.215 (4)
C5—C181.503 (4)C8B—C9B1.422 (4)
C6—C71.429 (4)C9B—C10B1.350 (4)
C7—C81.207 (4)C9B—C19B1.504 (4)
C8—C91.418 (4)C10B—C11B1.418 (4)
C9—C101.352 (4)C10B—H10B0.9300
C9—C191.507 (4)C11B—C12B1.351 (4)
C10—C111.434 (4)C11B—H11B0.9300
C10—H100.9300C12B—C13B1.434 (4)
C11—C121.347 (4)C12B—H12B0.9300
C11—H110.9300C13B—C14B1.360 (4)
C12—C131.437 (4)C13B—C20B1.513 (4)
C12—H120.9300C14B—C15B1.425 (4)
C13—C141.356 (4)C14B—H14B0.9300
C13—C201.496 (4)C15B—H15B0.9300
C14—C151.422 (4)C16B—H16D0.9600
C14—H140.9300C16B—H16E0.9600
C15—C15B1.349 (3)C16B—H16F0.9600
C15—H150.9300C17B—H17A0.9600
C16—H16A0.9600C17B—H17B0.9600
C16—H16B0.9600C17B—H17C0.9600
C16—H16C0.9600C18B—H18A0.9600
C17—H17D0.9600C18B—H18B0.9600
C17—H17E0.9600C18B—H18C0.9600
C17—H17F0.9600C19B—H19A0.9600
C18—H18D0.9600C19B—H19B0.9600
C18—H18E0.9600C19B—H19C0.9600
C18—H18F0.9600C20B—H20A0.9600
C19—H19D0.9600C20B—H20B0.9600
C19—H19E0.9600C20B—H20C0.9600
C19—H19F0.9600
C3—O3—H3109.5H20E—C20—H20F109.5
C3B—O3B—H3B109.5C16B—C1B—C2B108.0 (2)
C16—C1—C17109.4 (3)C16B—C1B—C17B109.1 (3)
C16—C1—C2108.4 (2)C2B—C1B—C17B111.5 (2)
C17—C1—C2111.0 (2)C16B—C1B—C6B110.9 (2)
C16—C1—C6109.4 (2)C2B—C1B—C6B109.9 (2)
C17—C1—C6109.4 (2)C17B—C1B—C6B107.5 (2)
C2—C1—C6109.3 (2)C3B—C2B—C1B113.2 (2)
C3—C2—C1112.0 (2)C3B—C2B—H2B1108.9
C3—C2—H2A109.2C1B—C2B—H2B1108.9
C1—C2—H2A109.2C3B—C2B—H2B2108.9
C3—C2—H2B109.2C1B—C2B—H2B2108.9
C1—C2—H2B109.2H2B1—C2B—H2B2107.8
H2A—C2—H2B107.9O3B—C3B—C2B110.8 (2)
O3—C3—C2112.2 (2)O3B—C3B—C4B109.8 (2)
O3—C3—C4110.5 (2)C2B—C3B—C4B111.1 (2)
C2—C3—C4109.1 (2)O3B—C3B—H3B1108.4
O3—C3—H3A108.3C2B—C3B—H3B1108.4
C2—C3—H3A108.3C4B—C3B—H3B1108.4
C4—C3—H3A108.3O4B—C4B—C5B122.9 (3)
O4—C4—C5123.2 (2)O4B—C4B—C3B118.9 (3)
O4—C4—C3119.1 (2)C5B—C4B—C3B118.2 (2)
C5—C4—C3117.6 (2)C6B—C5B—C4B119.9 (2)
C6—C5—C4119.6 (2)C6B—C5B—C18B123.5 (3)
C6—C5—C18123.0 (2)C4B—C5B—C18B116.5 (2)
C4—C5—C18117.4 (2)C5B—C6B—C7B119.8 (2)
C5—C6—C7119.3 (2)C5B—C6B—C1B124.1 (3)
C5—C6—C1124.6 (2)C7B—C6B—C1B116.1 (2)
C7—C6—C1116.1 (2)C8B—C7B—C6B177.0 (3)
C8—C7—C6174.7 (3)C7B—C8B—C9B178.0 (3)
C7—C8—C9176.1 (3)C10B—C9B—C8B118.5 (2)
C10—C9—C8119.3 (3)C10B—C9B—C19B124.9 (3)
C10—C9—C19124.6 (3)C8B—C9B—C19B116.6 (2)
C8—C9—C19116.1 (2)C9B—C10B—C11B127.8 (3)
C9—C10—C11127.7 (3)C9B—C10B—H10B116.1
C9—C10—H10116.2C11B—C10B—H10B116.1
C11—C10—H10116.2C12B—C11B—C10B122.6 (3)
C12—C11—C10122.6 (3)C12B—C11B—H11B118.7
C12—C11—H11118.7C10B—C11B—H11B118.7
C10—C11—H11118.7C11B—C12B—C13B127.8 (3)
C11—C12—C13127.8 (3)C11B—C12B—H12B116.1
C11—C12—H12116.1C13B—C12B—H12B116.1
C13—C12—H12116.1C14B—C13B—C12B118.9 (3)
C14—C13—C12117.8 (3)C14B—C13B—C20B123.2 (3)
C14—C13—C20123.5 (3)C12B—C13B—C20B117.9 (2)
C12—C13—C20118.7 (2)C13B—C14B—C15B128.4 (3)
C13—C14—C15128.5 (3)C13B—C14B—H14B115.8
C13—C14—H14115.7C15B—C14B—H14B115.8
C15—C14—H14115.7C15—C15B—C14B123.4 (2)
C15B—C15—C14123.0 (2)C15—C15B—H15B118.3
C15B—C15—H15118.5C14B—C15B—H15B118.3
C14—C15—H15118.5C1B—C16B—H16D109.5
C1—C16—H16A109.5C1B—C16B—H16E109.5
C1—C16—H16B109.5H16D—C16B—H16E109.5
H16A—C16—H16B109.5C1B—C16B—H16F109.5
C1—C16—H16C109.5H16D—C16B—H16F109.5
H16A—C16—H16C109.5H16E—C16B—H16F109.5
H16B—C16—H16C109.5C1B—C17B—H17A109.5
C1—C17—H17D109.5C1B—C17B—H17B109.5
C1—C17—H17E109.5H17A—C17B—H17B109.5
H17D—C17—H17E109.5C1B—C17B—H17C109.5
C1—C17—H17F109.5H17A—C17B—H17C109.5
H17D—C17—H17F109.5H17B—C17B—H17C109.5
H17E—C17—H17F109.5C5B—C18B—H18A109.5
C5—C18—H18D109.5C5B—C18B—H18B109.5
C5—C18—H18E109.5H18A—C18B—H18B109.5
H18D—C18—H18E109.5C5B—C18B—H18C109.5
C5—C18—H18F109.5H18A—C18B—H18C109.5
H18D—C18—H18F109.5H18B—C18B—H18C109.5
H18E—C18—H18F109.5C9B—C19B—H19A109.5
C9—C19—H19D109.5C9B—C19B—H19B109.5
C9—C19—H19E109.5H19A—C19B—H19B109.5
H19D—C19—H19E109.5C9B—C19B—H19C109.5
C9—C19—H19F109.5H19A—C19B—H19C109.5
H19D—C19—H19F109.5H19B—C19B—H19C109.5
H19E—C19—H19F109.5C13B—C20B—H20A109.5
C13—C20—H20D109.5C13B—C20B—H20B109.5
C13—C20—H20E109.5H20A—C20B—H20B109.5
H20D—C20—H20E109.5C13B—C20B—H20C109.5
C13—C20—H20F109.5H20A—C20B—H20C109.5
H20D—C20—H20F109.5H20B—C20B—H20C109.5
C16—C1—C2—C3165.6 (3)C17B—C1B—C2B—C3B71.3 (3)
C17—C1—C2—C374.2 (3)C6B—C1B—C2B—C3B47.7 (3)
C6—C1—C2—C346.5 (3)C1B—C2B—C3B—O3B177.6 (2)
C1—C2—C3—O3175.9 (2)C1B—C2B—C3B—C4B55.4 (3)
C1—C2—C3—C461.3 (3)O3B—C3B—C4B—O4B20.8 (4)
O3—C3—C4—O419.1 (4)C2B—C3B—C4B—O4B143.6 (3)
C2—C3—C4—O4142.8 (3)O3B—C3B—C4B—C5B159.5 (2)
O3—C3—C4—C5164.1 (2)C2B—C3B—C4B—C5B36.7 (3)
C2—C3—C4—C540.4 (3)O4B—C4B—C5B—C6B168.2 (3)
O4—C4—C5—C6177.8 (3)C3B—C4B—C5B—C6B12.0 (4)
C3—C4—C5—C65.6 (4)O4B—C4B—C5B—C18B9.4 (4)
O4—C4—C5—C184.7 (4)C3B—C4B—C5B—C18B170.3 (3)
C3—C4—C5—C18171.9 (3)C4B—C5B—C6B—C7B177.5 (2)
C4—C5—C6—C7169.1 (2)C18B—C5B—C6B—C7B0.0 (4)
C18—C5—C6—C78.2 (4)C4B—C5B—C6B—C1B5.4 (4)
C4—C5—C6—C19.9 (4)C18B—C5B—C6B—C1B177.2 (3)
C18—C5—C6—C1172.7 (3)C16B—C1B—C6B—C5B142.3 (3)
C16—C1—C6—C5129.2 (3)C2B—C1B—C6B—C5B23.0 (4)
C17—C1—C6—C5111.0 (3)C17B—C1B—C6B—C5B98.6 (3)
C2—C1—C6—C510.7 (4)C16B—C1B—C6B—C7B40.5 (3)
C16—C1—C6—C751.7 (3)C2B—C1B—C6B—C7B159.8 (2)
C17—C1—C6—C768.1 (3)C17B—C1B—C6B—C7B78.6 (3)
C2—C1—C6—C7170.2 (2)C5B—C6B—C7B—C8B145 (5)
C5—C6—C7—C878 (3)C1B—C6B—C7B—C8B37 (5)
C1—C6—C7—C8101 (3)C6B—C7B—C8B—C9B58 (11)
C6—C7—C8—C944 (7)C7B—C8B—C9B—C10B98 (8)
C7—C8—C9—C10148 (4)C7B—C8B—C9B—C19B82 (8)
C7—C8—C9—C1930 (5)C8B—C9B—C10B—C11B178.4 (3)
C8—C9—C10—C11175.2 (3)C19B—C9B—C10B—C11B0.9 (5)
C19—C9—C10—C112.8 (5)C9B—C10B—C11B—C12B179.9 (3)
C9—C10—C11—C12177.9 (3)C10B—C11B—C12B—C13B178.8 (3)
C10—C11—C12—C13177.8 (3)C11B—C12B—C13B—C14B178.0 (3)
C11—C12—C13—C14176.4 (3)C11B—C12B—C13B—C20B1.6 (4)
C11—C12—C13—C202.7 (4)C12B—C13B—C14B—C15B177.5 (2)
C12—C13—C14—C15179.2 (3)C20B—C13B—C14B—C15B2.1 (4)
C20—C13—C14—C150.2 (5)C14—C15—C15B—C14B179.5 (3)
C13—C14—C15—C15B178.4 (3)C13B—C14B—C15B—C15179.6 (3)
C16B—C1B—C2B—C3B168.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O40.822.172.648 (3)117
O3B—H3B···O4B0.822.192.629 (3)114

Experimental details

(s-cis-1)(s-trans-1)(2)(3)
Crystal data
Chemical formulaC44H56O6·0.44(C4H8O2)C44H56O6C40H50O4C40H48O4
Mr719.59680.89594.80592.78
Crystal system, space groupMonoclinic, C2/cMonoclinic, P21/cTriclinic, P1Triclinic, P1
Temperature (K)100100100100
a, b, c (Å)12.9673 (15), 10.7883 (13), 30.264 (4)10.6598 (10), 10.1683 (10), 18.2940 (18)7.7821 (4), 9.9578 (5), 11.4162 (5)7.4769 (14), 10.4729 (19), 11.633 (2)
α, β, γ (°)90, 101.796 (1), 9090, 100.700 (2), 9088.126 (1), 78.329 (1), 84.340 (1)75.606 (2), 85.901 (2), 76.389 (2)
V3)4144.3 (8)1948.4 (3)862.08 (7)857.5 (3)
Z4211
Radiation typeMo KαMo KαSynchrotron, λ = 0.6709 ÅSynchrotron, λ = 0.67100 Å
µ (mm1)0.080.080.070.07
Crystal size (mm)0.60 × 0.60 × 0.050.60 × 0.60 × 0.100.2 × 0.2 × 0.020.04 × 0.03 × 0.01
Data collection
DiffractometerBruker APEX CCD area detector
diffractometer
Bruker APEX CCD area detector
diffractometer
Bruker APEXII CCD area detector
diffractometer
Bruker APEXII CCD area detector
diffractometer
Absorption correctionMulti-scan
SADABS
Multi-scan
SADABS
Tmin, Tmax0.736, 1.0000.749, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
13064, 3632, 2913 9816, 3425, 2506 6688, 3029, 2910 14633, 4002, 2799
Rint0.0760.0720.0160.062
(sin θ/λ)max1)0.5950.5950.6020.655
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.085, 0.218, 1.11 0.065, 0.175, 1.08 0.046, 0.126, 1.08 0.042, 0.105, 1.01
No. of reflections3632342530294002
No. of parameters304305428409
No. of restraints117731433
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0625P)2 + 15.0678P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0489P)2 + 1.5414P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0747P)2 + 0.1591P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0581P)2]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.54, 0.280.39, 0.210.17, 0.160.19, 0.17

Computer programs: Bruker SMART, Bruker SAINT, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Bruker SHELXTL; PLATON (Spek,2003).

Hydrogen-bond geometry (Å, º) for (2) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O40.822.252.669 (4)111.8
Hydrogen-bond geometry (Å, º) for (3) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O40.822.172.648 (3)117.4
O3B—H3B···O4B0.822.192.629 (3)113.5
 

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