Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The crystal structures of the unbound carotenoids, synthetic astaxanthin (3S,3′S:3R,3′S:3R,3′R in a 1:2:1 ratio), canthaxanthin and (3R,3′S, meso)-zeaxanthin are compared with each other and the protein bound astaxanthin molecule in the carotenoprotein, β-crustacyanin. Three new crystal forms of astaxanthin have been obtained, using different crystallization conditions, comprising a chloroform solvate, a pyridine solvate and an unsolvated form. In each structure, the astaxanthin molecules, which are similar to one another, are centrosymmetric and adopt the 6-s-cis conformation; the end rings are bent out of the plane of the polyene chain by angles of −42.6 (5), −48.9 (5) and −50.4 (3)°, respectively, and are disordered, showing the presence of both R and S configurations (in a 1:1 ratio). In the crystal packing of the chloroform and pyridine solvates, the astaxanthin molecules show pair-wise end-to-end intermolecular hydrogen bonding of the adjacent 3-hydroxyl and 4-keto oxygens, whereas in the unsolvated crystal form, the hydrogen-bonding interaction is intermolecular. In addition, there are intermolecular C—H hydrogen bonds in all three structures. The canthaxanthin structure, measured at 100 and 293 K, also adopts the 6-s-cis conformation, but with disorder of one end ring only. The rotation of the end rings out of the plane of the polyene chains (ca −50 ° for each structure) is similar to that of astaxanthin. A number of possible C—H hydrogen bonds to the keto O atoms are also observed. (3R,3′S, meso)-zeaxanthin is centrosymmetric with a C5—C6—C7—C8 torsion angle of −74.9 (3)°; the molecules show pair-wise hydrogen bonding between the hydroxyl O atoms. In addition, for all the crystal structures the polyene chains were arranged one above the other, with intermolecular distances of 3.61–3.79 Å, indicating the presence of π-stacking interactions. Overall, these six crystal structures provide an ensemble of experimentally derived results that allow several key parameters, thought to influence colour tuning of the bathochromic shift of astaxanthin in crustacyanin, to be varied. The fact that the colour of each of the six crystals remains red, rather than turning blue, is therefore especially significant.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768106052633/bm5041sup1.cif
Contains datablocks axt-CL, axt-PY, AXT-un, canth-100K, canth-293, zea

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106052633/bm5041axt-CLsup2.hkl
Contains datablock astbm

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106052633/bm5041axt-PYsup3.hkl
Contains datablock axt-PY

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106052633/bm5041AXT-unsup4.hkl
Contains datablock AXT-un

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106052633/bm5041canth-100Ksup5.hkl
Contains datablock canth-100K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106052633/bm5041canth-293sup6.hkl
Contains datablock canth-293

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106052633/bm5041zeasup7.hkl
Contains datablock zea

CCDC references: 644719; 644720; 644721; 644722; 644723; 644724

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, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
(axt-CL) top
Crystal data top
C40H52O4·2(CHCl3)Z = 1
Mr = 835.55F(000) = 440
Triclinic, P1Dx = 1.303 Mg m3
Hall symbol: -P1Mo Kα radiation, λ = 0.71073 Å
a = 5.9588 (8) ÅCell parameters from 1032 reflections
b = 11.8583 (16) Åθ = 2.4–21.9°
c = 15.647 (2) ŵ = 0.44 mm1
α = 79.036 (2)°T = 100 K
β = 80.499 (3)°Needle, red
γ = 82.506 (2)°0.65 × 0.05 × 0.02 mm
V = 1065.0 (3) Å3
Data collection top
CCD area detector
diffractometer
1776 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.061
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
phi and ω scansh = 77
7182 measured reflectionsk = 1414
3634 independent reflectionsl = 1818
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 0.80 w = 1/[σ2(Fo2) + (0.0281P)2]
where P = (Fo2 + 2Fc2)/3
3634 reflections(Δ/σ)max = 0.005
259 parametersΔρmax = 0.54 e Å3
2 restraintsΔρmin = 0.57 e Å3
Crystal data top
C40H52O4·2(CHCl3)γ = 82.506 (2)°
Mr = 835.55V = 1065.0 (3) Å3
Triclinic, P1Z = 1
a = 5.9588 (8) ÅMo Kα radiation
b = 11.8583 (16) ŵ = 0.44 mm1
c = 15.647 (2) ÅT = 100 K
α = 79.036 (2)°0.65 × 0.05 × 0.02 mm
β = 80.499 (3)°
Data collection top
CCD area detector
diffractometer
1776 reflections with I > 2σ(I)
7182 measured reflectionsRint = 0.061
3634 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0482 restraints
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 0.80Δρmax = 0.54 e Å3
3634 reflectionsΔρmin = 0.57 e Å3
259 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)
O31.4708 (4)0.17695 (19)0.98503 (15)0.0380 (7)
H3O1.519 (6)0.119 (2)0.997 (2)0.057*
O41.2603 (4)0.03925 (19)0.95696 (15)0.0375 (7)
C11.1646 (6)0.1841 (3)0.7949 (2)0.0334 (10)
C2A1.2522 (13)0.2224 (6)0.8912 (5)0.024 (2)0.508 (8)
H2A1.11880.23270.93790.029*0.508 (8)
H2B1.34950.29700.89320.029*0.508 (8)
C3A1.3848 (13)0.1323 (6)0.9069 (5)0.018 (2)0.508 (8)
H3A1.51280.11680.85750.021*0.508 (8)
C2B1.3610 (10)0.2017 (5)0.8464 (4)0.024 (2)0.492 (8)
H2C1.41950.28450.85710.029*0.492 (8)
H2D1.48680.15720.81340.029*0.492 (8)
C3B1.2757 (10)0.1611 (5)0.9320 (4)0.025 (3)0.492 (8)
H3B1.14120.20070.96520.030*0.492 (8)
C41.2184 (6)0.0258 (3)0.9112 (2)0.0325 (9)
C51.0661 (5)0.0102 (3)0.8442 (2)0.0227 (8)
C61.0446 (5)0.0602 (3)0.7884 (2)0.0241 (8)
C70.9169 (5)0.0221 (3)0.7136 (2)0.0271 (9)
H70.98630.04620.65990.033*
C80.7147 (5)0.0423 (3)0.7113 (2)0.0227 (8)
H80.63560.06100.76550.027*
C90.6068 (5)0.0856 (3)0.6337 (2)0.0213 (8)
C100.4047 (5)0.1530 (3)0.6400 (2)0.0208 (8)
H100.33420.16130.69780.025*
C110.2852 (5)0.2130 (3)0.5699 (2)0.0223 (8)
H110.35310.20740.51130.027*
C120.0828 (5)0.2768 (2)0.5818 (2)0.0217 (8)
H120.01570.27850.64110.026*
C130.0445 (5)0.3431 (3)0.5147 (2)0.0206 (8)
C140.2506 (5)0.3999 (3)0.5391 (2)0.0231 (8)
H140.30300.38980.60050.028*
C150.3988 (5)0.4730 (3)0.4844 (2)0.0252 (8)
H150.35270.48450.42250.030*
C160.9822 (6)0.2684 (3)0.8116 (2)0.0321 (9)
H16A1.05590.34780.81870.048*
H16B0.89670.25420.76150.048*
H16C0.87700.25720.86510.048*
C171.3226 (6)0.2024 (3)0.7107 (3)0.0604 (14)
H17A1.43330.14490.69620.091*
H17B1.23210.19400.66250.091*
H17C1.40430.28000.71910.091*
C180.9535 (6)0.1329 (2)0.8413 (2)0.0286 (9)
H18A0.91350.16340.78240.043*
H18B1.05970.18120.85510.043*
H18C0.81460.13350.88470.043*
C190.7298 (5)0.0573 (3)0.5475 (2)0.0309 (9)
H19A0.63530.08870.50110.046*
H19B0.75890.02670.55180.046*
H19C0.87550.09140.53340.046*
C200.0634 (6)0.3457 (3)0.4203 (2)0.0298 (9)
H20A0.03910.39280.38140.045*
H20B0.08980.26680.40750.045*
H20C0.20950.37900.41060.045*
C1S0.4638 (6)0.3863 (3)0.8698 (2)0.0372 (10)
H1S0.50680.30490.89780.045*
Cl1S0.26261 (17)0.45298 (8)0.94431 (6)0.0479 (3)
Cl2S0.3449 (2)0.38433 (11)0.77444 (7)0.0714 (4)
Cl3S0.70928 (18)0.45829 (11)0.84040 (8)0.0687 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0517 (19)0.0321 (16)0.0325 (15)0.0125 (14)0.0241 (14)0.0068 (13)
O40.0426 (17)0.0325 (15)0.0398 (16)0.0089 (13)0.0187 (14)0.0101 (13)
C10.028 (2)0.020 (2)0.056 (3)0.0015 (18)0.022 (2)0.0064 (19)
C2A0.021 (5)0.014 (4)0.038 (6)0.004 (4)0.016 (4)0.003 (4)
C3A0.017 (5)0.017 (5)0.020 (5)0.002 (4)0.004 (4)0.004 (4)
C2B0.023 (5)0.021 (5)0.023 (5)0.003 (4)0.005 (4)0.003 (4)
C3B0.014 (6)0.028 (6)0.029 (5)0.003 (4)0.004 (4)0.006 (4)
C40.037 (2)0.036 (2)0.022 (2)0.005 (2)0.0028 (19)0.0064 (19)
C50.017 (2)0.023 (2)0.0233 (19)0.0049 (16)0.0010 (16)0.0003 (16)
C60.0131 (19)0.019 (2)0.038 (2)0.0014 (16)0.0051 (18)0.0020 (17)
C70.023 (2)0.023 (2)0.038 (2)0.0025 (17)0.0080 (18)0.0098 (17)
C80.021 (2)0.0194 (19)0.027 (2)0.0046 (16)0.0010 (17)0.0039 (16)
C90.017 (2)0.0168 (19)0.031 (2)0.0019 (16)0.0056 (17)0.0030 (16)
C100.017 (2)0.0198 (19)0.025 (2)0.0013 (16)0.0016 (16)0.0048 (16)
C110.022 (2)0.0189 (19)0.028 (2)0.0017 (16)0.0053 (17)0.0068 (16)
C120.021 (2)0.0193 (19)0.0248 (19)0.0024 (16)0.0042 (17)0.0020 (16)
C130.021 (2)0.0164 (19)0.025 (2)0.0025 (16)0.0084 (17)0.0013 (16)
C140.022 (2)0.0197 (19)0.027 (2)0.0020 (16)0.0057 (17)0.0021 (16)
C150.023 (2)0.023 (2)0.029 (2)0.0032 (16)0.0086 (18)0.0012 (16)
C160.036 (2)0.023 (2)0.034 (2)0.0011 (18)0.0039 (19)0.0025 (17)
C170.033 (3)0.021 (2)0.115 (4)0.0016 (19)0.021 (3)0.012 (2)
C180.033 (2)0.024 (2)0.027 (2)0.0060 (17)0.0053 (18)0.0036 (16)
C190.022 (2)0.032 (2)0.041 (2)0.0061 (17)0.0094 (18)0.0143 (18)
C200.030 (2)0.029 (2)0.033 (2)0.0034 (17)0.0119 (19)0.0086 (17)
C1S0.038 (3)0.030 (2)0.037 (2)0.0056 (19)0.000 (2)0.0012 (18)
Cl1S0.0488 (7)0.0465 (7)0.0408 (6)0.0145 (5)0.0004 (5)0.0076 (5)
Cl2S0.0767 (9)0.1042 (10)0.0465 (7)0.0446 (8)0.0001 (7)0.0294 (7)
Cl3S0.0407 (7)0.1008 (10)0.0723 (8)0.0212 (7)0.0011 (6)0.0311 (7)
Geometric parameters (Å, º) top
O3—C3A1.389 (8)C10—H100.9500
O3—C3B1.509 (6)C11—C121.342 (4)
O3—H3O0.834 (17)C11—H110.9500
O4—C41.220 (4)C12—C131.446 (4)
C1—C2B1.499 (7)C12—H120.9500
C1—C171.522 (5)C13—C141.355 (4)
C1—C161.530 (4)C13—C201.507 (4)
C1—C61.540 (4)C14—C151.425 (4)
C1—C2A1.640 (8)C14—H140.9500
C2A—C3A1.487 (9)C15—C15i1.351 (6)
C2A—H2A0.9900C15—H150.9500
C2A—H2B0.9900C16—H16A0.9800
C3A—C41.505 (8)C16—H16B0.9800
C3A—H3A1.0000C16—H16C0.9800
C2B—C3B1.4971C17—H17A0.9800
C2B—H2C0.9900C17—H17B0.9800
C2B—H2D0.9900C17—H17C0.9800
C3B—C41.579 (7)C18—H18A0.9800
C3B—H3B1.0000C18—H18B0.9800
C4—C51.466 (4)C18—H18C0.9800
C5—C61.349 (4)C19—H19A0.9800
C5—C181.517 (4)C19—H19B0.9800
C6—C71.469 (4)C19—H19C0.9800
C7—C81.341 (4)C20—H20A0.9800
C7—H70.9500C20—H20B0.9800
C8—C91.445 (4)C20—H20C0.9800
C8—H80.9500C1S—Cl3S1.742 (4)
C9—C101.356 (4)C1S—Cl1S1.751 (3)
C9—C191.499 (4)C1S—Cl2S1.759 (3)
C10—C111.430 (4)C1S—H1S1.0000
C3A—O3—H3O102 (2)C9—C10—C11127.7 (3)
C3B—O3—H3O120 (2)C9—C10—H10116.2
C2B—C1—C1792.1 (3)C11—C10—H10116.2
C2B—C1—C16122.5 (3)C12—C11—C10124.0 (3)
C17—C1—C16108.2 (3)C12—C11—H11118.0
C2B—C1—C6112.1 (3)C10—C11—H11118.0
C17—C1—C6112.1 (3)C11—C12—C13127.3 (3)
C16—C1—C6108.6 (3)C11—C12—H12116.3
C17—C1—C2A121.2 (4)C13—C12—H12116.3
C16—C1—C2A96.4 (4)C14—C13—C12119.2 (3)
C6—C1—C2A108.7 (4)C14—C13—C20123.6 (3)
C3A—C2A—C1109.7 (6)C12—C13—C20117.3 (3)
C3A—C2A—H2A109.7C13—C14—C15128.3 (3)
C1—C2A—H2A109.7C13—C14—H14115.8
C3A—C2A—H2B109.7C15—C14—H14115.8
C1—C2A—H2B109.7C15i—C15—C14123.7 (4)
H2A—C2A—H2B108.2C15i—C15—H15118.2
O3—C3A—C2A105.7 (6)C14—C15—H15118.2
O3—C3A—C4113.9 (5)C1—C16—H16A109.5
C2A—C3A—C4106.0 (5)C1—C16—H16B109.5
O3—C3A—H3A110.3H16A—C16—H16B109.5
C2A—C3A—H3A110.3C1—C16—H16C109.5
C4—C3A—H3A110.3H16A—C16—H16C109.5
C3B—C2B—C1107.8 (3)H16B—C16—H16C109.5
C3B—C2B—H2C110.2C1—C17—H17A109.5
C1—C2B—H2C110.2C1—C17—H17B109.5
C3B—C2B—H2D110.2H17A—C17—H17B109.5
C1—C2B—H2D110.2C1—C17—H17C109.5
H2C—C2B—H2D108.5H17A—C17—H17C109.5
C2B—C3B—O3108.9 (2)H17B—C17—H17C109.5
C2B—C3B—C4107.6 (2)C5—C18—H18A109.5
O3—C3B—C4103.6 (4)C5—C18—H18B109.5
C2B—C3B—H3B112.1H18A—C18—H18B109.5
O3—C3B—H3B112.1C5—C18—H18C109.5
C4—C3B—H3B112.1H18A—C18—H18C109.5
O4—C4—C5122.9 (3)H18B—C18—H18C109.5
O4—C4—C3A115.3 (4)C9—C19—H19A109.5
C5—C4—C3A119.3 (4)C9—C19—H19B109.5
O4—C4—C3B123.2 (3)H19A—C19—H19B109.5
C5—C4—C3B112.6 (3)C9—C19—H19C109.5
C6—C5—C4120.9 (3)H19A—C19—H19C109.5
C6—C5—C18125.2 (3)H19B—C19—H19C109.5
C4—C5—C18113.8 (3)C13—C20—H20A109.5
C5—C6—C7122.5 (3)C13—C20—H20B109.5
C5—C6—C1122.5 (3)H20A—C20—H20B109.5
C7—C6—C1114.9 (3)C13—C20—H20C109.5
C8—C7—C6128.2 (3)H20A—C20—H20C109.5
C8—C7—H7115.9H20B—C20—H20C109.5
C6—C7—H7115.9Cl3S—C1S—Cl1S111.22 (19)
C7—C8—C9125.7 (3)Cl3S—C1S—Cl2S109.04 (19)
C7—C8—H8117.2Cl1S—C1S—Cl2S109.92 (19)
C9—C8—H8117.2Cl3S—C1S—H1S108.9
C10—C9—C8119.8 (3)Cl1S—C1S—H1S108.9
C10—C9—C19122.3 (3)Cl2S—C1S—H1S108.9
C8—C9—C19117.9 (3)
C2B—C1—C2A—C3A51.0 (8)C3B—C4—C5—C620.4 (5)
C17—C1—C2A—C3A81.1 (6)O4—C4—C5—C183.9 (5)
C16—C1—C2A—C3A163.2 (5)C3A—C4—C5—C18164.8 (4)
C6—C1—C2A—C3A51.0 (6)C3B—C4—C5—C18163.3 (3)
C3B—O3—C3A—C2A39.7 (7)C4—C5—C6—C7172.1 (3)
C3B—O3—C3A—C476.3 (8)C18—C5—C6—C73.8 (5)
C1—C2A—C3A—O3174.2 (5)C4—C5—C6—C13.9 (5)
C1—C2A—C3A—C464.6 (7)C18—C5—C6—C1179.8 (3)
C17—C1—C2B—C3B166.22 (17)C2B—C1—C6—C519.3 (5)
C16—C1—C2B—C3B80.6 (3)C17—C1—C6—C5121.3 (4)
C6—C1—C2B—C3B51.3 (3)C16—C1—C6—C5119.2 (3)
C2A—C1—C2B—C3B39.1 (6)C2A—C1—C6—C515.4 (5)
C1—C2B—C3B—O3179.5 (5)C2B—C1—C6—C7156.9 (3)
C1—C2B—C3B—C467.8 (3)C17—C1—C6—C754.9 (4)
C3A—O3—C3B—C2B53.7 (8)C16—C1—C6—C764.5 (4)
C3A—O3—C3B—C460.6 (8)C2A—C1—C6—C7168.3 (4)
O3—C3A—C4—O435.5 (7)C5—C6—C7—C842.6 (5)
C2A—C3A—C4—O4151.3 (5)C1—C6—C7—C8141.1 (3)
O3—C3A—C4—C5162.2 (4)C6—C7—C8—C9174.2 (3)
C2A—C3A—C4—C546.5 (7)C7—C8—C9—C10178.0 (3)
O3—C3A—C4—C3B77.8 (9)C7—C8—C9—C190.3 (5)
C2A—C3A—C4—C3B38.0 (6)C8—C9—C10—C11173.0 (3)
C2B—C3B—C4—O4140.4 (3)C19—C9—C10—C114.6 (5)
O3—C3B—C4—O425.2 (5)C9—C10—C11—C12178.9 (3)
C2B—C3B—C4—C552.4 (3)C10—C11—C12—C13177.6 (3)
O3—C3B—C4—C5167.6 (3)C11—C12—C13—C14178.1 (3)
C2B—C3B—C4—C3A57.4 (8)C11—C12—C13—C202.5 (5)
O3—C3B—C4—C3A57.8 (7)C12—C13—C14—C15177.4 (3)
O4—C4—C5—C6172.4 (3)C20—C13—C14—C152.0 (5)
C3A—C4—C5—C611.6 (6)C13—C14—C15—C15i179.3 (4)
Symmetry code: (i) x1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18C···O3ii0.982.523.460 (4)161
C18—H18C···O4ii0.982.913.557 (4)124
C1S—H1S···O3ii1.002.163.061 (4)149
O3—H3O···O4iii0.83 (2)2.02 (2)2.790 (3)154 (3)
Symmetry codes: (ii) x+2, y, z+2; (iii) x+3, y, z+2.
(axt-PY) top
Crystal data top
C40H52O4·2(C5H5N)F(000) = 816
Mr = 755.02Dx = 1.156 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ynCell parameters from 1008 reflections
a = 18.568 (4) Åθ = 2.2–19.6°
b = 6.1926 (13) ŵ = 0.07 mm1
c = 19.803 (4) ÅT = 100 K
β = 107.746 (4)°Plate, red
V = 2168.7 (8) Å30.60 × 0.15 × 0.05 mm
Z = 2
Data collection top
CCD area detector
diffractometer
1400 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.148
Graphite monochromatorθmax = 23.3°, θmin = 1.3°
phi and ω scansh = 2020
12345 measured reflectionsk = 66
3104 independent reflectionsl = 2222
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.0351P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.77(Δ/σ)max < 0.001
3103 reflectionsΔρmax = 0.26 e Å3
292 parametersΔρmin = 0.17 e Å3
7 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0040 (9)
Crystal data top
C40H52O4·2(C5H5N)V = 2168.7 (8) Å3
Mr = 755.02Z = 2
Monoclinic, P21/nMo Kα radiation
a = 18.568 (4) ŵ = 0.07 mm1
b = 6.1926 (13) ÅT = 100 K
c = 19.803 (4) Å0.60 × 0.15 × 0.05 mm
β = 107.746 (4)°
Data collection top
CCD area detector
diffractometer
1400 reflections with I > 2σ(I)
12345 measured reflectionsRint = 0.148
3104 independent reflectionsθmax = 23.3°
Refinement top
R[F2 > 2σ(F2)] = 0.0497 restraints
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 0.77Δρmax = 0.26 e Å3
3103 reflectionsΔρmin = 0.17 e Å3
292 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)
O30.57811 (14)0.8999 (5)0.60122 (15)0.0528 (8)
H3O0.558 (3)0.989 (7)0.570 (2)0.18 (3)*
O40.45807 (13)0.7535 (4)0.49578 (13)0.0482 (7)
C10.48894 (17)0.5126 (5)0.69853 (16)0.0327 (9)
C2A0.5522 (6)0.6276 (17)0.6678 (6)0.025 (3)0.508 (16)
H2A0.59190.69410.70770.030*0.508 (16)
H2B0.57660.51580.64640.030*0.508 (16)
C3A0.5178 (8)0.801 (2)0.6122 (7)0.036 (3)0.508 (16)
H3A0.48830.90670.63140.044*0.508 (16)
C2B0.5248 (7)0.713 (2)0.6869 (5)0.034 (3)0.492 (16)
H2C0.49080.83610.68670.040*0.492 (16)
H2D0.57230.73500.72610.040*0.492 (16)
C3B0.5413 (8)0.705 (3)0.6198 (7)0.032 (3)0.492 (16)
H3B0.57490.57780.62090.039*0.492 (16)
C40.46642 (19)0.6753 (6)0.5545 (2)0.0366 (9)
C50.41454 (17)0.5161 (5)0.56773 (17)0.0312 (8)
C60.42262 (17)0.4456 (5)0.63385 (16)0.0290 (8)
C70.36648 (18)0.3087 (5)0.65139 (16)0.0323 (9)
H70.35150.35430.69090.039*
C80.33352 (17)0.1286 (5)0.61948 (17)0.0310 (9)
H80.35100.07190.58270.037*
C90.27369 (17)0.0130 (5)0.63610 (15)0.0279 (8)
C100.24396 (17)0.1670 (5)0.59864 (16)0.0324 (9)
H100.26780.21710.56540.039*
C110.18050 (17)0.2889 (5)0.60406 (16)0.0291 (8)
H110.15480.23830.63580.035*
C120.15466 (17)0.4716 (5)0.56696 (16)0.0316 (9)
H120.18200.52390.53680.038*
C130.08999 (17)0.5921 (5)0.56925 (16)0.0286 (8)
C140.07096 (18)0.7735 (5)0.52928 (17)0.0330 (9)
H140.10420.81310.50310.040*
C150.00756 (18)0.9129 (5)0.52135 (16)0.0337 (9)
H150.02600.88070.54780.040*
C160.53545 (19)0.3179 (5)0.72941 (19)0.0558 (12)
H16A0.58030.36300.76760.084*
H16B0.55120.24450.69240.084*
H16C0.50520.21890.74840.084*
C17B0.4597 (7)0.566 (2)0.7660 (6)0.043 (3)0.492 (16)
H17D0.49920.64420.80190.064*0.492 (16)
H17E0.44810.43080.78630.064*0.492 (16)
H17F0.41400.65530.75050.064*0.492 (16)
C17A0.4655 (6)0.662 (2)0.7422 (6)0.037 (3)0.508 (16)
H17A0.51010.72990.77530.055*0.508 (16)
H17B0.43660.58650.76880.055*0.508 (16)
H17C0.43380.77390.71240.055*0.508 (16)
C180.34977 (17)0.4544 (5)0.50338 (16)0.0402 (10)
H18A0.30770.39950.51860.060*
H18B0.36650.34220.47660.060*
H18C0.33310.58160.47320.060*
C190.24443 (18)0.1028 (5)0.69328 (16)0.0354 (9)
H19A0.20090.01740.69590.053*
H19B0.22890.25330.68230.053*
H19C0.28440.09640.73890.053*
C200.04498 (18)0.5103 (5)0.61525 (16)0.0369 (9)
H20A0.00010.60110.60860.055*
H20B0.02930.36110.60210.055*
H20C0.07610.51530.66500.055*
N1S0.8447 (2)1.2338 (7)0.60132 (18)0.0753 (11)
C1S0.8400 (2)1.4178 (7)0.6339 (2)0.0493 (11)
H1S0.87341.53170.63150.059*
C2S0.7904 (3)1.4516 (8)0.6701 (2)0.0700 (14)
H2S0.78961.58570.69310.084*
C3S0.7421 (3)1.2933 (12)0.6732 (3)0.106 (3)
H3S0.70681.31600.69850.127*
C4S0.7433 (3)1.1008 (11)0.6405 (4)0.116 (3)
H4S0.70970.98700.64260.139*
C5S0.7947 (4)1.0789 (8)0.6046 (2)0.0905 (19)
H5S0.79540.94690.58030.109*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0412 (17)0.0558 (19)0.0609 (19)0.0266 (16)0.0150 (15)0.0020 (16)
O40.0456 (16)0.0490 (17)0.0486 (18)0.0101 (13)0.0121 (14)0.0072 (14)
C10.033 (2)0.025 (2)0.034 (2)0.0012 (18)0.0014 (18)0.0067 (18)
C2A0.021 (5)0.020 (5)0.033 (6)0.003 (4)0.005 (4)0.004 (4)
C3A0.037 (8)0.030 (8)0.033 (6)0.001 (5)0.004 (5)0.016 (6)
C2B0.035 (6)0.038 (7)0.032 (5)0.006 (5)0.015 (4)0.003 (5)
C3B0.026 (7)0.033 (9)0.030 (6)0.015 (5)0.003 (6)0.016 (7)
C40.035 (2)0.036 (2)0.040 (2)0.0065 (19)0.013 (2)0.0054 (19)
C50.0262 (19)0.032 (2)0.035 (2)0.0069 (18)0.0085 (17)0.0086 (18)
C60.032 (2)0.022 (2)0.032 (2)0.0024 (16)0.0075 (16)0.0001 (16)
C70.040 (2)0.028 (2)0.025 (2)0.0039 (18)0.0041 (17)0.0013 (16)
C80.029 (2)0.029 (2)0.032 (2)0.0035 (18)0.0059 (16)0.0004 (17)
C90.0325 (19)0.023 (2)0.0253 (19)0.0005 (18)0.0051 (16)0.0029 (16)
C100.033 (2)0.031 (2)0.031 (2)0.0004 (18)0.0075 (17)0.0019 (17)
C110.027 (2)0.030 (2)0.029 (2)0.0012 (17)0.0059 (16)0.0057 (16)
C120.032 (2)0.032 (2)0.030 (2)0.0031 (18)0.0085 (16)0.0036 (17)
C130.027 (2)0.031 (2)0.0242 (19)0.0053 (18)0.0028 (15)0.0035 (16)
C140.031 (2)0.035 (2)0.031 (2)0.0076 (18)0.0080 (17)0.0011 (17)
C150.031 (2)0.037 (2)0.031 (2)0.0049 (19)0.0079 (17)0.0034 (15)
C160.052 (2)0.040 (2)0.054 (3)0.005 (2)0.016 (2)0.003 (2)
C17B0.049 (6)0.059 (9)0.023 (6)0.016 (6)0.015 (5)0.013 (5)
C17A0.037 (5)0.045 (7)0.032 (6)0.011 (5)0.017 (5)0.005 (5)
C180.035 (2)0.048 (2)0.034 (2)0.0042 (19)0.0050 (18)0.0006 (18)
C190.044 (2)0.031 (2)0.030 (2)0.0047 (18)0.0085 (17)0.0005 (16)
C200.038 (2)0.038 (2)0.031 (2)0.0050 (19)0.0058 (17)0.0015 (17)
N1S0.098 (3)0.070 (3)0.062 (3)0.016 (3)0.030 (2)0.013 (2)
C1S0.037 (2)0.052 (3)0.049 (3)0.007 (2)0.000 (2)0.000 (2)
C2S0.084 (4)0.089 (4)0.033 (3)0.043 (3)0.012 (3)0.004 (2)
C3S0.060 (4)0.174 (7)0.098 (5)0.050 (5)0.046 (4)0.103 (5)
C4S0.049 (4)0.127 (6)0.128 (6)0.045 (4)0.037 (4)0.096 (5)
C5S0.137 (6)0.042 (3)0.056 (3)0.025 (4)0.026 (3)0.002 (3)
Geometric parameters (Å, º) top
O3—C3A1.351 (14)C13—C141.358 (4)
O3—C3B1.489 (13)C13—C201.500 (4)
O3—H3O0.82 (2)C14—C151.429 (4)
O4—C41.225 (4)C14—H140.9500
C1—C17A1.423 (11)C15—C15i1.346 (6)
C1—C2B1.458 (9)C15—H150.9500
C1—C161.501 (4)C16—H16A0.9800
C1—C61.539 (4)C16—H16B0.9800
C1—C17B1.622 (11)C16—H16C0.9800
C1—C2A1.641 (11)C17B—H17D0.9800
C2A—C3A1.532 (19)C17B—H17E0.9800
C2A—H2A0.9900C17B—H17F0.9800
C2A—H2B0.9900C17A—H17A0.9800
C3A—C41.468 (13)C17A—H17B0.9800
C3A—H3A1.0000C17A—H17C0.9800
C2B—C3B1.45 (2)C18—H18A0.9800
C2B—H2C0.9900C18—H18B0.9800
C2B—H2D0.9900C18—H18C0.9800
C3B—C41.594 (13)C19—H19A0.9800
C3B—H3B1.0000C19—H19B0.9800
C4—C51.457 (4)C19—H19C0.9800
C5—C61.345 (4)C20—H20A0.9800
C5—C181.511 (4)C20—H20B0.9800
C6—C71.465 (4)C20—H20C0.9800
C7—C81.335 (4)N1S—C1S1.325 (4)
C7—H70.9500N1S—C5S1.351 (5)
C8—C91.442 (4)C1S—C2S1.345 (5)
C8—H80.9500C1S—H1S0.9500
C9—C101.359 (4)C2S—C3S1.343 (6)
C9—C191.504 (4)C2S—H2S0.9500
C10—C111.431 (4)C3S—C4S1.360 (6)
C10—H100.9500C3S—H3S0.9500
C11—C121.355 (4)C4S—C5S1.359 (6)
C11—H110.9500C4S—H4S0.9500
C12—C131.426 (4)C5S—H5S0.9500
C12—H120.9500
C3A—O3—H3O102 (5)C12—C11—H11117.9
C3B—O3—H3O126 (4)C10—C11—H11117.9
C17A—C1—C2B77.3 (5)C11—C12—C13125.6 (3)
C17A—C1—C16121.4 (6)C11—C12—H12117.2
C2B—C1—C16120.9 (6)C13—C12—H12117.2
C17A—C1—C6111.5 (5)C14—C13—C12119.1 (3)
C2B—C1—C6112.7 (4)C14—C13—C20122.6 (3)
C16—C1—C6109.7 (3)C12—C13—C20118.2 (3)
C2B—C1—C17B103.9 (5)C13—C14—C15128.5 (3)
C16—C1—C17B97.1 (6)C13—C14—H14115.7
C6—C1—C17B110.9 (5)C15—C14—H14115.7
C17A—C1—C2A109.1 (5)C15i—C15—C14124.1 (4)
C16—C1—C2A96.4 (5)C15i—C15—H15118.0
C6—C1—C2A106.9 (4)C14—C15—H15118.0
C17B—C1—C2A132.4 (5)C1—C16—H16A109.5
C3A—C2A—C1112.5 (10)C1—C16—H16B109.5
C3A—C2A—H2A109.1H16A—C16—H16B109.5
C1—C2A—H2A109.1C1—C16—H16C109.5
C3A—C2A—H2B109.1H16A—C16—H16C109.5
C1—C2A—H2B109.1H16B—C16—H16C109.5
H2A—C2A—H2B107.8C1—C17B—H17D109.5
O3—C3A—C4119.3 (10)C1—C17B—H17E109.5
O3—C3A—C2A104.4 (12)H17D—C17B—H17E109.5
C4—C3A—C2A102.6 (11)C1—C17B—H17F109.5
O3—C3A—H3A110.0H17D—C17B—H17F109.5
C4—C3A—H3A110.0H17E—C17B—H17F109.5
C2A—C3A—H3A110.0C1—C17A—H17A109.5
C3B—C2B—C1110.4 (13)C1—C17A—H17B109.5
C3B—C2B—H2C109.6C1—C17A—H17C109.5
C1—C2B—H2C109.6C5—C18—H18A109.5
C3B—C2B—H2D109.6C5—C18—H18B109.5
C1—C2B—H2D109.6H18A—C18—H18B109.5
H2C—C2B—H2D108.1C5—C18—H18C109.5
C2B—C3B—O3116.0 (12)H18A—C18—H18C109.5
C2B—C3B—C4111.8 (11)H18B—C18—H18C109.5
O3—C3B—C4104.2 (9)C9—C19—H19A109.5
C2B—C3B—H3B108.2C9—C19—H19B109.5
O3—C3B—H3B108.2H19A—C19—H19B109.5
C4—C3B—H3B108.2C9—C19—H19C109.5
O4—C4—C5122.6 (3)H19A—C19—H19C109.5
O4—C4—C3A113.2 (6)H19B—C19—H19C109.5
C5—C4—C3A121.8 (6)C13—C20—H20A109.5
O4—C4—C3B123.5 (6)C13—C20—H20B109.5
C5—C4—C3B113.1 (5)H20A—C20—H20B109.5
C6—C5—C4120.7 (3)C13—C20—H20C109.5
C6—C5—C18124.3 (3)H20A—C20—H20C109.5
C4—C5—C18114.8 (3)H20B—C20—H20C109.5
C5—C6—C7122.9 (3)C1S—N1S—C5S116.1 (4)
C5—C6—C1123.1 (3)N1S—C1S—C2S123.4 (4)
C7—C6—C1113.9 (3)N1S—C1S—H1S118.3
C8—C7—C6128.9 (3)C2S—C1S—H1S118.3
C8—C7—H7115.6C3S—C2S—C1S119.1 (5)
C6—C7—H7115.6C3S—C2S—H2S120.5
C7—C8—C9125.5 (3)C1S—C2S—H2S120.5
C7—C8—H8117.2C2S—C3S—C4S120.7 (6)
C9—C8—H8117.2C2S—C3S—H3S119.7
C10—C9—C8119.7 (3)C4S—C3S—H3S119.7
C10—C9—C19122.3 (3)C5S—C4S—C3S116.9 (6)
C8—C9—C19117.9 (3)C5S—C4S—H4S121.6
C9—C10—C11126.8 (3)C3S—C4S—H4S121.6
C9—C10—H10116.6N1S—C5S—C4S123.8 (5)
C11—C10—H10116.6N1S—C5S—H5S118.1
C12—C11—C10124.3 (3)C4S—C5S—H5S118.1
C17A—C1—C2A—C3A71.1 (14)C3B—C4—C5—C18169.7 (8)
C2B—C1—C2A—C3A56.3 (12)C4—C5—C6—C7171.5 (3)
C16—C1—C2A—C3A162.5 (10)C18—C5—C6—C73.5 (5)
C6—C1—C2A—C3A49.6 (12)C4—C5—C6—C14.6 (5)
C17B—C1—C2A—C3A91.7 (14)C18—C5—C6—C1179.5 (3)
C3B—O3—C3A—C483 (2)C17A—C1—C6—C5106.0 (7)
C3B—O3—C3A—C2A30.3 (17)C2B—C1—C6—C521.3 (9)
C1—C2A—C3A—O3170.8 (7)C16—C1—C6—C5116.6 (4)
C1—C2A—C3A—C464.2 (14)C17B—C1—C6—C5137.3 (7)
C17A—C1—C2B—C3B157.3 (16)C2A—C1—C6—C513.1 (6)
C16—C1—C2B—C3B83.6 (12)C17A—C1—C6—C770.3 (7)
C6—C1—C2B—C3B49.0 (16)C2B—C1—C6—C7155.1 (8)
C17B—C1—C2B—C3B169.1 (15)C16—C1—C6—C767.0 (4)
C2A—C1—C2B—C3B37.0 (13)C17B—C1—C6—C739.1 (7)
C1—C2B—C3B—O3180.0 (6)C2A—C1—C6—C7170.5 (6)
C1—C2B—C3B—C460.8 (19)C5—C6—C7—C848.9 (5)
C3A—O3—C3B—C2B68 (2)C1—C6—C7—C8134.6 (3)
C3A—O3—C3B—C455.4 (17)C6—C7—C8—C9174.2 (3)
O3—C3A—C4—O435.5 (14)C7—C8—C9—C10178.8 (3)
C2A—C3A—C4—O4150.2 (9)C7—C8—C9—C191.1 (5)
O3—C3A—C4—C5161.8 (8)C8—C9—C10—C11174.1 (3)
C2A—C3A—C4—C547.1 (15)C19—C9—C10—C113.5 (5)
O3—C3A—C4—C3B83 (2)C9—C10—C11—C12177.8 (3)
C2A—C3A—C4—C3B31.4 (18)C10—C11—C12—C13177.6 (3)
C2B—C3B—C4—O4146.9 (11)C11—C12—C13—C14179.7 (3)
O3—C3B—C4—O420.9 (14)C11—C12—C13—C201.3 (5)
C2B—C3B—C4—C543.3 (17)C12—C13—C14—C15177.4 (3)
O3—C3B—C4—C5169.3 (7)C20—C13—C14—C151.7 (5)
C2B—C3B—C4—C3A72 (2)C13—C14—C15—C15i178.1 (4)
O3—C3B—C4—C3A54.1 (17)C5S—N1S—C1S—C2S1.8 (6)
O4—C4—C5—C6175.3 (3)N1S—C1S—C2S—C3S0.9 (6)
C3A—C4—C5—C614.2 (9)C1S—C2S—C3S—C4S0.2 (7)
C3B—C4—C5—C614.8 (8)C2S—C3S—C4S—C5S0.6 (8)
O4—C4—C5—C180.2 (5)C1S—N1S—C5S—C4S2.2 (7)
C3A—C4—C5—C18161.3 (8)C3S—C4S—C5S—N1S1.6 (8)
Symmetry code: (i) x, y2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O4ii0.82 (2)2.03 (3)2.822 (4)161 (6)
C4S—H4S···O30.952.393.179 (6)140
Symmetry code: (ii) x+1, y+2, z+1.
(AXT-un) top
Crystal data top
C40H52O4Z = 1
Mr = 596.82F(000) = 324
Triclinic, P1Dx = 1.080 Mg m3
Hall symbol: -P1Mo Kα radiation, λ = 0.71073 Å
a = 8.5371 (10) ÅCell parameters from 1583 reflections
b = 8.6632 (11) Åθ = 2.4–23.8°
c = 13.2984 (16) ŵ = 0.07 mm1
α = 95.145 (2)°T = 100 K
β = 107.409 (2)°Plate, red
γ = 98.765 (2)°0.60 × 0.30 × 0.05 mm
V = 917.93 (19) Å3
Data collection top
CCD area detector
diffractometer
1991 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.050
Graphite monochromatorθmax = 25.0°, θmin = 1.6°
phi and ω scansh = 910
4780 measured reflectionsk = 1010
3188 independent reflectionsl = 158
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 0.84 w = 1/[σ2(Fo2) + (0.1154P)2]
where P = (Fo2 + 2Fc2)/3
3188 reflections(Δ/σ)max = 0.007
245 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C40H52O4γ = 98.765 (2)°
Mr = 596.82V = 917.93 (19) Å3
Triclinic, P1Z = 1
a = 8.5371 (10) ÅMo Kα radiation
b = 8.6632 (11) ŵ = 0.07 mm1
c = 13.2984 (16) ÅT = 100 K
α = 95.145 (2)°0.60 × 0.30 × 0.05 mm
β = 107.409 (2)°
Data collection top
CCD area detector
diffractometer
1991 reflections with I > 2σ(I)
4780 measured reflectionsRint = 0.050
3188 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.163H-atom parameters constrained
S = 0.84Δρmax = 0.20 e Å3
3188 reflectionsΔρmin = 0.15 e Å3
245 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)
O30.7363 (3)0.4422 (3)0.12625 (14)0.1312 (8)
H30.63450.45310.16110.197*
O40.4814 (2)0.3426 (2)0.08299 (14)0.1174 (7)
C10.9415 (2)0.2241 (2)0.15184 (17)0.0658 (6)
C20.9276 (10)0.2806 (12)0.0390 (6)0.0825 (19)0.601 (14)
H2A1.01910.33830.03840.099*0.601 (14)
H2B0.93980.18870.00080.099*0.601 (14)
C2B0.8855 (14)0.3571 (16)0.0537 (9)0.075 (3)0.399 (14)
H2C0.98580.37810.03610.091*0.399 (14)
H2D0.83420.45510.07360.091*0.399 (14)
C30.7613 (11)0.3878 (12)0.0177 (7)0.0791 (19)0.601 (14)
H3A0.75440.48210.02010.095*0.601 (14)
C3B0.7639 (18)0.3190 (19)0.0435 (10)0.083 (3)0.399 (14)
H3B0.81060.21700.06280.099*0.399 (14)
C40.6155 (3)0.3033 (3)0.01260 (18)0.0775 (6)
C50.6364 (2)0.2023 (2)0.08680 (16)0.0636 (5)
C60.7885 (2)0.1593 (2)0.16157 (15)0.0542 (5)
C70.8173 (2)0.0504 (2)0.25864 (15)0.0559 (5)
H70.87340.08210.32440.067*
C80.7712 (2)0.0903 (2)0.26249 (15)0.0564 (5)
H80.71430.12000.19620.068*
C90.7982 (2)0.20208 (19)0.35634 (14)0.0516 (5)
C100.7351 (2)0.3359 (2)0.34562 (15)0.0568 (5)
H100.68360.35380.27490.068*
C110.7373 (2)0.4529 (2)0.42864 (16)0.0571 (5)
H110.79270.44040.50010.069*
C120.6654 (2)0.58045 (19)0.41173 (16)0.0565 (5)
H120.62030.59530.33950.068*
C130.6493 (2)0.69649 (19)0.49042 (15)0.0553 (5)
C140.5691 (2)0.8153 (2)0.45675 (16)0.0598 (5)
H140.52960.81480.38190.072*
C150.5372 (2)0.94110 (19)0.52032 (17)0.0615 (5)
H150.57000.94200.59530.074*
C161.1033 (8)0.0958 (10)0.1987 (9)0.107 (3)0.601 (14)
H16A1.19550.13310.18040.161*0.601 (14)
H16B1.13150.07550.27630.161*0.601 (14)
H16C1.08490.00170.16880.161*0.601 (14)
C16B1.0580 (15)0.0836 (14)0.1310 (14)0.108 (4)0.399 (14)
H16D1.15410.12020.11780.163*0.399 (14)
H16E1.09720.00150.19330.163*0.399 (14)
H16F0.99630.04020.06870.163*0.399 (14)
C170.9633 (11)0.3615 (10)0.2214 (7)0.088 (2)0.601 (14)
H17A0.97310.32180.29480.131*0.601 (14)
H17B1.06450.40110.22040.131*0.601 (14)
H17C0.86590.44720.19230.131*0.601 (14)
C17B1.0301 (16)0.2869 (17)0.2475 (10)0.098 (3)0.399 (14)
H17D0.94900.35410.27140.147*0.399 (14)
H17E1.09220.19930.30420.147*0.399 (14)
H17F1.10810.34930.23090.147*0.399 (14)
C180.4767 (3)0.1584 (3)0.0981 (2)0.0916 (8)
H18A0.49230.12520.17350.137*
H18B0.38540.25000.07050.137*
H18C0.44920.07150.05780.137*
C190.8918 (2)0.1632 (2)0.46263 (15)0.0626 (5)
H19A0.82920.06800.47730.094*
H19B0.90540.25140.51800.094*
H19C1.00210.14480.46220.094*
C200.7194 (3)0.6800 (2)0.60621 (16)0.0679 (6)
H20A0.68720.75930.64950.102*
H20B0.84160.69580.62680.102*
H20C0.67510.57420.61770.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.1568 (18)0.1489 (17)0.0791 (12)0.0517 (15)0.0280 (12)0.0362 (12)
O40.1048 (13)0.1320 (15)0.0840 (12)0.0324 (12)0.0108 (11)0.0218 (11)
C10.0601 (12)0.0645 (12)0.0738 (13)0.0226 (10)0.0223 (10)0.0076 (10)
C20.089 (4)0.082 (5)0.086 (3)0.029 (4)0.039 (3)0.002 (3)
C2B0.076 (5)0.073 (6)0.080 (5)0.028 (5)0.027 (4)0.008 (5)
C30.090 (4)0.080 (5)0.063 (4)0.023 (4)0.021 (3)0.015 (3)
C3B0.104 (6)0.082 (7)0.061 (6)0.013 (6)0.031 (5)0.006 (5)
C40.0812 (15)0.0741 (14)0.0661 (14)0.0163 (12)0.0094 (12)0.0019 (11)
C50.0632 (12)0.0555 (11)0.0696 (13)0.0171 (9)0.0166 (10)0.0012 (10)
C60.0582 (11)0.0458 (10)0.0609 (11)0.0182 (8)0.0196 (9)0.0038 (8)
C70.0556 (10)0.0510 (10)0.0621 (11)0.0188 (8)0.0174 (9)0.0028 (9)
C80.0566 (11)0.0526 (11)0.0596 (11)0.0200 (8)0.0147 (9)0.0017 (9)
C90.0484 (9)0.0461 (10)0.0610 (11)0.0173 (8)0.0153 (8)0.0040 (8)
C100.0572 (10)0.0496 (10)0.0605 (11)0.0190 (8)0.0117 (9)0.0016 (9)
C110.0507 (10)0.0505 (10)0.0663 (12)0.0168 (8)0.0117 (9)0.0005 (9)
C120.0522 (10)0.0463 (10)0.0678 (12)0.0151 (8)0.0134 (9)0.0019 (9)
C130.0476 (9)0.0430 (10)0.0741 (13)0.0101 (8)0.0188 (9)0.0016 (9)
C140.0567 (11)0.0481 (10)0.0782 (13)0.0172 (8)0.0244 (10)0.0042 (9)
C150.0564 (11)0.0476 (11)0.0820 (14)0.0150 (8)0.0238 (10)0.0014 (10)
C160.064 (3)0.116 (4)0.132 (6)0.006 (3)0.037 (4)0.034 (5)
C16B0.074 (6)0.129 (6)0.120 (9)0.003 (5)0.044 (6)0.013 (8)
C170.102 (5)0.083 (5)0.085 (4)0.053 (3)0.024 (3)0.009 (3)
C17B0.086 (7)0.096 (8)0.108 (7)0.059 (6)0.011 (5)0.005 (6)
C180.0608 (13)0.0954 (17)0.1093 (19)0.0247 (12)0.0148 (13)0.0083 (15)
C190.0645 (12)0.0547 (11)0.0668 (12)0.0238 (9)0.0135 (10)0.0029 (9)
C200.0674 (12)0.0597 (12)0.0766 (14)0.0200 (10)0.0214 (11)0.0020 (10)
Geometric parameters (Å, º) top
O3—C3B1.401 (12)C10—H100.9500
O3—C31.419 (8)C11—C121.348 (2)
O3—H30.8400C11—H110.9500
O4—C41.219 (3)C12—C131.437 (2)
C1—C17B1.470 (12)C12—H120.9500
C1—C21.500 (7)C13—C141.357 (2)
C1—C61.533 (2)C13—C201.505 (3)
C1—C16B1.551 (11)C14—C151.428 (2)
C1—C161.557 (7)C14—H140.9500
C1—C2B1.565 (10)C15—C15i1.352 (3)
C1—C171.571 (8)C15—H150.9500
C2—C31.509 (16)C16—H16A0.9800
C2—H2A0.9900C16—H16B0.9800
C2—H2B0.9900C16—H16C0.9800
C2B—C3B1.49 (2)C16B—H16D0.9800
C2B—H2C0.9900C16B—H16E0.9800
C2B—H2D0.9900C16B—H16F0.9800
C3—C41.552 (9)C17—H17A0.9800
C3—H3A1.0000C17—H17B0.9800
C3B—C41.465 (14)C17—H17C0.9800
C3B—H3B1.0000C17B—H17D0.9800
C4—C51.466 (3)C17B—H17E0.9800
C5—C61.351 (2)C17B—H17F0.9800
C5—C181.516 (3)C18—H18A0.9800
C6—C71.462 (2)C18—H18B0.9800
C7—C81.338 (2)C18—H18C0.9800
C7—H70.9500C19—H19A0.9800
C8—C91.446 (2)C19—H19B0.9800
C8—H80.9500C19—H19C0.9800
C9—C101.352 (2)C20—H20A0.9800
C9—C191.497 (3)C20—H20B0.9800
C10—C111.424 (2)C20—H20C0.9800
C3B—O3—H3104.7C7—C8—H8116.4
C3—O3—H3109.5C9—C8—H8116.4
C17B—C1—C2126.7 (5)C10—C9—C8119.16 (17)
C17B—C1—C6113.3 (5)C10—C9—C19122.26 (16)
C2—C1—C6113.1 (3)C8—C9—C19118.57 (15)
C17B—C1—C16B110.3 (6)C9—C10—C11127.21 (18)
C2—C1—C16B80.4 (4)C9—C10—H10116.4
C6—C1—C16B105.7 (5)C11—C10—H10116.4
C17B—C1—C1678.5 (5)C12—C11—C10123.77 (18)
C2—C1—C16107.4 (4)C12—C11—H11118.1
C6—C1—C16110.9 (3)C10—C11—H11118.1
C17B—C1—C2B109.2 (5)C11—C12—C13127.41 (19)
C6—C1—C2B109.3 (4)C11—C12—H12116.3
C16B—C1—C2B109.0 (5)C13—C12—H12116.3
C16—C1—C2B131.3 (5)C14—C13—C12118.37 (18)
C2—C1—C17110.8 (4)C14—C13—C20122.84 (17)
C6—C1—C17107.5 (3)C12—C13—C20118.78 (16)
C16B—C1—C17136.4 (5)C13—C14—C15127.81 (19)
C16—C1—C17106.9 (4)C13—C14—H14116.1
C2B—C1—C1785.7 (4)C15—C14—H14116.1
C1—C2—C3110.9 (8)C15i—C15—C14123.6 (2)
C1—C2—H2A109.5C15i—C15—H15118.2
C3—C2—H2A109.5C14—C15—H15118.2
C1—C2—H2B109.5C1—C16—H16A109.5
C3—C2—H2B109.5C1—C16—H16B109.5
H2A—C2—H2B108.0C1—C16—H16C109.5
C3B—C2B—C1114.2 (11)C1—C16B—H16D109.5
C3B—C2B—H2C108.7C1—C16B—H16E109.5
C1—C2B—H2C108.7H16D—C16B—H16E109.5
C3B—C2B—H2D108.7C1—C16B—H16F109.5
C1—C2B—H2D108.7H16D—C16B—H16F109.5
H2C—C2B—H2D107.6H16E—C16B—H16F109.5
O3—C3—C2114.3 (8)C1—C17—H17A109.5
O3—C3—C4107.9 (6)C1—C17—H17B109.5
C2—C3—C4110.5 (7)C1—C17—H17C109.5
O3—C3—H3A107.9C1—C17B—H17D109.5
C2—C3—H3A107.9C1—C17B—H17E109.5
C4—C3—H3A107.9H17D—C17B—H17E109.5
O3—C3B—C4114.0 (10)C1—C17B—H17F109.5
O3—C3B—C2B107.6 (13)H17D—C17B—H17F109.5
C4—C3B—C2B104.7 (11)H17E—C17B—H17F109.5
O3—C3B—H3B110.1C5—C18—H18A109.5
C4—C3B—H3B110.1C5—C18—H18B109.5
C2B—C3B—H3B110.1H18A—C18—H18B109.5
O4—C4—C3B116.2 (5)C5—C18—H18C109.5
O4—C4—C5122.6 (2)H18A—C18—H18C109.5
C3B—C4—C5118.7 (5)H18B—C18—H18C109.5
O4—C4—C3118.9 (3)C9—C19—H19A109.5
C5—C4—C3117.5 (3)C9—C19—H19B109.5
C6—C5—C4120.33 (18)H19A—C19—H19B109.5
C6—C5—C18124.77 (18)C9—C19—H19C109.5
C4—C5—C18114.86 (19)H19A—C19—H19C109.5
C5—C6—C7122.15 (16)H19B—C19—H19C109.5
C5—C6—C1122.43 (16)C13—C20—H20A109.5
C7—C6—C1115.41 (16)C13—C20—H20B109.5
C8—C7—C6125.40 (18)H20A—C20—H20B109.5
C8—C7—H7117.3C13—C20—H20C109.5
C6—C7—H7117.3H20A—C20—H20C109.5
C7—C8—C9127.25 (18)H20B—C20—H20C109.5
C17B—C1—C2—C399.8 (12)C3—C4—C5—C613.4 (6)
C6—C1—C2—C349.0 (10)O4—C4—C5—C183.5 (3)
C16B—C1—C2—C3152.0 (11)C3B—C4—C5—C18164.6 (8)
C16—C1—C2—C3171.7 (10)C3—C4—C5—C18164.6 (5)
C2B—C1—C2—C339.5 (11)C4—C5—C6—C7175.87 (18)
C17—C1—C2—C371.8 (10)C18—C5—C6—C76.4 (3)
C17B—C1—C2B—C3B167.8 (15)C4—C5—C6—C15.6 (3)
C2—C1—C2B—C3B59.8 (14)C18—C5—C6—C1172.1 (2)
C6—C1—C2B—C3B43.3 (14)C17B—C1—C6—C5129.2 (7)
C16B—C1—C2B—C3B71.7 (15)C2—C1—C6—C523.9 (5)
C16—C1—C2B—C3B100.8 (14)C16B—C1—C6—C5109.9 (7)
C17—C1—C2B—C3B150.4 (14)C16—C1—C6—C5144.6 (5)
C3B—O3—C3—C261.8 (19)C2B—C1—C6—C57.2 (7)
C3B—O3—C3—C461.7 (16)C17—C1—C6—C598.8 (4)
C1—C2—C3—O3178.0 (4)C17B—C1—C6—C749.4 (7)
C1—C2—C3—C456.0 (12)C2—C1—C6—C7157.5 (5)
C3—O3—C3B—C476.3 (17)C16B—C1—C6—C771.4 (7)
C3—O3—C3B—C2B39.4 (17)C16—C1—C6—C736.8 (6)
C1—C2B—C3B—O3175.3 (7)C2B—C1—C6—C7171.4 (6)
C1—C2B—C3B—C463.1 (17)C17—C1—C6—C779.8 (4)
O3—C3B—C4—O430.5 (14)C5—C6—C7—C850.4 (3)
C2B—C3B—C4—O4147.9 (9)C1—C6—C7—C8131.0 (2)
O3—C3B—C4—C5167.1 (7)C6—C7—C8—C9179.43 (17)
C2B—C3B—C4—C549.8 (15)C7—C8—C9—C10176.63 (18)
O3—C3B—C4—C372.2 (16)C7—C8—C9—C191.8 (3)
C2B—C3B—C4—C345.2 (15)C8—C9—C10—C11174.64 (17)
O3—C3—C4—O427.2 (9)C19—C9—C10—C113.7 (3)
C2—C3—C4—O4152.9 (7)C9—C10—C11—C12177.12 (17)
O3—C3—C4—C3B64.5 (15)C10—C11—C12—C13174.24 (17)
C2—C3—C4—C3B61.2 (16)C11—C12—C13—C14178.72 (17)
O3—C3—C4—C5164.4 (4)C11—C12—C13—C200.4 (3)
C2—C3—C4—C538.6 (11)C12—C13—C14—C15179.16 (16)
O4—C4—C5—C6178.6 (2)C20—C13—C14—C150.1 (3)
C3B—C4—C5—C617.5 (8)C13—C14—C15—C15i176.8 (2)
Symmetry code: (i) x+1, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O40.842.172.653 (3)116
C10—H10···O4ii0.952.503.439 (3)168
Symmetry code: (ii) x+1, y, z.
(canth-100K) top
Crystal data top
C40H52O2Z = 2
Mr = 564.82F(000) = 616
Triclinic, P1Dx = 1.102 Mg m3
Hall symbol: -P1Mo Kα radiation, λ = 0.71073 Å
a = 8.5068 (9) ÅCell parameters from 1827 reflections
b = 14.2208 (16) Åθ = 2.5–25.9°
c = 15.5262 (17) ŵ = 0.07 mm1
α = 105.870 (2)°T = 100 K
β = 95.227 (2)°Block, dark red
γ = 106.512 (2)°0.50 × 0.35 × 0.30 mm
V = 1702.9 (3) Å3
Data collection top
CCD area detector
diffractometer
3448 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 26.4°, θmin = 1.4°
phi and ω scansh = 910
9834 measured reflectionsk = 1715
6781 independent reflectionsl = 1914
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 0.84 w = 1/[σ2(Fo2) + (0.0443P)2]
where P = (Fo2 + 2Fc2)/3
6779 reflections(Δ/σ)max < 0.001
419 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C40H52O2γ = 106.512 (2)°
Mr = 564.82V = 1702.9 (3) Å3
Triclinic, P1Z = 2
a = 8.5068 (9) ÅMo Kα radiation
b = 14.2208 (16) ŵ = 0.07 mm1
c = 15.5262 (17) ÅT = 100 K
α = 105.870 (2)°0.50 × 0.35 × 0.30 mm
β = 95.227 (2)°
Data collection top
CCD area detector
diffractometer
3448 reflections with I > 2σ(I)
9834 measured reflectionsRint = 0.031
6781 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 0.84Δρmax = 0.20 e Å3
6779 reflectionsΔρmin = 0.16 e Å3
419 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)
O40.8012 (2)0.26005 (11)0.13973 (10)0.0726 (5)
O4A1.1199 (2)1.70202 (11)0.63776 (10)0.0799 (6)
C11.0614 (2)0.06461 (16)0.18228 (15)0.0479 (6)
C21.1363 (3)0.15226 (18)0.14428 (16)0.0625 (7)
H2A1.11740.12430.07700.075*
H2B1.25830.18020.16680.075*
C31.0634 (3)0.23881 (17)0.17056 (16)0.0667 (7)
H3A1.10580.28850.13750.080*
H3B1.10140.27580.23660.080*
C40.8778 (3)0.20167 (17)0.14990 (14)0.0540 (6)
C50.7878 (2)0.09463 (15)0.14542 (13)0.0410 (5)
C60.8708 (2)0.02990 (14)0.15827 (12)0.0358 (5)
C70.7841 (2)0.07667 (14)0.15583 (12)0.0347 (5)
H70.82130.09790.20470.042*
C80.6578 (2)0.14661 (14)0.09121 (12)0.0332 (5)
H80.61980.12470.04300.040*
C90.5736 (2)0.25147 (14)0.08747 (12)0.0312 (4)
C100.4425 (2)0.31095 (14)0.01932 (12)0.0323 (5)
H100.41660.28040.02510.039*
C110.3382 (2)0.41443 (13)0.00627 (12)0.0316 (5)
H110.36180.44800.04860.038*
C120.2078 (2)0.46637 (13)0.06347 (12)0.0305 (4)
H120.19110.43200.10640.037*
C130.0911 (2)0.56834 (13)0.07995 (12)0.0291 (4)
C140.0305 (2)0.60802 (13)0.15524 (12)0.0305 (4)
H140.02930.56510.19270.037*
C150.1602 (2)0.70548 (13)0.18581 (13)0.0330 (5)
H150.17000.74860.14810.040*
C161.1275 (3)0.02439 (18)0.14175 (18)0.0742 (8)
H16A1.09210.04970.07540.111*
H16B1.24960.00020.15690.111*
H16C1.08310.08060.16700.111*
C171.1139 (3)0.10177 (16)0.28701 (15)0.0636 (7)
H17A1.05670.04720.31130.095*
H17B1.23480.11790.30320.095*
H17C1.08360.16380.31300.095*
C180.6019 (2)0.06910 (16)0.13239 (15)0.0592 (7)
H18A0.55400.01020.15370.089*
H18B0.57400.12890.16730.089*
H18C0.55630.05150.06760.089*
C190.6332 (2)0.28977 (14)0.16094 (12)0.0382 (5)
H19A0.57330.36370.14650.057*
H19B0.75300.27870.16500.057*
H19C0.61200.25200.21930.057*
C200.1085 (2)0.62449 (14)0.01252 (12)0.0362 (5)
H20A0.02240.69250.03280.054*
H20B0.21900.63310.00790.054*
H20C0.09560.58460.04720.054*
C1A1.4247 (3)1.53115 (16)0.67936 (14)0.0441 (5)
C2A1.5006 (4)1.6155 (3)0.6402 (3)0.0464 (11)0.610 (3)
H2E1.49701.58590.57410.056*0.610 (3)
H2F1.61861.65200.67030.056*0.610 (3)
C3A1.3948 (3)1.69507 (16)0.65704 (17)0.0683 (7)0.610 (3)
H3E1.43631.74320.71990.082*0.610 (3)
H3F1.41921.73650.61510.082*0.610 (3)
C16A1.5184 (4)1.4463 (3)0.6481 (3)0.0493 (11)0.610 (3)
H16D1.63941.48050.66430.074*0.610 (3)
H16E1.48651.41300.58200.074*0.610 (3)
H16F1.48591.39410.67900.074*0.610 (3)
C17A1.4757 (4)1.5686 (3)0.7839 (2)0.0445 (10)0.610 (3)
H17D1.42631.51190.80770.067*0.610 (3)
H17E1.43581.62660.80980.067*0.610 (3)
H17F1.59751.59090.80070.067*0.610 (3)
C2B1.4601 (7)1.6548 (4)0.7119 (4)0.0507 (18)0.390 (3)
H2G1.42021.67350.77020.061*0.390 (3)
H2H1.58241.68880.72480.061*0.390 (3)
C3B1.3948 (3)1.69507 (16)0.65704 (17)0.0683 (7)0.390 (3)
H3G1.43151.67820.59760.082*0.390 (3)
H3H1.42991.77110.68390.082*0.390 (3)
C16B1.4692 (6)1.4996 (5)0.5887 (4)0.058 (2)0.390 (3)
H16G1.59061.52560.59410.087*0.390 (3)
H16H1.41661.52830.54790.087*0.390 (3)
H16I1.43011.42410.56380.087*0.390 (3)
C17B1.4986 (7)1.5040 (5)0.7492 (4)0.0482 (17)0.390 (3)
H17G1.48141.42970.72880.072*0.390 (3)
H17H1.44761.52130.80300.072*0.390 (3)
H17I1.61841.54210.76480.072*0.390 (3)
C4A1.2116 (4)1.65008 (17)0.64499 (14)0.0633 (7)
C5A1.1370 (3)1.54047 (15)0.63926 (13)0.0504 (6)
C6A1.2354 (2)1.48430 (15)0.65311 (12)0.0410 (5)
C7A1.1655 (2)1.37372 (14)0.64427 (13)0.0365 (5)
H7A1.20041.35160.69300.044*
C8A1.0566 (2)1.30270 (14)0.57259 (13)0.0374 (5)
H8A1.02671.32560.52340.045*
C9A0.9792 (2)1.19409 (14)0.56191 (12)0.0342 (5)
C10A0.8587 (2)1.13568 (14)0.48766 (12)0.0359 (5)
H10A0.84241.16750.44270.043*
C11A0.7536 (2)1.03137 (14)0.46974 (13)0.0352 (5)
H11A0.77100.99610.51180.042*
C12A0.6308 (2)0.98059 (14)0.39571 (13)0.0358 (5)
H12A0.62141.01550.35230.043*
C13A0.5129 (2)0.87881 (14)0.37642 (13)0.0348 (5)
C14A0.3971 (2)0.83829 (14)0.29755 (13)0.0358 (5)
H14A0.40230.88100.25960.043*
C15A0.2696 (2)0.74004 (14)0.26506 (13)0.0351 (5)
H15A0.26120.69580.30180.042*
C18A0.9494 (3)1.50239 (17)0.62192 (15)0.0669 (7)
H18D0.90681.49480.55870.100*
H18E0.90911.55220.66330.100*
H18F0.91011.43540.63250.100*
C19A1.0299 (2)1.15310 (14)0.63478 (12)0.0387 (5)
H19D0.97381.07830.61640.058*
H19E0.99831.18650.69150.058*
H19F1.15101.16750.64430.058*
C20A0.5221 (2)0.82230 (14)0.44446 (13)0.0428 (5)
H20D0.42810.75780.42600.064*
H20E0.51710.86560.50460.064*
H20F0.62710.80670.44720.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0933 (13)0.0418 (10)0.0737 (12)0.0191 (10)0.0270 (9)0.0204 (9)
O4A0.1325 (16)0.0372 (10)0.0579 (11)0.0249 (11)0.0244 (10)0.0120 (8)
C10.0338 (12)0.0367 (13)0.0616 (16)0.0006 (10)0.0100 (10)0.0159 (11)
C20.0413 (13)0.0634 (17)0.0697 (18)0.0076 (13)0.0051 (12)0.0306 (14)
C30.0640 (16)0.0423 (15)0.0791 (19)0.0106 (13)0.0219 (13)0.0362 (13)
C40.0671 (16)0.0366 (13)0.0461 (14)0.0089 (12)0.0200 (11)0.0119 (11)
C50.0403 (12)0.0284 (12)0.0425 (13)0.0051 (10)0.0110 (9)0.0050 (10)
C60.0334 (11)0.0284 (11)0.0355 (12)0.0034 (9)0.0059 (9)0.0050 (9)
C70.0287 (11)0.0319 (12)0.0401 (12)0.0094 (9)0.0028 (9)0.0093 (9)
C80.0276 (11)0.0302 (11)0.0392 (12)0.0101 (9)0.0008 (9)0.0081 (9)
C90.0244 (10)0.0286 (11)0.0354 (12)0.0083 (9)0.0018 (9)0.0046 (9)
C100.0288 (10)0.0295 (11)0.0365 (12)0.0104 (9)0.0005 (9)0.0080 (9)
C110.0288 (11)0.0285 (11)0.0344 (12)0.0111 (9)0.0012 (9)0.0052 (9)
C120.0291 (11)0.0264 (11)0.0333 (12)0.0097 (9)0.0021 (9)0.0054 (9)
C130.0282 (10)0.0234 (10)0.0336 (12)0.0103 (9)0.0034 (9)0.0045 (9)
C140.0294 (10)0.0240 (11)0.0359 (12)0.0088 (9)0.0032 (9)0.0065 (9)
C150.0296 (11)0.0253 (11)0.0388 (12)0.0068 (9)0.0030 (9)0.0052 (9)
C160.0312 (13)0.0602 (17)0.123 (2)0.0119 (12)0.0080 (14)0.0215 (16)
C170.0545 (15)0.0450 (15)0.0753 (18)0.0095 (12)0.0243 (12)0.0319 (13)
C180.0451 (14)0.0394 (14)0.0803 (18)0.0177 (12)0.0129 (12)0.0020 (12)
C190.0336 (11)0.0285 (11)0.0428 (13)0.0066 (9)0.0069 (9)0.0042 (9)
C200.0370 (11)0.0281 (11)0.0396 (12)0.0109 (9)0.0021 (9)0.0057 (9)
C1A0.0460 (13)0.0328 (12)0.0386 (13)0.0049 (10)0.0031 (11)0.0075 (10)
C2A0.048 (2)0.038 (2)0.045 (3)0.0007 (18)0.0066 (19)0.0144 (19)
C3A0.095 (2)0.0250 (13)0.0630 (18)0.0088 (14)0.0120 (15)0.0100 (12)
C16A0.039 (2)0.042 (2)0.067 (3)0.0107 (18)0.0140 (18)0.018 (2)
C17A0.036 (2)0.039 (2)0.042 (2)0.0013 (19)0.0073 (17)0.005 (2)
C2B0.041 (3)0.044 (4)0.052 (4)0.006 (3)0.008 (3)0.017 (3)
C3B0.095 (2)0.0250 (13)0.0630 (18)0.0088 (14)0.0120 (15)0.0100 (12)
C16B0.038 (3)0.059 (4)0.069 (5)0.001 (3)0.004 (3)0.025 (4)
C17B0.038 (3)0.041 (4)0.051 (4)0.001 (3)0.006 (3)0.007 (3)
C4A0.110 (2)0.0294 (13)0.0371 (14)0.0141 (15)0.0208 (13)0.0091 (11)
C5A0.0617 (15)0.0275 (12)0.0466 (14)0.0034 (11)0.0224 (11)0.0093 (10)
C6A0.0475 (13)0.0296 (12)0.0321 (12)0.0021 (10)0.0096 (9)0.0086 (9)
C7A0.0346 (11)0.0275 (11)0.0392 (13)0.0022 (9)0.0058 (9)0.0097 (10)
C8A0.0393 (12)0.0284 (12)0.0384 (13)0.0057 (10)0.0051 (10)0.0107 (10)
C9A0.0328 (11)0.0249 (11)0.0367 (12)0.0038 (9)0.0016 (9)0.0051 (9)
C10A0.0388 (12)0.0250 (11)0.0382 (12)0.0056 (10)0.0028 (9)0.0091 (9)
C11A0.0344 (11)0.0238 (11)0.0427 (13)0.0077 (9)0.0003 (9)0.0072 (9)
C12A0.0343 (11)0.0254 (11)0.0390 (12)0.0052 (9)0.0035 (9)0.0046 (9)
C13A0.0313 (11)0.0251 (11)0.0410 (13)0.0062 (9)0.0006 (9)0.0041 (9)
C14A0.0324 (11)0.0274 (11)0.0404 (13)0.0065 (9)0.0012 (9)0.0044 (9)
C15A0.0293 (11)0.0260 (11)0.0435 (13)0.0053 (9)0.0011 (9)0.0062 (9)
C18A0.0643 (16)0.0425 (14)0.0789 (19)0.0169 (13)0.0281 (13)0.0090 (13)
C19A0.0356 (11)0.0271 (11)0.0434 (13)0.0036 (9)0.0073 (9)0.0069 (9)
C20A0.0360 (12)0.0308 (12)0.0505 (14)0.0007 (10)0.0044 (10)0.0099 (10)
Geometric parameters (Å, º) top
O4—C41.225 (2)C1A—C17A1.541 (4)
O4A—C4A1.235 (3)C1A—C2B1.620 (6)
C1—C21.526 (3)C1A—C16A1.620 (4)
C1—C161.532 (3)C2A—C3A1.619 (4)
C1—C61.532 (3)C2A—H2E0.9900
C1—C171.545 (3)C2A—H2F0.9900
C2—C31.507 (3)C3A—C4A1.479 (3)
C2—H2A0.9900C3A—H3E0.9900
C2—H2B0.9900C3A—H3F0.9900
C3—C41.489 (3)C16A—H16D0.9800
C3—H3A0.9900C16A—H16E0.9800
C3—H3B0.9900C16A—H16F0.9800
C4—C51.476 (3)C17A—H17D0.9800
C5—C61.352 (2)C17A—H17E0.9800
C5—C181.500 (3)C17A—H17F0.9800
C6—C71.473 (2)C2B—H2G0.9900
C7—C81.342 (2)C2B—H2H0.9900
C7—H70.9500C16B—H16G0.9800
C8—C91.441 (2)C16B—H16H0.9800
C8—H80.9500C16B—H16I0.9800
C9—C101.356 (2)C17B—H17G0.9800
C9—C191.499 (2)C17B—H17H0.9800
C10—C111.434 (2)C17B—H17I0.9800
C10—H100.9500C4A—C5A1.481 (3)
C11—C121.351 (2)C5A—C6A1.351 (3)
C11—H110.9500C5A—C18A1.505 (3)
C12—C131.444 (2)C6A—C7A1.477 (2)
C12—H120.9500C7A—C8A1.335 (2)
C13—C141.358 (2)C7A—H7A0.9500
C13—C201.501 (2)C8A—C9A1.452 (2)
C14—C151.428 (2)C8A—H8A0.9500
C14—H140.9500C9A—C10A1.359 (2)
C15—C15A1.350 (2)C9A—C19A1.490 (2)
C15—H150.9500C10A—C11A1.432 (2)
C16—H16A0.9800C10A—H10A0.9500
C16—H16B0.9800C11A—C12A1.354 (2)
C16—H16C0.9800C11A—H11A0.9500
C17—H17A0.9800C12A—C13A1.440 (2)
C17—H17B0.9800C12A—H12A0.9500
C17—H17C0.9800C13A—C14A1.369 (2)
C18—H18A0.9800C13A—C20A1.501 (2)
C18—H18B0.9800C14A—C15A1.427 (2)
C18—H18C0.9800C14A—H14A0.9500
C19—H19A0.9800C15A—H15A0.9500
C19—H19B0.9800C18A—H18D0.9800
C19—H19C0.9800C18A—H18E0.9800
C20—H20A0.9800C18A—H18F0.9800
C20—H20B0.9800C19A—H19D0.9800
C20—H20C0.9800C19A—H19E0.9800
C1A—C17B1.401 (6)C19A—H19F0.9800
C1A—C16B1.475 (6)C20A—H20D0.9800
C1A—C2A1.502 (4)C20A—H20E0.9800
C1A—C6A1.525 (3)C20A—H20F0.9800
C2—C1—C16108.47 (19)C6A—C1A—C2B104.7 (3)
C2—C1—C6109.58 (16)C17A—C1A—C2B73.6 (3)
C16—C1—C6111.10 (17)C17B—C1A—C16A63.9 (3)
C2—C1—C17110.09 (17)C16B—C1A—C16A55.5 (2)
C16—C1—C17108.96 (18)C2A—C1A—C16A105.6 (2)
C6—C1—C17108.64 (17)C6A—C1A—C16A112.6 (2)
C3—C2—C1112.97 (19)C17A—C1A—C16A102.7 (2)
C3—C2—H2A109.0C2B—C1A—C16A141.2 (3)
C1—C2—H2A109.0C1A—C2A—C3A108.0 (3)
C3—C2—H2B109.0C1A—C2A—H2E110.1
C1—C2—H2B109.0C3A—C2A—H2E110.1
H2A—C2—H2B107.8C1A—C2A—H2F110.1
C4—C3—C2112.67 (19)C3A—C2A—H2F110.1
C4—C3—H3A109.1H2E—C2A—H2F108.4
C2—C3—H3A109.1C4A—C3A—C2A117.2 (2)
C4—C3—H3B109.1C4A—C3A—H3E108.0
C2—C3—H3B109.1C2A—C3A—H3E108.0
H3A—C3—H3B107.8C4A—C3A—H3F108.0
O4—C4—C5120.6 (2)C2A—C3A—H3F108.0
O4—C4—C3120.5 (2)H3E—C3A—H3F107.2
C5—C4—C3118.87 (19)C1A—C16A—H16D109.5
C6—C5—C4121.29 (18)C1A—C16A—H16E109.5
C6—C5—C18124.62 (18)C1A—C16A—H16F109.5
C4—C5—C18113.96 (18)C1A—C17A—H17D109.5
C5—C6—C7122.41 (17)C1A—C17A—H17E109.5
C5—C6—C1122.16 (18)C1A—C17A—H17F109.5
C7—C6—C1115.32 (16)C1A—C2B—H2G107.7
C8—C7—C6126.25 (17)C1A—C2B—H2H107.7
C8—C7—H7116.9H2G—C2B—H2H107.1
C6—C7—H7116.9C1A—C16B—H16G109.5
C7—C8—C9126.72 (17)C1A—C16B—H16H109.5
C7—C8—H8116.6H16G—C16B—H16H109.5
C9—C8—H8116.6C1A—C16B—H16I109.5
C10—C9—C8119.30 (16)H16G—C16B—H16I109.5
C10—C9—C19122.47 (17)H16H—C16B—H16I109.5
C8—C9—C19118.21 (16)C1A—C17B—H17G109.5
C9—C10—C11127.76 (17)C1A—C17B—H17H109.5
C9—C10—H10116.1H17G—C17B—H17H109.5
C11—C10—H10116.1C1A—C17B—H17I109.5
C12—C11—C10123.02 (17)H17G—C17B—H17I109.5
C12—C11—H11118.5H17H—C17B—H17I109.5
C10—C11—H11118.5O4A—C4A—C3A120.9 (2)
C11—C12—C13127.16 (17)O4A—C4A—C5A119.5 (2)
C11—C12—H12116.4C3A—C4A—C5A119.5 (2)
C13—C12—H12116.4C6A—C5A—C4A120.4 (2)
C14—C13—C12118.19 (16)C6A—C5A—C18A125.12 (19)
C14—C13—C20123.24 (16)C4A—C5A—C18A114.4 (2)
C12—C13—C20118.56 (16)C5A—C6A—C7A121.85 (18)
C13—C14—C15128.83 (17)C5A—C6A—C1A122.18 (19)
C13—C14—H14115.6C7A—C6A—C1A115.97 (17)
C15—C14—H14115.6C8A—C7A—C6A124.57 (17)
C15A—C15—C14123.97 (17)C8A—C7A—H7A117.7
C15A—C15—H15118.0C6A—C7A—H7A117.7
C14—C15—H15118.0C7A—C8A—C9A126.84 (17)
C1—C16—H16A109.5C7A—C8A—H8A116.6
C1—C16—H16B109.5C9A—C8A—H8A116.6
H16A—C16—H16B109.5C10A—C9A—C8A118.27 (16)
C1—C16—H16C109.5C10A—C9A—C19A123.10 (17)
H16A—C16—H16C109.5C8A—C9A—C19A118.56 (16)
H16B—C16—H16C109.5C9A—C10A—C11A127.14 (17)
C1—C17—H17A109.5C9A—C10A—H10A116.4
C1—C17—H17B109.5C11A—C10A—H10A116.4
H17A—C17—H17B109.5C12A—C11A—C10A123.13 (18)
C1—C17—H17C109.5C12A—C11A—H11A118.4
H17A—C17—H17C109.5C10A—C11A—H11A118.4
H17B—C17—H17C109.5C11A—C12A—C13A126.30 (18)
C5—C18—H18A109.5C11A—C12A—H12A116.9
C5—C18—H18B109.5C13A—C12A—H12A116.9
H18A—C18—H18B109.5C14A—C13A—C12A118.76 (17)
C5—C18—H18C109.5C14A—C13A—C20A123.00 (17)
H18A—C18—H18C109.5C12A—C13A—C20A118.24 (16)
H18B—C18—H18C109.5C13A—C14A—C15A128.23 (18)
C9—C19—H19A109.5C13A—C14A—H14A115.9
C9—C19—H19B109.5C15A—C14A—H14A115.9
H19A—C19—H19B109.5C15—C15A—C14A124.59 (18)
C9—C19—H19C109.5C15—C15A—H15A117.7
H19A—C19—H19C109.5C14A—C15A—H15A117.7
H19B—C19—H19C109.5C5A—C18A—H18D109.5
C13—C20—H20A109.5C5A—C18A—H18E109.5
C13—C20—H20B109.5H18D—C18A—H18E109.5
H20A—C20—H20B109.5C5A—C18A—H18F109.5
C13—C20—H20C109.5H18D—C18A—H18F109.5
H20A—C20—H20C109.5H18E—C18A—H18F109.5
H20B—C20—H20C109.5C9A—C19A—H19D109.5
C17B—C1A—C16B117.9 (4)C9A—C19A—H19E109.5
C17B—C1A—C2A128.5 (3)H19D—C19A—H19E109.5
C16B—C1A—C2A62.9 (3)C9A—C19A—H19F109.5
C17B—C1A—C6A115.4 (3)H19D—C19A—H19F109.5
C16B—C1A—C6A99.5 (3)H19E—C19A—H19F109.5
C2A—C1A—C6A114.8 (2)C13A—C20A—H20D109.5
C16B—C1A—C17A149.5 (3)C13A—C20A—H20E109.5
C2A—C1A—C17A111.0 (2)H20D—C20A—H20E109.5
C6A—C1A—C17A109.4 (2)C13A—C20A—H20F109.5
C17B—C1A—C2B109.3 (4)H20D—C20A—H20F109.5
C16B—C1A—C2B108.9 (3)H20E—C20A—H20F109.5
C16—C1—C2—C3172.90 (18)C16A—C1A—C2A—C3A172.2 (2)
C6—C1—C2—C351.5 (2)C1A—C2A—C3A—C4A39.7 (4)
C17—C1—C2—C368.0 (2)C2A—C3A—C4A—O4A164.8 (2)
C1—C2—C3—C451.4 (3)C2A—C3A—C4A—C5A13.7 (3)
C2—C3—C4—O4157.0 (2)O4A—C4A—C5A—C6A175.5 (2)
C2—C3—C4—C525.3 (3)C3A—C4A—C5A—C6A6.0 (3)
O4—C4—C5—C6178.69 (19)O4A—C4A—C5A—C18A1.7 (3)
C3—C4—C5—C61.0 (3)C3A—C4A—C5A—C18A176.8 (2)
O4—C4—C5—C182.8 (3)C4A—C5A—C6A—C7A177.49 (18)
C3—C4—C5—C18174.9 (2)C18A—C5A—C6A—C7A5.6 (3)
C4—C5—C6—C7178.86 (18)C4A—C5A—C6A—C1A2.9 (3)
C18—C5—C6—C73.4 (3)C18A—C5A—C6A—C1A174.0 (2)
C4—C5—C6—C12.8 (3)C17B—C1A—C6A—C5A135.6 (4)
C18—C5—C6—C1172.68 (19)C16B—C1A—C6A—C5A97.2 (3)
C2—C1—C6—C527.7 (3)C2A—C1A—C6A—C5A32.7 (3)
C16—C1—C6—C5147.54 (19)C17A—C1A—C6A—C5A92.8 (3)
C17—C1—C6—C592.6 (2)C2B—C1A—C6A—C5A15.4 (3)
C2—C1—C6—C7155.95 (18)C16A—C1A—C6A—C5A153.7 (2)
C16—C1—C6—C736.1 (2)C17B—C1A—C6A—C7A44.1 (4)
C17—C1—C6—C783.7 (2)C16B—C1A—C6A—C7A83.2 (3)
C5—C6—C7—C848.8 (3)C2A—C1A—C6A—C7A147.6 (2)
C1—C6—C7—C8134.9 (2)C17A—C1A—C6A—C7A86.8 (3)
C6—C7—C8—C9179.07 (17)C2B—C1A—C6A—C7A164.2 (3)
C7—C8—C9—C10176.95 (18)C16A—C1A—C6A—C7A26.7 (3)
C7—C8—C9—C191.7 (3)C5A—C6A—C7A—C8A50.8 (3)
C8—C9—C10—C11176.70 (17)C1A—C6A—C7A—C8A129.6 (2)
C19—C9—C10—C111.9 (3)C6A—C7A—C8A—C9A177.41 (18)
C9—C10—C11—C12178.68 (18)C7A—C8A—C9A—C10A173.64 (19)
C10—C11—C12—C13176.77 (16)C7A—C8A—C9A—C19A3.6 (3)
C11—C12—C13—C14178.91 (18)C8A—C9A—C10A—C11A171.97 (18)
C11—C12—C13—C202.0 (3)C19A—C9A—C10A—C11A5.2 (3)
C12—C13—C14—C15179.39 (16)C9A—C10A—C11A—C12A176.7 (2)
C20—C13—C14—C150.4 (3)C10A—C11A—C12A—C13A175.28 (18)
C13—C14—C15—C15A175.93 (19)C11A—C12A—C13A—C14A179.34 (19)
C17B—C1A—C2A—C3A118.9 (4)C11A—C12A—C13A—C20A1.1 (3)
C16B—C1A—C2A—C3A135.7 (4)C12A—C13A—C14A—C15A179.90 (18)
C6A—C1A—C2A—C3A47.6 (3)C20A—C13A—C14A—C15A0.4 (3)
C17A—C1A—C2A—C3A77.2 (3)C14—C15—C15A—C14A178.35 (17)
C2B—C1A—C2A—C3A39.2 (3)C13A—C14A—C15A—C15179.69 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O4i0.952.583.438 (2)150
Symmetry code: (i) x1, y, z.
(canth-293) top
Crystal data top
C40H52O2Z = 2
Mr = 564.82F(000) = 616
Triclinic, P1Dx = 1.060 Mg m3
Hall symbol: -P1Mo Kα radiation, λ = 0.71073 Å
a = 8.5919 (11) ÅCell parameters from 1488 reflections
b = 14.3168 (18) Åθ = 2.5–21.4°
c = 15.9405 (19) ŵ = 0.06 mm1
α = 105.569 (2)°T = 293 K
β = 96.118 (3)°Block, dark red
γ = 107.024 (2)°0.50 × 0.35 × 0.30 mm
V = 1769.2 (4) Å3
Data collection top
CCD area detector
diffractometer
2591 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 25.0°, θmin = 1.4°
phi and ω scansh = 1010
9285 measured reflectionsk = 1617
6162 independent reflectionsl = 1318
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 0.82 w = 1/[σ2(Fo2) + (0.0587P)2]
where P = (Fo2 + 2Fc2)/3
6162 reflections(Δ/σ)max = 0.001
419 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.09 e Å3
Crystal data top
C40H52O2γ = 107.024 (2)°
Mr = 564.82V = 1769.2 (4) Å3
Triclinic, P1Z = 2
a = 8.5919 (11) ÅMo Kα radiation
b = 14.3168 (18) ŵ = 0.06 mm1
c = 15.9405 (19) ÅT = 293 K
α = 105.569 (2)°0.50 × 0.35 × 0.30 mm
β = 96.118 (3)°
Data collection top
CCD area detector
diffractometer
2591 reflections with I > 2σ(I)
9285 measured reflectionsRint = 0.025
6162 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.137H-atom parameters constrained
S = 0.82Δρmax = 0.18 e Å3
6162 reflectionsΔρmin = 0.09 e Å3
419 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)
O40.7883 (3)0.24981 (16)0.13741 (15)0.1373 (9)
O4A1.1282 (3)1.70598 (15)0.63877 (14)0.1228 (8)
C11.0470 (3)0.0592 (2)0.1824 (2)0.0852 (8)
C21.1216 (4)0.1462 (3)0.1470 (2)0.1199 (11)
H2A1.10680.11800.08170.144*
H2B1.24240.17570.17200.144*
C31.0495 (4)0.2300 (2)0.1676 (2)0.1192 (12)
H3A1.08990.27050.23130.143*
H3B1.08990.27660.13270.143*
C40.8644 (4)0.1929 (2)0.14804 (19)0.0969 (10)
C50.7750 (3)0.0862 (2)0.14470 (16)0.0759 (7)
C60.8580 (3)0.02363 (18)0.15774 (15)0.0659 (7)
C70.7722 (3)0.08266 (18)0.15511 (16)0.0661 (7)
H70.80820.10280.20380.079*
C80.6487 (3)0.15360 (18)0.09098 (15)0.0637 (7)
H80.61290.13230.04300.076*
C90.5630 (3)0.25871 (18)0.08576 (15)0.0576 (6)
C100.4352 (3)0.31776 (17)0.01676 (15)0.0613 (6)
H100.41300.28740.02730.074*
C110.3297 (3)0.42098 (17)0.00270 (15)0.0601 (6)
H110.35150.45470.04410.072*
C120.2009 (3)0.47230 (17)0.06669 (15)0.0579 (6)
H120.18660.43740.10840.070*
C130.0820 (3)0.57396 (17)0.08527 (15)0.0559 (6)
C140.0377 (3)0.61242 (17)0.16005 (15)0.0595 (6)
H140.03400.56910.19620.071*
C150.1687 (3)0.70950 (17)0.19157 (17)0.0660 (7)
H150.18020.75280.15510.079*
C161.1133 (4)0.0278 (2)0.1437 (3)0.1471 (14)
H16A1.07780.05300.07890.221*
H16B1.23490.00210.15960.221*
H16C1.06950.08420.16790.221*
C171.0985 (4)0.0953 (2)0.2844 (2)0.1277 (12)
H17A1.03420.04250.30750.191*
H17B1.21720.10680.30140.191*
H17C1.07670.15960.30920.191*
C180.5894 (3)0.0596 (2)0.1325 (2)0.1129 (11)
H18A0.54320.00110.15380.169*
H18B0.56300.11900.16650.169*
H18C0.54120.04140.06940.169*
C190.6170 (3)0.29690 (17)0.15875 (15)0.0703 (7)
H19A0.55680.37080.14360.106*
H19B0.73670.28490.16600.106*
H19C0.59280.26000.21440.106*
C200.0940 (3)0.63200 (18)0.02075 (15)0.0732 (7)
H20A0.00900.70050.04360.110*
H20B0.20430.63890.01310.110*
H20C0.07660.59450.03670.110*
C1A1.4272 (3)1.5346 (2)0.67757 (19)0.0706 (7)
C2A1.4929 (7)1.6216 (4)0.6392 (5)0.094 (2)0.682 (9)
H2E1.47881.59280.57400.113*0.682 (9)
H2F1.61311.65700.66440.113*0.682 (9)
C3A1.4008 (5)1.6992 (2)0.6604 (3)0.1113 (11)0.682 (9)
H3E1.44301.74230.72350.134*0.682 (9)
H3F1.42821.74510.62350.134*0.682 (9)
C16A1.5112 (6)1.4526 (4)0.6447 (5)0.103 (3)0.682 (9)
H16D1.63161.48660.65470.155*0.682 (9)
H16E1.46731.41670.58110.155*0.682 (9)
H16F1.48761.40290.67760.155*0.682 (9)
C17A1.4787 (6)1.5730 (5)0.7803 (4)0.0867 (19)0.682 (9)
H17D1.42831.51700.80360.130*0.682 (9)
H17E1.44031.63090.80450.130*0.682 (9)
H17F1.60001.59540.79770.130*0.682 (9)
C2B1.4756 (16)1.6527 (11)0.7048 (13)0.114 (6)0.318 (9)
H2G1.46311.67630.76720.136*0.318 (9)
H2H1.59571.68010.70490.136*0.318 (9)
C3B1.4008 (5)1.6992 (2)0.6604 (3)0.1113 (11)0.318 (9)
H3G1.43501.69270.60240.134*0.318 (9)
H3H1.43611.77340.69430.134*0.318 (9)
C16B1.4764 (12)1.4952 (11)0.5887 (8)0.110 (5)0.318 (9)
H16G1.59761.52090.59620.165*0.318 (9)
H16H1.42651.51970.54450.165*0.318 (9)
H16I1.43651.41980.56850.165*0.318 (9)
C17B1.5050 (13)1.5056 (12)0.7471 (10)0.100 (5)0.318 (9)
H17G1.48521.43140.72650.150*0.318 (9)
H17H1.45751.52270.80000.150*0.318 (9)
H17I1.62481.54310.76180.150*0.318 (9)
C4A1.2176 (5)1.6540 (2)0.64563 (18)0.0906 (9)
C5A1.1424 (3)1.54437 (19)0.63916 (16)0.0717 (7)
C6A1.2389 (3)1.48816 (18)0.65204 (14)0.0605 (6)
C7A1.1673 (3)1.37861 (17)0.64433 (15)0.0615 (6)
H7A1.20091.35790.69320.074*
C8A1.0597 (3)1.30650 (17)0.57479 (15)0.0637 (7)
H8A1.02991.32820.52590.076*
C9A0.9822 (3)1.19858 (17)0.56451 (16)0.0607 (6)
C10A0.8635 (3)1.13892 (18)0.49124 (16)0.0679 (7)
H10A0.84751.17000.44680.081*
C11A0.7596 (3)1.03461 (18)0.47310 (16)0.0674 (7)
H11A0.77720.99980.51430.081*
C12A0.6379 (3)0.98347 (17)0.40030 (16)0.0677 (7)
H12A0.62881.01840.35800.081*
C13A0.5199 (3)0.88129 (18)0.37977 (16)0.0632 (7)
C14A0.4060 (3)0.84179 (18)0.30252 (16)0.0681 (7)
H14A0.41280.88460.26570.082*
C15A0.2766 (3)0.74353 (17)0.26950 (16)0.0670 (7)
H15A0.26650.69940.30520.080*
C18A0.9547 (3)1.5063 (2)0.62221 (18)0.0987 (9)
H18D0.91041.49770.56030.148*
H18E0.91671.55640.66210.148*
H18F0.91511.44000.63320.148*
C19A1.0313 (3)1.15832 (17)0.63675 (15)0.0725 (7)
H19D0.97281.08400.61930.109*
H19E1.00171.19270.69160.109*
H19F1.15151.17190.64670.109*
C20A0.5282 (3)0.82449 (18)0.44586 (16)0.0807 (8)
H20D0.43330.76030.42730.121*
H20E0.52500.86740.50450.121*
H20F0.63180.80870.44890.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.160 (2)0.0962 (17)0.159 (2)0.0501 (16)0.0196 (16)0.0566 (15)
O4A0.161 (2)0.0803 (16)0.1271 (18)0.0460 (16)0.0067 (15)0.0412 (13)
C10.0585 (18)0.062 (2)0.116 (3)0.0020 (15)0.0073 (16)0.0272 (17)
C20.078 (2)0.106 (3)0.160 (3)0.001 (2)0.007 (2)0.058 (3)
C30.104 (3)0.081 (3)0.158 (3)0.001 (2)0.008 (2)0.062 (2)
C40.110 (3)0.078 (2)0.099 (2)0.029 (2)0.0132 (18)0.0361 (19)
C50.0700 (19)0.0564 (18)0.084 (2)0.0128 (15)0.0129 (14)0.0143 (14)
C60.0571 (17)0.0513 (17)0.0715 (18)0.0050 (14)0.0082 (12)0.0136 (13)
C70.0535 (16)0.0572 (17)0.0706 (18)0.0078 (14)0.0083 (13)0.0127 (14)
C80.0523 (15)0.0554 (17)0.0739 (18)0.0111 (14)0.0019 (13)0.0183 (14)
C90.0439 (14)0.0560 (17)0.0612 (17)0.0113 (13)0.0028 (12)0.0108 (13)
C100.0497 (15)0.0543 (17)0.0695 (18)0.0096 (13)0.0016 (12)0.0154 (13)
C110.0552 (15)0.0536 (17)0.0613 (17)0.0142 (13)0.0009 (12)0.0112 (13)
C120.0478 (14)0.0504 (16)0.0639 (17)0.0100 (13)0.0035 (12)0.0094 (13)
C130.0496 (15)0.0497 (16)0.0592 (17)0.0142 (13)0.0068 (12)0.0069 (13)
C140.0497 (15)0.0496 (16)0.0661 (17)0.0082 (13)0.0080 (13)0.0081 (13)
C150.0590 (16)0.0510 (17)0.0708 (18)0.0075 (14)0.0059 (14)0.0067 (13)
C160.063 (2)0.098 (3)0.257 (4)0.025 (2)0.023 (2)0.024 (3)
C170.097 (2)0.113 (3)0.130 (3)0.015 (2)0.044 (2)0.051 (2)
C180.081 (2)0.089 (2)0.144 (3)0.0347 (19)0.0216 (19)0.0081 (19)
C190.0612 (16)0.0627 (17)0.0740 (18)0.0132 (13)0.0048 (13)0.0160 (14)
C200.0735 (18)0.0602 (18)0.0781 (19)0.0178 (14)0.0084 (14)0.0169 (14)
C1A0.0596 (18)0.0556 (19)0.078 (2)0.0001 (15)0.0102 (15)0.0140 (16)
C2A0.095 (4)0.071 (4)0.087 (4)0.009 (3)0.020 (4)0.017 (3)
C3A0.114 (3)0.062 (2)0.136 (3)0.004 (2)0.017 (2)0.036 (2)
C16A0.072 (3)0.089 (4)0.143 (7)0.024 (3)0.034 (3)0.025 (4)
C17A0.068 (3)0.082 (4)0.079 (4)0.003 (3)0.009 (2)0.015 (3)
C2B0.073 (8)0.087 (10)0.142 (15)0.014 (6)0.029 (9)0.039 (10)
C3B0.114 (3)0.062 (2)0.136 (3)0.004 (2)0.017 (2)0.036 (2)
C16B0.076 (7)0.139 (13)0.106 (10)0.020 (7)0.027 (6)0.040 (8)
C17B0.057 (6)0.104 (11)0.113 (12)0.008 (7)0.009 (7)0.024 (10)
C4A0.118 (3)0.063 (2)0.080 (2)0.021 (2)0.0061 (18)0.0249 (16)
C5A0.0706 (19)0.0526 (18)0.0767 (19)0.0080 (15)0.0051 (14)0.0174 (14)
C6A0.0594 (16)0.0497 (16)0.0570 (16)0.0055 (14)0.0008 (12)0.0104 (12)
C7A0.0583 (16)0.0470 (16)0.0651 (17)0.0048 (13)0.0005 (13)0.0137 (13)
C8A0.0610 (16)0.0502 (17)0.0628 (17)0.0032 (13)0.0048 (13)0.0138 (13)
C9A0.0556 (15)0.0460 (16)0.0664 (17)0.0064 (13)0.0005 (13)0.0119 (13)
C10A0.0680 (17)0.0474 (17)0.0710 (19)0.0053 (14)0.0062 (14)0.0142 (13)
C11A0.0640 (16)0.0443 (16)0.0775 (19)0.0088 (14)0.0016 (14)0.0093 (13)
C12A0.0635 (17)0.0454 (16)0.0741 (19)0.0066 (14)0.0027 (14)0.0061 (13)
C13A0.0524 (16)0.0437 (16)0.0763 (19)0.0072 (13)0.0042 (13)0.0049 (14)
C14A0.0581 (16)0.0515 (17)0.0765 (19)0.0084 (14)0.0036 (14)0.0059 (14)
C15A0.0528 (15)0.0497 (17)0.0774 (19)0.0045 (13)0.0047 (14)0.0036 (13)
C18A0.074 (2)0.085 (2)0.126 (3)0.0244 (17)0.0067 (17)0.0275 (18)
C19A0.0695 (17)0.0553 (17)0.0766 (18)0.0098 (14)0.0086 (13)0.0164 (14)
C20A0.0759 (19)0.0544 (17)0.090 (2)0.0045 (14)0.0002 (15)0.0128 (15)
Geometric parameters (Å, º) top
O4—C41.218 (3)C1A—C2B1.542 (15)
O4A—C4A1.231 (3)C1A—C17A1.548 (6)
C1—C21.505 (3)C1A—C16A1.555 (5)
C1—C61.524 (3)C2A—C3A1.532 (7)
C1—C161.528 (4)C2A—H2E0.9900
C1—C171.539 (4)C2A—H2F0.9900
C2—C31.483 (4)C3A—C4A1.481 (4)
C2—H2A0.9900C3A—H3E0.9900
C2—H2B0.9900C3A—H3F0.9900
C3—C41.489 (4)C16A—H16D0.9800
C3—H3A0.9900C16A—H16E0.9800
C3—H3B0.9900C16A—H16F0.9800
C4—C51.480 (4)C17A—H17D0.9800
C5—C61.340 (3)C17A—H17E0.9800
C5—C181.504 (3)C17A—H17F0.9800
C6—C71.471 (3)C2B—H2G0.9900
C7—C81.335 (3)C2B—H2H0.9900
C7—H70.9500C16B—H16G0.9800
C8—C91.444 (3)C16B—H16H0.9800
C8—H80.9500C16B—H16I0.9800
C9—C101.353 (3)C17B—H17G0.9800
C9—C191.498 (3)C17B—H17H0.9800
C10—C111.432 (3)C17B—H17I0.9800
C10—H100.9500C4A—C5A1.482 (3)
C11—C121.347 (3)C5A—C6A1.349 (3)
C11—H110.9500C5A—C18A1.511 (3)
C12—C131.443 (3)C6A—C7A1.473 (3)
C12—H120.9500C7A—C8A1.326 (3)
C13—C141.355 (3)C7A—H7A0.9500
C13—C201.499 (3)C8A—C9A1.448 (3)
C14—C151.428 (3)C8A—H8A0.9500
C14—H140.9500C9A—C10A1.354 (3)
C15—C15A1.344 (3)C9A—C19A1.494 (3)
C15—H150.9500C10A—C11A1.430 (3)
C16—H16A0.9800C10A—H10A0.9500
C16—H16B0.9800C11A—C12A1.346 (3)
C16—H16C0.9800C11A—H11A0.9500
C17—H17A0.9800C12A—C13A1.442 (3)
C17—H17B0.9800C12A—H12A0.9500
C17—H17C0.9800C13A—C14A1.356 (3)
C18—H18A0.9800C13A—C20A1.501 (3)
C18—H18B0.9800C14A—C15A1.433 (3)
C18—H18C0.9800C14A—H14A0.9500
C19—H19A0.9800C15A—H15A0.9500
C19—H19B0.9800C18A—H18D0.9800
C19—H19C0.9800C18A—H18E0.9800
C20—H20A0.9800C18A—H18F0.9800
C20—H20B0.9800C19A—H19D0.9800
C20—H20C0.9800C19A—H19E0.9800
C1A—C17B1.448 (11)C19A—H19F0.9800
C1A—C2A1.521 (6)C20A—H20D0.9800
C1A—C6A1.520 (3)C20A—H20E0.9800
C1A—C16B1.530 (10)C20A—H20F0.9800
C2—C1—C6109.9 (2)C16B—C1A—C17A147.0 (5)
C2—C1—C16108.3 (3)C2B—C1A—C17A74.5 (6)
C6—C1—C16111.5 (2)C17B—C1A—C16A65.1 (6)
C2—C1—C17110.1 (2)C2A—C1A—C16A108.3 (3)
C6—C1—C17108.1 (2)C6A—C1A—C16A111.6 (3)
C16—C1—C17108.8 (3)C2B—C1A—C16A137.3 (7)
C3—C2—C1114.5 (3)C17A—C1A—C16A105.8 (4)
C3—C2—H2A108.6C1A—C2A—C3A111.0 (4)
C1—C2—H2A108.6C1A—C2A—H2E109.4
C3—C2—H2B108.6C3A—C2A—H2E109.4
C1—C2—H2B108.6C1A—C2A—H2F109.4
H2A—C2—H2B107.6C3A—C2A—H2F109.4
C2—C3—C4113.7 (3)H2E—C2A—H2F108.0
C2—C3—H3A108.8C4A—C3A—C2A115.4 (3)
C4—C3—H3A108.8C4A—C3A—H3E108.4
C2—C3—H3B108.8C2A—C3A—H3E108.4
C4—C3—H3B108.8C4A—C3A—H3F108.4
H3A—C3—H3B107.7C2A—C3A—H3F108.4
O4—C4—C5120.6 (3)H3E—C3A—H3F107.5
O4—C4—C3120.9 (3)C1A—C16A—H16D109.5
C5—C4—C3118.5 (3)C1A—C16A—H16E109.5
C6—C5—C4121.0 (3)C1A—C16A—H16F109.5
C6—C5—C18124.8 (3)C1A—C17A—H17D109.5
C4—C5—C18114.1 (2)C1A—C17A—H17E109.5
C5—C6—C7122.1 (2)C1A—C17A—H17F109.5
C5—C6—C1122.7 (2)C1A—C2B—H2G106.8
C7—C6—C1115.1 (2)C1A—C2B—H2H106.8
C8—C7—C6126.4 (2)H2G—C2B—H2H106.6
C8—C7—H7116.8C1A—C16B—H16G109.5
C6—C7—H7116.8C1A—C16B—H16H109.5
C7—C8—C9127.9 (2)H16G—C16B—H16H109.5
C7—C8—H8116.1C1A—C16B—H16I109.5
C9—C8—H8116.1H16G—C16B—H16I109.5
C10—C9—C8119.0 (2)H16H—C16B—H16I109.5
C10—C9—C19122.7 (2)C1A—C17B—H17G109.5
C8—C9—C19118.3 (2)C1A—C17B—H17H109.5
C9—C10—C11127.3 (2)H17G—C17B—H17H109.5
C9—C10—H10116.4C1A—C17B—H17I109.5
C11—C10—H10116.4H17G—C17B—H17I109.5
C12—C11—C10122.9 (2)H17H—C17B—H17I109.5
C12—C11—H11118.6O4A—C4A—C3A121.1 (3)
C10—C11—H11118.6O4A—C4A—C5A120.0 (3)
C11—C12—C13127.8 (2)C3A—C4A—C5A118.9 (3)
C11—C12—H12116.1C6A—C5A—C4A120.7 (3)
C13—C12—H12116.1C6A—C5A—C18A125.0 (2)
C14—C13—C12118.4 (2)C4A—C5A—C18A114.2 (2)
C14—C13—C20122.7 (2)C5A—C6A—C7A121.8 (2)
C12—C13—C20118.9 (2)C5A—C6A—C1A122.1 (2)
C13—C14—C15128.5 (2)C7A—C6A—C1A116.1 (2)
C13—C14—H14115.7C8A—C7A—C6A125.3 (2)
C15—C14—H14115.7C8A—C7A—H7A117.4
C15A—C15—C14124.2 (2)C6A—C7A—H7A117.4
C15A—C15—H15117.9C7A—C8A—C9A127.7 (2)
C14—C15—H15117.9C7A—C8A—H8A116.2
C1—C16—H16A109.5C9A—C8A—H8A116.2
C1—C16—H16B109.5C10A—C9A—C8A118.6 (2)
H16A—C16—H16B109.5C10A—C9A—C19A122.5 (2)
C1—C16—H16C109.5C8A—C9A—C19A118.8 (2)
H16A—C16—H16C109.5C9A—C10A—C11A127.5 (2)
H16B—C16—H16C109.5C9A—C10A—H10A116.3
C1—C17—H17A109.5C11A—C10A—H10A116.3
C1—C17—H17B109.5C12A—C11A—C10A123.0 (2)
H17A—C17—H17B109.5C12A—C11A—H11A118.5
C1—C17—H17C109.5C10A—C11A—H11A118.5
H17A—C17—H17C109.5C11A—C12A—C13A126.8 (2)
H17B—C17—H17C109.5C11A—C12A—H12A116.6
C5—C18—H18A109.5C13A—C12A—H12A116.6
C5—C18—H18B109.5C14A—C13A—C12A118.6 (2)
H18A—C18—H18B109.5C14A—C13A—C20A123.3 (2)
C5—C18—H18C109.5C12A—C13A—C20A118.1 (2)
H18A—C18—H18C109.5C13A—C14A—C15A128.1 (2)
H18B—C18—H18C109.5C13A—C14A—H14A116.0
C9—C19—H19A109.5C15A—C14A—H14A116.0
C9—C19—H19B109.5C15—C15A—C14A124.6 (2)
H19A—C19—H19B109.5C15—C15A—H15A117.7
C9—C19—H19C109.5C14A—C15A—H15A117.7
H19A—C19—H19C109.5C5A—C18A—H18D109.5
H19B—C19—H19C109.5C5A—C18A—H18E109.5
C13—C20—H20A109.5H18D—C18A—H18E109.5
C13—C20—H20B109.5C5A—C18A—H18F109.5
H20A—C20—H20B109.5H18D—C18A—H18F109.5
C13—C20—H20C109.5H18E—C18A—H18F109.5
H20A—C20—H20C109.5C9A—C19A—H19D109.5
H20B—C20—H20C109.5C9A—C19A—H19E109.5
C17B—C1A—C2A131.3 (5)H19D—C19A—H19E109.5
C17B—C1A—C6A115.6 (5)C9A—C19A—H19F109.5
C2A—C1A—C6A111.5 (3)H19D—C19A—H19F109.5
C17B—C1A—C16B112.0 (7)H19E—C19A—H19F109.5
C2A—C1A—C16B69.0 (5)C13A—C20A—H20D109.5
C6A—C1A—C16B101.3 (4)C13A—C20A—H20E109.5
C17B—C1A—C2B109.8 (7)H20D—C20A—H20E109.5
C6A—C1A—C2B108.3 (6)C13A—C20A—H20F109.5
C16B—C1A—C2B109.3 (7)H20D—C20A—H20F109.5
C2A—C1A—C17A111.0 (3)H20E—C20A—H20F109.5
C6A—C1A—C17A108.5 (3)
C6—C1—C2—C349.1 (4)C16A—C1A—C2A—C3A173.6 (5)
C16—C1—C2—C3171.1 (3)C1A—C2A—C3A—C4A45.5 (7)
C17—C1—C2—C370.0 (3)C2A—C3A—C4A—O4A161.8 (4)
C1—C2—C3—C448.0 (4)C2A—C3A—C4A—C5A18.2 (5)
C2—C3—C4—O4159.2 (3)O4A—C4A—C5A—C6A175.8 (3)
C2—C3—C4—C522.7 (4)C3A—C4A—C5A—C6A4.1 (4)
O4—C4—C5—C6178.9 (3)O4A—C4A—C5A—C18A1.2 (4)
C3—C4—C5—C60.9 (4)C3A—C4A—C5A—C18A178.8 (3)
O4—C4—C5—C183.2 (4)C4A—C5A—C6A—C7A178.8 (2)
C3—C4—C5—C18174.9 (3)C18A—C5A—C6A—C7A4.5 (4)
C4—C5—C6—C7179.8 (2)C4A—C5A—C6A—C1A2.7 (4)
C18—C5—C6—C74.5 (4)C18A—C5A—C6A—C1A174.0 (2)
C4—C5—C6—C14.0 (4)C17B—C1A—C6A—C5A136.0 (8)
C18—C5—C6—C1171.3 (3)C2A—C1A—C6A—C5A30.9 (4)
C2—C1—C6—C527.5 (4)C16B—C1A—C6A—C5A102.6 (7)
C16—C1—C6—C5147.6 (3)C2B—C1A—C6A—C5A12.3 (9)
C17—C1—C6—C592.8 (3)C17A—C1A—C6A—C5A91.6 (4)
C2—C1—C6—C7156.4 (3)C16A—C1A—C6A—C5A152.2 (4)
C16—C1—C6—C736.3 (3)C17B—C1A—C6A—C7A42.5 (8)
C17—C1—C6—C783.3 (3)C2A—C1A—C6A—C7A150.5 (3)
C5—C6—C7—C850.4 (4)C16B—C1A—C6A—C7A78.9 (7)
C1—C6—C7—C8133.4 (3)C2B—C1A—C6A—C7A166.2 (8)
C6—C7—C8—C9179.3 (2)C17A—C1A—C6A—C7A86.9 (4)
C7—C8—C9—C10177.1 (2)C16A—C1A—C6A—C7A29.3 (4)
C7—C8—C9—C191.3 (4)C5A—C6A—C7A—C8A53.4 (3)
C8—C9—C10—C11176.2 (2)C1A—C6A—C7A—C8A128.0 (3)
C19—C9—C10—C112.1 (4)C6A—C7A—C8A—C9A178.3 (2)
C9—C10—C11—C12177.3 (2)C7A—C8A—C9A—C10A174.1 (2)
C10—C11—C12—C13176.7 (2)C7A—C8A—C9A—C19A3.5 (4)
C11—C12—C13—C14179.0 (2)C8A—C9A—C10A—C11A172.5 (2)
C11—C12—C13—C201.9 (3)C19A—C9A—C10A—C11A5.0 (4)
C12—C13—C14—C15179.2 (2)C9A—C10A—C11A—C12A176.0 (2)
C20—C13—C14—C150.1 (4)C10A—C11A—C12A—C13A175.2 (2)
C13—C14—C15—C15A176.1 (2)C11A—C12A—C13A—C14A179.6 (2)
C17B—C1A—C2A—C3A113.8 (11)C11A—C12A—C13A—C20A1.2 (4)
C6A—C1A—C2A—C3A50.5 (6)C12A—C13A—C14A—C15A179.0 (2)
C16B—C1A—C2A—C3A144.8 (8)C20A—C13A—C14A—C15A0.2 (4)
C2B—C1A—C2A—C3A43.0 (7)C14—C15—C15A—C14A178.5 (2)
C17A—C1A—C2A—C3A70.6 (6)C13A—C14A—C15A—C15179.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O4i0.952.603.471 (3)152
Symmetry code: (i) x1, y, z.
(zea) top
Crystal data top
C40H56O2·(3H2O)F(000) = 1368
Mr = 622.90Dx = 1.046 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C2ycCell parameters from 2203 reflections
a = 49.670 (15) Åθ = 2.6–25.3°
b = 13.181 (4) ŵ = 0.07 mm1
c = 6.0588 (19) ÅT = 100 K
β = 94.425 (6)°Plate, orange
V = 3955 (2) Å30.90 × 0.15 × 0.05 mm
Z = 4
Data collection top
CCD area detector
diffractometer
3489 independent reflections
Radiation source: fine-focus sealed tube2285 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
phi and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
SADABS
h = 5658
Tmin = 0.807, Tmax = 1.000k = 1515
13818 measured reflectionsl = 77
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0727P)2 + 0.0665P]
where P = (Fo2 + 2Fc2)/3
3489 reflections(Δ/σ)max < 0.001
197 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C40H56O2·(3H2O)V = 3955 (2) Å3
Mr = 622.90Z = 4
Monoclinic, C2/cMo Kα radiation
a = 49.670 (15) ŵ = 0.07 mm1
b = 13.181 (4) ÅT = 100 K
c = 6.0588 (19) Å0.90 × 0.15 × 0.05 mm
β = 94.425 (6)°
Data collection top
CCD area detector
diffractometer
3489 independent reflections
Absorption correction: multi-scan
SADABS
2285 reflections with I > 2σ(I)
Tmin = 0.807, Tmax = 1.000Rint = 0.047
13818 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.137H-atom parameters constrained
S = 1.03Δρmax = 0.27 e Å3
3489 reflectionsΔρmin = 0.17 e Å3
197 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
O30.49569 (3)0.59866 (12)1.0311 (2)0.0439 (4)
H3O0.49720.60601.16590.066*
C10.44598 (4)0.80435 (14)0.8482 (3)0.0317 (5)
C20.47091 (4)0.75360 (16)0.9660 (4)0.0372 (5)
H2A0.48700.77980.90520.045*
H2B0.47190.77101.12200.045*
C30.47038 (4)0.64075 (15)0.9425 (3)0.0352 (5)
H30.46790.62400.78470.042*
C40.44678 (4)0.59864 (14)1.0556 (3)0.0321 (5)
H4A0.45080.60191.21470.039*
H4B0.44430.52791.01510.039*
C50.42081 (4)0.65563 (14)0.9948 (3)0.0299 (5)
C60.42044 (4)0.74649 (14)0.8974 (3)0.0273 (5)
C70.39466 (4)0.79947 (14)0.8268 (3)0.0306 (5)
H70.38950.85390.91170.037*
C80.37855 (4)0.77386 (15)0.6505 (3)0.0322 (5)
H80.38340.71630.57430.039*
C90.35424 (4)0.82534 (14)0.5632 (3)0.0281 (5)
C100.34115 (4)0.78971 (15)0.3747 (3)0.0328 (5)
H100.34880.73290.31320.039*
C110.31715 (4)0.82774 (15)0.2573 (3)0.0300 (5)
H110.30800.88130.31830.036*
C120.30723 (4)0.78887 (15)0.0615 (3)0.0318 (5)
H120.31700.73570.00580.038*
C130.28336 (4)0.81985 (14)0.0714 (3)0.0287 (5)
C140.27623 (4)0.76757 (15)0.2601 (3)0.0323 (5)
H140.28820.71700.29620.039*
C150.25288 (4)0.77958 (15)0.4105 (3)0.0299 (4)
H150.24090.83150.38330.036*
C160.44829 (4)0.80890 (16)0.5979 (3)0.0396 (5)
H16A0.43200.83690.52700.059*
H16B0.45100.74170.54250.059*
H16C0.46330.85090.56730.059*
C170.44485 (5)0.91283 (15)0.9372 (4)0.0417 (6)
H17A0.44120.91111.09050.063*
H17B0.43080.94970.85450.063*
H17C0.46190.94580.92250.063*
C180.39582 (4)0.60307 (16)1.0624 (4)0.0433 (6)
H18A0.38040.64621.03040.065*
H18B0.39780.58881.21820.065*
H18C0.39330.54070.98160.065*
C190.34552 (4)0.91735 (14)0.6819 (3)0.0312 (5)
H19A0.32850.94080.61410.047*
H19B0.35880.96970.67390.047*
H19C0.34360.90080.83410.047*
C200.26757 (4)0.90806 (14)0.0063 (3)0.0324 (5)
H20A0.25260.92160.09910.049*
H20B0.27900.96680.02060.049*
H20C0.26100.89230.14730.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0356 (8)0.0576 (10)0.0376 (9)0.0156 (7)0.0029 (7)0.0134 (8)
C10.0326 (11)0.0303 (11)0.0316 (11)0.0040 (9)0.0011 (9)0.0036 (8)
C20.0325 (12)0.0386 (12)0.0400 (13)0.0021 (9)0.0008 (10)0.0035 (10)
C30.0335 (12)0.0378 (12)0.0336 (12)0.0099 (9)0.0018 (9)0.0060 (9)
C40.0386 (12)0.0269 (10)0.0307 (11)0.0053 (9)0.0021 (9)0.0012 (8)
C50.0332 (11)0.0307 (11)0.0261 (11)0.0036 (9)0.0039 (9)0.0054 (8)
C60.0304 (11)0.0299 (11)0.0211 (10)0.0054 (8)0.0004 (8)0.0035 (8)
C70.0344 (11)0.0285 (11)0.0290 (11)0.0067 (9)0.0041 (9)0.0037 (8)
C80.0346 (12)0.0301 (11)0.0317 (11)0.0059 (9)0.0014 (9)0.0056 (9)
C90.0268 (10)0.0295 (11)0.0282 (11)0.0009 (8)0.0039 (9)0.0004 (8)
C100.0295 (11)0.0355 (11)0.0332 (12)0.0036 (9)0.0022 (9)0.0042 (9)
C110.0294 (11)0.0304 (11)0.0304 (11)0.0001 (9)0.0037 (9)0.0013 (9)
C120.0286 (10)0.0332 (11)0.0336 (12)0.0007 (9)0.0021 (9)0.0018 (9)
C130.0289 (10)0.0291 (11)0.0284 (11)0.0060 (8)0.0037 (8)0.0015 (9)
C140.0275 (11)0.0348 (11)0.0348 (12)0.0023 (9)0.0043 (9)0.0015 (9)
C150.0257 (10)0.0313 (11)0.0326 (11)0.0042 (9)0.0021 (9)0.0009 (8)
C160.0438 (13)0.0377 (12)0.0380 (13)0.0052 (10)0.0072 (10)0.0056 (10)
C170.0508 (14)0.0325 (12)0.0413 (13)0.0009 (10)0.0000 (11)0.0021 (10)
C180.0437 (13)0.0389 (13)0.0488 (14)0.0047 (10)0.0130 (11)0.0013 (10)
C190.0308 (11)0.0328 (11)0.0294 (11)0.0046 (9)0.0009 (9)0.0012 (9)
C200.0337 (11)0.0323 (11)0.0306 (11)0.0015 (9)0.0018 (9)0.0016 (9)
Geometric parameters (Å, º) top
O3—C31.440 (2)C11—C121.350 (3)
O3—H3O0.8200C11—H110.9300
C1—C61.529 (3)C12—C131.440 (3)
C1—C161.531 (3)C12—H120.9300
C1—C171.531 (3)C13—C141.358 (3)
C1—C21.534 (3)C13—C201.499 (3)
C2—C31.494 (3)C14—C151.427 (3)
C2—H2A0.9700C14—H140.9300
C2—H2B0.9700C15—C15i1.349 (4)
C3—C41.509 (3)C15—H150.9300
C3—H30.9800C16—H16A0.9600
C4—C51.513 (3)C16—H16B0.9600
C4—H4A0.9700C16—H16C0.9600
C4—H4B0.9700C17—H17A0.9600
C5—C61.335 (3)C17—H17B0.9600
C5—C181.506 (3)C17—H17C0.9600
C6—C71.492 (3)C18—H18A0.9600
C7—C81.328 (3)C18—H18B0.9600
C7—H70.9300C18—H18C0.9600
C8—C91.449 (3)C19—H19A0.9600
C8—H80.9300C19—H19B0.9600
C9—C101.354 (3)C19—H19C0.9600
C9—C191.491 (3)C20—H20A0.9600
C10—C111.431 (3)C20—H20B0.9600
C10—H100.9300C20—H20C0.9600
C3—O3—H3O109.5C12—C11—H11118.7
C6—C1—C16109.86 (16)C10—C11—H11118.7
C6—C1—C17110.10 (17)C11—C12—C13127.79 (19)
C16—C1—C17108.67 (16)C11—C12—H12116.1
C6—C1—C2110.09 (16)C13—C12—H12116.1
C16—C1—C2111.01 (17)C14—C13—C12118.49 (18)
C17—C1—C2107.07 (16)C14—C13—C20123.31 (18)
C3—C2—C1112.46 (17)C12—C13—C20118.20 (17)
C3—C2—H2A109.1C13—C14—C15128.87 (19)
C1—C2—H2A109.1C13—C14—H14115.6
C3—C2—H2B109.1C15—C14—H14115.6
C1—C2—H2B109.1C15i—C15—C14124.1 (2)
H2A—C2—H2B107.8C15i—C15—H15117.9
O3—C3—C2109.86 (17)C14—C15—H15117.9
O3—C3—C4112.08 (16)C1—C16—H16A109.5
C2—C3—C4109.35 (17)C1—C16—H16B109.5
O3—C3—H3108.5H16A—C16—H16B109.5
C2—C3—H3108.5C1—C16—H16C109.5
C4—C3—H3108.5H16A—C16—H16C109.5
C3—C4—C5112.60 (16)H16B—C16—H16C109.5
C3—C4—H4A109.1C1—C17—H17A109.5
C5—C4—H4A109.1C1—C17—H17B109.5
C3—C4—H4B109.1H17A—C17—H17B109.5
C5—C4—H4B109.1C1—C17—H17C109.5
H4A—C4—H4B107.8H17A—C17—H17C109.5
C6—C5—C18123.34 (18)H17B—C17—H17C109.5
C6—C5—C4122.38 (17)C5—C18—H18A109.5
C18—C5—C4114.23 (17)C5—C18—H18B109.5
C5—C6—C7121.95 (17)H18A—C18—H18B109.5
C5—C6—C1123.40 (17)C5—C18—H18C109.5
C7—C6—C1114.65 (16)H18A—C18—H18C109.5
C8—C7—C6124.22 (17)H18B—C18—H18C109.5
C8—C7—H7117.9C9—C19—H19A109.5
C6—C7—H7117.9C9—C19—H19B109.5
C7—C8—C9127.44 (18)H19A—C19—H19B109.5
C7—C8—H8116.3C9—C19—H19C109.5
C9—C8—H8116.3H19A—C19—H19C109.5
C10—C9—C8118.53 (18)H19B—C19—H19C109.5
C10—C9—C19123.41 (17)C13—C20—H20A109.5
C8—C9—C19118.02 (16)C13—C20—H20B109.5
C9—C10—C11128.68 (19)H20A—C20—H20B109.5
C9—C10—H10115.7C13—C20—H20C109.5
C11—C10—H10115.7H20A—C20—H20C109.5
C12—C11—C10122.50 (19)H20B—C20—H20C109.5
C6—C1—C2—C344.6 (2)C17—C1—C6—C751.3 (2)
C16—C1—C2—C377.2 (2)C2—C1—C6—C7169.14 (16)
C17—C1—C2—C3164.29 (18)C5—C6—C7—C874.9 (3)
C1—C2—C3—O3172.61 (16)C1—C6—C7—C8104.9 (2)
C1—C2—C3—C464.0 (2)C6—C7—C8—C9175.62 (19)
O3—C3—C4—C5169.44 (16)C7—C8—C9—C10177.1 (2)
C2—C3—C4—C547.4 (2)C7—C8—C9—C190.7 (3)
C3—C4—C5—C615.3 (3)C8—C9—C10—C11179.54 (19)
C3—C4—C5—C18167.20 (17)C19—C9—C10—C111.9 (3)
C18—C5—C6—C76.2 (3)C9—C10—C11—C12175.3 (2)
C4—C5—C6—C7176.53 (17)C10—C11—C12—C13179.66 (19)
C18—C5—C6—C1174.12 (18)C11—C12—C13—C14177.20 (19)
C4—C5—C6—C13.2 (3)C11—C12—C13—C202.5 (3)
C16—C1—C6—C5111.4 (2)C12—C13—C14—C15175.84 (18)
C17—C1—C6—C5128.96 (19)C20—C13—C14—C153.9 (3)
C2—C1—C6—C511.1 (3)C13—C14—C15—C15i177.1 (2)
C16—C1—C6—C768.3 (2)
Symmetry code: (i) x+1/2, y+3/2, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O3ii0.821.852.654 (3)169
Symmetry code: (ii) x+1, y, z+5/2.

Experimental details

(axt-CL)(axt-PY)(AXT-un)(canth-100K)
Crystal data
Chemical formulaC40H52O4·2(CHCl3)C40H52O4·2(C5H5N)C40H52O4C40H52O2
Mr835.55755.02596.82564.82
Crystal system, space groupTriclinic, P1Monoclinic, P21/nTriclinic, P1Triclinic, P1
Temperature (K)100100100100
a, b, c (Å)5.9588 (8), 11.8583 (16), 15.647 (2)18.568 (4), 6.1926 (13), 19.803 (4)8.5371 (10), 8.6632 (11), 13.2984 (16)8.5068 (9), 14.2208 (16), 15.5262 (17)
α, β, γ (°)79.036 (2), 80.499 (3), 82.506 (2)90, 107.746 (4), 9095.145 (2), 107.409 (2), 98.765 (2)105.870 (2), 95.227 (2), 106.512 (2)
V3)1065.0 (3)2168.7 (8)917.93 (19)1702.9 (3)
Z1212
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.440.070.070.07
Crystal size (mm)0.65 × 0.05 × 0.020.60 × 0.15 × 0.050.60 × 0.30 × 0.050.50 × 0.35 × 0.30
Data collection
DiffractometerCCD area detector
diffractometer
CCD area detector
diffractometer
CCD area detector
diffractometer
CCD area detector
diffractometer
Absorption correction
Tmin, Tmax
No. of measured, independent and
observed [I > 2σ(I)] reflections
7182, 3634, 1776 12345, 3104, 1400 4780, 3188, 1991 9834, 6781, 3448
Rint0.0610.1480.0500.031
θmax (°)25.023.325.026.4
(sin θ/λ)max1)0.5950.5560.5950.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.093, 0.80 0.049, 0.116, 0.77 0.052, 0.163, 0.84 0.050, 0.112, 0.84
No. of reflections3634310331886779
No. of parameters259292245419
No. of restraints2700
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.54, 0.570.26, 0.170.20, 0.150.20, 0.16


(canth-293)(zea)
Crystal data
Chemical formulaC40H52O2C40H56O2·(3H2O)
Mr564.82622.90
Crystal system, space groupTriclinic, P1Monoclinic, C2/c
Temperature (K)293100
a, b, c (Å)8.5919 (11), 14.3168 (18), 15.9405 (19)49.670 (15), 13.181 (4), 6.0588 (19)
α, β, γ (°)105.569 (2), 96.118 (3), 107.024 (2)90, 94.425 (6), 90
V3)1769.2 (4)3955 (2)
Z24
Radiation typeMo KαMo Kα
µ (mm1)0.060.07
Crystal size (mm)0.50 × 0.35 × 0.300.90 × 0.15 × 0.05
Data collection
DiffractometerCCD area detector
diffractometer
CCD area detector
diffractometer
Absorption correctionMulti-scan
SADABS
Tmin, Tmax0.807, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
9285, 6162, 2591 13818, 3489, 2285
Rint0.0250.047
θmax (°)25.025.0
(sin θ/λ)max1)0.5950.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.137, 0.82 0.051, 0.137, 1.03
No. of reflections61623489
No. of parameters419197
No. of restraints00
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.090.27, 0.17

Computer programs: Bruker SMART, Bruker SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), Bruker SHELXTL.

Hydrogen-bond geometry (Å, º) for (axt-CL) top
D—H···AD—HH···AD···AD—H···A
C18—H18C···O3i0.982.523.460 (4)161
C18—H18C···O4i0.982.913.557 (4)124
C1S—H1S···O3i1.002.163.061 (4)149
O3—H3O···O4ii0.834 (17)2.02 (2)2.790 (3)154 (3)
Symmetry codes: (i) x+2, y, z+2; (ii) x+3, y, z+2.
Hydrogen-bond geometry (Å, º) for (axt-PY) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O4i0.82 (2)2.03 (3)2.822 (4)161 (6)
C4S—H4S···O30.952.393.179 (6)140
Symmetry code: (i) x+1, y+2, z+1.
Hydrogen-bond geometry (Å, º) for (AXT-un) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O40.842.172.653 (3)116
C10—H10···O4i0.952.503.439 (3)168
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) for (canth-100K) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O4i0.952.583.438 (2)150
Symmetry code: (i) x1, y, z.
Hydrogen-bond geometry (Å, º) for (canth-293) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O4i0.952.603.471 (3)152
Symmetry code: (i) x1, y, z.
Hydrogen-bond geometry (Å, º) for (zea) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O3i0.821.852.654 (3)169
Symmetry code: (i) x+1, y, z+5/2.
 

Subscribe to Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds