Download citation
Download citation
link to html
Three crystal forms of the steroid 20-hydroxyecdysone were identified by single-crystal X-ray diffraction analysis: a solvent-free modification, a methanol solvate hydrate and a trihydrate. The structure of a closely related steroid, polypodine B (the 5,20-dihydroxy derivative of ecdysone), was determined in its monohydrate form. Since the unit-cell volume of unsolvated 20-hydroxyecdysone was found to be considerably smaller than that of ecdysone [Huber & Hoppe (1965). Chem. Ber. 98, 2403-2424], a new structure determination of ecdysone was performed, which confirmed the unexpected difference between the unit-cell volumes. The crystals of ecdysone and 20-hydroxyecdysone are isostructural, while the mixed solvate of 20-hydroxyecdysone is homostructural with the hydrate of polypodine B. A detailed analysis of the hydrogen-bond networks in these closely related crystal pairs highlights their packing similarities, demonstrates the role of solvent molecules, and explains the unexpectedly small cell volume of 20-hydroxyecdysone.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102005608/de0015sup1.cif
Contains datablocks I, II, III, IV, V, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102005608/de0015Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102005608/de0015IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102005608/de0015IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102005608/de0015IVsup5.hkl
Contains datablock IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102005608/de0015Vsup6.hkl
Contains datablock V

CCDC references: 193588; 193589; 193590; 193591; 193592

Computing details top

Data collection: CAD-4 EXPRESS for (I), (II), (IV), (V); Enraf-Nonius Express for (III). Cell refinement: CAD-4 EXPRESS for (I), (II), (IV), (V); Enraf-Nonius Express for (III). For all compounds, data reduction: XCAD4 (Harms, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
(I) 2β,3β,14α,22R,25-pentahydroxy-5β-cholest-7-en-6-one top
Crystal data top
C27H44O6Dx = 1.124 Mg m3
Mr = 464.62Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 7.750 (1) Åθ = 20.1–23.7°
b = 9.935 (1) ŵ = 0.62 mm1
c = 35.657 (1) ÅT = 293 K
V = 2745.5 (5) Å3Block, colorless
Z = 40.25 × 0.16 × 0.12 mm
F(000) = 1016
Data collection top
Enraf-Nonius CAD4
diffractometer
3946 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.013
Graphite monochromatorθmax = 74.7°, θmin = 4.6°
ω–2θ scansh = 89
Absorption correction: ψ scan
North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24 350-359
k = 1212
Tmin = 0.858, Tmax = 0.930l = 4444
6982 measured reflections3 standard reflections every 60 min
5410 independent reflections intensity decay: 9%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.035 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.109(Δ/σ)max = 0.001
S = 0.74Δρmax = 0.15 e Å3
5410 reflectionsΔρmin = 0.14 e Å3
376 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
290 restraintsExtinction coefficient: 0.0014 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.18 (17)
Crystal data top
C27H44O6V = 2745.5 (5) Å3
Mr = 464.62Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 7.750 (1) ŵ = 0.62 mm1
b = 9.935 (1) ÅT = 293 K
c = 35.657 (1) Å0.25 × 0.16 × 0.12 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
3946 reflections with I > 2σ(I)
Absorption correction: ψ scan
North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24 350-359
Rint = 0.013
Tmin = 0.858, Tmax = 0.9303 standard reflections every 60 min
6982 measured reflections intensity decay: 9%
5410 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109Δρmax = 0.15 e Å3
S = 0.74Δρmin = 0.14 e Å3
5410 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
376 parametersAbsolute structure parameter: 0.18 (17)
290 restraints
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)
O20.01505 (17)0.64110 (15)0.95659 (3)0.0517 (3)
H20.05670.68870.97310.067*
O30.29606 (18)0.69367 (14)0.99714 (3)0.0529 (3)
H30.26410.62731.00890.069*
O60.71094 (17)0.98389 (14)0.94469 (3)0.0532 (3)
O140.42685 (19)0.81146 (12)0.81321 (3)0.0496 (3)
H140.51140.77000.82080.065*
C10.1102 (2)0.8594 (2)0.94183 (5)0.0463 (4)
H1A0.09990.88580.96790.060*
H1B0.00390.88440.92930.060*
C20.1299 (2)0.7089 (2)0.93993 (4)0.0438 (4)
H2A0.13380.68350.91340.057*
C30.2976 (2)0.66325 (19)0.95779 (4)0.0437 (4)
H3A0.31110.56600.95430.057*
C40.4503 (2)0.73592 (17)0.94022 (5)0.0413 (4)
H4A0.46140.70890.91420.054*
H4B0.55530.71040.95320.054*
C50.4276 (2)0.88920 (17)0.94234 (4)0.0384 (4)
H50.42310.91410.96890.050*
C60.5838 (2)0.95673 (17)0.92548 (4)0.0388 (4)
C70.5804 (2)0.98136 (17)0.88521 (4)0.0397 (4)
H70.67911.01460.87360.052*
C80.4406 (2)0.95783 (17)0.86439 (4)0.0369 (3)
C90.2690 (2)0.91404 (19)0.88096 (4)0.0416 (4)
H90.26330.81630.87750.054*
C100.2601 (2)0.93820 (18)0.92401 (4)0.0411 (4)
C110.1128 (2)0.9719 (3)0.85996 (5)0.0625 (6)
H11A0.09901.06570.86690.081*
H11B0.00990.92430.86790.081*
C120.1277 (2)0.9622 (3)0.81702 (5)0.0572 (5)
H12A0.12500.86840.80950.074*
H12B0.02991.00710.80560.074*
C130.2942 (2)1.02651 (18)0.80304 (4)0.0428 (4)
C140.4461 (2)0.95220 (17)0.82200 (4)0.0380 (4)
C150.6042 (2)1.0056 (2)0.80135 (4)0.0456 (4)
H15A0.70010.94330.80320.059*
H15B0.63941.09240.81120.059*
C160.5399 (2)1.0181 (2)0.76035 (5)0.0517 (5)
H16A0.59080.94820.74490.067*
H16B0.57201.10490.75000.067*
C170.3406 (2)1.00334 (19)0.76112 (4)0.0448 (4)
H170.31350.90940.75510.058*
C180.3008 (3)1.1761 (2)0.81292 (5)0.0569 (5)
H18A0.19421.21810.80580.085*
H18B0.39451.21790.79970.085*
H18C0.31791.18620.83940.085*
C190.2357 (3)1.0875 (2)0.93360 (5)0.0588 (5)
H19A0.11851.11320.92870.088*
H19B0.31211.14090.91850.088*
H19C0.26121.10180.95960.088*
C200.2505 (3)1.0925 (2)0.73154 (5)0.0531 (5)
H200.28831.18520.73610.069*
C210.0527 (3)1.0925 (3)0.73363 (6)0.0801 (7)
H21A0.00651.13420.71150.120*
H21B0.01631.14190.75540.120*
H21C0.01171.00150.73530.120*
C220.3125 (3)1.05427 (19)0.69185 (4)0.0547 (5)
H22A0.43581.03260.69270.071*0.476 (18)
H22B0.43891.05320.69260.071*0.524 (18)
O22A0.287 (4)1.1734 (14)0.6693 (5)0.067 (5)0.476 (18)
H22C0.27331.14630.64780.087*0.476 (18)
C23A0.214 (2)0.9341 (13)0.6776 (3)0.072 (4)0.476 (18)
H23A0.09470.96040.67420.094*0.476 (18)
H23B0.21650.86520.69690.094*0.476 (18)
C24A0.279 (2)0.8710 (10)0.6408 (2)0.082 (4)0.476 (18)
H24A0.40120.88890.63870.107*0.476 (18)
H24B0.26460.77420.64270.107*0.476 (18)
C25A0.1914 (17)0.9180 (9)0.6047 (2)0.056 (3)0.476 (18)
O25A0.2267 (17)1.0604 (7)0.6015 (3)0.058 (4)0.476 (18)
H25A0.16851.09240.58440.075*0.476 (18)
C26A0.270 (3)0.8462 (13)0.5711 (2)0.109 (5)0.476 (18)
H26A0.22000.88070.54840.164*0.476 (18)
H26B0.24750.75140.57290.164*0.476 (18)
H26C0.39250.86120.57070.164*0.476 (18)
C27A0.0024 (18)0.8948 (12)0.6068 (3)0.094 (4)0.476 (18)
H27A0.05350.96140.62290.141*0.476 (18)
H27B0.02460.80680.61680.141*0.476 (18)
H27C0.05140.90170.58220.141*0.476 (18)
O22B0.263 (4)1.1654 (12)0.6676 (4)0.058 (3)0.524 (18)
H22D0.25201.13810.64610.075*0.524 (18)
C23B0.256 (2)0.9201 (11)0.6752 (3)0.059 (2)0.524 (18)
H23C0.13200.92260.67130.076*0.524 (18)
H23D0.27940.84960.69330.076*0.524 (18)
C24B0.3429 (12)0.8829 (7)0.63812 (18)0.0510 (16)0.524 (18)
H24C0.45350.92850.63740.066*0.524 (18)
H24D0.36660.78700.63870.066*0.524 (18)
C25B0.2511 (10)0.9127 (10)0.6016 (2)0.0566 (19)0.524 (18)
O25B0.2173 (15)1.0553 (8)0.6014 (2)0.057 (4)0.524 (18)
H25B0.16471.07540.58230.074*0.524 (18)
C26B0.3632 (14)0.8759 (9)0.5682 (2)0.078 (2)0.524 (18)
H26D0.31130.90970.54560.118*0.524 (18)
H26E0.37350.77970.56660.118*0.524 (18)
H26F0.47570.91490.57120.118*0.524 (18)
C27B0.0795 (14)0.8393 (11)0.5990 (2)0.086 (3)0.524 (18)
H27D0.00240.87300.61780.128*0.524 (18)
H27E0.09760.74470.60270.128*0.524 (18)
H27F0.03020.85390.57460.128*0.524 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0460 (7)0.0739 (9)0.0351 (6)0.0154 (6)0.0038 (5)0.0021 (6)
O30.0538 (8)0.0709 (9)0.0339 (5)0.0118 (7)0.0045 (6)0.0149 (6)
O60.0448 (7)0.0707 (8)0.0441 (6)0.0079 (7)0.0118 (6)0.0124 (6)
O140.0616 (8)0.0426 (7)0.0447 (6)0.0014 (6)0.0069 (6)0.0046 (5)
C10.0333 (9)0.0661 (12)0.0395 (8)0.0080 (8)0.0057 (7)0.0101 (8)
C20.0382 (9)0.0649 (11)0.0283 (7)0.0051 (8)0.0047 (7)0.0034 (7)
C30.0441 (10)0.0483 (9)0.0386 (8)0.0014 (8)0.0010 (8)0.0042 (7)
C40.0378 (9)0.0479 (9)0.0383 (8)0.0069 (8)0.0017 (7)0.0046 (7)
C50.0382 (9)0.0477 (9)0.0293 (7)0.0041 (7)0.0007 (7)0.0036 (7)
C60.0378 (9)0.0436 (9)0.0352 (7)0.0046 (7)0.0029 (7)0.0040 (7)
C70.0351 (9)0.0486 (9)0.0355 (7)0.0010 (8)0.0018 (6)0.0090 (7)
C80.0353 (8)0.0427 (9)0.0327 (7)0.0047 (7)0.0019 (6)0.0074 (6)
C90.0360 (9)0.0561 (10)0.0329 (7)0.0032 (8)0.0000 (6)0.0106 (7)
C100.0363 (10)0.0540 (10)0.0329 (8)0.0086 (8)0.0031 (6)0.0078 (7)
C110.0357 (10)0.1077 (18)0.0439 (9)0.0068 (11)0.0015 (7)0.0225 (11)
C120.0378 (10)0.0892 (15)0.0447 (9)0.0041 (10)0.0077 (8)0.0216 (10)
C130.0418 (9)0.0510 (10)0.0356 (7)0.0004 (8)0.0044 (7)0.0076 (7)
C140.0395 (9)0.0416 (9)0.0328 (8)0.0004 (7)0.0013 (6)0.0036 (6)
C150.0413 (9)0.0599 (11)0.0357 (8)0.0017 (9)0.0003 (7)0.0064 (8)
C160.0545 (11)0.0667 (12)0.0338 (8)0.0015 (9)0.0002 (7)0.0081 (8)
C170.0531 (10)0.0481 (10)0.0331 (7)0.0061 (8)0.0061 (7)0.0089 (7)
C180.0682 (13)0.0553 (11)0.0471 (9)0.0132 (11)0.0083 (10)0.0060 (9)
C190.0664 (14)0.0565 (11)0.0535 (10)0.0162 (10)0.0075 (10)0.0058 (8)
C200.0650 (14)0.0566 (11)0.0377 (9)0.0025 (9)0.0098 (8)0.0118 (8)
C210.0737 (16)0.109 (2)0.0575 (12)0.0155 (15)0.0185 (12)0.0265 (13)
C220.0781 (14)0.0504 (10)0.0355 (8)0.0101 (10)0.0147 (9)0.0121 (8)
O22A0.099 (7)0.064 (7)0.039 (4)0.033 (3)0.025 (3)0.014 (3)
C23A0.121 (10)0.051 (5)0.044 (4)0.007 (5)0.020 (4)0.018 (3)
C24A0.123 (9)0.063 (4)0.061 (4)0.003 (5)0.028 (5)0.011 (3)
C25A0.094 (7)0.036 (3)0.039 (3)0.004 (4)0.021 (3)0.001 (2)
O25A0.076 (8)0.037 (5)0.061 (6)0.010 (4)0.015 (5)0.019 (4)
C26A0.182 (14)0.092 (6)0.055 (4)0.041 (8)0.021 (6)0.010 (4)
C27A0.127 (8)0.064 (5)0.091 (5)0.047 (5)0.040 (5)0.017 (4)
O22B0.099 (8)0.035 (3)0.039 (3)0.013 (4)0.023 (3)0.009 (2)
C23B0.085 (5)0.042 (3)0.050 (4)0.009 (4)0.013 (3)0.002 (2)
C24B0.072 (4)0.034 (2)0.047 (3)0.002 (2)0.014 (2)0.0031 (18)
C25B0.070 (4)0.052 (3)0.048 (3)0.013 (3)0.014 (3)0.008 (2)
O25B0.074 (7)0.063 (6)0.034 (4)0.006 (5)0.024 (4)0.002 (3)
C26B0.113 (6)0.069 (4)0.054 (3)0.001 (4)0.005 (4)0.003 (2)
C27B0.102 (6)0.079 (5)0.075 (4)0.036 (5)0.026 (4)0.009 (4)
Geometric parameters (Å, º) top
O2—C21.438 (2)C13—C171.555 (2)
O3—C31.4351 (19)C14—C151.525 (2)
O6—C61.230 (2)C15—C161.550 (2)
O14—C141.441 (2)C16—C171.552 (3)
C1—C21.504 (3)C17—C201.544 (2)
C1—C101.538 (2)C20—C211.535 (3)
C2—C31.517 (3)C20—C221.542 (3)
C3—C41.521 (2)C22—O22A1.443 (10)
C4—C51.535 (2)C22—O22B1.454 (8)
C5—C61.508 (2)C22—C23A1.505 (11)
C5—C101.533 (2)C22—C23B1.524 (8)
C6—C71.457 (2)C23A—C24A1.538 (10)
C7—C81.334 (2)C24A—C25A1.529 (8)
C8—C141.513 (2)C25A—O25A1.446 (8)
C8—C91.519 (2)C25A—C27A1.521 (4)
C9—C111.535 (2)C25A—C26A1.522 (4)
C9—C101.555 (2)C23B—C24B1.530 (9)
C10—C191.534 (3)C24B—C25B1.512 (8)
C11—C121.538 (3)C25B—O25B1.441 (9)
C12—C131.523 (3)C25B—C27B1.519 (4)
C13—C181.528 (3)C25B—C26B1.521 (4)
C13—C141.545 (2)
C2—C1—C10114.26 (14)O14—C14—C13106.85 (14)
O2—C2—C1111.56 (15)C8—C14—C13113.46 (14)
O2—C2—C3110.85 (13)C15—C14—C13103.56 (12)
C1—C2—C3111.41 (15)C14—C15—C16103.02 (13)
O3—C3—C2109.90 (14)C15—C16—C17107.19 (14)
O3—C3—C4108.02 (14)C20—C17—C16112.57 (15)
C2—C3—C4110.59 (13)C20—C17—C13117.85 (15)
C3—C4—C5111.21 (15)C16—C17—C13103.49 (13)
C6—C5—C10111.62 (13)C21—C20—C22110.85 (17)
C6—C5—C4109.27 (14)C21—C20—C17114.76 (16)
C10—C5—C4113.02 (15)C22—C20—C17110.17 (16)
O6—C6—C7121.74 (16)O22A—C22—O22B8 (2)
O6—C6—C5121.23 (14)O22A—C22—C23A113.3 (11)
C7—C6—C5116.94 (15)O22B—C22—C23A105.6 (12)
C8—C7—C6122.25 (15)O22A—C22—C23B117.5 (12)
C7—C8—C14122.66 (15)O22B—C22—C23B110.9 (9)
C7—C8—C9123.01 (14)C23A—C22—C23B13.7 (12)
C14—C8—C9113.73 (14)O22A—C22—C20105.5 (9)
C8—C9—C11113.15 (13)O22B—C22—C20106.0 (7)
C8—C9—C10112.25 (14)C23A—C22—C20110.3 (5)
C11—C9—C10112.87 (15)C23B—C22—C20118.9 (4)
C5—C10—C19108.45 (16)C22—C23A—C24A116.5 (9)
C5—C10—C1107.56 (13)C25A—C24A—C23A116.9 (8)
C19—C10—C1107.89 (15)O25A—C25A—C27A109.8 (7)
C5—C10—C9109.51 (13)O25A—C25A—C26A108.7 (6)
C19—C10—C9112.02 (14)C27A—C25A—C26A111.4 (6)
C1—C10—C9111.27 (15)O25A—C25A—C24A106.4 (6)
C9—C11—C12113.76 (16)C27A—C25A—C24A110.3 (6)
C13—C12—C11111.28 (16)C26A—C25A—C24A110.1 (6)
C12—C13—C18111.14 (18)C22—C23B—C24B114.9 (7)
C12—C13—C14107.56 (13)C25B—C24B—C23B119.2 (7)
C18—C13—C14109.78 (15)O25B—C25B—C24B106.4 (5)
C12—C13—C17116.64 (15)O25B—C25B—C27B108.2 (6)
C18—C13—C17110.96 (14)C24B—C25B—C27B111.9 (6)
C14—C13—C17100.00 (13)O25B—C25B—C26B109.6 (6)
O14—C14—C8104.49 (13)C24B—C25B—C26B111.0 (6)
O14—C14—C15108.42 (14)C27B—C25B—C26B109.6 (5)
C8—C14—C15119.47 (14)
C10—C1—C2—O2179.26 (13)C12—C13—C14—O1455.96 (17)
C10—C1—C2—C356.27 (18)C18—C13—C14—O14177.02 (14)
O2—C2—C3—O360.48 (19)C17—C13—C14—O1466.27 (15)
C1—C2—C3—O364.39 (18)C12—C13—C14—C858.65 (19)
O2—C2—C3—C4179.65 (14)C18—C13—C14—C862.41 (19)
C1—C2—C3—C454.78 (18)C17—C13—C14—C8179.12 (14)
O3—C3—C4—C565.34 (17)C12—C13—C14—C15170.33 (15)
C2—C3—C4—C554.96 (18)C18—C13—C14—C1568.62 (17)
C3—C4—C5—C6178.60 (13)C17—C13—C14—C1548.10 (16)
C3—C4—C5—C1056.48 (17)O14—C14—C15—C1675.48 (17)
C10—C5—C6—O6145.52 (17)C8—C14—C15—C16165.11 (15)
C4—C5—C6—O688.75 (19)C13—C14—C15—C1637.76 (18)
C10—C5—C6—C737.7 (2)C14—C15—C16—C1712.7 (2)
C4—C5—C6—C788.01 (17)C15—C16—C17—C20144.97 (16)
O6—C6—C7—C8176.99 (17)C15—C16—C17—C1316.7 (2)
C5—C6—C7—C86.3 (2)C12—C13—C17—C2080.6 (2)
C6—C7—C8—C14165.68 (16)C18—C13—C17—C2048.0 (2)
C6—C7—C8—C94.9 (3)C14—C13—C17—C20163.83 (15)
C7—C8—C9—C11145.05 (19)C12—C13—C17—C16154.41 (16)
C14—C8—C9—C1143.6 (2)C18—C13—C17—C1676.96 (19)
C7—C8—C9—C1015.9 (2)C14—C13—C17—C1638.86 (17)
C14—C8—C9—C10172.75 (14)C16—C17—C20—C21174.2 (2)
C6—C5—C10—C1965.99 (17)C13—C17—C20—C2153.9 (3)
C4—C5—C10—C19170.37 (14)C16—C17—C20—C2259.8 (2)
C6—C5—C10—C1177.58 (15)C13—C17—C20—C22179.80 (16)
C4—C5—C10—C153.94 (18)C21—C20—C22—O22A77.0 (13)
C6—C5—C10—C956.53 (19)C17—C20—C22—O22A154.9 (13)
C4—C5—C10—C967.11 (18)C21—C20—C22—O22B68.2 (12)
C2—C1—C10—C554.37 (19)C17—C20—C22—O22B163.7 (12)
C2—C1—C10—C19171.18 (15)C21—C20—C22—C23A45.7 (8)
C2—C1—C10—C965.57 (19)C17—C20—C22—C23A82.4 (8)
C8—C9—C10—C545.51 (19)C21—C20—C22—C23B57.4 (8)
C11—C9—C10—C5174.83 (16)C17—C20—C22—C23B70.7 (7)
C8—C9—C10—C1974.86 (19)O22A—C22—C23A—C24A70.6 (16)
C11—C9—C10—C1954.5 (2)O22B—C22—C23A—C24A74.4 (15)
C8—C9—C10—C1164.29 (14)C23B—C22—C23A—C24A40 (3)
C11—C9—C10—C166.4 (2)C20—C22—C23A—C24A171.5 (8)
C8—C9—C11—C1245.2 (2)C22—C23A—C24A—C25A94.6 (12)
C10—C9—C11—C12174.02 (18)C23A—C24A—C25A—O25A62.3 (10)
C9—C11—C12—C1354.3 (3)C23A—C24A—C25A—C27A56.7 (10)
C11—C12—C13—C1861.2 (2)C23A—C24A—C25A—C26A179.9 (9)
C11—C12—C13—C1459.0 (2)O22A—C22—C23B—C24B58.7 (18)
C11—C12—C13—C17170.24 (17)O22B—C22—C23B—C24B64.6 (14)
C7—C8—C14—O14107.13 (18)C23A—C22—C23B—C24B134 (4)
C9—C8—C14—O1464.28 (18)C20—C22—C23B—C24B172.2 (6)
C7—C8—C14—C1514.3 (3)C22—C23B—C24B—C25B96.8 (10)
C9—C8—C14—C15174.33 (15)C23B—C24B—C25B—O25B57.4 (8)
C7—C8—C14—C13136.86 (17)C23B—C24B—C25B—C27B60.6 (9)
C9—C8—C14—C1351.73 (19)C23B—C24B—C25B—C26B176.6 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.821.952.7494 (19)165
O3—H3···O6i0.822.032.8019 (16)156
O14—H14···O22Aii0.821.862.68 (3)172
O14—H14···O22Bii0.822.082.89 (3)172
O22A—H22C···O25A0.821.892.71 (2)171
O25A—H25A···O2iii0.821.952.760 (10)171
O22B—H22D···O25B0.821.812.63 (2)172
O25B—H25B···O2iii0.821.922.733 (9)170
Symmetry codes: (i) x1/2, y+3/2, z+2; (ii) x+1, y1/2, z+3/2; (iii) x, y+1/2, z+3/2.
(II) 2β,3β,14α,20R,22R,25-hexahydroxy-5β-cholest-7-en-6-one top
Crystal data top
C27H44O7Dx = 1.195 Mg m3
Mr = 480.62Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 7.663 (1) Åθ = 30.6–34.6°
b = 10.541 (1) ŵ = 0.69 mm1
c = 33.084 (2) ÅT = 293 K
V = 2672.4 (5) Å3Block, colorless
Z = 40.45 × 0.30 × 0.20 mm
F(000) = 1048
Data collection top
Enraf-Nonius CAD4
diffractometer
4155 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.013
Graphite monochromatorθmax = 75.0°, θmin = 2.7°
ω–2θ scansh = 89
Absorption correction: ψ scan
North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24 350-359
k = 1311
Tmin = 0.748, Tmax = 0.875l = 3541
5611 measured reflections3 standard reflections every 60 min
4542 independent reflections intensity decay: 4%
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)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0671P)2 + 0.236P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.003
4542 reflectionsΔρmax = 0.25 e Å3
375 parametersΔρmin = 0.21 e Å3
244 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.19 (18)
Crystal data top
C27H44O7V = 2672.4 (5) Å3
Mr = 480.62Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 7.663 (1) ŵ = 0.69 mm1
b = 10.541 (1) ÅT = 293 K
c = 33.084 (2) Å0.45 × 0.30 × 0.20 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
4155 reflections with I > 2σ(I)
Absorption correction: ψ scan
North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24 350-359
Rint = 0.013
Tmin = 0.748, Tmax = 0.8753 standard reflections every 60 min
5611 measured reflections intensity decay: 4%
4542 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104Δρmax = 0.25 e Å3
S = 1.06Δρmin = 0.21 e Å3
4542 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
375 parametersAbsolute structure parameter: 0.19 (18)
244 restraints
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)
O20.0355 (2)0.62347 (15)0.96440 (4)0.0693 (4)
H20.01710.68110.97580.090*
O30.3608 (2)0.68324 (16)0.99655 (4)0.0748 (4)
H30.31090.63281.01150.097*
O60.75094 (19)0.93922 (15)0.92395 (4)0.0691 (4)
O140.41491 (16)0.75598 (10)0.78838 (4)0.0472 (3)
H140.50980.72040.79010.061*
O200.24557 (17)1.14640 (11)0.70634 (4)0.0536 (3)
H200.21141.18430.68620.070*
O220.1573 (2)1.06787 (13)0.63538 (4)0.0726 (4)
H220.17321.05030.61150.094*
C10.1477 (3)0.8181 (2)0.93521 (5)0.0564 (5)
H1A0.14480.85390.96220.073*
H1B0.03590.83570.92260.073*
C20.1684 (3)0.6761 (2)0.93878 (5)0.0557 (5)
H2A0.15660.63880.91180.072*
C30.3471 (3)0.6408 (2)0.95557 (6)0.0604 (5)
H3A0.36160.54850.95460.079*
C40.4922 (3)0.70360 (19)0.93144 (6)0.0569 (5)
H4A0.49380.66870.90430.074*
H4B0.60360.68490.94400.074*
C50.4678 (2)0.84785 (18)0.92906 (5)0.0500 (4)
H50.47150.88050.95680.065*
C60.6163 (2)0.90738 (18)0.90649 (6)0.0529 (4)
C70.5971 (2)0.92146 (17)0.86264 (6)0.0505 (4)
H70.69200.95030.84770.066*
C80.4482 (2)0.89443 (15)0.84327 (5)0.0423 (3)
C90.2848 (2)0.85086 (17)0.86540 (5)0.0448 (3)
H90.28510.75800.86420.058*
C100.2902 (2)0.88614 (16)0.91099 (5)0.0481 (4)
C110.1130 (2)0.8942 (2)0.84513 (5)0.0599 (5)
H11A0.01870.84140.85510.078*
H11B0.08880.98070.85350.078*
C120.1122 (2)0.8891 (2)0.79898 (5)0.0533 (4)
H12A0.00650.92880.78900.069*
H12B0.11200.80120.79030.069*
C130.2714 (2)0.95680 (15)0.78091 (5)0.0416 (3)
C140.4352 (2)0.88873 (14)0.79766 (5)0.0403 (3)
C150.5822 (2)0.94153 (17)0.77174 (5)0.0478 (4)
H15A0.68330.88630.77240.062*
H15B0.61621.02550.78070.062*
C160.5015 (2)0.94617 (17)0.72912 (5)0.0484 (4)
H16A0.54360.87590.71290.063*
H16B0.53221.02490.71570.063*
C170.2999 (2)0.93691 (15)0.73476 (5)0.0427 (3)
H170.27010.84800.72950.056*
C180.2756 (3)1.09734 (16)0.79339 (6)0.0533 (4)
H18A0.16651.13660.78650.080*
H18B0.36871.13960.77940.080*
H18C0.29411.10350.82200.080*
C190.2662 (3)1.0292 (2)0.91743 (6)0.0687 (5)
H19A0.29631.05060.94480.103*
H19B0.14681.05170.91240.103*
H19C0.34061.07470.89910.103*
C200.1935 (2)1.01479 (15)0.70384 (5)0.0460 (4)
C210.0027 (2)1.0076 (2)0.71122 (6)0.0599 (5)
H21A0.03161.05480.73510.090*
H21B0.03660.92060.71470.090*
H21C0.06351.04280.68850.090*
C220.2374 (3)0.97334 (16)0.66031 (5)0.0586 (5)
H22A0.36400.97140.65610.076*0.50
H22B0.36330.98670.65740.076*0.50
C23A0.1545 (15)0.8445 (7)0.6493 (3)0.065 (2)0.50
H23A0.02870.85510.64920.085*0.50
H23B0.18240.78480.67070.085*0.50
C24A0.2086 (14)0.7847 (9)0.6086 (2)0.099 (3)0.50
H24A0.33520.78470.60800.129*0.50
H24B0.17250.69650.60950.129*0.50
C25A0.1496 (11)0.8356 (8)0.5698 (2)0.074 (2)0.50
O25A0.2308 (17)0.9592 (9)0.5645 (3)0.081 (3)0.50
H25A0.16901.00350.55000.105*0.50
C26A0.0497 (9)0.8407 (7)0.5709 (3)0.091 (2)0.50
H26A0.09490.75790.57690.136*0.50
H26B0.09280.86810.54510.136*0.50
H26C0.08650.89940.59130.136*0.50
C27A0.1940 (11)0.7503 (8)0.5350 (2)0.094 (2)0.50
H27A0.31580.72920.53590.142*0.50
H27B0.16880.79290.51000.142*0.50
H27C0.12590.67400.53670.142*0.50
C23B0.2064 (16)0.8347 (7)0.6486 (3)0.076 (3)0.50
H23C0.08170.81990.64700.099*0.50
H23D0.25230.78070.66980.099*0.50
C24B0.2905 (13)0.7958 (8)0.6082 (2)0.090 (3)0.50
H24C0.41020.82540.60910.117*0.50
H24D0.29560.70390.60820.117*0.50
C25B0.2230 (11)0.8324 (9)0.5689 (3)0.079 (2)0.50
O25B0.2204 (15)0.9693 (9)0.5633 (3)0.072 (3)0.50
H25B0.13430.98920.55000.093*0.50
C26B0.0340 (14)0.7986 (12)0.5676 (5)0.177 (6)0.50
H26D0.02620.84080.58920.266*0.50
H26E0.02110.70850.57050.266*0.50
H26F0.01440.82470.54220.266*0.50
C27B0.3150 (15)0.7749 (8)0.5340 (2)0.132 (4)0.50
H27D0.25480.79650.50950.199*0.50
H27E0.31730.68430.53700.199*0.50
H27F0.43230.80660.53280.199*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0701 (9)0.0820 (10)0.0558 (7)0.0153 (8)0.0084 (7)0.0010 (7)
O30.0765 (10)0.0967 (11)0.0512 (7)0.0197 (9)0.0155 (7)0.0172 (7)
O60.0481 (7)0.0920 (10)0.0671 (8)0.0058 (7)0.0150 (7)0.0023 (7)
O140.0473 (6)0.0374 (5)0.0568 (6)0.0036 (5)0.0004 (5)0.0030 (5)
O200.0556 (7)0.0406 (5)0.0647 (7)0.0043 (5)0.0125 (6)0.0099 (5)
O220.1060 (12)0.0580 (8)0.0539 (7)0.0033 (8)0.0132 (8)0.0140 (6)
C10.0458 (10)0.0773 (13)0.0460 (9)0.0113 (9)0.0070 (7)0.0065 (8)
C20.0520 (10)0.0734 (12)0.0416 (8)0.0043 (9)0.0012 (8)0.0016 (8)
C30.0650 (12)0.0579 (11)0.0583 (11)0.0037 (10)0.0086 (9)0.0037 (9)
C40.0480 (10)0.0626 (11)0.0602 (10)0.0129 (8)0.0068 (8)0.0029 (9)
C50.0461 (9)0.0593 (10)0.0446 (8)0.0055 (8)0.0051 (7)0.0037 (8)
C60.0407 (9)0.0602 (10)0.0576 (10)0.0052 (8)0.0073 (8)0.0038 (8)
C70.0369 (8)0.0588 (10)0.0557 (9)0.0006 (8)0.0010 (7)0.0016 (8)
C80.0343 (8)0.0417 (8)0.0509 (8)0.0065 (6)0.0009 (6)0.0028 (7)
C90.0343 (8)0.0547 (8)0.0453 (8)0.0047 (7)0.0009 (7)0.0046 (7)
C100.0427 (9)0.0557 (10)0.0459 (8)0.0117 (8)0.0026 (7)0.0018 (7)
C110.0312 (8)0.0950 (15)0.0535 (10)0.0070 (9)0.0019 (7)0.0161 (10)
C120.0319 (8)0.0761 (12)0.0520 (9)0.0025 (8)0.0026 (7)0.0140 (9)
C130.0334 (7)0.0432 (8)0.0481 (8)0.0015 (7)0.0000 (6)0.0049 (6)
C140.0338 (8)0.0382 (7)0.0489 (8)0.0004 (6)0.0006 (6)0.0037 (7)
C150.0358 (8)0.0500 (9)0.0576 (9)0.0009 (7)0.0047 (7)0.0054 (7)
C160.0437 (9)0.0481 (9)0.0533 (9)0.0042 (7)0.0061 (7)0.0110 (7)
C170.0424 (8)0.0377 (7)0.0481 (8)0.0006 (7)0.0011 (7)0.0052 (6)
C180.0542 (10)0.0494 (9)0.0564 (9)0.0112 (8)0.0036 (8)0.0019 (7)
C190.0734 (14)0.0614 (11)0.0712 (12)0.0207 (11)0.0032 (11)0.0046 (9)
C200.0464 (9)0.0410 (8)0.0506 (8)0.0052 (7)0.0044 (7)0.0060 (7)
C210.0462 (10)0.0702 (12)0.0633 (11)0.0065 (9)0.0116 (8)0.0132 (9)
C220.0763 (13)0.0498 (9)0.0495 (9)0.0000 (10)0.0025 (9)0.0114 (7)
C23A0.092 (5)0.046 (3)0.057 (3)0.001 (3)0.013 (3)0.007 (2)
C24A0.165 (8)0.064 (3)0.068 (4)0.008 (5)0.005 (5)0.001 (3)
C25A0.114 (7)0.054 (3)0.053 (3)0.015 (4)0.001 (4)0.007 (2)
O25A0.112 (6)0.074 (5)0.056 (4)0.016 (4)0.014 (4)0.012 (3)
C26A0.104 (5)0.058 (3)0.110 (4)0.028 (3)0.039 (4)0.016 (3)
C27A0.134 (6)0.095 (4)0.054 (3)0.004 (5)0.003 (4)0.006 (3)
C23B0.123 (8)0.051 (3)0.055 (3)0.005 (4)0.001 (4)0.001 (3)
C24B0.155 (8)0.055 (3)0.061 (3)0.030 (4)0.020 (4)0.004 (3)
C25B0.109 (6)0.061 (3)0.067 (3)0.013 (4)0.005 (4)0.005 (3)
O25B0.086 (5)0.049 (3)0.081 (5)0.017 (3)0.017 (4)0.018 (3)
C26B0.190 (14)0.126 (10)0.215 (11)0.057 (9)0.025 (11)0.041 (9)
C27B0.230 (11)0.088 (5)0.079 (4)0.036 (7)0.033 (7)0.004 (4)
Geometric parameters (Å, º) top
O2—C21.437 (2)C13—C181.538 (2)
O3—C31.432 (2)C13—C141.548 (2)
O6—C61.229 (2)C13—C171.557 (2)
O14—C141.4409 (19)C14—C151.521 (2)
O20—C201.446 (2)C15—C161.540 (2)
O22—C221.432 (2)C16—C171.559 (2)
C1—C21.510 (3)C17—C201.544 (2)
C1—C101.532 (3)C20—C211.525 (3)
C2—C31.524 (3)C20—C221.542 (2)
C3—C41.520 (3)C22—C23B1.530 (6)
C4—C51.534 (3)C22—C23A1.542 (6)
C5—C61.499 (3)C23A—C24A1.544 (6)
C5—C101.540 (2)C24A—C25A1.466 (7)
C6—C71.466 (3)C25A—O25A1.454 (9)
C7—C81.339 (2)C25A—C27A1.500 (8)
C8—C141.513 (2)C25A—C26A1.528 (9)
C8—C91.522 (2)C23B—C24B1.541 (7)
C9—C111.547 (2)C24B—C25B1.449 (6)
C9—C101.554 (2)C25B—O25B1.456 (9)
C10—C191.534 (3)C25B—C27B1.484 (8)
C11—C121.528 (2)C25B—C26B1.492 (9)
C12—C131.534 (2)
C2—C1—C10115.45 (16)C8—C14—C15119.90 (14)
O2—C2—C1110.75 (16)O14—C14—C13106.64 (12)
O2—C2—C3109.14 (15)C8—C14—C13113.09 (13)
C1—C2—C3111.43 (17)C15—C14—C13103.23 (12)
O3—C3—C4107.91 (17)C14—C15—C16103.32 (14)
O3—C3—C2109.57 (16)C15—C16—C17106.63 (13)
C4—C3—C2111.05 (15)C20—C17—C13120.27 (13)
C3—C4—C5111.68 (16)C20—C17—C16114.24 (13)
C6—C5—C4110.35 (16)C13—C17—C16104.36 (13)
C6—C5—C10111.59 (14)O20—C20—C21108.11 (15)
C4—C5—C10112.79 (16)O20—C20—C22105.36 (13)
O6—C6—C7121.46 (18)C21—C20—C22110.53 (16)
O6—C6—C5121.17 (16)O20—C20—C17109.05 (13)
C7—C6—C5117.33 (15)C21—C20—C17112.82 (14)
C8—C7—C6122.53 (16)C22—C20—C17110.65 (14)
C7—C8—C14122.82 (15)O22—C22—C23B116.9 (5)
C7—C8—C9122.35 (15)O22—C22—C20104.31 (15)
C14—C8—C9114.41 (13)C23B—C22—C20118.2 (4)
C8—C9—C11113.75 (13)O22—C22—C23A107.5 (5)
C8—C9—C10111.90 (14)C20—C22—C23A112.3 (4)
C11—C9—C10111.88 (13)C22—C23A—C24A117.0 (6)
C1—C10—C19107.58 (16)C25A—C24A—C23A122.2 (8)
C1—C10—C5107.71 (14)O25A—C25A—C24A107.5 (8)
C19—C10—C5108.02 (17)O25A—C25A—C27A110.3 (7)
C1—C10—C9112.12 (15)C24A—C25A—C27A112.6 (7)
C19—C10—C9111.52 (14)O25A—C25A—C26A113.5 (8)
C5—C10—C9109.73 (13)C24A—C25A—C26A107.5 (7)
C12—C11—C9115.23 (14)C27A—C25A—C26A105.5 (7)
C11—C12—C13111.72 (15)C22—C23B—C24B114.1 (7)
C12—C13—C18111.09 (15)C25B—C24B—C23B123.9 (8)
C12—C13—C14106.82 (12)C24B—C25B—O25B112.5 (8)
C18—C13—C14109.46 (13)C24B—C25B—C27B114.8 (7)
C12—C13—C17115.55 (14)O25B—C25B—C27B108.1 (8)
C18—C13—C17112.96 (13)C24B—C25B—C26B108.1 (9)
C14—C13—C17100.08 (12)O25B—C25B—C26B102.7 (8)
O14—C14—C8104.96 (12)C27B—C25B—C26B109.9 (9)
O14—C14—C15108.35 (13)
C10—C1—C2—O2175.82 (15)C12—C13—C14—O1454.16 (16)
C10—C1—C2—C354.1 (2)C18—C13—C14—O14174.53 (13)
O2—C2—C3—O356.2 (2)C17—C13—C14—O1466.59 (14)
C1—C2—C3—O366.5 (2)C12—C13—C14—C860.70 (17)
O2—C2—C3—C4175.27 (17)C18—C13—C14—C859.67 (17)
C1—C2—C3—C452.7 (2)C17—C13—C14—C8178.56 (13)
O3—C3—C4—C565.5 (2)C12—C13—C14—C15168.23 (14)
C2—C3—C4—C554.6 (2)C18—C13—C14—C1571.40 (16)
C3—C4—C5—C6177.80 (15)C17—C13—C14—C1547.48 (15)
C3—C4—C5—C1056.6 (2)O14—C14—C15—C1672.36 (15)
C4—C5—C6—O687.5 (2)C8—C14—C15—C16167.35 (14)
C10—C5—C6—O6146.32 (18)C13—C14—C15—C1640.48 (16)
C4—C5—C6—C790.25 (19)C14—C15—C16—C1717.34 (17)
C10—C5—C6—C736.0 (2)C12—C13—C17—C2080.28 (19)
O6—C6—C7—C8175.98 (18)C18—C13—C17—C2049.19 (19)
C5—C6—C7—C86.3 (3)C14—C13—C17—C20165.48 (13)
C6—C7—C8—C14170.11 (16)C12—C13—C17—C16149.93 (14)
C6—C7—C8—C92.0 (3)C18—C13—C17—C1680.60 (16)
C7—C8—C9—C11147.80 (19)C14—C13—C17—C1635.68 (15)
C14—C8—C9—C1139.5 (2)C15—C16—C17—C20145.22 (14)
C7—C8—C9—C1019.8 (2)C15—C16—C17—C1311.92 (17)
C14—C8—C9—C10167.48 (13)C13—C17—C20—O2067.60 (18)
C2—C1—C10—C19169.54 (17)C16—C17—C20—O2057.68 (19)
C2—C1—C10—C553.3 (2)C13—C17—C20—C2152.5 (2)
C2—C1—C10—C967.50 (19)C16—C17—C20—C21177.82 (16)
C6—C5—C10—C1178.47 (15)C13—C17—C20—C22176.95 (14)
C4—C5—C10—C153.58 (19)C16—C17—C20—C2257.76 (19)
C6—C5—C10—C1965.60 (19)O20—C20—C22—O2251.49 (19)
C4—C5—C10—C19169.51 (16)C21—C20—C22—O2265.08 (19)
C6—C5—C10—C956.16 (19)C17—C20—C22—O22169.22 (15)
C4—C5—C10—C968.72 (19)O20—C20—C22—C23B176.7 (6)
C8—C9—C10—C1167.39 (14)C21—C20—C22—C23B66.7 (6)
C11—C9—C10—C163.61 (19)C17—C20—C22—C23B59.0 (6)
C8—C9—C10—C1971.90 (19)O20—C20—C22—C23A167.6 (5)
C11—C9—C10—C1957.1 (2)C21—C20—C22—C23A51.0 (5)
C8—C9—C10—C547.75 (19)C17—C20—C22—C23A74.7 (5)
C11—C9—C10—C5176.75 (15)O22—C22—C23A—C24A73.7 (9)
C8—C9—C11—C1239.5 (2)C20—C22—C23A—C24A172.2 (7)
C10—C9—C11—C12167.53 (17)C22—C23A—C24A—C25A72.2 (12)
C9—C11—C12—C1351.1 (2)C23A—C24A—C25A—O25A67.7 (11)
C11—C12—C13—C1859.8 (2)C23A—C24A—C25A—C27A170.6 (8)
C11—C12—C13—C1459.48 (19)C23A—C24A—C25A—C26A54.9 (10)
C11—C12—C13—C17169.79 (15)O22—C22—C23B—C24B66.8 (10)
C7—C8—C14—O14108.70 (17)C20—C22—C23B—C24B167.3 (6)
C9—C8—C14—O1463.98 (16)C22—C23B—C24B—C25B74.7 (12)
C7—C8—C14—C1513.3 (2)C23B—C24B—C25B—O25B61.0 (12)
C9—C8—C14—C15174.04 (14)C23B—C24B—C25B—C27B174.7 (8)
C7—C8—C14—C13135.44 (16)C23B—C24B—C25B—C26B51.7 (12)
C9—C8—C14—C1351.88 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.821.942.759 (2)179
O3—H3···O6i0.822.313.048 (2)150
O14—H14···O20ii0.822.032.8520 (17)175
O20—H20···O220.822.122.5795 (19)115
O22—H22···O25A0.821.882.671 (10)161
O22—H22···O25B0.821.842.645 (12)165
O25A—H25A···O2iii0.822.072.842 (14)157
O25B—H25B···O2iii0.821.982.707 (13)147
Symmetry codes: (i) x1/2, y+3/2, z+2; (ii) x+1, y1/2, z+3/2; (iii) x, y+1/2, z+3/2.
(III) 2β,3β,14α,20R,22R,25-hexahydroxy-5β-cholest-7-en-6-one methanol solvate hydrate top
Crystal data top
C27H44O7·CH4O·H2ODx = 1.224 Mg m3
Mr = 530.68Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 7.167 (1) Åθ = 20.1–23.9°
b = 9.703 (1) ŵ = 0.73 mm1
c = 41.412 (4) ÅT = 293 K
V = 2879.8 (6) Å3Prism, colorless
Z = 40.25 × 0.14 × 0.10 mm
F(000) = 1160
Data collection top
Enraf-Nonius CAD4
diffractometer
4751 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.012
Graphite monochromatorθmax = 75.0°, θmin = 2.1°
/w–2/q scansh = 88
Absorption correction: ψ scan
North A.C., Philips D.C. & Mathews F.(1968): Acta Cryst. A24 350-359
k = 1212
Tmin = 0.838, Tmax = 0.930l = 5151
6775 measured reflections3 standard reflections every 1hr min
5774 independent reflections intensity decay: 10%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.038 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.121(Δ/σ)max = 0.014
S = 0.86Δρmax = 0.23 e Å3
5774 reflectionsΔρmin = 0.15 e Å3
356 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraintsExtinction coefficient: 0.0017 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.09 (17)
Crystal data top
C27H44O7·CH4O·H2OV = 2879.8 (6) Å3
Mr = 530.68Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 7.167 (1) ŵ = 0.73 mm1
b = 9.703 (1) ÅT = 293 K
c = 41.412 (4) Å0.25 × 0.14 × 0.10 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
4751 reflections with I > 2σ(I)
Absorption correction: ψ scan
North A.C., Philips D.C. & Mathews F.(1968): Acta Cryst. A24 350-359
Rint = 0.012
Tmin = 0.838, Tmax = 0.9303 standard reflections every 1hr min
6775 measured reflections intensity decay: 10%
5774 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121Δρmax = 0.23 e Å3
S = 0.86Δρmin = 0.15 e Å3
5774 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
356 parametersAbsolute structure parameter: 0.09 (17)
3 restraints
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
O20.9975 (2)0.71492 (19)0.73477 (4)0.0510 (4)
H20.935 (3)0.771 (3)0.7274 (6)0.066*
O30.6431 (2)0.62436 (19)0.71560 (3)0.0489 (4)
H30.695 (3)0.629 (2)0.6965 (6)0.064*
O60.2328 (2)0.44281 (17)0.79407 (4)0.0489 (4)
O140.87180 (19)0.25902 (14)0.84914 (3)0.0349 (3)
H140.8108 (14)0.205 (2)0.8352 (4)0.045*
O200.8978 (2)0.41424 (15)0.96825 (3)0.0413 (3)
H200.824 (4)0.3647 (17)0.9769 (5)0.054*
O221.1230 (2)0.22470 (19)0.99697 (3)0.0511 (4)
H221.056 (4)0.284 (3)1.0055 (4)0.066*
O251.5492 (2)0.02393 (17)0.97293 (4)0.0535 (4)
H251.517 (2)0.002 (3)0.9950 (7)0.069*
C10.7907 (3)0.7172 (2)0.78106 (4)0.0382 (4)
H1A0.71790.78710.77000.050*
H1B0.88440.76410.79390.050*
C20.8888 (3)0.6295 (2)0.75594 (5)0.0391 (4)
H2A0.97500.56800.76730.051*
C30.7549 (3)0.5399 (2)0.73653 (4)0.0388 (4)
H3A0.82700.47480.72340.050*
C40.6247 (3)0.4601 (2)0.75867 (4)0.0373 (4)
H4A0.69640.39200.77050.048*
H4B0.53340.41140.74570.048*
C50.5227 (3)0.5540 (2)0.78275 (4)0.0344 (4)
H50.44720.61980.77040.045*
C60.3928 (3)0.4669 (2)0.80270 (5)0.0359 (4)
C70.4723 (3)0.4023 (2)0.83165 (4)0.0350 (4)
H70.39980.34030.84330.045*
C80.6454 (2)0.42965 (18)0.84177 (4)0.0287 (4)
C90.7730 (3)0.53426 (18)0.82557 (4)0.0310 (4)
H90.85230.48130.81080.040*
C100.6609 (3)0.63682 (19)0.80394 (4)0.0334 (4)
C110.9071 (3)0.6057 (2)0.84937 (5)0.0422 (5)
H11A1.00510.65070.83710.055*
H11B0.83880.67680.86090.055*
C120.9971 (3)0.5094 (2)0.87408 (4)0.0375 (4)
H12A1.06880.56340.88940.049*
H12B1.08210.44730.86310.049*
C130.8499 (2)0.42528 (18)0.89226 (4)0.0287 (4)
C140.7390 (3)0.34097 (18)0.86712 (4)0.0288 (4)
C150.6205 (3)0.2433 (2)0.88740 (4)0.0376 (4)
H15A0.58870.16090.87530.049*
H15B0.50650.28790.89450.049*
C160.7481 (3)0.2088 (2)0.91632 (4)0.0395 (4)
H16A0.78680.11310.91540.051*
H16B0.68210.22380.93650.051*
C170.9198 (3)0.30465 (18)0.91423 (4)0.0302 (4)
H171.01250.25460.90140.039*
C180.7151 (3)0.5220 (2)0.91005 (5)0.0438 (5)
H18A0.63990.57050.89460.066*
H18B0.78520.58700.92260.066*
H18C0.63600.46900.92400.066*
C190.5495 (4)0.7400 (2)0.82429 (5)0.0478 (5)
H19A0.63300.80710.83340.072*
H19B0.48650.69200.84140.072*
H19C0.45940.78560.81090.072*
C201.0148 (3)0.33427 (19)0.94712 (4)0.0316 (4)
C211.1908 (3)0.4202 (2)0.94328 (5)0.0415 (5)
H21A1.15720.51440.93920.062*
H21B1.26290.38540.92550.062*
H21C1.26330.41520.96270.062*
C221.0565 (3)0.1963 (2)0.96462 (4)0.0373 (4)
H22A0.94060.14310.96610.048*
C231.2044 (3)0.1075 (2)0.94880 (5)0.0417 (5)
H23A1.32470.15240.95100.054*
H23B1.17730.10000.92590.054*
C241.2163 (3)0.0369 (2)0.96324 (6)0.0470 (5)
H24A1.12080.09380.95340.061*
H24B1.18880.03110.98610.061*
C251.4053 (4)0.1082 (2)0.95899 (5)0.0485 (5)
C261.4584 (6)0.1249 (3)0.92376 (6)0.0750 (9)
H26A1.46020.03630.91350.112*
H26B1.36880.18300.91320.112*
H26C1.57990.16620.92230.112*
C271.4038 (5)0.2468 (3)0.97646 (7)0.0748 (9)
H27A1.51970.29370.97260.112*
H27B1.30250.30190.96850.112*
H27C1.38840.23190.99920.112*
O1W0.7315 (2)0.09113 (18)0.80330 (4)0.0529 (4)
H1W0.630 (2)0.1056 (4)0.79629 (17)0.069*
H2W0.8018 (16)0.1207 (7)0.7891 (3)0.069*
O2X1.1907 (2)0.1096 (2)0.84535 (5)0.0593 (5)
H2X1.107 (4)0.166 (3)0.8474 (8)0.077*
C3X1.1205 (5)0.0238 (3)0.85242 (7)0.0722 (8)
H3X11.08080.02720.87450.108*
H3X21.21680.09100.84890.108*
H3X31.01650.04350.83860.108*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0337 (8)0.0668 (10)0.0524 (8)0.0012 (8)0.0021 (7)0.0207 (8)
O30.0399 (8)0.0727 (10)0.0340 (7)0.0043 (8)0.0056 (6)0.0136 (7)
O60.0295 (7)0.0639 (9)0.0533 (8)0.0012 (7)0.0095 (6)0.0119 (7)
O140.0339 (7)0.0397 (7)0.0310 (6)0.0064 (6)0.0038 (5)0.0077 (5)
O200.0451 (8)0.0493 (8)0.0295 (6)0.0062 (7)0.0046 (6)0.0069 (6)
O220.0641 (10)0.0632 (10)0.0259 (6)0.0169 (9)0.0105 (7)0.0026 (6)
O250.0539 (10)0.0524 (9)0.0541 (9)0.0003 (8)0.0065 (8)0.0048 (8)
C10.0411 (11)0.0355 (9)0.0379 (9)0.0013 (9)0.0044 (8)0.0084 (8)
C20.0290 (10)0.0472 (11)0.0410 (10)0.0023 (8)0.0002 (8)0.0135 (9)
C30.0350 (10)0.0496 (11)0.0319 (8)0.0068 (9)0.0014 (8)0.0044 (8)
C40.0373 (10)0.0412 (10)0.0333 (9)0.0032 (9)0.0031 (8)0.0013 (8)
C50.0307 (9)0.0404 (10)0.0321 (8)0.0051 (8)0.0032 (7)0.0066 (7)
C60.0280 (9)0.0428 (10)0.0368 (9)0.0034 (8)0.0028 (8)0.0023 (8)
C70.0288 (9)0.0406 (10)0.0355 (9)0.0002 (8)0.0002 (7)0.0053 (8)
C80.0289 (9)0.0309 (8)0.0264 (7)0.0024 (7)0.0001 (7)0.0004 (7)
C90.0310 (9)0.0332 (9)0.0288 (8)0.0002 (8)0.0033 (7)0.0033 (7)
C100.0350 (10)0.0331 (8)0.0321 (8)0.0025 (7)0.0011 (8)0.0045 (7)
C110.0461 (12)0.0393 (10)0.0413 (10)0.0130 (10)0.0113 (9)0.0101 (8)
C120.0369 (10)0.0418 (10)0.0339 (8)0.0114 (9)0.0077 (8)0.0045 (8)
C130.0286 (9)0.0317 (8)0.0258 (8)0.0007 (7)0.0003 (6)0.0015 (7)
C140.0270 (9)0.0336 (8)0.0259 (7)0.0028 (7)0.0005 (7)0.0002 (7)
C150.0352 (10)0.0445 (10)0.0332 (9)0.0064 (9)0.0026 (8)0.0063 (8)
C160.0424 (11)0.0434 (10)0.0329 (9)0.0115 (10)0.0058 (8)0.0092 (8)
C170.0349 (9)0.0315 (8)0.0242 (8)0.0006 (7)0.0009 (7)0.0009 (7)
C180.0480 (12)0.0446 (11)0.0389 (10)0.0098 (10)0.0024 (9)0.0069 (8)
C190.0553 (13)0.0418 (11)0.0463 (11)0.0102 (10)0.0022 (10)0.0003 (9)
C200.0329 (9)0.0384 (9)0.0235 (7)0.0004 (8)0.0003 (7)0.0022 (7)
C210.0393 (11)0.0475 (11)0.0377 (10)0.0071 (9)0.0056 (8)0.0023 (9)
C220.0401 (10)0.0470 (11)0.0247 (8)0.0012 (9)0.0050 (7)0.0027 (8)
C230.0493 (12)0.0412 (10)0.0345 (9)0.0050 (9)0.0027 (9)0.0006 (8)
C240.0527 (13)0.0396 (10)0.0488 (11)0.0038 (10)0.0089 (10)0.0012 (9)
C250.0632 (14)0.0345 (10)0.0477 (11)0.0052 (10)0.0114 (11)0.0029 (9)
C260.104 (3)0.0658 (16)0.0549 (14)0.0262 (18)0.0065 (15)0.0165 (13)
C270.093 (2)0.0423 (13)0.089 (2)0.0043 (15)0.0193 (18)0.0125 (13)
O1W0.0441 (9)0.0674 (10)0.0471 (8)0.0051 (8)0.0033 (7)0.0136 (7)
O2X0.0423 (9)0.0720 (11)0.0636 (10)0.0092 (9)0.0017 (8)0.0152 (9)
C3X0.090 (2)0.0636 (16)0.0629 (15)0.0179 (17)0.0011 (16)0.0025 (13)
Geometric parameters (Å, º) top
O2—C21.436 (2)C9—C101.562 (2)
O3—C31.437 (2)C10—C191.533 (3)
O6—C61.224 (2)C11—C121.529 (3)
O14—C141.447 (2)C12—C131.532 (3)
O20—C201.439 (2)C13—C181.535 (3)
O22—C221.448 (2)C13—C141.544 (2)
O25—C251.437 (3)C13—C171.565 (2)
C1—C21.516 (3)C14—C151.524 (3)
C1—C101.540 (3)C15—C161.544 (3)
C2—C31.524 (3)C16—C171.545 (3)
C3—C41.520 (3)C17—C201.550 (2)
C4—C51.537 (3)C20—C211.520 (3)
C5—C61.505 (3)C20—C221.551 (3)
C5—C101.548 (3)C22—C231.515 (3)
C6—C71.468 (3)C23—C241.526 (3)
C7—C81.336 (3)C24—C251.531 (3)
C8—C141.514 (2)C25—C261.516 (3)
C8—C91.522 (2)C25—C271.527 (3)
C9—C111.541 (3)O2X—C3X1.420 (4)
C2—C1—C10114.73 (16)C12—C13—C17117.65 (15)
O2—C2—C1110.30 (17)C18—C13—C17112.31 (15)
O2—C2—C3110.40 (16)C14—C13—C1799.24 (13)
C1—C2—C3112.96 (16)O14—C14—C8104.29 (13)
O3—C3—C4108.18 (17)O14—C14—C15107.97 (15)
O3—C3—C2110.13 (16)C8—C14—C15119.24 (16)
C4—C3—C2111.04 (15)O14—C14—C13107.41 (14)
C3—C4—C5112.40 (16)C8—C14—C13113.23 (14)
C6—C5—C4108.50 (16)C15—C14—C13104.17 (14)
C6—C5—C10112.10 (15)C14—C15—C16103.43 (15)
C4—C5—C10111.79 (15)C15—C16—C17107.32 (14)
O6—C6—C7121.35 (19)C16—C17—C20114.36 (14)
O6—C6—C5121.79 (18)C16—C17—C13103.17 (14)
C7—C6—C5116.66 (16)C20—C17—C13120.87 (15)
C8—C7—C6122.09 (18)O20—C20—C21104.55 (15)
C7—C8—C14121.04 (17)O20—C20—C17112.23 (15)
C7—C8—C9123.54 (16)C21—C20—C17111.98 (15)
C14—C8—C9114.73 (14)O20—C20—C22107.06 (14)
C8—C9—C11113.13 (14)C21—C20—C22111.26 (16)
C8—C9—C10111.62 (15)C17—C20—C22109.59 (15)
C11—C9—C10113.63 (15)O22—C22—C23106.14 (16)
C19—C10—C1108.79 (16)O22—C22—C20109.36 (16)
C19—C10—C5108.50 (17)C23—C22—C20115.05 (16)
C1—C10—C5107.49 (14)C22—C23—C24113.07 (18)
C19—C10—C9111.65 (16)C23—C24—C25114.8 (2)
C1—C10—C9111.39 (16)O25—C25—C26105.5 (2)
C5—C10—C9108.89 (15)O25—C25—C27108.4 (2)
C12—C11—C9114.59 (16)C26—C25—C27111.3 (2)
C11—C12—C13111.36 (16)O25—C25—C24109.38 (16)
C12—C13—C18110.08 (16)C26—C25—C24112.4 (2)
C12—C13—C14107.81 (14)C27—C25—C24109.7 (2)
C18—C13—C14108.87 (15)
C10—C1—C2—O2176.70 (16)C9—C8—C14—O1465.92 (18)
C10—C1—C2—C352.6 (2)C7—C8—C14—C1515.6 (3)
O2—C2—C3—O354.2 (2)C9—C8—C14—C15173.59 (16)
C1—C2—C3—O369.8 (2)C7—C8—C14—C13138.69 (18)
O2—C2—C3—C4174.03 (16)C9—C8—C14—C1350.5 (2)
C1—C2—C3—C450.0 (2)C12—C13—C14—O1456.25 (17)
O3—C3—C4—C567.9 (2)C18—C13—C14—O14175.64 (14)
C2—C3—C4—C553.1 (2)C17—C13—C14—O1466.84 (15)
C3—C4—C5—C6178.02 (16)C12—C13—C14—C858.33 (19)
C3—C4—C5—C1057.9 (2)C18—C13—C14—C861.06 (19)
C4—C5—C6—O688.3 (2)C17—C13—C14—C8178.57 (14)
C10—C5—C6—O6147.8 (2)C12—C13—C14—C15170.62 (15)
C4—C5—C6—C786.6 (2)C18—C13—C14—C1569.99 (18)
C10—C5—C6—C737.3 (2)C17—C13—C14—C1547.53 (17)
O6—C6—C7—C8178.6 (2)O14—C14—C15—C1678.70 (18)
C5—C6—C7—C86.5 (3)C8—C14—C15—C16162.69 (16)
C6—C7—C8—C14166.89 (17)C13—C14—C15—C1635.28 (19)
C6—C7—C8—C93.1 (3)C14—C15—C16—C178.7 (2)
C7—C8—C9—C11148.24 (19)C15—C16—C17—C20153.64 (16)
C14—C8—C9—C1141.2 (2)C15—C16—C17—C1320.5 (2)
C7—C8—C9—C1018.6 (2)C12—C13—C17—C16156.55 (15)
C14—C8—C9—C10170.89 (15)C18—C13—C17—C1674.12 (18)
C2—C1—C10—C19171.32 (17)C14—C13—C17—C1640.77 (17)
C2—C1—C10—C554.0 (2)C12—C13—C17—C2074.2 (2)
C2—C1—C10—C965.2 (2)C18—C13—C17—C2055.2 (2)
C6—C5—C10—C1964.7 (2)C14—C13—C17—C20170.06 (15)
C4—C5—C10—C19173.26 (16)C16—C17—C20—O2067.0 (2)
C6—C5—C10—C1177.86 (15)C13—C17—C20—O2057.2 (2)
C4—C5—C10—C155.77 (19)C16—C17—C20—C21175.79 (16)
C6—C5—C10—C957.1 (2)C13—C17—C20—C2160.0 (2)
C4—C5—C10—C965.02 (19)C16—C17—C20—C2251.8 (2)
C8—C9—C10—C1972.8 (2)C13—C17—C20—C22176.01 (16)
C11—C9—C10—C1956.6 (2)O20—C20—C22—O2250.8 (2)
C8—C9—C10—C1165.35 (15)C21—C20—C22—O2262.9 (2)
C11—C9—C10—C165.3 (2)C17—C20—C22—O22172.72 (16)
C8—C9—C10—C546.98 (19)O20—C20—C22—C23170.08 (16)
C11—C9—C10—C5176.37 (15)C21—C20—C22—C2356.4 (2)
C8—C9—C11—C1242.9 (2)C17—C20—C22—C2368.0 (2)
C10—C9—C11—C12171.54 (17)O22—C22—C23—C2469.1 (2)
C9—C11—C12—C1353.3 (2)C20—C22—C23—C24169.82 (17)
C11—C12—C13—C1859.6 (2)C22—C23—C24—C25155.72 (18)
C11—C12—C13—C1459.0 (2)C23—C24—C25—O2557.2 (2)
C11—C12—C13—C17170.06 (16)C23—C24—C25—C2659.6 (3)
C7—C8—C14—O14104.87 (19)C23—C24—C25—C27176.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O6i0.772.243.007 (2)177
O3—H3···O2Xii0.881.922.794 (2)172
O14—H14···O1W0.891.812.696 (2)169
O20—H20···O22iii0.802.002.787 (2)169
O22—H22···O25iii0.832.503.204 (2)144
O22—H22···O200.832.292.721 (2)113
O25—H25···O20iv0.971.942.871 (2)161
O1W—H1W···O3v0.802.032.815 (2)171
O1W—H2W···O2vi0.831.972.775 (2)165
O2X—H2X···O140.821.912.711 (2)165
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+2, y+1/2, z+3/2; (iii) x1/2, y+1/2, z+2; (iv) x+1/2, y+1/2, z+2; (v) x+1, y1/2, z+3/2; (vi) x+2, y1/2, z+3/2.
(IV) 2β,3β,14α,20R,22R,25-hexahydroxy-5β-cholest-7-en-6-one trihydrate top
Crystal data top
C27H50O10Dx = 1.183 Mg m3
Mr = 534.67Mo Kα radiation, λ = 0.710730 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 11.293 (2) Åθ = 11.5–16.9°
b = 14.202 (2) ŵ = 0.09 mm1
c = 18.721 (3) ÅT = 293 K
V = 3002.5 (8) Å3Prism, colorless
Z = 40.6 × 0.6 × 0.4 mm
F(000) = 1168
Data collection top
Enraf-Nonius CAD4
diffractometer
6759 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.011
Graphite monochromatorθmax = 33.4°, θmin = 2.6°
ω–2θ scansh = 1717
Absorption correction: ψ scan
Reibenspies, J. (1989) DATCOR program for empirical (using intensity measurements) absorption correction, Texas A & M University, College Station, Tx, USA.
k = 2222
Tmin = 0.898, Tmax = 0.972l = 2929
13105 measured reflections2 standard reflections every 60 min
11655 independent reflections intensity decay: none
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)] = 0.054Riding
wR(F2) = 0.142 w = 1/[σ2(Fo2) + (0.0829P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max = 0.001
11655 reflectionsΔρmax = 0.26 e Å3
366 parametersΔρmin = 0.18 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.1 (7)
Crystal data top
C27H50O10V = 3002.5 (8) Å3
Mr = 534.67Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.293 (2) ŵ = 0.09 mm1
b = 14.202 (2) ÅT = 293 K
c = 18.721 (3) Å0.6 × 0.6 × 0.4 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
6759 reflections with I > 2σ(I)
Absorption correction: ψ scan
Reibenspies, J. (1989) DATCOR program for empirical (using intensity measurements) absorption correction, Texas A & M University, College Station, Tx, USA.
Rint = 0.011
Tmin = 0.898, Tmax = 0.9722 standard reflections every 60 min
13105 measured reflections intensity decay: none
11655 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.054Riding
wR(F2) = 0.142Δρmax = 0.26 e Å3
S = 0.92Δρmin = 0.18 e Å3
11655 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
366 parametersAbsolute structure parameter: 0.1 (7)
0 restraints
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)
C10.77408 (14)1.02561 (10)0.01392 (8)0.0322 (3)
H1A0.79741.07770.04440.042*
H1B0.73030.98120.04310.042*
C20.69256 (15)1.06274 (11)0.04407 (9)0.0366 (3)
H20.66311.00940.07210.048*
O20.59454 (13)1.10727 (10)0.00977 (8)0.0553 (4)
H2A0.55621.13700.03940.083*
C30.75590 (17)1.13027 (11)0.09369 (10)0.0415 (4)
H30.70221.14850.13240.054*
O30.78675 (15)1.21142 (9)0.05355 (8)0.0580 (4)
H3A0.80661.25380.08080.087*
C40.86436 (17)1.08198 (11)0.12542 (9)0.0399 (4)
H4A0.83911.02970.15500.052*
H4B0.90671.12620.15550.052*
C50.94797 (15)1.04552 (11)0.06683 (9)0.0356 (3)
H50.97551.10000.03930.046*
C61.05479 (15)1.00078 (12)0.10132 (10)0.0382 (4)
O61.14526 (12)1.04495 (9)0.11276 (9)0.0535 (4)
C71.03915 (15)0.90396 (11)0.12623 (10)0.0382 (4)
H71.09630.87770.15590.050*
C80.94543 (13)0.85215 (10)0.10763 (8)0.0282 (3)
C90.85479 (12)0.88334 (10)0.05330 (8)0.0269 (3)
H90.78130.89520.07970.035*
C100.88652 (13)0.97681 (10)0.01419 (8)0.0297 (3)
C110.82818 (15)0.80203 (10)0.00046 (9)0.0340 (3)
H11A0.76190.82000.02960.044*
H11B0.89640.79300.03030.044*
C120.79886 (14)0.70802 (10)0.03736 (9)0.0324 (3)
H12A0.72570.71440.06410.042*
H12B0.78760.65950.00150.042*
C130.89862 (13)0.67902 (9)0.08796 (7)0.0255 (3)
C140.91480 (13)0.75961 (10)0.14301 (8)0.0290 (3)
O140.80137 (11)0.77454 (8)0.17584 (6)0.0387 (3)
H140.80970.80620.21210.058*
C150.99788 (17)0.71733 (12)0.19799 (9)0.0398 (4)
H15A0.99450.75170.24270.052*
H15B1.07890.71680.18080.052*
C160.94966 (17)0.61677 (11)0.20676 (9)0.0390 (4)
H16A0.90230.61210.24980.051*
H16B1.01440.57210.21010.051*
C170.87246 (13)0.59560 (10)0.13985 (8)0.0276 (3)
H170.78990.60280.15500.036*
C180.97061 (16)0.96075 (14)0.04868 (10)0.0429 (4)
H18A1.03770.92480.03290.060*
H18B0.99691.02040.06690.060*
H18C0.93000.92700.08570.060*
C191.01479 (14)0.66523 (12)0.04681 (10)0.0367 (3)
H19A1.00040.62720.00530.051*
H19B1.07150.63440.07700.051*
H19C1.04520.72540.03240.051*
C200.88544 (13)0.49292 (10)0.11359 (8)0.0282 (3)
O201.00922 (10)0.46874 (8)0.10989 (7)0.0372 (3)
H201.02520.45040.06950.056*
C210.82629 (15)0.47459 (11)0.04189 (9)0.0344 (3)
H21A0.86860.50730.00500.048*
H21B0.74600.49670.04340.048*
H21C0.82700.40820.03210.048*
C220.83453 (14)0.42592 (10)0.17177 (9)0.0329 (3)
H220.86910.44370.21790.043*
O220.87121 (12)0.33132 (8)0.15558 (7)0.0429 (3)
H22A0.94180.33110.14540.064*
C230.70132 (16)0.42510 (14)0.17974 (11)0.0445 (4)
H23A0.66620.39970.13660.058*
H23B0.67340.48930.18530.058*
C240.66071 (19)0.3670 (2)0.24327 (13)0.0688 (7)
H24A0.70460.38750.28500.090*
H24B0.68150.30180.23450.090*
C250.5293 (2)0.3716 (2)0.26069 (13)0.0744 (8)
O250.46699 (15)0.34926 (16)0.19687 (10)0.0787 (5)
H250.39560.35380.20400.118*
C260.4892 (4)0.4702 (4)0.2812 (3)0.144 (2)
H26A0.51650.51440.24610.216*
H26B0.52150.48640.32700.216*
H26C0.40430.47210.28350.216*
C270.5023 (3)0.2994 (5)0.3186 (3)0.190 (3)
H27A0.43040.31660.34270.286*
H27B0.56630.29790.35240.286*
H27C0.49320.23840.29730.286*
O1W0.79973 (17)0.86856 (14)0.30794 (9)0.0773 (5)
H1WA0.85930.83960.31990.116*
H1WB0.84560.90570.32690.116*
O2WA0.7176 (3)1.27327 (19)0.08429 (16)0.0631 (7)0.60
O2WB0.6316 (6)1.2532 (3)0.0992 (3)0.0790 (14)0.40
O3WA0.4788 (5)1.2521 (4)0.0660 (3)0.105 (2)0.50
O3WB0.4589 (4)1.1938 (5)0.1076 (4)0.120 (2)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0360 (8)0.0272 (7)0.0335 (8)0.0010 (6)0.0089 (6)0.0001 (6)
C20.0363 (8)0.0316 (7)0.0417 (9)0.0049 (6)0.0086 (7)0.0047 (6)
O20.0475 (8)0.0567 (8)0.0618 (8)0.0213 (6)0.0204 (7)0.0186 (7)
C30.0516 (10)0.0322 (8)0.0408 (9)0.0069 (7)0.0113 (8)0.0074 (6)
O30.0854 (11)0.0266 (6)0.0621 (9)0.0017 (7)0.0295 (8)0.0008 (6)
C40.0497 (10)0.0292 (7)0.0408 (9)0.0010 (7)0.0144 (7)0.0044 (6)
C50.0367 (8)0.0260 (7)0.0442 (9)0.0096 (6)0.0095 (7)0.0036 (6)
C60.0334 (8)0.0366 (8)0.0446 (9)0.0079 (6)0.0076 (7)0.0012 (7)
O60.0380 (7)0.0457 (7)0.0768 (10)0.0164 (6)0.0158 (7)0.0059 (7)
C70.0319 (8)0.0323 (8)0.0504 (10)0.0026 (6)0.0125 (7)0.0011 (7)
C80.0280 (6)0.0253 (6)0.0313 (7)0.0014 (5)0.0050 (6)0.0023 (5)
C90.0239 (6)0.0238 (6)0.0329 (7)0.0012 (5)0.0054 (5)0.0011 (5)
C100.0286 (7)0.0287 (7)0.0318 (7)0.0036 (6)0.0031 (6)0.0019 (6)
C110.0394 (9)0.0268 (7)0.0359 (8)0.0011 (6)0.0135 (6)0.0004 (6)
C120.0313 (7)0.0274 (7)0.0385 (8)0.0025 (6)0.0113 (6)0.0013 (6)
C130.0251 (6)0.0230 (6)0.0283 (7)0.0011 (5)0.0005 (5)0.0015 (5)
C140.0293 (7)0.0261 (6)0.0317 (7)0.0015 (5)0.0032 (6)0.0028 (6)
O140.0413 (6)0.0347 (6)0.0402 (6)0.0013 (5)0.0085 (5)0.0061 (5)
C150.0469 (9)0.0342 (8)0.0383 (9)0.0041 (7)0.0162 (7)0.0004 (7)
C160.0529 (10)0.0315 (7)0.0326 (8)0.0023 (7)0.0112 (7)0.0003 (6)
C170.0295 (7)0.0247 (6)0.0285 (7)0.0007 (5)0.0018 (6)0.0008 (5)
C180.0410 (9)0.0452 (9)0.0426 (10)0.0059 (7)0.0060 (7)0.0023 (8)
C190.0310 (7)0.0343 (8)0.0446 (9)0.0015 (6)0.0084 (7)0.0032 (7)
C200.0271 (7)0.0254 (6)0.0320 (7)0.0010 (5)0.0031 (6)0.0006 (5)
O200.0303 (5)0.0386 (6)0.0426 (7)0.0057 (5)0.0007 (5)0.0036 (5)
C210.0396 (8)0.0287 (7)0.0349 (8)0.0004 (6)0.0054 (6)0.0007 (6)
C220.0362 (8)0.0270 (7)0.0357 (8)0.0025 (6)0.0061 (6)0.0023 (6)
O220.0436 (7)0.0260 (5)0.0591 (8)0.0025 (5)0.0090 (6)0.0064 (5)
C230.0345 (8)0.0451 (9)0.0539 (11)0.0042 (7)0.0035 (8)0.0115 (8)
C240.0457 (11)0.1024 (19)0.0585 (13)0.0175 (12)0.0019 (10)0.0344 (13)
C250.0476 (13)0.126 (2)0.0492 (12)0.0233 (14)0.0043 (10)0.0176 (14)
O250.0453 (9)0.1140 (15)0.0766 (11)0.0128 (10)0.0008 (8)0.0133 (11)
C260.086 (2)0.204 (5)0.142 (4)0.012 (3)0.044 (2)0.087 (4)
C270.071 (2)0.342 (8)0.158 (4)0.051 (3)0.004 (2)0.162 (5)
O1W0.0810 (12)0.0875 (12)0.0632 (10)0.0132 (10)0.0036 (9)0.0324 (9)
O2WA0.074 (2)0.0469 (14)0.0683 (17)0.0070 (14)0.0010 (15)0.0057 (12)
O2WB0.112 (4)0.047 (2)0.079 (3)0.018 (3)0.021 (3)0.015 (2)
O3WA0.107 (4)0.098 (4)0.112 (4)0.068 (3)0.038 (3)0.044 (3)
O3WB0.064 (3)0.161 (6)0.136 (5)0.037 (3)0.008 (3)0.077 (4)
Geometric parameters (Å, º) top
C1—C21.518 (2)C13—C191.534 (2)
C1—C101.539 (2)C13—C141.5511 (19)
C2—O21.428 (2)C13—C171.560 (2)
C2—C31.515 (2)C14—O141.4365 (19)
C3—O31.419 (2)C14—C151.517 (2)
C3—C41.524 (2)C15—C161.537 (2)
C4—C51.537 (3)C16—C171.555 (2)
C5—C61.509 (2)C17—C201.5459 (19)
C5—C101.551 (2)C20—O201.4411 (18)
C6—O61.218 (2)C20—C211.522 (2)
C6—C71.463 (2)C20—C221.556 (2)
C7—C81.335 (2)C22—O221.4383 (19)
C8—C91.509 (2)C22—C231.512 (2)
C8—C141.512 (2)C23—C241.518 (3)
C9—C111.550 (2)C24—C251.521 (3)
C9—C101.558 (2)C25—O251.422 (3)
C10—C181.529 (2)C25—C261.522 (6)
C11—C121.539 (2)C25—C271.523 (5)
C12—C131.528 (2)
C2—C1—C10114.34 (13)C12—C13—C17116.80 (12)
O2—C2—C3111.20 (13)C19—C13—C17112.20 (12)
O2—C2—C1107.60 (14)C14—C13—C1799.72 (11)
C3—C2—C1111.85 (15)O14—C14—C8105.26 (11)
O3—C3—C2107.78 (14)O14—C14—C15108.65 (13)
O3—C3—C4111.99 (16)C8—C14—C15120.00 (13)
C2—C3—C4109.48 (13)O14—C14—C13106.75 (11)
C3—C4—C5111.54 (14)C8—C14—C13112.17 (12)
C6—C5—C4109.12 (14)C15—C14—C13103.39 (12)
C6—C5—C10111.39 (13)C14—C15—C16102.78 (13)
C4—C5—C10112.99 (13)C15—C16—C17106.98 (13)
O6—C6—C7121.97 (16)C20—C17—C16112.66 (12)
O6—C6—C5121.95 (15)C20—C17—C13120.02 (12)
C7—C6—C5115.84 (14)C16—C17—C13104.39 (11)
C8—C7—C6122.05 (15)O20—C20—C21110.04 (12)
C7—C8—C9123.47 (13)O20—C20—C17109.39 (11)
C7—C8—C14123.11 (14)C21—C20—C17113.59 (12)
C9—C8—C14113.28 (12)O20—C20—C22104.26 (12)
C8—C9—C11110.05 (11)C21—C20—C22110.52 (12)
C8—C9—C10114.25 (11)C17—C20—C22108.61 (12)
C11—C9—C10112.30 (12)O22—C22—C23107.47 (13)
C18—C10—C1108.43 (13)O22—C22—C20108.49 (13)
C18—C10—C5107.76 (13)C23—C22—C20116.19 (13)
C1—C10—C5107.64 (12)C22—C23—C24112.46 (16)
C18—C10—C9112.18 (13)C23—C24—C25116.1 (2)
C1—C10—C9110.77 (12)O25—C25—C24107.0 (2)
C5—C10—C9109.91 (12)O25—C25—C26105.7 (3)
C12—C11—C9113.67 (13)C24—C25—C26112.6 (3)
C13—C12—C11110.69 (12)O25—C25—C27110.4 (3)
C12—C13—C19110.71 (13)C24—C25—C27108.6 (3)
C12—C13—C14107.44 (11)C26—C25—C27112.3 (4)
C19—C13—C14109.10 (12)
(V) 2β,3β,5β,14α,20R,22R,25-heptahydroxy-5β-cholest-7-en-6-one hydrate top
Crystal data top
C27H44O8·H2ODx = 1.243 Mg m3
Mr = 514.64Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 7.163 (1) Åθ = 25.0–29.0°
b = 10.303 (1) ŵ = 0.76 mm1
c = 37.254 (2) ÅT = 293 K
V = 2749.4 (5) Å3Block, colorless
Z = 40.50 × 0.15 × 0.10 mm
F(000) = 1120
Data collection top
Enraf-Nonius CAD4
diffractometer
4972 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.009
Graphite monochromatorθmax = 74.9°, θmin = 2.4°
ω–2θ scansh = 88
Absorption correction: ψ scan
North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24 350-359
k = 1212
Tmin = 0.896, Tmax = 0.927l = 4646
6667 measured reflections3 standard reflections every 60 min
5553 independent reflections intensity decay: 6%
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)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0701P)2 + 0.1608P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
5553 reflectionsΔρmax = 0.18 e Å3
338 parametersΔρmin = 0.20 e Å3
5 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (14)
Crystal data top
C27H44O8·H2OV = 2749.4 (5) Å3
Mr = 514.64Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 7.163 (1) ŵ = 0.76 mm1
b = 10.303 (1) ÅT = 293 K
c = 37.254 (2) Å0.50 × 0.15 × 0.10 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
4972 reflections with I > 2σ(I)
Absorption correction: ψ scan
North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24 350-359
Rint = 0.009
Tmin = 0.896, Tmax = 0.9273 standard reflections every 60 min
6667 measured reflections intensity decay: 6%
5553 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104Δρmax = 0.18 e Å3
S = 1.07Δρmin = 0.20 e Å3
5553 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
338 parametersAbsolute structure parameter: 0.03 (14)
5 restraints
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
O10.0959 (2)0.92930 (13)0.00774 (4)0.0557 (4)
H1C0.0563 (9)0.8524 (17)0.01101 (8)0.072*
H1D0.005 (2)0.9704 (9)0.00276 (12)0.072*
O20.15418 (18)0.9277 (2)0.28169 (4)0.0820 (7)
H20.247 (4)0.9256 (2)0.2679 (5)0.107*
O30.24014 (18)0.92163 (16)0.30623 (4)0.0579 (4)
H30.185 (2)0.9671 (18)0.3176 (4)0.075*
O50.48168 (18)0.95482 (14)0.25223 (4)0.0510 (3)
H50.4235 (17)0.9698 (5)0.2724 (6)0.066*
O60.67995 (19)0.7780 (2)0.21861 (5)0.0869 (7)
O140.05621 (15)0.55343 (11)0.16018 (3)0.0360 (2)
H140.1045 (13)0.5235 (8)0.1779 (5)0.047*
O200.02706 (18)0.66991 (11)0.02600 (3)0.0373 (3)
H200.110 (3)0.6260 (14)0.02110 (16)0.048*
O220.21964 (18)0.48018 (12)0.00109 (3)0.0412 (3)
H220.134 (2)0.4950 (4)0.0165 (4)0.054*
O250.4074 (2)0.02712 (11)0.04529 (4)0.0488 (3)
H250.311 (3)0.0061 (7)0.0357 (3)0.063*
C10.0713 (3)0.97569 (18)0.23495 (5)0.0495 (5)
H1A0.12391.04750.24840.064*
H1B0.03101.00920.22060.064*
C20.0037 (2)0.8765 (2)0.26085 (5)0.0482 (5)
H2A0.05240.80360.24680.063*
C30.1486 (2)0.8246 (2)0.28509 (5)0.0459 (4)
H3A0.09570.75860.30110.060*
C40.2962 (2)0.76195 (16)0.26122 (4)0.0387 (3)
H4A0.24120.68890.24870.050*
H4B0.39670.72910.27610.050*
C50.3769 (2)0.85759 (16)0.23365 (4)0.0371 (4)
C60.5153 (2)0.7822 (2)0.21054 (5)0.0477 (4)
C70.4439 (2)0.70988 (19)0.17994 (4)0.0410 (4)
H70.52290.65210.16820.053*
C80.2692 (2)0.72322 (15)0.16796 (4)0.0295 (3)
C90.1315 (2)0.81660 (15)0.18457 (4)0.0313 (3)
H90.05120.76370.20010.041*
C100.2223 (2)0.92006 (15)0.20971 (4)0.0379 (3)
C110.0006 (3)0.87767 (17)0.15644 (5)0.0454 (4)
H11A0.10100.92100.16880.059*
H11B0.06930.94310.14320.059*
C120.0813 (2)0.78043 (17)0.12988 (4)0.0378 (3)
H12A0.15540.82620.11210.049*
H12B0.16280.72070.14250.049*
C130.0740 (2)0.70370 (13)0.11091 (4)0.0274 (3)
C140.1860 (2)0.63243 (13)0.14041 (4)0.0274 (3)
C150.3136 (2)0.54142 (17)0.11929 (4)0.0384 (3)
H15A0.35050.46740.13370.050*
H15B0.42460.58640.11110.050*
C160.1904 (2)0.49880 (16)0.08727 (4)0.0389 (4)
H16A0.15790.40770.08940.051*
H16B0.25660.51150.06480.051*
C170.0121 (2)0.58396 (13)0.08828 (4)0.0272 (3)
H170.07670.53660.10340.035*
C180.2044 (3)0.79554 (17)0.09003 (4)0.0440 (4)
H18A0.13110.85410.07580.066*
H18B0.28430.74550.07460.066*
H18C0.27920.84420.10670.066*
C190.3113 (4)1.0307 (2)0.18779 (7)0.0725 (7)
H19A0.39260.99460.16990.109*
H19B0.38181.08590.20350.109*
H19C0.21491.08040.17630.109*
C200.0865 (2)0.60078 (14)0.05167 (4)0.0292 (3)
C210.2632 (2)0.68158 (15)0.05480 (4)0.0349 (3)
H21A0.23070.76970.06040.052*
H21B0.34070.64690.07350.052*
H21C0.32970.67930.03240.052*
C220.1308 (2)0.46514 (14)0.03528 (4)0.0331 (3)
H22A0.01250.41930.03160.043*
C230.2566 (3)0.37924 (15)0.05803 (4)0.0407 (4)
H23A0.37750.42060.06060.053*
H23B0.20270.37030.08180.053*
C240.2832 (3)0.24384 (16)0.04158 (5)0.0438 (4)
H24A0.35730.25260.01990.057*
H24B0.16180.21070.03460.057*
C250.3769 (3)0.14389 (15)0.06587 (5)0.0416 (4)
C260.5705 (4)0.1864 (2)0.07749 (7)0.0665 (6)
H26A0.64060.21330.05680.100*
H26B0.56020.25750.09400.100*
H26C0.63300.11520.08900.100*
C270.2587 (4)0.1112 (2)0.09810 (6)0.0748 (8)
H27A0.31830.04400.11180.112*
H27B0.24420.18710.11280.112*
H27C0.13820.08180.09030.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0459 (7)0.0464 (7)0.0748 (9)0.0086 (6)0.0195 (7)0.0107 (6)
O20.0226 (6)0.1515 (17)0.0721 (9)0.0175 (8)0.0110 (6)0.0741 (11)
O30.0294 (6)0.0905 (10)0.0539 (7)0.0081 (7)0.0108 (5)0.0383 (7)
O50.0305 (6)0.0640 (8)0.0586 (7)0.0110 (6)0.0107 (5)0.0226 (6)
O60.0183 (6)0.1614 (18)0.0811 (10)0.0048 (9)0.0111 (7)0.0575 (12)
O140.0298 (5)0.0454 (6)0.0327 (5)0.0090 (5)0.0052 (4)0.0121 (4)
O200.0388 (6)0.0397 (6)0.0334 (5)0.0006 (5)0.0040 (5)0.0052 (4)
O220.0423 (6)0.0488 (6)0.0324 (5)0.0002 (5)0.0071 (5)0.0029 (5)
O250.0456 (7)0.0323 (6)0.0685 (8)0.0017 (5)0.0018 (6)0.0121 (5)
C10.0432 (10)0.0446 (9)0.0606 (11)0.0160 (8)0.0234 (9)0.0252 (8)
C20.0207 (8)0.0731 (12)0.0509 (9)0.0072 (8)0.0069 (7)0.0349 (9)
C30.0292 (8)0.0656 (11)0.0429 (8)0.0006 (8)0.0026 (7)0.0158 (8)
C40.0303 (8)0.0467 (8)0.0392 (8)0.0081 (7)0.0067 (7)0.0067 (7)
C50.0216 (7)0.0467 (9)0.0429 (8)0.0049 (6)0.0077 (6)0.0130 (7)
C60.0208 (7)0.0760 (12)0.0463 (9)0.0008 (8)0.0042 (7)0.0146 (9)
C70.0204 (7)0.0626 (11)0.0399 (8)0.0026 (7)0.0016 (6)0.0110 (7)
C80.0211 (6)0.0367 (7)0.0308 (6)0.0017 (6)0.0011 (5)0.0002 (5)
C90.0249 (7)0.0338 (7)0.0351 (7)0.0019 (6)0.0074 (6)0.0070 (6)
C100.0330 (8)0.0347 (7)0.0460 (8)0.0041 (6)0.0120 (7)0.0068 (6)
C110.0462 (10)0.0435 (9)0.0466 (9)0.0163 (8)0.0194 (8)0.0140 (7)
C120.0312 (8)0.0424 (8)0.0398 (8)0.0119 (7)0.0122 (6)0.0097 (6)
C130.0252 (7)0.0282 (6)0.0288 (6)0.0007 (5)0.0031 (5)0.0016 (5)
C140.0199 (6)0.0323 (7)0.0300 (6)0.0007 (5)0.0002 (5)0.0027 (5)
C150.0288 (7)0.0458 (9)0.0405 (8)0.0113 (7)0.0044 (6)0.0060 (7)
C160.0388 (9)0.0398 (8)0.0381 (7)0.0132 (7)0.0067 (7)0.0066 (6)
C170.0260 (7)0.0267 (6)0.0288 (6)0.0013 (5)0.0008 (5)0.0008 (5)
C180.0501 (10)0.0427 (8)0.0392 (8)0.0167 (8)0.0045 (7)0.0085 (7)
C190.0853 (17)0.0542 (12)0.0781 (14)0.0321 (13)0.0261 (14)0.0119 (10)
C200.0296 (7)0.0296 (6)0.0284 (6)0.0007 (6)0.0000 (5)0.0014 (5)
C210.0317 (8)0.0353 (7)0.0377 (7)0.0049 (6)0.0062 (6)0.0003 (6)
C220.0342 (8)0.0334 (7)0.0318 (7)0.0027 (6)0.0046 (6)0.0028 (6)
C230.0497 (10)0.0317 (7)0.0407 (8)0.0037 (7)0.0010 (7)0.0032 (6)
C240.0534 (10)0.0347 (8)0.0432 (8)0.0035 (8)0.0000 (8)0.0053 (6)
C250.0490 (10)0.0275 (7)0.0483 (9)0.0023 (7)0.0013 (8)0.0038 (6)
C260.0588 (13)0.0462 (10)0.0945 (16)0.0001 (10)0.0250 (13)0.0136 (11)
C270.109 (2)0.0470 (10)0.0682 (13)0.0012 (13)0.0294 (15)0.0099 (10)
Geometric parameters (Å, º) top
O2—C21.430 (2)C9—C111.540 (2)
O3—C31.431 (2)C9—C101.561 (2)
O5—C51.4303 (18)C10—C191.540 (3)
O6—C61.218 (2)C11—C121.526 (2)
O14—C141.4386 (17)C12—C131.537 (2)
O20—C201.4432 (18)C13—C181.541 (2)
O22—C221.4321 (17)C13—C141.5463 (18)
O25—C251.4431 (19)C13—C171.5587 (19)
C1—C21.505 (3)C14—C151.527 (2)
C1—C101.544 (3)C15—C161.547 (2)
C2—C31.513 (2)C16—C171.550 (2)
C3—C41.525 (2)C17—C201.5454 (19)
C4—C51.536 (2)C20—C211.519 (2)
C5—C61.526 (2)C20—C221.558 (2)
C5—C101.561 (2)C22—C231.521 (2)
C6—C71.455 (2)C23—C241.536 (2)
C7—C81.335 (2)C24—C251.526 (2)
C8—C141.5109 (19)C25—C271.507 (3)
C8—C91.510 (2)C25—C261.517 (3)
C2—C1—C10112.86 (14)C12—C13—C14107.04 (11)
O2—C2—C1111.49 (18)C18—C13—C14109.62 (12)
O2—C2—C3110.48 (14)C12—C13—C17116.73 (13)
C1—C2—C3111.43 (15)C18—C13—C17112.68 (12)
O3—C3—C2114.32 (17)C14—C13—C1799.00 (10)
O3—C3—C4107.39 (14)O14—C14—C8104.91 (11)
C2—C3—C4107.54 (13)O14—C14—C15107.63 (12)
C3—C4—C5112.28 (14)C8—C14—C15119.63 (12)
O5—C5—C6106.78 (13)O14—C14—C13107.27 (11)
O5—C5—C4108.85 (13)C8—C14—C13113.17 (11)
C6—C5—C4107.16 (15)C15—C14—C13103.63 (11)
O5—C5—C10111.10 (14)C14—C15—C16103.33 (12)
C6—C5—C10110.41 (13)C15—C16—C17106.89 (12)
C4—C5—C10112.30 (13)C20—C17—C16114.74 (12)
O6—C6—C7121.08 (18)C20—C17—C13121.24 (11)
O6—C6—C5120.53 (16)C16—C17—C13103.09 (12)
C7—C6—C5118.30 (14)O20—C20—C21104.47 (11)
C8—C7—C6122.60 (16)O20—C20—C17112.49 (12)
C7—C8—C14122.17 (14)C21—C20—C17111.98 (11)
C7—C8—C9122.72 (14)O20—C20—C22107.33 (11)
C14—C8—C9114.53 (12)C21—C20—C22110.59 (13)
C8—C9—C11112.27 (12)C17—C20—C22109.79 (11)
C8—C9—C10114.13 (12)O22—C22—C23107.19 (13)
C11—C9—C10112.50 (13)O22—C22—C20110.01 (12)
C19—C10—C1109.78 (17)C23—C22—C20115.11 (12)
C19—C10—C5108.30 (15)C22—C23—C24112.33 (14)
C1—C10—C5107.59 (13)C25—C24—C23115.53 (14)
C19—C10—C9111.09 (14)O25—C25—C27108.79 (15)
C1—C10—C9109.10 (13)O25—C25—C26104.70 (16)
C5—C10—C9110.91 (12)C27—C25—C26110.52 (19)
C12—C11—C9114.02 (13)O25—C25—C24108.30 (14)
C11—C12—C13110.96 (14)C27—C25—C24112.10 (18)
C12—C13—C18110.80 (13)C26—C25—C24112.09 (16)
C10—C1—C2—O2174.95 (13)C11—C12—C13—C1459.46 (16)
C10—C1—C2—C361.10 (17)C11—C12—C13—C17169.19 (13)
O2—C2—C3—O365.4 (2)C7—C8—C14—O14107.02 (17)
C1—C2—C3—O359.13 (18)C9—C8—C14—O1464.51 (15)
O2—C2—C3—C4175.47 (17)C7—C8—C14—C1513.8 (2)
C1—C2—C3—C460.01 (19)C9—C8—C14—C15174.68 (13)
O3—C3—C4—C565.55 (18)C7—C8—C14—C13136.35 (16)
C2—C3—C4—C557.93 (19)C9—C8—C14—C1352.12 (16)
C3—C4—C5—O567.34 (17)C12—C13—C14—O1456.85 (14)
C3—C4—C5—C6177.53 (12)C18—C13—C14—O14177.09 (12)
C3—C4—C5—C1056.11 (17)C17—C13—C14—O1464.82 (12)
O5—C5—C6—O624.7 (3)C12—C13—C14—C858.38 (15)
C4—C5—C6—O691.8 (3)C18—C13—C14—C861.86 (15)
C10—C5—C6—O6145.6 (2)C17—C13—C14—C8179.96 (11)
O5—C5—C6—C7158.72 (18)C12—C13—C14—C15170.54 (13)
C4—C5—C6—C784.8 (2)C18—C13—C14—C1569.22 (15)
C10—C5—C6—C737.8 (2)C17—C13—C14—C1548.88 (13)
O6—C6—C7—C8172.5 (2)O14—C14—C15—C1677.27 (14)
C5—C6—C7—C810.9 (3)C8—C14—C15—C16163.29 (13)
C6—C7—C8—C14169.46 (16)C13—C14—C15—C1636.16 (15)
C6—C7—C8—C91.4 (3)C14—C15—C16—C178.96 (17)
C7—C8—C9—C11144.60 (17)C15—C16—C17—C20154.97 (13)
C14—C8—C9—C1143.92 (18)C15—C16—C17—C1321.06 (16)
C7—C8—C9—C1015.1 (2)C12—C13—C17—C2073.58 (16)
C14—C8—C9—C10173.45 (12)C18—C13—C17—C2056.33 (18)
C2—C1—C10—C19172.10 (14)C14—C13—C17—C20172.09 (12)
C2—C1—C10—C554.44 (17)C12—C13—C17—C16156.36 (13)
C2—C1—C10—C965.95 (16)C18—C13—C17—C1673.74 (15)
O5—C5—C10—C1948.1 (2)C14—C13—C17—C1642.03 (13)
C6—C5—C10—C1970.23 (19)C16—C17—C20—O2064.50 (16)
C4—C5—C10—C19170.23 (15)C13—C17—C20—O2060.34 (17)
O5—C5—C10—C170.56 (17)C16—C17—C20—C21178.19 (13)
C6—C5—C10—C1171.16 (14)C13—C17—C20—C2156.97 (17)
C4—C5—C10—C151.62 (17)C16—C17—C20—C2254.95 (17)
O5—C5—C10—C9170.20 (13)C13—C17—C20—C22179.78 (13)
C6—C5—C10—C951.91 (18)O20—C20—C22—O2256.56 (16)
C4—C5—C10—C967.62 (17)C21—C20—C22—O2256.82 (16)
C8—C9—C10—C1978.9 (2)C17—C20—C22—O22179.12 (12)
C11—C9—C10—C1950.5 (2)O20—C20—C22—C23177.76 (13)
C8—C9—C10—C1159.90 (13)C21—C20—C22—C2364.38 (16)
C11—C9—C10—C170.67 (18)C17—C20—C22—C2359.68 (17)
C8—C9—C10—C541.56 (18)O22—C22—C23—C2461.32 (18)
C11—C9—C10—C5170.99 (14)C20—C22—C23—C24175.96 (14)
C8—C9—C11—C1246.0 (2)C22—C23—C24—C25169.10 (15)
C10—C9—C11—C12176.37 (15)C23—C24—C25—O25174.50 (16)
C9—C11—C12—C1355.5 (2)C23—C24—C25—C2765.5 (2)
C11—C12—C13—C1860.02 (17)C23—C24—C25—C2659.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···O200.852.052.8950 (18)172
O1—H1D···O22i0.802.112.8705 (19)159
O2—H2···O5ii0.842.052.8437 (19)157
O2—H2···O6ii0.842.443.052 (2)130
O3—H3···O14iii0.742.112.8136 (17)157
O5—H5···O30.871.892.676 (2)149
O14—H14···O2iv0.811.832.6190 (17)164
O20—H20···O1i0.772.433.150 (2)156
O22—H22···O25v0.911.962.8275 (19)159
O25—H25···O1vi0.812.022.820 (2)170
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x1, y, z; (iii) x, y+1/2, z+1/2; (iv) x, y1/2, z+1/2; (v) x+1/2, y+1/2, z; (vi) x, y1, z.

Experimental details

(I)(II)(III)(IV)
Crystal data
Chemical formulaC27H44O6C27H44O7C27H44O7·CH4O·H2OC27H50O10
Mr464.62480.62530.68534.67
Crystal system, space groupOrthorhombic, P212121Orthorhombic, P212121Orthorhombic, P212121Orthorhombic, P212121
Temperature (K)293293293293
a, b, c (Å)7.750 (1), 9.935 (1), 35.657 (1)7.663 (1), 10.541 (1), 33.084 (2)7.167 (1), 9.703 (1), 41.412 (4)11.293 (2), 14.202 (2), 18.721 (3)
V3)2745.5 (5)2672.4 (5)2879.8 (6)3002.5 (8)
Z4444
Radiation typeCu KαCu KαCu KαMo Kα
µ (mm1)0.620.690.730.09
Crystal size (mm)0.25 × 0.16 × 0.120.45 × 0.30 × 0.200.25 × 0.14 × 0.100.6 × 0.6 × 0.4
Data collection
DiffractometerEnraf-Nonius CAD4
diffractometer
Enraf-Nonius CAD4
diffractometer
Enraf-Nonius CAD4
diffractometer
Enraf-Nonius CAD4
diffractometer
Absorption correctionψ scan
North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24 350-359
ψ scan
North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24 350-359
ψ scan
North A.C., Philips D.C. & Mathews F.(1968): Acta Cryst. A24 350-359
ψ scan
Reibenspies, J. (1989) DATCOR program for empirical (using intensity measurements) absorption correction, Texas A & M University, College Station, Tx, USA.
Tmin, Tmax0.858, 0.9300.748, 0.8750.838, 0.9300.898, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
6982, 5410, 3946 5611, 4542, 4155 6775, 5774, 4751 13105, 11655, 6759
Rint0.0130.0130.0120.011
(sin θ/λ)max1)0.6260.6260.6260.775
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.109, 0.74 0.036, 0.104, 1.06 0.038, 0.121, 0.86 0.054, 0.142, 0.92
No. of reflections54104542577411655
No. of parameters376375356366
No. of restraints29024430
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementRiding
Δρmax, Δρmin (e Å3)0.15, 0.140.25, 0.210.23, 0.150.26, 0.18
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter0.18 (17)0.19 (18)0.09 (17)0.1 (7)


(V)
Crystal data
Chemical formulaC27H44O8·H2O
Mr514.64
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)7.163 (1), 10.303 (1), 37.254 (2)
V3)2749.4 (5)
Z4
Radiation typeCu Kα
µ (mm1)0.76
Crystal size (mm)0.50 × 0.15 × 0.10
Data collection
DiffractometerEnraf-Nonius CAD4
diffractometer
Absorption correctionψ scan
North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24 350-359
Tmin, Tmax0.896, 0.927
No. of measured, independent and
observed [I > 2σ(I)] reflections
6667, 5553, 4972
Rint0.009
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.104, 1.07
No. of reflections5553
No. of parameters338
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.20
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter0.03 (14)

Computer programs: CAD-4 EXPRESS, Enraf-Nonius Express, XCAD4 (Harms, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.821.952.7494 (19)165.2
O3—H3···O6i0.822.032.8019 (16)156.2
O14—H14···O22Aii0.821.862.68 (3)171.6
O14—H14···O22Bii0.822.082.89 (3)172.1
O22A—H22C···O25A0.821.892.71 (2)171.3
O25A—H25A···O2iii0.821.952.760 (10)171.3
O22B—H22D···O25B0.821.812.63 (2)171.8
O25B—H25B···O2iii0.821.922.733 (9)169.6
Symmetry codes: (i) x1/2, y+3/2, z+2; (ii) x+1, y1/2, z+3/2; (iii) x, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.821.942.759 (2)179.0
O3—H3···O6i0.822.313.048 (2)149.5
O14—H14···O20ii0.822.032.8520 (17)175.3
O20—H20···O220.822.122.5795 (19)115.1
O22—H22···O25A0.821.882.671 (10)161.2
O22—H22···O25B0.821.842.645 (12)165.1
O25A—H25A···O2iii0.822.072.842 (14)156.9
O25B—H25B···O2iii0.821.982.707 (13)147.2
Symmetry codes: (i) x1/2, y+3/2, z+2; (ii) x+1, y1/2, z+3/2; (iii) x, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O6i0.772.243.007 (2)176.5
O3—H3···O2Xii0.881.922.794 (2)171.7
O14—H14···O1W0.891.812.696 (2)168.8
O20—H20···O22iii0.802.002.787 (2)168.5
O22—H22···O25iii0.832.503.204 (2)144.2
O22—H22···O200.832.292.721 (2)112.6
O25—H25···O20iv0.971.942.871 (2)160.8
O1W—H1W···O3v0.802.032.815 (2)170.9
O1W—H2W···O2vi0.831.972.775 (2)164.6
O2X—H2X···O140.821.912.711 (2)165.0
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+2, y+1/2, z+3/2; (iii) x1/2, y+1/2, z+2; (iv) x+1/2, y+1/2, z+2; (v) x+1, y1/2, z+3/2; (vi) x+2, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) for (V) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···O200.852.052.8950 (18)172.2
O1—H1D···O22i0.802.112.8705 (19)158.8
O2—H2···O5ii0.842.052.8437 (19)156.8
O2—H2···O6ii0.842.443.052 (2)130.2
O3—H3···O14iii0.742.112.8136 (17)156.9
O5—H5···O30.871.892.676 (2)149.4
O14—H14···O2iv0.811.832.6190 (17)163.8
O20—H20···O1i0.772.433.150 (2)155.7
O22—H22···O25v0.911.962.8275 (19)159.0
O25—H25···O1vi0.812.022.820 (2)170.2
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x1, y, z; (iii) x, y+1/2, z+1/2; (iv) x, y1/2, z+1/2; (v) x+1/2, y+1/2, z; (vi) x, y1, z.
 

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