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
CCDC references: 193588; 193589; 193590; 193591; 193592
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).
(I) 2
β,3
β,14
α,22
R,25-pentahydroxy-5
β-cholest-7-en-6-one
top
Crystal data top
C27H44O6 | Dx = 1.124 Mg m−3 |
Mr = 464.62 | Cu Kα radiation, λ = 1.54180 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 7.750 (1) Å | θ = 20.1–23.7° |
b = 9.935 (1) Å | µ = 0.62 mm−1 |
c = 35.657 (1) Å | T = 293 K |
V = 2745.5 (5) Å3 | Block, colorless |
Z = 4 | 0.25 × 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 tube | Rint = 0.013 |
Graphite monochromator | θmax = 74.7°, θmin = 4.6° |
ω–2θ scans | h = −8→9 |
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24 350-359 | k = −12→12 |
Tmin = 0.858, Tmax = 0.930 | l = −44→44 |
6982 measured reflections | 3 standard reflections every 60 min |
5410 independent reflections | intensity decay: 9% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H 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 = 0.74 | Δρmax = 0.15 e Å−3 |
5410 reflections | Δρmin = −0.14 e Å−3 |
376 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
290 restraints | Extinction coefficient: 0.0014 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.18 (17) |
Crystal data top
C27H44O6 | V = 2745.5 (5) Å3 |
Mr = 464.62 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 7.750 (1) Å | µ = 0.62 mm−1 |
b = 9.935 (1) Å | T = 293 K |
c = 35.657 (1) Å | 0.25 × 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 = 0.930 | 3 standard reflections every 60 min |
6982 measured reflections | intensity decay: 9% |
5410 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.109 | Δρmax = 0.15 e Å−3 |
S = 0.74 | Δρmin = −0.14 e Å−3 |
5410 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
376 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O2 | −0.01505 (17) | 0.64110 (15) | 0.95659 (3) | 0.0517 (3) | |
H2 | −0.0567 | 0.6887 | 0.9731 | 0.067* | |
O3 | 0.29606 (18) | 0.69367 (14) | 0.99714 (3) | 0.0529 (3) | |
H3 | 0.2641 | 0.6273 | 1.0089 | 0.069* | |
O6 | 0.71094 (17) | 0.98389 (14) | 0.94469 (3) | 0.0532 (3) | |
O14 | 0.42685 (19) | 0.81146 (12) | 0.81321 (3) | 0.0496 (3) | |
H14 | 0.5114 | 0.7700 | 0.8208 | 0.065* | |
C1 | 0.1102 (2) | 0.8594 (2) | 0.94183 (5) | 0.0463 (4) | |
H1A | 0.0999 | 0.8858 | 0.9679 | 0.060* | |
H1B | 0.0039 | 0.8844 | 0.9293 | 0.060* | |
C2 | 0.1299 (2) | 0.7089 (2) | 0.93993 (4) | 0.0438 (4) | |
H2A | 0.1338 | 0.6835 | 0.9134 | 0.057* | |
C3 | 0.2976 (2) | 0.66325 (19) | 0.95779 (4) | 0.0437 (4) | |
H3A | 0.3111 | 0.5660 | 0.9543 | 0.057* | |
C4 | 0.4503 (2) | 0.73592 (17) | 0.94022 (5) | 0.0413 (4) | |
H4A | 0.4614 | 0.7089 | 0.9142 | 0.054* | |
H4B | 0.5553 | 0.7104 | 0.9532 | 0.054* | |
C5 | 0.4276 (2) | 0.88920 (17) | 0.94234 (4) | 0.0384 (4) | |
H5 | 0.4231 | 0.9141 | 0.9689 | 0.050* | |
C6 | 0.5838 (2) | 0.95673 (17) | 0.92548 (4) | 0.0388 (4) | |
C7 | 0.5804 (2) | 0.98136 (17) | 0.88521 (4) | 0.0397 (4) | |
H7 | 0.6791 | 1.0146 | 0.8736 | 0.052* | |
C8 | 0.4406 (2) | 0.95783 (17) | 0.86439 (4) | 0.0369 (3) | |
C9 | 0.2690 (2) | 0.91404 (19) | 0.88096 (4) | 0.0416 (4) | |
H9 | 0.2633 | 0.8163 | 0.8775 | 0.054* | |
C10 | 0.2601 (2) | 0.93820 (18) | 0.92401 (4) | 0.0411 (4) | |
C11 | 0.1128 (2) | 0.9719 (3) | 0.85996 (5) | 0.0625 (6) | |
H11A | 0.0990 | 1.0657 | 0.8669 | 0.081* | |
H11B | 0.0099 | 0.9243 | 0.8679 | 0.081* | |
C12 | 0.1277 (2) | 0.9622 (3) | 0.81702 (5) | 0.0572 (5) | |
H12A | 0.1250 | 0.8684 | 0.8095 | 0.074* | |
H12B | 0.0299 | 1.0071 | 0.8056 | 0.074* | |
C13 | 0.2942 (2) | 1.02651 (18) | 0.80304 (4) | 0.0428 (4) | |
C14 | 0.4461 (2) | 0.95220 (17) | 0.82200 (4) | 0.0380 (4) | |
C15 | 0.6042 (2) | 1.0056 (2) | 0.80135 (4) | 0.0456 (4) | |
H15A | 0.7001 | 0.9433 | 0.8032 | 0.059* | |
H15B | 0.6394 | 1.0924 | 0.8112 | 0.059* | |
C16 | 0.5399 (2) | 1.0181 (2) | 0.76035 (5) | 0.0517 (5) | |
H16A | 0.5908 | 0.9482 | 0.7449 | 0.067* | |
H16B | 0.5720 | 1.1049 | 0.7500 | 0.067* | |
C17 | 0.3406 (2) | 1.00334 (19) | 0.76112 (4) | 0.0448 (4) | |
H17 | 0.3135 | 0.9094 | 0.7551 | 0.058* | |
C18 | 0.3008 (3) | 1.1761 (2) | 0.81292 (5) | 0.0569 (5) | |
H18A | 0.1942 | 1.2181 | 0.8058 | 0.085* | |
H18B | 0.3945 | 1.2179 | 0.7997 | 0.085* | |
H18C | 0.3179 | 1.1862 | 0.8394 | 0.085* | |
C19 | 0.2357 (3) | 1.0875 (2) | 0.93360 (5) | 0.0588 (5) | |
H19A | 0.1185 | 1.1132 | 0.9287 | 0.088* | |
H19B | 0.3121 | 1.1409 | 0.9185 | 0.088* | |
H19C | 0.2612 | 1.1018 | 0.9596 | 0.088* | |
C20 | 0.2505 (3) | 1.0925 (2) | 0.73154 (5) | 0.0531 (5) | |
H20 | 0.2883 | 1.1852 | 0.7361 | 0.069* | |
C21 | 0.0527 (3) | 1.0925 (3) | 0.73363 (6) | 0.0801 (7) | |
H21A | 0.0065 | 1.1342 | 0.7115 | 0.120* | |
H21B | 0.0163 | 1.1419 | 0.7554 | 0.120* | |
H21C | 0.0117 | 1.0015 | 0.7353 | 0.120* | |
C22 | 0.3125 (3) | 1.05427 (19) | 0.69185 (4) | 0.0547 (5) | |
H22A | 0.4358 | 1.0326 | 0.6927 | 0.071* | 0.476 (18) |
H22B | 0.4389 | 1.0532 | 0.6926 | 0.071* | 0.524 (18) |
O22A | 0.287 (4) | 1.1734 (14) | 0.6693 (5) | 0.067 (5) | 0.476 (18) |
H22C | 0.2733 | 1.1463 | 0.6478 | 0.087* | 0.476 (18) |
C23A | 0.214 (2) | 0.9341 (13) | 0.6776 (3) | 0.072 (4) | 0.476 (18) |
H23A | 0.0947 | 0.9604 | 0.6742 | 0.094* | 0.476 (18) |
H23B | 0.2165 | 0.8652 | 0.6969 | 0.094* | 0.476 (18) |
C24A | 0.279 (2) | 0.8710 (10) | 0.6408 (2) | 0.082 (4) | 0.476 (18) |
H24A | 0.4012 | 0.8889 | 0.6387 | 0.107* | 0.476 (18) |
H24B | 0.2646 | 0.7742 | 0.6427 | 0.107* | 0.476 (18) |
C25A | 0.1914 (17) | 0.9180 (9) | 0.6047 (2) | 0.056 (3) | 0.476 (18) |
O25A | 0.2267 (17) | 1.0604 (7) | 0.6015 (3) | 0.058 (4) | 0.476 (18) |
H25A | 0.1685 | 1.0924 | 0.5844 | 0.075* | 0.476 (18) |
C26A | 0.270 (3) | 0.8462 (13) | 0.5711 (2) | 0.109 (5) | 0.476 (18) |
H26A | 0.2200 | 0.8807 | 0.5484 | 0.164* | 0.476 (18) |
H26B | 0.2475 | 0.7514 | 0.5729 | 0.164* | 0.476 (18) |
H26C | 0.3925 | 0.8612 | 0.5707 | 0.164* | 0.476 (18) |
C27A | −0.0024 (18) | 0.8948 (12) | 0.6068 (3) | 0.094 (4) | 0.476 (18) |
H27A | −0.0535 | 0.9614 | 0.6229 | 0.141* | 0.476 (18) |
H27B | −0.0246 | 0.8068 | 0.6168 | 0.141* | 0.476 (18) |
H27C | −0.0514 | 0.9017 | 0.5822 | 0.141* | 0.476 (18) |
O22B | 0.263 (4) | 1.1654 (12) | 0.6676 (4) | 0.058 (3) | 0.524 (18) |
H22D | 0.2520 | 1.1381 | 0.6461 | 0.075* | 0.524 (18) |
C23B | 0.256 (2) | 0.9201 (11) | 0.6752 (3) | 0.059 (2) | 0.524 (18) |
H23C | 0.1320 | 0.9226 | 0.6713 | 0.076* | 0.524 (18) |
H23D | 0.2794 | 0.8496 | 0.6933 | 0.076* | 0.524 (18) |
C24B | 0.3429 (12) | 0.8829 (7) | 0.63812 (18) | 0.0510 (16) | 0.524 (18) |
H24C | 0.4535 | 0.9285 | 0.6374 | 0.066* | 0.524 (18) |
H24D | 0.3666 | 0.7870 | 0.6387 | 0.066* | 0.524 (18) |
C25B | 0.2511 (10) | 0.9127 (10) | 0.6016 (2) | 0.0566 (19) | 0.524 (18) |
O25B | 0.2173 (15) | 1.0553 (8) | 0.6014 (2) | 0.057 (4) | 0.524 (18) |
H25B | 0.1647 | 1.0754 | 0.5823 | 0.074* | 0.524 (18) |
C26B | 0.3632 (14) | 0.8759 (9) | 0.5682 (2) | 0.078 (2) | 0.524 (18) |
H26D | 0.3113 | 0.9097 | 0.5456 | 0.118* | 0.524 (18) |
H26E | 0.3735 | 0.7797 | 0.5666 | 0.118* | 0.524 (18) |
H26F | 0.4757 | 0.9149 | 0.5712 | 0.118* | 0.524 (18) |
C27B | 0.0795 (14) | 0.8393 (11) | 0.5990 (2) | 0.086 (3) | 0.524 (18) |
H27D | 0.0024 | 0.8730 | 0.6178 | 0.128* | 0.524 (18) |
H27E | 0.0976 | 0.7447 | 0.6027 | 0.128* | 0.524 (18) |
H27F | 0.0302 | 0.8539 | 0.5746 | 0.128* | 0.524 (18) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0460 (7) | 0.0739 (9) | 0.0351 (6) | −0.0154 (6) | 0.0038 (5) | −0.0021 (6) |
O3 | 0.0538 (8) | 0.0709 (9) | 0.0339 (5) | −0.0118 (7) | −0.0045 (6) | 0.0149 (6) |
O6 | 0.0448 (7) | 0.0707 (8) | 0.0441 (6) | −0.0079 (7) | −0.0118 (6) | 0.0124 (6) |
O14 | 0.0616 (8) | 0.0426 (7) | 0.0447 (6) | 0.0014 (6) | −0.0069 (6) | 0.0046 (5) |
C1 | 0.0333 (9) | 0.0661 (12) | 0.0395 (8) | 0.0080 (8) | 0.0057 (7) | 0.0101 (8) |
C2 | 0.0382 (9) | 0.0649 (11) | 0.0283 (7) | −0.0051 (8) | 0.0047 (7) | 0.0034 (7) |
C3 | 0.0441 (10) | 0.0483 (9) | 0.0386 (8) | −0.0014 (8) | −0.0010 (8) | 0.0042 (7) |
C4 | 0.0378 (9) | 0.0479 (9) | 0.0383 (8) | 0.0069 (8) | 0.0017 (7) | 0.0046 (7) |
C5 | 0.0382 (9) | 0.0477 (9) | 0.0293 (7) | 0.0041 (7) | 0.0007 (7) | 0.0036 (7) |
C6 | 0.0378 (9) | 0.0436 (9) | 0.0352 (7) | 0.0046 (7) | −0.0029 (7) | 0.0040 (7) |
C7 | 0.0351 (9) | 0.0486 (9) | 0.0355 (7) | −0.0010 (8) | 0.0018 (6) | 0.0090 (7) |
C8 | 0.0353 (8) | 0.0427 (9) | 0.0327 (7) | 0.0047 (7) | 0.0019 (6) | 0.0074 (6) |
C9 | 0.0360 (9) | 0.0561 (10) | 0.0329 (7) | 0.0032 (8) | 0.0000 (6) | 0.0106 (7) |
C10 | 0.0363 (10) | 0.0540 (10) | 0.0329 (8) | 0.0086 (8) | 0.0031 (6) | 0.0078 (7) |
C11 | 0.0357 (10) | 0.1077 (18) | 0.0439 (9) | 0.0068 (11) | −0.0015 (7) | 0.0225 (11) |
C12 | 0.0378 (10) | 0.0892 (15) | 0.0447 (9) | −0.0041 (10) | −0.0077 (8) | 0.0216 (10) |
C13 | 0.0418 (9) | 0.0510 (10) | 0.0356 (7) | 0.0004 (8) | −0.0044 (7) | 0.0076 (7) |
C14 | 0.0395 (9) | 0.0416 (9) | 0.0328 (8) | −0.0004 (7) | −0.0013 (6) | 0.0036 (6) |
C15 | 0.0413 (9) | 0.0599 (11) | 0.0357 (8) | −0.0017 (9) | 0.0003 (7) | 0.0064 (8) |
C16 | 0.0545 (11) | 0.0667 (12) | 0.0338 (8) | −0.0015 (9) | 0.0002 (7) | 0.0081 (8) |
C17 | 0.0531 (10) | 0.0481 (10) | 0.0331 (7) | −0.0061 (8) | −0.0061 (7) | 0.0089 (7) |
C18 | 0.0682 (13) | 0.0553 (11) | 0.0471 (9) | 0.0132 (11) | −0.0083 (10) | 0.0060 (9) |
C19 | 0.0664 (14) | 0.0565 (11) | 0.0535 (10) | 0.0162 (10) | 0.0075 (10) | 0.0058 (8) |
C20 | 0.0650 (14) | 0.0566 (11) | 0.0377 (9) | −0.0025 (9) | −0.0098 (8) | 0.0118 (8) |
C21 | 0.0737 (16) | 0.109 (2) | 0.0575 (12) | 0.0155 (15) | −0.0185 (12) | 0.0265 (13) |
C22 | 0.0781 (14) | 0.0504 (10) | 0.0355 (8) | −0.0101 (10) | −0.0147 (9) | 0.0121 (8) |
O22A | 0.099 (7) | 0.064 (7) | 0.039 (4) | −0.033 (3) | −0.025 (3) | 0.014 (3) |
C23A | 0.121 (10) | 0.051 (5) | 0.044 (4) | −0.007 (5) | −0.020 (4) | 0.018 (3) |
C24A | 0.123 (9) | 0.063 (4) | 0.061 (4) | 0.003 (5) | −0.028 (5) | 0.011 (3) |
C25A | 0.094 (7) | 0.036 (3) | 0.039 (3) | −0.004 (4) | −0.021 (3) | 0.001 (2) |
O25A | 0.076 (8) | 0.037 (5) | 0.061 (6) | −0.010 (4) | −0.015 (5) | 0.019 (4) |
C26A | 0.182 (14) | 0.092 (6) | 0.055 (4) | 0.041 (8) | −0.021 (6) | −0.010 (4) |
C27A | 0.127 (8) | 0.064 (5) | 0.091 (5) | −0.047 (5) | −0.040 (5) | 0.017 (4) |
O22B | 0.099 (8) | 0.035 (3) | 0.039 (3) | −0.013 (4) | −0.023 (3) | 0.009 (2) |
C23B | 0.085 (5) | 0.042 (3) | 0.050 (4) | −0.009 (4) | −0.013 (3) | 0.002 (2) |
C24B | 0.072 (4) | 0.034 (2) | 0.047 (3) | −0.002 (2) | −0.014 (2) | 0.0031 (18) |
C25B | 0.070 (4) | 0.052 (3) | 0.048 (3) | −0.013 (3) | −0.014 (3) | 0.008 (2) |
O25B | 0.074 (7) | 0.063 (6) | 0.034 (4) | −0.006 (5) | −0.024 (4) | −0.002 (3) |
C26B | 0.113 (6) | 0.069 (4) | 0.054 (3) | −0.001 (4) | 0.005 (4) | −0.003 (2) |
C27B | 0.102 (6) | 0.079 (5) | 0.075 (4) | −0.036 (5) | −0.026 (4) | 0.009 (4) |
Geometric parameters (Å, º) top
O2—C2 | 1.438 (2) | C13—C17 | 1.555 (2) |
O3—C3 | 1.4351 (19) | C14—C15 | 1.525 (2) |
O6—C6 | 1.230 (2) | C15—C16 | 1.550 (2) |
O14—C14 | 1.441 (2) | C16—C17 | 1.552 (3) |
C1—C2 | 1.504 (3) | C17—C20 | 1.544 (2) |
C1—C10 | 1.538 (2) | C20—C21 | 1.535 (3) |
C2—C3 | 1.517 (3) | C20—C22 | 1.542 (3) |
C3—C4 | 1.521 (2) | C22—O22A | 1.443 (10) |
C4—C5 | 1.535 (2) | C22—O22B | 1.454 (8) |
C5—C6 | 1.508 (2) | C22—C23A | 1.505 (11) |
C5—C10 | 1.533 (2) | C22—C23B | 1.524 (8) |
C6—C7 | 1.457 (2) | C23A—C24A | 1.538 (10) |
C7—C8 | 1.334 (2) | C24A—C25A | 1.529 (8) |
C8—C14 | 1.513 (2) | C25A—O25A | 1.446 (8) |
C8—C9 | 1.519 (2) | C25A—C27A | 1.521 (4) |
C9—C11 | 1.535 (2) | C25A—C26A | 1.522 (4) |
C9—C10 | 1.555 (2) | C23B—C24B | 1.530 (9) |
C10—C19 | 1.534 (3) | C24B—C25B | 1.512 (8) |
C11—C12 | 1.538 (3) | C25B—O25B | 1.441 (9) |
C12—C13 | 1.523 (3) | C25B—C27B | 1.519 (4) |
C13—C18 | 1.528 (3) | C25B—C26B | 1.521 (4) |
C13—C14 | 1.545 (2) | | |
| | | |
C2—C1—C10 | 114.26 (14) | O14—C14—C13 | 106.85 (14) |
O2—C2—C1 | 111.56 (15) | C8—C14—C13 | 113.46 (14) |
O2—C2—C3 | 110.85 (13) | C15—C14—C13 | 103.56 (12) |
C1—C2—C3 | 111.41 (15) | C14—C15—C16 | 103.02 (13) |
O3—C3—C2 | 109.90 (14) | C15—C16—C17 | 107.19 (14) |
O3—C3—C4 | 108.02 (14) | C20—C17—C16 | 112.57 (15) |
C2—C3—C4 | 110.59 (13) | C20—C17—C13 | 117.85 (15) |
C3—C4—C5 | 111.21 (15) | C16—C17—C13 | 103.49 (13) |
C6—C5—C10 | 111.62 (13) | C21—C20—C22 | 110.85 (17) |
C6—C5—C4 | 109.27 (14) | C21—C20—C17 | 114.76 (16) |
C10—C5—C4 | 113.02 (15) | C22—C20—C17 | 110.17 (16) |
O6—C6—C7 | 121.74 (16) | O22A—C22—O22B | 8 (2) |
O6—C6—C5 | 121.23 (14) | O22A—C22—C23A | 113.3 (11) |
C7—C6—C5 | 116.94 (15) | O22B—C22—C23A | 105.6 (12) |
C8—C7—C6 | 122.25 (15) | O22A—C22—C23B | 117.5 (12) |
C7—C8—C14 | 122.66 (15) | O22B—C22—C23B | 110.9 (9) |
C7—C8—C9 | 123.01 (14) | C23A—C22—C23B | 13.7 (12) |
C14—C8—C9 | 113.73 (14) | O22A—C22—C20 | 105.5 (9) |
C8—C9—C11 | 113.15 (13) | O22B—C22—C20 | 106.0 (7) |
C8—C9—C10 | 112.25 (14) | C23A—C22—C20 | 110.3 (5) |
C11—C9—C10 | 112.87 (15) | C23B—C22—C20 | 118.9 (4) |
C5—C10—C19 | 108.45 (16) | C22—C23A—C24A | 116.5 (9) |
C5—C10—C1 | 107.56 (13) | C25A—C24A—C23A | 116.9 (8) |
C19—C10—C1 | 107.89 (15) | O25A—C25A—C27A | 109.8 (7) |
C5—C10—C9 | 109.51 (13) | O25A—C25A—C26A | 108.7 (6) |
C19—C10—C9 | 112.02 (14) | C27A—C25A—C26A | 111.4 (6) |
C1—C10—C9 | 111.27 (15) | O25A—C25A—C24A | 106.4 (6) |
C9—C11—C12 | 113.76 (16) | C27A—C25A—C24A | 110.3 (6) |
C13—C12—C11 | 111.28 (16) | C26A—C25A—C24A | 110.1 (6) |
C12—C13—C18 | 111.14 (18) | C22—C23B—C24B | 114.9 (7) |
C12—C13—C14 | 107.56 (13) | C25B—C24B—C23B | 119.2 (7) |
C18—C13—C14 | 109.78 (15) | O25B—C25B—C24B | 106.4 (5) |
C12—C13—C17 | 116.64 (15) | O25B—C25B—C27B | 108.2 (6) |
C18—C13—C17 | 110.96 (14) | C24B—C25B—C27B | 111.9 (6) |
C14—C13—C17 | 100.00 (13) | O25B—C25B—C26B | 109.6 (6) |
O14—C14—C8 | 104.49 (13) | C24B—C25B—C26B | 111.0 (6) |
O14—C14—C15 | 108.42 (14) | C27B—C25B—C26B | 109.6 (5) |
C8—C14—C15 | 119.47 (14) | | |
| | | |
C10—C1—C2—O2 | −179.26 (13) | C12—C13—C14—O14 | 55.96 (17) |
C10—C1—C2—C3 | 56.27 (18) | C18—C13—C14—O14 | 177.02 (14) |
O2—C2—C3—O3 | −60.48 (19) | C17—C13—C14—O14 | −66.27 (15) |
C1—C2—C3—O3 | 64.39 (18) | C12—C13—C14—C8 | −58.65 (19) |
O2—C2—C3—C4 | −179.65 (14) | C18—C13—C14—C8 | 62.41 (19) |
C1—C2—C3—C4 | −54.78 (18) | C17—C13—C14—C8 | 179.12 (14) |
O3—C3—C4—C5 | −65.34 (17) | C12—C13—C14—C15 | 170.33 (15) |
C2—C3—C4—C5 | 54.96 (18) | C18—C13—C14—C15 | −68.62 (17) |
C3—C4—C5—C6 | 178.60 (13) | C17—C13—C14—C15 | 48.10 (16) |
C3—C4—C5—C10 | −56.48 (17) | O14—C14—C15—C16 | 75.48 (17) |
C10—C5—C6—O6 | 145.52 (17) | C8—C14—C15—C16 | −165.11 (15) |
C4—C5—C6—O6 | −88.75 (19) | C13—C14—C15—C16 | −37.76 (18) |
C10—C5—C6—C7 | −37.7 (2) | C14—C15—C16—C17 | 12.7 (2) |
C4—C5—C6—C7 | 88.01 (17) | C15—C16—C17—C20 | 144.97 (16) |
O6—C6—C7—C8 | −176.99 (17) | C15—C16—C17—C13 | 16.7 (2) |
C5—C6—C7—C8 | 6.3 (2) | C12—C13—C17—C20 | 80.6 (2) |
C6—C7—C8—C14 | −165.68 (16) | C18—C13—C17—C20 | −48.0 (2) |
C6—C7—C8—C9 | 4.9 (3) | C14—C13—C17—C20 | −163.83 (15) |
C7—C8—C9—C11 | 145.05 (19) | C12—C13—C17—C16 | −154.41 (16) |
C14—C8—C9—C11 | −43.6 (2) | C18—C13—C17—C16 | 76.96 (19) |
C7—C8—C9—C10 | 15.9 (2) | C14—C13—C17—C16 | −38.86 (17) |
C14—C8—C9—C10 | −172.75 (14) | C16—C17—C20—C21 | −174.2 (2) |
C6—C5—C10—C19 | −65.99 (17) | C13—C17—C20—C21 | −53.9 (3) |
C4—C5—C10—C19 | 170.37 (14) | C16—C17—C20—C22 | 59.8 (2) |
C6—C5—C10—C1 | 177.58 (15) | C13—C17—C20—C22 | −179.80 (16) |
C4—C5—C10—C1 | 53.94 (18) | C21—C20—C22—O22A | 77.0 (13) |
C6—C5—C10—C9 | 56.53 (19) | C17—C20—C22—O22A | −154.9 (13) |
C4—C5—C10—C9 | −67.11 (18) | C21—C20—C22—O22B | 68.2 (12) |
C2—C1—C10—C5 | −54.37 (19) | C17—C20—C22—O22B | −163.7 (12) |
C2—C1—C10—C19 | −171.18 (15) | C21—C20—C22—C23A | −45.7 (8) |
C2—C1—C10—C9 | 65.57 (19) | C17—C20—C22—C23A | 82.4 (8) |
C8—C9—C10—C5 | −45.51 (19) | C21—C20—C22—C23B | −57.4 (8) |
C11—C9—C10—C5 | −174.83 (16) | C17—C20—C22—C23B | 70.7 (7) |
C8—C9—C10—C19 | 74.86 (19) | O22A—C22—C23A—C24A | 70.6 (16) |
C11—C9—C10—C19 | −54.5 (2) | O22B—C22—C23A—C24A | 74.4 (15) |
C8—C9—C10—C1 | −164.29 (14) | C23B—C22—C23A—C24A | −40 (3) |
C11—C9—C10—C1 | 66.4 (2) | C20—C22—C23A—C24A | −171.5 (8) |
C8—C9—C11—C12 | 45.2 (2) | C22—C23A—C24A—C25A | −94.6 (12) |
C10—C9—C11—C12 | 174.02 (18) | C23A—C24A—C25A—O25A | 62.3 (10) |
C9—C11—C12—C13 | −54.3 (3) | C23A—C24A—C25A—C27A | −56.7 (10) |
C11—C12—C13—C18 | −61.2 (2) | C23A—C24A—C25A—C26A | 179.9 (9) |
C11—C12—C13—C14 | 59.0 (2) | O22A—C22—C23B—C24B | 58.7 (18) |
C11—C12—C13—C17 | 170.24 (17) | O22B—C22—C23B—C24B | 64.6 (14) |
C7—C8—C14—O14 | 107.13 (18) | C23A—C22—C23B—C24B | 134 (4) |
C9—C8—C14—O14 | −64.28 (18) | C20—C22—C23B—C24B | −172.2 (6) |
C7—C8—C14—C15 | −14.3 (3) | C22—C23B—C24B—C25B | −96.8 (10) |
C9—C8—C14—C15 | 174.33 (15) | C23B—C24B—C25B—O25B | 57.4 (8) |
C7—C8—C14—C13 | −136.86 (17) | C23B—C24B—C25B—C27B | −60.6 (9) |
C9—C8—C14—C13 | 51.73 (19) | C23B—C24B—C25B—C26B | 176.6 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3i | 0.82 | 1.95 | 2.7494 (19) | 165 |
O3—H3···O6i | 0.82 | 2.03 | 2.8019 (16) | 156 |
O14—H14···O22Aii | 0.82 | 1.86 | 2.68 (3) | 172 |
O14—H14···O22Bii | 0.82 | 2.08 | 2.89 (3) | 172 |
O22A—H22C···O25A | 0.82 | 1.89 | 2.71 (2) | 171 |
O25A—H25A···O2iii | 0.82 | 1.95 | 2.760 (10) | 171 |
O22B—H22D···O25B | 0.82 | 1.81 | 2.63 (2) | 172 |
O25B—H25B···O2iii | 0.82 | 1.92 | 2.733 (9) | 170 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x, y+1/2, −z+3/2. |
(II) 2
β,3
β,14
α,20
R,22
R,25-hexahydroxy-5
β-cholest-7-en-6-one
top
Crystal data top
C27H44O7 | Dx = 1.195 Mg m−3 |
Mr = 480.62 | Cu Kα radiation, λ = 1.54180 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 7.663 (1) Å | θ = 30.6–34.6° |
b = 10.541 (1) Å | µ = 0.69 mm−1 |
c = 33.084 (2) Å | T = 293 K |
V = 2672.4 (5) Å3 | Block, colorless |
Z = 4 | 0.45 × 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 tube | Rint = 0.013 |
Graphite monochromator | θmax = 75.0°, θmin = 2.7° |
ω–2θ scans | h = −8→9 |
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24 350-359 | k = −13→11 |
Tmin = 0.748, Tmax = 0.875 | l = −35→41 |
5611 measured reflections | 3 standard reflections every 60 min |
4542 independent reflections | intensity decay: 4% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H 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 reflections | Δρmax = 0.25 e Å−3 |
375 parameters | Δρmin = −0.21 e Å−3 |
244 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.19 (18) |
Crystal data top
C27H44O7 | V = 2672.4 (5) Å3 |
Mr = 480.62 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 7.663 (1) Å | µ = 0.69 mm−1 |
b = 10.541 (1) Å | T = 293 K |
c = 33.084 (2) Å | 0.45 × 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 = 0.875 | 3 standard reflections every 60 min |
5611 measured reflections | intensity decay: 4% |
4542 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.104 | Δρmax = 0.25 e Å−3 |
S = 1.06 | Δρmin = −0.21 e Å−3 |
4542 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
375 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O2 | 0.0355 (2) | 0.62347 (15) | 0.96440 (4) | 0.0693 (4) | |
H2 | −0.0171 | 0.6811 | 0.9758 | 0.090* | |
O3 | 0.3608 (2) | 0.68324 (16) | 0.99655 (4) | 0.0748 (4) | |
H3 | 0.3109 | 0.6328 | 1.0115 | 0.097* | |
O6 | 0.75094 (19) | 0.93922 (15) | 0.92395 (4) | 0.0691 (4) | |
O14 | 0.41491 (16) | 0.75598 (10) | 0.78838 (4) | 0.0472 (3) | |
H14 | 0.5098 | 0.7204 | 0.7901 | 0.061* | |
O20 | 0.24557 (17) | 1.14640 (11) | 0.70634 (4) | 0.0536 (3) | |
H20 | 0.2114 | 1.1843 | 0.6862 | 0.070* | |
O22 | 0.1573 (2) | 1.06787 (13) | 0.63538 (4) | 0.0726 (4) | |
H22 | 0.1732 | 1.0503 | 0.6115 | 0.094* | |
C1 | 0.1477 (3) | 0.8181 (2) | 0.93521 (5) | 0.0564 (5) | |
H1A | 0.1448 | 0.8539 | 0.9622 | 0.073* | |
H1B | 0.0359 | 0.8357 | 0.9226 | 0.073* | |
C2 | 0.1684 (3) | 0.6761 (2) | 0.93878 (5) | 0.0557 (5) | |
H2A | 0.1566 | 0.6388 | 0.9118 | 0.072* | |
C3 | 0.3471 (3) | 0.6408 (2) | 0.95557 (6) | 0.0604 (5) | |
H3A | 0.3616 | 0.5485 | 0.9546 | 0.079* | |
C4 | 0.4922 (3) | 0.70360 (19) | 0.93144 (6) | 0.0569 (5) | |
H4A | 0.4938 | 0.6687 | 0.9043 | 0.074* | |
H4B | 0.6036 | 0.6849 | 0.9440 | 0.074* | |
C5 | 0.4678 (2) | 0.84785 (18) | 0.92906 (5) | 0.0500 (4) | |
H5 | 0.4715 | 0.8805 | 0.9568 | 0.065* | |
C6 | 0.6163 (2) | 0.90738 (18) | 0.90649 (6) | 0.0529 (4) | |
C7 | 0.5971 (2) | 0.92146 (17) | 0.86264 (6) | 0.0505 (4) | |
H7 | 0.6920 | 0.9503 | 0.8477 | 0.066* | |
C8 | 0.4482 (2) | 0.89443 (15) | 0.84327 (5) | 0.0423 (3) | |
C9 | 0.2848 (2) | 0.85086 (17) | 0.86540 (5) | 0.0448 (3) | |
H9 | 0.2851 | 0.7580 | 0.8642 | 0.058* | |
C10 | 0.2902 (2) | 0.88614 (16) | 0.91099 (5) | 0.0481 (4) | |
C11 | 0.1130 (2) | 0.8942 (2) | 0.84513 (5) | 0.0599 (5) | |
H11A | 0.0187 | 0.8414 | 0.8551 | 0.078* | |
H11B | 0.0888 | 0.9807 | 0.8535 | 0.078* | |
C12 | 0.1122 (2) | 0.8891 (2) | 0.79898 (5) | 0.0533 (4) | |
H12A | 0.0065 | 0.9288 | 0.7890 | 0.069* | |
H12B | 0.1120 | 0.8012 | 0.7903 | 0.069* | |
C13 | 0.2714 (2) | 0.95680 (15) | 0.78091 (5) | 0.0416 (3) | |
C14 | 0.4352 (2) | 0.88873 (14) | 0.79766 (5) | 0.0403 (3) | |
C15 | 0.5822 (2) | 0.94153 (17) | 0.77174 (5) | 0.0478 (4) | |
H15A | 0.6833 | 0.8863 | 0.7724 | 0.062* | |
H15B | 0.6162 | 1.0255 | 0.7807 | 0.062* | |
C16 | 0.5015 (2) | 0.94617 (17) | 0.72912 (5) | 0.0484 (4) | |
H16A | 0.5436 | 0.8759 | 0.7129 | 0.063* | |
H16B | 0.5322 | 1.0249 | 0.7157 | 0.063* | |
C17 | 0.2999 (2) | 0.93691 (15) | 0.73476 (5) | 0.0427 (3) | |
H17 | 0.2701 | 0.8480 | 0.7295 | 0.056* | |
C18 | 0.2756 (3) | 1.09734 (16) | 0.79339 (6) | 0.0533 (4) | |
H18A | 0.1665 | 1.1366 | 0.7865 | 0.080* | |
H18B | 0.3687 | 1.1396 | 0.7794 | 0.080* | |
H18C | 0.2941 | 1.1035 | 0.8220 | 0.080* | |
C19 | 0.2662 (3) | 1.0292 (2) | 0.91743 (6) | 0.0687 (5) | |
H19A | 0.2963 | 1.0506 | 0.9448 | 0.103* | |
H19B | 0.1468 | 1.0517 | 0.9124 | 0.103* | |
H19C | 0.3406 | 1.0747 | 0.8991 | 0.103* | |
C20 | 0.1935 (2) | 1.01479 (15) | 0.70384 (5) | 0.0460 (4) | |
C21 | −0.0027 (2) | 1.0076 (2) | 0.71122 (6) | 0.0599 (5) | |
H21A | −0.0316 | 1.0548 | 0.7351 | 0.090* | |
H21B | −0.0366 | 0.9206 | 0.7147 | 0.090* | |
H21C | −0.0635 | 1.0428 | 0.6885 | 0.090* | |
C22 | 0.2374 (3) | 0.97334 (16) | 0.66031 (5) | 0.0586 (5) | |
H22A | 0.3640 | 0.9714 | 0.6561 | 0.076* | 0.50 |
H22B | 0.3633 | 0.9867 | 0.6574 | 0.076* | 0.50 |
C23A | 0.1545 (15) | 0.8445 (7) | 0.6493 (3) | 0.065 (2) | 0.50 |
H23A | 0.0287 | 0.8551 | 0.6492 | 0.085* | 0.50 |
H23B | 0.1824 | 0.7848 | 0.6707 | 0.085* | 0.50 |
C24A | 0.2086 (14) | 0.7847 (9) | 0.6086 (2) | 0.099 (3) | 0.50 |
H24A | 0.3352 | 0.7847 | 0.6080 | 0.129* | 0.50 |
H24B | 0.1725 | 0.6965 | 0.6095 | 0.129* | 0.50 |
C25A | 0.1496 (11) | 0.8356 (8) | 0.5698 (2) | 0.074 (2) | 0.50 |
O25A | 0.2308 (17) | 0.9592 (9) | 0.5645 (3) | 0.081 (3) | 0.50 |
H25A | 0.1690 | 1.0035 | 0.5500 | 0.105* | 0.50 |
C26A | −0.0497 (9) | 0.8407 (7) | 0.5709 (3) | 0.091 (2) | 0.50 |
H26A | −0.0949 | 0.7579 | 0.5769 | 0.136* | 0.50 |
H26B | −0.0928 | 0.8681 | 0.5451 | 0.136* | 0.50 |
H26C | −0.0865 | 0.8994 | 0.5913 | 0.136* | 0.50 |
C27A | 0.1940 (11) | 0.7503 (8) | 0.5350 (2) | 0.094 (2) | 0.50 |
H27A | 0.3158 | 0.7292 | 0.5359 | 0.142* | 0.50 |
H27B | 0.1688 | 0.7929 | 0.5100 | 0.142* | 0.50 |
H27C | 0.1259 | 0.6740 | 0.5367 | 0.142* | 0.50 |
C23B | 0.2064 (16) | 0.8347 (7) | 0.6486 (3) | 0.076 (3) | 0.50 |
H23C | 0.0817 | 0.8199 | 0.6470 | 0.099* | 0.50 |
H23D | 0.2523 | 0.7807 | 0.6698 | 0.099* | 0.50 |
C24B | 0.2905 (13) | 0.7958 (8) | 0.6082 (2) | 0.090 (3) | 0.50 |
H24C | 0.4102 | 0.8254 | 0.6091 | 0.117* | 0.50 |
H24D | 0.2956 | 0.7039 | 0.6082 | 0.117* | 0.50 |
C25B | 0.2230 (11) | 0.8324 (9) | 0.5689 (3) | 0.079 (2) | 0.50 |
O25B | 0.2204 (15) | 0.9693 (9) | 0.5633 (3) | 0.072 (3) | 0.50 |
H25B | 0.1343 | 0.9892 | 0.5500 | 0.093* | 0.50 |
C26B | 0.0340 (14) | 0.7986 (12) | 0.5676 (5) | 0.177 (6) | 0.50 |
H26D | −0.0262 | 0.8408 | 0.5892 | 0.266* | 0.50 |
H26E | 0.0211 | 0.7085 | 0.5705 | 0.266* | 0.50 |
H26F | −0.0144 | 0.8247 | 0.5422 | 0.266* | 0.50 |
C27B | 0.3150 (15) | 0.7749 (8) | 0.5340 (2) | 0.132 (4) | 0.50 |
H27D | 0.2548 | 0.7965 | 0.5095 | 0.199* | 0.50 |
H27E | 0.3173 | 0.6843 | 0.5370 | 0.199* | 0.50 |
H27F | 0.4323 | 0.8066 | 0.5328 | 0.199* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0701 (9) | 0.0820 (10) | 0.0558 (7) | −0.0153 (8) | 0.0084 (7) | 0.0010 (7) |
O3 | 0.0765 (10) | 0.0967 (11) | 0.0512 (7) | −0.0197 (9) | −0.0155 (7) | 0.0172 (7) |
O6 | 0.0481 (7) | 0.0920 (10) | 0.0671 (8) | −0.0058 (7) | −0.0150 (7) | −0.0023 (7) |
O14 | 0.0473 (6) | 0.0374 (5) | 0.0568 (6) | 0.0036 (5) | 0.0004 (5) | 0.0030 (5) |
O20 | 0.0556 (7) | 0.0406 (5) | 0.0647 (7) | −0.0043 (5) | −0.0125 (6) | 0.0099 (5) |
O22 | 0.1060 (12) | 0.0580 (8) | 0.0539 (7) | 0.0033 (8) | −0.0132 (8) | 0.0140 (6) |
C1 | 0.0458 (10) | 0.0773 (13) | 0.0460 (9) | 0.0113 (9) | 0.0070 (7) | 0.0065 (8) |
C2 | 0.0520 (10) | 0.0734 (12) | 0.0416 (8) | −0.0043 (9) | 0.0012 (8) | −0.0016 (8) |
C3 | 0.0650 (12) | 0.0579 (11) | 0.0583 (11) | 0.0037 (10) | −0.0086 (9) | 0.0037 (9) |
C4 | 0.0480 (10) | 0.0626 (11) | 0.0602 (10) | 0.0129 (8) | −0.0068 (8) | 0.0029 (9) |
C5 | 0.0461 (9) | 0.0593 (10) | 0.0446 (8) | 0.0055 (8) | −0.0051 (7) | −0.0037 (8) |
C6 | 0.0407 (9) | 0.0602 (10) | 0.0576 (10) | 0.0052 (8) | −0.0073 (8) | −0.0038 (8) |
C7 | 0.0369 (8) | 0.0588 (10) | 0.0557 (9) | −0.0006 (8) | −0.0010 (7) | 0.0016 (8) |
C8 | 0.0343 (8) | 0.0417 (8) | 0.0509 (8) | 0.0065 (6) | 0.0009 (6) | 0.0028 (7) |
C9 | 0.0343 (8) | 0.0547 (8) | 0.0453 (8) | 0.0047 (7) | 0.0009 (7) | 0.0046 (7) |
C10 | 0.0427 (9) | 0.0557 (10) | 0.0459 (8) | 0.0117 (8) | 0.0026 (7) | 0.0018 (7) |
C11 | 0.0312 (8) | 0.0950 (15) | 0.0535 (10) | 0.0070 (9) | 0.0019 (7) | 0.0161 (10) |
C12 | 0.0319 (8) | 0.0761 (12) | 0.0520 (9) | −0.0025 (8) | −0.0026 (7) | 0.0140 (9) |
C13 | 0.0334 (7) | 0.0432 (8) | 0.0481 (8) | 0.0015 (7) | 0.0000 (6) | 0.0049 (6) |
C14 | 0.0338 (8) | 0.0382 (7) | 0.0489 (8) | 0.0004 (6) | 0.0006 (6) | 0.0037 (7) |
C15 | 0.0358 (8) | 0.0500 (9) | 0.0576 (9) | 0.0009 (7) | 0.0047 (7) | 0.0054 (7) |
C16 | 0.0437 (9) | 0.0481 (9) | 0.0533 (9) | 0.0042 (7) | 0.0061 (7) | 0.0110 (7) |
C17 | 0.0424 (8) | 0.0377 (7) | 0.0481 (8) | −0.0006 (7) | 0.0011 (7) | 0.0052 (6) |
C18 | 0.0542 (10) | 0.0494 (9) | 0.0564 (9) | 0.0112 (8) | −0.0036 (8) | −0.0019 (7) |
C19 | 0.0734 (14) | 0.0614 (11) | 0.0712 (12) | 0.0207 (11) | 0.0032 (11) | −0.0046 (9) |
C20 | 0.0464 (9) | 0.0410 (8) | 0.0506 (8) | −0.0052 (7) | −0.0044 (7) | 0.0060 (7) |
C21 | 0.0462 (10) | 0.0702 (12) | 0.0633 (11) | −0.0065 (9) | −0.0116 (8) | 0.0132 (9) |
C22 | 0.0763 (13) | 0.0498 (9) | 0.0495 (9) | 0.0000 (10) | −0.0025 (9) | 0.0114 (7) |
C23A | 0.092 (5) | 0.046 (3) | 0.057 (3) | 0.001 (3) | −0.013 (3) | 0.007 (2) |
C24A | 0.165 (8) | 0.064 (3) | 0.068 (4) | −0.008 (5) | −0.005 (5) | −0.001 (3) |
C25A | 0.114 (7) | 0.054 (3) | 0.053 (3) | −0.015 (4) | 0.001 (4) | 0.007 (2) |
O25A | 0.112 (6) | 0.074 (5) | 0.056 (4) | 0.016 (4) | 0.014 (4) | 0.012 (3) |
C26A | 0.104 (5) | 0.058 (3) | 0.110 (4) | −0.028 (3) | −0.039 (4) | 0.016 (3) |
C27A | 0.134 (6) | 0.095 (4) | 0.054 (3) | −0.004 (5) | 0.003 (4) | −0.006 (3) |
C23B | 0.123 (8) | 0.051 (3) | 0.055 (3) | 0.005 (4) | −0.001 (4) | −0.001 (3) |
C24B | 0.155 (8) | 0.055 (3) | 0.061 (3) | 0.030 (4) | −0.020 (4) | 0.004 (3) |
C25B | 0.109 (6) | 0.061 (3) | 0.067 (3) | −0.013 (4) | 0.005 (4) | −0.005 (3) |
O25B | 0.086 (5) | 0.049 (3) | 0.081 (5) | −0.017 (3) | −0.017 (4) | 0.018 (3) |
C26B | 0.190 (14) | 0.126 (10) | 0.215 (11) | −0.057 (9) | −0.025 (11) | 0.041 (9) |
C27B | 0.230 (11) | 0.088 (5) | 0.079 (4) | 0.036 (7) | 0.033 (7) | 0.004 (4) |
Geometric parameters (Å, º) top
O2—C2 | 1.437 (2) | C13—C18 | 1.538 (2) |
O3—C3 | 1.432 (2) | C13—C14 | 1.548 (2) |
O6—C6 | 1.229 (2) | C13—C17 | 1.557 (2) |
O14—C14 | 1.4409 (19) | C14—C15 | 1.521 (2) |
O20—C20 | 1.446 (2) | C15—C16 | 1.540 (2) |
O22—C22 | 1.432 (2) | C16—C17 | 1.559 (2) |
C1—C2 | 1.510 (3) | C17—C20 | 1.544 (2) |
C1—C10 | 1.532 (3) | C20—C21 | 1.525 (3) |
C2—C3 | 1.524 (3) | C20—C22 | 1.542 (2) |
C3—C4 | 1.520 (3) | C22—C23B | 1.530 (6) |
C4—C5 | 1.534 (3) | C22—C23A | 1.542 (6) |
C5—C6 | 1.499 (3) | C23A—C24A | 1.544 (6) |
C5—C10 | 1.540 (2) | C24A—C25A | 1.466 (7) |
C6—C7 | 1.466 (3) | C25A—O25A | 1.454 (9) |
C7—C8 | 1.339 (2) | C25A—C27A | 1.500 (8) |
C8—C14 | 1.513 (2) | C25A—C26A | 1.528 (9) |
C8—C9 | 1.522 (2) | C23B—C24B | 1.541 (7) |
C9—C11 | 1.547 (2) | C24B—C25B | 1.449 (6) |
C9—C10 | 1.554 (2) | C25B—O25B | 1.456 (9) |
C10—C19 | 1.534 (3) | C25B—C27B | 1.484 (8) |
C11—C12 | 1.528 (2) | C25B—C26B | 1.492 (9) |
C12—C13 | 1.534 (2) | | |
| | | |
C2—C1—C10 | 115.45 (16) | C8—C14—C15 | 119.90 (14) |
O2—C2—C1 | 110.75 (16) | O14—C14—C13 | 106.64 (12) |
O2—C2—C3 | 109.14 (15) | C8—C14—C13 | 113.09 (13) |
C1—C2—C3 | 111.43 (17) | C15—C14—C13 | 103.23 (12) |
O3—C3—C4 | 107.91 (17) | C14—C15—C16 | 103.32 (14) |
O3—C3—C2 | 109.57 (16) | C15—C16—C17 | 106.63 (13) |
C4—C3—C2 | 111.05 (15) | C20—C17—C13 | 120.27 (13) |
C3—C4—C5 | 111.68 (16) | C20—C17—C16 | 114.24 (13) |
C6—C5—C4 | 110.35 (16) | C13—C17—C16 | 104.36 (13) |
C6—C5—C10 | 111.59 (14) | O20—C20—C21 | 108.11 (15) |
C4—C5—C10 | 112.79 (16) | O20—C20—C22 | 105.36 (13) |
O6—C6—C7 | 121.46 (18) | C21—C20—C22 | 110.53 (16) |
O6—C6—C5 | 121.17 (16) | O20—C20—C17 | 109.05 (13) |
C7—C6—C5 | 117.33 (15) | C21—C20—C17 | 112.82 (14) |
C8—C7—C6 | 122.53 (16) | C22—C20—C17 | 110.65 (14) |
C7—C8—C14 | 122.82 (15) | O22—C22—C23B | 116.9 (5) |
C7—C8—C9 | 122.35 (15) | O22—C22—C20 | 104.31 (15) |
C14—C8—C9 | 114.41 (13) | C23B—C22—C20 | 118.2 (4) |
C8—C9—C11 | 113.75 (13) | O22—C22—C23A | 107.5 (5) |
C8—C9—C10 | 111.90 (14) | C20—C22—C23A | 112.3 (4) |
C11—C9—C10 | 111.88 (13) | C22—C23A—C24A | 117.0 (6) |
C1—C10—C19 | 107.58 (16) | C25A—C24A—C23A | 122.2 (8) |
C1—C10—C5 | 107.71 (14) | O25A—C25A—C24A | 107.5 (8) |
C19—C10—C5 | 108.02 (17) | O25A—C25A—C27A | 110.3 (7) |
C1—C10—C9 | 112.12 (15) | C24A—C25A—C27A | 112.6 (7) |
C19—C10—C9 | 111.52 (14) | O25A—C25A—C26A | 113.5 (8) |
C5—C10—C9 | 109.73 (13) | C24A—C25A—C26A | 107.5 (7) |
C12—C11—C9 | 115.23 (14) | C27A—C25A—C26A | 105.5 (7) |
C11—C12—C13 | 111.72 (15) | C22—C23B—C24B | 114.1 (7) |
C12—C13—C18 | 111.09 (15) | C25B—C24B—C23B | 123.9 (8) |
C12—C13—C14 | 106.82 (12) | C24B—C25B—O25B | 112.5 (8) |
C18—C13—C14 | 109.46 (13) | C24B—C25B—C27B | 114.8 (7) |
C12—C13—C17 | 115.55 (14) | O25B—C25B—C27B | 108.1 (8) |
C18—C13—C17 | 112.96 (13) | C24B—C25B—C26B | 108.1 (9) |
C14—C13—C17 | 100.08 (12) | O25B—C25B—C26B | 102.7 (8) |
O14—C14—C8 | 104.96 (12) | C27B—C25B—C26B | 109.9 (9) |
O14—C14—C15 | 108.35 (13) | | |
| | | |
C10—C1—C2—O2 | 175.82 (15) | C12—C13—C14—O14 | 54.16 (16) |
C10—C1—C2—C3 | 54.1 (2) | C18—C13—C14—O14 | 174.53 (13) |
O2—C2—C3—O3 | −56.2 (2) | C17—C13—C14—O14 | −66.59 (14) |
C1—C2—C3—O3 | 66.5 (2) | C12—C13—C14—C8 | −60.70 (17) |
O2—C2—C3—C4 | −175.27 (17) | C18—C13—C14—C8 | 59.67 (17) |
C1—C2—C3—C4 | −52.7 (2) | C17—C13—C14—C8 | 178.56 (13) |
O3—C3—C4—C5 | −65.5 (2) | C12—C13—C14—C15 | 168.23 (14) |
C2—C3—C4—C5 | 54.6 (2) | C18—C13—C14—C15 | −71.40 (16) |
C3—C4—C5—C6 | 177.80 (15) | C17—C13—C14—C15 | 47.48 (15) |
C3—C4—C5—C10 | −56.6 (2) | O14—C14—C15—C16 | 72.36 (15) |
C4—C5—C6—O6 | −87.5 (2) | C8—C14—C15—C16 | −167.35 (14) |
C10—C5—C6—O6 | 146.32 (18) | C13—C14—C15—C16 | −40.48 (16) |
C4—C5—C6—C7 | 90.25 (19) | C14—C15—C16—C17 | 17.34 (17) |
C10—C5—C6—C7 | −36.0 (2) | C12—C13—C17—C20 | 80.28 (19) |
O6—C6—C7—C8 | −175.98 (18) | C18—C13—C17—C20 | −49.19 (19) |
C5—C6—C7—C8 | 6.3 (3) | C14—C13—C17—C20 | −165.48 (13) |
C6—C7—C8—C14 | −170.11 (16) | C12—C13—C17—C16 | −149.93 (14) |
C6—C7—C8—C9 | 2.0 (3) | C18—C13—C17—C16 | 80.60 (16) |
C7—C8—C9—C11 | 147.80 (19) | C14—C13—C17—C16 | −35.68 (15) |
C14—C8—C9—C11 | −39.5 (2) | C15—C16—C17—C20 | 145.22 (14) |
C7—C8—C9—C10 | 19.8 (2) | C15—C16—C17—C13 | 11.92 (17) |
C14—C8—C9—C10 | −167.48 (13) | C13—C17—C20—O20 | 67.60 (18) |
C2—C1—C10—C19 | −169.54 (17) | C16—C17—C20—O20 | −57.68 (19) |
C2—C1—C10—C5 | −53.3 (2) | C13—C17—C20—C21 | −52.5 (2) |
C2—C1—C10—C9 | 67.50 (19) | C16—C17—C20—C21 | −177.82 (16) |
C6—C5—C10—C1 | 178.47 (15) | C13—C17—C20—C22 | −176.95 (14) |
C4—C5—C10—C1 | 53.58 (19) | C16—C17—C20—C22 | 57.76 (19) |
C6—C5—C10—C19 | −65.60 (19) | O20—C20—C22—O22 | −51.49 (19) |
C4—C5—C10—C19 | 169.51 (16) | C21—C20—C22—O22 | 65.08 (19) |
C6—C5—C10—C9 | 56.16 (19) | C17—C20—C22—O22 | −169.22 (15) |
C4—C5—C10—C9 | −68.72 (19) | O20—C20—C22—C23B | 176.7 (6) |
C8—C9—C10—C1 | −167.39 (14) | C21—C20—C22—C23B | −66.7 (6) |
C11—C9—C10—C1 | 63.61 (19) | C17—C20—C22—C23B | 59.0 (6) |
C8—C9—C10—C19 | 71.90 (19) | O20—C20—C22—C23A | −167.6 (5) |
C11—C9—C10—C19 | −57.1 (2) | C21—C20—C22—C23A | −51.0 (5) |
C8—C9—C10—C5 | −47.75 (19) | C17—C20—C22—C23A | 74.7 (5) |
C11—C9—C10—C5 | −176.75 (15) | O22—C22—C23A—C24A | 73.7 (9) |
C8—C9—C11—C12 | 39.5 (2) | C20—C22—C23A—C24A | −172.2 (7) |
C10—C9—C11—C12 | 167.53 (17) | C22—C23A—C24A—C25A | −72.2 (12) |
C9—C11—C12—C13 | −51.1 (2) | C23A—C24A—C25A—O25A | 67.7 (11) |
C11—C12—C13—C18 | −59.8 (2) | C23A—C24A—C25A—C27A | −170.6 (8) |
C11—C12—C13—C14 | 59.48 (19) | C23A—C24A—C25A—C26A | −54.9 (10) |
C11—C12—C13—C17 | 169.79 (15) | O22—C22—C23B—C24B | 66.8 (10) |
C7—C8—C14—O14 | 108.70 (17) | C20—C22—C23B—C24B | −167.3 (6) |
C9—C8—C14—O14 | −63.98 (16) | C22—C23B—C24B—C25B | −74.7 (12) |
C7—C8—C14—C15 | −13.3 (2) | C23B—C24B—C25B—O25B | 61.0 (12) |
C9—C8—C14—C15 | 174.04 (14) | C23B—C24B—C25B—C27B | −174.7 (8) |
C7—C8—C14—C13 | −135.44 (16) | C23B—C24B—C25B—C26B | −51.7 (12) |
C9—C8—C14—C13 | 51.88 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3i | 0.82 | 1.94 | 2.759 (2) | 179 |
O3—H3···O6i | 0.82 | 2.31 | 3.048 (2) | 150 |
O14—H14···O20ii | 0.82 | 2.03 | 2.8520 (17) | 175 |
O20—H20···O22 | 0.82 | 2.12 | 2.5795 (19) | 115 |
O22—H22···O25A | 0.82 | 1.88 | 2.671 (10) | 161 |
O22—H22···O25B | 0.82 | 1.84 | 2.645 (12) | 165 |
O25A—H25A···O2iii | 0.82 | 2.07 | 2.842 (14) | 157 |
O25B—H25B···O2iii | 0.82 | 1.98 | 2.707 (13) | 147 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x, y+1/2, −z+3/2. |
(III) 2
β,3
β,14
α,20
R,22
R,25-hexahydroxy-5
β-cholest-7-en-6-one
methanol solvate hydrate
top
Crystal data top
C27H44O7·CH4O·H2O | Dx = 1.224 Mg m−3 |
Mr = 530.68 | Cu Kα radiation, λ = 1.54180 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 7.167 (1) Å | θ = 20.1–23.9° |
b = 9.703 (1) Å | µ = 0.73 mm−1 |
c = 41.412 (4) Å | T = 293 K |
V = 2879.8 (6) Å3 | Prism, colorless |
Z = 4 | 0.25 × 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 tube | Rint = 0.012 |
Graphite monochromator | θmax = 75.0°, θmin = 2.1° |
/w–2/q scans | h = −8→8 |
Absorption correction: ψ scan North A.C., Philips D.C. & Mathews F.(1968): Acta Cryst. A24 350-359 | k = −12→12 |
Tmin = 0.838, Tmax = 0.930 | l = −51→51 |
6775 measured reflections | 3 standard reflections every 1hr min |
5774 independent reflections | intensity decay: 10% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H 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 = 0.86 | Δρmax = 0.23 e Å−3 |
5774 reflections | Δρmin = −0.15 e Å−3 |
356 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.0017 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.09 (17) |
Crystal data top
C27H44O7·CH4O·H2O | V = 2879.8 (6) Å3 |
Mr = 530.68 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 7.167 (1) Å | µ = 0.73 mm−1 |
b = 9.703 (1) Å | T = 293 K |
c = 41.412 (4) Å | 0.25 × 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 = 0.930 | 3 standard reflections every 1hr min |
6775 measured reflections | intensity decay: 10% |
5774 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.121 | Δρmax = 0.23 e Å−3 |
S = 0.86 | Δρmin = −0.15 e Å−3 |
5774 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
356 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | |
O2 | 0.9975 (2) | 0.71492 (19) | 0.73477 (4) | 0.0510 (4) | |
H2 | 0.935 (3) | 0.771 (3) | 0.7274 (6) | 0.066* | |
O3 | 0.6431 (2) | 0.62436 (19) | 0.71560 (3) | 0.0489 (4) | |
H3 | 0.695 (3) | 0.629 (2) | 0.6965 (6) | 0.064* | |
O6 | 0.2328 (2) | 0.44281 (17) | 0.79407 (4) | 0.0489 (4) | |
O14 | 0.87180 (19) | 0.25902 (14) | 0.84914 (3) | 0.0349 (3) | |
H14 | 0.8108 (14) | 0.205 (2) | 0.8352 (4) | 0.045* | |
O20 | 0.8978 (2) | 0.41424 (15) | 0.96825 (3) | 0.0413 (3) | |
H20 | 0.824 (4) | 0.3647 (17) | 0.9769 (5) | 0.054* | |
O22 | 1.1230 (2) | 0.22470 (19) | 0.99697 (3) | 0.0511 (4) | |
H22 | 1.056 (4) | 0.284 (3) | 1.0055 (4) | 0.066* | |
O25 | 1.5492 (2) | −0.02393 (17) | 0.97293 (4) | 0.0535 (4) | |
H25 | 1.517 (2) | −0.002 (3) | 0.9950 (7) | 0.069* | |
C1 | 0.7907 (3) | 0.7172 (2) | 0.78106 (4) | 0.0382 (4) | |
H1A | 0.7179 | 0.7871 | 0.7700 | 0.050* | |
H1B | 0.8844 | 0.7641 | 0.7939 | 0.050* | |
C2 | 0.8888 (3) | 0.6295 (2) | 0.75594 (5) | 0.0391 (4) | |
H2A | 0.9750 | 0.5680 | 0.7673 | 0.051* | |
C3 | 0.7549 (3) | 0.5399 (2) | 0.73653 (4) | 0.0388 (4) | |
H3A | 0.8270 | 0.4748 | 0.7234 | 0.050* | |
C4 | 0.6247 (3) | 0.4601 (2) | 0.75867 (4) | 0.0373 (4) | |
H4A | 0.6964 | 0.3920 | 0.7705 | 0.048* | |
H4B | 0.5334 | 0.4114 | 0.7457 | 0.048* | |
C5 | 0.5227 (3) | 0.5540 (2) | 0.78275 (4) | 0.0344 (4) | |
H5 | 0.4472 | 0.6198 | 0.7704 | 0.045* | |
C6 | 0.3928 (3) | 0.4669 (2) | 0.80270 (5) | 0.0359 (4) | |
C7 | 0.4723 (3) | 0.4023 (2) | 0.83165 (4) | 0.0350 (4) | |
H7 | 0.3998 | 0.3403 | 0.8433 | 0.045* | |
C8 | 0.6454 (2) | 0.42965 (18) | 0.84177 (4) | 0.0287 (4) | |
C9 | 0.7730 (3) | 0.53426 (18) | 0.82557 (4) | 0.0310 (4) | |
H9 | 0.8523 | 0.4813 | 0.8108 | 0.040* | |
C10 | 0.6609 (3) | 0.63682 (19) | 0.80394 (4) | 0.0334 (4) | |
C11 | 0.9071 (3) | 0.6057 (2) | 0.84937 (5) | 0.0422 (5) | |
H11A | 1.0051 | 0.6507 | 0.8371 | 0.055* | |
H11B | 0.8388 | 0.6768 | 0.8609 | 0.055* | |
C12 | 0.9971 (3) | 0.5094 (2) | 0.87408 (4) | 0.0375 (4) | |
H12A | 1.0688 | 0.5634 | 0.8894 | 0.049* | |
H12B | 1.0821 | 0.4473 | 0.8631 | 0.049* | |
C13 | 0.8499 (2) | 0.42528 (18) | 0.89226 (4) | 0.0287 (4) | |
C14 | 0.7390 (3) | 0.34097 (18) | 0.86712 (4) | 0.0288 (4) | |
C15 | 0.6205 (3) | 0.2433 (2) | 0.88740 (4) | 0.0376 (4) | |
H15A | 0.5887 | 0.1609 | 0.8753 | 0.049* | |
H15B | 0.5065 | 0.2879 | 0.8945 | 0.049* | |
C16 | 0.7481 (3) | 0.2088 (2) | 0.91632 (4) | 0.0395 (4) | |
H16A | 0.7868 | 0.1131 | 0.9154 | 0.051* | |
H16B | 0.6821 | 0.2238 | 0.9365 | 0.051* | |
C17 | 0.9198 (3) | 0.30465 (18) | 0.91423 (4) | 0.0302 (4) | |
H17 | 1.0125 | 0.2546 | 0.9014 | 0.039* | |
C18 | 0.7151 (3) | 0.5220 (2) | 0.91005 (5) | 0.0438 (5) | |
H18A | 0.6399 | 0.5705 | 0.8946 | 0.066* | |
H18B | 0.7852 | 0.5870 | 0.9226 | 0.066* | |
H18C | 0.6360 | 0.4690 | 0.9240 | 0.066* | |
C19 | 0.5495 (4) | 0.7400 (2) | 0.82429 (5) | 0.0478 (5) | |
H19A | 0.6330 | 0.8071 | 0.8334 | 0.072* | |
H19B | 0.4865 | 0.6920 | 0.8414 | 0.072* | |
H19C | 0.4594 | 0.7856 | 0.8109 | 0.072* | |
C20 | 1.0148 (3) | 0.33427 (19) | 0.94712 (4) | 0.0316 (4) | |
C21 | 1.1908 (3) | 0.4202 (2) | 0.94328 (5) | 0.0415 (5) | |
H21A | 1.1572 | 0.5144 | 0.9392 | 0.062* | |
H21B | 1.2629 | 0.3854 | 0.9255 | 0.062* | |
H21C | 1.2633 | 0.4152 | 0.9627 | 0.062* | |
C22 | 1.0565 (3) | 0.1963 (2) | 0.96462 (4) | 0.0373 (4) | |
H22A | 0.9406 | 0.1431 | 0.9661 | 0.048* | |
C23 | 1.2044 (3) | 0.1075 (2) | 0.94880 (5) | 0.0417 (5) | |
H23A | 1.3247 | 0.1524 | 0.9510 | 0.054* | |
H23B | 1.1773 | 0.1000 | 0.9259 | 0.054* | |
C24 | 1.2163 (3) | −0.0369 (2) | 0.96324 (6) | 0.0470 (5) | |
H24A | 1.1208 | −0.0938 | 0.9534 | 0.061* | |
H24B | 1.1888 | −0.0311 | 0.9861 | 0.061* | |
C25 | 1.4053 (4) | −0.1082 (2) | 0.95899 (5) | 0.0485 (5) | |
C26 | 1.4584 (6) | −0.1249 (3) | 0.92376 (6) | 0.0750 (9) | |
H26A | 1.4602 | −0.0363 | 0.9135 | 0.112* | |
H26B | 1.3688 | −0.1830 | 0.9132 | 0.112* | |
H26C | 1.5799 | −0.1662 | 0.9223 | 0.112* | |
C27 | 1.4038 (5) | −0.2468 (3) | 0.97646 (7) | 0.0748 (9) | |
H27A | 1.5197 | −0.2937 | 0.9726 | 0.112* | |
H27B | 1.3025 | −0.3019 | 0.9685 | 0.112* | |
H27C | 1.3884 | −0.2319 | 0.9992 | 0.112* | |
O1W | 0.7315 (2) | 0.09113 (18) | 0.80330 (4) | 0.0529 (4) | |
H1W | 0.630 (2) | 0.1056 (4) | 0.79629 (17) | 0.069* | |
H2W | 0.8018 (16) | 0.1207 (7) | 0.7891 (3) | 0.069* | |
O2X | 1.1907 (2) | 0.1096 (2) | 0.84535 (5) | 0.0593 (5) | |
H2X | 1.107 (4) | 0.166 (3) | 0.8474 (8) | 0.077* | |
C3X | 1.1205 (5) | −0.0238 (3) | 0.85242 (7) | 0.0722 (8) | |
H3X1 | 1.0808 | −0.0272 | 0.8745 | 0.108* | |
H3X2 | 1.2168 | −0.0910 | 0.8489 | 0.108* | |
H3X3 | 1.0165 | −0.0435 | 0.8386 | 0.108* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0337 (8) | 0.0668 (10) | 0.0524 (8) | −0.0012 (8) | 0.0021 (7) | 0.0207 (8) |
O3 | 0.0399 (8) | 0.0727 (10) | 0.0340 (7) | 0.0043 (8) | −0.0056 (6) | 0.0136 (7) |
O6 | 0.0295 (7) | 0.0639 (9) | 0.0533 (8) | −0.0012 (7) | −0.0095 (6) | 0.0119 (7) |
O14 | 0.0339 (7) | 0.0397 (7) | 0.0310 (6) | 0.0064 (6) | −0.0038 (5) | −0.0077 (5) |
O20 | 0.0451 (8) | 0.0493 (8) | 0.0295 (6) | 0.0062 (7) | 0.0046 (6) | −0.0069 (6) |
O22 | 0.0641 (10) | 0.0632 (10) | 0.0259 (6) | 0.0169 (9) | −0.0105 (7) | −0.0026 (6) |
O25 | 0.0539 (10) | 0.0524 (9) | 0.0541 (9) | −0.0003 (8) | −0.0065 (8) | −0.0048 (8) |
C1 | 0.0411 (11) | 0.0355 (9) | 0.0379 (9) | −0.0013 (9) | −0.0044 (8) | 0.0084 (8) |
C2 | 0.0290 (10) | 0.0472 (11) | 0.0410 (10) | 0.0023 (8) | −0.0002 (8) | 0.0135 (9) |
C3 | 0.0350 (10) | 0.0496 (11) | 0.0319 (8) | 0.0068 (9) | 0.0014 (8) | 0.0044 (8) |
C4 | 0.0373 (10) | 0.0412 (10) | 0.0333 (9) | −0.0032 (9) | −0.0031 (8) | −0.0013 (8) |
C5 | 0.0307 (9) | 0.0404 (10) | 0.0321 (8) | 0.0051 (8) | −0.0032 (7) | 0.0066 (7) |
C6 | 0.0280 (9) | 0.0428 (10) | 0.0368 (9) | 0.0034 (8) | −0.0028 (8) | 0.0023 (8) |
C7 | 0.0288 (9) | 0.0406 (10) | 0.0355 (9) | −0.0002 (8) | 0.0002 (7) | 0.0053 (8) |
C8 | 0.0289 (9) | 0.0309 (8) | 0.0264 (7) | 0.0024 (7) | 0.0001 (7) | 0.0004 (7) |
C9 | 0.0310 (9) | 0.0332 (9) | 0.0288 (8) | −0.0002 (8) | −0.0033 (7) | 0.0033 (7) |
C10 | 0.0350 (10) | 0.0331 (8) | 0.0321 (8) | 0.0025 (7) | −0.0011 (8) | 0.0045 (7) |
C11 | 0.0461 (12) | 0.0393 (10) | 0.0413 (10) | −0.0130 (10) | −0.0113 (9) | 0.0101 (8) |
C12 | 0.0369 (10) | 0.0418 (10) | 0.0339 (8) | −0.0114 (9) | −0.0077 (8) | 0.0045 (8) |
C13 | 0.0286 (9) | 0.0317 (8) | 0.0258 (8) | 0.0007 (7) | −0.0003 (6) | −0.0015 (7) |
C14 | 0.0270 (9) | 0.0336 (8) | 0.0259 (7) | 0.0028 (7) | −0.0005 (7) | −0.0002 (7) |
C15 | 0.0352 (10) | 0.0445 (10) | 0.0332 (9) | −0.0064 (9) | −0.0026 (8) | 0.0063 (8) |
C16 | 0.0424 (11) | 0.0434 (10) | 0.0329 (9) | −0.0115 (10) | −0.0058 (8) | 0.0092 (8) |
C17 | 0.0349 (9) | 0.0315 (8) | 0.0242 (8) | 0.0006 (7) | −0.0009 (7) | 0.0009 (7) |
C18 | 0.0480 (12) | 0.0446 (11) | 0.0389 (10) | 0.0098 (10) | −0.0024 (9) | −0.0069 (8) |
C19 | 0.0553 (13) | 0.0418 (11) | 0.0463 (11) | 0.0102 (10) | 0.0022 (10) | 0.0003 (9) |
C20 | 0.0329 (9) | 0.0384 (9) | 0.0235 (7) | 0.0004 (8) | 0.0003 (7) | −0.0022 (7) |
C21 | 0.0393 (11) | 0.0475 (11) | 0.0377 (10) | −0.0071 (9) | −0.0056 (8) | −0.0023 (9) |
C22 | 0.0401 (10) | 0.0470 (11) | 0.0247 (8) | 0.0012 (9) | −0.0050 (7) | 0.0027 (8) |
C23 | 0.0493 (12) | 0.0412 (10) | 0.0345 (9) | 0.0050 (9) | −0.0027 (9) | −0.0006 (8) |
C24 | 0.0527 (13) | 0.0396 (10) | 0.0488 (11) | −0.0038 (10) | −0.0089 (10) | 0.0012 (9) |
C25 | 0.0632 (14) | 0.0345 (10) | 0.0477 (11) | 0.0052 (10) | −0.0114 (11) | −0.0029 (9) |
C26 | 0.104 (3) | 0.0658 (16) | 0.0549 (14) | 0.0262 (18) | −0.0065 (15) | −0.0165 (13) |
C27 | 0.093 (2) | 0.0423 (13) | 0.089 (2) | 0.0043 (15) | −0.0193 (18) | 0.0125 (13) |
O1W | 0.0441 (9) | 0.0674 (10) | 0.0471 (8) | −0.0051 (8) | −0.0033 (7) | −0.0136 (7) |
O2X | 0.0423 (9) | 0.0720 (11) | 0.0636 (10) | 0.0092 (9) | 0.0017 (8) | −0.0152 (9) |
C3X | 0.090 (2) | 0.0636 (16) | 0.0629 (15) | 0.0179 (17) | 0.0011 (16) | −0.0025 (13) |
Geometric parameters (Å, º) top
O2—C2 | 1.436 (2) | C9—C10 | 1.562 (2) |
O3—C3 | 1.437 (2) | C10—C19 | 1.533 (3) |
O6—C6 | 1.224 (2) | C11—C12 | 1.529 (3) |
O14—C14 | 1.447 (2) | C12—C13 | 1.532 (3) |
O20—C20 | 1.439 (2) | C13—C18 | 1.535 (3) |
O22—C22 | 1.448 (2) | C13—C14 | 1.544 (2) |
O25—C25 | 1.437 (3) | C13—C17 | 1.565 (2) |
C1—C2 | 1.516 (3) | C14—C15 | 1.524 (3) |
C1—C10 | 1.540 (3) | C15—C16 | 1.544 (3) |
C2—C3 | 1.524 (3) | C16—C17 | 1.545 (3) |
C3—C4 | 1.520 (3) | C17—C20 | 1.550 (2) |
C4—C5 | 1.537 (3) | C20—C21 | 1.520 (3) |
C5—C6 | 1.505 (3) | C20—C22 | 1.551 (3) |
C5—C10 | 1.548 (3) | C22—C23 | 1.515 (3) |
C6—C7 | 1.468 (3) | C23—C24 | 1.526 (3) |
C7—C8 | 1.336 (3) | C24—C25 | 1.531 (3) |
C8—C14 | 1.514 (2) | C25—C26 | 1.516 (3) |
C8—C9 | 1.522 (2) | C25—C27 | 1.527 (3) |
C9—C11 | 1.541 (3) | O2X—C3X | 1.420 (4) |
| | | |
C2—C1—C10 | 114.73 (16) | C12—C13—C17 | 117.65 (15) |
O2—C2—C1 | 110.30 (17) | C18—C13—C17 | 112.31 (15) |
O2—C2—C3 | 110.40 (16) | C14—C13—C17 | 99.24 (13) |
C1—C2—C3 | 112.96 (16) | O14—C14—C8 | 104.29 (13) |
O3—C3—C4 | 108.18 (17) | O14—C14—C15 | 107.97 (15) |
O3—C3—C2 | 110.13 (16) | C8—C14—C15 | 119.24 (16) |
C4—C3—C2 | 111.04 (15) | O14—C14—C13 | 107.41 (14) |
C3—C4—C5 | 112.40 (16) | C8—C14—C13 | 113.23 (14) |
C6—C5—C4 | 108.50 (16) | C15—C14—C13 | 104.17 (14) |
C6—C5—C10 | 112.10 (15) | C14—C15—C16 | 103.43 (15) |
C4—C5—C10 | 111.79 (15) | C15—C16—C17 | 107.32 (14) |
O6—C6—C7 | 121.35 (19) | C16—C17—C20 | 114.36 (14) |
O6—C6—C5 | 121.79 (18) | C16—C17—C13 | 103.17 (14) |
C7—C6—C5 | 116.66 (16) | C20—C17—C13 | 120.87 (15) |
C8—C7—C6 | 122.09 (18) | O20—C20—C21 | 104.55 (15) |
C7—C8—C14 | 121.04 (17) | O20—C20—C17 | 112.23 (15) |
C7—C8—C9 | 123.54 (16) | C21—C20—C17 | 111.98 (15) |
C14—C8—C9 | 114.73 (14) | O20—C20—C22 | 107.06 (14) |
C8—C9—C11 | 113.13 (14) | C21—C20—C22 | 111.26 (16) |
C8—C9—C10 | 111.62 (15) | C17—C20—C22 | 109.59 (15) |
C11—C9—C10 | 113.63 (15) | O22—C22—C23 | 106.14 (16) |
C19—C10—C1 | 108.79 (16) | O22—C22—C20 | 109.36 (16) |
C19—C10—C5 | 108.50 (17) | C23—C22—C20 | 115.05 (16) |
C1—C10—C5 | 107.49 (14) | C22—C23—C24 | 113.07 (18) |
C19—C10—C9 | 111.65 (16) | C23—C24—C25 | 114.8 (2) |
C1—C10—C9 | 111.39 (16) | O25—C25—C26 | 105.5 (2) |
C5—C10—C9 | 108.89 (15) | O25—C25—C27 | 108.4 (2) |
C12—C11—C9 | 114.59 (16) | C26—C25—C27 | 111.3 (2) |
C11—C12—C13 | 111.36 (16) | O25—C25—C24 | 109.38 (16) |
C12—C13—C18 | 110.08 (16) | C26—C25—C24 | 112.4 (2) |
C12—C13—C14 | 107.81 (14) | C27—C25—C24 | 109.7 (2) |
C18—C13—C14 | 108.87 (15) | | |
| | | |
C10—C1—C2—O2 | 176.70 (16) | C9—C8—C14—O14 | −65.92 (18) |
C10—C1—C2—C3 | 52.6 (2) | C7—C8—C14—C15 | −15.6 (3) |
O2—C2—C3—O3 | −54.2 (2) | C9—C8—C14—C15 | 173.59 (16) |
C1—C2—C3—O3 | 69.8 (2) | C7—C8—C14—C13 | −138.69 (18) |
O2—C2—C3—C4 | −174.03 (16) | C9—C8—C14—C13 | 50.5 (2) |
C1—C2—C3—C4 | −50.0 (2) | C12—C13—C14—O14 | 56.25 (17) |
O3—C3—C4—C5 | −67.9 (2) | C18—C13—C14—O14 | 175.64 (14) |
C2—C3—C4—C5 | 53.1 (2) | C17—C13—C14—O14 | −66.84 (15) |
C3—C4—C5—C6 | 178.02 (16) | C12—C13—C14—C8 | −58.33 (19) |
C3—C4—C5—C10 | −57.9 (2) | C18—C13—C14—C8 | 61.06 (19) |
C4—C5—C6—O6 | −88.3 (2) | C17—C13—C14—C8 | 178.57 (14) |
C10—C5—C6—O6 | 147.8 (2) | C12—C13—C14—C15 | 170.62 (15) |
C4—C5—C6—C7 | 86.6 (2) | C18—C13—C14—C15 | −69.99 (18) |
C10—C5—C6—C7 | −37.3 (2) | C17—C13—C14—C15 | 47.53 (17) |
O6—C6—C7—C8 | −178.6 (2) | O14—C14—C15—C16 | 78.70 (18) |
C5—C6—C7—C8 | 6.5 (3) | C8—C14—C15—C16 | −162.69 (16) |
C6—C7—C8—C14 | −166.89 (17) | C13—C14—C15—C16 | −35.28 (19) |
C6—C7—C8—C9 | 3.1 (3) | C14—C15—C16—C17 | 8.7 (2) |
C7—C8—C9—C11 | 148.24 (19) | C15—C16—C17—C20 | 153.64 (16) |
C14—C8—C9—C11 | −41.2 (2) | C15—C16—C17—C13 | 20.5 (2) |
C7—C8—C9—C10 | 18.6 (2) | C12—C13—C17—C16 | −156.55 (15) |
C14—C8—C9—C10 | −170.89 (15) | C18—C13—C17—C16 | 74.12 (18) |
C2—C1—C10—C19 | −171.32 (17) | C14—C13—C17—C16 | −40.77 (17) |
C2—C1—C10—C5 | −54.0 (2) | C12—C13—C17—C20 | 74.2 (2) |
C2—C1—C10—C9 | 65.2 (2) | C18—C13—C17—C20 | −55.2 (2) |
C6—C5—C10—C19 | −64.7 (2) | C14—C13—C17—C20 | −170.06 (15) |
C4—C5—C10—C19 | 173.26 (16) | C16—C17—C20—O20 | −67.0 (2) |
C6—C5—C10—C1 | 177.86 (15) | C13—C17—C20—O20 | 57.2 (2) |
C4—C5—C10—C1 | 55.77 (19) | C16—C17—C20—C21 | 175.79 (16) |
C6—C5—C10—C9 | 57.1 (2) | C13—C17—C20—C21 | −60.0 (2) |
C4—C5—C10—C9 | −65.02 (19) | C16—C17—C20—C22 | 51.8 (2) |
C8—C9—C10—C19 | 72.8 (2) | C13—C17—C20—C22 | 176.01 (16) |
C11—C9—C10—C19 | −56.6 (2) | O20—C20—C22—O22 | −50.8 (2) |
C8—C9—C10—C1 | −165.35 (15) | C21—C20—C22—O22 | 62.9 (2) |
C11—C9—C10—C1 | 65.3 (2) | C17—C20—C22—O22 | −172.72 (16) |
C8—C9—C10—C5 | −46.98 (19) | O20—C20—C22—C23 | −170.08 (16) |
C11—C9—C10—C5 | −176.37 (15) | C21—C20—C22—C23 | −56.4 (2) |
C8—C9—C11—C12 | 42.9 (2) | C17—C20—C22—C23 | 68.0 (2) |
C10—C9—C11—C12 | 171.54 (17) | O22—C22—C23—C24 | 69.1 (2) |
C9—C11—C12—C13 | −53.3 (2) | C20—C22—C23—C24 | −169.82 (17) |
C11—C12—C13—C18 | −59.6 (2) | C22—C23—C24—C25 | −155.72 (18) |
C11—C12—C13—C14 | 59.0 (2) | C23—C24—C25—O25 | 57.2 (2) |
C11—C12—C13—C17 | 170.06 (16) | C23—C24—C25—C26 | −59.6 (3) |
C7—C8—C14—O14 | 104.87 (19) | C23—C24—C25—C27 | 176.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O6i | 0.77 | 2.24 | 3.007 (2) | 177 |
O3—H3···O2Xii | 0.88 | 1.92 | 2.794 (2) | 172 |
O14—H14···O1W | 0.89 | 1.81 | 2.696 (2) | 169 |
O20—H20···O22iii | 0.80 | 2.00 | 2.787 (2) | 169 |
O22—H22···O25iii | 0.83 | 2.50 | 3.204 (2) | 144 |
O22—H22···O20 | 0.83 | 2.29 | 2.721 (2) | 113 |
O25—H25···O20iv | 0.97 | 1.94 | 2.871 (2) | 161 |
O1W—H1W···O3v | 0.80 | 2.03 | 2.815 (2) | 171 |
O1W—H2W···O2vi | 0.83 | 1.97 | 2.775 (2) | 165 |
O2X—H2X···O14 | 0.82 | 1.91 | 2.711 (2) | 165 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+2, y+1/2, −z+3/2; (iii) x−1/2, −y+1/2, −z+2; (iv) x+1/2, −y+1/2, −z+2; (v) −x+1, y−1/2, −z+3/2; (vi) −x+2, y−1/2, −z+3/2. |
(IV) 2
β,3
β,14
α,20
R,22
R,25-hexahydroxy-5
β-cholest-7-en-6-one
trihydrate
top
Crystal data top
C27H50O10 | Dx = 1.183 Mg m−3 |
Mr = 534.67 | Mo Kα radiation, λ = 0.710730 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 11.293 (2) Å | θ = 11.5–16.9° |
b = 14.202 (2) Å | µ = 0.09 mm−1 |
c = 18.721 (3) Å | T = 293 K |
V = 3002.5 (8) Å3 | Prism, colorless |
Z = 4 | 0.6 × 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 tube | Rint = 0.011 |
Graphite monochromator | θmax = 33.4°, θmin = 2.6° |
ω–2θ scans | h = −17→17 |
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 = −22→22 |
Tmin = 0.898, Tmax = 0.972 | l = −29→29 |
13105 measured reflections | 2 standard reflections every 60 min |
11655 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | Riding |
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 reflections | Δρmax = 0.26 e Å−3 |
366 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.1 (7) |
Crystal data top
C27H50O10 | V = 3002.5 (8) Å3 |
Mr = 534.67 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 11.293 (2) Å | µ = 0.09 mm−1 |
b = 14.202 (2) Å | T = 293 K |
c = 18.721 (3) Å | 0.6 × 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 = 0.972 | 2 standard reflections every 60 min |
13105 measured reflections | intensity decay: none |
11655 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.054 | Riding |
wR(F2) = 0.142 | Δρmax = 0.26 e Å−3 |
S = 0.92 | Δρmin = −0.18 e Å−3 |
11655 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
366 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.77408 (14) | 1.02561 (10) | −0.01392 (8) | 0.0322 (3) | |
H1A | 0.7974 | 1.0777 | −0.0444 | 0.042* | |
H1B | 0.7303 | 0.9812 | −0.0431 | 0.042* | |
C2 | 0.69256 (15) | 1.06274 (11) | 0.04407 (9) | 0.0366 (3) | |
H2 | 0.6631 | 1.0094 | 0.0721 | 0.048* | |
O2 | 0.59454 (13) | 1.10727 (10) | 0.00977 (8) | 0.0553 (4) | |
H2A | 0.5562 | 1.1370 | 0.0394 | 0.083* | |
C3 | 0.75590 (17) | 1.13027 (11) | 0.09369 (10) | 0.0415 (4) | |
H3 | 0.7022 | 1.1485 | 0.1324 | 0.054* | |
O3 | 0.78675 (15) | 1.21142 (9) | 0.05355 (8) | 0.0580 (4) | |
H3A | 0.8066 | 1.2538 | 0.0808 | 0.087* | |
C4 | 0.86436 (17) | 1.08198 (11) | 0.12542 (9) | 0.0399 (4) | |
H4A | 0.8391 | 1.0297 | 0.1550 | 0.052* | |
H4B | 0.9067 | 1.1262 | 0.1555 | 0.052* | |
C5 | 0.94797 (15) | 1.04552 (11) | 0.06683 (9) | 0.0356 (3) | |
H5 | 0.9755 | 1.1000 | 0.0393 | 0.046* | |
C6 | 1.05479 (15) | 1.00078 (12) | 0.10132 (10) | 0.0382 (4) | |
O6 | 1.14526 (12) | 1.04495 (9) | 0.11276 (9) | 0.0535 (4) | |
C7 | 1.03915 (15) | 0.90396 (11) | 0.12623 (10) | 0.0382 (4) | |
H7 | 1.0963 | 0.8777 | 0.1559 | 0.050* | |
C8 | 0.94543 (13) | 0.85215 (10) | 0.10763 (8) | 0.0282 (3) | |
C9 | 0.85479 (12) | 0.88334 (10) | 0.05330 (8) | 0.0269 (3) | |
H9 | 0.7813 | 0.8952 | 0.0797 | 0.035* | |
C10 | 0.88652 (13) | 0.97681 (10) | 0.01419 (8) | 0.0297 (3) | |
C11 | 0.82818 (15) | 0.80203 (10) | 0.00046 (9) | 0.0340 (3) | |
H11A | 0.7619 | 0.8200 | −0.0296 | 0.044* | |
H11B | 0.8964 | 0.7930 | −0.0303 | 0.044* | |
C12 | 0.79886 (14) | 0.70802 (10) | 0.03736 (9) | 0.0324 (3) | |
H12A | 0.7257 | 0.7144 | 0.0641 | 0.042* | |
H12B | 0.7876 | 0.6595 | 0.0015 | 0.042* | |
C13 | 0.89862 (13) | 0.67902 (9) | 0.08796 (7) | 0.0255 (3) | |
C14 | 0.91480 (13) | 0.75961 (10) | 0.14301 (8) | 0.0290 (3) | |
O14 | 0.80137 (11) | 0.77454 (8) | 0.17584 (6) | 0.0387 (3) | |
H14 | 0.8097 | 0.8062 | 0.2121 | 0.058* | |
C15 | 0.99788 (17) | 0.71733 (12) | 0.19799 (9) | 0.0398 (4) | |
H15A | 0.9945 | 0.7517 | 0.2427 | 0.052* | |
H15B | 1.0789 | 0.7168 | 0.1808 | 0.052* | |
C16 | 0.94966 (17) | 0.61677 (11) | 0.20676 (9) | 0.0390 (4) | |
H16A | 0.9023 | 0.6121 | 0.2498 | 0.051* | |
H16B | 1.0144 | 0.5721 | 0.2101 | 0.051* | |
C17 | 0.87246 (13) | 0.59560 (10) | 0.13985 (8) | 0.0276 (3) | |
H17 | 0.7899 | 0.6028 | 0.1550 | 0.036* | |
C18 | 0.97061 (16) | 0.96075 (14) | −0.04868 (10) | 0.0429 (4) | |
H18A | 1.0377 | 0.9248 | −0.0329 | 0.060* | |
H18B | 0.9969 | 1.0204 | −0.0669 | 0.060* | |
H18C | 0.9300 | 0.9270 | −0.0857 | 0.060* | |
C19 | 1.01479 (14) | 0.66523 (12) | 0.04681 (10) | 0.0367 (3) | |
H19A | 1.0004 | 0.6272 | 0.0053 | 0.051* | |
H19B | 1.0715 | 0.6344 | 0.0770 | 0.051* | |
H19C | 1.0452 | 0.7254 | 0.0324 | 0.051* | |
C20 | 0.88544 (13) | 0.49292 (10) | 0.11359 (8) | 0.0282 (3) | |
O20 | 1.00922 (10) | 0.46874 (8) | 0.10989 (7) | 0.0372 (3) | |
H20 | 1.0252 | 0.4504 | 0.0695 | 0.056* | |
C21 | 0.82629 (15) | 0.47459 (11) | 0.04189 (9) | 0.0344 (3) | |
H21A | 0.8686 | 0.5073 | 0.0050 | 0.048* | |
H21B | 0.7460 | 0.4967 | 0.0434 | 0.048* | |
H21C | 0.8270 | 0.4082 | 0.0321 | 0.048* | |
C22 | 0.83453 (14) | 0.42592 (10) | 0.17177 (9) | 0.0329 (3) | |
H22 | 0.8691 | 0.4437 | 0.2179 | 0.043* | |
O22 | 0.87121 (12) | 0.33132 (8) | 0.15558 (7) | 0.0429 (3) | |
H22A | 0.9418 | 0.3311 | 0.1454 | 0.064* | |
C23 | 0.70132 (16) | 0.42510 (14) | 0.17974 (11) | 0.0445 (4) | |
H23A | 0.6662 | 0.3997 | 0.1366 | 0.058* | |
H23B | 0.6734 | 0.4893 | 0.1853 | 0.058* | |
C24 | 0.66071 (19) | 0.3670 (2) | 0.24327 (13) | 0.0688 (7) | |
H24A | 0.7046 | 0.3875 | 0.2850 | 0.090* | |
H24B | 0.6815 | 0.3018 | 0.2345 | 0.090* | |
C25 | 0.5293 (2) | 0.3716 (2) | 0.26069 (13) | 0.0744 (8) | |
O25 | 0.46699 (15) | 0.34926 (16) | 0.19687 (10) | 0.0787 (5) | |
H25 | 0.3956 | 0.3538 | 0.2040 | 0.118* | |
C26 | 0.4892 (4) | 0.4702 (4) | 0.2812 (3) | 0.144 (2) | |
H26A | 0.5165 | 0.5144 | 0.2461 | 0.216* | |
H26B | 0.5215 | 0.4864 | 0.3270 | 0.216* | |
H26C | 0.4043 | 0.4721 | 0.2835 | 0.216* | |
C27 | 0.5023 (3) | 0.2994 (5) | 0.3186 (3) | 0.190 (3) | |
H27A | 0.4304 | 0.3166 | 0.3427 | 0.286* | |
H27B | 0.5663 | 0.2979 | 0.3524 | 0.286* | |
H27C | 0.4932 | 0.2384 | 0.2973 | 0.286* | |
O1W | 0.79973 (17) | 0.86856 (14) | 0.30794 (9) | 0.0773 (5) | |
H1WA | 0.8593 | 0.8396 | 0.3199 | 0.116* | |
H1WB | 0.8456 | 0.9057 | 0.3269 | 0.116* | |
O2WA | 0.7176 (3) | 1.27327 (19) | −0.08429 (16) | 0.0631 (7) | 0.60 |
O2WB | 0.6316 (6) | 1.2532 (3) | −0.0992 (3) | 0.0790 (14) | 0.40 |
O3WA | 0.4788 (5) | 1.2521 (4) | 0.0660 (3) | 0.105 (2) | 0.50 |
O3WB | 0.4589 (4) | 1.1938 (5) | 0.1076 (4) | 0.120 (2) | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0360 (8) | 0.0272 (7) | 0.0335 (8) | −0.0010 (6) | −0.0089 (6) | −0.0001 (6) |
C2 | 0.0363 (8) | 0.0316 (7) | 0.0417 (9) | 0.0049 (6) | −0.0086 (7) | −0.0047 (6) |
O2 | 0.0475 (8) | 0.0567 (8) | 0.0618 (8) | 0.0213 (6) | −0.0204 (7) | −0.0186 (7) |
C3 | 0.0516 (10) | 0.0322 (8) | 0.0408 (9) | 0.0069 (7) | −0.0113 (8) | −0.0074 (6) |
O3 | 0.0854 (11) | 0.0266 (6) | 0.0621 (9) | 0.0017 (7) | −0.0295 (8) | −0.0008 (6) |
C4 | 0.0497 (10) | 0.0292 (7) | 0.0408 (9) | −0.0010 (7) | −0.0144 (7) | −0.0044 (6) |
C5 | 0.0367 (8) | 0.0260 (7) | 0.0442 (9) | −0.0096 (6) | −0.0095 (7) | 0.0036 (6) |
C6 | 0.0334 (8) | 0.0366 (8) | 0.0446 (9) | −0.0079 (6) | −0.0076 (7) | −0.0012 (7) |
O6 | 0.0380 (7) | 0.0457 (7) | 0.0768 (10) | −0.0164 (6) | −0.0158 (7) | 0.0059 (7) |
C7 | 0.0319 (8) | 0.0323 (8) | 0.0504 (10) | −0.0026 (6) | −0.0125 (7) | 0.0011 (7) |
C8 | 0.0280 (6) | 0.0253 (6) | 0.0313 (7) | 0.0014 (5) | −0.0050 (6) | −0.0023 (5) |
C9 | 0.0239 (6) | 0.0238 (6) | 0.0329 (7) | −0.0012 (5) | −0.0054 (5) | −0.0011 (5) |
C10 | 0.0286 (7) | 0.0287 (7) | 0.0318 (7) | −0.0036 (6) | −0.0031 (6) | 0.0019 (6) |
C11 | 0.0394 (9) | 0.0268 (7) | 0.0359 (8) | −0.0011 (6) | −0.0135 (6) | 0.0004 (6) |
C12 | 0.0313 (7) | 0.0274 (7) | 0.0385 (8) | −0.0025 (6) | −0.0113 (6) | −0.0013 (6) |
C13 | 0.0251 (6) | 0.0230 (6) | 0.0283 (7) | −0.0011 (5) | −0.0005 (5) | −0.0015 (5) |
C14 | 0.0293 (7) | 0.0261 (6) | 0.0317 (7) | −0.0015 (5) | −0.0032 (6) | −0.0028 (6) |
O14 | 0.0413 (6) | 0.0347 (6) | 0.0402 (6) | 0.0013 (5) | 0.0085 (5) | −0.0061 (5) |
C15 | 0.0469 (9) | 0.0342 (8) | 0.0383 (9) | −0.0041 (7) | −0.0162 (7) | −0.0004 (7) |
C16 | 0.0529 (10) | 0.0315 (7) | 0.0326 (8) | −0.0023 (7) | −0.0112 (7) | 0.0003 (6) |
C17 | 0.0295 (7) | 0.0247 (6) | 0.0285 (7) | −0.0007 (5) | −0.0018 (6) | −0.0008 (5) |
C18 | 0.0410 (9) | 0.0452 (9) | 0.0426 (10) | −0.0059 (7) | 0.0060 (7) | 0.0023 (8) |
C19 | 0.0310 (7) | 0.0343 (8) | 0.0446 (9) | 0.0015 (6) | 0.0084 (7) | 0.0032 (7) |
C20 | 0.0271 (7) | 0.0254 (6) | 0.0320 (7) | 0.0010 (5) | −0.0031 (6) | 0.0006 (5) |
O20 | 0.0303 (5) | 0.0386 (6) | 0.0426 (7) | 0.0057 (5) | −0.0007 (5) | −0.0036 (5) |
C21 | 0.0396 (8) | 0.0287 (7) | 0.0349 (8) | 0.0004 (6) | −0.0054 (6) | −0.0007 (6) |
C22 | 0.0362 (8) | 0.0270 (7) | 0.0357 (8) | −0.0025 (6) | −0.0061 (6) | 0.0023 (6) |
O22 | 0.0436 (7) | 0.0260 (5) | 0.0591 (8) | −0.0025 (5) | −0.0090 (6) | 0.0064 (5) |
C23 | 0.0345 (8) | 0.0451 (9) | 0.0539 (11) | −0.0042 (7) | 0.0035 (8) | 0.0115 (8) |
C24 | 0.0457 (11) | 0.1024 (19) | 0.0585 (13) | −0.0175 (12) | −0.0019 (10) | 0.0344 (13) |
C25 | 0.0476 (13) | 0.126 (2) | 0.0492 (12) | −0.0233 (14) | 0.0043 (10) | 0.0176 (14) |
O25 | 0.0453 (9) | 0.1140 (15) | 0.0766 (11) | −0.0128 (10) | 0.0008 (8) | −0.0133 (11) |
C26 | 0.086 (2) | 0.204 (5) | 0.142 (4) | −0.012 (3) | 0.044 (2) | −0.087 (4) |
C27 | 0.071 (2) | 0.342 (8) | 0.158 (4) | −0.051 (3) | 0.004 (2) | 0.162 (5) |
O1W | 0.0810 (12) | 0.0875 (12) | 0.0632 (10) | −0.0132 (10) | 0.0036 (9) | −0.0324 (9) |
O2WA | 0.074 (2) | 0.0469 (14) | 0.0683 (17) | 0.0070 (14) | 0.0010 (15) | 0.0057 (12) |
O2WB | 0.112 (4) | 0.047 (2) | 0.079 (3) | 0.018 (3) | 0.021 (3) | 0.015 (2) |
O3WA | 0.107 (4) | 0.098 (4) | 0.112 (4) | 0.068 (3) | −0.038 (3) | −0.044 (3) |
O3WB | 0.064 (3) | 0.161 (6) | 0.136 (5) | 0.037 (3) | −0.008 (3) | −0.077 (4) |
Geometric parameters (Å, º) top
C1—C2 | 1.518 (2) | C13—C19 | 1.534 (2) |
C1—C10 | 1.539 (2) | C13—C14 | 1.5511 (19) |
C2—O2 | 1.428 (2) | C13—C17 | 1.560 (2) |
C2—C3 | 1.515 (2) | C14—O14 | 1.4365 (19) |
C3—O3 | 1.419 (2) | C14—C15 | 1.517 (2) |
C3—C4 | 1.524 (2) | C15—C16 | 1.537 (2) |
C4—C5 | 1.537 (3) | C16—C17 | 1.555 (2) |
C5—C6 | 1.509 (2) | C17—C20 | 1.5459 (19) |
C5—C10 | 1.551 (2) | C20—O20 | 1.4411 (18) |
C6—O6 | 1.218 (2) | C20—C21 | 1.522 (2) |
C6—C7 | 1.463 (2) | C20—C22 | 1.556 (2) |
C7—C8 | 1.335 (2) | C22—O22 | 1.4383 (19) |
C8—C9 | 1.509 (2) | C22—C23 | 1.512 (2) |
C8—C14 | 1.512 (2) | C23—C24 | 1.518 (3) |
C9—C11 | 1.550 (2) | C24—C25 | 1.521 (3) |
C9—C10 | 1.558 (2) | C25—O25 | 1.422 (3) |
C10—C18 | 1.529 (2) | C25—C26 | 1.522 (6) |
C11—C12 | 1.539 (2) | C25—C27 | 1.523 (5) |
C12—C13 | 1.528 (2) | | |
| | | |
C2—C1—C10 | 114.34 (13) | C12—C13—C17 | 116.80 (12) |
O2—C2—C3 | 111.20 (13) | C19—C13—C17 | 112.20 (12) |
O2—C2—C1 | 107.60 (14) | C14—C13—C17 | 99.72 (11) |
C3—C2—C1 | 111.85 (15) | O14—C14—C8 | 105.26 (11) |
O3—C3—C2 | 107.78 (14) | O14—C14—C15 | 108.65 (13) |
O3—C3—C4 | 111.99 (16) | C8—C14—C15 | 120.00 (13) |
C2—C3—C4 | 109.48 (13) | O14—C14—C13 | 106.75 (11) |
C3—C4—C5 | 111.54 (14) | C8—C14—C13 | 112.17 (12) |
C6—C5—C4 | 109.12 (14) | C15—C14—C13 | 103.39 (12) |
C6—C5—C10 | 111.39 (13) | C14—C15—C16 | 102.78 (13) |
C4—C5—C10 | 112.99 (13) | C15—C16—C17 | 106.98 (13) |
O6—C6—C7 | 121.97 (16) | C20—C17—C16 | 112.66 (12) |
O6—C6—C5 | 121.95 (15) | C20—C17—C13 | 120.02 (12) |
C7—C6—C5 | 115.84 (14) | C16—C17—C13 | 104.39 (11) |
C8—C7—C6 | 122.05 (15) | O20—C20—C21 | 110.04 (12) |
C7—C8—C9 | 123.47 (13) | O20—C20—C17 | 109.39 (11) |
C7—C8—C14 | 123.11 (14) | C21—C20—C17 | 113.59 (12) |
C9—C8—C14 | 113.28 (12) | O20—C20—C22 | 104.26 (12) |
C8—C9—C11 | 110.05 (11) | C21—C20—C22 | 110.52 (12) |
C8—C9—C10 | 114.25 (11) | C17—C20—C22 | 108.61 (12) |
C11—C9—C10 | 112.30 (12) | O22—C22—C23 | 107.47 (13) |
C18—C10—C1 | 108.43 (13) | O22—C22—C20 | 108.49 (13) |
C18—C10—C5 | 107.76 (13) | C23—C22—C20 | 116.19 (13) |
C1—C10—C5 | 107.64 (12) | C22—C23—C24 | 112.46 (16) |
C18—C10—C9 | 112.18 (13) | C23—C24—C25 | 116.1 (2) |
C1—C10—C9 | 110.77 (12) | O25—C25—C24 | 107.0 (2) |
C5—C10—C9 | 109.91 (12) | O25—C25—C26 | 105.7 (3) |
C12—C11—C9 | 113.67 (13) | C24—C25—C26 | 112.6 (3) |
C13—C12—C11 | 110.69 (12) | O25—C25—C27 | 110.4 (3) |
C12—C13—C19 | 110.71 (13) | C24—C25—C27 | 108.6 (3) |
C12—C13—C14 | 107.44 (11) | C26—C25—C27 | 112.3 (4) |
C19—C13—C14 | 109.10 (12) | | |
(V) 2
β,3
β,5
β,14
α,20
R,22
R,25-heptahydroxy-5
β-cholest-7-en-6-one
hydrate
top
Crystal data top
C27H44O8·H2O | Dx = 1.243 Mg m−3 |
Mr = 514.64 | Cu Kα radiation, λ = 1.54180 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 7.163 (1) Å | θ = 25.0–29.0° |
b = 10.303 (1) Å | µ = 0.76 mm−1 |
c = 37.254 (2) Å | T = 293 K |
V = 2749.4 (5) Å3 | Block, colorless |
Z = 4 | 0.50 × 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 tube | Rint = 0.009 |
Graphite monochromator | θmax = 74.9°, θmin = 2.4° |
ω–2θ scans | h = −8→8 |
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24 350-359 | k = −12→12 |
Tmin = 0.896, Tmax = 0.927 | l = −46→46 |
6667 measured reflections | 3 standard reflections every 60 min |
5553 independent reflections | intensity decay: 6% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H 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 reflections | Δρmax = 0.18 e Å−3 |
338 parameters | Δρmin = −0.20 e Å−3 |
5 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.03 (14) |
Crystal data top
C27H44O8·H2O | V = 2749.4 (5) Å3 |
Mr = 514.64 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 7.163 (1) Å | µ = 0.76 mm−1 |
b = 10.303 (1) Å | T = 293 K |
c = 37.254 (2) Å | 0.50 × 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 = 0.927 | 3 standard reflections every 60 min |
6667 measured reflections | intensity decay: 6% |
5553 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.104 | Δρmax = 0.18 e Å−3 |
S = 1.07 | Δρmin = −0.20 e Å−3 |
5553 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
338 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | |
O1 | −0.0959 (2) | 0.92930 (13) | 0.00774 (4) | 0.0557 (4) | |
H1C | −0.0563 (9) | 0.8524 (17) | 0.01101 (8) | 0.072* | |
H1D | −0.005 (2) | 0.9704 (9) | 0.00276 (12) | 0.072* | |
O2 | −0.15418 (18) | 0.9277 (2) | 0.28169 (4) | 0.0820 (7) | |
H2 | −0.247 (4) | 0.9256 (2) | 0.2679 (5) | 0.107* | |
O3 | 0.24014 (18) | 0.92163 (16) | 0.30623 (4) | 0.0579 (4) | |
H3 | 0.185 (2) | 0.9671 (18) | 0.3176 (4) | 0.075* | |
O5 | 0.48168 (18) | 0.95482 (14) | 0.25223 (4) | 0.0510 (3) | |
H5 | 0.4235 (17) | 0.9698 (5) | 0.2724 (6) | 0.066* | |
O6 | 0.67995 (19) | 0.7780 (2) | 0.21861 (5) | 0.0869 (7) | |
O14 | 0.05621 (15) | 0.55343 (11) | 0.16018 (3) | 0.0360 (2) | |
H14 | 0.1045 (13) | 0.5235 (8) | 0.1779 (5) | 0.047* | |
O20 | 0.02706 (18) | 0.66991 (11) | 0.02600 (3) | 0.0373 (3) | |
H20 | 0.110 (3) | 0.6260 (14) | 0.02110 (16) | 0.048* | |
O22 | −0.21964 (18) | 0.48018 (12) | 0.00109 (3) | 0.0412 (3) | |
H22 | −0.134 (2) | 0.4950 (4) | −0.0165 (4) | 0.054* | |
O25 | −0.4074 (2) | 0.02712 (11) | 0.04529 (4) | 0.0488 (3) | |
H25 | −0.311 (3) | 0.0061 (7) | 0.0357 (3) | 0.063* | |
C1 | 0.0713 (3) | 0.97569 (18) | 0.23495 (5) | 0.0495 (5) | |
H1A | 0.1239 | 1.0475 | 0.2484 | 0.064* | |
H1B | −0.0310 | 1.0092 | 0.2206 | 0.064* | |
C2 | −0.0037 (2) | 0.8765 (2) | 0.26085 (5) | 0.0482 (5) | |
H2A | −0.0524 | 0.8036 | 0.2468 | 0.063* | |
C3 | 0.1486 (2) | 0.8246 (2) | 0.28509 (5) | 0.0459 (4) | |
H3A | 0.0957 | 0.7586 | 0.3011 | 0.060* | |
C4 | 0.2962 (2) | 0.76195 (16) | 0.26122 (4) | 0.0387 (3) | |
H4A | 0.2412 | 0.6889 | 0.2487 | 0.050* | |
H4B | 0.3967 | 0.7291 | 0.2761 | 0.050* | |
C5 | 0.3769 (2) | 0.85759 (16) | 0.23365 (4) | 0.0371 (4) | |
C6 | 0.5153 (2) | 0.7822 (2) | 0.21054 (5) | 0.0477 (4) | |
C7 | 0.4439 (2) | 0.70988 (19) | 0.17994 (4) | 0.0410 (4) | |
H7 | 0.5229 | 0.6521 | 0.1682 | 0.053* | |
C8 | 0.2692 (2) | 0.72322 (15) | 0.16796 (4) | 0.0295 (3) | |
C9 | 0.1315 (2) | 0.81660 (15) | 0.18457 (4) | 0.0313 (3) | |
H9 | 0.0512 | 0.7637 | 0.2001 | 0.041* | |
C10 | 0.2223 (2) | 0.92006 (15) | 0.20971 (4) | 0.0379 (3) | |
C11 | 0.0006 (3) | 0.87767 (17) | 0.15644 (5) | 0.0454 (4) | |
H11A | −0.1010 | 0.9210 | 0.1688 | 0.059* | |
H11B | 0.0693 | 0.9431 | 0.1432 | 0.059* | |
C12 | −0.0813 (2) | 0.78043 (17) | 0.12988 (4) | 0.0378 (3) | |
H12A | −0.1554 | 0.8262 | 0.1121 | 0.049* | |
H12B | −0.1628 | 0.7207 | 0.1425 | 0.049* | |
C13 | 0.0740 (2) | 0.70370 (13) | 0.11091 (4) | 0.0274 (3) | |
C14 | 0.1860 (2) | 0.63243 (13) | 0.14041 (4) | 0.0274 (3) | |
C15 | 0.3136 (2) | 0.54142 (17) | 0.11929 (4) | 0.0384 (3) | |
H15A | 0.3505 | 0.4674 | 0.1337 | 0.050* | |
H15B | 0.4246 | 0.5864 | 0.1111 | 0.050* | |
C16 | 0.1904 (2) | 0.49880 (16) | 0.08727 (4) | 0.0389 (4) | |
H16A | 0.1579 | 0.4077 | 0.0894 | 0.051* | |
H16B | 0.2566 | 0.5115 | 0.0648 | 0.051* | |
C17 | 0.0121 (2) | 0.58396 (13) | 0.08828 (4) | 0.0272 (3) | |
H17 | −0.0767 | 0.5366 | 0.1034 | 0.035* | |
C18 | 0.2044 (3) | 0.79554 (17) | 0.09003 (4) | 0.0440 (4) | |
H18A | 0.1311 | 0.8541 | 0.0758 | 0.066* | |
H18B | 0.2843 | 0.7455 | 0.0746 | 0.066* | |
H18C | 0.2792 | 0.8442 | 0.1067 | 0.066* | |
C19 | 0.3113 (4) | 1.0307 (2) | 0.18779 (7) | 0.0725 (7) | |
H19A | 0.3926 | 0.9946 | 0.1699 | 0.109* | |
H19B | 0.3818 | 1.0859 | 0.2035 | 0.109* | |
H19C | 0.2149 | 1.0804 | 0.1763 | 0.109* | |
C20 | −0.0865 (2) | 0.60078 (14) | 0.05167 (4) | 0.0292 (3) | |
C21 | −0.2632 (2) | 0.68158 (15) | 0.05480 (4) | 0.0349 (3) | |
H21A | −0.2307 | 0.7697 | 0.0604 | 0.052* | |
H21B | −0.3407 | 0.6469 | 0.0735 | 0.052* | |
H21C | −0.3297 | 0.6793 | 0.0324 | 0.052* | |
C22 | −0.1308 (2) | 0.46514 (14) | 0.03528 (4) | 0.0331 (3) | |
H22A | −0.0125 | 0.4193 | 0.0316 | 0.043* | |
C23 | −0.2566 (3) | 0.37924 (15) | 0.05803 (4) | 0.0407 (4) | |
H23A | −0.3775 | 0.4206 | 0.0606 | 0.053* | |
H23B | −0.2027 | 0.3703 | 0.0818 | 0.053* | |
C24 | −0.2832 (3) | 0.24384 (16) | 0.04158 (5) | 0.0438 (4) | |
H24A | −0.3573 | 0.2526 | 0.0199 | 0.057* | |
H24B | −0.1618 | 0.2107 | 0.0346 | 0.057* | |
C25 | −0.3769 (3) | 0.14389 (15) | 0.06587 (5) | 0.0416 (4) | |
C26 | −0.5705 (4) | 0.1864 (2) | 0.07749 (7) | 0.0665 (6) | |
H26A | −0.6406 | 0.2133 | 0.0568 | 0.100* | |
H26B | −0.5602 | 0.2575 | 0.0940 | 0.100* | |
H26C | −0.6330 | 0.1152 | 0.0890 | 0.100* | |
C27 | −0.2587 (4) | 0.1112 (2) | 0.09810 (6) | 0.0748 (8) | |
H27A | −0.3183 | 0.0440 | 0.1118 | 0.112* | |
H27B | −0.2442 | 0.1871 | 0.1128 | 0.112* | |
H27C | −0.1382 | 0.0818 | 0.0903 | 0.112* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0459 (7) | 0.0464 (7) | 0.0748 (9) | 0.0086 (6) | 0.0195 (7) | 0.0107 (6) |
O2 | 0.0226 (6) | 0.1515 (17) | 0.0721 (9) | 0.0175 (8) | −0.0110 (6) | −0.0741 (11) |
O3 | 0.0294 (6) | 0.0905 (10) | 0.0539 (7) | 0.0081 (7) | −0.0108 (5) | −0.0383 (7) |
O5 | 0.0305 (6) | 0.0640 (8) | 0.0586 (7) | −0.0110 (6) | −0.0107 (5) | −0.0226 (6) |
O6 | 0.0183 (6) | 0.1614 (18) | 0.0811 (10) | 0.0048 (9) | −0.0111 (7) | −0.0575 (12) |
O14 | 0.0298 (5) | 0.0454 (6) | 0.0327 (5) | −0.0090 (5) | −0.0052 (4) | 0.0121 (4) |
O20 | 0.0388 (6) | 0.0397 (6) | 0.0334 (5) | −0.0006 (5) | 0.0040 (5) | 0.0052 (4) |
O22 | 0.0423 (6) | 0.0488 (6) | 0.0324 (5) | −0.0002 (5) | −0.0071 (5) | −0.0029 (5) |
O25 | 0.0456 (7) | 0.0323 (6) | 0.0685 (8) | −0.0017 (5) | 0.0018 (6) | −0.0121 (5) |
C1 | 0.0432 (10) | 0.0446 (9) | 0.0606 (11) | 0.0160 (8) | −0.0234 (9) | −0.0252 (8) |
C2 | 0.0207 (8) | 0.0731 (12) | 0.0509 (9) | 0.0072 (8) | −0.0069 (7) | −0.0349 (9) |
C3 | 0.0292 (8) | 0.0656 (11) | 0.0429 (8) | 0.0006 (8) | −0.0026 (7) | −0.0158 (8) |
C4 | 0.0303 (8) | 0.0467 (8) | 0.0392 (8) | 0.0081 (7) | −0.0067 (7) | −0.0067 (7) |
C5 | 0.0216 (7) | 0.0467 (9) | 0.0429 (8) | −0.0049 (6) | −0.0077 (6) | −0.0130 (7) |
C6 | 0.0208 (7) | 0.0760 (12) | 0.0463 (9) | −0.0008 (8) | −0.0042 (7) | −0.0146 (9) |
C7 | 0.0204 (7) | 0.0626 (11) | 0.0399 (8) | 0.0026 (7) | −0.0016 (6) | −0.0110 (7) |
C8 | 0.0211 (6) | 0.0367 (7) | 0.0308 (6) | −0.0017 (6) | −0.0011 (5) | 0.0002 (5) |
C9 | 0.0249 (7) | 0.0338 (7) | 0.0351 (7) | 0.0019 (6) | −0.0074 (6) | −0.0070 (6) |
C10 | 0.0330 (8) | 0.0347 (7) | 0.0460 (8) | −0.0041 (6) | −0.0120 (7) | −0.0068 (6) |
C11 | 0.0462 (10) | 0.0435 (9) | 0.0466 (9) | 0.0163 (8) | −0.0194 (8) | −0.0140 (7) |
C12 | 0.0312 (8) | 0.0424 (8) | 0.0398 (8) | 0.0119 (7) | −0.0122 (6) | −0.0097 (6) |
C13 | 0.0252 (7) | 0.0282 (6) | 0.0288 (6) | 0.0007 (5) | −0.0031 (5) | 0.0016 (5) |
C14 | 0.0199 (6) | 0.0323 (7) | 0.0300 (6) | −0.0007 (5) | −0.0002 (5) | 0.0027 (5) |
C15 | 0.0288 (7) | 0.0458 (9) | 0.0405 (8) | 0.0113 (7) | −0.0044 (6) | −0.0060 (7) |
C16 | 0.0388 (9) | 0.0398 (8) | 0.0381 (7) | 0.0132 (7) | −0.0067 (7) | −0.0066 (6) |
C17 | 0.0260 (7) | 0.0267 (6) | 0.0288 (6) | 0.0013 (5) | −0.0008 (5) | 0.0008 (5) |
C18 | 0.0501 (10) | 0.0427 (8) | 0.0392 (8) | −0.0167 (8) | −0.0045 (7) | 0.0085 (7) |
C19 | 0.0853 (17) | 0.0542 (12) | 0.0781 (14) | −0.0321 (13) | −0.0261 (14) | 0.0119 (10) |
C20 | 0.0296 (7) | 0.0296 (6) | 0.0284 (6) | 0.0007 (6) | 0.0000 (5) | 0.0014 (5) |
C21 | 0.0317 (8) | 0.0353 (7) | 0.0377 (7) | 0.0049 (6) | −0.0062 (6) | −0.0003 (6) |
C22 | 0.0342 (8) | 0.0334 (7) | 0.0318 (7) | 0.0027 (6) | −0.0046 (6) | −0.0028 (6) |
C23 | 0.0497 (10) | 0.0317 (7) | 0.0407 (8) | −0.0037 (7) | 0.0010 (7) | −0.0032 (6) |
C24 | 0.0534 (10) | 0.0347 (8) | 0.0432 (8) | −0.0035 (8) | 0.0000 (8) | −0.0053 (6) |
C25 | 0.0490 (10) | 0.0275 (7) | 0.0483 (9) | 0.0023 (7) | −0.0013 (8) | −0.0038 (6) |
C26 | 0.0588 (13) | 0.0462 (10) | 0.0945 (16) | 0.0001 (10) | 0.0250 (13) | −0.0136 (11) |
C27 | 0.109 (2) | 0.0470 (10) | 0.0682 (13) | 0.0012 (13) | −0.0294 (15) | 0.0099 (10) |
Geometric parameters (Å, º) top
O2—C2 | 1.430 (2) | C9—C11 | 1.540 (2) |
O3—C3 | 1.431 (2) | C9—C10 | 1.561 (2) |
O5—C5 | 1.4303 (18) | C10—C19 | 1.540 (3) |
O6—C6 | 1.218 (2) | C11—C12 | 1.526 (2) |
O14—C14 | 1.4386 (17) | C12—C13 | 1.537 (2) |
O20—C20 | 1.4432 (18) | C13—C18 | 1.541 (2) |
O22—C22 | 1.4321 (17) | C13—C14 | 1.5463 (18) |
O25—C25 | 1.4431 (19) | C13—C17 | 1.5587 (19) |
C1—C2 | 1.505 (3) | C14—C15 | 1.527 (2) |
C1—C10 | 1.544 (3) | C15—C16 | 1.547 (2) |
C2—C3 | 1.513 (2) | C16—C17 | 1.550 (2) |
C3—C4 | 1.525 (2) | C17—C20 | 1.5454 (19) |
C4—C5 | 1.536 (2) | C20—C21 | 1.519 (2) |
C5—C6 | 1.526 (2) | C20—C22 | 1.558 (2) |
C5—C10 | 1.561 (2) | C22—C23 | 1.521 (2) |
C6—C7 | 1.455 (2) | C23—C24 | 1.536 (2) |
C7—C8 | 1.335 (2) | C24—C25 | 1.526 (2) |
C8—C14 | 1.5109 (19) | C25—C27 | 1.507 (3) |
C8—C9 | 1.510 (2) | C25—C26 | 1.517 (3) |
| | | |
C2—C1—C10 | 112.86 (14) | C12—C13—C14 | 107.04 (11) |
O2—C2—C1 | 111.49 (18) | C18—C13—C14 | 109.62 (12) |
O2—C2—C3 | 110.48 (14) | C12—C13—C17 | 116.73 (13) |
C1—C2—C3 | 111.43 (15) | C18—C13—C17 | 112.68 (12) |
O3—C3—C2 | 114.32 (17) | C14—C13—C17 | 99.00 (10) |
O3—C3—C4 | 107.39 (14) | O14—C14—C8 | 104.91 (11) |
C2—C3—C4 | 107.54 (13) | O14—C14—C15 | 107.63 (12) |
C3—C4—C5 | 112.28 (14) | C8—C14—C15 | 119.63 (12) |
O5—C5—C6 | 106.78 (13) | O14—C14—C13 | 107.27 (11) |
O5—C5—C4 | 108.85 (13) | C8—C14—C13 | 113.17 (11) |
C6—C5—C4 | 107.16 (15) | C15—C14—C13 | 103.63 (11) |
O5—C5—C10 | 111.10 (14) | C14—C15—C16 | 103.33 (12) |
C6—C5—C10 | 110.41 (13) | C15—C16—C17 | 106.89 (12) |
C4—C5—C10 | 112.30 (13) | C20—C17—C16 | 114.74 (12) |
O6—C6—C7 | 121.08 (18) | C20—C17—C13 | 121.24 (11) |
O6—C6—C5 | 120.53 (16) | C16—C17—C13 | 103.09 (12) |
C7—C6—C5 | 118.30 (14) | O20—C20—C21 | 104.47 (11) |
C8—C7—C6 | 122.60 (16) | O20—C20—C17 | 112.49 (12) |
C7—C8—C14 | 122.17 (14) | C21—C20—C17 | 111.98 (11) |
C7—C8—C9 | 122.72 (14) | O20—C20—C22 | 107.33 (11) |
C14—C8—C9 | 114.53 (12) | C21—C20—C22 | 110.59 (13) |
C8—C9—C11 | 112.27 (12) | C17—C20—C22 | 109.79 (11) |
C8—C9—C10 | 114.13 (12) | O22—C22—C23 | 107.19 (13) |
C11—C9—C10 | 112.50 (13) | O22—C22—C20 | 110.01 (12) |
C19—C10—C1 | 109.78 (17) | C23—C22—C20 | 115.11 (12) |
C19—C10—C5 | 108.30 (15) | C22—C23—C24 | 112.33 (14) |
C1—C10—C5 | 107.59 (13) | C25—C24—C23 | 115.53 (14) |
C19—C10—C9 | 111.09 (14) | O25—C25—C27 | 108.79 (15) |
C1—C10—C9 | 109.10 (13) | O25—C25—C26 | 104.70 (16) |
C5—C10—C9 | 110.91 (12) | C27—C25—C26 | 110.52 (19) |
C12—C11—C9 | 114.02 (13) | O25—C25—C24 | 108.30 (14) |
C11—C12—C13 | 110.96 (14) | C27—C25—C24 | 112.10 (18) |
C12—C13—C18 | 110.80 (13) | C26—C25—C24 | 112.09 (16) |
| | | |
C10—C1—C2—O2 | −174.95 (13) | C11—C12—C13—C14 | 59.46 (16) |
C10—C1—C2—C3 | 61.10 (17) | C11—C12—C13—C17 | 169.19 (13) |
O2—C2—C3—O3 | −65.4 (2) | C7—C8—C14—O14 | 107.02 (17) |
C1—C2—C3—O3 | 59.13 (18) | C9—C8—C14—O14 | −64.51 (15) |
O2—C2—C3—C4 | 175.47 (17) | C7—C8—C14—C15 | −13.8 (2) |
C1—C2—C3—C4 | −60.01 (19) | C9—C8—C14—C15 | 174.68 (13) |
O3—C3—C4—C5 | −65.55 (18) | C7—C8—C14—C13 | −136.35 (16) |
C2—C3—C4—C5 | 57.93 (19) | C9—C8—C14—C13 | 52.12 (16) |
C3—C4—C5—O5 | 67.34 (17) | C12—C13—C14—O14 | 56.85 (14) |
C3—C4—C5—C6 | −177.53 (12) | C18—C13—C14—O14 | 177.09 (12) |
C3—C4—C5—C10 | −56.11 (17) | C17—C13—C14—O14 | −64.82 (12) |
O5—C5—C6—O6 | 24.7 (3) | C12—C13—C14—C8 | −58.38 (15) |
C4—C5—C6—O6 | −91.8 (3) | C18—C13—C14—C8 | 61.86 (15) |
C10—C5—C6—O6 | 145.6 (2) | C17—C13—C14—C8 | 179.96 (11) |
O5—C5—C6—C7 | −158.72 (18) | C12—C13—C14—C15 | 170.54 (13) |
C4—C5—C6—C7 | 84.8 (2) | C18—C13—C14—C15 | −69.22 (15) |
C10—C5—C6—C7 | −37.8 (2) | C17—C13—C14—C15 | 48.88 (13) |
O6—C6—C7—C8 | −172.5 (2) | O14—C14—C15—C16 | 77.27 (14) |
C5—C6—C7—C8 | 10.9 (3) | C8—C14—C15—C16 | −163.29 (13) |
C6—C7—C8—C14 | −169.46 (16) | C13—C14—C15—C16 | −36.16 (15) |
C6—C7—C8—C9 | 1.4 (3) | C14—C15—C16—C17 | 8.96 (17) |
C7—C8—C9—C11 | 144.60 (17) | C15—C16—C17—C20 | 154.97 (13) |
C14—C8—C9—C11 | −43.92 (18) | C15—C16—C17—C13 | 21.06 (16) |
C7—C8—C9—C10 | 15.1 (2) | C12—C13—C17—C20 | 73.58 (16) |
C14—C8—C9—C10 | −173.45 (12) | C18—C13—C17—C20 | −56.33 (18) |
C2—C1—C10—C19 | −172.10 (14) | C14—C13—C17—C20 | −172.09 (12) |
C2—C1—C10—C5 | −54.44 (17) | C12—C13—C17—C16 | −156.36 (13) |
C2—C1—C10—C9 | 65.95 (16) | C18—C13—C17—C16 | 73.74 (15) |
O5—C5—C10—C19 | 48.1 (2) | C14—C13—C17—C16 | −42.03 (13) |
C6—C5—C10—C19 | −70.23 (19) | C16—C17—C20—O20 | −64.50 (16) |
C4—C5—C10—C19 | 170.23 (15) | C13—C17—C20—O20 | 60.34 (17) |
O5—C5—C10—C1 | −70.56 (17) | C16—C17—C20—C21 | 178.19 (13) |
C6—C5—C10—C1 | 171.16 (14) | C13—C17—C20—C21 | −56.97 (17) |
C4—C5—C10—C1 | 51.62 (17) | C16—C17—C20—C22 | 54.95 (17) |
O5—C5—C10—C9 | 170.20 (13) | C13—C17—C20—C22 | 179.78 (13) |
C6—C5—C10—C9 | 51.91 (18) | O20—C20—C22—O22 | −56.56 (16) |
C4—C5—C10—C9 | −67.62 (17) | C21—C20—C22—O22 | 56.82 (16) |
C8—C9—C10—C19 | 78.9 (2) | C17—C20—C22—O22 | −179.12 (12) |
C11—C9—C10—C19 | −50.5 (2) | O20—C20—C22—C23 | −177.76 (13) |
C8—C9—C10—C1 | −159.90 (13) | C21—C20—C22—C23 | −64.38 (16) |
C11—C9—C10—C1 | 70.67 (18) | C17—C20—C22—C23 | 59.68 (17) |
C8—C9—C10—C5 | −41.56 (18) | O22—C22—C23—C24 | 61.32 (18) |
C11—C9—C10—C5 | −170.99 (14) | C20—C22—C23—C24 | −175.96 (14) |
C8—C9—C11—C12 | 46.0 (2) | C22—C23—C24—C25 | 169.10 (15) |
C10—C9—C11—C12 | 176.37 (15) | C23—C24—C25—O25 | 174.50 (16) |
C9—C11—C12—C13 | −55.5 (2) | C23—C24—C25—C27 | −65.5 (2) |
C11—C12—C13—C18 | −60.02 (17) | C23—C24—C25—C26 | 59.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1C···O20 | 0.85 | 2.05 | 2.8950 (18) | 172 |
O1—H1D···O22i | 0.80 | 2.11 | 2.8705 (19) | 159 |
O2—H2···O5ii | 0.84 | 2.05 | 2.8437 (19) | 157 |
O2—H2···O6ii | 0.84 | 2.44 | 3.052 (2) | 130 |
O3—H3···O14iii | 0.74 | 2.11 | 2.8136 (17) | 157 |
O5—H5···O3 | 0.87 | 1.89 | 2.676 (2) | 149 |
O14—H14···O2iv | 0.81 | 1.83 | 2.6190 (17) | 164 |
O20—H20···O1i | 0.77 | 2.43 | 3.150 (2) | 156 |
O22—H22···O25v | 0.91 | 1.96 | 2.8275 (19) | 159 |
O25—H25···O1vi | 0.81 | 2.02 | 2.820 (2) | 170 |
Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) x−1, y, z; (iii) −x, y+1/2, −z+1/2; (iv) −x, y−1/2, −z+1/2; (v) x+1/2, −y+1/2, −z; (vi) x, y−1, z. |
Experimental details
| (I) | (II) | (III) | (IV) |
Crystal data |
Chemical formula | C27H44O6 | C27H44O7 | C27H44O7·CH4O·H2O | C27H50O10 |
Mr | 464.62 | 480.62 | 530.68 | 534.67 |
Crystal system, space group | Orthorhombic, P212121 | Orthorhombic, P212121 | Orthorhombic, P212121 | Orthorhombic, P212121 |
Temperature (K) | 293 | 293 | 293 | 293 |
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) |
V (Å3) | 2745.5 (5) | 2672.4 (5) | 2879.8 (6) | 3002.5 (8) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Cu Kα | Cu Kα | Cu Kα | Mo Kα |
µ (mm−1) | 0.62 | 0.69 | 0.73 | 0.09 |
Crystal size (mm) | 0.25 × 0.16 × 0.12 | 0.45 × 0.30 × 0.20 | 0.25 × 0.14 × 0.10 | 0.6 × 0.6 × 0.4 |
|
Data collection |
Diffractometer | Enraf-Nonius CAD4 diffractometer | Enraf-Nonius CAD4 diffractometer | Enraf-Nonius CAD4 diffractometer | Enraf-Nonius CAD4 diffractometer |
Absorption correction | 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 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, Tmax | 0.858, 0.930 | 0.748, 0.875 | 0.838, 0.930 | 0.898, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6982, 5410, 3946 | 5611, 4542, 4155 | 6775, 5774, 4751 | 13105, 11655, 6759 |
Rint | 0.013 | 0.013 | 0.012 | 0.011 |
(sin θ/λ)max (Å−1) | 0.626 | 0.626 | 0.626 | 0.775 |
|
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 reflections | 5410 | 4542 | 5774 | 11655 |
No. of parameters | 376 | 375 | 356 | 366 |
No. of restraints | 290 | 244 | 3 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | Riding |
Δρmax, Δρmin (e Å−3) | 0.15, −0.14 | 0.25, −0.21 | 0.23, −0.15 | 0.26, −0.18 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | 0.18 (17) | −0.19 (18) | 0.09 (17) | −0.1 (7) |
| (V) |
Crystal data |
Chemical formula | C27H44O8·H2O |
Mr | 514.64 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 7.163 (1), 10.303 (1), 37.254 (2) |
V (Å3) | 2749.4 (5) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.76 |
Crystal size (mm) | 0.50 × 0.15 × 0.10 |
|
Data collection |
Diffractometer | Enraf-Nonius CAD4 diffractometer |
Absorption correction | ψ scan North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24 350-359 |
Tmin, Tmax | 0.896, 0.927 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6667, 5553, 4972 |
Rint | 0.009 |
(sin θ/λ)max (Å−1) | 0.626 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.104, 1.07 |
No. of reflections | 5553 |
No. of parameters | 338 |
No. of restraints | 5 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.18, −0.20 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | 0.03 (14) |
Hydrogen-bond geometry (Å, º) for (I) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3i | 0.82 | 1.95 | 2.7494 (19) | 165.2 |
O3—H3···O6i | 0.82 | 2.03 | 2.8019 (16) | 156.2 |
O14—H14···O22Aii | 0.82 | 1.86 | 2.68 (3) | 171.6 |
O14—H14···O22Bii | 0.82 | 2.08 | 2.89 (3) | 172.1 |
O22A—H22C···O25A | 0.82 | 1.89 | 2.71 (2) | 171.3 |
O25A—H25A···O2iii | 0.82 | 1.95 | 2.760 (10) | 171.3 |
O22B—H22D···O25B | 0.82 | 1.81 | 2.63 (2) | 171.8 |
O25B—H25B···O2iii | 0.82 | 1.92 | 2.733 (9) | 169.6 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x, y+1/2, −z+3/2. |
Hydrogen-bond geometry (Å, º) for (II) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3i | 0.82 | 1.94 | 2.759 (2) | 179.0 |
O3—H3···O6i | 0.82 | 2.31 | 3.048 (2) | 149.5 |
O14—H14···O20ii | 0.82 | 2.03 | 2.8520 (17) | 175.3 |
O20—H20···O22 | 0.82 | 2.12 | 2.5795 (19) | 115.1 |
O22—H22···O25A | 0.82 | 1.88 | 2.671 (10) | 161.2 |
O22—H22···O25B | 0.82 | 1.84 | 2.645 (12) | 165.1 |
O25A—H25A···O2iii | 0.82 | 2.07 | 2.842 (14) | 156.9 |
O25B—H25B···O2iii | 0.82 | 1.98 | 2.707 (13) | 147.2 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x, y+1/2, −z+3/2. |
Hydrogen-bond geometry (Å, º) for (III) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O6i | 0.77 | 2.24 | 3.007 (2) | 176.5 |
O3—H3···O2Xii | 0.88 | 1.92 | 2.794 (2) | 171.7 |
O14—H14···O1W | 0.89 | 1.81 | 2.696 (2) | 168.8 |
O20—H20···O22iii | 0.80 | 2.00 | 2.787 (2) | 168.5 |
O22—H22···O25iii | 0.83 | 2.50 | 3.204 (2) | 144.2 |
O22—H22···O20 | 0.83 | 2.29 | 2.721 (2) | 112.6 |
O25—H25···O20iv | 0.97 | 1.94 | 2.871 (2) | 160.8 |
O1W—H1W···O3v | 0.80 | 2.03 | 2.815 (2) | 170.9 |
O1W—H2W···O2vi | 0.83 | 1.97 | 2.775 (2) | 164.6 |
O2X—H2X···O14 | 0.82 | 1.91 | 2.711 (2) | 165.0 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+2, y+1/2, −z+3/2; (iii) x−1/2, −y+1/2, −z+2; (iv) x+1/2, −y+1/2, −z+2; (v) −x+1, y−1/2, −z+3/2; (vi) −x+2, y−1/2, −z+3/2. |
Hydrogen-bond geometry (Å, º) for (V) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1C···O20 | 0.85 | 2.05 | 2.8950 (18) | 172.2 |
O1—H1D···O22i | 0.80 | 2.11 | 2.8705 (19) | 158.8 |
O2—H2···O5ii | 0.84 | 2.05 | 2.8437 (19) | 156.8 |
O2—H2···O6ii | 0.84 | 2.44 | 3.052 (2) | 130.2 |
O3—H3···O14iii | 0.74 | 2.11 | 2.8136 (17) | 156.9 |
O5—H5···O3 | 0.87 | 1.89 | 2.676 (2) | 149.4 |
O14—H14···O2iv | 0.81 | 1.83 | 2.6190 (17) | 163.8 |
O20—H20···O1i | 0.77 | 2.43 | 3.150 (2) | 155.7 |
O22—H22···O25v | 0.91 | 1.96 | 2.8275 (19) | 159.0 |
O25—H25···O1vi | 0.81 | 2.02 | 2.820 (2) | 170.2 |
Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) x−1, y, z; (iii) −x, y+1/2, −z+1/2; (iv) −x, y−1/2, −z+1/2; (v) x+1/2, −y+1/2, −z; (vi) x, y−1, z. |