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In the title compound, C29H42O4·H2O, cyclo­hexane rings A and B are in the sofa conformation, ring C is in a chair conformation and the five-membered ring D is in an envelope conformation. The structure is stabilized by inter- and intramolecular C-H...O and O-H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007927/qb0203sup1.cif
Contains datablocks II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007927/qb0203IIsup2.hkl
Contains datablock II

CCDC reference: 147700

Comment top

1α,24(R)-Dihydroxy vitamin D3 [tacalcitol, (I); Takeshita et al., 1977; Ochi et al.,1979; Okamoto et al., 1995; Fall et al., 1997] displays antipsoriatic activity. The title compound, (II), which contains 1a,2a-epoxide ring and a 24-acetate group is the major intermediate in the synthesis of vitamin D3 [tacalcitol, (I)]. The absolute configuration at C-24 in these molecules was assigned by physical methods involving optical rotation (Klyne & Stokes,1954) and NMR spectra (Ikekawa et al.,1975; Koizumi et al., 1975; Seki et al., 1975; Koch et al., 1983; Meenakshi et al., 1997).

We have synthesized intermediates (III) [24(R)-hydroxycholesta-1,4-dien-3-one] and (IV) [24(S)-hydroxycholesta-1,4-dien-3-one], which are epimeric at C-24, from the corresponding ketones (V) [24(R)-hydroxycholestan-3-one] and (VI) [24(S)-hydroxycholestan-3-one]. The title compound, (II), was synthesized from (III) involving aceylation, bromination, dehydrobromination and epoxidation. The melting point (393–395 K; Ochi et al., 1979) of epimer (III) agrees with the reported values, while the melting point of the title compound is 373–375 K. There is a solvent water molecule present in the structure. The packing of the molecule is established by inter and intramolecular C—H···O and O—H···O hydrogen bonds. Water H atoms were fixed using the program HYDROGEN (Nardelli, 1999).

Rings A (C1–C10), B (C5–C10), C (C8–C14) and D (C13–C17) adopt sofa, sofa, chair and envelope conformations, respectively. Substituents at C8 and C9, and C13 and C14 are at diaxial positions in the cyclohexane rings leading to a trans conformation [torsion angles H8—C8—C9—H9 = 179° and C18—C13—C14—H14 = 177°]. The priority sequence attached to the chiral carbon C24 has an `R' designation as per the listed coordinates. The absolute conformation could not be determined unequivocally as the structure contains only light atoms. The side chain attached to the D ring is in an all-trans conformation.

The best plane passing through ring A makes a dihedral angle of 14.2 (1)° with the best plane passing through cyclohexane ring B. The dihedral angles between rings B and C, and between rings C and D are 8.7 (2) and 9.6 (2)°, respectively.

Experimental top

24(R)-Hydroxycoprastan-3-one, obtained from lithocholic acid on usual acetylation with acetic anhydride and pyridine, afforded 24(R)-acetoxycoprastan-3-one. This, on bromination with bromine and acetic acid and subsequent dehydrobromination (Wilds & Djerassi, 1946), afforded 24(R)-acetoxycholesta-1,4-dien-3-one. Further bromination using N-bromosuccinimide and dehydrobromination (Kaufmann et al., 1950) of the resulting bromide gave 24-(R)-acetoxycholesta-1,4,6-trien-3-one. Epoxidation of the trienone using 30% aqueous hydrodgen peroxide under alkaline conditions yielded the title compound. Single crystals were obtained by slow evaporation from a solution in methanol.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL and PARST (Nardelli, 1983).

1a,2a-Epoxy-24(R)-acyloxycholesta-4,6-dien-3-one hydrate top
Crystal data top
C29H42O4·H2OF(000) = 512
Mr = 472.64Dx = 1.206 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54180 Å
a = 10.642 (3) ÅCell parameters from 25 reflections
b = 11.719 (2) Åθ = 10–27°
c = 10.977 (3) ŵ = 0.64 mm1
β = 108.04 (2)°T = 293 K
V = 1301.7 (6) Å3Rectangle, colourless
Z = 20.20 × 0.15 × 0.10 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.016
Radiation source: fine-focus sealed tubeθmax = 74.9°, θmin = 4.2°
Graphite monochromatorh = 013
ω/2θ scansk = 013
2848 measured reflectionsl = 1313
2712 independent reflections3 standard reflections every 120 min
2262 reflections with I > 2σ(I) intensity decay: <3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: full with fixed elements per cycleHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.162Calculated w = 1/[σ2(Fo2) + (0.095P)2 + 0.2101P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.010
2712 reflectionsΔρmax = 0.27 e Å3
322 parametersΔρmin = 0.55 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0091 (15)
Crystal data top
C29H42O4·H2OV = 1301.7 (6) Å3
Mr = 472.64Z = 2
Monoclinic, P21Cu Kα radiation
a = 10.642 (3) ŵ = 0.64 mm1
b = 11.719 (2) ÅT = 293 K
c = 10.977 (3) Å0.20 × 0.15 × 0.10 mm
β = 108.04 (2)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.016
2848 measured reflections3 standard reflections every 120 min
2712 independent reflections intensity decay: <3%
2262 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0561 restraint
wR(F2) = 0.162H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.27 e Å3
2712 reflectionsΔρmin = 0.55 e Å3
322 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0854 (3)1.8844 (3)0.0756 (3)0.0670 (9)
O20.1021 (3)1.5957 (3)0.1111 (3)0.0555 (7)
O30.3554 (2)0.8864 (3)0.9399 (2)0.0453 (6)
O40.1624 (3)0.8141 (3)0.9464 (3)0.0678 (9)
C10.0359 (4)1.5926 (4)0.1243 (3)0.0478 (9)
H10.06101.53870.06770.057*
C20.0438 (4)1.6889 (4)0.0602 (4)0.0506 (9)
H20.06481.69380.03310.061*
C30.0375 (4)1.7967 (4)0.1312 (4)0.0477 (9)
C40.0241 (4)1.7899 (4)0.2703 (4)0.0494 (9)
H40.01301.85120.31990.059*
C50.0952 (4)1.7006 (4)0.3300 (3)0.0433 (8)
C60.1415 (5)1.6968 (4)0.4687 (4)0.0559 (11)
H60.12731.76020.51370.067*
C70.2039 (5)1.6063 (4)0.5356 (4)0.0537 (10)
H70.23071.60950.62460.064*
C80.2314 (4)1.5016 (4)0.4727 (3)0.0438 (8)
H80.32111.50830.46680.053*
C90.1357 (4)1.4910 (3)0.3352 (3)0.0390 (8)
H90.04701.48280.34340.047*
C100.1339 (3)1.6025 (4)0.2590 (3)0.0410 (8)
C110.1616 (5)1.3822 (4)0.2691 (3)0.0524 (10)
H11A0.09271.37400.18760.063*
H11B0.24511.39020.25170.063*
C120.1660 (5)1.2753 (4)0.3478 (3)0.0519 (10)
H12A0.19091.21110.30430.062*
H12B0.07831.26020.35330.062*
C130.2639 (4)1.2843 (3)0.4842 (3)0.0408 (8)
C140.2250 (4)1.3914 (4)0.5447 (3)0.0424 (8)
H140.13201.38130.53940.051*
C150.3035 (5)1.3823 (4)0.6861 (4)0.0582 (11)
H15A0.39131.41420.70270.070*
H15B0.25891.42180.73860.070*
C160.3102 (5)1.2547 (4)0.7126 (3)0.0537 (11)
H16A0.25931.23580.76950.064*
H16B0.40111.23140.75310.064*
C170.2524 (4)1.1927 (4)0.5825 (3)0.0436 (8)
H170.15791.18200.56980.052*
C180.4057 (4)1.2893 (5)0.4795 (5)0.0609 (12)
H18A0.42431.22170.43890.091*
H18B0.46561.29420.56500.091*
H18C0.41621.35520.43150.091*
C190.2694 (4)1.6302 (4)0.2444 (5)0.0599 (12)
H19A0.29571.56960.19870.090*
H19B0.33341.63810.32760.090*
H19C0.26391.70030.19770.090*
C200.3119 (4)1.0738 (4)0.5832 (3)0.0463 (9)
H200.40791.08330.60650.056*
C210.2671 (6)1.0148 (5)0.4531 (4)0.0696 (14)
H21A0.17291.02090.41730.104*
H21B0.29180.93570.46340.104*
H21C0.30851.05050.39670.104*
C220.2845 (4)0.9979 (4)0.6854 (4)0.0512 (10)
H22A0.28481.04500.75820.061*
H22B0.19690.96520.65090.061*
C230.3830 (4)0.9025 (4)0.7313 (4)0.0506 (10)
H23A0.46950.93570.77100.061*
H23B0.38750.85920.65740.061*
C240.3533 (4)0.8201 (4)0.8264 (3)0.0431 (9)
H240.26460.78830.78820.052*
C250.4510 (4)0.7234 (4)0.8664 (4)0.0512 (10)
H250.44990.68260.78810.061*
C260.4119 (5)0.6376 (5)0.9527 (5)0.0665 (12)
H26A0.42400.67121.03530.100*
H26B0.46630.57070.96210.100*
H26C0.32080.61670.91500.100*
C270.5931 (4)0.7633 (5)0.9299 (5)0.0678 (14)
H27A0.62400.80320.86830.102*
H27B0.64860.69840.96150.102*
H27C0.59580.81350.99980.102*
C280.2567 (4)0.8735 (4)0.9903 (4)0.0469 (9)
C290.2819 (5)0.9406 (5)1.1110 (4)0.0606 (11)
H29A0.20010.95251.12890.091*
H29B0.31971.01311.10110.091*
H29C0.34210.89961.18050.091*
O1W0.0684 (19)0.5921 (16)0.7944 (15)0.298 (8)
H1W0.095 (5)0.658 (5)0.846 (5)0.126 (14)*
H2W0.082 (5)0.520 (5)0.850 (5)0.125 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.083 (2)0.059 (2)0.0609 (18)0.0183 (19)0.0247 (16)0.0202 (17)
O20.0548 (16)0.0564 (19)0.0486 (14)0.0057 (14)0.0061 (12)0.0047 (14)
O30.0443 (13)0.0523 (16)0.0420 (12)0.0032 (13)0.0172 (10)0.0013 (12)
O40.0548 (17)0.075 (2)0.081 (2)0.0157 (17)0.0318 (16)0.0098 (19)
C10.057 (2)0.052 (2)0.0351 (17)0.0089 (19)0.0152 (16)0.0070 (17)
C20.056 (2)0.055 (3)0.0396 (17)0.0035 (19)0.0134 (16)0.0063 (19)
C30.0464 (19)0.048 (2)0.051 (2)0.0047 (18)0.0191 (16)0.0085 (19)
C40.053 (2)0.046 (2)0.050 (2)0.0008 (19)0.0175 (16)0.0020 (18)
C50.0432 (18)0.045 (2)0.0396 (17)0.0037 (16)0.0096 (14)0.0005 (16)
C60.068 (3)0.050 (3)0.0430 (19)0.001 (2)0.0083 (18)0.0088 (19)
C70.067 (3)0.049 (3)0.0355 (18)0.003 (2)0.0028 (17)0.0022 (18)
C80.0413 (18)0.048 (2)0.0377 (16)0.0021 (17)0.0066 (14)0.0011 (17)
C90.0404 (17)0.045 (2)0.0319 (15)0.0024 (15)0.0111 (13)0.0018 (15)
C100.0414 (17)0.046 (2)0.0375 (16)0.0006 (16)0.0146 (14)0.0039 (16)
C110.073 (3)0.052 (3)0.0299 (16)0.005 (2)0.0139 (16)0.0009 (18)
C120.071 (3)0.049 (3)0.0322 (17)0.005 (2)0.0112 (17)0.0005 (16)
C130.0447 (18)0.047 (2)0.0314 (16)0.0037 (17)0.0123 (14)0.0033 (15)
C140.0454 (18)0.049 (2)0.0318 (16)0.0012 (17)0.0098 (14)0.0019 (16)
C150.074 (3)0.056 (3)0.0367 (19)0.000 (2)0.0055 (18)0.0004 (19)
C160.068 (3)0.061 (3)0.0293 (17)0.008 (2)0.0111 (16)0.0047 (17)
C170.0399 (18)0.055 (2)0.0373 (16)0.0033 (17)0.0135 (14)0.0069 (17)
C180.057 (2)0.066 (3)0.070 (3)0.011 (2)0.034 (2)0.019 (2)
C190.052 (2)0.062 (3)0.075 (3)0.002 (2)0.033 (2)0.021 (2)
C200.0468 (19)0.055 (3)0.0399 (18)0.0019 (17)0.0170 (15)0.0068 (17)
C210.102 (4)0.057 (3)0.047 (2)0.009 (3)0.019 (2)0.004 (2)
C220.051 (2)0.057 (3)0.050 (2)0.007 (2)0.0226 (17)0.013 (2)
C230.0486 (19)0.061 (3)0.0473 (19)0.0073 (19)0.0224 (16)0.0138 (19)
C240.0443 (18)0.049 (2)0.0371 (17)0.0001 (16)0.0143 (14)0.0009 (16)
C250.057 (2)0.054 (3)0.0428 (18)0.007 (2)0.0154 (16)0.0069 (18)
C260.078 (3)0.054 (3)0.069 (3)0.011 (2)0.025 (2)0.016 (2)
C270.053 (2)0.082 (4)0.066 (3)0.014 (2)0.015 (2)0.024 (3)
C280.0479 (19)0.051 (2)0.0458 (18)0.0047 (19)0.0208 (15)0.0089 (18)
C290.076 (3)0.061 (3)0.051 (2)0.006 (2)0.029 (2)0.004 (2)
O1W0.349 (18)0.22 (2)0.308 (19)0.027 (17)0.074 (15)0.006 (18)
Geometric parameters (Å, º) top
O1—C31.223 (5)C16—C171.549 (5)
O2—C11.431 (5)C16—H16A0.9700
O2—C21.451 (5)C16—H16B0.9700
O3—C281.339 (4)C17—C201.530 (6)
O3—C241.462 (4)C17—H170.9800
O4—C281.194 (5)C18—H18A0.9600
C1—C21.456 (6)C18—H18B0.9600
C1—C101.526 (5)C18—H18C0.9600
C1—H10.9800C19—H19A0.9600
C2—C31.475 (6)C19—H19B0.9600
C2—H20.9800C19—H19C0.9600
C3—C41.465 (6)C20—C211.524 (6)
C4—C51.339 (6)C20—C221.529 (5)
C4—H40.9300C20—H200.9800
C5—C61.449 (5)C21—H21A0.9600
C5—C101.515 (6)C21—H21B0.9600
C6—C71.342 (6)C21—H21C0.9600
C6—H60.9300C22—C231.509 (6)
C7—C81.481 (6)C22—H22A0.9700
C7—H70.9300C22—H22B0.9700
C8—C141.527 (6)C23—C241.525 (5)
C8—C91.543 (5)C23—H23A0.9700
C8—H80.9800C23—H23B0.9700
C9—C111.533 (6)C24—C251.509 (6)
C9—C101.548 (5)C24—H240.9800
C9—H90.9800C25—C271.529 (6)
C10—C191.535 (5)C25—C261.526 (6)
C11—C121.515 (6)C25—H250.9800
C11—H11A0.9700C26—H26A0.9600
C11—H11B0.9700C26—H26B0.9600
C12—C131.541 (5)C26—H26C0.9600
C12—H12A0.9700C27—H27A0.9600
C12—H12B0.9700C27—H27B0.9600
C13—C181.527 (5)C27—H27C0.9600
C13—C141.535 (6)C28—C291.492 (6)
C13—C171.554 (5)C29—H29A0.9600
C14—C151.522 (5)C29—H29B0.9600
C14—H140.9800C29—H29C0.9600
C15—C161.522 (7)O1W—H1W0.94 (5)
C15—H15A0.9700O1W—H2W1.03 (5)
C15—H15B0.9700
C1—O2—C260.7 (3)C15—C16—H16B110.2
C28—O3—C24119.0 (3)C17—C16—H16B110.2
O2—C1—C260.3 (3)H16A—C16—H16B108.5
O2—C1—C10117.9 (3)C20—C17—C16112.2 (3)
C2—C1—C10122.0 (4)C20—C17—C13120.7 (3)
O2—C1—H1115.2C16—C17—C13102.9 (3)
C2—C1—H1115.2C20—C17—H17106.8
C10—C1—H1115.2C16—C17—H17106.8
O2—C2—C159.0 (3)C13—C17—H17106.8
O2—C2—C3113.3 (3)C13—C18—H18A109.5
C1—C2—C3118.9 (3)C13—C18—H18B109.5
O2—C2—H2117.4H18A—C18—H18B109.5
C1—C2—H2117.4C13—C18—H18C109.5
C3—C2—H2117.4H18A—C18—H18C109.5
O1—C3—C4123.3 (4)H18B—C18—H18C109.5
O1—C3—C2120.8 (4)C10—C19—H19A109.5
C4—C3—C2115.9 (4)C10—C19—H19B109.5
C5—C4—C3123.7 (4)H19A—C19—H19B109.5
C5—C4—H4118.1C10—C19—H19C109.5
C3—C4—H4118.1H19A—C19—H19C109.5
C4—C5—C6119.7 (4)H19B—C19—H19C109.5
C4—C5—C10122.9 (3)C21—C20—C17113.6 (3)
C6—C5—C10117.3 (4)C21—C20—C22110.4 (4)
C7—C6—C5123.3 (4)C17—C20—C22111.1 (3)
C7—C6—H6118.4C21—C20—H20107.1
C5—C6—H6118.4C17—C20—H20107.1
C6—C7—C8122.3 (3)C22—C20—H20107.1
C6—C7—H7118.8C20—C21—H21A109.5
C8—C7—H7118.8C20—C21—H21B109.5
C7—C8—C14114.4 (3)H21A—C21—H21B109.5
C7—C8—C9110.9 (3)C20—C21—H21C109.5
C14—C8—C9108.4 (3)H21A—C21—H21C109.5
C7—C8—H8107.6H21B—C21—H21C109.5
C14—C8—H8107.6C23—C22—C20113.9 (3)
C9—C8—H8107.6C23—C22—H22A108.8
C11—C9—C8111.6 (3)C20—C22—H22A108.8
C11—C9—C10114.8 (3)C23—C22—H22B108.8
C8—C9—C10110.8 (3)C20—C22—H22B108.8
C11—C9—H9106.3H22A—C22—H22B107.7
C8—C9—H9106.3C22—C23—C24115.3 (3)
C10—C9—H9106.3C22—C23—H23A108.4
C5—C10—C1110.1 (3)C24—C23—H23A108.4
C5—C10—C19107.8 (4)C22—C23—H23B108.4
C1—C10—C19107.3 (3)C24—C23—H23B108.4
C5—C10—C9108.8 (3)H23A—C23—H23B107.5
C1—C10—C9110.4 (3)O3—C24—C25108.9 (3)
C19—C10—C9112.4 (3)O3—C24—C23107.2 (3)
C12—C11—C9113.4 (3)C25—C24—C23113.8 (3)
C12—C11—H11A108.9O3—C24—H24109.0
C9—C11—H11A108.9C25—C24—H24109.0
C12—C11—H11B108.9C23—C24—H24109.0
C9—C11—H11B108.9C24—C25—C27113.5 (4)
H11A—C11—H11B107.7C24—C25—C26112.3 (4)
C11—C12—C13112.9 (4)C27—C25—C26109.9 (4)
C11—C12—H12A109.0C24—C25—H25106.9
C13—C12—H12A109.0C27—C25—H25106.9
C11—C12—H12B109.0C26—C25—H25106.9
C13—C12—H12B109.0C25—C26—H26A109.5
H12A—C12—H12B107.8C25—C26—H26B109.5
C18—C13—C14112.7 (4)H26A—C26—H26B109.5
C18—C13—C12110.3 (3)C25—C26—H26C109.5
C14—C13—C12106.6 (3)H26A—C26—H26C109.5
C18—C13—C17110.0 (3)H26B—C26—H26C109.5
C14—C13—C17100.1 (3)C25—C27—H27A109.5
C12—C13—C17116.9 (3)C25—C27—H27B109.5
C15—C14—C8119.2 (3)H27A—C27—H27B109.5
C15—C14—C13104.3 (3)C25—C27—H27C109.5
C8—C14—C13114.0 (3)H27A—C27—H27C109.5
C15—C14—H14106.1H27B—C27—H27C109.5
C8—C14—H14106.1O4—C28—O3124.6 (4)
C13—C14—H14106.1O4—C28—C29124.3 (4)
C16—C15—C14104.0 (3)O3—C28—C29111.0 (4)
C16—C15—H15A111.0C28—C29—H29A109.5
C14—C15—H15A111.0C28—C29—H29B109.5
C16—C15—H15B111.0H29A—C29—H29B109.5
C14—C15—H15B111.0C28—C29—H29C109.5
H15A—C15—H15B109.0H29A—C29—H29C109.5
C15—C16—C17107.6 (3)H29B—C29—H29C109.5
C15—C16—H16A110.2H1W—O1W—H2W111 (6)
C17—C16—H16A110.2
C2—O2—C1—C10112.9 (4)C9—C11—C12—C1353.3 (5)
C1—O2—C2—C3110.8 (4)C11—C12—C13—C1867.5 (5)
C10—C1—C2—O2106.2 (4)C11—C12—C13—C1455.1 (4)
O2—C1—C2—C3101.3 (4)C11—C12—C13—C17165.9 (3)
C10—C1—C2—C34.9 (6)C7—C8—C14—C1551.6 (5)
O2—C2—C3—O1125.7 (4)C9—C8—C14—C15175.9 (3)
C1—C2—C3—O1168.1 (4)C7—C8—C14—C13175.6 (3)
O2—C2—C3—C452.0 (5)C9—C8—C14—C1360.0 (4)
C1—C2—C3—C414.3 (6)C18—C13—C14—C1570.8 (4)
O1—C3—C4—C5168.8 (4)C12—C13—C14—C15168.1 (3)
C2—C3—C4—C513.6 (6)C17—C13—C14—C1545.9 (4)
C3—C4—C5—C6174.0 (4)C18—C13—C14—C860.9 (4)
C3—C4—C5—C107.6 (6)C12—C13—C14—C860.2 (4)
C4—C5—C6—C7174.4 (4)C17—C13—C14—C8177.6 (3)
C10—C5—C6—C77.2 (6)C8—C14—C15—C16162.1 (4)
C5—C6—C7—C80.2 (7)C13—C14—C15—C1633.5 (4)
C6—C7—C8—C14145.8 (4)C14—C15—C16—C177.6 (5)
C6—C7—C8—C922.8 (6)C15—C16—C17—C20151.7 (4)
C7—C8—C9—C11179.3 (4)C15—C16—C17—C1320.5 (5)
C14—C8—C9—C1152.9 (4)C18—C13—C17—C2047.0 (5)
C7—C8—C9—C1051.4 (4)C14—C13—C17—C20165.7 (3)
C14—C8—C9—C10177.8 (3)C12—C13—C17—C2079.8 (4)
C4—C5—C10—C125.0 (5)C18—C13—C17—C1678.9 (4)
C6—C5—C10—C1156.6 (4)C14—C13—C17—C1639.8 (4)
C4—C5—C10—C1991.7 (4)C12—C13—C17—C16154.3 (3)
C6—C5—C10—C1986.7 (4)C16—C17—C20—C21174.5 (4)
C4—C5—C10—C9146.1 (4)C13—C17—C20—C2153.1 (5)
C6—C5—C10—C935.4 (4)C16—C17—C20—C2260.3 (4)
O2—C1—C10—C547.5 (5)C13—C17—C20—C22178.3 (3)
C2—C1—C10—C523.3 (5)C21—C20—C22—C2377.8 (5)
O2—C1—C10—C19164.6 (4)C17—C20—C22—C23155.3 (4)
C2—C1—C10—C1993.8 (4)C20—C22—C23—C24175.9 (4)
O2—C1—C10—C972.7 (4)C28—O3—C24—C25103.7 (4)
C2—C1—C10—C9143.5 (4)C28—O3—C24—C23132.7 (3)
C11—C9—C10—C5175.0 (3)C22—C23—C24—O361.7 (4)
C8—C9—C10—C557.4 (4)C22—C23—C24—C25177.9 (4)
C11—C9—C10—C154.1 (4)O3—C24—C25—C2760.1 (4)
C8—C9—C10—C1178.3 (3)C23—C24—C25—C2759.4 (5)
C11—C9—C10—C1965.7 (4)O3—C24—C25—C2665.2 (5)
C8—C9—C10—C1961.9 (4)C23—C24—C25—C26175.3 (4)
C8—C9—C11—C1251.4 (5)C24—O3—C28—O43.0 (6)
C10—C9—C11—C12178.6 (4)C24—O3—C28—C29175.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O40.95 (6)2.15 (6)3.085 (18)174 (5)
O1W—H2W···O1i1.03 (6)1.78 (6)2.799 (18)170 (5)
C1—H1···O1ii0.982.463.430 (6)169
Symmetry codes: (i) x, y3/2, z+1; (ii) x, y1/2, z.

Experimental details

Crystal data
Chemical formulaC29H42O4·H2O
Mr472.64
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)10.642 (3), 11.719 (2), 10.977 (3)
β (°) 108.04 (2)
V3)1301.7 (6)
Z2
Radiation typeCu Kα
µ (mm1)0.64
Crystal size (mm)0.20 × 0.15 × 0.10
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2848, 2712, 2262
Rint0.016
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.162, 1.12
No. of reflections2712
No. of parameters322
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.55

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, XCAD4 (Harms, 1996), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXL and PARST (Nardelli, 1983).

Selected geometric parameters (Å, º) top
O1—C31.223 (5)O3—C241.462 (4)
O2—C11.431 (5)O4—C281.194 (5)
O2—C21.451 (5)O1W—H1W0.94 (5)
O3—C281.339 (4)O1W—H2W1.03 (5)
C1—O2—C260.7 (3)O2—C1—C10117.9 (3)
C28—O3—C24119.0 (3)O2—C2—C159.0 (3)
O2—C1—C260.3 (3)H1W—O1W—H2W111 (6)
C2—O2—C1—C10112.9 (4)C20—C22—C23—C24175.9 (4)
C1—O2—C2—C3110.8 (4)C22—C23—C24—C25177.9 (4)
O2—C1—C2—C3101.3 (4)C23—C24—C25—C26175.3 (4)
C13—C17—C20—C22178.3 (3)C24—O3—C28—C29175.4 (3)
C17—C20—C22—C23155.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O40.95 (6)2.15 (6)3.085 (18)174 (5)
O1W—H2W···O1i1.03 (6)1.78 (6)2.799 (18)170 (5)
C1—H1···O1ii0.982.463.430 (6)169
Symmetry codes: (i) x, y3/2, z+1; (ii) x, y1/2, z.
 

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