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3β-Hydr­oxy-7-drimen-12,11-olide hemihydrate, C15H22O3·0.5H2O, (I), has two sesquiterpene mol­ecules and one water mol­ecule in the asymmetric unit. The OH groups of both mol­ecules and both H atoms of the water mol­ecule are involved in near-linear inter­molecular hydrogen bonds, having O...O distances in the range 2.632 (3)–2.791 (2) Å. 3β-Acet­oxy-7-drimen-12,11-olide, C17H24O4, (II), has its ring system in very nearly the same conformation as the two mol­ecules of (I).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106007177/gz3003sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106007177/gz3003Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106007177/gz3003IIsup3.hkl
Contains datablock II

CCDC references: 605696; 605697

Comment top

Plants of the genus Warburgia are of interest because of their use by herbalists in Kenya for the treatment of a number of parasitic diseases (Kokwaro, 1976). Isolation of drimanolide-class sesquiterpenes (I) and (II) from the stem bark of Warburgia ugandensis Sprague (Canellaceae) has been described by Kioy et al. (1990). The molecular structures of 3β-hydroxy-7-drimen-12,11-olide hemihydrate, (I), and 3β-acetoxy-7-drimen-12,11-olide, (II), were determined in order to ascertain unambiguously the relative stereochemistry of the 3-OH and 3-OAc groups, respectively, as well as to confirm the relative configurations of the other asymmetric centers.

One of the two independent molecules of (I) is shown in Fig. 1. The OH group at C3 is seen to be β-oriented, and the configurations at the other chiral centers are confirmed to be those reported by Kioy et al. (1990). The conformations of the two independent molecules are nearly identical, with maximum deviation in an endocyclic torsion angle of 2.5 (6)°, about the double bond C7C8. The OH-carrying A ring has a chair conformation, the central B ring a half-chair conformation, and the lactone ring a C2 half-chair conformation, with the axis passing through C12 and bisecting C9—C11. The most notable difference in the conformations of the two molecules involves the OH group, in which the O—H bond is roughly parallel to C10—C15 in the A molecule and roughly antiparallel in the B molecule, in accordance with the hydrogen-bonding scheme. The OH group of the A molecule donates a hydrogen bond to the water molecule, while the OH of the B molecule instead donates to the OH group of the A molecule. The lactone carbonyl atom O2 of the A molecule accepts a hydrogen bond (from water), but that of the B molecule is not involved in hydrogen bonding. The acceptor for the second hydrogen bond donated by water is the OH group of the B molecule.

Compound (II) is shown in Fig. 2, and the configurations at all the chiral centers are seen to be the same as those of (I). The conformation of the ring system also agrees well with that of (I): the largest individual difference between an endocyclic torsion angle in (II) and the corresponding average value in (I) is 4.1 (5)°, for C7—C8—C9—C10. The conformations of the ring system in both title compounds agree fairly well with those of two molecules also having the drimanolide skeleton, insulicolide A (Rahbaek et al., 1997) and iresin dibromobenzoate (Rossman & Lipscomb, 1958). The cell dimensions of (II) at room temperature (299 K), measured on a Nonius CAD-4 diffractometer using Cu Kα radiation, are a = 6.8885 (6), b = 7.9753 (8) and c = 14.411 (2) Å, and β = 101.613 (7)°.

Experimental top

Compounds (I) and (II) were isolated from the stem bark of Warburgia ugandensis Sprague (Canellaceae) collected in Eldoret, Uasin Gishu District, Kenya. [Please give brief details of preparative procedure, or an appropriate reference] Crystals were grown from a solution in acetone–hexane (Ratio?).

Refinement top

H atoms were placed in calculated positions, guided by difference maps, with C—H bond distances in the range 0.95–1.00 Å and with Uiso(H) = 1.2Ueq(C), or 1.5Ueq(C) for methyl H, and thereafter treated as riding. Coordinates for OH H atoms were refined. A torsional parameter was refined for each OH group and each methyl group. The absolute configuration could not be established from the X-ray data, but was assigned based on the configuration of insulicolide A (Rahbaek et al., 1997). Friedel pairs were averaged.

Computing details top

For both compounds, data collection: COLLECT (Nonius, 1999); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. One of the two independent molecules (molecule A) in (I), showing the atom-numbering scheme and with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. A view of the acetate, (II), showing the atom-numbering scheme and with displacement ellipsoids drawn at the 50% probability level.
(I) 3β-Hydroxy-7-drimen-12,11-olide hemihydrate top
Crystal data top
C15H22O3·0.5H2OF(000) = 564
Mr = 259.33Dx = 1.238 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4619 reflections
a = 12.875 (3) Åθ = 2.5–32.0°
b = 6.153 (2) ŵ = 0.09 mm1
c = 18.268 (4) ÅT = 120 K
β = 106.031 (16)°Prism, colorless
V = 1390.9 (6) Å30.42 × 0.35 × 0.20 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector (with Oxford Cryostream)
diffractometer
3773 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
Graphite monochromatorθmax = 32.0°, θmin = 3.1°
ω scans with κ offsetsh = 1919
17077 measured reflectionsk = 89
5214 independent reflectionsl = 2726
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0505P)2 + 0.0592P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.003
5214 reflectionsΔρmax = 0.38 e Å3
353 parametersΔρmin = 0.23 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.007 (2)
Crystal data top
C15H22O3·0.5H2OV = 1390.9 (6) Å3
Mr = 259.33Z = 4
Monoclinic, P21Mo Kα radiation
a = 12.875 (3) ŵ = 0.09 mm1
b = 6.153 (2) ÅT = 120 K
c = 18.268 (4) Å0.42 × 0.35 × 0.20 mm
β = 106.031 (16)°
Data collection top
Nonius KappaCCD area-detector (with Oxford Cryostream)
diffractometer
3773 reflections with I > 2σ(I)
17077 measured reflectionsRint = 0.040
5214 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0491 restraint
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.38 e Å3
5214 reflectionsΔρmin = 0.23 e Å3
353 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
O1A0.53239 (11)0.8344 (3)1.01792 (8)0.0299 (3)
O2A0.37960 (12)0.8405 (3)0.92329 (10)0.0392 (4)
O3A1.01372 (13)0.5682 (3)0.83070 (10)0.0361 (4)
H3OA1.055 (2)0.678 (6)0.8468 (16)0.054*
C1A0.86114 (14)0.7138 (4)0.97246 (10)0.0210 (4)
H1A10.88240.79661.02080.025*
H1A20.84780.56150.98490.025*
C2A0.95405 (15)0.7185 (4)0.93584 (10)0.0240 (4)
H2A10.97130.87090.92630.029*
H2A21.01910.65220.97080.029*
C3A0.92312 (16)0.5942 (4)0.86133 (11)0.0244 (4)
H3A0.90130.44510.87310.029*
C4A0.82503 (16)0.6933 (4)0.80198 (10)0.0234 (4)
C5A0.73066 (15)0.7079 (3)0.83992 (9)0.0194 (4)
H5A0.71190.55320.84720.023*
C6A0.62630 (16)0.8045 (4)0.78670 (10)0.0302 (5)
H6A10.64260.94930.76900.036*
H6A20.60130.70980.74140.036*
C7A0.53695 (16)0.8271 (4)0.82450 (11)0.0289 (5)
H7A0.46690.86880.79490.035*
C8A0.55391 (15)0.7902 (3)0.89770 (11)0.0232 (4)
C9A0.66147 (14)0.7336 (3)0.95175 (9)0.0187 (4)
H9A0.66570.57180.95700.022*
C10A0.75600 (14)0.8099 (3)0.92124 (9)0.0166 (4)
C11A0.64940 (15)0.8286 (4)1.02673 (10)0.0245 (4)
H11A0.68640.73551.07040.029*
H11B0.68050.97661.03520.029*
C12A0.47787 (17)0.8244 (4)0.94392 (12)0.0288 (5)
C13A0.7910 (2)0.5376 (4)0.73353 (12)0.0361 (6)
H13A0.73210.60320.69380.054*
H13B0.76650.39980.74990.054*
H13C0.85280.51080.71330.054*
C14A0.85720 (19)0.9103 (4)0.77220 (12)0.0296 (5)
H14A0.88741.00790.81520.044*
H14B0.79320.97770.73770.044*
H14C0.91140.88340.74470.044*
C15A0.76189 (16)1.0592 (4)0.92026 (11)0.0231 (4)
H15A0.77901.11440.97260.035*
H15B0.69211.11790.89080.035*
H15C0.81831.10440.89680.035*
O1B0.46672 (11)0.6360 (3)0.50293 (8)0.0286 (4)
O2B0.37074 (12)0.5687 (4)0.38312 (7)0.0379 (4)
O3B0.10653 (15)0.2489 (3)0.77540 (9)0.0374 (4)
H3OB0.072 (2)0.334 (6)0.7943 (15)0.056*
C1B0.33611 (17)0.4662 (4)0.70622 (10)0.0244 (4)
H1B10.41520.45710.72900.029*
H1B20.31570.62180.70350.029*
C2B0.27970 (17)0.3486 (4)0.75802 (10)0.0284 (5)
H2B10.30490.19600.76490.034*
H2B20.29870.41940.80870.034*
C3B0.15803 (17)0.3530 (4)0.72424 (11)0.0275 (5)
H3B0.13450.50850.71900.033*
C4B0.11959 (17)0.2460 (4)0.64484 (12)0.0251 (4)
C5B0.18268 (15)0.3543 (4)0.59266 (10)0.0210 (4)
H5B0.15650.50800.58670.025*
C6B0.15093 (16)0.2614 (4)0.51106 (11)0.0291 (5)
H6B10.16020.10160.51380.035*
H6B20.07350.29200.48710.035*
C7B0.21586 (16)0.3525 (4)0.46151 (10)0.0282 (5)
H7B0.19580.31930.40870.034*
C8B0.30057 (16)0.4783 (4)0.49016 (10)0.0232 (4)
C9B0.34082 (15)0.5409 (3)0.57263 (10)0.0203 (4)
H9B0.30670.68280.57930.024*
C10B0.30801 (15)0.3729 (3)0.62499 (10)0.0190 (4)
C11B0.46115 (16)0.5840 (4)0.58015 (10)0.0261 (5)
H11C0.48800.70710.61510.031*
H11D0.50510.45370.59990.031*
C12B0.37772 (17)0.5612 (4)0.45014 (11)0.0270 (4)
C13B0.00170 (16)0.2957 (4)0.61230 (13)0.0352 (5)
H13D0.04080.24640.64830.053*
H13E0.02960.21980.56370.053*
H13F0.01190.45260.60430.053*
C14B0.13066 (18)0.0031 (4)0.65216 (13)0.0293 (5)
H14D0.20290.04020.68430.044*
H14E0.12010.06730.60150.044*
H14F0.07600.06010.67530.044*
C15B0.36673 (16)0.1566 (3)0.62423 (12)0.0249 (4)
H15D0.44430.17640.64780.037*
H15E0.35490.10760.57150.037*
H15F0.33850.04750.65280.037*
O1W0.15716 (15)0.8841 (4)0.85921 (11)0.0503 (5)
H1W0.229 (3)0.859 (7)0.8750 (17)0.076*
H2W0.149 (3)0.998 (7)0.8288 (19)0.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0251 (8)0.0298 (8)0.0410 (8)0.0014 (7)0.0194 (6)0.0033 (8)
O2A0.0196 (7)0.0308 (9)0.0681 (10)0.0000 (8)0.0136 (7)0.0024 (9)
O3A0.0326 (9)0.0296 (9)0.0571 (10)0.0033 (8)0.0306 (8)0.0094 (9)
C1A0.0169 (9)0.0271 (11)0.0188 (8)0.0011 (8)0.0045 (7)0.0019 (8)
C2A0.0177 (9)0.0246 (11)0.0299 (9)0.0030 (9)0.0072 (7)0.0018 (9)
C3A0.0233 (10)0.0206 (10)0.0354 (10)0.0004 (9)0.0181 (8)0.0008 (9)
C4A0.0293 (10)0.0231 (11)0.0200 (8)0.0035 (9)0.0107 (7)0.0026 (8)
C5A0.0202 (9)0.0200 (10)0.0185 (8)0.0038 (8)0.0062 (7)0.0012 (8)
C6A0.0266 (10)0.0399 (14)0.0203 (8)0.0032 (11)0.0002 (7)0.0007 (10)
C7A0.0189 (9)0.0297 (12)0.0327 (10)0.0032 (10)0.0017 (8)0.0001 (10)
C8A0.0154 (8)0.0201 (10)0.0327 (9)0.0002 (8)0.0044 (7)0.0016 (9)
C9A0.0178 (8)0.0183 (9)0.0211 (8)0.0009 (8)0.0076 (7)0.0019 (8)
C10A0.0156 (8)0.0157 (9)0.0182 (8)0.0000 (8)0.0043 (6)0.0005 (8)
C11A0.0224 (9)0.0263 (11)0.0276 (9)0.0004 (9)0.0117 (7)0.0027 (10)
C12A0.0226 (10)0.0184 (10)0.0474 (12)0.0003 (9)0.0130 (9)0.0004 (10)
C13A0.0458 (14)0.0381 (14)0.0294 (10)0.0103 (12)0.0190 (10)0.0108 (11)
C14A0.0375 (12)0.0284 (12)0.0264 (9)0.0023 (10)0.0148 (9)0.0020 (9)
C15A0.0220 (9)0.0185 (10)0.0284 (9)0.0002 (9)0.0064 (8)0.0006 (9)
O1B0.0296 (8)0.0350 (9)0.0232 (6)0.0089 (7)0.0105 (6)0.0003 (7)
O2B0.0359 (8)0.0586 (12)0.0220 (7)0.0074 (9)0.0126 (6)0.0011 (8)
O3B0.0558 (11)0.0265 (9)0.0441 (9)0.0108 (8)0.0374 (8)0.0108 (8)
C1B0.0311 (11)0.0235 (11)0.0190 (8)0.0013 (9)0.0074 (8)0.0028 (8)
C2B0.0376 (11)0.0292 (11)0.0216 (8)0.0015 (10)0.0134 (8)0.0016 (10)
C3B0.0396 (12)0.0200 (10)0.0304 (9)0.0068 (10)0.0224 (9)0.0064 (10)
C4B0.0243 (10)0.0228 (10)0.0321 (10)0.0042 (9)0.0142 (8)0.0055 (9)
C5B0.0224 (9)0.0193 (9)0.0223 (8)0.0011 (8)0.0080 (7)0.0012 (8)
C6B0.0246 (10)0.0354 (13)0.0267 (9)0.0073 (10)0.0063 (8)0.0041 (10)
C7B0.0271 (10)0.0380 (13)0.0199 (8)0.0022 (10)0.0071 (7)0.0052 (10)
C8B0.0259 (10)0.0262 (11)0.0188 (8)0.0003 (9)0.0082 (7)0.0001 (8)
C9B0.0235 (9)0.0191 (10)0.0194 (8)0.0001 (9)0.0076 (7)0.0014 (8)
C10B0.0225 (9)0.0171 (9)0.0177 (8)0.0006 (8)0.0063 (7)0.0016 (8)
C11B0.0296 (10)0.0311 (12)0.0177 (8)0.0065 (10)0.0065 (7)0.0019 (9)
C12B0.0293 (10)0.0299 (12)0.0231 (9)0.0033 (10)0.0096 (8)0.0025 (9)
C13B0.0248 (11)0.0367 (14)0.0479 (12)0.0037 (11)0.0164 (9)0.0105 (12)
C14B0.0295 (11)0.0208 (10)0.0428 (12)0.0005 (9)0.0185 (10)0.0007 (10)
C15B0.0249 (10)0.0206 (10)0.0314 (10)0.0026 (8)0.0112 (8)0.0007 (9)
O1W0.0266 (8)0.0432 (12)0.0734 (13)0.0053 (9)0.0007 (8)0.0288 (10)
Geometric parameters (Å, º) top
O1A—C12A1.342 (3)O1B—C11B1.467 (2)
O1A—C11A1.471 (2)O2B—C12B1.203 (2)
O2A—C12A1.220 (2)O3B—C3B1.437 (2)
O3A—C3A1.435 (2)O3B—H3OB0.82 (3)
O3A—H3OA0.86 (3)C1B—C2B1.525 (3)
C1A—C2A1.524 (3)C1B—C10B1.538 (2)
C1A—C10A1.536 (2)C1B—H1B10.9900
C1A—H1A10.9900C1B—H1B20.9900
C1A—H1A20.9900C2B—C3B1.517 (3)
C2A—C3A1.516 (3)C2B—H2B10.9900
C2A—H2A10.9900C2B—H2B20.9900
C2A—H2A20.9900C3B—C4B1.544 (3)
C3A—C4A1.545 (3)C3B—H3B1.0000
C3A—H3A1.0000C4B—C13B1.540 (3)
C4A—C13A1.539 (3)C4B—C14B1.542 (3)
C4A—C14A1.541 (3)C4B—C5B1.562 (3)
C4A—C5A1.559 (3)C5B—C6B1.543 (3)
C5A—C6A1.543 (3)C5B—C10B1.562 (3)
C5A—C10A1.562 (2)C5B—H5B1.0000
C5A—H5A1.0000C6B—C7B1.500 (3)
C6A—C7A1.503 (3)C6B—H6B10.9900
C6A—H6A10.9900C6B—H6B20.9900
C6A—H6A20.9900C7B—C8B1.322 (3)
C7A—C8A1.314 (3)C7B—H7B0.9500
C7A—H7A0.9500C8B—C12B1.477 (3)
C8A—C12A1.474 (3)C8B—C9B1.502 (3)
C8A—C9A1.503 (3)C9B—C11B1.540 (3)
C9A—C11A1.536 (3)C9B—C10B1.545 (3)
C9A—C10A1.545 (3)C9B—H9B1.0000
C9A—H9A1.0000C10B—C15B1.532 (3)
C10A—C15A1.536 (3)C11B—H11C0.9900
C11A—H11A0.9900C11B—H11D0.9900
C11A—H11B0.9900C13B—H13D0.9800
C13A—H13A0.9800C13B—H13E0.9800
C13A—H13B0.9800C13B—H13F0.9800
C13A—H13C0.9800C14B—H14D0.9800
C14A—H14A0.9800C14B—H14E0.9800
C14A—H14B0.9800C14B—H14F0.9800
C14A—H14C0.9800C15B—H15D0.9800
C15A—H15A0.9800C15B—H15E0.9800
C15A—H15B0.9800C15B—H15F0.9800
C15A—H15C0.9800O1W—H1W0.90 (3)
O1B—C12B1.358 (2)O1W—H2W0.88 (4)
C12A—O1A—C11A110.13 (15)C3B—O3B—H3OB113 (2)
C3A—O3A—H3OA106 (2)C2B—C1B—C10B113.31 (18)
C2A—C1A—C10A113.09 (15)C2B—C1B—H1B1108.9
C2A—C1A—H1A1109.0C10B—C1B—H1B1108.9
C10A—C1A—H1A1109.0C2B—C1B—H1B2108.9
C2A—C1A—H1A2109.0C10B—C1B—H1B2108.9
C10A—C1A—H1A2109.0H1B1—C1B—H1B2107.7
H1A1—C1A—H1A2107.8C3B—C2B—C1B110.76 (16)
C3A—C2A—C1A109.96 (16)C3B—C2B—H2B1109.5
C3A—C2A—H2A1109.7C1B—C2B—H2B1109.5
C1A—C2A—H2A1109.7C3B—C2B—H2B2109.5
C3A—C2A—H2A2109.7C1B—C2B—H2B2109.5
C1A—C2A—H2A2109.7H2B1—C2B—H2B2108.1
H2A1—C2A—H2A2108.2O3B—C3B—C2B109.73 (16)
O3A—C3A—C2A111.47 (17)O3B—C3B—C4B109.58 (18)
O3A—C3A—C4A111.42 (16)C2B—C3B—C4B113.67 (16)
C2A—C3A—C4A113.09 (17)O3B—C3B—H3B107.9
O3A—C3A—H3A106.8C2B—C3B—H3B107.9
C2A—C3A—H3A106.8C4B—C3B—H3B107.9
C4A—C3A—H3A106.8C13B—C4B—C14B106.9 (2)
C13A—C4A—C14A107.22 (16)C13B—C4B—C3B107.79 (17)
C13A—C4A—C3A108.58 (19)C14B—C4B—C3B110.14 (18)
C14A—C4A—C3A110.03 (17)C13B—C4B—C5B108.81 (16)
C13A—C4A—C5A108.38 (17)C14B—C4B—C5B115.19 (19)
C14A—C4A—C5A115.17 (18)C3B—C4B—C5B107.80 (17)
C3A—C4A—C5A107.30 (15)C6B—C5B—C10B111.29 (15)
C6A—C5A—C4A113.08 (15)C6B—C5B—C4B112.83 (17)
C6A—C5A—C10A111.19 (16)C10B—C5B—C4B117.22 (15)
C4A—C5A—C10A117.54 (15)C6B—C5B—H5B104.7
C6A—C5A—H5A104.5C10B—C5B—H5B104.7
C4A—C5A—H5A104.5C4B—C5B—H5B104.7
C10A—C5A—H5A104.5C7B—C6B—C5B113.67 (17)
C7A—C6A—C5A112.94 (16)C7B—C6B—H6B1108.8
C7A—C6A—H6A1109.0C5B—C6B—H6B1108.8
C5A—C6A—H6A1109.0C7B—C6B—H6B2108.8
C7A—C6A—H6A2109.0C5B—C6B—H6B2108.8
C5A—C6A—H6A2109.0H6B1—C6B—H6B2107.7
H6A1—C6A—H6A2107.8C8B—C7B—C6B121.09 (17)
C8A—C7A—C6A121.24 (18)C8B—C7B—H7B119.5
C8A—C7A—H7A119.4C6B—C7B—H7B119.5
C6A—C7A—H7A119.4C7B—C8B—C12B126.89 (18)
C7A—C8A—C12A127.48 (18)C7B—C8B—C9B124.46 (18)
C7A—C8A—C9A124.94 (18)C12B—C8B—C9B108.36 (17)
C12A—C8A—C9A107.10 (16)C8B—C9B—C11B101.17 (15)
C8A—C9A—C11A101.30 (16)C8B—C9B—C10B111.84 (16)
C8A—C9A—C10A111.54 (15)C11B—C9B—C10B120.03 (16)
C11A—C9A—C10A119.31 (16)C8B—C9B—H9B107.7
C8A—C9A—H9A108.0C11B—C9B—H9B107.7
C11A—C9A—H9A108.0C10B—C9B—H9B107.7
C10A—C9A—H9A108.0C15B—C10B—C1B110.35 (16)
C1A—C10A—C15A110.71 (16)C15B—C10B—C9B110.84 (16)
C1A—C10A—C9A108.22 (15)C1B—C10B—C9B108.40 (16)
C15A—C10A—C9A110.75 (16)C15B—C10B—C5B113.19 (16)
C1A—C10A—C5A110.01 (15)C1B—C10B—C5B109.59 (15)
C15A—C10A—C5A112.84 (16)C9B—C10B—C5B104.21 (14)
C9A—C10A—C5A104.03 (14)O1B—C11B—C9B105.47 (14)
O1A—C11A—C9A105.33 (15)O1B—C11B—H11C110.6
O1A—C11A—H11A110.7C9B—C11B—H11C110.6
C9A—C11A—H11A110.7O1B—C11B—H11D110.6
O1A—C11A—H11B110.7C9B—C11B—H11D110.6
C9A—C11A—H11B110.7H11C—C11B—H11D108.8
H11A—C11A—H11B108.8O2B—C12B—O1B121.4 (2)
O2A—C12A—O1A121.1 (2)O2B—C12B—C8B130.2 (2)
O2A—C12A—C8A129.1 (2)O1B—C12B—C8B108.44 (15)
O1A—C12A—C8A109.78 (16)C4B—C13B—H13D109.5
C4A—C13A—H13A109.5C4B—C13B—H13E109.5
C4A—C13A—H13B109.5H13D—C13B—H13E109.5
H13A—C13A—H13B109.5C4B—C13B—H13F109.5
C4A—C13A—H13C109.5H13D—C13B—H13F109.5
H13A—C13A—H13C109.5H13E—C13B—H13F109.5
H13B—C13A—H13C109.5C4B—C14B—H14D109.5
C4A—C14A—H14A109.5C4B—C14B—H14E109.5
C4A—C14A—H14B109.5H14D—C14B—H14E109.5
H14A—C14A—H14B109.5C4B—C14B—H14F109.5
C4A—C14A—H14C109.5H14D—C14B—H14F109.5
H14A—C14A—H14C109.5H14E—C14B—H14F109.5
H14B—C14A—H14C109.5C10B—C15B—H15D109.5
C10A—C15A—H15A109.5C10B—C15B—H15E109.5
C10A—C15A—H15B109.5H15D—C15B—H15E109.5
H15A—C15A—H15B109.5C10B—C15B—H15F109.5
C10A—C15A—H15C109.5H15D—C15B—H15F109.5
H15A—C15A—H15C109.5H15E—C15B—H15F109.5
H15B—C15A—H15C109.5H1W—O1W—H2W105 (3)
C12B—O1B—C11B110.67 (16)
C10A—C1A—C2A—C3A58.2 (2)C10B—C1B—C2B—C3B57.0 (2)
C1A—C2A—C3A—O3A171.62 (17)C1B—C2B—C3B—O3B177.73 (18)
C1A—C2A—C3A—C4A61.9 (2)C1B—C2B—C3B—C4B59.2 (3)
O3A—C3A—C4A—C13A61.4 (2)O3B—C3B—C4B—C13B66.1 (2)
C2A—C3A—C4A—C13A172.13 (17)C2B—C3B—C4B—C13B170.73 (19)
O3A—C3A—C4A—C14A55.7 (2)O3B—C3B—C4B—C14B50.2 (2)
C2A—C3A—C4A—C14A70.8 (2)C2B—C3B—C4B—C14B73.0 (2)
O3A—C3A—C4A—C5A178.32 (17)O3B—C3B—C4B—C5B176.61 (16)
C2A—C3A—C4A—C5A55.2 (2)C2B—C3B—C4B—C5B53.4 (2)
C13A—C4A—C5A—C6A62.8 (2)C13B—C4B—C5B—C6B63.1 (2)
C14A—C4A—C5A—C6A57.2 (2)C14B—C4B—C5B—C6B56.8 (2)
C3A—C4A—C5A—C6A179.89 (18)C3B—C4B—C5B—C6B179.76 (18)
C13A—C4A—C5A—C10A165.48 (18)C13B—C4B—C5B—C10B165.61 (18)
C14A—C4A—C5A—C10A74.5 (2)C14B—C4B—C5B—C10B74.4 (2)
C3A—C4A—C5A—C10A48.4 (2)C3B—C4B—C5B—C10B49.0 (2)
C4A—C5A—C6A—C7A177.59 (19)C10B—C5B—C6B—C7B42.0 (3)
C10A—C5A—C6A—C7A42.8 (3)C4B—C5B—C6B—C7B176.13 (18)
C5A—C6A—C7A—C8A7.3 (3)C5B—C6B—C7B—C8B8.2 (3)
C6A—C7A—C8A—C12A174.0 (2)C6B—C7B—C8B—C12B173.5 (2)
C6A—C7A—C8A—C9A3.0 (4)C6B—C7B—C8B—C9B0.5 (4)
C7A—C8A—C9A—C11A150.6 (2)C7B—C8B—C9B—C11B153.9 (2)
C12A—C8A—C9A—C11A21.9 (2)C12B—C8B—C9B—C11B20.3 (2)
C7A—C8A—C9A—C10A22.6 (3)C7B—C8B—C9B—C10B24.9 (3)
C12A—C8A—C9A—C10A149.91 (17)C12B—C8B—C9B—C10B149.20 (18)
C2A—C1A—C10A—C15A75.9 (2)C2B—C1B—C10B—C15B75.0 (2)
C2A—C1A—C10A—C9A162.57 (17)C2B—C1B—C10B—C9B163.49 (17)
C2A—C1A—C10A—C5A49.5 (2)C2B—C1B—C10B—C5B50.3 (2)
C8A—C9A—C10A—C1A170.75 (16)C8B—C9B—C10B—C15B67.7 (2)
C11A—C9A—C10A—C1A71.7 (2)C11B—C9B—C10B—C15B50.5 (2)
C8A—C9A—C10A—C15A67.7 (2)C8B—C9B—C10B—C1B171.07 (16)
C11A—C9A—C10A—C15A49.9 (2)C11B—C9B—C10B—C1B70.7 (2)
C8A—C9A—C10A—C5A53.8 (2)C8B—C9B—C10B—C5B54.40 (19)
C11A—C9A—C10A—C5A171.37 (17)C11B—C9B—C10B—C5B172.60 (17)
C6A—C5A—C10A—C1A179.03 (16)C6B—C5B—C10B—C15B56.4 (2)
C4A—C5A—C10A—C1A46.5 (2)C4B—C5B—C10B—C15B75.5 (2)
C6A—C5A—C10A—C15A54.8 (2)C6B—C5B—C10B—C1B179.92 (19)
C4A—C5A—C10A—C15A77.7 (2)C4B—C5B—C10B—C1B48.1 (2)
C6A—C5A—C10A—C9A65.3 (2)C6B—C5B—C10B—C9B64.1 (2)
C4A—C5A—C10A—C9A162.20 (17)C4B—C5B—C10B—C9B163.94 (17)
C12A—O1A—C11A—C9A19.5 (2)C12B—O1B—C11B—C9B20.1 (2)
C8A—C9A—C11A—O1A24.7 (2)C8B—C9B—C11B—O1B23.8 (2)
C10A—C9A—C11A—O1A147.45 (17)C10B—C9B—C11B—O1B147.30 (17)
C11A—O1A—C12A—O2A175.4 (2)C11B—O1B—C12B—O2B172.9 (2)
C11A—O1A—C12A—C8A5.3 (2)C11B—O1B—C12B—C8B7.1 (3)
C7A—C8A—C12A—O2A20.0 (4)C7B—C8B—C12B—O2B15.3 (4)
C9A—C8A—C12A—O2A167.8 (2)C9B—C8B—C12B—O2B170.7 (3)
C7A—C8A—C12A—O1A160.9 (2)C7B—C8B—C12B—O1B164.7 (2)
C9A—C8A—C12A—O1A11.4 (2)C9B—C8B—C12B—O1B9.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3A—H3OA···O1Wi0.86 (3)1.79 (3)2.632 (3)164 (3)
O3B—H3OB···O3Aii0.82 (3)1.83 (4)2.641 (2)168 (3)
O1W—H1W···O2A0.90 (3)1.90 (3)2.791 (2)169 (3)
O1W—H2W···O3Biii0.88 (4)1.83 (4)2.694 (3)166 (3)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x, y+1, z.
(II) 3β-Acetoxy-7-drimen-12,11-olide top
Crystal data top
C17H24O4F(000) = 316
Mr = 292.36Dx = 1.285 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2218 reflections
a = 6.802 (3) Åθ = 2.5–30.0°
b = 7.918 (4) ŵ = 0.09 mm1
c = 14.302 (8) ÅT = 120 K
β = 101.22 (2)°Prism, colorless
V = 755.6 (7) Å30.33 × 0.18 × 0.15 mm
Z = 2
Data collection top
Nonius KappaCCD area-detector (with Oxford Cryostream)
diffractometer
1456 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.057
Graphite monochromatorθmax = 30.0°, θmin = 2.9°
ω scans with κ offsetsh = 99
8695 measured reflectionsk = 1111
2353 independent reflectionsl = 2020
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0473P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
2353 reflectionsΔρmax = 0.22 e Å3
195 parametersΔρmin = 0.20 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.012 (3)
Crystal data top
C17H24O4V = 755.6 (7) Å3
Mr = 292.36Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.802 (3) ŵ = 0.09 mm1
b = 7.918 (4) ÅT = 120 K
c = 14.302 (8) Å0.33 × 0.18 × 0.15 mm
β = 101.22 (2)°
Data collection top
Nonius KappaCCD area-detector (with Oxford Cryostream)
diffractometer
1456 reflections with I > 2σ(I)
8695 measured reflectionsRint = 0.057
2353 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0511 restraint
wR(F2) = 0.108H-atom parameters constrained
S = 0.98Δρmax = 0.22 e Å3
2353 reflectionsΔρmin = 0.20 e Å3
195 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
O10.8176 (3)0.4883 (3)0.55905 (12)0.0373 (5)
O20.9004 (3)0.7238 (3)0.64502 (13)0.0466 (6)
O30.2946 (2)0.7821 (3)0.03214 (12)0.0303 (5)
O40.0282 (3)0.7133 (3)0.02549 (13)0.0421 (6)
C10.5137 (4)0.5137 (4)0.24430 (18)0.0291 (6)
H1A0.59110.40710.24880.035*
H1B0.38830.49100.26750.035*
C20.4608 (4)0.5684 (4)0.13965 (18)0.0281 (6)
H2A0.58480.58180.11380.034*
H2B0.37670.48110.10170.034*
C30.3484 (4)0.7340 (4)0.13273 (17)0.0272 (6)
H30.22270.71780.15810.033*
C40.4685 (4)0.8808 (4)0.18701 (18)0.0277 (6)
C50.5321 (4)0.8218 (4)0.29222 (18)0.0273 (6)
H50.40300.80750.31500.033*
C60.6462 (4)0.9594 (4)0.35766 (18)0.0314 (7)
H6A0.75801.00150.32900.038*
H6B0.55441.05530.36090.038*
C70.7284 (4)0.8995 (4)0.45640 (19)0.0307 (7)
H70.78730.97900.50330.037*
C80.7213 (4)0.7382 (4)0.48037 (18)0.0298 (7)
C90.6281 (4)0.6011 (4)0.41395 (19)0.0307 (7)
H90.48390.59190.41900.037*
C100.6365 (4)0.6465 (4)0.30899 (18)0.0265 (6)
C110.7360 (4)0.4441 (4)0.45954 (19)0.0327 (7)
H11A0.64130.34830.45620.039*
H11B0.84520.41170.42630.039*
C120.8213 (4)0.6600 (4)0.5705 (2)0.0337 (7)
C130.3243 (4)1.0323 (4)0.1838 (2)0.0392 (8)
H13A0.21831.00400.21870.059*
H13B0.26431.05810.11730.059*
H13C0.39881.13090.21320.059*
C140.6407 (4)0.9339 (4)0.1383 (2)0.0362 (7)
H14A0.73880.99990.18300.054*
H14B0.58771.00270.08210.054*
H14C0.70570.83300.11870.054*
C150.8545 (3)0.6492 (4)0.29435 (18)0.0310 (7)
H15A0.91300.53620.30630.047*
H15B0.93220.73000.33870.047*
H15C0.85730.68290.22870.047*
C160.1016 (4)0.7681 (4)0.01206 (18)0.0278 (6)
C170.0738 (4)0.8303 (4)0.11191 (18)0.0316 (7)
H17A0.04020.77200.15120.047*
H17B0.19530.80770.13710.047*
H17C0.04800.95210.11320.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0408 (11)0.0408 (15)0.0292 (11)0.0011 (10)0.0044 (8)0.0066 (10)
O20.0573 (12)0.0554 (15)0.0253 (10)0.0093 (13)0.0034 (9)0.0001 (11)
O30.0265 (9)0.0368 (13)0.0257 (9)0.0003 (9)0.0004 (7)0.0002 (8)
O40.0322 (10)0.0568 (15)0.0349 (12)0.0113 (11)0.0003 (8)0.0074 (11)
C10.0292 (13)0.0250 (16)0.0326 (15)0.0013 (12)0.0048 (12)0.0010 (13)
C20.0299 (13)0.0237 (17)0.0280 (14)0.0027 (13)0.0007 (11)0.0022 (13)
C30.0267 (12)0.0302 (17)0.0241 (14)0.0004 (13)0.0033 (10)0.0004 (13)
C40.0268 (12)0.0263 (16)0.0285 (15)0.0013 (12)0.0016 (11)0.0007 (13)
C50.0261 (12)0.0241 (16)0.0304 (15)0.0042 (12)0.0024 (11)0.0016 (13)
C60.0319 (13)0.0263 (17)0.0344 (15)0.0033 (13)0.0024 (12)0.0024 (13)
C70.0280 (14)0.0361 (19)0.0267 (14)0.0001 (13)0.0018 (11)0.0081 (14)
C80.0258 (13)0.0349 (19)0.0282 (15)0.0021 (13)0.0045 (11)0.0008 (14)
C90.0291 (12)0.0287 (17)0.0335 (15)0.0016 (13)0.0045 (11)0.0007 (13)
C100.0282 (12)0.0260 (16)0.0239 (13)0.0017 (12)0.0015 (10)0.0026 (12)
C110.0309 (14)0.0364 (19)0.0293 (15)0.0038 (14)0.0021 (12)0.0019 (13)
C120.0314 (14)0.043 (2)0.0285 (15)0.0039 (14)0.0095 (12)0.0001 (14)
C130.0440 (15)0.0298 (18)0.0390 (17)0.0096 (14)0.0038 (13)0.0043 (14)
C140.0384 (14)0.0350 (19)0.0325 (14)0.0072 (13)0.0000 (12)0.0020 (13)
C150.0294 (12)0.0306 (17)0.0325 (14)0.0012 (13)0.0045 (11)0.0027 (14)
C160.0271 (13)0.0242 (16)0.0299 (14)0.0004 (12)0.0003 (11)0.0063 (12)
C170.0316 (13)0.0296 (17)0.0300 (15)0.0028 (13)0.0034 (11)0.0010 (13)
Geometric parameters (Å, º) top
O1—C121.369 (4)C7—C81.326 (4)
O1—C111.466 (3)C7—H70.9500
O2—C121.207 (3)C8—C121.472 (4)
O3—C161.346 (3)C8—C91.499 (4)
O3—C31.464 (3)C9—C111.525 (4)
O4—C161.201 (3)C9—C101.555 (4)
C1—C21.532 (3)C9—H91.0000
C1—C101.536 (4)C10—C151.537 (3)
C1—H1A0.9900C11—H11A0.9900
C1—H1B0.9900C11—H11B0.9900
C2—C31.511 (4)C13—H13A0.9800
C2—H2A0.9900C13—H13B0.9800
C2—H2B0.9900C13—H13C0.9800
C3—C41.540 (4)C14—H14A0.9800
C3—H31.0000C14—H14B0.9800
C4—C131.544 (4)C14—H14C0.9800
C4—C141.534 (4)C15—H15A0.9800
C4—C51.555 (4)C15—H15B0.9800
C5—C61.544 (4)C15—H15C0.9800
C5—C101.556 (4)C16—C171.488 (4)
C5—H51.0000C17—H17A0.9800
C6—C71.492 (4)C17—H17B0.9800
C6—H6A0.9900C17—H17C0.9800
C6—H6B0.9900
C12—O1—C11110.4 (2)C11—C9—C10119.8 (2)
C16—O3—C3118.3 (2)C8—C9—H9107.9
C2—C1—C10113.0 (2)C11—C9—H9107.9
C2—C1—H1A109.0C10—C9—H9107.9
C10—C1—H1A109.0C1—C10—C15110.7 (2)
C2—C1—H1B109.0C1—C10—C9107.8 (2)
C10—C1—H1B109.0C15—C10—C9110.6 (2)
H1A—C1—H1B107.8C1—C10—C5109.84 (19)
C3—C2—C1109.2 (2)C15—C10—C5113.0 (2)
C3—C2—H2A109.8C9—C10—C5104.7 (2)
C1—C2—H2A109.8O1—C11—C9106.3 (2)
C3—C2—H2B109.8O1—C11—H11A110.5
C1—C2—H2B109.8C9—C11—H11A110.5
H2A—C2—H2B108.3O1—C11—H11B110.5
O3—C3—C2108.4 (2)C9—C11—H11B110.5
O3—C3—C4107.8 (2)H11A—C11—H11B108.7
C2—C3—C4114.20 (19)O2—C12—O1121.1 (3)
O3—C3—H3108.8O2—C12—C8130.3 (3)
C2—C3—H3108.8O1—C12—C8108.6 (2)
C4—C3—H3108.8C4—C13—H13A109.5
C14—C4—C3110.8 (2)C4—C13—H13B109.5
C13—C4—C14108.1 (2)H13A—C13—H13B109.5
C3—C4—C13107.4 (2)C4—C13—H13C109.5
C14—C4—C5115.4 (2)H13A—C13—H13C109.5
C3—C4—C5106.3 (2)H13B—C13—H13C109.5
C13—C4—C5108.6 (2)C4—C14—H14A109.5
C6—C5—C4112.8 (2)C4—C14—H14B109.5
C6—C5—C10112.05 (19)H14A—C14—H14B109.5
C4—C5—C10116.8 (2)C4—C14—H14C109.5
C6—C5—H5104.6H14A—C14—H14C109.5
C4—C5—H5104.6H14B—C14—H14C109.5
C10—C5—H5104.6C10—C15—H15A109.5
C7—C6—C5113.6 (3)C10—C15—H15B109.5
C7—C6—H6A108.8H15A—C15—H15B109.5
C5—C6—H6A108.8C10—C15—H15C109.5
C7—C6—H6B108.8H15A—C15—H15C109.5
C5—C6—H6B108.8H15B—C15—H15C109.5
H6A—C6—H6B107.7O4—C16—O3123.7 (2)
C8—C7—C6121.7 (3)O4—C16—C17125.6 (2)
C8—C7—H7119.1O3—C16—C17110.7 (2)
C6—C7—H7119.1C16—C17—H17A109.5
C7—C8—C12126.7 (3)C16—C17—H17B109.5
C7—C8—C9124.4 (3)H17A—C17—H17B109.5
C12—C8—C9108.5 (3)C16—C17—H17C109.5
C8—C9—C11102.2 (2)H17A—C17—H17C109.5
C8—C9—C10110.7 (2)H17B—C17—H17C109.5
C10—C1—C2—C356.9 (3)C2—C1—C10—C1574.8 (3)
C16—O3—C3—C2107.0 (2)C2—C1—C10—C9164.1 (2)
C16—O3—C3—C4128.9 (2)C2—C1—C10—C550.6 (3)
C1—C2—C3—O3178.54 (19)C8—C9—C10—C1172.3 (2)
C1—C2—C3—C461.2 (3)C11—C9—C10—C169.3 (3)
O3—C3—C4—C1366.7 (3)C8—C9—C10—C1566.6 (3)
C2—C3—C4—C13172.7 (2)C11—C9—C10—C1551.8 (3)
O3—C3—C4—C1451.1 (3)C8—C9—C10—C555.4 (3)
C2—C3—C4—C1469.5 (3)C11—C9—C10—C5173.8 (2)
O3—C3—C4—C5177.18 (19)C6—C5—C10—C1178.4 (2)
C2—C3—C4—C556.6 (3)C4—C5—C10—C149.4 (3)
C14—C4—C5—C659.5 (3)C6—C5—C10—C1557.5 (3)
C3—C4—C5—C6177.2 (2)C4—C5—C10—C1574.7 (3)
C13—C4—C5—C661.9 (3)C6—C5—C10—C962.9 (3)
C14—C4—C5—C1072.3 (3)C4—C5—C10—C9164.9 (2)
C3—C4—C5—C1050.9 (3)C12—O1—C11—C917.0 (3)
C13—C4—C5—C10166.2 (2)C8—C9—C11—O120.2 (3)
C4—C5—C6—C7173.6 (2)C10—C9—C11—O1142.9 (2)
C10—C5—C6—C739.4 (3)C11—O1—C12—O2173.0 (2)
C5—C6—C7—C87.1 (4)C11—O1—C12—C86.0 (3)
C6—C7—C8—C12170.7 (2)C7—C8—C12—O213.2 (5)
C6—C7—C8—C91.6 (4)C9—C8—C12—O2173.5 (3)
C7—C8—C9—C11156.4 (3)C7—C8—C12—O1165.6 (3)
C12—C8—C9—C1117.1 (3)C9—C8—C12—O17.6 (3)
C7—C8—C9—C1027.8 (4)C3—O3—C16—O42.5 (4)
C12—C8—C9—C10145.7 (2)C3—O3—C16—C17177.2 (2)

Experimental details

(I)(II)
Crystal data
Chemical formulaC15H22O3·0.5H2OC17H24O4
Mr259.33292.36
Crystal system, space groupMonoclinic, P21Monoclinic, P21
Temperature (K)120120
a, b, c (Å)12.875 (3), 6.153 (2), 18.268 (4)6.802 (3), 7.918 (4), 14.302 (8)
β (°) 106.031 (16) 101.22 (2)
V3)1390.9 (6)755.6 (7)
Z42
Radiation typeMo KαMo Kα
µ (mm1)0.090.09
Crystal size (mm)0.42 × 0.35 × 0.200.33 × 0.18 × 0.15
Data collection
DiffractometerNonius KappaCCD area-detector (with Oxford Cryostream)
diffractometer
Nonius KappaCCD area-detector (with Oxford Cryostream)
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
17077, 5214, 3773 8695, 2353, 1456
Rint0.0400.057
(sin θ/λ)max1)0.7460.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.112, 1.04 0.051, 0.108, 0.98
No. of reflections52142353
No. of parameters353195
No. of restraints11
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.230.22, 0.20

Computer programs: COLLECT (Nonius, 1999), HKL SCALEPACK (Otwinowski & Minor 1997), HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) for (I) top
O1A—C12A1.342 (3)O2B—C12B1.203 (2)
O2A—C12A1.220 (2)O3B—C3B1.437 (2)
C7A—C8A1.314 (3)C7B—C8B1.322 (3)
C10A—C1A—C2A—C3A58.2 (2)C10B—C1B—C2B—C3B57.0 (2)
C1A—C2A—C3A—C4A61.9 (2)C1B—C2B—C3B—C4B59.2 (3)
C2A—C3A—C4A—C5A55.2 (2)C2B—C3B—C4B—C5B53.4 (2)
C3A—C4A—C5A—C10A48.4 (2)C3B—C4B—C5B—C10B49.0 (2)
C10A—C5A—C6A—C7A42.8 (3)C10B—C5B—C6B—C7B42.0 (3)
C5A—C6A—C7A—C8A7.3 (3)C5B—C6B—C7B—C8B8.2 (3)
C6A—C7A—C8A—C9A3.0 (4)C6B—C7B—C8B—C9B0.5 (4)
C12A—C8A—C9A—C11A21.9 (2)C12B—C8B—C9B—C11B20.3 (2)
C7A—C8A—C9A—C10A22.6 (3)C7B—C8B—C9B—C10B24.9 (3)
C2A—C1A—C10A—C5A49.5 (2)C2B—C1B—C10B—C5B50.3 (2)
C8A—C9A—C10A—C5A53.8 (2)C8B—C9B—C10B—C5B54.40 (19)
C4A—C5A—C10A—C1A46.5 (2)C4B—C5B—C10B—C1B48.1 (2)
C6A—C5A—C10A—C9A65.3 (2)C6B—C5B—C10B—C9B64.1 (2)
C12A—O1A—C11A—C9A19.5 (2)C12B—O1B—C11B—C9B20.1 (2)
C8A—C9A—C11A—O1A24.7 (2)C8B—C9B—C11B—O1B23.8 (2)
C11A—O1A—C12A—C8A5.3 (2)C11B—O1B—C12B—C8B7.1 (3)
C9A—C8A—C12A—O1A11.4 (2)C9B—C8B—C12B—O1B9.3 (2)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O3A—H3OA···O1Wi0.86 (3)1.79 (3)2.632 (3)164 (3)
O3B—H3OB···O3Aii0.82 (3)1.83 (4)2.641 (2)168 (3)
O1W—H1W···O2A0.90 (3)1.90 (3)2.791 (2)169 (3)
O1W—H2W···O3Biii0.88 (4)1.83 (4)2.694 (3)166 (3)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x, y+1, z.
Selected geometric parameters (Å, º) for (II) top
O2—C121.207 (3)C7—C81.326 (4)
O4—C161.201 (3)
C10—C1—C2—C356.9 (3)C2—C1—C10—C550.6 (3)
C1—C2—C3—C461.2 (3)C8—C9—C10—C555.4 (3)
C2—C3—C4—C556.6 (3)C4—C5—C10—C149.4 (3)
C3—C4—C5—C1050.9 (3)C6—C5—C10—C962.9 (3)
C10—C5—C6—C739.4 (3)C12—O1—C11—C917.0 (3)
C5—C6—C7—C87.1 (4)C8—C9—C11—O120.2 (3)
C6—C7—C8—C91.6 (4)C11—O1—C12—C86.0 (3)
C12—C8—C9—C1117.1 (3)C9—C8—C12—O17.6 (3)
C7—C8—C9—C1027.8 (4)
 

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