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The ent-kaurene diterpene in the title compound, 7-epican­dicandiol ethanol solvate, C20H32O2·C2H6O, was isolated from the aerial parts of Sideritis ozturkii Aytaç & Aksoy. The mol­ecule has the usual conformation and stereochemistry found in related ent-kaurene derivatives. The methyl-substituted ring junction has a trans arrangement and the other junction is cis. The six-membered rings have chair or slightly distorted chair conformations and the five-membered ring has an envelope conformation. Inter­molecular hydrogen bonds link the 7-epicandicandiol and ethanol mol­ecules into two-dimensional networks, part of which comprise co-operative O—H...O—H...O—H... chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106008638/fg3006sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106008638/fg3006Isup2.hkl
Contains datablock I

CCDC reference: 609414

Comment top

The genus Sideritis L., of which 46 species are found in Turkey (Huber-Morath, 1982; Davis et al., 1988; Aytaç & Aksoy, 2000; Duman, 2000), is recognized as a rich source of biologically active diterpenoids and flavonoids. Our previous chemical studies of the aerial parts of a local endemic species, Sideritis ozturkii Aytaç & Aksoy, led to the isolation of ent-kaurene-type diterpenoids and flavonoids, as well as phenylethanoid glycosides. Among these, two diterpenes were identified on the basis of their spectroscopic data (MS, and one- and two-dimensional NMR) as the known compounds linearol and 7-epicandicandiol (Şahin et al., 2004, 2005). The crystal structure of linearol has been reported previously (Ergin et al., 1993; Hökelek et al., 1999), although in the latter report the inverse enantiomer was employed for the structure refinement model and the chemical diagram shows the incorrect stereochemistry at atom C4. The crystal structure of 7-epicandicandiol, (I), reported here, was determined in order to confirm the stereochemistry and molecular structure of the compound.

The molecular structure of compound (I) is shown in Fig. 1. The compound crystallizes from ethanol as its 1:1 e thanol solvate. All bond lengths and angles fall within normal ranges. The absolute configuration has not been determined, but was assigned to correspond with that usually depicted for 7-epicandicandiol and related ent-kaurenes. The crystal structures of 57 kaurene derivatives are reported in the Cambridge Structural Database (CSD; Release 5.27 with January 2006 updates; Allen, 2002). Of these, only the structure of (4α)-kaur-16-en-18-carbonyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (Mora et al., 2004) represents a definitive absolute configuration determination because of the known configuration of the α-D-glucopyranoside substituent. It is assumed that this structure establishes the absolute configuration of the core of this class of compounds. Although the configuration at the glucopyranoside-substituted C atom is opposite to that of the corresponding C atom in (I) and the hydroxy group at the 7-position is absent, the configurations of the remainder of the stereogenic centres correspond with those hitherto depicted for ent-kaurenes and also with those in (I).

The reported crystal structures of compounds most similar to (I) are those of epicandicandiol diacetate (ent-7α,18-diacetoxykaur-16-ene), which was synthesized directly from epicandicandiol (Hökelek et al., 2001), methyl ent-7α-hydroxykaur-16-en-19-oate (Le Quesne et al., 1985; Baynham et al., 1988) and (-)-ent-3β,7α-dihydroxy-18-acetoxykaur-16-ene (linearol; Ergin et al., 1993; Hökelek et al., 1999). The ring conformations in each of these structures are very similar to those observed in the structure of (I). The ring junction AB in (I) is trans, while BC is cis (see scheme). Rings A and B have almost normal chair conformations, with ring B being the more distorted, as shown by the puckering parameter (Cremer & Pople, 1975), θ, which has values of 176.7 (3) and 167.3 (3)° for the atom sequences C1–C5/C10 and C5–C10, respectively. The hydroxymethyl substituent at C4 in ring A lies in an equatorial position, while the hydroxy substituent at C7 ring B adopts an axial position. The conformation of ring C is that of a slightly more twisted chair, as a result of atoms C8, C13 and C14 also being part of the five-membered ring. For ring C, the puckering parameter Q is 0.631 (3) Å, θ is 23.7 (3)° and ϕ2 is 287.8 (8)° for the atom sequence C8–C10/C12–C14. The five-membered ring, D, has an envelope conformation, with atom C14 as the envelope flap and a value for the ϕ2 puckering parameter of 29.4 (4)° for the atom sequence C8/C14/C13/C16/C15. Atom C14 lies 0.687 (3) Å from the plane defined by the remaining four atoms of the ring.

It has been noted previously (Karle, 1972) that steric crowding of the methyl substituent at the AB ring junction by other substituents in axial or pseudo-axial positions, namely atoms C12, C14 and C19 in (I), causes convex buckling of the molecular plane so as to allow these substituents more room. Similar to the observations of Karle and the corresponding intramolecular distances quoted for the above-mentioned related compounds, the buckling has relieved the crowding at C20 in (I) and there are no intramolecular distances involving C20 that are less than 3.2 Å [C19···C20 = 3.214 (4) Å].

The H atom of the hydroxy substituent on the central six-membered ring, B, forms an intermolecular hydrogen bond with the O atom of the ethanol molecule (Table 1). In turn, the hydroxy H atom of the ethanol molecule forms an intermolecular hydrogen bond with the O atom of the hydroxymethyl substituent in ring A of a different neighbouring 7-epicandicandiol molecule. These two interactions link the ethanol and 7-epicandicandiol molecules in an alternating fashion into extended chains which run parallel to the [100] direction and can be described by a binary graph-set motif (Bernstein et al., 1995) of C22(10). The hydroxy H atom of the hydroxymethyl substituent forms its own intermolecular hydrogen bond with the hydroxy O atom on ring B of another neighbouring molecule. This interaction links the 7-epicandicandiol molecules into extended chains which also run parallel to the [100] direction and can be described by a graph-set motif of C(8). The combination of all hydrogen-bonding interactions links all the moieties in the structure into two-dimensional networks which lie parallel to the (001) plane. In addition, the three structurally different hydroxy groups form a cooperative O—H···O—H···O—H··· chain which runs parallel to the [010] direction (Fig. 2) and can be described by a ternary graph-set motif of C33(6).

Experimental top

The title compound was isolated from Sideritis ozturkii Aytaç & Aksoy as described by Şahin et al. (2004, 2005). Suitable crystals were obtained by slow evaporation of a solution of the compound in ethanol (m.p. 316 K).

Refinement top

The hydroxy H atoms were located in a difference Fourier map and their positions were refined freely along with individual isotropic displacement parameters. The methyl H atoms were constrained to an ideal geometry (C—H = 0.98 Å) with Uiso(H) = 1.5Ueq(C), but were allowed to rotate freely about the C—C bonds. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.99–1.00 Å and with Uiso(H) = 1.2Ueq(C). As there are no significant anomalous dispersion effects with this compound, Friedel opposites were merged prior to the final cycles of refinement. The enantiomer used in the refinement model was chosen so as to correspond with that usually depicted for 7-epicandicandiol, although there does not appear to have been a definitive determination of the absolute configuration of this compound. Two low-angle reflections were omitted from the final cycles of refinement because their observed intensities were much lower than the calculated values, as a result of being partially obscured by the beam stop.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented by circles of arbitrary size.
[Figure 2] Fig. 2. The crystal packing in (I), viewed along the a axis, showing the cooperative O—H···O—H···O—H.. chain. Most of the H atoms have been omitted for clarity. Hydrogen bonds are represented by thin lines.
ent-7α,18-hydroxykaur-16-ene ethanol solvate top
Crystal data top
C20H32O2·C2H6ODx = 1.153 Mg m3
Mr = 350.54Melting point: 316 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3806 reflections
a = 12.3391 (2) Åθ = 2.0–25.0°
b = 7.1780 (1) ŵ = 0.07 mm1
c = 22.8065 (4) ÅT = 160 K
V = 2019.97 (6) Å3Needle, colourless
Z = 40.30 × 0.12 × 0.12 mm
F(000) = 776
Data collection top
Nonius KappaCCD area-detector
diffractometer
1714 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generatorRint = 0.062
Horizontally mounted graphite crystal monochromatorθmax = 25.0°, θmin = 3.2°
Detector resolution: 9 pixels mm-1h = 1414
ϕ and ω scans with κ offsetsk = 88
20732 measured reflectionsl = 2727
2049 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: geom & difmap
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0544P)2 + 0.8216P]
where P = (Fo2 + 2Fc2)/3
2047 reflections(Δ/σ)max = 0.001
241 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C20H32O2·C2H6OV = 2019.97 (6) Å3
Mr = 350.54Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 12.3391 (2) ŵ = 0.07 mm1
b = 7.1780 (1) ÅT = 160 K
c = 22.8065 (4) Å0.30 × 0.12 × 0.12 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
1714 reflections with I > 2σ(I)
20732 measured reflectionsRint = 0.062
2049 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.50 e Å3
2047 reflectionsΔρmin = 0.26 e Å3
241 parameters
Special details top

Experimental. Solvent used: EtOH Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.430 (1) Frames collected: 1259 Seconds exposure per frame: 12 Degrees rotation per frame: 0.6 Crystal-Detector distance (mm): 60.0

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O70.28434 (17)0.4568 (3)0.45928 (9)0.0302 (5)
H70.297 (3)0.547 (6)0.4802 (16)0.052 (12)*
O180.73419 (18)0.3827 (3)0.49115 (11)0.0396 (6)
H180.744 (3)0.280 (6)0.5079 (16)0.046 (11)*
C10.4736 (2)0.0177 (4)0.36140 (13)0.0281 (7)
H110.43590.06330.39690.034*
H120.45200.09840.32820.034*
C20.5957 (2)0.0346 (4)0.37061 (13)0.0317 (7)
H210.61400.16570.37970.038*
H220.63350.00000.33390.038*
C30.6351 (3)0.0899 (4)0.42019 (13)0.0314 (7)
H310.71490.07990.42300.038*
H320.60420.04430.45760.038*
C40.6041 (2)0.2968 (4)0.41226 (12)0.0275 (7)
C50.4798 (2)0.3087 (4)0.39962 (12)0.0237 (6)
H50.44430.25840.43570.028*
C60.4363 (2)0.5080 (4)0.39359 (12)0.0259 (6)
H610.47000.58820.42380.031*
H620.45630.55820.35460.031*
C70.3136 (2)0.5123 (4)0.40054 (11)0.0248 (6)
H710.28810.64300.39410.030*
C80.2562 (2)0.3857 (4)0.35657 (12)0.0266 (6)
C90.3097 (2)0.1889 (4)0.35231 (11)0.0252 (6)
H90.29200.12700.39040.030*
C100.4365 (2)0.1842 (4)0.34865 (11)0.0240 (6)
C110.2507 (3)0.0704 (4)0.30520 (13)0.0325 (7)
H1110.30050.02980.29240.039*
H1120.18750.00980.32400.039*
C120.2107 (3)0.1736 (5)0.25040 (14)0.0402 (8)
H1210.15630.09600.22990.048*
H1220.27230.19380.22330.048*
C130.1599 (3)0.3623 (4)0.26623 (14)0.0401 (8)
H130.12800.42620.23130.048*
C140.2466 (3)0.4805 (4)0.29611 (13)0.0332 (7)
H1410.22320.61190.29990.040*
H1420.31610.47570.27440.040*
C150.1345 (2)0.3606 (4)0.37099 (14)0.0352 (7)
H1510.12370.25040.39640.042*
H1520.10630.47190.39160.042*
C160.0778 (3)0.3351 (5)0.31455 (15)0.0396 (8)
C170.0271 (3)0.2887 (5)0.30631 (19)0.0555 (10)
H1710.07300.26860.33910.067*
H1720.05490.27600.26770.067*
C180.6243 (2)0.3944 (4)0.47127 (13)0.0345 (7)
H1810.60410.52730.46750.041*
H1820.57640.33810.50130.041*
C190.6766 (2)0.3900 (5)0.36582 (14)0.0348 (7)
H1910.64510.51010.35450.052*
H1920.68150.30940.33120.052*
H1930.74910.40990.38210.052*
C200.4787 (2)0.2393 (4)0.28739 (12)0.0303 (7)
H2010.55420.19900.28320.045*
H2020.47450.37490.28280.045*
H2030.43430.17910.25720.045*
O230.3378 (2)0.7829 (4)0.51716 (12)0.0541 (7)
H230.311 (3)0.884 (7)0.5087 (19)0.067 (14)*
C210.4442 (5)0.6650 (8)0.5941 (2)0.104 (2)
H2110.38380.66000.62190.155*
H2120.51180.68860.61530.155*
H2130.44950.54600.57320.155*
C220.4260 (4)0.8097 (6)0.5534 (2)0.0819 (15)
H2210.41580.92760.57520.098*
H2220.49160.82380.52880.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O70.0406 (12)0.0252 (11)0.0248 (10)0.0022 (10)0.0072 (9)0.0034 (10)
O180.0406 (13)0.0267 (12)0.0515 (14)0.0024 (10)0.0157 (11)0.0040 (11)
C10.0396 (16)0.0174 (14)0.0273 (15)0.0021 (13)0.0020 (13)0.0004 (12)
C20.0398 (17)0.0193 (14)0.0361 (16)0.0054 (13)0.0036 (14)0.0001 (14)
C30.0324 (16)0.0261 (15)0.0357 (17)0.0050 (14)0.0012 (13)0.0026 (13)
C40.0327 (16)0.0213 (14)0.0284 (15)0.0002 (13)0.0025 (12)0.0007 (12)
C50.0306 (15)0.0176 (13)0.0229 (14)0.0002 (12)0.0035 (12)0.0006 (12)
C60.0340 (16)0.0178 (14)0.0260 (14)0.0019 (12)0.0015 (12)0.0006 (12)
C70.0299 (15)0.0199 (14)0.0246 (14)0.0016 (12)0.0046 (12)0.0011 (12)
C80.0309 (15)0.0211 (14)0.0278 (15)0.0008 (13)0.0019 (12)0.0018 (12)
C90.0341 (15)0.0178 (14)0.0237 (14)0.0003 (12)0.0024 (12)0.0007 (12)
C100.0306 (15)0.0173 (14)0.0243 (14)0.0030 (12)0.0041 (12)0.0008 (12)
C110.0366 (16)0.0239 (15)0.0371 (17)0.0008 (14)0.0009 (14)0.0059 (13)
C120.0447 (19)0.0364 (18)0.0395 (18)0.0010 (16)0.0075 (15)0.0082 (16)
C130.0485 (19)0.0345 (18)0.0373 (18)0.0029 (16)0.0113 (15)0.0011 (15)
C140.0432 (17)0.0251 (15)0.0312 (16)0.0041 (14)0.0034 (14)0.0016 (13)
C150.0345 (17)0.0269 (16)0.0441 (18)0.0043 (14)0.0007 (14)0.0054 (14)
C160.0397 (18)0.0293 (17)0.050 (2)0.0045 (14)0.0070 (16)0.0044 (16)
C170.040 (2)0.048 (2)0.079 (3)0.0033 (19)0.0157 (19)0.011 (2)
C180.0357 (16)0.0296 (16)0.0381 (18)0.0001 (14)0.0054 (14)0.0013 (14)
C190.0326 (16)0.0293 (16)0.0424 (18)0.0020 (14)0.0050 (14)0.0026 (15)
C200.0402 (16)0.0237 (15)0.0270 (15)0.0020 (13)0.0037 (13)0.0001 (13)
O230.0654 (17)0.0310 (14)0.0658 (18)0.0079 (13)0.0160 (14)0.0134 (13)
C210.142 (5)0.107 (4)0.061 (3)0.037 (4)0.036 (3)0.025 (3)
C220.079 (3)0.052 (3)0.115 (4)0.012 (2)0.042 (3)0.019 (3)
Geometric parameters (Å, º) top
O7—C71.444 (3)C11—H1110.9900
O7—H70.82 (4)C11—H1120.9900
O18—C181.433 (4)C12—C131.535 (4)
O18—H180.84 (4)C12—H1210.9900
C1—C21.525 (4)C12—H1220.9900
C1—C101.548 (4)C13—C161.510 (5)
C1—H110.9900C13—C141.526 (4)
C1—H120.9900C13—H131.0000
C2—C31.521 (4)C14—H1410.9900
C2—H210.9900C14—H1420.9900
C2—H220.9900C15—C161.476 (4)
C3—C41.544 (4)C15—H1510.9900
C3—H310.9900C15—H1520.9900
C3—H320.9900C16—C171.349 (5)
C4—C181.537 (4)C17—H1710.9500
C4—C191.539 (4)C17—H1720.9500
C4—C51.564 (4)C18—H1810.9900
C5—C61.534 (4)C18—H1820.9900
C5—C101.560 (4)C19—H1910.9800
C5—H51.0000C19—H1920.9800
C6—C71.523 (4)C19—H1930.9800
C6—H610.9900C20—H2010.9800
C6—H620.9900C20—H2020.9800
C7—C81.528 (4)C20—H2030.9800
C7—H711.0000O23—C221.380 (5)
C8—C141.542 (4)O23—H230.82 (5)
C8—C151.548 (4)C21—C221.410 (6)
C8—C91.563 (4)C21—H2110.9800
C9—C111.552 (4)C21—H2120.9800
C9—C101.567 (4)C21—H2130.9800
C9—H91.0000C22—H2210.9900
C10—C201.543 (4)C22—H2220.9900
C11—C121.535 (4)
C7—O7—H7106 (3)C12—C11—H112108.1
C18—O18—H18110 (2)C9—C11—H112108.1
C2—C1—C10113.1 (2)H111—C11—H112107.3
C2—C1—H11109.0C11—C12—C13111.5 (3)
C10—C1—H11109.0C11—C12—H121109.3
C2—C1—H12109.0C13—C12—H121109.3
C10—C1—H12109.0C11—C12—H122109.3
H11—C1—H12107.8C13—C12—H122109.3
C3—C2—C1111.8 (2)H121—C12—H122108.0
C3—C2—H21109.3C16—C13—C14102.5 (3)
C1—C2—H21109.3C16—C13—C12109.3 (3)
C3—C2—H22109.3C14—C13—C12108.0 (3)
C1—C2—H22109.3C16—C13—H13112.2
H21—C2—H22107.9C14—C13—H13112.2
C2—C3—C4113.5 (2)C12—C13—H13112.2
C2—C3—H31108.9C13—C14—C8102.0 (2)
C4—C3—H31108.9C13—C14—H141111.4
C2—C3—H32108.9C8—C14—H141111.4
C4—C3—H32108.9C13—C14—H142111.4
H31—C3—H32107.7C8—C14—H142111.4
C18—C4—C19108.1 (2)H141—C14—H142109.2
C18—C4—C3107.2 (2)C16—C15—C8106.8 (3)
C19—C4—C3110.8 (3)C16—C15—H151110.4
C18—C4—C5107.2 (2)C8—C15—H151110.4
C19—C4—C5114.8 (2)C16—C15—H152110.4
C3—C4—C5108.5 (2)C8—C15—H152110.4
C6—C5—C10110.3 (2)H151—C15—H152108.6
C6—C5—C4114.2 (2)C17—C16—C15127.3 (3)
C10—C5—C4116.2 (2)C17—C16—C13125.0 (3)
C6—C5—H5104.9C15—C16—C13107.6 (3)
C10—C5—H5104.9C16—C17—H171120.0
C4—C5—H5104.9C16—C17—H172120.0
C7—C6—C5110.9 (2)H171—C17—H172120.0
C7—C6—H61109.5O18—C18—C4113.8 (2)
C5—C6—H61109.5O18—C18—H181108.8
C7—C6—H62109.5C4—C18—H181108.8
C5—C6—H62109.5O18—C18—H182108.8
H61—C6—H62108.0C4—C18—H182108.8
O7—C7—C6109.8 (2)H181—C18—H182107.7
O7—C7—C8109.2 (2)C4—C19—H191109.5
C6—C7—C8112.4 (2)C4—C19—H192109.5
O7—C7—H71108.4H191—C19—H192109.5
C6—C7—H71108.4C4—C19—H193109.5
C8—C7—H71108.4H191—C19—H193109.5
C7—C8—C14111.1 (2)H192—C19—H193109.5
C7—C8—C15112.3 (2)C10—C20—H201109.5
C14—C8—C1599.6 (2)C10—C20—H202109.5
C7—C8—C9112.5 (2)H201—C20—H202109.5
C14—C8—C9112.1 (2)C10—C20—H203109.5
C15—C8—C9108.6 (2)H201—C20—H203109.5
C11—C9—C8109.9 (2)H202—C20—H203109.5
C11—C9—C10114.8 (2)C22—O23—H23110 (3)
C8—C9—C10116.4 (2)C22—C21—H211109.5
C11—C9—H9104.8C22—C21—H212109.5
C8—C9—H9104.8H211—C21—H212109.5
C10—C9—H9104.8C22—C21—H213109.5
C20—C10—C1108.1 (2)H211—C21—H213109.5
C20—C10—C5114.3 (2)H212—C21—H213109.5
C1—C10—C5107.1 (2)O23—C22—C21114.6 (4)
C20—C10—C9112.3 (2)O23—C22—H221108.6
C1—C10—C9107.8 (2)C21—C22—H221108.6
C5—C10—C9106.9 (2)O23—C22—H222108.6
C12—C11—C9116.8 (2)C21—C22—H222108.6
C12—C11—H111108.1H221—C22—H222107.6
C9—C11—H111108.1
C10—C1—C2—C357.3 (3)C6—C5—C10—C1174.1 (2)
C1—C2—C3—C455.3 (3)C4—C5—C10—C153.8 (3)
C2—C3—C4—C18166.6 (2)C6—C5—C10—C958.8 (3)
C2—C3—C4—C1975.7 (3)C4—C5—C10—C9169.1 (2)
C2—C3—C4—C551.2 (3)C11—C9—C10—C2054.5 (3)
C18—C4—C5—C661.8 (3)C8—C9—C10—C2075.9 (3)
C19—C4—C5—C658.2 (3)C11—C9—C10—C164.5 (3)
C3—C4—C5—C6177.3 (2)C8—C9—C10—C1165.1 (2)
C18—C4—C5—C10167.9 (2)C11—C9—C10—C5179.3 (2)
C19—C4—C5—C1072.1 (3)C8—C9—C10—C550.3 (3)
C3—C4—C5—C1052.4 (3)C8—C9—C11—C1236.5 (3)
C10—C5—C6—C764.6 (3)C10—C9—C11—C1297.0 (3)
C4—C5—C6—C7162.2 (2)C9—C11—C12—C1341.8 (4)
C5—C6—C7—O764.8 (3)C11—C12—C13—C1650.2 (3)
C5—C6—C7—C857.0 (3)C11—C12—C13—C1460.6 (3)
O7—C7—C8—C14157.5 (2)C16—C13—C14—C842.6 (3)
C6—C7—C8—C1480.3 (3)C12—C13—C14—C872.8 (3)
O7—C7—C8—C1546.9 (3)C7—C8—C14—C13163.3 (2)
C6—C7—C8—C15169.1 (2)C15—C8—C14—C1344.8 (3)
O7—C7—C8—C975.9 (3)C9—C8—C14—C1369.9 (3)
C6—C7—C8—C946.2 (3)C7—C8—C15—C16148.6 (3)
C7—C8—C9—C11177.7 (2)C14—C8—C15—C1631.0 (3)
C14—C8—C9—C1151.6 (3)C9—C8—C15—C1686.3 (3)
C15—C8—C9—C1157.4 (3)C8—C15—C16—C17172.3 (3)
C7—C8—C9—C1045.0 (3)C8—C15—C16—C135.3 (3)
C14—C8—C9—C1081.1 (3)C14—C13—C16—C17159.2 (3)
C15—C8—C9—C10169.9 (2)C12—C13—C16—C1786.3 (4)
C2—C1—C10—C2069.2 (3)C14—C13—C16—C1523.1 (3)
C2—C1—C10—C554.5 (3)C12—C13—C16—C1591.4 (3)
C2—C1—C10—C9169.1 (2)C19—C4—C18—O1860.2 (3)
C6—C5—C10—C2066.1 (3)C3—C4—C18—O1859.3 (3)
C4—C5—C10—C2066.0 (3)C5—C4—C18—O18175.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7···O230.82 (4)1.96 (4)2.767 (3)169 (4)
O18—H18···O7i0.84 (4)1.92 (4)2.757 (3)173 (4)
O23—H23···O18ii0.82 (5)1.92 (5)2.726 (3)166 (4)
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x1/2, y+3/2, z+1.

Experimental details

Crystal data
Chemical formulaC20H32O2·C2H6O
Mr350.54
Crystal system, space groupOrthorhombic, P212121
Temperature (K)160
a, b, c (Å)12.3391 (2), 7.1780 (1), 22.8065 (4)
V3)2019.97 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.30 × 0.12 × 0.12
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
20732, 2049, 1714
Rint0.062
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.112, 1.03
No. of reflections2047
No. of parameters241
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.50, 0.26

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97 and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7···O230.82 (4)1.96 (4)2.767 (3)169 (4)
O18—H18···O7i0.84 (4)1.92 (4)2.757 (3)173 (4)
O23—H23···O18ii0.82 (5)1.92 (5)2.726 (3)166 (4)
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x1/2, y+3/2, z+1.
 

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