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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o264
https://doi.org/10.1107/S1600536807064021

4-Hy­droxy-4,6a,6b,9,9,12a,14b-hepta­methylperhydropicen-3-one hemihydrate isolated from Adiantum incisum

Altaf Hussain,a Hamid Latif Siddiqui,a* Muhammad Zia-ur-Rehman,b Mark R. J. Elsegoodc and Khalid M. Khand

aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan, cChemistry Department, Loughborough University, Loughborough, Leicestershire, LE11 3TU, England, and dHEJ Research Institute of Chemistry, Karachi, Pakistan
*Correspondence e-mail: m.r.j.elsegood@lboro.ac.uk

(Received 20 November 2007; accepted 28 November 2007; online 12 December 2007)

The title compound, C29H48O2·0.5H2O, is a triterpenoid isolated from the stems and rhizomes of Adiantum incisum. The basic skeleton of the mol­ecule contains five six-membered rings, all adopting chair conformations, bearing a total of seven methyl, one hydroxyl and a keto group. There are two mol­ecules of the triterpene and one water molecule of crystallization in the asymmetric unit. The two unique triterpenoid mol­ecules hydrogen-bond directly via an O—H⋯O=C inter­action, and are also bridged by the water mol­ecule. The water also bridges to another pair of hydrogen-bonded triterpenoid mol­ecules.

Related literature

For related literature, see: Ageta et al. (1966[Ageta, H., Iwata, K. & Arai, Y. (1966). Tetrahedron Lett. 46, 5679-5684.]); Janaki et al. (1999[Janaki, S., Vijayasekaran, V., Viswanathan, S. & Balakrishna, K. (1999). J. Ethnopharmacol. 67, 45-51.]); Kshirsagar & Mehta (1972[Kshirsagar, M. K. & Mehta, A. R. (1972). Planta Med. 22, 386-390.]); Matsuda et al. (1999[Matsuda, H., Kageura, T., Toguchida, I., Murakami, T., Kishi, A. & Yoshikawa, M. (1999). Bioorg. Med. Chem. Lett. 9, 3081-3086.]); Wada et al. (1987[Wada, M., Shimizu, H. & Kondo, N. (1987). Bot. Mag. Tokyo, 100, 51-62.]).

[Scheme 1]

Experimental

Crystal data

  • C29H48O2·0.5H2O

  • Mr = 437.68

  • Monoclinic, P 21

  • a = 6.4432 (4) Å

  • b = 57.477 (8) Å

  • c = 7.2226 (6) Å

  • β = 114.725 (5)°

  • V = 2429.6 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 120 (2) K

  • 0.42 × 0.20 × 0.06 mm
Data collection

  • Bruker–Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.]) Tmin = 0.970, Tmax = 0.996

  • 12411 measured reflections

  • 3758 independent reflections

  • 2285 reflections with I > 2σ(I)

  • Rint = 0.064
Refinement

  • R[F2 > 2σ(F2)] = 0.071

  • wR(F2) = 0.147

  • S = 1.05

  • 3758 reflections

  • 584 parameters

  • 52 restraints

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O4 0.84 2.19 2.978 (8) 156
O3—H3⋯O5 0.84 2.06 2.896 (9) 176

Data collection: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). COLLECT. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000[Sheldrick, G. M. (2000). SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807064021/bt2638sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064021/bt2638Isup2.hkl

checkCIF report


Comment top

Triterpenoids represent an important class of natural products characterized by highly pronounced biological activities such as analgesic, anti-mutagenic, and anti-inflammatory (Matsuda et al. 1999; Janaki et al. 1999). Adiantum incisum, a fern, generally found in the Himalayas region is well known for its antibacterial, antiviral and antifungal activities (Kshirsagar et al. 1972; Wada et al. 1987). The plant for the present work was collected from the Murree hills of Pakistan and during its phytochemical investigations, title compound (I) was isolated and its crystal structure is being reported here for the first time. (I) has also been reported as one of the constituents of Adiantum monochlamys (Ageta et al. 1966).

The molecule (I) is shown in Fig.1 and contains five six membered rings, all adopting chair conformations, fused together in a trans fashion. All the rings at their juncture bear one methyl group while ring A has two extra methyl groups. Ring E is in a slightly distorted form due to the presence of one methyl and a hydroxyl group at one carbon, C1, and a keto group on the adjacent carbon, C2.

The arrangement of molecular units suggests that the three dimensional structure is stabilized by inter molecular hydrogen bonds. Carbonyl oxygen (O4) of one triterpenoid molecule is involved in hydrogen bonding with the hydroxyl hydrogen (H1) of the other while its hydroxyl hydrogen (H3) is H-bonded with the oxygen (O5) of the water molecule. The H atoms of the water molecule are involved in inter-molecular hydrogen bonding with hydroxyl oxygen O1 (O1···O5 = 3.009 (9) Å) and carbonyl oxygen O2i (O5···O2i = 2.834 (9) Å; symmetry operator i = x + 1, y, z + 1) of the adjacent pair of molecules making an infinite chain along [1 0 1] as shown in Figs 2 & 3.

Related literature top

For related literature, see: Ageta et al. (1966); Janaki et al. (1999); Kshirsagar & Mehta (1972); Matsuda et al. (1999); Wada et al. (1987).

Experimental top

The plant (Adiantum incisum) collected from Murree hills, Pakistan, was shade dried. The dried stems and rhizomes (2.9 kg) were dipped in ethanol for fifteen days and filtered. The filtrate was concentrated under reduced pressure to obtain the extract (51.33 g) followed by column chromatography using a gradient solvent system from hexane-chloroform-methanol. The eluted fractions were monitored by thin layer chromatography and combined to give 38 main fractions. Fraction 9 was rechromatographed on a silica-gel column with hexane-chloroform (1:1) to afford the pure title compound (I).

Refinement top

In the absence of anomalous scatterers Friedel pairs were merged and the absolute configuration of the compound was arbitrarily set. H atoms bound to C were placed in geometric positions (C—H distance = 0.99 Å for methylene; 1.00 Å for methyl H; 0.84 Å for OH) using a riding model. H atoms on the water molecules were not located in difference maps or included in the model. Uiso values were set to 1.2Ueq (1.5Ueq for methyl H and OH) of the carrier atom. The displacement parameters of the atoms C33 C36, C48, C51 and C53 were restrained to an isotropic behaviour.

Structure description top

Triterpenoids represent an important class of natural products characterized by highly pronounced biological activities such as analgesic, anti-mutagenic, and anti-inflammatory (Matsuda et al. 1999; Janaki et al. 1999). Adiantum incisum, a fern, generally found in the Himalayas region is well known for its antibacterial, antiviral and antifungal activities (Kshirsagar et al. 1972; Wada et al. 1987). The plant for the present work was collected from the Murree hills of Pakistan and during its phytochemical investigations, title compound (I) was isolated and its crystal structure is being reported here for the first time. (I) has also been reported as one of the constituents of Adiantum monochlamys (Ageta et al. 1966).

The molecule (I) is shown in Fig.1 and contains five six membered rings, all adopting chair conformations, fused together in a trans fashion. All the rings at their juncture bear one methyl group while ring A has two extra methyl groups. Ring E is in a slightly distorted form due to the presence of one methyl and a hydroxyl group at one carbon, C1, and a keto group on the adjacent carbon, C2.

The arrangement of molecular units suggests that the three dimensional structure is stabilized by inter molecular hydrogen bonds. Carbonyl oxygen (O4) of one triterpenoid molecule is involved in hydrogen bonding with the hydroxyl hydrogen (H1) of the other while its hydroxyl hydrogen (H3) is H-bonded with the oxygen (O5) of the water molecule. The H atoms of the water molecule are involved in inter-molecular hydrogen bonding with hydroxyl oxygen O1 (O1···O5 = 3.009 (9) Å) and carbonyl oxygen O2i (O5···O2i = 2.834 (9) Å; symmetry operator i = x + 1, y, z + 1) of the adjacent pair of molecules making an infinite chain along [1 0 1] as shown in Figs 2 & 3.

For related literature, see: Ageta et al. (1966); Janaki et al. (1999); Kshirsagar & Mehta (1972); Matsuda et al. (1999); Wada et al. (1987).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures top
[Figure 1] Fig. 1. Asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level, H atoms are represented by circles of arbitrary radius and hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. Close-up of the H-bonding motif in (I) showing showing the arrangement of three triterpenoid molecules H-bonded through one water molecule. Symmetry operator: i = x + 1, y, z + 1.
[Figure 3] Fig. 3. Packing plot of (I) viewed approximately along the chain propagation direction [1 0 1].
4-Hydroxy-4,6a,6 b,9,9,12a,14b-heptamethylperhydropicen-3-one hemihydrate top
Crystal data top
C29H48O2·0.5H2OF(000) = 972
Mr = 437.68Dx = 1.197 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 10245 reflections
a = 6.4432 (4) Åθ = 1.0–27.5°
b = 57.477 (8) ŵ = 0.07 mm−1
c = 7.2226 (6) ÅT = 120 K
β = 114.725 (5)°Plate, colourless
V = 2429.6 (4) Å30.42 × 0.20 × 0.06 mm
Z = 4
Data collection top
Bruker–Nonius Kappa CCD
diffractometer		3758 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode2285 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
Detector resolution: 9.091 pixels mm-1θmax = 25.0°, θmin = 5.0°
φ & ω scansh = −7→7
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		k = −68→68
Tmin = 0.970, Tmax = 0.996l = −8→8
12411 measured 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)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0174P)2 + 4.4271P]
where P = (Fo2 + 2Fc2)/3
3758 reflections(Δ/σ)max = 0.001
584 parametersΔρmax = 0.23 e Å−3
52 restraintsΔρmin = −0.32 e Å−3
Crystal data top
C29H48O2·0.5H2OV = 2429.6 (4) Å3
Mr = 437.68Z = 4
Monoclinic, P21Mo Kα radiation
a = 6.4432 (4) ŵ = 0.07 mm−1
b = 57.477 (8) ÅT = 120 K
c = 7.2226 (6) Å0.42 × 0.20 × 0.06 mm
β = 114.725 (5)°
Data collection top
Bruker–Nonius Kappa CCD
diffractometer		3758 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		2285 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 0.996Rint = 0.064
12411 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07152 restraints
wR(F2) = 0.147H-atom parameters constrained
S = 1.05Δρmax = 0.23 e Å−3
3758 reflectionsΔρmin = −0.32 e Å−3
584 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. Flack gave no indication of absolute structure, so Friedels merged. Material isolated from a plant, but no clear idea of absolute structure. Most likely this is correct however.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.9141 (13)0.15886 (12)0.0149 (12)0.0246 (19)
O10.8628 (10)0.16278 (9)0.1878 (9)0.0382 (16)
H10.80520.17610.17920.057*
C20.7039 (13)0.16394 (12)−0.1775 (13)0.027 (2)
O20.5468 (10)0.17554 (9)−0.1680 (9)0.0424 (16)
C30.6946 (15)0.15411 (12)−0.3734 (13)0.034 (2)
H3A0.80560.1625−0.41140.041*
H3B0.54010.1566−0.48320.041*
C40.7496 (14)0.12804 (12)−0.3550 (12)0.028 (2)
H4A0.75650.1226−0.48250.034*
H4B0.62420.1195−0.33970.034*
C50.9782 (13)0.12198 (12)−0.1726 (11)0.0199 (18)
C60.9908 (13)0.09486 (11)−0.1440 (12)0.0223 (19)
H60.84640.0904−0.13280.027*
C70.9876 (14)0.08129 (12)−0.3270 (12)0.027 (2)
H7A1.13120.0844−0.34150.033*
H7B0.85930.0869−0.45210.033*
C80.9619 (14)0.05492 (12)−0.3079 (12)0.027 (2)
H8A0.80920.0517−0.31210.032*
H8B0.97150.0470−0.42590.032*
C91.1456 (12)0.04490 (11)−0.1102 (11)0.0191 (18)
H91.29470.0493−0.11230.023*
C101.1479 (12)0.01764 (11)−0.1013 (11)0.0171 (18)
C111.2009 (13)0.00819 (12)−0.2769 (11)0.0231 (19)
H11A1.06920.0115−0.40800.028*
H11B1.33490.0166−0.27720.028*
C121.2498 (13)−0.01789 (12)−0.2628 (11)0.0234 (19)
H12A1.1109−0.0265−0.27670.028*
H12B1.2885−0.0226−0.37630.028*
C131.4462 (13)−0.02423 (12)−0.0607 (11)0.0239 (19)
H13A1.5889−0.0174−0.05730.029*
H13B1.4646−0.0413−0.05380.029*
C141.4153 (13)−0.01598 (12)0.1279 (12)0.0228 (19)
C151.3517 (13)0.01046 (11)0.1021 (11)0.0202 (18)
H151.48790.01830.09760.024*
C161.3269 (14)0.02130 (12)0.2849 (13)0.028 (2)
H16A1.45450.01610.41240.034*
H16B1.18210.01600.28790.034*
C171.3279 (13)0.04789 (11)0.2727 (12)0.025 (2)
H17A1.47850.05300.28150.030*
H17B1.30960.05440.39200.030*
C181.1388 (12)0.05814 (11)0.0761 (12)0.0178 (18)
C191.1891 (12)0.08532 (12)0.0555 (11)0.0174 (18)
C201.1912 (14)0.09901 (12)0.2401 (12)0.027 (2)
H20A1.33100.09490.36220.032*
H20B1.05790.09420.26560.032*
C211.1839 (14)0.12576 (11)0.2096 (12)0.026 (2)
H21A1.17980.13360.33010.031*
H21B1.32300.13090.19530.031*
C220.9710 (13)0.13238 (12)0.0179 (11)0.0207 (18)
H220.84180.12420.03300.025*
C231.1030 (13)0.17568 (12)0.0279 (13)0.034 (2)
H23A1.05590.19170.03830.051*
H23B1.13140.1742−0.09470.051*
H23C1.24320.17200.14850.051*
C241.1701 (13)0.13176 (12)−0.2263 (11)0.0236 (19)
H24A1.11630.1460−0.30770.035*
H24B1.21100.1201−0.30470.035*
H24C1.30450.1354−0.10050.035*
C250.9171 (12)0.00745 (12)−0.1252 (12)0.0259 (19)
H25A0.79270.0173−0.21720.039*
H25B0.91180.00680.00830.039*
H25C0.8998−0.0083−0.18200.039*
C261.2423 (14)−0.03148 (13)0.1681 (13)0.031 (2)
H26A1.1008−0.03270.04340.046*
H26B1.2090−0.02460.27680.046*
H26C1.3075−0.04700.20980.046*
C271.6484 (14)−0.01867 (13)0.3106 (12)0.030 (2)
H27A1.7076−0.03440.31050.045*
H27B1.6307−0.01620.43740.045*
H27C1.7555−0.00720.30020.045*
C280.9116 (12)0.05487 (12)0.0917 (12)0.0238 (19)
H28A0.89500.03850.12220.036*
H28B0.78590.0592−0.03800.036*
H28C0.90810.06480.20070.036*
C291.4230 (12)0.08909 (12)0.0534 (13)0.029 (2)
H29A1.41680.0844−0.07920.043*
H29B1.53760.07970.16110.043*
H29C1.46440.10560.07710.043*
C300.6577 (13)0.23570 (13)0.3874 (12)0.0249 (19)
O30.8893 (10)0.23628 (10)0.5368 (10)0.0515 (18)
H30.95120.22330.53990.077*
C310.6470 (14)0.22709 (12)0.1855 (13)0.029 (2)
O40.8017 (11)0.21414 (11)0.1883 (11)0.0571 (19)
C320.4497 (15)0.23372 (13)−0.0082 (13)0.036 (2)
H32A0.31540.2242−0.02400.043*
H32B0.48790.2302−0.12460.043*
C330.3868 (14)0.25972 (12)−0.0144 (12)0.0275 (18)
H33A0.24330.2627−0.13670.033*
H33B0.50860.2692−0.02670.033*
C340.3552 (13)0.26759 (12)0.1794 (11)0.0187 (15)
C350.3424 (13)0.29505 (11)0.1735 (11)0.0173 (15)
H350.48110.30030.15610.021*
C360.1399 (13)0.30474 (11)−0.0097 (12)0.0239 (18)
H36A−0.00290.30080.00350.029*
H36B0.13390.2972−0.13500.029*
C370.1517 (14)0.33131 (12)−0.0317 (12)0.026 (2)
H37A0.28040.3351−0.06750.031*
H37B0.00910.3367−0.14490.031*
C380.1835 (13)0.34441 (11)0.1616 (11)0.0205 (19)
H380.04820.34000.18810.025*
C390.1706 (13)0.37191 (12)0.1389 (11)0.0182 (18)
C40−0.0682 (13)0.37832 (12)−0.0267 (12)0.028 (2)
H40A−0.07950.3730−0.16090.034*
H40B−0.18610.37000.00180.034*
C41−0.1181 (14)0.40456 (12)−0.0376 (13)0.033 (2)
H41A−0.27460.4076−0.14200.040*
H41B−0.00930.4130−0.07780.040*
C42−0.0955 (14)0.41349 (13)0.1714 (13)0.036 (2)
H42A−0.12240.43050.16250.043*
H42B−0.21560.40610.20330.043*
C430.1355 (13)0.40857 (12)0.3442 (12)0.024 (2)
C440.1912 (13)0.38201 (12)0.3461 (12)0.0216 (19)
H440.06880.37400.37280.026*
C450.4146 (13)0.37456 (12)0.5217 (12)0.027 (2)
H45A0.42740.38200.64970.033*
H45B0.54560.37980.49440.033*
C460.4217 (14)0.34792 (12)0.5456 (12)0.027 (2)
H46A0.29760.34310.58400.033*
H46B0.56870.34350.65820.033*
C470.3952 (12)0.33463 (11)0.3490 (11)0.0167 (17)
C480.3570 (12)0.30739 (11)0.3748 (11)0.0161 (16)
C490.5583 (13)0.29709 (11)0.5616 (11)0.024 (2)
H49A0.70330.30300.56310.029*
H49B0.54790.30270.68710.029*
C500.5657 (14)0.27055 (12)0.5658 (11)0.0236 (19)
H50A0.42860.26440.57810.028*
H50B0.70260.26520.68520.028*
C510.5737 (13)0.26148 (11)0.3691 (11)0.0200 (16)
H510.69690.27080.35410.024*
C520.5191 (16)0.21872 (13)0.4547 (14)0.045 (3)
H52A0.59110.20330.47830.067*
H52B0.36320.21760.34790.067*
H52C0.51450.22440.58100.067*
C530.1367 (13)0.25633 (12)0.1725 (13)0.0317 (19)
H53A0.12620.24030.12360.048*
H53B0.00360.26520.08000.048*
H53C0.14040.25630.30960.048*
C540.3513 (14)0.38123 (13)0.0706 (13)0.035 (2)
H54A0.30170.39630.00350.052*
H54B0.36990.3702−0.02500.052*
H54C0.49730.38310.18990.052*
C550.1109 (14)0.41428 (13)0.5426 (13)0.032 (2)
H55A0.03530.42940.52860.048*
H55B0.26260.41490.65640.048*
H55C0.01910.40220.56870.048*
C560.3179 (13)0.42516 (12)0.3354 (13)0.032 (2)
H56A0.28030.44120.35660.048*
H56B0.32230.42390.20180.048*
H56C0.46750.42100.44230.048*
C570.6213 (13)0.33865 (12)0.3247 (13)0.028 (2)
H57A0.59460.33600.18240.042*
H57B0.73820.32780.41290.042*
H57C0.67350.35470.36330.042*
C580.1398 (13)0.30336 (12)0.4067 (13)0.029 (2)
H58A0.13970.28740.45530.044*
H58B0.00580.30560.27740.044*
H58C0.13460.31440.50800.044*
O51.1056 (14)0.19142 (14)0.5664 (13)0.094 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.022 (5)0.026 (4)0.025 (5)0.003 (3)0.009 (4)−0.003 (4)
O10.055 (4)0.029 (3)0.046 (4)0.014 (3)0.036 (3)−0.002 (3)
C20.017 (5)0.012 (4)0.048 (6)−0.001 (3)0.009 (4)0.008 (4)
O20.036 (4)0.034 (3)0.056 (5)0.006 (3)0.017 (3)0.002 (3)
C30.042 (6)0.022 (4)0.028 (6)0.001 (4)0.004 (4)0.000 (4)
C40.038 (5)0.022 (4)0.020 (5)0.004 (4)0.007 (4)0.001 (4)
C50.028 (5)0.021 (4)0.011 (5)0.006 (3)0.009 (4)0.004 (3)
C60.032 (5)0.019 (4)0.021 (5)−0.005 (3)0.017 (4)0.002 (3)
C70.037 (5)0.025 (4)0.012 (5)0.004 (4)0.003 (4)0.003 (4)
C80.046 (5)0.022 (4)0.015 (5)0.002 (4)0.016 (4)0.004 (3)
C90.025 (4)0.023 (4)0.014 (5)−0.005 (3)0.013 (4)0.001 (3)
C100.024 (4)0.018 (4)0.009 (5)−0.009 (3)0.007 (4)0.002 (3)
C110.034 (5)0.021 (4)0.013 (5)−0.004 (3)0.009 (4)−0.002 (3)
C120.038 (5)0.021 (4)0.019 (5)−0.003 (4)0.020 (4)−0.002 (4)
C130.033 (5)0.021 (4)0.019 (5)−0.004 (3)0.013 (4)−0.001 (3)
C140.021 (5)0.023 (4)0.021 (5)−0.001 (3)0.006 (4)−0.003 (4)
C150.022 (4)0.019 (4)0.022 (5)−0.002 (3)0.012 (4)0.000 (3)
C160.035 (5)0.023 (4)0.030 (6)0.000 (4)0.017 (4)0.004 (4)
C170.034 (5)0.015 (4)0.033 (6)0.007 (3)0.021 (4)0.000 (4)
C180.018 (4)0.017 (4)0.016 (5)−0.003 (3)0.006 (4)0.001 (3)
C190.026 (5)0.021 (4)0.007 (5)0.003 (3)0.010 (4)−0.003 (3)
C200.028 (5)0.025 (4)0.021 (5)0.004 (4)0.006 (4)0.002 (4)
C210.038 (5)0.020 (4)0.026 (5)0.001 (4)0.020 (4)−0.010 (3)
C220.022 (5)0.025 (4)0.017 (5)0.000 (3)0.010 (4)−0.001 (3)
C230.037 (5)0.023 (4)0.045 (6)−0.005 (4)0.021 (5)−0.005 (4)
C240.039 (5)0.023 (4)0.010 (5)0.000 (3)0.011 (4)0.004 (3)
C250.033 (5)0.026 (4)0.018 (5)0.002 (4)0.011 (4)0.002 (4)
C260.040 (5)0.022 (4)0.029 (6)0.001 (4)0.014 (5)0.003 (4)
C270.046 (6)0.018 (4)0.021 (5)0.005 (4)0.010 (4)−0.004 (4)
C280.025 (5)0.029 (4)0.024 (5)−0.004 (3)0.017 (4)−0.005 (4)
C290.024 (5)0.024 (4)0.044 (6)−0.003 (3)0.018 (4)0.002 (4)
C300.029 (5)0.026 (4)0.025 (5)0.012 (4)0.016 (4)0.000 (4)
O30.050 (4)0.035 (3)0.056 (5)0.024 (3)0.009 (4)−0.005 (3)
C310.040 (6)0.016 (4)0.037 (6)0.007 (4)0.023 (5)−0.002 (4)
O40.059 (5)0.038 (4)0.086 (6)0.009 (3)0.041 (4)−0.002 (4)
C320.055 (6)0.028 (4)0.029 (6)0.000 (4)0.022 (5)0.000 (4)
C330.043 (5)0.024 (4)0.015 (4)0.005 (4)0.011 (4)−0.002 (3)
C340.030 (4)0.018 (3)0.006 (4)0.002 (3)0.005 (3)0.002 (3)
C350.024 (4)0.020 (3)0.004 (4)0.004 (3)0.003 (3)−0.002 (3)
C360.031 (4)0.017 (4)0.014 (4)0.003 (3)−0.001 (3)−0.001 (3)
C370.031 (5)0.026 (4)0.009 (5)0.006 (4)−0.004 (4)−0.005 (3)
C380.019 (4)0.020 (4)0.014 (5)0.004 (3)−0.001 (4)0.002 (3)
C390.026 (5)0.020 (4)0.006 (5)0.000 (3)0.005 (4)−0.001 (3)
C400.035 (5)0.018 (4)0.016 (5)0.004 (4)−0.005 (4)−0.002 (3)
C410.036 (5)0.024 (4)0.028 (6)0.006 (4)0.002 (4)0.000 (4)
C420.033 (5)0.019 (4)0.051 (7)−0.001 (4)0.013 (5)0.003 (4)
C430.038 (5)0.019 (4)0.014 (5)0.005 (4)0.011 (4)0.002 (3)
C440.024 (4)0.013 (4)0.027 (5)−0.003 (3)0.009 (4)−0.004 (3)
C450.031 (5)0.021 (4)0.021 (5)0.000 (3)0.003 (4)−0.007 (4)
C460.027 (5)0.024 (4)0.021 (5)0.005 (3)0.000 (4)−0.002 (3)
C470.022 (4)0.018 (4)0.006 (5)0.003 (3)0.001 (4)−0.005 (3)
C480.017 (4)0.019 (3)0.008 (4)−0.003 (3)0.001 (3)−0.003 (3)
C490.038 (5)0.021 (4)0.007 (5)0.005 (4)0.003 (4)−0.005 (3)
C500.031 (5)0.028 (4)0.010 (5)0.005 (4)0.006 (4)0.001 (3)
C510.034 (4)0.016 (3)0.012 (4)0.003 (3)0.012 (3)−0.001 (3)
C520.082 (8)0.021 (4)0.036 (6)0.007 (5)0.030 (6)0.002 (4)
C530.038 (4)0.021 (4)0.035 (6)0.002 (3)0.014 (4)−0.002 (4)
C540.048 (6)0.024 (4)0.041 (6)−0.003 (4)0.028 (5)0.000 (4)
C550.046 (6)0.023 (4)0.033 (6)0.003 (4)0.022 (5)0.002 (4)
C560.038 (5)0.016 (4)0.039 (6)−0.004 (4)0.014 (5)−0.004 (4)
C570.027 (5)0.025 (4)0.033 (6)0.003 (4)0.015 (4)−0.001 (4)
C580.037 (5)0.020 (4)0.030 (6)0.008 (4)0.014 (4)−0.001 (4)
O50.109 (7)0.076 (5)0.115 (7)0.010 (5)0.065 (6)0.010 (5)
Geometric parameters (Å, º) top
C1—O11.437 (9)C30—O31.430 (9)
C1—C21.509 (11)C30—C311.514 (11)
C1—C231.526 (10)C30—C521.533 (11)
C1—C221.563 (10)C30—C511.564 (10)
O1—H10.8400O3—H30.8400
C2—O21.238 (9)C31—O41.238 (9)
C2—C31.501 (11)C31—C321.494 (11)
C3—C41.533 (10)C32—C331.544 (10)
C3—H3A0.9900C32—H32A0.9900
C3—H3B0.9900C32—H32B0.9900
C4—C51.550 (10)C33—C341.563 (10)
C4—H4A0.9900C33—H33A0.9900
C4—H4B0.9900C33—H33B0.9900
C5—C221.519 (10)C34—C531.531 (10)
C5—C241.548 (10)C34—C511.539 (10)
C5—C61.570 (9)C34—C351.580 (9)
C6—C71.527 (10)C35—C361.523 (9)
C6—C191.572 (10)C35—C481.585 (9)
C6—H61.0000C35—H351.0000
C7—C81.537 (9)C36—C371.541 (9)
C7—H7A0.9900C36—H36A0.9900
C7—H7B0.9900C36—H36B0.9900
C8—C91.535 (10)C37—C381.523 (10)
C8—H8A0.9900C37—H37A0.9900
C8—H8B0.9900C37—H37B0.9900
C9—C181.563 (10)C38—C471.570 (9)
C9—C101.568 (9)C38—C391.587 (9)
C9—H91.0000C38—H381.0000
C10—C251.539 (9)C39—C541.538 (10)
C10—C111.543 (10)C39—C401.547 (10)
C10—C151.562 (10)C39—C441.558 (10)
C11—C121.526 (9)C40—C411.537 (9)
C11—H11A0.9900C40—H40A0.9900
C11—H11B0.9900C40—H40B0.9900
C12—C131.523 (10)C41—C421.542 (12)
C12—H12A0.9900C41—H41A0.9900
C12—H12B0.9900C41—H41B0.9900
C13—C141.532 (10)C42—C431.516 (10)
C13—H13A0.9900C42—H42A0.9900
C13—H13B0.9900C42—H42B0.9900
C14—C271.537 (10)C43—C561.535 (10)
C14—C261.547 (10)C43—C551.541 (10)
C14—C151.565 (9)C43—C441.567 (9)
C15—C161.527 (10)C44—C451.529 (10)
C15—H151.0000C44—H441.0000
C16—C171.531 (9)C45—C461.539 (9)
C16—H16A0.9900C45—H45A0.9900
C16—H16B0.9900C45—H45B0.9900
C17—C181.549 (10)C46—C471.558 (9)
C17—H17A0.9900C46—H46A0.9900
C17—H17B0.9900C46—H46B0.9900
C18—C281.526 (10)C47—C571.556 (10)
C18—C191.615 (9)C47—C481.608 (9)
C19—C291.528 (10)C48—C581.529 (10)
C19—C201.544 (10)C48—C491.545 (10)
C20—C211.551 (9)C49—C501.527 (9)
C20—H20A0.9900C49—H49A0.9900
C20—H20B0.9900C49—H49B0.9900
C21—C221.534 (10)C50—C511.534 (10)
C21—H21A0.9900C50—H50A0.9900
C21—H21B0.9900C50—H50B0.9900
C22—H221.0000C51—H511.0000
C23—H23A0.9800C52—H52A0.9800
C23—H23B0.9800C52—H52B0.9800
C23—H23C0.9800C52—H52C0.9800
C24—H24A0.9800C53—H53A0.9800
C24—H24B0.9800C53—H53B0.9800
C24—H24C0.9800C53—H53C0.9800
C25—H25A0.9800C54—H54A0.9800
C25—H25B0.9800C54—H54B0.9800
C25—H25C0.9800C54—H54C0.9800
C26—H26A0.9800C55—H55A0.9800
C26—H26B0.9800C55—H55B0.9800
C26—H26C0.9800C55—H55C0.9800
C27—H27A0.9800C56—H56A0.9800
C27—H27B0.9800C56—H56B0.9800
C27—H27C0.9800C56—H56C0.9800
C28—H28A0.9800C57—H57A0.9800
C28—H28B0.9800C57—H57B0.9800
C28—H28C0.9800C57—H57C0.9800
C29—H29A0.9800C58—H58A0.9800
C29—H29B0.9800C58—H58B0.9800
C29—H29C0.9800C58—H58C0.9800
O1—C1—C2109.0 (6)O3—C30—C31110.3 (6)
O1—C1—C23108.3 (6)O3—C30—C52109.7 (7)
C2—C1—C23108.7 (6)C31—C30—C52107.4 (7)
O1—C1—C22106.1 (6)O3—C30—C51104.9 (6)
C2—C1—C22108.4 (6)C31—C30—C51110.7 (6)
C23—C1—C22116.1 (6)C52—C30—C51113.8 (6)
C1—O1—H1109.5C30—O3—H3109.5
O2—C2—C3123.0 (7)O4—C31—C32122.2 (8)
O2—C2—C1119.5 (8)O4—C31—C30117.9 (8)
C3—C2—C1117.5 (7)C32—C31—C30119.8 (7)
C2—C3—C4111.7 (7)C31—C32—C33112.6 (7)
C2—C3—H3A109.3C31—C32—H32A109.1
C4—C3—H3A109.3C33—C32—H32A109.1
C2—C3—H3B109.3C31—C32—H32B109.1
C4—C3—H3B109.3C33—C32—H32B109.1
H3A—C3—H3B107.9H32A—C32—H32B107.8
C3—C4—C5113.3 (6)C32—C33—C34112.6 (6)
C3—C4—H4A108.9C32—C33—H33A109.1
C5—C4—H4A108.9C34—C33—H33A109.1
C3—C4—H4B108.9C32—C33—H33B109.1
C5—C4—H4B108.9C34—C33—H33B109.1
H4A—C4—H4B107.7H33A—C33—H33B107.8
C22—C5—C24114.5 (6)C53—C34—C51114.8 (6)
C22—C5—C4107.7 (6)C53—C34—C33108.1 (6)
C24—C5—C4106.3 (6)C51—C34—C33108.5 (6)
C22—C5—C6106.9 (6)C53—C34—C35112.6 (6)
C24—C5—C6113.0 (6)C51—C34—C35105.7 (6)
C4—C5—C6108.2 (6)C33—C34—C35106.8 (6)
C7—C6—C5114.3 (6)C36—C35—C34113.9 (6)
C7—C6—C19109.1 (6)C36—C35—C48109.5 (6)
C5—C6—C19116.4 (6)C34—C35—C48116.1 (6)
C7—C6—H6105.3C36—C35—H35105.4
C5—C6—H6105.3C34—C35—H35105.4
C19—C6—H6105.3C48—C35—H35105.4
C6—C7—C8112.9 (6)C35—C36—C37113.0 (6)
C6—C7—H7A109.0C35—C36—H36A109.0
C8—C7—H7A109.0C37—C36—H36A109.0
C6—C7—H7B109.0C35—C36—H36B109.0
C8—C7—H7B109.0C37—C36—H36B109.0
H7A—C7—H7B107.8H36A—C36—H36B107.8
C9—C8—C7112.5 (6)C38—C37—C36112.9 (6)
C9—C8—H8A109.1C38—C37—H37A109.0
C7—C8—H8A109.1C36—C37—H37A109.0
C9—C8—H8B109.1C38—C37—H37B109.0
C7—C8—H8B109.1C36—C37—H37B109.0
H8A—C8—H8B107.8H37A—C37—H37B107.8
C8—C9—C18109.2 (6)C37—C38—C47110.4 (6)
C8—C9—C10113.8 (6)C37—C38—C39114.6 (6)
C18—C9—C10117.0 (6)C47—C38—C39115.8 (6)
C8—C9—H9105.2C37—C38—H38104.9
C18—C9—H9105.2C47—C38—H38104.9
C10—C9—H9105.2C39—C38—H38104.9
C25—C10—C11108.0 (6)C54—C39—C40108.1 (6)
C25—C10—C15113.4 (6)C54—C39—C44114.0 (6)
C11—C10—C15107.0 (6)C40—C39—C44108.1 (6)
C25—C10—C9112.5 (6)C54—C39—C38111.5 (6)
C11—C10—C9108.6 (6)C40—C39—C38108.0 (6)
C15—C10—C9107.0 (5)C44—C39—C38107.0 (6)
C12—C11—C10113.7 (6)C41—C40—C39113.1 (6)
C12—C11—H11A108.8C41—C40—H40A109.0
C10—C11—H11A108.8C39—C40—H40A109.0
C12—C11—H11B108.8C41—C40—H40B109.0
C10—C11—H11B108.8C39—C40—H40B109.0
H11A—C11—H11B107.7H40A—C40—H40B107.8
C13—C12—C11111.4 (6)C40—C41—C42110.1 (7)
C13—C12—H12A109.4C40—C41—H41A109.6
C11—C12—H12A109.4C42—C41—H41A109.6
C13—C12—H12B109.4C40—C41—H41B109.6
C11—C12—H12B109.4C42—C41—H41B109.6
H12A—C12—H12B108.0H41A—C41—H41B108.2
C12—C13—C14114.4 (6)C43—C42—C41113.7 (7)
C12—C13—H13A108.7C43—C42—H42A108.8
C14—C13—H13A108.7C41—C42—H42A108.8
C12—C13—H13B108.7C43—C42—H42B108.8
C14—C13—H13B108.7C41—C42—H42B108.8
H13A—C13—H13B107.6H42A—C42—H42B107.7
C13—C14—C27106.7 (6)C42—C43—C56110.8 (6)
C13—C14—C26111.1 (6)C42—C43—C55106.2 (7)
C27—C14—C26107.6 (6)C56—C43—C55106.5 (6)
C13—C14—C15108.6 (6)C42—C43—C44109.3 (6)
C27—C14—C15108.3 (6)C56—C43—C44115.4 (6)
C26—C14—C15114.1 (6)C55—C43—C44108.2 (6)
C16—C15—C10110.8 (6)C45—C44—C39111.4 (6)
C16—C15—C14114.2 (6)C45—C44—C43114.4 (6)
C10—C15—C14116.4 (6)C39—C44—C43115.3 (6)
C16—C15—H15104.7C45—C44—H44104.8
C10—C15—H15104.7C39—C44—H44104.8
C14—C15—H15104.7C43—C44—H44104.8
C15—C16—C17110.7 (6)C44—C45—C46110.2 (6)
C15—C16—H16A109.5C44—C45—H45A109.6
C17—C16—H16A109.5C46—C45—H45A109.6
C15—C16—H16B109.5C44—C45—H45B109.6
C17—C16—H16B109.5C46—C45—H45B109.6
H16A—C16—H16B108.1H45A—C45—H45B108.1
C16—C17—C18114.3 (6)C45—C46—C47113.5 (6)
C16—C17—H17A108.7C45—C46—H46A108.9
C18—C17—H17A108.7C47—C46—H46A108.9
C16—C17—H17B108.7C45—C46—H46B108.9
C18—C17—H17B108.7C47—C46—H46B108.9
H17A—C17—H17B107.6H46A—C46—H46B107.7
C28—C18—C17107.3 (6)C57—C47—C46106.2 (6)
C28—C18—C9112.1 (6)C57—C47—C38111.5 (6)
C17—C18—C9108.0 (6)C46—C47—C38109.6 (6)
C28—C18—C19111.2 (6)C57—C47—C48110.7 (5)
C17—C18—C19110.0 (5)C46—C47—C48109.6 (6)
C9—C18—C19108.2 (5)C38—C47—C48109.2 (5)
C29—C19—C20106.5 (6)C58—C48—C49107.3 (6)
C29—C19—C6111.6 (6)C58—C48—C35111.3 (6)
C20—C19—C6108.9 (6)C49—C48—C35109.6 (5)
C29—C19—C18112.0 (5)C58—C48—C47111.0 (5)
C20—C19—C18110.1 (6)C49—C48—C47111.1 (6)
C6—C19—C18107.7 (5)C35—C48—C47106.4 (6)
C19—C20—C21113.2 (6)C50—C49—C48114.1 (6)
C19—C20—H20A108.9C50—C49—H49A108.7
C21—C20—H20A108.9C48—C49—H49A108.7
C19—C20—H20B108.9C50—C49—H49B108.7
C21—C20—H20B108.9C48—C49—H49B108.7
H20A—C20—H20B107.7H49A—C49—H49B107.6
C22—C21—C20109.7 (6)C49—C50—C51109.5 (6)
C22—C21—H21A109.7C49—C50—H50A109.8
C20—C21—H21A109.7C51—C50—H50A109.8
C22—C21—H21B109.7C49—C50—H50B109.8
C20—C21—H21B109.7C51—C50—H50B109.8
H21A—C21—H21B108.2H50A—C50—H50B108.2
C5—C22—C21111.5 (6)C50—C51—C34112.0 (6)
C5—C22—C1117.8 (6)C50—C51—C30112.8 (6)
C21—C22—C1111.7 (6)C34—C51—C30116.5 (6)
C5—C22—H22104.9C50—C51—H51104.7
C21—C22—H22104.9C34—C51—H51104.7
C1—C22—H22104.9C30—C51—H51104.7
C1—C23—H23A109.5C30—C52—H52A109.5
C1—C23—H23B109.5C30—C52—H52B109.5
H23A—C23—H23B109.5H52A—C52—H52B109.5
C1—C23—H23C109.5C30—C52—H52C109.5
H23A—C23—H23C109.5H52A—C52—H52C109.5
H23B—C23—H23C109.5H52B—C52—H52C109.5
C5—C24—H24A109.5C34—C53—H53A109.5
C5—C24—H24B109.5C34—C53—H53B109.5
H24A—C24—H24B109.5H53A—C53—H53B109.5
C5—C24—H24C109.5C34—C53—H53C109.5
H24A—C24—H24C109.5H53A—C53—H53C109.5
H24B—C24—H24C109.5H53B—C53—H53C109.5
C10—C25—H25A109.5C39—C54—H54A109.5
C10—C25—H25B109.5C39—C54—H54B109.5
H25A—C25—H25B109.5H54A—C54—H54B109.5
C10—C25—H25C109.5C39—C54—H54C109.5
H25A—C25—H25C109.5H54A—C54—H54C109.5
H25B—C25—H25C109.5H54B—C54—H54C109.5
C14—C26—H26A109.5C43—C55—H55A109.5
C14—C26—H26B109.5C43—C55—H55B109.5
H26A—C26—H26B109.5H55A—C55—H55B109.5
C14—C26—H26C109.5C43—C55—H55C109.5
H26A—C26—H26C109.5H55A—C55—H55C109.5
H26B—C26—H26C109.5H55B—C55—H55C109.5
C14—C27—H27A109.5C43—C56—H56A109.5
C14—C27—H27B109.5C43—C56—H56B109.5
H27A—C27—H27B109.5H56A—C56—H56B109.5
C14—C27—H27C109.5C43—C56—H56C109.5
H27A—C27—H27C109.5H56A—C56—H56C109.5
H27B—C27—H27C109.5H56B—C56—H56C109.5
C18—C28—H28A109.5C47—C57—H57A109.5
C18—C28—H28B109.5C47—C57—H57B109.5
H28A—C28—H28B109.5H57A—C57—H57B109.5
C18—C28—H28C109.5C47—C57—H57C109.5
H28A—C28—H28C109.5H57A—C57—H57C109.5
H28B—C28—H28C109.5H57B—C57—H57C109.5
C19—C29—H29A109.5C48—C58—H58A109.5
C19—C29—H29B109.5C48—C58—H58B109.5
H29A—C29—H29B109.5H58A—C58—H58B109.5
C19—C29—H29C109.5C48—C58—H58C109.5
H29A—C29—H29C109.5H58A—C58—H58C109.5
H29B—C29—H29C109.5H58B—C58—H58C109.5
O1—C1—C2—O217.6 (9)O3—C30—C31—O426.7 (10)
C23—C1—C2—O2−100.3 (8)C52—C30—C31—O4−92.9 (8)
C22—C1—C2—O2132.7 (7)C51—C30—C31—O4142.3 (7)
O1—C1—C2—C3−161.4 (6)O3—C30—C31—C32−155.2 (7)
C23—C1—C2—C380.7 (8)C52—C30—C31—C3285.2 (8)
C22—C1—C2—C3−46.2 (9)C51—C30—C31—C32−39.6 (10)
O2—C2—C3—C4−128.5 (8)O4—C31—C32—C33−137.7 (8)
C1—C2—C3—C450.4 (9)C30—C31—C32—C3344.3 (10)
C2—C3—C4—C5−53.1 (9)C31—C32—C33—C34−51.2 (10)
C3—C4—C5—C2253.5 (9)C32—C33—C34—C53−69.9 (8)
C3—C4—C5—C24−69.6 (8)C32—C33—C34—C5155.1 (8)
C3—C4—C5—C6168.8 (7)C32—C33—C34—C35168.6 (6)
C22—C5—C6—C7177.2 (6)C53—C34—C35—C36−56.1 (9)
C24—C5—C6—C7−56.0 (9)C51—C34—C35—C36177.9 (6)
C4—C5—C6—C761.4 (8)C33—C34—C35—C3662.5 (8)
C22—C5—C6—C19−54.2 (8)C53—C34—C35—C4872.5 (8)
C24—C5—C6—C1972.7 (8)C51—C34—C35—C48−53.5 (8)
C4—C5—C6—C19−169.9 (6)C33—C34—C35—C48−168.9 (6)
C5—C6—C7—C8−170.9 (6)C34—C35—C36—C37−170.6 (6)
C19—C6—C7—C856.8 (8)C48—C35—C36—C3757.5 (8)
C6—C7—C8—C9−55.0 (9)C35—C36—C37—C38−53.4 (9)
C7—C8—C9—C1856.1 (8)C36—C37—C38—C4753.2 (8)
C7—C8—C9—C10−171.1 (6)C36—C37—C38—C39−173.9 (6)
C8—C9—C10—C25−57.9 (8)C37—C38—C39—C54−58.3 (9)
C18—C9—C10—C2571.1 (8)C47—C38—C39—C5472.0 (8)
C8—C9—C10—C1161.7 (8)C37—C38—C39—C4060.3 (8)
C18—C9—C10—C11−169.3 (6)C47—C38—C39—C40−169.4 (6)
C8—C9—C10—C15176.9 (6)C37—C38—C39—C44176.5 (6)
C18—C9—C10—C15−54.1 (8)C47—C38—C39—C44−53.2 (8)
C25—C10—C11—C12−67.9 (8)C54—C39—C40—C41−69.2 (9)
C15—C10—C11—C1254.5 (8)C44—C39—C40—C4154.6 (9)
C9—C10—C11—C12169.7 (6)C38—C39—C40—C41170.1 (7)
C10—C11—C12—C13−56.7 (8)C39—C40—C41—C42−57.2 (9)
C11—C12—C13—C1454.3 (8)C40—C41—C42—C4356.4 (9)
C12—C13—C14—C27−167.0 (6)C41—C42—C43—C5675.4 (8)
C12—C13—C14—C2675.9 (8)C41—C42—C43—C55−169.4 (6)
C12—C13—C14—C15−50.4 (8)C41—C42—C43—C44−52.9 (9)
C25—C10—C15—C16−67.1 (7)C54—C39—C44—C45−64.9 (8)
C11—C10—C15—C16173.9 (6)C40—C39—C44—C45174.9 (6)
C9—C10—C15—C1657.6 (7)C38—C39—C44—C4558.8 (8)
C25—C10—C15—C1465.6 (8)C54—C39—C44—C4367.6 (8)
C11—C10—C15—C14−53.4 (8)C40—C39—C44—C43−52.6 (8)
C9—C10—C15—C14−169.7 (6)C38—C39—C44—C43−168.7 (6)
C13—C14—C15—C16−177.2 (6)C42—C43—C44—C45−176.7 (7)
C27—C14—C15—C16−61.6 (8)C56—C43—C44—C4557.6 (9)
C26—C14—C15—C1658.2 (9)C55—C43—C44—C45−61.5 (9)
C13—C14—C15—C1051.7 (8)C42—C43—C44—C3952.2 (9)
C27—C14—C15—C10167.3 (6)C56—C43—C44—C39−73.5 (9)
C26—C14—C15—C10−72.9 (9)C55—C43—C44—C39167.4 (6)
C10—C15—C16—C17−61.2 (8)C39—C44—C45—C46−62.6 (8)
C14—C15—C16—C17165.0 (6)C43—C44—C45—C46164.4 (7)
C15—C16—C17—C1857.7 (9)C44—C45—C46—C4757.5 (9)
C16—C17—C18—C2871.4 (8)C45—C46—C47—C5771.0 (8)
C16—C17—C18—C9−49.6 (8)C45—C46—C47—C38−49.6 (9)
C16—C17—C18—C19−167.5 (6)C45—C46—C47—C48−169.4 (6)
C8—C9—C18—C2862.8 (7)C37—C38—C47—C5763.8 (7)
C10—C9—C18—C28−68.3 (8)C39—C38—C47—C57−68.5 (8)
C8—C9—C18—C17−179.2 (5)C37—C38—C47—C46−178.8 (6)
C10—C9—C18—C1749.6 (8)C39—C38—C47—C4648.8 (8)
C8—C9—C18—C19−60.2 (7)C37—C38—C47—C48−58.8 (8)
C10—C9—C18—C19168.6 (6)C39—C38—C47—C48168.9 (6)
C7—C6—C19—C2963.0 (7)C36—C35—C48—C5859.8 (8)
C5—C6—C19—C29−68.2 (8)C34—C35—C48—C58−70.8 (8)
C7—C6—C19—C20−179.8 (6)C36—C35—C48—C49178.4 (6)
C5—C6—C19—C2049.0 (8)C34—C35—C48—C4947.7 (8)
C7—C6—C19—C18−60.4 (7)C36—C35—C48—C47−61.3 (7)
C5—C6—C19—C18168.4 (6)C34—C35—C48—C47168.0 (6)
C28—C18—C19—C29176.3 (6)C57—C47—C48—C58177.9 (6)
C17—C18—C19—C2957.7 (8)C46—C47—C48—C5861.0 (8)
C9—C18—C19—C29−60.1 (7)C38—C47—C48—C58−59.0 (8)
C28—C18—C19—C2058.1 (8)C57—C47—C48—C4958.5 (8)
C17—C18—C19—C20−60.6 (7)C46—C47—C48—C49−58.3 (8)
C9—C18—C19—C20−178.3 (6)C38—C47—C48—C49−178.4 (6)
C28—C18—C19—C6−60.5 (7)C57—C47—C48—C35−60.8 (7)
C17—C18—C19—C6−179.2 (6)C46—C47—C48—C35−177.7 (6)
C9—C18—C19—C663.1 (7)C38—C47—C48—C3562.3 (7)
C29—C19—C20—C2171.3 (8)C58—C48—C49—C5073.2 (8)
C6—C19—C20—C21−49.2 (8)C35—C48—C49—C50−47.9 (9)
C18—C19—C20—C21−167.0 (6)C47—C48—C49—C50−165.3 (6)
C19—C20—C21—C2257.3 (8)C48—C49—C50—C5156.6 (9)
C24—C5—C22—C21−66.2 (8)C49—C50—C51—C34−64.2 (8)
C4—C5—C22—C21175.9 (6)C49—C50—C51—C30161.9 (6)
C6—C5—C22—C2159.7 (8)C53—C34—C51—C50−64.0 (8)
C24—C5—C22—C164.8 (8)C33—C34—C51—C50175.0 (6)
C4—C5—C22—C1−53.1 (8)C35—C34—C51—C5060.7 (8)
C6—C5—C22—C1−169.2 (6)C53—C34—C51—C3068.0 (8)
C20—C21—C22—C5−63.2 (8)C33—C34—C51—C30−53.0 (8)
C20—C21—C22—C1162.7 (6)C35—C34—C51—C30−167.3 (6)
O1—C1—C22—C5166.1 (6)O3—C30—C51—C50−64.9 (8)
C2—C1—C22—C549.0 (9)C31—C30—C51—C50176.1 (6)
C23—C1—C22—C5−73.5 (9)C52—C30—C51—C5055.0 (9)
O1—C1—C22—C21−63.0 (8)O3—C30—C51—C34163.5 (6)
C2—C1—C22—C21180.0 (7)C31—C30—C51—C3444.5 (9)
C23—C1—C22—C2157.4 (9)C52—C30—C51—C34−76.6 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.842.192.978 (8)156
O3—H3···O50.842.062.896 (9)176

Experimental details

Crystal data
Chemical formulaC29H48O2·0.5H2O
Mr437.68
Crystal system, space groupMonoclinic, P21
Temperature (K)120
a, b, c (Å)6.4432 (4), 57.477 (8), 7.2226 (6)
β (°) 114.725 (5)
V (Å3)2429.6 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.07
Crystal size (mm)0.42 × 0.20 × 0.06
Data collection
DiffractometerBruker–Nonius Kappa CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.970, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections		12411, 3758, 2285
Rint0.064
(sin θ/λ)max (Å−1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.071, 0.147, 1.05
No. of reflections3758
No. of parameters584
No. of restraints52
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.23, −0.32

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997) and COLLECT, DENZO and COLLECT, SHELXTL (Sheldrick, 2000), SHELXTL and local programs.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.842.192.978 (8)156.4
O3—H3···O50.842.062.896 (9)176.4
 

Acknowledgements

The authors acknowledge the EPSRC National Crystallography Service at the University of Southampton for the data collection.

References

First citationAgeta, H., Iwata, K. & Arai, Y. (1966). Tetrahedron Lett. 46, 5679–5684.  CrossRef Google Scholar
 First citationHooft, R. W. W. (1998). COLLECT. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
 First citationJanaki, S., Vijayasekaran, V., Viswanathan, S. & Balakrishna, K. (1999). J. Ethnopharmacol. 67, 45–51.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationKshirsagar, M. K. & Mehta, A. R. (1972). Planta Med. 22, 386–390.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationMatsuda, H., Kageura, T., Toguchida, I., Murakami, T., Kishi, A. & Yoshikawa, M. (1999). Bioorg. Med. Chem. Lett. 9, 3081–3086.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
 First citationSheldrick, G. M. (2000). SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationSheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.  Google Scholar
 First citationWada, M., Shimizu, H. & Kondo, N. (1987). Bot. Mag. Tokyo, 100, 51–62.  CrossRef CAS Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o264
https://doi.org/10.1107/S1600536807064021
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