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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 9| September 2012| Pages o2712-o2713

(20S)-Dammar-24-ene-3β,20-diol monohydrate from the bark of Aglaia exima (Meliaceae)

aDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Padjadjaran University, Jatinangor 45363, West Java, Indonesia, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my

(Received 7 August 2012; accepted 8 August 2012; online 15 August 2012)

In the title compound {systematic name: (1R,2R,5R,7R,10R,11R,14S,15R)-14-[(2S)-2-hy­droxy-6-methyl­hept-5-en-2-yl]-2,6,6,10,11-penta­methyl­tetra­cyclo­[8.7.0.02,7.011,15]hepta­decan-5-ol monohydrate}, C30H52O2·H2O, the three fused cyclo­hexane rings adopt chair conformations and the hy­droxy substituent of one of these occupies an axial position. The fused cyclo­pentane ring adopts an envelope conformation (with the flap atom being the C atom bearing the methyl group) and the 3-methyl­but-2-enyl portion of its substituent is disordered over three sets of sites in a 0.413 (7):0.250 (7):0.337 (7) ratio. The O atoms of both water mol­ecules occupy special positions of 2 site symmetry. In the crystal, Os—H⋯Ow and Ow—H⋯Os (s = steroid and w = water) hydrogen bonds link hy­droxy groups and water mol­ecules, forming a three-dimensional network. The crystal studied was found to be a non-merohedral twin with a 0.518 (1):0.482 (1) component ratio.

Related literature

For the isolation of 20S-dammar-24-ene-3β,20-diol from other plants, see: Anjaneyulu et al. (1985[Anjaneyulu, V., Prasad, K. H., Ravi, K. & Connolly, J. D. (1985). Phytochemistry, 24, 2359-2367.]); Bianchini et al. (1988[Bianchini, J. P., Gaydou, E. M., Rafaralahitsimba, G., Waegell, B. & Zahra, J. P. (1988). Phytochemistry, 27, 2301-2304.]); Huang et al. (2010[Huang, X. J., Yin, Z.-Q., Ye, W.-C. & Shen, W.-B. (2010). Zhongguo Zhongyao Zazhi, 35, 861-864.]); Leonti et al. (2004[Leonti, M., Heilmann, J., Heinrich, M. & Sticher, O. (2004). Rev. Latinoam. Quim. 32, 87-94.]); Pakhathirathien et al. (2005[Pakhathirathien, C., Karalai, C., Ponglimanont, C., Subhadhirasakul, S. & Chantrapromma, K. (2005). J. Nat. Prod. 68, 1787-1789.]); Ukiya et al. (2010[Ukiya, M., Kikuchi, T., Tokuda, H., Tabata, K., Kimura, Y., Arai, T., Ezaki, Y., Oseto, O., Suzuki, T. & Akihisa, T. (2010). Chem. Biodivers. 7, 1871-1884.]).

[Scheme 1]

Experimental

Crystal data
  • C30H52O2·H2O

  • Mr = 462.73

  • Tetragonal, P 42

  • a = 19.9229 (1) Å

  • c = 7.3302 (1) Å

  • V = 2909.52 (4) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.50 mm−1

  • T = 100 K

  • 0.30 × 0.10 × 0.05 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.864, Tmax = 0.975

  • 11893 measured reflections

  • 15153 independent reflections

  • 14049 reflections with I > 2σ(I)

  • Rint = 0.068

Refinement
  • R[F2 > 2σ(F2)] = 0.077

  • wR(F2) = 0.266

  • S = 1.15

  • 15153 reflections

  • 341 parameters

  • 45 restraints

  • H-atom parameters constrained

  • Δρmax = 1.15 e Å−3

  • Δρmin = −0.37 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2575 Friedel pairs

  • Flack parameter: 0.1 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O1w 0.84 1.96 2.745 (2) 154
O2—H2⋯O2w 0.84 2.03 2.809 (2) 154
O1w—H1w⋯O2i 0.84 1.88 2.712 (2) 171
O2w—H2w⋯O1ii 0.84 1.95 2.786 (2) 171
Symmetry codes: (i) [-y+1, x+1, z-{\script{1\over 2}}]; (ii) [-y+1, x, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The genus of Aglaia (Meliaceae family) comprises more than a hundred woody plant species, most of which are found in Indonesia. In this part of the world, the genus provides fruit and they are also used in traditional medicines. 20S-Dammar-24-ene-3β,20-diol has been isolated from several plants, e.g., Ceriops tagal (Pakhathirathien et al., 2005), Ligustrum lucidum (Huang et al., 2010), Olea madagascariensis (Bianchini et al., 1988), Mangifera indica (Anjaneyulu et al. (1985), Mosquitoxylum jamaicense (Anacardiaceae) (Leonti et al., 2004) and Shoreajavanica (Dipterocarpaceae) (Ukiya et al., 2010). The compound is also available commercially.

14-[(2S)-2-Hydroxy-6-methylhept-5-en-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.02,7.011,15]heptadecan-5-olcrystallizes as a monohydrate (Scheme I). The Flack parameter, calculated from 2574 Friedel pairs, is sufficiently well refined despite the somewhat large standard deviation. The few oxygen atoms together with twinning and disorder precluded a more accurate refinement; nevertheless, the absolute configuration is that expected from spectroscopic assignments.

The three cyclohexane rings that are fused together adopt chair conformations; the cyclopentane ring that is fused with a cyclohexane ring adopts an envelope conformation. The 3-methylbut-2-enyl portion of its substituent is disordered over three positions in an approximate 1:1:1 ratio. The O atoms of both water molecules lie on special positions of 2 site symmetry. Both hydroxy groups are hydrogen-bond donors to water molecules; the water molecules themselves are hydrogen-bond donors to hydroxy groups to generate a three-dimensional hydrogen-bonded network (Table 1).

Related literature top

For the isolation of 20S-dammar-24-ene-3β,20-diol from other plants, see: Anjaneyulu et al. (1985); Bianchini et al. (1988); Huang et al. (2010); Leonti et al. (2004); Pakhathirathien et al. (2005); Ukiya et al. (2010).

Experimental top

Aglaia exima was collected from the Bogor Botanical Garden, West Java, Indonesia in July 2006. The plant was identified by Herbarium Bogoriense of Bogor city. The dried and milled bark (3 kg) was extracted succesively by n-hexane, ethyl acetate and methanol at room temperature. The ethyl acetate extract (300 g) was subjected to vacuum chromatography on silica gel G 60 by using a step gradient of n-hexane–ethyl acetate–methanol. The fraction eluted by n-hexane/ethyl acetate (3:2) was further separated by column chromatography on silica gel (chloroform: methanol; 9.5:0.5) to give a colorless solid (63 mg). Colourless prisms were obtained by recrystallization from ethyl acetate solution. The chemical structure was established by NMR spectroscopic analysis; however, the analysis did not note the presence of water.

Refinement top

Carbon- and oxygen-bound H-atoms were placed in calculated positions [C–H 0.98 to 1.00 Å, O–H 0.84 Å, Uiso(H) 1.2 to 1.5Ueq(C,O)] and were included in the refinement in the riding model approximation.

The 3-methylbut-2-enyl chain is disordered over three sites in a 0.413 (7): 0.250: 0.337 ratio. The temperature factors of the singly-primed and doubly-primed atoms were set to those of the unprimed ones; the anisotropic temperature factors were restrained to be nearly isotropic. The 1,2-related distances were restrained to within 0.01 Å.

The final difference Fourier map had a peak at 3.64 Å from H1c. The peak, which is close to a special position, could not be refined as a half oxygen atom.

The Flack parameter was calculated from 2574 Friedel pairs. The few oxygen atoms together with twinning and disorder precluded a more accurate refinement. The absolute configuration is that expected from spectroscopic assignments. Twinning and disorder probably contributed to the large weighting scheme.

The structure is a non-merohedral twin [twin law: -0.9998 - 0.0165 - 0.0977, 0.0160 - 0.9976 - 0.0931, -0.0130 - 0.0127) with a minor component of 48.2 (1)%.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
The molecular structure of the title compound at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the 3-methylbut-2-enyl chain is not shown.
(1R,2R,5R,7R,10R,11R,14S, 15R)-14-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2,6,6,10,11- pentamethyltetracyclo[8.7.0.02,7.011,15]heptadecan-5-ol monohydrate top
Crystal data top
C30H52O2·H2ODx = 1.056 Mg m3
Mr = 462.73Cu Kα radiation, λ = 1.54184 Å
Tetragonal, P42Cell parameters from 37417 reflections
Hall symbol: P 4cθ = 3.1–76.4°
a = 19.9229 (1) ŵ = 0.50 mm1
c = 7.3302 (1) ÅT = 100 K
V = 2909.52 (4) Å3Prism, colorless
Z = 40.30 × 0.10 × 0.05 mm
F(000) = 1032
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
15153 independent reflections
Radiation source: SuperNova (Cu) X-ray Source14049 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.068
Detector resolution: 10.4041 pixels mm-1θmax = 76.9°, θmin = 3.1°
ω scanh = 2525
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 2524
Tmin = 0.864, Tmax = 0.975l = 97
11893 measured reflections
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)] = 0.077H-atom parameters constrained
wR(F2) = 0.266 w = 1/[σ2(Fo2) + (0.1593P)2 + 2.3284P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max = 0.001
15153 reflectionsΔρmax = 1.15 e Å3
341 parametersΔρmin = 0.36 e Å3
45 restraintsAbsolute structure: Flack (1983), 2575 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.1 (3)
Crystal data top
C30H52O2·H2OZ = 4
Mr = 462.73Cu Kα radiation
Tetragonal, P42µ = 0.50 mm1
a = 19.9229 (1) ÅT = 100 K
c = 7.3302 (1) Å0.30 × 0.10 × 0.05 mm
V = 2909.52 (4) Å3
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
15153 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
14049 reflections with I > 2σ(I)
Tmin = 0.864, Tmax = 0.975Rint = 0.068
11893 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.077H-atom parameters constrained
wR(F2) = 0.266Δρmax = 1.15 e Å3
S = 1.15Δρmin = 0.36 e Å3
15153 reflectionsAbsolute structure: Flack (1983), 2575 Friedel pairs
341 parametersAbsolute structure parameter: 0.1 (3)
45 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.40677 (8)0.95002 (8)0.4154 (3)0.0199 (3)
H10.42420.96930.32510.030*
O20.08964 (8)0.54803 (8)0.4294 (3)0.0208 (4)
H20.07430.53230.33160.031*
O1W0.50001.00000.1754 (4)0.0197 (5)
H1W0.48371.03030.10930.030*
O2W0.00000.50000.1640 (4)0.0203 (5)
H2W0.01640.46940.09870.031*
C10.23302 (12)1.02383 (11)0.3489 (4)0.0233 (5)
H1A0.25031.06990.35280.035*
H1B0.21211.01290.46620.035*
H1C0.19961.02000.25130.035*
C20.32326 (12)0.99569 (11)0.1298 (4)0.0204 (5)
H2A0.33681.04290.13640.031*
H2B0.29050.98990.03140.031*
H2C0.36270.96770.10560.031*
C30.29148 (12)0.97463 (11)0.3120 (3)0.0177 (5)
C40.34506 (11)0.98337 (11)0.4633 (4)0.0184 (5)
H40.35431.03230.47970.022*
C50.32263 (12)0.95406 (11)0.6451 (3)0.0195 (5)
H5A0.28300.97920.68990.023*
H5B0.35910.95940.73560.023*
C60.30465 (11)0.87956 (11)0.6280 (3)0.0179 (5)
H6A0.28990.86270.74860.022*
H6B0.34540.85420.59250.022*
C70.18212 (12)0.89138 (12)0.5695 (4)0.0201 (5)
H7A0.18540.93970.59260.030*
H7B0.17320.86790.68440.030*
H7C0.14550.88270.48350.030*
C80.24895 (10)0.86580 (11)0.4874 (3)0.0151 (4)
C90.26992 (11)0.89986 (11)0.3032 (3)0.0148 (4)
H90.31150.87550.26560.018*
C100.21932 (11)0.88426 (11)0.1525 (3)0.0182 (5)
H10A0.23180.90880.04010.022*
H10B0.17410.89940.19040.022*
C110.21803 (11)0.80866 (11)0.1139 (3)0.0173 (4)
H11A0.26230.79500.06490.021*
H11B0.18390.79950.01880.021*
C120.12674 (11)0.77502 (12)0.3267 (4)0.0189 (5)
H12A0.09980.76000.22240.028*
H12B0.11760.82250.35080.028*
H12C0.11500.74840.43450.028*
C130.20209 (11)0.76580 (11)0.2830 (3)0.0149 (4)
C140.24821 (11)0.78826 (10)0.4463 (3)0.0151 (4)
H140.29480.77820.40370.018*
C150.23867 (12)0.74306 (11)0.6142 (4)0.0196 (5)
H15A0.27010.75740.71120.024*
H15B0.19240.74870.66120.024*
C160.25069 (11)0.66882 (11)0.5715 (3)0.0181 (5)
H16A0.29810.66190.53570.022*
H16B0.24160.64140.68140.022*
C170.20446 (11)0.64684 (10)0.4162 (3)0.0166 (4)
H170.15750.65720.45550.020*
C180.29079 (11)0.67911 (11)0.1759 (4)0.0197 (5)
H18A0.29840.63130.15260.030*
H18B0.32240.69490.26900.030*
H18C0.29760.70450.06300.030*
C190.21845 (11)0.68953 (11)0.2437 (3)0.0166 (4)
C200.17282 (12)0.65349 (11)0.1054 (4)0.0201 (5)
H20A0.18500.66570.02130.024*
H20B0.12510.66480.12650.024*
C210.18623 (12)0.57823 (11)0.1420 (4)0.0212 (5)
H21A0.22370.56180.06530.025*
H21B0.14570.55120.11510.025*
C220.20476 (11)0.57331 (11)0.3489 (3)0.0172 (5)
H220.25170.55590.35850.021*
C230.15811 (11)0.52502 (11)0.4544 (4)0.0199 (5)
C240.17163 (13)0.52639 (12)0.6588 (4)0.0247 (5)
H24A0.14090.49550.72070.037*
H24B0.16460.57200.70530.037*
H24C0.21810.51260.68210.037*
C250.16250 (12)0.45282 (11)0.3808 (4)0.0230 (5)
H25A0.14540.45280.25400.028*0.413 (3)
H25B0.13190.42440.45400.028*0.413 (3)
H25C0.13580.45040.26710.028*0.250 (7)
H25D0.14080.42270.47070.028*0.250 (7)
H25E0.15590.45420.24700.028*0.337 (7)
H25F0.12490.42660.43320.028*0.337 (7)
C260.2328 (3)0.4192 (5)0.3806 (13)0.0196 (19)0.413 (3)
H26A0.25920.43660.48500.024*0.413 (3)
H26B0.22740.37020.39730.024*0.413 (3)
C270.2701 (7)0.4317 (7)0.2113 (18)0.036 (2)0.413 (3)
H270.24150.41940.11310.043*0.413 (3)
C280.3265 (4)0.4528 (5)0.1393 (15)0.0416 (18)0.413 (3)
C290.3498 (5)0.4646 (7)0.0560 (17)0.059 (2)0.413 (3)
H29A0.39270.44170.07590.089*0.413 (3)
H29B0.35540.51280.07690.089*0.413 (3)
H29C0.31620.44680.14090.089*0.413 (3)
C300.3800 (6)0.4710 (7)0.277 (2)0.074 (3)0.413 (3)
H30A0.36310.46230.40030.112*0.413 (3)
H30B0.39130.51860.26460.112*0.413 (3)
H30C0.42010.44370.25500.112*0.413 (3)
C26'0.2338 (6)0.4245 (11)0.340 (2)0.0196 (19)0.250 (7)
H26C0.26320.44080.43950.024*0.250 (7)
H26D0.23050.37520.35500.024*0.250 (7)
C27'0.2706 (9)0.4359 (15)0.170 (2)0.036 (2)0.250 (7)
H27'0.25160.43530.05090.043*0.250 (7)
C28'0.3390 (7)0.4479 (8)0.211 (3)0.0416 (18)0.250 (7)
C29'0.3714 (9)0.4563 (11)0.024 (3)0.059 (2)0.250 (7)
H29D0.33640.45760.06960.089*0.250 (7)
H29E0.40160.41850.00070.089*0.250 (7)
H29F0.39700.49830.02150.089*0.250 (7)
C30'0.3828 (10)0.4522 (13)0.380 (4)0.074 (3)0.250 (7)
H30D0.35460.44920.48890.112*0.250 (7)
H30E0.40680.49510.37990.112*0.250 (7)
H30F0.41520.41520.37920.112*0.250 (7)
C26"0.2285 (6)0.4150 (10)0.423 (2)0.0196 (19)0.337 (7)
H26E0.24610.42960.54260.024*0.337 (7)
H26F0.21940.36620.42930.024*0.337 (7)
C27"0.2785 (6)0.4279 (7)0.2825 (19)0.036 (2)0.337 (7)
H27"0.26480.41870.16090.043*0.337 (7)
C28"0.3442 (5)0.4520 (5)0.3021 (19)0.0416 (18)0.337 (7)
C29"0.3880 (6)0.4653 (7)0.136 (2)0.059 (2)0.337 (7)
H29G0.35980.46740.02700.089*0.337 (7)
H29H0.42080.42900.12340.089*0.337 (7)
H29I0.41160.50810.15220.089*0.337 (7)
C30"0.3691 (7)0.4694 (9)0.493 (2)0.074 (3)0.337 (7)
H30G0.36060.51700.51740.112*0.337 (7)
H30H0.41740.46060.50050.112*0.337 (7)
H30I0.34540.44180.58270.112*0.337 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0214 (8)0.0221 (8)0.0162 (9)0.0034 (6)0.0000 (7)0.0006 (7)
O20.0198 (8)0.0223 (8)0.0202 (10)0.0020 (6)0.0014 (7)0.0015 (7)
O1W0.0230 (11)0.0194 (11)0.0168 (13)0.0029 (8)0.0000.000
O2W0.0254 (11)0.0196 (11)0.0161 (13)0.0054 (8)0.0000.000
C10.0280 (12)0.0164 (10)0.0255 (14)0.0030 (8)0.0015 (10)0.0008 (9)
C20.0240 (11)0.0194 (10)0.0179 (13)0.0032 (8)0.0001 (9)0.0031 (9)
C30.0223 (11)0.0163 (10)0.0145 (12)0.0017 (8)0.0011 (9)0.0016 (9)
C40.0227 (11)0.0160 (10)0.0164 (13)0.0021 (8)0.0011 (9)0.0029 (9)
C50.0273 (11)0.0195 (10)0.0116 (13)0.0055 (8)0.0018 (9)0.0019 (9)
C60.0234 (11)0.0191 (10)0.0113 (12)0.0031 (8)0.0019 (9)0.0002 (9)
C70.0225 (11)0.0215 (11)0.0162 (13)0.0019 (8)0.0048 (9)0.0021 (9)
C80.0170 (10)0.0138 (10)0.0145 (12)0.0001 (7)0.0002 (8)0.0013 (8)
C90.0181 (10)0.0146 (9)0.0118 (12)0.0011 (7)0.0012 (8)0.0009 (8)
C100.0231 (11)0.0176 (10)0.0140 (13)0.0008 (8)0.0025 (9)0.0018 (9)
C110.0230 (10)0.0195 (10)0.0093 (11)0.0023 (8)0.0023 (9)0.0001 (9)
C120.0173 (10)0.0219 (11)0.0175 (13)0.0020 (8)0.0016 (9)0.0029 (9)
C130.0156 (10)0.0179 (10)0.0110 (11)0.0023 (7)0.0000 (8)0.0007 (8)
C140.0162 (10)0.0178 (10)0.0112 (12)0.0002 (7)0.0016 (8)0.0014 (9)
C150.0244 (11)0.0200 (11)0.0144 (13)0.0052 (8)0.0022 (9)0.0010 (9)
C160.0209 (11)0.0187 (10)0.0148 (12)0.0022 (8)0.0024 (9)0.0025 (9)
C170.0191 (10)0.0159 (10)0.0149 (12)0.0034 (7)0.0019 (9)0.0015 (9)
C180.0205 (10)0.0170 (10)0.0218 (13)0.0022 (8)0.0035 (9)0.0019 (9)
C190.0175 (10)0.0184 (11)0.0140 (12)0.0026 (8)0.0013 (9)0.0002 (9)
C200.0261 (11)0.0200 (10)0.0142 (12)0.0034 (8)0.0011 (9)0.0015 (9)
C210.0280 (12)0.0197 (11)0.0158 (13)0.0045 (8)0.0011 (10)0.0030 (9)
C220.0194 (10)0.0156 (10)0.0167 (13)0.0001 (7)0.0004 (9)0.0020 (9)
C230.0203 (11)0.0193 (11)0.0200 (14)0.0015 (8)0.0002 (9)0.0016 (9)
C240.0303 (12)0.0227 (11)0.0210 (14)0.0059 (9)0.0026 (11)0.0041 (10)
C250.0251 (11)0.0187 (11)0.0253 (15)0.0039 (8)0.0015 (10)0.0028 (10)
C260.0337 (17)0.014 (3)0.012 (6)0.0011 (16)0.004 (3)0.009 (4)
C270.034 (2)0.021 (2)0.053 (6)0.0028 (16)0.018 (3)0.000 (5)
C280.028 (3)0.041 (2)0.057 (5)0.0006 (19)0.002 (3)0.007 (4)
C290.029 (3)0.075 (4)0.073 (6)0.002 (3)0.010 (3)0.002 (4)
C300.038 (3)0.093 (5)0.091 (7)0.014 (3)0.020 (5)0.019 (5)
C26'0.0337 (17)0.014 (3)0.012 (6)0.0011 (16)0.004 (3)0.009 (4)
C27'0.034 (2)0.021 (2)0.053 (6)0.0028 (16)0.018 (3)0.000 (5)
C28'0.028 (3)0.041 (2)0.057 (5)0.0006 (19)0.002 (3)0.007 (4)
C29'0.029 (3)0.075 (4)0.073 (6)0.002 (3)0.010 (3)0.002 (4)
C30'0.038 (3)0.093 (5)0.091 (7)0.014 (3)0.020 (5)0.019 (5)
C26"0.0337 (17)0.014 (3)0.012 (6)0.0011 (16)0.004 (3)0.009 (4)
C27"0.034 (2)0.021 (2)0.053 (6)0.0028 (16)0.018 (3)0.000 (5)
C28"0.028 (3)0.041 (2)0.057 (5)0.0006 (19)0.002 (3)0.007 (4)
C29"0.029 (3)0.075 (4)0.073 (6)0.002 (3)0.010 (3)0.002 (4)
C30"0.038 (3)0.093 (5)0.091 (7)0.014 (3)0.020 (5)0.019 (5)
Geometric parameters (Å, º) top
O1—C41.441 (3)C20—H20A0.9900
O1—H10.8400C20—H20B0.9900
O2—C231.451 (3)C21—C221.564 (4)
O2—H20.8400C21—H21A0.9900
O1W—H1W0.8400C21—H21B0.9900
O2W—H2W0.8400C22—C231.545 (3)
C1—C31.546 (3)C22—H221.0000
C1—H1A0.9800C23—C241.523 (4)
C1—H1B0.9800C23—C251.539 (3)
C1—H1C0.9800C24—H24A0.9800
C2—C31.536 (3)C24—H24B0.9800
C2—H2A0.9800C24—H24C0.9800
C2—H2B0.9800C25—C26"1.547 (7)
C2—H2C0.9800C25—C261.553 (6)
C3—C41.549 (3)C25—C26'1.557 (8)
C3—C91.552 (3)C25—H25A0.9900
C4—C51.522 (3)C25—H25B0.9900
C4—H41.0000C25—H25C0.9900
C5—C61.532 (3)C25—H25D0.9902
C5—H5A0.9900C25—H25E0.9900
C5—H5B0.9900C25—H25F0.9901
C6—C81.539 (3)C26—C271.467 (8)
C6—H6A0.9900C26—H26A0.9900
C6—H6B0.9900C26—H26B0.9900
C7—C81.547 (3)C27—C281.311 (13)
C7—H7A0.9800C27—H270.9500
C7—H7B0.9800C28—C301.510 (14)
C7—H7C0.9800C28—C291.523 (13)
C8—C91.567 (3)C29—H29A0.9800
C8—C141.574 (3)C29—H29B0.9800
C9—C101.528 (3)C29—H29C0.9800
C9—H91.0000C30—H30A0.9800
C10—C111.533 (3)C30—H30B0.9800
C10—H10A0.9900C30—H30C0.9800
C10—H10B0.9900C26'—C27'1.465 (10)
C11—C131.539 (3)C26'—H26C0.9900
C11—H11A0.9900C26'—H26D0.9900
C11—H11B0.9900C27'—C28'1.417 (16)
C12—C131.546 (3)C27'—H27'0.9500
C12—H12A0.9800C28'—C30'1.514 (16)
C12—H12B0.9800C28'—C29'1.523 (14)
C12—H12C0.9800C29'—H29D0.9800
C13—C141.574 (3)C29'—H29E0.9800
C13—C191.581 (3)C29'—H29F0.9800
C14—C151.537 (3)C30'—H30D0.9800
C14—H141.0000C30'—H30E0.9800
C15—C161.531 (3)C30'—H30F0.9800
C15—H15A0.9900C26"—C27"1.454 (9)
C15—H15B0.9900C26"—H26E0.9900
C16—C171.528 (3)C26"—H26F0.9900
C16—H16A0.9900C27"—C28"1.401 (14)
C16—H16B0.9900C27"—H27"0.9500
C17—C221.546 (3)C28"—C29"1.518 (14)
C17—C191.549 (3)C28"—C30"1.522 (15)
C17—H171.0000C29"—H29G0.9800
C18—C191.538 (3)C29"—H29H0.9800
C18—H18A0.9800C29"—H29I0.9800
C18—H18B0.9800C30"—H30G0.9800
C18—H18C0.9800C30"—H30H0.9800
C19—C201.540 (3)C30"—H30I0.9800
C20—C211.547 (3)
C4—O1—H1109.5H18A—C18—H18B109.5
C23—O2—H2109.5C19—C18—H18C109.5
C3—C1—H1A109.5H18A—C18—H18C109.5
C3—C1—H1B109.5H18B—C18—H18C109.5
H1A—C1—H1B109.5C18—C19—C20106.1 (2)
C3—C1—H1C109.5C18—C19—C17110.99 (19)
H1A—C1—H1C109.5C20—C19—C17100.09 (18)
H1B—C1—H1C109.5C18—C19—C13112.45 (17)
C3—C2—H2A109.5C20—C19—C13116.53 (19)
C3—C2—H2B109.5C17—C19—C13109.99 (19)
H2A—C2—H2B109.5C19—C20—C21103.65 (19)
C3—C2—H2C109.5C19—C20—H20A111.0
H2A—C2—H2C109.5C21—C20—H20A111.0
H2B—C2—H2C109.5C19—C20—H20B111.0
C2—C3—C1106.84 (19)C21—C20—H20B111.0
C2—C3—C4107.92 (19)H20A—C20—H20B109.0
C1—C3—C4108.8 (2)C20—C21—C22105.65 (19)
C2—C3—C9109.91 (19)C20—C21—H21A110.6
C1—C3—C9114.03 (19)C22—C21—H21A110.6
C4—C3—C9109.15 (18)C20—C21—H21B110.6
O1—C4—C5106.67 (19)C22—C21—H21B110.6
O1—C4—C3111.20 (19)H21A—C21—H21B108.7
C5—C4—C3112.43 (18)C23—C22—C17115.33 (19)
O1—C4—H4108.8C23—C22—C21112.48 (19)
C5—C4—H4108.8C17—C22—C21104.44 (18)
C3—C4—H4108.8C23—C22—H22108.1
C4—C5—C6111.6 (2)C17—C22—H22108.1
C4—C5—H5A109.3C21—C22—H22108.1
C6—C5—H5A109.3O2—C23—C24106.6 (2)
C4—C5—H5B109.3O2—C23—C25107.73 (18)
C6—C5—H5B109.3C24—C23—C25110.6 (2)
H5A—C5—H5B108.0O2—C23—C22107.80 (18)
C5—C6—C8113.33 (19)C24—C23—C22112.02 (19)
C5—C6—H6A108.9C25—C23—C22111.9 (2)
C8—C6—H6A108.9C23—C24—H24A109.5
C5—C6—H6B108.9C23—C24—H24B109.5
C8—C6—H6B108.9H24A—C24—H24B109.5
H6A—C6—H6B107.7C23—C24—H24C109.5
C8—C7—H7A109.5H24A—C24—H24C109.5
C8—C7—H7B109.5H24B—C24—H24C109.5
H7A—C7—H7B109.5C23—C25—C26"115.7 (9)
C8—C7—H7C109.5C23—C25—C26117.0 (5)
H7A—C7—H7C109.5C23—C25—C26'117.3 (10)
H7B—C7—H7C109.5C23—C25—H25A108.0
C6—C8—C7107.5 (2)C26—C25—H25A108.0
C6—C8—C9107.90 (17)C23—C25—H25B108.0
C7—C8—C9114.95 (18)C26—C25—H25B108.0
C6—C8—C14108.04 (17)H25A—C25—H25B107.3
C7—C8—C14112.92 (17)C23—C25—H25C108.1
C9—C8—C14105.23 (18)C26—C25—H25C117.6
C10—C9—C3114.06 (18)C26'—C25—H25C108.1
C10—C9—C8111.03 (18)C23—C25—H25D107.9
C3—C9—C8117.00 (19)C23—C25—H25E108.4
C10—C9—H9104.4C26"—C25—H25E108.8
C3—C9—H9104.4C23—C25—H25F108.3
C8—C9—H9104.4C26"—C25—H25F108.0
C9—C10—C11110.16 (18)H25E—C25—H25F107.4
C9—C10—H10A109.6C27—C26—C25112.6 (7)
C11—C10—H10A109.6C27—C26—H26A109.1
C9—C10—H10B109.6C25—C26—H26A109.1
C11—C10—H10B109.6C27—C26—H26B109.1
H10A—C10—H10B108.1C25—C26—H26B109.1
C10—C11—C13113.6 (2)H26A—C26—H26B107.8
C10—C11—H11A108.9C28—C27—C26145.9 (14)
C13—C11—H11A108.9C28—C27—H27107.0
C10—C11—H11B108.9C26—C27—H27107.0
C13—C11—H11B108.9C27—C28—C30114.4 (12)
H11A—C11—H11B107.7C27—C28—C29133.5 (11)
C13—C12—H12A109.5C30—C28—C29112.1 (9)
C13—C12—H12B109.5C27'—C26'—C25124.3 (14)
H12A—C12—H12B109.5C27'—C26'—H26C106.2
C13—C12—H12C109.5C25—C26'—H26C106.2
H12A—C12—H12C109.5C27'—C26'—H26D106.2
H12B—C12—H12C109.5C25—C26'—H26D106.2
C11—C13—C12107.53 (19)H26C—C26'—H26D106.4
C11—C13—C14109.55 (17)C28'—C27'—C26'109.0 (16)
C12—C13—C14112.08 (19)C28'—C27'—H27'125.5
C11—C13—C19110.12 (19)C26'—C27'—H27'125.5
C12—C13—C19110.62 (17)C27'—C28'—C30'137.5 (17)
C14—C13—C19106.95 (17)C27'—C28'—C29'103.5 (14)
C15—C14—C13111.72 (17)C30'—C28'—C29'118.9 (15)
C15—C14—C8115.04 (19)C28'—C29'—H29D109.5
C13—C14—C8115.47 (18)C28'—C29'—H29E109.5
C15—C14—H14104.3H29D—C29'—H29E109.5
C13—C14—H14104.3C28'—C29'—H29F109.5
C8—C14—H14104.3H29D—C29'—H29F109.5
C16—C15—C14112.5 (2)H29E—C29'—H29F109.5
C16—C15—H15A109.1C28'—C30'—H30D109.5
C14—C15—H15A109.1C28'—C30'—H30E109.5
C16—C15—H15B109.1H30D—C30'—H30E109.5
C14—C15—H15B109.1C28'—C30'—H30F109.5
H15A—C15—H15B107.8H30D—C30'—H30F109.5
C17—C16—C15109.57 (18)H30E—C30'—H30F109.5
C17—C16—H16A109.8C27"—C26"—C25110.9 (9)
C15—C16—H16A109.8C27"—C26"—H26E109.5
C17—C16—H16B109.8C25—C26"—H26E109.5
C15—C16—H16B109.8C27"—C26"—H26F109.5
H16A—C16—H16B108.2C25—C26"—H26F109.5
C16—C17—C22120.46 (19)H26E—C26"—H26F108.1
C16—C17—C19110.00 (17)C28"—C27"—C26"128.9 (14)
C22—C17—C19105.02 (19)C28"—C27"—H27"115.5
C16—C17—H17106.9C26"—C27"—H27"115.5
C22—C17—H17106.9C27"—C28"—C29"121.0 (11)
C19—C17—H17106.9C27"—C28"—C30"118.5 (11)
C19—C18—H18A109.5C29"—C28"—C30"120.4 (11)
C19—C18—H18B109.5
C2—C3—C4—O151.8 (2)C11—C13—C19—C1854.0 (3)
C1—C3—C4—O1167.36 (18)C12—C13—C19—C18172.7 (2)
C9—C3—C4—O167.6 (2)C14—C13—C19—C1865.0 (2)
C2—C3—C4—C5171.33 (18)C11—C13—C19—C2068.8 (2)
C1—C3—C4—C573.1 (2)C12—C13—C19—C2049.9 (3)
C9—C3—C4—C551.9 (2)C14—C13—C19—C20172.23 (19)
O1—C4—C5—C665.2 (2)C11—C13—C19—C17178.24 (18)
C3—C4—C5—C656.9 (3)C12—C13—C19—C1763.0 (2)
C4—C5—C6—C858.0 (3)C14—C13—C19—C1759.3 (2)
C5—C6—C8—C772.1 (2)C18—C19—C20—C2171.1 (2)
C5—C6—C8—C952.4 (2)C17—C19—C20—C2144.3 (2)
C5—C6—C8—C14165.72 (19)C13—C19—C20—C21162.83 (19)
C2—C3—C9—C1059.2 (2)C19—C20—C21—C2229.7 (2)
C1—C3—C9—C1060.8 (3)C16—C17—C22—C2386.4 (3)
C4—C3—C9—C10177.36 (19)C19—C17—C22—C23148.94 (19)
C2—C3—C9—C8168.87 (18)C16—C17—C22—C21149.6 (2)
C1—C3—C9—C871.2 (3)C19—C17—C22—C2125.0 (2)
C4—C3—C9—C850.7 (2)C20—C21—C22—C23122.9 (2)
C6—C8—C9—C10176.04 (17)C20—C21—C22—C172.9 (2)
C7—C8—C9—C1064.0 (2)C17—C22—C23—O262.8 (3)
C14—C8—C9—C1060.9 (2)C21—C22—C23—O256.9 (2)
C6—C8—C9—C350.6 (2)C17—C22—C23—C2454.1 (3)
C7—C8—C9—C369.3 (2)C21—C22—C23—C24173.8 (2)
C14—C8—C9—C3165.81 (18)C17—C22—C23—C25179.0 (2)
C3—C9—C10—C11161.98 (19)C21—C22—C23—C2561.4 (2)
C8—C9—C10—C1163.3 (2)O2—C23—C25—C26"170.6 (5)
C9—C10—C11—C1356.8 (2)C24—C23—C25—C26"54.5 (6)
C10—C11—C13—C1272.8 (2)C22—C23—C25—C26"71.1 (6)
C10—C11—C13—C1449.3 (2)O2—C23—C25—C26175.8 (4)
C10—C11—C13—C19166.64 (17)C24—C23—C25—C2668.1 (4)
C11—C13—C14—C15175.11 (18)C22—C23—C25—C2657.5 (5)
C12—C13—C14—C1565.6 (2)O2—C23—C25—C26'162.7 (7)
C19—C13—C14—C1555.8 (2)C24—C23—C25—C26'81.2 (7)
C11—C13—C14—C850.9 (2)C22—C23—C25—C26'44.4 (7)
C12—C13—C14—C868.4 (2)C23—C25—C26—C2789.5 (10)
C19—C13—C14—C8170.25 (18)C26"—C25—C26—C27176 (6)
C6—C8—C14—C1556.6 (2)C26'—C25—C26—C275 (5)
C7—C8—C14—C1562.2 (3)C25—C26—C27—C28127.9 (19)
C9—C8—C14—C15171.71 (18)C26—C27—C28—C303 (3)
C6—C8—C14—C13170.91 (19)C26—C27—C28—C29175.1 (16)
C7—C8—C14—C1370.3 (3)C23—C25—C26'—C27'84 (2)
C9—C8—C14—C1355.8 (2)C26"—C25—C26'—C27'177 (6)
C13—C14—C15—C1655.9 (2)C26—C25—C26'—C27'176 (7)
C8—C14—C15—C16169.89 (17)C25—C26'—C27'—C28'139 (2)
C14—C15—C16—C1756.4 (2)C26'—C27'—C28'—C30'0 (4)
C15—C16—C17—C22178.3 (2)C26'—C27'—C28'—C29'178.1 (19)
C15—C16—C17—C1959.5 (2)C23—C25—C26"—C27"87.7 (15)
C16—C17—C19—C1862.3 (2)C26—C25—C26"—C27"11 (4)
C22—C17—C19—C1868.7 (2)C26'—C25—C26"—C27"12 (3)
C16—C17—C19—C20174.03 (18)C25—C26"—C27"—C28"125.6 (15)
C22—C17—C19—C2043.0 (2)C26"—C27"—C28"—C29"177.1 (14)
C16—C17—C19—C1362.8 (2)C26"—C27"—C28"—C30"1 (2)
C22—C17—C19—C13166.21 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1w0.841.962.745 (2)154
O2—H2···O2w0.842.032.809 (2)154
O1w—H1w···O2i0.841.882.712 (2)171
O2w—H2w···O1ii0.841.952.786 (2)171
Symmetry codes: (i) y+1, x+1, z1/2; (ii) y+1, x, z1/2.

Experimental details

Crystal data
Chemical formulaC30H52O2·H2O
Mr462.73
Crystal system, space groupTetragonal, P42
Temperature (K)100
a, c (Å)19.9229 (1), 7.3302 (1)
V3)2909.52 (4)
Z4
Radiation typeCu Kα
µ (mm1)0.50
Crystal size (mm)0.30 × 0.10 × 0.05
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with an Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2012)
Tmin, Tmax0.864, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
11893, 15153, 14049
Rint0.068
(sin θ/λ)max1)0.632
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.077, 0.266, 1.15
No. of reflections15153
No. of parameters341
No. of restraints45
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.15, 0.36
Absolute structureFlack (1983), 2575 Friedel pairs
Absolute structure parameter0.1 (3)

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1w0.841.962.745 (2)154
O2—H2···O2w0.842.032.809 (2)154
O1w—H1w···O2i0.841.882.712 (2)171
O2w—H2w···O1ii0.841.952.786 (2)171
Symmetry codes: (i) y+1, x+1, z1/2; (ii) y+1, x, z1/2.
 

Acknowledgements

We thank Padjadjaran University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

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Volume 68| Part 9| September 2012| Pages o2712-o2713
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