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

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ISSN: 2056-9890

17-(5-Ethyl-6-methyl­heptan-2-yl)-10,13-di­methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra­deca­hydro-1H-cyclo­penta[a]phenanthrene-3,7-diol from Chisocheton tomentosus (Meliaceae)

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 12 October 2008; accepted 13 October 2008; online 22 October 2008)

The asymmetric unit of the title compound, C29H50O2, contains two mol­ecules; one mol­ecule is linked to the other by two O—H⋯O hydrogen bonds, whereas only one of the hydr­oxy groups of the second mol­ecule is involved in hydrogen bonding. This gives rise to a chain that runs along the a axis of the monoclinic unit cell.

Related literature

This study is the first on Chisocheton tomentosus. For literature on other Chisocheton species, see: Awang et al. (2007[Awang, K., Lim, C. S., Mohamad, K., Morita, H., Hirasawa, Y., Takeya, K., Thoison, O. & Hadi, A. H. A. (2007). Bioorg. Med. Chem. 15, 5997-6002.]); Bordoloi et al. (1993[Bordoloi, M., Saikia, B., Mathur, R. K. & Goswami, B. N. (1993). Phytochemistry, 34, 583-584.]); Gunning et al. (1994[Gunning, P. J., Jeffs, L. B., Isman, M. B. & Towers, G. H. N. (1994). Phytochemistry, 36, 1245-1248.]); Inada et al. (1993[Inada, A., Somekawa, M., Murata, H., Nakanishi, T., Tokuda, H., Nishino, H., Iwashima, A., Darnaedi, D. & Jurata, J. (1993). Chem. Pharm. Bull. 41, 617-619.]); Phongmaykin et al. (2008[Phongmaykin, J., Kumamoto, T., Ishikawa, T., Suttisri, R. & Saifah, E. (2008). Arch. Pharm. Res. 31, 21-27.]); Tzouros et al. (2004[Tzouros, M., Bigler, L., Bienz, S., Hesse, M., Inada, A., Murata, H., Inatomi, Y., Nakanishi, T. & Darnaedi, D. (2004). Helv. Chim. Acta, 87, 1411-1425.]).

[Scheme 1]

Experimental

Crystal data
  • C29H50O2

  • Mr = 430.69

  • Monoclinic, P 21

  • a = 8.1690 (1) Å

  • b = 12.2369 (2) Å

  • c = 25.6945 (4) Å

  • β = 93.652 (1)°

  • V = 2563.29 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 100 (2) K

  • 0.45 × 0.15 × 0.03 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 21218 measured reflections

  • 6154 independent reflections

  • 5389 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.172

  • S = 1.11

  • 6154 reflections

  • 575 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.46 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1O⋯O4 0.84 1.92 2.762 (3) 178
O2—H2O⋯O3 0.84 1.87 2.686 (3) 165
O3—H3O⋯O1i 0.84 1.86 2.694 (3) 170
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Related literature top

This study is the first on Chisocheton tomentosus. For literature on other Chisocheton species, see: Awang et al. (2007); Bordoloi et al. (1993); Gunning et al. (1994); Inada et al. (1993); Phongmaykin et al. (2008); Tzouros et al. (2004).

Experimental top

Dried ground bark of Chisocheton tomentosus (3.5 kg) was defatted with hexane for 5 days. The solvent was removed and the plant material dried before being extracted with dichloromethane for another 5 days. The dichloromethane was removed by evaporation to give a crude material (10 g) that was subjected to column chromatography over silica gel. Separation was effected with hexane/dichloromethane (95:5 v/v). The polarity was increased with acetone, and finally with acetone/methanol to give 24 fractions. One of the later fractions was subjected to column chromatography (25:25:50 v/v acetone/dichloromethane/hexane) to give five other fractions. The third fraction yielded colorless crystals when the solvents were allowed to evaporate.

Refinement top

In the absence of significant anomalous dispersion effects, Friedel pairs were averaged. Carbon- and oxygen-bound H-atoms were placed in calculated positions (C—H 0.95–1.00, O–H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C,O).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2008).

Figures top
[Figure 1] Fig. 1. 70% Probability displacement ellipsoid plot (Barbour, 2001) of C29H50O2. Hydrogen atoms are drawn as spheres of arbitrary radii.
17-(5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl- 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H- cyclopenta[a]phenanthrene-3,7-diol top
Crystal data top
C29H50O2F(000) = 960
Mr = 430.69Dx = 1.116 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 7107 reflections
a = 8.1690 (1) Åθ = 2.3–28.3°
b = 12.2369 (2) ŵ = 0.07 mm1
c = 25.6945 (4) ÅT = 100 K
β = 93.652 (1)°Prism, colourless
V = 2563.29 (7) Å30.45 × 0.15 × 0.03 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
5389 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 27.5°, θmin = 0.8°
ω scansh = 1010
21218 measured reflectionsk = 1415
6154 independent reflectionsl = 3333
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.1065P)2 + 0.6901P]
where P = (Fo2 + 2Fc2)/3
6154 reflections(Δ/σ)max = 0.001
575 parametersΔρmax = 0.46 e Å3
1 restraintΔρmin = 0.27 e Å3
Crystal data top
C29H50O2V = 2563.29 (7) Å3
Mr = 430.69Z = 4
Monoclinic, P21Mo Kα radiation
a = 8.1690 (1) ŵ = 0.07 mm1
b = 12.2369 (2) ÅT = 100 K
c = 25.6945 (4) Å0.45 × 0.15 × 0.03 mm
β = 93.652 (1)°
Data collection top
Bruker SMART APEX
diffractometer
5389 reflections with I > 2σ(I)
21218 measured reflectionsRint = 0.039
6154 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0601 restraint
wR(F2) = 0.172H-atom parameters constrained
S = 1.11Δρmax = 0.46 e Å3
6154 reflectionsΔρmin = 0.27 e Å3
575 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6382 (2)0.7500 (2)0.97759 (9)0.0231 (5)
H1O0.61620.73290.94630.035*
O20.0206 (3)0.7449 (2)1.12076 (9)0.0297 (6)
H2O0.01180.73381.08880.045*
O30.0524 (3)0.7160 (2)1.01700 (9)0.0293 (6)
H3O0.14370.73261.00220.044*
O40.5741 (3)0.6943 (2)0.87412 (9)0.0243 (5)
H4O0.64880.67840.85440.036*
C10.5203 (3)0.7010 (3)1.00956 (12)0.0204 (6)
H10.41140.69960.98950.024*
C20.5068 (4)0.7730 (3)1.05748 (12)0.0222 (6)
H2A0.61580.77911.07640.027*
H2B0.47160.84721.04630.027*
C30.3855 (4)0.7269 (2)1.09368 (11)0.0188 (6)
C40.4110 (3)0.6076 (2)1.11020 (12)0.0171 (6)
C50.5651 (4)0.6019 (3)1.14821 (12)0.0227 (6)
H5A0.54060.63431.18170.034*
H5B0.65490.64241.13350.034*
H5C0.59750.52541.15350.034*
C60.4381 (4)0.5384 (3)1.06090 (12)0.0197 (6)
H6A0.47370.46411.07200.024*
H6B0.33210.53111.04030.024*
C70.5650 (4)0.5859 (3)1.02586 (13)0.0218 (6)
H7A0.67430.58581.04490.026*
H7B0.57120.53960.99450.026*
C80.2635 (4)0.7893 (3)1.10964 (12)0.0230 (6)
H80.25490.86171.09650.028*
C90.1395 (4)0.7532 (3)1.14665 (12)0.0214 (6)
H90.13420.81121.17390.026*
C100.1912 (4)0.6469 (2)1.17448 (11)0.0178 (6)
H100.28230.66371.20110.021*
C110.2546 (4)0.5652 (2)1.13538 (12)0.0175 (6)
H110.16720.55891.10650.021*
C120.0496 (4)0.5984 (3)1.20216 (12)0.0197 (6)
H120.03820.58171.17440.024*
C130.0879 (4)0.4906 (3)1.23062 (12)0.0193 (6)
C140.2300 (4)0.5024 (3)1.27277 (13)0.0235 (6)
H14A0.19410.54721.30150.035*
H14B0.32370.53751.25760.035*
H14C0.26250.42991.28600.035*
C150.1318 (4)0.4089 (3)1.18813 (13)0.0234 (7)
H15A0.15950.33741.20440.028*
H15B0.03570.39851.16310.028*
C160.2773 (4)0.4499 (2)1.15891 (13)0.0228 (7)
H16A0.29710.39791.13050.027*
H16B0.37630.45001.18320.027*
C170.0307 (4)0.6698 (3)1.24235 (13)0.0272 (7)
H17A0.10210.72621.22510.033*
H17B0.05290.70591.26600.033*
C180.1323 (4)0.5869 (3)1.27215 (13)0.0278 (7)
H18A0.25070.59681.26270.033*
H18B0.11310.59791.31020.033*
C190.0770 (4)0.4705 (3)1.25683 (13)0.0229 (6)
H190.15840.44301.22910.028*
C200.0783 (4)0.3906 (3)1.30303 (14)0.0249 (7)
H200.00440.42111.33200.030*
C210.0136 (5)0.2765 (3)1.28981 (17)0.0370 (9)
H21A0.03350.22591.31830.056*
H21B0.10440.28071.28520.056*
H21C0.07060.25031.25750.056*
C220.2509 (4)0.3809 (3)1.32302 (14)0.0310 (8)
H22A0.29940.45491.32430.037*
H22B0.32000.33741.29760.037*
C230.2574 (5)0.3286 (4)1.37654 (16)0.0406 (9)
H23A0.19830.37691.40230.049*
H23B0.19660.25861.37630.049*
C240.4290 (5)0.3056 (4)1.39556 (15)0.0391 (9)
H240.48610.25701.36890.047*
C250.4156 (6)0.2408 (4)1.44664 (18)0.0487 (11)
H25A0.33760.27871.47160.058*
H25B0.52410.24061.46180.058*
C260.3607 (10)0.1263 (6)1.4410 (3)0.081 (2)
H26A0.36550.08841.47450.122*
H26B0.24770.12541.43030.122*
H26C0.43260.08921.41460.122*
C270.5338 (5)0.4085 (5)1.39847 (17)0.0471 (11)
H270.53630.44381.36330.057*
C280.4660 (8)0.4907 (6)1.4369 (3)0.0713 (16)
H28A0.52730.55931.43230.107*
H28B0.35010.50381.43120.107*
H28C0.47600.46311.47230.107*
C290.7116 (6)0.3790 (7)1.4087 (2)0.076 (2)
H29A0.78200.44301.40200.114*
H29B0.71730.35611.44510.114*
H29C0.74910.31921.38550.114*
C300.0493 (4)0.6698 (3)0.97992 (12)0.0235 (7)
H300.16160.66290.99750.028*
C310.0640 (4)0.7452 (3)0.93332 (12)0.0224 (6)
H31A0.04600.75650.91570.027*
H31B0.10600.81710.94570.027*
C320.1777 (3)0.6986 (3)0.89473 (11)0.0181 (6)
C330.1431 (3)0.5817 (3)0.87644 (11)0.0160 (6)
C340.0179 (4)0.5826 (3)0.84128 (12)0.0222 (6)
H34A0.09940.62830.85730.033*
H34B0.06000.50790.83730.033*
H34C0.00360.61230.80700.033*
C350.1201 (4)0.5101 (3)0.92521 (12)0.0209 (6)
H35A0.08270.43660.91360.025*
H35B0.22780.50150.94470.025*
C360.0024 (4)0.5562 (3)0.96208 (13)0.0255 (7)
H36A0.11290.55920.94400.031*
H36B0.00780.50760.99270.031*
C370.3035 (4)0.7581 (3)0.87996 (12)0.0199 (6)
H370.31740.82950.89410.024*
C380.4237 (3)0.7196 (3)0.84267 (12)0.0185 (6)
H380.44610.78030.81810.022*
C390.3607 (3)0.6209 (2)0.81143 (11)0.0153 (5)
H390.27130.64610.78590.018*
C400.2885 (3)0.5349 (2)0.84685 (11)0.0152 (6)
H400.37710.51620.87400.018*
C410.4956 (3)0.5704 (3)0.78089 (11)0.0175 (6)
H410.57980.54180.80740.021*
C420.4398 (4)0.4716 (3)0.74682 (11)0.0178 (6)
C430.3011 (4)0.5023 (3)0.70591 (12)0.0232 (6)
H43A0.34120.55720.68200.035*
H43B0.20810.53220.72350.035*
H43C0.26600.43700.68620.035*
C440.3826 (4)0.3852 (3)0.78485 (12)0.0206 (6)
H44A0.47670.36230.80850.025*
H44B0.34260.32010.76500.025*
C450.2451 (4)0.4284 (2)0.81739 (12)0.0198 (6)
H45A0.21800.37180.84290.024*
H45B0.14590.44100.79400.024*
C460.5878 (4)0.6436 (3)0.74431 (13)0.0255 (7)
H46A0.66950.68970.76410.031*
H46B0.51100.69140.72340.031*
C470.6719 (4)0.5619 (3)0.70931 (13)0.0250 (7)
H47A0.79200.56210.71760.030*
H47B0.65080.58200.67220.030*
C480.6003 (4)0.4470 (3)0.71962 (12)0.0205 (6)
H480.67730.40970.74570.025*
C490.5895 (4)0.3761 (3)0.66984 (12)0.0239 (7)
H490.51600.41450.64320.029*
C500.5169 (5)0.2628 (3)0.67837 (15)0.0329 (8)
H50A0.53040.21740.64750.049*
H50B0.40000.26980.68420.049*
H50C0.57390.22860.70890.049*
C510.7592 (4)0.3659 (3)0.64791 (13)0.0287 (7)
H51A0.82120.43420.65550.034*
H51B0.81970.30550.66610.034*
C520.7534 (5)0.3448 (4)0.58952 (15)0.0406 (10)
H52A0.67660.39770.57200.049*
H52B0.70840.27070.58270.049*
C530.9195 (5)0.3535 (4)0.56493 (15)0.0391 (9)
H530.89840.33810.52690.047*
C540.9931 (6)0.4687 (5)0.5694 (2)0.0570 (13)
H54A1.03900.47950.60570.068*
H54B1.08540.47320.54630.068*
C550.8742 (9)0.5623 (6)0.5556 (3)0.0802 (19)
H55A0.93020.63230.56190.120*
H55B0.78000.55750.57730.120*
H55C0.83600.55700.51870.120*
C561.0435 (5)0.2673 (4)0.58622 (16)0.0432 (10)
H561.06620.28190.62430.052*
C570.9728 (7)0.1508 (4)0.58050 (19)0.0544 (12)
H57A1.05480.09790.59410.082*
H57B0.94420.13560.54360.082*
H57C0.87430.14500.60020.082*
C581.2071 (6)0.2763 (5)0.5601 (2)0.0560 (13)
H58A1.25440.34900.56670.084*
H58B1.18790.26520.52240.084*
H58C1.28320.22050.57440.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0131 (10)0.0272 (12)0.0290 (11)0.0035 (9)0.0025 (8)0.0003 (9)
O20.0222 (11)0.0439 (15)0.0234 (11)0.0218 (11)0.0041 (9)0.0031 (10)
O30.0111 (10)0.0516 (16)0.0254 (11)0.0018 (11)0.0026 (8)0.0117 (11)
O40.0097 (9)0.0317 (13)0.0318 (11)0.0049 (9)0.0049 (8)0.0071 (10)
C10.0096 (13)0.0225 (16)0.0292 (15)0.0020 (12)0.0015 (11)0.0021 (13)
C20.0234 (15)0.0126 (14)0.0305 (16)0.0035 (12)0.0007 (12)0.0002 (12)
C30.0200 (14)0.0137 (14)0.0225 (14)0.0033 (11)0.0006 (11)0.0019 (11)
C40.0135 (13)0.0091 (13)0.0283 (15)0.0058 (10)0.0006 (11)0.0015 (11)
C50.0163 (14)0.0205 (16)0.0309 (16)0.0035 (12)0.0031 (12)0.0014 (12)
C60.0143 (14)0.0124 (13)0.0328 (16)0.0034 (11)0.0036 (11)0.0045 (12)
C70.0152 (13)0.0184 (15)0.0326 (16)0.0020 (12)0.0064 (11)0.0045 (13)
C80.0292 (17)0.0153 (15)0.0245 (15)0.0075 (13)0.0019 (12)0.0018 (11)
C90.0264 (16)0.0141 (14)0.0236 (14)0.0114 (12)0.0024 (11)0.0014 (11)
C100.0187 (14)0.0133 (14)0.0212 (14)0.0065 (11)0.0010 (11)0.0013 (11)
C110.0143 (13)0.0130 (13)0.0253 (14)0.0040 (11)0.0024 (11)0.0048 (11)
C120.0167 (14)0.0189 (15)0.0234 (14)0.0088 (12)0.0013 (11)0.0026 (12)
C130.0144 (13)0.0166 (15)0.0269 (14)0.0000 (12)0.0019 (11)0.0017 (12)
C140.0159 (14)0.0213 (16)0.0329 (16)0.0002 (12)0.0003 (12)0.0035 (13)
C150.0223 (15)0.0120 (14)0.0368 (17)0.0002 (12)0.0083 (13)0.0036 (12)
C160.0213 (15)0.0101 (14)0.0381 (17)0.0046 (12)0.0101 (13)0.0023 (12)
C170.0305 (17)0.0228 (17)0.0289 (16)0.0114 (14)0.0061 (13)0.0008 (13)
C180.0268 (16)0.0286 (18)0.0288 (16)0.0105 (14)0.0067 (13)0.0002 (14)
C190.0158 (14)0.0237 (16)0.0295 (16)0.0000 (12)0.0033 (12)0.0033 (13)
C200.0201 (15)0.0212 (16)0.0340 (17)0.0039 (13)0.0064 (12)0.0009 (13)
C210.037 (2)0.0208 (18)0.056 (2)0.0044 (15)0.0200 (17)0.0009 (16)
C220.0230 (16)0.036 (2)0.0348 (18)0.0072 (15)0.0071 (13)0.0037 (15)
C230.032 (2)0.049 (3)0.041 (2)0.0006 (18)0.0103 (16)0.0056 (19)
C240.041 (2)0.047 (2)0.0302 (18)0.0129 (19)0.0089 (15)0.0036 (17)
C250.049 (3)0.052 (3)0.046 (2)0.009 (2)0.0087 (19)0.006 (2)
C260.104 (5)0.067 (4)0.075 (4)0.018 (4)0.028 (4)0.010 (3)
C270.031 (2)0.068 (3)0.042 (2)0.004 (2)0.0075 (16)0.015 (2)
C280.077 (4)0.059 (4)0.078 (4)0.013 (3)0.011 (3)0.007 (3)
C290.037 (3)0.125 (6)0.067 (3)0.003 (3)0.014 (2)0.041 (4)
C300.0089 (13)0.0367 (19)0.0254 (15)0.0018 (13)0.0035 (11)0.0044 (13)
C310.0128 (13)0.0237 (16)0.0310 (15)0.0025 (12)0.0045 (11)0.0070 (13)
C320.0110 (13)0.0177 (15)0.0256 (14)0.0021 (11)0.0014 (10)0.0009 (12)
C330.0083 (12)0.0187 (14)0.0216 (13)0.0023 (11)0.0049 (10)0.0007 (11)
C340.0111 (13)0.0264 (16)0.0293 (15)0.0025 (12)0.0028 (11)0.0038 (13)
C350.0160 (14)0.0205 (16)0.0270 (15)0.0044 (12)0.0073 (11)0.0012 (12)
C360.0175 (15)0.0321 (19)0.0279 (16)0.0020 (13)0.0092 (12)0.0006 (13)
C370.0165 (14)0.0139 (14)0.0297 (15)0.0013 (11)0.0041 (11)0.0021 (12)
C380.0125 (13)0.0170 (15)0.0264 (14)0.0039 (11)0.0037 (11)0.0011 (11)
C390.0099 (12)0.0136 (13)0.0230 (14)0.0025 (10)0.0055 (10)0.0013 (11)
C400.0093 (12)0.0151 (14)0.0214 (13)0.0025 (10)0.0040 (10)0.0010 (11)
C410.0112 (12)0.0198 (15)0.0221 (13)0.0047 (11)0.0046 (10)0.0007 (11)
C420.0139 (13)0.0195 (15)0.0206 (13)0.0003 (11)0.0057 (10)0.0013 (11)
C430.0158 (14)0.0285 (17)0.0253 (15)0.0012 (13)0.0021 (11)0.0004 (13)
C440.0188 (14)0.0170 (15)0.0266 (15)0.0016 (12)0.0058 (11)0.0024 (12)
C450.0199 (14)0.0113 (14)0.0291 (15)0.0043 (11)0.0085 (12)0.0006 (11)
C460.0214 (15)0.0267 (18)0.0295 (16)0.0060 (13)0.0105 (12)0.0010 (13)
C470.0199 (15)0.0253 (17)0.0311 (16)0.0034 (13)0.0106 (12)0.0017 (13)
C480.0145 (13)0.0229 (16)0.0246 (15)0.0005 (12)0.0044 (11)0.0013 (12)
C490.0225 (15)0.0270 (17)0.0229 (14)0.0042 (13)0.0072 (12)0.0017 (13)
C500.039 (2)0.0231 (18)0.0377 (19)0.0024 (15)0.0105 (15)0.0058 (15)
C510.0243 (16)0.0340 (19)0.0287 (16)0.0080 (14)0.0087 (13)0.0002 (14)
C520.0312 (19)0.059 (3)0.0323 (19)0.0000 (19)0.0087 (15)0.0003 (18)
C530.040 (2)0.048 (2)0.0308 (18)0.0008 (19)0.0120 (15)0.0002 (17)
C540.048 (3)0.066 (3)0.059 (3)0.000 (2)0.015 (2)0.011 (3)
C550.086 (5)0.073 (4)0.082 (4)0.003 (4)0.008 (3)0.028 (4)
C560.045 (2)0.053 (3)0.0323 (19)0.005 (2)0.0090 (16)0.0046 (18)
C570.064 (3)0.049 (3)0.053 (3)0.005 (2)0.020 (2)0.002 (2)
C580.040 (2)0.068 (3)0.062 (3)0.011 (2)0.018 (2)0.001 (3)
Geometric parameters (Å, º) top
O1—C11.436 (4)C28—H28C0.9800
O1—H1O0.8400C29—H29A0.9800
O2—C91.433 (4)C29—H29B0.9800
O2—H2O0.8400C29—H29C0.9800
O3—C301.421 (4)C30—C361.515 (5)
O3—H3O0.8400C30—C311.522 (5)
O4—C381.460 (4)C30—H301.0000
O4—H4O0.8400C31—C321.513 (4)
C1—C71.507 (5)C31—H31A0.9900
C1—C21.523 (4)C31—H31B0.9900
C1—H11.0000C32—C371.334 (4)
C2—C31.511 (4)C32—C331.526 (4)
C2—H2A0.9900C33—C341.548 (4)
C2—H2B0.9900C33—C351.550 (4)
C3—C81.340 (4)C33—C401.559 (4)
C3—C41.531 (4)C34—H34A0.9800
C4—C51.545 (4)C34—H34B0.9800
C4—C61.552 (4)C34—H34C0.9800
C4—C111.558 (4)C35—C361.529 (4)
C5—H5A0.9800C35—H35A0.9900
C5—H5B0.9800C35—H35B0.9900
C5—H5C0.9800C36—H36A0.9900
C6—C71.531 (4)C36—H36B0.9900
C6—H6A0.9900C37—C381.491 (4)
C6—H6B0.9900C37—H370.9500
C7—H7A0.9900C38—C391.522 (4)
C7—H7B0.9900C38—H381.0000
C8—C91.499 (5)C39—C411.524 (4)
C8—H80.9500C39—C401.533 (4)
C9—C101.531 (4)C39—H391.0000
C9—H91.0000C40—C451.537 (4)
C10—C121.517 (4)C40—H401.0000
C10—C111.531 (4)C41—C461.531 (4)
C10—H101.0000C41—C421.544 (4)
C11—C161.542 (4)C41—H411.0000
C11—H111.0000C42—C441.533 (4)
C12—C131.531 (4)C42—C431.542 (4)
C12—C171.531 (4)C42—C481.554 (4)
C12—H121.0000C43—H43A0.9800
C13—C151.540 (4)C43—H43B0.9800
C13—C141.543 (4)C43—H43C0.9800
C13—C191.564 (4)C44—C451.536 (4)
C14—H14A0.9800C44—H44A0.9900
C14—H14B0.9800C44—H44B0.9900
C14—H14C0.9800C45—H45A0.9900
C15—C161.531 (4)C45—H45B0.9900
C15—H15A0.9900C46—C471.537 (5)
C15—H15B0.9900C46—H46A0.9900
C16—H16A0.9900C46—H46B0.9900
C16—H16B0.9900C47—C481.552 (5)
C17—C181.544 (5)C47—H47A0.9900
C17—H17A0.9900C47—H47B0.9900
C17—H17B0.9900C48—C491.543 (4)
C18—C191.553 (5)C48—H481.0000
C18—H18A0.9900C49—C501.529 (5)
C18—H18B0.9900C49—C511.534 (4)
C19—C201.538 (5)C49—H491.0000
C19—H191.0000C50—H50A0.9800
C20—C221.536 (5)C50—H50B0.9800
C20—C211.538 (5)C50—H50C0.9800
C20—H201.0000C51—C521.520 (5)
C21—H21A0.9800C51—H51A0.9900
C21—H21B0.9800C51—H51B0.9900
C21—H21C0.9800C52—C531.536 (5)
C22—C231.521 (5)C52—H52A0.9900
C22—H22A0.9900C52—H52B0.9900
C22—H22B0.9900C53—C541.535 (7)
C23—C241.540 (6)C53—C561.538 (6)
C23—H23A0.9900C53—H531.0000
C23—H23B0.9900C54—C551.529 (9)
C24—C271.527 (7)C54—H54A0.9900
C24—C251.531 (6)C54—H54B0.9900
C24—H241.0000C55—H55A0.9800
C25—C261.481 (9)C55—H55B0.9800
C25—H25A0.9900C55—H55C0.9800
C25—H25B0.9900C56—C581.537 (6)
C26—H26A0.9800C56—C571.542 (7)
C26—H26B0.9800C56—H561.0000
C26—H26C0.9800C57—H57A0.9800
C27—C281.492 (8)C57—H57B0.9800
C27—C291.535 (6)C57—H57C0.9800
C27—H271.0000C58—H58A0.9800
C28—H28A0.9800C58—H58B0.9800
C28—H28B0.9800C58—H58C0.9800
C1—O1—H1O109.5H29A—C29—H29C109.5
C9—O2—H2O109.5H29B—C29—H29C109.5
C30—O3—H3O109.5O3—C30—C36113.9 (3)
C38—O4—H4O109.5O3—C30—C31111.4 (3)
O1—C1—C7112.9 (2)C36—C30—C31110.6 (3)
O1—C1—C2107.9 (3)O3—C30—H30106.8
C7—C1—C2110.1 (3)C36—C30—H30106.8
O1—C1—H1108.6C31—C30—H30106.8
C7—C1—H1108.6C32—C31—C30111.7 (3)
C2—C1—H1108.6C32—C31—H31A109.3
C3—C2—C1111.5 (3)C30—C31—H31A109.3
C3—C2—H2A109.3C32—C31—H31B109.3
C1—C2—H2A109.3C30—C31—H31B109.3
C3—C2—H2B109.3H31A—C31—H31B107.9
C1—C2—H2B109.3C37—C32—C31119.8 (3)
H2A—C2—H2B108.0C37—C32—C33123.7 (3)
C8—C3—C2120.4 (3)C31—C32—C33116.5 (3)
C8—C3—C4123.3 (3)C32—C33—C34107.9 (2)
C2—C3—C4116.3 (3)C32—C33—C35108.1 (2)
C3—C4—C5108.1 (2)C34—C33—C35109.5 (2)
C3—C4—C6108.6 (2)C32—C33—C40111.2 (2)
C5—C4—C6109.8 (2)C34—C33—C40111.3 (2)
C3—C4—C11109.4 (2)C35—C33—C40108.8 (2)
C5—C4—C11112.3 (2)C33—C34—H34A109.5
C6—C4—C11108.7 (2)C33—C34—H34B109.5
C4—C5—H5A109.5H34A—C34—H34B109.5
C4—C5—H5B109.5C33—C34—H34C109.5
H5A—C5—H5B109.5H34A—C34—H34C109.5
C4—C5—H5C109.5H34B—C34—H34C109.5
H5A—C5—H5C109.5C36—C35—C33114.2 (3)
H5B—C5—H5C109.5C36—C35—H35A108.7
C7—C6—C4114.2 (3)C33—C35—H35A108.7
C7—C6—H6A108.7C36—C35—H35B108.7
C4—C6—H6A108.7C33—C35—H35B108.7
C7—C6—H6B108.7H35A—C35—H35B107.6
C4—C6—H6B108.7C30—C36—C35110.2 (3)
H6A—C6—H6B107.6C30—C36—H36A109.6
C1—C7—C6111.0 (3)C35—C36—H36A109.6
C1—C7—H7A109.4C30—C36—H36B109.6
C6—C7—H7A109.4C35—C36—H36B109.6
C1—C7—H7B109.4H36A—C36—H36B108.1
C6—C7—H7B109.4C32—C37—C38124.1 (3)
H7A—C7—H7B108.0C32—C37—H37117.9
C3—C8—C9124.9 (3)C38—C37—H37117.9
C3—C8—H8117.5O4—C38—C37106.1 (2)
C9—C8—H8117.5O4—C38—C39111.6 (2)
O2—C9—C8111.1 (2)C37—C38—C39112.0 (2)
O2—C9—C10111.9 (3)O4—C38—H38109.0
C8—C9—C10111.6 (3)C37—C38—H38109.0
O2—C9—H9107.3C39—C38—H38109.0
C8—C9—H9107.3C38—C39—C41111.2 (2)
C10—C9—H9107.3C38—C39—C40111.2 (2)
C12—C10—C11110.6 (2)C41—C39—C40110.2 (2)
C12—C10—C9110.8 (2)C38—C39—H39108.0
C11—C10—C9110.1 (2)C41—C39—H39108.0
C12—C10—H10108.4C40—C39—H39108.0
C11—C10—H10108.4C39—C40—C45112.0 (2)
C9—C10—H10108.4C39—C40—C33111.8 (2)
C10—C11—C16112.2 (2)C45—C40—C33113.1 (2)
C10—C11—C4112.1 (2)C39—C40—H40106.5
C16—C11—C4112.7 (2)C45—C40—H40106.5
C10—C11—H11106.4C33—C40—H40106.5
C16—C11—H11106.4C39—C41—C46118.6 (3)
C4—C11—H11106.4C39—C41—C42114.4 (2)
C10—C12—C13115.0 (2)C46—C41—C42104.4 (2)
C10—C12—C17117.8 (3)C39—C41—H41106.2
C13—C12—C17104.6 (2)C46—C41—H41106.2
C10—C12—H12106.2C42—C41—H41106.2
C13—C12—H12106.2C44—C42—C43111.2 (2)
C17—C12—H12106.2C44—C42—C41105.6 (2)
C12—C13—C15105.7 (2)C43—C42—C41112.0 (3)
C12—C13—C14112.1 (3)C44—C42—C48116.9 (3)
C15—C13—C14111.1 (3)C43—C42—C48110.2 (2)
C12—C13—C19100.7 (2)C41—C42—C48100.4 (2)
C15—C13—C19116.7 (3)C42—C43—H43A109.5
C14—C13—C19110.0 (2)C42—C43—H43B109.5
C13—C14—H14A109.5H43A—C43—H43B109.5
C13—C14—H14B109.5C42—C43—H43C109.5
H14A—C14—H14B109.5H43A—C43—H43C109.5
C13—C14—H14C109.5H43B—C43—H43C109.5
H14A—C14—H14C109.5C42—C44—C45111.9 (3)
H14B—C14—H14C109.5C42—C44—H44A109.2
C16—C15—C13111.0 (3)C45—C44—H44A109.2
C16—C15—H15A109.4C42—C44—H44B109.2
C13—C15—H15A109.4C45—C44—H44B109.2
C16—C15—H15B109.4H44A—C44—H44B107.9
C13—C15—H15B109.4C44—C45—C40114.0 (2)
H15A—C15—H15B108.0C44—C45—H45A108.8
C15—C16—C11114.5 (3)C40—C45—H45A108.8
C15—C16—H16A108.6C44—C45—H45B108.8
C11—C16—H16A108.6C40—C45—H45B108.8
C15—C16—H16B108.6H45A—C45—H45B107.7
C11—C16—H16B108.6C41—C46—C47103.5 (3)
H16A—C16—H16B107.6C41—C46—H46A111.1
C12—C17—C18103.1 (3)C47—C46—H46A111.1
C12—C17—H17A111.1C41—C46—H46B111.1
C18—C17—H17A111.1C47—C46—H46B111.1
C12—C17—H17B111.1H46A—C46—H46B109.0
C18—C17—H17B111.1C46—C47—C48107.6 (2)
H17A—C17—H17B109.1C46—C47—H47A110.2
C17—C18—C19107.6 (3)C48—C47—H47A110.2
C17—C18—H18A110.2C46—C47—H47B110.2
C19—C18—H18A110.2C48—C47—H47B110.2
C17—C18—H18B110.2H47A—C47—H47B108.5
C19—C18—H18B110.2C49—C48—C47111.7 (3)
H18A—C18—H18B108.5C49—C48—C42118.5 (3)
C20—C19—C18111.8 (3)C47—C48—C42103.8 (3)
C20—C19—C13118.7 (3)C49—C48—H48107.4
C18—C19—C13103.7 (3)C47—C48—H48107.4
C20—C19—H19107.4C42—C48—H48107.4
C18—C19—H19107.4C50—C49—C51110.3 (3)
C13—C19—H19107.4C50—C49—C48113.1 (3)
C22—C20—C21109.8 (3)C51—C49—C48110.2 (3)
C22—C20—C19111.0 (3)C50—C49—H49107.7
C21—C20—C19112.8 (3)C51—C49—H49107.7
C22—C20—H20107.7C48—C49—H49107.7
C21—C20—H20107.7C49—C50—H50A109.5
C19—C20—H20107.7C49—C50—H50B109.5
C20—C21—H21A109.5H50A—C50—H50B109.5
C20—C21—H21B109.5C49—C50—H50C109.5
H21A—C21—H21B109.5H50A—C50—H50C109.5
C20—C21—H21C109.5H50B—C50—H50C109.5
H21A—C21—H21C109.5C52—C51—C49113.8 (3)
H21B—C21—H21C109.5C52—C51—H51A108.8
C23—C22—C20114.9 (3)C49—C51—H51A108.8
C23—C22—H22A108.6C52—C51—H51B108.8
C20—C22—H22A108.6C49—C51—H51B108.8
C23—C22—H22B108.6H51A—C51—H51B107.7
C20—C22—H22B108.6C51—C52—C53114.9 (3)
H22A—C22—H22B107.5C51—C52—H52A108.5
C22—C23—C24116.7 (3)C53—C52—H52A108.5
C22—C23—H23A108.1C51—C52—H52B108.5
C24—C23—H23A108.1C53—C52—H52B108.5
C22—C23—H23B108.1H52A—C52—H52B107.5
C24—C23—H23B108.1C54—C53—C52112.6 (4)
H23A—C23—H23B107.3C54—C53—C56110.9 (4)
C27—C24—C25113.3 (3)C52—C53—C56112.7 (4)
C27—C24—C23112.9 (4)C54—C53—H53106.7
C25—C24—C23110.5 (4)C52—C53—H53106.7
C27—C24—H24106.6C56—C53—H53106.7
C25—C24—H24106.6C55—C54—C53115.5 (5)
C23—C24—H24106.6C55—C54—H54A108.4
C26—C25—C24114.3 (4)C53—C54—H54A108.4
C26—C25—H25A108.7C55—C54—H54B108.4
C24—C25—H25A108.7C53—C54—H54B108.4
C26—C25—H25B108.7H54A—C54—H54B107.5
C24—C25—H25B108.7C54—C55—H55A109.5
H25A—C25—H25B107.6C54—C55—H55B109.5
C25—C26—H26A109.5H55A—C55—H55B109.5
C25—C26—H26B109.5C54—C55—H55C109.5
H26A—C26—H26B109.5H55A—C55—H55C109.5
C25—C26—H26C109.5H55B—C55—H55C109.5
H26A—C26—H26C109.5C58—C56—C53111.5 (4)
H26B—C26—H26C109.5C58—C56—C57110.8 (4)
C28—C27—C24113.8 (4)C53—C56—C57111.4 (4)
C28—C27—C29111.1 (5)C58—C56—H56107.6
C24—C27—C29110.8 (5)C53—C56—H56107.6
C28—C27—H27106.9C57—C56—H56107.6
C24—C27—H27106.9C56—C57—H57A109.5
C29—C27—H27106.9C56—C57—H57B109.5
C27—C28—H28A109.5H57A—C57—H57B109.5
C27—C28—H28B109.5C56—C57—H57C109.5
H28A—C28—H28B109.5H57A—C57—H57C109.5
C27—C28—H28C109.5H57B—C57—H57C109.5
H28A—C28—H28C109.5C56—C58—H58A109.5
H28B—C28—H28C109.5C56—C58—H58B109.5
C27—C29—H29A109.5H58A—C58—H58B109.5
C27—C29—H29B109.5C56—C58—H58C109.5
H29A—C29—H29B109.5H58A—C58—H58C109.5
C27—C29—H29C109.5H58B—C58—H58C109.5
O1—C1—C2—C3179.6 (2)O3—C30—C31—C32177.6 (2)
C7—C1—C2—C356.0 (3)C36—C30—C31—C3254.6 (3)
C1—C2—C3—C8127.2 (3)C30—C31—C32—C37125.8 (3)
C1—C2—C3—C452.8 (3)C30—C31—C32—C3352.0 (3)
C8—C3—C4—C5108.6 (3)C37—C32—C33—C34112.4 (3)
C2—C3—C4—C571.4 (3)C31—C32—C33—C3470.0 (3)
C8—C3—C4—C6132.3 (3)C37—C32—C33—C35129.4 (3)
C2—C3—C4—C647.6 (3)C31—C32—C33—C3548.3 (3)
C8—C3—C4—C1113.9 (4)C37—C32—C33—C4010.0 (4)
C2—C3—C4—C11166.0 (2)C31—C32—C33—C40167.7 (2)
C3—C4—C6—C748.7 (3)C32—C33—C35—C3650.8 (3)
C5—C4—C6—C769.2 (3)C34—C33—C35—C3666.4 (3)
C11—C4—C6—C7167.6 (2)C40—C33—C35—C36171.7 (2)
O1—C1—C7—C6178.6 (2)O3—C30—C36—C35176.2 (3)
C2—C1—C7—C657.9 (3)C31—C30—C36—C3557.4 (3)
C4—C6—C7—C156.2 (3)C33—C35—C36—C3057.4 (3)
C2—C3—C8—C9178.1 (3)C31—C32—C37—C38179.3 (3)
C4—C3—C8—C92.0 (5)C33—C32—C37—C381.7 (5)
C3—C8—C9—O2111.9 (3)C32—C37—C38—O4105.2 (3)
C3—C8—C9—C1013.7 (4)C32—C37—C38—C3916.8 (4)
O2—C9—C10—C1242.1 (3)O4—C38—C39—C4151.0 (3)
C8—C9—C10—C12167.3 (3)C37—C38—C39—C41169.8 (2)
O2—C9—C10—C1180.6 (3)O4—C38—C39—C4072.2 (3)
C8—C9—C10—C1144.6 (3)C37—C38—C39—C4046.5 (3)
C12—C10—C11—C1646.3 (3)C38—C39—C40—C45172.5 (2)
C9—C10—C11—C16169.1 (3)C41—C39—C40—C4548.6 (3)
C12—C10—C11—C4174.3 (2)C38—C39—C40—C3359.4 (3)
C9—C10—C11—C462.9 (3)C41—C39—C40—C33176.7 (2)
C3—C4—C11—C1045.6 (3)C32—C33—C40—C3939.8 (3)
C5—C4—C11—C1074.3 (3)C34—C33—C40—C3980.6 (3)
C6—C4—C11—C10164.0 (2)C35—C33—C40—C39158.7 (2)
C3—C4—C11—C16173.3 (2)C32—C33—C40—C45167.3 (2)
C5—C4—C11—C1653.4 (3)C34—C33—C40—C4547.0 (3)
C6—C4—C11—C1668.3 (3)C35—C33—C40—C4573.8 (3)
C11—C10—C12—C1356.7 (3)C38—C39—C41—C4654.3 (3)
C9—C10—C12—C13179.1 (2)C40—C39—C41—C46178.1 (3)
C11—C10—C12—C17179.2 (3)C38—C39—C41—C42178.2 (2)
C9—C10—C12—C1756.9 (3)C40—C39—C41—C4258.0 (3)
C10—C12—C13—C1561.8 (3)C39—C41—C42—C4461.4 (3)
C17—C12—C13—C15167.4 (3)C46—C41—C42—C44167.4 (2)
C10—C12—C13—C1459.3 (3)C39—C41—C42—C4359.7 (3)
C17—C12—C13—C1471.4 (3)C46—C41—C42—C4371.5 (3)
C10—C12—C13—C19176.3 (2)C39—C41—C42—C48176.6 (2)
C17—C12—C13—C1945.6 (3)C46—C41—C42—C4845.4 (3)
C12—C13—C15—C1658.3 (3)C43—C42—C44—C4564.1 (3)
C14—C13—C15—C1663.5 (3)C41—C42—C44—C4557.6 (3)
C19—C13—C15—C16169.3 (3)C48—C42—C44—C45168.2 (3)
C13—C15—C16—C1154.6 (4)C42—C44—C45—C4054.5 (3)
C10—C11—C16—C1547.4 (4)C39—C40—C45—C4448.5 (3)
C4—C11—C16—C15175.1 (3)C33—C40—C45—C44176.0 (2)
C10—C12—C17—C18165.3 (3)C39—C41—C46—C47163.5 (3)
C13—C12—C17—C1836.2 (3)C42—C41—C46—C4734.9 (3)
C12—C17—C18—C1912.4 (3)C41—C46—C47—C4810.5 (3)
C17—C18—C19—C20144.2 (3)C46—C47—C48—C49146.1 (3)
C17—C18—C19—C1315.1 (3)C46—C47—C48—C4217.3 (3)
C12—C13—C19—C20161.2 (3)C44—C42—C48—C4984.2 (3)
C15—C13—C19—C2085.0 (4)C43—C42—C48—C4944.0 (4)
C14—C13—C19—C2042.7 (4)C41—C42—C48—C49162.2 (3)
C12—C13—C19—C1836.5 (3)C44—C42—C48—C47151.3 (3)
C15—C13—C19—C18150.3 (3)C43—C42—C48—C4780.5 (3)
C14—C13—C19—C1882.0 (3)C41—C42—C48—C4737.7 (3)
C18—C19—C20—C2259.9 (4)C47—C48—C49—C50179.1 (3)
C13—C19—C20—C22179.5 (3)C42—C48—C49—C5058.5 (4)
C18—C19—C20—C21176.4 (3)C47—C48—C49—C5156.9 (3)
C13—C19—C20—C2155.7 (4)C42—C48—C49—C51177.5 (3)
C21—C20—C22—C2370.0 (4)C50—C49—C51—C5280.5 (4)
C19—C20—C22—C23164.7 (3)C48—C49—C51—C52153.8 (3)
C20—C22—C23—C24173.5 (3)C49—C51—C52—C53170.2 (4)
C22—C23—C24—C2758.9 (5)C51—C52—C53—C5463.0 (5)
C22—C23—C24—C25173.2 (4)C51—C52—C53—C5663.3 (5)
C27—C24—C25—C26162.0 (5)C52—C53—C54—C5545.6 (6)
C23—C24—C25—C2670.2 (6)C56—C53—C54—C55172.9 (4)
C25—C24—C27—C2863.1 (5)C54—C53—C56—C5854.0 (5)
C23—C24—C27—C2863.4 (5)C52—C53—C56—C58178.7 (4)
C25—C24—C27—C2962.9 (5)C54—C53—C56—C57178.4 (4)
C23—C24—C27—C29170.6 (4)C52—C53—C56—C5754.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O40.841.922.762 (3)178
O2—H2O···O30.841.872.686 (3)165
O3—H3O···O1i0.841.862.694 (3)170
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC29H50O2
Mr430.69
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)8.1690 (1), 12.2369 (2), 25.6945 (4)
β (°) 93.652 (1)
V3)2563.29 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.45 × 0.15 × 0.03
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
21218, 6154, 5389
Rint0.039
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.172, 1.11
No. of reflections6154
No. of parameters575
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.46, 0.27

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O40.841.922.762 (3)178
O2—H2O···O30.841.872.686 (3)165
O3—H3O···O1i0.841.862.694 (3)170
Symmetry code: (i) x1, y, z.
 

Acknowledgements

The authors thank the University of Malaya (PPP P8198-2008A) for supporting this study.

References

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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTzouros, M., Bigler, L., Bienz, S., Hesse, M., Inada, A., Murata, H., Inatomi, Y., Nakanishi, T. & Darnaedi, D. (2004). Helv. Chim. Acta, 87, 1411–1425.  Web of Science CrossRef CAS Google Scholar
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