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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2541.
Published online 2010 September 11. doi:  10.1107/S1600536810035208
PMCID: PMC2983197

Cabraleahy­droxy­lactone from the leaves of Aglaia exima

Abstract

Cabraleahy­droxy­lactone, C27H44O3, isolated from the leaves of Aglaia exima, has three six-membered rings fused together that adopt chair conformations. Its two five-membered rings are enveloped shaped. The hy­droxy group is in an axial position. It is a hydrogen-bond donor to the carbonyl O atom of an adjacent mol­ecule; the O—H(...)O inter­actions lead to the formation of a helical chain that runs along the b axis. There are two independent mol­ecules in the asymmetric unit.

Related literature

For the isolation and spectroscopic characterization of cabraleahy­droxy­lactone from other Alglaia species, see: Su et al. (2006 [triangle]); Yang et al. (2008 [triangle]). For another compound from Aglaia exima, see: Awang et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2541-scheme1.jpg

Experimental

Crystal data

  • C27H44O3
  • M r = 416.62
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2541-efi1.jpg
  • a = 7.2077 (5) Å
  • b = 20.8363 (15) Å
  • c = 30.464 (2) Å
  • V = 4575.2 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100 K
  • 0.30 × 0.05 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 36097 measured reflections
  • 4573 independent reflections
  • 3803 reflections with I > 2σ(I)
  • R int = 0.098

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.121
  • S = 1.07
  • 4573 reflections
  • 555 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035208/bt5334sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035208/bt5334Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The Aglaia genus consists of some 130 species of trees and shrubs distributed mainly in the tropical rain forests of Southeast Asia. Cabraleahydroxylactone (Scheme I) has been isolated from Aglaia crassinervia (Su et al., 2006) and Aglaia perviridis (Yang et al., 2008) as well as from other plants, and the structure and absolute configuration have been established from spectroscopic measurements. The structural assignment is confirmed by the present crystal structure analysis of the compound isolated from Aglaia exima. There are two independent cabraleahydroxylactone molecules in the asymmetric unit. Each molecule has three six-membered rings fused together that adopt chair conformations. The two five-membered rings are enveloped-shaped (Figs. 1 and 2). The hydroxy unit is axial; this unit is hydrogen-bond donor to the double-bond oxygen atom of an adjacent molecule. The O–H···O interactions lead to the formation of a chain that runs along the longest axis of the orthorhombic unit cell.

Experimental

The leaves of Algaia exima were collected from Kampung Kepayang, Pahang, Malaysia. The leaves (1 kg) were soaked in n-hexane for 4 days. The solution was decanted and then evaporated to leave a residue of 25 g; a 15 g portion was subjected to column chromatography over silica gel at a gradient mixture of n-hexane and ethyl acetate. Of the 123 fractions, fractions 94–100 were separated by column chromatography (7:3 n-hexane:ethyl acetate) to give a colorless solid. Single crystals of cabraleahydroxylactone were obtained by recrystallization from ethyl acetate.

Refinement

Carbon-bound H-atoms were placed in calculated positions [C—H 0.95 to 1.00 Å, U(H) 1.2 to 1.5U(C)] and were included in the refinement in the riding model approximation. The torsion angles of the methyl groups were refined. The hydroxy H-atoms were similarly placed [O–H 0.84 Å] and their displacement parameters were set to 1.5U(O).

3940 Friedel pairs were merged.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of one of the two independent molecules of C27H44O3 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of the second independent molecule of C27H44O3 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C27H44O3F(000) = 1840
Mr = 416.62Dx = 1.210 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4625 reflections
a = 7.2077 (5) Åθ = 2.2–24.2°
b = 20.8363 (15) ŵ = 0.08 mm1
c = 30.464 (2) ÅT = 100 K
V = 4575.2 (6) Å3Prism, colorless
Z = 80.30 × 0.05 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer3803 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.098
graphiteθmax = 25.0°, θmin = 1.2°
ω scansh = −8→8
36097 measured reflectionsk = −24→23
4573 independent reflectionsl = −36→36

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0442P)2 + 4.0407P] where P = (Fo2 + 2Fc2)/3
4573 reflections(Δ/σ)max = 0.001
555 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = −0.25 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.2796 (5)0.58659 (13)0.38176 (9)0.0281 (7)
H10.29110.54710.37700.042*
O20.4571 (4)1.09025 (13)0.60025 (8)0.0251 (7)
O30.3075 (4)1.06676 (12)0.53818 (8)0.0171 (6)
O40.7658 (4)1.04183 (13)0.64896 (8)0.0204 (6)
H40.67261.05940.63760.031*
O50.9808 (4)0.79695 (14)1.01455 (9)0.0278 (7)
O60.9900 (4)0.79834 (12)0.94154 (8)0.0176 (6)
C10.2089 (6)0.61757 (19)0.34291 (12)0.0191 (9)
H1A0.19120.58420.31970.023*
C20.3559 (6)0.66442 (19)0.32737 (13)0.0208 (9)
H2A0.31990.68170.29830.025*
H2B0.47530.64150.32390.025*
C30.3817 (5)0.72036 (19)0.35968 (13)0.0178 (8)
H3A0.42730.70330.38800.021*
H3B0.47730.74990.34800.021*
C40.2018 (5)0.75810 (18)0.36769 (12)0.0143 (8)
C50.1559 (6)0.79549 (19)0.32509 (11)0.0185 (9)
H5A0.20780.77270.29980.028*
H5B0.20980.83860.32670.028*
H5C0.02100.79880.32180.028*
C60.0509 (5)0.70880 (18)0.38243 (12)0.0142 (8)
H60.09930.69050.41050.017*
C70.0202 (5)0.64947 (18)0.35207 (12)0.0170 (8)
C8−0.0750 (6)0.6656 (2)0.30844 (12)0.0211 (9)
H8A0.00710.69280.29070.032*
H8B−0.19110.68860.31420.032*
H8C−0.10180.62590.29250.032*
C9−0.1035 (6)0.59982 (19)0.37536 (13)0.0246 (10)
H9A−0.09860.55900.35940.037*
H9B−0.23170.61540.37610.037*
H9C−0.05900.59340.40540.037*
C10−0.1287 (5)0.74284 (18)0.39526 (12)0.0160 (8)
H10A−0.22430.71060.40300.019*
H10B−0.17520.76820.37010.019*
C11−0.0943 (5)0.78739 (19)0.43454 (12)0.0154 (8)
H11A−0.05670.76110.46010.019*
H11B−0.21180.80930.44220.019*
C120.0556 (5)0.83837 (18)0.42601 (12)0.0129 (8)
C13−0.0256 (6)0.88744 (18)0.39315 (12)0.0187 (9)
H13A−0.11710.91450.40810.028*
H13B−0.08570.86450.36890.028*
H13C0.07440.91440.38160.028*
C140.2335 (5)0.80400 (18)0.40804 (11)0.0122 (8)
H140.27340.77490.43240.015*
C150.3967 (5)0.85132 (19)0.40226 (13)0.0173 (8)
H15A0.50850.82720.39310.021*
H15B0.36600.88220.37870.021*
C160.4400 (5)0.88847 (19)0.44474 (13)0.0175 (8)
H16A0.48630.85840.46740.021*
H16B0.53810.92070.43900.021*
C170.2675 (5)0.92170 (17)0.46118 (12)0.0139 (8)
H170.22420.95050.43700.017*
C180.1089 (5)0.87326 (18)0.46999 (12)0.0138 (8)
C190.1657 (6)0.82524 (19)0.50616 (12)0.0199 (9)
H19A0.23780.84760.52870.030*
H19B0.24110.79100.49330.030*
H19C0.05410.80670.51940.030*
C20−0.0365 (6)0.91833 (18)0.49069 (12)0.0188 (9)
H20A−0.09750.94490.46800.023*
H20B−0.13240.89350.50660.023*
C210.0764 (5)0.96028 (19)0.52249 (13)0.0186 (8)
H21A0.07750.94100.55220.022*
H21B0.02211.00380.52440.022*
C220.2785 (5)0.96349 (17)0.50328 (12)0.0149 (8)
H220.36460.94210.52450.018*
C230.3445 (5)1.03260 (18)0.49629 (12)0.0155 (8)
C240.2401 (6)1.06900 (18)0.46072 (12)0.0192 (9)
H24A0.27211.11470.46220.029*
H24B0.10621.06380.46510.029*
H24C0.27461.05200.43190.029*
C250.5553 (6)1.03897 (18)0.49164 (12)0.0184 (9)
H25A0.60831.00140.47620.022*
H25B0.58851.07840.47530.022*
C260.6246 (6)1.0423 (2)0.53885 (13)0.0216 (9)
H26A0.65810.99920.55000.026*
H26B0.73361.07090.54140.026*
C270.4611 (6)1.06908 (18)0.56309 (13)0.0184 (9)
C280.8607 (6)1.08736 (18)0.67638 (12)0.0162 (8)
H280.87331.12850.65970.019*
C291.0527 (5)1.06106 (18)0.68467 (12)0.0176 (8)
H29A1.12961.09490.69840.021*
H29B1.11041.04970.65620.021*
C301.0532 (5)1.00155 (17)0.71448 (11)0.0154 (8)
H30A1.18310.98840.71990.019*
H30B0.99040.96580.69900.019*
C310.9560 (5)1.01284 (17)0.75894 (12)0.0139 (8)
C321.0809 (6)1.05702 (18)0.78677 (13)0.0187 (9)
H32A1.14861.08640.76740.028*
H32B1.16951.03090.80340.028*
H32C1.00411.08180.80720.028*
C330.7601 (5)1.04067 (17)0.74876 (12)0.0140 (8)
H330.69761.00650.73110.017*
C340.7524 (6)1.10136 (17)0.71919 (12)0.0157 (8)
C350.8312 (6)1.16297 (18)0.74021 (13)0.0216 (9)
H35A0.79601.20020.72240.032*
H35B0.96671.16000.74170.032*
H35C0.78081.16790.76990.032*
C360.5499 (6)1.11633 (19)0.70719 (13)0.0202 (9)
H36A0.54691.14700.68280.030*
H36B0.48661.13490.73270.030*
H36C0.48691.07670.69840.030*
C370.6416 (5)1.04637 (18)0.79052 (12)0.0162 (8)
H37A0.70451.07490.81180.019*
H37B0.52011.06570.78310.019*
C380.6115 (5)0.98016 (18)0.81121 (12)0.0165 (8)
H38A0.53580.98520.83810.020*
H38B0.54040.95310.79050.020*
C390.7913 (5)0.94578 (18)0.82302 (12)0.0137 (8)
C400.8788 (6)0.98119 (18)0.86242 (12)0.0165 (8)
H40A0.87591.02760.85710.025*
H40B1.00770.96720.86610.025*
H40C0.80850.97130.88910.025*
C410.9237 (5)0.94567 (17)0.78171 (12)0.0134 (8)
H410.85490.92000.75920.016*
C421.1012 (5)0.90678 (17)0.79026 (12)0.0152 (8)
H42A1.17590.90560.76300.018*
H42B1.17550.92880.81300.018*
C431.0627 (5)0.83765 (18)0.80528 (12)0.0160 (8)
H43A1.00200.81340.78130.019*
H43B1.18090.81600.81260.019*
C440.9364 (5)0.83886 (18)0.84565 (12)0.0147 (8)
H441.00120.86530.86830.018*
C450.7527 (5)0.87339 (18)0.83525 (12)0.0145 (8)
C460.6461 (6)0.83813 (19)0.79815 (13)0.0198 (9)
H46A0.66650.79180.80080.030*
H46B0.69130.85300.76960.030*
H46C0.51320.84730.80070.030*
C470.6450 (6)0.86004 (18)0.87787 (12)0.0181 (9)
H47A0.51120.86930.87420.022*
H47B0.69410.88600.90250.022*
C480.6785 (5)0.78814 (19)0.88553 (13)0.0185 (9)
H48A0.58700.76210.86910.022*
H48B0.66860.77760.91710.022*
C490.8794 (5)0.77520 (18)0.86838 (12)0.0162 (8)
H490.87260.74090.84540.019*
C501.0103 (6)0.75229 (18)0.90459 (12)0.0168 (8)
C511.2139 (5)0.75294 (19)0.89235 (13)0.0187 (9)
H51A1.25290.79710.88620.028*
H51B1.23330.72640.86620.028*
H51C1.28740.73580.91670.028*
C520.9517 (6)0.68784 (18)0.92501 (12)0.0197 (9)
H52A0.81790.67970.92030.024*
H52B1.02390.65190.91240.024*
C530.9947 (6)0.69623 (19)0.97360 (13)0.0239 (9)
H53A0.90100.67430.99200.029*
H53B1.11910.67910.98080.029*
C540.9876 (5)0.76753 (19)0.98025 (12)0.0190 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0374 (19)0.0199 (15)0.0270 (16)0.0070 (15)−0.0114 (14)−0.0033 (13)
O20.0267 (17)0.0304 (16)0.0183 (14)0.0063 (14)−0.0016 (13)−0.0066 (12)
O30.0152 (14)0.0202 (14)0.0161 (13)0.0014 (12)−0.0013 (11)−0.0061 (11)
O40.0211 (16)0.0233 (15)0.0169 (14)0.0035 (13)−0.0060 (12)−0.0032 (11)
O50.0351 (19)0.0317 (16)0.0164 (15)−0.0028 (15)0.0027 (13)0.0005 (13)
O60.0212 (15)0.0183 (14)0.0133 (13)−0.0027 (12)0.0012 (12)−0.0005 (11)
C10.019 (2)0.022 (2)0.016 (2)−0.0013 (18)−0.0033 (17)−0.0042 (16)
C20.0093 (19)0.028 (2)0.025 (2)0.0007 (18)0.0018 (17)−0.0101 (18)
C30.0091 (19)0.024 (2)0.020 (2)0.0003 (17)−0.0013 (16)−0.0040 (17)
C40.0081 (18)0.020 (2)0.0145 (18)−0.0009 (16)0.0009 (15)−0.0016 (15)
C50.022 (2)0.022 (2)0.0112 (18)−0.0013 (18)0.0020 (17)−0.0011 (16)
C60.0093 (18)0.0196 (19)0.0136 (18)−0.0005 (17)−0.0027 (15)0.0004 (15)
C70.0107 (19)0.021 (2)0.0191 (19)−0.0022 (17)0.0003 (16)−0.0002 (16)
C80.016 (2)0.028 (2)0.019 (2)−0.0044 (19)0.0032 (17)−0.0059 (17)
C90.032 (3)0.020 (2)0.022 (2)−0.0082 (19)0.0024 (19)−0.0029 (17)
C100.0109 (19)0.021 (2)0.0162 (19)−0.0009 (17)−0.0009 (16)0.0005 (16)
C110.0061 (19)0.024 (2)0.0160 (19)0.0005 (17)0.0038 (15)−0.0009 (16)
C120.0067 (18)0.0164 (19)0.0158 (18)0.0016 (16)−0.0002 (15)0.0010 (15)
C130.019 (2)0.0172 (19)0.020 (2)0.0053 (17)−0.0036 (17)0.0006 (16)
C140.0068 (18)0.0188 (19)0.0110 (17)−0.0002 (16)0.0012 (15)−0.0003 (15)
C150.0082 (19)0.023 (2)0.021 (2)−0.0038 (16)0.0027 (16)−0.0060 (17)
C160.0085 (19)0.021 (2)0.023 (2)−0.0008 (17)0.0016 (16)−0.0057 (17)
C170.0129 (19)0.0165 (19)0.0124 (17)−0.0002 (17)0.0021 (15)−0.0012 (15)
C180.0106 (19)0.0179 (19)0.0129 (18)0.0013 (16)0.0045 (15)0.0009 (15)
C190.024 (2)0.023 (2)0.0124 (19)−0.0044 (18)0.0005 (17)0.0002 (16)
C200.014 (2)0.022 (2)0.020 (2)−0.0010 (18)0.0049 (16)−0.0044 (16)
C210.017 (2)0.022 (2)0.0174 (19)0.0003 (17)0.0063 (17)−0.0013 (16)
C220.016 (2)0.0170 (19)0.0119 (18)0.0046 (17)−0.0032 (16)−0.0011 (15)
C230.015 (2)0.018 (2)0.0132 (18)0.0048 (17)0.0008 (16)−0.0066 (15)
C240.020 (2)0.018 (2)0.0198 (19)−0.0003 (18)−0.0023 (17)−0.0001 (16)
C250.019 (2)0.0148 (19)0.021 (2)0.0011 (17)0.0029 (17)−0.0036 (16)
C260.014 (2)0.021 (2)0.030 (2)0.0013 (18)−0.0030 (18)−0.0064 (18)
C270.018 (2)0.0152 (19)0.022 (2)0.0025 (17)−0.0041 (17)−0.0011 (16)
C280.018 (2)0.0168 (19)0.0137 (18)−0.0003 (17)−0.0001 (16)0.0004 (15)
C290.014 (2)0.023 (2)0.0167 (19)−0.0014 (18)0.0061 (16)0.0000 (16)
C300.0111 (19)0.020 (2)0.0155 (18)0.0000 (17)−0.0010 (16)0.0010 (15)
C310.0079 (19)0.0154 (19)0.0183 (19)−0.0017 (16)0.0012 (16)−0.0023 (15)
C320.017 (2)0.019 (2)0.020 (2)−0.0034 (17)−0.0013 (17)0.0014 (16)
C330.0115 (19)0.0171 (19)0.0135 (18)−0.0004 (17)0.0019 (16)−0.0029 (15)
C340.015 (2)0.0149 (19)0.0168 (19)0.0009 (17)0.0024 (17)0.0005 (15)
C350.026 (2)0.017 (2)0.021 (2)0.0003 (19)−0.0001 (18)0.0000 (16)
C360.018 (2)0.022 (2)0.021 (2)0.0013 (18)0.0021 (17)0.0018 (16)
C370.0122 (19)0.020 (2)0.0161 (19)0.0028 (17)0.0027 (16)−0.0011 (16)
C380.0103 (19)0.022 (2)0.0169 (19)0.0025 (17)0.0030 (16)−0.0010 (16)
C390.0094 (19)0.019 (2)0.0123 (18)0.0012 (16)0.0004 (15)−0.0023 (15)
C400.017 (2)0.019 (2)0.0131 (18)0.0025 (17)−0.0004 (16)0.0002 (15)
C410.0076 (18)0.0174 (19)0.0152 (18)0.0019 (16)−0.0016 (15)−0.0014 (15)
C420.0092 (19)0.020 (2)0.0167 (19)0.0011 (16)0.0035 (15)0.0002 (15)
C430.0114 (19)0.0181 (19)0.0184 (19)0.0027 (17)−0.0004 (16)−0.0008 (16)
C440.0105 (19)0.0189 (19)0.0149 (18)−0.0013 (17)−0.0005 (16)−0.0007 (15)
C450.0075 (18)0.021 (2)0.0148 (18)−0.0001 (17)−0.0002 (16)−0.0025 (15)
C460.016 (2)0.020 (2)0.023 (2)−0.0026 (18)−0.0007 (18)0.0002 (17)
C470.013 (2)0.025 (2)0.0165 (19)−0.0029 (17)0.0002 (17)0.0028 (16)
C480.013 (2)0.024 (2)0.0183 (19)−0.0026 (17)0.0003 (16)0.0012 (17)
C490.016 (2)0.0168 (19)0.0158 (19)−0.0032 (17)0.0002 (16)0.0011 (15)
C500.019 (2)0.0140 (19)0.0172 (19)−0.0017 (17)−0.0017 (17)−0.0010 (15)
C510.019 (2)0.020 (2)0.017 (2)−0.0007 (18)0.0003 (17)0.0019 (16)
C520.016 (2)0.018 (2)0.026 (2)−0.0023 (17)0.0002 (18)0.0035 (16)
C530.023 (2)0.025 (2)0.024 (2)−0.0038 (19)0.0006 (19)0.0075 (17)
C540.016 (2)0.027 (2)0.0141 (19)−0.0037 (18)0.0009 (16)0.0053 (17)

Geometric parameters (Å, °)

O1—C11.441 (5)C25—H25A0.9900
O1—H10.8400C25—H25B0.9900
O2—C271.216 (4)C26—C271.499 (6)
O3—C271.343 (5)C26—H26A0.9900
O3—C231.485 (4)C26—H26B0.9900
O4—C281.437 (5)C28—C291.510 (5)
O4—H40.8400C28—C341.548 (5)
O5—C541.213 (5)C28—H281.0000
O6—C541.343 (4)C29—C301.537 (5)
O6—C501.486 (4)C29—H29A0.9900
C1—C21.516 (6)C29—H29B0.9900
C1—C71.539 (5)C30—C311.543 (5)
C1—H1A1.0000C30—H30A0.9900
C2—C31.537 (5)C30—H30B0.9900
C2—H2A0.9900C31—C321.542 (5)
C2—H2B0.9900C31—C331.557 (5)
C3—C41.536 (5)C31—C411.579 (5)
C3—H3A0.9900C32—H32A0.9800
C3—H3B0.9900C32—H32B0.9800
C4—C51.549 (5)C32—H32C0.9800
C4—C61.562 (5)C33—C371.537 (5)
C4—C141.574 (5)C33—C341.554 (5)
C5—H5A0.9800C33—H331.0000
C5—H5B0.9800C34—C361.537 (6)
C5—H5C0.9800C34—C351.543 (5)
C6—C101.527 (5)C35—H35A0.9800
C6—C71.560 (5)C35—H35B0.9800
C6—H61.0000C35—H35C0.9800
C7—C81.533 (5)C36—H36A0.9800
C7—C91.539 (5)C36—H36B0.9800
C8—H8A0.9800C36—H36C0.9800
C8—H8B0.9800C37—C381.532 (5)
C8—H8C0.9800C37—H37A0.9900
C9—H9A0.9800C37—H37B0.9900
C9—H9B0.9800C38—C391.524 (5)
C9—H9C0.9800C38—H38A0.9900
C10—C111.535 (5)C38—H38B0.9900
C10—H10A0.9900C39—C401.544 (5)
C10—H10B0.9900C39—C411.579 (5)
C11—C121.537 (5)C39—C451.578 (5)
C11—H11A0.9900C40—H40A0.9800
C11—H11B0.9900C40—H40B0.9800
C12—C131.546 (5)C40—H40C0.9800
C12—C141.567 (5)C41—C421.536 (5)
C12—C181.572 (5)C41—H411.0000
C13—H13A0.9800C42—C431.537 (5)
C13—H13B0.9800C42—H42A0.9900
C13—H13C0.9800C42—H42B0.9900
C14—C151.545 (5)C43—C441.530 (5)
C14—H141.0000C43—H43A0.9900
C15—C161.540 (5)C43—H43B0.9900
C15—H15A0.9900C44—C451.540 (5)
C15—H15B0.9900C44—C491.552 (5)
C16—C171.509 (5)C44—H441.0000
C16—H16A0.9900C45—C471.538 (5)
C16—H16B0.9900C45—C461.551 (5)
C17—C181.548 (5)C46—H46A0.9800
C17—C221.552 (5)C46—H46B0.9800
C17—H171.0000C46—H46C0.9800
C18—C201.542 (5)C47—C481.535 (5)
C18—C191.544 (5)C47—H47A0.9900
C19—H19A0.9800C47—H47B0.9900
C19—H19B0.9800C48—C491.563 (5)
C19—H19C0.9800C48—H48A0.9900
C20—C211.538 (5)C48—H48B0.9900
C20—H20A0.9900C49—C501.528 (5)
C20—H20B0.9900C49—H491.0000
C21—C221.572 (5)C50—C511.514 (6)
C21—H21A0.9900C50—C521.539 (5)
C21—H21B0.9900C51—H51A0.9800
C22—C231.531 (5)C51—H51B0.9800
C22—H221.0000C51—H51C0.9800
C23—C241.522 (5)C52—C531.523 (5)
C23—C251.532 (6)C52—H52A0.9900
C24—H24A0.9800C52—H52B0.9900
C24—H24B0.9800C53—C541.500 (6)
C24—H24C0.9800C53—H53A0.9900
C25—C261.524 (5)C53—H53B0.9900
C1—O1—H1109.5O2—C27—C26127.8 (4)
C27—O3—C23110.8 (3)O3—C27—C26110.9 (3)
C28—O4—H4109.5O4—C28—C29107.1 (3)
C54—O6—C50111.0 (3)O4—C28—C34112.0 (3)
O1—C1—C2107.3 (3)C29—C28—C34112.9 (3)
O1—C1—C7110.9 (3)O4—C28—H28108.2
C2—C1—C7113.3 (3)C29—C28—H28108.2
O1—C1—H1A108.4C34—C28—H28108.2
C2—C1—H1A108.4C28—C29—C30113.2 (3)
C7—C1—H1A108.4C28—C29—H29A108.9
C1—C2—C3111.9 (3)C30—C29—H29A108.9
C1—C2—H2A109.2C28—C29—H29B108.9
C3—C2—H2A109.2C30—C29—H29B108.9
C1—C2—H2B109.2H29A—C29—H29B107.8
C3—C2—H2B109.2C29—C30—C31113.2 (3)
H2A—C2—H2B107.9C29—C30—H30A108.9
C4—C3—C2112.8 (3)C31—C30—H30A108.9
C4—C3—H3A109.0C29—C30—H30B108.9
C2—C3—H3A109.0C31—C30—H30B108.9
C4—C3—H3B109.0H30A—C30—H30B107.7
C2—C3—H3B109.0C30—C31—C32108.0 (3)
H3A—C3—H3B107.8C30—C31—C33107.1 (3)
C3—C4—C5107.8 (3)C32—C31—C33114.6 (3)
C3—C4—C6107.3 (3)C30—C31—C41108.5 (3)
C5—C4—C6115.0 (3)C32—C31—C41111.9 (3)
C3—C4—C14108.2 (3)C33—C31—C41106.5 (3)
C5—C4—C14112.3 (3)C31—C32—H32A109.5
C6—C4—C14106.0 (3)C31—C32—H32B109.5
C4—C5—H5A109.5H32A—C32—H32B109.5
C4—C5—H5B109.5C31—C32—H32C109.5
H5A—C5—H5B109.5H32A—C32—H32C109.5
C4—C5—H5C109.5H32B—C32—H32C109.5
H5A—C5—H5C109.5C37—C33—C34113.4 (3)
H5B—C5—H5C109.5C37—C33—C31111.6 (3)
C10—C6—C7113.5 (3)C34—C33—C31116.8 (3)
C10—C6—C4111.0 (3)C37—C33—H33104.5
C7—C6—C4116.7 (3)C34—C33—H33104.5
C10—C6—H6104.7C31—C33—H33104.5
C7—C6—H6104.7C36—C34—C35106.2 (3)
C4—C6—H6104.7C36—C34—C28108.5 (3)
C8—C7—C9106.7 (3)C35—C34—C28108.7 (3)
C8—C7—C1109.5 (3)C36—C34—C33109.7 (3)
C9—C7—C1107.8 (3)C35—C34—C33115.1 (3)
C8—C7—C6113.8 (3)C28—C34—C33108.5 (3)
C9—C7—C6110.0 (3)C34—C35—H35A109.5
C1—C7—C6108.9 (3)C34—C35—H35B109.5
C7—C8—H8A109.5H35A—C35—H35B109.5
C7—C8—H8B109.5C34—C35—H35C109.5
H8A—C8—H8B109.5H35A—C35—H35C109.5
C7—C8—H8C109.5H35B—C35—H35C109.5
H8A—C8—H8C109.5C34—C36—H36A109.5
H8B—C8—H8C109.5C34—C36—H36B109.5
C7—C9—H9A109.5H36A—C36—H36B109.5
C7—C9—H9B109.5C34—C36—H36C109.5
H9A—C9—H9B109.5H36A—C36—H36C109.5
C7—C9—H9C109.5H36B—C36—H36C109.5
H9A—C9—H9C109.5C38—C37—C33110.5 (3)
H9B—C9—H9C109.5C38—C37—H37A109.6
C6—C10—C11110.1 (3)C33—C37—H37A109.6
C6—C10—H10A109.6C38—C37—H37B109.6
C11—C10—H10A109.6C33—C37—H37B109.6
C6—C10—H10B109.6H37A—C37—H37B108.1
C11—C10—H10B109.6C39—C38—C37113.6 (3)
H10A—C10—H10B108.2C39—C38—H38A108.9
C10—C11—C12113.6 (3)C37—C38—H38A108.9
C10—C11—H11A108.9C39—C38—H38B108.9
C12—C11—H11A108.9C37—C38—H38B108.9
C10—C11—H11B108.9H38A—C38—H38B107.7
C12—C11—H11B108.9C38—C39—C40107.8 (3)
H11A—C11—H11B107.7C38—C39—C41109.1 (3)
C11—C12—C13107.5 (3)C40—C39—C41111.9 (3)
C11—C12—C14108.6 (3)C38—C39—C45110.8 (3)
C13—C12—C14112.7 (3)C40—C39—C45110.2 (3)
C11—C12—C18110.3 (3)C41—C39—C45107.1 (3)
C13—C12—C18109.8 (3)C39—C40—H40A109.5
C14—C12—C18108.0 (3)C39—C40—H40B109.5
C12—C13—H13A109.5H40A—C40—H40B109.5
C12—C13—H13B109.5C39—C40—H40C109.5
H13A—C13—H13B109.5H40A—C40—H40C109.5
C12—C13—H13C109.5H40B—C40—H40C109.5
H13A—C13—H13C109.5C42—C41—C39111.6 (3)
H13B—C13—H13C109.5C42—C41—C31114.8 (3)
C15—C14—C12111.8 (3)C39—C41—C31115.9 (3)
C15—C14—C4114.2 (3)C42—C41—H41104.3
C12—C14—C4115.6 (3)C39—C41—H41104.3
C15—C14—H14104.6C31—C41—H41104.3
C12—C14—H14104.6C43—C42—C41113.2 (3)
C4—C14—H14104.6C43—C42—H42A108.9
C16—C15—C14112.3 (3)C41—C42—H42A108.9
C16—C15—H15A109.1C43—C42—H42B108.9
C14—C15—H15A109.1C41—C42—H42B108.9
C16—C15—H15B109.1H42A—C42—H42B107.7
C14—C15—H15B109.1C44—C43—C42109.3 (3)
H15A—C15—H15B107.9C44—C43—H43A109.8
C17—C16—C15110.0 (3)C42—C43—H43A109.8
C17—C16—H16A109.7C44—C43—H43B109.8
C15—C16—H16A109.7C42—C43—H43B109.8
C17—C16—H16B109.7H43A—C43—H43B108.3
C15—C16—H16B109.7C43—C44—C45110.7 (3)
H16A—C16—H16B108.2C43—C44—C49120.1 (3)
C16—C17—C18111.5 (3)C45—C44—C49105.3 (3)
C16—C17—C22119.3 (3)C43—C44—H44106.6
C18—C17—C22105.1 (3)C45—C44—H44106.6
C16—C17—H17106.7C49—C44—H44106.6
C18—C17—H17106.7C47—C45—C44100.1 (3)
C22—C17—H17106.7C47—C45—C46106.2 (3)
C20—C18—C19106.4 (3)C44—C45—C46110.7 (3)
C20—C18—C17100.1 (3)C47—C45—C39117.5 (3)
C19—C18—C17110.5 (3)C44—C45—C39110.1 (3)
C20—C18—C12117.7 (3)C46—C45—C39111.6 (3)
C19—C18—C12111.9 (3)C45—C46—H46A109.5
C17—C18—C12109.5 (3)C45—C46—H46B109.5
C18—C19—H19A109.5H46A—C46—H46B109.5
C18—C19—H19B109.5C45—C46—H46C109.5
H19A—C19—H19B109.5H46A—C46—H46C109.5
C18—C19—H19C109.5H46B—C46—H46C109.5
H19A—C19—H19C109.5C45—C47—C48103.0 (3)
H19B—C19—H19C109.5C45—C47—H47A111.2
C21—C20—C18104.1 (3)C48—C47—H47A111.2
C21—C20—H20A110.9C45—C47—H47B111.2
C18—C20—H20A110.9C48—C47—H47B111.2
C21—C20—H20B110.9H47A—C47—H47B109.1
C18—C20—H20B110.9C47—C48—C49105.3 (3)
H20A—C20—H20B108.9C47—C48—H48A110.7
C20—C21—C22106.3 (3)C49—C48—H48A110.7
C20—C21—H21A110.5C47—C48—H48B110.7
C22—C21—H21A110.5C49—C48—H48B110.7
C20—C21—H21B110.5H48A—C48—H48B108.8
C22—C21—H21B110.5C50—C49—C44115.2 (3)
H21A—C21—H21B108.7C50—C49—C48112.6 (3)
C23—C22—C17115.4 (3)C44—C49—C48104.3 (3)
C23—C22—C21112.3 (3)C50—C49—H49108.1
C17—C22—C21103.7 (3)C44—C49—H49108.1
C23—C22—H22108.4C48—C49—H49108.1
C17—C22—H22108.4O6—C50—C51106.0 (3)
C21—C22—H22108.4O6—C50—C49106.5 (3)
O3—C23—C24106.5 (3)C51—C50—C49114.7 (3)
O3—C23—C25102.5 (3)O6—C50—C52103.3 (3)
C24—C23—C25112.4 (3)C51—C50—C52111.9 (3)
O3—C23—C22106.0 (3)C49—C50—C52113.3 (3)
C24—C23—C22114.5 (3)C50—C51—H51A109.5
C25—C23—C22113.7 (3)C50—C51—H51B109.5
C23—C24—H24A109.5H51A—C51—H51B109.5
C23—C24—H24B109.5C50—C51—H51C109.5
H24A—C24—H24B109.5H51A—C51—H51C109.5
C23—C24—H24C109.5H51B—C51—H51C109.5
H24A—C24—H24C109.5C53—C52—C50103.7 (3)
H24B—C24—H24C109.5C53—C52—H52A111.0
C26—C25—C23104.0 (3)C50—C52—H52A111.0
C26—C25—H25A111.0C53—C52—H52B111.0
C23—C25—H25A111.0C50—C52—H52B111.0
C26—C25—H25B111.0H52A—C52—H52B109.0
C23—C25—H25B111.0C54—C53—C52103.8 (3)
H25A—C25—H25B109.0C54—C53—H53A111.0
C27—C26—C25103.0 (3)C52—C53—H53A111.0
C27—C26—H26A111.2C54—C53—H53B111.0
C25—C26—H26A111.2C52—C53—H53B111.0
C27—C26—H26B111.2H53A—C53—H53B109.0
C25—C26—H26B111.2O5—C54—O6121.0 (3)
H26A—C26—H26B109.1O5—C54—C53128.2 (4)
O2—C27—O3121.3 (4)O6—C54—C53110.8 (3)
O1—C1—C2—C3−67.4 (4)O4—C28—C29—C30−69.8 (4)
C7—C1—C2—C355.4 (4)C34—C28—C29—C3053.9 (4)
C1—C2—C3—C4−57.9 (4)C28—C29—C30—C31−55.4 (4)
C2—C3—C4—C5−70.1 (4)C29—C30—C31—C32−71.5 (4)
C2—C3—C4—C654.3 (4)C29—C30—C31—C3352.4 (4)
C2—C3—C4—C14168.3 (3)C29—C30—C31—C41167.0 (3)
C3—C4—C6—C10174.8 (3)C30—C31—C33—C37173.2 (3)
C5—C4—C6—C10−65.4 (4)C32—C31—C33—C37−67.0 (4)
C14—C4—C6—C1059.3 (4)C41—C31—C33—C3757.3 (4)
C3—C4—C6—C7−53.0 (4)C30—C31—C33—C34−54.0 (4)
C5—C4—C6—C766.8 (4)C32—C31—C33—C3465.7 (4)
C14—C4—C6—C7−168.4 (3)C41—C31—C33—C34−170.0 (3)
O1—C1—C7—C8−164.7 (3)O4—C28—C34—C36−49.2 (4)
C2—C1—C7—C874.5 (4)C29—C28—C34—C36−170.2 (3)
O1—C1—C7—C9−49.0 (4)O4—C28—C34—C35−164.3 (3)
C2—C1—C7—C9−169.8 (3)C29—C28—C34—C3574.7 (4)
O1—C1—C7—C670.3 (4)O4—C28—C34—C3369.9 (4)
C2—C1—C7—C6−50.5 (4)C29—C28—C34—C33−51.1 (4)
C10—C6—C7—C859.9 (4)C37—C33—C34—C36−56.2 (4)
C4—C6—C7—C8−71.2 (4)C31—C33—C34—C36171.9 (3)
C10—C6—C7—C9−59.8 (4)C37—C33—C34—C3563.5 (5)
C4—C6—C7—C9169.1 (3)C31—C33—C34—C35−68.4 (4)
C10—C6—C7—C1−177.7 (3)C37—C33—C34—C28−174.5 (3)
C4—C6—C7—C151.2 (4)C31—C33—C34—C2853.6 (4)
C7—C6—C10—C11164.0 (3)C34—C33—C37—C38164.2 (3)
C4—C6—C10—C11−62.2 (4)C31—C33—C37—C38−61.4 (4)
C6—C10—C11—C1258.0 (4)C33—C37—C38—C3958.1 (4)
C10—C11—C12—C1370.9 (4)C37—C38—C39—C4070.5 (4)
C10—C11—C12—C14−51.3 (4)C37—C38—C39—C41−51.2 (4)
C10—C11—C12—C18−169.4 (3)C37—C38—C39—C45−168.8 (3)
C11—C12—C14—C15−175.2 (3)C38—C39—C41—C42−175.3 (3)
C13—C12—C14—C1565.8 (4)C40—C39—C41—C4265.5 (4)
C18—C12—C14—C15−55.6 (4)C45—C39—C41—C42−55.4 (4)
C11—C12—C14—C451.9 (4)C38—C39—C41—C3150.7 (4)
C13—C12—C14—C4−67.0 (4)C40—C39—C41—C31−68.5 (4)
C18—C12—C14—C4171.6 (3)C45—C39—C41—C31170.7 (3)
C3—C4—C14—C1557.8 (4)C30—C31—C41—C4259.1 (4)
C5—C4—C14—C15−61.0 (4)C32—C31—C41—C42−60.0 (4)
C6—C4—C14—C15172.6 (3)C33—C31—C41—C42174.0 (3)
C3—C4—C14—C12−170.5 (3)C30—C31—C41—C39−168.4 (3)
C5—C4—C14—C1270.7 (4)C32—C31—C41—C3972.6 (4)
C6—C4—C14—C12−55.7 (4)C33—C31—C41—C39−53.4 (4)
C12—C14—C15—C1654.6 (4)C39—C41—C42—C4355.0 (4)
C4—C14—C15—C16−171.9 (3)C31—C41—C42—C43−170.5 (3)
C14—C15—C16—C17−54.7 (4)C41—C42—C43—C44−54.9 (4)
C15—C16—C17—C1858.4 (4)C42—C43—C44—C4558.5 (4)
C15—C16—C17—C22−178.7 (3)C42—C43—C44—C49−178.4 (3)
C16—C17—C18—C20174.1 (3)C43—C44—C45—C47172.8 (3)
C22—C17—C18—C2043.4 (3)C49—C44—C45—C4741.5 (3)
C16—C17—C18—C1962.1 (4)C43—C44—C45—C4661.0 (4)
C22—C17—C18—C19−68.5 (4)C49—C44—C45—C46−70.3 (4)
C16—C17—C18—C12−61.6 (4)C43—C44—C45—C39−62.9 (4)
C22—C17—C18—C12167.7 (3)C49—C44—C45—C39165.8 (3)
C11—C12—C18—C20−69.8 (4)C38—C39—C45—C47−68.2 (4)
C13—C12—C18—C2048.5 (4)C40—C39—C45—C4751.1 (4)
C14—C12—C18—C20171.7 (3)C41—C39—C45—C47173.0 (3)
C11—C12—C18—C1954.0 (4)C38—C39—C45—C44178.2 (3)
C13—C12—C18—C19172.2 (3)C40—C39—C45—C44−62.5 (4)
C14—C12—C18—C19−64.6 (4)C41—C39—C45—C4459.4 (4)
C11—C12—C18—C17176.9 (3)C38—C39—C45—C4654.8 (4)
C13—C12—C18—C17−64.9 (4)C40—C39—C45—C46174.1 (3)
C14—C12—C18—C1758.4 (4)C41—C39—C45—C46−64.0 (4)
C19—C18—C20—C2171.8 (4)C44—C45—C47—C48−46.3 (4)
C17—C18—C20—C21−43.3 (4)C46—C45—C47—C4868.9 (4)
C12—C18—C20—C21−161.8 (3)C39—C45—C47—C48−165.4 (3)
C18—C20—C21—C2227.6 (4)C45—C47—C48—C4934.1 (4)
C16—C17—C22—C2384.2 (4)C43—C44—C49—C5089.6 (4)
C18—C17—C22—C23−149.9 (3)C45—C44—C49—C50−144.8 (3)
C16—C17—C22—C21−152.6 (3)C43—C44—C49—C48−146.5 (3)
C18—C17—C22—C21−26.7 (4)C45—C44—C49—C48−20.8 (4)
C20—C21—C22—C23124.6 (3)C47—C48—C49—C50117.4 (3)
C20—C21—C22—C17−0.6 (4)C47—C48—C49—C44−8.2 (4)
C27—O3—C23—C24−140.5 (3)C54—O6—C50—C51−98.6 (4)
C27—O3—C23—C25−22.2 (4)C54—O6—C50—C49138.8 (3)
C27—O3—C23—C2297.2 (3)C54—O6—C50—C5219.2 (4)
C17—C22—C23—O3168.6 (3)C44—C49—C50—O669.1 (4)
C21—C22—C23—O350.1 (4)C48—C49—C50—O6−50.3 (4)
C17—C22—C23—C2451.5 (4)C44—C49—C50—C51−47.8 (5)
C21—C22—C23—C24−67.0 (4)C48—C49—C50—C51−167.3 (3)
C17—C22—C23—C25−79.6 (4)C44—C49—C50—C52−178.0 (3)
C21—C22—C23—C25161.9 (3)C48—C49—C50—C5262.6 (4)
O3—C23—C25—C2629.3 (4)O6—C50—C52—C53−26.6 (4)
C24—C23—C25—C26143.3 (3)C51—C50—C52—C5387.0 (4)
C22—C23—C25—C26−84.6 (4)C49—C50—C52—C53−141.5 (3)
C23—C25—C26—C27−26.3 (4)C50—C52—C53—C5424.8 (4)
C23—O3—C27—O2−173.8 (3)C50—O6—C54—O5176.5 (4)
C23—O3—C27—C265.6 (4)C50—O6—C54—C53−3.4 (4)
C25—C26—C27—O2−167.0 (4)C52—C53—C54—O5166.0 (4)
C25—C26—C27—O313.6 (4)C52—C53—C54—O6−14.1 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O4i0.842.022.836 (4)163
O4—H4···O20.842.032.858 (4)169

Symmetry codes: (i) x−1/2, −y+3/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5334).

References

  • Awang, K., Loong, X. M., Mohamad, K., Chong, S. L. & Ng, S. W. (2010). Acta Cryst. E66, o2142. [PMC free article] [PubMed]
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Su, B.-N., Chai, H., Mi, Q., Riswan, S., Kardono, L. B. S., Afriastini, J. J., Santarsiero, B. D., Mesecar, A. D., Farnsworth, N. R., Cordell, G. A., Swanson, S. M. & Kinghorn, A. D. (2006). Bioorg. Med. Chem.14, 960–972. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.
  • Yang, S.-M., Tan, C.-H., Luo, H.-F., Wang, D.-X. & Zhu, D.-Y. (2008). Helv. Chim. Acta, 91, 333–337.

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