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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1332.
Published online 2008 June 25. doi:  10.1107/S1600536808018151
PMCID: PMC2961863

6-[(E)-3,7-Dimethyl­octa-2,6-dien­yl]-5,7-dihydr­oxy-8-(2-methyl­butano­yl)-4-phenyl-2H-chromen-2-one from Mesua kunstleri King (Kosterm)

Abstract

The title compound, C30H34O5, crystallizes with two symmetry-independent mol­ecules in the asymmetric unit. In the crystal structure, the two independent mol­ecules are disposed about a pseudo-center of inversion. An intra­molecular O—H(...)O hydrogen bond is observed in each independent mol­ecule. The crystal structure is stabilized by C—H(...)O hydrogen bonds.

Related literature

For the spectroscopic analysis of the title compound, see: Verotta et al. (2004 [triangle]).

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Object name is e-64-o1332-scheme1.jpg

Experimental

Crystal data

  • C30H34O5
  • M r = 474.57
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1332-efi1.jpg
  • a = 5.6729 (1) Å
  • b = 13.4350 (3) Å
  • c = 16.8404 (3) Å
  • α = 87.550 (1)°
  • β = 82.243 (1)°
  • γ = 85.332 (1)°
  • V = 1266.88 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100 (2) K
  • 0.40 × 0.08 × 0.04 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 16336 measured reflections
  • 5783 independent reflections
  • 4459 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.070
  • wR(F 2) = 0.210
  • S = 1.04
  • 5783 reflections
  • 645 parameters
  • 65 restraints
  • H-atom parameters constrained
  • Δρmax = 1.21 e Å−3
  • Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018151/ci2600sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018151/ci2600Isup2.hkl

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

Acknowledgments

The authors thank the University of Malaya (PPP PS156/2007B) for supporting this study.

supplementary crystallographic information

Comment

The title compound, previously isolated from Mesua ferrea, has been evaluated as a multidrug-resistant antibacterial. The structure was elucidated from spectroscopic measurements (Verotta et al., 2004). Locally, the bark of Mesua kunstleri (King) Kosterm is used for the treatment of dyspepsis and renal diseases. The identical compound is isloated from the bark of this plant; the compound features the common coumarin skeleton, and is an 8-acyl-6-prenyl derivative. The spectroscopic assignment is now confirmed in the crystal structure analysis.

The title compound contains two independent molecules that are disposed over a false center of inversion (Fig. 1). An intramolecular O—H···O hydrogen bond is observed in each independent molecule. The crystal structure is stabilized by C—H···O hydrogen bonds (Table 1).

Experimental

One-and-a-half kg of the bark of Mesua kunstleri King (Kosterm), (Clusiaceae), collected at Hutan Simpanan Rimba Teloi, Kedah, Malaysia [voucher specimen number KL4485], were extracted by maceration in hexane (6 L) for 72 h to yield a gummy residue (103 g). A portion (10 g) was column chromatographed over silica gel (300 g, 40–63 µm) by using hexane-ethyl acetate as eluents to give six fractions. The first fraction (6 g) was further chromatographed over silica gel (180 g, 5–40 µm) by using hexane:ethyl acetate (95:5). The title compound (1.5 g) was eluted with hexane:ethyl acetate (96:4).

Refinement

For the 2-methylbutanoyl fragments, 1,2-related C–C distances were restrained to 1.54 (1) Å and 1,3-related ones to 2.51 (1) Å; the anisotropic displacement parameters of the carbon atoms (except the double-bond ones) were restrained to be nearly isotropic. H-atoms were placed in calculated positions (O—H = 0.84 Å and C—H = 0.95–0.99 Å) and were included in the refinement in the riding-model approximation, with U(H) set to 1.2–1.5Ueq(C,O). The torsion angles of the hydroxy groups were refined. The final difference Fourier map had a large peak in the vicinity of the 2-methylbutanoyl fragment of a independent molecule. The chirality of the compound is assumed from the reported optical activity measurements (Verotta et al., 2004).

Figures

Fig. 1.
An ORTEP plot of the title compound, showing 70% probability displacement ellipsoids and the atomic numbering scheme. Hydrogen atoms are drawn as spheres of arbitrary radii. The two independent molecules are disposed over a false center of inversion.

Crystal data

C30H34O5Z = 2
Mr = 474.57F000 = 508
Triclinic, P1Dx = 1.244 Mg m3
Hall symbol: P 1Mo Kα radiation λ = 0.71073 Å
a = 5.6729 (1) ÅCell parameters from 3286 reflections
b = 13.4350 (3) Åθ = 2.4–28.2º
c = 16.8404 (3) ŵ = 0.08 mm1
α = 87.550 (1)ºT = 100 (2) K
β = 82.243 (1)ºPrism, colourless
γ = 85.332 (1)º0.40 × 0.08 × 0.04 mm
V = 1266.88 (4) Å3

Data collection

Bruker SMART APEX diffractometer4459 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
Monochromator: graphiteθmax = 27.5º
T = 100(2) Kθmin = 1.2º
ω scansh = −7→7
Absorption correction: Nonek = −17→13
16336 measured reflectionsl = −21→21
5783 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.070H-atom parameters constrained
wR(F2) = 0.210  w = 1/[σ2(Fo2) + (0.111P)2 + 1.3027P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
5783 reflectionsΔρmax = 1.21 e Å3
645 parametersΔρmin = −0.44 e Å3
65 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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.

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

xyzUiso*/Ueq
O10.5000 (7)0.5000 (3)0.5000 (2)0.0199 (9)
O20.8130 (8)0.4223 (3)0.5477 (3)0.0251 (10)
O30.2134 (7)0.8422 (3)0.5466 (3)0.0248 (10)
H3O0.33560.84190.56980.037*
O4−0.1436 (8)0.6584 (4)0.3762 (3)0.0291 (10)
H4O−0.15060.59990.36140.044*
O50.0088 (10)0.4887 (4)0.3416 (4)0.0476 (15)
O6−0.5997 (7)1.4425 (3)0.7678 (3)0.0224 (9)
O7−0.9094 (8)1.5196 (4)0.7193 (3)0.0327 (12)
O8−0.2864 (8)1.1053 (3)0.7113 (3)0.0260 (10)
H8O−0.35741.11330.67050.039*
O90.0561 (8)1.2875 (4)0.8869 (3)0.0291 (11)
H9O0.02881.33780.91560.044*
O10−0.1233 (12)1.4518 (5)0.9302 (4)0.060 (2)
C10.6762 (10)0.4958 (5)0.5509 (3)0.0185 (12)
C20.6655 (10)0.5786 (5)0.6033 (4)0.0202 (12)
H20.77050.57660.64290.024*
C30.5081 (10)0.6595 (5)0.5972 (4)0.0207 (13)
C40.4912 (10)0.7375 (5)0.6583 (4)0.0191 (12)
C50.6800 (10)0.7969 (5)0.6608 (4)0.0227 (13)
H50.82150.78670.62400.027*
C60.6627 (11)0.8711 (5)0.7168 (4)0.0253 (14)
H60.79240.91110.71850.030*
C70.4530 (11)0.8868 (5)0.7710 (4)0.0278 (14)
H70.43860.93900.80810.033*
C80.2727 (12)0.8279 (7)0.7702 (5)0.0399 (19)
H80.13410.83660.80850.048*
C90.2875 (12)0.7538 (7)0.7133 (5)0.0380 (18)
H90.15660.71420.71230.046*
C100.3524 (10)0.6652 (4)0.5356 (4)0.0180 (12)
C110.3452 (10)0.5805 (4)0.4900 (3)0.0180 (12)
C120.2028 (10)0.7510 (5)0.5160 (4)0.0202 (13)
C130.0372 (10)0.7467 (5)0.4626 (4)0.0203 (12)
C14−0.1347 (10)0.8390 (5)0.4488 (4)0.0216 (13)
H14A−0.28710.81650.43630.026*
H14B−0.16910.87690.49870.026*
C15−0.0330 (10)0.9071 (5)0.3812 (4)0.0200 (12)
H150.10830.93700.38860.024*
C16−0.1191 (11)0.9300 (5)0.3123 (4)0.0233 (13)
C17−0.3265 (12)0.8834 (5)0.2859 (5)0.0329 (16)
H17A−0.36090.82350.31940.049*
H17B−0.28690.86500.22970.049*
H17C−0.46690.93140.29140.049*
C18−0.0055 (11)1.0067 (5)0.2547 (4)0.0286 (15)
H18A0.05260.97500.20300.034*
H18B0.13431.02930.27630.034*
C19−0.1767 (12)1.0977 (6)0.2398 (4)0.0316 (15)
H19A−0.29991.07750.20870.038*
H19B−0.25841.12180.29200.038*
C20−0.0517 (12)1.1810 (5)0.1955 (4)0.0292 (14)
H200.07871.20200.21880.035*
C21−0.0959 (11)1.2300 (5)0.1281 (4)0.0260 (13)
C220.0533 (13)1.3134 (5)0.0928 (4)0.0330 (15)
H22A0.18361.31930.12460.049*
H22B−0.04681.37640.09340.049*
H22C0.11971.29850.03740.049*
C23−0.2890 (12)1.2083 (6)0.0812 (4)0.0300 (14)
H23A−0.38671.15840.11070.045*
H23B−0.21821.18240.02910.045*
H23C−0.38921.26980.07300.045*
C240.0277 (10)0.6593 (5)0.4246 (3)0.0195 (13)
C250.1865 (11)0.5725 (5)0.4348 (4)0.0215 (13)
C260.1610 (13)0.4843 (5)0.3891 (5)0.044 (2)
C270.3025 (12)0.3828 (5)0.3980 (5)0.072 (3)
H270.33970.37710.45450.086*
C280.148 (2)0.2962 (6)0.3877 (7)0.074 (3)
H28A0.23730.23240.39820.111*
H28B0.10850.29840.33280.111*
H28C0.00130.30270.42560.111*
C290.5363 (14)0.3846 (7)0.3452 (5)0.075 (3)
H29A0.62870.31940.35000.089*
H29B0.62940.43680.36290.089*
C300.4987 (19)0.4062 (8)0.2566 (5)0.104 (4)
H30A0.65320.40030.22250.156*
H30B0.42400.47410.25070.156*
H30C0.39500.35800.24040.156*
C31−0.7703 (10)1.4460 (5)0.7166 (4)0.0234 (13)
C32−0.7549 (10)1.3652 (5)0.6628 (4)0.0238 (13)
H32−0.86271.36700.62410.029*
C33−0.5920 (10)1.2867 (5)0.6654 (4)0.0201 (13)
C34−0.5701 (10)1.2096 (5)0.6026 (4)0.0218 (13)
C35−0.3631 (11)1.1987 (6)0.5479 (5)0.0331 (17)
H35−0.23821.24130.54940.040*
C36−0.3404 (11)1.1258 (6)0.4915 (5)0.0353 (17)
H36−0.19751.11690.45510.042*
C37−0.5277 (11)1.0645 (5)0.4875 (4)0.0267 (14)
H37−0.51291.01500.44810.032*
C38−0.7304 (11)1.0768 (5)0.5406 (4)0.0261 (14)
H38−0.85671.03500.53870.031*
C40−0.4357 (10)1.2785 (5)0.7283 (3)0.0194 (13)
C41−0.4404 (10)1.3618 (5)0.7759 (4)0.0213 (13)
C42−0.2805 (10)1.1951 (4)0.7452 (4)0.0191 (13)
C39−0.7539 (10)1.1500 (5)0.5975 (4)0.0202 (12)
H39−0.89791.15920.63330.024*
C43−0.1161 (11)1.1979 (5)0.7973 (4)0.0217 (13)
C440.0599 (11)1.1120 (5)0.8118 (4)0.0237 (13)
H44A0.20831.13880.82370.028*
H44B0.09981.07430.76190.028*
C45−0.0254 (10)1.0410 (4)0.8791 (4)0.0202 (12)
H45−0.16011.00620.87210.024*
C460.0662 (11)1.0211 (5)0.9474 (4)0.0231 (13)
C470.2795 (12)1.0687 (6)0.9704 (5)0.0323 (15)
H47A0.32471.12210.93110.048*
H47B0.41371.01800.97120.048*
H47C0.23821.09681.02370.048*
C48−0.0360 (11)0.9436 (5)1.0062 (4)0.0257 (14)
H48A−0.17720.91950.98650.031*
H48B−0.09100.97551.05810.031*
C490.1398 (12)0.8531 (5)1.0205 (4)0.0303 (15)
H49A0.22250.82990.96820.036*
H49B0.26170.87391.05200.036*
C500.0163 (14)0.7689 (5)1.0643 (4)0.0346 (16)
H50−0.11330.74691.04110.042*
C510.0647 (12)0.7206 (5)1.1317 (4)0.0292 (14)
C52−0.0778 (16)0.6359 (7)1.1650 (5)0.047 (2)
H52A−0.17550.61691.12520.071*
H52B−0.18170.65661.21370.071*
H52C0.03040.57861.17790.071*
C530.2580 (14)0.7435 (6)1.1803 (5)0.0422 (19)
H53A0.33480.80271.15700.063*
H53B0.37710.68641.17980.063*
H53C0.18740.75621.23570.063*
C54−0.1128 (12)1.2858 (5)0.8400 (4)0.0256 (14)
C55−0.2840 (12)1.3680 (5)0.8344 (4)0.0264 (14)
C56−0.2909 (14)1.4498 (5)0.8911 (4)0.045 (2)
C57−0.5006 (13)1.5287 (5)0.9073 (4)0.059 (2)
H57−0.63601.50030.88580.071*
C58−0.583 (2)1.5373 (11)0.9978 (5)0.090 (4)
H58C−0.73241.57961.00620.136*
H58D−0.46021.56701.02290.136*
H58E−0.60781.47061.02180.136*
C59−0.4514 (18)1.6215 (6)0.8552 (6)0.082 (3)
H59A−0.59431.66940.86090.098*
H59B−0.41601.60330.79830.098*
C60−0.2386 (17)1.6704 (7)0.8803 (6)0.075 (3)
H60A−0.23791.73940.85890.112*
H60B−0.08991.63270.85900.112*
H60C−0.25221.67020.93890.112*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.025 (2)0.015 (2)0.0197 (19)0.0034 (16)−0.0062 (15)−0.0007 (16)
O20.026 (2)0.018 (2)0.032 (2)0.0049 (17)−0.0069 (17)−0.0085 (18)
O30.023 (2)0.011 (2)0.040 (3)0.0011 (17)−0.0022 (18)−0.0050 (19)
O40.041 (2)0.023 (3)0.025 (2)0.006 (2)−0.0127 (19)−0.003 (2)
O50.060 (3)0.030 (3)0.061 (3)0.019 (2)−0.043 (3)−0.022 (3)
O60.025 (2)0.014 (2)0.029 (2)0.0039 (16)−0.0088 (17)−0.0078 (17)
O70.022 (2)0.029 (3)0.048 (3)0.0103 (19)−0.0116 (19)−0.016 (2)
O80.032 (2)0.014 (2)0.030 (2)0.0008 (18)−0.0002 (19)−0.0053 (19)
O90.039 (3)0.022 (3)0.026 (2)0.013 (2)−0.0130 (19)−0.003 (2)
O100.097 (5)0.038 (3)0.054 (3)0.037 (3)−0.058 (3)−0.026 (3)
C10.019 (3)0.017 (3)0.019 (3)0.001 (2)−0.004 (2)0.002 (2)
C20.016 (3)0.018 (3)0.026 (3)0.002 (2)−0.001 (2)−0.006 (2)
C30.020 (3)0.020 (3)0.021 (3)−0.002 (2)0.001 (2)−0.009 (2)
C40.017 (3)0.015 (3)0.025 (3)0.001 (2)−0.002 (2)−0.005 (2)
C50.024 (3)0.018 (3)0.023 (3)0.004 (2)0.003 (2)0.000 (2)
C60.024 (3)0.018 (3)0.034 (4)0.001 (2)−0.005 (2)−0.001 (3)
C70.028 (3)0.026 (4)0.030 (3)0.010 (3)−0.008 (3)−0.012 (3)
C80.027 (3)0.050 (5)0.041 (4)−0.005 (3)0.010 (3)−0.024 (4)
C90.024 (3)0.051 (5)0.039 (4)−0.007 (3)0.005 (3)−0.026 (4)
C100.021 (3)0.008 (3)0.024 (3)0.000 (2)0.001 (2)−0.001 (2)
C110.025 (3)0.012 (3)0.016 (3)0.003 (2)0.001 (2)0.000 (2)
C120.020 (3)0.018 (3)0.021 (3)0.001 (2)0.003 (2)0.000 (2)
C130.021 (3)0.020 (3)0.019 (3)0.002 (2)0.002 (2)0.002 (2)
C140.025 (3)0.016 (3)0.021 (3)0.011 (2)0.001 (2)0.001 (2)
C150.019 (3)0.019 (3)0.021 (3)0.003 (2)0.001 (2)−0.004 (2)
C160.027 (3)0.018 (3)0.024 (3)0.008 (2)−0.005 (2)0.000 (2)
C170.031 (3)0.026 (4)0.043 (4)0.001 (3)−0.014 (3)0.001 (3)
C180.030 (3)0.026 (4)0.025 (3)0.010 (3)0.004 (2)0.007 (3)
C190.033 (3)0.034 (4)0.024 (3)0.011 (3)0.000 (2)0.002 (3)
C200.036 (3)0.027 (4)0.025 (3)0.002 (3)−0.007 (2)−0.007 (3)
C210.030 (3)0.027 (3)0.021 (3)0.002 (2)−0.003 (2)−0.004 (2)
C220.042 (4)0.028 (4)0.029 (3)−0.001 (3)−0.009 (3)0.007 (3)
C230.030 (3)0.030 (4)0.031 (3)0.001 (3)−0.008 (2)0.003 (3)
C240.025 (3)0.020 (3)0.012 (3)0.003 (2)−0.002 (2)0.005 (2)
C250.029 (3)0.016 (3)0.019 (3)0.008 (2)−0.008 (2)0.000 (2)
C260.059 (4)0.026 (4)0.052 (4)0.020 (3)−0.040 (4)−0.017 (3)
C270.077 (5)0.062 (5)0.087 (5)0.045 (4)−0.065 (5)−0.053 (4)
C280.101 (7)0.054 (5)0.062 (5)0.006 (5)−0.002 (5)0.002 (4)
C290.095 (6)0.065 (5)0.069 (5)−0.007 (5)−0.025 (5)−0.014 (4)
C300.093 (6)0.121 (7)0.105 (6)0.081 (5)−0.064 (5)−0.100 (6)
C310.017 (3)0.023 (3)0.030 (3)−0.003 (2)−0.002 (2)−0.007 (3)
C320.020 (3)0.025 (4)0.028 (3)−0.002 (2)−0.006 (2)−0.008 (3)
C330.016 (3)0.017 (3)0.027 (3)−0.004 (2)0.000 (2)0.000 (2)
C340.022 (3)0.019 (3)0.024 (3)0.000 (2)−0.002 (2)−0.004 (3)
C350.021 (3)0.033 (4)0.045 (4)−0.010 (3)0.006 (3)−0.022 (3)
C360.017 (3)0.043 (5)0.046 (4)0.000 (3)0.001 (3)−0.029 (3)
C370.029 (3)0.018 (3)0.036 (4)0.003 (2)−0.013 (3)−0.011 (3)
C380.029 (3)0.019 (3)0.033 (3)−0.005 (3)−0.013 (3)−0.002 (3)
C400.023 (3)0.020 (3)0.014 (3)−0.003 (2)0.001 (2)0.000 (2)
C410.026 (3)0.014 (3)0.022 (3)0.003 (2)0.000 (2)0.001 (2)
C420.023 (3)0.010 (3)0.021 (3)−0.002 (2)0.009 (2)−0.001 (2)
C390.016 (3)0.018 (3)0.027 (3)−0.008 (2)−0.003 (2)0.000 (2)
C430.029 (3)0.011 (3)0.021 (3)0.004 (2)0.007 (2)0.002 (2)
C440.026 (3)0.015 (3)0.029 (3)−0.001 (2)0.001 (2)0.000 (3)
C450.022 (3)0.010 (3)0.026 (3)0.004 (2)−0.001 (2)0.001 (2)
C460.024 (3)0.018 (3)0.025 (3)0.005 (2)0.002 (2)−0.003 (2)
C470.030 (3)0.032 (4)0.036 (4)0.007 (3)−0.013 (3)−0.002 (3)
C480.030 (3)0.026 (4)0.019 (3)0.003 (3)−0.003 (2)0.001 (2)
C490.041 (4)0.017 (3)0.030 (3)0.006 (3)−0.001 (3)0.006 (3)
C500.057 (4)0.021 (4)0.027 (3)0.003 (3)−0.018 (3)0.003 (3)
C510.045 (4)0.021 (3)0.021 (3)0.004 (3)−0.005 (2)0.002 (2)
C520.065 (5)0.043 (5)0.036 (4)−0.008 (4)−0.013 (3)0.010 (3)
C530.046 (4)0.041 (5)0.040 (4)0.014 (3)−0.018 (3)0.000 (3)
C540.034 (3)0.022 (4)0.020 (3)0.003 (3)−0.004 (2)−0.001 (3)
C550.045 (4)0.013 (3)0.021 (3)0.004 (3)−0.007 (3)−0.004 (2)
C560.075 (5)0.029 (4)0.032 (3)0.022 (4)−0.026 (3)−0.015 (3)
C570.087 (5)0.054 (5)0.041 (4)0.036 (4)−0.037 (4)−0.027 (3)
C580.094 (7)0.109 (8)0.063 (5)0.028 (6)−0.009 (5)−0.010 (6)
C590.122 (7)0.056 (5)0.075 (5)0.022 (5)−0.054 (5)−0.010 (4)
C600.098 (6)0.063 (5)0.075 (6)0.017 (5)−0.059 (5)−0.030 (4)

Geometric parameters (Å, °)

O1—C111.357 (7)C28—H28B0.98
O1—C11.399 (7)C28—H28C0.98
O2—C11.203 (8)C29—C301.548 (8)
O3—C121.358 (8)C29—H29A0.99
O3—H3O0.84C29—H29B0.99
O4—C241.352 (8)C30—H30A0.98
O4—H4O0.84C30—H30B0.98
O5—C261.251 (8)C30—H30C0.98
O6—C411.369 (7)C31—C321.433 (9)
O6—C311.378 (7)C32—C331.348 (9)
O7—C311.212 (8)C32—H320.95
O8—C421.361 (7)C33—C401.466 (9)
O8—H8O0.84C33—C341.497 (9)
O9—C541.324 (8)C34—C391.379 (8)
O9—H9O0.84C34—C351.393 (9)
O10—C561.230 (9)C35—C361.381 (9)
C1—C21.442 (8)C35—H350.95
C2—C31.359 (9)C36—C371.406 (9)
C2—H20.95C36—H360.95
C3—C101.445 (9)C37—C381.362 (10)
C3—C41.489 (8)C37—H370.95
C4—C91.389 (9)C38—C391.389 (9)
C4—C51.393 (9)C38—H380.95
C5—C61.390 (9)C40—C411.400 (9)
C5—H50.95C40—C421.411 (9)
C6—C71.405 (9)C41—C551.421 (10)
C6—H60.95C42—C431.368 (9)
C7—C81.346 (10)C39—H390.95
C7—H70.95C43—C541.411 (9)
C8—C91.401 (10)C43—C441.497 (9)
C8—H80.95C44—C451.506 (8)
C9—H90.95C44—H44A0.99
C10—C111.406 (8)C44—H44B0.99
C10—C121.429 (8)C45—C461.332 (9)
C11—C251.392 (8)C45—H450.95
C12—C131.392 (9)C46—C481.502 (9)
C13—C241.369 (9)C46—C471.516 (10)
C13—C141.543 (8)C47—H47A0.98
C14—C151.513 (8)C47—H47B0.98
C14—H14A0.99C47—H47C0.98
C14—H14B0.99C48—C491.540 (9)
C15—C161.332 (8)C48—H48A0.99
C15—H150.95C48—H48B0.99
C16—C171.503 (9)C49—C501.495 (10)
C16—C181.508 (9)C49—H49A0.99
C17—H17A0.98C49—H49B0.99
C17—H17B0.98C50—C511.333 (9)
C17—H17C0.98C50—H500.95
C18—C191.533 (9)C51—C521.496 (11)
C18—H18A0.99C51—C531.512 (10)
C18—H18B0.99C52—H52A0.98
C19—C201.492 (10)C52—H52B0.98
C19—H19A0.99C52—H52C0.98
C19—H19B0.99C53—H53A0.98
C20—C211.330 (9)C53—H53B0.98
C20—H200.95C53—H53C0.98
C21—C231.488 (9)C54—C551.420 (10)
C21—C221.512 (9)C55—C561.481 (9)
C22—H22A0.98C56—C571.531 (7)
C22—H22B0.98C57—C591.516 (8)
C22—H22C0.98C57—C581.538 (8)
C23—H23A0.98C57—H571.00
C23—H23B0.98C58—H58C0.98
C23—H23C0.98C58—H58D0.98
C24—C251.433 (8)C58—H58E0.98
C25—C261.466 (9)C59—C601.535 (8)
C26—C271.537 (7)C59—H59A0.99
C27—C291.495 (8)C59—H59B0.99
C27—C281.540 (8)C60—H60A0.98
C27—H271.00C60—H60B0.98
C28—H28A0.98C60—H60C0.98
C11—O1—C1124.6 (5)C29—C30—H30C109.5
C12—O3—H3O109.5H30A—C30—H30C109.5
C24—O4—H4O109.5H30B—C30—H30C109.5
C41—O6—C31123.3 (5)O7—C31—O6116.3 (6)
C42—O8—H8O109.5O7—C31—C32127.2 (6)
C54—O9—H9O109.5O6—C31—C32116.4 (5)
O2—C1—O1116.4 (6)C33—C32—C31122.0 (6)
O2—C1—C2127.9 (5)C33—C32—H32119.0
O1—C1—C2115.7 (5)C31—C32—H32119.0
C3—C2—C1121.2 (6)C32—C33—C40119.9 (6)
C3—C2—H2119.4C32—C33—C34119.3 (6)
C1—C2—H2119.4C40—C33—C34120.8 (5)
C2—C3—C10120.1 (6)C39—C34—C35119.4 (6)
C2—C3—C4118.1 (5)C39—C34—C33120.8 (5)
C10—C3—C4121.7 (5)C35—C34—C33119.8 (5)
C9—C4—C5118.4 (6)C36—C35—C34119.7 (6)
C9—C4—C3121.3 (6)C36—C35—H35120.1
C5—C4—C3120.3 (5)C34—C35—H35120.1
C6—C5—C4120.4 (5)C35—C36—C37120.4 (6)
C6—C5—H5119.8C35—C36—H36119.8
C4—C5—H5119.8C37—C36—H36119.8
C5—C6—C7119.9 (6)C38—C37—C36119.3 (6)
C5—C6—H6120.0C38—C37—H37120.3
C7—C6—H6120.0C36—C37—H37120.3
C8—C7—C6119.9 (7)C37—C38—C39120.5 (6)
C8—C7—H7120.1C37—C38—H38119.8
C6—C7—H7120.1C39—C38—H38119.8
C7—C8—C9120.5 (6)C41—C40—C42117.0 (6)
C7—C8—H8119.7C41—C40—C33116.8 (6)
C9—C8—H8119.7C42—C40—C33126.2 (6)
C4—C9—C8120.8 (6)O6—C41—C40120.6 (6)
C4—C9—H9119.6O6—C41—C55116.4 (6)
C8—C9—H9119.6C40—C41—C55123.0 (6)
C11—C10—C12116.0 (6)O8—C42—C43115.1 (5)
C11—C10—C3118.6 (5)O8—C42—C40122.1 (6)
C12—C10—C3125.4 (6)C43—C42—C40122.8 (6)
O1—C11—C25116.7 (5)C34—C39—C38120.6 (6)
O1—C11—C10118.9 (5)C34—C39—H39119.7
C25—C11—C10124.4 (5)C38—C39—H39119.7
O3—C12—C13115.2 (5)C42—C43—C54118.5 (6)
O3—C12—C10123.1 (6)C42—C43—C44123.3 (6)
C13—C12—C10121.7 (6)C54—C43—C44118.2 (6)
C24—C13—C12118.8 (5)C43—C44—C45114.5 (5)
C24—C13—C14121.5 (5)C43—C44—H44A108.6
C12—C13—C14119.7 (6)C45—C44—H44A108.6
C15—C14—C13112.3 (5)C43—C44—H44B108.6
C15—C14—H14A109.2C45—C44—H44B108.6
C13—C14—H14A109.2H44A—C44—H44B107.6
C15—C14—H14B109.2C46—C45—C44127.5 (6)
C13—C14—H14B109.2C46—C45—H45116.2
H14A—C14—H14B107.9C44—C45—H45116.2
C16—C15—C14127.3 (6)C45—C46—C48120.0 (6)
C16—C15—H15116.3C45—C46—C47124.6 (6)
C14—C15—H15116.3C48—C46—C47115.3 (6)
C15—C16—C17124.5 (6)C46—C47—H47A109.5
C15—C16—C18119.9 (6)C46—C47—H47B109.5
C17—C16—C18115.7 (6)H47A—C47—H47B109.5
C16—C17—H17A109.5C46—C47—H47C109.5
C16—C17—H17B109.5H47A—C47—H47C109.5
H17A—C17—H17B109.5H47B—C47—H47C109.5
C16—C17—H17C109.5C46—C48—C49114.3 (5)
H17A—C17—H17C109.5C46—C48—H48A108.7
H17B—C17—H17C109.5C49—C48—H48A108.7
C16—C18—C19113.0 (5)C46—C48—H48B108.7
C16—C18—H18A109.0C49—C48—H48B108.7
C19—C18—H18A109.0H48A—C48—H48B107.6
C16—C18—H18B109.0C50—C49—C48111.9 (6)
C19—C18—H18B109.0C50—C49—H49A109.2
H18A—C18—H18B107.8C48—C49—H49A109.2
C20—C19—C18112.4 (6)C50—C49—H49B109.2
C20—C19—H19A109.1C48—C49—H49B109.2
C18—C19—H19A109.1H49A—C49—H49B107.9
C20—C19—H19B109.1C51—C50—C49128.3 (7)
C18—C19—H19B109.1C51—C50—H50115.9
H19A—C19—H19B107.9C49—C50—H50115.9
C21—C20—C19129.5 (7)C50—C51—C52119.9 (7)
C21—C20—H20115.2C50—C51—C53125.6 (7)
C19—C20—H20115.2C52—C51—C53114.5 (6)
C20—C21—C23124.2 (7)C51—C52—H52A109.5
C20—C21—C22121.2 (6)C51—C52—H52B109.5
C23—C21—C22114.6 (6)H52A—C52—H52B109.5
C21—C22—H22A109.5C51—C52—H52C109.5
C21—C22—H22B109.5H52A—C52—H52C109.5
H22A—C22—H22B109.5H52B—C52—H52C109.5
C21—C22—H22C109.5C51—C53—H53A109.5
H22A—C22—H22C109.5C51—C53—H53B109.5
H22B—C22—H22C109.5H53A—C53—H53B109.5
C21—C23—H23A109.5C51—C53—H53C109.5
C21—C23—H23B109.5H53A—C53—H53C109.5
H23A—C23—H23B109.5H53B—C53—H53C109.5
C21—C23—H23C109.5O9—C54—C43116.8 (6)
H23A—C23—H23C109.5O9—C54—C55121.2 (6)
H23B—C23—H23C109.5C43—C54—C55122.0 (6)
O4—C24—C13116.0 (5)C54—C55—C41115.9 (6)
O4—C24—C25120.7 (6)C54—C55—C56118.0 (6)
C13—C24—C25123.3 (6)C41—C55—C56126.0 (6)
C11—C25—C24115.3 (6)O10—C56—C55118.1 (6)
C11—C25—C26126.8 (5)O10—C56—C57118.0 (6)
C24—C25—C26117.8 (5)C55—C56—C57123.8 (7)
O5—C26—C25119.2 (5)C59—C57—C56109.6 (6)
O5—C26—C27116.2 (6)C59—C57—C58120.3 (8)
C25—C26—C27124.5 (5)C56—C57—C58111.1 (6)
C29—C27—C26108.7 (6)C59—C57—H57104.8
C29—C27—C28117.0 (7)C56—C57—H57104.8
C26—C27—C28111.0 (6)C58—C57—H57104.8
C29—C27—H27106.5C57—C58—H58C109.5
C26—C27—H27106.5C57—C58—H58D109.5
C28—C27—H27106.6H58C—C58—H58D109.5
C27—C28—H28A109.5C57—C58—H58E109.5
C27—C28—H28B109.5H58C—C58—H58E109.5
H28A—C28—H28B109.5H58D—C58—H58E109.5
C27—C28—H28C109.5C57—C59—C60110.0 (6)
H28A—C28—H28C109.5C57—C59—H59A109.7
H28B—C28—H28C109.5C60—C59—H59A109.7
C27—C29—C30110.9 (6)C57—C59—H59B109.7
C27—C29—H29A109.4C60—C59—H59B109.7
C30—C29—H29A109.4H59A—C59—H59B108.2
C27—C29—H29B109.4C59—C60—H60A109.5
C30—C29—H29B109.4C59—C60—H60B109.5
H29A—C29—H29B108.0H60A—C60—H60B109.5
C29—C30—H30A109.5C59—C60—H60C109.5
C29—C30—H30B109.5H60A—C60—H60C109.5
H30A—C30—H30B109.5H60B—C60—H60C109.5
C11—O1—C1—O2−173.5 (5)C41—O6—C31—O7175.4 (6)
C11—O1—C1—C28.8 (8)C41—O6—C31—C32−8.2 (8)
O2—C1—C2—C3176.4 (6)O7—C31—C32—C33−180.0 (7)
O1—C1—C2—C3−6.3 (8)O6—C31—C32—C334.1 (9)
C1—C2—C3—C10−2.0 (9)C31—C32—C33—C404.6 (9)
C1—C2—C3—C4174.2 (5)C31—C32—C33—C34−174.3 (6)
C2—C3—C4—C9−112.4 (7)C32—C33—C34—C39−65.7 (8)
C10—C3—C4—C963.7 (9)C40—C33—C34—C39115.5 (7)
C2—C3—C4—C568.5 (8)C32—C33—C34—C35113.4 (7)
C10—C3—C4—C5−115.5 (7)C40—C33—C34—C35−65.4 (8)
C9—C4—C5—C6−0.5 (10)C39—C34—C35—C36−2.7 (11)
C3—C4—C5—C6178.7 (6)C33—C34—C35—C36178.2 (7)
C4—C5—C6—C7−0.4 (10)C34—C35—C36—C371.9 (12)
C5—C6—C7—C82.2 (11)C35—C36—C37—C38−1.0 (11)
C6—C7—C8—C9−3.0 (12)C36—C37—C38—C390.9 (10)
C5—C4—C9—C8−0.3 (12)C32—C33—C40—C41−9.4 (8)
C3—C4—C9—C8−179.5 (7)C34—C33—C40—C41169.5 (5)
C7—C8—C9—C42.1 (13)C32—C33—C40—C42170.9 (6)
C2—C3—C10—C118.3 (8)C34—C33—C40—C42−10.3 (9)
C4—C3—C10—C11−167.7 (5)C31—O6—C41—C403.2 (9)
C2—C3—C10—C12−171.2 (6)C31—O6—C41—C55−176.8 (5)
C4—C3—C10—C1212.8 (9)C42—C40—C41—O6−174.7 (5)
C1—O1—C11—C25178.0 (5)C33—C40—C41—O65.6 (8)
C1—O1—C11—C10−2.7 (8)C42—C40—C41—C555.4 (9)
C12—C10—C11—O1173.5 (5)C33—C40—C41—C55−174.4 (6)
C3—C10—C11—O1−6.1 (8)C41—C40—C42—O8170.0 (5)
C12—C10—C11—C25−7.2 (8)C33—C40—C42—O8−10.3 (9)
C3—C10—C11—C25173.2 (6)C41—C40—C42—C43−9.1 (8)
C11—C10—C12—O3−170.7 (5)C33—C40—C42—C43170.6 (5)
C3—C10—C12—O38.8 (9)C35—C34—C39—C382.7 (10)
C11—C10—C12—C138.3 (8)C33—C34—C39—C38−178.3 (6)
C3—C10—C12—C13−172.2 (5)C37—C38—C39—C34−1.8 (10)
O3—C12—C13—C24175.3 (5)O8—C42—C43—C54−174.7 (5)
C10—C12—C13—C24−3.8 (8)C40—C42—C43—C544.5 (8)
O3—C12—C13—C14−6.1 (8)O8—C42—C43—C444.9 (8)
C10—C12—C13—C14174.9 (5)C40—C42—C43—C44−176.0 (5)
C24—C13—C14—C15−91.3 (7)C42—C43—C44—C45−90.6 (7)
C12—C13—C14—C1590.1 (7)C54—C43—C44—C4588.9 (7)
C13—C14—C15—C16116.9 (7)C43—C44—C45—C46−116.6 (7)
C14—C15—C16—C17−5.9 (10)C44—C45—C46—C48−176.9 (6)
C14—C15—C16—C18174.6 (5)C44—C45—C46—C470.3 (10)
C15—C16—C18—C19−118.4 (7)C45—C46—C48—C49116.9 (7)
C17—C16—C18—C1962.1 (8)C47—C46—C48—C49−60.6 (8)
C16—C18—C19—C20169.2 (6)C46—C48—C49—C50−167.1 (6)
C18—C19—C20—C21125.9 (8)C48—C49—C50—C51−125.9 (8)
C19—C20—C21—C23−0.9 (11)C49—C50—C51—C52−178.5 (7)
C19—C20—C21—C22179.7 (7)C49—C50—C51—C531.4 (13)
C12—C13—C24—O4177.2 (5)C42—C43—C54—O9−176.8 (6)
C14—C13—C24—O4−1.4 (8)C44—C43—C54—O93.6 (8)
C12—C13—C24—C25−2.4 (9)C42—C43—C54—C554.2 (9)
C14—C13—C24—C25178.9 (5)C44—C43—C54—C55−175.3 (6)
O1—C11—C25—C24−179.1 (5)O9—C54—C55—C41173.6 (6)
C10—C11—C25—C241.6 (9)C43—C54—C55—C41−7.5 (10)
O1—C11—C25—C263.3 (10)O9—C54—C55—C56−8.7 (10)
C10—C11—C25—C26−176.0 (7)C43—C54—C55—C56170.2 (6)
O4—C24—C25—C11−176.1 (5)O6—C41—C55—C54−177.4 (6)
C13—C24—C25—C113.5 (9)C40—C41—C55—C542.5 (9)
O4—C24—C25—C261.8 (9)O6—C41—C55—C565.1 (10)
C13—C24—C25—C26−178.6 (6)C40—C41—C55—C56−175.0 (7)
C11—C25—C26—O5179.9 (7)C54—C55—C56—O1012.7 (11)
C24—C25—C26—O52.3 (11)C41—C55—C56—O10−169.8 (7)
C11—C25—C26—C272.7 (12)C54—C55—C56—C57−163.7 (7)
C24—C25—C26—C27−174.9 (6)C41—C55—C56—C5713.8 (12)
O5—C26—C27—C2997.4 (8)O10—C56—C57—C5987.9 (9)
C25—C26—C27—C29−85.3 (9)C55—C56—C57—C59−95.7 (9)
O5—C26—C27—C28−32.5 (10)O10—C56—C57—C58−47.5 (12)
C25—C26—C27—C28144.7 (8)C55—C56—C57—C58128.9 (9)
C26—C27—C29—C30−58.6 (9)C56—C57—C59—C60−65.9 (9)
C28—C27—C29—C3067.9 (10)C58—C57—C59—C6064.8 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H4O···O50.841.702.438 (8)145
O9—H9O···O100.841.712.452 (9)147
C29—H29B···O5i0.992.293.115 (10)140
C32—H32···O2ii0.952.433.347 (8)161
C35—H35···O2iii0.952.473.242 (9)138
C39—H39···O8iv0.952.553.434 (8)155

Symmetry codes: (i) x+1, y, z; (ii) x−2, y+1, z; (iii) x−1, y+1, z; (iv) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2600).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Verotta, L., Lovaglio, E., Vidari, G., Finzi, P. V., Neri, M. G., Raimondi, A., Parapini, S., Taramelli, D., Riva, A. & Bombardelli, E. (2004). Phytochemistry, 65, 2867–2879. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

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