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

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ISSN: 2056-9890

12α-Hy­dr­oxy-3,27-dioxooleanano-28,13-lactone

aCenter of Separation Technology, School of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, People's Republic of China
*Correspondence e-mail: hjy741110@yahoo.com.cn

(Received 7 April 2012; accepted 21 April 2012; online 2 May 2012)

There are two independent mol­ecules in the asymmetric unit of the title compound, C30H44O5. They comprise a triterpenoid skeleton of five six-membered rings and a five-membered lactone ring. The five six-membered rings are all trans-fused. In both independent mol­ecules the D rings adopt a slightly distorted half-chair conformation due the presence of the lactone ring while the other four six-membered rings all adopt chair conformations. The characteristic carbon–carbon double bond of the oleanoic skeleton is absent. Inter­molecular O—H⋯O hydrogen bonds between the hy­droxy and carbonyl groups occur in the crystal structure.

Related literature

For the pharmacological properties of penta­cyclic triterpene acids, see: Gene et al. (1996[Gene, R. M., Cartana, C., Adzet, T., Marin, E., Parella, T. & Canigueral, S. (1996). Planta Med. 62, 232-235.]); Hu et al. (2009[Hu, J. Y., Yao, Z., Xu, Y. Q. & Duan, H. Q. (2009). J. Asian Nat. Prod. Res. 11, 236-242.]); Xu et al. (2007[Xu, Y. Q., Yao, Z., Hu, J. Y., Jie, T. & Duan, H. Q. (2007). J. Asian Nat. Prod. Res. 9, 637-642.]).

[Scheme 1]

Experimental

Crystal data
  • C30H44O5

  • Mr = 484.65

  • Orthorhombic, P 21 21 21

  • a = 12.4457 (3) Å

  • b = 15.5804 (4) Å

  • c = 27.1710 (8) Å

  • V = 5268.7 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 113 K

  • 0.32 × 0.30 × 0.26 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2007[Rigaku (2007). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.975, Tmax = 0.979

  • 46805 measured reflections

  • 6391 independent reflections

  • 6106 reflections with I > 2σ(I)

  • Rint = 0.054

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.095

  • S = 1.10

  • 6391 reflections

  • 649 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O4i 0.86 (3) 1.94 (3) 2.782 (2) 167 (3)
O7—H7⋯O6ii 0.90 (3) 1.91 (3) 2.803 (2) 172 (2)
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (ii) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2007[Rigaku (2007). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: CrystalStructure (Rigaku, 2007[Rigaku (2007). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Supporting information


Comment top

Pentacyclic triterpene acids such as oleanolic acid, crataegolic acid and ursolic acid and their glycosides are widely distributed in the plant kingdom. They exhibit a variety of pharmacological properties such as analgesic (Gene et al., 1996), cytotoxic (Hu et al., 2009), and immunosuppressive activities (Xu et al., 2007). Recently, our laboratories have disclosed the design and synthesis of a novel series of oleanolic acid derivatives. Herewith, we report the synthesis and crystal structure of the title compound. The title compound crystallizes with two molecules per asymmetric unit (Fig. 1). Each molecule contains a five-membered lactone ring and five trans-fused cyclohexane rings via A(C1—C5, C10), B(C5—C10), C(C8, C9, C11—C14), D(C13—C18) and E(C17—C22) in the molecule A, respectively, and A'(C31—C35, C40), B'(C35—C40), C'(C38, C39, C41—C44), D'(C43—C48) and E'(C47—C52) in the molecule B, respectively. The characteristical carbon double bond of oleanoic skeleton is absent in the title compound. Ring A(A'), B(B'), C(C') and E(E') adopt chair conformations, while ring D(D') adopts a slightly distorted half-chair conformation as a result of the formation of the lactone ring. The hydroxy groups attached to atom C12 and C42 are equatorial. The intermolecular O—H···O hydrogen bonds were observed between the hydroxy groups and carbonyl groups (Table 1) which stablize the crystal structure.

Related literature top

For the pharmacological properties of pentacyclic triterpene acids, see: Gene et al. (1996); Hu et al. (2009); Xu et al. (2007).

Experimental top

Commercially available oleanolic acid and Jones reagent in dry CH2Cl2/acetone (1/1) was stirred at 278 K for 1 h to give 3-oxoolean-12-en-28-oic acid. Reaction of 3-oxoolean-12-en-28-oic acid with O3 in CH2Cl2/MeOH (1:1) at 223 K gave 12-hydroxy-3-oxooleanano -28,13-lactone. A stream of NOCl was introduced to an ice-cold solution of 12-hydroxy-3-oxooleanano-28,13-lactone in pyridine at 233 K over 30 min to give lactone nitrite. A solution of lactone nitrite in acetone was irradiated by high pressure Hg lamp through a Pyrex filter under nitrogen atmosphere for 1 h to give oxime. To a solution of oxime in dioxane and AcOH, aqueous TiCl3 was added under ice, keeping temperature of 299 K by cooling, for 4 h to give imine. To imine in dioxane and AcOH, an aqueous solution of NaNO2 was added for 1 h to obtain the title compound. Crystals suitable for X-ray structure analysis were obtained by slow evaporation of a solution in methanol at room temperature.

Refinement top

H atoms of the hydroxy group were located in a difference density map and refined freely. Other H atoms were positioned geometrically and refined as riding (C—H = 0.95–1.00 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq or 1.5Ueq (parent). The absolute configuration could not be established because of the absence of significant anomalous effects. Friedel pairs were merged for the final cycles of refinement.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 2007).

Figures top
[Figure 1] Fig. 1. The two molecules of an asymmetric unit of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 60% probability level and H atoms have been omitted for clarity.
12α-Hydroxy-3,27-dioxooleanano-28,13-lactone top
Crystal data top
C30H44O5F(000) = 2112
Mr = 484.65Dx = 1.222 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 11606 reflections
a = 12.4457 (3) Åθ = 1.5–27.1°
b = 15.5804 (4) ŵ = 0.08 mm1
c = 27.1710 (8) ÅT = 113 K
V = 5268.7 (2) Å3Block, colourless
Z = 80.32 × 0.30 × 0.26 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
6391 independent reflections
Radiation source: rotating anode6106 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.054
Detector resolution: 7.31 pixels mm-1θmax = 27.1°, θmin = 1.5°
ϕ and ω scansh = 1515
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2007)
k = 1919
Tmin = 0.975, Tmax = 0.979l = 3432
46805 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0492P)2 + 0.7562P]
where P = (Fo2 + 2Fc2)/3
6391 reflections(Δ/σ)max < 0.001
649 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C30H44O5V = 5268.7 (2) Å3
Mr = 484.65Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 12.4457 (3) ŵ = 0.08 mm1
b = 15.5804 (4) ÅT = 113 K
c = 27.1710 (8) Å0.32 × 0.30 × 0.26 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
6391 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2007)
6106 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.979Rint = 0.054
46805 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.18 e Å3
6391 reflectionsΔρmin = 0.23 e Å3
649 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.58097 (18)0.75511 (12)0.07251 (8)0.0470 (5)
O20.58149 (12)0.28995 (10)0.04638 (6)0.0201 (3)
H20.537 (2)0.3181 (17)0.0285 (10)0.030*
O30.85004 (12)0.21425 (9)0.02152 (5)0.0187 (3)
O40.96348 (12)0.10366 (10)0.01557 (6)0.0285 (4)
O50.74482 (14)0.30826 (11)0.17851 (6)0.0293 (4)
O60.94971 (13)0.54315 (10)0.28292 (6)0.0263 (4)
O70.85259 (13)0.05664 (10)0.26587 (5)0.0204 (3)
H70.916 (2)0.0577 (16)0.2496 (10)0.031*
O80.81857 (12)0.02374 (9)0.39691 (5)0.0188 (3)
O90.78339 (14)0.06106 (11)0.46169 (6)0.0287 (4)
O100.52822 (12)0.08913 (10)0.29367 (6)0.0258 (4)
C10.62798 (17)0.55293 (14)0.01435 (9)0.0225 (5)
H1A0.61430.52660.01820.027*
H1B0.57570.52830.03790.027*
C20.6088 (2)0.65032 (14)0.01065 (9)0.0276 (5)
H2A0.65100.67320.01730.033*
H2B0.53190.66070.00350.033*
C30.6392 (2)0.69874 (14)0.05659 (10)0.0301 (6)
C40.7475 (2)0.67756 (14)0.08065 (9)0.0284 (5)
C50.76449 (19)0.57790 (14)0.08003 (8)0.0217 (5)
H50.70900.55530.10330.026*
C60.8717 (2)0.54981 (14)0.10253 (9)0.0256 (5)
H6A0.88750.58510.13190.031*
H6B0.93020.55850.07840.031*
C70.86607 (19)0.45489 (14)0.11710 (8)0.0245 (5)
H7A0.80950.44750.14240.029*
H7B0.93540.43790.13200.029*
C80.84185 (17)0.39469 (13)0.07335 (8)0.0179 (4)
C90.74243 (17)0.43067 (12)0.04433 (7)0.0162 (4)
H90.68020.42330.06720.019*
C100.74303 (17)0.52904 (13)0.03119 (7)0.0177 (4)
C110.71794 (16)0.37080 (13)0.00072 (7)0.0170 (4)
H11A0.66160.39680.02030.020*
H11B0.78340.36330.01950.020*
C120.67976 (17)0.28344 (13)0.01944 (8)0.0165 (4)
H120.66810.24480.00940.020*
C130.76031 (16)0.24126 (13)0.05412 (7)0.0157 (4)
C140.81068 (16)0.30106 (13)0.09439 (8)0.0172 (4)
C150.90918 (18)0.25408 (14)0.11685 (9)0.0238 (5)
H15A0.97070.25960.09400.029*
H15B0.92920.28260.14810.029*
C160.88884 (18)0.15814 (15)0.12701 (9)0.0249 (5)
H16A0.84340.15260.15680.030*
H16B0.95830.12970.13390.030*
C170.83308 (17)0.11138 (14)0.08360 (8)0.0201 (4)
C180.72330 (16)0.15241 (13)0.07333 (8)0.0166 (4)
H180.69380.12150.04400.020*
C190.64336 (17)0.13627 (13)0.11489 (8)0.0179 (4)
H19A0.57290.16160.10620.021*
H19B0.66910.16420.14540.021*
C200.63048 (17)0.03816 (14)0.12369 (8)0.0204 (4)
C210.74144 (19)0.00440 (15)0.13175 (9)0.0252 (5)
H21A0.77110.01570.16350.030*
H21B0.73140.06730.13420.030*
C220.82348 (19)0.01443 (14)0.09095 (9)0.0263 (5)
H22A0.89430.00970.10010.032*
H22B0.80010.01300.05990.032*
C230.7453 (3)0.70955 (16)0.13443 (10)0.0451 (8)
H23A0.72810.77090.13500.068*
H23B0.81590.70030.14950.068*
H23C0.69060.67780.15290.068*
C240.8352 (2)0.72879 (16)0.05322 (10)0.0329 (6)
H24A0.83120.71620.01790.049*
H24B0.90610.71230.06580.049*
H24C0.82390.79030.05860.049*
C250.82047 (17)0.55160 (14)0.01128 (8)0.0211 (4)
H25A0.82050.50500.03550.032*
H25B0.89320.55930.00180.032*
H25C0.79680.60490.02710.032*
C260.94445 (17)0.39040 (15)0.04132 (9)0.0235 (5)
H26A0.95820.44690.02670.035*
H26B0.93440.34800.01510.035*
H26C1.00570.37370.06190.035*
C270.72566 (19)0.31387 (13)0.13495 (8)0.0201 (4)
H270.65420.32690.12520.024*
C280.89023 (17)0.13821 (14)0.03740 (9)0.0211 (5)
C290.56350 (19)0.02642 (16)0.17039 (9)0.0281 (5)
H29A0.49220.05160.16550.042*
H29B0.59930.05500.19800.042*
H29C0.55610.03490.17760.042*
C300.5710 (2)0.00436 (15)0.08081 (9)0.0256 (5)
H30A0.56010.06540.08810.038*
H30B0.61360.00150.05070.038*
H30C0.50110.02350.07620.038*
C310.93563 (18)0.31539 (14)0.27350 (8)0.0207 (5)
H31A1.00920.30150.28480.025*
H31B0.91390.27070.24960.025*
C320.93773 (19)0.40317 (13)0.24707 (8)0.0217 (5)
H32A1.01230.41540.23650.026*
H32B0.89280.39940.21710.026*
C330.89835 (17)0.47677 (13)0.27798 (8)0.0194 (4)
C340.78608 (17)0.46634 (13)0.29976 (8)0.0189 (4)
C350.75950 (16)0.36869 (13)0.30709 (8)0.0166 (4)
H350.73150.34830.27460.020*
C360.66828 (17)0.35359 (13)0.34393 (8)0.0209 (5)
H36A0.60680.39130.33560.025*
H36B0.69320.36870.37740.025*
C370.63149 (17)0.25966 (13)0.34323 (8)0.0196 (4)
H37A0.60460.24540.30990.024*
H37B0.57120.25240.36660.024*
C380.72235 (17)0.19660 (13)0.35705 (7)0.0164 (4)
C390.81945 (16)0.21624 (13)0.32225 (7)0.0154 (4)
H390.79280.20170.28860.018*
C400.85859 (16)0.31201 (13)0.31817 (8)0.0164 (4)
C410.91204 (16)0.15334 (13)0.33136 (8)0.0179 (4)
H41A0.97520.17050.31150.021*
H41B0.93280.15490.36650.021*
C420.87781 (16)0.06313 (13)0.31740 (8)0.0170 (4)
H420.93830.02290.32490.020*
C430.77906 (16)0.03404 (13)0.34572 (7)0.0159 (4)
C440.68267 (16)0.09932 (13)0.34798 (7)0.0157 (4)
C450.60343 (17)0.06770 (13)0.38805 (8)0.0190 (4)
H45A0.63220.08360.42080.023*
H45B0.53400.09780.38370.023*
C460.58308 (17)0.03024 (14)0.38704 (8)0.0203 (4)
H46A0.53620.04430.35870.024*
H46B0.54480.04720.41750.024*
C470.68880 (17)0.08248 (13)0.38292 (8)0.0187 (4)
C480.74607 (17)0.05958 (13)0.33453 (7)0.0177 (4)
H480.81430.09340.33450.021*
C490.68355 (18)0.08948 (13)0.28927 (8)0.0208 (4)
H49A0.72400.07450.25910.025*
H49B0.61320.05990.28800.025*
C500.66565 (19)0.18817 (14)0.29135 (9)0.0244 (5)
C510.6154 (2)0.21427 (14)0.34126 (9)0.0270 (5)
H51A0.54000.19400.34200.032*
H51B0.61390.27770.34320.032*
C520.67319 (19)0.17968 (14)0.38724 (9)0.0247 (5)
H52A0.63020.19280.41690.030*
H52B0.74400.20810.39070.030*
C530.70908 (18)0.50268 (14)0.26005 (8)0.0241 (5)
H53A0.72440.56370.25490.036*
H53B0.63460.49580.27100.036*
H53C0.71960.47140.22910.036*
C540.77561 (19)0.52216 (14)0.34640 (8)0.0238 (5)
H54A0.82340.49980.37210.036*
H54B0.70120.52070.35810.036*
H54C0.79570.58150.33860.036*
C550.92374 (19)0.34467 (15)0.36309 (8)0.0234 (5)
H55A0.96490.39570.35360.035*
H55B0.97320.29960.37410.035*
H55C0.87440.35930.38990.035*
C560.7498 (2)0.21010 (14)0.41173 (8)0.0227 (5)
H56A0.78430.26610.41600.034*
H56B0.79880.16470.42270.034*
H56C0.68370.20800.43130.034*
C570.62456 (18)0.09857 (13)0.29812 (8)0.0187 (4)
H570.66630.10590.26920.022*
C580.76600 (18)0.04329 (13)0.41932 (8)0.0208 (4)
C590.5866 (2)0.21247 (16)0.25044 (10)0.0358 (6)
H59A0.61600.19510.21850.054*
H59B0.51790.18320.25600.054*
H59C0.57510.27470.25070.054*
C600.7720 (2)0.23523 (15)0.28285 (10)0.0312 (6)
H60A0.75890.29720.28160.047*
H60B0.82160.22230.30990.047*
H60C0.80360.21630.25160.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0551 (13)0.0287 (10)0.0571 (13)0.0092 (9)0.0241 (11)0.0036 (9)
O20.0134 (7)0.0236 (8)0.0234 (8)0.0006 (6)0.0006 (6)0.0030 (6)
O30.0178 (7)0.0174 (7)0.0208 (8)0.0013 (6)0.0064 (6)0.0019 (6)
O40.0199 (8)0.0227 (8)0.0428 (10)0.0033 (6)0.0124 (8)0.0032 (7)
O50.0394 (10)0.0310 (9)0.0175 (8)0.0095 (8)0.0004 (7)0.0018 (7)
O60.0283 (9)0.0209 (8)0.0298 (9)0.0069 (7)0.0069 (7)0.0031 (7)
O70.0213 (8)0.0233 (8)0.0166 (7)0.0007 (6)0.0041 (6)0.0003 (6)
O80.0218 (7)0.0194 (7)0.0151 (7)0.0010 (6)0.0020 (6)0.0032 (6)
O90.0332 (9)0.0328 (9)0.0201 (8)0.0006 (8)0.0014 (7)0.0096 (7)
O100.0188 (8)0.0247 (8)0.0338 (9)0.0008 (6)0.0039 (7)0.0014 (7)
C10.0212 (10)0.0185 (10)0.0278 (12)0.0006 (9)0.0013 (9)0.0035 (9)
C20.0281 (12)0.0206 (11)0.0340 (13)0.0022 (9)0.0061 (10)0.0041 (10)
C30.0382 (14)0.0152 (11)0.0369 (14)0.0014 (10)0.0175 (11)0.0020 (10)
C40.0447 (15)0.0177 (11)0.0227 (12)0.0048 (10)0.0050 (11)0.0006 (9)
C50.0279 (11)0.0190 (10)0.0180 (10)0.0045 (9)0.0040 (9)0.0010 (8)
C60.0328 (12)0.0224 (11)0.0216 (11)0.0105 (10)0.0024 (10)0.0024 (9)
C70.0275 (12)0.0235 (11)0.0224 (11)0.0094 (9)0.0078 (9)0.0007 (9)
C80.0170 (10)0.0178 (10)0.0189 (10)0.0023 (8)0.0024 (8)0.0000 (8)
C90.0171 (10)0.0166 (10)0.0149 (10)0.0028 (8)0.0006 (8)0.0014 (8)
C100.0182 (10)0.0163 (10)0.0187 (10)0.0027 (8)0.0040 (8)0.0004 (8)
C110.0160 (9)0.0183 (10)0.0166 (10)0.0008 (8)0.0022 (8)0.0015 (8)
C120.0173 (10)0.0159 (10)0.0164 (10)0.0007 (8)0.0005 (8)0.0017 (8)
C130.0141 (9)0.0177 (10)0.0152 (10)0.0001 (8)0.0027 (8)0.0004 (8)
C140.0149 (10)0.0200 (10)0.0169 (10)0.0031 (8)0.0020 (8)0.0003 (8)
C150.0190 (11)0.0259 (11)0.0266 (12)0.0044 (9)0.0063 (9)0.0054 (9)
C160.0179 (11)0.0258 (11)0.0308 (13)0.0017 (9)0.0055 (9)0.0096 (10)
C170.0161 (10)0.0204 (10)0.0239 (11)0.0011 (8)0.0018 (9)0.0031 (9)
C180.0158 (10)0.0161 (9)0.0178 (10)0.0011 (8)0.0002 (8)0.0003 (8)
C190.0175 (10)0.0212 (10)0.0150 (10)0.0034 (8)0.0002 (8)0.0003 (8)
C200.0199 (10)0.0218 (11)0.0196 (10)0.0050 (9)0.0001 (9)0.0014 (9)
C210.0257 (11)0.0206 (10)0.0292 (12)0.0042 (9)0.0026 (10)0.0069 (9)
C220.0223 (11)0.0190 (11)0.0375 (14)0.0016 (9)0.0031 (10)0.0068 (10)
C230.082 (2)0.0208 (12)0.0325 (14)0.0022 (14)0.0119 (15)0.0060 (11)
C240.0432 (15)0.0216 (12)0.0339 (14)0.0113 (11)0.0007 (12)0.0006 (10)
C250.0232 (11)0.0217 (11)0.0184 (10)0.0021 (9)0.0018 (9)0.0010 (9)
C260.0161 (10)0.0233 (11)0.0312 (13)0.0022 (9)0.0005 (9)0.0054 (10)
C270.0256 (11)0.0141 (9)0.0207 (11)0.0046 (9)0.0001 (9)0.0027 (8)
C280.0180 (10)0.0162 (10)0.0289 (12)0.0006 (8)0.0015 (9)0.0011 (9)
C290.0289 (12)0.0299 (12)0.0256 (12)0.0106 (10)0.0020 (10)0.0032 (10)
C300.0281 (12)0.0236 (11)0.0251 (12)0.0086 (9)0.0026 (10)0.0007 (9)
C310.0197 (10)0.0184 (10)0.0241 (11)0.0005 (8)0.0059 (9)0.0008 (9)
C320.0256 (11)0.0201 (10)0.0195 (11)0.0014 (9)0.0057 (9)0.0007 (9)
C330.0231 (11)0.0181 (10)0.0169 (10)0.0001 (9)0.0011 (8)0.0038 (8)
C340.0232 (10)0.0131 (10)0.0203 (10)0.0007 (8)0.0044 (9)0.0007 (8)
C350.0173 (10)0.0140 (9)0.0183 (10)0.0011 (8)0.0020 (8)0.0009 (8)
C360.0208 (10)0.0150 (10)0.0270 (12)0.0020 (8)0.0051 (9)0.0017 (9)
C370.0164 (10)0.0155 (10)0.0268 (12)0.0014 (8)0.0068 (9)0.0001 (9)
C380.0174 (10)0.0148 (9)0.0170 (10)0.0011 (8)0.0018 (8)0.0017 (8)
C390.0136 (9)0.0166 (10)0.0159 (10)0.0005 (8)0.0009 (8)0.0007 (8)
C400.0163 (10)0.0158 (10)0.0171 (10)0.0004 (8)0.0001 (8)0.0003 (8)
C410.0149 (10)0.0184 (10)0.0203 (11)0.0002 (8)0.0008 (8)0.0015 (8)
C420.0150 (9)0.0186 (10)0.0173 (10)0.0019 (8)0.0005 (8)0.0009 (8)
C430.0158 (9)0.0176 (10)0.0143 (9)0.0009 (8)0.0011 (8)0.0019 (8)
C440.0174 (9)0.0149 (9)0.0148 (10)0.0002 (8)0.0031 (8)0.0003 (8)
C450.0192 (10)0.0169 (10)0.0209 (11)0.0002 (8)0.0041 (8)0.0019 (8)
C460.0202 (10)0.0188 (10)0.0218 (11)0.0005 (9)0.0043 (9)0.0016 (9)
C470.0211 (10)0.0168 (10)0.0183 (10)0.0005 (8)0.0027 (9)0.0019 (8)
C480.0189 (10)0.0153 (9)0.0189 (10)0.0014 (8)0.0022 (8)0.0009 (8)
C490.0248 (11)0.0164 (10)0.0213 (11)0.0020 (9)0.0007 (9)0.0032 (9)
C500.0275 (12)0.0169 (10)0.0288 (12)0.0033 (9)0.0020 (10)0.0019 (9)
C510.0306 (12)0.0175 (10)0.0331 (13)0.0048 (9)0.0074 (11)0.0016 (10)
C520.0253 (11)0.0182 (11)0.0306 (13)0.0013 (9)0.0059 (10)0.0033 (9)
C530.0267 (11)0.0181 (10)0.0276 (12)0.0015 (9)0.0011 (10)0.0027 (9)
C540.0278 (11)0.0182 (10)0.0254 (11)0.0023 (9)0.0053 (10)0.0030 (9)
C550.0253 (11)0.0211 (11)0.0238 (12)0.0037 (9)0.0058 (9)0.0018 (9)
C560.0317 (12)0.0186 (10)0.0178 (10)0.0038 (9)0.0025 (9)0.0007 (8)
C570.0217 (11)0.0138 (10)0.0207 (11)0.0001 (8)0.0003 (9)0.0008 (8)
C580.0220 (11)0.0207 (11)0.0196 (11)0.0039 (9)0.0023 (9)0.0033 (9)
C590.0450 (15)0.0247 (12)0.0376 (14)0.0110 (11)0.0002 (13)0.0069 (11)
C600.0365 (14)0.0181 (11)0.0391 (14)0.0009 (10)0.0091 (12)0.0041 (10)
Geometric parameters (Å, º) top
O1—C31.218 (3)C27—H270.9500
O2—C121.429 (2)C29—H29A0.9800
O2—H20.86 (3)C29—H29B0.9800
O3—C281.356 (3)C29—H29C0.9800
O3—C131.486 (2)C30—H30A0.9800
O4—C281.213 (3)C30—H30B0.9800
O5—C271.210 (3)C30—H30C0.9800
O6—C331.223 (3)C31—C321.545 (3)
O7—C421.438 (2)C31—C401.548 (3)
O7—H70.90 (3)C31—H31A0.9900
O8—C581.375 (3)C31—H31B0.9900
O8—C431.484 (2)C32—C331.504 (3)
O9—C581.204 (3)C32—H32A0.9900
O10—C571.214 (3)C32—H32B0.9900
C1—C21.539 (3)C33—C341.526 (3)
C1—C101.549 (3)C34—C541.542 (3)
C1—H1A0.9900C34—C531.550 (3)
C1—H1B0.9900C34—C351.570 (3)
C2—C31.507 (4)C35—C361.532 (3)
C2—H2A0.9900C35—C401.547 (3)
C2—H2B0.9900C35—H351.0000
C3—C41.534 (4)C36—C371.534 (3)
C4—C241.544 (3)C36—H36A0.9900
C4—C231.544 (3)C36—H36B0.9900
C4—C51.567 (3)C37—C381.544 (3)
C5—C61.531 (3)C37—H37A0.9900
C5—C101.553 (3)C37—H37B0.9900
C5—H51.0000C38—C561.539 (3)
C6—C71.532 (3)C38—C391.565 (3)
C6—H6A0.9900C38—C441.613 (3)
C6—H6B0.9900C39—C411.533 (3)
C7—C81.544 (3)C39—C401.573 (3)
C7—H7A0.9900C39—H391.0000
C7—H7B0.9900C40—C551.551 (3)
C8—C261.547 (3)C41—C421.517 (3)
C8—C91.571 (3)C41—H41A0.9900
C8—C141.614 (3)C41—H41B0.9900
C9—C111.538 (3)C42—C431.519 (3)
C9—C101.574 (3)C42—H421.0000
C9—H91.0000C43—C481.546 (3)
C10—C251.544 (3)C43—C441.574 (3)
C11—C121.529 (3)C44—C571.536 (3)
C11—H11A0.9900C44—C451.550 (3)
C11—H11B0.9900C45—C461.547 (3)
C12—C131.525 (3)C45—H45A0.9900
C12—H121.0000C45—H45B0.9900
C13—C181.550 (3)C46—C471.551 (3)
C13—C141.568 (3)C46—H46A0.9900
C14—C271.541 (3)C46—H46B0.9900
C14—C151.553 (3)C47—C581.508 (3)
C15—C161.541 (3)C47—C521.531 (3)
C15—H15A0.9900C47—C481.538 (3)
C15—H15B0.9900C48—C491.528 (3)
C16—C171.550 (3)C48—H481.0000
C16—H16A0.9900C49—C501.555 (3)
C16—H16B0.9900C49—H49A0.9900
C17—C281.502 (3)C49—H49B0.9900
C17—C221.528 (3)C50—C601.530 (3)
C17—C181.534 (3)C50—C591.532 (3)
C18—C191.526 (3)C50—C511.548 (3)
C18—H181.0000C51—C521.539 (3)
C19—C201.555 (3)C51—H51A0.9900
C19—H19A0.9900C51—H51B0.9900
C19—H19B0.9900C52—H52A0.9900
C20—C291.529 (3)C52—H52B0.9900
C20—C301.531 (3)C53—H53A0.9800
C20—C211.547 (3)C53—H53B0.9800
C21—C221.536 (3)C53—H53C0.9800
C21—H21A0.9900C54—H54A0.9800
C21—H21B0.9900C54—H54B0.9800
C22—H22A0.9900C54—H54C0.9800
C22—H22B0.9900C55—H55A0.9800
C23—H23A0.9800C55—H55B0.9800
C23—H23B0.9800C55—H55C0.9800
C23—H23C0.9800C56—H56A0.9800
C24—H24A0.9800C56—H56B0.9800
C24—H24B0.9800C56—H56C0.9800
C24—H24C0.9800C57—H570.9500
C25—H25A0.9800C59—H59A0.9800
C25—H25B0.9800C59—H59B0.9800
C25—H25C0.9800C59—H59C0.9800
C26—H26A0.9800C60—H60A0.9800
C26—H26B0.9800C60—H60B0.9800
C26—H26C0.9800C60—H60C0.9800
C12—O2—H2107.6 (18)H30A—C30—H30C109.5
C28—O3—C13109.56 (15)H30B—C30—H30C109.5
C42—O7—H7106.5 (17)C32—C31—C40113.90 (17)
C58—O8—C43109.85 (15)C32—C31—H31A108.8
C2—C1—C10113.53 (18)C40—C31—H31A108.8
C2—C1—H1A108.9C32—C31—H31B108.8
C10—C1—H1A108.9C40—C31—H31B108.8
C2—C1—H1B108.9H31A—C31—H31B107.7
C10—C1—H1B108.9C33—C32—C31114.20 (17)
H1A—C1—H1B107.7C33—C32—H32A108.7
C3—C2—C1113.6 (2)C31—C32—H32A108.7
C3—C2—H2A108.8C33—C32—H32B108.7
C1—C2—H2A108.8C31—C32—H32B108.7
C3—C2—H2B108.8H32A—C32—H32B107.6
C1—C2—H2B108.8O6—C33—C32122.40 (19)
H2A—C2—H2B107.7O6—C33—C34121.72 (19)
O1—C3—C2120.4 (3)C32—C33—C34115.72 (18)
O1—C3—C4121.8 (2)C33—C34—C54109.62 (18)
C2—C3—C4117.7 (2)C33—C34—C53104.90 (17)
C3—C4—C24107.71 (19)C54—C34—C53108.28 (17)
C3—C4—C23108.6 (2)C33—C34—C35110.20 (17)
C24—C4—C23107.6 (2)C54—C34—C35115.13 (17)
C3—C4—C5109.11 (19)C53—C34—C35108.18 (17)
C24—C4—C5114.3 (2)C36—C35—C40112.09 (16)
C23—C4—C5109.41 (19)C36—C35—C34112.83 (16)
C6—C5—C10110.54 (18)C40—C35—C34114.22 (17)
C6—C5—C4113.37 (19)C36—C35—H35105.6
C10—C5—C4118.14 (18)C40—C35—H35105.6
C6—C5—H5104.4C34—C35—H35105.6
C10—C5—H5104.4C35—C36—C37111.09 (17)
C4—C5—H5104.4C35—C36—H36A109.4
C5—C6—C7109.83 (18)C37—C36—H36A109.4
C5—C6—H6A109.7C35—C36—H36B109.4
C7—C6—H6A109.7C37—C36—H36B109.4
C5—C6—H6B109.7H36A—C36—H36B108.0
C7—C6—H6B109.7C36—C37—C38112.67 (17)
H6A—C6—H6B108.2C36—C37—H37A109.1
C6—C7—C8113.35 (18)C38—C37—H37A109.1
C6—C7—H7A108.9C36—C37—H37B109.1
C8—C7—H7A108.9C38—C37—H37B109.1
C6—C7—H7B108.9H37A—C37—H37B107.8
C8—C7—H7B108.9C56—C38—C37108.07 (17)
H7A—C7—H7B107.7C56—C38—C39112.67 (17)
C7—C8—C26107.35 (17)C37—C38—C39107.11 (16)
C7—C8—C9108.87 (17)C56—C38—C44110.11 (16)
C26—C8—C9112.54 (17)C37—C38—C44109.66 (16)
C7—C8—C14108.87 (16)C39—C38—C44109.14 (16)
C26—C8—C14111.02 (17)C41—C39—C38110.99 (16)
C9—C8—C14108.12 (16)C41—C39—C40112.64 (16)
C11—C9—C8109.04 (16)C38—C39—C40117.86 (16)
C11—C9—C10114.63 (16)C41—C39—H39104.6
C8—C9—C10117.24 (17)C38—C39—H39104.6
C11—C9—H9104.9C40—C39—H39104.6
C8—C9—H9104.9C35—C40—C31108.78 (16)
C10—C9—H9104.9C35—C40—C55112.50 (17)
C25—C10—C1107.56 (17)C31—C40—C55106.38 (17)
C25—C10—C5114.81 (17)C35—C40—C39107.96 (16)
C1—C10—C5107.07 (18)C31—C40—C39106.22 (16)
C25—C10—C9113.22 (17)C55—C40—C39114.67 (17)
C1—C10—C9107.26 (16)C42—C41—C39109.93 (17)
C5—C10—C9106.52 (16)C42—C41—H41A109.7
C12—C11—C9110.20 (16)C39—C41—H41A109.7
C12—C11—H11A109.6C42—C41—H41B109.7
C9—C11—H11A109.6C39—C41—H41B109.7
C12—C11—H11B109.6H41A—C41—H41B108.2
C9—C11—H11B109.6O7—C42—C41111.71 (17)
H11A—C11—H11B108.1O7—C42—C43107.19 (16)
O2—C12—C13106.06 (16)C41—C42—C43112.14 (17)
O2—C12—C11111.91 (16)O7—C42—H42108.6
C13—C12—C11112.64 (17)C41—C42—H42108.6
O2—C12—H12108.7C43—C42—H42108.6
C13—C12—H12108.7O8—C43—C42103.83 (15)
C11—C12—H12108.7O8—C43—C4899.81 (15)
O3—C13—C12104.34 (15)C42—C43—C48113.37 (17)
O3—C13—C1899.85 (15)O8—C43—C44106.62 (15)
C12—C13—C18113.44 (17)C42—C43—C44116.33 (16)
O3—C13—C14106.49 (15)C48—C43—C44114.52 (16)
C12—C13—C14115.98 (17)C57—C44—C45108.53 (17)
C18—C13—C14114.50 (16)C57—C44—C43108.65 (16)
C27—C14—C15108.79 (18)C45—C44—C43107.88 (16)
C27—C14—C13107.55 (16)C57—C44—C38106.63 (16)
C15—C14—C13108.05 (17)C45—C44—C38112.72 (16)
C27—C14—C8107.53 (16)C43—C44—C38112.32 (16)
C15—C14—C8112.05 (16)C46—C45—C44113.91 (17)
C13—C14—C8112.71 (16)C46—C45—H45A108.8
C16—C15—C14113.45 (18)C44—C45—H45A108.8
C16—C15—H15A108.9C46—C45—H45B108.8
C14—C15—H15A108.9C44—C45—H45B108.8
C16—C15—H15B108.9H45A—C45—H45B107.7
C14—C15—H15B108.9C45—C46—C47112.33 (17)
H15A—C15—H15B107.7C45—C46—H46A109.1
C15—C16—C17113.14 (18)C47—C46—H46A109.1
C15—C16—H16A109.0C45—C46—H46B109.1
C17—C16—H16A109.0C47—C46—H46B109.1
C15—C16—H16B109.0H46A—C46—H46B107.9
C17—C16—H16B109.0C58—C47—C52115.53 (18)
H16A—C16—H16B107.8C58—C47—C4899.88 (17)
C28—C17—C22114.91 (19)C52—C47—C48110.73 (17)
C28—C17—C1898.85 (17)C58—C47—C46106.30 (17)
C22—C17—C18111.47 (18)C52—C47—C46113.94 (18)
C28—C17—C16107.05 (17)C48—C47—C46109.46 (17)
C22—C17—C16113.57 (19)C49—C48—C47112.42 (17)
C18—C17—C16109.96 (18)C49—C48—C43125.55 (17)
C19—C18—C17112.18 (17)C47—C48—C43100.01 (16)
C19—C18—C13126.18 (17)C49—C48—H48105.8
C17—C18—C1399.71 (16)C47—C48—H48105.8
C19—C18—H18105.7C43—C48—H48105.8
C17—C18—H18105.7C48—C49—C50110.19 (18)
C13—C18—H18105.7C48—C49—H49A109.6
C18—C19—C20110.06 (17)C50—C49—H49A109.6
C18—C19—H19A109.6C48—C49—H49B109.6
C20—C19—H19A109.6C50—C49—H49B109.6
C18—C19—H19B109.6H49A—C49—H49B108.1
C20—C19—H19B109.6C60—C50—C59109.1 (2)
H19A—C19—H19B108.2C60—C50—C51110.8 (2)
C29—C20—C30108.42 (18)C59—C50—C51108.13 (19)
C29—C20—C21108.53 (18)C60—C50—C49110.14 (19)
C30—C20—C21110.72 (19)C59—C50—C49108.05 (19)
C29—C20—C19107.54 (18)C51—C50—C49110.47 (18)
C30—C20—C19110.98 (18)C52—C51—C50115.50 (18)
C21—C20—C19110.54 (17)C52—C51—H51A108.4
C22—C21—C20114.17 (18)C50—C51—H51A108.4
C22—C21—H21A108.7C52—C51—H51B108.4
C20—C21—H21A108.7C50—C51—H51B108.4
C22—C21—H21B108.7H51A—C51—H51B107.5
C20—C21—H21B108.7C47—C52—C51110.08 (19)
H21A—C21—H21B107.6C47—C52—H52A109.6
C17—C22—C21109.58 (19)C51—C52—H52A109.6
C17—C22—H22A109.8C47—C52—H52B109.6
C21—C22—H22A109.8C51—C52—H52B109.6
C17—C22—H22B109.8H52A—C52—H52B108.2
C21—C22—H22B109.8C34—C53—H53A109.5
H22A—C22—H22B108.2C34—C53—H53B109.5
C4—C23—H23A109.5H53A—C53—H53B109.5
C4—C23—H23B109.5C34—C53—H53C109.5
H23A—C23—H23B109.5H53A—C53—H53C109.5
C4—C23—H23C109.5H53B—C53—H53C109.5
H23A—C23—H23C109.5C34—C54—H54A109.5
H23B—C23—H23C109.5C34—C54—H54B109.5
C4—C24—H24A109.5H54A—C54—H54B109.5
C4—C24—H24B109.5C34—C54—H54C109.5
H24A—C24—H24B109.5H54A—C54—H54C109.5
C4—C24—H24C109.5H54B—C54—H54C109.5
H24A—C24—H24C109.5C40—C55—H55A109.5
H24B—C24—H24C109.5C40—C55—H55B109.5
C10—C25—H25A109.5H55A—C55—H55B109.5
C10—C25—H25B109.5C40—C55—H55C109.5
H25A—C25—H25B109.5H55A—C55—H55C109.5
C10—C25—H25C109.5H55B—C55—H55C109.5
H25A—C25—H25C109.5C38—C56—H56A109.5
H25B—C25—H25C109.5C38—C56—H56B109.5
C8—C26—H26A109.5H56A—C56—H56B109.5
C8—C26—H26B109.5C38—C56—H56C109.5
H26A—C26—H26B109.5H56A—C56—H56C109.5
C8—C26—H26C109.5H56B—C56—H56C109.5
H26A—C26—H26C109.5O10—C57—C44123.6 (2)
H26B—C26—H26C109.5O10—C57—H57118.2
O5—C27—C14123.7 (2)C44—C57—H57118.2
O5—C27—H27118.2O9—C58—O8120.8 (2)
C14—C27—H27118.2O9—C58—C47130.4 (2)
O4—C28—O3120.6 (2)O8—C58—C47108.69 (17)
O4—C28—C17129.8 (2)C50—C59—H59A109.5
O3—C28—C17109.52 (18)C50—C59—H59B109.5
C20—C29—H29A109.5H59A—C59—H59B109.5
C20—C29—H29B109.5C50—C59—H59C109.5
H29A—C29—H29B109.5H59A—C59—H59C109.5
C20—C29—H29C109.5H59B—C59—H59C109.5
H29A—C29—H29C109.5C50—C60—H60A109.5
H29B—C29—H29C109.5C50—C60—H60B109.5
C20—C30—H30A109.5H60A—C60—H60B109.5
C20—C30—H30B109.5C50—C60—H60C109.5
H30A—C30—H30B109.5H60A—C60—H60C109.5
C20—C30—H30C109.5H60B—C60—H60C109.5
C10—C1—C2—C352.1 (3)C40—C31—C32—C3320.7 (3)
C1—C2—C3—O1136.9 (2)C31—C32—C33—O6129.2 (2)
C1—C2—C3—C446.1 (3)C31—C32—C33—C3455.3 (3)
O1—C3—C4—C2494.2 (3)O6—C33—C34—C5429.2 (3)
C2—C3—C4—C2482.8 (2)C32—C33—C34—C54155.27 (18)
O1—C3—C4—C2322.1 (3)O6—C33—C34—C5386.9 (2)
C2—C3—C4—C23161.0 (2)C32—C33—C34—C5388.7 (2)
O1—C3—C4—C5141.2 (2)O6—C33—C34—C35156.9 (2)
C2—C3—C4—C541.8 (3)C32—C33—C34—C3527.6 (2)
C3—C4—C5—C6179.02 (18)C33—C34—C35—C36160.31 (17)
C24—C4—C5—C658.4 (3)C54—C34—C35—C3635.7 (3)
C23—C4—C5—C662.3 (3)C53—C34—C35—C3685.5 (2)
C3—C4—C5—C1047.4 (3)C33—C34—C35—C4030.8 (2)
C24—C4—C5—C1073.3 (3)C54—C34—C35—C4093.8 (2)
C23—C4—C5—C10166.0 (2)C53—C34—C35—C40144.92 (18)
C10—C5—C6—C764.5 (2)C40—C35—C36—C3759.4 (2)
C4—C5—C6—C7160.22 (19)C34—C35—C36—C37169.95 (18)
C5—C6—C7—C859.5 (3)C35—C36—C37—C3860.4 (2)
C6—C7—C8—C2672.8 (2)C36—C37—C38—C5668.0 (2)
C6—C7—C8—C949.3 (2)C36—C37—C38—C3953.6 (2)
C6—C7—C8—C14166.96 (18)C36—C37—C38—C44171.93 (17)
C7—C8—C9—C11179.94 (17)C56—C38—C39—C4164.3 (2)
C26—C8—C9—C1161.2 (2)C37—C38—C39—C41176.96 (16)
C14—C8—C9—C1161.8 (2)C44—C38—C39—C4158.3 (2)
C7—C8—C9—C1047.7 (2)C56—C38—C39—C4067.7 (2)
C26—C8—C9—C1071.2 (2)C37—C38—C39—C4051.0 (2)
C14—C8—C9—C10165.84 (16)C44—C38—C39—C40169.70 (16)
C2—C1—C10—C2570.1 (2)C36—C35—C40—C31167.31 (17)
C2—C1—C10—C553.8 (2)C34—C35—C40—C3162.8 (2)
C2—C1—C10—C9167.77 (18)C36—C35—C40—C5575.1 (2)
C6—C5—C10—C2567.3 (2)C34—C35—C40—C5554.8 (2)
C4—C5—C10—C2565.6 (3)C36—C35—C40—C3952.4 (2)
C6—C5—C10—C1173.35 (17)C34—C35—C40—C39177.64 (16)
C4—C5—C10—C153.7 (2)C32—C31—C40—C3534.5 (2)
C6—C5—C10—C958.8 (2)C32—C31—C40—C5586.9 (2)
C4—C5—C10—C9168.26 (19)C32—C31—C40—C39150.53 (18)
C11—C9—C10—C2555.1 (2)C41—C39—C40—C35177.88 (17)
C8—C9—C10—C2574.7 (2)C38—C39—C40—C3550.9 (2)
C11—C9—C10—C163.4 (2)C41—C39—C40—C3161.3 (2)
C8—C9—C10—C1166.82 (17)C38—C39—C40—C31167.41 (17)
C11—C9—C10—C5177.79 (17)C41—C39—C40—C5555.8 (2)
C8—C9—C10—C552.4 (2)C38—C39—C40—C5575.4 (2)
C8—C9—C11—C1266.6 (2)C38—C39—C41—C4265.1 (2)
C10—C9—C11—C12159.71 (17)C40—C39—C41—C42160.27 (17)
C9—C11—C12—O262.9 (2)C39—C41—C42—O762.6 (2)
C9—C11—C12—C1356.5 (2)C39—C41—C42—C4357.8 (2)
C28—O3—C13—C12143.36 (17)C58—O8—C43—C42145.75 (16)
C28—O3—C13—C1825.91 (19)C58—O8—C43—C4828.54 (19)
C28—O3—C13—C1493.46 (18)C58—O8—C43—C4490.88 (18)
O2—C12—C13—O3165.17 (14)O7—C42—C43—O8167.71 (15)
C11—C12—C13—O372.09 (19)C41—C42—C43—O869.34 (19)
O2—C12—C13—C1857.5 (2)O7—C42—C43—C4860.4 (2)
C11—C12—C13—C18179.75 (16)C41—C42—C43—C48176.65 (16)
O2—C12—C13—C1478.1 (2)O7—C42—C43—C4475.5 (2)
C11—C12—C13—C1444.7 (2)C41—C42—C43—C4447.4 (2)
O3—C13—C14—C27167.75 (15)O8—C43—C44—C57168.79 (15)
C12—C13—C14—C2776.7 (2)C42—C43—C44—C5776.0 (2)
C18—C13—C14—C2758.4 (2)C48—C43—C44—C5759.4 (2)
O3—C13—C14—C1550.5 (2)O8—C43—C44—C4551.3 (2)
C12—C13—C14—C15166.03 (17)C42—C43—C44—C45166.53 (17)
C18—C13—C14—C1558.9 (2)C48—C43—C44—C4558.0 (2)
O3—C13—C14—C873.90 (19)O8—C43—C44—C3873.51 (19)
C12—C13—C14—C841.7 (2)C42—C43—C44—C3841.7 (2)
C18—C13—C14—C8176.77 (16)C48—C43—C44—C38177.12 (16)
C7—C8—C14—C2748.9 (2)C56—C38—C44—C57162.64 (17)
C26—C8—C14—C27166.90 (17)C37—C38—C44—C5743.8 (2)
C9—C8—C14—C2769.2 (2)C39—C38—C44—C5773.20 (19)
C7—C8—C14—C1570.6 (2)C56—C38—C44—C4543.7 (2)
C26—C8—C14—C1547.4 (2)C37—C38—C44—C4575.1 (2)
C9—C8—C14—C15171.30 (17)C39—C38—C44—C45167.81 (17)
C7—C8—C14—C13167.30 (17)C56—C38—C44—C4378.5 (2)
C26—C8—C14—C1374.7 (2)C37—C38—C44—C43162.75 (16)
C9—C8—C14—C1349.2 (2)C39—C38—C44—C4345.7 (2)
C27—C14—C15—C1673.7 (2)C57—C44—C45—C4674.7 (2)
C13—C14—C15—C1642.8 (2)C43—C44—C45—C4642.9 (2)
C8—C14—C15—C16167.52 (18)C38—C44—C45—C46167.45 (17)
C14—C15—C16—C1745.9 (3)C44—C45—C46—C4746.9 (2)
C15—C16—C17—C2845.8 (2)C45—C46—C47—C5845.5 (2)
C15—C16—C17—C22173.74 (19)C45—C46—C47—C52173.92 (19)
C15—C16—C17—C1860.6 (2)C45—C46—C47—C4861.5 (2)
C28—C17—C18—C19179.91 (17)C58—C47—C48—C49178.29 (17)
C22—C17—C18—C1958.6 (2)C52—C47—C48—C4959.5 (2)
C16—C17—C18—C1968.2 (2)C46—C47—C48—C4967.0 (2)
C28—C17—C18—C1344.32 (19)C58—C47—C48—C4342.94 (18)
C22—C17—C18—C13165.60 (18)C52—C47—C48—C43165.19 (17)
C16—C17—C18—C1367.5 (2)C46—C47—C48—C4368.39 (19)
O3—C13—C18—C19170.07 (18)O8—C43—C48—C49170.64 (19)
C12—C13—C18—C1979.5 (2)C42—C43—C48—C4979.6 (2)
C14—C13—C18—C1956.8 (3)C44—C43—C48—C4957.2 (3)
O3—C13—C18—C1743.22 (18)O8—C43—C48—C4743.61 (17)
C12—C13—C18—C17153.66 (17)C42—C43—C48—C47153.42 (16)
C14—C13—C18—C1770.1 (2)C44—C43—C48—C4769.8 (2)
C17—C18—C19—C2056.9 (2)C47—C48—C49—C5058.1 (2)
C13—C18—C19—C20178.49 (19)C43—C48—C49—C50179.81 (19)
C18—C19—C20—C29171.52 (17)C48—C49—C50—C6070.7 (2)
C18—C19—C20—C3070.0 (2)C48—C49—C50—C59170.21 (19)
C18—C19—C20—C2153.2 (2)C48—C49—C50—C5152.1 (2)
C29—C20—C21—C22170.98 (19)C60—C50—C51—C5271.6 (2)
C30—C20—C21—C2270.1 (2)C59—C50—C51—C52168.9 (2)
C19—C20—C21—C2253.3 (3)C49—C50—C51—C5250.8 (3)
C28—C17—C22—C21166.31 (19)C58—C47—C52—C51166.46 (19)
C18—C17—C22—C2154.9 (3)C48—C47—C52—C5153.9 (2)
C16—C17—C22—C2170.0 (2)C46—C47—C52—C5170.0 (2)
C20—C21—C22—C1753.7 (3)C50—C51—C52—C4751.6 (3)
C15—C14—C27—O517.2 (3)C45—C44—C57—O1011.7 (3)
C13—C14—C27—O5134.0 (2)C43—C44—C57—O10128.7 (2)
C8—C14—C27—O5104.4 (2)C38—C44—C57—O10110.0 (2)
C13—O3—C28—O4179.0 (2)C43—O8—C58—O9177.56 (19)
C13—O3—C28—C172.9 (2)C43—O8—C58—C471.0 (2)
C22—C17—C28—O432.7 (3)C52—C47—C58—O935.7 (3)
C18—C17—C28—O4151.5 (2)C48—C47—C58—O9154.5 (2)
C16—C17—C28—O494.4 (3)C46—C47—C58—O991.7 (3)
C22—C17—C28—O3149.32 (19)C52—C47—C58—O8145.88 (18)
C18—C17—C28—O330.6 (2)C48—C47—C58—O827.1 (2)
C16—C17—C28—O383.6 (2)C46—C47—C58—O886.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O4i0.86 (3)1.94 (3)2.782 (2)167 (3)
O7—H7···O6ii0.90 (3)1.91 (3)2.803 (2)172 (2)
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC30H44O5
Mr484.65
Crystal system, space groupOrthorhombic, P212121
Temperature (K)113
a, b, c (Å)12.4457 (3), 15.5804 (4), 27.1710 (8)
V3)5268.7 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.32 × 0.30 × 0.26
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2007)
Tmin, Tmax0.975, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
46805, 6391, 6106
Rint0.054
(sin θ/λ)max1)0.641
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.095, 1.10
No. of reflections6391
No. of parameters649
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.23

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku, 2007).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O4i0.86 (3)1.94 (3)2.782 (2)167 (3)
O7—H7···O6ii0.90 (3)1.91 (3)2.803 (2)172 (2)
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+2, y1/2, z+1/2.
 

Acknowledgements

This project was granted financial support from the Science and Technology Department of Liaoning Province Science Foundation (2010226003), the Higher Education Department of Liaoning Province Research Foundation (LS2020089) and the Graduate Education Innovation Program 2010.

References

First citationGene, R. M., Cartana, C., Adzet, T., Marin, E., Parella, T. & Canigueral, S. (1996). Planta Med. 62, 232–235.  CAS PubMed Web of Science Google Scholar
First citationHu, J. Y., Yao, Z., Xu, Y. Q. & Duan, H. Q. (2009). J. Asian Nat. Prod. Res. 11, 236–242.  Web of Science CrossRef PubMed CAS Google Scholar
First citationRigaku (2007). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationXu, Y. Q., Yao, Z., Hu, J. Y., Jie, T. & Duan, H. Q. (2007). J. Asian Nat. Prod. Res. 9, 637–642.  Web of Science CSD CrossRef PubMed CAS Google Scholar

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