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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o723.
Published online 2008 March 20. doi:  10.1107/S1600536808006831
PMCID: PMC2960924

1-(5a,5b,8,8,11a,13b-Hexamethyl­eicosa­hydro-1H-cyclo­penta­[a]chrysen-3-yl)-1-ethanone

Abstract

The title compound, C29H48O, is a triterpenoid isolated from Adiantum incisum forssk. In the crystal structure, the asymmetric unit contains two independent mol­ecules which are not significantly different. Each mol­ecule contains four six-membered rings, all adopting chair conformations, and a five-membered ring in an envelope conformation. In the mol­ecular structure, non-classical intra­molecular C—H(...)O hydrogen bonds are observed.

Related literature

For related literature, see: Ageta & Iwata (1966 [triangle]); Brahmachari et al. (2003 [triangle]); Bresciani et al. (2003 [triangle]); Hussain et al. (2007 [triangle], 2008 [triangle]); Nadkarni & Nadkarni (1982 [triangle]); Reddy et al. (2001 [triangle]).

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Object name is e-64-0o723-scheme1.jpg

Experimental

Crystal data

  • C29H48O
  • M r = 412.67
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o723-efi1.jpg
  • a = 6.581 (3) Å
  • b = 7.260 (4) Å
  • c = 27.908 (14) Å
  • α = 84.98 (2)°
  • β = 86.48 (3)°
  • γ = 64.01 (3)°
  • V = 1193.6 (10) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 173 (2) K
  • 0.12 × 0.10 × 0.05 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (SORTAV; Blessing, 1997 [triangle]) T min = 0.992, T max = 0.997
  • 7958 measured reflections
  • 4272 independent reflections
  • 3161 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.069
  • wR(F 2) = 0.177
  • S = 1.05
  • 4272 reflections
  • 555 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: COLLECT (Hooft, 1998 [triangle]); cell refinement: DENZO (Otwinowski & Minor, 1997 [triangle]); data reduction: SCALEPACK (Otwinowski & Minor, 1997 [triangle]); program(s) used to solve structure: SAPI91 (Fan, 1991 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPII (Johnson, 1976 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808006831/is2277sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006831/is2277Isup2.hkl

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

Acknowledgments

The authors acknowledge the Higher Education Commission of Pakistan and the University of the Punjab, Lahore for finnacial support.

supplementary crystallographic information

Comment

Triterpenoids are an important class of natural products and are recognized for their ethnobotanical nature i.e. analgesic, anti-microbial and anti-inflammatory (Brahmachari et al., 2003; Bresciani et al., 2003; Reddy et al., 2001). Adiantum incisum forssk, syn. Adiantum caudatum L., a fern, used in ayurvedic medicines, is well known for its use against diabetes and skin diseases (Nadkarni & Nadkarni, 1982). During its phytochemical investigations, the title compound (I), along with other compounds (Hussain et al., 2007, 2008), was isolated and its crystal structure is hereby reported; it has been reported as one of the constituents of Adiantum pedatum (Ageta & Iwata, 1966).

The asymmetric unit of (I) contains two independent molecules A and B, presented in Figs. 1 and 2, respectively. There are no significant differences in the molecular dimensions of the two molecules. Both molecules contain four six-membered rings, all adopting chair conformations and a five-membered ring adopting envelope conformation with atoms C18 and C48, 0.656 (9) and 0.684 (9) Å out of the planes formed by the remaining ring atoms, C17/C19/C20/C21 and C47/C49/C50/C51, respectively. The acetyl groups bonded to the five membered rings show intramolecular H-bonding interactions, C20—H20···O30 and C50—H50···O60 (Table 1).

Experimental

Adiantum incisum forssk was collected from Murree hills, Pakistan, during September 2003. After shade drying, pinnae were separated from rachis. The dried rhizomes, stipes and rachis (2.9 kg) were soaked in ethanol (20 L) for fifteen days and filtered. The filtrate was concentrated at 313 K under reduced pressure to give 51.33 g of ethanolic extract, which was subjected to silica-gel column chromatography eluting gradient solvent system hexane-chloroform-methanol. More than 300 fractions were monitored by thin layer chromatography and combined to give 38 main fractions. Fraction 5 was further purified by silica-gel column chromatography with hexane-chloroform (10:1) and preparative TLC with dichloromethane and petroleum ether (2:3) to give the pure title compound (I). X-ray quality crystals were grown from a solution of hexane-chloroform (9:1) at room temperature.

Refinement

H atoms were included in the refinements at geometrically idealized positions with C—H distances 0.95 - 1.00 Å, and with Uiso(H) = 1.2Ueq(C), allowing for free rotation of the methyl groups. The final difference map was free of any chemically significant features. In the absence of significant anomalous scattering effects, an absolute structure could not be established in this analysis and therefore, Friedel pairs were merged.

Figures

Fig. 1.
ORTEPII (Johnson, 1976) drawing of molecule A with displacement ellipsoids plotted at the 30% probability level.
Fig. 2.
ORTEPII (Johnson, 1976) drawing of molecule B with displacement ellipsoids plotted at the 30% probability level.

Crystal data

C29H48OZ = 2
Mr = 412.67F000 = 460
Triclinic, P1Dx = 1.148 Mg m3
Hall symbol: P 1Melting point = 495–497 K
a = 6.581 (3) ÅMo Kα radiation λ = 0.71073 Å
b = 7.260 (4) ÅCell parameters from 1724 reflections
c = 27.908 (14) Åθ = 3.1–25.3º
α = 84.98 (2)ºµ = 0.07 mm1
β = 86.48 (3)ºT = 173 (2) K
γ = 64.01 (3)ºPlate, colorless
V = 1193.6 (10) Å30.12 × 0.10 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer4272 independent reflections
Radiation source: fine-focus sealed tube3161 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.050
T = 173(2) Kθmax = 25.3º
ω and [var phi] scansθmin = 3.1º
Absorption correction: multi-scan(SORTAV; Blessing, 1997)h = −7→7
Tmin = 0.992, Tmax = 0.997k = −8→8
7958 measured reflectionsl = −33→33

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.177  w = 1/[σ2(Fo2) + (0.08P)2 + 0.9P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.003
4272 reflectionsΔρmax = 0.25 e Å3
555 parametersΔρmin = −0.30 e Å3
3 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.
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)

xyzUiso*/Ueq
C11.1950 (11)0.7924 (9)0.6895 (2)0.0430 (16)
H1A1.20290.66180.67950.052*
H1B1.31320.81970.67100.052*
C21.2449 (11)0.7675 (9)0.7428 (2)0.0458 (16)
H2A1.13650.72630.76130.055*
H2B1.39900.65690.74830.055*
C31.2281 (10)0.9646 (9)0.7610 (2)0.0396 (14)
H3A1.34930.99590.74520.047*
H3B1.25420.94330.79600.047*
C40.9981 (10)1.1510 (8)0.7517 (2)0.0371 (14)
C50.9477 (9)1.1644 (8)0.6975 (2)0.0312 (12)
H51.07201.18920.68030.037*
C60.7297 (10)1.3533 (8)0.6823 (2)0.0387 (14)
H6A0.59681.33210.69480.046*
H6B0.72361.47590.69660.046*
C70.7201 (10)1.3899 (8)0.6279 (2)0.0380 (14)
H7A0.84531.42420.61630.046*
H7B0.57641.51030.61960.046*
C80.7368 (9)1.2052 (7)0.6010 (2)0.0298 (12)
C90.9473 (9)1.0093 (8)0.6205 (2)0.0303 (12)
H91.08191.03400.61010.036*
C100.9619 (9)0.9668 (8)0.6769 (2)0.0325 (13)
C110.9744 (11)0.8186 (8)0.5939 (2)0.0395 (14)
H11A1.11580.69940.60420.047*
H11B0.84680.78480.60360.047*
C120.9811 (11)0.8525 (8)0.5399 (2)0.0408 (15)
H12A0.98050.73320.52540.049*
H12B1.12360.86090.52970.049*
C130.7792 (9)1.0501 (8)0.5211 (2)0.0294 (12)
H130.64221.03620.53480.035*
C140.7750 (9)1.2403 (7)0.5449 (2)0.0307 (13)
C150.5757 (10)1.4435 (8)0.5244 (2)0.0357 (14)
H15A0.43211.45250.53970.043*
H15B0.59721.56190.53380.043*
C160.5533 (10)1.4622 (8)0.4699 (2)0.0365 (14)
H16A0.41721.58820.46020.044*
H16B0.68741.47100.45380.044*
C170.5338 (9)1.2735 (8)0.4552 (2)0.0323 (13)
H170.41391.26150.47720.039*
C180.7506 (9)1.0735 (8)0.4665 (2)0.0332 (13)
C190.6834 (12)0.9156 (9)0.4482 (2)0.0423 (15)
H19A0.58480.88280.47230.051*
H19B0.81910.78730.44170.051*
C200.5545 (11)1.0187 (9)0.4013 (2)0.0412 (14)
H20A0.42610.98390.39870.049*
H20B0.65670.97080.37280.049*
C210.4672 (10)1.2545 (8)0.4038 (2)0.0340 (13)
H210.29831.31610.40370.041*
C220.5414 (10)1.3552 (9)0.3616 (2)0.0406 (14)
C230.4498 (12)1.5885 (9)0.3589 (2)0.0454 (16)
H23A0.32361.64520.38210.055*
H23B0.39691.64430.32640.055*
H23C0.56991.62570.36640.055*
C241.0309 (13)1.3405 (10)0.7627 (3)0.0529 (18)
H24A0.88301.45890.76520.064*
H24B1.12151.37020.73670.064*
H24C1.10911.31270.79320.064*
C250.8197 (11)1.1357 (10)0.7870 (2)0.0465 (16)
H25A0.67101.24590.77880.056*
H25B0.85581.14900.81970.056*
H25C0.81741.00230.78540.056*
C260.5133 (10)1.1867 (9)0.6118 (2)0.0393 (14)
H26A0.54231.04210.61240.047*
H26B0.40521.26590.58670.047*
H26C0.45041.24040.64310.047*
C270.7810 (11)0.9017 (10)0.6983 (2)0.0432 (15)
H27A0.63841.02400.70280.052*
H27B0.83040.82520.72940.052*
H27C0.75880.81410.67640.052*
C280.9935 (10)1.2664 (9)0.5329 (2)0.0390 (14)
H28A0.98591.33100.50030.047*
H28B1.12421.13150.53480.047*
H28C1.00901.35340.55600.047*
C290.9562 (10)1.0664 (9)0.4360 (2)0.0415 (15)
H29A0.94021.04220.40270.050*
H29B1.09450.95490.44910.050*
H29C0.96491.19750.43670.050*
O300.6564 (8)1.2631 (6)0.32799 (17)0.0533 (12)
C310.2889 (11)0.9966 (8)−0.0337 (2)0.0380 (14)
H31A0.15591.1231−0.02490.046*
H31B0.41870.9845−0.01540.046*
C320.3420 (11)1.0165 (8)−0.0873 (2)0.0397 (15)
H32A0.20911.0375−0.10580.048*
H32B0.37271.1381−0.09440.048*
C330.5454 (10)0.8262 (9)−0.1030 (2)0.0390 (14)
H33A0.68100.8159−0.08720.047*
H33B0.56950.8421−0.13820.047*
C340.5221 (10)0.6230 (8)−0.0909 (2)0.0359 (14)
C350.4492 (10)0.6168 (8)−0.0372 (2)0.0304 (12)
H350.57960.6082−0.01900.037*
C360.4218 (10)0.4208 (8)−0.0203 (2)0.0373 (14)
H36A0.28180.4289−0.03350.045*
H36B0.55100.3000−0.03290.045*
C370.4107 (10)0.3926 (8)0.0342 (2)0.0339 (13)
H37A0.55700.37140.04700.041*
H37B0.38950.26710.04330.041*
C380.2185 (9)0.5761 (8)0.0580 (2)0.0298 (12)
C390.2278 (9)0.7806 (7)0.0369 (2)0.0304 (12)
H390.37390.77140.04790.037*
C400.2399 (9)0.8093 (7)−0.0192 (2)0.0294 (12)
C410.0424 (10)0.9667 (8)0.0609 (2)0.0361 (13)
H41A0.06211.09140.04980.043*
H41B−0.10720.98660.05040.043*
C420.0455 (11)0.9435 (8)0.1160 (2)0.0390 (14)
H42A0.18310.94880.12690.047*
H42B−0.08741.06030.12900.047*
C430.0415 (9)0.7436 (7)0.1361 (2)0.0297 (12)
H43−0.09410.74290.12200.036*
C440.2496 (9)0.5564 (8)0.1153 (2)0.0293 (12)
C450.2555 (10)0.3504 (8)0.1369 (2)0.0349 (13)
H45A0.14060.32540.12090.042*
H45B0.40530.23850.12920.042*
C460.2121 (10)0.3379 (8)0.1917 (2)0.0333 (13)
H46A0.20360.20750.20200.040*
H46B0.33670.34310.20880.040*
C47−0.0109 (9)0.5200 (8)0.2032 (2)0.0305 (12)
H47−0.12180.51850.18050.037*
C480.0036 (9)0.7260 (8)0.1906 (2)0.0319 (13)
C49−0.2381 (10)0.8751 (9)0.2069 (2)0.0394 (14)
H49A−0.24661.01200.21140.047*
H49B−0.34950.89060.18270.047*
C50−0.2841 (10)0.7765 (9)0.2548 (2)0.0418 (15)
H50A−0.44530.80380.25800.050*
H50B−0.24660.83270.28230.050*
C51−0.1296 (10)0.5406 (9)0.2538 (2)0.0365 (13)
H51−0.23320.47310.25330.044*
C520.0131 (10)0.4465 (9)0.2969 (2)0.0397 (14)
C530.1511 (11)0.2139 (9)0.3016 (2)0.0459 (16)
H53A0.08150.14940.28290.055*
H53B0.15490.16470.33550.055*
H53C0.30570.17810.28930.055*
C540.7616 (11)0.4468 (10)−0.0980 (2)0.0480 (17)
H54A0.75390.3146−0.09380.058*
H54B0.86280.4512−0.07430.058*
H54C0.81970.4632−0.13050.058*
C550.3667 (12)0.6029 (10)−0.1267 (2)0.0476 (16)
H55A0.33830.4834−0.11660.057*
H55B0.43950.5851−0.15880.057*
H55C0.22300.7272−0.12780.057*
C56−0.0049 (10)0.5719 (9)0.0467 (2)0.0384 (14)
H56A−0.12810.71100.04740.046*
H56B−0.03640.48060.07080.046*
H56C0.00720.52160.01470.046*
C570.0192 (10)0.8489 (9)−0.0428 (2)0.0405 (14)
H57A0.01090.7182−0.04480.049*
H57B0.01490.9139−0.07520.049*
H57C−0.10940.9398−0.02340.049*
C580.4763 (10)0.5523 (9)0.1273 (2)0.0372 (14)
H58A0.50850.50600.16120.045*
H58B0.46780.69050.12140.045*
H58C0.59710.45760.10700.045*
C590.1696 (10)0.7535 (9)0.2215 (2)0.0386 (14)
H59A0.11220.76850.25480.046*
H59B0.18720.87670.20930.046*
H59C0.31650.63310.22010.046*
O600.0185 (8)0.5464 (7)0.32916 (17)0.0546 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.048 (4)0.027 (3)0.034 (3)0.001 (3)0.000 (3)0.000 (2)
C20.045 (4)0.038 (4)0.038 (4)−0.001 (3)−0.003 (3)−0.006 (3)
C30.043 (4)0.038 (3)0.033 (3)−0.014 (3)−0.002 (3)0.001 (3)
C40.043 (3)0.025 (3)0.043 (4)−0.014 (3)0.001 (3)−0.001 (3)
C50.030 (3)0.023 (3)0.037 (3)−0.008 (2)0.003 (2)−0.007 (2)
C60.046 (4)0.018 (3)0.040 (3)−0.002 (3)0.000 (3)−0.003 (2)
C70.045 (4)0.017 (3)0.043 (3)−0.004 (3)−0.001 (3)−0.005 (2)
C80.031 (3)0.013 (2)0.041 (3)−0.005 (2)0.000 (2)−0.003 (2)
C90.030 (3)0.021 (3)0.037 (3)−0.009 (2)0.001 (2)−0.001 (2)
C100.038 (3)0.022 (3)0.035 (3)−0.011 (3)0.003 (2)−0.004 (2)
C110.046 (3)0.016 (3)0.046 (4)−0.003 (2)−0.001 (3)−0.007 (2)
C120.045 (4)0.019 (3)0.043 (4)0.000 (3)−0.005 (3)−0.005 (2)
C130.029 (3)0.016 (3)0.038 (3)−0.005 (2)−0.002 (2)−0.001 (2)
C140.034 (3)0.012 (2)0.038 (3)−0.003 (2)−0.003 (2)−0.003 (2)
C150.040 (3)0.013 (3)0.044 (3)−0.003 (2)−0.006 (3)0.001 (2)
C160.040 (3)0.017 (3)0.044 (3)−0.005 (2)−0.004 (3)−0.003 (2)
C170.032 (3)0.024 (3)0.041 (3)−0.012 (2)−0.004 (2)0.000 (2)
C180.038 (3)0.017 (3)0.041 (3)−0.010 (2)−0.001 (3)−0.002 (2)
C190.065 (4)0.022 (3)0.042 (4)−0.021 (3)−0.004 (3)−0.001 (3)
C200.061 (4)0.031 (3)0.038 (3)−0.026 (3)0.000 (3)−0.004 (3)
C210.035 (3)0.022 (3)0.043 (3)−0.012 (2)0.003 (3)−0.004 (2)
C220.045 (4)0.037 (3)0.042 (4)−0.019 (3)−0.001 (3)−0.004 (3)
C230.059 (4)0.028 (3)0.053 (4)−0.022 (3)−0.002 (3)0.001 (3)
C240.077 (5)0.041 (4)0.049 (4)−0.033 (4)−0.009 (4)−0.002 (3)
C250.053 (4)0.037 (3)0.042 (4)−0.012 (3)0.008 (3)−0.011 (3)
C260.033 (3)0.035 (3)0.043 (4)−0.009 (3)0.000 (3)−0.001 (3)
C270.052 (4)0.034 (3)0.044 (4)−0.019 (3)0.002 (3)0.000 (3)
C280.039 (3)0.036 (3)0.043 (4)−0.018 (3)−0.003 (3)0.002 (3)
C290.041 (3)0.035 (3)0.038 (3)−0.008 (3)0.007 (3)−0.006 (3)
O300.069 (3)0.037 (2)0.049 (3)−0.020 (2)0.011 (2)−0.002 (2)
C310.054 (4)0.021 (3)0.039 (3)−0.016 (3)−0.001 (3)−0.002 (2)
C320.060 (4)0.018 (3)0.042 (4)−0.018 (3)−0.004 (3)−0.001 (2)
C330.043 (4)0.035 (3)0.037 (3)−0.015 (3)−0.004 (3)−0.002 (3)
C340.043 (3)0.025 (3)0.036 (3)−0.011 (3)−0.001 (3)−0.004 (2)
C350.035 (3)0.021 (3)0.035 (3)−0.011 (2)−0.004 (2)−0.002 (2)
C360.047 (4)0.014 (3)0.047 (4)−0.010 (3)0.003 (3)−0.005 (2)
C370.041 (3)0.016 (3)0.038 (3)−0.007 (2)0.002 (3)−0.001 (2)
C380.033 (3)0.015 (3)0.038 (3)−0.007 (2)−0.004 (2)−0.001 (2)
C390.034 (3)0.015 (3)0.041 (3)−0.008 (2)−0.002 (2)−0.005 (2)
C400.034 (3)0.013 (3)0.039 (3)−0.008 (2)−0.001 (2)−0.004 (2)
C410.045 (3)0.015 (3)0.043 (3)−0.009 (2)0.008 (3)−0.002 (2)
C420.052 (4)0.017 (3)0.045 (4)−0.012 (3)0.009 (3)−0.008 (2)
C430.031 (3)0.014 (3)0.041 (3)−0.009 (2)−0.002 (2)0.001 (2)
C440.030 (3)0.013 (2)0.041 (3)−0.006 (2)0.002 (2)0.000 (2)
C450.041 (3)0.019 (3)0.041 (3)−0.011 (2)0.002 (3)−0.006 (2)
C460.036 (3)0.020 (3)0.041 (3)−0.010 (2)−0.001 (2)0.002 (2)
C470.033 (3)0.021 (3)0.034 (3)−0.009 (2)0.000 (2)−0.001 (2)
C480.032 (3)0.019 (3)0.044 (3)−0.010 (2)0.000 (2)−0.005 (2)
C490.039 (3)0.027 (3)0.044 (4)−0.006 (3)0.004 (3)−0.006 (3)
C500.035 (3)0.033 (3)0.045 (4)−0.004 (3)0.004 (3)−0.004 (3)
C510.034 (3)0.029 (3)0.046 (4)−0.014 (3)0.001 (3)0.001 (3)
C520.043 (3)0.038 (3)0.034 (3)−0.015 (3)0.006 (3)−0.004 (3)
C530.051 (4)0.027 (3)0.045 (4)−0.006 (3)−0.003 (3)0.008 (3)
C540.052 (4)0.032 (3)0.045 (4)−0.005 (3)0.004 (3)−0.003 (3)
C550.078 (5)0.032 (3)0.038 (3)−0.028 (3)−0.008 (3)−0.002 (3)
C560.052 (4)0.025 (3)0.040 (3)−0.019 (3)0.000 (3)0.001 (3)
C570.044 (4)0.029 (3)0.044 (4)−0.011 (3)−0.005 (3)0.000 (3)
C580.037 (3)0.036 (3)0.035 (3)−0.013 (3)−0.001 (2)−0.005 (3)
C590.041 (3)0.029 (3)0.049 (4)−0.018 (3)−0.001 (3)−0.005 (3)
O600.063 (3)0.042 (3)0.052 (3)−0.014 (2)−0.017 (2)−0.006 (2)

Geometric parameters (Å, °)

C1—C21.522 (8)C31—C321.523 (8)
C1—C101.539 (8)C31—C401.546 (8)
C1—H1A0.9900C31—H31A0.9900
C1—H1B0.9900C31—H31B0.9900
C2—C31.516 (9)C32—C331.518 (8)
C2—H2A0.9900C32—H32A0.9900
C2—H2B0.9900C32—H32B0.9900
C3—C41.543 (8)C33—C341.555 (8)
C3—H3A0.9900C33—H33A0.9900
C3—H3B0.9900C33—H33B0.9900
C4—C251.522 (9)C34—C551.534 (9)
C4—C241.542 (8)C34—C351.547 (8)
C4—C51.553 (8)C34—C541.549 (8)
C5—C61.539 (8)C35—C361.542 (8)
C5—C101.556 (7)C35—C401.566 (7)
C5—H51.0000C35—H351.0000
C6—C71.519 (8)C36—C371.516 (8)
C6—H6A0.9900C36—H36A0.9900
C6—H6B0.9900C36—H36B0.9900
C7—C81.553 (7)C37—C381.546 (7)
C7—H7A0.9900C37—H37A0.9900
C7—H7B0.9900C37—H37B0.9900
C8—C261.543 (8)C38—C561.536 (8)
C8—C91.571 (7)C38—C391.574 (7)
C8—C141.588 (8)C38—C441.610 (8)
C9—C111.564 (7)C39—C411.542 (7)
C9—C101.577 (8)C39—C401.563 (8)
C9—H91.0000C39—H391.0000
C10—C271.534 (8)C40—C571.530 (8)
C11—C121.507 (8)C41—C421.533 (8)
C11—H11A0.9900C41—H41A0.9900
C11—H11B0.9900C41—H41B0.9900
C12—C131.544 (7)C42—C431.520 (7)
C12—H12A0.9900C42—H42A0.9900
C12—H12B0.9900C42—H42B0.9900
C13—C181.531 (8)C43—C481.529 (8)
C13—C141.573 (7)C43—C441.572 (7)
C13—H131.0000C43—H431.0000
C14—C281.544 (8)C44—C581.536 (8)
C14—C151.572 (7)C44—C451.548 (7)
C15—C161.526 (8)C45—C461.540 (8)
C15—H15A0.9900C45—H45A0.9900
C15—H15B0.9900C45—H45B0.9900
C16—C171.523 (8)C46—C471.524 (7)
C16—H16A0.9900C46—H46A0.9900
C16—H16B0.9900C46—H46B0.9900
C17—C181.550 (8)C47—C481.548 (8)
C17—C211.559 (8)C47—C511.558 (8)
C17—H171.0000C47—H471.0000
C18—C191.532 (8)C48—C591.521 (8)
C18—C291.538 (8)C48—C491.548 (8)
C19—C201.551 (9)C49—C501.538 (9)
C19—H19A0.9900C49—H49A0.9900
C19—H19B0.9900C49—H49B0.9900
C20—C211.556 (8)C50—C511.564 (8)
C20—H20A0.9900C50—H50A0.9900
C20—H20B0.9900C50—H50B0.9900
C21—C221.501 (8)C51—C521.492 (9)
C21—H211.0000C51—H511.0000
C22—O301.216 (7)C52—O601.217 (7)
C22—C231.525 (9)C52—C531.525 (8)
C23—H23A0.9800C53—H53A0.9800
C23—H23B0.9800C53—H53B0.9800
C23—H23C0.9800C53—H53C0.9800
C24—H24A0.9800C54—H54A0.9800
C24—H24B0.9800C54—H54B0.9800
C24—H24C0.9800C54—H54C0.9800
C25—H25A0.9800C55—H55A0.9800
C25—H25B0.9800C55—H55B0.9800
C25—H25C0.9800C55—H55C0.9800
C26—H26A0.9800C56—H56A0.9800
C26—H26B0.9800C56—H56B0.9800
C26—H26C0.9800C56—H56C0.9800
C27—H27A0.9800C57—H57A0.9800
C27—H27B0.9800C57—H57B0.9800
C27—H27C0.9800C57—H57C0.9800
C28—H28A0.9800C58—H58A0.9800
C28—H28B0.9800C58—H58B0.9800
C28—H28C0.9800C58—H58C0.9800
C29—H29A0.9800C59—H59A0.9800
C29—H29B0.9800C59—H59B0.9800
C29—H29C0.9800C59—H59C0.9800
C2—C1—C10113.4 (5)C32—C31—C40113.0 (5)
C2—C1—H1A108.9C32—C31—H31A109.0
C10—C1—H1A108.9C40—C31—H31A109.0
C2—C1—H1B108.9C32—C31—H31B109.0
C10—C1—H1B108.9C40—C31—H31B109.0
H1A—C1—H1B107.7H31A—C31—H31B107.8
C3—C2—C1111.7 (5)C33—C32—C31111.3 (5)
C3—C2—H2A109.3C33—C32—H32A109.4
C1—C2—H2A109.3C31—C32—H32A109.4
C3—C2—H2B109.3C33—C32—H32B109.4
C1—C2—H2B109.3C31—C32—H32B109.4
H2A—C2—H2B107.9H32A—C32—H32B108.0
C2—C3—C4113.7 (5)C32—C33—C34114.0 (5)
C2—C3—H3A108.8C32—C33—H33A108.8
C4—C3—H3A108.8C34—C33—H33A108.8
C2—C3—H3B108.8C32—C33—H33B108.8
C4—C3—H3B108.8C34—C33—H33B108.8
H3A—C3—H3B107.7H33A—C33—H33B107.6
C25—C4—C24107.7 (5)C55—C34—C35115.7 (5)
C25—C4—C3109.8 (5)C55—C34—C54107.7 (5)
C24—C4—C3105.7 (5)C35—C34—C54108.9 (5)
C25—C4—C5116.0 (5)C55—C34—C33110.1 (5)
C24—C4—C5109.5 (5)C35—C34—C33108.0 (4)
C3—C4—C5107.7 (4)C54—C34—C33106.1 (5)
C6—C5—C4113.3 (4)C36—C35—C34113.3 (4)
C6—C5—C10111.2 (5)C36—C35—C40109.5 (4)
C4—C5—C10117.1 (4)C34—C35—C40117.6 (4)
C6—C5—H5104.6C36—C35—H35105.1
C4—C5—H5104.6C34—C35—H35105.1
C10—C5—H5104.6C40—C35—H35105.1
C7—C6—C5111.0 (4)C37—C36—C35111.8 (5)
C7—C6—H6A109.4C37—C36—H36A109.3
C5—C6—H6A109.4C35—C36—H36A109.3
C7—C6—H6B109.4C37—C36—H36B109.3
C5—C6—H6B109.4C35—C36—H36B109.3
H6A—C6—H6B108.0H36A—C36—H36B107.9
C6—C7—C8114.5 (5)C36—C37—C38113.7 (5)
C6—C7—H7A108.6C36—C37—H37A108.8
C8—C7—H7A108.6C38—C37—H37A108.8
C6—C7—H7B108.6C36—C37—H37B108.8
C8—C7—H7B108.6C38—C37—H37B108.8
H7A—C7—H7B107.6H37A—C37—H37B107.7
C26—C8—C7106.9 (5)C56—C38—C37107.0 (4)
C26—C8—C9112.2 (4)C56—C38—C39111.7 (4)
C7—C8—C9107.6 (4)C37—C38—C39108.9 (4)
C26—C8—C14111.1 (4)C56—C38—C44110.4 (4)
C7—C8—C14110.7 (4)C37—C38—C44110.5 (4)
C9—C8—C14108.3 (4)C39—C38—C44108.4 (4)
C11—C9—C8109.8 (4)C41—C39—C40114.1 (4)
C11—C9—C10113.0 (4)C41—C39—C38110.3 (4)
C8—C9—C10116.5 (4)C40—C39—C38115.8 (4)
C11—C9—H9105.5C41—C39—H39105.2
C8—C9—H9105.5C40—C39—H39105.2
C10—C9—H9105.5C38—C39—H39105.2
C27—C10—C1107.8 (5)C57—C40—C31107.3 (4)
C27—C10—C5113.3 (5)C57—C40—C39113.0 (5)
C1—C10—C5107.2 (5)C31—C40—C39109.1 (4)
C27—C10—C9112.4 (5)C57—C40—C35113.4 (4)
C1—C10—C9109.2 (4)C31—C40—C35106.4 (4)
C5—C10—C9106.7 (4)C39—C40—C35107.3 (4)
C12—C11—C9113.2 (5)C42—C41—C39113.4 (5)
C12—C11—H11A108.9C42—C41—H41A108.9
C9—C11—H11A108.9C39—C41—H41A108.9
C12—C11—H11B108.9C42—C41—H41B108.9
C9—C11—H11B108.9C39—C41—H41B108.9
H11A—C11—H11B107.8H41A—C41—H41B107.7
C11—C12—C13112.6 (5)C43—C42—C41112.5 (4)
C11—C12—H12A109.1C43—C42—H42A109.1
C13—C12—H12A109.1C41—C42—H42A109.1
C11—C12—H12B109.1C43—C42—H42B109.1
C13—C12—H12B109.1C41—C42—H42B109.1
H12A—C12—H12B107.8H42A—C42—H42B107.8
C18—C13—C12115.3 (4)C42—C43—C48115.4 (4)
C18—C13—C14116.3 (4)C42—C43—C44109.8 (4)
C12—C13—C14109.6 (4)C48—C43—C44115.1 (4)
C18—C13—H13104.8C42—C43—H43105.1
C12—C13—H13104.8C48—C43—H43105.1
C14—C13—H13104.8C44—C43—H43105.1
C28—C14—C15106.0 (5)C58—C44—C45106.2 (5)
C28—C14—C13111.7 (4)C58—C44—C43112.3 (4)
C15—C14—C13110.0 (4)C45—C44—C43110.9 (4)
C28—C14—C8112.5 (4)C58—C44—C38111.2 (4)
C15—C14—C8110.2 (4)C45—C44—C38109.8 (4)
C13—C14—C8106.5 (4)C43—C44—C38106.5 (4)
C16—C15—C14115.1 (4)C46—C45—C44115.4 (4)
C16—C15—H15A108.5C46—C45—H45A108.4
C14—C15—H15A108.5C44—C45—H45A108.4
C16—C15—H15B108.5C46—C45—H45B108.4
C14—C15—H15B108.5C44—C45—H45B108.4
H15A—C15—H15B107.5H45A—C45—H45B107.5
C17—C16—C15108.3 (5)C47—C46—C45107.7 (4)
C17—C16—H16A110.0C47—C46—H46A110.2
C15—C16—H16A110.0C45—C46—H46A110.2
C17—C16—H16B110.0C47—C46—H46B110.2
C15—C16—H16B110.0C45—C46—H46B110.2
H16A—C16—H16B108.4H46A—C46—H46B108.5
C16—C17—C18111.8 (5)C46—C47—C48111.2 (5)
C16—C17—C21123.3 (5)C46—C47—C51122.5 (5)
C18—C17—C21105.4 (4)C48—C47—C51105.6 (4)
C16—C17—H17104.9C46—C47—H47105.4
C18—C17—H17104.9C48—C47—H47105.4
C21—C17—H17104.9C51—C47—H47105.4
C13—C18—C19113.1 (5)C59—C48—C43116.4 (5)
C13—C18—C29115.6 (5)C59—C48—C49107.7 (5)
C19—C18—C29107.4 (5)C43—C48—C49112.4 (5)
C13—C18—C17107.4 (4)C59—C48—C47112.8 (5)
C19—C18—C17100.1 (5)C43—C48—C47107.2 (4)
C29—C18—C17112.2 (5)C49—C48—C4799.0 (4)
C18—C19—C20105.3 (4)C50—C49—C48105.3 (5)
C18—C19—H19A110.7C50—C49—H49A110.7
C20—C19—H19A110.7C48—C49—H49A110.7
C18—C19—H19B110.7C50—C49—H49B110.7
C20—C19—H19B110.7C48—C49—H49B110.7
H19A—C19—H19B108.8H49A—C49—H49B108.8
C19—C20—C21106.9 (4)C49—C50—C51106.3 (5)
C19—C20—H20A110.4C49—C50—H50A110.5
C21—C20—H20A110.4C51—C50—H50A110.5
C19—C20—H20B110.4C49—C50—H50B110.5
C21—C20—H20B110.4C51—C50—H50B110.5
H20A—C20—H20B108.6H50A—C50—H50B108.7
C22—C21—C20113.7 (5)C52—C51—C47118.6 (5)
C22—C21—C17118.5 (5)C52—C51—C50114.7 (5)
C20—C21—C17103.1 (4)C47—C51—C50103.3 (4)
C22—C21—H21107.0C52—C51—H51106.5
C20—C21—H21107.0C47—C51—H51106.5
C17—C21—H21107.0C50—C51—H51106.5
O30—C22—C21123.7 (6)O60—C52—C51122.9 (6)
O30—C22—C23118.4 (6)O60—C52—C53118.5 (6)
C21—C22—C23117.7 (5)C51—C52—C53118.5 (5)
C22—C23—H23A109.5C52—C53—H53A109.5
C22—C23—H23B109.5C52—C53—H53B109.5
H23A—C23—H23B109.5H53A—C53—H53B109.5
C22—C23—H23C109.5C52—C53—H53C109.5
H23A—C23—H23C109.5H53A—C53—H53C109.5
H23B—C23—H23C109.5H53B—C53—H53C109.5
C4—C24—H24A109.5C34—C54—H54A109.5
C4—C24—H24B109.5C34—C54—H54B109.5
H24A—C24—H24B109.5H54A—C54—H54B109.5
C4—C24—H24C109.5C34—C54—H54C109.5
H24A—C24—H24C109.5H54A—C54—H54C109.5
H24B—C24—H24C109.5H54B—C54—H54C109.5
C4—C25—H25A109.5C34—C55—H55A109.5
C4—C25—H25B109.5C34—C55—H55B109.5
H25A—C25—H25B109.5H55A—C55—H55B109.5
C4—C25—H25C109.5C34—C55—H55C109.5
H25A—C25—H25C109.5H55A—C55—H55C109.5
H25B—C25—H25C109.5H55B—C55—H55C109.5
C8—C26—H26A109.5C38—C56—H56A109.5
C8—C26—H26B109.5C38—C56—H56B109.5
H26A—C26—H26B109.5H56A—C56—H56B109.5
C8—C26—H26C109.5C38—C56—H56C109.5
H26A—C26—H26C109.5H56A—C56—H56C109.5
H26B—C26—H26C109.5H56B—C56—H56C109.5
C10—C27—H27A109.5C40—C57—H57A109.5
C10—C27—H27B109.5C40—C57—H57B109.5
H27A—C27—H27B109.5H57A—C57—H57B109.5
C10—C27—H27C109.5C40—C57—H57C109.5
H27A—C27—H27C109.5H57A—C57—H57C109.5
H27B—C27—H27C109.5H57B—C57—H57C109.5
C14—C28—H28A109.5C44—C58—H58A109.5
C14—C28—H28B109.5C44—C58—H58B109.5
H28A—C28—H28B109.5H58A—C58—H58B109.5
C14—C28—H28C109.5C44—C58—H58C109.5
H28A—C28—H28C109.5H58A—C58—H58C109.5
H28B—C28—H28C109.5H58B—C58—H58C109.5
C18—C29—H29A109.5C48—C59—H59A109.5
C18—C29—H29B109.5C48—C59—H59B109.5
H29A—C29—H29B109.5H59A—C59—H59B109.5
C18—C29—H29C109.5C48—C59—H59C109.5
H29A—C29—H29C109.5H59A—C59—H59C109.5
H29B—C29—H29C109.5H59B—C59—H59C109.5
C10—C1—C2—C3−56.8 (8)C40—C31—C32—C33−58.7 (7)
C1—C2—C3—C455.7 (7)C31—C32—C33—C3455.6 (7)
C2—C3—C4—C2575.5 (7)C32—C33—C34—C5577.0 (6)
C2—C3—C4—C24−168.6 (5)C32—C33—C34—C35−50.1 (6)
C2—C3—C4—C5−51.6 (6)C32—C33—C34—C54−166.7 (5)
C25—C4—C5—C660.6 (7)C55—C34—C35—C3656.7 (6)
C24—C4—C5—C6−61.6 (7)C54—C34—C35—C36−64.7 (6)
C3—C4—C5—C6−176.0 (5)C33—C34—C35—C36−179.5 (5)
C25—C4—C5—C10−71.0 (6)C55—C34—C35—C40−72.7 (6)
C24—C4—C5—C10166.9 (5)C54—C34—C35—C40165.9 (5)
C3—C4—C5—C1052.4 (6)C33—C34—C35—C4051.1 (6)
C4—C5—C6—C7165.2 (5)C34—C35—C36—C37165.2 (5)
C10—C5—C6—C7−60.4 (6)C40—C35—C36—C37−61.4 (6)
C5—C6—C7—C857.1 (7)C35—C36—C37—C3857.2 (7)
C6—C7—C8—C2670.3 (6)C36—C37—C38—C5671.7 (6)
C6—C7—C8—C9−50.4 (6)C36—C37—C38—C39−49.2 (6)
C6—C7—C8—C14−168.6 (5)C36—C37—C38—C44−168.1 (5)
C26—C8—C9—C1163.6 (6)C56—C38—C39—C4163.7 (6)
C7—C8—C9—C11−179.1 (5)C37—C38—C39—C41−178.4 (5)
C14—C8—C9—C11−59.3 (6)C44—C38—C39—C41−58.1 (6)
C26—C8—C9—C10−66.4 (6)C56—C38—C39—C40−67.8 (6)
C7—C8—C9—C1050.9 (6)C37—C38—C39—C4050.2 (6)
C14—C8—C9—C10170.6 (4)C44—C38—C39—C40170.5 (4)
C2—C1—C10—C27−69.1 (7)C32—C31—C40—C57−66.6 (6)
C2—C1—C10—C553.2 (7)C32—C31—C40—C39170.6 (5)
C2—C1—C10—C9168.5 (5)C32—C31—C40—C3555.1 (6)
C6—C5—C10—C27−66.9 (6)C41—C39—C40—C57−59.4 (6)
C4—C5—C10—C2765.6 (7)C38—C39—C40—C5770.3 (6)
C6—C5—C10—C1174.2 (5)C41—C39—C40—C3159.9 (6)
C4—C5—C10—C1−53.2 (6)C38—C39—C40—C31−170.4 (4)
C6—C5—C10—C957.3 (6)C41—C39—C40—C35174.8 (4)
C4—C5—C10—C9−170.1 (4)C38—C39—C40—C35−55.5 (6)
C11—C9—C10—C27−58.8 (6)C36—C35—C40—C57−67.0 (6)
C8—C9—C10—C2769.7 (6)C34—C35—C40—C5764.1 (6)
C11—C9—C10—C160.8 (6)C36—C35—C40—C31175.2 (4)
C8—C9—C10—C1−170.7 (5)C34—C35—C40—C31−53.6 (6)
C11—C9—C10—C5176.4 (5)C36—C35—C40—C3958.5 (5)
C8—C9—C10—C5−55.1 (6)C34—C35—C40—C39−170.4 (5)
C8—C9—C11—C1253.2 (7)C40—C39—C41—C42−175.2 (5)
C10—C9—C11—C12−175.0 (5)C38—C39—C41—C4252.4 (6)
C9—C11—C12—C13−52.3 (7)C39—C41—C42—C43−52.5 (7)
C11—C12—C13—C18−169.1 (5)C41—C42—C43—C48−170.0 (5)
C11—C12—C13—C1457.5 (7)C41—C42—C43—C4458.0 (6)
C18—C13—C14—C28−72.6 (6)C42—C43—C44—C5858.9 (6)
C12—C13—C14—C2860.4 (6)C48—C43—C44—C58−73.2 (6)
C18—C13—C14—C1544.8 (6)C42—C43—C44—C45177.5 (5)
C12—C13—C14—C15177.7 (5)C48—C43—C44—C4545.4 (6)
C18—C13—C14—C8164.2 (4)C42—C43—C44—C38−63.0 (5)
C12—C13—C14—C8−62.9 (6)C48—C43—C44—C38164.8 (4)
C26—C8—C14—C28178.2 (5)C56—C38—C44—C58177.9 (5)
C7—C8—C14—C2859.6 (6)C37—C38—C44—C5859.8 (6)
C9—C8—C14—C28−58.2 (5)C39—C38—C44—C58−59.5 (5)
C26—C8—C14—C1560.1 (5)C56—C38—C44—C4560.7 (5)
C7—C8—C14—C15−58.5 (6)C37—C38—C44—C45−57.4 (6)
C9—C8—C14—C15−176.2 (5)C39—C38—C44—C45−176.7 (4)
C26—C8—C14—C13−59.2 (5)C56—C38—C44—C43−59.4 (5)
C7—C8—C14—C13−177.7 (4)C37—C38—C44—C43−177.6 (4)
C9—C8—C14—C1364.5 (5)C39—C38—C44—C4363.2 (5)
C28—C14—C15—C1675.6 (6)C58—C44—C45—C4677.5 (6)
C13—C14—C15—C16−45.3 (7)C43—C44—C45—C46−44.8 (6)
C8—C14—C15—C16−162.4 (5)C38—C44—C45—C46−162.2 (4)
C14—C15—C16—C1755.1 (7)C44—C45—C46—C4754.2 (6)
C15—C16—C17—C18−63.6 (6)C45—C46—C47—C48−63.8 (6)
C15—C16—C17—C21169.2 (5)C45—C46—C47—C51170.2 (5)
C12—C13—C18—C1967.6 (7)C42—C43—C48—C59−56.4 (6)
C14—C13—C18—C19−162.1 (5)C44—C43—C48—C5973.1 (6)
C12—C13—C18—C29−56.8 (7)C42—C43—C48—C4968.5 (6)
C14—C13—C18—C2973.4 (6)C44—C43—C48—C49−162.0 (5)
C12—C13—C18—C17177.0 (5)C42—C43—C48—C47176.2 (5)
C14—C13—C18—C17−52.7 (6)C44—C43—C48—C47−54.3 (6)
C16—C17—C18—C1362.0 (6)C46—C47—C48—C59−65.3 (6)
C21—C17—C18—C13−161.7 (4)C51—C47—C48—C5969.6 (6)
C16—C17—C18—C19−179.8 (5)C46—C47—C48—C4364.2 (6)
C21—C17—C18—C19−43.5 (5)C51—C47—C48—C43−160.9 (4)
C16—C17—C18—C29−66.1 (6)C46—C47—C48—C49−178.9 (5)
C21—C17—C18—C2970.2 (6)C51—C47—C48—C49−43.9 (5)
C13—C18—C19—C20153.6 (5)C59—C48—C49—C50−75.5 (6)
C29—C18—C19—C20−77.7 (6)C43—C48—C49—C50155.0 (5)
C17—C18—C19—C2039.6 (6)C47—C48—C49—C5042.1 (6)
C18—C19—C20—C21−22.0 (7)C48—C49—C50—C51−25.3 (6)
C19—C20—C21—C22124.5 (5)C46—C47—C51—C5229.5 (8)
C19—C20—C21—C17−5.1 (6)C48—C47—C51—C52−99.0 (6)
C16—C17—C21—C2233.5 (8)C46—C47—C51—C50157.7 (5)
C18—C17—C21—C22−96.4 (6)C48—C47—C51—C5029.2 (6)
C16—C17—C21—C20160.1 (5)C49—C50—C51—C52128.2 (5)
C18—C17—C21—C2030.2 (6)C49—C50—C51—C47−2.3 (6)
C20—C21—C22—O301.0 (9)C47—C51—C52—O60119.0 (7)
C17—C21—C22—O30122.3 (6)C50—C51—C52—O60−3.6 (8)
C20—C21—C22—C23175.4 (5)C47—C51—C52—C53−63.6 (7)
C17—C21—C22—C23−63.3 (7)C50—C51—C52—C53173.9 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C20—H20B···O300.992.372.832 (7)108
C50—H50B···O600.992.392.837 (7)107

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2277).

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