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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o154.
Published online 2009 December 16. doi:  10.1107/S1600536809053380
PMCID: PMC2980194

Ethyl (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-methyl­ene-14-oxotetra­cyclo­[11.2.1.01,10.04,9]hexa­decane-5-carboxyl­ate

Abstract

The title compound, C22H34O3, was synthesized from isosteviol. The asymmetric unit contains of two independent mol­ecules with the same absolute configurations. In both the mol­ecules, the three six-membered rings adopt chair conformations, the stereochemistry of the A/B and B/C ring junctions are trans, and the five-membered ring D adopts an envelope conformation.

Related literature

Since the title compound was prepared from isosteviol, the configuration can be deduced from the known chirality of the isosteviol, see: Rodrigues & Lechat (1988 [triangle]), Xue et al. (1993 [triangle]). For the pharmacological activity of isosteviol, see: Liu et al. (2001 [triangle]); Mizushina et al. (2005 [triangle]); Wong et al. (2004 [triangle]); Zhang & Xu (2004 [triangle]). For ring conformations, see: Cremer & Pople (1975 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o154-scheme1.jpg

Experimental

Crystal data

  • C22H34O3
  • M r = 346.49
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o154-efi1.jpg
  • a = 6.5365 (9) Å
  • b = 12.5639 (15) Å
  • c = 13.1212 (16) Å
  • α = 69.174 (1)°
  • β = 87.518 (2)°
  • γ = 79.018 (1)°
  • V = 988.4 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.49 × 0.42 × 0.15 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1999 [triangle]) T min = 0.964, T max = 0.989
  • 5226 measured reflections
  • 3451 independent reflections
  • 1824 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 0.189
  • S = 0.90
  • 3451 reflections
  • 459 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT (Bruker, 1999 [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: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 nd PLATON (Spek, 2009 [triangle]).

Table 1
Comparison of the puckering parameters (Å, °) for the six and five-membered rings in mol­ecules 1 and 2

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053380/dn2514sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053380/dn2514Isup2.hkl

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

Acknowledgments

This material is based upon work funded by the Zhejiang Provincial Natural Science Foundation of China under grant No. Y2090552 and the Open Foundation of Key Disciplines within the Zhejiang Provincial Key Disciplines.

supplementary crystallographic information

Comment

Since the natural diterpenoid isosteviol has good pharmacological activity against a number of significant diseases including ischemia–reperfusion injury, hypertension, and cancer (Liu, et al., 2001; Mizushina et al., 2005; Wong et al., 2004; Zhang & Xu, 2004), the title compound was derived from it. Two independent molecules with identical absolute configuration are present in the asymmetric unit . Both molecule 1 (Fig.1) and molecule 2 (Fig.2) are built up from three six-membered rings and one five-membered ring. Some geometrical features (puckering parameters, Cremer & Pople, 1975) of these rings were investigated (Table 1) using PLATON (Spek, 2009).

Since the title compound was prepared from isosteviol, the configuration can be deduced from the known chirality of the isosteviol (Rodrigues & Lechat, 1988; Xue et al., 1993), and thus Fig. 1 and Fig. 2 represents the correct absolute configuration.

Experimental

A mixture of isosteviol (1 mmol), K2CO3 (2 mmol) and 10 mL of DMSO was transferred into a flask connected with refluxing equipment. After stirring for 5 min, bromoethane (1.2 mmol) was added, then stirring at 40°C for 6 h, the reaction mixture was poured into 40 mL water, extracted with 3×30 mL e thyl acetate, the ethyl acetate layer was washed with 3×30 mL water, then dryed with anhydrous Na2SO4, purified with silion colum and the title compound was gained. Crystals suitable for X-ray structure analysis were obtained by slow evaporation from a solution of isopropyl alcohol at room temperature.

Refinement

All H atoms were placed in geometrical positions and constrained to ride on their parent atoms with C–H distances in the range 0.96–0.98 Å, They were treated as riding atoms, with Uiso(H) = 1.5Ueq(C) for methyl H and 1.2Ueq(C) for other H atoms). Friedel reflections were merged before the final refinement and the stereochemistry is added according to the starting material.

Figures

Fig. 1.
Molecular view of molecule 1 with the atom labeling scheme. Ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
Fig. 2.
Molecular view of molecule 2 with the atom labeling scheme. Ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
Fig. 3.
The formation of the title compound

Crystal data

C22H34O3Z = 2
Mr = 346.49F(000) = 380
Triclinic, P1Dx = 1.164 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.5365 (9) ÅCell parameters from 1056 reflections
b = 12.5639 (15) Åθ = 3.2–19.4°
c = 13.1212 (16) ŵ = 0.08 mm1
α = 69.174 (1)°T = 293 K
β = 87.518 (2)°Plate, colorless
γ = 79.018 (1)°0.49 × 0.42 × 0.15 mm
V = 988.4 (2) Å3

Data collection

Bruker SMART CCD area-detector diffractometer3451 independent reflections
Radiation source: fine-focus sealed tube1824 reflections with I > 2σ(I)
graphiteRint = 0.034
[var phi] and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1999)h = −7→5
Tmin = 0.964, Tmax = 0.989k = −14→14
5226 measured reflectionsl = −14→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-atom parameters constrained
S = 0.90w = 1/[σ2(Fo2) + (0.1087P)2] where P = (Fo2 + 2Fc2)/3
3451 reflections(Δ/σ)max = 0.001
459 parametersΔρmax = 0.26 e Å3
3 restraintsΔρmin = −0.27 e Å3

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
O10.5517 (6)0.8839 (4)0.5497 (4)0.0762 (13)
O20.4744 (8)0.7550 (4)0.7036 (4)0.0915 (16)
O30.3864 (9)0.1982 (5)0.6485 (6)0.111 (2)
O40.5700 (8)0.2697 (5)0.1516 (6)0.1072 (19)
O50.6802 (9)0.3579 (5)0.2518 (5)0.1071 (19)
O60.7199 (9)0.9816 (6)0.0024 (6)0.120 (2)
C10.5924 (9)0.7852 (5)0.6322 (6)0.0558 (16)
C20.8169 (9)0.7176 (5)0.6312 (5)0.0536 (15)
C30.9253 (9)0.7692 (5)0.5244 (5)0.0617 (17)
H3A0.90440.85260.50520.074*
H3B1.07390.73900.53510.074*
C40.8461 (11)0.7427 (6)0.4310 (5)0.0693 (18)
H4A0.92720.77270.36710.083*
H4B0.70210.78170.41370.083*
C50.8601 (10)0.6134 (5)0.4585 (5)0.0616 (16)
H5A1.00590.57630.46560.074*
H5B0.79870.60120.39850.074*
C60.7511 (9)0.5552 (5)0.5634 (5)0.0525 (15)
C70.8269 (9)0.5851 (5)0.6582 (5)0.0524 (15)
H70.97620.55180.66660.063*
C80.7371 (10)0.5226 (5)0.7664 (5)0.0613 (16)
H8A0.58600.54210.76160.074*
H8B0.78460.54600.82280.074*
C90.8091 (11)0.3925 (5)0.7942 (5)0.0702 (19)
H9A0.95910.37410.80590.084*
H9B0.74750.35240.86230.084*
C100.7553 (10)0.3465 (5)0.7091 (5)0.0586 (16)
C110.8168 (9)0.4196 (5)0.5961 (5)0.0536 (15)
H110.96950.40420.59840.064*
C120.7574 (10)0.3752 (5)0.5104 (5)0.0615 (16)
H12A0.82220.41250.44240.074*
H12B0.60750.39590.49790.074*
C130.8246 (12)0.2435 (6)0.5439 (6)0.077 (2)
H13A0.76140.21760.49360.093*
H13B0.97470.22460.53880.093*
C140.7626 (10)0.1792 (5)0.6594 (6)0.0686 (18)
C150.5375 (11)0.2305 (6)0.6695 (6)0.077 (2)
C160.5268 (10)0.3286 (6)0.7102 (6)0.0718 (18)
H16A0.47340.30890.78340.086*
H16B0.43780.39810.66260.086*
C170.8666 (11)0.2207 (5)0.7359 (6)0.0700 (19)
H17A1.01450.21640.72250.084*
H17B0.84810.17470.81150.084*
C180.9342 (11)0.7363 (6)0.7214 (6)0.076 (2)
H18A0.94320.81660.69990.114*
H18B1.07200.69010.73210.114*
H18C0.86010.71370.78820.114*
C190.5141 (9)0.5991 (5)0.5419 (5)0.0595 (16)
H19A0.46740.57130.48930.089*
H19B0.48510.68240.51430.089*
H19C0.44230.57100.60880.089*
C200.8070 (13)0.0479 (6)0.6884 (8)0.099 (3)
H20A0.76980.01100.76250.149*
H20B0.95270.02200.68030.149*
H20C0.72650.02810.64060.149*
C210.3467 (11)0.9488 (7)0.5513 (7)0.090 (2)
H21A0.34590.99350.59840.108*
H21B0.24830.89690.57870.108*
C220.2882 (17)1.0272 (11)0.4378 (9)0.168 (6)
H22A0.37591.08430.41480.252*
H22B0.14531.06520.43450.252*
H22C0.30570.98300.39050.252*
C230.5436 (12)0.3482 (7)0.2027 (7)0.081 (2)
C240.3229 (11)0.4178 (6)0.1861 (6)0.0723 (19)
C250.2018 (12)0.4081 (7)0.0929 (7)0.083 (2)
H25A0.21790.32690.10180.100*
H25B0.05480.43700.09860.100*
C260.2701 (12)0.4730 (7)−0.0187 (6)0.083 (2)
H26A0.18300.4657−0.07300.099*
H26B0.41280.4393−0.02800.099*
C270.2558 (11)0.5991 (6)−0.0361 (5)0.075 (2)
H27A0.11020.6344−0.03620.090*
H27B0.30930.6371−0.10730.090*
C280.3773 (9)0.6210 (5)0.0515 (5)0.0566 (16)
C290.3104 (10)0.5473 (5)0.1658 (5)0.0648 (18)
H290.16080.57740.16640.078*
C300.4034 (11)0.5761 (6)0.2556 (5)0.0703 (19)
H30A0.36230.52790.32630.084*
H30B0.55440.56000.25350.084*
C310.3289 (12)0.7015 (6)0.2403 (6)0.076 (2)
H31A0.39170.71780.29760.091*
H31B0.17920.71460.24930.091*
C320.3777 (10)0.7881 (5)0.1293 (5)0.0619 (17)
C330.3076 (9)0.7516 (5)0.0370 (5)0.0557 (15)
H330.15500.76480.03870.067*
C340.3586 (11)0.8358 (6)−0.0715 (5)0.0726 (19)
H34A0.29220.8222−0.12930.087*
H34B0.50800.8208−0.08090.087*
C350.2887 (12)0.9627 (6)−0.0830 (6)0.080 (2)
H35A0.35091.0110−0.14690.095*
H35B0.13850.9837−0.09390.095*
C360.3494 (11)0.9864 (6)0.0168 (6)0.075 (2)
C370.5793 (12)0.9336 (7)0.0401 (6)0.080 (2)
C380.5995 (11)0.8116 (6)0.1176 (6)0.074 (2)
H38A0.65720.80330.18750.089*
H38B0.68870.75860.08870.089*
C390.2545 (11)0.9088 (6)0.1149 (6)0.0697 (18)
H39A0.10740.91390.10190.084*
H39B0.27080.92880.17860.084*
C400.2126 (13)0.3628 (7)0.2935 (7)0.099 (3)
H40A0.07700.40900.29240.148*
H40B0.29390.35950.35420.148*
H40C0.19860.28580.30070.148*
C410.6102 (10)0.5876 (6)0.0341 (6)0.0737 (18)
H41A0.64830.6416−0.03320.111*
H41B0.63950.51090.03110.111*
H41C0.68890.58930.09340.111*
C420.2981 (15)1.1158 (6)−0.0020 (8)0.107 (3)
H42A0.37621.1567−0.06200.161*
H42B0.33401.12810.06260.161*
H42C0.15171.1440−0.01840.161*
C430.7800 (16)0.2039 (9)0.1625 (10)0.136 (4)
H43A0.87440.23960.18920.163*
H43B0.82780.20000.09270.163*
C440.7712 (17)0.0848 (11)0.2426 (11)0.152 (4)
H44A0.74010.08910.31340.228*
H44B0.90350.03470.24600.228*
H44C0.66460.05460.21960.228*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.058 (3)0.067 (3)0.084 (3)0.002 (2)0.002 (2)−0.010 (3)
O20.085 (4)0.084 (3)0.088 (4)−0.005 (3)0.036 (3)−0.019 (3)
O30.073 (4)0.108 (4)0.167 (6)−0.031 (3)0.005 (4)−0.058 (4)
O40.072 (4)0.091 (4)0.158 (6)−0.001 (3)−0.011 (3)−0.050 (4)
O50.070 (3)0.099 (4)0.142 (5)0.009 (3)−0.041 (3)−0.038 (3)
O60.073 (4)0.125 (5)0.158 (6)−0.036 (4)0.008 (4)−0.038 (4)
C10.052 (4)0.051 (4)0.068 (5)0.001 (3)0.000 (3)−0.030 (3)
C20.049 (4)0.054 (4)0.056 (4)−0.006 (3)−0.006 (3)−0.019 (3)
C30.053 (4)0.053 (4)0.071 (5)−0.008 (3)0.005 (3)−0.013 (3)
C40.071 (4)0.070 (4)0.056 (4)−0.013 (3)0.015 (3)−0.011 (3)
C50.064 (4)0.066 (4)0.051 (4)−0.007 (3)0.009 (3)−0.019 (3)
C60.053 (4)0.060 (4)0.044 (4)−0.007 (3)0.001 (3)−0.020 (3)
C70.052 (4)0.055 (4)0.047 (4)−0.005 (3)−0.006 (3)−0.016 (3)
C80.070 (4)0.068 (4)0.045 (4)−0.008 (3)0.002 (3)−0.022 (3)
C90.081 (5)0.066 (4)0.057 (4)−0.009 (3)−0.001 (3)−0.016 (3)
C100.057 (4)0.055 (4)0.062 (4)−0.009 (3)−0.003 (3)−0.018 (3)
C110.048 (3)0.060 (4)0.055 (4)−0.009 (3)0.003 (3)−0.024 (3)
C120.061 (4)0.065 (4)0.063 (4)−0.006 (3)0.003 (3)−0.032 (3)
C130.077 (5)0.076 (4)0.088 (5)−0.015 (3)0.000 (4)−0.039 (4)
C140.063 (4)0.062 (4)0.083 (5)−0.014 (3)0.001 (4)−0.027 (4)
C150.057 (4)0.070 (4)0.101 (6)−0.021 (3)0.001 (4)−0.022 (4)
C160.057 (4)0.071 (4)0.085 (5)−0.011 (3)0.010 (3)−0.027 (4)
C170.064 (4)0.061 (4)0.076 (5)−0.009 (3)−0.004 (3)−0.014 (3)
C180.067 (4)0.071 (4)0.091 (5)−0.010 (3)−0.020 (4)−0.029 (4)
C190.058 (4)0.064 (4)0.059 (4)−0.011 (3)−0.006 (3)−0.023 (3)
C200.092 (6)0.069 (5)0.142 (8)−0.019 (4)0.002 (5)−0.041 (5)
C210.064 (5)0.086 (5)0.106 (6)0.008 (4)−0.003 (4)−0.029 (5)
C220.108 (8)0.145 (9)0.155 (11)0.053 (7)0.023 (7)0.023 (8)
C230.061 (5)0.077 (5)0.097 (6)−0.012 (4)−0.007 (4)−0.022 (4)
C240.060 (4)0.071 (5)0.085 (5)−0.015 (3)0.000 (4)−0.025 (4)
C250.066 (5)0.087 (5)0.103 (6)−0.017 (4)−0.012 (4)−0.038 (5)
C260.081 (5)0.097 (6)0.081 (6)−0.020 (4)−0.016 (4)−0.041 (4)
C270.079 (5)0.088 (5)0.059 (4)−0.019 (4)−0.012 (3)−0.025 (4)
C280.051 (4)0.065 (4)0.054 (4)−0.010 (3)−0.008 (3)−0.020 (3)
C290.056 (4)0.074 (5)0.060 (4)−0.009 (3)−0.004 (3)−0.020 (3)
C300.078 (5)0.077 (5)0.049 (4)−0.010 (3)0.000 (3)−0.016 (3)
C310.088 (5)0.077 (5)0.059 (5)−0.010 (4)−0.004 (4)−0.022 (4)
C320.062 (4)0.070 (4)0.050 (4)−0.004 (3)−0.005 (3)−0.019 (3)
C330.050 (4)0.069 (4)0.044 (4)−0.005 (3)−0.004 (3)−0.017 (3)
C340.074 (5)0.080 (5)0.059 (4)−0.015 (4)−0.007 (3)−0.016 (3)
C350.079 (5)0.076 (5)0.066 (5)−0.006 (4)−0.001 (4)−0.006 (4)
C360.068 (5)0.070 (5)0.078 (5)−0.014 (3)−0.005 (4)−0.016 (4)
C370.066 (5)0.089 (5)0.084 (5)−0.021 (4)0.000 (4)−0.026 (4)
C380.067 (5)0.082 (5)0.072 (5)−0.011 (4)−0.013 (4)−0.027 (4)
C390.068 (4)0.072 (4)0.065 (4)−0.002 (3)−0.003 (3)−0.024 (4)
C400.088 (6)0.083 (5)0.104 (7)−0.024 (4)0.024 (5)−0.006 (5)
C410.056 (4)0.093 (5)0.069 (4)−0.003 (3)0.006 (3)−0.031 (4)
C420.115 (7)0.075 (6)0.122 (7)−0.014 (5)−0.005 (6)−0.025 (5)
C430.094 (7)0.109 (8)0.172 (11)0.015 (6)0.010 (7)−0.027 (8)
C440.100 (8)0.138 (10)0.179 (11)0.021 (6)0.000 (7)−0.031 (9)

Geometric parameters (Å, °)

O1—C11.314 (7)C21—H21B0.9700
O1—C211.434 (8)C22—H22A0.9600
O2—C11.189 (8)C22—H22B0.9600
O3—C151.213 (7)C22—H22C0.9600
O4—C231.360 (10)C23—C241.518 (10)
O4—C431.445 (11)C24—C251.538 (9)
O5—C231.171 (8)C24—C291.539 (9)
O6—C371.188 (8)C24—C401.547 (11)
C1—C21.551 (8)C25—C261.497 (11)
C2—C31.526 (9)C25—H25A0.9700
C2—C181.545 (8)C25—H25B0.9700
C2—C71.562 (8)C26—C271.504 (10)
C3—C41.514 (9)C26—H26A0.9700
C3—H3A0.9700C26—H26B0.9700
C3—H3B0.9700C27—C281.554 (8)
C4—C51.519 (9)C27—H27A0.9700
C4—H4A0.9700C27—H27B0.9700
C4—H4B0.9700C28—C411.530 (9)
C5—C61.528 (9)C28—C291.551 (8)
C5—H5A0.9700C28—C331.561 (8)
C5—H5B0.9700C29—C301.530 (8)
C6—C191.545 (8)C29—H290.9800
C6—C71.546 (8)C30—C311.501 (9)
C6—C111.578 (8)C30—H30A0.9700
C7—C81.512 (8)C30—H30B0.9700
C7—H70.9800C31—C321.541 (9)
C8—C91.524 (8)C31—H31A0.9700
C8—H8A0.9700C31—H31B0.9700
C8—H8B0.9700C32—C381.524 (9)
C9—C101.508 (8)C32—C391.526 (9)
C9—H9A0.9700C32—C331.553 (8)
C9—H9B0.9700C33—C341.510 (9)
C10—C111.524 (8)C33—H330.9800
C10—C171.529 (9)C34—C351.527 (10)
C10—C161.551 (9)C34—H34A0.9700
C11—C121.515 (8)C34—H34B0.9700
C11—H110.9800C35—C361.525 (9)
C12—C131.531 (9)C35—H35A0.9700
C12—H12A0.9700C35—H35B0.9700
C12—H12B0.9700C36—C391.504 (10)
C13—C141.521 (10)C36—C371.519 (10)
C13—H13A0.9700C36—C421.527 (10)
C13—H13B0.9700C37—C381.492 (10)
C14—C151.510 (10)C38—H38A0.9700
C14—C171.519 (9)C38—H38B0.9700
C14—C201.528 (9)C39—H39A0.9700
C15—C161.497 (10)C39—H39B0.9700
C16—H16A0.9700C40—H40A0.9600
C16—H16B0.9700C40—H40B0.9600
C17—H17A0.9700C40—H40C0.9600
C17—H17B0.9700C41—H41A0.9600
C18—H18A0.9600C41—H41B0.9600
C18—H18B0.9600C41—H41C0.9600
C18—H18C0.9600C42—H42A0.9600
C19—H19A0.9600C42—H42B0.9600
C19—H19B0.9600C42—H42C0.9600
C19—H19C0.9600C43—C441.502 (15)
C20—H20A0.9600C43—H43A0.9700
C20—H20B0.9600C43—H43B0.9700
C20—H20C0.9600C44—H44A0.9600
C21—C221.483 (12)C44—H44B0.9600
C21—H21A0.9700C44—H44C0.9600
C1—O1—C21113.3 (5)H22B—C22—H22C109.5
C23—O4—C43113.4 (7)O5—C23—O4121.7 (7)
O2—C1—O1123.4 (5)O5—C23—C24126.8 (8)
O2—C1—C2123.7 (6)O4—C23—C24111.5 (6)
O1—C1—C2112.7 (6)C23—C24—C25113.1 (7)
C3—C2—C18107.0 (5)C23—C24—C29113.9 (6)
C3—C2—C1112.5 (5)C25—C24—C29108.1 (6)
C18—C2—C1103.7 (5)C23—C24—C40105.0 (6)
C3—C2—C7110.3 (5)C25—C24—C40107.6 (6)
C18—C2—C7109.8 (4)C29—C24—C40108.9 (6)
C1—C2—C7113.1 (5)C26—C25—C24114.1 (6)
C4—C3—C2113.0 (5)C26—C25—H25A108.7
C4—C3—H3A109.0C24—C25—H25A108.7
C2—C3—H3A109.0C26—C25—H25B108.7
C4—C3—H3B109.0C24—C25—H25B108.7
C2—C3—H3B109.0H25A—C25—H25B107.6
H3A—C3—H3B107.8C25—C26—C27111.2 (7)
C3—C4—C5111.9 (5)C25—C26—H26A109.4
C3—C4—H4A109.2C27—C26—H26A109.4
C5—C4—H4A109.2C25—C26—H26B109.4
C3—C4—H4B109.2C27—C26—H26B109.4
C5—C4—H4B109.2H26A—C26—H26B108.0
H4A—C4—H4B107.9C26—C27—C28113.9 (5)
C4—C5—C6113.6 (5)C26—C27—H27A108.8
C4—C5—H5A108.8C28—C27—H27A108.8
C6—C5—H5A108.8C26—C27—H27B108.8
C4—C5—H5B108.8C28—C27—H27B108.8
C6—C5—H5B108.8H27A—C27—H27B107.7
H5A—C5—H5B107.7C41—C28—C29112.3 (5)
C5—C6—C19107.6 (4)C41—C28—C27107.7 (6)
C5—C6—C7110.2 (5)C29—C28—C27108.3 (5)
C19—C6—C7110.9 (5)C41—C28—C33113.1 (5)
C5—C6—C11108.6 (5)C29—C28—C33108.0 (5)
C19—C6—C11113.1 (5)C27—C28—C33107.2 (5)
C7—C6—C11106.4 (4)C30—C29—C24116.3 (5)
C8—C7—C6112.8 (5)C30—C29—C28111.0 (5)
C8—C7—C2115.1 (5)C24—C29—C28115.7 (6)
C6—C7—C2114.0 (4)C30—C29—H29104.0
C8—C7—H7104.5C24—C29—H29104.0
C6—C7—H7104.5C28—C29—H29104.0
C2—C7—H7104.5C31—C30—C29110.2 (5)
C7—C8—C9108.5 (5)C31—C30—H30A109.6
C7—C8—H8A110.0C29—C30—H30A109.6
C9—C8—H8A110.0C31—C30—H30B109.6
C7—C8—H8B110.0C29—C30—H30B109.6
C9—C8—H8B110.0H30A—C30—H30B108.1
H8A—C8—H8B108.4C30—C31—C32115.1 (6)
C10—C9—C8115.1 (5)C30—C31—H31A108.5
C10—C9—H9A108.5C32—C31—H31A108.5
C8—C9—H9A108.5C30—C31—H31B108.5
C10—C9—H9B108.5C32—C31—H31B108.5
C8—C9—H9B108.5H31A—C31—H31B107.5
H9A—C9—H9B107.5C38—C32—C39100.6 (5)
C9—C10—C11110.9 (5)C38—C32—C31115.8 (5)
C9—C10—C17110.4 (5)C39—C32—C31109.4 (6)
C11—C10—C17109.2 (5)C38—C32—C33113.5 (5)
C9—C10—C16114.7 (6)C39—C32—C33108.1 (5)
C11—C10—C16112.0 (5)C31—C32—C33109.0 (5)
C17—C10—C1698.9 (5)C34—C33—C32108.7 (5)
C12—C11—C10110.9 (5)C34—C33—C28114.8 (5)
C12—C11—C6113.4 (4)C32—C33—C28116.1 (4)
C10—C11—C6116.3 (5)C34—C33—H33105.4
C12—C11—H11105.0C32—C33—H33105.4
C10—C11—H11105.0C28—C33—H33105.4
C6—C11—H11105.0C33—C34—C35113.5 (6)
C11—C12—C13112.2 (5)C33—C34—H34A108.9
C11—C12—H12A109.2C35—C34—H34A108.9
C13—C12—H12A109.2C33—C34—H34B108.9
C11—C12—H12B109.2C35—C34—H34B108.9
C13—C12—H12B109.2H34A—C34—H34B107.7
H12A—C12—H12B107.9C36—C35—C34112.5 (5)
C14—C13—C12112.5 (6)C36—C35—H35A109.1
C14—C13—H13A109.1C34—C35—H35A109.1
C12—C13—H13A109.1C36—C35—H35B109.1
C14—C13—H13B109.1C34—C35—H35B109.1
C12—C13—H13B109.1H35A—C35—H35B107.8
H13A—C13—H13B107.8C39—C36—C37100.8 (6)
C15—C14—C17100.1 (6)C39—C36—C35108.0 (5)
C15—C14—C13106.8 (5)C37—C36—C35106.2 (6)
C17—C14—C13107.6 (5)C39—C36—C42116.0 (7)
C15—C14—C20114.4 (6)C37—C36—C42113.8 (6)
C17—C14—C20114.5 (6)C35—C36—C42111.2 (6)
C13—C14—C20112.5 (6)O6—C37—C38125.7 (7)
O3—C15—C16124.3 (6)O6—C37—C36125.5 (7)
O3—C15—C14126.1 (7)C38—C37—C36108.8 (6)
C16—C15—C14109.6 (5)C37—C38—C32104.8 (5)
C15—C16—C10104.6 (5)C37—C38—H38A110.8
C15—C16—H16A110.8C32—C38—H38A110.8
C10—C16—H16A110.8C37—C38—H38B110.8
C15—C16—H16B110.8C32—C38—H38B110.8
C10—C16—H16B110.8H38A—C38—H38B108.9
H16A—C16—H16B108.9C36—C39—C32103.4 (6)
C14—C17—C10104.1 (5)C36—C39—H39A111.1
C14—C17—H17A110.9C32—C39—H39A111.1
C10—C17—H17A110.9C36—C39—H39B111.1
C14—C17—H17B110.9C32—C39—H39B111.1
C10—C17—H17B110.9H39A—C39—H39B109.0
H17A—C17—H17B109.0C24—C40—H40A109.5
C2—C18—H18A109.5C24—C40—H40B109.5
C2—C18—H18B109.5H40A—C40—H40B109.5
H18A—C18—H18B109.5C24—C40—H40C109.5
C2—C18—H18C109.5H40A—C40—H40C109.5
H18A—C18—H18C109.5H40B—C40—H40C109.5
H18B—C18—H18C109.5C28—C41—H41A109.5
C6—C19—H19A109.5C28—C41—H41B109.5
C6—C19—H19B109.5H41A—C41—H41B109.5
H19A—C19—H19B109.5C28—C41—H41C109.5
C6—C19—H19C109.5H41A—C41—H41C109.5
H19A—C19—H19C109.5H41B—C41—H41C109.5
H19B—C19—H19C109.5C36—C42—H42A109.5
C14—C20—H20A109.5C36—C42—H42B109.5
C14—C20—H20B109.5H42A—C42—H42B109.5
H20A—C20—H20B109.5C36—C42—H42C109.5
C14—C20—H20C109.5H42A—C42—H42C109.5
H20A—C20—H20C109.5H42B—C42—H42C109.5
H20B—C20—H20C109.5O4—C43—C44106.1 (8)
O1—C21—C22107.3 (7)O4—C43—H43A110.5
O1—C21—H21A110.3C44—C43—H43A110.5
C22—C21—H21A110.3O4—C43—H43B110.5
O1—C21—H21B110.2C44—C43—H43B110.5
C22—C21—H21B110.2H43A—C43—H43B108.7
H21A—C21—H21B108.5C43—C44—H44A109.5
C21—C22—H22A109.5C43—C44—H44B109.5
C21—C22—H22B109.5H44A—C44—H44B109.5
H22A—C22—H22B109.5C43—C44—H44C109.5
C21—C22—H22C109.5H44A—C44—H44C109.5
H22A—C22—H22C109.5H44B—C44—H44C109.5
C21—O1—C1—O2−3.1 (9)C43—O4—C23—O5−1.3 (12)
C21—O1—C1—C2−178.3 (5)C43—O4—C23—C24178.2 (7)
O2—C1—C2—C3174.0 (6)O5—C23—C24—C25163.8 (8)
O1—C1—C2—C3−10.7 (7)O4—C23—C24—C25−15.7 (9)
O2—C1—C2—C18−70.7 (7)O5—C23—C24—C2939.9 (11)
O1—C1—C2—C18104.5 (6)O4—C23—C24—C29−139.6 (7)
O2—C1—C2—C748.2 (8)O5—C23—C24—C40−79.1 (10)
O1—C1—C2—C7−136.6 (5)O4—C23—C24—C40101.4 (7)
C18—C2—C3—C4172.0 (5)C23—C24—C25—C26−73.0 (8)
C1—C2—C3—C4−74.7 (6)C29—C24—C25—C2654.0 (9)
C7—C2—C3—C452.6 (6)C40—C24—C25—C26171.4 (6)
C2—C3—C4—C5−54.8 (7)C24—C25—C26—C27−56.5 (9)
C3—C4—C5—C654.5 (7)C25—C26—C27—C2855.0 (8)
C4—C5—C6—C1969.2 (6)C26—C27—C28—C4170.2 (8)
C4—C5—C6—C7−51.9 (6)C26—C27—C28—C29−51.4 (8)
C4—C5—C6—C11−168.0 (5)C26—C27—C28—C33−167.8 (6)
C5—C6—C7—C8−175.6 (5)C23—C24—C29—C30−59.2 (9)
C19—C6—C7—C865.4 (6)C25—C24—C29—C30174.2 (6)
C11—C6—C7—C8−58.0 (6)C40—C24—C29—C3057.6 (8)
C5—C6—C7—C250.7 (6)C23—C24—C29—C2873.9 (8)
C19—C6—C7—C2−68.4 (6)C25—C24—C29—C28−52.7 (7)
C11—C6—C7—C2168.3 (5)C40—C24—C29—C28−169.3 (5)
C3—C2—C7—C8176.0 (5)C41—C28—C29—C3068.4 (7)
C18—C2—C7—C858.3 (7)C27—C28—C29—C30−172.9 (5)
C1—C2—C7—C8−57.0 (6)C33—C28—C29—C30−57.1 (6)
C3—C2—C7—C6−51.4 (6)C41—C28—C29—C24−67.1 (7)
C18—C2—C7—C6−169.1 (5)C27—C28—C29—C2451.6 (7)
C1—C2—C7—C675.6 (7)C33—C28—C29—C24167.4 (5)
C6—C7—C8—C961.7 (6)C24—C29—C30—C31−164.2 (6)
C2—C7—C8—C9−165.1 (5)C28—C29—C30—C3160.6 (7)
C7—C8—C9—C10−56.3 (7)C29—C30—C31—C32−57.4 (8)
C8—C9—C10—C1148.9 (7)C30—C31—C32—C38−79.5 (8)
C8—C9—C10—C17170.1 (6)C30—C31—C32—C39167.8 (5)
C8—C9—C10—C16−79.2 (7)C30—C31—C32—C3349.7 (7)
C9—C10—C11—C12−178.5 (5)C38—C32—C33—C34−48.7 (7)
C17—C10—C11—C1259.6 (6)C39—C32—C33—C3461.9 (7)
C16—C10—C11—C12−48.9 (6)C31—C32—C33—C34−179.2 (5)
C9—C10—C11—C6−47.0 (7)C38—C32—C33—C2882.6 (7)
C17—C10—C11—C6−168.9 (5)C39—C32—C33—C28−166.8 (5)
C16—C10—C11—C682.6 (6)C31—C32—C33—C28−47.9 (7)
C5—C6—C11—C12−60.3 (6)C41—C28—C33—C3455.9 (7)
C19—C6—C11—C1259.1 (7)C29—C28—C33—C34−179.2 (5)
C7—C6—C11—C12−178.9 (5)C27—C28—C33—C34−62.6 (7)
C5—C6—C11—C10169.4 (5)C41—C28—C33—C32−72.4 (7)
C19—C6—C11—C10−71.2 (6)C29—C28—C33—C3252.5 (6)
C7—C6—C11—C1050.8 (6)C27—C28—C33—C32169.0 (5)
C10—C11—C12—C13−47.5 (7)C32—C33—C34—C35−48.0 (7)
C6—C11—C12—C13179.5 (6)C28—C33—C34—C35−179.9 (5)
C11—C12—C13—C1448.3 (7)C33—C34—C35—C3647.0 (8)
C12—C13—C14—C1547.1 (7)C34—C35—C36—C39−57.7 (8)
C12—C13—C14—C17−59.6 (7)C34—C35—C36—C3749.7 (8)
C12—C13—C14—C20173.4 (5)C34—C35—C36—C42174.0 (7)
C17—C14—C15—O3−158.8 (8)C39—C36—C37—O6−158.6 (8)
C13—C14—C15—O389.2 (8)C35—C36—C37—O688.9 (9)
C20—C14—C15—O3−35.9 (11)C42—C36—C37—O6−33.8 (12)
C17—C14—C15—C1621.1 (7)C39—C36—C37—C3821.6 (8)
C13—C14—C15—C16−90.9 (7)C35—C36—C37—C38−90.9 (7)
C20—C14—C15—C16144.0 (7)C42—C36—C37—C38146.5 (7)
O3—C15—C16—C10−172.4 (7)O6—C37—C38—C32−173.1 (8)
C14—C15—C16—C107.7 (8)C36—C37—C38—C326.6 (8)
C9—C10—C16—C15−150.3 (5)C39—C32—C38—C37−31.7 (7)
C11—C10—C16—C1582.1 (6)C31—C32—C38—C37−149.5 (6)
C17—C10—C16—C15−32.9 (7)C33—C32—C38—C3783.4 (6)
C15—C14—C17—C10−42.7 (6)C37—C36—C39—C32−41.8 (7)
C13—C14—C17—C1068.6 (7)C35—C36—C39—C3269.4 (6)
C20—C14—C17—C10−165.6 (6)C42—C36—C39—C32−165.1 (6)
C9—C10—C17—C14168.1 (6)C38—C32—C39—C3646.3 (6)
C11—C10—C17—C14−69.7 (6)C31—C32—C39—C36168.7 (5)
C16—C10—C17—C1447.4 (7)C33—C32—C39—C36−72.8 (6)
C1—O1—C21—C22−156.5 (8)C23—O4—C43—C44105.9 (10)

Table 1 Comparison of the puckering parameters (Å, °) for the six and five-membered rings in molecules 1 and 2

Molecule12
Puckering parametersQθ[var phi]Qθ[var phi]
Ring A1, A20.536 (7)180.0 (7)273 (27)0.545 (8)177.2 (8)251 (29)
Ring B1, B20.557 (7)9.5 (7)72 (4)0.561 (7)7.8 (7)71 (5)
Ring C1, C20.633 (7)164.8 (6)120 (3)0.646 (8)163.2 (7)131 (2)
Puckering parametersq2[var phi]2q2[var phi]2
Ring D1, D20.467 (8)333.7 (10)0.452 (8)332.2 (11)

Ring A1 atoms C2–C7, A2 C24–C29, B1 C6–C11, B2 C28–C33, C1 C10–C14/C17, C2 C32–C36/C39, D1 C14–C16/C10/C17, and D2 C36–C38/C32/C39.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2514).

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