supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

Acta Cryst. (2007). E63, o3980    [ doi:10.1107/S160053680703944X ]

3[beta]-Acetoxy-17-ethylenedioxyandrost-5-ene

Y.-M. Xu, S.-G. Tang, Y.-X. Zhou, S. Liu and C. Guo

Abstract top

In the molecule of the title compound, C23H34O4, the six-membered rings A, B and C have chair, flattened boat and chair conformations, respectively, while the two five-membered rings D and E have envelope conformations. Intramolecular C-H...O hydrogen bonds result in the formation of three more five-membered rings.

Comment top

The title compound, (I), is an intermediate product of drospirenone, which is a new oral contraceptive (Mohr & Nickisch, 2005). We report herein its crystal structure.

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987).

Rings A (C4—C9), B (C7/C8/C10—C13) and C (C10/C11/C14—C17) are not planar, having total puckering amplitudes, QT, of 0.547 (3), 0.477 (2) and 0.676 (3) Å, respectively, and chair, flattened boat and chair conformations, respectively [φ = −173.98 (3)°, θ = 169.83 (3)°; φ = −16.01 (2)°, θ = 115.71 (3)° and φ = −147.03 (3)°, θ = 86.92 (3)°, respectively] (Cremer & Pople, 1975). Rings D (C16/C17/C19—C21) and E (O3/O4/C19/C24/C25) have envelope conformations with atoms C16 and C19 displaced by 0.646 (3) Å and 0.220 (2) Å from the planes of the other four ring atoms, respectively. Rings D and E have pseudo twofold axis and pseudo mirror plane, respectively, running through atom C20 and midpoint of C16—C17 bond (for ring D) and atom C19 and midpoint of C24—C25 bond (for ring E), as can be deduced from the torsion angles (Table 1).

The intramolecular C—H···O hydrogen bonds (Table 2, Fig. 1) result in the formation of three more five-membered rings F (O1/O2/C3/C4/H4A), G (C15/C16/C19/O4/H15A) and H (O3/C16/C19/C23/H23B), in which they may be effective in the stabilization of the structure.

As can be seen from the packing diagram (Fig. 2), the molecules of (I) are elongated along the c axis, and stacked along the a axis. Dipole-dipole and van der Waals interactions may be effective in the molecular packing.

Related literature top

For related literature, see: Mohr & Nickisch (2005); Kelly & Sykes (1968). For general background, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound, (I), was prepared by a literature method (Kelly & Sykes, 1968). The crystals were obtained by dissolving (I) (1.0 g, 2.5 mmol) in methanol (50 ml), and evaporating the solvent slowly at room temperature for about 15 d.

Refinement top

H atoms were positioned geometrically, with C—H = 0.93, 0.98, 0.96 and 0.97 Å for aromatic, methine, methyl and methylene H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 methyl H, and x = 1.2 for all other H atoms.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. A drawing of the title molecular structure, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Intramolecular hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. A packing diagram for (I). Intramolecular hydrogen bonds are shown as dashed lines.
3β-Acetoxy-17-ethylenedioxyandrost-5-ene top
Crystal data top
C23H34O4F000 = 816
Mr = 374.50Dx = 1.207 Mg m−3
Monoclinic, C2Mo Kα radiation
λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 25 reflections
a = 10.197 (2) Åθ = 9–12º
b = 7.5370 (15) ŵ = 0.08 mm−1
c = 27.143 (5) ÅT = 298 (2) K
β = 99.04 (3)ºBlock, colorless
V = 2060.2 (7) Å30.40 × 0.30 × 0.10 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.065
Radiation source: fine-focus sealed tubeθmax = 26.0º
Monochromator: graphiteθmin = 1.5º
T = 298(2) Kh = −12→12
ω/2θ scansk = 0→9
Absorption correction: ψ scan
(North et al., 1968)		l = 0→33
Tmin = 0.976, Tmax = 0.9903 standard reflections
2324 measured reflections every 120 min
2189 independent reflections intensity decay: none
1420 reflections with I > 2σ(I)
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.078H-atom parameters constrained
wR(F2) = 0.199  w = 1/[σ2(Fo2) + (0.06P)2 + 5P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.012
2189 reflectionsΔρmax = 0.48 e Å−3
227 parametersΔρmin = −0.33 e Å−3
62 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C23H34O4V = 2060.2 (7) Å3
Mr = 374.50Z = 4
Monoclinic, C2Mo Kα
a = 10.197 (2) ŵ = 0.08 mm−1
b = 7.5370 (15) ÅT = 298 (2) K
c = 27.143 (5) Å0.40 × 0.30 × 0.10 mm
β = 99.04 (3)º
Data collection top
Enraf–Nonius CAD-4
diffractometer		1420 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.065
Tmin = 0.976, Tmax = 0.9903 standard reflections
2324 measured reflections every 120 min
2189 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.078H-atom parameters constrained
wR(F2) = 0.199Δρmax = 0.48 e Å−3
S = 1.04Δρmin = −0.33 e Å−3
2189 reflectionsAbsolute structure: ?
227 parametersFlack parameter: ?
62 restraintsRogers parameter: ?
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
O1−0.1505 (5)−0.0998 (10)0.05652 (17)0.095 (2)
O2−0.3488 (7)−0.0028 (10)0.0652 (2)0.109
O30.3844 (5)0.0504 (10)0.44585 (17)0.0851 (18)
O40.1664 (4)0.1086 (8)0.42607 (16)0.0675 (14)
C2−0.3092 (10)−0.0908 (17)−0.0154 (3)0.108
H2A−0.2345−0.0601−0.03120.162*
H2B−0.3834−0.0169−0.02820.162*
H2C−0.3321−0.2129−0.02200.162*
C3−0.2745 (8)−0.0634 (13)0.0394 (3)0.078 (2)
C4−0.1026 (7)−0.0719 (15)0.1084 (2)0.078 (3)
H4A−0.1720−0.01560.12420.094*
C5−0.0628 (8)−0.2437 (12)0.1339 (2)0.069 (2)
H5A0.0052−0.29960.11790.083*
H5B−0.1389−0.32250.13040.083*
C6−0.0101 (7)−0.2169 (11)0.1891 (2)0.0611 (19)
H6A0.0189−0.33060.20360.073*
H6B−0.0822−0.17540.20550.073*
C70.1070 (6)−0.0832 (10)0.1997 (2)0.0470 (16)
C80.0725 (6)0.0808 (9)0.1667 (2)0.0465 (15)
C90.0181 (7)0.0490 (11)0.1131 (2)0.0637 (19)
H9A0.0859−0.00520.09660.076*
H9B−0.00670.16130.09680.076*
C100.1242 (5)−0.0273 (8)0.2554 (2)0.0393 (13)
H10A0.0351−0.00080.26270.047*
C110.2064 (6)0.1409 (9)0.2669 (2)0.0449 (15)
H11A0.29460.12200.25790.054*
C120.1398 (6)0.2947 (10)0.2366 (2)0.0528 (16)
H12A0.06660.33780.25210.063*
H12B0.20310.39070.23660.063*
C130.0893 (6)0.2431 (10)0.1843 (2)0.0538 (17)
H13A0.06710.33500.16160.065*
C140.1793 (7)−0.1834 (10)0.2906 (2)0.0566 (18)
H14A0.1186−0.28300.28480.068*
H14B0.2640−0.22110.28220.068*
C150.1978 (7)−0.1332 (10)0.3463 (2)0.0550 (17)
H15A0.1117−0.11100.35600.066*
H15B0.2387−0.23140.36610.066*
C160.2849 (6)0.0321 (9)0.3568 (2)0.0473 (15)
C170.2215 (5)0.1801 (8)0.3228 (2)0.0434 (14)
H17A0.13080.19180.33010.052*
C190.2886 (6)0.1226 (11)0.4089 (3)0.0588 (17)
C200.3178 (8)0.3188 (13)0.3994 (3)0.076 (2)
H20A0.40920.34640.41310.092*
H20B0.26020.39430.41540.092*
C210.2937 (7)0.3518 (11)0.3427 (3)0.0630 (19)
H21A0.23850.45550.33420.076*
H21B0.37670.36640.32990.076*
C220.2318 (6)−0.1720 (12)0.1853 (2)0.066 (2)
H22A0.2554−0.27310.20630.099*
H22B0.3039−0.08860.18940.099*
H22C0.2137−0.20940.15110.099*
C230.4290 (6)−0.0059 (12)0.3500 (3)0.068 (2)
H23A0.4298−0.06410.31860.102*
H23B0.4702−0.08100.37660.102*
H23C0.47710.10380.35060.102*
C240.1802 (8)−0.0145 (15)0.4659 (3)0.088 (3)
H24A0.1344−0.12440.45560.105*
H24B0.14450.03360.49420.105*
C250.3240 (9)−0.0442 (17)0.4786 (4)0.103
H25B0.3553−0.00510.51250.123*
H25A0.3440−0.16940.47630.123*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.080 (4)0.156 (6)0.043 (3)0.023 (4)−0.014 (2)−0.027 (4)
O20.1090.1090.1090.0000.0170.000
O30.056 (2)0.141 (5)0.052 (3)0.003 (3)−0.012 (2)0.003 (3)
O40.057 (2)0.104 (4)0.044 (2)0.006 (3)0.0146 (19)−0.004 (3)
C20.1080.1080.1080.0000.0170.000
C30.069 (4)0.100 (6)0.056 (4)0.010 (4)−0.020 (3)0.000 (4)
C40.063 (4)0.132 (8)0.037 (4)0.015 (5)0.000 (3)−0.015 (5)
C50.075 (5)0.087 (6)0.047 (4)−0.024 (5)0.012 (3)−0.026 (4)
C60.064 (4)0.067 (5)0.052 (4)−0.010 (4)0.009 (3)−0.018 (4)
C70.043 (3)0.069 (4)0.030 (3)0.003 (3)0.009 (2)0.002 (3)
C80.047 (3)0.058 (4)0.035 (3)0.000 (3)0.008 (2)−0.003 (3)
C90.074 (5)0.072 (5)0.045 (4)−0.003 (4)0.007 (3)−0.004 (4)
C100.038 (3)0.047 (3)0.035 (3)0.002 (3)0.009 (2)−0.004 (3)
C110.037 (3)0.066 (4)0.033 (3)0.001 (3)0.010 (2)−0.004 (3)
C120.054 (4)0.060 (4)0.045 (4)0.001 (3)0.011 (3)−0.001 (3)
C130.054 (4)0.066 (5)0.041 (4)0.006 (4)0.005 (3)0.011 (3)
C140.064 (4)0.058 (4)0.046 (4)−0.008 (4)0.004 (3)0.006 (3)
C150.062 (4)0.052 (4)0.051 (4)−0.004 (3)0.007 (3)0.010 (3)
C160.046 (3)0.057 (4)0.038 (3)0.001 (3)0.005 (3)−0.003 (3)
C170.033 (3)0.050 (4)0.047 (3)0.003 (3)0.008 (2)0.000 (3)
C190.045 (3)0.076 (5)0.056 (4)0.001 (3)0.007 (3)−0.003 (3)
C200.075 (5)0.094 (7)0.058 (4)−0.014 (5)0.002 (4)−0.027 (5)
C210.060 (4)0.065 (5)0.062 (4)−0.009 (4)0.005 (3)−0.007 (4)
C220.065 (4)0.090 (6)0.045 (4)0.022 (4)0.013 (3)−0.001 (4)
C230.044 (3)0.095 (6)0.065 (4)0.005 (4)0.011 (3)0.001 (4)
C240.080 (4)0.117 (6)0.067 (4)−0.015 (5)0.014 (4)0.008 (4)
C250.1030.1030.1030.0000.0160.000
Geometric parameters (Å, °) top
O1—C31.307 (8)C12—C131.483 (9)
O1—C41.432 (7)C12—H12A0.9700
O4—C191.402 (8)C12—H12B0.9700
O4—C241.414 (10)C13—H13A0.9300
O3—C251.361 (11)C14—C151.540 (8)
O3—C191.396 (8)C14—H14A0.9700
O2—C31.201 (10)C14—H14B0.9700
C2—C31.487 (11)C15—C161.530 (9)
C2—H2A0.9600C15—H15A0.9700
C2—H2B0.9600C15—H15B0.9700
C2—H2C0.9600C16—C171.526 (9)
C4—C51.494 (13)C16—C231.537 (8)
C4—C91.521 (11)C16—C191.564 (9)
C4—H4A0.9800C17—C211.544 (10)
C5—C61.523 (9)C17—H17A0.9800
C5—H5A0.9700C19—C201.538 (12)
C5—H5B0.9700C20—C211.539 (10)
C6—C71.555 (9)C20—H20A0.9700
C6—H6A0.9700C20—H20B0.9700
C6—H6B0.9700C21—H21A0.9700
C7—C81.535 (9)C21—H21B0.9700
C7—C221.542 (8)C22—H22A0.9600
C7—C101.552 (7)C22—H22B0.9600
C8—C131.314 (10)C22—H22C0.9600
C8—C91.494 (8)C23—H23A0.9600
C9—H9A0.9700C23—H23B0.9600
C9—H9B0.9700C23—H23C0.9600
C10—C111.525 (8)C24—C251.470 (11)
C10—C141.563 (9)C24—H24A0.9700
C10—H10A0.9800C24—H24B0.9700
C11—C121.519 (9)C25—H25B0.9700
C11—C171.528 (8)C25—H25A0.9700
C11—H11A0.9800
C3—O1—C4118.7 (6)C15—C14—C10113.0 (6)
C19—O4—C24108.5 (6)C15—C14—H14A109.0
C25—O3—C19109.7 (6)C10—C14—H14A109.0
C3—C2—H2A109.5C15—C14—H14B109.0
C3—C2—H2B109.5C10—C14—H14B109.0
H2A—C2—H2B109.5H14A—C14—H14B107.8
C3—C2—H2C109.5C16—C15—C14111.2 (5)
H2A—C2—H2C109.5C16—C15—H15A109.4
H2B—C2—H2C109.5C14—C15—H15A109.4
O2—C3—O1122.4 (7)C16—C15—H15B109.4
O2—C3—C2124.4 (8)C14—C15—H15B109.4
O1—C3—C2113.1 (8)H15A—C15—H15B108.0
O1—C4—C5110.7 (8)C15—C16—C17107.7 (5)
O1—C4—C9108.5 (7)C15—C16—C23111.3 (6)
C5—C4—C9108.9 (6)C17—C16—C23112.7 (5)
O1—C4—H4A109.6C15—C16—C19117.1 (5)
C5—C4—H4A109.6C17—C16—C19100.2 (5)
C9—C4—H4A109.6C23—C16—C19107.6 (5)
C4—C5—C6111.7 (7)C16—C17—C11115.3 (5)
C4—C5—H5A109.3C16—C17—C21105.5 (5)
C6—C5—H5A109.3C11—C17—C21118.6 (5)
C4—C5—H5B109.3C16—C17—H17A105.5
C6—C5—H5B109.3C11—C17—H17A105.5
H5A—C5—H5B108.0C21—C17—H17A105.5
C5—C6—C7114.3 (6)O3—C19—O4106.8 (6)
C5—C6—H6A108.7O3—C19—C20111.3 (7)
C7—C6—H6A108.7O4—C19—C20109.5 (6)
C5—C6—H6B108.7O3—C19—C16113.2 (6)
C7—C6—H6B108.7O4—C19—C16111.8 (5)
H6A—C6—H6B107.6C20—C19—C16104.2 (6)
C8—C7—C22108.9 (5)C19—C20—C21108.6 (6)
C8—C7—C10109.3 (5)C19—C20—H20A110.0
C22—C7—C10113.2 (5)C21—C20—H20A110.0
C8—C7—C6108.4 (5)C19—C20—H20B110.0
C22—C7—C6108.2 (6)C21—C20—H20B110.0
C10—C7—C6108.9 (5)H20A—C20—H20B108.4
C13—C8—C9120.7 (6)C17—C21—C20102.0 (6)
C13—C8—C7122.2 (5)C17—C21—H21A111.4
C9—C8—C7117.1 (6)C20—C21—H21A111.4
C8—C9—C4110.4 (5)C17—C21—H21B111.4
C8—C9—H9A109.6C20—C21—H21B111.4
C4—C9—H9A109.6H21A—C21—H21B109.2
C8—C9—H9B109.6C7—C22—H22A109.5
C4—C9—H9B109.6C7—C22—H22B109.5
H9A—C9—H9B108.1H22A—C22—H22B109.5
C11—C10—C7113.6 (5)C7—C22—H22C109.5
C11—C10—C14111.5 (4)H22A—C22—H22C109.5
C7—C10—C14111.4 (5)H22B—C22—H22C109.5
C11—C10—H10A106.6C16—C23—H23A109.5
C7—C10—H10A106.6C16—C23—H23B109.5
C14—C10—H10A106.6H23A—C23—H23B109.5
C12—C11—C10109.8 (5)C16—C23—H23C109.5
C12—C11—C17111.0 (5)H23A—C23—H23C109.5
C10—C11—C17109.3 (5)H23B—C23—H23C109.5
C12—C11—H11A108.9O4—C24—C25104.8 (7)
C10—C11—H11A108.9O4—C24—H24A110.8
C17—C11—H11A108.9C25—C24—H24A110.8
C13—C12—C11112.2 (6)O4—C24—H24B110.8
C13—C12—H12A109.2C25—C24—H24B110.8
C11—C12—H12A109.2H24A—C24—H24B108.9
C13—C12—H12B109.2O3—C25—C24107.7 (8)
C11—C12—H12B109.2O3—C25—H25B110.2
H12A—C12—H12B107.9C24—C25—H25B110.2
C8—C13—C12126.6 (6)O3—C25—H25A110.2
C8—C13—H13A116.7C24—C25—H25A110.2
C12—C13—H13A116.7H25B—C25—H25A108.5
C4—O1—C3—O22.1 (15)C14—C15—C16—C1755.8 (7)
C4—O1—C3—C2177.4 (10)C14—C15—C16—C23−68.2 (7)
C3—O1—C4—C5115.6 (9)C14—C15—C16—C19167.5 (6)
C3—O1—C4—C9−125.0 (9)C15—C16—C17—C11−59.4 (7)
O1—C4—C5—C6179.4 (5)C23—C16—C17—C1163.7 (7)
C9—C4—C5—C660.2 (8)C19—C16—C17—C11177.7 (5)
C4—C5—C6—C7−55.3 (9)C15—C16—C17—C21167.8 (5)
C5—C6—C7—C845.2 (8)C23—C16—C17—C21−69.1 (7)
C5—C6—C7—C22−72.6 (8)C19—C16—C17—C2144.9 (6)
C5—C6—C7—C10163.9 (6)C12—C11—C17—C16178.8 (5)
C22—C7—C8—C13−108.8 (7)C10—C11—C17—C1657.6 (6)
C10—C7—C8—C1315.3 (8)C12—C11—C17—C21−54.8 (7)
C6—C7—C8—C13133.7 (7)C10—C11—C17—C21−176.1 (5)
C22—C7—C8—C971.3 (7)C25—O3—C19—O414.6 (9)
C10—C7—C8—C9−164.6 (5)C25—O3—C19—C20134.1 (8)
C6—C7—C8—C9−46.1 (7)C25—O3—C19—C16−108.9 (8)
C13—C8—C9—C4−125.4 (8)C24—O4—C19—O3−16.4 (8)
C7—C8—C9—C454.4 (8)C24—O4—C19—C20−137.0 (7)
O1—C4—C9—C8−179.5 (6)C24—O4—C19—C16108.0 (7)
C5—C4—C9—C8−58.9 (8)C15—C16—C19—O387.0 (7)
C8—C7—C10—C11−44.8 (6)C17—C16—C19—O3−157.0 (6)
C22—C7—C10—C1176.7 (7)C23—C16—C19—O3−39.1 (8)
C6—C7—C10—C11−163.0 (5)C15—C16—C19—O4−33.7 (8)
C8—C7—C10—C14−171.8 (5)C17—C16—C19—O482.3 (7)
C22—C7—C10—C14−50.3 (7)C23—C16—C19—O4−159.9 (6)
C6—C7—C10—C1470.1 (7)C15—C16—C19—C20−151.9 (6)
C7—C10—C11—C1260.1 (6)C17—C16—C19—C20−35.9 (6)
C14—C10—C11—C12−172.9 (5)C23—C16—C19—C2082.0 (7)
C7—C10—C11—C17−177.9 (5)O3—C19—C20—C21137.3 (6)
C14—C10—C11—C17−51.0 (6)O4—C19—C20—C21−104.8 (6)
C10—C11—C12—C13−42.8 (7)C16—C19—C20—C2115.0 (8)
C17—C11—C12—C13−163.8 (5)C16—C17—C21—C20−35.8 (7)
C9—C8—C13—C12178.9 (6)C11—C17—C21—C20−166.7 (6)
C7—C8—C13—C12−0.9 (10)C19—C20—C21—C1712.0 (8)
C11—C12—C13—C815.1 (10)C19—O4—C24—C2511.9 (9)
C11—C10—C14—C1551.9 (7)C19—O3—C25—C24−7.1 (11)
C7—C10—C14—C15180.0 (5)O4—C24—C25—O3−3.0 (11)
C10—C14—C15—C16−54.5 (7)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O20.982.222.650 (10)105
C15—H15A···O40.972.522.886 (8)102
C23—H23B···O30.962.412.744 (9)100
Table 1
Selected geometric parameters (°) top
O3—C19—O4106.8 (6)O4—C19—C16111.8 (5)
O3—C19—C20111.3 (7)O4—C24—C25104.8 (7)
O4—C19—C20109.5 (6)O3—C25—C24107.7 (8)
O3—C19—C16113.2 (6)
C19—C16—C17—C2144.9 (6)C16—C17—C21—C20−35.8 (7)
C25—O3—C19—O414.6 (9)C19—C20—C21—C1712.0 (8)
C24—O4—C19—O3−16.4 (8)C19—O4—C24—C2511.9 (9)
C17—C16—C19—C20−35.9 (6)C19—O3—C25—C24−7.1 (11)
C16—C19—C20—C2115.0 (8)O4—C24—C25—O3−3.0 (11)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O20.982.222.650 (10)105
C15—H15A···O40.972.522.886 (8)102
C23—H23B···O30.962.412.744 (9)100
Acknowledgements top

The authors thank the Modern Analysis Center of Nanjing University for support.

references
References top

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Bruker (2000). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.

Enraf–Nonius (1985). CAD-4 Software. Version 5.0. Enraf–Nonius, Delft, The Netherlands.

Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.

Kelly, R. W. & Sykes, P. J. (1968). J. Chem. Soc. C. Org. 4, 416–421.

Mohr, J. T. & Nickisch, K. (2005). US Patent No. 6 933 395.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.