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Acta Cryst. (2007). E63, o3924    [ doi:10.1107/S160053680704175X ]

9-(1,3-Benzodioxol-5-yl)-10-(4-chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione

Q. Liu, Z. Tang and X. Du

Abstract top

The title compound, C30H30ClNO4, was synthesized by the reaction of dimedone with 1,3-benzodioxole-5-carbaldehyde and 4-chlorobenzenamine in water. The dihydropyridine ring adopts a boat conformation, while the two cyclohexenone rings have envelope conformations.

Comment top

Many of the natural and synthetic compounds containing the acridine skeleton display interesting biological and physical activities, such as antimalaria (Wysocka-Skrzela & Ledochowski, 1976; Reil et al., 1994; Mandi et al., 1994; Thull & Testa, 1994) and antitumor agents (Khurana et al., 1990), and multi- hydroacridineone derivatives have been reported to have high fluorescence efficiency and can be used as fluorescent molecular probes for monitoring of polymerization process (Popielarz et al., 1997). They are also increasingly receiving attention, due to their likeness in properties with those of 1,4-dihydropyridines, which have similarities in structure to the biologically important compounds such as NADH and NADPH (Srividya et al., 1996). As a consequence, the interest of organic chemists in the synthesis or structure modifications of acridinedione derivatives remains high (Tu et al., 2004; 2006). We report herein the structure of the title compound, (I).

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

Rings A (C1—C6), B (N1/C1/C6—C8/C13) and C (C8—C13) are not planar, having total puckering amplitudes, QT, of 0.490 (3), 0.226 (2) and 0.486 (2) Å, respectively. Ring B adopts boat conformation [φ = -2.14 (3)° and θ = 104.81 (3)°] (Cremer & Pople, 1975). Rings A and C have envelope conformations with atoms C3 and C11 displaced by 0.678 (2) Å and 0.668 (2) Å from the planes of the other ring atoms, respectively. Rings D (C14—C19), E (C24—C29) and F (O3/O4/C26/C27/C30) are, of course, planar and rings E and F are also coplanar with a dihedral angle of 0.76 (2)° and ring D is oriented with respect to the coplanar rings system at a dihedral angle of 11.06 (3)°.

In the crystal structure, the molecules are elongated along the c axis (Fig. 2).

Related literature top

For related literature, see: Wysocka-Skrzela & Ledochowski (1976); Reil et al. (1994); Mandi et al. (1994); Thull & Testa (1994); Khurana et al. (1990); Popielarz et al. (1997); Srividya et al. (1996); Tu et al. (2004, 2006). For general background, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the reaction of dimedone (280 mg, 2 mmol) with 1,3-benzodioxole-5-carbaldehyde (150 mg, 1 mmol) and 4-chlorobenzen- amine (130 mg, 1 mmol) at 413 K under microwave irradiation (maximum power 150 W, initial power 100 W) for 10 min. Single crystals suitable for X-ray diffraction were obtained from an ethanol solution by slow evaporation (yield; 440 mg, 86%; m.p. 560–561 K).

Refinement top

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

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram for (I). Hydrogen atoms are omitted for clarity.
9-(1,3-Benzodioxol-5-yl)-10-(4-chlorophenyl)-3,3,6,6-tetramethyl-\ 3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione top
Crystal data top
C30H30ClNO4F000 = 1064
Mr = 504.00Dx = 1.278 Mg m−3
Monoclinic, P21/cMelting point = 560–561 K
Hall symbol: -P 2ybcMo Kα radiation
λ = 0.71073 Å
a = 12.339 (2) ÅCell parameters from 2146 reflections
b = 10.991 (2) Åθ = 2.4–27.8º
c = 19.753 (3) ŵ = 0.18 mm−1
β = 102.054 (2)ºT = 298 (2) K
V = 2619.8 (8) Å3Block, pale yellow
Z = 40.21 × 0.18 × 0.15 mm
Data collection top
Bruker CCD area-detector
diffractometer		4537 independent reflections
Radiation source: fine-focus sealed tube2041 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.061
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.7º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→14
Tmin = 0.963, Tmax = 0.973k = −13→12
10447 measured reflectionsl = −20→23
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)] = 0.069H-atom parameters constrained
wR(F2) = 0.200  w = 1/[σ2(Fo2) + (0.078P)2 + 0.7779P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4537 reflectionsΔρmax = 0.32 e Å−3
325 parametersΔρmin = −0.37 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C30H30ClNO4V = 2619.8 (8) Å3
Mr = 504.00Z = 4
Monoclinic, P21/cMo Kα
a = 12.339 (2) ŵ = 0.18 mm−1
b = 10.991 (2) ÅT = 298 (2) K
c = 19.753 (3) Å0.21 × 0.18 × 0.15 mm
β = 102.054 (2)º
Data collection top
Bruker CCD area-detector
diffractometer		4537 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2041 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.973Rint = 0.061
10447 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.069325 parameters
wR(F2) = 0.200H-atom parameters constrained
S = 1.04Δρmax = 0.32 e Å−3
4537 reflectionsΔρmin = −0.37 e Å−3
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
Cl10.63239 (16)1.52738 (15)0.23984 (8)0.0964 (7)
N10.7985 (3)1.0541 (3)0.36537 (18)0.0380 (9)
O10.9268 (3)0.8116 (3)0.56215 (17)0.0621 (10)
O20.9340 (3)0.6660 (3)0.32234 (18)0.0641 (11)
O30.6752 (3)0.4195 (3)0.4549 (2)0.0705 (11)
O40.4981 (3)0.4951 (3)0.41699 (19)0.0687 (11)
C10.8183 (4)1.0340 (4)0.4368 (2)0.0373 (11)
C20.8007 (4)1.1398 (4)0.4815 (2)0.0465 (13)
H2A0.74051.18960.45660.056*
H2B0.86711.18950.49090.056*
C30.7732 (4)1.0995 (4)0.5509 (2)0.0445 (12)
C40.8625 (4)1.0098 (4)0.5835 (2)0.0542 (14)
H4A0.93131.05410.59850.065*
H4B0.84230.97560.62440.065*
C50.8830 (4)0.9069 (4)0.5377 (2)0.0422 (12)
C60.8509 (4)0.9237 (4)0.4620 (2)0.0367 (11)
C70.8551 (4)0.8137 (4)0.4177 (2)0.0395 (12)
H70.92260.76810.43720.047*
C80.8617 (4)0.8552 (4)0.3454 (2)0.0352 (11)
C90.9045 (4)0.7688 (4)0.3016 (2)0.0428 (12)
C100.9162 (4)0.8107 (4)0.2313 (2)0.0509 (14)
H10A0.91430.74040.20140.061*
H10B0.98780.84960.23520.061*
C110.8254 (4)0.8998 (4)0.1980 (2)0.0488 (13)
C120.8287 (4)1.0068 (4)0.2482 (2)0.0493 (13)
H12A0.89431.05520.24780.059*
H12B0.76451.05800.23230.059*
C130.8302 (4)0.9670 (4)0.3218 (2)0.0366 (11)
C140.7585 (4)1.1721 (4)0.3375 (2)0.0451 (13)
C150.6474 (4)1.1843 (5)0.3061 (3)0.0553 (14)
H150.59851.11960.30530.066*
C160.6102 (5)1.2960 (6)0.2757 (3)0.0606 (15)
H160.53641.30490.25350.073*
C170.6813 (5)1.3918 (5)0.2784 (2)0.0482 (13)
C180.7907 (5)1.3809 (4)0.3102 (3)0.0512 (14)
H180.83861.44670.31200.061*
C190.8288 (4)1.2708 (4)0.3395 (2)0.0485 (13)
H190.90311.26280.36090.058*
C200.7766 (4)1.2110 (5)0.5983 (2)0.0627 (16)
H20A0.72441.27070.57590.094*
H20B0.84981.24520.60760.094*
H20C0.75771.18660.64110.094*
C210.6601 (4)1.0405 (5)0.5397 (3)0.0646 (16)
H21A0.65840.97070.51030.097*
H21B0.60471.09770.51820.097*
H21C0.64531.01560.58350.097*
C220.7141 (5)0.8362 (5)0.1861 (3)0.0776 (18)
H22A0.65600.89490.17250.116*
H22B0.70550.79700.22810.116*
H22C0.71020.77650.15020.116*
C230.8478 (5)0.9489 (5)0.1293 (3)0.0778 (19)
H23A0.91850.98900.13760.117*
H23B0.79081.00580.10970.117*
H23C0.84810.88260.09770.117*
C240.7569 (4)0.7316 (4)0.4168 (2)0.0367 (11)
C250.7729 (4)0.6100 (4)0.4390 (2)0.0412 (12)
H250.84350.57830.45480.049*
C260.6803 (5)0.5407 (4)0.4362 (2)0.0456 (13)
C270.5756 (4)0.5854 (5)0.4145 (2)0.0469 (13)
C280.5562 (4)0.7023 (5)0.3925 (2)0.0526 (14)
H280.48490.73250.37720.063*
C290.6500 (4)0.7736 (4)0.3946 (2)0.0494 (13)
H290.64010.85410.38020.059*
C300.5615 (5)0.3901 (5)0.4419 (3)0.0703 (17)
H30A0.54160.36170.48420.084*
H30B0.54590.32540.40790.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1397 (16)0.0704 (11)0.0800 (12)0.0544 (11)0.0247 (11)0.0268 (9)
N10.054 (3)0.026 (2)0.036 (2)0.0083 (19)0.0150 (19)0.0030 (17)
O10.073 (3)0.052 (2)0.057 (2)0.006 (2)0.006 (2)0.0148 (18)
O20.074 (3)0.046 (2)0.074 (3)0.025 (2)0.019 (2)0.0100 (19)
O30.082 (3)0.035 (2)0.097 (3)−0.012 (2)0.026 (2)0.015 (2)
O40.065 (3)0.062 (3)0.081 (3)−0.024 (2)0.017 (2)−0.003 (2)
C10.033 (3)0.035 (3)0.045 (3)−0.002 (2)0.009 (2)0.005 (2)
C20.059 (3)0.036 (3)0.048 (3)−0.001 (2)0.020 (3)−0.001 (2)
C30.054 (3)0.042 (3)0.042 (3)−0.001 (3)0.019 (3)−0.003 (2)
C40.066 (4)0.051 (3)0.048 (3)−0.010 (3)0.016 (3)0.002 (3)
C50.034 (3)0.040 (3)0.050 (3)−0.005 (2)0.004 (2)0.011 (2)
C60.037 (3)0.036 (3)0.037 (3)−0.002 (2)0.008 (2)0.003 (2)
C70.041 (3)0.030 (3)0.050 (3)0.003 (2)0.016 (2)0.007 (2)
C80.035 (3)0.030 (3)0.042 (3)−0.001 (2)0.012 (2)−0.002 (2)
C90.038 (3)0.039 (3)0.053 (3)0.003 (2)0.014 (2)−0.001 (2)
C100.068 (4)0.041 (3)0.050 (3)0.009 (3)0.024 (3)−0.002 (2)
C110.072 (4)0.030 (3)0.046 (3)0.005 (3)0.018 (3)−0.003 (2)
C120.073 (4)0.035 (3)0.045 (3)−0.003 (3)0.025 (3)0.000 (2)
C130.040 (3)0.027 (3)0.047 (3)−0.002 (2)0.017 (2)0.001 (2)
C140.054 (4)0.032 (3)0.053 (3)0.002 (3)0.020 (3)−0.002 (2)
C150.047 (4)0.050 (3)0.070 (4)0.000 (3)0.014 (3)−0.007 (3)
C160.058 (4)0.073 (4)0.047 (3)0.028 (3)0.003 (3)−0.001 (3)
C170.063 (4)0.040 (3)0.044 (3)0.021 (3)0.017 (3)0.005 (2)
C180.063 (4)0.036 (3)0.060 (3)0.007 (3)0.025 (3)0.009 (3)
C190.049 (3)0.041 (3)0.056 (3)0.002 (3)0.013 (3)0.004 (3)
C200.083 (4)0.056 (4)0.053 (3)0.002 (3)0.021 (3)−0.007 (3)
C210.056 (4)0.079 (4)0.065 (4)−0.001 (3)0.026 (3)−0.002 (3)
C220.082 (5)0.063 (4)0.076 (4)0.003 (4)−0.012 (4)0.007 (3)
C230.148 (6)0.047 (3)0.045 (3)0.004 (4)0.035 (4)−0.006 (3)
C240.040 (3)0.033 (3)0.038 (3)0.002 (2)0.009 (2)0.008 (2)
C250.041 (3)0.034 (3)0.047 (3)0.001 (2)0.007 (2)0.003 (2)
C260.065 (4)0.030 (3)0.045 (3)−0.001 (3)0.020 (3)0.003 (2)
C270.053 (4)0.041 (3)0.050 (3)−0.014 (3)0.019 (3)−0.006 (2)
C280.040 (3)0.057 (4)0.061 (3)0.002 (3)0.011 (3)0.010 (3)
C290.051 (3)0.042 (3)0.055 (3)0.005 (3)0.011 (3)0.017 (2)
C300.089 (5)0.046 (4)0.088 (4)−0.016 (4)0.047 (4)−0.006 (3)
Geometric parameters (Å, °) top
Cl1—C171.725 (5)C12—H12A0.9700
N1—C131.397 (5)C12—H12B0.9700
N1—C11.399 (5)C14—C191.385 (6)
N1—C141.455 (5)C14—C151.388 (6)
O1—C51.231 (5)C15—C161.400 (7)
O2—C91.231 (5)C15—H150.9300
O3—C261.387 (5)C16—C171.364 (7)
O3—C301.410 (6)C16—H160.9300
O4—C271.386 (5)C17—C181.369 (7)
O4—C301.424 (6)C18—C191.380 (6)
C1—C61.339 (6)C18—H180.9300
C1—C21.504 (6)C19—H190.9300
C2—C31.543 (6)C20—H20A0.9600
C2—H2A0.9700C20—H20B0.9600
C2—H2B0.9700C20—H20C0.9600
C3—C211.513 (6)C21—H21A0.9600
C3—C41.518 (6)C21—H21B0.9600
C3—C201.538 (6)C21—H21C0.9600
C4—C51.502 (6)C22—H22A0.9600
C4—H4A0.9700C22—H22B0.9600
C4—H4B0.9700C22—H22C0.9600
C5—C61.477 (6)C23—H23A0.9600
C6—C71.499 (6)C23—H23B0.9600
C7—C241.508 (6)C23—H23C0.9600
C7—C81.518 (6)C24—C291.379 (6)
C7—H70.9800C24—C251.407 (6)
C8—C131.343 (6)C25—C261.365 (6)
C8—C91.455 (6)C25—H250.9300
C9—C101.498 (6)C26—C271.365 (6)
C10—C111.530 (6)C27—C281.362 (6)
C10—H10A0.9700C28—C291.392 (6)
C10—H10B0.9700C28—H280.9300
C11—C221.514 (7)C29—H290.9300
C11—C121.534 (6)C30—H30A0.9700
C11—C231.539 (6)C30—H30B0.9700
C12—C131.514 (6)
C13—N1—C1120.1 (4)C19—C14—N1121.8 (5)
C13—N1—C14119.7 (4)C15—C14—N1118.7 (4)
C1—N1—C14119.8 (4)C14—C15—C16118.7 (5)
C26—O3—C30105.7 (4)C14—C15—H15120.7
C27—O4—C30105.1 (4)C16—C15—H15120.7
C6—C1—N1119.5 (4)C17—C16—C15120.6 (5)
C6—C1—C2123.5 (4)C17—C16—H16119.7
N1—C1—C2117.0 (4)C15—C16—H16119.7
C1—C2—C3112.6 (4)C16—C17—C18121.0 (5)
C1—C2—H2A109.1C16—C17—Cl1119.1 (5)
C3—C2—H2A109.1C18—C17—Cl1119.9 (4)
C1—C2—H2B109.1C17—C18—C19119.1 (5)
C3—C2—H2B109.1C17—C18—H18120.5
H2A—C2—H2B107.8C19—C18—H18120.5
C21—C3—C4110.5 (4)C18—C19—C14121.2 (5)
C21—C3—C20109.7 (4)C18—C19—H19119.4
C4—C3—C20109.5 (4)C14—C19—H19119.4
C21—C3—C2111.1 (4)C3—C20—H20A109.5
C4—C3—C2106.8 (4)C3—C20—H20B109.5
C20—C3—C2109.2 (4)H20A—C20—H20B109.5
C5—C4—C3115.6 (4)C3—C20—H20C109.5
C5—C4—H4A108.4H20A—C20—H20C109.5
C3—C4—H4A108.4H20B—C20—H20C109.5
C5—C4—H4B108.4C3—C21—H21A109.5
C3—C4—H4B108.4C3—C21—H21B109.5
H4A—C4—H4B107.4H21A—C21—H21B109.5
O1—C5—C6120.4 (4)C3—C21—H21C109.5
O1—C5—C4121.3 (4)H21A—C21—H21C109.5
C6—C5—C4118.2 (4)H21B—C21—H21C109.5
C1—C6—C5119.0 (4)C11—C22—H22A109.5
C1—C6—C7123.9 (4)C11—C22—H22B109.5
C5—C6—C7117.1 (4)H22A—C22—H22B109.5
C6—C7—C24111.4 (4)C11—C22—H22C109.5
C6—C7—C8108.8 (3)H22A—C22—H22C109.5
C24—C7—C8111.7 (4)H22B—C22—H22C109.5
C6—C7—H7108.3C11—C23—H23A109.5
C24—C7—H7108.3C11—C23—H23B109.5
C8—C7—H7108.3H23A—C23—H23B109.5
C13—C8—C9120.3 (4)C11—C23—H23C109.5
C13—C8—C7122.2 (4)H23A—C23—H23C109.5
C9—C8—C7117.5 (4)H23B—C23—H23C109.5
O2—C9—C8121.3 (4)C29—C24—C25118.7 (4)
O2—C9—C10120.8 (4)C29—C24—C7121.0 (4)
C8—C9—C10117.9 (4)C25—C24—C7120.3 (4)
C9—C10—C11113.0 (4)C26—C25—C24117.1 (4)
C9—C10—H10A109.0C26—C25—H25121.4
C11—C10—H10A109.0C24—C25—H25121.4
C9—C10—H10B109.0C25—C26—C27122.7 (4)
C11—C10—H10B109.0C25—C26—O3127.6 (5)
H10A—C10—H10B107.8C27—C26—O3109.7 (5)
C22—C11—C10109.3 (4)C28—C27—C26122.2 (5)
C22—C11—C12110.8 (4)C28—C27—O4127.6 (5)
C10—C11—C12107.1 (4)C26—C27—O4110.2 (4)
C22—C11—C23110.4 (5)C27—C28—C29115.6 (5)
C10—C11—C23110.7 (4)C27—C28—H28122.2
C12—C11—C23108.4 (4)C29—C28—H28122.2
C13—C12—C11113.1 (4)C24—C29—C28123.7 (5)
C13—C12—H12A109.0C24—C29—H29118.2
C11—C12—H12A109.0C28—C29—H29118.2
C13—C12—H12B109.0O3—C30—O4109.3 (4)
C11—C12—H12B109.0O3—C30—H30A109.8
H12A—C12—H12B107.8O4—C30—H30A109.8
C8—C13—N1120.8 (4)O3—C30—H30B109.8
C8—C13—C12122.8 (4)O4—C30—H30B109.8
N1—C13—C12116.4 (4)H30A—C30—H30B108.3
C19—C14—C15119.5 (5)
C13—N1—C1—C6−10.8 (6)C7—C8—C13—C12−175.6 (4)
C14—N1—C1—C6177.3 (4)C1—N1—C13—C811.7 (6)
C13—N1—C1—C2169.5 (4)C14—N1—C13—C8−176.4 (4)
C14—N1—C1—C2−2.4 (6)C1—N1—C13—C12−167.2 (4)
C6—C1—C2—C3−25.2 (6)C14—N1—C13—C124.7 (6)
N1—C1—C2—C3154.4 (4)C11—C12—C13—C820.6 (7)
C1—C2—C3—C21−68.6 (5)C11—C12—C13—N1−160.5 (4)
C1—C2—C3—C451.9 (5)C13—N1—C14—C19−93.0 (5)
C1—C2—C3—C20170.2 (4)C1—N1—C14—C1978.9 (5)
C21—C3—C4—C569.5 (5)C13—N1—C14—C1584.7 (5)
C20—C3—C4—C5−169.5 (4)C1—N1—C14—C15−103.3 (5)
C2—C3—C4—C5−51.4 (5)C19—C14—C15—C161.5 (7)
C3—C4—C5—O1−158.2 (4)N1—C14—C15—C16−176.3 (4)
C3—C4—C5—C622.8 (6)C14—C15—C16—C17−1.6 (7)
N1—C1—C6—C5173.5 (4)C15—C16—C17—C180.7 (8)
C2—C1—C6—C5−6.8 (7)C15—C16—C17—Cl1179.6 (4)
N1—C1—C6—C7−7.6 (7)C16—C17—C18—C190.3 (7)
C2—C1—C6—C7172.0 (4)Cl1—C17—C18—C19−178.6 (4)
O1—C5—C6—C1−170.5 (4)C17—C18—C19—C14−0.3 (7)
C4—C5—C6—C18.5 (6)C15—C14—C19—C18−0.6 (7)
O1—C5—C6—C710.6 (6)N1—C14—C19—C18177.2 (4)
C4—C5—C6—C7−170.4 (4)C6—C7—C24—C2958.3 (6)
C1—C6—C7—C24−101.7 (5)C8—C7—C24—C29−63.6 (5)
C5—C6—C7—C2477.2 (5)C6—C7—C24—C25−121.5 (4)
C1—C6—C7—C821.9 (6)C8—C7—C24—C25116.6 (4)
C5—C6—C7—C8−159.2 (4)C29—C24—C25—C260.7 (6)
C6—C7—C8—C13−20.6 (6)C7—C24—C25—C26−179.5 (4)
C24—C7—C8—C13102.7 (5)C24—C25—C26—C27−1.3 (7)
C6—C7—C8—C9159.1 (4)C24—C25—C26—O3179.7 (4)
C24—C7—C8—C9−77.5 (5)C30—O3—C26—C25−179.5 (5)
C13—C8—C9—O2179.8 (5)C30—O3—C26—C271.4 (5)
C7—C8—C9—O20.1 (7)C25—C26—C27—C281.4 (8)
C13—C8—C9—C102.5 (7)O3—C26—C27—C28−179.5 (4)
C7—C8—C9—C10−177.3 (4)C25—C26—C27—O4179.9 (4)
O2—C9—C10—C11147.9 (5)O3—C26—C27—O4−0.9 (5)
C8—C9—C10—C11−34.7 (6)C30—O4—C27—C28178.5 (5)
C9—C10—C11—C22−63.5 (5)C30—O4—C27—C260.0 (5)
C9—C10—C11—C1256.6 (5)C26—C27—C28—C29−0.8 (7)
C9—C10—C11—C23174.6 (4)O4—C27—C28—C29−179.1 (4)
C22—C11—C12—C1369.9 (5)C25—C24—C29—C28−0.2 (7)
C10—C11—C12—C13−49.2 (5)C7—C24—C29—C28180.0 (4)
C23—C11—C12—C13−168.7 (4)C27—C28—C29—C240.2 (7)
C9—C8—C13—N1−174.2 (4)C26—O3—C30—O4−1.4 (6)
C7—C8—C13—N15.6 (7)C27—O4—C30—O30.9 (5)
C9—C8—C13—C124.7 (7)
Acknowledgements top

The authors thank the Nature Science Foundation of China (grant No. 20672090) and the Nature Science Foundation of Jiangsu Province (grant No. BK2006033).

references
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