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Acta Cryst. (2012). E68, o2045    [ doi:10.1107/S160053681202572X ]

9-[(2-Methoxybenzyl)amino]-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one

S. Shi, D. Tian, G. Luo, T. Ai and H. Chen

Abstract top

In the title compound, C30H31NO8, the tetrahydrofuran ring and the six-membered ring fused to it both display envelope conformations, both having the same C atom as the flap. The dihedral angles between the benzene ring of the benzo[d][1,3]dioxole ring system and the other two benzene rings are 53.73 (3) and 83.30 (2)°. An intramolecular N-H...O hydrogen bond is present. In the crystal, weak intermolecular C-H...O hydrogen bonds link the molecules into chains parallel to the c axis.

Comment top

Podophyllotoxin is well known for its antitumor activity. Based on the structure-activity relationships of podophyllotoxins and in order to find compounds with superior bioactivity and overcoming multidrug resistance, in continuation of our structural study of new derivatives of podophyllotoxin (Luo et al., 2011; Li et al., 2011), we report here the crystal structure of title compound.

In title compound (Fig. 1), bond lengths and angles are normal and in good agreement with those reported previously for related compounds (Luo et al., 2011; Li et al., 2011). The tetrahydrofuran ring (C18—C21/O4) and the six-membered ring (C9—C10/C16—C18/C21) fused to it both display envelope conformations, with atom C21 displaced by 0.590 (4) and 0.614 (4) Å from the mean planes through O4/C18–C20 and C9/C10/C16–C18, respectively. The dihedral angles between the benzene ring (C10—C16) of the benzo[d]-[1,3]dioxole ring system and the other two benzene rings (C2—C7 and C22—C27) are 53.73 (3) and 83.30 (2) °, respectively. The molecular conformation is enforced by an intramolecular N—H···O hydrogen bond (Table 1). There are weaker C—H···O intermolecular interactions, linking molecules into chains parallel to [0 0 1].

Related literature top

For the crystal structures of related podophyllotoxin derivatives, see: Luo et al. (2011); Li et al. (2011).

Experimental top

4β-Aminopodophyllotoxin (1.0 mmol), 2-methoxybenaldehyde (1.0 mmol) and ethylic acid (0.01 mmol) were dissolved in 95% ethanol. The mixture was stirred at room temperature for 6 h. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (1:1 v/v) as eluent. Then the obtained compound (1 mmol) and NaBH4 (4 mmol) were dissolved in dry methanol. The mixture was stirred at 0°C for 3 h. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (1:1 v/v) as eluent. Single crystals suitable for X-ray diffraction were prepared by evaporation of the solution at room temperature.

Refinement top

The amine H atom was located in a difference Fourier map and refined isotropically with the N—H distance constrained to be 0.91 (1) Å. All other H atoms were found on difference maps, and included in the final cycles of refinement using a riding model, with C—H = 0.93–0.98 Å and with Uiso(H) = 1.2Ueq(C) for aryl and methylene H atoms and 1.5Ueq(C) for the methyl H atoms. In the absence of significant anomalous scatterers in the molecule, 877 Friedel pairs were merged before the final 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the title compound, with displacement ellipsoids drawn at the 30% probability level.
9-[(2-Methoxybenzyl)amino]-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9- tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one top
Crystal data top
C30H31NO8F(000) = 1128
Mr = 533.56Dx = 1.349 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6120 reflections
a = 9.6203 (19) Åθ = 2.5–28.0°
b = 12.870 (3) ŵ = 0.10 mm−1
c = 21.227 (4) ÅT = 293 K
V = 2628.1 (9) Å3Prism, colorless
Z = 40.30 × 0.20 × 0.10 mm
Data collection top
Rigaku Saturn
diffractometer		2641 independent reflections
Radiation source: rotating anode1618 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.088
ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2007)		h = −11→11
Tmin = 0.971, Tmax = 0.990k = −15→15
22214 measured reflectionsl = −25→25
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)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0574P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max < 0.001
2641 reflectionsΔρmax = 0.23 e Å−3
361 parametersΔρmin = −0.26 e Å−3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0157 (16)
Crystal data top
C30H31NO8V = 2628.1 (9) Å3
Mr = 533.56Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 9.6203 (19) ŵ = 0.10 mm−1
b = 12.870 (3) ÅT = 293 K
c = 21.227 (4) Å0.30 × 0.20 × 0.10 mm
Data collection top
Rigaku Saturn
diffractometer		1618 reflections with I > 2σ(I)
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2007)		Rint = 0.088
Tmin = 0.971, Tmax = 0.990θmax = 25.0°
22214 measured reflectionsStandard reflections: 0
2641 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114Δρmax = 0.23 e Å−3
S = 0.89Δρmin = −0.26 e Å−3
2641 reflectionsAbsolute structure: ?
361 parametersFlack parameter: ?
1 restraintRogers 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
O11.3087 (4)0.1036 (3)0.80717 (14)0.0614 (9)
O20.8443 (3)0.0045 (3)0.74461 (14)0.0665 (10)
O30.6445 (3)0.0879 (3)0.77780 (14)0.0571 (9)
O41.0753 (4)0.0957 (3)1.12178 (13)0.0585 (9)
O50.8792 (4)0.1874 (3)1.13695 (14)0.0635 (10)
O60.5983 (3)−0.2184 (2)1.02072 (14)0.0537 (8)
O70.4290 (3)−0.1483 (2)1.11232 (14)0.0531 (8)
O80.4348 (3)0.0507 (2)1.14883 (12)0.0443 (8)
N11.1935 (4)0.1096 (3)0.93580 (16)0.0435 (9)
C11.3003 (7)0.1341 (5)0.7425 (2)0.0874 (19)
H1A1.38670.11900.72190.131*
H1B1.28190.20730.74000.131*
H1C1.22660.09650.72230.131*
C21.3413 (4)0.0025 (4)0.8201 (2)0.0456 (11)
C31.3595 (5)−0.0736 (4)0.7748 (2)0.0631 (14)
H31.3507−0.05770.73230.076*
C41.3908 (6)−0.1730 (5)0.7937 (3)0.0794 (18)
H41.4017−0.22480.76350.095*
C51.4062 (6)−0.1971 (4)0.8552 (3)0.0763 (17)
H51.4290−0.26440.86740.092*
C61.3874 (5)−0.1201 (4)0.8997 (2)0.0609 (14)
H61.3970−0.13690.94210.073*
C71.3549 (4)−0.0195 (3)0.8835 (2)0.0433 (11)
C81.3346 (4)0.0647 (4)0.93241 (19)0.0481 (12)
H8A1.35780.03620.97340.058*
H8B1.39990.12030.92370.058*
C91.0832 (4)0.0336 (3)0.94942 (18)0.0382 (10)
H91.1187−0.03630.94070.046*
C100.9577 (4)0.0532 (3)0.90818 (17)0.0332 (9)
C110.9684 (4)0.0190 (3)0.84537 (18)0.0425 (11)
H111.0492−0.01230.83060.051*
C120.8573 (4)0.0331 (4)0.80700 (19)0.0457 (11)
C130.7038 (5)0.0262 (5)0.7288 (2)0.0695 (16)
H13A0.6522−0.03810.72430.083*
H13B0.69960.06340.68910.083*
C140.7386 (4)0.0824 (3)0.82683 (19)0.0397 (10)
C150.7246 (4)0.1178 (3)0.88648 (18)0.0389 (10)
H150.64390.15150.89930.047*
C160.8360 (4)0.1020 (3)0.92869 (17)0.0333 (9)
C170.8108 (4)0.1312 (3)0.99722 (17)0.0373 (10)
H170.77010.20100.99840.045*
C180.9513 (4)0.1347 (3)1.03028 (17)0.0382 (10)
H181.00160.19441.01290.046*
C190.9569 (5)0.1447 (3)1.1010 (2)0.0493 (12)
C201.1526 (5)0.0526 (4)1.06892 (19)0.0508 (12)
H20A1.1940−0.01371.07980.061*
H20B1.22500.09981.05510.061*
C211.0407 (4)0.0397 (3)1.01841 (17)0.0380 (10)
H210.9859−0.02221.02850.046*
C220.7088 (4)0.0558 (3)1.02781 (18)0.0376 (10)
C230.7037 (4)−0.0481 (3)1.00894 (19)0.0425 (10)
H230.7621−0.07180.97710.051*
C240.6120 (5)−0.1156 (3)1.03751 (19)0.0415 (11)
C250.5238 (4)−0.0815 (3)1.08588 (18)0.0395 (10)
C260.5260 (4)0.0226 (3)1.10325 (18)0.0380 (10)
C270.6187 (4)0.0907 (3)1.07381 (18)0.0408 (10)
H270.61970.16041.08540.049*
C280.6889 (5)−0.2543 (3)0.9721 (2)0.0652 (15)
H28A0.6730−0.21460.93440.098*
H28B0.6709−0.32640.96380.098*
H28C0.7837−0.24590.98520.098*
C290.4876 (6)−0.2235 (4)1.1542 (3)0.0791 (18)
H29A0.5529−0.26591.13160.119*
H29B0.4149−0.26651.17090.119*
H29C0.5343−0.18861.18810.119*
C300.4447 (5)0.1544 (4)1.1727 (2)0.0624 (14)
H30A0.53740.16681.18770.094*
H30B0.38000.16321.20680.094*
H30C0.42330.20291.13970.094*
H11.181 (4)0.134 (3)0.8961 (8)0.034 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.074 (2)0.065 (2)0.0459 (18)−0.0055 (19)−0.0023 (17)0.0037 (17)
O20.051 (2)0.107 (3)0.0417 (19)0.0120 (19)−0.0044 (15)−0.0175 (18)
O30.0455 (19)0.078 (2)0.0483 (17)0.0075 (16)−0.0163 (16)−0.0041 (17)
O40.068 (2)0.069 (2)0.0390 (17)0.0026 (18)−0.0069 (16)−0.0055 (16)
O50.082 (3)0.063 (2)0.0452 (19)0.003 (2)0.0101 (18)−0.0183 (17)
O60.063 (2)0.0339 (17)0.065 (2)−0.0061 (15)0.0148 (18)−0.0082 (15)
O70.047 (2)0.0513 (19)0.0613 (19)−0.0114 (16)0.0073 (16)0.0073 (16)
O80.0394 (18)0.0526 (19)0.0410 (16)0.0017 (15)0.0101 (14)−0.0049 (14)
N10.042 (2)0.044 (2)0.045 (2)−0.0039 (18)0.0038 (18)−0.0020 (19)
C10.094 (5)0.108 (5)0.060 (3)−0.016 (4)−0.017 (3)0.025 (3)
C20.034 (3)0.055 (3)0.048 (3)−0.008 (2)0.004 (2)−0.006 (2)
C30.057 (3)0.077 (4)0.055 (3)−0.005 (3)0.000 (3)−0.020 (3)
C40.066 (4)0.074 (4)0.098 (5)0.005 (3)−0.006 (4)−0.041 (4)
C50.082 (4)0.056 (3)0.090 (4)0.021 (3)−0.005 (4)−0.015 (3)
C60.049 (3)0.068 (4)0.065 (3)0.007 (3)−0.007 (3)0.000 (3)
C70.034 (2)0.055 (3)0.042 (2)−0.003 (2)−0.003 (2)−0.005 (2)
C80.036 (3)0.063 (3)0.045 (2)−0.007 (2)−0.004 (2)−0.011 (2)
C90.034 (2)0.036 (2)0.045 (2)−0.0021 (19)−0.0015 (19)−0.007 (2)
C100.031 (2)0.034 (2)0.035 (2)−0.0017 (19)0.0006 (18)0.0000 (18)
C110.032 (2)0.059 (3)0.036 (2)0.005 (2)−0.002 (2)−0.009 (2)
C120.042 (3)0.060 (3)0.035 (2)0.000 (2)0.001 (2)−0.006 (2)
C130.051 (3)0.110 (5)0.047 (3)0.007 (3)−0.013 (3)−0.014 (3)
C140.034 (2)0.043 (3)0.042 (2)−0.001 (2)−0.008 (2)0.003 (2)
C150.035 (2)0.041 (2)0.041 (2)0.0063 (19)0.000 (2)0.002 (2)
C160.039 (2)0.029 (2)0.032 (2)−0.0042 (19)0.0016 (19)0.0005 (18)
C170.043 (3)0.031 (2)0.038 (2)0.0038 (19)0.0060 (19)0.0030 (18)
C180.047 (3)0.032 (2)0.036 (2)−0.005 (2)0.003 (2)0.0012 (19)
C190.063 (3)0.040 (3)0.045 (3)−0.013 (2)0.000 (3)−0.005 (2)
C200.057 (3)0.055 (3)0.040 (2)0.002 (2)−0.002 (2)−0.003 (2)
C210.044 (2)0.036 (2)0.034 (2)−0.0007 (19)−0.003 (2)0.002 (2)
C220.041 (2)0.033 (2)0.038 (2)−0.0031 (19)0.003 (2)−0.003 (2)
C230.047 (3)0.036 (2)0.045 (2)0.002 (2)0.012 (2)−0.002 (2)
C240.042 (3)0.032 (2)0.051 (3)−0.005 (2)−0.005 (2)−0.001 (2)
C250.035 (2)0.043 (3)0.040 (2)−0.006 (2)0.000 (2)0.002 (2)
C260.035 (2)0.043 (2)0.036 (2)0.000 (2)0.003 (2)−0.002 (2)
C270.044 (3)0.035 (2)0.043 (2)0.004 (2)0.001 (2)−0.002 (2)
C280.086 (4)0.037 (3)0.073 (4)−0.004 (3)0.020 (3)−0.017 (2)
C290.085 (4)0.065 (4)0.088 (4)0.004 (3)0.018 (4)0.029 (3)
C300.068 (4)0.052 (3)0.067 (3)0.001 (3)0.020 (3)−0.009 (3)
Geometric parameters (Å, º) top
O1—C21.367 (5)C10—C111.408 (5)
O1—C11.429 (5)C11—C121.356 (5)
O2—C121.381 (5)C11—H110.9300
O2—C131.421 (5)C12—C141.373 (6)
O3—C141.381 (5)C13—H13A0.9700
O3—C131.427 (5)C13—H13B0.9700
O4—C191.375 (6)C14—C151.352 (5)
O4—C201.456 (5)C15—C161.412 (5)
O5—C191.200 (5)C15—H150.9300
O6—C241.378 (4)C16—C171.522 (5)
O6—C281.428 (5)C17—C181.524 (5)
O7—C251.372 (5)C17—C221.525 (5)
O7—C291.429 (5)C17—H170.9800
O8—C261.355 (4)C18—C191.509 (5)
O8—C301.431 (5)C18—C211.516 (5)
N1—C91.471 (5)C18—H180.9800
N1—C81.477 (5)C20—C211.528 (5)
N1—H10.907 (10)C20—H20A0.9700
C1—H1A0.9600C20—H20B0.9700
C1—H1B0.9600C21—H210.9800
C1—H1C0.9600C22—C271.381 (6)
C2—C71.382 (6)C22—C231.397 (5)
C2—C31.383 (6)C23—C241.378 (6)
C3—C41.375 (7)C23—H230.9300
C3—H30.9300C24—C251.402 (5)
C4—C51.351 (7)C25—C261.390 (5)
C4—H40.9300C26—C271.398 (6)
C5—C61.380 (7)C27—H270.9300
C5—H50.9300C28—H28A0.9600
C6—C71.375 (6)C28—H28B0.9600
C6—H60.9300C28—H28C0.9600
C7—C81.512 (6)C29—H29A0.9600
C8—H8A0.9700C29—H29B0.9600
C8—H8B0.9700C29—H29C0.9600
C9—C101.513 (5)C30—H30A0.9600
C9—C211.522 (5)C30—H30B0.9600
C9—H90.9800C30—H30C0.9600
C10—C161.398 (5)
C2—O1—C1117.9 (4)C10—C16—C15120.2 (3)
C12—O2—C13105.1 (3)C10—C16—C17122.8 (3)
C14—O3—C13105.0 (3)C15—C16—C17116.7 (3)
C19—O4—C20110.6 (3)C16—C17—C18107.8 (3)
C24—O6—C28116.1 (3)C16—C17—C22110.6 (3)
C25—O7—C29114.6 (3)C18—C17—C22113.2 (3)
C26—O8—C30117.3 (3)C16—C17—H17108.4
C9—N1—C8114.4 (3)C18—C17—H17108.4
C9—N1—H1109 (2)C22—C17—H17108.4
C8—N1—H1102 (2)C19—C18—C21102.4 (3)
O1—C1—H1A109.5C19—C18—C17119.5 (4)
O1—C1—H1B109.5C21—C18—C17113.8 (3)
H1A—C1—H1B109.5C19—C18—H18106.8
O1—C1—H1C109.5C21—C18—H18106.8
H1A—C1—H1C109.5C17—C18—H18106.8
H1B—C1—H1C109.5O5—C19—O4121.5 (4)
O1—C2—C7114.3 (4)O5—C19—C18130.5 (5)
O1—C2—C3124.3 (4)O4—C19—C18108.0 (4)
C7—C2—C3121.4 (5)O4—C20—C21102.9 (3)
C4—C3—C2119.0 (5)O4—C20—H20A111.2
C4—C3—H3120.5C21—C20—H20A111.2
C2—C3—H3120.5O4—C20—H20B111.2
C5—C4—C3121.2 (5)C21—C20—H20B111.2
C5—C4—H4119.4H20A—C20—H20B109.1
C3—C4—H4119.4C18—C21—C9110.7 (3)
C4—C5—C6118.9 (5)C18—C21—C20101.3 (3)
C4—C5—H5120.6C9—C21—C20119.4 (3)
C6—C5—H5120.6C18—C21—H21108.3
C7—C6—C5122.3 (5)C9—C21—H21108.3
C7—C6—H6118.8C20—C21—H21108.3
C5—C6—H6118.8C27—C22—C23119.5 (4)
C6—C7—C2117.2 (4)C27—C22—C17119.8 (4)
C6—C7—C8122.2 (4)C23—C22—C17120.7 (4)
C2—C7—C8120.6 (4)C24—C23—C22120.0 (4)
N1—C8—C7115.6 (3)C24—C23—H23120.0
N1—C8—H8A108.4C22—C23—H23120.0
C7—C8—H8A108.4O6—C24—C23123.5 (4)
N1—C8—H8B108.4O6—C24—C25115.6 (4)
C7—C8—H8B108.4C23—C24—C25120.9 (4)
H8A—C8—H8B107.4O7—C25—C26120.3 (4)
N1—C9—C10110.6 (3)O7—C25—C24120.4 (4)
N1—C9—C21110.4 (3)C26—C25—C24119.1 (4)
C10—C9—C21109.5 (3)O8—C26—C25115.9 (4)
N1—C9—H9108.8O8—C26—C27124.4 (4)
C10—C9—H9108.8C25—C26—C27119.7 (4)
C21—C9—H9108.8C22—C27—C26120.8 (4)
C16—C10—C11119.8 (4)C22—C27—H27119.6
C16—C10—C9124.3 (3)C26—C27—H27119.6
C11—C10—C9116.0 (3)O6—C28—H28A109.5
C12—C11—C10118.0 (4)O6—C28—H28B109.5
C12—C11—H11121.0H28A—C28—H28B109.5
C10—C11—H11121.0O6—C28—H28C109.5
C11—C12—C14122.3 (4)H28A—C28—H28C109.5
C11—C12—O2127.7 (4)H28B—C28—H28C109.5
C14—C12—O2110.0 (4)O7—C29—H29A109.5
O2—C13—O3108.5 (4)O7—C29—H29B109.5
O2—C13—H13A110.0H29A—C29—H29B109.5
O3—C13—H13A110.0O7—C29—H29C109.5
O2—C13—H13B110.0H29A—C29—H29C109.5
O3—C13—H13B110.0H29B—C29—H29C109.5
H13A—C13—H13B108.4O8—C30—H30A109.5
C15—C14—C12121.7 (4)O8—C30—H30B109.5
C15—C14—O3128.5 (4)H30A—C30—H30B109.5
C12—C14—O3109.8 (4)O8—C30—H30C109.5
C14—C15—C16118.0 (4)H30A—C30—H30C109.5
C14—C15—H15121.0H30B—C30—H30C109.5
C16—C15—H15121.0
C1—O1—C2—C7176.6 (4)C16—C17—C18—C19−170.2 (3)
C1—O1—C2—C3−3.6 (7)C22—C17—C18—C19−47.5 (5)
O1—C2—C3—C4−179.4 (5)C16—C17—C18—C21−49.0 (4)
C7—C2—C3—C40.5 (7)C22—C17—C18—C2173.7 (4)
C2—C3—C4—C5−1.1 (9)C20—O4—C19—O5−178.7 (4)
C3—C4—C5—C61.1 (9)C20—O4—C19—C180.3 (5)
C4—C5—C6—C7−0.6 (9)C21—C18—C19—O5−157.9 (5)
C5—C6—C7—C20.0 (7)C17—C18—C19—O5−31.2 (7)
C5—C6—C7—C8−179.9 (5)C21—C18—C19—O423.3 (4)
O1—C2—C7—C6179.9 (4)C17—C18—C19—O4150.0 (4)
C3—C2—C7—C60.0 (6)C19—O4—C20—C21−23.6 (5)
O1—C2—C7—C8−0.2 (6)C19—C18—C21—C9−163.7 (3)
C3—C2—C7—C8180.0 (4)C17—C18—C21—C966.0 (4)
C9—N1—C8—C758.7 (5)C19—C18—C21—C20−36.0 (4)
C6—C7—C8—N1−116.0 (5)C17—C18—C21—C20−166.4 (3)
C2—C7—C8—N164.0 (5)N1—C9—C21—C1875.7 (4)
C8—N1—C9—C10−137.2 (3)C10—C9—C21—C18−46.3 (4)
C8—N1—C9—C21101.5 (4)N1—C9—C21—C20−41.3 (5)
N1—C9—C10—C16−102.6 (4)C10—C9—C21—C20−163.2 (4)
C21—C9—C10—C1619.2 (5)O4—C20—C21—C1836.5 (4)
N1—C9—C10—C1177.3 (4)O4—C20—C21—C9158.2 (3)
C21—C9—C10—C11−160.8 (4)C16—C17—C22—C27−147.0 (4)
C16—C10—C11—C12−1.3 (6)C18—C17—C22—C2791.9 (5)
C9—C10—C11—C12178.8 (4)C16—C17—C22—C2331.8 (5)
C10—C11—C12—C142.3 (7)C18—C17—C22—C23−89.4 (5)
C10—C11—C12—O2−179.0 (4)C27—C22—C23—C24−1.9 (6)
C13—O2—C12—C11173.7 (5)C17—C22—C23—C24179.3 (4)
C13—O2—C12—C14−7.5 (5)C28—O6—C24—C231.8 (6)
C12—O2—C13—O312.4 (5)C28—O6—C24—C25−179.2 (4)
C14—O3—C13—O2−12.6 (5)C22—C23—C24—O6178.5 (4)
C11—C12—C14—C15−1.4 (7)C22—C23—C24—C25−0.5 (6)
O2—C12—C14—C15179.6 (4)C29—O7—C25—C26−110.3 (5)
C11—C12—C14—O3178.6 (4)C29—O7—C25—C2474.8 (5)
O2—C12—C14—O3−0.4 (5)O6—C24—C25—O7−1.7 (5)
C13—O3—C14—C15−172.0 (5)C23—C24—C25—O7177.4 (4)
C13—O3—C14—C128.0 (5)O6—C24—C25—C26−176.6 (4)
C12—C14—C15—C16−0.5 (6)C23—C24—C25—C262.5 (6)
O3—C14—C15—C16179.5 (4)C30—O8—C26—C25173.3 (4)
C11—C10—C16—C15−0.6 (6)C30—O8—C26—C27−6.8 (6)
C9—C10—C16—C15179.4 (3)O7—C25—C26—O82.9 (6)
C11—C10—C16—C17173.6 (4)C24—C25—C26—O8177.8 (3)
C9—C10—C16—C17−6.4 (6)O7—C25—C26—C27−177.0 (4)
C14—C15—C16—C101.5 (6)C24—C25—C26—C27−2.1 (6)
C14—C15—C16—C17−173.1 (4)C23—C22—C27—C262.3 (6)
C10—C16—C17—C1819.9 (5)C17—C22—C27—C26−178.9 (4)
C15—C16—C17—C18−165.7 (3)O8—C26—C27—C22179.8 (4)
C10—C16—C17—C22−104.3 (4)C25—C26—C27—C22−0.3 (6)
C15—C16—C17—C2270.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.91 (1)2.28 (3)2.947 (5)130 (3)
C3—H3···O4i0.932.503.321 (6)147
Symmetry code: (i) −x+5/2, −y, z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.907 (10)2.28 (3)2.947 (5)130 (3)
C3—H3···O4i0.932.503.321 (6)147.4
Symmetry code: (i) −x+5/2, −y, z−1/2.
Acknowledgements top

This work was supported by the National Natural Science Foundation of China (No. 30873363), the Great Program of the Science Foundation of Tianjin (09ZCKFNC01200) and the Program of the Science Foundation of Tianjin (08JCYBJC070000)

references
References top

Li, Y., Wang, H., Chen, H., Chen, L.-T. & Liu, J. (2011). Acta Cryst. E67, o1538–o1539.

Luo, G., Chen, H., Zhou, J., Tian, D.-L. & Zhang, S. (2011). Acta Cryst. E67, o2087.

Rigaku. (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.