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Acta Cryst. (2011). E67, o402    [ doi:10.1107/S1600536811001231 ]

(-)-Crebanine

T. Duangthongyou, A. Makarasen, S. Techasakul, N. Chimnoi and S. Siripaisarnpipat

Abstract top

The asymmetric unit of the title compound [systematic name: 9,10-dimethoxy-7-methyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]benzodioxolo[6,5,4-de]quinoline], C20H21NO4, contains two independent molecules with very similar bond lengths and angles. The crystal packing exhibits voids of 131 Å3.

Comment top

Crebanine is an aporphine alkaloid (Israilov et al., 1980; Blanchfield et al., 2003). It was isolated from the crude hexane extract of the dried tuber of Stephania venosa, which is native to Thailand and commonly used for treatment of variety of aliments under the local name "sabulead" (Montririttigri et al., 2008; Semwal et al.,2010). S. venosa tuber and leaves were collected from Prachuabkirikhan province in the southern part of Thailand.

The asymmetric unit of the title compound [systematic name: 9,10-dimethoxy-7-methyl-6,7,7a,8-tetrahydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]benzo[g]quinoline], C20H21NO4, contains two independent molecules. There is very little difference between the bond lengths and angles of these molecules. The molecules are nearly planar (r.m.s deviation = 0.2894Å and 0.2413 Å). The molecule consists of four fused-rings (A, B, C and D). The six membered-rings B and C are both in distorted half-chair conformations. The porous crystal packing exhibits voids of 131 Å3. The structure is devoid of any classical hydrogen bonds.

Related literature top

For related structures, see: Israilov et al. (1980); Blanchfield et al. (2003). For the chemistry, pharmacology and traditional uses of the title compound, see; Montririttigri et al. (2008) and Semwal et al. (2010).

Experimental top

Crebanine was isolated from the crude hexane extract of the dried tuber of Stephania venosa. After purification by classical liquid chromatography on silica gel and recrystallization from hexane-dichloromethane, crebanine was obtained as colorless needles, m.p. 115–116.5°C.

Refinement top

All H atoms were geometrically positioned and treated as riding atoms with distances C—H = 0.96 Å (CH3), 0.97 Å (CH2), 0.93 Å (CH), and Uiso(H) = 1.20 Ueq(C) for methylene and aromatic, 1.50 Ueq(C) for methyl. The absolute structure could not be determined from the X-ray analysis, but it was known from earlier work on related compounds (Israilov et al., 1980; Blanchfield et al., 2003). 3,504 Friedel pairs were merged before the final refinement. The crystal structure contained solvent accessible voids of 131 Å3 and showed no electrons in the voids.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of molecule 1 of crebanine showing 50% displacement ellipsoids.
[Figure 2] Fig. 2. The structure of molecule 2 of crebanine showing 50% displacement ellipsoids.
9,10-dimethoxy-7-methyl-6,7,7a,8-tetrahydro-5H- benzo[g][1,3]benzodioxolo[6,5,4-de]quinoline top
Crystal data top
C20H21NO4F(000) = 1440
Mr = 339.38Dx = 1.256 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 254 reflections
a = 4.4029 (3) Åθ = 25–35°
b = 20.5847 (15) ŵ = 0.09 mm−1
c = 39.612 (3) ÅT = 298 K
V = 3590.2 (4) Å3Needle, colorless
Z = 80.22 × 0.16 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3592 reflections with I > 2σ(I)
Radiation source: Mo KαRint = 0.071
graphiteθmax = 28.3°, θmin = 1.4°
φ and ω scansh = −5→5
31211 measured reflectionsk = −26→26
5054 independent reflectionsl = −51→52
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.102P)2 + 1.8904P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.105(Δ/σ)max < 0.001
wR(F2) = 0.249Δρmax = 0.55 e Å−3
S = 1.2Δρmin = −0.25 e Å−3
5054 reflectionsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
453 parametersExtinction coefficient: 0.0011 (10)
0 restraints
Crystal data top
C20H21NO4V = 3590.2 (4) Å3
Mr = 339.38Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 4.4029 (3) ŵ = 0.09 mm−1
b = 20.5847 (15) ÅT = 298 K
c = 39.612 (3) Å0.22 × 0.16 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3592 reflections with I > 2σ(I)
31211 measured reflectionsRint = 0.071
5054 independent reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.105H-atom parameters constrained
wR(F2) = 0.249Δρmax = 0.55 e Å−3
S = 1.2Δρmin = −0.25 e Å−3
5054 reflectionsAbsolute structure: ?
453 parametersFlack parameter: ?
0 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1−0.0157 (14)−0.29778 (18)0.91783 (10)0.0651 (14)
O20.2100 (12)−0.22350 (17)0.88249 (9)0.0559 (12)
O30.4781 (12)0.06920 (18)0.82737 (10)0.0585 (12)
O40.1040 (10)0.09746 (18)0.87877 (11)0.0541 (11)
O50.6133 (16)1.07654 (18)0.71607 (10)0.0742 (17)
O60.4220 (18)1.14827 (19)0.67722 (12)0.089 (2)
O70.9437 (13)0.78611 (19)0.77372 (10)0.0602 (13)
O80.5931 (10)0.75386 (17)0.72165 (10)0.0479 (10)
N1−0.2107 (12)−0.0207 (2)0.98698 (12)0.0476 (12)
N20.2578 (11)0.8658 (2)0.61320 (11)0.0434 (11)
C10.1036 (14)−0.1925 (2)0.91134 (12)0.0401 (13)
C2−0.0304 (15)−0.2372 (2)0.93191 (14)0.0451 (14)
C3−0.1577 (16)−0.2198 (3)0.96193 (15)0.0521 (16)
H3A−0.2482−0.25060.97580.062*
C4−0.1484 (14)−0.1539 (3)0.97130 (14)0.0448 (14)
C5−0.2810 (18)−0.1329 (3)1.00402 (14)0.0589 (17)
H5A−0.225−0.16381.02140.071*
H5B−0.5008−0.13271.00220.071*
C6−0.1727 (17)−0.0660 (3)1.01402 (15)0.065 (2)
H6A−0.2863−0.05121.03350.078*
H6B0.0402−0.0681.02030.078*
C7−0.0060 (13)−0.0364 (3)0.95844 (12)0.0386 (12)
H7A0.2024−0.02610.96530.046*
C8−0.0189 (12)−0.1080 (2)0.94904 (13)0.0364 (12)
C90.1075 (13)−0.1262 (2)0.91788 (12)0.0349 (12)
C100.173 (2)−0.2903 (3)0.88925 (18)0.082 (3)
H10A0.3693−0.31010.89350.098*
H10B0.0819−0.31170.86990.098*
C11−0.0825 (13)0.0045 (2)0.92741 (13)0.0407 (13)
H11A−0.292−0.00290.92090.049*
H11B−0.05970.05030.93280.049*
C120.1226 (12)−0.0127 (2)0.89867 (13)0.0353 (12)
C130.2230 (12)−0.0770 (2)0.89452 (12)0.0320 (11)
C140.4221 (14)−0.0913 (3)0.86779 (13)0.0398 (13)
H14A0.4952−0.13330.86520.048*
C150.5107 (15)−0.0432 (3)0.84522 (13)0.0444 (14)
H15A0.6409−0.05350.82750.053*
C160.4091 (14)0.0190 (2)0.84870 (13)0.0387 (13)
C170.2161 (13)0.0345 (2)0.87532 (14)0.0389 (12)
C18−0.158 (2)0.0464 (3)0.99844 (17)0.077 (2)
H18A−0.28570.05551.01750.115*
H18B−0.20520.0760.98050.115*
H18C0.05090.05141.00480.115*
C190.674 (2)0.0563 (3)0.80014 (17)0.070 (2)
H19A0.70340.09530.78720.105*
H19B0.58680.02340.7860.105*
H19C0.86660.04150.80860.105*
C200.319 (2)0.1428 (3)0.8904 (2)0.083 (2)
H20A0.2260.18490.89210.124*
H20B0.48640.14480.87490.124*
H20C0.39150.12980.91230.124*
C210.5342 (18)1.0426 (3)0.68717 (13)0.0518 (16)
C220.413 (2)1.0858 (3)0.66409 (16)0.064 (2)
C230.3093 (19)1.0661 (3)0.63356 (16)0.0607 (19)
H23A0.23221.09570.6180.073*
C240.3227 (15)0.9997 (3)0.62627 (14)0.0482 (15)
C250.2002 (17)0.9756 (3)0.59241 (15)0.0595 (18)
H25A−0.020.9760.5930.071*
H25B0.26531.0050.57470.071*
C260.3056 (17)0.9090 (3)0.58427 (13)0.0528 (16)
H26A0.19470.89260.56490.063*
H26B0.51970.910.57850.063*
C270.4581 (12)0.8834 (2)0.64149 (12)0.0350 (12)
H27A0.66770.87310.63510.042*
C280.4386 (13)0.9565 (2)0.64921 (12)0.0382 (13)
C290.5500 (14)0.9766 (2)0.68092 (13)0.0400 (13)
C300.525 (4)1.1408 (3)0.7099 (2)0.126 (5)
H30A0.3661.1530.72550.152*
H30B0.69711.16940.71360.152*
C310.3784 (14)0.8450 (2)0.67290 (12)0.0396 (13)
H31A0.16850.85320.6790.048*
H31B0.40020.79890.66830.048*
C320.5819 (13)0.8637 (2)0.70186 (12)0.0357 (12)
C330.6691 (13)0.9292 (2)0.70569 (12)0.0367 (12)
C340.8646 (16)0.9456 (3)0.73220 (13)0.0463 (15)
H34A0.93180.98830.73430.056*
C350.9600 (16)0.8996 (3)0.75542 (14)0.0502 (15)
H35A1.08480.91160.77330.06*
C360.8682 (15)0.8351 (3)0.75186 (13)0.0440 (14)
C370.6859 (14)0.8179 (2)0.72494 (13)0.0382 (13)
C380.310 (2)0.7977 (3)0.60256 (18)0.075 (2)
H38A0.17690.78730.58410.112*
H38B0.26950.76910.62120.112*
H38C0.51710.79260.59550.112*
C391.115 (2)0.8034 (4)0.80296 (16)0.082 (3)
H39A1.15370.76520.81620.123*
H39B1.00240.83420.81620.123*
H39C1.30460.82240.79620.123*
C400.8261 (19)0.7140 (3)0.7071 (2)0.070 (2)
H40A0.75370.67010.70510.105*
H40B1.00260.71480.72130.105*
H40C0.87780.73030.68510.105*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.103 (4)0.039 (2)0.053 (2)−0.013 (3)0.001 (3)0.0042 (18)
O20.095 (4)0.0325 (19)0.040 (2)−0.010 (2)0.005 (2)−0.0030 (16)
O30.075 (3)0.043 (2)0.057 (2)−0.002 (2)0.012 (3)0.0129 (19)
O40.054 (3)0.035 (2)0.073 (3)0.007 (2)0.002 (2)0.0077 (19)
O50.136 (5)0.036 (2)0.051 (2)0.011 (3)0.000 (3)−0.0004 (19)
O60.167 (6)0.036 (2)0.064 (3)0.024 (3)−0.002 (4)0.006 (2)
O70.089 (4)0.046 (2)0.045 (2)0.012 (3)−0.012 (3)0.0082 (18)
O80.049 (2)0.036 (2)0.059 (2)−0.0048 (19)0.004 (2)0.0129 (17)
N10.045 (3)0.053 (3)0.045 (3)0.009 (2)0.001 (2)−0.010 (2)
N20.042 (3)0.044 (2)0.044 (3)−0.002 (2)−0.003 (2)0.002 (2)
C10.050 (3)0.038 (3)0.032 (3)−0.011 (3)−0.008 (3)0.001 (2)
C20.059 (4)0.035 (3)0.042 (3)−0.005 (3)−0.009 (3)0.003 (2)
C30.057 (4)0.051 (3)0.048 (3)−0.003 (3)−0.004 (3)0.023 (3)
C40.041 (3)0.046 (3)0.047 (3)0.000 (3)−0.005 (3)0.008 (2)
C50.065 (4)0.068 (4)0.044 (3)0.005 (4)0.010 (3)0.008 (3)
C60.057 (4)0.099 (5)0.038 (3)0.017 (4)0.008 (3)−0.003 (3)
C70.029 (3)0.049 (3)0.038 (3)0.005 (3)−0.004 (2)−0.006 (2)
C80.030 (3)0.039 (3)0.040 (3)−0.001 (2)−0.010 (2)0.000 (2)
C90.039 (3)0.036 (3)0.030 (2)−0.003 (2)−0.008 (2)0.001 (2)
C100.139 (8)0.034 (3)0.072 (5)−0.025 (5)0.013 (6)−0.007 (3)
C110.036 (3)0.037 (3)0.048 (3)0.005 (2)0.003 (3)0.001 (2)
C120.031 (3)0.036 (3)0.039 (3)−0.003 (2)−0.007 (2)−0.001 (2)
C130.033 (3)0.030 (2)0.033 (2)−0.009 (2)−0.006 (2)0.000 (2)
C140.045 (3)0.034 (3)0.040 (3)−0.004 (3)−0.002 (3)−0.001 (2)
C150.052 (4)0.048 (3)0.033 (3)−0.004 (3)0.002 (3)0.000 (2)
C160.053 (3)0.028 (2)0.035 (3)−0.004 (3)−0.007 (3)0.004 (2)
C170.039 (3)0.030 (3)0.047 (3)0.001 (2)−0.009 (3)0.002 (2)
C180.094 (6)0.076 (5)0.061 (4)0.008 (5)0.016 (4)−0.029 (4)
C190.085 (5)0.064 (4)0.061 (4)0.001 (4)0.019 (4)0.022 (3)
C200.081 (6)0.044 (4)0.123 (7)−0.002 (4)0.005 (6)−0.018 (4)
C210.079 (5)0.041 (3)0.035 (3)0.008 (3)0.011 (3)0.006 (2)
C220.097 (6)0.038 (3)0.057 (4)0.018 (4)0.014 (4)0.010 (3)
C230.083 (5)0.048 (4)0.051 (4)0.020 (4)0.002 (4)0.023 (3)
C240.057 (4)0.047 (3)0.040 (3)0.003 (3)0.005 (3)0.008 (3)
C250.061 (4)0.065 (4)0.053 (4)0.000 (4)−0.008 (3)0.020 (3)
C260.061 (4)0.061 (4)0.037 (3)0.003 (3)−0.006 (3)0.005 (3)
C270.029 (3)0.038 (3)0.038 (3)0.006 (2)0.000 (2)0.001 (2)
C280.044 (3)0.038 (3)0.033 (3)0.002 (3)0.012 (3)0.012 (2)
C290.044 (3)0.033 (3)0.043 (3)0.005 (3)0.010 (3)0.007 (2)
C300.262 (16)0.037 (4)0.079 (5)0.022 (7)−0.040 (9)−0.004 (4)
C310.042 (3)0.037 (3)0.040 (3)0.001 (3)0.001 (3)0.007 (2)
C320.036 (3)0.035 (3)0.036 (3)0.002 (2)0.009 (2)0.000 (2)
C330.045 (3)0.035 (3)0.030 (3)0.006 (3)0.010 (2)0.004 (2)
C340.062 (4)0.036 (3)0.041 (3)0.001 (3)0.000 (3)−0.002 (2)
C350.058 (4)0.052 (3)0.041 (3)0.006 (3)−0.006 (3)−0.005 (3)
C360.056 (4)0.041 (3)0.035 (3)0.010 (3)0.003 (3)0.004 (2)
C370.049 (3)0.030 (3)0.036 (3)0.001 (2)0.012 (3)0.006 (2)
C380.094 (6)0.065 (4)0.067 (4)−0.005 (5)−0.020 (5)−0.012 (3)
C390.119 (7)0.074 (5)0.052 (4)0.034 (5)−0.026 (5)0.004 (3)
C400.071 (5)0.043 (3)0.095 (5)0.000 (4)0.004 (5)−0.001 (3)
Geometric parameters (Å, °) top
O1—C21.367 (6)C15—H15A0.93
O1—C101.413 (9)C16—C171.391 (8)
O2—C11.390 (7)C18—H18A0.96
O2—C101.411 (7)C18—H18B0.96
O3—C161.370 (6)C18—H18C0.96
O3—C191.407 (8)C19—H19A0.96
O4—C171.393 (6)C19—H19B0.96
O4—C201.408 (8)C19—H19C0.96
O5—C211.386 (7)C20—H20A0.96
O5—C301.400 (8)C20—H20B0.96
O6—C221.389 (7)C20—H20C0.96
O6—C301.380 (9)C21—C291.382 (7)
O7—C361.371 (6)C21—C221.383 (9)
O7—C391.428 (8)C22—C231.354 (9)
O8—C371.385 (6)C23—C241.399 (8)
O8—C401.435 (8)C23—H23A0.93
N1—C61.430 (8)C24—C281.370 (7)
N1—C181.472 (8)C24—C251.529 (8)
N1—C71.481 (7)C25—C261.482 (8)
N2—C261.466 (7)C25—H25A0.97
N2—C271.472 (7)C25—H25B0.97
N2—C381.481 (8)C26—H26A0.97
C1—C21.364 (7)C26—H26B0.97
C1—C91.390 (7)C27—C311.515 (7)
C2—C31.362 (8)C27—C281.538 (7)
C3—C41.406 (8)C27—H27A0.98
C3—H3A0.93C28—C291.410 (8)
C4—C81.412 (7)C29—C331.480 (7)
C4—C51.486 (8)C30—H30A0.97
C5—C61.511 (9)C30—H30B0.97
C5—H5A0.97C31—C321.506 (7)
C5—H5B0.97C31—H31A0.97
C6—H6A0.97C31—H31B0.97
C6—H6B0.97C32—C371.391 (7)
C7—C81.523 (7)C32—C331.409 (7)
C7—C111.528 (7)C33—C341.400 (8)
C7—H7A0.98C34—C351.386 (8)
C8—C91.405 (7)C34—H34A0.93
C9—C131.464 (7)C35—C361.394 (8)
C10—H10A0.97C35—H35A0.93
C10—H10B0.97C36—C371.381 (8)
C11—C121.496 (7)C38—H38A0.96
C11—H11A0.97C38—H38B0.96
C11—H11B0.97C38—H38C0.96
C12—C171.403 (7)C39—H39A0.96
C12—C131.404 (7)C39—H39B0.96
C13—C141.406 (7)C39—H39C0.96
C14—C151.390 (7)C40—H40A0.96
C14—H14A0.93C40—H40B0.96
C15—C161.362 (7)C40—H40C0.96
C2—O1—C10104.8 (4)H19B—C19—H19C109.5
C1—O2—C10104.6 (5)O4—C20—H20A109.5
C16—O3—C19117.8 (5)O4—C20—H20B109.5
C17—O4—C20114.3 (5)H20A—C20—H20B109.5
C21—O5—C30105.2 (5)O4—C20—H20C109.5
C22—O6—C30104.9 (5)H20A—C20—H20C109.5
C36—O7—C39117.2 (5)H20B—C20—H20C109.5
C37—O8—C40111.8 (5)C29—C21—O5129.1 (5)
C6—N1—C18111.2 (5)C29—C21—C22122.2 (6)
C6—N1—C7111.0 (5)O5—C21—C22108.6 (5)
C18—N1—C7110.1 (5)C23—C22—C21121.9 (6)
C26—N2—C27111.1 (4)C23—C22—O6128.4 (6)
C26—N2—C38109.2 (5)C21—C22—O6109.7 (6)
C27—N2—C38110.9 (5)C22—C23—C24117.5 (5)
C2—C1—C9123.8 (5)C22—C23—H23A121.3
C2—C1—O2109.1 (4)C24—C23—H23A121.3
C9—C1—O2126.9 (5)C28—C24—C23120.9 (6)
C3—C2—O1128.0 (5)C28—C24—C25120.2 (5)
C3—C2—C1121.5 (5)C23—C24—C25118.9 (5)
O1—C2—C1110.5 (5)C26—C25—C24112.4 (5)
C2—C3—C4118.2 (5)C26—C25—H25A109.1
C2—C3—H3A120.9C24—C25—H25A109.1
C4—C3—H3A120.9C26—C25—H25B109.1
C3—C4—C8119.4 (5)C24—C25—H25B109.1
C3—C4—C5120.0 (5)H25A—C25—H25B107.9
C8—C4—C5120.6 (5)N2—C26—C25110.3 (5)
C4—C5—C6111.7 (5)N2—C26—H26A109.6
C4—C5—H5A109.3C25—C26—H26A109.6
C6—C5—H5A109.3N2—C26—H26B109.6
C4—C5—H5B109.3C25—C26—H26B109.6
C6—C5—H5B109.3H26A—C26—H26B108.1
H5A—C5—H5B107.9N2—C27—C31111.0 (4)
N1—C6—C5111.1 (5)N2—C27—C28111.1 (4)
N1—C6—H6A109.4C31—C27—C28109.5 (4)
C5—C6—H6A109.4N2—C27—H27A108.4
N1—C6—H6B109.4C31—C27—H27A108.4
C5—C6—H6B109.4C28—C27—H27A108.4
H6A—C6—H6B108C24—C28—C29122.0 (5)
N1—C7—C8112.0 (5)C24—C28—C27121.6 (5)
N1—C7—C11111.1 (4)C29—C28—C27116.4 (4)
C8—C7—C11109.2 (4)C21—C29—C28115.5 (5)
N1—C7—H7A108.1C21—C29—C33123.2 (5)
C8—C7—H7A108.1C28—C29—C33121.3 (4)
C11—C7—H7A108.1O6—C30—O5111.1 (5)
C9—C8—C4122.1 (5)O6—C30—H30A109.4
C9—C8—C7117.3 (5)O5—C30—H30A109.4
C4—C8—C7120.7 (5)O6—C30—H30B109.4
C1—C9—C8114.9 (5)O5—C30—H30B109.4
C1—C9—C13124.5 (5)H30A—C30—H30B108
C8—C9—C13120.6 (4)C32—C31—C27110.8 (4)
O2—C10—O1109.0 (5)C32—C31—H31A109.5
O2—C10—H10A109.9C27—C31—H31A109.5
O1—C10—H10A109.9C32—C31—H31B109.5
O2—C10—H10B109.9C27—C31—H31B109.5
O1—C10—H10B109.9H31A—C31—H31B108.1
H10A—C10—H10B108.3C37—C32—C33119.2 (5)
C12—C11—C7110.4 (4)C37—C32—C31121.5 (5)
C12—C11—H11A109.6C33—C32—C31119.3 (5)
C7—C11—H11A109.6C34—C33—C32118.7 (5)
C12—C11—H11B109.6C34—C33—C29123.7 (5)
C7—C11—H11B109.6C32—C33—C29117.6 (5)
H11A—C11—H11B108.1C35—C34—C33121.3 (5)
C17—C12—C13118.9 (5)C35—C34—H34A119.4
C17—C12—C11121.0 (5)C33—C34—H34A119.4
C13—C12—C11120.2 (5)C34—C35—C36119.7 (6)
C14—C13—C12118.8 (5)C34—C35—H35A120.1
C14—C13—C9123.2 (5)C36—C35—H35A120.1
C12—C13—C9118.0 (5)O7—C36—C37116.0 (5)
C15—C14—C13120.7 (5)O7—C36—C35124.5 (5)
C15—C14—H14A119.7C37—C36—C35119.5 (5)
C13—C14—H14A119.7C36—C37—O8119.3 (5)
C16—C15—C14120.8 (5)C36—C37—C32121.6 (5)
C16—C15—H15A119.6O8—C37—C32119.1 (5)
C14—C15—H15A119.6N2—C38—H38A109.5
C15—C16—O3125.0 (5)N2—C38—H38B109.5
C15—C16—C17119.6 (5)H38A—C38—H38B109.5
O3—C16—C17115.4 (5)N2—C38—H38C109.5
O4—C17—C16120.3 (5)H38A—C38—H38C109.5
O4—C17—C12118.4 (5)H38B—C38—H38C109.5
C16—C17—C12121.3 (5)O7—C39—H39A109.5
N1—C18—H18A109.5O7—C39—H39B109.5
N1—C18—H18B109.5H39A—C39—H39B109.5
H18A—C18—H18B109.5O7—C39—H39C109.5
N1—C18—H18C109.5H39A—C39—H39C109.5
H18A—C18—H18C109.5H39B—C39—H39C109.5
H18B—C18—H18C109.5O8—C40—H40A109.5
O3—C19—H19A109.5O8—C40—H40B109.5
O3—C19—H19B109.5H40A—C40—H40B109.5
H19A—C19—H19B109.5O8—C40—H40C109.5
O3—C19—H19C109.5H40A—C40—H40C109.5
H19A—C19—H19C109.5H40B—C40—H40C109.5
C10—O2—C1—C2−8.6 (8)C30—O5—C21—C29−174.6 (9)
C10—O2—C1—C9176.2 (7)C30—O5—C21—C222.0 (11)
C10—O1—C2—C3−172.4 (7)C29—C21—C22—C23−1.8 (13)
C10—O1—C2—C17.9 (8)O5—C21—C22—C23−178.7 (8)
C9—C1—C2—C3−3.8 (10)C29—C21—C22—O6179.1 (7)
O2—C1—C2—C3−179.3 (6)O5—C21—C22—O62.2 (10)
C9—C1—C2—O1175.9 (6)C30—O6—C22—C23175.5 (11)
O2—C1—C2—O10.4 (7)C30—O6—C22—C21−5.4 (11)
O1—C2—C3—C4−179.5 (6)C21—C22—C23—C241.5 (13)
C1—C2—C3—C40.2 (10)O6—C22—C23—C24−179.6 (8)
C2—C3—C4—C82.3 (9)C22—C23—C24—C28−0.5 (11)
C2—C3—C4—C5−179.2 (6)C22—C23—C24—C25178.4 (7)
C3—C4—C5—C6163.8 (6)C28—C24—C25—C26−17.2 (9)
C8—C4—C5—C6−17.8 (8)C23—C24—C25—C26163.9 (6)
C18—N1—C6—C5169.7 (6)C27—N2—C26—C25−67.8 (7)
C7—N1—C6—C5−67.3 (7)C38—N2—C26—C25169.5 (6)
C4—C5—C6—N150.5 (8)C24—C25—C26—N248.9 (8)
C6—N1—C7—C848.1 (6)C26—N2—C27—C31172.1 (5)
C18—N1—C7—C8171.7 (5)C38—N2—C27—C31−66.2 (6)
C6—N1—C7—C11170.5 (5)C26—N2—C27—C2850.0 (6)
C18—N1—C7—C11−65.9 (6)C38—N2—C27—C28171.7 (5)
C3—C4—C8—C9−1.3 (9)C23—C24—C28—C29−0.3 (9)
C5—C4—C8—C9−179.8 (6)C25—C24—C28—C29−179.1 (6)
C3—C4—C8—C7179.9 (5)C23—C24—C28—C27−179.4 (6)
C5—C4—C8—C71.4 (8)C25—C24—C28—C271.8 (9)
N1—C7—C8—C9165.5 (5)N2—C27—C28—C24−17.9 (7)
C11—C7—C8—C942.0 (7)C31—C27—C28—C24−140.8 (5)
N1—C7—C8—C4−15.6 (7)N2—C27—C28—C29163.0 (5)
C11—C7—C8—C4−139.1 (5)C31—C27—C28—C2940.0 (7)
C2—C1—C9—C84.6 (9)O5—C21—C29—C28177.2 (7)
O2—C1—C9—C8179.2 (5)C22—C21—C29—C281.0 (10)
C2—C1—C9—C13−173.5 (5)O5—C21—C29—C33−1.6 (12)
O2—C1—C9—C131.1 (10)C22—C21—C29—C33−177.8 (7)
C4—C8—C9—C1−2.0 (8)C24—C28—C29—C210.0 (9)
C7—C8—C9—C1176.8 (5)C27—C28—C29—C21179.2 (6)
C4—C8—C9—C13176.2 (5)C24—C28—C29—C33178.8 (6)
C7—C8—C9—C13−4.9 (7)C27—C28—C29—C33−2.0 (8)
C1—O2—C10—O113.5 (8)C22—O6—C30—O56.8 (14)
C2—O1—C10—O2−13.3 (8)C21—O5—C30—O6−5.5 (14)
N1—C7—C11—C12−179.0 (4)N2—C27—C31—C32−179.4 (4)
C8—C7—C11—C12−55.0 (6)C28—C27—C31—C32−56.4 (6)
C7—C11—C12—C17−146.2 (5)C27—C31—C32—C37−142.4 (5)
C7—C11—C12—C1334.3 (7)C27—C31—C32—C3337.6 (7)
C17—C12—C13—C142.2 (7)C37—C32—C33—C341.6 (8)
C11—C12—C13—C14−178.3 (5)C31—C32—C33—C34−178.4 (5)
C17—C12—C13—C9−176.2 (5)C37—C32—C33—C29−179.1 (5)
C11—C12—C13—C93.3 (7)C31—C32—C33—C290.9 (7)
C1—C9—C13—C14−19.7 (8)C21—C29—C33—C34−22.0 (9)
C8—C9—C13—C14162.3 (5)C28—C29—C33—C34159.3 (6)
C1—C9—C13—C12158.6 (6)C21—C29—C33—C32158.8 (6)
C8—C9—C13—C12−19.4 (7)C28—C29—C33—C32−19.9 (8)
C12—C13—C14—C15−2.0 (8)C32—C33—C34—C35−3.3 (9)
C9—C13—C14—C15176.3 (5)C29—C33—C34—C35177.6 (6)
C13—C14—C15—C160.6 (9)C33—C34—C35—C362.1 (10)
C14—C15—C16—O3−178.5 (5)C39—O7—C36—C37−176.0 (6)
C14—C15—C16—C170.5 (9)C39—O7—C36—C353.4 (10)
C19—O3—C16—C15−1.5 (9)C34—C35—C36—O7−178.5 (6)
C19—O3—C16—C17179.5 (6)C34—C35—C36—C370.8 (10)
C20—O4—C17—C16−74.0 (7)O7—C36—C37—O8−0.1 (8)
C20—O4—C17—C12107.8 (6)C35—C36—C37—O8−179.5 (6)
C15—C16—C17—O4−178.4 (5)O7—C36—C37—C32177.0 (5)
O3—C16—C17—O40.6 (8)C35—C36—C37—C32−2.4 (9)
C15—C16—C17—C12−0.3 (8)C40—O8—C37—C36−80.1 (7)
O3—C16—C17—C12178.8 (5)C40—O8—C37—C32102.8 (6)
C13—C12—C17—O4177.1 (5)C33—C32—C37—C361.2 (8)
C11—C12—C17—O4−2.4 (8)C31—C32—C37—C36−178.8 (5)
C13—C12—C17—C16−1.1 (8)C33—C32—C37—O8178.2 (5)
C11—C12—C17—C16179.4 (5)C31—C32—C37—O8−1.8 (8)
Acknowledgements top

The authors thank Dr Narongsuk Chaichit, Department of Physics, Faculty of Science, Thammasart University, for the data collection and the Department of Chemistry, Faculty of Science, Kasetsart University, for financial support.

references
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