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Acta Cryst. (2007). E63, o3671    [ doi:10.1107/S1600536807033053 ]

9-Ethyl-3,6-bis(2-thienyl)carbazole

P. Wang, Y. Ju, S. Y. Tang, J. Y. Wu and H. P. Zhou

Abstract top

The asymmetric unit of the title compound, C22H17NS2, contains three crystallographically independent molecules. In the crystal structure, molecules are stacked through C-H...[pi] interactions, with H...centroid distances ranging from 2.69 to 3.18 Å. Weak H...S interactions (2.91 Å) also contribute to the stabilization of the crystal structure. Four thiophene rings are disordered over two positions each; site occupancy factors range from 0.26 to 0.75.

Comment top

The derivatives of thiophene have been studied so far mainly for their semiconductor and charge-transport properties such as high-field-effect charge mobility (Horowitz et al., 1989). The derivatives of carbazole complexes are being explored for a multitude of optoelectronic and photocatalytic applications, including organic light emitting diodes (OLEDs) (Mi et al., 2003). The two derivatives both have excellent optical-electronic properties. A new molecule was designed and synthesized combining the two derivatives in order to get a new compound with excellent electrochemical properties. We herein report its crystal structure.

The asymmetric unit of the title compound, (I), contains three crystallographically independent molecules (Fig. 1). The bond lengths and angles are generally within normal ranges (Allen et al., 1987).

When the crystal structure was solved,the atoms C10, C20, C54, C64, H10, H20, H54, H64, S1, S2, S5 and S6 were found to be disordered. So, for instance, the position of C10 atom may be occupied by S1 atom. It could be elucidated that the thiophene ring is linked to the benzene ring by a single bond, which spins so fast that the configuration is turn from one to another. In fact, it may not be possible to separate S atoms from C atoms, and that is the reason why the the C—S bonds are longer than C═C bonds, but shorter than normal C—S single bonds. The dihedral angles between the planar thiophen and benzene rings are between 1.71 (3)–27.17 (3) °.

In the crystal structure, the molecules are stacked through C—H···π interactions with H···centroid distances in the range 2.69–3.18 Å. Weak H···S interactions also contribute to the stabilization of the crystal structure, e.g. H56···S2 = 2.91 Å.

Related literature top

For bond length data, see: Allen et al. (1987). For related literature, see: Horowitz et al. (1989); Mi et al. (2003).

Experimental top

For the preparation of the title compound, (I), a mixture of 9-ethyl-3,6 -diiodo-carbazole (0.44 g, 1 mmol), sodium carbonate (0.42 g, 4 mmol) and 2-thiophenyl boronic acid (0.32 g, 2.5 mmol) was heated at 333 K with DMF (20 ml) and water (10 ml) as solvents. Then, the mixture was heated for 0.5 h, palladium acetate (0.0076 g, 0.05 mmol) was added to the mixture with the temperature up to 353 K for 3 h. Then, it was cooled and poured into water (1000 ml). The precipitated yellow solid was filtered off and washed with water, dried over anhydrous magnesium sulfate, and eluted with petroleum ether/ethyl acetate (15:1). The product was obtained as yellow solid (yield; 0.2 g, 56%). Single crystals of (I) were grown by slow evaporation of a dichloromethane/ethyl acetate (1:1) solution.

Refinement top

When the crystal structure was solved,the atoms C10, C20, C54, C64, H10, H20, H54, H64, S1, S2, S5 and S6 were found to be disordered. During refinement with isotropic thermal parameters, the occupancies of disordered H atoms were refined as H10 = 0.742 (4), H10' = 0.258 (4), H20 = 0.548 (4), H20' = 0.452 (4), H54 = 0.694 (4), H54' = 0.306 (4), H64 = 0.310 (5) and H64' = 0.690 (5). The remaining site occupancy factors were also refined as C10 = 0.724 (4), C10' = 0.258 (4), C20 = 0.548 (4), C20' = 0.452 (4), C54 = 0.694 (4), C54' = 0.306 (4), C64 = 0.310 (5), C64' = 0.690 (5), S1 = 0.742 (4), S1' = 0.258 (4), S2 = 0.548 (4), S2' = 0.452 (4), S5 = 0.694 (4), S5' = 0.306 (4), S6 = 0.310 (5) and S6' = 0.690 (5) during anisotropic refinement. H11, H12, H21, H22, H55, H56, H65 and H66 atoms were located in difference syntheses and refined isotropically [C—H = 0.86 (4)–1.09 (5) Å and Uiso(H) = 0.096 (12)–0.132 (18) Å2]. The remaining H atoms were positioned geometrically with C—H = 0.93, 0.97 and 0.96 Å for aromatic, 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: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: WinGX (Farrugia, 1999).

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 of (I). The interactions are shown as dashed lines.
9-Ethyl-3,6-bis(2-thienyl)carbazole top
Crystal data top
C22H17NS2Z = 6
Mr = 359.51F000 = 1128
Triclinic, P1Dx = 1.316 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71069 Å
a = 13.826 (5) ÅCell parameters from 12368 reflections
b = 14.436 (5) Åθ = 1.5–27.7º
c = 15.525 (5) ŵ = 0.30 mm−1
α = 70.674 (5)ºT = 298 (2) K
β = 69.206 (5)ºPlate, yellow
γ = 87.850 (5)º0.50 × 0.50 × 0.28 mm
V = 2722.3 (16) Å3
Data collection top
Bruker APEX II CCD area-detector
diffractometer		12368 independent reflections
Radiation source: fine-focus sealed tube8498 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.019
T = 298(2) Kθmax = 27.7º
φ and ω scansθmin = 1.5º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −16→18
Tmin = 0.866, Tmax = 0.922k = −18→18
25041 measured reflectionsl = −20→15
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)] = 0.065H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.202  w = 1/[σ2(Fo2) + (0.0912P)2 + 1.7033P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.012
12368 reflectionsΔρmax = 0.76 e Å−3
716 parametersΔρmin = −0.64 e Å−3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0022 (7)
Crystal data top
C22H17NS2γ = 87.850 (5)º
Mr = 359.51V = 2722.3 (16) Å3
Triclinic, P1Z = 6
a = 13.826 (5) ÅMo Kα
b = 14.436 (5) ŵ = 0.30 mm−1
c = 15.525 (5) ÅT = 298 (2) K
α = 70.674 (5)º0.50 × 0.50 × 0.28 mm
β = 69.206 (5)º
Data collection top
Bruker APEX II CCD area-detector
diffractometer		12368 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		8498 reflections with I > 2σ(I)
Tmin = 0.866, Tmax = 0.922Rint = 0.019
25041 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0651 restraint
wR(F2) = 0.202H atoms treated by a mixture of
independent and constrained refinement
S = 1.03Δρmax = 0.76 e Å−3
12368 reflectionsΔρmin = −0.64 e Å−3
716 parameters
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 > 2sigma(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*/UeqOcc. (<1)
S10.71244 (10)0.73415 (7)−0.10946 (9)0.0812 (4)0.742 (4)
S1'0.61263 (17)0.59080 (15)−0.12592 (16)0.0828 (8)0.258 (4)
S20.51077 (10)0.03050 (9)0.11620 (10)0.0719 (5)0.548 (4)
S2'0.58974 (13)−0.10133 (10)0.23914 (13)0.0822 (6)0.452 (4)
S30.80073 (9)0.72853 (8)0.19477 (7)0.0992 (4)
S40.57467 (7)0.42975 (8)0.71323 (7)0.0831 (3)
S51.19353 (8)0.99255 (10)0.17451 (9)0.0808 (5)0.694 (4)
S5'1.04342 (18)0.90629 (16)0.14985 (16)0.0941 (9)0.306 (4)
S60.39927 (16)0.64444 (17)0.67458 (19)0.0977 (9)0.310 (5)
S6'0.49871 (12)0.65660 (11)0.48471 (11)0.0940 (6)0.690 (5)
N10.8483 (2)0.31631 (19)0.1567 (2)0.0810 (9)
N21.04847 (17)0.38998 (17)0.42305 (17)0.0573 (5)
N30.7489 (2)1.01317 (19)0.53198 (19)0.0673 (6)
C10.8887 (4)0.3126 (4)0.2850 (6)0.143 (2)
H1A0.85680.37300.28420.214*
H1B0.93680.30500.31830.214*
H1C0.83610.25810.31860.214*
C20.9394 (6)0.3151 (3)0.1930 (4)0.128 (2)
H2A0.97700.25730.19130.154*
H2B0.98730.37390.15470.154*
C30.8148 (2)0.3983 (2)0.1017 (2)0.0633 (7)
C40.73899 (19)0.36810 (18)0.07278 (17)0.0471 (5)
C50.69553 (19)0.43772 (18)0.01479 (18)0.0477 (5)
H50.64580.4179−0.00460.057*
C60.7267 (2)0.53743 (18)−0.01424 (19)0.0528 (6)
C70.8000 (3)0.5648 (2)0.0185 (2)0.0682 (8)
H70.81890.63150.00110.082*
C80.8451 (3)0.4974 (2)0.0750 (3)0.0755 (9)
H80.89440.51760.09480.091*
C90.6841 (2)0.61193 (19)−0.0791 (2)0.0585 (7)
C100.61263 (17)0.59080 (15)−0.12592 (16)0.0828 (8)0.742 (4)
H100.58700.5300−0.12130.099*0.742 (4)
C10'0.71244 (10)0.73415 (7)−0.10946 (9)0.0812 (4)0.258 (4)
H10'0.75370.7701−0.09340.097*0.258 (4)
C110.5931 (3)0.6909 (3)−0.1812 (3)0.0905 (12)
H110.550 (3)0.698 (3)−0.216 (3)0.105 (14)*
C120.6414 (3)0.7662 (3)−0.1768 (3)0.0944 (13)
H120.636 (3)0.839 (3)−0.206 (3)0.114 (14)*
C130.7929 (2)0.2335 (2)0.1665 (2)0.0606 (7)
C140.72440 (19)0.26127 (18)0.11561 (17)0.0465 (5)
C150.65954 (18)0.18905 (17)0.11686 (17)0.0440 (5)
H150.61380.20680.08350.053*
C160.66299 (18)0.09035 (17)0.16788 (18)0.0460 (5)
C170.7337 (2)0.0654 (2)0.2172 (2)0.0619 (7)
H170.7364−0.00060.25090.074*
C180.7985 (3)0.1348 (2)0.2172 (3)0.0745 (9)
H180.84470.11690.24990.089*
C190.59496 (19)0.01153 (18)0.17285 (18)0.0487 (5)
C200.58974 (13)−0.10133 (10)0.23914 (13)0.0822 (6)0.548 (4)
H200.6243−0.13150.28130.099*0.548 (4)
C20'0.51077 (10)0.03050 (9)0.11620 (10)0.0719 (5)0.452 (4)
H20'0.49350.08770.07700.086*0.452 (4)
C210.5085 (3)−0.1447 (3)0.2107 (3)0.0852 (11)
H210.491 (3)−0.208 (3)0.237 (3)0.096 (12)*
C220.4697 (3)−0.0816 (3)0.1512 (3)0.0828 (10)
H220.416 (4)−0.097 (3)0.130 (3)0.128 (16)*
C231.1401 (3)0.2518 (3)0.3855 (3)0.0884 (11)
H23A1.08390.20500.43480.133*
H23B1.20450.22230.37900.133*
H23C1.13010.27130.32400.133*
C241.1428 (2)0.3390 (2)0.4140 (2)0.0667 (8)
H24A1.15280.31880.47610.080*
H24B1.20180.38450.36540.080*
C251.0308 (2)0.46353 (19)0.34844 (19)0.0521 (6)
C260.93146 (19)0.49525 (18)0.38463 (18)0.0469 (5)
C270.8959 (2)0.56896 (18)0.32279 (18)0.0484 (5)
H270.83070.59040.34710.058*
C280.9580 (2)0.61119 (19)0.22376 (18)0.0517 (6)
C291.0566 (2)0.5771 (2)0.1899 (2)0.0614 (7)
H291.09790.60460.12390.074*
C301.0940 (2)0.5054 (2)0.2497 (2)0.0601 (7)
H301.15970.48490.22540.072*
C310.9213 (2)0.6882 (2)0.1564 (2)0.0593 (7)
C320.9754 (3)0.7401 (2)0.0557 (2)0.0681 (8)
H321.04220.73010.01950.082*
C330.9120 (4)0.8099 (3)0.0179 (3)0.0912 (12)
H330.93420.8512−0.04710.109*
C340.8199 (4)0.8116 (3)0.0819 (3)0.1027 (13)
H340.77080.85350.06710.123*
C350.9612 (2)0.37190 (19)0.5078 (2)0.0524 (6)
C360.88737 (19)0.43696 (17)0.48713 (18)0.0469 (5)
C370.79393 (19)0.43471 (18)0.56199 (18)0.0480 (5)
H370.74530.47790.54890.058*
C380.7725 (2)0.36834 (18)0.65638 (18)0.0492 (5)
C390.8477 (2)0.30319 (19)0.6736 (2)0.0573 (6)
H390.83360.25820.73640.069*
C400.9404 (2)0.3039 (2)0.6014 (2)0.0592 (7)
H400.98840.25980.61450.071*
C410.6749 (2)0.36582 (18)0.73637 (19)0.0517 (6)
C420.6492 (2)0.31051 (18)0.84272 (17)0.0502 (6)
H420.69170.27170.87230.060*
C430.5429 (3)0.3306 (3)0.8902 (2)0.0728 (8)
H430.50820.30320.95760.087*
C440.4976 (3)0.3902 (3)0.8324 (2)0.0763 (9)
H440.43050.40800.85570.092*
C450.7056 (5)1.1735 (3)0.5483 (4)0.1303 (19)
H45A0.75531.20760.48410.195*
H45B0.69891.21210.58960.195*
H45C0.63951.16360.54380.195*
C460.7408 (3)1.0782 (3)0.5898 (3)0.0829 (10)
H46A0.69251.04590.65610.100*
H46B0.80811.08860.59300.100*
C470.8363 (2)1.0072 (2)0.4559 (2)0.0573 (6)
C480.8150 (2)0.93445 (18)0.42109 (18)0.0495 (6)
C490.8915 (2)0.91588 (18)0.34354 (18)0.0494 (6)
H490.87820.86730.32100.059*
C500.9881 (2)0.96989 (18)0.2995 (2)0.0526 (6)
C511.0070 (2)1.0402 (2)0.3377 (2)0.0637 (7)
H511.07221.07490.30970.076*
C520.9331 (3)1.0597 (2)0.4145 (2)0.0663 (7)
H520.94751.10680.43810.080*
C531.0670 (2)0.95582 (19)0.2127 (2)0.0568 (6)
C541.04342 (18)0.90629 (16)0.14985 (16)0.0941 (9)0.694 (4)
H540.98010.87860.15710.113*0.694 (4)
C54'1.19353 (8)0.99255 (10)0.17451 (9)0.0808 (5)0.306 (4)
H54'1.23121.02280.19860.097*0.306 (4)
C551.1501 (3)0.9132 (3)0.0715 (3)0.0892 (11)
H551.152 (4)0.889 (3)0.021 (3)0.120 (16)*
C561.2267 (3)0.9560 (3)0.0796 (3)0.0928 (13)
H561.290 (4)0.964 (3)0.040 (3)0.117 (15)*
C570.6711 (2)0.9463 (2)0.5461 (2)0.0598 (7)
C580.7091 (2)0.89398 (19)0.48028 (19)0.0518 (6)
C590.6470 (2)0.8165 (2)0.48735 (19)0.0541 (6)
H590.67250.78080.44520.065*
C600.5466 (2)0.7918 (2)0.5575 (2)0.0583 (6)
C610.5089 (3)0.8504 (2)0.6172 (2)0.0700 (8)
H610.44050.83690.66120.084*
C620.5689 (3)0.9260 (2)0.6129 (2)0.0733 (9)
H620.54220.96310.65350.088*
C630.4823 (2)0.7047 (2)0.5730 (2)0.0635 (7)
C640.49871 (12)0.65660 (11)0.48471 (11)0.0940 (6)0.310 (5)
H640.54390.67360.41990.113*0.310 (5)
C64'0.39927 (16)0.64444 (17)0.67458 (19)0.0977 (9)0.690 (5)
H64'0.37960.65420.73460.117*0.690 (5)
C650.4048 (3)0.5678 (4)0.5558 (4)0.1007 (14)
H650.396 (4)0.522 (4)0.533 (4)0.132 (18)*
C660.3597 (3)0.5652 (3)0.6472 (4)0.0968 (12)
H660.300 (4)0.511 (3)0.708 (3)0.119 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0917 (8)0.0497 (5)0.0826 (8)0.0056 (5)−0.0222 (6)−0.0080 (5)
S1'0.0875 (15)0.0686 (12)0.0853 (15)0.0189 (10)−0.0396 (12)−0.0098 (10)
S20.0766 (8)0.0641 (7)0.0823 (9)0.0009 (6)−0.0368 (7)−0.0249 (6)
S2'0.0918 (11)0.0548 (8)0.1083 (13)0.0041 (7)−0.0453 (10)−0.0280 (8)
S30.0994 (7)0.0981 (7)0.0698 (6)0.0341 (6)−0.0243 (5)−0.0001 (5)
S40.0743 (5)0.0946 (6)0.0649 (5)0.0193 (5)−0.0127 (4)−0.0226 (5)
S50.0552 (6)0.1086 (10)0.0667 (7)0.0035 (6)−0.0151 (5)−0.0223 (6)
S5'0.0909 (15)0.0976 (15)0.0767 (14)0.0044 (11)0.0012 (10)−0.0421 (11)
S60.0665 (12)0.1033 (16)0.1164 (19)−0.0115 (10)−0.0153 (11)−0.0462 (14)
S6'0.0980 (10)0.1008 (10)0.0908 (10)−0.0029 (7)−0.0298 (8)−0.0455 (8)
N10.100 (2)0.0581 (14)0.096 (2)−0.0127 (14)−0.0713 (18)−0.0002 (14)
N20.0479 (12)0.0613 (13)0.0558 (13)0.0112 (10)−0.0150 (10)−0.0159 (11)
N30.0773 (17)0.0634 (14)0.0626 (15)0.0079 (12)−0.0161 (13)−0.0334 (12)
C10.108 (4)0.122 (4)0.229 (8)0.020 (3)−0.071 (5)−0.088 (5)
C20.232 (7)0.069 (2)0.107 (4)−0.016 (3)−0.104 (4)−0.008 (2)
C30.0728 (18)0.0553 (15)0.0615 (17)−0.0086 (13)−0.0344 (15)−0.0069 (13)
C40.0490 (13)0.0483 (12)0.0397 (12)−0.0006 (10)−0.0135 (10)−0.0117 (10)
C50.0477 (13)0.0481 (12)0.0424 (13)0.0032 (10)−0.0128 (10)−0.0131 (10)
C60.0539 (14)0.0476 (13)0.0456 (14)0.0026 (11)−0.0084 (11)−0.0120 (11)
C70.082 (2)0.0468 (14)0.0695 (19)−0.0109 (14)−0.0268 (16)−0.0117 (13)
C80.093 (2)0.0573 (17)0.081 (2)−0.0144 (16)−0.0485 (19)−0.0084 (15)
C90.0576 (15)0.0487 (14)0.0520 (15)0.0082 (11)−0.0066 (12)−0.0103 (11)
C100.0875 (15)0.0686 (12)0.0853 (15)0.0189 (10)−0.0396 (12)−0.0098 (10)
C10'0.0917 (8)0.0497 (5)0.0826 (8)0.0056 (5)−0.0222 (6)−0.0080 (5)
C110.082 (2)0.093 (3)0.085 (3)0.026 (2)−0.035 (2)−0.012 (2)
C120.093 (3)0.058 (2)0.090 (3)0.0197 (19)−0.007 (2)−0.0029 (18)
C130.0649 (17)0.0555 (15)0.0635 (17)−0.0030 (13)−0.0355 (14)−0.0088 (13)
C140.0479 (13)0.0483 (12)0.0405 (12)0.0022 (10)−0.0160 (10)−0.0115 (10)
C150.0438 (12)0.0499 (12)0.0385 (12)0.0071 (10)−0.0147 (10)−0.0159 (10)
C160.0450 (12)0.0479 (12)0.0424 (13)0.0061 (10)−0.0131 (10)−0.0154 (10)
C170.0703 (18)0.0480 (14)0.0668 (18)0.0039 (12)−0.0374 (15)−0.0053 (12)
C180.084 (2)0.0582 (16)0.090 (2)0.0009 (15)−0.061 (2)−0.0032 (15)
C190.0469 (13)0.0530 (13)0.0459 (13)0.0079 (10)−0.0117 (11)−0.0225 (11)
C200.0918 (11)0.0548 (8)0.1083 (13)0.0041 (7)−0.0453 (10)−0.0280 (8)
C20'0.0766 (8)0.0641 (7)0.0823 (9)0.0009 (6)−0.0368 (7)−0.0249 (6)
C210.105 (3)0.0528 (18)0.100 (3)−0.0048 (18)−0.039 (2)−0.0255 (19)
C220.073 (2)0.096 (3)0.096 (3)0.0035 (19)−0.035 (2)−0.049 (2)
C230.092 (3)0.095 (3)0.100 (3)0.037 (2)−0.050 (2)−0.047 (2)
C240.0520 (16)0.0754 (19)0.0690 (19)0.0160 (14)−0.0199 (14)−0.0233 (15)
C250.0475 (13)0.0551 (14)0.0517 (14)0.0045 (11)−0.0149 (11)−0.0190 (12)
C260.0454 (12)0.0482 (12)0.0445 (13)0.0001 (10)−0.0128 (10)−0.0160 (10)
C270.0482 (13)0.0483 (13)0.0450 (13)0.0021 (10)−0.0130 (11)−0.0152 (10)
C280.0579 (15)0.0502 (13)0.0433 (13)−0.0039 (11)−0.0153 (11)−0.0138 (11)
C290.0596 (16)0.0674 (17)0.0428 (14)−0.0038 (13)−0.0042 (12)−0.0151 (12)
C300.0475 (14)0.0715 (17)0.0536 (16)0.0044 (12)−0.0074 (12)−0.0232 (13)
C310.0751 (18)0.0517 (14)0.0453 (14)−0.0013 (13)−0.0175 (13)−0.0132 (11)
C320.097 (2)0.0541 (15)0.0468 (15)−0.0025 (15)−0.0254 (15)−0.0082 (12)
C330.140 (4)0.069 (2)0.0528 (19)0.002 (2)−0.036 (2)−0.0034 (16)
C340.133 (4)0.088 (3)0.073 (3)0.032 (3)−0.045 (3)−0.004 (2)
C350.0509 (14)0.0525 (14)0.0516 (14)0.0056 (11)−0.0177 (12)−0.0161 (11)
C360.0484 (13)0.0445 (12)0.0455 (13)0.0031 (10)−0.0167 (11)−0.0129 (10)
C370.0476 (13)0.0472 (12)0.0475 (14)0.0041 (10)−0.0171 (11)−0.0142 (10)
C380.0531 (14)0.0454 (12)0.0456 (13)0.0003 (10)−0.0152 (11)−0.0136 (10)
C390.0646 (17)0.0505 (14)0.0485 (15)0.0039 (12)−0.0192 (13)−0.0076 (11)
C400.0600 (16)0.0544 (14)0.0585 (16)0.0122 (12)−0.0236 (14)−0.0118 (12)
C410.0572 (15)0.0488 (13)0.0457 (14)−0.0021 (11)−0.0146 (12)−0.0155 (11)
C420.0479 (13)0.0521 (13)0.0372 (12)−0.0123 (10)0.0043 (10)−0.0181 (10)
C430.079 (2)0.077 (2)0.0494 (16)−0.0069 (16)−0.0092 (15)−0.0192 (15)
C440.0642 (19)0.090 (2)0.064 (2)0.0040 (17)−0.0041 (16)−0.0340 (18)
C450.182 (5)0.090 (3)0.126 (4)0.045 (3)−0.050 (4)−0.056 (3)
C460.093 (3)0.086 (2)0.077 (2)0.0097 (19)−0.0221 (19)−0.0463 (19)
C470.0650 (17)0.0531 (14)0.0547 (16)0.0120 (12)−0.0210 (13)−0.0211 (12)
C480.0535 (14)0.0480 (13)0.0461 (13)0.0116 (11)−0.0178 (11)−0.0160 (10)
C490.0527 (14)0.0465 (12)0.0485 (14)0.0115 (10)−0.0195 (11)−0.0152 (11)
C500.0529 (14)0.0468 (13)0.0551 (15)0.0123 (11)−0.0222 (12)−0.0115 (11)
C510.0577 (16)0.0584 (16)0.0730 (19)0.0055 (13)−0.0238 (15)−0.0198 (14)
C520.076 (2)0.0588 (16)0.0719 (19)0.0060 (14)−0.0304 (16)−0.0277 (15)
C530.0527 (15)0.0508 (14)0.0543 (15)0.0103 (11)−0.0148 (12)−0.0078 (12)
C540.0909 (15)0.0976 (15)0.0767 (14)0.0044 (11)0.0012 (10)−0.0421 (11)
C54'0.0552 (6)0.1086 (10)0.0667 (7)0.0035 (6)−0.0151 (5)−0.0223 (6)
C550.081 (3)0.099 (3)0.069 (2)0.010 (2)−0.0033 (19)−0.032 (2)
C560.064 (2)0.114 (3)0.063 (2)0.018 (2)−0.0053 (18)−0.005 (2)
C570.0699 (18)0.0585 (15)0.0491 (15)0.0123 (13)−0.0157 (13)−0.0230 (12)
C580.0575 (15)0.0518 (13)0.0449 (13)0.0135 (11)−0.0174 (12)−0.0172 (11)
C590.0560 (15)0.0610 (15)0.0468 (14)0.0122 (12)−0.0160 (12)−0.0237 (12)
C600.0567 (15)0.0647 (16)0.0497 (15)0.0094 (12)−0.0156 (12)−0.0193 (12)
C610.0643 (18)0.077 (2)0.0550 (17)0.0066 (15)−0.0028 (14)−0.0262 (15)
C620.078 (2)0.076 (2)0.0568 (18)0.0126 (16)−0.0044 (15)−0.0338 (15)
C630.0533 (15)0.0745 (18)0.0644 (18)0.0110 (13)−0.0226 (14)−0.0252 (15)
C640.0980 (10)0.1008 (10)0.0908 (10)−0.0029 (7)−0.0298 (8)−0.0455 (8)
C64'0.0665 (12)0.1033 (16)0.1164 (19)−0.0115 (10)−0.0153 (11)−0.0462 (14)
C650.077 (3)0.115 (3)0.135 (4)0.007 (2)−0.043 (3)−0.069 (3)
C660.060 (2)0.107 (3)0.115 (4)−0.005 (2)−0.019 (2)−0.040 (3)
Geometric parameters (Å, °) top
S1—C91.691 (3)C29—H290.9300
S1—C121.627 (5)C30—H300.9300
S1'—C91.509 (4)C31—C321.415 (4)
S1'—C111.487 (4)C31—S31.710 (3)
S2—C191.658 (3)C32—C331.427 (5)
S2—C221.583 (4)C32—H320.9300
S2'—C191.602 (3)C33—C341.313 (6)
S2'—C211.561 (4)C33—H330.9300
S5—C531.679 (3)C34—S31.698 (4)
S5—C561.637 (5)C34—H340.9300
S5'—C531.509 (4)C35—N21.387 (3)
S5'—C551.523 (4)C35—C401.392 (4)
S6—C631.564 (4)C35—C361.410 (3)
S6—C661.526 (5)C36—C371.390 (3)
S6'—C631.677 (3)C37—C381.392 (3)
S6'—C651.649 (5)C37—H370.9300
C1—C21.338 (8)C38—C391.412 (4)
C1—H1A0.9600C38—C411.466 (4)
C1—H1B0.9600C39—C401.370 (4)
C1—H1C0.9600C39—H390.9300
C2—N11.550 (6)C40—H400.9300
C2—H2A0.9700C41—C421.491 (4)
C2—H2B0.9700C41—S41.714 (3)
C3—N11.384 (4)C42—C431.459 (4)
C3—C81.387 (4)C42—H420.9300
C3—C41.410 (4)C43—C441.336 (5)
C4—C51.386 (3)C43—H430.9300
C4—C141.453 (3)C44—S41.683 (3)
C5—C61.393 (3)C44—H440.9300
C5—H50.9300C45—C461.460 (6)
C6—C71.404 (4)C45—H45A0.9600
C6—C91.474 (4)C45—H45B0.9600
C7—C81.372 (4)C45—H45C0.9600
C7—H70.9300C46—N31.475 (4)
C8—H80.9300C46—H46A0.9700
C9—C101.509 (4)C46—H46B0.9700
C9—C10'1.691 (3)C47—N31.381 (4)
C10—C111.487 (4)C47—C521.386 (4)
C10—H100.9300C47—C481.412 (4)
C10'—H10'0.9300C48—C491.389 (4)
C11—C121.329 (6)C48—C581.443 (4)
C11—H110.92 (4)C49—C501.391 (4)
C12—C10'1.627 (5)C49—H490.9300
C12—H121.01 (4)C50—C511.406 (4)
C13—N11.380 (4)C50—C531.473 (4)
C13—C181.395 (4)C51—C521.371 (4)
C13—C141.405 (3)C51—H510.9300
C14—C151.391 (3)C52—H520.9300
C15—C161.391 (3)C53—C541.508 (4)
C15—H150.9300C53—C54'1.678 (3)
C16—C171.413 (4)C54—C551.523 (4)
C16—C191.468 (3)C54—H540.9300
C17—C181.369 (4)C54'—H54'0.9300
C17—H170.9300C55—C561.309 (6)
C18—H180.9300C55—H550.95 (5)
C19—C201.602 (3)C56—C54'1.636 (5)
C19—C20'1.657 (3)C56—H560.86 (5)
C20—C211.561 (4)C57—N31.382 (4)
C20—H200.9300C57—C621.395 (4)
C20'—H20'0.9300C57—C581.411 (4)
C21—C221.315 (6)C58—C591.386 (4)
C21—H210.86 (4)C59—C601.396 (4)
C22—C20'1.582 (4)C59—H590.9300
C22—H220.97 (5)C60—C611.410 (4)
C23—C241.472 (5)C60—C631.470 (4)
C23—H23A0.9600C61—C621.366 (5)
C23—H23B0.9600C61—H610.9300
C23—H23C0.9600C62—H620.9300
C24—N21.459 (3)C63—C64'1.563 (4)
C24—H24A0.9700C63—C641.676 (3)
C24—H24B0.9700C64—C651.649 (5)
C25—N21.377 (3)C64—H640.9300
C25—C301.398 (4)C64'—H64'0.9300
C25—C261.409 (3)C65—C661.320 (7)
C26—C271.384 (3)C65—H650.87 (5)
C26—C361.441 (3)C66—C64'1.524 (5)
C27—C281.398 (4)C66—H661.09 (5)
C27—H270.9300C10'—H10'0.9300
C28—C291.410 (4)C20'—H20'0.9300
C28—C311.467 (4)C54'—H54'0.9300
C29—C301.367 (4)C64'—H64'0.9300
C12—S1—C9C32—C31—C28
C9—S1'—H10C32—C31—S3
C11—S1'—C9C28—C31—S3
C11—S1'—H10C31—C32—C33
C22—S2—C19C31—C32—H32
C21—S2'—C19C33—C32—H32
C21—S2'—H20C34—C33—C32
C19—S2'—H20C34—C33—H33
C34—S3—C31C32—C33—H33
C44—S4—C41C33—C34—S3
C56—S5—C53C33—C34—H34
C53—S5'—C55S3—C34—H34
C53—S5—H54N2—C35—C40
C66—S6—C63N2—C35—C36
C63—S6'—H64C40—C35—C36
C65—S6'—H64C37—C36—C35
C65—S6'—C63C37—C36—C26
C13—N1—C3C35—C36—C26
C13—N1—C2C36—C37—C38
C3—N1—C2C36—C37—H37
C25—N2—C35C38—C37—H37
C25—N2—C24C37—C38—C39
C35—N2—C24C37—C38—C41
C47—N3—C57C39—C38—C41
C47—N3—C46C40—C39—C38
C57—N3—C46C40—C39—H39
C2—C1—H1AC38—C39—H39
C2—C1—H1BC39—C40—C35
H1A—C1—H1BC39—C40—H40
C2—C1—H1CC35—C40—H40
H1A—C1—H1CC38—C41—C42
H1B—C1—H1CC38—C41—S4
C1—C2—N1C42—C41—S4
C1—C2—H2AC43—C42—C41
N1—C2—H2AC43—C42—H42
C1—C2—H2BC41—C42—H42
N1—C2—H2BC44—C43—C42
H2A—C2—H2BC44—C43—H43
N1—C3—C8C42—C43—H43
N1—C3—C4C43—C44—S4
C8—C3—C4C43—C44—H44
C5—C4—C3S4—C44—H44
C5—C4—C14C46—C45—H45A
C3—C4—C14C46—C45—H45B
C4—C5—C6H45A—C45—H45B
C4—C5—H5C46—C45—H45C
C6—C5—H5H45A—C45—H45C
C5—C6—C7H45B—C45—H45C
C5—C6—C9C45—C46—N3
C7—C6—C9C45—C46—H46A
C8—C7—C6N3—C46—H46A
C8—C7—H7C45—C46—H46B
C6—C7—H7N3—C46—H46B
C7—C8—C3H46A—C46—H46B
C7—C8—H8N3—C47—C52
C3—C8—H8N3—C47—C48
C6—C9—S1C52—C47—C48
C10—C9—S1C49—C48—C47
C6—C9—C10C49—C48—C58
C6—C9—C10'C47—C48—C58
C10—C9—C10'C48—C49—C50
C11—C10—C9C48—C49—H49
C11—C10—H10C50—C49—H49
C9—C10—H10C49—C50—C51
C12—C11—S1'C49—C50—C53
S1'—C11—H11C51—C50—C53
C12—C11—C10C52—C51—C50
C12—C11—H11C52—C51—H51
C10—C11—H11C50—C51—H51
S1—C12—H12C51—C52—C47
C11—C12—S1C51—C52—H52
C11—C12—C10'C47—C52—H52
C11—C12—H12C50—C53—S5
C10'—C12—H12C50—C53—S5'
N1—C13—C18C54—C53—S5
N1—C13—C14C50—C53—C54
C18—C13—C14C50—C53—C54'
C15—C14—C13C54—C53—C54'
C15—C14—C4C53—C54—C55
C13—C14—C4C53—C54—H54
C16—C15—C14C55—C54—H54
C16—C15—H15C56—C55—S5'
C14—C15—H15S5'—C55—H55
C15—C16—C17C56—C55—C54
C15—C16—C19C56—C55—H55
C17—C16—C19C54—C55—H55
C18—C17—C16S5—C56—H56
C18—C17—H17C55—C56—S5
C16—C17—H17C55—C56—C54'
C17—C18—C13C55—C56—H56
C17—C18—H18C54'—C56—H56
C13—C18—H18N3—C57—C62
C16—C19—S2'N3—C57—C58
C16—C19—S2C62—C57—C58
C20—C19—S2C59—C58—C57
C16—C19—C20C59—C58—C48
C16—C19—C20'C57—C58—C48
C20—C19—C20'C58—C59—C60
C21—C20—C19C58—C59—H59
C21—C20—H20C60—C59—H59
C19—C20—H20C59—C60—C61
C22—C21—S2'C59—C60—C63
S2'—C21—H21C61—C60—C63
C22—C21—C20C62—C61—C60
C22—C21—H21C62—C61—H61
C20—C21—H21C60—C61—H61
S2—C22—H22C61—C62—C57
C21—C22—S2C61—C62—H62
C21—C22—C20'C57—C62—H62
C21—C22—H22S6—C63—C64
C20'—C22—H22C60—C63—S6
C24—C23—H23AC60—C63—S6'
C24—C23—H23BC60—C63—C64'
H23A—C23—H23BC60—C63—C64
C24—C23—H23CC64'—C63—C64
H23A—C23—H23CC65—C64—C63
H23B—C23—H23CC65—C64—H64
N2—C24—C23C63—C64—H64
N2—C24—H24AC66—C65—C64
C23—C24—H24AC66—C65—H65
N2—C24—H24BC64—C65—H65
C23—C24—H24BS6—C66—H66
H24A—C24—H24BC65—C66—S6
N2—C25—C30C65—C66—C64'
N2—C25—C26C65—C66—H66
C30—C25—C26C64'—C66—H66
C27—C26—C25C12—C10'—C9
C27—C26—C36C12—C10'—H10'
C25—C26—C36C9—C10'—H10'
C26—C27—C28C22—C20'—C19
C26—C27—H27C22—C20'—H20'
C28—C27—H27C19—C20'—H20'
C27—C28—C29C56—C54'—C53
C27—C28—C31C56—C54'—H54'
C29—C28—C31C53—C54'—H54'
C30—C29—C28C66—C64'—C63
C30—C29—H29C66—C64'—H64'
C28—C29—H29C63—C64'—H64'
C29—C30—C25C66—C65—S6'
C29—C30—H30S6'—C65—H65
C25—C30—H30
N1—C3—C4—C5−178.5 (3)C52—C47—C48—C49−0.7 (4)
C8—C3—C4—C51.6 (5)N3—C47—C48—C58−0.5 (3)
N1—C3—C4—C141.6 (3)C52—C47—C48—C58179.3 (3)
C8—C3—C4—C14−178.3 (3)C47—C48—C49—C50−1.0 (4)
C3—C4—C5—C6−0.3 (4)C58—C48—C49—C50178.9 (3)
C14—C4—C5—C6179.5 (3)C48—C49—C50—C512.3 (4)
C4—C5—C6—C7−1.6 (4)C48—C49—C50—C53−175.5 (2)
C4—C5—C6—C9177.6 (2)C49—C50—C51—C52−2.0 (4)
C5—C6—C7—C82.3 (5)C53—C50—C51—C52175.8 (3)
C9—C6—C7—C8−176.8 (3)C50—C51—C52—C470.3 (5)
C6—C7—C8—C3−1.1 (5)N3—C47—C52—C51−179.1 (3)
N1—C3—C8—C7179.3 (4)C48—C47—C52—C511.1 (4)
C4—C3—C8—C7−0.9 (5)C49—C50—C53—C5416.8 (4)
C5—C6—C9—C10−4.9 (4)C51—C50—C53—C54−160.9 (2)
C7—C6—C9—C10174.2 (3)C49—C50—C53—C54'−162.4 (2)
C5—C6—C9—C10'175.3 (2)C51—C50—C53—C54'19.9 (4)
C7—C6—C9—C10'−5.6 (4)C50—C53—C54—C55179.1 (3)
C6—C9—C10—C11179.0 (3)C54'—C53—C54—C55−1.6 (3)
C10'—C9—C10—C11−1.1 (3)C53—C54—C55—C560.4 (4)
C9—C10—C11—C121.2 (4)C54—C55—C56—C54'1.1 (5)
C10—C11—C12—C10'−0.9 (5)N3—C57—C58—C59174.1 (2)
N1—C13—C14—C15−179.1 (3)C62—C57—C58—C59−5.2 (4)
C18—C13—C14—C150.9 (4)N3—C57—C58—C48−2.0 (3)
N1—C13—C14—C4−0.4 (3)C62—C57—C58—C48178.7 (3)
C18—C13—C14—C4179.7 (3)C49—C48—C58—C596.3 (5)
C5—C4—C14—C15−2.1 (5)C47—C48—C58—C59−173.8 (3)
C3—C4—C14—C15177.7 (3)C49—C48—C58—C57−178.4 (3)
C5—C4—C14—C13179.4 (3)C47—C48—C58—C571.5 (3)
C3—C4—C14—C13−0.8 (3)C57—C58—C59—C601.6 (4)
C13—C14—C15—C16−0.2 (4)C48—C58—C59—C60176.4 (3)
C4—C14—C15—C16−178.5 (3)C58—C59—C60—C612.8 (4)
C14—C15—C16—C17−0.5 (4)C58—C59—C60—C63−174.3 (3)
C14—C15—C16—C19178.9 (2)C59—C60—C61—C62−4.0 (5)
C15—C16—C17—C180.5 (5)C63—C60—C61—C62173.2 (3)
C19—C16—C17—C18−179.0 (3)C60—C61—C62—C570.5 (5)
C16—C17—C18—C130.3 (5)N3—C57—C62—C61−175.1 (3)
N1—C13—C18—C17179.0 (4)C58—C57—C62—C614.1 (5)
C14—C13—C18—C17−1.0 (5)C59—C60—C63—C64'149.2 (3)
C15—C16—C19—C20−174.1 (2)C61—C60—C63—C64'−27.9 (4)
C17—C16—C19—C205.4 (3)C59—C60—C63—C64−25.9 (4)
C15—C16—C19—C20'2.1 (3)C61—C60—C63—C64156.9 (3)
C17—C16—C19—C20'−178.4 (2)C60—C63—C64—C65179.5 (3)
C16—C19—C20—C21−178.9 (2)C64'—C63—C64—C654.0 (3)
C20'—C19—C20—C214.6 (2)C63—C64—C65—C66−2.7 (4)
C19—C20—C21—C22−2.9 (4)C64—C65—C66—C64'0.5 (6)
C20—C21—C22—C20'0.0 (5)C11—C12—C10'—C90.1 (3)
N2—C25—C26—C27−179.8 (2)C6—C9—C10'—C12−179.5 (3)
C30—C25—C26—C27−0.6 (4)C10—C9—C10'—C120.6 (2)
N2—C25—C26—C360.0 (3)C21—C22—C20'—C192.7 (3)
C30—C25—C26—C36179.2 (2)C16—C19—C20'—C22179.0 (2)
C25—C26—C27—C280.9 (4)C20—C19—C20'—C22−4.5 (2)
C36—C26—C27—C28−178.9 (3)C55—C56—C54'—C53−1.9 (4)
C26—C27—C28—C29−0.3 (4)C50—C53—C54'—C56−178.6 (2)
C26—C27—C28—C31178.9 (2)C54—C53—C54'—C562.1 (2)
C27—C28—C29—C30−0.6 (4)C65—C66—C64'—C632.1 (5)
C31—C28—C29—C30−179.8 (3)C60—C63—C64'—C66−179.5 (3)
C28—C29—C30—C250.9 (4)C64—C63—C64'—C66−4.0 (3)
N2—C25—C30—C29178.8 (3)C18—C13—N1—C3−178.7 (4)
C26—C25—C30—C29−0.3 (4)C14—C13—N1—C31.4 (4)
C27—C28—C31—C32177.9 (3)C18—C13—N1—C26.8 (6)
C29—C28—C31—C32−2.9 (4)C14—C13—N1—C2−173.1 (4)
C27—C28—C31—S3−1.1 (4)C8—C3—N1—C13178.0 (4)
C29—C28—C31—S3178.2 (2)C4—C3—N1—C13−1.9 (4)
C28—C31—C32—C33−179.0 (3)C8—C3—N1—C2−7.6 (7)
S3—C31—C32—C330.0 (3)C4—C3—N1—C2172.5 (4)
C31—C32—C33—C34−0.1 (5)C1—C2—N1—C13−88.4 (5)
C32—C33—C34—S30.1 (5)C1—C2—N1—C398.1 (5)
N2—C35—C36—C37−178.2 (2)C30—C25—N2—C35−178.3 (3)
C40—C35—C36—C371.8 (4)C26—C25—N2—C350.8 (3)
N2—C35—C36—C261.3 (3)C30—C25—N2—C241.1 (5)
C40—C35—C36—C26−178.7 (2)C26—C25—N2—C24−179.8 (2)
C27—C26—C36—C37−1.6 (5)C40—C35—N2—C25178.6 (3)
C25—C26—C36—C37178.6 (3)C36—C35—N2—C25−1.3 (3)
C27—C26—C36—C35179.0 (3)C40—C35—N2—C24−0.8 (5)
C25—C26—C36—C35−0.8 (3)C36—C35—N2—C24179.2 (2)
C35—C36—C37—C38−0.7 (4)C23—C24—N2—C25−88.5 (4)
C26—C36—C37—C38180.0 (3)C23—C24—N2—C3590.8 (4)
C36—C37—C38—C39−0.5 (4)C52—C47—N3—C57179.4 (3)
C36—C37—C38—C41179.3 (2)C48—C47—N3—C57−0.7 (3)
C37—C38—C39—C400.6 (4)C52—C47—N3—C46−1.8 (5)
C41—C38—C39—C40−179.2 (3)C48—C47—N3—C46178.0 (3)
C38—C39—C40—C350.5 (4)C62—C57—N3—C47−179.0 (3)
N2—C35—C40—C39178.3 (3)C58—C57—N3—C471.7 (3)
C36—C35—C40—C39−1.7 (4)C62—C57—N3—C462.2 (5)
C37—C38—C41—C42−169.6 (2)C58—C57—N3—C46−177.0 (3)
C39—C38—C41—C4210.2 (4)C45—C46—N3—C4790.8 (5)
C37—C38—C41—S410.8 (3)C45—C46—N3—C57−90.7 (5)
C39—C38—C41—S4−169.4 (2)C33—C34—S3—C310.0 (4)
C38—C41—C42—C43−178.7 (2)C32—C31—S3—C340.0 (3)
S4—C41—C42—C430.9 (3)C28—C31—S3—C34179.1 (3)
C41—C42—C43—C44−1.0 (4)C43—C44—S4—C410.0 (3)
C42—C43—C44—S40.7 (4)C38—C41—S4—C44179.1 (2)
N3—C47—C48—C49179.4 (2)C42—C41—S4—C44−0.6 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C29—H29···S2i0.932.693.096 (3)107
Symmetry codes: (i) −x, −y, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C29—H29···S2i0.932.693.096 (3)107
Symmetry codes: (i) −x, −y, −z.
Acknowledgements top

The work was supported by the National Natural Science Foundation of China (grant Nos. 50532030, 50325311 and 50335050), the Doctoral Program Foundation of the Ministry of Education of China, the Education Committee of Anhui Province (grant Nos. 2006 K J032A and 2006 K J135B), the Persons With Ability Foundation of Anhui Province (grant No. 2002Z021), the Team for Scientific Innovation Foundation of Anhui Province (grant No. 2006 K J007TD), and the Key Laboratory of Opto-Electronic Information Acquisition and Manipulation (Anhui University), Ministry of Education.

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.

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435–?.

Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

Horowitz, G., Fichou, D., Peng, X., Xu, Z. & Garnier, F. (1989). Solid State Commun. 72, 381–384.

Mi, B. X., Wang, P. F., Liu, M. W., Kwong, H. L., Wong, N. B., Lee, C. S. & Lee, S. T. (2003). Chem. Mater. 15, 3148–3151.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

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

Sheldrick, G. M. (1997b). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.