Literature DB >> 21578093

Diacetonitrile[N,N'-bis(2,6-diisopropyl-phenyl)ethane-1,2-diimine]dichloridochromium(II) acetonitrile solvate.

Stephan Peitz1, Normen Peulecke, Bernd H Müller, Anke Spannenberg, Uwe Rosenthal.   

Abstract

The title compound, [CrCl(2)(CH(3)CN)(2)(C(26)H(36)N(2))]·CH(3)CN, was synthesized by the reaction of CrCl(2)(THF)(2) with N,N'-bis-(2,6-diisopropyl-phen-yl)ethane-1,2-diimine in dichloro-methane/acetonitrile. The chromium center is coordinated by two N atoms of the chelating diimine ligand, two chloride ions in a trans configuration with respect to each other, and by two N atoms of two acetonitrile mol-ecules in a distorted octa-hedral geometry.

Entities:  

Year:  2009        PMID: 21578093      PMCID: PMC2971420          DOI: 10.1107/S1600536809040094

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For derivatives of the title compound, see: Turki et al. (2006 ▶); Kreisel et al. (2007 ▶); Ghosh et al. (2008 ▶). For catalytic features of diimine and PNP ligands, see: tom Dieck & Kinzel (1979 ▶); Bart et al. (2004 ▶); Huang et al. (2007 ▶); Wöhl et al. (2009 ▶).

Experimental

Crystal data

[CrCl2(C2H3N)2(C26H36N2)]·C2H3N M = 622.63 Monoclinic, a = 18.7305 (6) Å b = 13.2462 (5) Å c = 13.9582 (4) Å β = 97.838 (2)° V = 3430.8 (2) Å3 Z = 4 Mo Kα radiation μ = 0.52 mm−1 T = 200 K 0.5 × 0.5 × 0.4 mm

Data collection

Stoe IPDSII diffractometer Absorption correction: numerical ( and ; Stoe & Cie, 2005 ▶) T min = 0.761, T max = 0.847 53468 measured reflections 7489 independent reflections 6233 reflections with I > 2σ(I) R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.108 S = 1.20 7489 reflections 364 parameters H-atom parameters constrained Δρmax = 0.47 e Å−3 Δρmin = −0.40 e Å−3 Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809040094/im2148sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040094/im2148Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[CrCl2(C2H3N)2(C26H36N2)]·C2H3NF(000) = 1320
Mr = 622.63Dx = 1.205 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 12659 reflections
a = 18.7305 (6) Åθ = 2.1–29.6°
b = 13.2462 (5) ŵ = 0.52 mm1
c = 13.9582 (4) ÅT = 200 K
β = 97.838 (2)°Prism, brown
V = 3430.8 (2) Å30.5 × 0.5 × 0.4 mm
Z = 4
Stoe IPDSII diffractometer7489 independent reflections
Radiation source: fine-focus sealed tube6233 reflections with I > 2σ(I)
graphiteRint = 0.036
ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)h = −23→23
Tmin = 0.761, Tmax = 0.847k = −16→16
53468 measured reflectionsl = −17→17
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.20w = 1/[σ2(Fo2) + (0.0286P)2 + 3.9005P] where P = (Fo2 + 2Fc2)/3
7489 reflections(Δ/σ)max = 0.001
364 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = −0.40 e Å3
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.
xyzUiso*/Ueq
N50.1588 (3)0.3180 (4)0.4602 (4)0.1140 (18)
C310.1283 (3)0.3863 (4)0.4315 (3)0.0728 (13)
C320.0890 (2)0.4750 (3)0.3954 (3)0.0679 (11)
H32A0.12130.53360.40200.102*
H32B0.04900.48660.43250.102*
H32C0.07000.46520.32710.102*
C10.27829 (12)0.77519 (18)0.13545 (17)0.0227 (5)
H1A0.28940.81900.08570.027*
C20.24076 (12)0.68549 (18)0.11524 (18)0.0225 (5)
H2A0.22360.66560.05080.027*
C30.32484 (13)0.89587 (17)0.25385 (17)0.0215 (5)
C40.27698 (13)0.96797 (18)0.28368 (18)0.0249 (5)
C50.30411 (14)1.06144 (19)0.3145 (2)0.0301 (6)
H5A0.27291.11010.33650.036*
C60.37644 (15)1.0852 (2)0.3138 (2)0.0329 (6)
H6A0.39451.14900.33690.039*
C70.42186 (14)1.0162 (2)0.2795 (2)0.0315 (6)
H7A0.47051.03430.27620.038*
C80.39764 (13)0.91987 (19)0.24949 (19)0.0264 (5)
C90.19649 (13)0.9481 (2)0.2747 (2)0.0320 (6)
H9A0.18930.87320.27160.038*
C100.16000 (18)0.9923 (3)0.1792 (3)0.0591 (10)
H10A0.18310.96540.12570.089*
H10B0.16471.06600.18090.089*
H10C0.10880.97400.16990.089*
C110.16168 (17)0.9872 (3)0.3605 (3)0.0514 (9)
H11A0.18630.95790.42050.077*
H11B0.11070.96790.35240.077*
H11C0.16571.06090.36360.077*
C120.44939 (14)0.8477 (2)0.2111 (2)0.0335 (6)
H12A0.42340.78260.19520.040*
C130.47405 (18)0.8879 (3)0.1183 (3)0.0487 (8)
H13A0.43190.90120.07030.073*
H13B0.50490.83770.09270.073*
H13C0.50120.95070.13240.073*
C140.51433 (16)0.8257 (3)0.2870 (3)0.0483 (8)
H14A0.49770.79950.34570.073*
H14B0.54170.88800.30220.073*
H14C0.54530.77540.26160.073*
C150.17107 (13)0.55834 (18)0.17315 (17)0.0223 (5)
C160.09994 (13)0.5968 (2)0.15552 (18)0.0257 (5)
C170.04407 (15)0.5284 (2)0.1314 (2)0.0344 (6)
H17A−0.00400.55260.11850.041*
C180.05677 (16)0.4263 (2)0.1257 (2)0.0390 (7)
H18A0.01770.38120.10890.047*
C190.12614 (16)0.3896 (2)0.1445 (2)0.0374 (7)
H19A0.13420.31900.14130.045*
C200.18483 (14)0.45424 (19)0.16800 (19)0.0282 (5)
C210.08221 (13)0.7084 (2)0.1614 (2)0.0293 (6)
H21A0.12750.74490.18720.035*
C220.05521 (16)0.7513 (2)0.0607 (2)0.0401 (7)
H22A0.09130.73880.01740.060*
H22B0.04740.82420.06570.060*
H22C0.00980.71840.03480.060*
C230.02642 (16)0.7285 (3)0.2299 (2)0.0448 (8)
H23A0.04400.70120.29400.067*
H23B−0.01920.69570.20460.067*
H23C0.01880.80140.23480.067*
C240.26105 (15)0.4138 (2)0.1798 (2)0.0331 (6)
H24A0.29300.46470.21730.040*
C250.28633 (18)0.4018 (3)0.0804 (3)0.0496 (8)
H25A0.28070.46620.04560.074*
H25B0.25730.34990.04330.074*
H25C0.33710.38170.08890.074*
C260.2691 (2)0.3140 (2)0.2351 (3)0.0593 (10)
H26A0.25310.32270.29850.089*
H26B0.31980.29320.24370.089*
H26C0.23970.26220.19840.089*
Cl10.39614 (3)0.60550 (5)0.26626 (5)0.03066 (15)
Cl20.19247 (3)0.71492 (5)0.38646 (4)0.02861 (14)
Cr10.29054 (2)0.67426 (3)0.31096 (3)0.01897 (9)
N10.29772 (10)0.79602 (14)0.22866 (14)0.0200 (4)
N20.23010 (10)0.62865 (14)0.19125 (14)0.0191 (4)
N30.35525 (11)0.75068 (17)0.42260 (15)0.0273 (5)
C270.38699 (14)0.8105 (2)0.46731 (19)0.0298 (6)
C280.42740 (19)0.8893 (3)0.5229 (2)0.0474 (8)
H28A0.47900.87370.52930.071*
H28B0.41230.89320.58730.071*
H28C0.41830.95410.48980.071*
N40.29488 (12)0.54279 (17)0.39918 (16)0.0306 (5)
C290.30724 (16)0.4809 (2)0.4545 (2)0.0364 (6)
C300.3258 (2)0.4026 (3)0.5276 (3)0.0606 (10)
H30A0.37280.37350.52000.091*
H30B0.28910.34940.51960.091*
H30C0.32790.43230.59230.091*
U11U22U33U12U13U23
N50.094 (3)0.100 (4)0.139 (5)−0.025 (3)−0.018 (3)0.045 (3)
C310.072 (3)0.080 (3)0.063 (3)−0.039 (3)0.000 (2)0.012 (2)
C320.075 (3)0.072 (3)0.056 (2)−0.030 (2)0.005 (2)0.004 (2)
C10.0220 (11)0.0240 (12)0.0226 (12)0.0000 (9)0.0053 (9)0.0049 (9)
C20.0225 (11)0.0237 (12)0.0212 (11)0.0004 (9)0.0028 (9)0.0000 (9)
C30.0218 (11)0.0196 (11)0.0223 (12)−0.0035 (9)0.0004 (9)0.0033 (9)
C40.0244 (12)0.0209 (11)0.0284 (13)−0.0001 (9)0.0005 (10)0.0035 (10)
C50.0306 (13)0.0212 (12)0.0386 (15)0.0017 (10)0.0050 (11)0.0013 (11)
C60.0366 (14)0.0213 (12)0.0397 (15)−0.0096 (11)0.0020 (12)−0.0012 (11)
C70.0254 (13)0.0298 (14)0.0388 (15)−0.0088 (10)0.0028 (11)0.0012 (11)
C80.0235 (12)0.0268 (12)0.0290 (13)−0.0027 (10)0.0039 (10)0.0030 (10)
C90.0222 (12)0.0241 (13)0.0491 (17)0.0017 (10)0.0028 (11)−0.0021 (12)
C100.0368 (17)0.059 (2)0.075 (3)0.0022 (16)−0.0151 (17)0.0134 (19)
C110.0326 (16)0.0463 (18)0.079 (3)0.0003 (14)0.0208 (16)−0.0147 (17)
C120.0227 (12)0.0334 (14)0.0460 (16)−0.0069 (10)0.0104 (11)−0.0077 (12)
C130.0465 (18)0.053 (2)0.0511 (19)−0.0157 (15)0.0244 (15)−0.0143 (16)
C140.0292 (15)0.0533 (19)0.063 (2)0.0093 (14)0.0066 (14)−0.0056 (17)
C150.0253 (12)0.0227 (12)0.0188 (11)−0.0049 (9)0.0026 (9)−0.0016 (9)
C160.0210 (11)0.0328 (13)0.0232 (12)−0.0038 (10)0.0023 (9)−0.0027 (10)
C170.0255 (13)0.0437 (16)0.0335 (15)−0.0083 (12)0.0027 (11)−0.0029 (12)
C180.0350 (15)0.0412 (16)0.0402 (16)−0.0197 (13)0.0034 (13)−0.0052 (13)
C190.0450 (17)0.0249 (13)0.0415 (16)−0.0119 (12)0.0035 (13)−0.0029 (12)
C200.0345 (14)0.0241 (12)0.0254 (13)−0.0051 (10)0.0028 (10)−0.0013 (10)
C210.0205 (12)0.0336 (14)0.0332 (14)0.0015 (10)0.0013 (10)−0.0064 (11)
C220.0350 (15)0.0423 (16)0.0419 (17)0.0061 (13)0.0013 (13)0.0014 (13)
C230.0336 (15)0.059 (2)0.0427 (17)0.0101 (14)0.0077 (13)−0.0114 (15)
C240.0373 (15)0.0211 (12)0.0394 (15)0.0021 (11)−0.0006 (12)−0.0004 (11)
C250.0441 (18)0.054 (2)0.051 (2)0.0076 (15)0.0073 (15)−0.0061 (16)
C260.062 (2)0.0332 (17)0.081 (3)0.0076 (16)0.004 (2)0.0178 (17)
Cl10.0237 (3)0.0302 (3)0.0383 (4)0.0063 (2)0.0051 (2)0.0025 (3)
Cl20.0267 (3)0.0366 (3)0.0235 (3)−0.0023 (2)0.0070 (2)−0.0041 (2)
Cr10.01892 (18)0.01898 (18)0.01855 (18)−0.00166 (14)0.00090 (13)0.00088 (15)
N10.0169 (9)0.0181 (9)0.0250 (10)−0.0013 (7)0.0035 (8)−0.0003 (8)
N20.0195 (9)0.0176 (9)0.0205 (10)−0.0011 (7)0.0032 (8)−0.0017 (8)
N30.0277 (11)0.0304 (11)0.0227 (11)−0.0039 (9)−0.0009 (9)0.0016 (9)
C270.0304 (13)0.0353 (15)0.0234 (13)−0.0050 (11)0.0024 (10)0.0041 (11)
C280.057 (2)0.0473 (18)0.0369 (17)−0.0224 (16)0.0029 (15)−0.0106 (14)
N40.0340 (12)0.0283 (11)0.0291 (12)−0.0043 (9)0.0029 (9)0.0024 (10)
C290.0433 (16)0.0306 (14)0.0344 (15)−0.0051 (12)0.0018 (12)0.0042 (12)
C300.078 (3)0.046 (2)0.054 (2)−0.0021 (18)−0.0039 (19)0.0248 (17)
N5—C311.115 (6)C16—C171.391 (4)
C31—C321.441 (7)C16—C211.519 (4)
C32—H32A0.9800C17—C181.376 (4)
C32—H32B0.9800C17—H17A0.9500
C32—H32C0.9800C18—C191.379 (4)
C1—N11.331 (3)C18—H18A0.9500
C1—C21.390 (3)C19—C201.397 (4)
C1—H1A0.9500C19—H19A0.9500
C2—N21.338 (3)C20—C241.512 (4)
C2—H2A0.9500C21—C231.533 (4)
C3—C81.409 (3)C21—C221.537 (4)
C3—C41.411 (3)C21—H21A1.0000
C3—N11.443 (3)C22—H22A0.9800
C4—C51.384 (3)C22—H22B0.9800
C4—C91.519 (3)C22—H22C0.9800
C5—C61.392 (4)C23—H23A0.9800
C5—H5A0.9500C23—H23B0.9800
C6—C71.379 (4)C23—H23C0.9800
C6—H6A0.9500C24—C261.528 (4)
C7—C81.399 (4)C24—C251.534 (4)
C7—H7A0.9500C24—H24A1.0000
C8—C121.511 (4)C25—H25A0.9800
C9—C101.529 (4)C25—H25B0.9800
C9—C111.530 (4)C25—H25C0.9800
C9—H9A1.0000C26—H26A0.9800
C10—H10A0.9800C26—H26B0.9800
C10—H10B0.9800C26—H26C0.9800
C10—H10C0.9800Cl1—Cr12.3382 (7)
C11—H11A0.9800Cl2—Cr12.3029 (7)
C11—H11B0.9800Cr1—N21.9806 (19)
C11—H11C0.9800Cr1—N11.995 (2)
C12—C141.528 (4)Cr1—N32.099 (2)
C12—C131.530 (4)Cr1—N42.128 (2)
C12—H12A1.0000N3—C271.127 (3)
C13—H13A0.9800C27—C281.450 (4)
C13—H13B0.9800C28—H28A0.9800
C13—H13C0.9800C28—H28B0.9800
C14—H14A0.9800C28—H28C0.9800
C14—H14B0.9800N4—C291.128 (4)
C14—H14C0.9800C29—C301.465 (4)
C15—C201.406 (3)C30—H30A0.9800
C15—C161.417 (3)C30—H30B0.9800
C15—N21.441 (3)C30—H30C0.9800
N5—C31—C32179.4 (6)C18—C19—C20121.3 (3)
C31—C32—H32A109.5C18—C19—H19A119.3
C31—C32—H32B109.5C20—C19—H19A119.3
H32A—C32—H32B109.5C19—C20—C15118.0 (3)
C31—C32—H32C109.5C19—C20—C24120.6 (2)
H32A—C32—H32C109.5C15—C20—C24121.2 (2)
H32B—C32—H32C109.5C16—C21—C23112.0 (2)
N1—C1—C2116.0 (2)C16—C21—C22111.0 (2)
N1—C1—H1A122.0C23—C21—C22109.8 (2)
C2—C1—H1A122.0C16—C21—H21A108.0
N2—C2—C1116.5 (2)C23—C21—H21A108.0
N2—C2—H2A121.7C22—C21—H21A108.0
C1—C2—H2A121.8C21—C22—H22A109.5
C8—C3—C4121.2 (2)C21—C22—H22B109.5
C8—C3—N1120.4 (2)H22A—C22—H22B109.5
C4—C3—N1118.4 (2)C21—C22—H22C109.5
C5—C4—C3118.4 (2)H22A—C22—H22C109.5
C5—C4—C9119.9 (2)H22B—C22—H22C109.5
C3—C4—C9121.4 (2)C21—C23—H23A109.5
C4—C5—C6121.1 (2)C21—C23—H23B109.5
C4—C5—H5A119.4H23A—C23—H23B109.5
C6—C5—H5A119.4C21—C23—H23C109.5
C7—C6—C5119.9 (2)H23A—C23—H23C109.5
C7—C6—H6A120.0H23B—C23—H23C109.5
C5—C6—H6A120.0C20—C24—C26112.8 (3)
C6—C7—C8121.3 (2)C20—C24—C25110.0 (2)
C6—C7—H7A119.4C26—C24—C25110.2 (3)
C8—C7—H7A119.4C20—C24—H24A107.9
C7—C8—C3118.0 (2)C26—C24—H24A107.9
C7—C8—C12119.1 (2)C25—C24—H24A107.9
C3—C8—C12122.9 (2)C24—C25—H25A109.5
C4—C9—C10109.0 (2)C24—C25—H25B109.5
C4—C9—C11113.6 (2)H25A—C25—H25B109.5
C10—C9—C11111.4 (3)C24—C25—H25C109.5
C4—C9—H9A107.5H25A—C25—H25C109.5
C10—C9—H9A107.5H25B—C25—H25C109.5
C11—C9—H9A107.5C24—C26—H26A109.5
C9—C10—H10A109.5C24—C26—H26B109.5
C9—C10—H10B109.5H26A—C26—H26B109.5
H10A—C10—H10B109.5C24—C26—H26C109.5
C9—C10—H10C109.5H26A—C26—H26C109.5
H10A—C10—H10C109.5H26B—C26—H26C109.5
H10B—C10—H10C109.5N2—Cr1—N180.59 (8)
C9—C11—H11A109.5N2—Cr1—N3168.26 (8)
C9—C11—H11B109.5N1—Cr1—N387.72 (8)
H11A—C11—H11B109.5N2—Cr1—N4102.18 (8)
C9—C11—H11C109.5N1—Cr1—N4173.95 (8)
H11A—C11—H11C109.5N3—Cr1—N489.57 (9)
H11B—C11—H11C109.5N2—Cr1—Cl293.30 (6)
C8—C12—C14111.3 (2)N1—Cr1—Cl2101.24 (6)
C8—C12—C13111.2 (2)N3—Cr1—Cl287.90 (6)
C14—C12—C13110.5 (2)N4—Cr1—Cl284.06 (7)
C8—C12—H12A107.9N2—Cr1—Cl193.62 (6)
C14—C12—H12A107.9N1—Cr1—Cl192.03 (6)
C13—C12—H12A107.9N3—Cr1—Cl187.83 (6)
C12—C13—H13A109.5N4—Cr1—Cl182.46 (7)
C12—C13—H13B109.5Cl2—Cr1—Cl1165.88 (3)
H13A—C13—H13B109.5C1—N1—C3117.9 (2)
C12—C13—H13C109.5C1—N1—Cr1111.36 (15)
H13A—C13—H13C109.5C3—N1—Cr1130.52 (15)
H13B—C13—H13C109.5C2—N2—C15114.74 (19)
C12—C14—H14A109.5C2—N2—Cr1111.55 (15)
C12—C14—H14B109.5C15—N2—Cr1132.96 (15)
H14A—C14—H14B109.5C27—N3—Cr1163.3 (2)
C12—C14—H14C109.5N3—C27—C28178.6 (3)
H14A—C14—H14C109.5C27—C28—H28A109.5
H14B—C14—H14C109.5C27—C28—H28B109.5
C20—C15—C16121.2 (2)H28A—C28—H28B109.5
C20—C15—N2120.1 (2)C27—C28—H28C109.5
C16—C15—N2118.6 (2)H28A—C28—H28C109.5
C17—C16—C15117.8 (2)H28B—C28—H28C109.5
C17—C16—C21119.0 (2)C29—N4—Cr1168.1 (2)
C15—C16—C21123.2 (2)N4—C29—C30177.9 (3)
C18—C17—C16121.6 (3)C29—C30—H30A109.5
C18—C17—H17A119.2C29—C30—H30B109.5
C16—C17—H17A119.2H30A—C30—H30B109.5
C17—C18—C19120.1 (3)C29—C30—H30C109.5
C17—C18—H18A120.0H30A—C30—H30C109.5
C19—C18—H18A120.0H30B—C30—H30C109.5
  3 in total

1.  The shortest metal-metal bond yet: molecular and electronic structure of a dinuclear chromium diazadiene complex.

Authors:  Kevin A Kreisel; Glenn P A Yap; Olga Dmitrenko; Clark R Landis; Klaus H Theopold
Journal:  J Am Chem Soc       Date:  2007-10-30       Impact factor: 15.419

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  (Alpha-diimine)chromium complexes: molecular and electronic structures; a combined experimental and density functional theoretical study.

Authors:  Meenakshi Ghosh; Stephen Sproules; Thomas Weyhermüller; Karl Wieghardt
Journal:  Inorg Chem       Date:  2008-05-28       Impact factor: 5.165

  3 in total
  1 in total

1.  Bis[N,N'-bis-(2,6-diisopropyl-phen-yl)ethane-1,2-diimine]-1κN,N';2κN,N'-tri-μ-trichlorido-1:2κCl:Cl-chlorido-1κCl-tetra-hydro-furan-2κO-dichromium(II) dichloro-methane 4.5-solvate.

Authors:  Stephan Peitz; Normen Peulecke; Bernd H Müller; Anke Spannenberg; Uwe Rosenthal
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-11-14
  1 in total

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