Literature DB >> 21523119

Tris(biphenyl-4-yl)arsane.

Omar Bin Shawkataly, Imthyaz Ahmed Khan, Siti Syaida Sirat, Chin Sing Yeap, Hoong-Kun Fun.   

Abstract

The asymmetric unit of title compound, C(36)H(27)As, contains two crystallographically independent mol-ecules, A and B, with similar conformations. The two phenyl rings of each biphenyl unit are twisted slightly away from each other with dihedral angles of 6.0 (2), 27.7 (3) and 33.4 (2)° in mol-ecule A and 5.7 (3), 27.5 (2) and 33.0 (2)° in mol-ecule B. The As-bonded phenyl rings make dihedral angles of 54.9 (2), 76.0 (2) and 88.2 (2),° with each other in mol-ecule A, and 60.3 (2), 78.1 (2) and 79.5 (2)° in mol-ecule B. In the crystal, the mol-ecules are stacked down the b axis. Weak inter-molecular C-H⋯π inter-actions stabilize the crystal structure. The crystal studied was a racemic twin, the refined ratio of twin components being 0.461 (7):0.539 (7).

Entities:  

Year:  2011        PMID: 21523119      PMCID: PMC3051659          DOI: 10.1107/S160053681100211X

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


Related literature

For structures of related tris­aryl arsane derivatives, see: Cullen et al. (1995 ▶); Shawkataly et al. (2010a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C36H27As M = 534.50 Monoclinic, a = 17.3718 (19) Å b = 5.9561 (8) Å c = 27.727 (3) Å β = 114.762 (5)° V = 2605.1 (5) Å3 Z = 4 Mo Kα radiation μ = 1.33 mm−1 T = 100 K 0.33 × 0.07 × 0.03 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.671, T max = 0.961 23087 measured reflections 11576 independent reflections 8126 reflections with I > 2σ(I)’ R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.045 wR(F 2) = 0.093 S = 1.01 11576 reflections 668 parameters 2 restraints H-atom parameters constrained Δρmax = 0.56 e Å−3 Δρmin = −0.75 e Å−3 Absolute structure: Flack (1983 ▶), 5634 Friedel pairs Flack parameter: 0.461 (7) Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681100211X/ng5092sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053681100211X/ng5092Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C36H27AsF(000) = 1104
Mr = 534.50Dx = 1.363 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 4340 reflections
a = 17.3718 (19) Åθ = 2.4–26.2°
b = 5.9561 (8) ŵ = 1.33 mm1
c = 27.727 (3) ÅT = 100 K
β = 114.762 (5)°Needle, colourless
V = 2605.1 (5) Å30.33 × 0.07 × 0.03 mm
Z = 4
Bruker APEXII DUO CCD area-detector diffractometer11576 independent reflections
Radiation source: fine-focus sealed tube8126 reflections with I > 2σ(I)'
graphiteRint = 0.057
φ and ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −22→22
Tmin = 0.671, Tmax = 0.961k = −7→7
23087 measured reflectionsl = −35→36
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.093w = 1/[σ2(Fo2) + (0.0318P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
11576 reflectionsΔρmax = 0.56 e Å3
668 parametersΔρmin = −0.75 e Å3
2 restraintsAbsolute structure: Flack (1983), 5634 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.461 (7)
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.
xyzUiso*/Ueq
As1A0.194411 (19)0.60795 (9)0.860597 (14)0.01986 (13)
C1A0.0224 (3)0.2913 (8)0.90946 (16)0.0243 (10)
H1A−0.03050.32820.90810.029*
C2A0.0615 (3)0.4369 (8)0.88744 (16)0.0239 (11)
H2A0.03450.57010.87190.029*
C3A0.1404 (3)0.3872 (9)0.88811 (19)0.0193 (13)
C4A0.1800 (3)0.1885 (8)0.91370 (15)0.0215 (10)
H4A0.23350.15270.91590.026*
C5A0.1410 (3)0.0459 (7)0.93548 (15)0.0212 (10)
H5A0.1687−0.08500.95200.025*
C6A0.0607 (3)0.0928 (8)0.93336 (15)0.0176 (9)
C7A0.0188 (3)−0.0670 (8)0.95564 (16)0.0237 (10)
C8A0.0649 (3)−0.2009 (8)0.99967 (16)0.0273 (10)
H8A0.1236−0.18761.01580.033*
C9A0.0260 (3)−0.3526 (8)1.02006 (18)0.0346 (12)
H9A0.0585−0.43931.04950.042*
C10A−0.0613 (3)−0.3752 (9)0.99666 (19)0.0397 (13)
H10A−0.0882−0.47411.01060.048*
C11A−0.1079 (4)−0.2480 (10)0.9522 (2)0.0341 (14)
H11A−0.1664−0.26530.93570.041*
C12A−0.0698 (3)−0.0975 (9)0.9320 (2)0.0288 (13)
H12A−0.1028−0.01370.90220.035*
C13A−0.0044 (3)0.9509 (8)0.73934 (16)0.0196 (10)
H13A−0.02941.09080.73700.024*
C14A0.0582 (2)0.8804 (8)0.78741 (15)0.0231 (9)
H14A0.07370.97410.81680.028*
C15A0.0985 (3)0.6743 (8)0.79307 (18)0.0194 (11)
C16A0.0697 (3)0.5329 (8)0.74858 (16)0.0224 (10)
H16A0.09380.39140.75120.027*
C17A0.0061 (3)0.6006 (8)0.70083 (16)0.0225 (9)
H17A−0.01300.50150.67230.027*
C18A−0.0302 (3)0.8138 (8)0.69438 (16)0.0200 (9)
C19A−0.0926 (2)0.8984 (8)0.64179 (15)0.0220 (9)
C20A−0.0917 (3)0.8198 (10)0.59537 (18)0.0487 (16)
H20A−0.05290.70980.59660.058*
C21A−0.1487 (4)0.9040 (11)0.54635 (19)0.063 (2)
H21A−0.14720.85110.51520.075*
C22A−0.2074 (3)1.0657 (10)0.54385 (18)0.0485 (16)
H22A−0.24571.12070.51120.058*
C23A−0.2088 (3)1.1427 (8)0.58916 (17)0.0283 (11)
H23A−0.24851.25030.58770.034*
C24A−0.1514 (3)1.0629 (8)0.63790 (17)0.0275 (11)
H24A−0.15231.12100.66880.033*
C25A0.3887 (3)0.4234 (8)0.81806 (15)0.0216 (10)
H25A0.43780.49630.82080.026*
C26A0.3378 (3)0.5241 (8)0.83881 (15)0.0216 (10)
H26A0.35350.66330.85520.026*
C27A0.2637 (3)0.4242 (8)0.83604 (16)0.0189 (11)
C28A0.2452 (3)0.2124 (8)0.81276 (16)0.0212 (10)
H28A0.19710.13800.81110.025*
C29A0.2958 (3)0.1095 (8)0.79215 (17)0.0216 (10)
H29A0.2815−0.03290.77730.026*
C30A0.3684 (3)0.2149 (8)0.79310 (15)0.0183 (9)
C31A0.4232 (2)0.1064 (8)0.77069 (14)0.0181 (9)
C32A0.3995 (3)−0.0934 (8)0.74170 (16)0.0230 (10)
H32A0.3476−0.15810.73580.028*
C33A0.4514 (3)−0.1994 (9)0.72121 (18)0.0281 (12)
H33A0.4349−0.33480.70310.034*
C34A0.5278 (3)−0.1000 (8)0.72826 (15)0.0245 (10)
H34A0.5625−0.16730.71440.029*
C35A0.5515 (3)0.0987 (8)0.75584 (16)0.0279 (10)
H35A0.60230.16610.76030.033*
C36A0.5009 (3)0.2000 (8)0.77705 (16)0.0249 (10)
H36A0.51890.33320.79600.030*
As1B0.42591 (2)−0.11085 (9)0.505294 (14)0.02100 (13)
C1B0.5352 (3)0.1100 (9)0.40554 (17)0.0323 (11)
H1BA0.53530.05480.37420.039*
C2B0.4891 (3)−0.0029 (8)0.42850 (16)0.0280 (11)
H2BA0.4597−0.13280.41270.034*
C3B0.4866 (3)0.0761 (9)0.4747 (2)0.0210 (12)
C4B0.5299 (3)0.2709 (8)0.49691 (18)0.0355 (13)
H4BA0.52770.32910.52740.043*
C6B0.5810 (3)0.3018 (8)0.42787 (17)0.0195 (10)
C7B0.6335 (3)0.4195 (8)0.40412 (15)0.0202 (9)
C8B0.6727 (3)0.6205 (9)0.4241 (2)0.0333 (15)
H8BA0.66640.68630.45260.040*
C9B0.7224 (4)0.7278 (11)0.4019 (2)0.0391 (15)
H9BA0.74910.86290.41610.047*
C10B0.7315 (3)0.6348 (10)0.35979 (18)0.0393 (13)
H10B0.76430.70620.34520.047*
C11B0.6919 (3)0.4344 (9)0.33885 (18)0.0390 (13)
H11B0.69790.37040.31000.047*
C12B0.6430 (3)0.3281 (9)0.36081 (17)0.0336 (12)
H12B0.61620.19340.34630.040*
C13B0.3642 (2)0.2341 (7)0.61791 (15)0.0207 (10)
H13B0.37830.22220.65410.025*
C14B0.4049 (2)0.0969 (8)0.59546 (14)0.0205 (9)
H14B0.4450−0.00650.61650.025*
C15B0.3863 (3)0.1127 (8)0.54223 (17)0.0201 (11)
C16B0.3278 (3)0.2738 (8)0.51198 (16)0.0238 (10)
H16B0.31650.29060.47630.029*
C17B0.2864 (3)0.4092 (8)0.53410 (16)0.0238 (10)
H17B0.24720.51450.51300.029*
C18B0.3027 (3)0.3896 (8)0.58774 (17)0.0187 (10)
C19B0.2561 (3)0.5226 (8)0.61262 (16)0.0191 (10)
C20B0.2213 (3)0.7349 (8)0.59293 (17)0.0265 (11)
H20B0.22840.79580.56420.032*
C21B0.1770 (3)0.8532 (8)0.61548 (18)0.0315 (11)
H21B0.15430.99290.60200.038*
C22B0.1660 (3)0.7640 (9)0.6586 (2)0.0331 (13)
H22B0.13550.84380.67360.040*
C23B0.2001 (3)0.5589 (8)0.67895 (18)0.0292 (11)
H23B0.19360.50050.70810.035*
C24B0.2442 (3)0.4392 (7)0.65571 (16)0.0219 (10)
H24B0.26640.29930.66940.026*
C25B0.6718 (3)−0.3161 (8)0.61583 (16)0.0244 (10)
H25B0.7279−0.29260.62150.029*
C26B0.6075 (3)−0.2017 (7)0.57495 (16)0.0219 (9)
H26B0.6207−0.10310.55350.026*
C27B0.5232 (3)−0.2357 (8)0.56627 (18)0.0201 (11)
C28B0.5052 (2)−0.3878 (7)0.59828 (14)0.0194 (9)
H28B0.4492−0.41620.59200.023*
C29B0.5700 (3)−0.4972 (8)0.63944 (16)0.0208 (10)
H29B0.5569−0.59370.66130.025*
C30B0.6540 (3)−0.4650 (8)0.64851 (18)0.0215 (11)
C31B0.7221 (3)−0.5891 (8)0.69188 (15)0.0209 (9)
C32B0.7091 (3)−0.8021 (8)0.70683 (16)0.0267 (10)
H32B0.6574−0.87330.68810.032*
C33B0.7726 (3)−0.9123 (9)0.74970 (17)0.0325 (12)
H33B0.7627−1.05530.75930.039*
C34B0.8492 (3)−0.8102 (10)0.77748 (17)0.0338 (12)
H34B0.8912−0.88300.80610.041*
C35B0.8638 (3)−0.5993 (10)0.76277 (17)0.0348 (12)
H35B0.9159−0.52990.78120.042*
C36B0.8010 (3)−0.4914 (9)0.72080 (17)0.0272 (11)
H36B0.8117−0.34860.71140.033*
C56B0.5767 (3)0.3802 (9)0.47409 (19)0.0343 (12)
H56A0.60610.50990.49010.041*
U11U22U33U12U13U23
As1A0.0202 (3)0.0222 (3)0.0152 (3)−0.0001 (3)0.0055 (2)−0.0024 (3)
C1A0.022 (2)0.031 (3)0.021 (2)0.006 (2)0.010 (2)0.003 (2)
C2A0.022 (2)0.027 (3)0.021 (2)0.008 (2)0.0072 (18)0.0036 (19)
C3A0.021 (3)0.026 (3)0.010 (2)−0.003 (2)0.006 (2)−0.005 (2)
C4A0.018 (2)0.026 (3)0.018 (2)0.0065 (19)0.0052 (18)0.0014 (19)
C5A0.027 (2)0.020 (3)0.012 (2)0.0010 (19)0.0043 (18)−0.0027 (17)
C6A0.020 (2)0.020 (3)0.010 (2)−0.001 (2)0.0040 (17)−0.0006 (19)
C7A0.025 (2)0.025 (3)0.022 (2)−0.002 (2)0.0112 (19)−0.002 (2)
C8A0.027 (2)0.028 (3)0.020 (2)−0.001 (2)0.0039 (19)0.002 (2)
C9A0.038 (3)0.035 (3)0.028 (2)0.000 (2)0.011 (2)0.009 (2)
C10A0.043 (3)0.040 (3)0.038 (3)−0.006 (3)0.018 (2)0.008 (3)
C11A0.029 (3)0.042 (4)0.034 (3)−0.012 (3)0.016 (2)0.001 (3)
C12A0.019 (2)0.042 (4)0.021 (2)0.001 (3)0.004 (2)0.003 (2)
C13A0.024 (2)0.018 (3)0.020 (2)0.004 (2)0.012 (2)0.003 (2)
C14A0.026 (2)0.025 (3)0.021 (2)−0.008 (2)0.0121 (18)−0.009 (2)
C15A0.021 (2)0.020 (3)0.022 (2)−0.004 (2)0.014 (2)−0.003 (2)
C16A0.024 (2)0.021 (2)0.022 (2)0.0019 (19)0.0093 (19)0.0019 (19)
C17A0.030 (2)0.020 (2)0.018 (2)0.000 (2)0.0109 (18)−0.006 (2)
C18A0.019 (2)0.019 (2)0.021 (2)−0.0030 (18)0.0086 (19)−0.0041 (19)
C19A0.021 (2)0.025 (2)0.019 (2)0.003 (2)0.0061 (17)0.001 (2)
C20A0.065 (4)0.054 (4)0.021 (2)0.035 (3)0.012 (2)−0.002 (2)
C21A0.083 (4)0.076 (5)0.019 (3)0.048 (4)0.011 (3)−0.001 (3)
C22A0.055 (3)0.058 (4)0.017 (2)0.023 (3)0.000 (2)0.004 (3)
C23A0.025 (2)0.033 (3)0.026 (2)0.008 (2)0.010 (2)0.005 (2)
C24A0.030 (3)0.033 (3)0.021 (2)−0.001 (2)0.011 (2)0.000 (2)
C25A0.020 (2)0.030 (3)0.016 (2)−0.001 (2)0.0076 (17)0.0003 (19)
C26A0.022 (2)0.022 (3)0.015 (2)−0.0044 (19)0.0025 (18)−0.0039 (19)
C27A0.022 (3)0.021 (3)0.008 (2)−0.001 (2)0.0004 (19)0.0051 (19)
C28A0.020 (2)0.023 (3)0.020 (2)−0.005 (2)0.0087 (19)−0.003 (2)
C29A0.024 (2)0.020 (2)0.024 (3)0.002 (2)0.013 (2)0.001 (2)
C30A0.021 (2)0.024 (3)0.0082 (19)0.006 (2)0.0052 (17)0.0048 (19)
C31A0.021 (2)0.021 (2)0.0103 (18)0.000 (2)0.0048 (16)0.0037 (19)
C32A0.028 (2)0.020 (3)0.023 (2)0.000 (2)0.013 (2)0.001 (2)
C33A0.033 (3)0.031 (3)0.019 (2)0.000 (2)0.009 (2)−0.006 (2)
C34A0.025 (2)0.035 (3)0.016 (2)0.007 (2)0.0110 (18)0.004 (2)
C35A0.025 (2)0.041 (3)0.023 (2)−0.005 (2)0.0146 (19)−0.004 (2)
C36A0.024 (2)0.032 (3)0.021 (2)0.000 (2)0.0116 (19)−0.004 (2)
As1B0.0238 (3)0.0237 (3)0.0139 (2)−0.0034 (3)0.0064 (2)−0.0017 (3)
C1B0.048 (3)0.034 (3)0.021 (2)−0.014 (3)0.020 (2)−0.009 (2)
C2B0.036 (3)0.028 (3)0.018 (2)−0.011 (2)0.009 (2)−0.010 (2)
C3B0.024 (3)0.021 (3)0.016 (3)0.004 (2)0.006 (2)0.003 (2)
C4B0.069 (4)0.026 (3)0.023 (2)−0.016 (3)0.031 (3)−0.015 (2)
C6B0.024 (2)0.023 (3)0.013 (2)0.001 (2)0.0090 (19)0.001 (2)
C7B0.021 (2)0.024 (3)0.014 (2)0.001 (2)0.0065 (17)0.0011 (19)
C8B0.044 (4)0.034 (4)0.028 (3)−0.008 (3)0.021 (3)−0.005 (3)
C9B0.041 (3)0.044 (4)0.032 (3)−0.005 (3)0.015 (3)0.007 (3)
C10B0.033 (3)0.056 (4)0.032 (3)0.003 (3)0.016 (2)0.014 (3)
C11B0.048 (3)0.052 (4)0.024 (2)−0.005 (3)0.022 (2)−0.001 (2)
C12B0.041 (3)0.039 (3)0.027 (2)−0.003 (3)0.020 (2)−0.004 (2)
C13B0.026 (2)0.025 (3)0.0091 (19)0.002 (2)0.0049 (17)0.0058 (18)
C14B0.021 (2)0.026 (2)0.0121 (18)0.002 (2)0.0037 (16)0.0028 (19)
C15B0.017 (2)0.026 (3)0.014 (2)−0.005 (2)0.0028 (19)−0.002 (2)
C16B0.027 (2)0.027 (3)0.014 (2)−0.006 (2)0.0055 (19)−0.002 (2)
C17B0.023 (2)0.026 (3)0.018 (2)−0.002 (2)0.0034 (18)0.005 (2)
C18B0.015 (2)0.020 (2)0.020 (2)−0.003 (2)0.0070 (18)−0.001 (2)
C19B0.016 (2)0.022 (3)0.018 (2)−0.0008 (19)0.0058 (18)−0.0010 (19)
C20B0.031 (3)0.022 (3)0.025 (2)−0.001 (2)0.010 (2)0.003 (2)
C21B0.033 (3)0.025 (3)0.033 (3)0.005 (2)0.012 (2)−0.002 (2)
C22B0.033 (3)0.042 (4)0.029 (3)0.003 (3)0.018 (2)−0.001 (3)
C23B0.028 (2)0.035 (3)0.027 (2)−0.001 (2)0.014 (2)0.000 (2)
C24B0.024 (2)0.021 (3)0.022 (2)0.0000 (19)0.0108 (19)0.0031 (19)
C25B0.023 (2)0.024 (3)0.026 (2)−0.002 (2)0.0107 (19)−0.004 (2)
C26B0.027 (2)0.020 (2)0.020 (2)−0.004 (2)0.0112 (19)−0.0031 (19)
C27B0.025 (2)0.020 (3)0.016 (2)0.000 (2)0.009 (2)−0.002 (2)
C28B0.022 (2)0.017 (2)0.0171 (19)−0.006 (2)0.0051 (16)−0.0068 (19)
C29B0.027 (2)0.017 (2)0.022 (2)−0.0008 (19)0.014 (2)−0.0042 (19)
C30B0.022 (2)0.019 (3)0.021 (2)0.000 (2)0.006 (2)−0.002 (2)
C31B0.022 (2)0.026 (3)0.015 (2)0.005 (2)0.0089 (18)−0.004 (2)
C32B0.030 (2)0.030 (3)0.024 (2)0.002 (2)0.015 (2)0.000 (2)
C33B0.043 (3)0.036 (3)0.028 (2)0.016 (3)0.023 (2)0.010 (2)
C34B0.032 (3)0.052 (4)0.020 (2)0.019 (3)0.014 (2)0.007 (2)
C35B0.027 (3)0.051 (4)0.028 (2)0.000 (3)0.013 (2)−0.014 (3)
C36B0.027 (3)0.026 (3)0.025 (2)0.004 (2)0.008 (2)−0.005 (2)
C56B0.053 (3)0.024 (3)0.037 (3)−0.018 (3)0.030 (3)−0.010 (2)
As1A—C3A1.947 (5)As1B—C3B1.954 (5)
As1A—C27A1.949 (5)As1B—C27B1.968 (5)
As1A—C15A1.955 (5)As1B—C15B1.971 (5)
C1A—C6A1.382 (6)C1B—C6B1.381 (6)
C1A—C2A1.391 (6)C1B—C2B1.387 (6)
C1A—H1A0.9300C1B—H1BA0.9300
C2A—C3A1.394 (6)C2B—C3B1.383 (6)
C2A—H2A0.9300C2B—H2BA0.9300
C3A—C4A1.403 (6)C3B—C4B1.380 (7)
C4A—C5A1.373 (6)C4B—C56B1.383 (6)
C4A—H4A0.9300C4B—H4BA0.9300
C5A—C6A1.400 (6)C6B—C56B1.395 (6)
C5A—H5A0.9300C6B—C7B1.503 (6)
C6A—C7A1.482 (6)C7B—C8B1.374 (7)
C7A—C8A1.396 (6)C7B—C12B1.390 (6)
C7A—C12A1.409 (6)C8B—C9B1.405 (7)
C8A—C9A1.383 (6)C8B—H8BA0.9300
C8A—H8A0.9300C9B—C10B1.360 (7)
C9A—C10A1.384 (6)C9B—H9BA0.9300
C9A—H9A0.9300C10B—C11B1.379 (7)
C10A—C11A1.383 (7)C10B—H10B0.9300
C10A—H10A0.9300C11B—C12B1.387 (6)
C11A—C12A1.365 (7)C11B—H11B0.9300
C11A—H11A0.9300C12B—H12B0.9300
C12A—H12A0.9300C13B—C14B1.387 (5)
C13A—C14A1.386 (6)C13B—C18B1.396 (6)
C13A—C18A1.398 (6)C13B—H13B0.9300
C13A—H13A0.9300C14B—C15B1.376 (6)
C14A—C15A1.390 (6)C14B—H14B0.9300
C14A—H14A0.9300C15B—C16B1.393 (6)
C15A—C16A1.401 (6)C16B—C17B1.384 (6)
C16A—C17A1.383 (5)C16B—H16B0.9300
C16A—H16A0.9300C17B—C18B1.397 (5)
C17A—C18A1.395 (6)C17B—H17B0.9300
C17A—H17A0.9300C18B—C19B1.493 (6)
C18A—C19A1.494 (5)C19B—C24B1.387 (5)
C19A—C20A1.376 (6)C19B—C20B1.409 (6)
C19A—C24A1.387 (6)C20B—C21B1.372 (6)
C20A—C21A1.397 (7)C20B—H20B0.9300
C20A—H20A0.9300C21B—C22B1.391 (7)
C21A—C22A1.384 (7)C21B—H21B0.9300
C21A—H21A0.9300C22B—C23B1.372 (7)
C22A—C23A1.347 (6)C22B—H22B0.9300
C22A—H22A0.9300C23B—C24B1.387 (6)
C23A—C24A1.385 (6)C23B—H23B0.9300
C23A—H23A0.9300C24B—H24B0.9300
C24A—H24A0.9300C25B—C26B1.391 (6)
C25A—C26A1.378 (6)C25B—C30B1.392 (6)
C25A—C30A1.393 (6)C25B—H25B0.9300
C25A—H25A0.9300C26B—C27B1.397 (6)
C26A—C27A1.391 (6)C26B—H26B0.9300
C26A—H26A0.9300C27B—C28B1.392 (6)
C27A—C28A1.392 (6)C28B—C29B1.384 (6)
C28A—C29A1.378 (6)C28B—H28B0.9300
C28A—H28A0.9300C29B—C30B1.387 (6)
C29A—C30A1.399 (6)C29B—H29B0.9300
C29A—H29A0.9300C30B—C31B1.483 (6)
C30A—C31A1.484 (6)C31B—C32B1.382 (6)
C31A—C32A1.398 (6)C31B—C36B1.394 (6)
C31A—C36A1.402 (6)C32B—C33B1.401 (6)
C32A—C33A1.401 (6)C32B—H32B0.9300
C32A—H32A0.9300C33B—C34B1.370 (7)
C33A—C34A1.390 (6)C33B—H33B0.9300
C33A—H33A0.9300C34B—C35B1.376 (7)
C34A—C35A1.375 (6)C34B—H34B0.9300
C34A—H34A0.9300C35B—C36B1.376 (6)
C35A—C36A1.383 (6)C35B—H35B0.9300
C35A—H35A0.9300C36B—H36B0.9300
C36A—H36A0.9300C56B—H56A0.9300
C3A—As1A—C27A103.1 (2)C3B—As1B—C27B99.4 (2)
C3A—As1A—C15A98.9 (2)C3B—As1B—C15B102.1 (2)
C27A—As1A—C15A100.48 (18)C27B—As1B—C15B99.78 (19)
C6A—C1A—C2A121.2 (4)C6B—C1B—C2B122.0 (4)
C6A—C1A—H1A119.4C6B—C1B—H1BA119.0
C2A—C1A—H1A119.4C2B—C1B—H1BA119.0
C1A—C2A—C3A121.3 (4)C3B—C2B—C1B120.6 (5)
C1A—C2A—H2A119.3C3B—C2B—H2BA119.7
C3A—C2A—H2A119.3C1B—C2B—H2BA119.7
C2A—C3A—C4A117.2 (5)C4B—C3B—C2B118.4 (5)
C2A—C3A—As1A118.9 (4)C4B—C3B—As1B125.3 (4)
C4A—C3A—As1A123.6 (4)C2B—C3B—As1B116.1 (4)
C5A—C4A—C3A121.1 (4)C3B—C4B—C56B120.4 (4)
C5A—C4A—H4A119.5C3B—C4B—H4BA119.8
C3A—C4A—H4A119.5C56B—C4B—H4BA119.8
C4A—C5A—C6A121.6 (4)C1B—C6B—C56B116.5 (4)
C4A—C5A—H5A119.2C1B—C6B—C7B122.0 (4)
C6A—C5A—H5A119.2C56B—C6B—C7B121.5 (4)
C1A—C6A—C5A117.5 (4)C8B—C7B—C12B118.0 (4)
C1A—C6A—C7A121.8 (4)C8B—C7B—C6B121.3 (4)
C5A—C6A—C7A120.7 (4)C12B—C7B—C6B120.6 (4)
C8A—C7A—C12A116.6 (4)C7B—C8B—C9B120.9 (5)
C8A—C7A—C6A121.9 (4)C7B—C8B—H8BA119.6
C12A—C7A—C6A121.4 (4)C9B—C8B—H8BA119.6
C9A—C8A—C7A122.0 (4)C10B—C9B—C8B120.2 (6)
C9A—C8A—H8A119.0C10B—C9B—H9BA119.9
C7A—C8A—H8A119.0C8B—C9B—H9BA119.9
C8A—C9A—C10A120.0 (4)C9B—C10B—C11B119.8 (5)
C8A—C9A—H9A120.0C9B—C10B—H10B120.1
C10A—C9A—H9A120.0C11B—C10B—H10B120.1
C11A—C10A—C9A118.8 (5)C10B—C11B—C12B120.0 (5)
C11A—C10A—H10A120.6C10B—C11B—H11B120.0
C9A—C10A—H10A120.6C12B—C11B—H11B120.0
C12A—C11A—C10A121.5 (5)C11B—C12B—C7B121.1 (5)
C12A—C11A—H11A119.3C11B—C12B—H12B119.5
C10A—C11A—H11A119.3C7B—C12B—H12B119.5
C11A—C12A—C7A121.1 (5)C14B—C13B—C18B121.8 (4)
C11A—C12A—H12A119.4C14B—C13B—H13B119.1
C7A—C12A—H12A119.4C18B—C13B—H13B119.1
C14A—C13A—C18A120.7 (4)C15B—C14B—C13B120.4 (4)
C14A—C13A—H13A119.6C15B—C14B—H14B119.8
C18A—C13A—H13A119.6C13B—C14B—H14B119.8
C13A—C14A—C15A122.1 (4)C14B—C15B—C16B118.5 (4)
C13A—C14A—H14A119.0C14B—C15B—As1B122.3 (4)
C15A—C14A—H14A119.0C16B—C15B—As1B118.5 (3)
C14A—C15A—C16A117.0 (4)C17B—C16B—C15B121.2 (4)
C14A—C15A—As1A118.3 (3)C17B—C16B—H16B119.4
C16A—C15A—As1A124.6 (4)C15B—C16B—H16B119.4
C17A—C16A—C15A121.0 (4)C16B—C17B—C18B120.8 (4)
C17A—C16A—H16A119.5C16B—C17B—H17B119.6
C15A—C16A—H16A119.5C18B—C17B—H17B119.6
C16A—C17A—C18A121.7 (4)C13B—C18B—C17B117.2 (4)
C16A—C17A—H17A119.2C13B—C18B—C19B120.1 (4)
C18A—C17A—H17A119.2C17B—C18B—C19B122.7 (4)
C17A—C18A—C13A117.3 (4)C24B—C19B—C20B117.4 (4)
C17A—C18A—C19A122.4 (4)C24B—C19B—C18B120.9 (4)
C13A—C18A—C19A120.3 (4)C20B—C19B—C18B121.7 (4)
C20A—C19A—C24A117.7 (4)C21B—C20B—C19B121.0 (4)
C20A—C19A—C18A120.7 (4)C21B—C20B—H20B119.5
C24A—C19A—C18A121.6 (4)C19B—C20B—H20B119.5
C19A—C20A—C21A120.4 (5)C20B—C21B—C22B120.0 (5)
C19A—C20A—H20A119.8C20B—C21B—H21B120.0
C21A—C20A—H20A119.8C22B—C21B—H21B120.0
C22A—C21A—C20A120.4 (5)C23B—C22B—C21B120.2 (5)
C22A—C21A—H21A119.8C23B—C22B—H22B119.9
C20A—C21A—H21A119.8C21B—C22B—H22B119.9
C23A—C22A—C21A119.4 (5)C22B—C23B—C24B119.5 (4)
C23A—C22A—H22A120.3C22B—C23B—H23B120.2
C21A—C22A—H22A120.3C24B—C23B—H23B120.2
C22A—C23A—C24A120.5 (5)C19B—C24B—C23B121.8 (4)
C22A—C23A—H23A119.8C19B—C24B—H24B119.1
C24A—C23A—H23A119.8C23B—C24B—H24B119.1
C23A—C24A—C19A121.6 (4)C26B—C25B—C30B121.4 (4)
C23A—C24A—H24A119.2C26B—C25B—H25B119.3
C19A—C24A—H24A119.2C30B—C25B—H25B119.3
C26A—C25A—C30A121.4 (4)C25B—C26B—C27B119.7 (4)
C26A—C25A—H25A119.3C25B—C26B—H26B120.1
C30A—C25A—H25A119.3C27B—C26B—H26B120.1
C25A—C26A—C27A122.1 (4)C28B—C27B—C26B118.9 (4)
C25A—C26A—H26A118.9C28B—C27B—As1B116.9 (3)
C27A—C26A—H26A118.9C26B—C27B—As1B123.7 (3)
C26A—C27A—C28A116.2 (4)C29B—C28B—C27B120.7 (4)
C26A—C27A—As1A115.7 (4)C29B—C28B—H28B119.6
C28A—C27A—As1A127.9 (3)C27B—C28B—H28B119.6
C29A—C28A—C27A122.1 (4)C28B—C29B—C30B120.9 (4)
C29A—C28A—H28A118.9C28B—C29B—H29B119.5
C27A—C28A—H28A118.9C30B—C29B—H29B119.5
C28A—C29A—C30A121.3 (4)C29B—C30B—C25B118.3 (4)
C28A—C29A—H29A119.3C29B—C30B—C31B120.0 (4)
C30A—C29A—H29A119.3C25B—C30B—C31B121.7 (4)
C25A—C30A—C29A116.6 (4)C32B—C31B—C36B117.1 (4)
C25A—C30A—C31A121.5 (4)C32B—C31B—C30B121.7 (4)
C29A—C30A—C31A121.8 (4)C36B—C31B—C30B121.1 (4)
C32A—C31A—C36A116.5 (4)C31B—C32B—C33B121.0 (4)
C32A—C31A—C30A121.7 (4)C31B—C32B—H32B119.5
C36A—C31A—C30A121.8 (4)C33B—C32B—H32B119.5
C31A—C32A—C33A122.2 (4)C34B—C33B—C32B120.2 (5)
C31A—C32A—H32A118.9C34B—C33B—H33B119.9
C33A—C32A—H32A118.9C32B—C33B—H33B119.9
C34A—C33A—C32A119.3 (5)C33B—C34B—C35B119.6 (5)
C34A—C33A—H33A120.3C33B—C34B—H34B120.2
C32A—C33A—H33A120.3C35B—C34B—H34B120.2
C35A—C34A—C33A119.4 (4)C36B—C35B—C34B119.9 (5)
C35A—C34A—H34A120.3C36B—C35B—H35B120.0
C33A—C34A—H34A120.3C34B—C35B—H35B120.0
C34A—C35A—C36A121.1 (4)C35B—C36B—C31B122.1 (5)
C34A—C35A—H35A119.5C35B—C36B—H36B118.9
C36A—C35A—H35A119.5C31B—C36B—H36B118.9
C35A—C36A—C31A121.5 (4)C4B—C56B—C6B122.0 (5)
C35A—C36A—H36A119.2C4B—C56B—H56A119.0
C31A—C36A—H36A119.2C6B—C56B—H56A119.0
C6A—C1A—C2A—C3A0.7 (7)C6B—C1B—C2B—C3B0.9 (8)
C1A—C2A—C3A—C4A−2.3 (7)C1B—C2B—C3B—C4B0.9 (8)
C1A—C2A—C3A—As1A−176.1 (3)C1B—C2B—C3B—As1B−175.8 (4)
C27A—As1A—C3A—C2A−151.9 (3)C27B—As1B—C3B—C4B−70.3 (5)
C15A—As1A—C3A—C2A−48.9 (4)C15B—As1B—C3B—C4B31.9 (5)
C27A—As1A—C3A—C4A34.7 (4)C27B—As1B—C3B—C2B106.1 (4)
C15A—As1A—C3A—C4A137.8 (4)C15B—As1B—C3B—C2B−151.6 (4)
C2A—C3A—C4A—C5A2.2 (6)C2B—C3B—C4B—C56B−1.8 (8)
As1A—C3A—C4A—C5A175.6 (3)As1B—C3B—C4B—C56B174.6 (4)
C3A—C4A—C5A—C6A−0.3 (6)C2B—C1B—C6B—C56B−1.7 (7)
C2A—C1A—C6A—C5A1.2 (6)C2B—C1B—C6B—C7B177.7 (4)
C2A—C1A—C6A—C7A−178.2 (4)C1B—C6B—C7B—C8B174.3 (5)
C4A—C5A—C6A—C1A−1.4 (6)C56B—C6B—C7B—C8B−6.3 (7)
C4A—C5A—C6A—C7A178.1 (4)C1B—C6B—C7B—C12B−5.1 (7)
C1A—C6A—C7A—C8A−148.3 (4)C56B—C6B—C7B—C12B174.3 (5)
C5A—C6A—C7A—C8A32.2 (6)C12B—C7B—C8B—C9B−1.2 (8)
C1A—C6A—C7A—C12A34.2 (7)C6B—C7B—C8B—C9B179.3 (5)
C5A—C6A—C7A—C12A−145.3 (5)C7B—C8B—C9B—C10B0.7 (9)
C12A—C7A—C8A—C9A−1.4 (7)C8B—C9B—C10B—C11B−0.1 (8)
C6A—C7A—C8A—C9A−179.0 (4)C9B—C10B—C11B—C12B−0.1 (8)
C7A—C8A—C9A—C10A0.0 (7)C10B—C11B—C12B—C7B−0.4 (8)
C8A—C9A—C10A—C11A1.6 (8)C8B—C7B—C12B—C11B1.1 (7)
C9A—C10A—C11A—C12A−1.8 (8)C6B—C7B—C12B—C11B−179.5 (4)
C10A—C11A—C12A—C7A0.4 (9)C18B—C13B—C14B—C15B0.9 (7)
C8A—C7A—C12A—C11A1.2 (8)C13B—C14B—C15B—C16B1.9 (6)
C6A—C7A—C12A—C11A178.8 (5)C13B—C14B—C15B—As1B−168.8 (3)
C18A—C13A—C14A—C15A0.8 (7)C3B—As1B—C15B—C14B−124.3 (4)
C13A—C14A—C15A—C16A−3.7 (6)C27B—As1B—C15B—C14B−22.4 (4)
C13A—C14A—C15A—As1A173.2 (3)C3B—As1B—C15B—C16B64.9 (4)
C3A—As1A—C15A—C14A107.7 (4)C27B—As1B—C15B—C16B166.8 (4)
C27A—As1A—C15A—C14A−147.1 (4)C14B—C15B—C16B—C17B−2.7 (7)
C3A—As1A—C15A—C16A−75.6 (4)As1B—C15B—C16B—C17B168.4 (3)
C27A—As1A—C15A—C16A29.6 (4)C15B—C16B—C17B—C18B0.6 (7)
C14A—C15A—C16A—C17A2.3 (6)C14B—C13B—C18B—C17B−2.9 (6)
As1A—C15A—C16A—C17A−174.4 (3)C14B—C13B—C18B—C19B175.7 (4)
C15A—C16A—C17A—C18A2.0 (6)C16B—C17B—C18B—C13B2.1 (6)
C16A—C17A—C18A—C13A−4.9 (6)C16B—C17B—C18B—C19B−176.4 (4)
C16A—C17A—C18A—C19A173.6 (4)C13B—C18B—C19B—C24B−27.3 (6)
C14A—C13A—C18A—C17A3.5 (6)C17B—C18B—C19B—C24B151.1 (4)
C14A—C13A—C18A—C19A−175.1 (4)C13B—C18B—C19B—C20B153.7 (4)
C17A—C18A—C19A—C20A−27.3 (7)C17B—C18B—C19B—C20B−27.8 (6)
C13A—C18A—C19A—C20A151.2 (5)C24B—C19B—C20B—C21B−0.4 (6)
C17A—C18A—C19A—C24A154.8 (4)C18B—C19B—C20B—C21B178.6 (4)
C13A—C18A—C19A—C24A−26.8 (6)C19B—C20B—C21B—C22B0.2 (7)
C24A—C19A—C20A—C21A−0.2 (8)C20B—C21B—C22B—C23B0.6 (7)
C18A—C19A—C20A—C21A−178.3 (5)C21B—C22B—C23B—C24B−1.1 (7)
C19A—C20A—C21A—C22A−0.8 (10)C20B—C19B—C24B—C23B−0.2 (6)
C20A—C21A—C22A—C23A0.5 (10)C18B—C19B—C24B—C23B−179.1 (4)
C21A—C22A—C23A—C24A0.7 (9)C22B—C23B—C24B—C19B0.9 (7)
C22A—C23A—C24A—C19A−1.7 (8)C30B—C25B—C26B—C27B0.1 (6)
C20A—C19A—C24A—C23A1.4 (7)C25B—C26B—C27B—C28B−1.3 (6)
C18A—C19A—C24A—C23A179.5 (4)C25B—C26B—C27B—As1B−173.0 (3)
C30A—C25A—C26A—C27A0.0 (6)C3B—As1B—C27B—C28B−178.3 (4)
C25A—C26A—C27A—C28A2.2 (6)C15B—As1B—C27B—C28B77.6 (4)
C25A—C26A—C27A—As1A−173.5 (3)C3B—As1B—C27B—C26B−6.4 (4)
C3A—As1A—C27A—C26A−149.4 (3)C15B—As1B—C27B—C26B−110.5 (4)
C15A—As1A—C27A—C26A108.8 (3)C26B—C27B—C28B—C29B2.5 (6)
C3A—As1A—C27A—C28A35.5 (4)As1B—C27B—C28B—C29B174.8 (3)
C15A—As1A—C27A—C28A−66.3 (4)C27B—C28B—C29B—C30B−2.6 (7)
C26A—C27A—C28A—C29A−1.8 (6)C28B—C29B—C30B—C25B1.3 (7)
As1A—C27A—C28A—C29A173.2 (3)C28B—C29B—C30B—C31B−178.2 (4)
C27A—C28A—C29A—C30A−0.8 (6)C26B—C25B—C30B—C29B−0.1 (7)
C26A—C25A—C30A—C29A−2.5 (6)C26B—C25B—C30B—C31B179.5 (4)
C26A—C25A—C30A—C31A180.0 (4)C29B—C30B—C31B—C32B31.7 (6)
C28A—C29A—C30A—C25A2.9 (6)C25B—C30B—C31B—C32B−147.8 (4)
C28A—C29A—C30A—C31A−179.6 (4)C29B—C30B—C31B—C36B−145.6 (4)
C25A—C30A—C31A—C32A−174.5 (4)C25B—C30B—C31B—C36B34.9 (6)
C29A—C30A—C31A—C32A8.1 (6)C36B—C31B—C32B—C33B0.8 (6)
C25A—C30A—C31A—C36A4.9 (6)C30B—C31B—C32B—C33B−176.6 (4)
C29A—C30A—C31A—C36A−172.5 (4)C31B—C32B—C33B—C34B−0.3 (6)
C36A—C31A—C32A—C33A1.8 (6)C32B—C33B—C34B—C35B−0.5 (6)
C30A—C31A—C32A—C33A−178.8 (4)C33B—C34B—C35B—C36B0.8 (7)
C31A—C32A—C33A—C34A−2.1 (7)C34B—C35B—C36B—C31B−0.3 (7)
C32A—C33A—C34A—C35A0.9 (7)C32B—C31B—C36B—C35B−0.5 (6)
C33A—C34A—C35A—C36A0.6 (6)C30B—C31B—C36B—C35B176.9 (4)
C34A—C35A—C36A—C31A−0.9 (7)C3B—C4B—C56B—C6B1.0 (8)
C32A—C31A—C36A—C35A−0.3 (6)C1B—C6B—C56B—C4B0.7 (8)
C30A—C31A—C36A—C35A−179.6 (4)C7B—C6B—C56B—C4B−178.7 (5)
Cg1, Cg2, Cg3, Cg4, Cg5, Cg6 and Cg7 are the centroids of the C25B–C30B, C19B–C24B, C7B–C12B, C31A–C36A, C1A–C6A, C31B–C36B and C13B–C18B benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
C4B—H4BA···Cg1i0.932.773.583 (6)147
C9A—H9A···Cg2ii0.932.993.872 (6)160
C11A—H11A···Cg3iii0.932.883.723 (7)153
C13B—H13B···Cg40.932.793.596 (5)147
C14A—H14A···Cg5i0.932.933.834 (5)172
C24A—H24A···Cg6iv0.932.703.582 (6)160
C28B—H28B···Cg7v0.932.563.313 (6)139
C36A—H36A···Cg3vi0.932.963.651 (6)133
Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3, Cg4, Cg5, Cg6 and Cg7 are the centroids of the C25B–C30B, C19B–C24B, C7B–C12B, C31A–C36A, C1A–C6A, C31B–C36B and C13B–C18B benzene rings, respectively.

D—H⋯AD—HH⋯ADAD—H⋯A
C4B—H4BACg1i0.932.773.583 (6)147
C9A—H9ACg2ii0.932.993.872 (6)160
C11A—H11ACg3iii0.932.883.723 (7)153
C13B—H13BCg40.932.793.596 (5)147
C14A—H14ACg5i0.932.933.834 (5)172
C24A—H24ACg6iv0.932.703.582 (6)160
C28B—H28BCg7v0.932.563.313 (6)139
C36A—H36ACg3vi0.932.963.651 (6)133

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

  4 in total

1.  A short history of SHELX.

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

2.  Bis{[μ-bis-(diphenyl-arsino)methane-1:2κAs:As']nona-carbonyl-1κC,2κC,3κC-[tris-(4-methoxy-phen-yl)arsine-3κAs]-triangulo-triruthenium(0)} dichloro-methane solvate.

Authors:  Omar Bin Shawkataly; Imthyaz Ahmed Khan; Chin Sing Yeap; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-01-16

3.  Bis{[μ-bis-(diphenyl-phosphino)methane-1:2κP:P']nona-carbonyl-1κC,2κC,3κC-[tris-(4-methoxy-phen-yl)arsine-3κAs]-triangulo-triruthenium(0)} dichloro-methane solvate.

Authors:  Omar Bin Shawkataly; Imthyaz Ahmed Khan; Chin Sing Yeap; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-12-09

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total
  2 in total

1.  [μ-Bis(diphenyl-phosphan-yl)methane-1:2κP:P']nona-carbonyl-1κC,2κC,3κC-[tris-(biphenyl-4-yl)arsane-3κAs]-triangulo-triruthenium(0).

Authors:  Omar Bin Shawkataly; Imthyaz Ahmed Khan; Siti Syaida Sirat; Chin Sing Yeap; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-01-15

2.  [μ-Bis(diphenyl-arsan-yl)methane-1:2κAs:As']nona-carbonyl-1κC,2κC,3κC-[tris-(biphenyl-4-yl)arsane-3κAs]-triangulo-triruthenium(0).

Authors:  Omar Bin Shawkataly; Imthyaz Ahmed Khan; Siti Syaida Sirat; Chin Sing Yeap; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-01-15
  2 in total

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