Literature DB >> 21581819

Bis(2,2'-bipyridine){ethyl 4'-[N-(4-carbamoylphen-yl)carbamo-yl]-2,2'-bi-pyridine-4-carboxyl-ate}ruthenium(II) bis-[hexa-fluorido-phosphate(V)].

Masanari Hirahara1, Shigeyuki Masaoka, Ken Sakai.   

Abstract

In the title compound, [Ru(C(10)H(8)N(2))(2)(C(21)H(18)N(4)O(4))](PF(6))(2), the Ru(II) complex cation reveals a slightly distorted octa-hedral coordination. The coordination bonds of the 4,4'-substituted bipyridyl donors [Ru-N = 2.038 (3) and 2.051 (3) Å] are shorter than those of the 2,2'-bipyridyl donors [Ru-N1 = 2.065 (3)-2.077 (3) Å], due to the electron-withdrawing effects of the substituents at the 4,4'-positions. The angles between the pyridyl planes of the three bipyridyl ligands are 1.5 (2), 6.3 (3) and 8.7 (2)°, respectively. The cations are connected by anions via N-H⋯F inter-actions.

Entities:  

Year:  2009        PMID： 21581819      PMCID： PMC2968400          DOI： 10.1107/S1600536809002360

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


Related literature

For related literature, see: Gillaizeau-Gauthier et al. (2001 ▶); Ozawa & Sakai (2007 ▶); Ozawa et al. (2006 ▶, 2007 ▶); Sakai & Ozawa (2007 ▶); Sakai et al. (1993 ▶). For discussion of attractive inter­actions between negatively-charged atoms and alpha C atoms from heterocyclic rings, see: Schottel et al. (2008 ▶).

Experimental

Crystal data

[Ru(C10H8N2)2(C21H18N4O4)](PF6)2 M = 1093.77 Monoclinic, a = 18.400 (3) Å b = 13.187 (2) Å c = 18.863 (3) Å β = 111.344 (2)° V = 4262.9 (11) Å3 Z = 4 Mo Kα radiation μ = 0.55 mm−1 T = 100 (s.u.?) K 0.20 × 0.10 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.717, T max = 0.986 23329 measured reflections 9357 independent reflections 6405 reflections with I > 2σ(I) R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.113 S = 1.00 9357 reflections 614 parameters H-atom parameters constrained Δρmax = 0.79 e Å−3 Δρmin = −0.48 e Å−3 Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: KENX (Sakai, 2004 ▶); software used to prepare material for publication: SHELXL97, TEXSAN (Molecular Structure Corporation, 2001 ▶), KENX and ORTEPII (Johnson, 1976 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002360/kp2198sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002360/kp2198Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Ru(C10H8N2)2(C21H18N4O4)](PF6)2F(000) = 2200
Mr = 1093.77Dx = 1.704 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7706 reflections
a = 18.400 (3) Åθ = 2.2–27.5°
b = 13.187 (2) ŵ = 0.55 mm−1
c = 18.863 (3) ÅT = 100 K
β = 111.344 (2)°Block, red
V = 4262.9 (11) Å30.2 × 0.1 × 0.03 mm
Z = 4
Bruker SMART APEXII CCD area-detector diffractometer9357 independent reflections
Radiation source: rotating anode with a mirror focusing unit6405 reflections with I > 2σ(I)
graphiteRint = 0.047
φ and ω scansθmax = 27.1°, θmin = 2.2°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)h = −23→19
Tmin = 0.717, Tmax = 0.986k = −16→16
23329 measured reflectionsl = −24→24
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) = 0.113H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0524P)2 + 2.5961P] where P = (Fo2 + 2Fc2)/3
9357 reflections(Δ/σ)max = 0.001
614 parametersΔρmax = 0.79 e Å−3
0 restraintsΔρmin = −0.48 e Å−3
Experimental. The first 50 frames were rescanned at the end of data collection to evaluate any possible decay phenomenon. Since it was judged to be negligible, no decay correction was applied to the data.
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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)- 12.7740 (0.0188) x - 4.2078 (0.0170) y + 16.1006 (0.0145) z = 0.0050 (0.0090)* -0.0058 (0.0021) N1 * 0.0092 (0.0023) C1 * -0.0056 (0.0026) C2 * -0.0010 (0.0026) C3 * 0.0042 (0.0024) C4 * -0.0009 (0.0022) C5Rms deviation of fitted atoms = 0.0053-12.4144 (0.0196) x - 4.3031 (0.0184) y + 16.2635 (0.0138) z = 0.1580 (0.0125)Angle to previous plane (with approximate e.s.d.) = 1.54 (1/5)* 0.0017 (0.0022) N2 * -0.0044 (0.0023) C6 * 0.0017 (0.0025) C7 * 0.0035 (0.0027) C8 * -0.0061 (0.0027) C9 * 0.0036 (0.0025) C10Rms deviation of fitted atoms = 0.00388.6305 (0.0228) x + 5.1793 (0.0182) y + 10.6773 (0.0218) z = 5.3175 (0.0062)Angle to previous plane (with approximate e.s.d.) = 85.47 (0.09)* 0.0065 (0.0022) N3 * 0.0045 (0.0024) C11 * -0.0115 (0.0026) C12 * 0.0077 (0.0027) C13 * 0.0033 (0.0025) C14 * -0.0105 (0.0023) C15Rms deviation of fitted atoms = 0.00799.8523 (0.0240) x + 4.0319 (0.0188) y + 10.1554 (0.0254) z = 5.7461 (0.0068)Angle to previous plane (with approximate e.s.d.) = 6.28 (0.26)* 0.0018 (0.0023) N4 * -0.0026 (0.0024) C16 * 0.0007 (0.0026) C17 * 0.0019 (0.0028) C18 * -0.0026 (0.0028) C19 * 0.0009 (0.0026) C20Rms deviation of fitted atoms = 0.00195.2914 (0.0916) x - 12.4015 (0.0303) y + 1.2118 (0.0485) z = 1.7169 (0.0084)Angle to previous plane (with approximate e.s.d.) = 89.47 (0.22)* 0.0000 (0.0000) C31 * 0.0000 (0.0000) O1 * 0.0000 (0.0000) O2Rms deviation of fitted atoms = 0.00006.6694 (0.0231) x - 12.0776 (0.0072) y + 0.5442 (0.0266) z = 1.6902 (0.0034)Angle to previous plane (with approximate e.s.d.) = 4.54 (0.40)* -0.0271 (0.0023) N5 * 0.0077 (0.0025) C21 * 0.0156 (0.0025) C22 * -0.0197 (0.0024) C23 * 0.0005 (0.0024) C24 * 0.0229 (0.0023) C25Rms deviation of fitted atoms = 0.01819.0772 (0.0232) x - 11.3634 (0.0101) y - 1.3032 (0.0274) z = 1.6621 (0.0095)Angle to previous plane (with approximate e.s.d.) = 8.69 (0.16)* 0.0155 (0.0024) N6 * -0.0114 (0.0024) C26 * -0.0060 (0.0026) C27 * 0.0191 (0.0026) C28 * -0.0152 (0.0027) C29 * -0.0021 (0.0026) C30Rms deviation of fitted atoms = 0.01295.9317 (0.1164) x - 12.4552 (0.0320) y - 3.3218 (0.1161) z = 0.5112 (0.0477)Angle to previous plane (with approximate e.s.d.) = 15.10 (0.48)* 0.0000 (0.0000) C34 * 0.0000 (0.0000) O3 * 0.0000 (0.0000) N7Rms deviation of fitted atoms = 0.00002.1032 (0.0288) x + 12.8237 (0.0053) y + 2.7844 (0.0287) z = 0.1928 (0.0183)Angle to previous plane (with approximate e.s.d.) = 26.56 (0.29)* 0.0082 (0.0027) C35 * -0.0073 (0.0028) C36 * 0.0001 (0.0028) C37 * 0.0062 (0.0027) C38 * -0.0054 (0.0027) C39 * -0.0018 (0.0027) C40Rms deviation of fitted atoms = 0.0056-0.9384 (0.1032) x - 13.1238 (0.0039) y - 1.1164 (0.1264) z = 1.0753 (0.0983)Angle to previous plane (with approximate e.s.d.) = 7.87 (0.23)* 0.0000 (0.0000) C41 * 0.0000 (0.0000) O4 * 0.0000 (0.0000) N8Rms deviation of fitted atoms = 0.00002.1032 (0.0288) x + 12.8237 (0.0053) y + 2.7844 (0.0287) z = 0.1928 (0.0183)Angle to previous plane (with approximate e.s.d.) = 7.87 (0.23)* 0.0082 (0.0027) C35 * -0.0073 (0.0028) C36 * 0.0001 (0.0028) C37 * 0.0062 (0.0027) C38 * -0.0054 (0.0027) C39 * -0.0018 (0.0027) C40Rms deviation of fitted atoms = 0.00569.0772 (0.0232) x - 11.3634 (0.0101) y - 1.3032 (0.0274) z = 1.6621 (0.0095)Angle to previous plane (with approximate e.s.d.) = 40.76 (0.09)* 0.0155 (0.0024) N6 * -0.0114 (0.0024) C26 * -0.0060 (0.0026) C27 * 0.0191 (0.0026) C28 * -0.0152 (0.0027) C29 * -0.0021 (0.0026) C30Rms deviation of fitted atoms = 0.0129
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
Ru10.294461 (16)0.04801 (2)0.250977 (15)0.02158 (8)
P10.35302 (6)0.46905 (8)0.15958 (6)0.0353 (2)
P20.29204 (6)0.62723 (9)0.45315 (6)0.0387 (3)
F10.26565 (15)0.4258 (2)0.12279 (15)0.0540 (7)
F20.32351 (14)0.57383 (17)0.11340 (13)0.0438 (6)
F30.43974 (13)0.51275 (18)0.19471 (13)0.0428 (6)
F40.38170 (15)0.36573 (18)0.20517 (13)0.0478 (6)
F50.37108 (15)0.42579 (18)0.08811 (13)0.0496 (6)
F60.33452 (15)0.51482 (18)0.22961 (13)0.0472 (6)
F70.26997 (18)0.5185 (2)0.47525 (18)0.0704 (9)
F80.37419 (15)0.5834 (2)0.45629 (16)0.0562 (7)
F90.31532 (17)0.7367 (2)0.43274 (16)0.0643 (8)
F100.20992 (15)0.6720 (2)0.44945 (17)0.0688 (8)
F110.25655 (19)0.5986 (3)0.36555 (15)0.0821 (10)
F120.32822 (17)0.6553 (2)0.54043 (14)0.0601 (7)
O1−0.03074 (15)−0.15596 (19)−0.04502 (13)0.0319 (6)
O2−0.06958 (14)−0.16271 (19)0.05549 (14)0.0318 (6)
O30.03822 (16)−0.1340 (2)0.41695 (15)0.0451 (7)
O4−0.06524 (18)−0.1397 (2)0.73340 (17)0.0510 (8)
N10.24580 (17)0.1913 (2)0.24496 (16)0.0242 (6)
N20.38261 (16)0.1246 (2)0.33484 (16)0.0261 (7)
N30.35294 (16)0.0746 (2)0.17716 (15)0.0232 (6)
N40.35305 (16)−0.0874 (2)0.25818 (16)0.0246 (6)
N50.19777 (16)−0.0206 (2)0.17421 (15)0.0231 (6)
N60.23667 (16)0.0047 (2)0.31992 (15)0.0240 (6)
N70.14210 (19)−0.1138 (2)0.52667 (16)0.0342 (8)
H70.1919−0.10610.54380.041*
N80.0512 (2)−0.1560 (3)0.82715 (18)0.0451 (9)
H8A0.0302−0.15730.86110.054*
H8B0.1010−0.16070.84050.054*
C10.1751 (2)0.2201 (3)0.1973 (2)0.0296 (8)
H10.14480.17310.16230.036*
C20.1449 (2)0.3159 (3)0.1975 (2)0.0360 (9)
H20.09610.33350.16260.043*
C30.1892 (2)0.3850 (3)0.2510 (2)0.0396 (10)
H30.17020.44990.25280.048*
C40.2621 (2)0.3569 (3)0.3018 (2)0.0343 (9)
H40.29220.40280.33810.041*
C50.2899 (2)0.2597 (3)0.2982 (2)0.0260 (8)
C60.3667 (2)0.2223 (3)0.3481 (2)0.0272 (8)
C70.4208 (2)0.2798 (3)0.4051 (2)0.0346 (9)
H7A0.40930.34620.41400.042*
C80.4918 (2)0.2374 (3)0.4481 (2)0.0409 (10)
H80.52820.27520.48640.049*
C90.5087 (2)0.1396 (3)0.4345 (2)0.0402 (10)
H90.55660.11060.46270.048*
C100.4523 (2)0.0848 (3)0.3776 (2)0.0328 (9)
H100.46320.01820.36880.039*
C110.3504 (2)0.1599 (3)0.1376 (2)0.0277 (8)
H110.31730.21190.14010.033*
C120.3955 (2)0.1735 (3)0.0931 (2)0.0339 (9)
H120.39150.23290.06540.041*
C130.4458 (2)0.0983 (3)0.0907 (2)0.0344 (9)
H130.47750.10680.06240.041*
C140.4490 (2)0.0100 (3)0.1306 (2)0.0303 (8)
H140.4827−0.04190.12910.036*
C150.4019 (2)−0.0014 (3)0.17289 (19)0.0247 (7)
C160.3991 (2)−0.0939 (3)0.21569 (19)0.0267 (8)
C170.4383 (2)−0.1823 (3)0.2130 (2)0.0325 (9)
H170.4696−0.18540.18400.039*
C180.4307 (2)−0.2657 (3)0.2536 (2)0.0376 (9)
H180.4569−0.32550.25230.045*
C190.3840 (2)−0.2599 (3)0.2962 (2)0.0379 (9)
H190.3779−0.31560.32370.045*
C200.3464 (2)−0.1700 (3)0.2973 (2)0.0324 (9)
H200.3151−0.16620.32630.039*
C210.1834 (2)−0.0348 (3)0.09948 (19)0.0260 (8)
H210.2217−0.01620.08060.031*
C220.1148 (2)−0.0756 (3)0.04975 (19)0.0264 (8)
H220.1072−0.0845−0.00140.032*
C230.05712 (19)−0.1033 (2)0.07734 (19)0.0228 (7)
C240.07228 (19)−0.0931 (2)0.15475 (18)0.0217 (7)
H240.0350−0.11270.17470.026*
C250.14324 (19)−0.0536 (3)0.20223 (18)0.0220 (7)
C260.16747 (19)−0.0442 (3)0.28556 (18)0.0228 (7)
C270.1254 (2)−0.0832 (3)0.3282 (2)0.0276 (8)
H270.0784−0.11680.30400.033*
C280.1542 (2)−0.0714 (3)0.40656 (19)0.0271 (8)
C290.2228 (2)−0.0174 (3)0.4403 (2)0.0323 (9)
H290.2419−0.00540.49250.039*
C300.2623 (2)0.0180 (3)0.3961 (2)0.0303 (8)
H300.30890.05280.41970.036*
C31−0.0182 (2)−0.1441 (3)0.0220 (2)0.0260 (8)
C32−0.1427 (2)−0.2112 (3)0.0082 (2)0.0359 (9)
H32A−0.1322−0.2763−0.01000.043*
H32B−0.1702−0.1689−0.03550.043*
C33−0.1909 (2)−0.2249 (3)0.0568 (2)0.0429 (10)
H33A−0.1612−0.26120.10220.064*
H33B−0.2372−0.26270.02900.064*
H33C−0.2053−0.15980.07020.064*
C340.1056 (2)−0.1108 (3)0.4501 (2)0.0315 (9)
C350.1075 (2)−0.1283 (3)0.5818 (2)0.0308 (8)
C360.0286 (2)−0.1128 (3)0.5644 (2)0.0378 (9)
H36−0.0040−0.09780.51490.045*
C37−0.0014 (2)−0.1198 (3)0.6221 (2)0.0348 (9)
H37−0.0544−0.10850.61040.042*
C380.0448 (2)−0.1430 (3)0.6962 (2)0.0319 (9)
C390.1243 (2)−0.1606 (3)0.7128 (2)0.0348 (9)
H390.1565−0.17730.76220.042*
C400.1555 (2)−0.1530 (3)0.6560 (2)0.0335 (9)
H400.2085−0.16460.66750.040*
C410.0065 (2)−0.1465 (3)0.7539 (2)0.0341 (9)
U11U22U33U12U13U23
Ru10.01934 (14)0.02957 (16)0.01735 (14)−0.00295 (12)0.00850 (10)−0.00124 (11)
P10.0359 (6)0.0409 (6)0.0276 (5)−0.0005 (5)0.0101 (4)0.0018 (4)
P20.0341 (6)0.0527 (7)0.0279 (6)−0.0078 (5)0.0097 (5)0.0066 (5)
F10.0469 (16)0.0628 (17)0.0498 (16)−0.0160 (12)0.0143 (13)−0.0035 (12)
F20.0455 (15)0.0457 (14)0.0387 (14)0.0057 (11)0.0135 (12)0.0049 (10)
F30.0342 (13)0.0524 (15)0.0399 (14)0.0004 (11)0.0113 (11)0.0025 (11)
F40.0603 (17)0.0414 (14)0.0410 (14)0.0030 (12)0.0178 (13)0.0071 (11)
F50.0636 (17)0.0508 (16)0.0392 (14)0.0076 (12)0.0245 (13)−0.0018 (11)
F60.0551 (16)0.0537 (15)0.0400 (14)−0.0018 (12)0.0258 (13)−0.0037 (11)
F70.085 (2)0.0571 (18)0.089 (2)−0.0241 (15)0.0552 (19)−0.0047 (15)
F80.0436 (16)0.0684 (18)0.0612 (17)0.0038 (13)0.0246 (14)0.0138 (14)
F90.071 (2)0.0601 (18)0.0712 (19)0.0054 (14)0.0375 (16)0.0281 (15)
F100.0386 (16)0.092 (2)0.076 (2)−0.0015 (15)0.0206 (15)0.0006 (17)
F110.076 (2)0.119 (3)0.0323 (15)0.0066 (19)−0.0030 (15)−0.0111 (16)
F120.074 (2)0.0638 (18)0.0302 (13)0.0033 (14)0.0043 (13)0.0000 (12)
O10.0321 (15)0.0444 (16)0.0177 (13)−0.0067 (12)0.0075 (11)−0.0026 (11)
O20.0277 (14)0.0437 (16)0.0232 (13)−0.0095 (11)0.0083 (11)−0.0018 (11)
O30.0375 (17)0.075 (2)0.0254 (15)−0.0233 (15)0.0148 (13)−0.0040 (14)
O40.048 (2)0.075 (2)0.0376 (17)0.0021 (16)0.0254 (16)0.0076 (15)
N10.0264 (16)0.0279 (16)0.0231 (15)−0.0044 (12)0.0149 (13)−0.0010 (12)
N20.0201 (15)0.0392 (18)0.0212 (15)−0.0069 (13)0.0102 (13)−0.0022 (12)
N30.0225 (15)0.0300 (17)0.0166 (14)−0.0072 (12)0.0066 (12)−0.0024 (11)
N40.0213 (15)0.0286 (16)0.0228 (15)−0.0019 (12)0.0066 (12)0.0000 (12)
N50.0227 (15)0.0296 (17)0.0181 (14)−0.0035 (12)0.0088 (12)−0.0030 (11)
N60.0240 (16)0.0301 (16)0.0187 (15)−0.0019 (12)0.0088 (12)0.0007 (12)
N70.0313 (18)0.052 (2)0.0209 (16)−0.0144 (15)0.0118 (14)−0.0006 (14)
N80.047 (2)0.072 (3)0.0225 (18)−0.0069 (18)0.0205 (17)−0.0020 (16)
C10.0241 (19)0.039 (2)0.0270 (19)−0.0012 (16)0.0113 (16)0.0035 (16)
C20.030 (2)0.041 (2)0.039 (2)0.0045 (18)0.0141 (19)0.0054 (18)
C30.042 (3)0.036 (2)0.049 (3)0.0061 (18)0.026 (2)0.0044 (18)
C40.038 (2)0.035 (2)0.035 (2)−0.0044 (17)0.0192 (19)−0.0051 (17)
C50.0273 (19)0.031 (2)0.0248 (19)−0.0051 (15)0.0161 (16)−0.0002 (14)
C60.028 (2)0.037 (2)0.0233 (18)−0.0071 (16)0.0172 (16)−0.0057 (15)
C70.033 (2)0.043 (2)0.032 (2)−0.0116 (17)0.0164 (18)−0.0117 (17)
C80.029 (2)0.065 (3)0.029 (2)−0.014 (2)0.0116 (18)−0.0170 (19)
C90.024 (2)0.063 (3)0.031 (2)−0.0044 (19)0.0069 (17)−0.0087 (19)
C100.025 (2)0.047 (2)0.028 (2)0.0003 (17)0.0110 (16)−0.0025 (17)
C110.029 (2)0.029 (2)0.0257 (19)−0.0028 (15)0.0111 (16)−0.0026 (15)
C120.037 (2)0.037 (2)0.032 (2)−0.0074 (17)0.0170 (18)0.0010 (16)
C130.034 (2)0.044 (2)0.031 (2)−0.0093 (18)0.0193 (18)0.0002 (17)
C140.027 (2)0.039 (2)0.028 (2)−0.0009 (16)0.0133 (16)−0.0057 (16)
C150.0215 (18)0.032 (2)0.0191 (17)−0.0036 (15)0.0059 (15)−0.0048 (14)
C160.0234 (19)0.036 (2)0.0192 (18)−0.0033 (15)0.0057 (15)−0.0044 (15)
C170.032 (2)0.039 (2)0.027 (2)0.0024 (17)0.0118 (17)−0.0041 (16)
C180.041 (2)0.033 (2)0.035 (2)0.0064 (18)0.0092 (19)−0.0026 (17)
C190.041 (2)0.035 (2)0.038 (2)−0.0015 (18)0.0141 (19)0.0076 (17)
C200.032 (2)0.034 (2)0.031 (2)0.0028 (16)0.0105 (17)0.0042 (16)
C210.0257 (18)0.035 (2)0.0215 (17)−0.0024 (15)0.0132 (15)−0.0013 (14)
C220.029 (2)0.035 (2)0.0182 (17)−0.0023 (15)0.0119 (15)−0.0032 (14)
C230.0239 (18)0.0220 (18)0.0227 (18)0.0014 (14)0.0087 (15)0.0003 (13)
C240.0218 (18)0.0244 (18)0.0208 (17)−0.0014 (14)0.0102 (14)0.0005 (13)
C250.0246 (17)0.0242 (18)0.0189 (16)−0.0013 (14)0.0099 (14)−0.0013 (13)
C260.0219 (17)0.0287 (19)0.0190 (17)−0.0008 (15)0.0087 (14)−0.0026 (14)
C270.0275 (19)0.034 (2)0.0238 (19)−0.0088 (15)0.0118 (16)−0.0020 (15)
C280.030 (2)0.033 (2)0.0209 (18)−0.0034 (15)0.0115 (16)0.0007 (14)
C290.037 (2)0.043 (2)0.0173 (18)−0.0094 (17)0.0108 (16)−0.0038 (15)
C300.027 (2)0.044 (2)0.0201 (18)−0.0108 (16)0.0078 (15)−0.0031 (15)
C310.0248 (19)0.027 (2)0.0241 (19)−0.0011 (14)0.0070 (15)0.0018 (14)
C320.027 (2)0.049 (3)0.027 (2)−0.0105 (17)0.0040 (17)0.0000 (17)
C330.036 (2)0.055 (3)0.040 (2)−0.005 (2)0.016 (2)0.008 (2)
C340.032 (2)0.042 (2)0.0246 (19)−0.0125 (17)0.0154 (17)−0.0040 (16)
C350.037 (2)0.035 (2)0.0250 (19)−0.0136 (17)0.0166 (17)−0.0004 (15)
C360.040 (2)0.051 (3)0.025 (2)−0.0049 (19)0.0137 (18)0.0051 (17)
C370.032 (2)0.043 (2)0.031 (2)−0.0001 (17)0.0130 (18)0.0044 (17)
C380.044 (2)0.033 (2)0.0236 (19)−0.0080 (17)0.0173 (18)−0.0026 (15)
C390.039 (2)0.042 (2)0.0223 (19)−0.0121 (18)0.0102 (18)−0.0018 (16)
C400.033 (2)0.039 (2)0.027 (2)−0.0105 (17)0.0085 (17)−0.0013 (16)
C410.039 (2)0.037 (2)0.028 (2)−0.0061 (18)0.0153 (18)0.0008 (16)
Ru1—N12.077 (3)C9—C101.392 (5)
Ru1—N22.070 (3)C9—H90.9300
Ru1—N32.076 (3)C10—H100.9300
Ru1—N42.065 (3)C11—C121.389 (5)
Ru1—N52.051 (3)C11—H110.9300
Ru1—N62.038 (3)C12—C131.369 (5)
P1—F41.595 (2)C12—H120.9300
P1—F31.596 (2)C13—C141.376 (5)
P1—F61.598 (2)C13—H130.9300
P1—F51.606 (2)C14—C151.384 (5)
P1—F11.606 (3)C14—H140.9300
P1—F21.618 (2)C15—C161.474 (5)
P2—F121.579 (3)C16—C171.381 (5)
P2—F111.585 (3)C17—C181.376 (5)
P2—F71.587 (3)C17—H170.9300
P2—F91.592 (3)C18—C191.375 (5)
P2—F81.599 (3)C18—H180.9300
P2—F101.600 (3)C19—C201.376 (5)
O1—C311.210 (4)C19—H190.9300
O2—C311.337 (4)C20—H200.9300
O2—C321.463 (4)C21—C221.380 (5)
O3—C341.208 (4)C21—H210.9300
O4—C411.237 (5)C22—C231.389 (4)
N1—C11.338 (4)C22—H220.9300
N1—C51.373 (4)C23—C241.390 (4)
N2—C101.348 (5)C23—C311.499 (5)
N2—C61.364 (5)C24—C251.388 (4)
N3—C111.341 (4)C24—H240.9300
N3—C151.369 (4)C25—C261.475 (4)
N4—C201.345 (4)C26—C271.401 (4)
N4—C161.364 (4)C27—C281.386 (5)
N5—C211.349 (4)C27—H270.9300
N5—C251.364 (4)C28—C291.386 (5)
N6—C301.351 (4)C28—C341.509 (5)
N6—C261.363 (4)C29—C301.372 (5)
N7—C341.354 (5)C29—H290.9300
N7—C351.415 (4)C30—H300.9300
N7—H70.8600C32—C331.502 (5)
N8—C411.332 (5)C32—H32A0.9700
N8—H8A0.8600C32—H32B0.9700
N8—H8B0.8600C33—H33A0.9600
C1—C21.381 (5)C33—H33B0.9600
C1—H10.9300C33—H33C0.9600
C2—C31.384 (6)C35—C361.384 (5)
C2—H20.9300C35—C401.394 (5)
C3—C41.384 (5)C36—C371.391 (5)
C3—H30.9300C36—H360.9300
C4—C51.392 (5)C37—C381.380 (5)
C4—H40.9300C37—H370.9300
C5—C61.468 (5)C38—C391.399 (5)
C6—C71.394 (5)C38—C411.497 (5)
C7—C81.380 (6)C39—C401.392 (5)
C7—H7A0.9300C39—H390.9300
C8—C91.373 (6)C40—H400.9300
C8—H80.9300
N6—Ru1—N578.87 (11)N3—C11—C12122.5 (3)
N6—Ru1—N495.56 (11)N3—C11—H11118.8
N5—Ru1—N487.86 (11)C12—C11—H11118.8
N6—Ru1—N295.43 (11)C13—C12—C11119.1 (4)
N5—Ru1—N2172.71 (11)C13—C12—H12120.5
N4—Ru1—N297.28 (11)C11—C12—H12120.5
N6—Ru1—N3173.37 (11)C12—C13—C14119.4 (3)
N5—Ru1—N397.42 (11)C12—C13—H13120.3
N4—Ru1—N378.73 (11)C14—C13—H13120.3
N2—Ru1—N388.68 (10)C13—C14—C15119.7 (3)
N6—Ru1—N188.57 (11)C13—C14—H14120.2
N5—Ru1—N196.73 (11)C15—C14—H14120.2
N4—Ru1—N1174.36 (11)N3—C15—C14121.2 (3)
N2—Ru1—N178.46 (12)N3—C15—C16114.8 (3)
N3—Ru1—N197.36 (11)C14—C15—C16124.0 (3)
F4—P1—F390.00 (14)N4—C16—C17121.2 (3)
F4—P1—F690.29 (13)N4—C16—C15115.0 (3)
F3—P1—F690.11 (13)C17—C16—C15123.8 (3)
F4—P1—F591.16 (13)C18—C17—C16119.6 (3)
F3—P1—F589.76 (14)C18—C17—H17120.2
F6—P1—F5178.54 (15)C16—C17—H17120.2
F4—P1—F190.70 (14)C19—C18—C17119.5 (4)
F3—P1—F1179.00 (15)C19—C18—H18120.3
F6—P1—F190.59 (14)C17—C18—H18120.3
F5—P1—F189.52 (14)C18—C19—C20118.7 (4)
F4—P1—F2179.71 (15)C18—C19—H19120.6
F3—P1—F290.23 (13)C20—C19—H19120.6
F6—P1—F289.53 (13)N4—C20—C19122.9 (3)
F5—P1—F289.02 (13)N4—C20—H20118.5
F1—P1—F289.07 (14)C19—C20—H20118.5
F12—P2—F11179.42 (19)N5—C21—C22123.1 (3)
F12—P2—F789.37 (16)N5—C21—H21118.4
F11—P2—F790.63 (19)C22—C21—H21118.4
F12—P2—F989.49 (16)C21—C22—C23118.9 (3)
F11—P2—F990.51 (18)C21—C22—H22120.6
F7—P2—F9178.83 (19)C23—C22—H22120.6
F12—P2—F890.69 (16)C22—C23—C24118.6 (3)
F11—P2—F888.73 (17)C22—C23—C31118.2 (3)
F7—P2—F889.58 (16)C24—C23—C31123.2 (3)
F9—P2—F890.15 (15)C25—C24—C23119.7 (3)
F12—P2—F1089.54 (16)C25—C24—H24120.1
F11—P2—F1091.04 (17)C23—C24—H24120.1
F7—P2—F1090.98 (17)N5—C25—C24121.4 (3)
F9—P2—F1089.30 (16)N5—C25—C26114.0 (3)
F8—P2—F10179.40 (17)C24—C25—C26124.6 (3)
C31—O2—C32116.3 (3)N6—C26—C27121.1 (3)
C1—N1—C5118.4 (3)N6—C26—C25114.5 (3)
C1—N1—Ru1126.1 (2)C27—C26—C25124.4 (3)
C5—N1—Ru1115.4 (2)C28—C27—C26119.6 (3)
C10—N2—C6118.6 (3)C28—C27—H27120.2
C10—N2—Ru1125.3 (3)C26—C27—H27120.2
C6—N2—Ru1116.1 (2)C27—C28—C29118.6 (3)
C11—N3—C15118.1 (3)C27—C28—C34118.0 (3)
C11—N3—Ru1126.4 (2)C29—C28—C34123.2 (3)
C15—N3—Ru1115.4 (2)C30—C29—C28119.4 (3)
C20—N4—C16118.1 (3)C30—C29—H29120.3
C20—N4—Ru1126.0 (2)C28—C29—H29120.3
C16—N4—Ru1115.9 (2)N6—C30—C29123.0 (3)
C21—N5—C25118.0 (3)N6—C30—H30118.5
C21—N5—Ru1126.0 (2)C29—C30—H30118.5
C25—N5—Ru1116.0 (2)O1—C31—O2124.8 (3)
C30—N6—C26118.1 (3)O1—C31—C23123.4 (3)
C30—N6—Ru1125.5 (2)O2—C31—C23111.8 (3)
C26—N6—Ru1116.3 (2)O2—C32—C33107.3 (3)
C34—N7—C35127.4 (3)O2—C32—H32A110.3
C34—N7—H7116.3C33—C32—H32A110.3
C35—N7—H7116.3O2—C32—H32B110.3
C41—N8—H8A120.0C33—C32—H32B110.3
C41—N8—H8B120.0H32A—C32—H32B108.5
H8A—N8—H8B120.0C32—C33—H33A109.5
N1—C1—C2123.5 (4)C32—C33—H33B109.5
N1—C1—H1118.3H33A—C33—H33B109.5
C2—C1—H1118.3C32—C33—H33C109.5
C1—C2—C3118.3 (4)H33A—C33—H33C109.5
C1—C2—H2120.9H33B—C33—H33C109.5
C3—C2—H2120.9O3—C34—N7124.2 (3)
C2—C3—C4119.6 (4)O3—C34—C28120.4 (3)
C2—C3—H3120.2N7—C34—C28115.4 (3)
C4—C3—H3120.2C36—C35—C40120.0 (3)
C3—C4—C5119.6 (4)C36—C35—N7121.3 (3)
C3—C4—H4120.2C40—C35—N7118.6 (3)
C5—C4—H4120.2C35—C36—C37119.1 (4)
N1—C5—C4120.7 (3)C35—C36—H36120.4
N1—C5—C6115.0 (3)C37—C36—H36120.4
C4—C5—C6124.3 (3)C38—C37—C36122.2 (4)
N2—C6—C7120.9 (3)C38—C37—H37118.9
N2—C6—C5114.8 (3)C36—C37—H37118.9
C7—C6—C5124.2 (3)C37—C38—C39118.2 (3)
C8—C7—C6119.4 (4)C37—C38—C41117.6 (4)
C8—C7—H7A120.3C39—C38—C41124.2 (3)
C6—C7—H7A120.3C40—C39—C38120.4 (4)
C9—C8—C7120.0 (4)C40—C39—H39119.8
C9—C8—H8120.0C38—C39—H39119.8
C7—C8—H8120.0C39—C40—C35120.1 (4)
C8—C9—C10118.4 (4)C39—C40—H40120.0
C8—C9—H9120.8C35—C40—H40120.0
C10—C9—H9120.8O4—C41—N8121.1 (4)
N2—C10—C9122.6 (4)O4—C41—C38120.2 (4)
N2—C10—H10118.7N8—C41—C38118.8 (4)
C9—C10—H10118.7
C5—N1—C1—C21.7 (5)C21—N5—C25—C26174.2 (3)
N1—C1—C2—C3−1.7 (5)C23—C24—C25—N52.6 (5)
C1—C2—C3—C40.7 (6)C23—C24—C25—C26−176.7 (3)
C2—C3—C4—C50.3 (5)C30—N6—C26—C27−2.4 (5)
C1—N1—C5—C4−0.7 (5)C30—N6—C26—C25178.9 (3)
C1—N1—C5—C6−180.0 (3)N5—C25—C26—N66.1 (4)
C3—C4—C5—N1−0.3 (5)C24—C25—C26—N6−174.6 (3)
C3—C4—C5—C6178.9 (3)N5—C25—C26—C27−172.6 (3)
C10—N2—C6—C7−0.5 (5)C24—C25—C26—C276.7 (6)
C10—N2—C6—C5179.2 (3)N6—C26—C27—C280.4 (5)
N1—C5—C6—N2−0.6 (4)C25—C26—C27—C28179.0 (3)
C4—C5—C6—N2−179.8 (3)C26—C27—C28—C292.5 (6)
N1—C5—C6—C7179.1 (3)C26—C27—C28—C34177.6 (3)
C4—C5—C6—C7−0.2 (5)C27—C28—C29—C30−3.4 (6)
N2—C6—C7—C80.5 (5)C34—C28—C29—C30−178.2 (4)
C5—C6—C7—C8−179.1 (3)C26—N6—C30—C291.5 (6)
C6—C7—C8—C90.3 (6)C28—C29—C30—N61.4 (6)
C7—C8—C9—C10−1.0 (6)C32—O2—C31—O16.9 (5)
C6—N2—C10—C9−0.3 (5)C32—O2—C31—C23−174.8 (3)
C8—C9—C10—N21.0 (6)C22—C23—C31—O11.5 (5)
C15—N3—C11—C12−0.1 (5)C24—C23—C31—O1−177.7 (3)
N3—C11—C12—C13−1.6 (6)C22—C23—C31—O2−176.9 (3)
C11—C12—C13—C141.9 (6)C24—C23—C31—O24.0 (5)
C12—C13—C14—C15−0.5 (6)C31—O2—C32—C33179.9 (3)
C11—N3—C15—C141.6 (5)C35—N7—C34—O3−10.7 (7)
C11—N3—C15—C16−177.9 (3)C35—N7—C34—C28166.9 (3)
C13—C14—C15—N3−1.3 (5)C27—C28—C34—O3−13.6 (6)
C13—C14—C15—C16178.1 (3)C29—C28—C34—O3161.2 (4)
C20—N4—C16—C17−0.4 (5)C27—C28—C34—N7168.7 (3)
C20—N4—C16—C15178.5 (3)C29—C28—C34—N7−16.4 (6)
N3—C15—C16—N4−5.1 (4)C34—N7—C35—C36−18.7 (6)
C14—C15—C16—N4175.5 (3)C34—N7—C35—C40165.0 (4)
N3—C15—C16—C17173.8 (3)C40—C35—C36—C371.5 (6)
C14—C15—C16—C17−5.6 (6)N7—C35—C36—C37−174.7 (4)
N4—C16—C17—C180.3 (5)C35—C36—C37—C38−0.8 (6)
C15—C16—C17—C18−178.5 (3)C36—C37—C38—C39−0.5 (6)
C16—C17—C18—C190.1 (6)C36—C37—C38—C41178.8 (4)
C17—C18—C19—C20−0.4 (6)C37—C38—C39—C401.0 (6)
C16—N4—C20—C190.1 (5)C41—C38—C39—C40−178.3 (4)
C18—C19—C20—N40.3 (6)C38—C39—C40—C35−0.2 (6)
C25—N5—C21—C223.7 (5)C36—C35—C40—C39−1.0 (6)
N5—C21—C22—C230.3 (5)N7—C35—C40—C39175.3 (3)
C21—C22—C23—C24−2.9 (5)C37—C38—C41—O47.6 (6)
C21—C22—C23—C31177.9 (3)C39—C38—C41—O4−173.1 (4)
C22—C23—C24—C251.5 (5)C37—C38—C41—N8−171.6 (4)
C31—C23—C24—C25−179.3 (3)C39—C38—C41—N87.7 (6)
C21—N5—C25—C24−5.2 (5)
D—H···AD—HH···AD···AD—H···A
N7—H7···F2i0.862.343.181 (4)168
N8—H8B···F10i0.862.292.999 (5)139
Table 1

Selected bond lengths (Å)

Ru1—N12.077 (3)
Ru1—N22.070 (3)
Ru1—N32.076 (3)
Ru1—N42.065 (3)
Ru1—N52.051 (3)
Ru1—N62.038 (3)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N7—H7⋯F2i0.862.343.181 (4)168
N8—H8B⋯F10i0.862.292.999 (5)139

Symmetry code: (i) .

  5 in total

1.  Phosphonate-based bipyridine dyes for stable photovoltaic devices.

Authors:  I Gillaizeau-Gauthier; F Odobel; M Alebbi; R Argazzi; E Costa; C A Bignozzi; P Qu; G J Meyer
Journal:  Inorg Chem       Date:  2001-11-05       Impact factor: 5.165

Review 2.  Anion-pi interactions.

Authors:  Brandi L Schottel; Helen T Chifotides; Kim R Dunbar
Journal:  Chem Soc Rev       Date:  2007-09-12       Impact factor: 54.564

3.  A short history of SHELX.

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

4.  A photo-hydrogen-evolving molecular device driving visible-light-induced EDTA-reduction of water into molecular hydrogen.

Authors:  Hironobu Ozawa; Masa-aki Haga; Ken Sakai
Journal:  J Am Chem Soc       Date:  2006-04-19       Impact factor: 15.419

5.  Syntheses, characterization, and photo-hydrogen-evolving properties of tris(2,2'-bipyridine)ruthenium(II) derivatives tethered to a cis-Pt(II)Cl2 unit: insights into the structure-activity relationship.

Authors:  Hironobu Ozawa; Yuki Yokoyama; Masa-aki Haga; Ken Sakai
Journal:  Dalton Trans       Date:  2007-02-14       Impact factor: 4.390
  5 in total

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