supplementary materials


su2644 scheme

Acta Cryst. (2013). E69, m640-m641    [ doi:10.1107/S1600536813029462 ]

Bis(2,2'-bipyridine)[1,9-bis(diphenylphos­phanyl)-1,2,3,4,6,7,8,9-octahydropyrim­ido[1,2-a]pyrimidin-5-ium]ruthenium(II) hexa­fluorido­phosphate dibromide di­chloro­methane disolvate monohydrate

C. Shang, L. Vendier, P. Sutra and A. Igau

Abstract top

In the cation of the title complex, [Ru(C31H32N3P2)(C10H8N2)2](PF6)(Br)2·2CH2Cl2·H2O, the ruthenium ion is coordinated in a distorted octa­hedral geometry by two 2,2'-bi­pyridine (bpy) ligands and a chelating cationic N-di­phenyl­phosphino-1,3,4,6,7,8-hexa­hydro-2-pyrimido[1,2-a]pyrimidine [(PPh2)2-hpp] ligand. The tricationic charge of the complex is balanced by two bromide and one hexa­fluorido­phosphate counter-anions. The compound crystallized with two mol­ecules of di­chloro­methane (one of which is equally disordered about a Cl atom) and a water mol­ecule. In the crystal, one of the Br anions bridges two water mol­ecules via O-H...Br hydrogen bonds, forming a centrosymmetric diamond-shaped R42(8) motif. The cation and anions and the solvent mol­ecules are linked via C-H...F, C-H...Br, C-H...Cl and C-H...O hydrogen bonds, forming a three-dimensional network.

Comment top

In our efforts to functionnalize bisphosphino bisbipyridine ruthenium complexes we investigated the reaction of 1,2-dibromoethane with [Ru(bpy)2(PHPh2)]2+ in the presence of a base in order to form the ruthenium complex incorporating a chelating diphenylphosphino ethane ligand. This compound was previously obtained by (Sullivan et al., 1978) through coordination of the corresponding diphenylphosphino ethane (dppe) on the [Ru(bpy)2Cl2]2+ complex with a silver salt as a choride abstractor. The addition of an excess of BrCH2CH2Br into an acetonitrile solution of the precursor complex [Ru(bpy)2(PHR2)]2+ in the presence of 4 equivalents of 1,3,4,6,7,8-hexahydro-2-pyrimido[1,2-a]pyrimidine (H-hpp) gave the title compound as the major component.

In the cation of the title compound, Fig. 1, the ruthenium ion is coordinated in a distorted octahedral geometry to two 2,2'-bipyridine (bpy) ligands and a chelating cationic N-diphenylphosphino-1,3,4,6,7,8-hexahydro-2-pyrimido[1,2-a]pyrimidine [(PPh2)2-hpp] ligand. The tricationic charge of the complex is balanced by two bromide and one hexafluorophosphate counter anions. The compound crystallized as a dichloromethane disolvate and monohydrate.

In the crystal, one Br anion bridges two water molecules via O-H···Br hydrogen bonds forming a centrosymmetric diamond shaped R42(8) motif (Table 1). The cation and anions and the solvent molecules are linked via C-H···F, C-H···Br, C-H···Cl and C-H···O hydrogen bonds forming a three-dimensional structure (Table 1).

Instead of the expected insertion of the ethane fragment as a unit bridging the two coordinated diphenylphosphino ligands, we observed the formal insertion of a guanidinate fragment linking the two phosphorus atoms. This resulting complex was characterized in 31P NMR by a sharp singlet at 118.1 p.p.m. associated to the functionalized Ph2P—N group. The analysis of the crude mixture by 1H NMR revealed the formation of bromoethylene in the course of the reaction. The formation of this by-product implies a dehydrobromation of the initial dibromoethane reagent and the release of HBr probably trapped by an H-hpp molecule to form the corresponding guanidinium bromide. The latter guanidinium may act as a potential reagent in the formation of the title complex. The complete understanding of the particular reactivity of the [Ru(bpy)2(PHR2)]2+ complex with dibromoethane and H-hpp requires further studies that are currently under progress.

Related literature top

For the synthesis of the precursor, [Ru(bpy)2(Ph2PH)2](PF6)2, see: Sullivan et al. (1978).

Experimental top

All manipulations were carried out in dry solvents and under dry argon atmosphere. The precursor complex [Ru(bpy)2(Ph2PH)2](PF6)2 was prepared according to a previously described procedure (Sullivan et al., 1978). 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine (H-hpp) (Sigma-Aldrich) was used without further purification. This precursor complex [Ru(bpy)2(Ph2PH)2](PF6)2 (50 mg, 0.046 mmol) was dissolved in acetonitrile (3 ml) and transferred onto 4 equivalents of H-hpp (26 mg, 0.18 mmol) using a standard Schlenk-line and cannula techniques under a dry argon atmosphere. After further addition of a ten-fold excess of BrCH2CH2Br (40 µL, 0.46 mmol) under argon, the reaction mixture was stirred for 30 min at room temperature. Addition of the crude mixture to 50 ml of Et2O induced precipitation of a light yellow/orange solid which was isolated by filtration and dried under vacuum. Dissolution of 15 mg of this solid in 0.5 ml of dry CH2Cl2 followed by careful addition of 3 ml of diethylether as a non-solvent afforded, after 3 days at room temperature, yellow needle-like crystals of the title compound, suitable for X-ray diffraction analysis.

Refinement top

The water H atoms were located in a difference Fourier map and freely refined. The C-bound H atoms were positioned geometrically (C—H = 0.95 - 1.00 Å) and refined as riding on their parent atoms, with Uiso(H) = 1.2Ueq(C). One of the dichloromethane molecules is disordered about a Cl atom, viz. atom Cl3 (occupancy 0.5).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The molecule structure of the title cation, with the atom labelling. The displacement ellipsoids are drawn at the 50% probability level. The H atoms and the anions and solvent molecules of crystallization have been omitted for clarity.
Bis(2,2'-bipyridine)[1,9-bis(diphenylphosphanyl)-1,2,3,4,6,7,8,9-octahydropyrimido[1,2-a]pyrimidin-5-ium]ruthenium(II) hexafluoridophosphate dibromide dichloromethane disolvate monohydrate top
Crystal data top
[Ru(C31H32N3P2)(C10H8N2)2](PF6)Br2·2CH2Cl2·H2OF(000) = 2840
Mr = 1414.63Dx = 1.671 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6399 reflections
a = 16.1770 (4) Åθ = 2.9–29.3°
b = 20.9840 (5) ŵ = 2.04 mm1
c = 16.6730 (4) ÅT = 100 K
β = 96.654 (2)°Needle, yellow
V = 5621.7 (2) Å30.18 × 0.05 × 0.04 mm
Z = 4
Data collection top
Agilent Xcalibur (Eos, Gemini ultra)
diffractometer
10285 independent reflections
Graphite monochromator7429 reflections with I > 2σ(I)
Detector resolution: 16.1978 pixels mm-1Rint = 0.079
ω scansθmax = 25.4°, θmin = 3.1°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
h = 1919
Tmin = 0.964, Tmax = 1.0k = 2525
44290 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0435P)2 + 24.738P]
where P = (Fo2 + 2Fc2)/3
10285 reflections(Δ/σ)max = 0.003
718 parametersΔρmax = 1.72 e Å3
3 restraintsΔρmin = 1.69 e Å3
Crystal data top
[Ru(C31H32N3P2)(C10H8N2)2](PF6)Br2·2CH2Cl2·H2OV = 5621.7 (2) Å3
Mr = 1414.63Z = 4
Monoclinic, P21/nMo Kα radiation
a = 16.1770 (4) ŵ = 2.04 mm1
b = 20.9840 (5) ÅT = 100 K
c = 16.6730 (4) Å0.18 × 0.05 × 0.04 mm
β = 96.654 (2)°
Data collection top
Agilent Xcalibur (Eos, Gemini ultra)
diffractometer
10285 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
7429 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 1.0Rint = 0.079
44290 measured reflectionsθmax = 25.4°
Refinement top
R[F2 > 2σ(F2)] = 0.055 w = 1/[σ2(Fo2) + (0.0435P)2 + 24.738P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.131Δρmax = 1.72 e Å3
S = 1.04Δρmin = 1.69 e Å3
10285 reflectionsAbsolute structure: ?
718 parametersAbsolute structure parameter: ?
3 restraintsRogers parameter: ?
H atoms treated by a mixture of independent and constrained refinement
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ru10.16075 (2)0.18750 (2)1.06626 (2)0.0086 (1)
P10.22497 (8)0.28461 (7)1.07860 (8)0.0112 (4)
P20.13101 (8)0.20991 (6)0.93213 (8)0.0087 (4)
N10.0950 (2)0.0986 (2)1.0652 (2)0.0092 (12)
N20.0410 (3)0.2163 (2)1.0855 (3)0.0118 (12)
N30.1887 (3)0.1558 (2)1.1890 (3)0.0129 (12)
N40.2769 (2)0.1431 (2)1.0649 (3)0.0101 (12)
N50.1981 (3)0.26713 (19)0.8966 (3)0.0100 (12)
N60.1841 (3)0.3392 (2)1.0031 (3)0.0114 (12)
N70.2028 (3)0.3769 (2)0.8750 (3)0.0126 (12)
C10.1953 (3)0.3287 (2)0.9243 (3)0.0108 (17)
C20.2373 (3)0.2608 (3)0.8204 (3)0.0149 (17)
C30.1907 (3)0.3027 (3)0.7566 (3)0.0167 (17)
C40.1973 (3)0.3714 (3)0.7859 (3)0.0166 (17)
C50.2185 (4)0.4437 (2)0.9020 (3)0.0183 (17)
C60.2187 (4)0.4516 (3)0.9929 (3)0.0196 (17)
C70.1565 (3)0.4053 (2)1.0204 (3)0.0151 (17)
C80.0097 (3)0.2764 (3)1.0803 (3)0.0169 (17)
C90.0705 (4)0.2905 (3)1.0931 (4)0.029 (2)
C100.1216 (4)0.2419 (3)1.1140 (5)0.035 (2)
C110.0916 (4)0.1801 (3)1.1182 (4)0.0271 (19)
C120.0108 (3)0.1683 (3)1.1030 (3)0.0134 (17)
C130.0222 (3)0.1033 (3)1.0976 (3)0.0120 (17)
C140.0164 (3)0.0498 (3)1.1255 (3)0.0167 (17)
C150.0178 (3)0.0095 (3)1.1163 (3)0.0152 (17)
C160.0899 (3)0.0148 (2)1.0796 (3)0.0129 (17)
C170.1272 (3)0.0404 (2)1.0555 (3)0.0116 (17)
C180.1387 (3)0.1613 (3)1.2482 (3)0.0152 (17)
C190.1509 (3)0.1268 (3)1.3195 (3)0.0175 (17)
C200.2170 (3)0.0845 (3)1.3298 (3)0.0214 (17)
C210.2690 (3)0.0778 (3)1.2701 (3)0.0176 (17)
C220.2534 (3)0.1136 (3)1.1996 (3)0.0144 (17)
C230.3046 (3)0.1093 (3)1.1319 (3)0.0137 (17)
C240.3792 (3)0.0758 (3)1.1392 (3)0.0175 (17)
C250.4279 (3)0.0772 (3)1.0759 (4)0.0199 (19)
C260.4020 (3)0.1139 (3)1.0089 (3)0.0175 (17)
C270.3265 (3)0.1452 (2)1.0050 (3)0.0127 (17)
C280.3367 (3)0.2821 (3)1.0734 (3)0.0135 (17)
C290.3789 (3)0.3049 (3)1.0110 (3)0.0171 (17)
C300.4642 (3)0.2938 (3)1.0125 (4)0.0217 (17)
C310.5067 (4)0.2608 (3)1.0762 (4)0.0251 (19)
C320.4660 (3)0.2390 (3)1.1396 (4)0.0207 (17)
C330.3824 (4)0.2502 (3)1.1390 (3)0.0180 (17)
C340.2233 (4)0.3333 (3)1.1694 (3)0.0161 (17)
C350.1644 (4)0.3244 (3)1.2224 (3)0.0206 (17)
C360.1653 (4)0.3621 (3)1.2915 (4)0.0261 (19)
C370.2240 (4)0.4105 (3)1.3059 (4)0.0269 (19)
C380.2830 (4)0.4191 (3)1.2531 (3)0.0239 (19)
C390.2835 (4)0.3807 (3)1.1861 (3)0.0181 (17)
C400.1329 (3)0.1473 (2)0.8561 (3)0.0113 (17)
C410.1784 (3)0.0913 (3)0.8701 (3)0.0126 (17)
C420.1763 (3)0.0439 (3)0.8122 (3)0.0140 (17)
C430.1275 (3)0.0513 (3)0.7391 (3)0.0185 (17)
C440.0819 (4)0.1069 (3)0.7233 (3)0.0191 (17)
C450.0841 (3)0.1541 (3)0.7813 (3)0.0145 (17)
C460.0257 (3)0.2402 (2)0.9035 (3)0.0110 (17)
C470.0047 (3)0.3013 (3)0.8753 (3)0.0146 (17)
C480.0788 (3)0.3179 (3)0.8561 (3)0.0171 (17)
C490.1411 (3)0.2750 (3)0.8654 (3)0.0191 (17)
C500.1211 (3)0.2139 (3)0.8935 (3)0.0190 (17)
C510.0386 (3)0.1967 (3)0.9116 (3)0.0147 (17)
P40.17252 (9)0.41418 (7)0.54217 (9)0.0184 (5)
F10.2120 (3)0.3586 (2)0.4949 (2)0.0469 (17)
F20.1156 (2)0.36512 (19)0.5839 (2)0.0416 (14)
F30.2447 (2)0.40650 (16)0.6163 (2)0.0260 (11)
F40.1330 (2)0.47123 (18)0.5888 (2)0.0353 (12)
F50.2283 (2)0.46563 (19)0.5014 (2)0.0386 (12)
F60.1007 (2)0.42265 (18)0.4683 (2)0.0349 (12)
Cl30.2960 (2)0.70831 (18)0.9915 (3)0.0480 (14)0.500
Cl40.36669 (13)0.57601 (10)0.97660 (11)0.0510 (7)
Cl70.4359 (2)0.4762 (2)1.0914 (4)0.0715 (19)0.500
C1050.4601 (11)0.5292 (12)1.0141 (11)0.081 (8)0.500
C1060.2731 (9)0.6301 (7)0.9517 (14)0.067 (7)0.500
Cl10.1583 (2)0.60233 (13)0.7607 (3)0.172 (3)
Cl20.04304 (17)0.69559 (13)0.68604 (15)0.0795 (10)
C1000.0559 (8)0.6172 (5)0.7220 (7)0.096 (5)
Br10.48199 (5)0.01025 (4)0.34126 (4)0.0422 (3)
Br20.07640 (4)0.88384 (3)0.67696 (4)0.0315 (2)
O10.9184 (3)0.4281 (2)0.0087 (3)0.0417 (19)
H2A0.235000.215800.802300.0180*
H2B0.296400.274000.829700.0180*
H3A0.131500.289600.747300.0200*
H3B0.215100.298500.705100.0200*
H4A0.247300.391100.767300.0200*
H4B0.148000.395400.761400.0200*
H5A0.175000.471600.873800.0220*
H5B0.272900.457700.886500.0220*
H6A0.274900.442801.020900.0240*
H6B0.203200.495801.005700.0240*
H7A0.153300.410401.079000.0180*
H7B0.100600.413500.991400.0180*
H80.044900.310101.067200.0200*
H90.090700.333001.087700.0350*
H100.176600.250901.125400.0420*
H110.126200.146101.131500.0320*
H140.066000.054001.150500.0200*
H150.007900.046501.135200.0190*
H160.113400.055401.071100.0160*
H170.177300.036901.031200.0140*
H180.093100.190101.240600.0180*
H190.114900.132001.360200.0210*
H200.226600.060001.377900.0260*
H210.314700.049101.277100.0210*
H240.396700.052301.186900.0210*
H250.478100.053401.078600.0240*
H260.435600.117600.966100.0210*
H270.308600.169400.958000.0150*
H290.349700.327900.967600.0210*
H300.492900.308900.969700.0260*
H310.564600.253001.076600.0300*
H320.495700.216401.183100.0250*
H330.354900.236401.183200.0220*
H350.123000.292401.211700.0250*
H360.125900.354801.328600.0320*
H370.223600.437401.351700.0320*
H380.323600.451801.263000.0290*
H390.325100.386601.150900.0220*
H410.211600.085500.920400.0150*
H420.208300.006200.822800.0170*
H430.125100.018400.699700.0220*
H440.049300.112500.672600.0230*
H450.052100.191700.770400.0180*
H470.047200.331600.869200.0170*
H480.092700.359500.836400.0200*
H490.197700.287100.852700.0230*
H500.163900.184100.900200.0230*
H510.025200.154700.929800.0170*
H10C0.258800.632500.892400.0800*0.500
H10D0.224600.612300.975300.0800*0.500
H9980.480200.504800.971800.0990*0.500
H9990.504800.556601.036400.0990*0.500
H10A0.019200.610000.764700.1140*
H10B0.039200.587100.677400.1140*
H1A0.947 (4)0.450 (3)0.0569 (19)0.0500*
H1B0.936 (4)0.446 (3)0.0423 (17)0.0500*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.0088 (2)0.0082 (2)0.0089 (2)0.0012 (2)0.0011 (2)0.0006 (2)
P10.0142 (7)0.0113 (7)0.0080 (7)0.0026 (6)0.0006 (5)0.0000 (6)
P20.0085 (6)0.0080 (6)0.0096 (7)0.0009 (5)0.0009 (5)0.0003 (5)
N10.009 (2)0.009 (2)0.009 (2)0.0032 (18)0.0009 (17)0.0001 (18)
N20.010 (2)0.015 (2)0.010 (2)0.0014 (19)0.0011 (17)0.0031 (19)
N30.012 (2)0.011 (2)0.015 (2)0.003 (2)0.0016 (18)0.0007 (19)
N40.009 (2)0.010 (2)0.011 (2)0.0048 (18)0.0005 (17)0.0010 (18)
N50.012 (2)0.007 (2)0.012 (2)0.0003 (18)0.0053 (18)0.0006 (18)
N60.014 (2)0.008 (2)0.012 (2)0.0022 (19)0.0005 (18)0.0009 (18)
N70.013 (2)0.012 (2)0.013 (2)0.0024 (19)0.0030 (18)0.0016 (19)
C10.010 (3)0.012 (3)0.010 (3)0.002 (2)0.000 (2)0.001 (2)
C20.015 (3)0.015 (3)0.016 (3)0.000 (2)0.008 (2)0.000 (2)
C30.019 (3)0.021 (3)0.010 (3)0.001 (2)0.001 (2)0.004 (2)
C40.016 (3)0.020 (3)0.014 (3)0.002 (2)0.003 (2)0.007 (2)
C50.027 (3)0.007 (3)0.020 (3)0.006 (2)0.001 (2)0.003 (2)
C60.027 (3)0.011 (3)0.020 (3)0.003 (3)0.001 (3)0.000 (2)
C70.022 (3)0.010 (3)0.013 (3)0.002 (2)0.001 (2)0.001 (2)
C80.019 (3)0.011 (3)0.022 (3)0.001 (2)0.008 (2)0.006 (2)
C90.026 (3)0.013 (3)0.053 (5)0.010 (3)0.023 (3)0.005 (3)
C100.024 (3)0.022 (3)0.065 (5)0.008 (3)0.030 (3)0.006 (3)
C110.022 (3)0.023 (3)0.039 (4)0.003 (3)0.015 (3)0.003 (3)
C120.013 (3)0.015 (3)0.012 (3)0.002 (2)0.001 (2)0.000 (2)
C130.012 (3)0.017 (3)0.007 (3)0.000 (2)0.001 (2)0.000 (2)
C140.016 (3)0.021 (3)0.014 (3)0.006 (3)0.006 (2)0.001 (2)
C150.015 (3)0.011 (3)0.020 (3)0.003 (2)0.004 (2)0.004 (2)
C160.016 (3)0.007 (3)0.015 (3)0.000 (2)0.001 (2)0.001 (2)
C170.011 (3)0.014 (3)0.010 (3)0.001 (2)0.002 (2)0.001 (2)
C180.015 (3)0.018 (3)0.013 (3)0.004 (2)0.003 (2)0.001 (2)
C190.020 (3)0.021 (3)0.011 (3)0.003 (3)0.000 (2)0.004 (2)
C200.020 (3)0.028 (3)0.015 (3)0.007 (3)0.003 (2)0.011 (3)
C210.016 (3)0.014 (3)0.022 (3)0.002 (2)0.001 (2)0.003 (2)
C220.013 (3)0.014 (3)0.015 (3)0.007 (2)0.003 (2)0.002 (2)
C230.012 (3)0.013 (3)0.015 (3)0.004 (2)0.003 (2)0.002 (2)
C240.016 (3)0.018 (3)0.017 (3)0.002 (2)0.004 (2)0.001 (2)
C250.010 (3)0.015 (3)0.034 (4)0.005 (2)0.000 (2)0.001 (3)
C260.014 (3)0.019 (3)0.020 (3)0.005 (2)0.004 (2)0.003 (2)
C270.013 (3)0.011 (3)0.014 (3)0.006 (2)0.001 (2)0.001 (2)
C280.014 (3)0.012 (3)0.014 (3)0.005 (2)0.001 (2)0.001 (2)
C290.016 (3)0.017 (3)0.017 (3)0.003 (2)0.004 (2)0.001 (2)
C300.015 (3)0.020 (3)0.030 (3)0.006 (3)0.002 (3)0.005 (3)
C310.016 (3)0.019 (3)0.039 (4)0.004 (3)0.002 (3)0.006 (3)
C320.016 (3)0.017 (3)0.026 (3)0.004 (3)0.011 (3)0.001 (3)
C330.025 (3)0.016 (3)0.012 (3)0.007 (3)0.002 (2)0.001 (2)
C340.026 (3)0.011 (3)0.010 (3)0.001 (2)0.003 (2)0.002 (2)
C350.030 (3)0.015 (3)0.017 (3)0.002 (3)0.004 (2)0.003 (2)
C360.040 (4)0.024 (3)0.016 (3)0.002 (3)0.011 (3)0.001 (3)
C370.044 (4)0.021 (3)0.015 (3)0.004 (3)0.000 (3)0.002 (3)
C380.033 (4)0.016 (3)0.020 (3)0.001 (3)0.008 (3)0.000 (3)
C390.024 (3)0.018 (3)0.011 (3)0.005 (3)0.003 (2)0.002 (2)
C400.013 (3)0.012 (3)0.009 (3)0.003 (2)0.002 (2)0.001 (2)
C410.010 (3)0.018 (3)0.010 (3)0.000 (2)0.002 (2)0.002 (2)
C420.010 (3)0.012 (3)0.021 (3)0.002 (2)0.006 (2)0.000 (2)
C430.026 (3)0.015 (3)0.015 (3)0.000 (3)0.005 (2)0.005 (2)
C440.025 (3)0.021 (3)0.010 (3)0.003 (3)0.003 (2)0.002 (2)
C450.015 (3)0.013 (3)0.015 (3)0.001 (2)0.000 (2)0.001 (2)
C460.010 (3)0.014 (3)0.008 (3)0.003 (2)0.003 (2)0.006 (2)
C470.011 (3)0.017 (3)0.015 (3)0.004 (2)0.002 (2)0.000 (2)
C480.022 (3)0.015 (3)0.014 (3)0.004 (3)0.001 (2)0.005 (2)
C490.007 (3)0.027 (3)0.023 (3)0.005 (3)0.000 (2)0.001 (3)
C500.018 (3)0.021 (3)0.018 (3)0.003 (3)0.002 (2)0.003 (3)
C510.019 (3)0.012 (3)0.013 (3)0.002 (2)0.002 (2)0.002 (2)
P40.0195 (8)0.0192 (8)0.0169 (8)0.0051 (7)0.0034 (6)0.0010 (6)
F10.049 (3)0.047 (3)0.043 (3)0.017 (2)0.002 (2)0.023 (2)
F20.036 (2)0.043 (2)0.046 (3)0.0156 (19)0.0063 (19)0.017 (2)
F30.0264 (18)0.0282 (19)0.0229 (19)0.0014 (16)0.0006 (15)0.0011 (16)
F40.033 (2)0.034 (2)0.039 (2)0.0078 (18)0.0045 (17)0.0063 (18)
F50.034 (2)0.049 (2)0.033 (2)0.0179 (19)0.0050 (17)0.0101 (19)
F60.032 (2)0.043 (2)0.027 (2)0.0096 (18)0.0079 (16)0.0055 (18)
Cl30.036 (2)0.044 (2)0.067 (3)0.0024 (17)0.0193 (19)0.014 (2)
Cl40.0671 (13)0.0561 (13)0.0310 (10)0.0170 (11)0.0108 (9)0.0011 (9)
Cl70.029 (2)0.039 (2)0.141 (5)0.0029 (18)0.013 (2)0.029 (3)
C1050.047 (11)0.16 (2)0.038 (10)0.004 (13)0.017 (8)0.021 (13)
C1060.027 (8)0.028 (9)0.145 (19)0.014 (7)0.006 (10)0.032 (10)
Cl10.128 (3)0.0528 (17)0.372 (7)0.0370 (18)0.190 (4)0.051 (3)
Cl20.103 (2)0.0839 (18)0.0588 (15)0.0530 (16)0.0399 (14)0.0097 (13)
C1000.159 (12)0.057 (6)0.087 (8)0.038 (7)0.083 (8)0.014 (6)
Br10.0423 (4)0.0485 (5)0.0337 (4)0.0147 (4)0.0046 (3)0.0042 (4)
Br20.0248 (3)0.0341 (4)0.0367 (4)0.0028 (3)0.0085 (3)0.0162 (3)
O10.065 (4)0.025 (3)0.036 (3)0.009 (2)0.010 (3)0.001 (2)
Geometric parameters (Å, º) top
Ru1—P12.2857 (15)C35—C361.396 (8)
Ru1—P22.2813 (14)C36—C371.392 (9)
Ru1—N12.147 (4)C37—C381.383 (9)
Ru1—N22.089 (5)C38—C391.378 (8)
Ru1—N32.150 (5)C40—C411.392 (7)
Ru1—N42.100 (4)C40—C451.404 (7)
Cl3—C1061.793 (16)C41—C421.384 (8)
Cl4—C1061.899 (15)C42—C431.382 (7)
Cl4—C1051.85 (2)C43—C441.389 (9)
Cl7—C1051.78 (2)C44—C451.382 (8)
Cl1—C1001.735 (13)C46—C471.394 (7)
Cl2—C1001.755 (11)C46—C511.402 (7)
P1—C281.820 (5)C47—C481.396 (7)
P1—C341.829 (6)C48—C491.373 (8)
P1—N61.772 (5)C49—C501.390 (9)
P2—C461.829 (5)C50—C511.382 (7)
P2—N51.766 (5)C2—H2B0.9900
P2—C401.828 (5)C2—H2A0.9900
P4—F41.601 (4)C3—H3B0.9900
P4—F51.608 (4)C3—H3A0.9900
P4—F61.602 (4)C4—H4A0.9900
P4—F31.607 (4)C4—H4B0.9900
P4—F21.594 (4)C5—H5B0.9900
P4—F11.583 (4)C5—H5A0.9900
N1—C171.345 (6)C6—H6A0.9900
N1—C131.355 (6)C6—H6B0.9900
N2—C81.358 (7)C7—H7A0.9900
N2—C121.363 (7)C7—H7B0.9900
N3—C181.352 (7)C8—H80.9500
N3—C221.367 (7)C9—H90.9500
N4—C231.355 (7)C10—H100.9500
N4—C271.352 (7)C11—H110.9500
N5—C21.490 (7)C14—H140.9500
N5—C11.375 (6)C15—H150.9500
N6—C71.495 (6)C16—H160.9500
N6—C11.365 (7)C17—H170.9500
N7—C11.318 (6)C18—H180.9500
N7—C41.482 (7)C19—H190.9500
N7—C51.485 (6)C20—H200.9500
O1—H1A0.99 (5)C21—H210.9500
O1—H1B1.00 (4)C24—H240.9500
C2—C31.512 (8)C25—H250.9500
C3—C41.522 (9)C26—H260.9500
C5—C61.524 (7)C27—H270.9500
C6—C71.508 (8)C29—H290.9500
C8—C91.371 (8)C30—H300.9500
C9—C101.383 (9)C31—H310.9500
C10—C111.384 (9)C32—H320.9500
C11—C121.382 (8)C33—H330.9500
C12—C131.471 (9)C35—H350.9500
C13—C141.391 (8)C36—H360.9500
C14—C151.378 (9)C37—H370.9500
C15—C161.383 (7)C38—H380.9500
C16—C171.387 (6)C39—H390.9500
C18—C191.386 (8)C41—H410.9500
C19—C201.385 (8)C42—H420.9500
C20—C211.383 (7)C43—H430.9500
C21—C221.393 (8)C44—H440.9500
C22—C231.478 (7)C45—H450.9500
C23—C241.390 (7)C47—H470.9500
C24—C251.389 (8)C48—H480.9500
C25—C261.381 (8)C49—H490.9500
C26—C271.382 (7)C50—H500.9500
C28—C291.394 (7)C51—H510.9500
C28—C331.416 (8)C105—H9980.9600
C29—C301.397 (7)C105—H9990.9600
C30—C311.382 (9)C106—H10D0.9900
C31—C321.386 (9)C106—H10C0.9900
C32—C331.372 (8)C100—H10B0.9900
C34—C351.385 (8)C100—H10A0.9900
C34—C391.397 (9)
P1—Ru1—P286.93 (5)C47—C46—C51118.5 (5)
P1—Ru1—N1174.37 (10)P2—C46—C47126.2 (4)
P1—Ru1—N298.52 (12)C46—C47—C48119.9 (5)
P1—Ru1—N398.45 (12)C47—C48—C49120.9 (6)
P1—Ru1—N489.92 (12)C48—C49—C50119.8 (5)
P2—Ru1—N197.07 (10)C49—C50—C51119.7 (5)
P2—Ru1—N289.82 (14)C46—C51—C50121.2 (5)
P2—Ru1—N3173.86 (12)C3—C2—H2A110.00
P2—Ru1—N499.68 (14)N5—C2—H2A110.00
N1—Ru1—N277.60 (15)H2A—C2—H2B108.00
N1—Ru1—N377.78 (15)N5—C2—H2B110.00
N1—Ru1—N493.30 (15)C3—C2—H2B110.00
N2—Ru1—N392.28 (19)C2—C3—H3B110.00
N2—Ru1—N4167.64 (18)C2—C3—H3A110.00
N3—Ru1—N477.48 (19)C4—C3—H3B110.00
C105—Cl4—C106172.2 (9)C4—C3—H3A110.00
Ru1—P1—C28114.4 (2)H3A—C3—H3B108.00
Ru1—P1—C34121.5 (2)N7—C4—H4B109.00
N6—P1—C28106.0 (2)C3—C4—H4A109.00
N6—P1—C34100.8 (2)C3—C4—H4B109.00
C28—P1—C3499.5 (3)H4A—C4—H4B108.00
Ru1—P1—N6112.58 (16)N7—C4—H4A109.00
Ru1—P2—N5113.64 (17)N7—C5—H5A109.00
Ru1—P2—C46114.31 (17)N7—C5—H5B109.00
N5—P2—C40101.3 (2)C6—C5—H5B109.00
N5—P2—C46105.4 (2)H5A—C5—H5B108.00
C40—P2—C4699.1 (2)C6—C5—H5A109.00
Ru1—P2—C40120.86 (16)C5—C6—H6B110.00
F4—P4—F689.75 (19)C7—C6—H6A110.00
F5—P4—F689.60 (19)H6A—C6—H6B108.00
F1—P4—F390.6 (2)C7—C6—H6B110.00
F1—P4—F4179.0 (2)C5—C6—H6A110.00
F1—P4—F590.3 (2)N6—C7—H7B110.00
F1—P4—F689.9 (2)C6—C7—H7A110.00
F2—P4—F390.26 (18)H7A—C7—H7B108.00
F2—P4—F489.3 (2)C6—C7—H7B110.00
F2—P4—F5178.0 (2)N6—C7—H7A110.00
F2—P4—F690.18 (19)C9—C8—H8119.00
F3—P4—F489.83 (18)N2—C8—H8119.00
F3—P4—F589.95 (18)C10—C9—H9120.00
F3—P4—F6179.4 (2)C8—C9—H9121.00
F4—P4—F588.8 (2)C9—C10—H10120.00
F1—P4—F291.6 (2)C11—C10—H10120.00
Ru1—N1—C13112.7 (4)C12—C11—H11120.00
Ru1—N1—C17126.3 (3)C10—C11—H11120.00
C13—N1—C17118.7 (4)C13—C14—H14120.00
Ru1—N2—C12115.0 (3)C15—C14—H14120.00
Ru1—N2—C8127.2 (4)C14—C15—H15120.00
C8—N2—C12117.8 (5)C16—C15—H15120.00
C18—N3—C22118.4 (5)C15—C16—H16121.00
Ru1—N3—C18126.2 (4)C17—C16—H16121.00
Ru1—N3—C22113.4 (4)C16—C17—H17119.00
C23—N4—C27117.3 (4)N1—C17—H17119.00
Ru1—N4—C23115.7 (3)N3—C18—H18119.00
Ru1—N4—C27127.0 (3)C19—C18—H18119.00
C1—N5—C2113.8 (4)C18—C19—H19121.00
P2—N5—C1118.7 (4)C20—C19—H19121.00
P2—N5—C2124.3 (4)C21—C20—H20120.00
C1—N6—C7114.3 (4)C19—C20—H20120.00
P1—N6—C1120.0 (3)C20—C21—H21120.00
P1—N6—C7123.9 (4)C22—C21—H21121.00
C1—N7—C5124.1 (5)C25—C24—H24120.00
C4—N7—C5111.4 (4)C23—C24—H24120.00
C1—N7—C4124.5 (4)C26—C25—H25121.00
H1A—O1—H1B111 (4)C24—C25—H25121.00
N6—C1—N7120.6 (4)C27—C26—H26120.00
N5—C1—N6119.2 (4)C25—C26—H26120.00
N5—C1—N7120.2 (5)C26—C27—H27118.00
N5—C2—C3108.7 (4)N4—C27—H27118.00
C2—C3—C4108.3 (4)C28—C29—H29120.00
N7—C4—C3112.9 (4)C30—C29—H29120.00
N7—C5—C6112.6 (4)C31—C30—H30120.00
C5—C6—C7107.9 (5)C29—C30—H30120.00
N6—C7—C6108.3 (4)C30—C31—H31120.00
N2—C8—C9122.9 (5)C32—C31—H31120.00
C8—C9—C10119.0 (6)C33—C32—H32120.00
C9—C10—C11119.2 (6)C31—C32—H32120.00
C10—C11—C12119.5 (6)C28—C33—H33120.00
N2—C12—C11121.6 (6)C32—C33—H33120.00
N2—C12—C13115.8 (4)C34—C35—H35120.00
C11—C12—C13122.3 (5)C36—C35—H35120.00
N1—C13—C14121.3 (5)C37—C36—H36120.00
C12—C13—C14123.2 (5)C35—C36—H36120.00
N1—C13—C12115.5 (5)C38—C37—H37120.00
C13—C14—C15119.4 (5)C36—C37—H37120.00
C14—C15—C16119.5 (5)C37—C38—H38120.00
C15—C16—C17118.6 (4)C39—C38—H38120.00
N1—C17—C16122.4 (4)C38—C39—H39120.00
N3—C18—C19123.0 (5)C34—C39—H39120.00
C18—C19—C20118.2 (5)C40—C41—H41119.00
C19—C20—C21120.1 (5)C42—C41—H41119.00
C20—C21—C22119.1 (5)C43—C42—H42120.00
N3—C22—C21121.3 (5)C41—C42—H42120.00
C21—C22—C23123.3 (5)C44—C43—H43120.00
N3—C22—C23115.4 (5)C42—C43—H43120.00
N4—C23—C24122.5 (4)C45—C44—H44120.00
C22—C23—C24121.5 (5)C43—C44—H44120.00
N4—C23—C22115.9 (5)C40—C45—H45120.00
C23—C24—C25119.1 (5)C44—C45—H45119.00
C24—C25—C26118.7 (5)C48—C47—H47120.00
C25—C26—C27119.1 (5)C46—C47—H47120.00
N4—C27—C26123.1 (4)C47—C48—H48119.00
C29—C28—C33118.8 (5)C49—C48—H48120.00
P1—C28—C33114.2 (4)C50—C49—H49120.00
P1—C28—C29126.9 (4)C48—C49—H49120.00
C28—C29—C30119.9 (5)C49—C50—H50120.00
C29—C30—C31120.0 (6)C51—C50—H50120.00
C30—C31—C32120.9 (6)C50—C51—H51119.00
C31—C32—C33119.5 (6)C46—C51—H51119.00
C28—C33—C32120.9 (5)Cl4—C105—Cl7109.7 (9)
P1—C34—C39119.1 (4)Cl3—C106—Cl4109.9 (9)
P1—C34—C35122.0 (5)Cl4—C105—H998112.00
C35—C34—C39118.9 (5)Cl7—C105—H998109.00
C34—C35—C36120.5 (6)Cl7—C105—H999108.00
C35—C36—C37119.8 (6)H998—C105—H999107.00
C36—C37—C38119.5 (6)Cl4—C105—H999111.00
C37—C38—C39120.6 (6)Cl3—C106—H10C110.00
C34—C39—C38120.6 (6)Cl4—C106—H10C110.00
P2—C40—C41122.8 (4)Cl4—C106—H10D110.00
C41—C40—C45117.8 (5)Cl3—C106—H10D110.00
P2—C40—C45119.3 (4)H10C—C106—H10D108.00
C40—C41—C42121.3 (5)Cl1—C100—Cl2111.5 (7)
C41—C42—C43120.0 (5)Cl1—C100—H10A109.00
C42—C43—C44119.9 (5)Cl1—C100—H10B109.00
C43—C44—C45120.0 (5)Cl2—C100—H10B109.00
C40—C45—C44121.0 (5)H10A—C100—H10B108.00
P2—C46—C51115.3 (4)Cl2—C100—H10A109.00
P2—Ru1—P1—N626.11 (18)C12—N2—C8—C91.1 (8)
N2—Ru1—P1—N663.3 (2)Ru1—N2—C12—C11179.2 (4)
N3—Ru1—P1—N6156.9 (2)Ru1—N2—C8—C9179.2 (4)
N4—Ru1—P1—N6125.8 (2)Ru1—N2—C12—C136.0 (6)
P2—Ru1—P1—C2895.00 (19)Ru1—N3—C18—C19163.8 (4)
N2—Ru1—P1—C28175.6 (2)C18—N3—C22—C23179.0 (5)
N3—Ru1—P1—C2882.0 (2)Ru1—N3—C22—C2314.1 (6)
N4—Ru1—P1—C284.7 (2)C22—N3—C18—C191.0 (8)
P2—Ru1—P1—C34145.6 (2)Ru1—N3—C22—C21166.2 (4)
N2—Ru1—P1—C3456.2 (3)C18—N3—C22—C211.2 (8)
N3—Ru1—P1—C3437.4 (3)C27—N4—C23—C22173.7 (5)
N4—Ru1—P1—C34114.7 (3)C27—N4—C23—C242.3 (8)
P1—Ru1—P2—N522.53 (17)Ru1—N4—C23—C24178.2 (4)
N1—Ru1—P2—N5161.45 (19)Ru1—N4—C23—C225.8 (6)
N2—Ru1—P2—N5121.1 (2)Ru1—N4—C27—C26179.4 (4)
N4—Ru1—P2—N566.9 (2)C23—N4—C27—C261.2 (7)
P1—Ru1—P2—C40143.22 (19)C2—N5—C1—N719.4 (7)
N1—Ru1—P2—C4040.8 (2)C2—N5—C1—N6161.0 (5)
N2—Ru1—P2—C40118.2 (2)P2—N5—C1—N638.0 (6)
N4—Ru1—P2—C4053.8 (2)P2—N5—C1—N7141.6 (4)
P1—Ru1—P2—C4698.57 (16)C1—N5—C2—C356.9 (6)
N1—Ru1—P2—C4677.45 (19)P2—N5—C2—C3102.9 (5)
N2—Ru1—P2—C460.0 (2)C1—N6—C7—C655.9 (6)
N4—Ru1—P2—C46172.04 (19)P1—N6—C7—C6108.5 (4)
P2—Ru1—N1—C13104.8 (3)C7—N6—C1—N5162.4 (4)
N2—Ru1—N1—C1316.6 (3)C7—N6—C1—N717.2 (7)
N3—Ru1—N1—C1378.6 (3)P1—N6—C1—N532.6 (6)
N4—Ru1—N1—C13155.0 (3)P1—N6—C1—N7147.8 (4)
P2—Ru1—N1—C1792.7 (4)C1—N7—C5—C64.3 (8)
N2—Ru1—N1—C17179.1 (4)C4—N7—C5—C6176.2 (5)
N3—Ru1—N1—C1784.0 (4)C5—N7—C4—C3173.7 (4)
N4—Ru1—N1—C177.5 (4)C4—N7—C1—N513.1 (8)
P1—Ru1—N2—C818.0 (5)C4—N7—C1—N6166.5 (5)
P2—Ru1—N2—C868.9 (5)C1—N7—C4—C35.9 (7)
N1—Ru1—N2—C8166.2 (5)C5—N7—C1—N5166.5 (5)
N3—Ru1—N2—C8116.9 (5)C5—N7—C1—N614.0 (8)
P1—Ru1—N2—C12163.9 (4)N5—C2—C3—C460.8 (5)
P2—Ru1—N2—C12109.2 (4)C2—C3—C4—N731.1 (5)
N1—Ru1—N2—C1212.0 (4)N7—C5—C6—C733.7 (7)
N3—Ru1—N2—C1265.0 (4)C5—C6—C7—N662.1 (6)
P1—Ru1—N3—C1895.4 (4)N2—C8—C9—C101.5 (9)
N1—Ru1—N3—C1880.3 (5)C8—C9—C10—C112.6 (11)
N2—Ru1—N3—C183.5 (5)C9—C10—C11—C121.3 (11)
N4—Ru1—N3—C18176.5 (5)C10—C11—C12—N21.4 (9)
P1—Ru1—N3—C22101.1 (4)C10—C11—C12—C13173.1 (6)
N1—Ru1—N3—C2283.2 (4)C11—C12—C13—N1166.0 (5)
N2—Ru1—N3—C22160.0 (4)N2—C12—C13—N18.8 (7)
N4—Ru1—N3—C2213.1 (4)C11—C12—C13—C1415.7 (8)
P1—Ru1—N4—C23108.8 (4)N2—C12—C13—C14169.5 (5)
P2—Ru1—N4—C23164.4 (4)C12—C13—C14—C15178.5 (5)
N1—Ru1—N4—C2366.6 (4)N1—C13—C14—C153.3 (7)
N3—Ru1—N4—C2310.1 (4)C13—C14—C15—C160.1 (7)
P1—Ru1—N4—C2770.7 (4)C14—C15—C16—C172.1 (7)
P2—Ru1—N4—C2716.2 (4)C15—C16—C17—N11.2 (7)
N1—Ru1—N4—C27113.9 (4)N3—C18—C19—C200.6 (9)
N3—Ru1—N4—C27169.4 (4)C18—C19—C20—C210.4 (8)
C34—P1—C28—C3364.6 (5)C19—C20—C21—C220.6 (9)
C34—P1—N6—C1162.1 (4)C20—C21—C22—C23179.2 (5)
Ru1—P1—N6—C7129.5 (4)C20—C21—C22—N31.1 (8)
C28—P1—N6—C7104.7 (4)C21—C22—C23—C249.5 (9)
C34—P1—N6—C71.4 (5)N3—C22—C23—C24170.2 (5)
N6—P1—C34—C3975.5 (5)C21—C22—C23—N4174.4 (5)
Ru1—P1—N6—C167.0 (4)N3—C22—C23—N45.8 (7)
C28—P1—N6—C158.8 (5)N4—C23—C24—C250.5 (9)
Ru1—P1—C28—C29109.9 (5)C22—C23—C24—C25175.3 (6)
N6—P1—C28—C2914.8 (6)C23—C24—C25—C262.4 (9)
Ru1—P1—C34—C3520.2 (6)C24—C25—C26—C273.5 (9)
N6—P1—C28—C33168.7 (4)C25—C26—C27—N41.7 (8)
Ru1—P1—C28—C3366.6 (5)P1—C28—C29—C30173.8 (5)
C28—P1—C34—C3933.0 (5)P1—C28—C33—C32173.6 (5)
C34—P1—C28—C29119.0 (6)C29—C28—C33—C323.2 (9)
C28—P1—C34—C35146.7 (5)C33—C28—C29—C302.6 (9)
N6—P1—C34—C35104.9 (5)C28—C29—C30—C310.6 (9)
Ru1—P1—C34—C39159.4 (4)C29—C30—C31—C320.8 (10)
C40—P2—N5—C1162.1 (4)C30—C31—C32—C330.2 (10)
C46—P2—N5—C159.2 (5)C31—C32—C33—C281.8 (9)
Ru1—P2—N5—C2134.4 (4)C39—C34—C35—C360.2 (9)
Ru1—P2—N5—C166.8 (4)P1—C34—C35—C36179.5 (5)
N5—P2—C40—C41103.4 (4)C35—C34—C39—C381.7 (9)
N5—P2—C46—C4712.1 (5)P1—C34—C39—C38178.7 (5)
C40—P2—N5—C23.2 (5)C34—C35—C36—C372.3 (9)
Ru1—P2—C40—C4123.2 (5)C35—C36—C37—C382.5 (10)
C46—P2—N5—C299.7 (4)C36—C37—C38—C390.7 (9)
C40—P2—C46—C47116.6 (5)C37—C38—C39—C341.4 (9)
C46—P2—C40—C41148.8 (4)P2—C40—C41—C42177.8 (4)
C46—P2—C40—C4528.6 (4)C41—C40—C45—C440.5 (8)
C40—P2—C46—C5163.6 (4)C45—C40—C41—C420.4 (7)
Ru1—P2—C46—C5166.4 (4)P2—C40—C45—C44178.0 (4)
Ru1—P2—C46—C47113.4 (4)C40—C41—C42—C430.8 (8)
N5—P2—C40—C4579.3 (4)C41—C42—C43—C441.3 (8)
N5—P2—C46—C51168.1 (4)C42—C43—C44—C451.3 (9)
Ru1—P2—C40—C45154.2 (3)C43—C44—C45—C401.0 (9)
Ru1—N1—C13—C1218.6 (5)P2—C46—C47—C48179.7 (4)
C13—N1—C17—C161.9 (7)C51—C46—C47—C480.2 (7)
Ru1—N1—C17—C16159.7 (4)P2—C46—C51—C50178.8 (4)
Ru1—N1—C13—C14159.8 (4)C47—C46—C51—C501.1 (8)
C17—N1—C13—C144.2 (7)C46—C47—C48—C490.7 (8)
C17—N1—C13—C12177.5 (4)C47—C48—C49—C500.7 (8)
C8—N2—C12—C112.5 (8)C48—C49—C50—C510.2 (8)
C8—N2—C12—C13172.3 (5)C49—C50—C51—C461.1 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···Br1i0.99 (5)2.31 (5)3.300 (5)173 (3)
O1—H1B···Br1ii1.00 (4)2.35 (4)3.345 (5)178 (6)
C4—H4A···Br2iii0.992.903.651 (5)133
C6—H6A···Cl70.992.823.738 (8)155
C6—H6B···O1iv0.992.523.358 (8)142
C9—H9···O1v0.952.403.208 (8)142
C10—H10···Cl3vi0.952.723.316 (8)122
C100—H10A···Br1vii0.992.923.618 (11)128
C106—H10C···Cl10.992.653.54 (2)150
C106—H10D···O1iv0.992.513.464 (16)162
C11—H11···F3vii0.952.353.209 (7)150
C17—H17···F5iii0.952.253.056 (6)142
C21—H21···Br1viii0.952.913.787 (5)154
C24—H24···Br1viii0.952.913.835 (5)164
C25—H25···F4ix0.952.543.453 (6)160
C31—H31···Cl3x0.952.763.566 (7)143
C42—H42···F3iii0.952.413.319 (7)160
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z1/2; (iii) x+1/2, y1/2, z+3/2; (iv) x+1, y+1, z+1; (v) x1, y, z+1; (vi) x, y+1, z+2; (vii) x1/2, y+1/2, z+1/2; (viii) x, y, z+1; (ix) x+1/2, y+1/2, z+1/2; (x) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···Br1i0.99 (5)2.31 (5)3.300 (5)173 (3)
O1—H1B···Br1ii1.00 (4)2.35 (4)3.345 (5)178 (6)
C4—H4A···Br2iii0.992.903.651 (5)133
C6—H6A···Cl70.992.823.738 (8)155
C6—H6B···O1iv0.992.523.358 (8)142
C9—H9···O1v0.952.403.208 (8)142
C10—H10···Cl3vi0.952.723.316 (8)122
C100—H10A···Br1vii0.992.923.618 (11)128
C106—H10C···Cl10.992.653.54 (2)150
C106—H10D···O1iv0.992.513.464 (16)162
C11—H11···F3vii0.952.353.209 (7)150
C17—H17···F5iii0.952.253.056 (6)142
C21—H21···Br1viii0.952.913.787 (5)154
C24—H24···Br1viii0.952.913.835 (5)164
C25—H25···F4ix0.952.543.453 (6)160
C31—H31···Cl3x0.952.763.566 (7)143
C42—H42···F3iii0.952.413.319 (7)160
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z1/2; (iii) x+1/2, y1/2, z+3/2; (iv) x+1, y+1, z+1; (v) x1, y, z+1; (vi) x, y+1, z+2; (vii) x1/2, y+1/2, z+1/2; (viii) x, y, z+1; (ix) x+1/2, y+1/2, z+1/2; (x) x+1, y+1, z+2.
Acknowledgements top

CS is grateful to the Université de Toulouse and the Région Midi-Pyrénées for a doctoral fellowship. Johnson Matthey is greatly acknowledged for a gift of RuCl3.xH2O.

references
References top

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435–436.

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Sullivan, B. P., Salmon, D. J. & Meyer, T. J. (1978). Inorg. Chem. 17, 3334–3341.