metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 2| February 2013| Pages m77-m78

cis-Bis(2,2′-bi­pyridine-κ2N,N′)bis­­(pyridin-4-amine-κN1)ruthenium(II) bis­­(hexa­fluoridophosphate) aceto­nitrile monosolvate

aUniversidade Federal de São Carlos, Departamento de Química, CP 676, CEP 13565-905, São Carlos/SP, Brazil, bUniversidade Federal de Goias, Instituto de Química, Campus Samambaia, CP 131, CEP 74001-970, Goiania/GO, Brazil, cUniversidade Federal de Alagoas, Centro de Ciências Exatas e Naturais, Departamento de Química, CEP 57072-970, Maceió/AL, Brazil, and dUniversidade de São Paulo, Instituto de Física de Sao Carlos, CP 369, CEP 13560-970, São Carlos/SP, Brazil
*Correspondence e-mail: rosem@ufscar.br

(Received 7 December 2012; accepted 28 December 2012; online 9 January 2013)

In the title complex, [Ru(C10H8N2)2(C5H6N2)2](PF6)2·CH3CN, the RuII atom is bonded to two α-diimine ligands, viz. 2,2′-bipyridine, in a cis configuration and to two 4-amino­pyridine (4Apy) ligands in the expected distorted octa­hedral configuration. The compound is isostructural with [Ru(C10H8N2)2(C5H6N2)2](ClO4)2·CH3CN [Duan et al. (1999[Duan, C.-Y., Lu, Z.-L., You, X.-Z. & Mak, T. C. W. (1999). J. Coord. Chem. 46, 301-312.]). J. Coord. Chem. 46, 301–312] and both structures are stabilized by classical hydrogen bonds between 4Apy ligands as donors and counter-ions and acetonitrile solvent mol­ecules as acceptors. Indeed, N—H⋯F inter­actions give rise to an inter­molecularly locked assembly of two centrosymmetric complex mol­ecules and two PF6 counter-ions, which can be considered as the building units of both crystal architectures. The building blocks are connected to one another through hydrogen bonds between 4Apy and the connecting pieces made up of two centrosymmetric motifs with PF6 ions and acetonitrile mol­ecules, giving rise to ribbons running parallel to [011]. 21-Screw-axis-related complex mol­ecules and PF6 counter-ions alternate in helical chains formed along the a axis by means of these contacts.

Related literature

For compounds with similar properties, see: Stoyanov et al. (2002[Stoyanov, S. R., Villegas, J. M. & Rillema, D. P. (2002). Inorg. Chem. 41, 2941-2945.]); Duan et al. (1999[Duan, C.-Y., Lu, Z.-L., You, X.-Z. & Mak, T. C. W. (1999). J. Coord. Chem. 46, 301-312.]); Salassa et al. (2009[Salassa, L., Garino, C., Salassa, G., Nervi, C., Gobetto, R., Lamberti, C., Gianolio, D., Bizzarri, R. & Sadler, P. J. (2009). Inorg. Chem. 48, 1469-1481.]). For use of 4Apy, see: Sinha & Shrivastava (2012[Sinha, S. K. & Shrivastava, S. K. (2012). Med. Chem. Res. 21, 4395-4402.]). For the synthesis of the starting materials, see: Bonneson et al. (1983[Bonneson, P. J., Walsh, L., Pennington, W. T., Cordes, A. W. & Durham, B. (1983). Inorg. Chem. 22, 1761-1765.]).

[Scheme 1]

Experimental

Crystal data
  • [Ru(C10H8N2)2(C5H6N2)2](PF6)2·C2H3N

  • Mr = 932.67

  • Triclinic, [P \overline 1]

  • a = 10.8290 (3) Å

  • b = 11.8890 (3) Å

  • c = 16.1020 (4) Å

  • α = 104.073 (1)°

  • β = 99.114 (2)°

  • γ = 107.761 (2)°

  • V = 1853.32 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.61 mm−1

  • T = 298 K

  • 0.21 × 0.11 × 0.09 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.935, Tmax = 0.950

  • 14506 measured reflections

  • 7906 independent reflections

  • 6142 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.148

  • S = 1.06

  • 7906 reflections

  • 506 parameters

  • H-atom parameters constrained

  • Δρmax = 0.90 e Å−3

  • Δρmin = −0.58 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N4—H4A⋯F4i 0.86 2.19 2.871 (8) 135
N4—H4B⋯F6Aii 0.86 2.47 2.962 (7) 117
N4A—H4A1⋯F5iii 0.86 2.44 3.184 (8) 145
N4A—H4A2⋯N1Siv 0.86 2.34 3.162 (13) 161
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+1; (iii) -x, -y, -z+1; (iv) -x+1, -y, -z.

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Comment top

The structure cis-bis(4-Aminopyridine)-bis(2,2'-bipyridine)-ruthenium(II) diperchlorate acetonitrile solvate (Duan et al., 1999) have been reported previously. We present herein the crystal structure of the compound (I) with the hexafluorophosphate counterions.

Asymmetric units of complex (I) is shown in Fig. 1 and each Ru atom is coordinated to six nitrogen atoms from four ligand molecules. The compound (I) crystallizes in the noncentrosymmetric orthorhombic space group P21cn, with one Ru(II) atom, two 2,2-bipyridine (bpy) ligands, two 4-aminopyridine (4Apy) and two PF6- counterions in the asymmetric unit. The complex (I) is also present with one acetonitrile molecule in its asymmetric unit. Both compounds (I) and [Ru(C10H8N2)2(C5H6N2)2](ClO4)2 acetonitrile solvate [P-1 space group, cell parameters a =10.585 (2) Å, b = 11.615 (2) Å, c = 15.992 (3) Å, α = 104.44°, β = 99.76 (3)° and γ = 106.27°; Duan et al., 1999] are isostructural: they crystallize in the centrosymmetric triclinic space group with very similar cell parameters and crystal packing features. Their crystal assemblies are stabilized by van der Waals interactions and classical hydrogen bonds whose NH2 groups of both 4Apy ligands are donors to either fluorine atoms (or oxygens of perchlorate in the antecedent isostructure) of the counterion or nitrogen one of acetonitrile solvent (Fig. 2). Indeed, four N—H···F interactions give rise to an intermolecularly-locked assembly of two centrosymmetric complex molecules and two PF6 counterions (Fig. 2). Two of them are related by a centrosymmetry to two independent ones, namely, the N4—H4A···F4 and N4A—H4A1···F5 contacts. These contacts involve both 4Apy moieties of (I) and one of the two crystallographically independent PF6 units. Such an assembly can be considered as the building unit of both crystal architectures of (I) and the perchlorate analogue. However, in the former two oxygens of one perchlorate unit, which has occupancy sites of some oxygen atoms disordered over two positions, substitute for F4 and F5 fluorine atoms of (I). It is important to observe such a disorder as that reported for the perchlorate analogue can be related to this packing feature described above. In (I), the F4—P1—F5 angle is 89.7 (7)°, while tetrahedral geometry of the four oxygens around chlorine atom of the perchlorate counterion imposes O—Cl—O angles to be near to 109°. No disorder is found for the positions of the fluorine supramolecular functionalities in (I), which is in agreement with the favorable geometric orientation of both F4 and F5 atoms to accept the hydrogen bonding from two inversion-related coordination complexes. In contrast, the expected angle values for ClO4 are much more enlarged than that of the cis-fluorine atoms acting as hydrogen bonding acceptors in N4—H4A···F4 and N4A—H4A1···F5, which clearly reveals the tendency for disordering the positions of the perchlorate oxygens in order to favor geometrically the formation of such contacts since the same intermolecular arrangement is kept in (I) and in the perchlorate analogue. No coordinates of the hydrogen atoms is available for the former structure, and therefore more detailed comparisons concerning the oxygen fractions involved in the hydrogen bonding interactions can not be accurately performed. The connection between the building blocks occurs along the [011] direction by mean of hydrogen bonding donation from both complex units of the centrosymmetric assembly to the other crystallographically independent PF6 fragment and to the acetonitrile solvent through the N4—H4B···F6A and N4A—H4A2···N1S contacts, respectively. In addition, there is a non-classical hydrogen bonding between this PF6 counterion and the solvent molecule through the C2S—H1S···F6A contact. In fact, two centrosymmetric motifs made up of hydrogen-bonded PF6 and acetonitrile molecules can be understood as the connecting pieces between the building units, giving rise to infinite one-dimensional ribbons running parallel to the [011] direction. Geometric parameters of the classical hydrogen bonding interactions are shown in Table 1.

The complex shows the Ru atom bonded to two bpy ligands in a cis configuration with the two 4Apy ligands in the expected distorted-octahedral fashion. The trans N—Ru—N angles (mean values of 175 (1)° (I), deviate slightly from the ideal value of 180°. Corresponding cis angles show similar small deviations from 90°: 91 (7)°. The mean Ru—N(α-diimine) distance [2.057 (7) Å] is similar to that found in a related coordination complex with the [Ru(bpy)3)]2+ moiety (2.056 Å) (Stoyanov et al., 2002).

In the complex (I), the α-diimine coordinated ligands are approximately planar with deviation from the least-square planes less than 2°. The two bpy ligands are nearly perpendicular, as indicated by the dihedral angle between their least square planes, 82.71 (8)° in (I). The pyridine subunits in each bpy ligand are distorted by 2.7 (2)° [bpy(1)] and 6.1 (2)° [bpy(2)].

The dihedral angles do not show any significant distortions in the structure of the complex to relieve the steric hindrance imposed by bpy ligand. Fig. 1 shows a very neat twisted location of the 4Apy ligands with respect to the planes of the bpy ligands. The dihedral angles between the least-squares planes calculated through 4Apy and bpy ligands are 85.9 (1)° between [4Apy(1) and bpy(1)] and [4Apy(2) and bpy(2)].

Related literature top

For compounds with similar properties, see: Stoyanov et al. (2002); Duan et al. (1999); Salassa et al. (2009). For use of 4Apy, see: Sinha & Shrivastava (2012). For the synthesis of the starting materials, see: Bonneson et al. (1983).

Experimental top

The compound (I) was synthesized from the corresponding aquo-complex (Bonneson et al., 1983) cis-[Ru(α-diimine)2(OH2)2](PF6)2 [α-diimine = 2,2-bipyridine (bpy)] by reacting the latter with 4-Aminopyridine in 1:1 EtOH/H2O mixture under nitrogen atmosphere and for 8 h under reflux. A stoichiometric amount of ammonium hexafluorophosphate was added to precipitate the complex. Single crystals suitable for X-ray diffraction measurement were obtained after 10 days on slow evaporation of an acetonitrile solution at room temperature. Elemental analysis (%) for (I) RuC30H32N8P2F12O2: calculated: C, 38.84, N, 12.08; H, 3.48; found: C, 38.70; N, 11.80; H, 3.54.

Refinement top

The H atoms were located from the difference Fourier synthesis and refined using the riding model on their parent atoms with C—H = 0.93 Å for aromatic moieties or 0.96 Å for methyl group of acetonitrile, N—H = 0.86 Å and Uiso(H) = 1.2Ueq for phenyl and amine H atoms or 1.5Ueq for methyl ones.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. ORTEP-3 drawing of (I). Ellipsoids for non-H atoms are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of (I). In this figure, three building units of (I) are shown on the left of the panel, which are joined together on the right along the [011] direction through hydrogen bonds with the connecting pieces (detached on the box). Hydrogen bonds are shown as dashed lines. [Symmetry codes: (a) (i) x, -y + 3/2, z - 1/2; (ii) x + 1/2, y + 1/2, -z + 3/2; (iii) x + 1/2, -y + 2, -z + 1; (iv) x + 1, -y + 3/2, z - 1/2; (v) x - 1/2, -y + 1, -z + 1; (vi) x + 1/2, y - 1/2, -z + 3/2; (b) (i) x, y + 1, z; (ii) -x + 1, -y + 1, -z + 1; (iii) -x, -y, -z + 1; (iv) -x + 1, -y, -z; (v) -x, -y + 1, -z + 1; (vi) x - 1, y, z; (vii) x - 1, y + 1, z + 1].
cis-Bis(2,2'-bipyridine-κ2N,N')bis(pyridin-4-amine- κN1)ruthenium(II) bis(hexafluoridophosphate) acetonitrile monosolvate top
Crystal data top
[Ru(C10H8N2)2(C5H6N2)2](PF6)2·C2H3NZ = 2
Mr = 932.67F(000) = 936
Triclinic, P1Dx = 1.671 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.8290 (3) ÅCell parameters from 14506 reflections
b = 11.8890 (3) Åθ = 2.9–27.2°
c = 16.1020 (4) ŵ = 0.61 mm1
α = 104.073 (1)°T = 298 K
β = 99.114 (2)°Prism, red
γ = 107.761 (2)°0.21 × 0.11 × 0.09 mm
V = 1853.32 (8) Å3
Data collection top
Nonius KappaCCD
diffractometer
6142 reflections with I > 2σ(I)
CCD scansRint = 0.033
Absorption correction: multi-scan
(Blessing, 1995)
θmax = 27.2°, θmin = 2.9°
Tmin = 0.935, Tmax = 0.950h = 1312
14506 measured reflectionsk = 1414
7906 independent reflectionsl = 2020
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.053 w = 1/[σ2(Fo2) + (0.081P)2 + 1.5061P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.148(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.90 e Å3
7906 reflectionsΔρmin = 0.58 e Å3
506 parameters
Crystal data top
[Ru(C10H8N2)2(C5H6N2)2](PF6)2·C2H3Nγ = 107.761 (2)°
Mr = 932.67V = 1853.32 (8) Å3
Triclinic, P1Z = 2
a = 10.8290 (3) ÅMo Kα radiation
b = 11.8890 (3) ŵ = 0.61 mm1
c = 16.1020 (4) ÅT = 298 K
α = 104.073 (1)°0.21 × 0.11 × 0.09 mm
β = 99.114 (2)°
Data collection top
Nonius KappaCCD
diffractometer
7906 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
6142 reflections with I > 2σ(I)
Tmin = 0.935, Tmax = 0.950Rint = 0.033
14506 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.148H-atom parameters constrained
S = 1.06Δρmax = 0.90 e Å3
7906 reflectionsΔρmin = 0.58 e Å3
506 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ru0.31099 (3)0.67417 (3)0.268302 (19)0.03972 (12)
N10.3873 (3)0.8658 (3)0.3076 (2)0.0457 (7)
N20.4801 (3)0.7109 (3)0.3647 (2)0.0473 (7)
N2A0.4008 (3)0.6761 (3)0.1657 (2)0.0444 (7)
N1A0.1542 (3)0.6540 (3)0.1681 (2)0.0428 (7)
N30.2084 (3)0.6776 (3)0.3689 (2)0.0427 (7)
N40.0286 (5)0.6996 (5)0.5798 (3)0.0827 (13)
H4A0.01340.75010.59090.099*
H4B0.03330.65240.61220.099*
N3A0.2449 (3)0.4776 (3)0.2282 (2)0.0420 (7)
N4A0.0979 (5)0.0921 (4)0.1192 (3)0.0834 (14)
H4A10.0170.0490.11710.1*
H4A20.14880.05580.0980.1*
C10.3343 (5)0.9383 (4)0.2738 (3)0.0588 (11)
H10.25310.90090.23120.071*
C20.3946 (6)1.0650 (4)0.2994 (4)0.0705 (13)
H20.35461.11240.27480.085*
C30.5142 (6)1.1206 (5)0.3616 (4)0.0785 (15)
H30.5581.20630.37910.094*
C40.5690 (5)1.0480 (5)0.3980 (4)0.0727 (14)
H40.64941.08460.44150.087*
C50.5051 (4)0.9214 (4)0.3701 (3)0.0510 (10)
C60.5564 (4)0.8353 (4)0.4037 (3)0.0526 (10)
C70.6732 (5)0.8742 (5)0.4703 (3)0.0750 (14)
H70.72310.95840.49660.09*
C80.7141 (5)0.7874 (6)0.4966 (4)0.0846 (17)
H80.79260.81190.54040.102*
C90.6390 (6)0.6658 (6)0.4582 (4)0.0856 (18)
H90.66470.60580.4760.103*
C100.5253 (5)0.6317 (5)0.3930 (3)0.0693 (13)
H100.47630.54730.36680.083*
C10A0.5286 (4)0.6843 (4)0.1691 (3)0.0577 (11)
H10A0.58290.68920.22170.069*
C9A0.5807 (5)0.6855 (5)0.0966 (4)0.0733 (14)
H9A0.66940.69210.10080.088*
C8A0.5032 (6)0.6772 (6)0.0192 (4)0.0804 (15)
H8A0.5370.67530.03050.097*
C7A0.3718 (5)0.6716 (5)0.0148 (3)0.0713 (14)
H7A0.31750.66780.03740.086*
C6A0.3240 (4)0.6716 (4)0.0888 (3)0.0497 (9)
C5A0.1874 (4)0.6646 (4)0.0911 (3)0.0475 (9)
C4A0.0962 (5)0.6651 (5)0.0210 (3)0.0609 (11)
H4A30.12120.67420.03030.073*
C3A0.0327 (5)0.6521 (5)0.0278 (3)0.0712 (14)
H3A0.09480.65440.01820.085*
C2A0.0675 (4)0.6356 (5)0.1033 (3)0.0635 (12)
H2A0.15480.62280.10820.076*
C1A0.0277 (4)0.6383 (4)0.1717 (3)0.0506 (9)
H1A0.00310.62880.2230.061*
C110.2122 (5)0.6049 (4)0.4215 (3)0.0607 (11)
H110.25570.54870.40940.073*
C120.1551 (5)0.6104 (5)0.4914 (3)0.0642 (12)
H120.16040.5590.52610.077*
C130.0881 (4)0.6942 (4)0.5106 (3)0.0564 (10)
C140.0837 (4)0.7662 (4)0.4576 (3)0.0595 (11)
H140.040.82260.46770.071*
C150.1447 (4)0.7554 (4)0.3884 (3)0.0558 (10)
H150.14060.80630.35320.067*
C11A0.3199 (4)0.4140 (4)0.1952 (3)0.0501 (9)
H11A0.40750.45930.19680.06*
C12A0.2760 (4)0.2877 (4)0.1598 (3)0.0533 (10)
H12A0.33320.24970.13870.064*
C13A0.1447 (4)0.2160 (4)0.1555 (3)0.0544 (10)
C14A0.0678 (4)0.2799 (4)0.1908 (3)0.0558 (10)
H14A0.01940.23620.19120.067*
C15A0.1186 (4)0.4061 (4)0.2248 (3)0.0485 (9)
H15A0.06340.44570.2470.058*
P10.07844 (14)0.04876 (12)0.70888 (9)0.0660 (3)
P1A0.71818 (12)0.40171 (12)0.25261 (9)0.0604 (3)
F10.0516 (5)0.0689 (5)0.7229 (5)0.158 (2)
F20.1439 (5)0.1892 (3)0.7154 (3)0.1230 (15)
F30.2117 (6)0.0324 (7)0.6988 (4)0.172 (3)
F40.0089 (7)0.0907 (4)0.7029 (3)0.160 (2)
F50.1258 (5)0.0774 (5)0.8116 (3)0.1387 (18)
F60.0318 (6)0.0146 (5)0.6062 (3)0.148 (2)
F6A0.7482 (4)0.2948 (4)0.2846 (3)0.1114 (12)
F4A0.6327 (5)0.4106 (5)0.3225 (3)0.1294 (15)
F1A0.6852 (5)0.5050 (4)0.2214 (4)0.1450 (19)
F2A0.8037 (3)0.3839 (5)0.1829 (2)0.1177 (15)
F5A0.5890 (3)0.3042 (4)0.1804 (2)0.1011 (11)
F3A0.8512 (4)0.4961 (4)0.3229 (3)0.1229 (15)
C2S0.6126 (9)0.0190 (7)0.1288 (5)0.112 (2)
H3S0.58920.06030.13890.168*
H2S0.53330.03810.11520.168*
H1S0.67420.08180.1810.168*
C1S0.6767 (9)0.0151 (7)0.0534 (8)0.124 (3)
N1S0.7190 (10)0.0059 (9)0.0082 (8)0.189 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru0.03023 (16)0.03983 (18)0.04288 (19)0.01056 (12)0.00455 (11)0.00750 (12)
N10.0382 (16)0.0436 (17)0.0499 (18)0.0110 (14)0.0133 (14)0.0083 (14)
N20.0422 (17)0.0511 (19)0.0462 (18)0.0193 (15)0.0089 (14)0.0085 (15)
N2A0.0359 (16)0.0404 (16)0.0518 (18)0.0096 (13)0.0121 (14)0.0099 (14)
N1A0.0353 (15)0.0386 (16)0.0456 (17)0.0104 (13)0.0058 (13)0.0038 (13)
N30.0407 (16)0.0438 (17)0.0430 (17)0.0165 (14)0.0083 (13)0.0117 (13)
N40.097 (3)0.095 (3)0.070 (3)0.043 (3)0.039 (3)0.029 (2)
N3A0.0344 (15)0.0393 (16)0.0504 (18)0.0122 (13)0.0104 (13)0.0118 (13)
N4A0.080 (3)0.043 (2)0.116 (4)0.010 (2)0.043 (3)0.010 (2)
C10.057 (3)0.052 (2)0.066 (3)0.017 (2)0.014 (2)0.019 (2)
C20.088 (4)0.047 (3)0.079 (3)0.021 (2)0.028 (3)0.023 (2)
C30.080 (4)0.045 (3)0.093 (4)0.001 (2)0.025 (3)0.014 (3)
C40.051 (3)0.060 (3)0.078 (3)0.002 (2)0.009 (2)0.003 (2)
C50.0359 (19)0.054 (2)0.050 (2)0.0053 (17)0.0118 (16)0.0071 (18)
C60.0354 (19)0.062 (3)0.046 (2)0.0087 (18)0.0082 (16)0.0034 (19)
C70.044 (2)0.085 (4)0.066 (3)0.009 (2)0.004 (2)0.001 (3)
C80.057 (3)0.105 (5)0.069 (3)0.035 (3)0.016 (2)0.000 (3)
C90.079 (4)0.105 (5)0.075 (3)0.059 (4)0.006 (3)0.014 (3)
C100.064 (3)0.073 (3)0.065 (3)0.036 (3)0.004 (2)0.010 (2)
C10A0.039 (2)0.062 (3)0.067 (3)0.0166 (19)0.0152 (19)0.012 (2)
C9A0.050 (3)0.085 (4)0.092 (4)0.027 (2)0.033 (3)0.024 (3)
C8A0.072 (3)0.104 (4)0.070 (3)0.032 (3)0.035 (3)0.024 (3)
C7A0.060 (3)0.092 (4)0.054 (3)0.017 (3)0.020 (2)0.018 (2)
C6A0.041 (2)0.051 (2)0.048 (2)0.0099 (17)0.0080 (17)0.0097 (18)
C5A0.042 (2)0.048 (2)0.045 (2)0.0130 (17)0.0066 (16)0.0086 (17)
C4A0.055 (3)0.072 (3)0.050 (2)0.019 (2)0.0047 (19)0.020 (2)
C3A0.059 (3)0.090 (4)0.060 (3)0.034 (3)0.007 (2)0.018 (3)
C2A0.041 (2)0.075 (3)0.066 (3)0.027 (2)0.001 (2)0.008 (2)
C1A0.037 (2)0.055 (2)0.055 (2)0.0171 (17)0.0059 (17)0.0096 (19)
C110.069 (3)0.064 (3)0.050 (2)0.028 (2)0.012 (2)0.015 (2)
C120.074 (3)0.065 (3)0.052 (3)0.024 (2)0.012 (2)0.020 (2)
C130.055 (2)0.056 (2)0.048 (2)0.015 (2)0.0139 (19)0.0045 (19)
C140.055 (3)0.055 (3)0.061 (3)0.022 (2)0.007 (2)0.006 (2)
C150.052 (2)0.055 (2)0.055 (2)0.019 (2)0.0071 (19)0.0100 (19)
C11A0.0355 (19)0.052 (2)0.062 (2)0.0144 (17)0.0129 (17)0.0172 (19)
C12A0.049 (2)0.048 (2)0.065 (3)0.0211 (19)0.020 (2)0.0151 (19)
C13A0.055 (2)0.047 (2)0.058 (2)0.0147 (19)0.0173 (19)0.0139 (19)
C14A0.042 (2)0.053 (2)0.064 (3)0.0072 (18)0.0164 (19)0.013 (2)
C15A0.039 (2)0.051 (2)0.056 (2)0.0157 (17)0.0149 (17)0.0159 (18)
P10.0642 (8)0.0582 (7)0.0740 (8)0.0224 (6)0.0170 (6)0.0175 (6)
P1A0.0514 (6)0.0643 (7)0.0654 (7)0.0217 (6)0.0145 (5)0.0186 (6)
F10.099 (3)0.173 (5)0.260 (7)0.081 (3)0.076 (4)0.105 (5)
F20.141 (4)0.070 (2)0.132 (3)0.005 (2)0.034 (3)0.027 (2)
F30.157 (4)0.269 (7)0.213 (6)0.147 (5)0.121 (4)0.149 (5)
F40.271 (7)0.063 (2)0.164 (4)0.047 (3)0.119 (5)0.042 (2)
F50.119 (3)0.183 (5)0.088 (3)0.015 (3)0.015 (2)0.054 (3)
F60.181 (5)0.123 (4)0.082 (3)0.003 (3)0.002 (3)0.021 (2)
F6A0.124 (3)0.105 (3)0.116 (3)0.056 (2)0.015 (2)0.044 (2)
F4A0.151 (4)0.158 (4)0.112 (3)0.080 (3)0.075 (3)0.042 (3)
F1A0.171 (5)0.104 (3)0.177 (5)0.064 (3)0.015 (4)0.074 (3)
F2A0.0598 (19)0.208 (5)0.081 (2)0.044 (2)0.0248 (17)0.038 (3)
F5A0.0564 (18)0.117 (3)0.102 (3)0.0137 (18)0.0072 (17)0.016 (2)
F3A0.107 (3)0.113 (3)0.086 (2)0.016 (2)0.014 (2)0.017 (2)
C2S0.136 (7)0.096 (5)0.105 (5)0.060 (5)0.026 (5)0.012 (4)
C1S0.100 (6)0.089 (5)0.161 (9)0.049 (5)0.011 (5)0.007 (5)
N1S0.179 (9)0.139 (7)0.257 (12)0.057 (6)0.133 (9)0.027 (7)
Geometric parameters (Å, º) top
Ru—N2A2.047 (3)C8A—H8A0.93
Ru—N22.059 (3)C7A—C6A1.372 (6)
Ru—N1A2.058 (3)C7A—H7A0.93
Ru—N12.063 (3)C6A—C5A1.463 (5)
Ru—N32.104 (3)C5A—C4A1.380 (6)
Ru—N3A2.119 (3)C4A—C3A1.381 (7)
N1—C11.341 (5)C4A—H4A30.93
N1—C51.354 (5)C3A—C2A1.370 (7)
N2—C101.324 (6)C3A—H3A0.93
N2—C61.379 (5)C2A—C1A1.371 (6)
N2A—C10A1.349 (5)C2A—H2A0.93
N2A—C6A1.358 (5)C1A—H1A0.93
N1A—C1A1.338 (5)C11—C121.365 (7)
N1A—C5A1.369 (5)C11—H110.93
N3—C151.321 (5)C12—C131.406 (7)
N3—C111.353 (6)C12—H120.93
N4—C131.372 (6)C13—C141.353 (7)
N4—H4A0.86C14—C151.382 (6)
N4—H4B0.86C14—H140.93
N3A—C11A1.352 (5)C15—H150.93
N3A—C15A1.357 (5)C11A—C12A1.367 (6)
N4A—C13A1.342 (6)C11A—H11A0.93
N4A—H4A10.86C12A—C13A1.398 (6)
N4A—H4A20.86C12A—H12A0.93
C1—C21.371 (6)C13A—C14A1.386 (6)
C1—H10.93C14A—C15A1.362 (6)
C2—C31.365 (8)C14A—H14A0.93
C2—H20.93C15A—H15A0.93
C3—C41.374 (8)P1—F11.540 (4)
C3—H30.93P1—F31.542 (5)
C4—C51.372 (6)P1—F61.561 (4)
C4—H40.93P1—F51.570 (4)
C5—C61.474 (6)P1—F41.570 (4)
C6—C71.391 (6)P1—F21.572 (4)
C7—C81.369 (8)P1A—F1A1.548 (4)
C7—H70.93P1A—F4A1.570 (4)
C8—C91.349 (9)P1A—F5A1.579 (3)
C8—H80.93P1A—F3A1.580 (4)
C9—C101.364 (7)P1A—F2A1.581 (4)
C9—H90.93P1A—F6A1.582 (4)
C10—H100.93C2S—C1S1.489 (13)
C10A—C9A1.376 (7)C2S—H3S0.96
C10A—H10A0.93C2S—H2S0.96
C9A—C8A1.350 (8)C2S—H1S0.96
C9A—H9A0.93C1S—N1S1.152 (13)
C8A—C7A1.392 (7)
N2A—Ru—N296.95 (13)C7A—C6A—C5A123.4 (4)
N2A—Ru—N1A78.94 (12)N1A—C5A—C4A121.6 (4)
N2—Ru—N1A173.63 (13)N1A—C5A—C6A114.8 (3)
N2A—Ru—N187.84 (12)C4A—C5A—C6A123.5 (4)
N2—Ru—N179.24 (13)C5A—C4A—C3A119.4 (4)
N1A—Ru—N195.66 (12)C5A—C4A—H4A3120.3
N2A—Ru—N3175.56 (12)C3A—C4A—H4A3120.3
N2—Ru—N386.83 (12)C2A—C3A—C4A118.9 (4)
N1A—Ru—N397.09 (12)C2A—C3A—H3A120.6
N1—Ru—N390.57 (12)C4A—C3A—H3A120.6
N2A—Ru—N3A90.07 (12)C3A—C2A—C1A119.3 (4)
N2—Ru—N3A98.16 (12)C3A—C2A—H2A120.3
N1A—Ru—N3A86.77 (12)C1A—C2A—H2A120.3
N1—Ru—N3A176.43 (11)N1A—C1A—C2A123.2 (4)
N3—Ru—N3A91.72 (12)N1A—C1A—H1A118.4
C1—N1—C5117.9 (4)C2A—C1A—H1A118.4
C1—N1—Ru126.0 (3)N3—C11—C12123.0 (4)
C5—N1—Ru116.0 (3)N3—C11—H11118.5
C10—N2—C6116.5 (4)C12—C11—H11118.5
C10—N2—Ru128.8 (3)C11—C12—C13119.5 (4)
C6—N2—Ru114.7 (3)C11—C12—H12120.2
C10A—N2A—C6A118.3 (4)C13—C12—H12120.2
C10A—N2A—Ru125.7 (3)C14—C13—N4122.4 (5)
C6A—N2A—Ru116.0 (3)C14—C13—C12117.4 (4)
C1A—N1A—C5A117.4 (3)N4—C13—C12120.2 (5)
C1A—N1A—Ru127.5 (3)C13—C14—C15119.5 (4)
C5A—N1A—Ru114.9 (2)C13—C14—H14120.3
C15—N3—C11116.2 (4)C15—C14—H14120.3
C15—N3—Ru122.6 (3)N3—C15—C14124.4 (4)
C11—N3—Ru121.0 (3)N3—C15—H15117.8
C13—N4—H4A120C14—C15—H15117.8
C13—N4—H4B120N3A—C11A—C12A124.6 (4)
H4A—N4—H4B120N3A—C11A—H11A117.7
C11A—N3A—C15A114.8 (3)C12A—C11A—H11A117.7
C11A—N3A—Ru122.7 (3)C11A—C12A—C13A119.5 (4)
C15A—N3A—Ru122.1 (3)C11A—C12A—H12A120.2
C13A—N4A—H4A1120C13A—C12A—H12A120.2
C13A—N4A—H4A2120N4A—C13A—C14A122.8 (4)
H4A1—N4A—H4A2120N4A—C13A—C12A120.9 (4)
N1—C1—C2122.9 (5)C14A—C13A—C12A116.4 (4)
N1—C1—H1118.5C15A—C14A—C13A120.6 (4)
C2—C1—H1118.5C15A—C14A—H14A119.7
C3—C2—C1118.9 (5)C13A—C14A—H14A119.7
C3—C2—H2120.5N3A—C15A—C14A124.0 (4)
C1—C2—H2120.5N3A—C15A—H15A118
C2—C3—C4119.0 (5)C14A—C15A—H15A118
C2—C3—H3120.5F1—P1—F3177.6 (4)
C4—C3—H3120.5F1—P1—F693.1 (4)
C5—C4—C3120.0 (5)F3—P1—F689.1 (4)
C5—C4—H4120F1—P1—F588.2 (3)
C3—C4—H4120F3—P1—F589.7 (3)
N1—C5—C4121.2 (4)F6—P1—F5177.5 (3)
N1—C5—C6114.5 (3)F1—P1—F488.0 (3)
C4—C5—C6124.2 (4)F3—P1—F493.1 (4)
N2—C6—C7121.2 (4)F6—P1—F490.4 (3)
N2—C6—C5115.4 (3)F5—P1—F487.5 (3)
C7—C6—C5123.4 (4)F1—P1—F290.2 (3)
C8—C7—C6119.3 (5)F3—P1—F288.7 (3)
C8—C7—H7120.3F6—P1—F289.7 (2)
C6—C7—H7120.3F5—P1—F292.4 (3)
C9—C8—C7119.2 (5)F4—P1—F2178.2 (3)
C9—C8—H8120.4F1A—P1A—F4A91.9 (3)
C7—C8—H8120.4F1A—P1A—F5A88.0 (3)
C8—C9—C10119.6 (5)F4A—P1A—F5A89.8 (2)
C8—C9—H9120.2F1A—P1A—F3A93.4 (3)
C10—C9—H9120.2F4A—P1A—F3A92.3 (3)
N2—C10—C9124.2 (5)F5A—P1A—F3A177.5 (3)
N2—C10—H10117.9F1A—P1A—F2A91.8 (3)
C9—C10—H10117.9F4A—P1A—F2A176.1 (3)
N2A—C10A—C9A121.7 (4)F5A—P1A—F2A89.1 (2)
N2A—C10A—H10A119.2F3A—P1A—F2A88.7 (2)
C9A—C10A—H10A119.2F1A—P1A—F6A178.6 (3)
C8A—C9A—C10A120.1 (5)F4A—P1A—F6A87.1 (3)
C8A—C9A—H9A120F5A—P1A—F6A91.1 (2)
C10A—C9A—H9A120F3A—P1A—F6A87.6 (2)
C9A—C8A—C7A119.2 (5)F2A—P1A—F6A89.2 (2)
C9A—C8A—H8A120.4C1S—C2S—H3S109.5
C7A—C8A—H8A120.4C1S—C2S—H2S109.5
C6A—C7A—C8A118.9 (5)H3S—C2S—H2S109.5
C6A—C7A—H7A120.6C1S—C2S—H1S109.5
C8A—C7A—H7A120.6H3S—C2S—H1S109.5
N2A—C6A—C7A121.8 (4)H2S—C2S—H1S109.5
N2A—C6A—C5A114.8 (4)N1S—C1S—C2S175.7 (10)
N2A—Ru—N1—C181.4 (3)Ru—N2—C6—C7179.7 (3)
N2—Ru—N1—C1178.9 (4)C10—N2—C6—C5179.1 (4)
N1A—Ru—N1—C12.8 (3)Ru—N2—C6—C50.2 (4)
N3—Ru—N1—C194.4 (3)N1—C5—C6—N22.2 (5)
N2A—Ru—N1—C595.1 (3)C4—C5—C6—N2177.4 (4)
N2—Ru—N1—C52.4 (3)N1—C5—C6—C7177.6 (4)
N1A—Ru—N1—C5173.7 (3)C4—C5—C6—C72.7 (7)
N3—Ru—N1—C589.1 (3)N2—C6—C7—C80.9 (7)
N2A—Ru—N2—C1093.8 (4)C5—C6—C7—C8179.3 (5)
N1—Ru—N2—C10179.7 (4)C6—C7—C8—C90.9 (9)
N3—Ru—N2—C1088.5 (4)C7—C8—C9—C101.0 (10)
N3A—Ru—N2—C102.7 (4)C6—N2—C10—C91.3 (7)
N2A—Ru—N2—C685.3 (3)Ru—N2—C10—C9179.6 (4)
N1—Ru—N2—C61.1 (3)C8—C9—C10—N21.3 (9)
N3—Ru—N2—C692.3 (3)C6A—N2A—C10A—C9A1.4 (6)
N3A—Ru—N2—C6176.4 (3)Ru—N2A—C10A—C9A179.7 (4)
N2—Ru—N2A—C10A7.0 (4)N2A—C10A—C9A—C8A0.6 (8)
N1A—Ru—N2A—C10A177.9 (4)C10A—C9A—C8A—C7A2.1 (9)
N1—Ru—N2A—C10A85.9 (3)C9A—C8A—C7A—C6A1.5 (9)
N3A—Ru—N2A—C10A91.2 (3)C10A—N2A—C6A—C7A2.0 (6)
N2—Ru—N2A—C6A171.3 (3)Ru—N2A—C6A—C7A179.6 (4)
N1A—Ru—N2A—C6A3.8 (3)C10A—N2A—C6A—C5A179.2 (4)
N1—Ru—N2A—C6A92.4 (3)Ru—N2A—C6A—C5A0.7 (4)
N3A—Ru—N2A—C6A90.5 (3)C8A—C7A—C6A—N2A0.5 (8)
N2A—Ru—N1A—C1A177.3 (3)C8A—C7A—C6A—C5A179.3 (5)
N1—Ru—N1A—C1A96.0 (3)C1A—N1A—C5A—C4A3.0 (6)
N3—Ru—N1A—C1A4.7 (3)Ru—N1A—C5A—C4A173.7 (3)
N3A—Ru—N1A—C1A86.6 (3)C1A—N1A—C5A—C6A175.4 (4)
N2A—Ru—N1A—C5A6.4 (3)Ru—N1A—C5A—C6A7.9 (4)
N1—Ru—N1A—C5A80.3 (3)N2A—C6A—C5A—N1A4.7 (5)
N3—Ru—N1A—C5A171.6 (3)C7A—C6A—C5A—N1A174.1 (4)
N3A—Ru—N1A—C5A97.1 (3)N2A—C6A—C5A—C4A176.9 (4)
N2—Ru—N3—C15121.1 (3)C7A—C6A—C5A—C4A4.3 (7)
N1A—Ru—N3—C1553.9 (3)N1A—C5A—C4A—C3A1.4 (7)
N1—Ru—N3—C1541.9 (3)C6A—C5A—C4A—C3A176.9 (4)
N3A—Ru—N3—C15140.8 (3)C5A—C4A—C3A—C2A1.7 (8)
N2—Ru—N3—C1154.3 (3)C4A—C3A—C2A—C1A3.0 (8)
N1A—Ru—N3—C11130.7 (3)C5A—N1A—C1A—C2A1.7 (6)
N1—Ru—N3—C11133.5 (3)Ru—N1A—C1A—C2A174.6 (3)
N3A—Ru—N3—C1143.8 (3)C3A—C2A—C1A—N1A1.3 (7)
N2A—Ru—N3A—C11A37.0 (3)C15—N3—C11—C120.4 (6)
N2—Ru—N3A—C11A60.1 (3)Ru—N3—C11—C12175.3 (4)
N1A—Ru—N3A—C11A115.9 (3)N3—C11—C12—C130.4 (7)
N3—Ru—N3A—C11A147.1 (3)C11—C12—C13—C140.0 (7)
N2A—Ru—N3A—C15A135.8 (3)C11—C12—C13—N4179.1 (4)
N2—Ru—N3A—C15A127.2 (3)N4—C13—C14—C15179.4 (4)
N1A—Ru—N3A—C15A56.9 (3)C12—C13—C14—C150.3 (7)
N3—Ru—N3A—C15A40.1 (3)C11—N3—C15—C140.1 (6)
C5—N1—C1—C20.5 (6)Ru—N3—C15—C14175.5 (3)
Ru—N1—C1—C2176.0 (4)C13—C14—C15—N30.3 (7)
N1—C1—C2—C30.4 (8)C15A—N3A—C11A—C12A0.6 (6)
C1—C2—C3—C41.4 (8)Ru—N3A—C11A—C12A172.6 (3)
C2—C3—C4—C51.6 (8)N3A—C11A—C12A—C13A0.5 (7)
C1—N1—C5—C40.3 (6)C11A—C12A—C13A—N4A178.4 (5)
Ru—N1—C5—C4176.5 (3)C11A—C12A—C13A—C14A1.8 (7)
C1—N1—C5—C6180.0 (4)N4A—C13A—C14A—C15A178.2 (5)
Ru—N1—C5—C63.2 (4)C12A—C13A—C14A—C15A2.1 (7)
C3—C4—C5—N10.7 (7)C11A—N3A—C15A—C14A0.4 (6)
C3—C4—C5—C6178.9 (5)Ru—N3A—C15A—C14A172.9 (3)
C10—N2—C6—C71.1 (6)C13A—C14A—C15A—N3A1.0 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···F4i0.862.192.871 (8)135
N4—H4B···F6Aii0.862.472.962 (7)117
N4A—H4A1···F5iii0.862.443.184 (8)145
N4A—H4A2···N1Siv0.862.343.162 (13)161
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z+1; (iii) x, y, z+1; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formula[Ru(C10H8N2)2(C5H6N2)2](PF6)2·C2H3N
Mr932.67
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)10.8290 (3), 11.8890 (3), 16.1020 (4)
α, β, γ (°)104.073 (1), 99.114 (2), 107.761 (2)
V3)1853.32 (8)
Z2
Radiation typeMo Kα
µ (mm1)0.61
Crystal size (mm)0.21 × 0.11 × 0.09
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.935, 0.950
No. of measured, independent and
observed [I > 2σ(I)] reflections
14506, 7906, 6142
Rint0.033
(sin θ/λ)max1)0.642
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.148, 1.06
No. of reflections7906
No. of parameters506
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.90, 0.58

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···F4i0.862.192.871 (8)135
N4—H4B···F6Aii0.862.472.962 (7)117
N4A—H4A1···F5iii0.862.443.184 (8)145
N4A—H4A2···N1Siv0.862.343.162 (13)161
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z+1; (iii) x, y, z+1; (iv) x+1, y, z.
 

Footnotes

Part II. Ruthenium(II) coordination complexes with 4-amino­pyridine and α-diimine ligands.

Acknowledgements

The authors wish to thank FAPESP (Proc. 2009/08218–0; 2008/52859–7), CNPq (Universal 470890/2010–0) and CAPES for the grants and fellowships given to this research.

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Volume 69| Part 2| February 2013| Pages m77-m78
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