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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): m575–m576.
Published online 2008 March 29. doi:  10.1107/S1600536808007228
PMCID: PMC2960910

Tetra­chlorido(2,3-di-2-pyridylpyrazine-κ2 N 1,N 2)platinum(IV)

Abstract

In the title complex, [PtCl4(C14H10N4)], the PtIV atom is six-coordinated in an octa­hedral configuration by two N atoms from one 2,3-di-2-pyridylpyrazine ligand and four terminal Cl atoms. Inter­molecular C—H(...)Cl and C—H(...)N hydrogen bonds stabilize the crystal structure.

Related literature

For general background, see: Hedin (1886 [triangle]); Joergensen (1900 [triangle]); Bajusaz et al. (1989 [triangle]); Vorobevdesyatovskii et al. (1991 [triangle]). For related structures, see: Bokach et al. (2003 [triangle]); Casas et al. (2005 [triangle]); Crowder et al. (2004 [triangle]); Gaballa et al. (2003 [triangle]); Garnovskii et al. (2001 [triangle]); Gonzalez et al. (2002 [triangle]); Hafizovic et al. (2006 [triangle]); Hambley (1986 [triangle]); Kuduk-Jaworska et al. (1988 [triangle], 1990 [triangle]); Junicke et al. (1997 [triangle]); Khripun et al. (2006 [triangle]); Kukushkin et al. (1998 [triangle]); Luzyanin, Haukka et al. (2002 [triangle]); Luzyanin, Kukushkin et al. (2002 [triangle]); Witkowski et al. (1997 [triangle]); Yousefi et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m575-scheme1.jpg

Experimental

Crystal data

  • [PtCl4(C14H10N4)]
  • M r = 571.14
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m575-efi1.jpg
  • a = 6.6849 (4) Å
  • b = 14.9604 (12) Å
  • c = 16.2761 (10) Å
  • V = 1627.75 (19) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 9.28 mm−1
  • T = 120 (2) K
  • 0.40 × 0.26 × 0.14 mm

Data collection

  • Stoe IPDSII diffractometer
  • Absorption correction: numerical (X-SHAPE and X-RED; Stoe & Cie, 2005 [triangle]) T min = 0.070, T max = 0.270
  • 9336 measured reflections
  • 4374 independent reflections
  • 4327 reflections with I > 2σ(I)
  • R int = 0.064

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.087
  • S = 1.10
  • 4374 reflections
  • 209 parameters
  • H-atom parameters constrained
  • Δρmax = 1.44 e Å−3
  • Δρmin = −1.82 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1849 Friedel pairs
  • Flack parameter: 0.005 (9)

Data collection: X-AREA (Stoe & Cie, 2005 [triangle]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808007228/xu2404sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007228/xu2404Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We are grateful to Payam Nor University for financial support.

supplementary crystallographic information

Comment

Amine platinum(IV) complexes have been known since the end of the last century (Hedin, 1886; Joergensen, 1900). Some of them have cancerostatic properties from which new interest aroused in these complexes (Bajusaz et al., 1989; Vorobevdesyatovskii et al., 1991). Due to the kinetic inertness of hexachloro-platinate(IV), cis- and trans-[PtC14L2] complexes (L=N, O, P, S donor ligand) were mainly prepared by oxidation reactions of the corresponding platinum(II) complexes [PtCl2L2] (Hedin, 1886; Joergensen, 1900).

Several PtIV complexes, with formula [PtCl4(N—N)], such as [PtCl4(bipyi)] (II) (Gaballa et al., 2003), [PtCl4(Me2bim)] (III) (Casas et al., 2005), [PtCl4(bipy)] (IV) (Hambley, 1986), [PtCl4(dcbipy)].H2O (V) (Hafizovic et al., 2006) and [PtCl4(dpk)] (VI) (Crowder et al., 2004) [where bipyi is 2,2'-bipyrimidinyl, Me2bim is 1,1'-dimethyl-2,2'-bi-imidazolyl, bipy is 2,2'-bipyridine, dcbipy is 2,2'-bipyridine-5,5'-dicarboxylic acid and dpk is bis(2-pyridyl)ketone] have been synthesized and characterized by single-crystal X-ray diffraction method.

There are also several PtIV complexes with formula [PtCl4L2], such as cis- and trans-[PtCl4(py)2] (VII) (Junicke et al., 1997), cis- and trans-[PtCl4(PzH)2] (VIII) (Khripun et al., 2006), trans-[PtCl4(NH3)2](1-Mu) (IX) (Witkowski et al., 1997), trans-[PtCl4(1-Prim)2] (X) (Kuduk-Jaworska et al., 1988), cis-[PtCl4(1-Etim)2] (XI) (Kuduk-Jaworska et al., 1990), trans-[PtCl4{NH=C(NMe2)OH}2] (XII) (Bokach et al., 2003), trans-[PtCl4{NH=C(Me)ON=CMe2}2] (XIII) (Kukushkin et al., 1998), cis-[PtCl4{NH=C(Et)N=CPh2}2] (XIV) (Garnovskii et al., 2001), trans- [PtCl4{NH=C(Et)ON=C(OH)Ph}2].2DMSO (XV) (Luzyanin, Kukushkin et al., 2002), trans-[PtCl4{NH=C(OMe)But}2] (XVI) (Gonzalez et al., 2002), trans-[PtCl4{NH=C(OH)Et}2] (XVII) (Luzyanin, Haukka et al., 2002) and trans- [PtCl4(pz)2] (XVIII) (Yousefi et al., 2007) [where PzH is pyrazole, 1-Mu is 1-methyluracil, 1-Prim is 1-propylimidazole 1-Etim is 1-ethylimidazoyl and Pz is pyrazine] have been synthesized and characterized by single-crystal X-ray diffraction method. We report herein the synthesis and crystal structure of the title compound.

In the mononuclear title compound (Fig. 1), the PtIV atom is six-coordinated in octahedral configuration by two N atoms from one 2,3-di-2-pyridylpyrazine ligand and four terminal Cl atoms. The Pt—Cl and Pt—N bond lengths and angles (Table 1) are in good agreement with the corresponding values in (II), (III) and (V).

In the crystal structure, intermolecular C—H···Cl and C—H···N hydrogen bonds (Table 2) seem to be effective in the stabilization of the crystal structure (Fig. 2).

Experimental

For the preparation of the title compound, a solution of 2,3-di-2-pyridylpyrazine (0.09 g, 0.37 mmol) in methanol (10 ml) was added to a solution of H2PtCl6.6H2O, (0.20 g, 0.37 mmol) in methanol (10 ml) at room temperature. The suitable crystals for X-ray diffraction experiment were obtained by methanol diffusion in a solution of orange precipitated in DMSO after one week (yield 0.18 g).

Refinement

H atoms were positioned geometrically with C—H = 0.93 Å and constrained to ride on their parent atoms with Uiso(H)=1.2Ueq(C). The highest peak is 0.4 Å aprat from the Pt1 atom.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
A packing diagram for (I). Hydrogen bonds are shown as dashed lines.

Crystal data

[PtCl4(C14H10N4)]Dx = 2.331 Mg m3
Mr = 571.14Melting point: 565-566 K K
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1050 reflections
a = 6.6849 (4) Åθ = 1.9–29.2º
b = 14.9604 (12) ŵ = 9.28 mm1
c = 16.2761 (10) ÅT = 120 (2) K
V = 1627.75 (19) Å3Block, orange
Z = 40.40 × 0.26 × 0.14 mm
F000 = 1072

Data collection

Stoe IPDSII diffractometer4374 independent reflections
Radiation source: fine-focus sealed tube4327 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.064
Detector resolution: 0.15 mm pixels mm-1θmax = 29.2º
T = 120(2) Kθmin = 1.9º
rotation method scansh = −7→9
Absorption correction: Numerical(X-SHAPE and X-RED; Stoe & Cie, 2005)k = −20→17
Tmin = 0.070, Tmax = 0.270l = −22→22
9336 measured reflections

Refinement

Refinement on F2H-atom parameters constrained
Least-squares matrix: full  w = 1/[σ2(Fo2) + (0.0439P)2 + 6.2735P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.033(Δ/σ)max = 0.012
wR(F2) = 0.087Δρmax = 1.44 e Å3
S = 1.10Δρmin = −1.82 e Å3
4374 reflectionsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
209 parametersExtinction coefficient: 0.0011 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1849 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.005 (9)
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.2795 (10)−0.5902 (5)−0.4681 (4)0.0286 (13)
H10.3170−0.6300−0.50920.034*
C20.3870 (11)−0.5866 (6)−0.3975 (4)0.0331 (15)
H20.4966−0.6241−0.39010.040*
C30.3330 (11)−0.5272 (6)−0.3366 (4)0.0331 (14)
H30.4084−0.5231−0.28870.040*
C40.1659 (10)−0.4738 (5)−0.3472 (4)0.0275 (12)
H40.1233−0.4358−0.30550.033*
C50.0622 (8)−0.4780 (4)−0.4217 (4)0.0221 (10)
C6−0.1195 (9)−0.4247 (4)−0.4420 (4)0.0218 (11)
C7−0.3997 (8)−0.4210 (5)−0.5265 (4)0.0245 (12)
H7−0.4677−0.4395−0.57330.029*
C8−0.4867 (9)−0.3598 (5)−0.4741 (5)0.0315 (14)
H8−0.6191−0.3433−0.48280.038*
C9−0.1996 (9)−0.3519 (4)−0.3978 (4)0.0244 (12)
C10−0.0817 (10)−0.2972 (4)−0.3392 (4)0.0262 (12)
C11−0.1610 (11)−0.2695 (5)−0.2651 (5)0.0314 (14)
H11−0.2912−0.2840−0.25000.038*
C12−0.0403 (15)−0.2197 (5)−0.2143 (5)0.0403 (17)
H12−0.0855−0.2024−0.16270.048*
C130.1475 (13)−0.1955 (5)−0.2404 (5)0.0372 (16)
H130.2293−0.1601−0.20750.045*
C140.2123 (12)−0.2246 (5)−0.3161 (6)0.0378 (17)
H140.3391−0.2073−0.33340.045*
Cl10.1281 (2)−0.41434 (11)−0.62538 (10)0.0272 (3)
Cl20.1441 (2)−0.63100 (12)−0.65809 (10)0.0299 (3)
Cl3−0.2674 (2)−0.52425 (12)−0.69333 (11)0.0312 (3)
Cl4−0.2288 (3)−0.65930 (12)−0.53083 (13)0.0338 (4)
N10.1199 (7)−0.5372 (4)−0.4799 (3)0.0236 (10)
N2−0.2178 (7)−0.4537 (4)−0.5100 (4)0.0240 (10)
N3−0.3883 (8)−0.3242 (4)−0.4123 (5)0.0299 (12)
N40.1041 (8)−0.2763 (4)−0.3664 (4)0.0301 (12)
Pt1−0.05541 (3)−0.537445 (15)−0.582177 (14)0.02145 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.027 (3)0.033 (3)0.026 (3)0.013 (3)0.003 (3)0.001 (2)
C20.026 (3)0.046 (4)0.027 (3)0.005 (3)0.000 (3)0.004 (3)
C30.028 (3)0.044 (4)0.027 (3)−0.001 (3)−0.007 (3)0.005 (3)
C40.026 (3)0.037 (3)0.020 (3)0.001 (3)0.000 (2)0.002 (2)
C50.016 (2)0.030 (3)0.020 (2)−0.005 (2)0.003 (2)0.001 (2)
C60.018 (2)0.024 (3)0.023 (3)−0.004 (2)0.001 (2)0.001 (2)
C70.013 (2)0.029 (3)0.032 (3)−0.002 (2)0.000 (2)0.004 (2)
C80.017 (3)0.035 (3)0.043 (4)0.005 (2)0.001 (3)0.004 (3)
C90.021 (3)0.025 (3)0.027 (3)0.001 (2)0.002 (2)−0.002 (2)
C100.023 (3)0.027 (3)0.028 (3)0.004 (2)0.003 (2)0.003 (2)
C110.032 (3)0.029 (3)0.033 (3)0.002 (3)0.006 (3)−0.001 (3)
C120.057 (5)0.033 (3)0.031 (3)0.008 (4)−0.005 (4)−0.011 (3)
C130.039 (4)0.034 (4)0.038 (4)0.001 (3)−0.005 (3)−0.004 (3)
C140.034 (4)0.031 (4)0.049 (5)−0.005 (3)−0.004 (3)0.004 (3)
Cl10.0207 (6)0.0351 (8)0.0258 (7)−0.0030 (6)−0.0009 (6)0.0029 (6)
Cl20.0255 (7)0.0362 (8)0.0278 (7)0.0049 (6)0.0011 (6)−0.0056 (6)
Cl30.0239 (6)0.0386 (9)0.0312 (7)0.0024 (6)−0.0081 (6)−0.0064 (7)
Cl40.0282 (7)0.0296 (8)0.0437 (9)−0.0046 (6)0.0073 (7)−0.0032 (7)
N10.0149 (19)0.033 (3)0.022 (2)−0.002 (2)−0.0005 (17)0.003 (2)
N20.0113 (19)0.029 (3)0.031 (3)0.0035 (19)0.0002 (18)0.002 (2)
N30.019 (2)0.030 (3)0.040 (3)0.0024 (19)0.001 (2)−0.002 (3)
N40.025 (3)0.034 (3)0.031 (3)−0.007 (2)0.002 (2)0.001 (2)
Pt10.01531 (11)0.02622 (12)0.02281 (12)0.00055 (8)−0.00071 (8)−0.00174 (9)

Geometric parameters (Å, °)

C1—N11.342 (8)C9—N31.349 (8)
C1—C21.357 (10)C9—C101.484 (9)
C1—H10.9300C10—N41.355 (9)
C2—C31.379 (11)C10—C111.382 (10)
C2—H20.9300C11—C121.373 (11)
C3—C41.385 (9)C11—H110.9300
C3—H30.9300C12—C131.374 (13)
C4—C51.398 (8)C12—H120.9300
C4—H40.9300C13—C141.377 (12)
C5—N11.353 (8)C13—H130.9300
C5—C61.490 (8)C14—N41.339 (10)
C6—N21.359 (8)C14—H140.9300
C6—C91.411 (9)Cl1—Pt12.3219 (16)
C7—N21.338 (7)Cl2—Pt12.2945 (16)
C7—C81.379 (10)Cl3—Pt12.3066 (16)
C7—H70.9300Cl4—Pt12.3164 (18)
C8—N31.315 (10)N1—Pt12.036 (5)
C8—H80.9300N2—Pt12.032 (6)
N1—C1—C2121.2 (7)C11—C12—C13119.6 (8)
N1—C1—H1119.4C11—C12—H12120.2
C2—C1—H1119.4C13—C12—H12120.2
C1—C2—C3119.7 (7)C12—C13—C14118.7 (8)
C1—C2—H2120.2C12—C13—H13120.6
C3—C2—H2120.2C14—C13—H13120.6
C2—C3—C4119.6 (7)N4—C14—C13124.1 (8)
C2—C3—H3120.2N4—C14—H14118.0
C4—C3—H3120.2C13—C14—H14118.0
C3—C4—C5118.8 (6)C1—N1—C5120.9 (6)
C3—C4—H4120.6C1—N1—Pt1125.0 (5)
C5—C4—H4120.6C5—N1—Pt1114.1 (4)
N1—C5—C4119.7 (6)C7—N2—C6119.1 (6)
N1—C5—C6115.3 (5)C7—N2—Pt1126.5 (5)
C4—C5—C6124.9 (6)C6—N2—Pt1114.2 (4)
N2—C6—C9118.6 (6)C8—N3—C9118.5 (6)
N2—C6—C5113.8 (5)C14—N4—C10115.4 (7)
C9—C6—C5127.6 (6)N2—Pt1—N180.4 (2)
N2—C7—C8120.1 (7)N2—Pt1—Cl2176.45 (16)
N2—C7—H7119.9N1—Pt1—Cl296.12 (17)
C8—C7—H7119.9N2—Pt1—Cl394.15 (16)
N3—C8—C7122.1 (6)N1—Pt1—Cl3174.20 (18)
N3—C8—H8119.0Cl2—Pt1—Cl389.26 (6)
C7—C8—H8119.0N2—Pt1—Cl490.54 (17)
N3—C9—C6120.2 (6)N1—Pt1—Cl489.68 (17)
N3—C9—C10116.1 (6)Cl2—Pt1—Cl490.30 (6)
C6—C9—C10123.5 (6)Cl3—Pt1—Cl492.45 (7)
N4—C10—C11124.6 (7)N2—Pt1—Cl188.17 (17)
N4—C10—C9113.8 (6)N1—Pt1—Cl186.68 (17)
C11—C10—C9121.5 (6)Cl2—Pt1—Cl190.78 (6)
C12—C11—C10117.6 (7)Cl3—Pt1—Cl191.11 (6)
C12—C11—H11121.2Cl4—Pt1—Cl1176.30 (7)
C10—C11—H11121.2
N1—C1—C2—C3−0.5 (12)C8—C7—N2—C6−1.0 (10)
C1—C2—C3—C42.0 (11)C8—C7—N2—Pt1−175.7 (5)
C2—C3—C4—C5−3.6 (10)C9—C6—N2—C7−9.1 (9)
C3—C4—C5—N13.6 (9)C5—C6—N2—C7169.0 (5)
C3—C4—C5—C6180.0 (6)C9—C6—N2—Pt1166.1 (5)
N1—C5—C6—N29.9 (8)C5—C6—N2—Pt1−15.7 (7)
C4—C5—C6—N2−166.6 (6)C7—C8—N3—C9−3.2 (11)
N1—C5—C6—C9−172.2 (6)C6—C9—N3—C8−7.3 (10)
C4—C5—C6—C911.3 (10)C10—C9—N3—C8167.8 (7)
N2—C7—C8—N37.7 (11)C13—C14—N4—C102.0 (11)
N2—C6—C9—N313.6 (10)C11—C10—N4—C14−0.5 (10)
C5—C6—C9—N3−164.2 (6)C9—C10—N4—C14178.0 (6)
N2—C6—C9—C10−161.1 (6)C7—N2—Pt1—N1−172.4 (6)
C5—C6—C9—C1021.1 (10)C6—N2—Pt1—N112.8 (5)
N3—C9—C10—N4−132.2 (7)C7—N2—Pt1—Cl39.7 (6)
C6—C9—C10—N442.7 (9)C6—N2—Pt1—Cl3−165.2 (4)
N3—C9—C10—C1146.4 (9)C7—N2—Pt1—Cl4−82.8 (5)
C6—C9—C10—C11−138.7 (7)C6—N2—Pt1—Cl4102.3 (4)
N4—C10—C11—C12−2.2 (11)C7—N2—Pt1—Cl1100.7 (5)
C9—C10—C11—C12179.4 (7)C6—N2—Pt1—Cl1−74.2 (4)
C10—C11—C12—C133.4 (11)C1—N1—Pt1—N2172.5 (6)
C11—C12—C13—C14−2.1 (12)C5—N1—Pt1—N2−7.1 (4)
C12—C13—C14—N4−0.7 (12)C1—N1—Pt1—Cl2−8.3 (6)
C2—C1—N1—C50.5 (11)C5—N1—Pt1—Cl2172.0 (4)
C2—C1—N1—Pt1−179.1 (6)C1—N1—Pt1—Cl481.9 (6)
C4—C5—N1—C1−2.1 (9)C5—N1—Pt1—Cl4−97.7 (4)
C6—C5—N1—C1−178.8 (6)C1—N1—Pt1—Cl1−98.8 (6)
C4—C5—N1—Pt1177.5 (5)C5—N1—Pt1—Cl181.6 (4)
C6—C5—N1—Pt10.8 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1···Cl20.932.683.279 (7)122
C3—H3···Cl1i0.932.833.557 (7)136
C4—H4···N40.932.593.000 (10)107
C7—H7···Cl30.932.693.247 (7)120
C14—H14···Cl1ii0.932.743.599 (8)154

Symmetry codes: (i) −x+1/2, −y−1, z+1/2; (ii) x+1/2, −y−1/2, −z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2404).

References

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