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Acta Cryst. (2007). E63, m3114-m3115    [ doi:10.1107/S1600536807059594 ]

Bis(2,9-dimethyl-1,10-phenanthrolinium) hexachloridoplatinate(IV)

M. Yousefi, R. Ahmadi, V. Amani and H. R. Khavasi

Abstract top

The asymmetric unit of the title compound, (C14H13N2)2[PtCl6], contains one independent protonated 2,9-dimethyl-1,10-phenanthrolinium cation and half of a centrosymmetric [PtCl6]2- anion. The Pt ion has an octahedral coordination. Intramolecular N-H...Cl and N-H...N hydrogen bonds help to stabilize the structure.

Comment top

We reported the synthesis and crystal structure of [(H2DA18C6)Cl2], (II), (Yousefi et al., 2007), [H2DA18C6][PtCl6]·2H2O, (III), (Yousefi et al., 2007a) and [TBA]3[PtCl6]Cl, (IV), (Yousefi et al., 2007b) [where H2DA18C6 is 1,10-Diazonia-18-crown-6 and TBA is tribenzylammonium], recently. We have also, reported the synthesis and crystal structure of [PtCl4(pz)2], (V), (Yousefi et al., 2007c) [where pz is pyrazine]. Several proton transfer systems using 2,9-dimethyl-1,10-phenanthroline, with proton donor molecules, such as [Dmphen](ClO4), (VI), (Morsali, 2005), [Dmphen](NO3), (VII), (Yu et al., 2006), [Dmphen][Ru(CO)3Cl3], (VIII), (Moreno et al., 2006) and [Dmphen] [FeCl4], (IX), (Veidis et al., 1981) [where Dmphen is 2,9-dimethyl-1,10 -phenanthrolinium] have been synthesized and characterized by single-crystal X-ray diffraction methods.

There are also several proton transfer systems using H2[PtCl6] with proton acceptor molecules, such as [HpyBr-3]2[PtCl6]·2H2O, (X), and [HpyI-3]2 [PtCl6]·2H2O, (XI), (Zordan & Brammer, 2004), [BMIM]2[PtCl6], (XII), and [EMIM]2[PtCl6], (XIII), (Hasan et al., 2001), {(DABCO)H2[PtCl6]}, (XIV), (Juan et al., 1998), {p-C6H4(CH2ImMe)2[PtCl6]}, (XV), (Li & Liu, 2003), [het][PtCl6]·2H2O, (XVI), (Hu et al., 2003), [9-MeGuaH]2 [PtCl6]·2H2O, (XVII), (Terzis & Mentzafos, 1983), [H10[30]aneN10] [PtCl6]2Cl6·2H2O, (XVIII), (Bencini et al., 1992), [H2Me2ppz] [PtCl6], (XIX), (Ciccarese et al., 1998), [PA]2[PtCl6]Cl, (XX), (Delafontaine et al., 1987), [DEA]2[PtCl6], (XXI), (Bokach et al., 2003) and [HpyCl-3]3[PtCl6]Cl, (XXII), (Zordan et al., 2005) [where hpy is halopyridinium, BMIM+ is 1-n-butyl-3-methylimidazolium, EMIM+ is 1-ethyl −3-methylimidazolium, DABCO is 1,4-diazabicyclooctane, Im is imidazolium, het is 2-(α-hydroxyethyl)thiamine, 9-MeGuaH is 9-methylguaninium, [H10[30]aneN10] is [C20H60N10]10+ cation, H2Me2ppz is N,N'-dimethylpiperazinium, PA is pentane-1,5-diammonium and DEA is diethyl- ammonium] have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound, (I).

The asymmetric unit of (I), (Fig. 1) contains one independent protonated 2,9-dimethyl-1,10-phenanthroline cation and one half PtCl2−6 anion. The Pt ion has an octahedral coordination (Table 1). In cation, the bond lengths and angles are in good agreement with the corresponding values in (VI) and (VII). In PtCl2−6 anion, the Pt—Cl bond lengths and Cl—Pt—Cl bond angles (Table 1) are also within normal ranges, as in (III) and (IV).

The intramolecular N—H···Cl and N—H···N hydrogen bonds (Table 2) seem to be effective in the stabilization of the structure.

Related literature top

For related literature, see: Yousefi, Amani et al. (2007); Yousefi, Teimouri et al. (2007a,b,c); Morsali (2005); Yu et al. (2006); Moreno et al. (2006); Veidis et al. (1981); Zordan & Brammer (2004); Hasan et al. (2001); Juan et al. (1998); Li & Liu (2003); Hu et al. (2003); Terzis & Mentzafos (1983); Bencini et al. (1992); Ciccarese et al. (1998); Delafontaine et al. (1987); Bokach et al. (2003); Zordan et al. (2005).

For related literature, see: Delafontaine et al. (1987).

Experimental top

For the preparation of the title compound, (I), a solution of 2,9-dimethyl-1,10 -phenanthroline (0.31 g, 1.48 mmol) in methanol (10 ml) was added to a solution of H2PtCl6·6H2O, (0.38 g, 0.74 mmol) in methanol (10 ml) at room temperature. The suitable crystals for X-ray analysis were obtained by methanol diffusion in a solution of yellow precipitate in DMSO after one week (yield; 0.51 g, 83.4%).

Refinement top

H atom (for NH) was located in difference syntheses and refined isotropically [N—H = 0.93 (7) Å and Uiso(H) = 0.021 (14) Å2]. The remaining H atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å, for aromatic and methyl H atoms and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Bis(2,9-dimethyl-1,10-phenanthrolinium) hexachloridoplatinate(IV) top
Crystal data top
(C14H13N2)2[PtCl6]Z = 1
Mr = 826.31F000 = 402
Triclinic, P1Dx = 1.862 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 8.9617 (10) ÅCell parameters from 4500 reflections
b = 9.2179 (10) Åθ = 2.3–29.2º
c = 9.9930 (11) ŵ = 5.33 mm−1
α = 78.427 (9)ºT = 120 (2) K
β = 66.464 (8)ºBlock, orange
γ = 79.540 (9)º0.50 × 0.27 × 0.25 mm
V = 736.70 (14) Å3
Data collection top
Stoe IPDSII
diffractometer		3817 independent reflections
Radiation source: fine-focus sealed tube3813 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.073
Detector resolution: 0.15 mm pixels mm-1θmax = 29.2º
T = 120(2) Kθmin = 2.3º
rotation method scansh = −12→12
Absorption correction: numerical
(shape of crystal determined optically)		k = −11→12
Tmin = 0.195, Tmax = 0.265l = −13→13
8112 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.037  w = 1/[σ2(Fo2) + (0.0772P)2 + 0.2717P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.100(Δ/σ)max = 0.015
S = 1.10Δρmax = 2.93 e Å−3
3817 reflectionsΔρmin = −3.20 e Å−3
183 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.061 (6)
Secondary atom site location: difference Fourier map
Crystal data top
(C14H13N2)2[PtCl6]γ = 79.540 (9)º
Mr = 826.31V = 736.70 (14) Å3
Triclinic, P1Z = 1
a = 8.9617 (10) ÅMo Kα
b = 9.2179 (10) ŵ = 5.33 mm−1
c = 9.9930 (11) ÅT = 120 (2) K
α = 78.427 (9)º0.50 × 0.27 × 0.25 mm
β = 66.464 (8)º
Data collection top
Stoe IPDSII
diffractometer		3817 independent reflections
Absorption correction: numerical
(shape of crystal determined optically)		3813 reflections with I > 2σ(I)
Tmin = 0.195, Tmax = 0.265Rint = 0.073
8112 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037183 parameters
wR(F2) = 0.100H atoms treated by a mixture of
independent and constrained refinement
S = 1.10Δρmax = 2.93 e Å−3
3817 reflectionsΔρmin = −3.20 e Å−3
Special details top

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 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R– factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pt10.00000.50000.00000.01485 (12)
Cl1−0.24815 (12)0.59692 (11)−0.02163 (13)0.0257 (2)
Cl2−0.03063 (12)0.26384 (11)−0.02698 (12)0.02210 (19)
Cl3−0.13725 (14)0.43950 (12)0.25290 (11)0.0255 (2)
N1−0.2722 (5)0.1814 (4)0.5578 (4)0.0221 (6)
N2−0.3408 (4)0.1347 (4)0.3301 (4)0.0205 (6)
H2−0.349 (8)0.228 (7)0.356 (7)0.021 (14)*
C1−0.2682 (9)0.3619 (6)0.7008 (6)0.0383 (12)
H1A−0.38210.39740.72500.046*
H1B−0.20350.42450.61570.046*
H1C−0.23850.36440.78250.046*
C2−0.2375 (6)0.2055 (5)0.6681 (5)0.0254 (8)
C3−0.1730 (6)0.0873 (5)0.7538 (5)0.0254 (8)
H3−0.14840.10820.82950.031*
C4−0.1473 (6)−0.0565 (5)0.7255 (5)0.0243 (8)
H4−0.1068−0.13380.78190.029*
C5−0.1839 (5)−0.0844 (5)0.6073 (4)0.0210 (7)
C6−0.1628 (6)−0.2299 (5)0.5680 (5)0.0244 (8)
H6−0.1193−0.31090.61860.029*
C7−0.2057 (6)−0.2517 (5)0.4571 (5)0.0238 (7)
H7−0.1934−0.34740.43470.029*
C8−0.2693 (5)−0.1287 (5)0.3755 (4)0.0203 (7)
C9−0.3174 (5)−0.1435 (5)0.2607 (5)0.0250 (8)
H9−0.3103−0.23730.23610.030*
C10−0.3751 (5)−0.0186 (6)0.1850 (5)0.0257 (8)
H10−0.4069−0.02880.10980.031*
C11−0.3858 (5)0.1233 (5)0.2207 (5)0.0228 (7)
C12−0.4467 (6)0.2634 (6)0.1432 (5)0.0288 (9)
H12A−0.36300.32940.10030.035*
H12B−0.54250.31110.21280.035*
H12C−0.47380.23950.06710.035*
C13−0.2848 (5)0.0152 (4)0.4093 (4)0.0178 (6)
C14−0.2458 (5)0.0393 (4)0.5291 (4)0.0185 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pt10.01930 (15)0.01366 (15)0.01486 (14)−0.00114 (7)−0.01009 (9)−0.00206 (7)
Cl10.0245 (4)0.0221 (4)0.0365 (5)−0.0005 (3)−0.0191 (4)−0.0028 (4)
Cl20.0259 (4)0.0170 (4)0.0267 (5)−0.0028 (3)−0.0117 (4)−0.0061 (3)
Cl30.0373 (5)0.0220 (4)0.0172 (4)−0.0047 (4)−0.0099 (4)−0.0026 (3)
N10.0298 (17)0.0175 (15)0.0190 (15)−0.0037 (12)−0.0090 (13)−0.0023 (12)
N20.0219 (15)0.0207 (16)0.0194 (15)−0.0020 (12)−0.0093 (12)−0.0008 (12)
C10.072 (4)0.020 (2)0.029 (2)−0.007 (2)−0.025 (2)−0.0055 (17)
C20.038 (2)0.0199 (18)0.0201 (18)−0.0067 (15)−0.0115 (17)−0.0014 (14)
C30.036 (2)0.025 (2)0.0188 (17)−0.0073 (16)−0.0135 (16)−0.0022 (15)
C40.034 (2)0.0250 (19)0.0174 (17)−0.0060 (15)−0.0140 (16)0.0009 (14)
C50.0282 (18)0.0202 (18)0.0165 (16)−0.0053 (14)−0.0102 (14)−0.0004 (13)
C60.032 (2)0.0170 (17)0.0227 (18)−0.0015 (14)−0.0115 (16)0.0012 (14)
C70.033 (2)0.0176 (17)0.0222 (18)−0.0003 (14)−0.0122 (16)−0.0044 (14)
C80.0226 (17)0.0197 (17)0.0192 (17)−0.0024 (13)−0.0076 (14)−0.0050 (14)
C90.0238 (18)0.028 (2)0.0247 (19)−0.0057 (15)−0.0082 (16)−0.0060 (16)
C100.0239 (18)0.036 (2)0.0210 (18)−0.0054 (16)−0.0100 (15)−0.0068 (16)
C110.0170 (15)0.031 (2)0.0208 (18)−0.0020 (14)−0.0097 (14)−0.0012 (15)
C120.0261 (19)0.034 (2)0.028 (2)0.0002 (16)−0.0165 (17)0.0040 (17)
C130.0207 (16)0.0188 (17)0.0153 (15)−0.0017 (12)−0.0087 (13)−0.0019 (12)
C140.0243 (17)0.0177 (17)0.0154 (15)−0.0047 (13)−0.0085 (13)−0.0023 (13)
Geometric parameters (Å, °) top
Pt1—Cl12.3184 (10)C6—C71.369 (6)
Pt1—Cl1i2.3184 (10)C6—H60.9300
Pt1—Cl22.3235 (9)C7—C81.429 (6)
Pt1—Cl2i2.3235 (9)C7—H70.9300
Pt1—Cl3i2.3263 (11)C8—C131.403 (5)
Pt1—Cl32.3263 (11)C8—C91.414 (6)
N2—H20.93 (7)C9—C101.383 (7)
C1—C21.495 (6)C9—H90.9300
C1—H1A0.9600C10—C111.400 (6)
C1—H1B0.9600C10—H100.9300
C1—H1C0.9600C11—N21.336 (5)
C2—N11.325 (6)C11—C121.498 (6)
C2—C31.432 (6)C12—H12A0.9600
C3—C41.370 (6)C12—H12B0.9600
C3—H30.9300C12—H12C0.9600
C4—C51.426 (6)C13—N21.364 (5)
C4—H40.9300C13—C141.441 (5)
C5—C141.407 (6)C14—N11.355 (5)
C5—C61.431 (6)
Cl1—Pt1—Cl1i180C7—C6—H6119.5
Cl1—Pt1—Cl291.41 (4)C5—C6—H6119.5
Cl1i—Pt1—Cl288.59 (4)C6—C7—C8120.6 (4)
Cl1—Pt1—Cl2i88.59 (4)C6—C7—H7119.7
Cl1i—Pt1—Cl2i91.41 (4)C8—C7—H7119.7
Cl2—Pt1—Cl2i180C13—C8—C9117.6 (4)
Cl1—Pt1—Cl3i90.59 (4)C13—C8—C7118.9 (4)
Cl1i—Pt1—Cl3i89.41 (4)C9—C8—C7123.5 (4)
Cl2—Pt1—Cl3i91.76 (4)C10—C9—C8120.0 (4)
Cl2i—Pt1—Cl3i88.24 (4)C10—C9—H9120.0
Cl1—Pt1—Cl389.41 (4)C8—C9—H9120.0
Cl1i—Pt1—Cl390.59 (4)C9—C10—C11120.5 (4)
Cl2—Pt1—Cl388.24 (4)C9—C10—H10119.7
Cl2i—Pt1—Cl391.76 (4)C11—C10—H10119.7
Cl3i—Pt1—Cl3180N2—C11—C10118.5 (4)
C2—C1—H1A109.5N2—C11—C12118.1 (4)
C2—C1—H1B109.5C10—C11—C12123.4 (4)
H1A—C1—H1B109.5C11—C12—H12A109.5
C2—C1—H1C109.5C11—C12—H12B109.5
H1A—C1—H1C109.5H12A—C12—H12B109.5
H1B—C1—H1C109.5C11—C12—H12C109.5
N1—C2—C3121.8 (4)H12A—C12—H12C109.5
N1—C2—C1117.6 (4)H12B—C12—H12C109.5
C3—C2—C1120.5 (4)N2—C13—C8120.0 (4)
C4—C3—C2120.6 (4)N2—C13—C14118.9 (3)
C4—C3—H3119.7C8—C13—C14121.1 (4)
C2—C3—H3119.7N1—C14—C5124.9 (4)
C3—C4—C5118.3 (4)N1—C14—C13116.8 (4)
C3—C4—H4120.9C5—C14—C13118.3 (4)
C5—C4—H4120.9C2—N1—C14117.6 (4)
C14—C5—C4116.8 (4)C11—N2—C13123.4 (4)
C14—C5—C6120.0 (4)C11—N2—H2119 (4)
C4—C5—C6123.3 (4)C13—N2—H2117 (4)
C7—C6—C5121.0 (4)
N1—C2—C3—C4−1.0 (7)C7—C8—C13—C14−3.2 (6)
C1—C2—C3—C4179.0 (5)C4—C5—C14—N10.2 (6)
C2—C3—C4—C50.9 (7)C6—C5—C14—N1179.3 (4)
C3—C4—C5—C14−0.5 (6)C4—C5—C14—C13−179.8 (4)
C3—C4—C5—C6−179.6 (4)C6—C5—C14—C13−0.6 (6)
C14—C5—C6—C7−1.6 (7)N2—C13—C14—N11.8 (5)
C4—C5—C6—C7177.5 (4)C8—C13—C14—N1−176.9 (4)
C5—C6—C7—C81.4 (7)N2—C13—C14—C5−178.3 (4)
C6—C7—C8—C130.9 (6)C8—C13—C14—C53.1 (6)
C6—C7—C8—C9−179.4 (4)C3—C2—N1—C140.6 (7)
C13—C8—C9—C100.9 (6)C1—C2—N1—C14−179.4 (4)
C7—C8—C9—C10−178.8 (4)C5—C14—N1—C2−0.2 (6)
C8—C9—C10—C110.2 (6)C13—C14—N1—C2179.8 (4)
C9—C10—C11—N2−0.7 (6)C10—C11—N2—C130.0 (6)
C9—C10—C11—C12179.9 (4)C12—C11—N2—C13179.4 (4)
C9—C8—C13—N2−1.6 (6)C8—C13—N2—C111.2 (6)
C7—C8—C13—N2178.1 (4)C14—C13—N2—C11−177.5 (4)
C9—C8—C13—C14177.1 (4)
Symmetry codes: (i) −x, −y+1, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···Cl30.93 (7)2.73 (7)3.418 (4)132 (5)
N2—H2···N10.93 (7)2.32 (7)2.711 (6)105 (5)
Selected geometric parameters (Å, °) top
Pt1—Cl12.3184 (10)Pt1—Cl32.3263 (11)
Pt1—Cl22.3235 (9)
Cl1—Pt1—Cl291.41 (4)Cl2—Pt1—Cl3i91.76 (4)
Cl1—Pt1—Cl2i88.59 (4)Cl1—Pt1—Cl389.41 (4)
Cl1—Pt1—Cl3i90.59 (4)Cl2—Pt1—Cl388.24 (4)
Symmetry codes: (i) −x, −y+1, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···Cl30.93 (7)2.73 (7)3.418 (4)132 (5)
N2—H2···N10.93 (7)2.32 (7)2.711 (6)105 (5)
Acknowledgements top

The authors are grateful to Islamic Azad University, Shahr-e-Rey Branch, the Research Institute in Education and Shahid Beheshti University for financial support.

references
References top

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