Tetra­chlorido(1,10-phenanthroline-κ2N,N′)platinum(IV) acetonitrile hemisolvate

Kim, N.-H.; Hwang, I.-C.; Ha, K.

doi:10.1107/S1600536809002359

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m224

doi:10.1107/S1600536809002359

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Tetrachlorido(1,10-phenanthroline-κ²N,N′)platinum(IV) acetonitrile hemisolvate

Nam-Ho Kim,^a In-Chul Hwang ^b and Kwang Ha ^a ^*

^aSchool of Applied Chemical Engineering, Research Institute of Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea, and ^bDepartment of Chemistry, Pohang University of Science and Technology, Pohang 790-784, Republic of Korea
^*Correspondence e-mail: hakwang@chonnam.ac.kr

(Received 7 January 2009; accepted 19 January 2009; online 23 January 2009)

The asymmetric unit of the title compound, [PtCl₄(C₁₂H₈N₂)]·0.5CH₃CN, contains two crystallographically independent Pt^IV complexes with very similar geometry and one solvent molecule. In the complexes, each Pt^IV ion is six-coordinated in a distorted octahedral environment by two N atoms of the 1,10-phenanthroline ligand and four Cl atoms. Because of the different trans effects of the N and Cl atoms, the Pt—Cl bonds trans to the N atom are slightly shorter than those trans to the Cl atom. The compound displays numerous intermolecular π–π interactions between six-membered rings, with a shortest centroid-to-centroid distance of 3.654 Å. There are also weak intra- and intermolecular C—H⋯Cl hydrogen bonds.

Related literature

For details of some other Pt–phenanthroline complexes, see: Buse et al. (1977 ); Fanizzi et al. (1996 ). For related Pt–bipyridine complexes, see: Hambley (1986 ); Hojjat Kashani et al. (2008 ).

Experimental

Crystal data

[PtCl₄(C₁₂H₈N₂)]·0.5C₂H₃N
M_r = 1075.24
Triclinic, $[P \overline 1]$
a = 7.671 (5) Å
b = 12.619 (8) Å
c = 16.63 (1) Å
α = 89.70 (1)°
β = 87.46 (1)°
γ = 78.797 (7)°
V = 1577 (2) Å³
Z = 2
Mo Kα radiation
μ = 9.56 mm⁻¹
T = 293 (2) K
0.55 × 0.30 × 0.30 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.035, T_max = 0.057
8700 measured reflections
5856 independent reflections
5250 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.104
S = 1.09
5856 reflections
372 parameters
H-atom parameters constrained
Δρ_max = 1.97 e Å⁻³
Δρ_min = −2.05 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl2	0.93	2.68	3.243 (7)	120
C1—H1⋯Cl6	0.93	2.75	3.632 (7)	158
C6—H6⋯Cl8ⁱ	0.93	2.74	3.637 (8)	163
C10—H10⋯Cl1	0.93	2.72	3.275 (9)	120
C13—H13⋯Cl6	0.93	2.68	3.248 (9)	120
C15—H15⋯Cl1ⁱⁱ	0.93	2.79	3.669 (9)	159
C21—H21⋯Cl2ⁱⁱⁱ	0.93	2.72	3.451 (9)	136
C22—H22⋯Cl5	0.93	2.74	3.297 (9)	120
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z; (iii) x, y-1, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002359/im2096sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002359/im2096Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title compound, [PtCl₄(C₁₂H₈N₂)].0.5CH₃CN, contains two crystallographically independent Pt^IV complexes with identical geometry and a CH₃CN solvent molecule (Fig. 1 and 2). In the complexes, each Pt⁴⁺ ion is six-coordinated in a distorted octahedral environment by two N atoms of the 1,10-phenanthroline ligand and four Cl atoms. The main contributions to the distortion are the tight N—Pt—N chelate angles (82.0 (2)° and 80.9 (2)°), which result in non-linear trans axes (Cl—Pt—N = 174.7 (2)–175.7 (2)°, Cl—Pt—Cl = 177.57 (8)° and 175.68 (7)°). Because of the different trans effects of the N and Cl atoms, the Pt—Cl bonds trans to the N atom (lengths: 2.294 (2), 2.297 (2), 2.301 (2) and 2.298 (2) Å; mean length: 2.298 (2) Å) are slightly shorter than bond lengths to mutually trans Cl atoms (lengths: 2.322 (2), 2.312 (2), 2.302 (2) and 2.309 (2) Å; mean length: 2.311 (2) Å). The compound displays numerous intermolecular π–π interactions between six-membered rings, with a shortest centroid–centroid distance of 3.654 Å. There are also weak intra- and intermolecular C—H···Cl hydrogen bonds (Table 1).

Related literature top

For details of some other Pt–phenanthroline complexes, see: Buse et al. (1977); Fanizzi et al. (1996). For related Pt–bipyridine complexes, see: Hambley (1986); Hojjat Kashani et al. (2008).

Experimental top

To a solution of K₂PtCl₆ (0.2026 g, 0.417 mmol) in H₂O (10 ml) was added 1,10-phenanthroline (0.2162 g, 1.200 mmol) in MeOH (10 ml), and stirred for 5 h at room temperature. The formed precipitate was separated by filtration and washed with water and MeOH and dried under vacuum, to give a yellow powder (0.1710 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from a CH₃CN solution.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound, with displacement ellipsoids drawn at the 30% probability level for non-H atoms.
	Fig. 2. View of the unit-cell contents of the title compound. Hydrogen-bond interactions are drawn with dashed lines.

Tetrachlorido(1,10-phenanthroline-κ²N,N')platinum(IV) acetonitrile hemisolvate top

Crystal data top

[PtCl₄(C₁₂H₈N₂)]·0.5C₂H₃N	Z = 2
M_r = 1075.24	F(000) = 1004
Triclinic, P1	D_x = 2.264 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.671 (5) Å	Cell parameters from 907 reflections
b = 12.619 (8) Å	θ = 3.0–26.4°
c = 16.63 (1) Å	µ = 9.56 mm⁻¹
α = 89.70 (1)°	T = 293 K
β = 87.46 (1)°	Rod, yellow
γ = 78.797 (7)°	0.55 × 0.30 × 0.30 mm
V = 1577 (2) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	5856 independent reflections
Radiation source: fine-focus sealed tube	5250 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.7°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
T_min = 0.035, T_max = 0.057	k = −15→14
8700 measured reflections	l = −9→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0696P)² + 1.1983P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
5856 reflections	Δρ_max = 1.97 e Å⁻³
372 parameters	Δρ_min = −2.05 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0069 (3)

Crystal data top

[PtCl₄(C₁₂H₈N₂)]·0.5C₂H₃N	γ = 78.797 (7)°
M_r = 1075.24	V = 1577 (2) Å³
Triclinic, P1	Z = 2
a = 7.671 (5) Å	Mo Kα radiation
b = 12.619 (8) Å	µ = 9.56 mm⁻¹
c = 16.63 (1) Å	T = 293 K
α = 89.70 (1)°	0.55 × 0.30 × 0.30 mm
β = 87.46 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	5856 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	5250 reflections with I > 2σ(I)
T_min = 0.035, T_max = 0.057	R_int = 0.027
8700 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.09	Δρ_max = 1.97 e Å⁻³
5856 reflections	Δρ_min = −2.05 e Å⁻³
372 parameters

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 > 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

	x	y	z	U_iso*/U_eq
Pt1	0.22405 (3)	0.743662 (18)	0.348926 (14)	0.03174 (12)
Cl1	0.1723 (3)	0.90349 (15)	0.27957 (12)	0.0592 (6)
Cl2	0.4276 (3)	0.66204 (15)	0.25175 (12)	0.0586 (6)
Cl3	0.4436 (2)	0.80367 (14)	0.41769 (12)	0.0440 (4)
Cl4	−0.0011 (3)	0.68354 (17)	0.28563 (13)	0.0604 (6)
N1	0.2550 (6)	0.6080 (4)	0.4184 (3)	0.0259 (10)
N2	0.0449 (7)	0.8027 (4)	0.4402 (3)	0.0329 (12)
C1	0.3525 (9)	0.5108 (5)	0.4027 (4)	0.0336 (14)
H1	0.4154	0.4982	0.3534	0.040*
C2	0.3624 (9)	0.4275 (5)	0.4583 (4)	0.0379 (15)
H2	0.4316	0.3602	0.4456	0.046*
C3	0.2724 (9)	0.4430 (6)	0.5313 (5)	0.0406 (17)
H3	0.2806	0.3871	0.5685	0.049*
C4	0.1658 (9)	0.5460 (5)	0.5493 (4)	0.0336 (14)
C5	0.0584 (10)	0.5727 (7)	0.6212 (4)	0.0442 (18)
H5	0.0636	0.5217	0.6621	0.053*
C6	−0.0497 (10)	0.6690 (7)	0.6318 (4)	0.0466 (18)
H6	−0.1184	0.6834	0.6794	0.056*
C7	−0.0609 (9)	0.7500 (6)	0.5710 (4)	0.0408 (16)
C8	−0.1779 (10)	0.8520 (7)	0.5756 (6)	0.053 (2)
H8	−0.2517	0.8709	0.6213	0.064*
C9	−0.1814 (10)	0.9223 (7)	0.5128 (6)	0.056 (2)
H9	−0.2594	0.9887	0.5151	0.067*
C10	−0.0692 (10)	0.8948 (6)	0.4460 (5)	0.0457 (18)
H10	−0.0745	0.9432	0.4034	0.055*
C11	0.0471 (8)	0.7290 (5)	0.5010 (4)	0.0321 (14)
C12	0.1595 (8)	0.6274 (5)	0.4905 (4)	0.0272 (12)
Pt2	0.66093 (3)	0.20111 (2)	0.213982 (14)	0.03046 (12)
Cl5	0.6389 (3)	0.17427 (19)	0.35077 (11)	0.0554 (5)
Cl6	0.6342 (3)	0.38351 (16)	0.23497 (13)	0.0553 (5)
Cl7	0.9662 (2)	0.17316 (15)	0.21686 (12)	0.0454 (4)
Cl8	0.3574 (2)	0.21957 (18)	0.20343 (12)	0.0523 (5)
N3	0.6888 (7)	0.2128 (4)	0.0925 (3)	0.0320 (12)
N4	0.6814 (7)	0.0429 (4)	0.1845 (3)	0.0317 (12)
C13	0.6842 (12)	0.3021 (7)	0.0489 (5)	0.052 (2)
H13	0.6623	0.3694	0.0740	0.063*
C14	0.7131 (14)	0.2939 (9)	−0.0360 (5)	0.068 (3)
H14	0.7111	0.3558	−0.0668	0.081*
C15	0.7435 (13)	0.1957 (8)	−0.0718 (5)	0.061 (2)
H15	0.7643	0.1910	−0.1273	0.073*
C16	0.7445 (10)	0.1033 (6)	−0.0286 (4)	0.0454 (17)
C17	0.7660 (13)	−0.0050 (8)	−0.0609 (5)	0.065 (3)
H17	0.7849	−0.0152	−0.1162	0.078*
C18	0.7596 (13)	−0.0894 (8)	−0.0150 (6)	0.070 (3)
H18	0.7768	−0.1575	−0.0386	0.084*
C19	0.7265 (10)	−0.0793 (6)	0.0715 (5)	0.0491 (19)
C20	0.7087 (12)	−0.1636 (7)	0.1247 (7)	0.060 (2)
H20	0.7216	−0.2339	0.1054	0.073*
C21	0.6734 (12)	−0.1430 (7)	0.2032 (7)	0.064 (3)
H21	0.6576	−0.1989	0.2377	0.077*
C22	0.6599 (10)	−0.0387 (6)	0.2342 (5)	0.0478 (19)
H22	0.6362	−0.0258	0.2890	0.057*
C23	0.7100 (8)	0.0249 (5)	0.1044 (4)	0.0338 (14)
C24	0.7161 (8)	0.1149 (5)	0.0555 (4)	0.0340 (14)
N5	0.225 (2)	0.4009 (12)	0.0069 (10)	0.153 (6)
C25	0.0741 (19)	0.4592 (9)	0.1403 (7)	0.094 (4)
H26A	0.1404	0.5048	0.1669	0.140*
H26B	0.0692	0.3965	0.1726	0.140*
H26C	−0.0445	0.4984	0.1328	0.140*
C26	0.159 (2)	0.4266 (10)	0.0640 (8)	0.098 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.04667 (19)	0.02322 (16)	0.02332 (16)	−0.00292 (11)	0.00364 (11)	−0.00038 (10)
Cl1	0.1033 (17)	0.0321 (9)	0.0373 (10)	−0.0022 (9)	0.0031 (11)	0.0082 (8)
Cl2	0.0919 (15)	0.0362 (9)	0.0423 (11)	−0.0070 (9)	0.0334 (11)	−0.0047 (8)
Cl3	0.0463 (9)	0.0337 (8)	0.0532 (11)	−0.0113 (7)	−0.0004 (8)	−0.0019 (8)
Cl4	0.0792 (14)	0.0493 (11)	0.0543 (12)	−0.0101 (10)	−0.0322 (11)	−0.0024 (9)
N1	0.030 (3)	0.028 (3)	0.021 (2)	−0.008 (2)	−0.002 (2)	−0.001 (2)
N2	0.036 (3)	0.030 (3)	0.030 (3)	−0.001 (2)	0.000 (2)	−0.004 (2)
C1	0.036 (3)	0.030 (3)	0.035 (4)	−0.007 (3)	0.001 (3)	−0.005 (3)
C2	0.039 (4)	0.031 (3)	0.045 (4)	−0.010 (3)	−0.009 (3)	0.001 (3)
C3	0.040 (4)	0.039 (4)	0.048 (4)	−0.017 (3)	−0.017 (3)	0.014 (3)
C4	0.036 (3)	0.044 (4)	0.027 (3)	−0.020 (3)	−0.005 (3)	0.000 (3)
C5	0.055 (4)	0.062 (5)	0.024 (3)	−0.034 (4)	−0.004 (3)	0.001 (3)
C6	0.051 (4)	0.063 (5)	0.032 (4)	−0.029 (4)	0.009 (3)	−0.010 (3)
C7	0.034 (3)	0.058 (4)	0.035 (4)	−0.019 (3)	0.005 (3)	−0.015 (3)
C8	0.038 (4)	0.060 (5)	0.060 (5)	−0.010 (3)	0.013 (4)	−0.033 (4)
C9	0.042 (4)	0.039 (4)	0.085 (7)	−0.005 (3)	0.011 (4)	−0.026 (4)
C10	0.046 (4)	0.036 (4)	0.053 (5)	−0.001 (3)	−0.003 (4)	−0.014 (3)
C11	0.026 (3)	0.040 (3)	0.031 (3)	−0.008 (3)	0.001 (3)	−0.011 (3)
C12	0.029 (3)	0.031 (3)	0.024 (3)	−0.010 (2)	−0.005 (2)	0.004 (2)
Pt2	0.02315 (16)	0.04333 (18)	0.02481 (16)	−0.00705 (10)	0.00409 (10)	−0.01164 (11)
Cl5	0.0534 (11)	0.0889 (15)	0.0243 (8)	−0.0158 (10)	0.0042 (8)	−0.0096 (9)
Cl6	0.0596 (12)	0.0453 (10)	0.0580 (12)	−0.0041 (8)	0.0057 (10)	−0.0247 (9)
Cl7	0.0250 (8)	0.0594 (11)	0.0528 (11)	−0.0107 (7)	0.0002 (7)	−0.0201 (9)
Cl8	0.0228 (8)	0.0838 (14)	0.0487 (11)	−0.0072 (8)	0.0031 (7)	−0.0119 (10)
N3	0.031 (3)	0.039 (3)	0.028 (3)	−0.011 (2)	0.005 (2)	−0.006 (2)
N4	0.027 (3)	0.038 (3)	0.033 (3)	−0.013 (2)	0.001 (2)	−0.007 (2)
C13	0.068 (5)	0.044 (4)	0.046 (5)	−0.014 (4)	0.003 (4)	0.001 (4)
C14	0.089 (7)	0.075 (6)	0.042 (5)	−0.024 (5)	0.004 (5)	0.018 (5)
C15	0.080 (6)	0.075 (6)	0.025 (4)	−0.010 (5)	0.002 (4)	−0.002 (4)
C16	0.048 (4)	0.053 (4)	0.033 (4)	−0.004 (3)	0.002 (3)	−0.013 (3)
C17	0.073 (6)	0.076 (6)	0.036 (4)	0.007 (5)	−0.002 (4)	−0.024 (4)
C18	0.078 (6)	0.061 (6)	0.064 (6)	0.008 (5)	−0.016 (5)	−0.038 (5)
C19	0.046 (4)	0.042 (4)	0.059 (5)	−0.005 (3)	−0.008 (4)	−0.016 (4)
C20	0.059 (5)	0.038 (4)	0.084 (7)	−0.006 (4)	−0.018 (5)	−0.012 (4)
C21	0.063 (6)	0.047 (5)	0.086 (7)	−0.016 (4)	−0.024 (5)	0.015 (5)
C22	0.040 (4)	0.056 (5)	0.052 (5)	−0.018 (3)	−0.007 (4)	0.015 (4)
C23	0.027 (3)	0.039 (4)	0.035 (4)	−0.005 (3)	0.000 (3)	−0.013 (3)
C24	0.029 (3)	0.043 (4)	0.029 (3)	−0.004 (3)	0.002 (3)	−0.012 (3)
N5	0.179 (15)	0.133 (12)	0.121 (12)	0.031 (10)	0.022 (11)	−0.030 (10)
C25	0.127 (10)	0.069 (7)	0.081 (8)	−0.015 (7)	0.027 (8)	−0.008 (6)
C26	0.131 (12)	0.073 (8)	0.075 (8)	0.017 (7)	−0.010 (8)	−0.020 (7)

Geometric parameters (Å, º) top

Pt1—N1	2.041 (5)	Pt2—Cl5	2.301 (2)
Pt1—N2	2.044 (5)	Pt2—Cl7	2.302 (2)
Pt1—Cl1	2.294 (2)	Pt2—Cl8	2.309 (2)
Pt1—Cl2	2.297 (2)	N3—C13	1.332 (10)
Pt1—Cl4	2.312 (2)	N3—C24	1.358 (8)
Pt1—Cl3	2.322 (2)	N4—C22	1.348 (9)
N1—C1	1.327 (8)	N4—C23	1.353 (8)
N1—C12	1.374 (8)	C13—C14	1.421 (12)
N2—C10	1.313 (9)	C13—H13	0.9300
N2—C11	1.369 (9)	C14—C15	1.351 (14)
C1—C2	1.390 (10)	C14—H14	0.9300
C1—H1	0.9300	C15—C16	1.365 (12)
C2—C3	1.365 (11)	C15—H15	0.9300
C2—H2	0.9300	C16—C24	1.410 (10)
C3—C4	1.420 (10)	C16—C17	1.448 (12)
C3—H3	0.9300	C17—C18	1.315 (14)
C4—C12	1.411 (9)	C17—H17	0.9300
C4—C5	1.425 (10)	C18—C19	1.451 (13)
C5—C6	1.339 (11)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.404 (13)
C6—C7	1.427 (11)	C19—C23	1.408 (10)
C6—H6	0.9300	C20—C21	1.336 (14)
C7—C11	1.393 (9)	C20—H20	0.9300
C7—C8	1.420 (11)	C21—C22	1.400 (12)
C8—C9	1.364 (13)	C21—H21	0.9300
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.378 (12)	C23—C24	1.400 (10)
C9—H9	0.9300	N5—C26	1.077 (17)
C10—H10	0.9300	C25—C26	1.425 (18)
C11—C12	1.407 (9)	C25—H26A	0.9600
Pt2—N3	2.030 (5)	C25—H26B	0.9600
Pt2—N4	2.032 (5)	C25—H26C	0.9600
Pt2—Cl6	2.298 (2)

N1—Pt1—N2	82.0 (2)	N4—Pt2—Cl5	95.07 (17)
N1—Pt1—Cl1	174.98 (15)	Cl6—Pt2—Cl5	90.10 (8)
N2—Pt1—Cl1	92.96 (16)	N3—Pt2—Cl7	87.56 (15)
N1—Pt1—Cl2	92.78 (15)	N4—Pt2—Cl7	89.02 (15)
N2—Pt1—Cl2	174.77 (15)	Cl6—Pt2—Cl7	91.93 (7)
Cl1—Pt1—Cl2	92.23 (8)	Cl5—Pt2—Cl7	90.84 (7)
N1—Pt1—Cl4	88.58 (15)	N3—Pt2—Cl8	89.53 (15)
N2—Pt1—Cl4	88.78 (17)	N4—Pt2—Cl8	87.37 (15)
Cl1—Pt1—Cl4	91.60 (9)	Cl6—Pt2—Cl8	91.46 (8)
Cl2—Pt1—Cl4	90.38 (10)	Cl5—Pt2—Cl8	91.84 (7)
N1—Pt1—Cl3	90.10 (15)	Cl7—Pt2—Cl8	175.68 (7)
N2—Pt1—Cl3	89.02 (17)	C13—N3—C24	120.0 (6)
Cl1—Pt1—Cl3	89.54 (8)	C13—N3—Pt2	127.6 (5)
Cl2—Pt1—Cl3	91.72 (9)	C24—N3—Pt2	112.3 (4)
Cl4—Pt1—Cl3	177.57 (8)	C22—N4—C23	120.1 (6)
C1—N1—C12	120.0 (5)	C22—N4—Pt2	127.4 (5)
C1—N1—Pt1	128.9 (4)	C23—N4—Pt2	112.4 (4)
C12—N1—Pt1	111.2 (4)	N3—C13—C14	119.6 (8)
C10—N2—C11	118.9 (6)	N3—C13—H13	120.2
C10—N2—Pt1	129.9 (5)	C14—C13—H13	120.2
C11—N2—Pt1	111.1 (4)	C15—C14—C13	119.7 (9)
N1—C1—C2	121.3 (6)	C15—C14—H14	120.2
N1—C1—H1	119.4	C13—C14—H14	120.2
C2—C1—H1	119.4	C14—C15—C16	121.8 (8)
C3—C2—C1	121.1 (7)	C14—C15—H15	119.1
C3—C2—H2	119.5	C16—C15—H15	119.1
C1—C2—H2	119.5	C15—C16—C24	116.8 (7)
C2—C3—C4	118.7 (6)	C15—C16—C17	126.4 (8)
C2—C3—H3	120.6	C24—C16—C17	116.8 (7)
C4—C3—H3	120.6	C18—C17—C16	122.4 (8)
C12—C4—C3	117.9 (6)	C18—C17—H17	118.8
C12—C4—C5	117.0 (6)	C16—C17—H17	118.8
C3—C4—C5	125.1 (7)	C17—C18—C19	121.8 (8)
C6—C5—C4	122.1 (7)	C17—C18—H18	119.1
C6—C5—H5	119.0	C19—C18—H18	119.1
C4—C5—H5	119.0	C20—C19—C23	117.4 (8)
C5—C6—C7	120.8 (7)	C20—C19—C18	125.9 (8)
C5—C6—H6	119.6	C23—C19—C18	116.7 (8)
C7—C6—H6	119.6	C21—C20—C19	120.1 (8)
C11—C7—C8	116.4 (7)	C21—C20—H20	120.0
C11—C7—C6	119.1 (7)	C19—C20—H20	120.0
C8—C7—C6	124.5 (7)	C20—C21—C22	121.1 (8)
C9—C8—C7	119.7 (7)	C20—C21—H21	119.5
C9—C8—H8	120.2	C22—C21—H21	119.5
C7—C8—H8	120.2	N4—C22—C21	119.9 (8)
C8—C9—C10	119.9 (7)	N4—C22—H22	120.1
C8—C9—H9	120.0	C21—C22—H22	120.1
C10—C9—H9	120.0	N4—C23—C24	117.1 (6)
N2—C10—C9	122.4 (8)	N4—C23—C19	121.4 (7)
N2—C10—H10	118.8	C24—C23—C19	121.4 (7)
C9—C10—H10	118.8	N3—C24—C23	117.1 (6)
N2—C11—C7	122.6 (6)	N3—C24—C16	122.1 (7)
N2—C11—C12	117.9 (6)	C23—C24—C16	120.8 (6)
C7—C11—C12	119.5 (6)	C26—C25—H26A	109.5
N1—C12—C11	117.4 (5)	C26—C25—H26B	109.5
N1—C12—C4	121.1 (6)	H26A—C25—H26B	109.5
C11—C12—C4	121.4 (6)	C26—C25—H26C	109.5
N3—Pt2—N4	80.9 (2)	H26A—C25—H26C	109.5
N3—Pt2—Cl6	93.96 (16)	H26B—C25—H26C	109.5
N4—Pt2—Cl6	174.73 (16)	N5—C26—C25	178.9 (18)
N3—Pt2—Cl5	175.68 (16)

N2—Pt1—N1—C1	175.1 (6)	N4—Pt2—N3—C13	177.0 (6)
Cl2—Pt1—N1—C1	−4.2 (5)	Cl6—Pt2—N3—C13	−1.8 (6)
Cl4—Pt1—N1—C1	86.1 (5)	Cl7—Pt2—N3—C13	−93.6 (6)
Cl3—Pt1—N1—C1	−95.9 (5)	Cl8—Pt2—N3—C13	89.6 (6)
N2—Pt1—N1—C12	−5.8 (4)	N4—Pt2—N3—C24	−3.5 (4)
Cl2—Pt1—N1—C12	174.9 (4)	Cl6—Pt2—N3—C24	177.7 (4)
Cl4—Pt1—N1—C12	−94.8 (4)	Cl7—Pt2—N3—C24	85.9 (4)
Cl3—Pt1—N1—C12	83.1 (4)	Cl8—Pt2—N3—C24	−90.9 (4)
N1—Pt1—N2—C10	−172.5 (6)	N3—Pt2—N4—C22	−173.2 (6)
Cl1—Pt1—N2—C10	7.8 (6)	Cl5—Pt2—N4—C22	8.3 (5)
Cl4—Pt1—N2—C10	−83.8 (6)	Cl7—Pt2—N4—C22	99.1 (5)
Cl3—Pt1—N2—C10	97.3 (6)	Cl8—Pt2—N4—C22	−83.3 (5)
N1—Pt1—N2—C11	4.8 (4)	N3—Pt2—N4—C23	2.8 (4)
Cl1—Pt1—N2—C11	−174.9 (4)	Cl5—Pt2—N4—C23	−175.7 (4)
Cl4—Pt1—N2—C11	93.5 (4)	Cl7—Pt2—N4—C23	−84.9 (4)
Cl3—Pt1—N2—C11	−85.5 (4)	Cl8—Pt2—N4—C23	92.7 (4)
C12—N1—C1—C2	−0.8 (9)	C24—N3—C13—C14	−1.8 (12)
Pt1—N1—C1—C2	178.1 (5)	Pt2—N3—C13—C14	177.7 (6)
N1—C1—C2—C3	−0.2 (10)	N3—C13—C14—C15	0.5 (15)
C1—C2—C3—C4	0.7 (10)	C13—C14—C15—C16	1.1 (16)
C2—C3—C4—C12	−0.3 (9)	C14—C15—C16—C24	−1.3 (14)
C2—C3—C4—C5	177.1 (6)	C14—C15—C16—C17	176.5 (10)
C12—C4—C5—C6	2.7 (10)	C15—C16—C17—C18	−177.8 (10)
C3—C4—C5—C6	−174.7 (7)	C24—C16—C17—C18	0.0 (13)
C4—C5—C6—C7	−0.5 (11)	C16—C17—C18—C19	1.4 (15)
C5—C6—C7—C11	−2.2 (10)	C17—C18—C19—C20	176.7 (9)
C5—C6—C7—C8	176.9 (7)	C17—C18—C19—C23	−3.0 (13)
C11—C7—C8—C9	1.0 (11)	C23—C19—C20—C21	1.5 (12)
C6—C7—C8—C9	−178.1 (7)	C18—C19—C20—C21	−178.2 (9)
C7—C8—C9—C10	−1.2 (12)	C19—C20—C21—C22	−2.4 (14)
C11—N2—C10—C9	3.1 (11)	C23—N4—C22—C21	2.3 (10)
Pt1—N2—C10—C9	−179.8 (6)	Pt2—N4—C22—C21	178.0 (5)
C8—C9—C10—N2	−0.9 (12)	C20—C21—C22—N4	0.5 (12)
C10—N2—C11—C7	−3.3 (10)	C22—N4—C23—C24	174.7 (6)
Pt1—N2—C11—C7	179.1 (5)	Pt2—N4—C23—C24	−1.6 (7)
C10—N2—C11—C12	174.6 (6)	C22—N4—C23—C19	−3.1 (9)
Pt1—N2—C11—C12	−3.0 (7)	Pt2—N4—C23—C19	−179.4 (5)
C8—C7—C11—N2	1.2 (10)	C20—C19—C23—N4	1.2 (10)
C6—C7—C11—N2	−179.6 (6)	C18—C19—C23—N4	−179.1 (7)
C8—C7—C11—C12	−176.7 (6)	C20—C19—C23—C24	−176.5 (7)
C6—C7—C11—C12	2.5 (9)	C18—C19—C23—C24	3.2 (11)
C1—N1—C12—C11	−174.8 (6)	C13—N3—C24—C23	−176.7 (6)
Pt1—N1—C12—C11	6.1 (7)	Pt2—N3—C24—C23	3.8 (7)
C1—N1—C12—C4	1.3 (9)	C13—N3—C24—C16	1.5 (10)
Pt1—N1—C12—C4	−177.9 (4)	Pt2—N3—C24—C16	−178.0 (5)
N2—C11—C12—N1	−2.1 (8)	N4—C23—C24—N3	−1.5 (9)
C7—C11—C12—N1	175.9 (6)	C19—C23—C24—N3	176.3 (6)
N2—C11—C12—C4	−178.2 (6)	N4—C23—C24—C16	−179.7 (6)
C7—C11—C12—C4	−0.2 (9)	C19—C23—C24—C16	−1.9 (10)
C3—C4—C12—N1	−0.7 (9)	C15—C16—C24—N3	0.0 (11)
C5—C4—C12—N1	−178.3 (5)	C17—C16—C24—N3	−178.0 (7)
C3—C4—C12—C11	175.2 (6)	C15—C16—C24—C23	178.2 (7)
C5—C4—C12—C11	−2.4 (9)	C17—C16—C24—C23	0.2 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl2	0.93	2.68	3.243 (7)	120
C1—H1···Cl6	0.93	2.75	3.632 (7)	158
C6—H6···Cl8ⁱ	0.93	2.74	3.637 (8)	163
C10—H10···Cl1	0.93	2.72	3.275 (9)	120
C13—H13···Cl6	0.93	2.68	3.248 (9)	120
C15—H15···Cl1ⁱⁱ	0.93	2.79	3.669 (9)	159
C21—H21···Cl2ⁱⁱⁱ	0.93	2.72	3.451 (9)	136
C22—H22···Cl5	0.93	2.74	3.297 (9)	120

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

Experimental details

Crystal data
Chemical formula	[PtCl₄(C₁₂H₈N₂)]·0.5C₂H₃N
M_r	1075.24
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.671 (5), 12.619 (8), 16.63 (1)
α, β, γ (°)	89.70 (1), 87.46 (1), 78.797 (7)
V (Å³)	1577 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	9.56
Crystal size (mm)	0.55 × 0.30 × 0.30

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.035, 0.057
No. of measured, independent and observed [I > 2σ(I)] reflections	8700, 5856, 5250
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.104, 1.09
No. of reflections	5856
No. of parameters	372
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.97, −2.05

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl2	0.93	2.68	3.243 (7)	120.0
C1—H1···Cl6	0.93	2.75	3.632 (7)	157.7
C6—H6···Cl8ⁱ	0.93	2.74	3.637 (8)	163.2
C10—H10···Cl1	0.93	2.72	3.275 (9)	119.5
C13—H13···Cl6	0.93	2.68	3.248 (9)	120.0
C15—H15···Cl1ⁱⁱ	0.93	2.79	3.669 (9)	158.6
C21—H21···Cl2ⁱⁱⁱ	0.93	2.72	3.451 (9)	135.9
C22—H22···Cl5	0.93	2.74	3.297 (9)	119.7

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

Acknowledgements

This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MOEHRD) (grant No. KRF-2007-412-J02001).

References

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