Tetra-n-butyl­ammonium bis­(1,1-dicyano­ethyl­ene-2,2-dithiol­ato)platinum(II)

Kanganga, N.; Mann, K.R.; Janzen, D.E.

doi:10.1107/S1600536808036726

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1552

doi:10.1107/S1600536808036726

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Tetra-n-butylammonium bis(1,1-dicyanoethylene-2,2-dithiolato)platinum(II)

Nyasha Kanganga,^a Kent R. Mann ^b and Daron E. Janzen ^a ^*

^aCollege of St Catherine, St Paul, Minnesota 55105, USA, and ^bDepartment of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA
^*Correspondence e-mail: dejanzen@stkate.edu

(Received 7 October 2008; accepted 7 November 2008; online 13 November 2008)

In the title compound, (C₁₆H₃₆N)₂[Pt(C₄N₂S₂)₂], the Pt^II center adopts a distorted square-planar geometry due to the 4-membered chelate rings formed by coordination to the S atoms of the 1,1-dicyanoethylene-2,2-dithiolate (i-mnt) ligands [bite angle 74.35 (4)°]. The bond distances in the coordinated i-mnt ligands indicate some delocalization of the π-system.

Related literature

For general background on the salts of metal complexes of [Pt(i-mnt)₂]²⁻ (i-mnt=1,1-dicyanoethylene-2,2-dithiolate), see: Cummings & Eisenberg (1996 ); Fackler & Coucouvanis (1966 ); Werden et al. (1966 ). For related structures, see: Gao et al. (2005 , 2006 ); Hummel (1987 ); Li et al. (2004 ); Sun et al. (2006 ).

Experimental

Crystal data

(C₁₆H₃₆N)₂[Pt(C₄N₂S₂)₂]
M_r = 960.40
Monoclinic, P 2₁ /n
a = 9.8687 (6) Å
b = 16.9556 (11) Å
c = 13.8274 (9) Å
β = 92.840 (1)°
V = 2310.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 3.25 mm⁻¹
T = 173 (2) K
0.40 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2003 ) T_min = 0.468, T_max = 0.612
22256 measured reflections
4087 independent reflections
3226 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.077
S = 1.09
4087 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 1.02 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: SMART (Bruker,2003); cell refinement: SAINT (Bruker, 2006 ); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808036726/pk2127sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808036726/pk2127Isup2.hkl

checkCIF report

Comment top

Salts of metal complexes of [Pt(i-mnt)₂]^2- (i-mnt=1,1-dicyanoethylene-2,2-dithiolate) have been studied for their interesting electronic properties including their photoluminescence (Cummings & Eisenberg, 1996) and their redox behavior especially in relation to the analagous isomeric ligand 1,2-dicyanoethylene-1,2-dithiolate (mnt^2-) complexes (Fackler & Coucouvanis, 1966; Werden et al., 1966). In sharp contrast to mnt complexes of the form [M(mnt)₂]^2- (M= Ni^II, Pd^II, Pt^II) which do exhibit reversible oxidation behavior, analagous i-mnt complexes of the form [M(i-mnt)₂]^2- do not. This effect is attributed to better π-delocalization of the five-membered rings formed by complexation of mnt compared with four-membered chelate rings of i-mnt complexes. Salts of [Pt(i-mnt)₂]^2- have also been studied as supramolecular linker groups in organic-inorganic hybrid coordination polymers (Gao et al. 2005, 2006; Li et al. 2004; Sun et al. 2006). While several x-ray structures of [Pt(i-mnt)₂]^2- with alkali metal-complexed crown ether salts have been reported, only one other simple non-coordinating cation salt (tetraethylammonium, Hummel 1987) has been structurally characterized.

The structure of the anion in the title compound (C₁₆H₃₆N)₂[Pt(S₂C₄N₂)₂] shows significant distortions from a square planar environment as forced by the four-membered chelate rings of the i-mnt ligands, with the i-mnt bite angle S(2)—Pt(1)—S(1) = 74.35 (4)°. As the Pt sits on the special position (1/2, 1/2, 1/2) in the space group P2₁/n, Z' = 0.5, the anion is quite planar, with a calculated r.m.s. deviation from a least-squares plane formed by all atoms of the complex anion of 0.042 (3) Å. The bond lengths within coordinated i-mnt ligand, in particular the bonds C(1)—C(2) 1.361 (6) Å, C(2)—C(3) 1.429 (6) Å, and C(2)—C(4) 1.430 (6)Å are very similar to those observed in the tetraethylammonium salt, showing significant π-delocalization. No columnar stacking is observed amongst the complex anions. As expected, upon comparison of the structure of the title compound and the tetraethylammonium salt, little effect was observed on the intramolecular features of the complex anion.

Related literature top

For general background on salts of metal complexes of [Pt(i-mnt)₂]^2- (i-mnt=1,1-dicyanoethylene-2,2-dithiolate), see: Cummings & Eisenberg (1996); Fackler & Coucouvanis (1966); Werden et al. (1966). For related structures, see: Gao et al. (2005, 2006); Hummel (1987); Li et al. (2004); Sun et al. (2006).

Experimental top

The title compound (C₁₆H₃₆N)₂[Pt(S₂C₄N₂)₂] was prepared using a procedure similar to that described by Fackler and Coucouvanis (1966) subsituting the use of tetra-n-propylammonium iodide with tetra-n-butylammonium bromide. The title compound has been previously characterized by Werden et al.(1966). Spectroscopic analysis of the present sample obtained by this procedure was consistent with the data previously reported. Crystals were obtained by diffusion of diethyl ether into a concentrated solution of the title compound dissolved in dichloromethane.

Computing details top

Data collection: SMART (Bruker,2003); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (C₁₆H₃₆N)₂[Pt(S₂C₄N₂)₂] showing 50% displacement ellipsoids for the non-hydrogen atoms. Only the crystallographically independent atoms are labelled.

Tetra-n-butylammonium bis(1,1-dicyanoethylene-2,2-dithiolato)platinum(II) top

Crystal data top

(C₁₆H₃₆N)₂[Pt(C₄N₂S₂)₂]	F(000) = 992
M_r = 960.40	D_x = 1.380 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 3207 reflections
a = 9.8687 (6) Å	θ = 5.5–50.0°
b = 16.9556 (11) Å	µ = 3.25 mm⁻¹
c = 13.8274 (9) Å	T = 173 K
β = 92.840 (1)°	Plate, yellow
V = 2310.9 (3) Å³	0.4 × 0.2 × 0.15 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	4087 independent reflections
Radiation source: normal-focus sealed tube	3226 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ scans	θ_max = 25.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker 2003)	h = −11→11
T_min = 0.468, T_max = 0.612	k = −20→20
22256 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0339P)² + 3.6638P] where P = (F_o² + 2F_c²)/3
4087 reflections	(Δ/σ)_max = 0.001
236 parameters	Δρ_max = 1.02 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³
0 constraints

Crystal data top

(C₁₆H₃₆N)₂[Pt(C₄N₂S₂)₂]	V = 2310.9 (3) Å³
M_r = 960.40	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.8687 (6) Å	µ = 3.25 mm⁻¹
b = 16.9556 (11) Å	T = 173 K
c = 13.8274 (9) Å	0.4 × 0.2 × 0.15 mm
β = 92.840 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4087 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2003)	3226 reflections with I > 2σ(I)
T_min = 0.468, T_max = 0.612	R_int = 0.033
22256 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.09	Δρ_max = 1.02 e Å⁻³
4087 reflections	Δρ_min = −0.33 e Å⁻³
236 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	0.5000	0.5000	0.5000	0.03643 (9)
S1	0.56122 (11)	0.43791 (7)	0.64610 (8)	0.0434 (3)
S2	0.30447 (11)	0.49674 (7)	0.58620 (8)	0.0439 (2)
C1	0.3957 (4)	0.4489 (2)	0.6793 (3)	0.0365 (9)
C2	0.3440 (4)	0.4241 (2)	0.7636 (3)	0.0395 (9)
C3	0.2028 (5)	0.4321 (2)	0.7797 (3)	0.0432 (10)
C4	0.4294 (5)	0.3889 (2)	0.8383 (3)	0.0419 (10)
N1	0.0899 (4)	0.4381 (3)	0.7927 (3)	0.0585 (11)
N2	0.4951 (5)	0.3608 (2)	0.8982 (3)	0.0558 (10)
N3	0.6156 (3)	0.15041 (17)	0.7976 (2)	0.0311 (7)
C5	0.6718 (4)	0.0849 (2)	0.7366 (3)	0.0325 (8)
H5A	0.5998	0.0449	0.7250	0.039*
H5B	0.7471	0.0592	0.7747	0.039*
C6	0.7239 (5)	0.1092 (3)	0.6392 (3)	0.0513 (12)
H6A	0.6473	0.1284	0.5965	0.062*
H6B	0.7899	0.1528	0.6485	0.062*
C7	0.7915 (5)	0.0399 (3)	0.5914 (3)	0.0530 (12)
H7A	0.8370	0.0594	0.5338	0.064*
H7B	0.8626	0.0185	0.6372	0.064*
C8	0.6986 (7)	−0.0250 (4)	0.5610 (5)	0.088 (2)
H8A	0.7497	−0.0664	0.5293	0.131*
H8B	0.6276	−0.0047	0.5156	0.131*
H8C	0.6568	−0.0470	0.6180	0.131*
C9	0.7213 (4)	0.2133 (2)	0.8215 (3)	0.0364 (9)
H9A	0.6795	0.2539	0.8620	0.044*
H9B	0.7446	0.2391	0.7603	0.044*
C10	0.8523 (4)	0.1859 (2)	0.8736 (3)	0.0407 (10)
H10A	0.8317	0.1624	0.9368	0.049*
H10B	0.8954	0.1448	0.8346	0.049*
C11	0.9494 (5)	0.2548 (3)	0.8897 (3)	0.0454 (10)
H11A	0.9651	0.2796	0.8264	0.054*
H11B	0.9063	0.2947	0.9305	0.054*
C12	1.0841 (5)	0.2320 (3)	0.9372 (4)	0.0548 (12)
H12A	1.1439	0.2781	0.9408	0.082*
H12B	1.1256	0.1905	0.8991	0.082*
H12C	1.0706	0.2124	1.0027	0.082*
C13	0.5705 (4)	0.1106 (2)	0.8892 (3)	0.0321 (8)
H13A	0.5059	0.0680	0.8703	0.039*
H13B	0.6507	0.0855	0.9223	0.039*
C14	0.5040 (5)	0.1638 (2)	0.9614 (3)	0.0416 (10)
H14A	0.5685	0.2056	0.9834	0.050*
H14B	0.4234	0.1896	0.9297	0.050*
C15	0.4618 (4)	0.1166 (2)	1.0474 (3)	0.0389 (9)
H15A	0.5434	0.0922	1.0794	0.047*
H15B	0.4007	0.0736	1.0242	0.047*
C16	0.3900 (5)	0.1654 (3)	1.1214 (3)	0.0499 (11)
H16A	0.3599	0.1309	1.1729	0.075*
H16B	0.3112	0.1916	1.0897	0.075*
H16C	0.4526	0.2052	1.1492	0.075*
C17	0.4978 (4)	0.1918 (2)	0.7443 (3)	0.0354 (9)
H17A	0.4689	0.2363	0.7848	0.042*
H17B	0.5309	0.2145	0.6839	0.042*
C18	0.3751 (4)	0.1418 (2)	0.7184 (3)	0.0395 (9)
H18A	0.3417	0.1178	0.7780	0.047*
H18B	0.4014	0.0985	0.6750	0.047*
C19	0.2614 (5)	0.1896 (3)	0.6683 (3)	0.0517 (12)
H19A	0.2422	0.2362	0.7084	0.062*
H19B	0.2914	0.2086	0.6052	0.062*
C20	0.1329 (5)	0.1419 (3)	0.6520 (4)	0.0549 (12)
H20A	0.0649	0.1735	0.6153	0.082*
H20B	0.0979	0.1273	0.7146	0.082*
H20C	0.1526	0.0941	0.6154	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.03067 (12)	0.04558 (14)	0.03345 (13)	−0.00168 (10)	0.00587 (8)	−0.00881 (11)
S1	0.0354 (5)	0.0561 (6)	0.0392 (6)	0.0020 (5)	0.0066 (4)	−0.0062 (5)
S2	0.0336 (5)	0.0607 (7)	0.0379 (5)	0.0017 (5)	0.0067 (4)	−0.0022 (5)
C1	0.037 (2)	0.033 (2)	0.040 (2)	0.0008 (17)	0.0046 (17)	−0.0123 (17)
C2	0.040 (2)	0.034 (2)	0.045 (2)	0.0013 (18)	0.0059 (19)	−0.0068 (18)
C3	0.049 (3)	0.039 (2)	0.043 (2)	−0.001 (2)	0.009 (2)	−0.0047 (19)
C4	0.053 (3)	0.032 (2)	0.043 (3)	−0.0012 (19)	0.014 (2)	−0.0088 (19)
N1	0.045 (2)	0.063 (3)	0.069 (3)	0.001 (2)	0.022 (2)	0.004 (2)
N2	0.071 (3)	0.047 (2)	0.050 (2)	0.006 (2)	0.008 (2)	0.0006 (19)
N3	0.0361 (17)	0.0295 (16)	0.0282 (17)	0.0022 (13)	0.0071 (13)	0.0044 (13)
C5	0.038 (2)	0.0298 (19)	0.031 (2)	0.0043 (16)	0.0081 (16)	−0.0007 (15)
C6	0.067 (3)	0.047 (3)	0.041 (3)	0.003 (2)	0.024 (2)	0.007 (2)
C7	0.060 (3)	0.056 (3)	0.045 (3)	0.002 (2)	0.026 (2)	0.000 (2)
C8	0.080 (4)	0.102 (5)	0.083 (4)	−0.016 (4)	0.034 (4)	−0.046 (4)
C9	0.043 (2)	0.030 (2)	0.037 (2)	−0.0031 (17)	0.0095 (18)	0.0057 (17)
C10	0.041 (2)	0.038 (2)	0.043 (2)	−0.0033 (18)	0.0023 (19)	0.0032 (18)
C11	0.053 (3)	0.041 (2)	0.043 (2)	−0.007 (2)	0.000 (2)	0.0058 (19)
C12	0.054 (3)	0.057 (3)	0.052 (3)	−0.011 (2)	−0.008 (2)	−0.004 (2)
C13	0.039 (2)	0.030 (2)	0.028 (2)	0.0020 (16)	0.0077 (16)	0.0059 (15)
C14	0.053 (3)	0.033 (2)	0.039 (2)	0.0041 (18)	0.0141 (19)	0.0023 (18)
C15	0.047 (2)	0.042 (2)	0.028 (2)	0.0022 (19)	0.0080 (18)	−0.0009 (17)
C16	0.055 (3)	0.055 (3)	0.040 (3)	0.003 (2)	0.016 (2)	0.000 (2)
C17	0.041 (2)	0.034 (2)	0.032 (2)	0.0081 (17)	0.0054 (17)	0.0061 (16)
C18	0.042 (2)	0.039 (2)	0.037 (2)	0.0074 (18)	0.0019 (18)	0.0018 (18)
C19	0.049 (3)	0.055 (3)	0.051 (3)	0.012 (2)	−0.001 (2)	0.008 (2)
C20	0.044 (3)	0.068 (3)	0.052 (3)	0.012 (2)	−0.003 (2)	0.001 (2)

Geometric parameters (Å, º) top

Pt1—S2	2.3184 (10)	C10—H10B	0.9900
Pt1—S2ⁱ	2.3185 (10)	C11—C12	1.504 (6)
Pt1—S1	2.3310 (11)	C11—H11A	0.9900
Pt1—S1ⁱ	2.3310 (11)	C11—H11B	0.9900
S1—C1	1.729 (4)	C12—H12A	0.9800
S2—C1	1.735 (4)	C12—H12B	0.9800
C1—C2	1.361 (6)	C12—H12C	0.9800
C2—C3	1.429 (6)	C13—C14	1.519 (5)
C2—C4	1.430 (6)	C13—H13A	0.9900
C3—N1	1.142 (5)	C13—H13B	0.9900
C4—N2	1.132 (6)	C14—C15	1.509 (6)
N3—C9	1.516 (5)	C14—H14A	0.9900
N3—C5	1.516 (4)	C14—H14B	0.9900
N3—C17	1.518 (5)	C15—C16	1.517 (6)
N3—C13	1.522 (4)	C15—H15A	0.9900
C5—C6	1.522 (5)	C15—H15B	0.9900
C5—H5A	0.9900	C16—H16A	0.9800
C5—H5B	0.9900	C16—H16B	0.9800
C6—C7	1.518 (6)	C16—H16C	0.9800
C6—H6A	0.9900	C17—C18	1.508 (6)
C6—H6B	0.9900	C17—H17A	0.9900
C7—C8	1.480 (8)	C17—H17B	0.9900
C7—H7A	0.9900	C18—C19	1.522 (6)
C7—H7B	0.9900	C18—H18A	0.9900
C8—H8A	0.9800	C18—H18B	0.9900
C8—H8B	0.9800	C19—C20	1.511 (7)
C8—H8C	0.9800	C19—H19A	0.9900
C9—C10	1.521 (6)	C19—H19B	0.9900
C9—H9A	0.9900	C20—H20A	0.9800
C9—H9B	0.9900	C20—H20B	0.9800
C10—C11	1.521 (6)	C20—H20C	0.9800
C10—H10A	0.9900

S2—Pt1—S2ⁱ	180.0	C12—C11—H11A	108.8
S2—Pt1—S1	74.35 (4)	C10—C11—H11A	108.8
S2ⁱ—Pt1—S1	105.65 (4)	C12—C11—H11B	108.8
S2—Pt1—S1ⁱ	105.65 (4)	C10—C11—H11B	108.8
S2ⁱ—Pt1—S1ⁱ	74.35 (4)	H11A—C11—H11B	107.7
S1—Pt1—S1ⁱ	180.0	C11—C12—H12A	109.5
C1—S1—Pt1	88.49 (15)	C11—C12—H12B	109.5
C1—S2—Pt1	88.74 (14)	H12A—C12—H12B	109.5
C2—C1—S1	126.4 (3)	C11—C12—H12C	109.5
C2—C1—S2	125.2 (3)	H12A—C12—H12C	109.5
S1—C1—S2	108.4 (2)	H12B—C12—H12C	109.5
C1—C2—C3	120.9 (4)	C14—C13—N3	115.9 (3)
C1—C2—C4	121.0 (4)	C14—C13—H13A	108.3
C3—C2—C4	118.1 (4)	N3—C13—H13A	108.3
N1—C3—C2	179.6 (5)	C14—C13—H13B	108.3
N2—C4—C2	178.8 (5)	N3—C13—H13B	108.3
C9—N3—C5	111.7 (3)	H13A—C13—H13B	107.4
C9—N3—C17	106.4 (3)	C15—C14—C13	110.3 (3)
C5—N3—C17	111.2 (3)	C15—C14—H14A	109.6
C9—N3—C13	110.9 (3)	C13—C14—H14A	109.6
C5—N3—C13	105.6 (3)	C15—C14—H14B	109.6
C17—N3—C13	111.2 (3)	C13—C14—H14B	109.6
N3—C5—C6	116.3 (3)	H14A—C14—H14B	108.1
N3—C5—H5A	108.2	C14—C15—C16	113.5 (4)
C6—C5—H5A	108.2	C14—C15—H15A	108.9
N3—C5—H5B	108.2	C16—C15—H15A	108.9
C6—C5—H5B	108.2	C14—C15—H15B	108.9
H5A—C5—H5B	107.4	C16—C15—H15B	108.9
C7—C6—C5	110.5 (4)	H15A—C15—H15B	107.7
C7—C6—H6A	109.5	C15—C16—H16A	109.5
C5—C6—H6A	109.5	C15—C16—H16B	109.5
C7—C6—H6B	109.5	H16A—C16—H16B	109.5
C5—C6—H6B	109.5	C15—C16—H16C	109.5
H6A—C6—H6B	108.1	H16A—C16—H16C	109.5
C8—C7—C6	114.8 (5)	H16B—C16—H16C	109.5
C8—C7—H7A	108.6	C18—C17—N3	116.2 (3)
C6—C7—H7A	108.6	C18—C17—H17A	108.2
C8—C7—H7B	108.6	N3—C17—H17A	108.2
C6—C7—H7B	108.6	C18—C17—H17B	108.2
H7A—C7—H7B	107.5	N3—C17—H17B	108.2
C7—C8—H8A	109.5	H17A—C17—H17B	107.4
C7—C8—H8B	109.5	C17—C18—C19	112.0 (3)
H8A—C8—H8B	109.5	C17—C18—H18A	109.2
C7—C8—H8C	109.5	C19—C18—H18A	109.2
H8A—C8—H8C	109.5	C17—C18—H18B	109.2
H8B—C8—H8C	109.5	C19—C18—H18B	109.2
N3—C9—C10	116.6 (3)	H18A—C18—H18B	107.9
N3—C9—H9A	108.1	C20—C19—C18	112.2 (4)
C10—C9—H9A	108.1	C20—C19—H19A	109.2
N3—C9—H9B	108.1	C18—C19—H19A	109.2
C10—C9—H9B	108.1	C20—C19—H19B	109.2
H9A—C9—H9B	107.3	C18—C19—H19B	109.2
C11—C10—C9	110.5 (3)	H19A—C19—H19B	107.9
C11—C10—H10A	109.6	C19—C20—H20A	109.5
C9—C10—H10A	109.6	C19—C20—H20B	109.5
C11—C10—H10B	109.6	H20A—C20—H20B	109.5
C9—C10—H10B	109.6	C19—C20—H20C	109.5
H10A—C10—H10B	108.1	H20A—C20—H20C	109.5
C12—C11—C10	113.8 (4)	H20B—C20—H20C	109.5

S2—Pt1—S1—C1	0.38 (13)	C5—C6—C7—C8	67.3 (6)
S2ⁱ—Pt1—S1—C1	−179.62 (13)	C5—N3—C9—C10	−57.1 (4)
S1—Pt1—S2—C1	−0.38 (13)	C17—N3—C9—C10	−178.6 (3)
S1ⁱ—Pt1—S2—C1	179.62 (13)	C13—N3—C9—C10	60.4 (4)
Pt1—S1—C1—C2	179.1 (4)	N3—C9—C10—C11	178.2 (3)
Pt1—S1—C1—S2	−0.52 (17)	C9—C10—C11—C12	−177.5 (4)
Pt1—S2—C1—C2	−179.1 (3)	C9—N3—C13—C14	61.4 (4)
Pt1—S2—C1—S1	0.52 (17)	C5—N3—C13—C14	−177.5 (3)
S1—C1—C2—C3	−175.8 (3)	C17—N3—C13—C14	−56.8 (4)
S2—C1—C2—C3	3.8 (6)	N3—C13—C14—C15	178.8 (3)
S1—C1—C2—C4	3.9 (6)	C13—C14—C15—C16	−178.0 (4)
S2—C1—C2—C4	−176.6 (3)	C9—N3—C17—C18	−176.2 (3)
C9—N3—C5—C6	−59.8 (4)	C5—N3—C17—C18	62.0 (4)
C17—N3—C5—C6	58.9 (4)	C13—N3—C17—C18	−55.3 (4)
C13—N3—C5—C6	179.6 (4)	N3—C17—C18—C19	178.0 (3)
N3—C5—C6—C7	173.5 (4)	C17—C18—C19—C20	−173.8 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	(C₁₆H₃₆N)₂[Pt(C₄N₂S₂)₂]
M_r	960.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.8687 (6), 16.9556 (11), 13.8274 (9)
β (°)	92.840 (1)
V (Å³)	2310.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.25
Crystal size (mm)	0.4 × 0.2 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 2003)
T_min, T_max	0.468, 0.612
No. of measured, independent and observed [I > 2σ(I)] reflections	22256, 4087, 3226
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.077, 1.09
No. of reflections	4087
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.02, −0.33

Computer programs: SMART (Bruker,2003), SAINT (Bruker, 2006), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by funding from the NSF through a Research Site for Educators in Chemistry grant. The authors acknowledge Victor G. Young, Jr and the X-ray Crystallographic Laboratory in the Department of Chemistry at the University of Minnesota.

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