Structural study of four complexes of the M-N₂S₂ type derived from diethylphenylazothioformamide and the metals palladium, platinum, copper and nickel

The four electron-transfer complexes trans-(di(N,N-diethyl-(2-phenyldiazenyl)thioformamide-κS,κN²))nickel, trans-(di(N,N-diethyl-(2-phenyldiazenyl)thioformamide-κS,κN²))copper, trans-(di(N,N-diethyl-(2-phenyldiazenyl)thioformamide-κS,κN²))palladium and trans-(di(N,N-diethyl-(2-phenyldiazenyl)thioformamide-κS,κN²))platinum have been crystallized, and their structures have been determined at low temperature. All the complexes are of the M-N₂S₂ type. The crystals of both the nickel and the copper complex belong to the tetragonal P4₁2₁2 system, in which the central metal ion lies on a twofold axis. The tetrahedral molecular symmetry around the central metal ion is unusual for the M-N₂S₂ electron-transfer complexes. The crystals of the palladium and platinum complexes on the other hand belong to the monoclinic C2/c system in which the metal ion lies on an inversion centre. The molecular symmetry around these metal ions is square planar. It is demonstrated that the π electron density in the ligand planes has a high degree of delocalization. Furthermore, unusually large line broadening of the ¹H NMR spectra was observed and investigated as a function of temperature for the palladium complex.

Computing details

Data collection: Bruker SMART (Bruker AXS,1998) for NiL20; Bruker SMART for CuL20, PdL20, PtL20. Cell refinement: Bruker SMART (Bruker AXS,1998) for NiL20; Bruker SMART for CuL20, PdL20, PtL20. Data reduction: Bruker SHELXTL (Sheldrick,2001) for NiL20; Bruker SHELXTL for CuL20, PdL20, PtL20. Program(s) used to solve structure: Bruker SHELXTL (Sheldrick,2001) for NiL20; Bruker SHELXTL for CuL20, PdL20, PtL20. Program(s) used to refine structure: Bruker SHELXTL (Sheldrick,2001) for NiL20; Bruker SHELXTL for CuL20, PdL20, PtL20. Molecular graphics: Bruker SHELXTL (Sheldrick,2001) for NiL20; Bruker SHELXTL for CuL20, PdL20, PtL20. For all compounds, software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures

(NiL20) Trans-(di(N,N-diethyl-(2-phenyldiazenyl)thioformamide-κS,κN²))nickel

Crystal data

C22H30N6NiS2	Dx = 1.413 Mg m^−3
Mr = 501.35	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212	Cell parameters from 12044 reflections
a = 10.2852 (3) Å	θ = 2.7–31.0°
c = 22.2862 (13) Å	µ = 1.02 mm^−1
V = 2357.55 (17) Å^3	T = 118 K
Z = 4	Quadratic bi-pyramidal shaped, brown
F(000) = 1056	0.50 × 0.30 × 0.05 mm

Data collection

CCD area detector diffractometer	3630 independent reflections
Radiation source: fine-focus sealed tube	3436 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 8.192 pixels mm^-1	θmax = 31.0°, θmin = 2.2°
ω scans	h = −13→14
Absorption correction: empirical (using intensity measurements) SADABS,ver2.03 (Sheldrick,2001)	k = −14→14
Tmin = 0.74, Tmax = 0.96	l = −31→30
31608 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0407P)^2 + 0.3442P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 0.001
3630 reflections	Δρmax = 0.61 e Å^−3
201 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.021 (12)

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 (Ų)

	x	y	z	Uiso*/Ueq
Ni	0.14902 (2)	0.14902 (2)	0.0000	0.01454 (8)
S	−0.01504 (4)	0.16012 (4)	0.06373 (2)	0.01851 (10)
N1	0.07768 (13)	0.29876 (13)	−0.03467 (6)	0.0129 (3)
N2	−0.03902 (13)	0.34689 (14)	−0.02047 (6)	0.0142 (3)
N3	−0.20611 (14)	0.33344 (15)	0.04815 (6)	0.0169 (3)
C1	−0.09112 (16)	0.28819 (16)	0.02852 (7)	0.0138 (3)
C2	−0.27465 (17)	0.44026 (18)	0.01804 (8)	0.0191 (4)
H2A	−0.2119	0.4955	−0.0021	0.023*
H2B	−0.3196	0.4925	0.0478	0.023*
C3	−0.3721 (2)	0.3900 (2)	−0.02740 (9)	0.0263 (4)
H3A	−0.4151	0.4621	−0.0462	0.039*
H3B	−0.4352	0.3365	−0.0075	0.039*
H3C	−0.3277	0.3395	−0.0573	0.039*
C4	−0.27118 (18)	0.2763 (2)	0.10021 (8)	0.0210 (4)
H4A	−0.2535	0.1837	0.1013	0.025*
H4B	−0.3644	0.2879	0.0961	0.025*
C5	−0.2266 (2)	0.3375 (3)	0.15886 (9)	0.0325 (5)
H5A	−0.2714	0.2973	0.1918	0.049*
H5B	−0.2456	0.4289	0.1583	0.049*
H5C	−0.1347	0.3249	0.1635	0.049*
C6	0.13032 (15)	0.35289 (16)	−0.08777 (7)	0.0136 (3)
C7	0.05541 (18)	0.41279 (17)	−0.13203 (8)	0.0180 (3)
H7	−0.0337	0.4227	−0.1267	0.022*
C8	0.11433 (19)	0.45755 (18)	−0.18413 (9)	0.0219 (4)
H8	0.0641	0.4958	−0.2140	0.026*
C9	0.24787 (19)	0.44559 (18)	−0.19198 (9)	0.0219 (4)
H9	0.2868	0.4761	−0.2269	0.026*
C10	0.32319 (17)	0.38794 (17)	−0.14757 (8)	0.0193 (4)
H10	0.4127	0.3810	−0.1526	0.023*
C11	0.26524 (16)	0.34072 (17)	−0.09572 (8)	0.0161 (3)
H11	0.3157	0.3011	−0.0663	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.01353 (10)	0.01353 (10)	0.01657 (15)	0.00528 (11)	−0.00051 (8)	0.00051 (8)
S	0.01692 (19)	0.0200 (2)	0.0186 (2)	0.00595 (16)	0.00190 (15)	0.00582 (17)
N1	0.0119 (6)	0.0121 (6)	0.0146 (7)	0.0022 (5)	−0.0013 (5)	−0.0006 (5)
N2	0.0108 (6)	0.0150 (6)	0.0169 (6)	0.0035 (5)	0.0008 (5)	0.0000 (6)
N3	0.0133 (6)	0.0196 (7)	0.0177 (7)	0.0042 (5)	0.0025 (5)	0.0028 (6)
C1	0.0126 (7)	0.0148 (7)	0.0142 (8)	0.0018 (6)	−0.0016 (6)	−0.0007 (6)
C2	0.0150 (8)	0.0188 (8)	0.0235 (9)	0.0067 (6)	0.0032 (7)	0.0015 (7)
C3	0.0301 (11)	0.0274 (9)	0.0214 (9)	0.0130 (8)	−0.0049 (8)	−0.0004 (8)
C4	0.0147 (9)	0.0277 (10)	0.0206 (8)	0.0023 (6)	0.0049 (7)	0.0038 (8)
C5	0.0294 (10)	0.0487 (14)	0.0194 (9)	0.0000 (10)	0.0022 (8)	0.0008 (10)
C6	0.0146 (7)	0.0113 (6)	0.0151 (7)	0.0004 (6)	0.0003 (6)	−0.0016 (6)
C7	0.0161 (8)	0.0172 (8)	0.0208 (9)	0.0030 (6)	0.0000 (7)	−0.0002 (7)
C8	0.0275 (9)	0.0197 (8)	0.0184 (8)	0.0030 (7)	−0.0005 (7)	0.0034 (7)
C9	0.0295 (10)	0.0158 (9)	0.0205 (9)	−0.0016 (7)	0.0079 (8)	−0.0008 (7)
C10	0.0162 (8)	0.0154 (8)	0.0262 (9)	−0.0016 (6)	0.0054 (7)	−0.0048 (7)
C11	0.0153 (7)	0.0144 (8)	0.0187 (8)	0.0011 (6)	0.0003 (6)	−0.0018 (7)

Geometric parameters (Å, º)

Ni—N1^i	1.8728 (14)	C4—C5	1.521 (3)
Ni—N1	1.8728 (14)	C4—H4A	0.9700
Ni—S^i	2.2085 (4)	C4—H4B	0.9700
Ni—S	2.2085 (4)	C5—H5A	0.9600
S—C1	1.7213 (17)	C5—H5B	0.9600
N1—N2	1.3363 (19)	C5—H5C	0.9600
N1—C6	1.415 (2)	C6—C7	1.395 (2)
N2—C1	1.358 (2)	C6—C11	1.405 (2)
N3—C1	1.344 (2)	C7—C8	1.388 (2)
N3—C4	1.463 (2)	C7—H7	0.9300
N3—C2	1.468 (2)	C8—C9	1.390 (3)
C2—C3	1.515 (3)	C8—H8	0.9300
C2—H2A	0.9700	C9—C10	1.390 (3)
C2—H2B	0.9700	C9—H9	0.9300
C3—H3A	0.9600	C10—C11	1.388 (2)
C3—H3B	0.9600	C10—H10	0.9300
C3—H3C	0.9600	C11—H11	0.9300
N1^i—Ni—N1	144.55 (9)	N3—C4—H4A	109.2
N1^i—Ni—S^i	85.61 (4)	C5—C4—H4A	109.2
N1—Ni—S^i	112.53 (4)	N3—C4—H4B	109.2
N1^i—Ni—S	112.53 (4)	C5—C4—H4B	109.2
N1—Ni—S	85.61 (4)	H4A—C4—H4B	107.9
S^i—Ni—S	119.50 (3)	C4—C5—H5A	109.5
C1—S—Ni	95.38 (6)	C4—C5—H5B	109.5
N2—N1—C6	113.32 (13)	H5A—C5—H5B	109.5
N2—N1—Ni	123.97 (11)	C4—C5—H5C	109.5
C6—N1—Ni	121.23 (11)	H5A—C5—H5C	109.5
N1—N2—C1	112.35 (13)	H5B—C5—H5C	109.5
C1—N3—C4	121.45 (15)	C7—C6—C11	119.72 (16)
C1—N3—C2	122.21 (14)	C7—C6—N1	123.62 (15)
C4—N3—C2	116.32 (14)	C11—C6—N1	116.64 (15)
N3—C1—N2	117.06 (14)	C8—C7—C6	119.79 (17)
N3—C1—S	121.11 (13)	C8—C7—H7	120.1
N2—C1—S	121.83 (12)	C6—C7—H7	120.1
N3—C2—C3	111.58 (16)	C9—C8—C7	120.49 (18)
N3—C2—H2A	109.3	C9—C8—H8	119.8
C3—C2—H2A	109.3	C7—C8—H8	119.8
N3—C2—H2B	109.3	C8—C9—C10	119.92 (17)
C3—C2—H2B	109.3	C8—C9—H9	120.0
H2A—C2—H2B	108.0	C10—C9—H9	120.0
C2—C3—H3A	109.5	C11—C10—C9	120.19 (17)
C2—C3—H3B	109.5	C11—C10—H10	119.9
H3A—C3—H3B	109.5	C9—C10—H10	119.9
C2—C3—H3C	109.5	C10—C11—C6	119.88 (16)
H3A—C3—H3C	109.5	C10—C11—H11	120.1
H3B—C3—H3C	109.5	C6—C11—H11	120.1
N3—C4—C5	112.19 (17)
N1^i—Ni—S—C1	153.90 (8)	Ni—S—C1—N2	−2.51 (14)
N1—Ni—S—C1	5.38 (7)	C1—N3—C2—C3	93.7 (2)
S^i—Ni—S—C1	−108.08 (6)	C4—N3—C2—C3	−85.0 (2)
N1^i—Ni—N1—N2	−133.45 (13)	C1—N3—C4—C5	87.1 (2)
S^i—Ni—N1—N2	110.45 (12)	C2—N3—C4—C5	−94.2 (2)
S—Ni—N1—N2	−9.75 (12)	N2—N1—C6—C7	−21.5 (2)
N1^i—Ni—N1—C6	61.33 (12)	Ni—N1—C6—C7	145.13 (14)
S^i—Ni—N1—C6	−54.77 (13)	N2—N1—C6—C11	160.30 (15)
S—Ni—N1—C6	−174.97 (12)	Ni—N1—C6—C11	−33.0 (2)
C6—N1—N2—C1	176.32 (13)	C11—C6—C7—C8	1.3 (3)
Ni—N1—N2—C1	10.06 (19)	N1—C6—C7—C8	−176.80 (16)
C4—N3—C1—N2	179.44 (16)	C6—C7—C8—C9	−1.4 (3)
C2—N3—C1—N2	0.8 (2)	C7—C8—C9—C10	0.3 (3)
C4—N3—C1—S	0.2 (2)	C8—C9—C10—C11	0.8 (3)
C2—N3—C1—S	−178.39 (14)	C9—C10—C11—C6	−0.9 (3)
N1—N2—C1—N3	177.19 (14)	C7—C6—C11—C10	−0.2 (3)
N1—N2—C1—S	−3.6 (2)	N1—C6—C11—C10	178.04 (15)
Ni—S—C1—N3	176.68 (13)

Symmetry code: (i) y, x, −z.

(CuL20) Trans-(di(N,N-diethyl-(2-phenyldiazenyl)thioformamide-κS,κN²))copper

Crystal data

C22H30CuN6S2	Dx = 1.428 Mg m^−3
Mr = 506.18	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212	Cell parameters from 10241 reflections
a = 10.2643 (4) Å	θ = 2.7–28.0°
c = 22.3519 (13) Å	µ = 1.13 mm^−1
V = 2354.90 (19) Å^3	T = 118 K
Z = 4	Quadratic bi-pyramidal shaped, black
F(000) = 1060	0.40 × 0.35 × 0.15 mm

Data collection

CCD area detector diffractometer	2832 independent reflections
Radiation source: fine-focus sealed tube	2788 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8.192 pixels mm^-1	θmax = 28.0°, θmin = 2.2°
ω scans	h = −13→12
Absorption correction: empirical (using intensity measurements) SADABS,ver2.03 (Sheldrick,2001)	k = −13→13
Tmin = 0.661, Tmax = 0.849	l = −28→28
16807 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H-atom parameters constrained
wR(F^2) = 0.070	w = 1/[σ^2(Fo^2) + (0.P)^2 + 0.1079P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
2832 reflections	Δρmax = 0.36 e Å^−3
141 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881, 1132 Fridel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.012 (9)

Special details

Experimental. SADABS

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu	0.151860 (16)	0.151860 (16)	0.0000	0.01397 (9)
S	−0.01348 (3)	0.16903 (4)	0.067367 (18)	0.01868 (10)
C1	−0.08987 (14)	0.29169 (14)	0.02823 (7)	0.0139 (3)
C2	−0.27499 (14)	0.44307 (15)	0.01431 (7)	0.0193 (3)
H2A	−0.2115	0.4959	−0.0086	0.023*
H2B	−0.3180	0.5009	0.0437	0.023*
C3	−0.37665 (16)	0.38819 (17)	−0.02821 (8)	0.0244 (3)
H3A	−0.4209	0.4599	−0.0488	0.037*
H3B	−0.4405	0.3373	−0.0055	0.037*
H3C	−0.3341	0.3320	−0.0578	0.037*
C4	−0.27172 (15)	0.28546 (16)	0.09915 (7)	0.0199 (3)
H4A	−0.2523	0.1912	0.1024	0.024*
H4B	−0.3670	0.2953	0.0941	0.024*
C5	−0.23001 (17)	0.35315 (19)	0.15659 (8)	0.0293 (4)
H5A	−0.2765	0.3147	0.1906	0.044*
H5B	−0.2507	0.4462	0.1540	0.044*
H5C	−0.1360	0.3421	0.1622	0.044*
C6	0.12967 (13)	0.35602 (13)	−0.08980 (7)	0.0140 (3)
C7	0.05412 (15)	0.41548 (14)	−0.13431 (7)	0.0179 (3)
H7	−0.0371	0.4257	−0.1290	0.022*
C8	0.11421 (15)	0.45922 (15)	−0.18616 (7)	0.0215 (3)
H8	0.0631	0.4980	−0.2168	0.026*
C9	0.24836 (16)	0.44715 (14)	−0.19406 (7)	0.0206 (3)
H9	0.2882	0.4780	−0.2297	0.025*
C10	0.32348 (15)	0.38972 (14)	−0.14959 (7)	0.0180 (3)
H10	0.4150	0.3818	−0.1546	0.022*
C11	0.26463 (14)	0.34395 (14)	−0.09783 (7)	0.0157 (3)
H11	0.3161	0.3041	−0.0676	0.019*
N1	0.07845 (11)	0.30528 (11)	−0.03596 (6)	0.0128 (2)
N2	−0.04083 (11)	0.34544 (12)	−0.02319 (5)	0.0142 (2)
N3	−0.20557 (12)	0.33844 (12)	0.04624 (6)	0.0162 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.01257 (10)	0.01257 (10)	0.01677 (15)	0.00385 (8)	−0.00076 (6)	0.00076 (6)
S	0.01651 (17)	0.02061 (19)	0.0189 (2)	0.00520 (13)	0.00276 (14)	0.00644 (14)
C1	0.0132 (6)	0.0147 (6)	0.0140 (7)	0.0002 (5)	−0.0012 (5)	−0.0015 (5)
C2	0.0161 (7)	0.0176 (7)	0.0243 (8)	0.0069 (5)	0.0016 (6)	0.0014 (6)
C3	0.0250 (8)	0.0267 (8)	0.0216 (8)	0.0102 (6)	−0.0030 (6)	−0.0019 (6)
C4	0.0151 (7)	0.0250 (8)	0.0195 (8)	0.0017 (6)	0.0039 (6)	0.0010 (6)
C5	0.0271 (8)	0.0413 (10)	0.0196 (8)	−0.0002 (7)	0.0014 (7)	−0.0027 (8)
C6	0.0150 (6)	0.0121 (6)	0.0147 (6)	0.0011 (5)	−0.0002 (5)	−0.0016 (5)
C7	0.0156 (6)	0.0174 (7)	0.0208 (8)	0.0039 (5)	−0.0013 (6)	0.0004 (6)
C8	0.0260 (8)	0.0211 (7)	0.0175 (8)	0.0041 (6)	−0.0017 (6)	0.0027 (6)
C9	0.0293 (8)	0.0154 (7)	0.0171 (7)	−0.0004 (6)	0.0055 (6)	−0.0015 (6)
C10	0.0173 (7)	0.0149 (6)	0.0219 (8)	−0.0009 (5)	0.0029 (6)	−0.0050 (6)
C11	0.0149 (6)	0.0146 (6)	0.0177 (7)	0.0011 (5)	0.0001 (5)	−0.0017 (6)
N1	0.0107 (5)	0.0122 (5)	0.0156 (6)	0.0013 (4)	−0.0001 (5)	−0.0016 (5)
N2	0.0126 (5)	0.0138 (5)	0.0161 (6)	0.0017 (5)	0.0000 (4)	−0.0006 (5)
N3	0.0133 (5)	0.0178 (6)	0.0175 (6)	0.0032 (5)	0.0026 (5)	0.0017 (5)

Geometric parameters (Å, º)

Cu—N1^i	1.9219 (12)	C4—H4B	0.9900
Cu—N1	1.9219 (12)	C5—H5A	0.9800
Cu—S^i	2.2756 (4)	C5—H5B	0.9800
Cu—S	2.2756 (4)	C5—H5C	0.9800
S—C1	1.7220 (15)	C6—C7	1.401 (2)
C1—N3	1.3427 (18)	C6—C11	1.4024 (19)
C1—N2	1.3706 (18)	C6—N1	1.4128 (19)
C2—N3	1.4733 (18)	C7—C8	1.387 (2)
C2—C3	1.520 (2)	C7—H7	0.9500
C2—H2A	0.9900	C8—C9	1.394 (2)
C2—H2B	0.9900	C8—H8	0.9500
C3—H3A	0.9800	C9—C10	1.389 (2)
C3—H3B	0.9800	C9—H9	0.9500
C3—H3C	0.9800	C10—C11	1.387 (2)
C4—N3	1.4682 (19)	C10—H10	0.9500
C4—C5	1.521 (2)	C11—H11	0.9500
C4—H4A	0.9900	N1—N2	1.3230 (16)
N1^i—Cu—N1	144.83 (7)	H5A—C5—H5B	109.5
N1^i—Cu—S^i	85.46 (4)	C4—C5—H5C	109.5
N1—Cu—S^i	111.39 (4)	H5A—C5—H5C	109.5
N1^i—Cu—S	111.39 (4)	H5B—C5—H5C	109.5
N1—Cu—S	85.46 (4)	C7—C6—C11	119.62 (14)
S^i—Cu—S	123.60 (2)	C7—C6—N1	124.01 (12)
C1—S—Cu	93.44 (5)	C11—C6—N1	116.36 (13)
N3—C1—N2	115.62 (12)	C8—C7—C6	119.20 (13)
N3—C1—S	120.77 (11)	C8—C7—H7	120.4
N2—C1—S	123.58 (10)	C6—C7—H7	120.4
N3—C2—C3	111.40 (13)	C7—C8—C9	121.08 (14)
N3—C2—H2A	109.3	C7—C8—H8	119.5
C3—C2—H2A	109.3	C9—C8—H8	119.5
N3—C2—H2B	109.3	C10—C9—C8	119.70 (15)
C3—C2—H2B	109.3	C10—C9—H9	120.2
H2A—C2—H2B	108.0	C8—C9—H9	120.2
C2—C3—H3A	109.5	C11—C10—C9	119.92 (14)
C2—C3—H3B	109.5	C11—C10—H10	120.0
H3A—C3—H3B	109.5	C9—C10—H10	120.0
C2—C3—H3C	109.5	C10—C11—C6	120.46 (14)
H3A—C3—H3C	109.5	C10—C11—H11	119.8
H3B—C3—H3C	109.5	C6—C11—H11	119.8
N3—C4—C5	112.36 (13)	N2—N1—C6	114.41 (11)
N3—C4—H4A	109.1	N2—N1—Cu	121.86 (9)
C5—C4—H4A	109.1	C6—N1—Cu	120.82 (9)
N3—C4—H4B	109.1	N1—N2—C1	113.29 (12)
C5—C4—H4B	109.1	C1—N3—C4	121.22 (12)
H4A—C4—H4B	107.9	C1—N3—C2	122.89 (12)
C4—C5—H5A	109.5	C4—N3—C2	115.88 (11)
C4—C5—H5B	109.5

Symmetry code: (i) y, x, −z.

(PdL20) Trans-(di(N,N-diethyl-(2-phenyldiazenyl)thioformamide-κS,κN²))palladium

Crystal data

C22H30N6PdS2	F(000) = 1128
Mr = 549.04	Dx = 1.508 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.0360 (16) Å	Cell parameters from 2763 reflections
b = 12.4564 (13) Å	θ = 2.5–27.8°
c = 12.3311 (12) Å	µ = 0.96 mm^−1
β = 100.952 (2)°	T = 118 K
V = 2418.3 (4) Å^3	Plate, green
Z = 4	0.30 × 0.25 × 0.01 mm

Data collection

CCD area detector diffractometer	2847 independent reflections
Radiation source: fine-focus sealed tube	2431 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 8.192 pixels mm^-1	θmax = 28.0°, θmin = 2.1°
ω scans	h = −19→21
Absorption correction: empirical (using intensity measurements) SADABS,ver2.03 (Sheldrick,2001)	k = −16→16
Tmin = 0.761, Tmax = 0.990	l = −9→16
8430 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0337P)^2 + 16.6377P] where P = (Fo^2 + 2Fc^2)/3
2847 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 1.47 e Å^−3
0 restraints	Δρmin = −2.28 e Å^−3

Special details

Experimental. SADABS

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 (Ų)

	x	y	z	Uiso*/Ueq
Pd	0.2500	0.2500	0.0000	0.00766 (12)
S	0.20585 (6)	0.09864 (8)	−0.10047 (9)	0.0124 (2)
N1	0.3590 (2)	0.2174 (3)	−0.0483 (3)	0.0105 (7)
N2	0.3672 (2)	0.1407 (3)	−0.1216 (3)	0.0130 (7)
N3	0.3036 (2)	−0.0007 (3)	−0.2235 (3)	0.0166 (8)
C1	0.2987 (2)	0.0782 (3)	−0.1514 (3)	0.0133 (8)
C2	0.2362 (3)	−0.0810 (3)	−0.2519 (4)	0.0181 (9)
H2A	0.2348	−0.1059	−0.3268	0.022*
H2B	0.1819	−0.0479	−0.2494	0.022*
C3	0.2491 (3)	−0.1763 (4)	−0.1742 (4)	0.0267 (11)
H3A	0.2037	−0.2268	−0.1956	0.040*
H3B	0.2495	−0.1523	−0.1001	0.040*
H3C	0.3023	−0.2102	−0.1775	0.040*
C4	0.3812 (3)	−0.0184 (4)	−0.2689 (4)	0.0223 (10)
H4A	0.3859	−0.0940	−0.2854	0.027*
H4B	0.4304	0.0014	−0.2138	0.027*
C5	0.3810 (3)	0.0463 (4)	−0.3727 (4)	0.0310 (12)
H5A	0.4325	0.0327	−0.3995	0.046*
H5B	0.3774	0.1213	−0.3566	0.046*
H5C	0.3331	0.0259	−0.4281	0.046*
C6	0.4352 (2)	0.2783 (3)	−0.0210 (3)	0.0119 (8)
C7	0.4701 (2)	0.3000 (3)	0.0893 (3)	0.0133 (8)
H7	0.4440	0.2741	0.1453	0.016*
C8	0.5442 (3)	0.3608 (3)	0.1151 (4)	0.0166 (9)
H8	0.5675	0.3756	0.1886	0.020*
C9	0.5835 (3)	0.3992 (3)	0.0325 (4)	0.0198 (9)
H9	0.6330	0.4394	0.0502	0.024*
C10	0.5486 (3)	0.3774 (3)	−0.0775 (4)	0.0185 (9)
H10	0.5745	0.4041	−0.1333	0.022*
C11	0.4749 (3)	0.3156 (3)	−0.1045 (4)	0.0148 (8)
H11	0.4525	0.2995	−0.1779	0.018*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd	0.00897 (19)	0.00730 (18)	0.0072 (2)	−0.00099 (16)	0.00277 (14)	−0.00066 (17)
S	0.0122 (4)	0.0116 (4)	0.0139 (5)	−0.0023 (4)	0.0042 (4)	−0.0043 (4)
N1	0.0113 (15)	0.0103 (14)	0.0109 (17)	−0.0001 (12)	0.0041 (13)	−0.0014 (12)
N2	0.0140 (16)	0.0126 (15)	0.0131 (18)	0.0014 (12)	0.0043 (13)	−0.0014 (13)
N3	0.0166 (17)	0.0146 (17)	0.020 (2)	−0.0006 (13)	0.0072 (15)	−0.0078 (15)
C1	0.0140 (18)	0.0126 (18)	0.014 (2)	0.0013 (14)	0.0033 (16)	−0.0006 (15)
C2	0.018 (2)	0.018 (2)	0.019 (2)	−0.0026 (16)	0.0047 (17)	−0.0100 (17)
C3	0.030 (2)	0.017 (2)	0.034 (3)	−0.0007 (18)	0.007 (2)	−0.006 (2)
C4	0.017 (2)	0.026 (2)	0.027 (3)	0.0016 (17)	0.0103 (19)	−0.013 (2)
C5	0.026 (2)	0.042 (3)	0.027 (3)	−0.005 (2)	0.011 (2)	−0.008 (2)
C6	0.0139 (18)	0.0079 (17)	0.014 (2)	0.0016 (13)	0.0038 (16)	−0.0008 (14)
C7	0.0159 (19)	0.0139 (18)	0.012 (2)	0.0009 (15)	0.0066 (16)	0.0028 (16)
C8	0.017 (2)	0.019 (2)	0.013 (2)	−0.0020 (16)	−0.0019 (17)	−0.0029 (16)
C9	0.017 (2)	0.017 (2)	0.026 (3)	−0.0064 (16)	0.0046 (18)	−0.0021 (18)
C10	0.018 (2)	0.018 (2)	0.022 (2)	−0.0045 (16)	0.0100 (18)	−0.0005 (18)
C11	0.018 (2)	0.0145 (19)	0.013 (2)	−0.0024 (15)	0.0045 (16)	−0.0020 (16)

Geometric parameters (Å, º)

Pd—N1^i	1.993 (3)	C4—C5	1.512 (7)
Pd—N1	1.993 (3)	C4—H4A	0.9700
Pd—S	2.2930 (10)	C4—H4B	0.9700
Pd—S^i	2.2930 (10)	C5—H5A	0.9600
S—C1	1.741 (4)	C5—H5B	0.9600
N1—N2	1.339 (5)	C5—H5C	0.9600
N1—C6	1.423 (5)	C6—C11	1.389 (6)
N2—C1	1.340 (5)	C6—C7	1.396 (6)
N3—C1	1.338 (5)	C7—C8	1.395 (6)
N3—C2	1.465 (5)	C7—H7	0.9300
N3—C4	1.476 (5)	C8—C9	1.381 (6)
C2—C3	1.515 (6)	C8—H8	0.9300
C2—H2A	0.9700	C9—C10	1.392 (6)
C2—H2B	0.9700	C9—H9	0.9300
C3—H3A	0.9600	C10—C11	1.397 (6)
C3—H3B	0.9600	C10—H10	0.9300
C3—H3C	0.9600	C11—H11	0.9300
N1^i—Pd—N1	180.0	N3—C4—H4A	109.2
N1^i—Pd—S	97.51 (9)	C5—C4—H4A	109.2
N1—Pd—S	82.49 (9)	N3—C4—H4B	109.2
N1^i—Pd—S^i	82.49 (9)	C5—C4—H4B	109.2
N1—Pd—S^i	97.51 (9)	H4A—C4—H4B	107.9
S—Pd—S^i	180.00 (5)	C4—C5—H5A	109.5
C1—S—Pd	96.75 (14)	C4—C5—H5B	109.5
N2—N1—C6	110.5 (3)	H5A—C5—H5B	109.5
N2—N1—Pd	123.5 (2)	C4—C5—H5C	109.5
C6—N1—Pd	125.7 (3)	H5A—C5—H5C	109.5
N1—N2—C1	114.8 (3)	H5B—C5—H5C	109.5
C1—N3—C2	121.8 (4)	C11—C6—C7	120.2 (4)
C1—N3—C4	121.5 (3)	C11—C6—N1	119.8 (4)
C2—N3—C4	116.4 (3)	C7—C6—N1	120.1 (4)
N3—C1—N2	117.4 (4)	C8—C7—C6	119.6 (4)
N3—C1—S	120.6 (3)	C8—C7—H7	120.2
N2—C1—S	122.0 (3)	C6—C7—H7	120.2
N3—C2—C3	112.2 (4)	C9—C8—C7	120.5 (4)
N3—C2—H2A	109.2	C9—C8—H8	119.7
C3—C2—H2A	109.2	C7—C8—H8	119.7
N3—C2—H2B	109.2	C8—C9—C10	119.8 (4)
C3—C2—H2B	109.2	C8—C9—H9	120.1
H2A—C2—H2B	107.9	C10—C9—H9	120.1
C2—C3—H3A	109.5	C9—C10—C11	120.3 (4)
C2—C3—H3B	109.5	C9—C10—H10	119.9
H3A—C3—H3B	109.5	C11—C10—H10	119.9
C2—C3—H3C	109.5	C6—C11—C10	119.6 (4)
H3A—C3—H3C	109.5	C6—C11—H11	120.2
H3B—C3—H3C	109.5	C10—C11—H11	120.2
N3—C4—C5	112.1 (4)

Symmetry code: (i) −x+1/2, −y+1/2, −z.

(PtL20) Trans-(di(N,N-diethyl-(2-phenyldiazenyl)thioformamide-κS,κN²))platinum

Crystal data

C22H30N6PtS2	F(000) = 1256
Mr = 637.73	Dx = 1.745 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.9317 (7) Å	Cell parameters from 9821 reflections
b = 12.5300 (5) Å	θ = 2.5–28.0°
c = 12.3798 (5) Å	µ = 5.97 mm^−1
β = 100.755 (1)°	T = 118 K
V = 2427.90 (17) Å^3	Plate, dark green
Z = 4	0.25 × 0.20 × 0.15 mm

Data collection

CCD area detector diffractometer	2937 independent reflections
Radiation source: fine-focus sealed tube	2632 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.120
Detector resolution: 8.192 pixels mm^-1	θmax = 28.0°, θmin = 2.1°
ω scans	h = −21→21
Absorption correction: empirical (using intensity measurements) SADABS,ver2.03 (Sheldrick,2001)	k = −16→16
Tmin = 0.255, Tmax = 0.408	l = −16→16
14253 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0604P)^2] where P = (Fo^2 + 2Fc^2)/3
2937 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 3.08 e Å^−3
0 restraints	Δρmin = −4.14 e Å^−3

Special details

Experimental. SADABS

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 (Ų)

	x	y	z	Uiso*/Ueq
Pt1	0.2500	0.2500	0.5000	0.01078 (10)
S1	0.20567 (4)	0.09968 (5)	0.39979 (5)	0.01557 (15)
N1	0.35741 (13)	0.2183 (2)	0.45030 (17)	0.0132 (4)
N2	0.36679 (13)	0.14186 (17)	0.37671 (16)	0.0161 (4)
N3	0.30312 (14)	0.00106 (18)	0.27523 (17)	0.0219 (5)
C1	0.29868 (15)	0.08026 (19)	0.34732 (19)	0.0164 (5)
C2	0.23519 (17)	−0.0786 (2)	0.2480 (2)	0.0230 (5)
H2A	0.2332	−0.1033	0.1732	0.028*
H2B	0.1807	−0.0456	0.2514	0.028*
C3	0.2486 (2)	−0.1735 (2)	0.3253 (3)	0.0314 (6)
H3A	0.3031	−0.2055	0.3233	0.047*
H3B	0.2042	−0.2249	0.3027	0.047*
H3C	0.2472	−0.1501	0.3987	0.047*
C4	0.38099 (17)	−0.0158 (2)	0.2293 (2)	0.0270 (6)
H4A	0.3861	−0.0911	0.2131	0.032*
H4B	0.4305	0.0043	0.2837	0.032*
C5	0.38013 (19)	0.0485 (3)	0.1252 (2)	0.0381 (7)
H5A	0.3276	0.0358	0.0747	0.057*
H5B	0.4274	0.0273	0.0919	0.057*
H5C	0.3849	0.1231	0.1430	0.057*
C6	0.43498 (17)	0.2789 (3)	0.4786 (2)	0.0153 (5)
C7	0.47029 (16)	0.2975 (2)	0.58875 (19)	0.0178 (5)
H7	0.4440	0.2705	0.6440	0.021*
C8	0.54517 (16)	0.3568 (2)	0.6154 (2)	0.0204 (5)
H8	0.5691	0.3688	0.6888	0.025*
C9	0.58436 (16)	0.3981 (2)	0.5334 (2)	0.0225 (5)
H9	0.6339	0.4386	0.5514	0.027*
C10	0.54854 (17)	0.3783 (2)	0.4236 (2)	0.0222 (5)
H10	0.5746	0.4058	0.3683	0.027*
C11	0.47520 (16)	0.3185 (2)	0.39599 (19)	0.0193 (5)
H11	0.4525	0.3045	0.3226	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.01491 (14)	0.00946 (15)	0.00856 (15)	−0.00097 (3)	0.00371 (9)	−0.00063 (3)
S1	0.0192 (3)	0.0136 (3)	0.0150 (3)	−0.0025 (2)	0.0058 (2)	−0.0044 (2)
N1	0.0152 (11)	0.0119 (10)	0.0132 (11)	−0.0016 (10)	0.0042 (8)	−0.0002 (10)
N2	0.0202 (10)	0.0158 (10)	0.0132 (9)	0.0009 (8)	0.0051 (8)	−0.0035 (8)
N3	0.0237 (11)	0.0210 (11)	0.0227 (11)	−0.0027 (9)	0.0088 (9)	−0.0097 (9)
C1	0.0216 (11)	0.0151 (12)	0.0139 (11)	0.0022 (9)	0.0067 (9)	−0.0005 (9)
C2	0.0266 (13)	0.0212 (13)	0.0211 (13)	−0.0022 (11)	0.0041 (10)	−0.0104 (10)
C3	0.0376 (16)	0.0213 (14)	0.0353 (16)	−0.0019 (12)	0.0064 (13)	−0.0048 (12)
C4	0.0248 (13)	0.0286 (15)	0.0297 (15)	0.0013 (11)	0.0104 (11)	−0.0141 (11)
C5	0.0330 (16)	0.052 (2)	0.0322 (16)	−0.0060 (15)	0.0139 (13)	−0.0101 (15)
C6	0.0150 (13)	0.0126 (11)	0.0180 (13)	−0.0004 (12)	0.0025 (10)	−0.0022 (12)
C7	0.0234 (12)	0.0178 (13)	0.0131 (11)	0.0006 (10)	0.0058 (9)	0.0011 (9)
C8	0.0229 (12)	0.0206 (13)	0.0165 (12)	−0.0008 (10)	0.0003 (9)	−0.0015 (10)
C9	0.0192 (11)	0.0225 (13)	0.0263 (13)	−0.0054 (10)	0.0053 (10)	−0.0022 (10)
C10	0.0257 (12)	0.0228 (13)	0.0210 (13)	−0.0045 (10)	0.0120 (10)	0.0003 (10)
C11	0.0243 (12)	0.0213 (12)	0.0129 (11)	−0.0015 (10)	0.0051 (9)	−0.0011 (9)

Geometric parameters (Å, º)

Pt1—N1^i	1.964 (2)	C4—C5	1.518 (4)
Pt1—N1	1.964 (2)	C4—H4A	0.9700
Pt1—S1	2.2932 (6)	C4—H4B	0.9700
Pt1—S1^i	2.2932 (6)	C5—H5A	0.9600
S1—C1	1.743 (2)	C5—H5B	0.9600
N1—N2	1.349 (3)	C5—H5C	0.9600
N1—C6	1.437 (4)	C6—C7	1.394 (4)
N2—C1	1.326 (3)	C6—C11	1.395 (4)
N3—C1	1.345 (3)	C7—C8	1.392 (4)
N3—C2	1.465 (3)	C7—H7	0.9300
N3—C4	1.474 (3)	C8—C9	1.387 (3)
C2—C3	1.516 (4)	C8—H8	0.9300
C2—H2A	0.9700	C9—C10	1.395 (4)
C2—H2B	0.9700	C9—H9	0.9300
C3—H3A	0.9600	C10—C11	1.376 (4)
C3—H3B	0.9600	C10—H10	0.9300
C3—H3C	0.9600	C11—H11	0.9300
N1^i—Pt1—N1	180.0	N3—C4—H4A	109.2
N1^i—Pt1—S1	97.89 (7)	C5—C4—H4A	109.2
N1—Pt1—S1	82.11 (7)	N3—C4—H4B	109.2
N1^i—Pt1—S1^i	82.11 (7)	C5—C4—H4B	109.2
N1—Pt1—S1^i	97.89 (7)	H4A—C4—H4B	107.9
S1—Pt1—S1^i	180.000 (17)	C4—C5—H5A	109.5
C1—S1—Pt1	96.82 (8)	C4—C5—H5B	109.5
N2—N1—C6	109.9 (2)	H5A—C5—H5B	109.5
N2—N1—Pt1	124.60 (17)	C4—C5—H5C	109.5
C6—N1—Pt1	125.2 (2)	H5A—C5—H5C	109.5
C1—N2—N1	114.23 (19)	H5B—C5—H5C	109.5
C1—N3—C2	121.9 (2)	C7—C6—C11	120.0 (3)
C1—N3—C4	121.0 (2)	C7—C6—N1	119.9 (2)
C2—N3—C4	116.9 (2)	C11—C6—N1	120.1 (2)
N2—C1—N3	118.0 (2)	C8—C7—C6	119.5 (2)
N2—C1—S1	121.71 (18)	C8—C7—H7	120.2
N3—C1—S1	120.26 (19)	C6—C7—H7	120.2
N3—C2—C3	112.2 (2)	C9—C8—C7	120.6 (2)
N3—C2—H2A	109.2	C9—C8—H8	119.7
C3—C2—H2A	109.2	C7—C8—H8	119.7
N3—C2—H2B	109.2	C8—C9—C10	119.2 (2)
C3—C2—H2B	109.2	C8—C9—H9	120.4
H2A—C2—H2B	107.9	C10—C9—H9	120.4
C2—C3—H3A	109.5	C11—C10—C9	120.9 (2)
C2—C3—H3B	109.5	C11—C10—H10	119.6
H3A—C3—H3B	109.5	C9—C10—H10	119.6
C2—C3—H3C	109.5	C10—C11—C6	119.8 (2)
H3A—C3—H3C	109.5	C10—C11—H11	120.1
H3B—C3—H3C	109.5	C6—C11—H11	120.1
N3—C4—C5	112.1 (2)
N1^i—Pt1—S1—C1	175.13 (10)	C1—N3—C2—C3	−88.5 (3)
N1—Pt1—S1—C1	−4.87 (10)	C4—N3—C2—C3	85.2 (3)
S1—Pt1—N1—N2	7.3 (2)	C1—N3—C4—C5	−88.9 (3)
S1^i—Pt1—N1—N2	−172.7 (2)	C2—N3—C4—C5	97.4 (3)
S1—Pt1—N1—C6	−178.8 (2)	N2—N1—C6—C7	−130.9 (3)
S1^i—Pt1—N1—C6	1.2 (2)	Pt1—N1—C6—C7	54.5 (4)
C6—N1—N2—C1	178.7 (2)	N2—N1—C6—C11	48.7 (4)
Pt1—N1—N2—C1	−6.6 (3)	Pt1—N1—C6—C11	−125.9 (2)
N1—N2—C1—N3	−179.1 (2)	C11—C6—C7—C8	0.8 (4)
N1—N2—C1—S1	0.7 (3)	N1—C6—C7—C8	−179.6 (3)
C2—N3—C1—N2	172.6 (2)	C6—C7—C8—C9	0.6 (4)
C4—N3—C1—N2	−0.8 (4)	C7—C8—C9—C10	−0.9 (4)
C2—N3—C1—S1	−7.2 (3)	C8—C9—C10—C11	0.0 (4)
C4—N3—C1—S1	179.4 (2)	C9—C10—C11—C6	1.3 (4)
Pt1—S1—C1—N2	3.8 (2)	C7—C6—C11—C10	−1.7 (4)
Pt1—S1—C1—N3	−176.34 (19)	N1—C6—C11—C10	178.7 (3)

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.