Chlorido{5-chloro-2-[2-(methyl-sulfanyl)phenyl-diazen-yl]phenyl}-platinum(II).

The title compound, [Pt(C(13)H(10)ClN(2)S)Cl], contains a Pt atom tetra-coordinated by a benzene C, a diazene N, a Cl and an S atom in an approximately square-planar geometry. The mol-ecules dimerize through a nonbonded S⋯S inter-action [S⋯S = 3.523 (18) Å]. There are no hydrogen bonds and the crystal packing is stabilized by four inter-molecular π-π inter-actions; the centroid-centroid distances are 3.804 (3), 3.638 (3), 3.804 (3) and 3.638 (3) Å, and the corresponding perpendicular distances are 3.369, 3.448, 3.406 and 3.466 Å.

Related literature

For related literature, see: Bagchi et al. (2007 ▶); Chattopadhyay et al. (1991 ▶); Dupont et al. (2005 ▶); Buraway & Vellins (1954 ▶).

Experimental

Crystal data

[Pt(C13H10ClN2S)Cl]

M = 492.28

Triclinic,

a = 7.424 (2) Å

b = 8.777 (3) Å

c = 11.069 (3) Å

α = 105.428 (4)°

β = 91.798 (4)°

γ = 96.641 (4)°

V = 689.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 10.70 mm−1

T = 273 (2) K

0.42 × 0.28 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.035, T max = 0.134

6783 measured reflections

2544 independent reflections

2472 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.018

wR(F 2) = 0.043

S = 1.05

2544 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.89 e Å−3

Δρmin = −0.89 e Å−3

Data collection: SMART (Bruker, 1998 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808000767/at2531sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000767/at2531Isup2.hkl

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

[Pt(C13H10ClN2S)Cl]	Z = 2
Mr = 492.28	F000 = 460.0
Triclinic, P1	Dx = 2.372 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.424 (2) Å	Cell parameters from 2472 reflections
b = 8.777 (3) Å	θ = 1.0–25.5º
c = 11.069 (3) Å	µ = 10.70 mm−1
α = 105.428 (4)º	T = 273 (2) K
β = 91.798 (4)º	Block, pink
γ = 96.641 (4)º	0.42 × 0.28 × 0.19 mm
V = 689.1 (4) Å3

Bruker SMART CCD area-detector diffractometer	2544 independent reflections
Radiation source: fine-focus sealed tube	2472 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 273(2) K	θmax = 25.5º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.035, Tmax = 0.134	k = −10→10
6783 measured reflections	l = −13→13

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)] = 0.018	H-atom parameters constrained
wR(F2) = 0.043	w = 1/[σ2(Fo2) + (0.0209P)2 + 0.4377P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.002
2544 reflections	Δρmax = 0.89 e Å−3
173 parameters	Δρmin = −0.89 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
C8	0.3562 (5)	0.2238 (4)	−0.1887 (4)	0.0399 (8)
H8	0.3666	0.1521	−0.1411	0.048*
C9	0.3852 (5)	0.1810 (4)	−0.3149 (4)	0.0432 (9)
H9	0.4144	0.0802	−0.3542	0.052*
Pt1	0.216802 (16)	0.685427 (14)	−0.091569 (11)	0.03068 (6)
Cl2	0.40740 (17)	0.23872 (14)	−0.54110 (10)	0.0599 (3)
Cl1	0.19823 (17)	0.81788 (12)	−0.24323 (10)	0.0529 (3)
N1	0.2327 (4)	0.5583 (4)	0.0285 (3)	0.0311 (6)
N2	0.2763 (4)	0.4162 (3)	−0.0062 (3)	0.0356 (6)
C1	0.1910 (4)	0.6209 (4)	0.1559 (3)	0.0322 (7)
C7	0.3111 (4)	0.3755 (4)	−0.1328 (3)	0.0329 (7)
C10	0.3698 (5)	0.2924 (4)	−0.3816 (3)	0.0390 (8)
C2	0.1378 (5)	0.7727 (4)	0.1893 (3)	0.0347 (7)
C11	0.3267 (5)	0.4437 (4)	−0.3279 (3)	0.0370 (8)
H11	0.3186	0.5149	−0.3763	0.044*
C5	0.1648 (6)	0.6038 (5)	0.3660 (4)	0.0480 (10)
H5	0.1715	0.5467	0.4254	0.058*
S1	0.10822 (13)	0.87598 (11)	0.07262 (8)	0.0362 (2)
C12	0.2953 (5)	0.4887 (4)	−0.2005 (3)	0.0326 (7)
C4	0.1152 (6)	0.7564 (6)	0.4010 (4)	0.0515 (10)
H4	0.0924	0.8021	0.4841	0.062*
C6	0.2041 (5)	0.5359 (5)	0.2441 (4)	0.0412 (8)
H6	0.2389	0.4342	0.2213	0.049*
C3	0.0998 (5)	0.8407 (5)	0.3127 (4)	0.0454 (9)
H3	0.0643	0.9421	0.3358	0.054*
C13	0.2718 (6)	1.0531 (5)	0.1290 (4)	0.0519 (10)
H13A	0.2399	1.1140	0.2093	0.078*
H13B	0.2714	1.1164	0.0704	0.078*
H13C	0.3908	1.0227	0.1371	0.078*

	U11	U22	U33	U12	U13	U23
C8	0.041 (2)	0.0332 (19)	0.048 (2)	0.0096 (15)	0.0056 (17)	0.0131 (17)
C9	0.043 (2)	0.0313 (19)	0.052 (2)	0.0099 (15)	0.0065 (18)	0.0042 (17)
Pt1	0.03822 (9)	0.02666 (9)	0.02684 (9)	0.00541 (6)	0.00145 (6)	0.00626 (6)
Cl2	0.0827 (8)	0.0549 (6)	0.0349 (5)	0.0134 (6)	0.0109 (5)	−0.0030 (5)
Cl1	0.0879 (8)	0.0395 (5)	0.0383 (5)	0.0191 (5)	0.0114 (5)	0.0174 (4)
N1	0.0315 (15)	0.0336 (16)	0.0279 (15)	0.0057 (12)	0.0014 (12)	0.0074 (12)
N2	0.0366 (15)	0.0343 (16)	0.0374 (17)	0.0074 (12)	0.0041 (13)	0.0112 (13)
C1	0.0314 (17)	0.0361 (18)	0.0274 (17)	0.0024 (14)	−0.0006 (13)	0.0069 (14)
C7	0.0318 (17)	0.0315 (18)	0.0350 (19)	0.0042 (14)	0.0018 (14)	0.0082 (15)
C10	0.0388 (19)	0.040 (2)	0.0324 (19)	0.0039 (15)	0.0053 (15)	0.0006 (16)
C2	0.0356 (18)	0.0370 (19)	0.0294 (18)	0.0031 (14)	0.0004 (14)	0.0065 (15)
C11	0.044 (2)	0.0319 (18)	0.0340 (19)	0.0031 (15)	0.0027 (16)	0.0081 (15)
C5	0.052 (2)	0.063 (3)	0.033 (2)	0.006 (2)	−0.0015 (17)	0.0205 (19)
S1	0.0434 (5)	0.0343 (5)	0.0302 (5)	0.0113 (4)	0.0005 (4)	0.0054 (4)
C12	0.0334 (17)	0.0279 (17)	0.0330 (19)	0.0020 (13)	−0.0012 (14)	0.0033 (14)
C4	0.049 (2)	0.073 (3)	0.031 (2)	0.008 (2)	0.0055 (17)	0.011 (2)
C6	0.043 (2)	0.046 (2)	0.037 (2)	0.0049 (16)	−0.0015 (16)	0.0164 (17)
C3	0.048 (2)	0.053 (2)	0.034 (2)	0.0100 (18)	0.0056 (17)	0.0071 (18)
C13	0.070 (3)	0.034 (2)	0.047 (2)	0.0003 (19)	−0.005 (2)	0.0070 (18)

C8—C9	1.378 (6)	C10—C11	1.382 (5)
C8—C7	1.394 (5)	C2—C3	1.390 (5)
C8—H8	0.9300	C2—S1	1.785 (4)
C9—C10	1.385 (6)	C11—C12	1.395 (5)
C9—H9	0.9300	C11—H11	0.9300
Pt1—N1	1.959 (3)	C5—C6	1.378 (6)
Pt1—C12	1.986 (3)	C5—C4	1.388 (6)
Pt1—Cl1	2.2911 (11)	C5—H5	0.9300
Pt1—S1	2.3529 (10)	S1—C13	1.811 (4)
Cl2—C10	1.742 (4)	C4—C3	1.383 (6)
N1—N2	1.286 (4)	C4—H4	0.9300
N1—C1	1.429 (4)	C6—H6	0.9300
N2—C7	1.391 (5)	C3—H3	0.9300
C1—C6	1.385 (5)	C13—H13A	0.9600
C1—C2	1.391 (5)	C13—H13B	0.9600
C7—C12	1.407 (5)	C13—H13C	0.9600
C9—C8—C7	119.5 (4)	C10—C11—C12	119.4 (3)
C9—C8—H8	120.3	C10—C11—H11	120.3
C7—C8—H8	120.3	C12—C11—H11	120.3
C8—C9—C10	118.2 (3)	C6—C5—C4	120.7 (4)
C8—C9—H9	120.9	C6—C5—H5	119.7
C10—C9—H9	120.9	C4—C5—H5	119.7
N1—Pt1—C12	79.26 (14)	C2—S1—C13	102.24 (19)
N1—Pt1—Cl1	175.94 (9)	C2—S1—Pt1	95.61 (12)
C12—Pt1—Cl1	96.84 (11)	C13—S1—Pt1	111.80 (16)
N1—Pt1—S1	86.25 (9)	C11—C12—C7	117.3 (3)
C12—Pt1—S1	165.07 (11)	C11—C12—Pt1	131.9 (3)
Cl1—Pt1—S1	97.57 (4)	C7—C12—Pt1	110.7 (3)
N2—N1—C1	118.9 (3)	C3—C4—C5	120.2 (4)
N2—N1—Pt1	120.9 (2)	C3—C4—H4	119.9
C1—N1—Pt1	120.2 (2)	C5—C4—H4	119.9
N1—N2—C7	110.8 (3)	C5—C6—C1	119.2 (4)
C6—C1—C2	120.7 (3)	C5—C6—H6	120.4
C6—C1—N1	121.9 (3)	C1—C6—H6	120.4
C2—C1—N1	117.4 (3)	C4—C3—C2	119.5 (4)
N2—C7—C8	119.2 (3)	C4—C3—H3	120.2
N2—C7—C12	118.3 (3)	C2—C3—H3	120.2
C8—C7—C12	122.4 (3)	S1—C13—H13A	109.5
C11—C10—C9	123.3 (3)	S1—C13—H13B	109.5
C11—C10—Cl2	118.5 (3)	H13A—C13—H13B	109.5
C9—C10—Cl2	118.2 (3)	S1—C13—H13C	109.5
C3—C2—C1	119.7 (3)	H13A—C13—H13C	109.5
C3—C2—S1	120.1 (3)	H13B—C13—H13C	109.5
C1—C2—S1	120.1 (3)
C7—C8—C9—C10	0.6 (6)	C1—C2—S1—Pt1	−6.0 (3)
C12—Pt1—N1—N2	−1.8 (3)	N1—Pt1—S1—C2	4.51 (14)
S1—Pt1—N1—N2	174.6 (3)	C12—Pt1—S1—C2	18.4 (4)
C12—Pt1—N1—C1	179.9 (3)	Cl1—Pt1—S1—C2	−176.89 (12)
S1—Pt1—N1—C1	−3.7 (2)	N1—Pt1—S1—C13	110.10 (18)
C1—N1—N2—C7	179.6 (3)	C12—Pt1—S1—C13	124.0 (4)
Pt1—N1—N2—C7	1.4 (4)	Cl1—Pt1—S1—C13	−71.30 (16)
N2—N1—C1—C6	3.0 (5)	C10—C11—C12—C7	0.5 (5)
Pt1—N1—C1—C6	−178.7 (3)	C10—C11—C12—Pt1	−175.7 (3)
N2—N1—C1—C2	−177.6 (3)	N2—C7—C12—C11	−178.5 (3)
Pt1—N1—C1—C2	0.6 (4)	C8—C7—C12—C11	0.1 (5)
N1—N2—C7—C8	−178.4 (3)	N2—C7—C12—Pt1	−1.6 (4)
N1—N2—C7—C12	0.2 (4)	C8—C7—C12—Pt1	177.0 (3)
C9—C8—C7—N2	178.0 (3)	N1—Pt1—C12—C11	178.0 (4)
C9—C8—C7—C12	−0.6 (5)	Cl1—Pt1—C12—C11	−0.8 (3)
C8—C9—C10—C11	0.0 (6)	S1—Pt1—C12—C11	163.9 (2)
C8—C9—C10—Cl2	179.7 (3)	N1—Pt1—C12—C7	1.7 (2)
C6—C1—C2—C3	0.9 (5)	Cl1—Pt1—C12—C7	−177.2 (2)
N1—C1—C2—C3	−178.5 (3)	S1—Pt1—C12—C7	−12.4 (6)
C6—C1—C2—S1	−176.2 (3)	C6—C5—C4—C3	1.8 (6)
N1—C1—C2—S1	4.4 (4)	C4—C5—C6—C1	−1.0 (6)
C9—C10—C11—C12	−0.5 (6)	C2—C1—C6—C5	−0.4 (5)
Cl2—C10—C11—C12	179.7 (3)	N1—C1—C6—C5	179.0 (3)
C3—C2—S1—C13	63.1 (4)	C5—C4—C3—C2	−1.3 (6)
C1—C2—S1—C13	−119.8 (3)	C1—C2—C3—C4	−0.1 (6)
C3—C2—S1—Pt1	176.9 (3)	S1—C2—C3—C4	177.0 (3)

Pt1—N1	1.959 (3)
Pt1—C12	1.986 (3)
Pt1—Cl1	2.2911 (11)
Pt1—S1	2.3529 (10)

N1—Pt1—C12	79.26 (14)
C12—Pt1—Cl1	96.84 (11)
N1—Pt1—S1	86.25 (9)
Cl1—Pt1—S1	97.57 (4)