Chlorido{5-chloro-2-[2-(methyl­sulfanyl)phenyl­diazen­yl]phenyl}­platinum(II)

Bagchi, V.; Bandyopadhyay, D.

doi:10.1107/S1600536808000767

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m359

doi:10.1107/S1600536808000767

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Chlorido{5-chloro-2-[2-(methylsulfanyl)phenyldiazenyl]phenyl}platinum(II)

Vivek Bagchi ^a and Debkumar Bandyopadhyay ^a ^*

^aDepartment of Chemistry, Indian Institute of Technology, New Delhi 110 016, India
^*Correspondence e-mail: dkbp@chemistry.iitd.ac.in

(Received 3 January 2008; accepted 9 January 2008; online 16 January 2008)

The title compound, [Pt(C₁₃H₁₀ClN₂S)Cl], contains a Pt atom tetracoordinated by a benzene C, a diazene N, a Cl and an S atom in an approximately square-planar geometry. The molecules dimerize through a nonbonded S⋯S interaction [S⋯S = 3.523 (18) Å]. There are no hydrogen bonds and the crystal packing is stabilized by four intermolecular π–π interactions; 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_r = 492.28
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.018
wR(F²) = 0.043
S = 1.05
2544 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.89 e Å⁻³
Δρ_min = −0.89 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

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)

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.

Supporting information

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

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

checkCIF report

Comment top

Cyclometallated compounds have numerous applications (Dupont et al., 2005) in organic synthesis, catalysis and metallomesogen chemistry. Although a number of cycloplatinated complexes have been reported in the literature, report of platinum complexes with sulfur as auxiliary donor and the existence of C–Pt bond are sparse. Herein we report the crystal structure of (I) having such features.

The molecular structure of the title compound, (I), is shown in Fig. 1, with the atom numbering scheme. The platinum atom along with donor set of four atoms lie almost in one plane. Selected bond lengths, bond angles are listed in Table 1. The packing arrangement of (I) is shown in Fig. 2. The N?N bond length is similar of other cycloplatinated azoarenes (Chattopadhyay et al., 1991).

The metal carbon bond length, 1.986 (3) Å, is slightly lower than the reported values of other ortho-metallated azoarenes (Chattopadhyay et al., 1991). The molecules are found to dimerize through non-bonded S···S interaction; having S···Sⁱ [symmetry code: (i) -x, 2 - y, -z] distance of 3.523 (18) Å (Bagchi et al. 2007) (Fig.3).The crystal packing is stabilized by four inter-molecular π-π interactions; the Cg3—Cg4ⁱⁱ, Cg3—Cg4ⁱⁱⁱ, Cg4—Cg3ⁱⁱ, Cg4—Cg3ⁱⁱⁱ, [symmetry codes: (ii) -x, 1 - y, -z, (iii) 1 - x, 1 - y, -z. Cg3 and Cg4 are the centroids of C1—C6 and C7—C12 rings, respectively] distances are 3.638 (3), 3.804 (3), 3.638 (3) and 3.804 (3) Å, respectively; the corresponding perpendicular distances are 3.448, 3.369, 3.466 and 3.406 Å, respectively (Fig. 4).

Related literature top

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

Experimental top

2-(Methylsulfanyl)diazenyl-4-chlorobenzene was prepared by coupling 2-(methylsulfanyl)aniline with 4-nitroso-chlorobenzene. The ligand thus obtained was reacted with K₂PtCl₄ following a reported method (Buraway & Vellins, 1954). The product was purified by column chromatographic technique using silica gel column and methanol and dichloromethane (1:9 v/v) mixture as eluent. The solvent was evaporated in vacuum to obtain the pure product (78.3%). Suitable crystals of (I) were grown from a dichloromethane–hexane solution by slow evaporation.

Computing details top

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

Figures top

	Fig. 1. The asymmetric unit of (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The molecular arrangement of (I) in the unitcell.
	Fig. 3. The intermolecular S···S interaction for (I), indicated by dotted line [symmetry code: (i) -x, 2 - y, -z].
	Fig. 4. The intermolecular π—π interactions for (I), indicated by the dotted lines. [Symmetry codes: (ii) -x, 1 - y, -z, (iii) 1 - x, 1 - y, -z]. Cg3 and Cg4 are centroids of C1—C6 and C7—C12 rings, respectively.

Chlorido{5-chloro-2-[2-(methylsulfanyl)phenyldiazenyl]phenyl}platinum(II) top

Crystal data top

[Pt(C₁₃H₁₀ClN₂S)Cl]	Z = 2
M_r = 492.28	F(000) = 460.0
Triclinic, P1	D_x = 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 = 1.0–25.5°
c = 11.069 (3) Å	µ = 10.70 mm⁻¹
α = 105.428 (4)°	T = 273 K
β = 91.798 (4)°	Block, pink
γ = 96.641 (4)°	0.42 × 0.28 × 0.19 mm
V = 689.1 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2544 independent reflections
Radiation source: fine-focus sealed tube	2472 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.035, T_max = 0.134	k = −10→10
6783 measured reflections	l = −13→13

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.043	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0209P)² + 0.4377P] where P = (F_o² + 2F_c²)/3
2544 reflections	(Δ/σ)_max = 0.002
173 parameters	Δρ_max = 0.89 e Å⁻³
0 restraints	Δρ_min = −0.89 e Å⁻³

Crystal data top

[Pt(C₁₃H₁₀ClN₂S)Cl]	γ = 96.641 (4)°
M_r = 492.28	V = 689.1 (4) Å³
Triclinic, P1	Z = 2
a = 7.424 (2) Å	Mo Kα radiation
b = 8.777 (3) Å	µ = 10.70 mm⁻¹
c = 11.069 (3) Å	T = 273 K
α = 105.428 (4)°	0.42 × 0.28 × 0.19 mm
β = 91.798 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2544 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2472 reflections with I > 2σ(I)
T_min = 0.035, T_max = 0.134	R_int = 0.025
6783 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	0 restraints
wR(F²) = 0.043	H-atom parameters constrained
S = 1.05	Δρ_max = 0.89 e Å⁻³
2544 reflections	Δρ_min = −0.89 e Å⁻³
173 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	[Pt(C₁₃H₁₀ClN₂S)Cl]
M_r	492.28
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	7.424 (2), 8.777 (3), 11.069 (3)
α, β, γ (°)	105.428 (4), 91.798 (4), 96.641 (4)
V (Å³)	689.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	10.70
Crystal size (mm)	0.42 × 0.28 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.035, 0.134
No. of measured, independent and observed [I > 2σ(I)] reflections	6783, 2544, 2472
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.043, 1.05
No. of reflections	2544
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.89, −0.89

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

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

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

Acknowledgements

We thank the Department of Science and Technology, India (project No. SR/S1/IC-04/2007), for funding and CSIR for a fellowship to VB. The single-crystal X-ray diffractometer facility provided by IITD is gratefully acknowledged.

References

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