Chlorido(dimethyl sulfoxide)(pyridine-2-thiol­ato N-oxide-κ2S,O)platinum(II)

Ravindran Durai Nayagam, B.; Jebas, S.R.; Selvarathy Grace, P.; Schollmeyer, D.

doi:10.1107/S1600536808019041

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Pages m975-m976

doi:10.1107/S1600536808019041

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Chlorido(dimethyl sulfoxide)(pyridine-2-thiolato N-oxide-κ²S,O)platinum(II)

B. Ravindran Durai Nayagam,^a ^* Samuel Robinson Jebas,^b P. Selvarathy Grace ^a and Dieter Schollmeyer ^c

^aDepartment of Chemistry, Popes College, Sawyerpuram 628 251, Tamilnadu, India, ^bDepartment of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India, and ^cInstitut für Organische Chemie, Universität Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: b_ravidurai@yahoo.com

(Received 11 June 2008; accepted 24 June 2008; online 28 June 2008)

The asymmetric unit of the title compound, [Pt(C₅H₄NOS)Cl(C₂H₆OS)], contains two independent complex molecules having similar geometries. Each Pt^II atom is four-coordinated in a distorted square-planar geometry by S and O atoms of one pyridine N-oxide ligand, the S atom of one dimethyl sulfoxide molecule and one terminal Cl⁻ ion. The molecules are linked into a three-dimensional framework by C—H⋯O and C—H⋯Cl hydrogen bonds.

Related literature

For biological activities of platinum, see: Weiss & Christian (1993 ); Loehrer et al. (1988 ); For biological activities of N-oxide derivatives, see: Bovin et al. (1992 ); Katsuyuki et al. (1991 ); Leonard et al. (1955 ); Lobana & Bhatia (1989 ); Symons & West (1985 ). For related literature, see: Jebas et al. (2005 ); Ravindran et al. (2008 ); Dyksterhouse et al. (2000 ); Ohms et al. (1982 ); Ravindran et al. (2008). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Pt(C₅H₄NOS)Cl(C₂H₆OS)]
M_r = 434.82
Triclinic, $[P \overline 1]$
a = 10.2407 (5) Å
b = 10.9703 (5) Å
c = 10.9772 (6) Å
α = 82.950 (1)°
β = 76.720 (1)°
γ = 76.554 (1)°
V = 1164.21 (10) Å³
Z = 4
Mo Kα radiation
μ = 12.61 mm⁻¹
T = 173 (2) K
0.47 × 0.31 × 0.15 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: Gaussian (Coppens, 1970 ) T_min = 0.5, T_max = 1.0
22889 measured reflections
5542 independent reflections
5032 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.070
S = 1.03
5542 reflections
257 parameters
H-atom parameters constrained
Δρ_max = 5.99 e Å⁻³
Δρ_min = −1.02 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Pt1—O7	2.020 (4)
Pt1—S2	2.1826 (13)
Pt1—S1	2.2495 (15)
Pt1—Cl1	2.3461 (13)
Pt2—O17	2.005 (4)
Pt2—S4	2.1850 (14)
Pt2—S3	2.2543 (14)
Pt2—Cl2	2.3402 (14)

O7—Pt1—S2	179.05 (12)
O7—Pt1—S1	86.29 (11)
S2—Pt1—S1	93.15 (5)
O7—Pt1—Cl1	89.02 (11)
S2—Pt1—Cl1	91.57 (5)
S1—Pt1—Cl1	174.53 (5)
O17—Pt2—S4	179.35 (11)
O17—Pt2—S3	86.41 (11)
S4—Pt2—S3	94.02 (5)
O17—Pt2—Cl2	87.69 (11)
S4—Pt2—Cl2	91.89 (5)
S3—Pt2—Cl2	174.07 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O17ⁱ	0.98	2.43	3.351 (8)	157
C9—H9B⋯Cl1	0.98	2.73	3.350 (6)	121
C10—H10A⋯Cl1ⁱⁱ	0.98	2.73	3.601 (7)	149
C13—H13⋯O7ⁱⁱⁱ	0.95	2.37	3.268 (8)	158
C15—H15⋯O8^iv	0.95	2.39	3.271 (7)	155
C19—H19A⋯O8^v	0.98	2.54	3.456 (7)	155
C20—H20A⋯O18^vi	0.98	2.49	3.460 (8)	172
C20—H20B⋯Cl2	0.98	2.75	3.366 (7)	122
Symmetry codes: (i) x, y+1, z-1; (ii) -x+1, -y+1, -z; (iii) x-1, y, z+1; (iv) x, y-1, z+1; (v) x, y-1, z; (vi) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2006); 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 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019041/ci2615sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808019041/ci2615Isup2.hkl

checkCIF report

Comment top

The platinum complex, cis-diamminedichloroplatinum(II) (cisplatin) is one of the most widely used antitumor drugs in the world (Weiss & Christian, 1993; Loehrer et al., 1988). N-Oxides and their derivatives show a broad spectrum of biological activity, such as antifungal, antibacterial, antimicrobial and antibacterial activities (Lobana & Bhatia, 1989; Symons et al., 1985). These compounds are also found to be involved in DNA strand scission under physiological conditions (Katsuyuki et al., 1991; Bovin et al., 1992). Pyridine N-oxides bearing a sulfur group in position 2 display significant antimicrobial activity (Leonard et al., 1955). In view of the importance of the metal platinum and N-oxides, we have previously reported the crystal structures of N-oxide derivatives (Jebas et al., 2005; Ravindran et al., 2008). As an extension of our work on these derivatives, we report here the crystal structure of the title compound (Fig. 1).

The asymmetric unit of the title compound contains two independent complex molecules having similar geometries (Fig. 1 and Table 1). Each Pt^II atom is four-coordinated in a distorted square-planar geometry by S and O atoms of one pyridine N-oxide ligand, S atom of one dimethyl sulfoxide molecule and one terminal Cl^- ion. The average Pt—O [2.013 (4) Å] and Pt—S [2.218 (14) Å] distances are comparable with the values reported in the literature (Dyksterhouse et al., 2000; Ravindran et al., 2008). The mean C—S bond distance [1.755 (6) Å] is slightly longer than that reported for the uncoordinated thione molecule [1.692 (2)–1.698 (2) Å; Ohms et al.,1982]. The N—O bond length is in good agreement with the mean value of 1.304 (15) Å reported in the literature for N-oxides (Allen et al., 1987). The dihedral angle between the two pyridine rings is 26.0 (3)°. The dihedral angle between the Pt1/S1/C1/N6/O7 and N6/C1-C5 planes is 0.6 (2)° and that between the Pt2/S3/C11/N16/O17 and N16/C11-C15 planes is 4.4 (2) Å, respectively.

The crystal packing is stabilized by intermolecular C—H··· O and C—H···Cl hydrogen bonding (Fig. 2).

Related literature top

For biological activities of platinum, see: Weiss & Christian (1993); Loehrer et al. (1988); For biological activities of N-oxide derivatives, see: Bovin et al. (1992); Katsuyuki et al. (1991); Leonard et al. (1955); Lobana & Bhatia (1989); Symons & West (1985). For related literature, see: Jebas et al. (2005); Ravindran et al. (2008); Dyksterhouse et al. (2000); Ohms et al.(1982); Ravindran et al.(2008). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 2-benzylsulfanyl pyridine N-oxide, (0.219 g 1 mmol) and potassium tetrachloroplatinate(II) (0.415 g, 1 mmol) in water (20 ml) and methanol (20 ml) was heated at 333 K with stirring for 30 min. A yellow colour mass formed was dissolved in DMSO (10 ml) and kept at 278 K for a week. The compound formed was filtered off and dried. The compound was dissolved in chloroform and allowed to undergo slow evaporation. Fine crystals were obtained after a week.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

Chlorido(dimethyl sulfoxide)(pyridine-2-thiolato N-oxide-κ²S,O)platinum(II) top

Crystal data top

[Pt(C₅H₄NOS)Cl(C₂H₆OS)]	Z = 4
M_r = 434.82	F(000) = 808
Triclinic, P1	D_x = 2.481 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2407 (5) Å	Cell parameters from 9909 reflections
b = 10.9703 (5) Å	θ = 2.5–27.8°
c = 10.9772 (6) Å	µ = 12.61 mm⁻¹
α = 82.950 (1)°	T = 173 K
β = 76.720 (1)°	Plate, colourless
γ = 76.554 (1)°	0.47 × 0.31 × 0.15 mm
V = 1164.21 (10) Å³

Data collection top

Bruker Kappa APEXII area-detector diffractometer	5542 independent reflections
Radiation source: sealed Tube	5032 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω and ϕ scans	θ_max = 27.9°, θ_min = 1.9°
Absorption correction: gaussian (Coppens, 1970)	h = −13→13
T_min = 0.5, T_max = 1.0	k = −14→14
22889 measured reflections	l = −14→14

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0265P)² + 7.1392P] where P = (F_o² + 2F_c²)/3
5542 reflections	(Δ/σ)_max = 0.001
257 parameters	Δρ_max = 5.99 e Å⁻³
0 restraints	Δρ_min = −1.02 e Å⁻³

Crystal data top

[Pt(C₅H₄NOS)Cl(C₂H₆OS)]	γ = 76.554 (1)°
M_r = 434.82	V = 1164.21 (10) Å³
Triclinic, P1	Z = 4
a = 10.2407 (5) Å	Mo Kα radiation
b = 10.9703 (5) Å	µ = 12.61 mm⁻¹
c = 10.9772 (6) Å	T = 173 K
α = 82.950 (1)°	0.47 × 0.31 × 0.15 mm
β = 76.720 (1)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	5542 independent reflections
Absorption correction: gaussian (Coppens, 1970)	5032 reflections with I > 2σ(I)
T_min = 0.5, T_max = 1.0	R_int = 0.034
22889 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 1.03	Δρ_max = 5.99 e Å⁻³
5542 reflections	Δρ_min = −1.02 e Å⁻³
257 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	0.659125 (19)	0.633021 (18)	0.106453 (19)	0.02604 (6)
Cl1	0.77432 (14)	0.58127 (13)	−0.09729 (13)	0.0340 (3)
S1	0.55837 (15)	0.66420 (15)	0.30825 (14)	0.0370 (3)
S2	0.48807 (13)	0.75691 (12)	0.03633 (12)	0.0275 (3)
C1	0.6869 (6)	0.5686 (5)	0.3749 (5)	0.0326 (11)
C2	0.6782 (7)	0.5500 (6)	0.5051 (6)	0.0412 (14)
H2	0.5983	0.5897	0.5608	0.049*
C3	0.7857 (7)	0.4741 (6)	0.5520 (6)	0.0435 (14)
H3	0.7805	0.4622	0.6401	0.052*
C4	0.9021 (7)	0.4147 (6)	0.4701 (6)	0.0399 (13)
H4	0.9763	0.3618	0.5020	0.048*
C5	0.9085 (6)	0.4330 (5)	0.3449 (6)	0.0343 (12)
H5	0.9875	0.3931	0.2884	0.041*
N6	0.8014 (5)	0.5089 (4)	0.2998 (4)	0.0299 (9)
O7	0.8176 (4)	0.5207 (4)	0.1729 (4)	0.0319 (8)
O8	0.3857 (4)	0.8369 (4)	0.1274 (4)	0.0389 (10)
C9	0.5470 (6)	0.8558 (5)	−0.0944 (6)	0.0355 (12)
H9A	0.4686	0.9050	−0.1282	0.053*
H9B	0.6103	0.8044	−0.1591	0.053*
H9C	0.5946	0.9127	−0.0682	0.053*
C10	0.4004 (6)	0.6700 (6)	−0.0310 (6)	0.0373 (13)
H10A	0.3568	0.6143	0.0344	0.056*
H10B	0.4659	0.6197	−0.0955	0.056*
H10C	0.3300	0.7280	−0.0693	0.056*
Pt2	0.23052 (2)	−0.015106 (18)	0.666962 (18)	0.02707 (6)
Cl2	0.36326 (16)	−0.21985 (13)	0.65722 (14)	0.0391 (3)
S3	0.10091 (15)	0.17934 (13)	0.69804 (14)	0.0340 (3)
S4	0.23267 (14)	0.00092 (13)	0.46616 (13)	0.0307 (3)
C11	0.0802 (5)	0.1703 (5)	0.8589 (5)	0.0299 (11)
C12	−0.0046 (6)	0.2637 (5)	0.9339 (6)	0.0358 (12)
H12	−0.0528	0.3375	0.8955	0.043*
C13	−0.0197 (6)	0.2510 (6)	1.0616 (6)	0.0384 (13)
H13	−0.0784	0.3150	1.1116	0.046*
C14	0.0521 (6)	0.1429 (6)	1.1175 (6)	0.0376 (13)
H14	0.0432	0.1331	1.2060	0.045*
C15	0.1349 (6)	0.0516 (5)	1.0449 (5)	0.0314 (11)
H15	0.1839	−0.0224	1.0824	0.038*
N16	0.1469 (4)	0.0670 (4)	0.9177 (4)	0.0272 (9)
O17	0.2309 (4)	−0.0305 (4)	0.8508 (4)	0.0315 (8)
O18	0.1467 (5)	0.1149 (4)	0.4162 (4)	0.0430 (10)
C19	0.4043 (6)	−0.0135 (6)	0.3803 (5)	0.0359 (12)
H19A	0.4095	−0.0330	0.2943	0.054*
H19B	0.4645	−0.0812	0.4206	0.054*
H19C	0.4336	0.0657	0.3784	0.054*
C20	0.1896 (6)	−0.1328 (6)	0.4240 (6)	0.0377 (13)
H20A	0.0948	−0.1359	0.4656	0.057*
H20B	0.2517	−0.2088	0.4502	0.057*
H20C	0.1985	−0.1279	0.3328	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.02424 (10)	0.02261 (10)	0.02981 (11)	−0.00326 (7)	−0.00512 (7)	−0.00053 (7)
Cl1	0.0327 (6)	0.0314 (6)	0.0334 (7)	−0.0040 (5)	−0.0012 (5)	−0.0018 (5)
S1	0.0320 (7)	0.0393 (8)	0.0333 (7)	0.0038 (6)	−0.0052 (5)	−0.0030 (6)
S2	0.0264 (6)	0.0248 (6)	0.0306 (6)	−0.0041 (5)	−0.0065 (5)	0.0000 (5)
C1	0.033 (3)	0.028 (3)	0.035 (3)	−0.006 (2)	−0.005 (2)	−0.001 (2)
C2	0.044 (3)	0.042 (3)	0.035 (3)	−0.006 (3)	−0.009 (3)	0.001 (3)
C3	0.051 (4)	0.046 (4)	0.037 (3)	−0.016 (3)	−0.015 (3)	0.007 (3)
C4	0.042 (3)	0.036 (3)	0.046 (3)	−0.012 (3)	−0.020 (3)	0.004 (3)
C5	0.032 (3)	0.027 (3)	0.047 (3)	−0.006 (2)	−0.015 (2)	0.000 (2)
N6	0.031 (2)	0.025 (2)	0.033 (2)	−0.0056 (18)	−0.0087 (18)	0.0007 (18)
O7	0.0277 (18)	0.031 (2)	0.033 (2)	0.0014 (15)	−0.0066 (15)	−0.0017 (16)
O8	0.036 (2)	0.038 (2)	0.037 (2)	0.0083 (17)	−0.0090 (17)	−0.0050 (17)
C9	0.034 (3)	0.025 (3)	0.044 (3)	−0.006 (2)	−0.007 (2)	0.008 (2)
C10	0.035 (3)	0.033 (3)	0.047 (3)	−0.010 (2)	−0.015 (3)	0.003 (2)
Pt2	0.02632 (10)	0.02645 (11)	0.02760 (11)	−0.00455 (8)	−0.00562 (7)	−0.00071 (7)
Cl2	0.0442 (8)	0.0317 (7)	0.0354 (7)	0.0031 (6)	−0.0071 (6)	−0.0041 (5)
S3	0.0385 (7)	0.0286 (7)	0.0342 (7)	−0.0022 (5)	−0.0130 (6)	0.0009 (5)
S4	0.0302 (6)	0.0327 (7)	0.0292 (6)	−0.0079 (5)	−0.0064 (5)	0.0001 (5)
C11	0.027 (2)	0.026 (3)	0.038 (3)	−0.006 (2)	−0.009 (2)	−0.003 (2)
C12	0.032 (3)	0.026 (3)	0.050 (3)	−0.003 (2)	−0.012 (2)	−0.009 (2)
C13	0.034 (3)	0.036 (3)	0.046 (3)	−0.001 (2)	−0.009 (2)	−0.016 (3)
C14	0.034 (3)	0.042 (3)	0.037 (3)	−0.008 (2)	−0.005 (2)	−0.010 (2)
C15	0.029 (3)	0.033 (3)	0.033 (3)	−0.007 (2)	−0.009 (2)	0.000 (2)
N16	0.023 (2)	0.027 (2)	0.031 (2)	−0.0025 (17)	−0.0061 (17)	−0.0047 (17)
O17	0.0299 (19)	0.0267 (19)	0.035 (2)	0.0031 (15)	−0.0077 (15)	−0.0055 (15)
O18	0.043 (2)	0.047 (3)	0.036 (2)	−0.0002 (19)	−0.0122 (18)	0.0021 (19)
C19	0.034 (3)	0.043 (3)	0.032 (3)	−0.015 (2)	−0.003 (2)	−0.003 (2)
C20	0.037 (3)	0.045 (3)	0.038 (3)	−0.018 (3)	−0.009 (2)	−0.007 (3)

Geometric parameters (Å, º) top

Pt1—O7	2.020 (4)	Pt2—O17	2.005 (4)
Pt1—S2	2.1826 (13)	Pt2—S4	2.1850 (14)
Pt1—S1	2.2495 (15)	Pt2—S3	2.2543 (14)
Pt1—Cl1	2.3461 (13)	Pt2—Cl2	2.3402 (14)
S1—C1	1.727 (6)	S3—C11	1.723 (6)
S2—O8	1.475 (4)	S4—O18	1.477 (4)
S2—C9	1.767 (6)	S4—C20	1.767 (6)
S2—C10	1.771 (6)	S4—C19	1.774 (6)
C1—N6	1.346 (7)	C11—N16	1.353 (7)
C1—C2	1.403 (8)	C11—C12	1.394 (8)
C2—C3	1.379 (9)	C12—C13	1.368 (9)
C2—H2	0.95	C12—H12	0.95
C3—C4	1.394 (10)	C13—C14	1.396 (9)
C3—H3	0.95	C13—H13	0.95
C4—C5	1.353 (9)	C14—C15	1.359 (8)
C4—H4	0.95	C14—H14	0.95
C5—N6	1.366 (7)	C15—N16	1.366 (7)
C5—H5	0.95	C15—H15	0.95
N6—O7	1.358 (6)	N16—O17	1.378 (5)
C9—H9A	0.98	C19—H19A	0.98
C9—H9B	0.98	C19—H19B	0.98
C9—H9C	0.98	C19—H19C	0.98
C10—H10A	0.98	C20—H20A	0.98
C10—H10B	0.98	C20—H20B	0.98
C10—H10C	0.98	C20—H20C	0.98

O7—Pt1—S2	179.05 (12)	O17—Pt2—S4	179.35 (11)
O7—Pt1—S1	86.29 (11)	O17—Pt2—S3	86.41 (11)
S2—Pt1—S1	93.15 (5)	S4—Pt2—S3	94.02 (5)
O7—Pt1—Cl1	89.02 (11)	O17—Pt2—Cl2	87.69 (11)
S2—Pt1—Cl1	91.57 (5)	S4—Pt2—Cl2	91.89 (5)
S1—Pt1—Cl1	174.53 (5)	S3—Pt2—Cl2	174.07 (5)
C1—S1—Pt1	97.4 (2)	C11—S3—Pt2	97.42 (19)
O8—S2—C9	107.7 (3)	O18—S4—C20	108.9 (3)
O8—S2—C10	108.1 (3)	O18—S4—C19	108.9 (3)
C9—S2—C10	101.3 (3)	C20—S4—C19	101.1 (3)
O8—S2—Pt1	116.54 (17)	O18—S4—Pt2	117.14 (19)
C9—S2—Pt1	111.3 (2)	C20—S4—Pt2	110.2 (2)
C10—S2—Pt1	110.8 (2)	C19—S4—Pt2	109.4 (2)
N6—C1—C2	117.9 (5)	N16—C11—C12	117.2 (5)
N6—C1—S1	119.2 (4)	N16—C11—S3	119.3 (4)
C2—C1—S1	122.9 (5)	C12—C11—S3	123.5 (4)
C3—C2—C1	119.9 (6)	C13—C12—C11	121.3 (6)
C3—C2—H2	120.1	C13—C12—H12	119.4
C1—C2—H2	120.1	C11—C12—H12	119.4
C2—C3—C4	119.9 (6)	C12—C13—C14	119.2 (5)
C2—C3—H3	120.0	C12—C13—H13	120.4
C4—C3—H3	120.0	C14—C13—H13	120.4
C5—C4—C3	119.4 (6)	C15—C14—C13	119.8 (6)
C5—C4—H4	120.3	C15—C14—H14	120.1
C3—C4—H4	120.3	C13—C14—H14	120.1
C4—C5—N6	120.0 (6)	C14—C15—N16	119.4 (5)
C4—C5—H5	120.0	C14—C15—H15	120.3
N6—C5—H5	120.0	N16—C15—H15	120.3
C1—N6—O7	121.7 (4)	C11—N16—C15	123.0 (5)
C1—N6—C5	122.9 (5)	C11—N16—O17	120.9 (4)
O7—N6—C5	115.4 (5)	C15—N16—O17	116.0 (4)
N6—O7—Pt1	115.3 (3)	N16—O17—Pt2	115.4 (3)
S2—C9—H9A	109.5	S4—C19—H19A	109.5
S2—C9—H9B	109.5	S4—C19—H19B	109.5
H9A—C9—H9B	109.5	H19A—C19—H19B	109.5
S2—C9—H9C	109.5	S4—C19—H19C	109.5
H9A—C9—H9C	109.5	H19A—C19—H19C	109.5
H9B—C9—H9C	109.5	H19B—C19—H19C	109.5
S2—C10—H10A	109.5	S4—C20—H20A	109.5
S2—C10—H10B	109.5	S4—C20—H20B	109.5
H10A—C10—H10B	109.5	H20A—C20—H20B	109.5
S2—C10—H10C	109.5	S4—C20—H20C	109.5
H10A—C10—H10C	109.5	H20A—C20—H20C	109.5
H10B—C10—H10C	109.5	H20B—C20—H20C	109.5

O7—Pt1—S1—C1	−0.8 (2)	O17—Pt2—S3—C11	−5.7 (2)
S2—Pt1—S1—C1	180.0 (2)	S4—Pt2—S3—C11	174.82 (19)
S1—Pt1—S2—O8	12.4 (2)	S3—Pt2—S4—O18	−5.8 (2)
Cl1—Pt1—S2—O8	−170.4 (2)	Cl2—Pt2—S4—O18	173.6 (2)
S1—Pt1—S2—C9	136.5 (2)	S3—Pt2—S4—C20	−131.0 (2)
Cl1—Pt1—S2—C9	−46.3 (2)	Cl2—Pt2—S4—C20	48.5 (2)
S1—Pt1—S2—C10	−111.7 (2)	S3—Pt2—S4—C19	118.7 (2)
Cl1—Pt1—S2—C10	65.5 (2)	Cl2—Pt2—S4—C19	−61.8 (2)
Pt1—S1—C1—N6	1.1 (5)	Pt2—S3—C11—N16	4.8 (4)
Pt1—S1—C1—C2	−179.1 (5)	Pt2—S3—C11—C12	−174.0 (5)
N6—C1—C2—C3	0.9 (9)	N16—C11—C12—C13	−0.1 (8)
S1—C1—C2—C3	−178.9 (5)	S3—C11—C12—C13	178.7 (5)
C1—C2—C3—C4	−0.8 (10)	C11—C12—C13—C14	0.5 (9)
C2—C3—C4—C5	0.4 (10)	C12—C13—C14—C15	−0.5 (9)
C3—C4—C5—N6	−0.1 (9)	C13—C14—C15—N16	0.2 (9)
C2—C1—N6—O7	179.4 (5)	C12—C11—N16—C15	−0.3 (8)
S1—C1—N6—O7	−0.9 (7)	S3—C11—N16—C15	−179.1 (4)
C2—C1—N6—C5	−0.7 (8)	C12—C11—N16—O17	178.9 (5)
S1—C1—N6—C5	179.1 (4)	S3—C11—N16—O17	0.0 (7)
C4—C5—N6—C1	0.3 (9)	C14—C15—N16—C11	0.2 (8)
C4—C5—N6—O7	−179.7 (5)	C14—C15—N16—O17	−178.9 (5)
C1—N6—O7—Pt1	0.0 (6)	C11—N16—O17—Pt2	−5.9 (6)
C5—N6—O7—Pt1	−180.0 (4)	C15—N16—O17—Pt2	173.3 (4)
S1—Pt1—O7—N6	0.6 (3)	S3—Pt2—O17—N16	7.0 (3)
Cl1—Pt1—O7—N6	−176.6 (3)	Cl2—Pt2—O17—N16	−172.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O17ⁱ	0.98	2.43	3.351 (8)	157
C9—H9B···Cl1	0.98	2.73	3.350 (6)	121
C10—H10A···Cl1ⁱⁱ	0.98	2.73	3.601 (7)	149
C13—H13···O7ⁱⁱⁱ	0.95	2.37	3.268 (8)	158
C15—H15···O8^iv	0.95	2.39	3.271 (7)	155
C19—H19A···O8^v	0.98	2.54	3.456 (7)	155
C20—H20A···O18^vi	0.98	2.49	3.460 (8)	172
C20—H20B···Cl2	0.98	2.75	3.366 (7)	122

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

Experimental details

Crystal data
Chemical formula	[Pt(C₅H₄NOS)Cl(C₂H₆OS)]
M_r	434.82
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	10.2407 (5), 10.9703 (5), 10.9772 (6)
α, β, γ (°)	82.950 (1), 76.720 (1), 76.554 (1)
V (Å³)	1164.21 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	12.61
Crystal size (mm)	0.47 × 0.31 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Gaussian (Coppens, 1970)
T_min, T_max	0.5, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	22889, 5542, 5032
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.070, 1.03
No. of reflections	5542
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	5.99, −1.02

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

Pt1—O7	2.020 (4)	Pt2—O17	2.005 (4)
Pt1—S2	2.1826 (13)	Pt2—S4	2.1850 (14)
Pt1—S1	2.2495 (15)	Pt2—S3	2.2543 (14)
Pt1—Cl1	2.3461 (13)	Pt2—Cl2	2.3402 (14)

O7—Pt1—S2	179.05 (12)	O17—Pt2—S4	179.35 (11)
O7—Pt1—S1	86.29 (11)	O17—Pt2—S3	86.41 (11)
S2—Pt1—S1	93.15 (5)	S4—Pt2—S3	94.02 (5)
O7—Pt1—Cl1	89.02 (11)	O17—Pt2—Cl2	87.69 (11)
S2—Pt1—Cl1	91.57 (5)	S4—Pt2—Cl2	91.89 (5)
S1—Pt1—Cl1	174.53 (5)	S3—Pt2—Cl2	174.07 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O17ⁱ	0.98	2.43	3.351 (8)	157
C9—H9B···Cl1	0.98	2.73	3.350 (6)	121
C10—H10A···Cl1ⁱⁱ	0.98	2.73	3.601 (7)	149
C13—H13···O7ⁱⁱⁱ	0.95	2.37	3.268 (8)	158
C15—H15···O8^iv	0.95	2.39	3.271 (7)	155
C19—H19A···O8^v	0.98	2.54	3.456 (7)	155
C20—H20A···O18^vi	0.98	2.49	3.460 (8)	172
C20—H20B···Cl2	0.98	2.75	3.366 (7)	122

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

Acknowledgements

RDN thanks the University Grants Commission, India, for a Teacher Fellowship.

References

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