Di-chlorido-diphenyl-bis-(thio-urea-κS)tin(IV).

The title compound, [Sn(C6H5)2Cl2(CH4N2S)2], has been obtained from the reaction between Sn(C6H5)2Cl2 and SC(NH2)2. The asymmetric unit consists of one half of the mol-ecular unit, the remainder generated by a twofold rotation axis located along the Cl-Sn-Cl bonds. The Sn(IV) atom is coordinated by two phenyl groups, two Cl atoms and two thio-urea ligands in an all trans octa-hedral C2Cl2S2 environment. Individual mol-ecules are connected through N-H⋯Cl hydrogen bonds, leading to a three-dimensional network structure. Intra-molecular N-H⋯Cl hydrogen bonds are also present.

Related literature

For background to organotin(IV) chemistry, see: Kapoor et al. (2005 ▶); Sadiq-ur-Rehman et al. (2007) ▶; Zhang et al. (2006 ▶). For organotin(IV) compounds exhibiting biological activity, see: Nath et al. (2001 ▶); Pellerito & Nagy (2002 ▶). For chlorido­tin(IV) complexes, see: Amini et al. (2002 ▶); Müller et al. (2008 ▶). For tin(IV) complexes containing thio­urea groups, see: Donaldson et al. (1984 ▶); Sow et al. (2012 ▶); Wirth et al. (1998 ▶).

Experimental

Crystal data

[Sn(C6H5)2Cl2(CH4N2S)2]

M = 496.03

Tetragonal,

a = 14.6401 (2) Å

c = 17.7899 (3) Å

V = 3812.95 (10) Å3

Z = 8

Mo Kα radiation

μ = 1.84 mm−1

T = 150 K

0.35 × 0.35 × 0.25 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.565, T max = 0.656

23870 measured reflections

2183 independent reflections

1892 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.051

S = 1.06

2183 reflections

123 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.72 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813024343/wm2764sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024343/wm2764Isup2.hkl

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

[Sn(C6H5)2Cl2(CH4N2S)2]	Dx = 1.728 Mg m−3
Mr = 496.03	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 13789 reflections
Hall symbol: -I 4ad	θ = 2.9–27.5°
a = 14.6401 (2) Å	µ = 1.84 mm−1
c = 17.7899 (3) Å	T = 150 K
V = 3812.95 (10) Å3	Block, colourless
Z = 8	0.35 × 0.35 × 0.25 mm
F(000) = 1968

Nonius KappaCCD diffractometer	2183 independent reflections
Radiation source: fine-focus sealed tube	1892 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
152 2.0 degree images with ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −18→18
Tmin = 0.565, Tmax = 0.656	k = −18→18
23870 measured reflections	l = −23→23

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)] = 0.019	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.051	w = 1/[σ2(Fo2) + (0.0219P)2 + 4.1509P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2183 reflections	Δρmax = 0.40 e Å−3
123 parameters	Δρmin = −0.72 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00076 (6)

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
Sn	0.0000	0.2500	0.371721 (7)	0.01479 (8)
Cl1	0.0000	0.2500	0.22431 (3)	0.01928 (13)
Cl2	0.0000	0.2500	0.51334 (3)	0.02256 (13)
S	0.15011 (3)	0.35281 (3)	0.35755 (3)	0.02464 (11)
N1	0.22306 (14)	0.26557 (13)	0.47461 (10)	0.0378 (4)
H1A	0.2663 (18)	0.2448 (17)	0.4972 (14)	0.054 (8)*
H1B	0.1685 (19)	0.2538 (17)	0.4898 (14)	0.052 (7)*
N2	0.32157 (12)	0.32246 (17)	0.38782 (12)	0.0463 (5)
H2A	0.3644 (18)	0.3077 (18)	0.4143 (15)	0.056 (7)*
H2B	0.331 (2)	0.348 (2)	0.3459 (19)	0.076 (10)*
C1	0.07672 (12)	0.12407 (11)	0.36491 (8)	0.0191 (3)
C2	0.15058 (11)	0.11573 (11)	0.31618 (9)	0.0220 (3)
H2	0.1712	0.1675	0.2888	0.026*
C3	0.19442 (12)	0.03197 (13)	0.30729 (10)	0.0287 (4)
H3	0.2448	0.0266	0.2739	0.034*
C4	0.16417 (13)	−0.04356 (13)	0.34738 (11)	0.0325 (4)
H4	0.1930	−0.1011	0.3406	0.039*
C5	0.09216 (13)	−0.03516 (12)	0.39710 (11)	0.0303 (4)
H5	0.0724	−0.0867	0.4252	0.036*
C6	0.04852 (11)	0.04849 (11)	0.40608 (9)	0.0231 (3)
H6	−0.0008	0.0540	0.4405	0.028*
C7	0.23733 (12)	0.30925 (11)	0.41088 (10)	0.0247 (4)

	U11	U22	U33	U12	U13	U23
Sn	0.01624 (10)	0.01267 (10)	0.01545 (10)	−0.00079 (5)	0.000	0.000
Cl1	0.0222 (3)	0.0212 (3)	0.0144 (2)	−0.00041 (19)	0.000	0.000
Cl2	0.0323 (3)	0.0204 (3)	0.0150 (3)	−0.0046 (2)	0.000	0.000
S	0.0184 (2)	0.0218 (2)	0.0337 (2)	−0.00452 (16)	−0.00682 (17)	0.00877 (17)
N1	0.0324 (10)	0.0431 (10)	0.0380 (9)	−0.0012 (8)	−0.0151 (8)	0.0110 (8)
N2	0.0187 (9)	0.0828 (16)	0.0373 (10)	0.0101 (9)	−0.0039 (8)	0.0048 (10)
C1	0.0211 (8)	0.0180 (8)	0.0183 (7)	−0.0031 (6)	−0.0033 (6)	−0.0004 (6)
C2	0.0198 (8)	0.0217 (8)	0.0246 (8)	−0.0008 (6)	0.0003 (6)	0.0015 (6)
C3	0.0201 (9)	0.0310 (10)	0.0352 (10)	0.0061 (7)	0.0019 (7)	−0.0032 (7)
C4	0.0295 (10)	0.0244 (9)	0.0437 (11)	0.0092 (7)	−0.0056 (8)	0.0005 (8)
C5	0.0331 (10)	0.0210 (9)	0.0368 (9)	0.0020 (7)	−0.0030 (8)	0.0084 (7)
C6	0.0246 (8)	0.0216 (8)	0.0231 (8)	0.0003 (6)	−0.0003 (6)	0.0036 (6)
C7	0.0238 (8)	0.0231 (8)	0.0271 (9)	0.0021 (6)	−0.0058 (7)	−0.0057 (7)

Sn—C1	2.1622 (17)	N2—H2B	0.85 (3)
Sn—C1i	2.1622 (17)	C1—C6	1.390 (2)
Sn—Cl2	2.5194 (6)	C1—C2	1.391 (2)
Sn—Cl1	2.6224 (6)	C2—C3	1.393 (2)
Sn—Si	2.6755 (4)	C2—H2	0.9500
Sn—S	2.6755 (4)	C3—C4	1.388 (3)
S—C7	1.7137 (17)	C3—H3	0.9500
N1—C7	1.318 (2)	C4—C5	1.382 (3)
N1—H1A	0.81 (3)	C4—H4	0.9500
N1—H1B	0.86 (3)	C5—C6	1.391 (2)
N2—C7	1.314 (2)	C5—H5	0.9500
N2—H2A	0.81 (3)	C6—H6	0.9500
C1—Sn—C1i	173.57 (8)	C6—C1—C2	119.30 (16)
C1—Sn—Cl2	93.21 (4)	C6—C1—Sn	119.67 (12)
C1i—Sn—Cl2	93.21 (4)	C2—C1—Sn	120.90 (12)
C1—Sn—Cl1	86.79 (4)	C1—C2—C3	120.40 (16)
C1i—Sn—Cl1	86.79 (4)	C1—C2—H2	119.8
Cl2—Sn—Cl1	180.0	C3—C2—H2	119.8
C1—Sn—Si	86.66 (4)	C4—C3—C2	119.72 (16)
C1i—Sn—Si	92.73 (4)	C4—C3—H3	120.1
Cl2—Sn—Si	95.405 (10)	C2—C3—H3	120.1
Cl1—Sn—Si	84.595 (10)	C5—C4—C3	120.09 (17)
C1—Sn—S	92.73 (4)	C5—C4—H4	120.0
C1i—Sn—S	86.66 (4)	C3—C4—H4	120.0
Cl2—Sn—S	95.405 (10)	C4—C5—C6	120.17 (16)
Cl1—Sn—S	84.595 (10)	C4—C5—H5	119.9
Si—Sn—S	169.19 (2)	C6—C5—H5	119.9
C7—S—Sn	110.52 (6)	C1—C6—C5	120.28 (16)
C7—N1—H1A	119.0 (18)	C1—C6—H6	119.9
C7—N1—H1B	120.9 (17)	C5—C6—H6	119.9
H1A—N1—H1B	120 (2)	N2—C7—N1	119.24 (18)
C7—N2—H2A	120.3 (19)	N2—C7—S	118.15 (15)
C7—N2—H2B	119 (2)	N1—C7—S	122.58 (15)
H2A—N2—H2B	120 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···Cl2	0.86 (3)	2.50 (3)	3.345 (2)	166 (2)
N2—H2A···Cl1ii	0.81 (3)	2.41 (3)	3.2119 (19)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯Cl2	0.86 (3)	2.50 (3)	3.345 (2)	166 (2)
N2—H2A⋯Cl1i	0.81 (3)	2.41 (3)	3.2119 (19)	170 (3)

Symmetry code: (i) .