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

The title compound, [Sn(CH3)2Cl2(CH4N2S)2], crystallizes with two half-mol-ecules in the asymmetric unit. Both mol-ecules are completed by inversion symmetry with the two Sn(IV) atoms located on inversion centers. The metal atoms have distorted octa-hedral coordination environments defined by two Cl atoms, two C atoms of methyl groups and two thio-urea S atoms. In the crystal, mol-ecules are linked via N-H⋯Cl and N-H⋯S hydrogen bonds, forming a three-dimensional structure.

Related literature

For the applications and biological activity of organotin(IV) compounds, see: Davies (2010 ▶); Evans & Karpel (1984 ▶); Hadjikakou & Hadjiliadis (2009 ▶). For the crystal structures of related compounds, see: Calogero et al. (1984 ▶); Sow et al. (2012 ▶, 2013 ▶).

Experimental

Crystal data

[Sn(CH3)2Cl2(CH4N2S)2]

M = 371.90

Triclinic,

a = 6.4461 (1) Å

b = 8.4063 (2) Å

c = 12.4249 (2) Å

α = 82.172 (1)°

β = 78.240 (1)°

γ = 89.465 (1)°

V = 652.89 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.65 mm−1

T = 296 K

0.32 × 0.19 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: integration (by face-indexing with XPREP; Bruker, 2005 ▶) T min = 0.533, T max = 0.827

12611 measured reflections

3250 independent reflections

2917 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.053

S = 1.06

3250 reflections

156 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.54 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-NT (Bruker, 2005 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2013 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814002025/wm5003sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002025/wm5003Isup2.hkl

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Sn(CH3)2Cl2(CH4N2S)2]	Z = 2
Mr = 371.90	F(000) = 364
Triclinic, P1	Dx = 1.892 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4461 (1) Å	Cell parameters from 8182 reflections
b = 8.4063 (2) Å	θ = 2.5–28.3°
c = 12.4249 (2) Å	µ = 2.65 mm−1
α = 82.172 (1)°	T = 296 K
β = 78.240 (1)°	Block, colourless
γ = 89.465 (1)°	0.32 × 0.19 × 0.06 mm
V = 652.89 (2) Å3

Bruker APEXII CCD diffractometer	3250 independent reflections
Radiation source: sealed tube	2917 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
φ and ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: integration (face-indexed absorption correction carried out with XPREP; Bruker, 2005)	h = −8→8
Tmin = 0.533, Tmax = 0.827	k = −11→11
12611 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.053	w = 1/[σ2(Fo2) + (0.0263P)2 + 0.0565P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
3250 reflections	Δρmax = 0.57 e Å−3
156 parameters	Δρmin = −0.54 e Å−3
8 restraints	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: heavy-atom method	Extinction coefficient: 0.0077 (7)

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.

	x	y	z	Uiso*/Ueq
Sn1	0.5000	0.5000	0.5000	0.01799 (7)
Sn2	0.0000	0.0000	0.0000	0.01831 (7)
Cl1	0.70413 (9)	0.23120 (6)	0.47747 (4)	0.03146 (13)
Cl2	−0.11932 (8)	0.29624 (5)	−0.05524 (4)	0.02409 (11)
S1	0.36555 (8)	0.49581 (6)	0.30643 (4)	0.02033 (11)
S2	0.19978 (8)	0.15451 (6)	0.13272 (4)	0.02269 (11)
N1	0.5850 (3)	0.5545 (2)	0.10178 (15)	0.0250 (4)
H1A	0.473 (3)	0.606 (2)	0.0937 (19)	0.026 (6)*
H1B	0.691 (3)	0.561 (3)	0.0492 (19)	0.052 (9)*
N2	0.7433 (3)	0.3848 (2)	0.21896 (16)	0.0300 (4)
H2A	0.846 (3)	0.385 (3)	0.1668 (17)	0.034 (7)*
H2B	0.739 (4)	0.333 (3)	0.2837 (15)	0.030 (6)*
N3	0.2675 (3)	0.0996 (2)	0.33626 (16)	0.0313 (4)
H3A	0.283 (4)	0.197 (2)	0.334 (2)	0.030 (7)*
H3B	0.290 (4)	0.040 (3)	0.3937 (16)	0.036 (7)*
N4	0.1851 (3)	−0.1227 (2)	0.26787 (15)	0.0261 (4)
H4A	0.198 (4)	−0.169 (3)	0.3298 (15)	0.030 (6)*
H4B	0.166 (4)	−0.169 (3)	0.2126 (16)	0.026 (6)*
C1	0.5832 (3)	0.4767 (2)	0.20191 (16)	0.0202 (4)
C2	0.2200 (3)	0.3664 (3)	0.58135 (18)	0.0294 (5)
H2D	0.2568	0.2592	0.6075	0.044*
H2E	0.1275	0.3626	0.5302	0.044*
H2F	0.1494	0.4172	0.6431	0.044*
C3	0.2172 (3)	0.0340 (2)	0.25425 (16)	0.0200 (4)
C4	0.2713 (3)	0.0400 (3)	−0.12940 (17)	0.0261 (4)
H4D	0.3432	0.1368	−0.1233	0.039*
H4E	0.2290	0.0503	−0.1997	0.039*
H4F	0.3648	−0.0489	−0.1239	0.039*

	U11	U22	U33	U12	U13	U23
Sn1	0.01928 (10)	0.01734 (10)	0.01622 (10)	−0.00096 (7)	−0.00255 (7)	0.00007 (7)
Sn2	0.01640 (10)	0.01877 (10)	0.01806 (11)	0.00430 (7)	−0.00106 (7)	−0.00052 (7)
Cl1	0.0455 (3)	0.0274 (3)	0.0217 (3)	0.0133 (2)	−0.0094 (2)	−0.0012 (2)
Cl2	0.0289 (3)	0.0200 (2)	0.0240 (3)	0.00809 (19)	−0.0076 (2)	−0.00258 (19)
S1	0.0230 (2)	0.0217 (2)	0.0166 (2)	0.00450 (19)	−0.00449 (18)	−0.00357 (18)
S2	0.0292 (3)	0.0181 (2)	0.0216 (2)	0.00022 (19)	−0.0098 (2)	0.00136 (19)
N1	0.0265 (9)	0.0296 (9)	0.0183 (9)	0.0052 (8)	−0.0047 (7)	−0.0009 (7)
N2	0.0308 (10)	0.0398 (11)	0.0181 (9)	0.0166 (8)	−0.0029 (8)	−0.0037 (8)
N3	0.0539 (13)	0.0191 (9)	0.0235 (10)	−0.0018 (9)	−0.0149 (9)	−0.0005 (8)
N4	0.0379 (10)	0.0195 (9)	0.0221 (10)	−0.0003 (7)	−0.0115 (8)	0.0012 (7)
C1	0.0258 (10)	0.0181 (9)	0.0173 (9)	0.0014 (8)	−0.0052 (7)	−0.0039 (7)
C2	0.0271 (11)	0.0343 (12)	0.0244 (11)	−0.0083 (9)	−0.0016 (9)	−0.0003 (9)
C3	0.0182 (9)	0.0201 (9)	0.0215 (10)	0.0036 (7)	−0.0037 (7)	−0.0020 (8)
C4	0.0232 (10)	0.0272 (10)	0.0247 (11)	0.0024 (8)	0.0014 (8)	−0.0021 (9)

Sn1—C2i	2.127 (2)	N1—H1B	0.838 (17)
Sn1—C2	2.127 (2)	N2—C1	1.318 (3)
Sn1—Cl1i	2.6234 (5)	N2—H2A	0.828 (16)
Sn1—Cl1	2.6234 (5)	N2—H2B	0.855 (16)
Sn1—S1	2.7221 (5)	N3—C3	1.319 (3)
Sn1—S1i	2.7222 (5)	N3—H3A	0.818 (16)
Sn2—C4	2.115 (2)	N3—H3B	0.853 (16)
Sn2—C4ii	2.115 (2)	N4—C3	1.318 (3)
Sn2—Cl2ii	2.6416 (4)	N4—H4A	0.835 (16)
Sn2—Cl2	2.6416 (4)	N4—H4B	0.863 (15)
Sn2—S2ii	2.7468 (5)	C2—H2D	0.9600
Sn2—S2	2.7468 (5)	C2—H2E	0.9600
S1—C1	1.729 (2)	C2—H2F	0.9600
S2—C3	1.723 (2)	C4—H4D	0.9600
N1—C1	1.322 (3)	C4—H4E	0.9600
N1—H1A	0.853 (15)	C4—H4F	0.9600
C2i—Sn1—C2	180.0	C3—S2—Sn2	112.12 (7)
C2i—Sn1—Cl1i	89.90 (7)	C1—N1—H1A	116.1 (16)
C2—Sn1—Cl1i	90.10 (7)	C1—N1—H1B	124 (2)
C2i—Sn1—Cl1	90.10 (7)	H1A—N1—H1B	120 (2)
C2—Sn1—Cl1	89.90 (7)	C1—N2—H2A	117.5 (18)
Cl1i—Sn1—Cl1	180.00 (2)	C1—N2—H2B	118.6 (16)
C2i—Sn1—S1	92.49 (6)	H2A—N2—H2B	124 (2)
C2—Sn1—S1	87.51 (6)	C3—N3—H3A	123.0 (17)
Cl1i—Sn1—S1	88.204 (15)	C3—N3—H3B	119.6 (17)
Cl1—Sn1—S1	91.796 (15)	H3A—N3—H3B	117 (2)
C2i—Sn1—S1i	87.51 (6)	C3—N4—H4A	114.2 (16)
C2—Sn1—S1i	92.49 (6)	C3—N4—H4B	119.5 (16)
Cl1i—Sn1—S1i	91.795 (15)	H4A—N4—H4B	126 (2)
Cl1—Sn1—S1i	88.204 (15)	N2—C1—N1	119.65 (19)
S1—Sn1—S1i	180.0	N2—C1—S1	121.92 (15)
C4—Sn2—C4ii	180.0	N1—C1—S1	118.41 (15)
C4—Sn2—Cl2ii	90.67 (6)	Sn1—C2—H2D	109.5
C4ii—Sn2—Cl2ii	89.33 (6)	Sn1—C2—H2E	109.5
C4—Sn2—Cl2	89.33 (6)	H2D—C2—H2E	109.5
C4ii—Sn2—Cl2	90.67 (6)	Sn1—C2—H2F	109.5
Cl2ii—Sn2—Cl2	180.00 (2)	H2D—C2—H2F	109.5
C4—Sn2—S2ii	90.20 (6)	H2E—C2—H2F	109.5
C4ii—Sn2—S2ii	89.80 (6)	N4—C3—N3	118.47 (18)
Cl2ii—Sn2—S2ii	81.026 (14)	N4—C3—S2	122.29 (15)
Cl2—Sn2—S2ii	98.974 (14)	N3—C3—S2	119.23 (15)
C4—Sn2—S2	89.80 (6)	Sn2—C4—H4D	109.5
C4ii—Sn2—S2	90.20 (6)	Sn2—C4—H4E	109.5
Cl2ii—Sn2—S2	98.975 (14)	H4D—C4—H4E	109.5
Cl2—Sn2—S2	81.025 (14)	Sn2—C4—H4F	109.5
S2ii—Sn2—S2	180.0	H4D—C4—H4F	109.5
C1—S1—Sn1	108.77 (6)	H4E—C4—H4F	109.5
Sn1—S1—C1—N2	37.99 (18)	Sn2—S2—C3—N4	15.2 (2)
Sn1—S1—C1—N1	−143.46 (14)	Sn2—S2—C3—N3	−165.86 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl2iii	0.85 (2)	2.53 (2)	3.3703 (19)	168 (2)
N1—H1B···Cl2iv	0.84 (2)	2.87 (2)	3.4224 (19)	125 (2)
N2—H2A···Cl2iv	0.83 (2)	2.92 (2)	3.5205 (19)	131 (2)
N2—H2A···S2iv	0.83 (2)	2.98 (2)	3.5677 (19)	130 (2)
N2—H2B···Cl1	0.86 (2)	2.41 (2)	3.255 (2)	170 (2)
N3—H3A···S1	0.82 (2)	2.54 (2)	3.3522 (19)	173 (2)
N3—H3B···Cl1v	0.85 (2)	2.60 (2)	3.396 (2)	155 (2)
N4—H4A···Cl1v	0.84 (2)	2.58 (2)	3.3876 (18)	162 (2)
N4—H4B···Cl2ii	0.86 (2)	2.42 (2)	3.2871 (18)	179 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl2i	0.85 (2)	2.53 (2)	3.3703 (19)	168 (2)
N1—H1B⋯Cl2ii	0.84 (2)	2.87 (2)	3.4224 (19)	125 (2)
N2—H2A⋯Cl2ii	0.83 (2)	2.92 (2)	3.5205 (19)	131 (2)
N2—H2A⋯S2ii	0.83 (2)	2.98 (2)	3.5677 (19)	130 (2)
N2—H2B⋯Cl1	0.86 (2)	2.41 (2)	3.255 (2)	170 (2)
N3—H3A⋯S1	0.82 (2)	2.54 (2)	3.3522 (19)	173 (2)
N3—H3B⋯Cl1iii	0.85 (2)	2.60 (2)	3.396 (2)	155 (2)
N4—H4A⋯Cl1iii	0.84 (2)	2.58 (2)	3.3876 (18)	162 (2)
N4—H4B⋯Cl2iv	0.86 (2)	2.42 (2)	3.2871 (18)	179 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .