Di­chlorido­dimethyl­bis­(thio­urea-κS)tin(IV)

Sow, Y.; Diop, L.; Fernandes, M.A.; Stoeckli-Evans, H.

doi:10.1107/S1600536814002025

metal-organic compounds

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Volume 70| Part 3| March 2014| Page m83

doi:10.1107/S1600536814002025

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Dichloridodimethylbis(thiourea-κS)tin(IV)

Yaya Sow,^a ^* Libasse Diop,^a Manuel A. Fernandes ^b and Helen Stoeckli-Evans ^c

^aLaboratoire de Chimie Minerale et Analytique, Departement de Chimie, Faculte des Sciences et Techniques, Universite Cheikh Anta Diop, Dakar, Senegal, ^bSchool of Chemistry, Molecular Sciences Institute, University of the Witwatersrand, Private Bag 3, Wits 2050, Johannesburg, South Africa, and ^cInstitute of Physics, University of Neuchâtel, Rue Emile-Argand 11, CH-2000 Neuchâtel, Switzerland
^*Correspondence e-mail: yayasow81@yahoo.fr

(Received 26 January 2014; accepted 28 January 2014; online 8 February 2014)

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

CCDC reference: 984032

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_r = 371.90
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.021
wR(F²) = 0.053
S = 1.06
3250 reflections
156 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.54 e Å⁻³

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⋯Cl2^iv	0.86 (2)	2.42 (2)	3.2871 (18)	179 (2)
Symmetry codes: (i) -x, -y+1, -z; (ii) x+1, y, z; (iii) -x+1, -y, -z+1; (iv) -x, -y, -z.

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).

Supporting information

CCDC reference: 984032

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814002025/wm5003sup1.cif

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

checkCIF report

Comment top

Organotin(IV) compounds have been shown to have several applications in modern technology, for example as catalysis in polymer chemistry (Davies, 2010; Evans & Karpel, 1984). The antiproliferative and anti-tumor activities of organotin(IV) compounds have been reviewed by Hadjikakou & Hadjiliadis (2009). The crystal structures of a number of such compounds involving thiourea ligands have been reported, e.g. Dichloridodimethylbis(1,3-dimethylthiourea-κS)tin(IV) (Calogero et al., 1984), Dichloridodiphenylbis(thiourea-κS)tin(IV) (Sow et al., 2013) and µ₂-oxalato-bis[triphenyl(thiourea-κS)tin(IV)] (Sow et al., 2012). Herein we report on the synthesis and crystal structure of the title compound, [Sn(CH₃)₂Cl₂(CH₄N₂S)₂].

The molecular structure of the two independent molecules of the title compound is illustrated in Fig. 1. The compound crystallizes with two half molecules in the asymmetric unit. Both molecules possess inversion symmetry with atoms Sn1 and Sn2 located on inversion centers, both with distorted octahedral coordination geometries resulting from two Cl atoms, two C atoms of methyl groups and two thiourea S atoms. The bond lengths and angles are similar to those observed for dichloridodimethylbis(1,3-dimethylthiourea-κS)tin(IV) (Calogero et al., 1984).

In the crystal, molecules are linked via N—H···Cl and N—H···S hydrogen bonds into a three-dimensional structure (Table 1 and Fig. 2).

Related literature top

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 top

The title compound was synthesized by the reaction of dichloridodimethyltin(IV) with thiourea in a solution of absolute ethanol in a 1:2 molar ratio. After stirring for two hours, a clear solution was obtained. It was allowed to evaporate slowly at room temperature, yielding colourless block-like crystals (yield 63%; m.p. 512 K). Analytical data calculated for C₄H₁₄Cl₂N₄S₂Sn: C 12.92; H: 3.79; N: 15.06; S:17.24; Sn: 31.9 2%: found: C: 12.87; H: 3.63; N: 15.06; S: 16.95; Sn: 31.99%.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-NT (Bruker, 2005); data reduction: SAINT-NT (Bruker, 2005); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the structures of the two independent molecules of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Both atoms Sn1 and Sn2 occupy inversion centers. Non-labelled atoms are generated by symmetry codes -x + 1, -y + 1, -z + 1 (Sn1) and -x, -y, -z (Sn2).
	Fig. 2. A view along the a axis of the crystal structure of the title compound, showing the crystal packing. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

Dichloridodimethylbis(thiourea-κS)tin(IV) top

Crystal data top

[Sn(CH₃)₂Cl₂(CH₄N₂S)₂]	Z = 2
M_r = 371.90	F(000) = 364
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0263P)² + 0.0565P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3250 reflections	Δρ_max = 0.57 e Å⁻³
156 parameters	Δρ_min = −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)

Crystal data top

[Sn(CH₃)₂Cl₂(CH₄N₂S)₂]	γ = 89.465 (1)°
M_r = 371.90	V = 652.89 (2) Å³
Triclinic, P1	Z = 2
a = 6.4461 (1) Å	Mo Kα radiation
b = 8.4063 (2) Å	µ = 2.65 mm⁻¹
c = 12.4249 (2) Å	T = 296 K
α = 82.172 (1)°	0.32 × 0.19 × 0.06 mm
β = 78.240 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3250 independent reflections
Absorption correction: integration (face-indexed absorption correction carried out with XPREP; Bruker, 2005)	2917 reflections with I > 2σ(I)
T_min = 0.533, T_max = 0.827	R_int = 0.058
12611 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	8 restraints
wR(F²) = 0.053	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.57 e Å⁻³
3250 reflections	Δρ_min = −0.54 e Å⁻³
156 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

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

Hydrogen-bond geometry (Å, º) top

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···Cl2^iv	0.84 (2)	2.87 (2)	3.4224 (19)	125 (2)
N2—H2A···Cl2^iv	0.83 (2)	2.92 (2)	3.5205 (19)	131 (2)
N2—H2A···S2^iv	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···Cl1^v	0.85 (2)	2.60 (2)	3.396 (2)	155 (2)
N4—H4A···Cl1^v	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)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl2ⁱ	0.853 (15)	2.533 (16)	3.3703 (19)	168 (2)
N1—H1B···Cl2ⁱⁱ	0.838 (17)	2.87 (2)	3.4224 (19)	125 (2)
N2—H2A···Cl2ⁱⁱ	0.828 (16)	2.92 (2)	3.5205 (19)	131 (2)
N2—H2A···S2ⁱⁱ	0.828 (16)	2.98 (2)	3.5677 (19)	130 (2)
N2—H2B···Cl1	0.855 (16)	2.409 (16)	3.255 (2)	170 (2)
N3—H3A···S1	0.818 (16)	2.539 (16)	3.3522 (19)	173 (2)
N3—H3B···Cl1ⁱⁱⁱ	0.853 (16)	2.603 (18)	3.396 (2)	155 (2)
N4—H4A···Cl1ⁱⁱⁱ	0.835 (16)	2.582 (17)	3.3876 (18)	162 (2)
N4—H4B···Cl2^iv	0.863 (15)	2.424 (16)	3.2871 (18)	179 (2)

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

References

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Volume 70| Part 3| March 2014| Page m83

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