Bis(N-isopropyl-N-methyl­dithio­carbamato-κ2S,S′)diphenyl­tin(IV)

Muthalib, A.F.; Baba, I.; Farina, Y.; Ng, S.W.

doi:10.1107/S1600536810007415

metal-organic compounds

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Volume 66| Part 4| April 2010| Page m354

doi:10.1107/S1600536810007415

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Bis(N-isopropyl-N-methyldithiocarbamato-κ²S,S′)diphenyltin(IV)

Amirah Faizah Muthalib,^a Ibrahim Baba,^a Yang Farina ^a and Seik Weng Ng ^b ^*

^aSchool of Chemical Sciences, Universiti Kebangbaan Malaysia, 43600 Bangi, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 21 February 2010; accepted 26 February 2010; online 3 March 2010)

The dithiocarbamate anions in the title compound, [Sn(C₆H₅)₂(C₅H₁₀NS₂)₂], chelate to the Sn^IV atom, which is six-coordinated in a skew-trapezoidal-bipyramidal geometry. The molecule lies across a twofold rotation axis.

Related literature

For other diphenyltin bis(dithiocarbamate) compounds, see: Alcock et al. (1992 ); Farina et al. (2001a ,b ); Hook et al. (1994 ). For a discussion of the geometry of tin in diorganotin bischelates, see: Ng et al. (1987 ).

Experimental

Crystal data

[Sn(C₆H₅)₂(C₅H₁₀NS₂)₂]
M_r = 569.41
Orthorhombic, P b c n
a = 18.8797 (10) Å
b = 9.2067 (5) Å
c = 14.5694 (8) Å
V = 2532.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.35 mm⁻¹
T = 293 K
0.35 × 0.35 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.649, T_max = 0.774
15127 measured reflections
2785 independent reflections
2291 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.089
S = 1.10
2785 reflections
135 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—C1	2.167 (3)
Sn1—S1	2.5820 (7)
Sn1—S2	2.6910 (8)

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810007415/ci5039sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007415/ci5039Isup2.hkl

checkCIF report

Related literature top

For other diphenyltin bis(dithiocarbamate) compounds, see: Alcock et al. (1992); Farina et al. (2001a,b); Hook et al. (1994). For a discussion of the geometry of tin in diorganotin bischelates, see: Ng et al. (1987).

Experimental top

Diphenyltin dichloride (10 mmol), isopropylmethylamine (10 mmol) and carbon disulfide (10 mmol) were reacted in ethanol (50 ml) at 277 K to produce a white solid. The mixture was stirred for 1 h. The solid was collected and recrystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of [Sn(C₆H₅)₂(C₅H₁₀NS₂)₂] at the 50% probability level. H atoms are drawn as spheres of arbitrary radii. Unlabelled atoms are related to labelled atoms by the symmetry operation (1 - x, y, 1/2 - z).

Bis(N-isopropyl-N-methyldithiocarbamato- κ²S,S')diphenyltin(IV) top

Crystal data top

[Sn(C₆H₅)₂(C₅H₁₀NS₂)₂]	F(000) = 1160
M_r = 569.41	D_x = 1.493 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 6898 reflections
a = 18.8797 (10) Å	θ = 2.4–28.3°
b = 9.2067 (5) Å	µ = 1.35 mm⁻¹
c = 14.5694 (8) Å	T = 293 K
V = 2532.4 (2) Å³	Block, colourless
Z = 4	0.35 × 0.35 × 0.20 mm

Data collection top

Bruker SMART APEX diffractometer	2785 independent reflections
Radiation source: fine-focus sealed tube	2291 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
T_min = 0.649, T_max = 0.774	k = −11→11
15127 measured reflections	l = −13→18

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.044P)² + 2.0829P] where P = (F_o² + 2F_c²)/3
2785 reflections	(Δ/σ)_max = 0.001
135 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Sn(C₆H₅)₂(C₅H₁₀NS₂)₂]	V = 2532.4 (2) Å³
M_r = 569.41	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 18.8797 (10) Å	µ = 1.35 mm⁻¹
b = 9.2067 (5) Å	T = 293 K
c = 14.5694 (8) Å	0.35 × 0.35 × 0.20 mm

Data collection top

Bruker SMART APEX diffractometer	2785 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2291 reflections with I > 2σ(I)
T_min = 0.649, T_max = 0.774	R_int = 0.022
15127 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.10	Δρ_max = 0.29 e Å⁻³
2785 reflections	Δρ_min = −0.30 e Å⁻³
135 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.5000	0.71348 (3)	0.2500	0.03365 (10)
S1	0.44810 (4)	0.65957 (8)	0.41039 (4)	0.04395 (18)
S2	0.40918 (5)	0.48826 (9)	0.24740 (4)	0.04373 (19)
N1	0.36739 (12)	0.4240 (3)	0.41754 (14)	0.0388 (5)
C1	0.42071 (15)	0.8630 (3)	0.19862 (19)	0.0404 (6)
C2	0.44326 (19)	0.9844 (4)	0.1519 (3)	0.0648 (10)
H2	0.4911	0.9945	0.1382	0.078*
C3	0.3962 (2)	1.0925 (4)	0.1246 (3)	0.0802 (12)
H3	0.4128	1.1745	0.0941	0.096*
C4	0.3258 (2)	1.0776 (4)	0.1429 (3)	0.0722 (11)
H4	0.2943	1.1505	0.1258	0.087*
C5	0.3015 (2)	0.9560 (4)	0.1861 (3)	0.0692 (10)
H5	0.2533	0.9448	0.1969	0.083*
C6	0.34853 (18)	0.8492 (4)	0.2139 (2)	0.0544 (8)
H6	0.3314	0.7668	0.2434	0.065*
C7	0.40355 (14)	0.5130 (3)	0.36386 (17)	0.0356 (5)
C8	0.36473 (18)	0.4480 (4)	0.51766 (19)	0.0518 (8)
H8A	0.4088	0.4889	0.5379	0.078*
H8B	0.3568	0.3571	0.5482	0.078*
H8C	0.3268	0.5137	0.5319	0.078*
C9	0.33678 (18)	0.2865 (3)	0.3824 (2)	0.0486 (7)
H9	0.3324	0.2958	0.3156	0.058*
C10	0.2637 (2)	0.2584 (5)	0.4203 (3)	0.0784 (12)
H10A	0.2425	0.1787	0.3880	0.118*
H10B	0.2351	0.3437	0.4128	0.118*
H10C	0.2672	0.2350	0.4844	0.118*
C11	0.3871 (3)	0.1643 (5)	0.4012 (4)	0.1013 (17)
H11A	0.3723	0.0795	0.3681	0.152*
H11B	0.3875	0.1436	0.4658	0.152*
H11C	0.4339	0.1916	0.3818	0.152*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03059 (17)	0.03725 (15)	0.03310 (15)	0.000	0.00153 (9)	0.000
S1	0.0463 (4)	0.0523 (4)	0.0332 (3)	−0.0086 (3)	0.0028 (3)	−0.0052 (3)
S2	0.0555 (5)	0.0467 (4)	0.0290 (3)	−0.0106 (3)	0.0052 (3)	−0.0015 (3)
N1	0.0427 (13)	0.0454 (12)	0.0282 (10)	−0.0041 (10)	0.0043 (9)	0.0025 (9)
C1	0.0377 (16)	0.0452 (14)	0.0383 (14)	−0.0004 (11)	−0.0031 (11)	−0.0004 (11)
C2	0.050 (2)	0.063 (2)	0.082 (2)	−0.0027 (17)	−0.0015 (18)	0.0269 (19)
C3	0.085 (3)	0.062 (2)	0.093 (3)	0.006 (2)	−0.007 (2)	0.037 (2)
C4	0.072 (3)	0.072 (2)	0.073 (2)	0.029 (2)	−0.021 (2)	0.0082 (19)
C5	0.042 (2)	0.082 (3)	0.084 (3)	0.0168 (18)	−0.0038 (18)	0.008 (2)
C6	0.0450 (19)	0.0591 (19)	0.0591 (19)	0.0038 (15)	0.0025 (15)	0.0092 (16)
C7	0.0346 (14)	0.0408 (13)	0.0315 (12)	0.0029 (11)	0.0014 (10)	0.0024 (10)
C8	0.057 (2)	0.0659 (19)	0.0327 (13)	−0.0092 (16)	0.0060 (13)	0.0025 (13)
C9	0.060 (2)	0.0449 (16)	0.0413 (15)	−0.0084 (13)	0.0040 (14)	0.0043 (12)
C10	0.058 (3)	0.090 (3)	0.087 (3)	−0.026 (2)	0.004 (2)	0.004 (2)
C11	0.103 (4)	0.052 (2)	0.148 (5)	0.016 (2)	−0.014 (3)	−0.014 (3)

Geometric parameters (Å, º) top

Sn1—C1ⁱ	2.167 (3)	C4—C5	1.364 (6)
Sn1—C1	2.167 (3)	C4—H4	0.93
Sn1—S1ⁱ	2.5820 (7)	C5—C6	1.386 (5)
Sn1—S1	2.5820 (7)	C5—H5	0.93
Sn1—S2	2.6910 (8)	C6—H6	0.93
Sn1—S2ⁱ	2.6909 (8)	C8—H8A	0.96
S1—C7	1.728 (3)	C8—H8B	0.96
S2—C7	1.715 (3)	C8—H8C	0.96
N1—C7	1.323 (3)	C9—C10	1.508 (5)
N1—C8	1.476 (3)	C9—C11	1.498 (5)
N1—C9	1.483 (4)	C9—H9	0.98
C1—C2	1.376 (4)	C10—H10A	0.96
C1—C6	1.387 (4)	C10—H10B	0.96
C2—C3	1.392 (5)	C10—H10C	0.96
C2—H2	0.93	C11—H11A	0.96
C3—C4	1.362 (6)	C11—H11B	0.96
C3—H3	0.93	C11—H11C	0.96

C1ⁱ—Sn1—C1	101.13 (15)	C4—C5—H5	119.9
C1ⁱ—Sn1—S1ⁱ	99.94 (8)	C6—C5—H5	119.9
C1—Sn1—S1ⁱ	94.10 (7)	C1—C6—C5	121.1 (3)
C1ⁱ—Sn1—S1	94.10 (7)	C1—C6—H6	119.4
C1—Sn1—S1	99.94 (8)	C5—C6—H6	119.4
S1ⁱ—Sn1—S1	157.84 (4)	N1—C7—S2	122.3 (2)
C1ⁱ—Sn1—S2	159.15 (7)	N1—C7—S1	120.20 (19)
C1—Sn1—S2	92.55 (8)	S2—C7—S1	117.49 (15)
S1ⁱ—Sn1—S2	94.64 (2)	N1—C8—H8A	109.5
S1—Sn1—S2	67.84 (2)	N1—C8—H8B	109.5
C1ⁱ—Sn1—S2ⁱ	92.55 (8)	H8A—C8—H8B	109.5
C1—Sn1—S2ⁱ	159.15 (7)	N1—C8—H8C	109.5
S1ⁱ—Sn1—S2ⁱ	67.84 (2)	H8A—C8—H8C	109.5
S1—Sn1—S2ⁱ	94.64 (2)	H8B—C8—H8C	109.5
S2—Sn1—S2ⁱ	79.19 (4)	N1—C9—C10	112.1 (3)
C7—S1—Sn1	88.84 (9)	N1—C9—C11	109.3 (3)
C7—S2—Sn1	85.58 (10)	C10—C9—C11	112.6 (3)
C7—N1—C8	120.6 (2)	N1—C9—H9	107.5
C7—N1—C9	121.7 (2)	C10—C9—H9	107.5
C8—N1—C9	117.1 (2)	C11—C9—H9	107.5
C2—C1—C6	117.3 (3)	C9—C10—H10A	109.5
C2—C1—Sn1	118.2 (2)	C9—C10—H10B	109.5
C6—C1—Sn1	124.4 (2)	H10A—C10—H10B	109.5
C1—C2—C3	121.7 (3)	C9—C10—H10C	109.5
C1—C2—H2	119.2	H10A—C10—H10C	109.5
C3—C2—H2	119.2	H10B—C10—H10C	109.5
C4—C3—C2	119.6 (4)	C9—C11—H11A	109.5
C4—C3—H3	120.2	C9—C11—H11B	109.5
C2—C3—H3	120.2	H11A—C11—H11B	109.5
C3—C4—C5	120.1 (3)	C9—C11—H11C	109.5
C3—C4—H4	120.0	H11A—C11—H11C	109.5
C5—C4—H4	120.0	H11B—C11—H11C	109.5
C4—C5—C6	120.2 (3)

C1ⁱ—Sn1—S1—C7	−166.32 (12)	C6—C1—C2—C3	2.9 (6)
C1—Sn1—S1—C7	91.61 (12)	Sn1—C1—C2—C3	−173.6 (3)
S1ⁱ—Sn1—S1—C7	−36.91 (9)	C1—C2—C3—C4	−1.2 (7)
S2—Sn1—S1—C7	2.91 (9)	C2—C3—C4—C5	−1.3 (7)
S2ⁱ—Sn1—S1—C7	−73.43 (9)	C3—C4—C5—C6	1.9 (6)
C1ⁱ—Sn1—S2—C7	28.6 (2)	C2—C1—C6—C5	−2.2 (5)
C1—Sn1—S2—C7	−102.64 (12)	Sn1—C1—C6—C5	174.0 (3)
S1ⁱ—Sn1—S2—C7	163.03 (9)	C4—C5—C6—C1	−0.1 (6)
S1—Sn1—S2—C7	−2.94 (9)	C8—N1—C7—S2	179.1 (2)
S2ⁱ—Sn1—S2—C7	96.66 (9)	C9—N1—C7—S2	7.8 (4)
C1ⁱ—Sn1—C1—C2	41.2 (2)	C8—N1—C7—S1	−0.2 (4)
S1ⁱ—Sn1—C1—C2	−59.7 (3)	C9—N1—C7—S1	−171.5 (2)
S1—Sn1—C1—C2	137.5 (3)	Sn1—S2—C7—N1	−174.7 (2)
S2—Sn1—C1—C2	−154.6 (3)	Sn1—S2—C7—S1	4.59 (14)
S2ⁱ—Sn1—C1—C2	−88.8 (3)	Sn1—S1—C7—N1	174.6 (2)
C1ⁱ—Sn1—C1—C6	−135.0 (3)	Sn1—S1—C7—S2	−4.77 (15)
S1ⁱ—Sn1—C1—C6	124.0 (3)	C7—N1—C9—C10	−139.3 (3)
S1—Sn1—C1—C6	−38.8 (3)	C8—N1—C9—C10	49.2 (4)
S2—Sn1—C1—C6	29.2 (3)	C7—N1—C9—C11	95.2 (4)
S2ⁱ—Sn1—C1—C6	94.9 (3)	C8—N1—C9—C11	−76.4 (4)

Symmetry code: (i) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₂(C₅H₁₀NS₂)₂]
M_r	569.41
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	293
a, b, c (Å)	18.8797 (10), 9.2067 (5), 14.5694 (8)
V (Å³)	2532.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.35
Crystal size (mm)	0.35 × 0.35 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.649, 0.774
No. of measured, independent and observed [I > 2σ(I)] reflections	15127, 2785, 2291
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.089, 1.10
No. of reflections	2785
No. of parameters	135
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.30

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Sn1—C1	2.167 (3)	Sn1—S2	2.6910 (8)
Sn1—S1	2.5820 (7)

Acknowledgements

The authors thank Universiti Kebangsaan Malaysia (UKM-GUP-NBT-08-27-111 and 06-01-02-SF0539) and the University of Malaya for supporting this study.

References

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