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

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

doi:10.1107/S1600536810007427

metal-organic compounds

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Volume 66| Part 4| April 2010| Page m355

doi:10.1107/S1600536810007427

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

Amirah Faizah Muthalib,^a Ibrahim Baba ^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(C₄H₈NS₂)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(C₄H₈NS₂)₂]
M_r = 541.36
Monoclinic, C 2/c
a = 17.7925 (11) Å
b = 7.0928 (5) Å
c = 18.8889 (12) Å
β = 91.2716 (9)°
V = 2383.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.43 mm⁻¹
T = 293 K
0.35 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.634, T_max = 0.814
9577 measured reflections
2739 independent reflections
2493 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.058
S = 1.04
2739 reflections
123 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—C1	2.1239 (19)
Sn1—S1	2.5043 (5)
Sn1—S2	3.0167 (5)

C1—Sn1—C1ⁱ	128.41 (11)
Symmetry code: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ .

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/S1600536810007427/ci5040sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007427/ci5040Isup2.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), ethylmethylamine (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(C₄H₈NS₂)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, 3/2 - z).

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

Crystal data top

[Sn(C₆H₅)₂(C₄H₈NS₂)₂]	F(000) = 1096
M_r = 541.36	D_x = 1.509 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5306 reflections
a = 17.7925 (11) Å	θ = 2.2–28.2°
b = 7.0928 (5) Å	µ = 1.43 mm⁻¹
c = 18.8889 (12) Å	T = 293 K
β = 91.2716 (9)°	Block, colourless
V = 2383.2 (3) Å³	0.35 × 0.25 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	2739 independent reflections
Radiation source: fine-focus sealed tube	2493 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→22
T_min = 0.634, T_max = 0.814	k = −9→9
9577 measured reflections	l = −24→24

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.058	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0314P)² + 0.7977P] where P = (F_o² + 2F_c²)/3
2739 reflections	(Δ/σ)_max = 0.001
123 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Sn(C₆H₅)₂(C₄H₈NS₂)₂]	V = 2383.2 (3) Å³
M_r = 541.36	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.7925 (11) Å	µ = 1.43 mm⁻¹
b = 7.0928 (5) Å	T = 293 K
c = 18.8889 (12) Å	0.35 × 0.25 × 0.15 mm
β = 91.2716 (9)°

Data collection top

Bruker SMART APEX diffractometer	2739 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2493 reflections with I > 2σ(I)
T_min = 0.634, T_max = 0.814	R_int = 0.023
9577 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.058	H-atom parameters constrained
S = 1.04	Δρ_max = 0.42 e Å⁻³
2739 reflections	Δρ_min = −0.38 e Å⁻³
123 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.5000	0.38413 (2)	0.7500	0.04035 (7)
S1	0.45891 (3)	0.65032 (7)	0.67111 (3)	0.04919 (13)
S2	0.42774 (4)	0.27299 (7)	0.61016 (3)	0.05418 (14)
N1	0.41100 (11)	0.5964 (2)	0.53945 (9)	0.0507 (4)
C1	0.40305 (11)	0.2538 (3)	0.79172 (9)	0.0443 (4)
C2	0.40685 (16)	0.0719 (4)	0.81763 (14)	0.0662 (6)
H2	0.4526	0.0086	0.8191	0.079*
C3	0.3429 (2)	−0.0169 (5)	0.84136 (16)	0.0955 (11)
H3	0.3455	−0.1399	0.8583	0.115*
C4	0.2756 (2)	0.0781 (7)	0.83971 (16)	0.1033 (14)
H4	0.2327	0.0193	0.8563	0.124*
C5	0.27101 (15)	0.2563 (6)	0.81423 (15)	0.0919 (11)
H5	0.2250	0.3185	0.8127	0.110*
C6	0.33506 (13)	0.3464 (4)	0.79027 (13)	0.0645 (6)
H6	0.3319	0.4693	0.7733	0.077*
C7	0.43002 (10)	0.5087 (3)	0.59980 (10)	0.0414 (4)
C8	0.38489 (14)	0.4917 (4)	0.47687 (11)	0.0607 (6)
H8A	0.4069	0.3666	0.4777	0.073*
H8B	0.4016	0.5554	0.4346	0.073*
C9	0.30029 (16)	0.4746 (5)	0.47381 (15)	0.0858 (9)
H9A	0.2852	0.4060	0.4321	0.129*
H9B	0.2783	0.5982	0.4724	0.129*
H9C	0.2836	0.4088	0.5150	0.129*
C10	0.41159 (17)	0.8023 (3)	0.53227 (13)	0.0695 (7)
H10A	0.3976	0.8361	0.4846	0.104*
H10B	0.4611	0.8492	0.5432	0.104*
H10C	0.3764	0.8564	0.5643	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03637 (11)	0.03690 (11)	0.04792 (12)	0.000	0.00416 (7)	0.000
S1	0.0589 (3)	0.0391 (2)	0.0490 (3)	−0.0011 (2)	−0.0102 (2)	−0.0020 (2)
S2	0.0672 (4)	0.0414 (3)	0.0535 (3)	0.0006 (2)	−0.0079 (2)	−0.0050 (2)
N1	0.0552 (11)	0.0531 (10)	0.0437 (9)	0.0031 (8)	−0.0019 (8)	0.0021 (7)
C1	0.0397 (10)	0.0543 (11)	0.0390 (9)	−0.0084 (9)	0.0005 (7)	−0.0025 (8)
C2	0.0691 (16)	0.0583 (14)	0.0713 (15)	−0.0173 (12)	0.0015 (12)	0.0073 (11)
C3	0.112 (3)	0.097 (2)	0.0778 (19)	−0.060 (2)	−0.0050 (18)	0.0196 (17)
C4	0.072 (2)	0.182 (4)	0.0552 (15)	−0.066 (2)	0.0015 (14)	0.0113 (19)
C5	0.0418 (14)	0.171 (4)	0.0633 (16)	−0.0129 (19)	0.0031 (11)	−0.001 (2)
C6	0.0431 (12)	0.0930 (18)	0.0575 (13)	0.0025 (12)	0.0011 (10)	0.0039 (12)
C7	0.0349 (10)	0.0461 (10)	0.0431 (9)	0.0031 (8)	0.0006 (7)	−0.0019 (8)
C8	0.0657 (15)	0.0760 (16)	0.0402 (10)	0.0081 (12)	−0.0037 (10)	−0.0055 (11)
C9	0.076 (2)	0.108 (2)	0.0727 (17)	−0.0121 (18)	−0.0087 (14)	−0.0172 (17)
C10	0.089 (2)	0.0547 (13)	0.0646 (14)	0.0013 (13)	−0.0086 (13)	0.0156 (11)

Geometric parameters (Å, º) top

Sn1—C1	2.1239 (19)	C3—H3	0.93
Sn1—C1ⁱ	2.1239 (19)	C4—C5	1.354 (5)
Sn1—S1ⁱ	2.5043 (5)	C4—H4	0.93
Sn1—S1	2.5043 (5)	C5—C6	1.391 (4)
Sn1—S2	3.0167 (5)	C5—H5	0.93
S1—C7	1.7485 (19)	C6—H6	0.93
S2—C7	1.684 (2)	C8—C9	1.510 (4)
N1—C7	1.336 (2)	C8—H8A	0.97
N1—C10	1.467 (3)	C8—H8B	0.97
N1—C8	1.463 (3)	C9—H9A	0.96
C1—C6	1.376 (3)	C9—H9B	0.96
C1—C2	1.382 (3)	C9—H9C	0.96
C2—C3	1.383 (4)	C10—H10A	0.96
C2—H2	0.93	C10—H10B	0.96
C3—C4	1.374 (5)	C10—H10C	0.96

C1—Sn1—C1ⁱ	128.41 (11)	C4—C5—C6	120.1 (3)
C1—Sn1—S1ⁱ	109.64 (5)	C4—C5—H5	119.9
C1ⁱ—Sn1—S1ⁱ	108.67 (6)	C6—C5—H5	119.9
C1—Sn1—S1	108.67 (6)	C1—C6—C5	120.0 (3)
C1ⁱ—Sn1—S1	109.64 (5)	C1—C6—H6	120.0
S1ⁱ—Sn1—S1	82.14 (2)	C5—C6—H6	120.0
C1—Sn1—S2	82.95 (5)	N1—C7—S2	123.74 (15)
C1ⁱ—Sn1—S2	83.99 (5)	N1—C7—S1	117.02 (15)
S1ⁱ—Sn1—S2	146.217 (16)	S2—C7—S1	119.24 (11)
S1—Sn1—S2	64.079 (15)	N1—C8—C9	111.7 (2)
C7—S1—Sn1	95.86 (7)	N1—C8—H8A	109.3
C7—S2—Sn1	80.30 (6)	C9—C8—H8A	109.3
C7—N1—C10	122.72 (18)	N1—C8—H8B	109.3
C7—N1—C8	121.53 (19)	C9—C8—H8B	109.3
C10—N1—C8	115.70 (18)	H8A—C8—H8B	107.9
C6—C1—C2	119.3 (2)	C8—C9—H9A	109.5
C6—C1—Sn1	120.37 (17)	C8—C9—H9B	109.5
C2—C1—Sn1	120.29 (17)	H9A—C9—H9B	109.5
C1—C2—C3	120.4 (3)	C8—C9—H9C	109.5
C1—C2—H2	119.8	H9A—C9—H9C	109.5
C3—C2—H2	119.8	H9B—C9—H9C	109.5
C4—C3—C2	119.5 (3)	N1—C10—H10A	109.5
C4—C3—H3	120.2	N1—C10—H10B	109.5
C2—C3—H3	120.2	H10A—C10—H10B	109.5
C5—C4—C3	120.7 (3)	N1—C10—H10C	109.5
C5—C4—H4	119.6	H10A—C10—H10C	109.5
C3—C4—H4	119.6	H10B—C10—H10C	109.5

C1—Sn1—S1—C7	−76.24 (8)	Sn1—C1—C2—C3	−176.6 (2)
C1ⁱ—Sn1—S1—C7	68.53 (9)	C1—C2—C3—C4	−0.7 (4)
S1ⁱ—Sn1—S1—C7	175.62 (7)	C2—C3—C4—C5	0.9 (5)
S2—Sn1—S1—C7	−4.19 (6)	C3—C4—C5—C6	−0.9 (5)
C1—Sn1—S2—C7	119.15 (9)	C2—C1—C6—C5	−0.5 (3)
C1ⁱ—Sn1—S2—C7	−110.88 (9)	Sn1—C1—C6—C5	176.56 (19)
S1ⁱ—Sn1—S2—C7	4.05 (8)	C4—C5—C6—C1	0.7 (4)
S1—Sn1—S2—C7	4.39 (7)	C10—N1—C7—S2	178.37 (19)
C1ⁱ—Sn1—C1—C6	−153.86 (19)	C8—N1—C7—S2	1.1 (3)
S1ⁱ—Sn1—C1—C6	70.36 (18)	C10—N1—C7—S1	−1.8 (3)
S1—Sn1—C1—C6	−17.76 (18)	C8—N1—C7—S1	−179.01 (16)
S2—Sn1—C1—C6	−77.32 (17)	Sn1—S2—C7—N1	173.36 (18)
C1ⁱ—Sn1—C1—C2	23.16 (16)	Sn1—S2—C7—S1	−6.49 (10)
S1ⁱ—Sn1—C1—C2	−112.61 (17)	Sn1—S1—C7—N1	−172.10 (15)
S1—Sn1—C1—C2	159.26 (16)	Sn1—S1—C7—S2	7.75 (12)
S2—Sn1—C1—C2	99.71 (17)	C7—N1—C8—C9	92.6 (3)
C6—C1—C2—C3	0.5 (4)	C10—N1—C8—C9	−84.8 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₂(C₄H₈NS₂)₂]
M_r	541.36
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	17.7925 (11), 7.0928 (5), 18.8889 (12)
β (°)	91.2716 (9)
V (Å³)	2383.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.43
Crystal size (mm)	0.35 × 0.25 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.634, 0.814
No. of measured, independent and observed [I > 2σ(I)] reflections	9577, 2739, 2493
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.058, 1.04
No. of reflections	2739
No. of parameters	123
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.38

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

Selected geometric parameters (Å, º) top

Sn1—C1	2.1239 (19)	Sn1—S2	3.0167 (5)
Sn1—S1	2.5043 (5)

C1—Sn1—C1ⁱ	128.41 (11)

Symmetry code: (i) −x+1, y, −z+3/2.

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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