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

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.022
• wR factor = 0.058
• Data-to-parameter ratio = 22.3

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PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K

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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).

S1. Experimental

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.

S2. Refinement

H atoms were placed in calculated positions (C–H = 0.93 to 0.96 Å) and were included in the refinement in the riding model approximation, with U_iso(H) set to 1.2–1.5U_eq(C).

Computing details

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

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)

Crystal data

[Sn(C6H5)2(C4H8NS2)2]	F(000) = 1096
Mr = 541.36	Dx = 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) Å^3	0.35 × 0.25 × 0.15 mm
Z = 4

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.058	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0314P)^2 + 0.7977P] where P = (Fo^2 + 2Fc^2)/3
2739 reflections	(Δ/σ)max = 0.001
123 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Sn1—C1	2.1239 (19)	C3—H3	0.93
Sn1—C1^i	2.1239 (19)	C4—C5	1.354 (5)
Sn1—S1^i	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—C1^i	128.41 (11)	C4—C5—C6	120.1 (3)
C1—Sn1—S1^i	109.64 (5)	C4—C5—H5	119.9
C1^i—Sn1—S1^i	108.67 (6)	C6—C5—H5	119.9
C1—Sn1—S1	108.67 (6)	C1—C6—C5	120.0 (3)
C1^i—Sn1—S1	109.64 (5)	C1—C6—H6	120.0
S1^i—Sn1—S1	82.14 (2)	C5—C6—H6	120.0
C1—Sn1—S2	82.95 (5)	N1—C7—S2	123.74 (15)
C1^i—Sn1—S2	83.99 (5)	N1—C7—S1	117.02 (15)
S1^i—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)
C1^i—Sn1—S1—C7	68.53 (9)	C1—C2—C3—C4	−0.7 (4)
S1^i—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)
C1^i—Sn1—S2—C7	−110.88 (9)	Sn1—C1—C6—C5	176.56 (19)
S1^i—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)
C1^i—Sn1—C1—C6	−153.86 (19)	C8—N1—C7—S2	1.1 (3)
S1^i—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)
C1^i—Sn1—C1—C2	23.16 (16)	Sn1—S2—C7—S1	−6.49 (10)
S1^i—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.