Di-n-butyl-bis(N-n-butyl-N-ethyl-dithio-carbamato-κS)tin(IV).

The Sn atom in the title compound, [Sn(C(4)H(9))(2)(C(7)H(14)NS(2))(2)], exists in a tetra-hedral C(2)S(2)Sn coordination geometry. The geometry is distorted towards skew-trapezoidal-bipyramidal owing to the proximity of the double-bond S atoms [Sn-S = 2.521 (2) and Sn⋯S = 2.933 (2) Å]. The Sn atom lies on a special position of mm2 site symmetry and the tin-bound n-butyl chain is disordered about a mirror plane. The ethyl and n-butyl groups of the dithio-carbamate unit are disordered about another mirror plane.

Related literature

For other di-n-butyl­tin dithio­carbamates, see: Farina et al. (2000 ▶); Lokaj et al. (1986 ▶); Menezes et al. (2005 ▶); Vrábel et al. (1992a ▶,b ▶); Vrábel & Kellö (1993 ▶); Zia-ur-Rehman et al. (2006 ▶). For a review of the applications and structures of tin dithio­carbamates, see: Tiekink (2008 ▶).

Experimental

Crystal data

[Sn(C4H9)2(C7H14NS2)2]

M = 585.54

Orthorhombic,

a = 11.1317 (2) Å

b = 19.4349 (3) Å

c = 7.7262 (1) Å

V = 1671.51 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.02 mm−1

T = 123 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.749, T max = 0.821

11224 measured reflections

2072 independent reflections

1667 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.239

S = 1.11

2072 reflections

131 parameters

55 restraints

H-atom parameters constrained

Δρmax = 1.03 e Å−3

Δρmin = −0.66 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014883/tk2428sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014883/tk2428Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Sn(C4H9)2(C7H14NS2)2]	F(000) = 612
Mr = 585.54	Dx = 1.163 Mg m−3
Orthorhombic, Pmmn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2a	Cell parameters from 5407 reflections
a = 11.1317 (2) Å	θ = 2.8–28.2°
b = 19.4349 (3) Å	µ = 1.02 mm−1
c = 7.7262 (1) Å	T = 123 K
V = 1671.51 (5) Å3	Block, colorless
Z = 2	0.30 × 0.25 × 0.20 mm

Bruker SMART APEX diffractometer	2072 independent reflections
Radiation source: fine-focus sealed tube	1667 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.749, Tmax = 0.821	k = −24→25
11224 measured reflections	l = −10→9

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.239	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.1484P)2 + 2.8257P] where P = (Fo2 + 2Fc2)/3
2072 reflections	(Δ/σ)max = 0.001
131 parameters	Δρmax = 1.03 e Å−3
55 restraints	Δρmin = −0.66 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sn1	0.7500	0.2500	0.43290 (7)	0.0602 (4)
S1	0.7500	0.33480 (11)	0.6798 (2)	0.0659 (6)
S2	0.7500	0.39534 (11)	0.3309 (3)	0.0852 (9)
N1	0.7500	0.4700 (4)	0.6210 (11)	0.0661 (18)
C1	0.5831 (12)	0.257 (4)	0.3153 (12)	0.085 (10)	0.50
H1A	0.5315	0.2190	0.3580	0.102*	0.50
H1B	0.5448	0.3008	0.3488	0.102*	0.50
C2	0.5905 (11)	0.2529 (13)	0.1171 (11)	0.100 (5)	0.50
H2A	0.6437	0.2901	0.0752	0.120*	0.50
H2B	0.6277	0.2085	0.0843	0.120*	0.50
C3	0.4697 (14)	0.2591 (17)	0.0264 (19)	0.107 (9)	0.50
H3A	0.4814	0.2581	−0.1006	0.129*	0.50
H3B	0.4314	0.3034	0.0573	0.129*	0.50
C4	0.3882 (18)	0.1990 (16)	0.082 (3)	0.130 (9)	0.50
H4A	0.3075	0.2058	0.0345	0.195*	0.50
H4B	0.3839	0.1973	0.2087	0.195*	0.50
H4C	0.4215	0.1557	0.0384	0.195*	0.50
C5	0.7500	0.4065 (5)	0.5500 (10)	0.0576 (18)
C6	0.744 (3)	0.4806 (13)	0.8169 (16)	0.085 (4)	0.25
H6A	0.7181	0.5282	0.8426	0.102*	0.25
H6B	0.6849	0.4485	0.8678	0.102*	0.25
C7	0.865 (3)	0.4679 (13)	0.8947 (16)	0.049 (4)	0.25
H7A	0.8610	0.4755	1.0200	0.074*	0.25
H7B	0.9235	0.4996	0.8437	0.074*	0.25
H7C	0.8896	0.4204	0.8716	0.074*	0.25
C6'	0.732 (3)	0.4781 (19)	0.8168 (18)	0.085 (4)	0.25
H6'1	0.6980	0.4354	0.8668	0.102*	0.25
H6'2	0.6764	0.5166	0.8415	0.102*	0.25
C7'	0.857 (3)	0.4929 (13)	0.895 (3)	0.049 (4)	0.25
H7'1	0.8499	0.4994	1.0199	0.074*	0.25
H7'2	0.8904	0.5346	0.8419	0.074*	0.25
H7'3	0.9108	0.4539	0.8711	0.074*	0.25
C8	0.7479 (19)	0.5360 (8)	0.521 (3)	0.083 (4)	0.50
H8A	0.7211	0.5739	0.5971	0.100*	0.25
H8B	0.6901	0.5321	0.4240	0.100*	0.25
C9	0.8705 (19)	0.5520 (8)	0.451 (3)	0.047 (4)	0.25
H9A	0.8942	0.5147	0.3706	0.056*	0.25
H9B	0.9283	0.5519	0.5483	0.056*	0.25
C10	0.8813 (14)	0.6206 (8)	0.356 (3)	0.042 (3)	0.25
H10A	0.9489	0.6186	0.2727	0.050*	0.25
H10B	0.8979	0.6579	0.4398	0.050*	0.25
C11	0.764 (3)	0.6359 (14)	0.259 (4)	0.102 (6)	0.25
H11A	0.7647	0.6837	0.2178	0.153*	0.25
H11B	0.6955	0.6291	0.3365	0.153*	0.25
H11C	0.7567	0.6048	0.1592	0.153*	0.25
C8'	0.734 (3)	0.5340 (12)	0.513 (5)	0.083 (4)	0.25
H8C	0.6770	0.5655	0.5725	0.100*	0.25
H8D	0.6985	0.5215	0.3999	0.100*	0.25
C9'	0.8539 (19)	0.5710 (11)	0.485 (3)	0.047 (4)	0.25
H9C	0.8873	0.5851	0.5982	0.056*	0.25
H9D	0.9114	0.5388	0.4302	0.056*	0.25
C10'	0.8399 (14)	0.6346 (8)	0.370 (3)	0.042 (3)	0.25
H10C	0.8562	0.6218	0.2482	0.050*	0.25
H10D	0.8999	0.6696	0.4046	0.050*	0.25
C11'	0.7130 (18)	0.6661 (16)	0.383 (4)	0.102 (6)	0.25
H11D	0.7018	0.6997	0.2898	0.153*	0.25
H11E	0.7037	0.6889	0.4951	0.153*	0.25
H11F	0.6528	0.6295	0.3717	0.153*	0.25

	U11	U22	U33	U12	U13	U23
Sn1	0.1059 (7)	0.0502 (5)	0.0245 (4)	0.000	0.000	0.000
S1	0.1097 (17)	0.0588 (11)	0.0292 (8)	0.000	0.000	−0.0063 (7)
S2	0.172 (3)	0.0471 (11)	0.0367 (9)	0.000	0.000	−0.0001 (8)
N1	0.080 (4)	0.055 (4)	0.064 (4)	0.000	0.000	−0.018 (3)
C1	0.112 (9)	0.08 (3)	0.062 (6)	0.03 (2)	−0.015 (6)	−0.007 (11)
C2	0.135 (11)	0.112 (11)	0.053 (5)	0.075 (14)	0.011 (7)	0.029 (11)
C3	0.145 (13)	0.11 (2)	0.070 (7)	0.041 (19)	−0.030 (9)	0.006 (12)
C4	0.137 (18)	0.16 (2)	0.089 (13)	0.024 (18)	−0.032 (12)	0.002 (13)
C5	0.073 (5)	0.057 (4)	0.043 (4)	0.000	0.000	−0.006 (3)
C6	0.086 (8)	0.091 (6)	0.077 (6)	0.000 (8)	−0.029 (8)	−0.042 (5)
C7	0.048 (5)	0.066 (11)	0.034 (4)	0.002 (9)	−0.017 (4)	0.016 (6)
C6'	0.086 (8)	0.091 (6)	0.077 (6)	0.000 (8)	−0.029 (8)	−0.042 (5)
C7'	0.048 (5)	0.066 (11)	0.034 (4)	0.002 (9)	−0.017 (4)	0.016 (6)
C8	0.068 (7)	0.063 (5)	0.118 (7)	−0.021 (8)	0.010 (9)	0.001 (5)
C9	0.040 (6)	0.057 (8)	0.044 (7)	0.002 (6)	0.011 (5)	0.013 (7)
C10	0.031 (8)	0.035 (6)	0.058 (6)	0.010 (5)	0.014 (6)	0.005 (5)
C11	0.119 (11)	0.092 (9)	0.095 (9)	0.039 (9)	−0.007 (8)	0.002 (7)
C8'	0.068 (7)	0.063 (5)	0.118 (7)	−0.021 (8)	0.010 (9)	0.001 (5)
C9'	0.040 (6)	0.057 (8)	0.044 (7)	0.002 (6)	0.011 (5)	0.013 (7)
C10'	0.031 (8)	0.035 (6)	0.058 (6)	0.010 (5)	0.014 (6)	0.005 (5)
C11'	0.119 (11)	0.092 (9)	0.095 (9)	0.039 (9)	−0.007 (8)	0.002 (7)

Sn1—C1	2.073 (13)	C7—H7B	0.9800
Sn1—C1i	2.073 (13)	C7—H7C	0.9800
Sn1—C1ii	2.073 (13)	C6'—C7'	1.545 (10)
Sn1—C1iii	2.073 (13)	C6'—H6'1	0.9900
Sn1—S1	2.5211 (19)	C6'—H6'2	0.9900
Sn1—S1iii	2.5211 (19)	C7'—H7'1	0.9800
S1—C5	1.718 (9)	C7'—H7'2	0.9800
S2—C5	1.707 (8)	C7'—H7'3	0.9800
N1—C5	1.350 (11)	C8—C9	1.4998
N1—C8	1.499 (14)	C8—H8A	0.9900
N1—C8'	1.508 (15)	C8—H8B	0.9900
N1—C8'ii	1.508 (15)	C9—C10	1.527 (9)
N1—C6	1.528 (14)	C9—H9A	0.9900
N1—C6ii	1.528 (14)	C9—H9B	0.9900
N1—C6'ii	1.534 (15)	C10—C11	1.536 (10)
N1—C6'	1.534 (15)	C10—H10A	0.9900
C1—C2	1.536 (9)	C10—H10B	0.9900
C1—H1A	0.9900	C11—H11A	0.9800
C1—H1B	0.9900	C11—H11B	0.9800
C2—C3	1.520 (9)	C11—H11C	0.9800
C2—H2A	0.9900	C8'—C9'	1.536 (10)
C2—H2B	0.9900	C8'—H8C	0.9900
C3—C4	1.540 (10)	C8'—H8D	0.9900
C3—H3A	0.9900	C9'—C10'	1.529 (10)
C3—H3B	0.9900	C9'—H9C	0.9900
C4—H4A	0.9800	C9'—H9D	0.9900
C4—H4B	0.9800	C10'—C11'	1.543 (10)
C4—H4C	0.9800	C10'—H10C	0.9900
C6—C7	1.4925	C10'—H10D	0.9900
C6—H6A	0.9900	C11'—H11D	0.9800
C6—H6B	0.9900	C11'—H11E	0.9800
C7—H7A	0.9800	C11'—H11F	0.9800
C1—Sn1—C1ii	127.4 (9)	C6—C7—H7A	109.5
C1i—Sn1—C1ii	128.0 (6)	C6—C7—H7B	109.5
C1—Sn1—C1iii	128.0 (6)	H7A—C7—H7B	109.5
C1i—Sn1—C1iii	127.4 (9)	C6—C7—H7C	109.5
C1—Sn1—S1	106.9 (14)	H7A—C7—H7C	109.5
C1i—Sn1—S1	111.9 (15)	H7B—C7—H7C	109.5
C1ii—Sn1—S1	106.9 (14)	N1—C6'—C7'	106.5 (19)
C1iii—Sn1—S1	111.9 (15)	N1—C6'—H6'1	110.4
C1—Sn1—S1iii	111.9 (15)	C7'—C6'—H6'1	110.4
C1i—Sn1—S1iii	106.9 (14)	N1—C6'—H6'2	110.4
C1ii—Sn1—S1iii	111.9 (15)	C7'—C6'—H6'2	110.4
C1iii—Sn1—S1iii	106.9 (14)	H6'1—C6'—H6'2	108.6
S1—Sn1—S1iii	81.64 (10)	C6'—C7'—H7'1	109.5
C5—S1—Sn1	95.1 (3)	C6'—C7'—H7'2	109.5
C5—N1—C8	124.9 (12)	H7'1—C7'—H7'2	109.5
C5—N1—C8'	122.0 (17)	C6'—C7'—H7'3	109.5
C5—N1—C8'ii	122.0 (17)	H7'1—C7'—H7'3	109.5
C5—N1—C6	121.7 (12)	H7'2—C7'—H7'3	109.5
C8—N1—C6	113.3 (14)	N1—C8—C9	110.5 (8)
C8'—N1—C6	115.5 (18)	N1—C8—H8A	109.6
C8'ii—N1—C6	116.1 (19)	C9—C8—H8A	109.6
C5—N1—C6ii	121.7 (12)	N1—C8—H8B	109.6
C8—N1—C6ii	113.4 (14)	C9—C8—H8B	109.6
C8'—N1—C6ii	116.1 (19)	H8A—C8—H8B	108.1
C8'ii—N1—C6ii	115.5 (18)	C8—C9—C10	115.2 (9)
C5—N1—C6'ii	119.7 (16)	C8—C9—H9A	108.5
C8—N1—C6'ii	115.1 (18)	C10—C9—H9A	108.5
C8'—N1—C6'ii	118 (2)	C8—C9—H9B	108.5
C8'ii—N1—C6'ii	116 (2)	C10—C9—H9B	108.5
C5—N1—C6'	119.7 (16)	H9A—C9—H9B	107.5
C8—N1—C6'	114.8 (18)	C9—C10—C11	109.7 (12)
C8'—N1—C6'	116 (2)	C9—C10—H10A	109.7
C8'ii—N1—C6'	118 (2)	C11—C10—H10A	109.7
C2—C1—Sn1	112.7 (9)	C9—C10—H10B	109.7
C2—C1—H1A	109.1	C11—C10—H10B	109.7
Sn1—C1—H1A	109.1	H10A—C10—H10B	108.2
C2—C1—H1B	109.1	C10—C11—H11A	109.5
Sn1—C1—H1B	109.1	C10—C11—H11B	109.5
H1A—C1—H1B	107.8	H11A—C11—H11B	109.5
C3—C2—C1	114.1 (9)	C10—C11—H11C	109.5
C3—C2—H2A	108.7	H11A—C11—H11C	109.5
C1—C2—H2A	108.7	H11B—C11—H11C	109.5
C3—C2—H2B	108.7	N1—C8'—C9'	111.1 (17)
C1—C2—H2B	108.7	N1—C8'—H8C	109.4
H2A—C2—H2B	107.6	C9'—C8'—H8C	109.4
C2—C3—C4	109.4 (13)	N1—C8'—H8D	109.4
C2—C3—H3A	109.8	C9'—C8'—H8D	109.4
C4—C3—H3A	109.8	H8C—C8'—H8D	108.0
C2—C3—H3B	109.8	C10'—C9'—C8'	111.9 (11)
C4—C3—H3B	109.8	C10'—C9'—H9C	109.2
H3A—C3—H3B	108.2	C8'—C9'—H9C	109.2
C3—C4—H4A	109.5	C10'—C9'—H9D	109.2
C3—C4—H4B	109.5	C8'—C9'—H9D	109.2
H4A—C4—H4B	109.5	H9C—C9'—H9D	107.9
C3—C4—H4C	109.5	C9'—C10'—C11'	112.1 (12)
H4A—C4—H4C	109.5	C9'—C10'—H10C	109.2
H4B—C4—H4C	109.5	C11'—C10'—H10C	109.2
N1—C5—S2	121.3 (7)	C9'—C10'—H10D	109.2
N1—C5—S1	120.3 (6)	C11'—C10'—H10D	109.2
S2—C5—S1	118.4 (5)	H10C—C10'—H10D	107.9
C7—C6—N1	109.8 (11)	C10'—C11'—H11D	109.5
C7—C6—H6A	109.7	C10'—C11'—H11E	109.5
N1—C6—H6A	109.7	H11D—C11'—H11E	109.5
C7—C6—H6B	109.7	C10'—C11'—H11F	109.5
N1—C6—H6B	109.7	H11D—C11'—H11F	109.5
H6A—C6—H6B	108.2	H11E—C11'—H11F	109.5
C1—Sn1—S1—C5	−69.5 (16)	C6'ii—N1—C5—S1	8.7 (14)
C1i—Sn1—S1—C5	−75.1 (16)	C6'—N1—C5—S1	−8.7 (14)
C1ii—Sn1—S1—C5	69.5 (16)	Sn1—S1—C5—N1	180.000 (3)
C1iii—Sn1—S1—C5	75.1 (16)	Sn1—S1—C5—S2	0.000 (2)
S1iii—Sn1—S1—C5	180.000 (2)	C5—N1—C6—C7	78.1 (9)
C8—N1—C5—S2	1.1 (10)	C8—N1—C6—C7	−105.3 (10)
C8'—N1—C5—S2	8.2 (12)	C8'—N1—C6—C7	−112.2 (12)
C8'ii—N1—C5—S2	−8.2 (12)	C8'ii—N1—C6—C7	−96.8 (13)
C6—N1—C5—S2	177.2 (14)	C6ii—N1—C6—C7	−13.4 (4)
C6ii—N1—C5—S2	−177.2 (14)	C5—N1—C8—C9	−78.2 (8)
C6'ii—N1—C5—S2	−171.3 (14)	C8'—N1—C8—C9	−144 (19)
C6'—N1—C5—S2	171.3 (14)	C8'ii—N1—C8—C9	−6(15)
C8—N1—C5—S1	−178.9 (10)	C6—N1—C8—C9	105.4 (14)
C8'—N1—C5—S1	−171.8 (12)	C6ii—N1—C8—C9	100.2 (14)
C8'ii—N1—C5—S1	171.8 (12)	C6'ii—N1—C8—C9	94.5 (15)
C6—N1—C5—S1	−2.8 (14)	C6'—N1—C8—C9	111.1 (14)
C6ii—N1—C5—S1	2.8 (14)