Di-n-butyl­bis(N-n-butyl-N-ethyl­dithio­carbamato-κS)tin(IV)

Baba, I.; Dzulkefli, N.N.; Ng, S.W.

doi:10.1107/S1600536809014883

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m594

doi:10.1107/S1600536809014883

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Di-n-butylbis(N-n-butyl-N-ethyldithiocarbamato-κS)tin(IV)

Ibrahim Baba,^a Nur Nadia Dzulkefli ^a and Seik Weng Ng ^b ^*

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

(Received 17 April 2009; accepted 22 April 2009; online 30 April 2009)

The Sn atom in the title compound, [Sn(C₄H₉)₂(C₇H₁₄NS₂)₂], exists in a tetrahedral C₂S₂Sn 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 dithiocarbamate 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_r = 585.54
Orthorhombic, P m m n
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[F² > 2σ(F²)] = 0.066
wR(F²) = 0.239
S = 1.11
2072 reflections
131 parameters
55 restraints
H-atom parameters constrained
Δρ_max = 1.03 e Å⁻³
Δρ_min = −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 ).

Supporting information

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

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

checkCIF report

Related literature top

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 top

Carbon disulfide (4 ml, 0.06 mol) was added to n-butylisopropylamine (8 ml, 0.06 mol) in ethanol (50 ml) at 277 K. Dibutyltin dichloride (9.1 g, 0.03 mol) dissolved in ethanol (50 ml) was added. The white solid that precipitated was collected and recrystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of dibutyldi(N-butyl-N-ethylbutyldithiocarbamato)tin at the 70% probability level; the disorder is not shown. Unlabelled atoms are related by a 2-fold axis. Hydrogen atoms are drawn as spheres of arbitrary radius.

Di-n-butylbis(N-n-butyl-N-ethyldithiocarbamato- κS)tin(IV) top

Crystal data top

[Sn(C₄H₉)₂(C₇H₁₄NS₂)₂]	F(000) = 612
M_r = 585.54	D_x = 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

Data collection top

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

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.239	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.1484P)² + 2.8257P] where P = (F_o² + 2F_c²)/3
2072 reflections	(Δ/σ)_max = 0.001
131 parameters	Δρ_max = 1.03 e Å⁻³
55 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

[Sn(C₄H₉)₂(C₇H₁₄NS₂)₂]	V = 1671.51 (5) Å³
M_r = 585.54	Z = 2
Orthorhombic, Pmmn	Mo Kα radiation
a = 11.1317 (2) Å	µ = 1.02 mm⁻¹
b = 19.4349 (3) Å	T = 123 K
c = 7.7262 (1) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEX diffractometer	2072 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1667 reflections with I > 2σ(I)
T_min = 0.749, T_max = 0.821	R_int = 0.024
11224 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	55 restraints
wR(F²) = 0.239	H-atom parameters constrained
S = 1.11	Δρ_max = 1.03 e Å⁻³
2072 reflections	Δρ_min = −0.66 e Å⁻³
131 parameters

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

	x	y	z	U_iso*/U_eq	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

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry codes: (i) x, −y+1/2, z; (ii) −x+3/2, y, z; (iii) −x+3/2, −y+1/2, z.

Experimental details

Crystal data
Chemical formula	[Sn(C₄H₉)₂(C₇H₁₄NS₂)₂]
M_r	585.54
Crystal system, space group	Orthorhombic, Pmmn
Temperature (K)	123
a, b, c (Å)	11.1317 (2), 19.4349 (3), 7.7262 (1)
V (Å³)	1671.51 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.02
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.749, 0.821
No. of measured, independent and observed [I > 2σ(I)] reflections	11224, 2072, 1667
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.239, 1.11
No. of reflections	2072
No. of parameters	131
No. of restraints	55
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.03, −0.66

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

Acknowledgements

We thank Universiti Kebangsaan Malaysia and the University of Malaya for supporting this study.

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