Tricyclo­hexyl(piperidine-1-dithio­carboxyl­ato-κS)tin(IV)

Hao, L.; Mu, C.; Kong, B.

doi:10.1107/S1600536808021909

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page m1035

doi:10.1107/S1600536808021909

Open

access

Tricyclohexyl(piperidine-1-dithiocarboxylato-κS)tin(IV)

Lujiang Hao,^a ^* Chunhua Mu ^b and Binbin Kong ^a

^aCollege of Food and Biological Engineering, Shandong Institute of Light Industry, Jinan 250353, People's Republic of China, and ^bMaize Research Insitute, Shandong Academy of Agricultural Science, Jinan 250100, People's Republic of China
^*Correspondence e-mail: lujianghao001@yahoo.com.cn

(Received 28 June 2008; accepted 14 July 2008; online 16 July 2008)

In the title compound, [Sn(C₆H₁₁)₃(C₆H₁₀NS₂)], the Sn^IV atom is tetracoordinated by three C atoms from cyclohexyl groups and one S atom from a piperidinedithiocarboxylate anion. The coordination geometry is distorted tetrahedral, with Sn—C bond lengths in the range 2.133 (6)–2.188 (6) Å and with an Sn—S bond length of 2.4516 (19) Å. The nonbonded S atom of the piperidinedithiocarboxylate anion makes an Sn⋯S contact of 3.174 (3) Å.

Related literature

For related literature, see: Church & Halvorson (1959 ); Chung et al. (1971 ); Okabe & Oya (2000 ); Serre et al. (2005 ); Pocker & Fong (1980 ); Scapin et al. (1997 ).

Experimental

Crystal data

[Sn(C₆H₁₁)₃(C₆H₁₀NS₂)]
M_r = 528.40
Monoclinic, P 2₁ /c
a = 17.227 (8) Å
b = 7.676 (4) Å
c = 20.827 (10) Å
β = 109.598 (8)°
V = 2594 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 295 (2) K
0.26 × 0.20 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.753, T_max = 0.874
22395 measured reflections
4846 independent reflections
3085 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.141
S = 1.04
4846 reflections
253 parameters
36 restraints
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021909/bi2291sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021909/bi2291Isup2.hkl

checkCIF report

Comment top

Organotin esters of thiocarboxylic acids are widely used as biocides, fungicides and homogeneous catalysts in industry (Church & Halvorson, 1959; Chung et al., 1971). Recently, pharmaceutical properties of organotin esters of carboxylic acids have been investigated for their anti-tumour activity (Okabe & Oya, 2000; Serre et al., 2005). Studies on organotin compounds containing carboxylate ligands with additional donor atoms (e.g. N, O, or S) that are available for coordination to the Sn atom have revealed that new structural types may lead to different activities (Pocker & Fong, 1980; Scapin et al., 1997).

Related literature top

For related literature, see: Church & Halvorson (1959); Chung et al. (1971); Okabe & Oya (2000); Serre et al. (2005); Pocker & Fong (1980); Scapin et al. (1997).

Experimental top

A mixture of tricyclohexyltin bromide (0.5 mmol) and piperidinothiocarboxylic acid (0.5 mmol) in 20 ml methanol solution was refluxed for one hour. The resulting filtrate was evaporated at room temperature for three days. Colourless crystals were obtained with a yield of 21%. Elemental analysis calculated: C 54.50, H 8.14, N 2.65%; found: C 54.44, H 8.12, N 2.58%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with 30% probability displacement ellipsoids for the non-H atoms.

Tricyclohexyl(piperidine-1-dithiocarboxylato-κS)tin(IV) top

Crystal data top

[Sn(C₆H₁₁)₃(C₆H₁₀NS₂)]	F(000) = 1104
M_r = 528.40	D_x = 1.353 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4846 reflections
a = 17.227 (8) Å	θ = 1.3–25.9°
b = 7.676 (4) Å	µ = 1.16 mm⁻¹
c = 20.827 (10) Å	T = 295 K
β = 109.598 (8)°	Block, colorless
V = 2594 (2) Å³	0.26 × 0.20 × 0.12 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4846 independent reflections
Radiation source: fine-focus sealed tube	3085 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
ϕ and ω scans	θ_max = 25.7°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −21→21
T_min = 0.753, T_max = 0.874	k = −9→9
22395 measured reflections	l = −25→25

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0663P)²] where P = (F_o² + 2F_c²)/3
4846 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.76 e Å⁻³
36 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

[Sn(C₆H₁₁)₃(C₆H₁₀NS₂)]	V = 2594 (2) Å³
M_r = 528.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.227 (8) Å	µ = 1.16 mm⁻¹
b = 7.676 (4) Å	T = 295 K
c = 20.827 (10) Å	0.26 × 0.20 × 0.12 mm
β = 109.598 (8)°

Data collection top

Bruker APEXII CCD diffractometer	4846 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3085 reflections with I > 2σ(I)
T_min = 0.753, T_max = 0.874	R_int = 0.081
22395 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	36 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.04	Δρ_max = 0.76 e Å⁻³
4846 reflections	Δρ_min = −0.66 e Å⁻³
253 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Sn1	0.21447 (3)	0.20684 (5)	0.93872 (2)	0.05978 (19)
S1	0.29048 (10)	0.4803 (2)	0.97369 (9)	0.0736 (5)
S2	0.40599 (12)	0.1842 (2)	1.02151 (12)	0.0911 (6)
N1	0.4422 (3)	0.5166 (7)	1.0553 (3)	0.0670 (13)
C1	0.2069 (3)	0.0560 (7)	1.0235 (3)	0.0602 (15)
H1A	0.2511	−0.0307	1.0336	0.072*
C2	0.1285 (4)	−0.0421 (8)	1.0036 (3)	0.082 (2)
H2A	0.1246	−0.1152	0.9646	0.098*
H2B	0.0828	0.0393	0.9900	0.098*
C3	0.1217 (5)	−0.1548 (9)	1.0610 (4)	0.102 (3)
H3A	0.0680	−0.2103	1.0470	0.122*
H3B	0.1632	−0.2456	1.0709	0.122*
C4	0.1330 (5)	−0.0499 (10)	1.1237 (4)	0.104 (3)
H4A	0.0876	0.0315	1.1153	0.125*
H4B	0.1322	−0.1267	1.1604	0.125*
C5	0.2108 (5)	0.0466 (10)	1.1443 (3)	0.101 (2)
H5A	0.2562	−0.0355	1.1591	0.121*
H5B	0.2136	0.1204	1.1829	0.121*
C6	0.2207 (4)	0.1582 (8)	1.0879 (3)	0.0805 (19)
H6A	0.1816	0.2537	1.0788	0.097*
H6B	0.2757	0.2074	1.1025	0.097*
C7	0.2408 (6)	0.0636 (8)	0.8607 (4)	0.109 (3)
H7A	0.1857	0.0637	0.8261	0.131*
C8	0.2528 (7)	−0.1148 (9)	0.8691 (5)	0.161 (5)
H8A	0.2072	−0.1634	0.8806	0.193*
H8B	0.3025	−0.1345	0.9077	0.193*
C9	0.2603 (7)	−0.2145 (9)	0.8092 (5)	0.125 (4)
H9A	0.2824	−0.3296	0.8239	0.150*
H9B	0.2062	−0.2284	0.7751	0.150*
C10	0.3153 (7)	−0.1220 (10)	0.7786 (5)	0.153 (5)
H10A	0.3715	−0.1293	0.8098	0.184*
H10B	0.3131	−0.1813	0.7369	0.184*
C11	0.2952 (7)	0.0542 (11)	0.7636 (4)	0.146 (4)
H11A	0.2438	0.0607	0.7257	0.175*
H11B	0.3376	0.1075	0.7490	0.175*
C12	0.2866 (4)	0.1581 (8)	0.8223 (3)	0.083 (2)
H12A	0.3410	0.1873	0.8533	0.099*
H12B	0.2581	0.2662	0.8049	0.099*
C13	0.0980 (4)	0.3417 (7)	0.8883 (3)	0.0646 (16)
H13A	0.0558	0.2509	0.8735	0.078*
C14	0.0716 (4)	0.4589 (8)	0.9331 (3)	0.0723 (18)
H14A	0.1141	0.5457	0.9522	0.087*
H14B	0.0654	0.3919	0.9706	0.087*
C15	−0.0088 (4)	0.5499 (9)	0.8960 (3)	0.089 (2)
H15A	−0.0529	0.4647	0.8829	0.106*
H15B	−0.0208	0.6330	0.9265	0.106*
C16	−0.0060 (4)	0.6428 (8)	0.8339 (3)	0.084 (2)
H16A	−0.0597	0.6927	0.8100	0.101*
H16B	0.0335	0.7374	0.8473	0.101*
C17	0.0175 (4)	0.5240 (9)	0.7877 (3)	0.090 (2)
H17A	0.0230	0.5897	0.7497	0.108*
H17B	−0.0254	0.4377	0.7697	0.108*
C18	0.0983 (4)	0.4331 (8)	0.8250 (3)	0.0762 (18)
H18A	0.1097	0.3489	0.7946	0.091*
H18B	0.1423	0.5185	0.8370	0.091*
C19	0.3871 (4)	0.3993 (8)	1.0215 (3)	0.0638 (15)
C20	0.4243 (4)	0.6994 (8)	1.0636 (4)	0.079 (2)
H20A	0.3724	0.7314	1.0293	0.095*
H20B	0.4673	0.7721	1.0573	0.095*
C21	0.4195 (6)	0.7289 (11)	1.1325 (5)	0.112 (3)
H21A	0.3723	0.6671	1.1368	0.135*
H21B	0.4120	0.8522	1.1389	0.135*
C22	0.4978 (6)	0.6655 (15)	1.1871 (5)	0.132 (4)
H22A	0.5428	0.7433	1.1887	0.158*
H22B	0.4901	0.6700	1.2311	0.158*
C23	0.5204 (5)	0.4844 (13)	1.1745 (4)	0.112 (3)
H23A	0.4805	0.4035	1.1812	0.135*
H23B	0.5740	0.4559	1.2071	0.135*
C24	0.5228 (4)	0.4648 (10)	1.1035 (3)	0.082 (2)
H24A	0.5658	0.5379	1.0975	0.098*
H24B	0.5345	0.3447	1.0954	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0764 (3)	0.0486 (3)	0.0632 (3)	−0.0086 (2)	0.0351 (2)	−0.0032 (2)
S1	0.0691 (10)	0.0512 (9)	0.0971 (13)	−0.0085 (8)	0.0233 (9)	0.0023 (9)
S2	0.0931 (13)	0.0608 (11)	0.1322 (18)	0.0064 (9)	0.0547 (13)	0.0058 (11)
N1	0.063 (3)	0.067 (3)	0.075 (4)	−0.007 (3)	0.029 (3)	0.002 (3)
C1	0.070 (4)	0.049 (3)	0.069 (4)	0.004 (3)	0.034 (3)	0.008 (3)
C2	0.092 (5)	0.077 (5)	0.078 (5)	−0.027 (4)	0.030 (4)	0.005 (4)
C3	0.122 (6)	0.087 (5)	0.112 (7)	−0.029 (5)	0.060 (5)	0.010 (5)
C4	0.135 (7)	0.109 (6)	0.089 (6)	−0.007 (6)	0.065 (5)	0.015 (5)
C5	0.137 (7)	0.102 (6)	0.066 (5)	−0.016 (5)	0.039 (5)	0.000 (4)
C6	0.102 (5)	0.073 (4)	0.070 (4)	−0.018 (4)	0.034 (4)	−0.007 (4)
C7	0.193 (9)	0.063 (4)	0.121 (7)	−0.025 (5)	0.119 (7)	−0.027 (4)
C8	0.311 (15)	0.068 (5)	0.196 (11)	−0.029 (7)	0.206 (11)	−0.026 (6)
C9	0.203 (10)	0.075 (5)	0.147 (9)	−0.026 (6)	0.123 (8)	−0.029 (5)
C10	0.274 (13)	0.083 (6)	0.185 (10)	0.034 (8)	0.187 (11)	0.022 (7)
C11	0.242 (12)	0.128 (8)	0.126 (8)	−0.010 (8)	0.138 (9)	−0.002 (7)
C12	0.112 (6)	0.064 (4)	0.090 (5)	−0.017 (4)	0.059 (5)	−0.008 (4)
C13	0.072 (4)	0.059 (4)	0.062 (4)	−0.015 (3)	0.021 (3)	0.000 (3)
C14	0.076 (4)	0.083 (5)	0.067 (4)	0.007 (4)	0.036 (4)	0.017 (4)
C15	0.089 (5)	0.104 (6)	0.084 (5)	0.010 (4)	0.044 (4)	0.017 (4)
C16	0.105 (5)	0.069 (4)	0.080 (5)	0.008 (4)	0.035 (4)	0.013 (4)
C17	0.111 (6)	0.084 (5)	0.066 (5)	0.005 (4)	0.019 (4)	0.007 (4)
C18	0.098 (5)	0.074 (4)	0.063 (4)	0.000 (4)	0.035 (4)	−0.002 (3)
C19	0.063 (4)	0.069 (4)	0.068 (4)	−0.008 (3)	0.034 (3)	0.002 (3)
C20	0.078 (4)	0.068 (4)	0.099 (6)	−0.015 (4)	0.038 (4)	−0.004 (4)
C21	0.102 (7)	0.117 (7)	0.135 (8)	−0.005 (5)	0.062 (6)	−0.034 (6)
C22	0.116 (8)	0.190 (11)	0.099 (7)	−0.008 (8)	0.048 (6)	−0.039 (7)
C23	0.093 (6)	0.162 (9)	0.085 (6)	0.015 (6)	0.034 (5)	0.025 (6)
C24	0.060 (4)	0.105 (6)	0.082 (5)	−0.002 (4)	0.026 (4)	−0.002 (4)

Geometric parameters (Å, º) top

Sn1—C7	2.133 (6)	C10—H10B	0.970
Sn1—C1	2.151 (5)	C11—C12	1.509 (7)
Sn1—C13	2.188 (6)	C11—H11A	0.970
Sn1—S1	2.4516 (19)	C11—H11B	0.970
Sn1—S2	3.174 (3)	C12—H12A	0.970
S1—C19	1.742 (6)	C12—H12B	0.970
S2—C19	1.683 (7)	C13—C14	1.475 (6)
N1—C19	1.327 (7)	C13—C18	1.493 (6)
N1—C20	1.459 (8)	C13—H13A	0.980
N1—C24	1.469 (8)	C14—C15	1.512 (7)
C1—C2	1.480 (7)	C14—H14A	0.970
C1—C6	1.502 (7)	C14—H14B	0.970
C1—H1A	0.980	C15—C16	1.492 (7)
C2—C3	1.512 (7)	C15—H15A	0.970
C2—H2A	0.970	C15—H15B	0.970
C2—H2B	0.970	C16—C17	1.477 (7)
C3—C4	1.490 (8)	C16—H16A	0.970
C3—H3A	0.970	C16—H16B	0.970
C3—H3B	0.970	C17—C18	1.517 (7)
C4—C5	1.463 (7)	C17—H17A	0.970
C4—H4A	0.970	C17—H17B	0.970
C4—H4B	0.970	C18—H18A	0.970
C5—C6	1.510 (7)	C18—H18B	0.970
C5—H5A	0.970	C20—C21	1.484 (11)
C5—H5B	0.970	C20—H20A	0.970
C6—H6A	0.970	C20—H20B	0.970
C6—H6B	0.970	C21—C22	1.523 (12)
C7—C8	1.387 (7)	C21—H21A	0.970
C7—C12	1.487 (6)	C21—H21B	0.970
C7—H7A	0.980	C22—C23	1.490 (11)
C8—C9	1.506 (8)	C22—H22A	0.970
C8—H8A	0.970	C22—H22B	0.970
C8—H8B	0.970	C23—C24	1.501 (10)
C9—C10	1.487 (8)	C23—H23A	0.970
C9—H9A	0.970	C23—H23B	0.970
C9—H9B	0.970	C24—H24A	0.970
C10—C11	1.405 (8)	C24—H24B	0.970
C10—H10A	0.970

C7—Sn1—C1	115.8 (2)	C10—C11—H11B	108.7
C7—Sn1—C13	105.8 (3)	C12—C11—H11B	108.7
C1—Sn1—C13	110.5 (2)	H11A—C11—H11B	107.6
C7—Sn1—S1	116.04 (19)	C7—C12—C11	113.1 (5)
C1—Sn1—S1	112.96 (15)	C7—C12—H12A	109.0
C13—Sn1—S1	92.86 (16)	C11—C12—H12A	109.0
C7—Sn1—S2	86.4 (3)	C7—C12—H12B	109.0
C1—Sn1—S2	82.11 (15)	C11—C12—H12B	109.0
C13—Sn1—S2	154.88 (16)	H12A—C12—H12B	107.8
S1—Sn1—S2	62.03 (5)	C14—C13—C18	111.4 (5)
C19—S1—Sn1	100.2 (2)	C14—C13—Sn1	114.4 (4)
C19—S2—Sn1	77.3 (2)	C18—C13—Sn1	111.9 (4)
C19—N1—C20	124.9 (6)	C14—C13—H13A	106.2
C19—N1—C24	121.6 (6)	C18—C13—H13A	106.2
C20—N1—C24	111.6 (6)	Sn1—C13—H13A	106.2
C2—C1—C6	111.8 (5)	C13—C14—C15	112.5 (5)
C2—C1—Sn1	110.2 (4)	C13—C14—H14A	109.1
C6—C1—Sn1	114.6 (4)	C15—C14—H14A	109.1
C2—C1—H1A	106.6	C13—C14—H14B	109.1
C6—C1—H1A	106.6	C15—C14—H14B	109.1
Sn1—C1—H1A	106.6	H14A—C14—H14B	107.8
C1—C2—C3	112.0 (5)	C16—C15—C14	111.9 (5)
C1—C2—H2A	109.2	C16—C15—H15A	109.2
C3—C2—H2A	109.2	C14—C15—H15A	109.2
C1—C2—H2B	109.2	C16—C15—H15B	109.2
C3—C2—H2B	109.2	C14—C15—H15B	109.2
H2A—C2—H2B	107.9	H15A—C15—H15B	107.9
C4—C3—C2	111.2 (6)	C17—C16—C15	111.4 (5)
C4—C3—H3A	109.4	C17—C16—H16A	109.3
C2—C3—H3A	109.4	C15—C16—H16A	109.3
C4—C3—H3B	109.4	C17—C16—H16B	109.3
C2—C3—H3B	109.4	C15—C16—H16B	109.3
H3A—C3—H3B	108.0	H16A—C16—H16B	108.0
C5—C4—C3	111.6 (6)	C16—C17—C18	110.8 (5)
C5—C4—H4A	109.3	C16—C17—H17A	109.5
C3—C4—H4A	109.3	C18—C17—H17A	109.5
C5—C4—H4B	109.3	C16—C17—H17B	109.5
C3—C4—H4B	109.3	C18—C17—H17B	109.5
H4A—C4—H4B	108.0	H17A—C17—H17B	108.1
C4—C5—C6	112.9 (6)	C13—C18—C17	113.3 (5)
C4—C5—H5A	109.0	C13—C18—H18A	108.9
C6—C5—H5A	109.0	C17—C18—H18A	108.9
C4—C5—H5B	109.0	C13—C18—H18B	108.9
C6—C5—H5B	109.0	C17—C18—H18B	108.9
H5A—C5—H5B	107.8	H18A—C18—H18B	107.7
C1—C6—C5	112.0 (5)	N1—C19—S2	124.2 (5)
C1—C6—H6A	109.2	N1—C19—S1	116.0 (5)
C5—C6—H6A	109.2	S2—C19—S1	119.8 (4)
C1—C6—H6B	109.2	N1—C20—C21	110.1 (6)
C5—C6—H6B	109.2	N1—C20—H20A	109.6
H6A—C6—H6B	107.9	C21—C20—H20A	109.6
C8—C7—C12	117.7 (6)	N1—C20—H20B	109.6
C8—C7—Sn1	118.3 (5)	C21—C20—H20B	109.6
C12—C7—Sn1	116.4 (4)	H20A—C20—H20B	108.2
C8—C7—H7A	99.2	C20—C21—C22	110.5 (7)
C12—C7—H7A	99.2	C20—C21—H21A	109.5
Sn1—C7—H7A	99.2	C22—C21—H21A	109.5
C7—C8—C9	116.6 (7)	C20—C21—H21B	109.5
C7—C8—H8A	108.1	C22—C21—H21B	109.5
C9—C8—H8A	108.1	H21A—C21—H21B	108.1
C7—C8—H8B	108.1	C23—C22—C21	112.7 (8)
C9—C8—H8B	108.1	C23—C22—H22A	109.1
H8A—C8—H8B	107.3	C21—C22—H22A	109.1
C10—C9—C8	110.9 (6)	C23—C22—H22B	109.1
C10—C9—H9A	109.5	C21—C22—H22B	109.1
C8—C9—H9A	109.5	H22A—C22—H22B	107.8
C10—C9—H9B	109.5	C22—C23—C24	111.3 (7)
C8—C9—H9B	109.5	C22—C23—H23A	109.4
H9A—C9—H9B	108.0	C24—C23—H23A	109.4
C11—C10—C9	114.2 (7)	C22—C23—H23B	109.4
C11—C10—H10A	108.7	C24—C23—H23B	109.4
C9—C10—H10A	108.7	H23A—C23—H23B	108.0
C11—C10—H10B	108.7	N1—C24—C23	108.3 (5)
C9—C10—H10B	108.7	N1—C24—H24A	110.0
H10A—C10—H10B	107.6	C23—C24—H24A	110.0
C10—C11—C12	114.4 (7)	N1—C24—H24B	110.0
C10—C11—H11A	108.7	C23—C24—H24B	110.0
C12—C11—H11A	108.7	H24A—C24—H24B	108.4

C7—Sn1—S1—C19	−74.8 (4)	C9—C10—C11—C12	51.7 (14)
C1—Sn1—S1—C19	62.3 (3)	C8—C7—C12—C11	36.6 (13)
C13—Sn1—S1—C19	176.1 (2)	Sn1—C7—C12—C11	−174.2 (6)
S2—Sn1—S1—C19	−4.49 (19)	C10—C11—C12—C7	−42.7 (12)
C7—Sn1—S2—C19	126.8 (3)	C7—Sn1—C13—C14	−176.0 (4)
C1—Sn1—S2—C19	−116.6 (2)	C1—Sn1—C13—C14	57.9 (5)
C13—Sn1—S2—C19	6.0 (4)	S1—Sn1—C13—C14	−57.9 (4)
S1—Sn1—S2—C19	4.69 (19)	S2—Sn1—C13—C14	−59.0 (6)
C7—Sn1—C1—C2	−75.0 (5)	C7—Sn1—C13—C18	−48.1 (5)
C13—Sn1—C1—C2	45.3 (5)	C1—Sn1—C13—C18	−174.2 (4)
S1—Sn1—C1—C2	147.8 (4)	S1—Sn1—C13—C18	70.0 (4)
S2—Sn1—C1—C2	−157.2 (4)	S2—Sn1—C13—C18	68.8 (6)
C7—Sn1—C1—C6	157.8 (5)	C18—C13—C14—C15	51.6 (7)
C13—Sn1—C1—C6	−81.9 (5)	Sn1—C13—C14—C15	179.7 (4)
S1—Sn1—C1—C6	20.6 (5)	C13—C14—C15—C16	−53.7 (8)
S2—Sn1—C1—C6	75.6 (4)	C14—C15—C16—C17	55.2 (8)
C6—C1—C2—C3	−53.1 (7)	C15—C16—C17—C18	−54.7 (8)
Sn1—C1—C2—C3	178.1 (5)	C14—C13—C18—C17	−52.1 (7)
C1—C2—C3—C4	55.0 (9)	Sn1—C13—C18—C17	178.4 (4)
C2—C3—C4—C5	−55.1 (9)	C16—C17—C18—C13	53.9 (8)
C3—C4—C5—C6	54.0 (9)	C20—N1—C19—S2	−171.2 (5)
C2—C1—C6—C5	51.1 (8)	C24—N1—C19—S2	−8.1 (8)
Sn1—C1—C6—C5	177.5 (5)	C20—N1—C19—S1	9.9 (8)
C4—C5—C6—C1	−51.9 (9)	C24—N1—C19—S1	173.1 (4)
C1—Sn1—C7—C8	−1.1 (9)	Sn1—S2—C19—N1	174.5 (5)
C13—Sn1—C7—C8	−123.9 (8)	Sn1—S2—C19—S1	−6.7 (3)
S1—Sn1—C7—C8	134.8 (8)	Sn1—S1—C19—N1	−172.4 (4)
S2—Sn1—C7—C8	78.4 (9)	Sn1—S1—C19—S2	8.6 (4)
C1—Sn1—C7—C12	−150.1 (6)	C19—N1—C20—C21	101.8 (8)
C13—Sn1—C7—C12	87.1 (7)	C24—N1—C20—C21	−62.8 (7)
S1—Sn1—C7—C12	−14.3 (8)	N1—C20—C21—C22	54.6 (9)
S2—Sn1—C7—C12	−70.7 (7)	C20—C21—C22—C23	−50.4 (10)
C12—C7—C8—C9	−39.0 (14)	C21—C22—C23—C24	51.7 (10)
Sn1—C7—C8—C9	172.4 (7)	C19—N1—C24—C23	−102.5 (7)
C7—C8—C9—C10	44.6 (14)	C20—N1—C24—C23	62.7 (7)
C8—C9—C10—C11	−51.1 (13)	C22—C23—C24—N1	−56.4 (9)

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₁₁)₃(C₆H₁₀NS₂)]
M_r	528.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	17.227 (8), 7.676 (4), 20.827 (10)
β (°)	109.598 (8)
V (Å³)	2594 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.16
Crystal size (mm)	0.26 × 0.20 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.753, 0.874
No. of measured, independent and observed [I > 2σ(I)] reflections	22395, 4846, 3085
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.141, 1.04
No. of reflections	4846
No. of parameters	253
No. of restraints	36
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.66

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work is supported by the Natural Science Foundation of Shandong Province (grant No. Y2007D39).

References

Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chung, L., Rajan, K. S., Merdinger, E. & Crecz, N. (1971). Biophys. J. 11, 469–475. CrossRef CAS Web of Science PubMed Google Scholar
Church, B. S. & Halvorson, H. (1959). Nature (London), 183, 124–125. CrossRef PubMed CAS Web of Science Google Scholar
Okabe, N. & Oya, N. (2000). Acta Cryst. C56, 1416–1417. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Pocker, Y. & Fong, C. T. O. (1980). Biochemistry, 19, 2045–2049. CrossRef CAS PubMed Web of Science Google Scholar
Scapin, G., Reddy, S. G., Zheng, R. & Blanchard, J. S. (1997). Biochemistry, 36, 15081–15088. CrossRef CAS PubMed Web of Science Google Scholar
Serre, C., Marrot, J. & Ferey, G. (2005). Inorg. Chem. 44, 654–658. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar