metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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 SnIV 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[Church, B. S. & Halvorson, H. (1959). Nature (London), 183, 124-125.]); Chung et al. (1971[Chung, L., Rajan, K. S., Merdinger, E. & Crecz, N. (1971). Biophys. J. 11, 469-475.]); Okabe & Oya (2000[Okabe, N. & Oya, N. (2000). Acta Cryst. C56, 1416-1417.]); Serre et al. (2005[Serre, C., Marrot, J. & Ferey, G. (2005). Inorg. Chem. 44, 654-658.]); Pocker & Fong (1980[Pocker, Y. & Fong, C. T. O. (1980). Biochemistry, 19, 2045-2049.]); Scapin et al. (1997[Scapin, G., Reddy, S. G., Zheng, R. & Blanchard, J. S. (1997). Biochemistry, 36, 15081-15088.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C6H11)3(C6H10NS2)]

  • Mr = 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[Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.753, Tmax = 0.874

  • 22395 measured reflections

  • 4846 independent reflections

  • 3085 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.76 e Å−3

  • Δρmin = −0.66 e Å−3

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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%.

Refinement top

All H atoms were placed in calculated positions with C—H = 0.97 or 0.98 Å and refined as riding with Uiso(H) = 1.2Ueq(C). The 1,2 and 1,3 C—C distances in all cyclohexane rings were restrained to be equivalent with an esd of 0.01 Å.

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
[Figure 1] 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
Mr = 528.40Dx = 1.353 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4846 reflections
a = 17.227 (8) Åθ = 1.3–25.9°
b = 7.676 (4) ŵ = 1.16 mm1
c = 20.827 (10) ÅT = 295 K
β = 109.598 (8)°Block, colorless
V = 2594 (2) Å30.26 × 0.20 × 0.12 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
4846 independent reflections
Radiation source: fine-focus sealed tube3085 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.081
ϕ and ω scansθmax = 25.7°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 2121
Tmin = 0.753, Tmax = 0.874k = 99
22395 measured reflectionsl = 2525
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0663P)2]
where P = (Fo2 + 2Fc2)/3
4846 reflections(Δ/σ)max = 0.001
253 parametersΔρmax = 0.76 e Å3
36 restraintsΔρmin = 0.66 e Å3
Crystal data top
[Sn(C6H11)3(C6H10NS2)]V = 2594 (2) Å3
Mr = 528.40Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.227 (8) ŵ = 1.16 mm1
b = 7.676 (4) ÅT = 295 K
c = 20.827 (10) Å0.26 × 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)
Tmin = 0.753, Tmax = 0.874Rint = 0.081
22395 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05336 restraints
wR(F2) = 0.141H-atom parameters constrained
S = 1.04Δρmax = 0.76 e Å3
4846 reflectionsΔρmin = 0.66 e Å3
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
xyzUiso*/Ueq
Sn10.21447 (3)0.20684 (5)0.93872 (2)0.05978 (19)
S10.29048 (10)0.4803 (2)0.97369 (9)0.0736 (5)
S20.40599 (12)0.1842 (2)1.02151 (12)0.0911 (6)
N10.4422 (3)0.5166 (7)1.0553 (3)0.0670 (13)
C10.2069 (3)0.0560 (7)1.0235 (3)0.0602 (15)
H1A0.25110.03071.03360.072*
C20.1285 (4)0.0421 (8)1.0036 (3)0.082 (2)
H2A0.12460.11520.96460.098*
H2B0.08280.03930.99000.098*
C30.1217 (5)0.1548 (9)1.0610 (4)0.102 (3)
H3A0.06800.21031.04700.122*
H3B0.16320.24561.07090.122*
C40.1330 (5)0.0499 (10)1.1237 (4)0.104 (3)
H4A0.08760.03151.11530.125*
H4B0.13220.12671.16040.125*
C50.2108 (5)0.0466 (10)1.1443 (3)0.101 (2)
H5A0.25620.03551.15910.121*
H5B0.21360.12041.18290.121*
C60.2207 (4)0.1582 (8)1.0879 (3)0.0805 (19)
H6A0.18160.25371.07880.097*
H6B0.27570.20741.10250.097*
C70.2408 (6)0.0636 (8)0.8607 (4)0.109 (3)
H7A0.18570.06370.82610.131*
C80.2528 (7)0.1148 (9)0.8691 (5)0.161 (5)
H8A0.20720.16340.88060.193*
H8B0.30250.13450.90770.193*
C90.2603 (7)0.2145 (9)0.8092 (5)0.125 (4)
H9A0.28240.32960.82390.150*
H9B0.20620.22840.77510.150*
C100.3153 (7)0.1220 (10)0.7786 (5)0.153 (5)
H10A0.37150.12930.80980.184*
H10B0.31310.18130.73690.184*
C110.2952 (7)0.0542 (11)0.7636 (4)0.146 (4)
H11A0.24380.06070.72570.175*
H11B0.33760.10750.74900.175*
C120.2866 (4)0.1581 (8)0.8223 (3)0.083 (2)
H12A0.34100.18730.85330.099*
H12B0.25810.26620.80490.099*
C130.0980 (4)0.3417 (7)0.8883 (3)0.0646 (16)
H13A0.05580.25090.87350.078*
C140.0716 (4)0.4589 (8)0.9331 (3)0.0723 (18)
H14A0.11410.54570.95220.087*
H14B0.06540.39190.97060.087*
C150.0088 (4)0.5499 (9)0.8960 (3)0.089 (2)
H15A0.05290.46470.88290.106*
H15B0.02080.63300.92650.106*
C160.0060 (4)0.6428 (8)0.8339 (3)0.084 (2)
H16A0.05970.69270.81000.101*
H16B0.03350.73740.84730.101*
C170.0175 (4)0.5240 (9)0.7877 (3)0.090 (2)
H17A0.02300.58970.74970.108*
H17B0.02540.43770.76970.108*
C180.0983 (4)0.4331 (8)0.8250 (3)0.0762 (18)
H18A0.10970.34890.79460.091*
H18B0.14230.51850.83700.091*
C190.3871 (4)0.3993 (8)1.0215 (3)0.0638 (15)
C200.4243 (4)0.6994 (8)1.0636 (4)0.079 (2)
H20A0.37240.73141.02930.095*
H20B0.46730.77211.05730.095*
C210.4195 (6)0.7289 (11)1.1325 (5)0.112 (3)
H21A0.37230.66711.13680.135*
H21B0.41200.85221.13890.135*
C220.4978 (6)0.6655 (15)1.1871 (5)0.132 (4)
H22A0.54280.74331.18870.158*
H22B0.49010.67001.23110.158*
C230.5204 (5)0.4844 (13)1.1745 (4)0.112 (3)
H23A0.48050.40351.18120.135*
H23B0.57400.45591.20710.135*
C240.5228 (4)0.4648 (10)1.1035 (3)0.082 (2)
H24A0.56580.53791.09750.098*
H24B0.53450.34471.09540.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0764 (3)0.0486 (3)0.0632 (3)0.0086 (2)0.0351 (2)0.0032 (2)
S10.0691 (10)0.0512 (9)0.0971 (13)0.0085 (8)0.0233 (9)0.0023 (9)
S20.0931 (13)0.0608 (11)0.1322 (18)0.0064 (9)0.0547 (13)0.0058 (11)
N10.063 (3)0.067 (3)0.075 (4)0.007 (3)0.029 (3)0.002 (3)
C10.070 (4)0.049 (3)0.069 (4)0.004 (3)0.034 (3)0.008 (3)
C20.092 (5)0.077 (5)0.078 (5)0.027 (4)0.030 (4)0.005 (4)
C30.122 (6)0.087 (5)0.112 (7)0.029 (5)0.060 (5)0.010 (5)
C40.135 (7)0.109 (6)0.089 (6)0.007 (6)0.065 (5)0.015 (5)
C50.137 (7)0.102 (6)0.066 (5)0.016 (5)0.039 (5)0.000 (4)
C60.102 (5)0.073 (4)0.070 (4)0.018 (4)0.034 (4)0.007 (4)
C70.193 (9)0.063 (4)0.121 (7)0.025 (5)0.119 (7)0.027 (4)
C80.311 (15)0.068 (5)0.196 (11)0.029 (7)0.206 (11)0.026 (6)
C90.203 (10)0.075 (5)0.147 (9)0.026 (6)0.123 (8)0.029 (5)
C100.274 (13)0.083 (6)0.185 (10)0.034 (8)0.187 (11)0.022 (7)
C110.242 (12)0.128 (8)0.126 (8)0.010 (8)0.138 (9)0.002 (7)
C120.112 (6)0.064 (4)0.090 (5)0.017 (4)0.059 (5)0.008 (4)
C130.072 (4)0.059 (4)0.062 (4)0.015 (3)0.021 (3)0.000 (3)
C140.076 (4)0.083 (5)0.067 (4)0.007 (4)0.036 (4)0.017 (4)
C150.089 (5)0.104 (6)0.084 (5)0.010 (4)0.044 (4)0.017 (4)
C160.105 (5)0.069 (4)0.080 (5)0.008 (4)0.035 (4)0.013 (4)
C170.111 (6)0.084 (5)0.066 (5)0.005 (4)0.019 (4)0.007 (4)
C180.098 (5)0.074 (4)0.063 (4)0.000 (4)0.035 (4)0.002 (3)
C190.063 (4)0.069 (4)0.068 (4)0.008 (3)0.034 (3)0.002 (3)
C200.078 (4)0.068 (4)0.099 (6)0.015 (4)0.038 (4)0.004 (4)
C210.102 (7)0.117 (7)0.135 (8)0.005 (5)0.062 (6)0.034 (6)
C220.116 (8)0.190 (11)0.099 (7)0.008 (8)0.048 (6)0.039 (7)
C230.093 (6)0.162 (9)0.085 (6)0.015 (6)0.034 (5)0.025 (6)
C240.060 (4)0.105 (6)0.082 (5)0.002 (4)0.026 (4)0.002 (4)
Geometric parameters (Å, º) top
Sn1—C72.133 (6)C10—H10B0.970
Sn1—C12.151 (5)C11—C121.509 (7)
Sn1—C132.188 (6)C11—H11A0.970
Sn1—S12.4516 (19)C11—H11B0.970
Sn1—S23.174 (3)C12—H12A0.970
S1—C191.742 (6)C12—H12B0.970
S2—C191.683 (7)C13—C141.475 (6)
N1—C191.327 (7)C13—C181.493 (6)
N1—C201.459 (8)C13—H13A0.980
N1—C241.469 (8)C14—C151.512 (7)
C1—C21.480 (7)C14—H14A0.970
C1—C61.502 (7)C14—H14B0.970
C1—H1A0.980C15—C161.492 (7)
C2—C31.512 (7)C15—H15A0.970
C2—H2A0.970C15—H15B0.970
C2—H2B0.970C16—C171.477 (7)
C3—C41.490 (8)C16—H16A0.970
C3—H3A0.970C16—H16B0.970
C3—H3B0.970C17—C181.517 (7)
C4—C51.463 (7)C17—H17A0.970
C4—H4A0.970C17—H17B0.970
C4—H4B0.970C18—H18A0.970
C5—C61.510 (7)C18—H18B0.970
C5—H5A0.970C20—C211.484 (11)
C5—H5B0.970C20—H20A0.970
C6—H6A0.970C20—H20B0.970
C6—H6B0.970C21—C221.523 (12)
C7—C81.387 (7)C21—H21A0.970
C7—C121.487 (6)C21—H21B0.970
C7—H7A0.980C22—C231.490 (11)
C8—C91.506 (8)C22—H22A0.970
C8—H8A0.970C22—H22B0.970
C8—H8B0.970C23—C241.501 (10)
C9—C101.487 (8)C23—H23A0.970
C9—H9A0.970C23—H23B0.970
C9—H9B0.970C24—H24A0.970
C10—C111.405 (8)C24—H24B0.970
C10—H10A0.970
C7—Sn1—C1115.8 (2)C10—C11—H11B108.7
C7—Sn1—C13105.8 (3)C12—C11—H11B108.7
C1—Sn1—C13110.5 (2)H11A—C11—H11B107.6
C7—Sn1—S1116.04 (19)C7—C12—C11113.1 (5)
C1—Sn1—S1112.96 (15)C7—C12—H12A109.0
C13—Sn1—S192.86 (16)C11—C12—H12A109.0
C7—Sn1—S286.4 (3)C7—C12—H12B109.0
C1—Sn1—S282.11 (15)C11—C12—H12B109.0
C13—Sn1—S2154.88 (16)H12A—C12—H12B107.8
S1—Sn1—S262.03 (5)C14—C13—C18111.4 (5)
C19—S1—Sn1100.2 (2)C14—C13—Sn1114.4 (4)
C19—S2—Sn177.3 (2)C18—C13—Sn1111.9 (4)
C19—N1—C20124.9 (6)C14—C13—H13A106.2
C19—N1—C24121.6 (6)C18—C13—H13A106.2
C20—N1—C24111.6 (6)Sn1—C13—H13A106.2
C2—C1—C6111.8 (5)C13—C14—C15112.5 (5)
C2—C1—Sn1110.2 (4)C13—C14—H14A109.1
C6—C1—Sn1114.6 (4)C15—C14—H14A109.1
C2—C1—H1A106.6C13—C14—H14B109.1
C6—C1—H1A106.6C15—C14—H14B109.1
Sn1—C1—H1A106.6H14A—C14—H14B107.8
C1—C2—C3112.0 (5)C16—C15—C14111.9 (5)
C1—C2—H2A109.2C16—C15—H15A109.2
C3—C2—H2A109.2C14—C15—H15A109.2
C1—C2—H2B109.2C16—C15—H15B109.2
C3—C2—H2B109.2C14—C15—H15B109.2
H2A—C2—H2B107.9H15A—C15—H15B107.9
C4—C3—C2111.2 (6)C17—C16—C15111.4 (5)
C4—C3—H3A109.4C17—C16—H16A109.3
C2—C3—H3A109.4C15—C16—H16A109.3
C4—C3—H3B109.4C17—C16—H16B109.3
C2—C3—H3B109.4C15—C16—H16B109.3
H3A—C3—H3B108.0H16A—C16—H16B108.0
C5—C4—C3111.6 (6)C16—C17—C18110.8 (5)
C5—C4—H4A109.3C16—C17—H17A109.5
C3—C4—H4A109.3C18—C17—H17A109.5
C5—C4—H4B109.3C16—C17—H17B109.5
C3—C4—H4B109.3C18—C17—H17B109.5
H4A—C4—H4B108.0H17A—C17—H17B108.1
C4—C5—C6112.9 (6)C13—C18—C17113.3 (5)
C4—C5—H5A109.0C13—C18—H18A108.9
C6—C5—H5A109.0C17—C18—H18A108.9
C4—C5—H5B109.0C13—C18—H18B108.9
C6—C5—H5B109.0C17—C18—H18B108.9
H5A—C5—H5B107.8H18A—C18—H18B107.7
C1—C6—C5112.0 (5)N1—C19—S2124.2 (5)
C1—C6—H6A109.2N1—C19—S1116.0 (5)
C5—C6—H6A109.2S2—C19—S1119.8 (4)
C1—C6—H6B109.2N1—C20—C21110.1 (6)
C5—C6—H6B109.2N1—C20—H20A109.6
H6A—C6—H6B107.9C21—C20—H20A109.6
C8—C7—C12117.7 (6)N1—C20—H20B109.6
C8—C7—Sn1118.3 (5)C21—C20—H20B109.6
C12—C7—Sn1116.4 (4)H20A—C20—H20B108.2
C8—C7—H7A99.2C20—C21—C22110.5 (7)
C12—C7—H7A99.2C20—C21—H21A109.5
Sn1—C7—H7A99.2C22—C21—H21A109.5
C7—C8—C9116.6 (7)C20—C21—H21B109.5
C7—C8—H8A108.1C22—C21—H21B109.5
C9—C8—H8A108.1H21A—C21—H21B108.1
C7—C8—H8B108.1C23—C22—C21112.7 (8)
C9—C8—H8B108.1C23—C22—H22A109.1
H8A—C8—H8B107.3C21—C22—H22A109.1
C10—C9—C8110.9 (6)C23—C22—H22B109.1
C10—C9—H9A109.5C21—C22—H22B109.1
C8—C9—H9A109.5H22A—C22—H22B107.8
C10—C9—H9B109.5C22—C23—C24111.3 (7)
C8—C9—H9B109.5C22—C23—H23A109.4
H9A—C9—H9B108.0C24—C23—H23A109.4
C11—C10—C9114.2 (7)C22—C23—H23B109.4
C11—C10—H10A108.7C24—C23—H23B109.4
C9—C10—H10A108.7H23A—C23—H23B108.0
C11—C10—H10B108.7N1—C24—C23108.3 (5)
C9—C10—H10B108.7N1—C24—H24A110.0
H10A—C10—H10B107.6C23—C24—H24A110.0
C10—C11—C12114.4 (7)N1—C24—H24B110.0
C10—C11—H11A108.7C23—C24—H24B110.0
C12—C11—H11A108.7H24A—C24—H24B108.4
C7—Sn1—S1—C1974.8 (4)C9—C10—C11—C1251.7 (14)
C1—Sn1—S1—C1962.3 (3)C8—C7—C12—C1136.6 (13)
C13—Sn1—S1—C19176.1 (2)Sn1—C7—C12—C11174.2 (6)
S2—Sn1—S1—C194.49 (19)C10—C11—C12—C742.7 (12)
C7—Sn1—S2—C19126.8 (3)C7—Sn1—C13—C14176.0 (4)
C1—Sn1—S2—C19116.6 (2)C1—Sn1—C13—C1457.9 (5)
C13—Sn1—S2—C196.0 (4)S1—Sn1—C13—C1457.9 (4)
S1—Sn1—S2—C194.69 (19)S2—Sn1—C13—C1459.0 (6)
C7—Sn1—C1—C275.0 (5)C7—Sn1—C13—C1848.1 (5)
C13—Sn1—C1—C245.3 (5)C1—Sn1—C13—C18174.2 (4)
S1—Sn1—C1—C2147.8 (4)S1—Sn1—C13—C1870.0 (4)
S2—Sn1—C1—C2157.2 (4)S2—Sn1—C13—C1868.8 (6)
C7—Sn1—C1—C6157.8 (5)C18—C13—C14—C1551.6 (7)
C13—Sn1—C1—C681.9 (5)Sn1—C13—C14—C15179.7 (4)
S1—Sn1—C1—C620.6 (5)C13—C14—C15—C1653.7 (8)
S2—Sn1—C1—C675.6 (4)C14—C15—C16—C1755.2 (8)
C6—C1—C2—C353.1 (7)C15—C16—C17—C1854.7 (8)
Sn1—C1—C2—C3178.1 (5)C14—C13—C18—C1752.1 (7)
C1—C2—C3—C455.0 (9)Sn1—C13—C18—C17178.4 (4)
C2—C3—C4—C555.1 (9)C16—C17—C18—C1353.9 (8)
C3—C4—C5—C654.0 (9)C20—N1—C19—S2171.2 (5)
C2—C1—C6—C551.1 (8)C24—N1—C19—S28.1 (8)
Sn1—C1—C6—C5177.5 (5)C20—N1—C19—S19.9 (8)
C4—C5—C6—C151.9 (9)C24—N1—C19—S1173.1 (4)
C1—Sn1—C7—C81.1 (9)Sn1—S2—C19—N1174.5 (5)
C13—Sn1—C7—C8123.9 (8)Sn1—S2—C19—S16.7 (3)
S1—Sn1—C7—C8134.8 (8)Sn1—S1—C19—N1172.4 (4)
S2—Sn1—C7—C878.4 (9)Sn1—S1—C19—S28.6 (4)
C1—Sn1—C7—C12150.1 (6)C19—N1—C20—C21101.8 (8)
C13—Sn1—C7—C1287.1 (7)C24—N1—C20—C2162.8 (7)
S1—Sn1—C7—C1214.3 (8)N1—C20—C21—C2254.6 (9)
S2—Sn1—C7—C1270.7 (7)C20—C21—C22—C2350.4 (10)
C12—C7—C8—C939.0 (14)C21—C22—C23—C2451.7 (10)
Sn1—C7—C8—C9172.4 (7)C19—N1—C24—C23102.5 (7)
C7—C8—C9—C1044.6 (14)C20—N1—C24—C2362.7 (7)
C8—C9—C10—C1151.1 (13)C22—C23—C24—N156.4 (9)

Experimental details

Crystal data
Chemical formula[Sn(C6H11)3(C6H10NS2)]
Mr528.40
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)17.227 (8), 7.676 (4), 20.827 (10)
β (°) 109.598 (8)
V3)2594 (2)
Z4
Radiation typeMo Kα
µ (mm1)1.16
Crystal size (mm)0.26 × 0.20 × 0.12
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.753, 0.874
No. of measured, independent and
observed [I > 2σ(I)] reflections
22395, 4846, 3085
Rint0.081
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.141, 1.04
No. of reflections4846
No. of parameters253
No. of restraints36
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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

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