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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page m938
https://doi.org/10.1107/S1600536810027303

Di-n-butyl­bis­­(N-cyclo­hexyl-N-ethyl­di­thio­carbamato-κ2S,S′)tin(IV)

Normah Awang,a Ibrahim Baba,a Bohari M. Yamina and Seik Weng Ngb*

aSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangbaan Malaysia, 43600 Bangi, Malaysia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 2 July 2010; accepted 9 July 2010; online 17 July 2010)

The SnIV atom in the title compound, [Sn(C4H9)2(C9H16NS2)2], is chelated by the two dithio­carbamate ions in a six-coordinate skew-trapezoidal-bipyramidal geometry. The two butyl groups are disordered over two positions in a 1:1 ratio.

Related literature

For a discussion on six-coordinate, skew-trapezoidal-bipyram­idal diorganotin(IV) bis­(chelates), see: Ng et al. (1987[Ng, S. W., Chen, W., Kumar Das, V. G. & Mak, T. C. W. (1987). J. Organomet. Chem. 334, 295-305.]).

[Scheme 1]

Experimental

Crystal data

  • [Sn(C4H9)2(C9H16NS2)2]

  • Mr = 637.67

  • Triclinic, [P \overline 1]

  • a = 10.2809 (4) Å

  • b = 12.5462 (4) Å

  • c = 13.3823 (5) Å

  • α = 103.103 (1)°

  • β = 108.125 (1)°

  • γ = 90.655 (1)°

  • V = 1591.5 (1) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.08 mm−1

  • T = 293 K

  • 0.35 × 0.25 × 0.25 mm
Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.703, Tmax = 0.774

  • 20772 measured reflections

  • 7294 independent reflections

  • 6264 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.125

  • S = 1.03

  • 7294 reflections

  • 316 parameters

  • 56 restraints

  • H-atom parameters constrained

  • Δρmax = 1.65 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Selected geometric parameters (Å, °)

Sn1—C1 2.128 (4)
Sn1—C5 2.134 (4)
Sn1—S3 2.5292 (9)
Sn1—S1 2.5425 (9)
Sn1—S4 2.8927 (9)
Sn1—S2 2.9257 (10)
C1—Sn1—C5 145.4 (2)

Data collection: SMART (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810027303/zs2050sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027303/zs2050Isup2.hkl

checkCIF report


Comment top

Diorganotin(IV) bis(chelates) generally adopt six-coordinate geometries at tin, a geometry for which the carbon–tin–carbon bond angle is about 135° (Ng et al., 1987). The dithiocarbamate ion is an example of a chelating ligand that imposes such a geometry on the tin atom in diorganotin(IV) compounds. The angle at tin is generally unafffected by the size of the organic group bonded to the metal atom or the steric size of the dithiocarbamate ion. In the title compound (I) (Scheme I, Fig. 1), this angle is 145.4 (2)° and the angle formed by the formally neutral sulfur atom is opened up to 144.13 (3)°.

Related literature top

For a discussion on six-coordinate, skew-trapezoidal-bipyramidal diorganotin(IV) bis(chelates), see: Ng et al. (1987).

Experimental top

Cabon disulfide (30 mmol) was dropped into an ethanol solution (100 ml) of N-cyclohexyl-N-ethylamine (30 mmol). The solution was kept at 273 K for an hour. Dibutyltin dichloride (15 mmol) dissolved in ethanol (100 ml) was added to give a white precipitate. This was collected and recrystallized from a chloroform/ethanol (1/1) mixture.

Refinement top

The carbon atoms of the butyl chains (except for the carbon atoms connected to the tin atom) show large thermal ellipsoids. The disorder could not be refined, and was assumed to be a 1:1 disorder. The 1,2-related carbon-carbon distances were restrained to 1.54±0.01 Å and the 1,3-related ones to 2.51±0.01 Å. The temperature factors of the primed atoms were set to those of the unprimed ones; the anisotropic temperature factors of the disordered atoms were restrained to be nearly isotropic. Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 to 1.5Ueq(C). The final difference Fourier map had a peak in the vicinity of Sn1.

Structure description top

Diorganotin(IV) bis(chelates) generally adopt six-coordinate geometries at tin, a geometry for which the carbon–tin–carbon bond angle is about 135° (Ng et al., 1987). The dithiocarbamate ion is an example of a chelating ligand that imposes such a geometry on the tin atom in diorganotin(IV) compounds. The angle at tin is generally unafffected by the size of the organic group bonded to the metal atom or the steric size of the dithiocarbamate ion. In the title compound (I) (Scheme I, Fig. 1), this angle is 145.4 (2)° and the angle formed by the formally neutral sulfur atom is opened up to 144.13 (3)°.

For a discussion on six-coordinate, skew-trapezoidal-bipyramidal diorganotin(IV) bis(chelates), see: Ng et al. (1987).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (I) at the 50% probability level. The disorder in the butyl chains is not shown.
Di-n-butylbis(N-cyclohexyl-N-ethyldithiocarbamato- κ2S,S')tin(IV) top
Crystal data top
[Sn(C4H9)2(C9H16NS2)2]Z = 2
Mr = 637.67F(000) = 668
Triclinic, P1Dx = 1.331 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.2809 (4) ÅCell parameters from 7406 reflections
b = 12.5462 (4) Åθ = 2.6–26.6°
c = 13.3823 (5) ŵ = 1.08 mm−1
α = 103.103 (1)°T = 293 K
β = 108.125 (1)°Block, colorless
γ = 90.655 (1)°0.35 × 0.25 × 0.25 mm
V = 1591.5 (1) Å3
Data collection top
Bruker SMART CCD
diffractometer		7294 independent reflections
Radiation source: fine-focus sealed tube6264 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.703, Tmax = 0.774k = −16→16
20772 measured reflectionsl = −17→17
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0681P)2 + 0.9862P]
where P = (Fo2 + 2Fc2)/3
7294 reflections(Δ/σ)max = 0.001
316 parametersΔρmax = 1.65 e Å−3
56 restraintsΔρmin = −0.45 e Å−3
Crystal data top
[Sn(C4H9)2(C9H16NS2)2]γ = 90.655 (1)°
Mr = 637.67V = 1591.5 (1) Å3
Triclinic, P1Z = 2
a = 10.2809 (4) ÅMo Kα radiation
b = 12.5462 (4) ŵ = 1.08 mm−1
c = 13.3823 (5) ÅT = 293 K
α = 103.103 (1)°0.35 × 0.25 × 0.25 mm
β = 108.125 (1)°
Data collection top
Bruker SMART CCD
diffractometer		7294 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		6264 reflections with I > 2σ(I)
Tmin = 0.703, Tmax = 0.774Rint = 0.024
20772 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04556 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 1.03Δρmax = 1.65 e Å−3
7294 reflectionsΔρmin = −0.45 e Å−3
316 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.42811 (2)0.309809 (17)0.227305 (19)0.05422 (10)
S10.36710 (10)0.17378 (7)0.04359 (7)0.0581 (2)
S20.30272 (14)0.09498 (9)0.21583 (9)0.0814 (3)
S30.52115 (11)0.43790 (7)0.13954 (7)0.0623 (2)
S40.54453 (12)0.52211 (7)0.36982 (8)0.0670 (3)
N10.2738 (3)−0.0314 (2)0.0204 (2)0.0509 (6)
N20.6358 (3)0.6359 (2)0.2562 (2)0.0563 (7)
C10.6110 (4)0.2555 (3)0.3212 (3)0.0633 (9)
H1A0.61360.17800.29070.076*0.50
H1B0.68950.29470.31580.076*0.50
H1C0.62390.18350.28200.076*0.50
H1D0.68830.30520.32860.076*0.50
C20.625 (3)0.2722 (19)0.4410 (9)0.065 (3)0.50
H2A0.62110.34930.47230.078*0.50
H2B0.54900.23090.44780.078*0.50
C30.761 (4)0.234 (3)0.5023 (15)0.082 (4)0.50
H3A0.83650.27480.49500.098*0.50
H3B0.76410.15670.47160.098*0.50
C40.775 (7)0.252 (5)0.6223 (16)0.114 (5)0.50
H4A0.86210.23130.66070.171*0.50
H4B0.70260.20810.62960.171*0.50
H4C0.76770.32820.65180.171*0.50
C2'0.613 (3)0.249 (2)0.4344 (9)0.065 (3)0.50
H2'A0.56500.30740.46340.078*0.50
H2'B0.56640.17920.42980.078*0.50
C3'0.761 (4)0.258 (3)0.5103 (14)0.082 (4)0.50
H3'A0.80510.32990.52070.098*0.50
H3'B0.81180.20330.47830.098*0.50
C4'0.762 (7)0.240 (5)0.6199 (18)0.114 (5)0.50
H4'A0.85510.24200.66580.171*0.50
H4'B0.71520.16910.60920.171*0.50
H4'C0.71600.29610.65340.171*0.50
C50.2343 (4)0.3697 (4)0.2261 (4)0.0931 (15)
H5A0.23530.44230.21230.112*0.50
H5B0.16500.32300.16410.112*0.50
H5C0.22680.43860.20420.112*0.50
H5D0.16070.31720.17450.112*0.50
C60.1859 (17)0.379 (3)0.3209 (12)0.121 (4)0.50
H6A0.25090.42680.38460.146*0.50
H6B0.17850.30680.33540.146*0.50
C70.0420 (10)0.4260 (15)0.2955 (10)0.135 (4)0.50
H7A0.04910.49740.28020.162*0.50
H7B−0.02330.37740.23230.162*0.50
C8−0.0064 (13)0.4363 (14)0.3911 (11)0.138 (4)0.50
H8A−0.09220.46890.37780.207*0.50
H8B0.06060.48190.45400.207*0.50
H8C−0.01860.36480.40310.207*0.50
C6'0.2218 (15)0.387 (3)0.3376 (10)0.121 (4)0.50
H6'A0.30500.42750.39040.146*0.50
H6'B0.21340.31590.35360.146*0.50
C7'0.0965 (11)0.4501 (14)0.3491 (13)0.135 (4)0.50
H7'A0.11240.48500.42490.162*0.50
H7'B0.08650.50730.30980.162*0.50
C8'−0.0339 (12)0.3750 (14)0.3060 (13)0.138 (4)0.50
H8'A−0.11010.41730.30980.207*0.50
H8'B−0.02720.32200.34870.207*0.50
H8'C−0.04750.33760.23200.207*0.50
C90.3098 (3)0.0674 (3)0.0880 (3)0.0513 (7)
C100.2289 (4)−0.1252 (3)0.0557 (3)0.0516 (7)
H100.2508−0.10090.13450.062*
C110.0772 (4)−0.1549 (3)0.0106 (4)0.0732 (11)
H11A0.0505−0.1835−0.06730.088*
H11B0.0294−0.08990.02510.088*
C120.0375 (4)−0.2408 (4)0.0621 (5)0.0866 (14)
H12A0.0563−0.20920.13890.104*
H12B−0.0604−0.26200.02990.104*
C130.1141 (4)−0.3410 (3)0.0475 (4)0.0741 (11)
H13A0.0918−0.39070.08690.089*
H13B0.0854−0.3787−0.02870.089*
C140.2659 (4)−0.3117 (3)0.0872 (4)0.0748 (11)
H14A0.3121−0.37720.07100.090*
H14B0.2964−0.28340.16530.090*
C150.3059 (4)−0.2258 (3)0.0350 (4)0.0719 (11)
H15A0.4041−0.20550.06530.086*
H15B0.2835−0.2560−0.04230.086*
C160.2768 (4)−0.0508 (3)−0.0916 (3)0.0628 (9)
H16A0.2857−0.1282−0.11760.075*
H16B0.3576−0.0099−0.09130.075*
C170.1515 (5)−0.0186 (5)−0.1699 (4)0.0913 (14)
H17A0.1607−0.0339−0.24090.137*
H17B0.14320.0585−0.14630.137*
H17C0.0709−0.0599−0.17220.137*
C180.5741 (3)0.5428 (3)0.2578 (3)0.0504 (7)
C190.6807 (4)0.7283 (3)0.3531 (3)0.0683 (10)
H190.65620.70440.41020.082*
C200.6089 (6)0.8281 (4)0.3381 (6)0.118 (2)
H20A0.51040.80960.31400.142*
H20B0.63120.85540.28270.142*
C210.6511 (6)0.9177 (5)0.4444 (6)0.127 (2)
H21A0.60800.98390.43140.153*
H21B0.61870.89350.49710.153*
C220.8011 (6)0.9428 (4)0.4886 (5)0.1024 (17)
H22A0.83150.97740.44080.123*
H22B0.82430.99460.55870.123*
C230.8737 (7)0.8449 (5)0.5006 (6)0.129 (3)
H23A0.85280.81580.55570.154*
H23B0.97190.86480.52480.154*
C240.8344 (5)0.7562 (4)0.3952 (5)0.107 (2)
H24A0.86370.78190.34180.128*
H24B0.88040.69100.40750.128*
C250.6604 (4)0.6495 (3)0.1565 (3)0.0649 (9)
H25A0.66850.72730.15940.078*
H25B0.58090.61600.09480.078*
C260.7854 (5)0.6009 (4)0.1381 (4)0.0879 (13)
H26A0.79460.61420.07270.132*
H26B0.77680.52310.13170.132*
H26C0.86510.63400.19820.132*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.05327 (15)0.04494 (14)0.06159 (16)−0.00580 (9)0.02086 (11)0.00446 (10)
S10.0651 (5)0.0473 (4)0.0591 (5)−0.0115 (4)0.0193 (4)0.0092 (4)
S20.1208 (9)0.0606 (6)0.0617 (6)−0.0339 (6)0.0472 (6)−0.0101 (4)
S30.0791 (6)0.0469 (4)0.0528 (5)−0.0110 (4)0.0154 (4)0.0054 (3)
S40.0905 (7)0.0472 (4)0.0623 (5)−0.0179 (4)0.0334 (5)0.0003 (4)
N10.0617 (16)0.0433 (13)0.0463 (14)−0.0040 (11)0.0205 (12)0.0045 (11)
N20.0621 (16)0.0435 (14)0.0628 (17)−0.0069 (12)0.0213 (13)0.0106 (12)
C10.068 (2)0.059 (2)0.062 (2)0.0050 (17)0.0214 (17)0.0114 (16)
C20.077 (4)0.043 (8)0.071 (3)−0.001 (5)0.024 (3)0.007 (3)
C30.092 (3)0.072 (11)0.079 (4)0.009 (7)0.026 (3)0.015 (5)
C40.135 (10)0.124 (10)0.074 (3)0.007 (8)0.015 (4)0.036 (4)
C2'0.077 (4)0.043 (8)0.071 (3)−0.001 (5)0.024 (3)0.007 (3)
C3'0.092 (3)0.072 (11)0.079 (4)0.009 (7)0.026 (3)0.015 (5)
C4'0.135 (10)0.124 (10)0.074 (3)0.007 (8)0.015 (4)0.036 (4)
C50.061 (2)0.086 (3)0.114 (4)−0.004 (2)0.025 (2)−0.006 (3)
C60.078 (8)0.148 (7)0.139 (7)−0.012 (9)0.059 (6)0.002 (7)
C70.061 (7)0.148 (10)0.171 (13)−0.010 (7)0.044 (7)−0.021 (9)
C80.107 (7)0.180 (12)0.127 (9)0.003 (7)0.056 (7)0.010 (7)
C6'0.078 (8)0.148 (7)0.139 (7)−0.012 (9)0.059 (6)0.002 (7)
C7'0.061 (7)0.148 (10)0.171 (13)−0.010 (7)0.044 (7)−0.021 (9)
C8'0.107 (7)0.180 (12)0.127 (9)0.003 (7)0.056 (7)0.010 (7)
C90.0493 (16)0.0474 (16)0.0535 (17)−0.0075 (13)0.0177 (14)0.0039 (13)
C100.0616 (19)0.0418 (15)0.0483 (16)−0.0053 (13)0.0161 (14)0.0077 (12)
C110.054 (2)0.070 (2)0.113 (3)0.0130 (17)0.033 (2)0.047 (2)
C120.057 (2)0.084 (3)0.136 (4)0.006 (2)0.035 (3)0.058 (3)
C130.076 (3)0.053 (2)0.090 (3)−0.0098 (18)0.018 (2)0.0249 (19)
C140.067 (2)0.060 (2)0.105 (3)0.0150 (18)0.025 (2)0.038 (2)
C150.056 (2)0.062 (2)0.109 (3)0.0129 (17)0.033 (2)0.036 (2)
C160.087 (3)0.0499 (18)0.0525 (19)−0.0011 (17)0.0286 (18)0.0061 (14)
C170.100 (4)0.104 (4)0.061 (2)−0.012 (3)0.013 (2)0.020 (2)
C180.0471 (16)0.0411 (15)0.0593 (18)−0.0013 (12)0.0149 (14)0.0084 (13)
C190.083 (3)0.0443 (17)0.073 (2)−0.0192 (17)0.029 (2)0.0007 (16)
C200.078 (3)0.082 (3)0.143 (5)0.021 (3)0.003 (3)−0.027 (3)
C210.106 (4)0.079 (3)0.162 (6)0.002 (3)0.041 (4)−0.036 (4)
C220.109 (4)0.059 (3)0.120 (4)−0.021 (3)0.033 (3)−0.010 (3)
C230.112 (4)0.080 (3)0.129 (5)0.000 (3)−0.016 (4)−0.027 (3)
C240.078 (3)0.072 (3)0.121 (4)0.011 (2)−0.009 (3)−0.019 (3)
C250.080 (2)0.0527 (19)0.067 (2)−0.0031 (17)0.0260 (19)0.0206 (16)
C260.086 (3)0.091 (3)0.095 (3)−0.006 (2)0.046 (3)0.017 (3)
Geometric parameters (Å, º) top
Sn1—C12.128 (4)C6'—C7'1.551 (9)
Sn1—C52.134 (4)C6'—H6'A0.9700
Sn1—S32.5292 (9)C6'—H6'B0.9700
Sn1—S12.5425 (9)C7'—C8'1.504 (9)
Sn1—S42.8927 (9)C7'—H7'A0.9700
Sn1—S22.9257 (10)C7'—H7'B0.9700
S1—C91.744 (3)C8'—H8'A0.9600
S2—C91.691 (3)C8'—H8'B0.9600
S3—C181.743 (3)C8'—H8'C0.9600
S4—C181.693 (4)C10—C111.494 (5)
N1—C91.329 (4)C10—C151.516 (5)
N1—C161.472 (4)C10—H100.9800
N1—C101.482 (4)C11—C121.519 (5)
N2—C181.330 (4)C11—H11A0.9700
N2—C191.474 (5)C11—H11B0.9700
N2—C251.479 (5)C12—C131.499 (6)
C1—C21.529 (8)C12—H12A0.9700
C1—C2'1.530 (9)C12—H12B0.9700
C1—H1A0.9700C13—C141.496 (6)
C1—H1B0.9700C13—H13A0.9700
C1—H1C0.9700C13—H13B0.9700
C1—H1D0.9700C14—C151.526 (5)
C2—C31.527 (9)C14—H14A0.9700
C2—H2A0.9700C14—H14B0.9700
C2—H2B0.9700C15—H15A0.9700
C3—C41.530 (10)C15—H15B0.9700
C3—H3A0.9700C16—C171.512 (6)
C3—H3B0.9700C16—H16A0.9700
C4—H4A0.9600C16—H16B0.9700
C4—H4B0.9600C17—H17A0.9600
C4—H4C0.9600C17—H17B0.9600
C2'—C3'1.526 (9)C17—H17C0.9600
C2'—H2'A0.9700C19—C201.481 (7)
C2'—H2'B0.9700C19—C241.510 (6)
C3'—C4'1.531 (10)C19—H190.9800
C3'—H3'A0.9700C20—C211.534 (8)
C3'—H3'B0.9700C20—H20A0.9700
C4'—H4'A0.9600C20—H20B0.9700
C4'—H4'B0.9600C21—C221.471 (8)
C4'—H4'C0.9600C21—H21A0.9700
C5—C61.484 (9)C21—H21B0.9700
C5—C6'1.505 (9)C22—C231.459 (8)
C5—H5A0.9700C22—H22A0.9700
C5—H5B0.9700C22—H22B0.9700
C5—H5C0.9700C23—C241.521 (7)
C5—H5D0.9700C23—H23A0.9700
C6—C71.567 (9)C23—H23B0.9700
C6—H6A0.9700C24—H24A0.9700
C6—H6B0.9700C24—H24B0.9700
C7—C81.491 (9)C25—C261.493 (6)
C7—H7A0.9700C25—H25A0.9700
C7—H7B0.9700C25—H25B0.9700
C8—H8A0.9600C26—H26A0.9600
C8—H8B0.9600C26—H26B0.9600
C8—H8C0.9600C26—H26C0.9600
C1—Sn1—C5145.4 (2)C8'—C7'—C6'111.6 (10)
C1—Sn1—S3102.1 (1)C8'—C7'—H7'A109.3
C5—Sn1—S3102.5 (2)C6'—C7'—H7'A109.3
C1—Sn1—S1103.7 (1)C8'—C7'—H7'B109.3
C5—Sn1—S1102.1 (1)C6'—C7'—H7'B109.3
S3—Sn1—S185.37 (3)H7'A—C7'—H7'B108.0
C1—Sn1—S483.1 (1)C7'—C8'—H8'A109.5
C5—Sn1—S485.3 (1)C7'—C8'—H8'B109.5
S3—Sn1—S465.63 (3)H8'A—C8'—H8'B109.5
S1—Sn1—S4151.00 (3)C7'—C8'—H8'C109.5
C1—Sn1—S284.4 (1)H8'A—C8'—H8'C109.5
C5—Sn1—S286.2 (2)H8'B—C8'—H8'C109.5
S3—Sn1—S2150.15 (3)N1—C9—S2123.0 (2)
S1—Sn1—S264.83 (3)N1—C9—S1118.8 (2)
S4—Sn1—S2144.13 (3)S2—C9—S1118.26 (18)
C9—S1—Sn194.1 (1)N1—C10—C11113.2 (3)
C9—S2—Sn182.6 (1)N1—C10—C15113.6 (3)
C18—S3—Sn193.3 (1)C11—C10—C15110.6 (3)
C18—S4—Sn182.4 (1)N1—C10—H10106.3
C9—N1—C16121.2 (3)C11—C10—H10106.3
C9—N1—C10120.7 (3)C15—C10—H10106.3
C16—N1—C10118.2 (3)C10—C11—C12109.9 (3)
C18—N2—C19121.2 (3)C10—C11—H11A109.7
C18—N2—C25120.6 (3)C12—C11—H11A109.7
C19—N2—C25118.2 (3)C10—C11—H11B109.7
C2—C1—Sn1114.1 (11)C12—C11—H11B109.7
C2'—C1—Sn1114.9 (11)H11A—C11—H11B108.2
C2—C1—H1A108.7C13—C12—C11112.1 (4)
Sn1—C1—H1A108.7C13—C12—H12A109.2
C2—C1—H1B108.7C11—C12—H12A109.2
C2'—C1—H1B117.4C13—C12—H12B109.2
Sn1—C1—H1B108.7C11—C12—H12B109.2
H1A—C1—H1B107.6H12A—C12—H12B107.9
C2—C1—H1C118.2C14—C13—C12111.3 (3)
C2'—C1—H1C108.5C14—C13—H13A109.4
Sn1—C1—H1C108.5C12—C13—H13A109.4
C2'—C1—H1D108.5C14—C13—H13B109.4
Sn1—C1—H1D108.5C12—C13—H13B109.4
H1C—C1—H1D107.5H13A—C13—H13B108.0
C3—C2—C1110.4 (8)C13—C14—C15111.7 (3)
C3—C2—H2A109.6C13—C14—H14A109.3
C1—C2—H2A109.6C15—C14—H14A109.3
C3—C2—H2B109.6C13—C14—H14B109.3
C1—C2—H2B109.6C15—C14—H14B109.3
H2A—C2—H2B108.1H14A—C14—H14B107.9
C2—C3—C4110.1 (9)C10—C15—C14109.5 (3)
C2—C3—H3A109.6C10—C15—H15A109.8
C4—C3—H3A109.6C14—C15—H15A109.8
C2—C3—H3B109.6C10—C15—H15B109.8
C4—C3—H3B109.6C14—C15—H15B109.8
H3A—C3—H3B108.2H15A—C15—H15B108.2
C3—C4—H4A109.5N1—C16—C17114.3 (3)
C3—C4—H4B109.5N1—C16—H16A108.7
H4A—C4—H4B109.5C17—C16—H16A108.7
C3—C4—H4C109.5N1—C16—H16B108.7
H4A—C4—H4C109.5C17—C16—H16B108.7
H4B—C4—H4C109.5H16A—C16—H16B107.6
C3'—C2'—C1110.7 (8)C16—C17—H17A109.5
C3'—C2'—H2'A109.5C16—C17—H17B109.5
C1—C2'—H2'A109.5H17A—C17—H17B109.5
C3'—C2'—H2'B109.5C16—C17—H17C109.5
C1—C2'—H2'B109.5H17A—C17—H17C109.5
H2'A—C2'—H2'B108.1H17B—C17—H17C109.5
C2'—C3'—C4'110.1 (9)N2—C18—S4122.8 (3)
C2'—C3'—H3'A109.6N2—C18—S3118.6 (3)
C4'—C3'—H3'A109.6S4—C18—S3118.62 (18)
C2'—C3'—H3'B109.6N2—C19—C20113.3 (4)
C4'—C3'—H3'B109.6N2—C19—C24113.1 (4)
H3'A—C3'—H3'B108.1C20—C19—C24110.3 (4)
C3'—C4'—H4'A109.5N2—C19—H19106.5
C3'—C4'—H4'B109.5C20—C19—H19106.5
H4'A—C4'—H4'B109.5C24—C19—H19106.5
C3'—C4'—H4'C109.5C19—C20—C21110.8 (5)
H4'A—C4'—H4'C109.5C19—C20—H20A109.5
H4'B—C4'—H4'C109.5C21—C20—H20A109.5
C6—C5—Sn1121.0 (6)C19—C20—H20B109.5
C6'—C5—Sn1109.5 (5)C21—C20—H20B109.5
C6—C5—H5A107.1H20A—C20—H20B108.1
C6'—C5—H5A105.6C22—C21—C20111.5 (5)
Sn1—C5—H5A107.1C22—C21—H21A109.3
C6—C5—H5B107.1C20—C21—H21A109.3
C6'—C5—H5B120.2C22—C21—H21B109.3
Sn1—C5—H5B107.1C20—C21—H21B109.3
H5A—C5—H5B106.8H21A—C21—H21B108.0
C6—C5—H5C109.8C23—C22—C21112.4 (5)
C6'—C5—H5C109.8C23—C22—H22A109.1
Sn1—C5—H5C109.8C21—C22—H22A109.1
C6'—C5—H5D109.8C23—C22—H22B109.1
Sn1—C5—H5D109.8C21—C22—H22B109.1
H5C—C5—H5D108.2H22A—C22—H22B107.9
C5—C6—C7108.7 (8)C22—C23—C24112.2 (5)
C5—C6—H6A109.9C22—C23—H23A109.2
C7—C6—H6A109.9C24—C23—H23A109.2
C5—C6—H6B109.9C22—C23—H23B109.2
C7—C6—H6B109.9C24—C23—H23B109.2
H6A—C6—H6B108.3H23A—C23—H23B107.9
C8—C7—C6108.9 (8)C19—C24—C23109.9 (5)
C8—C7—H7A109.9C19—C24—H24A109.7
C6—C7—H7A109.9C23—C24—H24A109.7
C8—C7—H7B109.9C19—C24—H24B109.7
C6—C7—H7B109.9C23—C24—H24B109.7
H7A—C7—H7B108.3H24A—C24—H24B108.2
C7—C8—H8A109.5N2—C25—C26114.8 (3)
C7—C8—H8B109.5N2—C25—H25A108.6
H8A—C8—H8B109.5C26—C25—H25A108.6
C7—C8—H8C109.5N2—C25—H25B108.6
H8A—C8—H8C109.5C26—C25—H25B108.6
H8B—C8—H8C109.5H25A—C25—H25B107.5
C5—C6'—C7'112.6 (9)C25—C26—H26A109.5
C5—C6'—H6'A109.1C25—C26—H26B109.5
C7'—C6'—H6'A109.1H26A—C26—H26B109.5
C5—C6'—H6'B109.1C25—C26—H26C109.5
C7'—C6'—H6'B109.1H26A—C26—H26C109.5
H6'A—C6'—H6'B107.8H26B—C26—H26C109.5
C1—Sn1—S1—C974.03 (16)C5—C6—C7—C8−179.4 (18)
C5—Sn1—S1—C9−82.86 (19)C6—C5—C6'—C7'−44 (8)
S3—Sn1—S1—C9175.33 (12)Sn1—C5—C6'—C7'169.4 (12)
S4—Sn1—S1—C9174.78 (12)C5—C6'—C7'—C8'82 (2)
S2—Sn1—S1—C9−2.95 (12)C16—N1—C9—S2177.7 (3)
C1—Sn1—S2—C9−104.97 (16)C10—N1—C9—S2−1.9 (5)
C5—Sn1—S2—C9108.35 (19)C16—N1—C9—S1−2.3 (5)
S3—Sn1—S2—C9−0.38 (16)C10—N1—C9—S1178.0 (2)
S1—Sn1—S2—C93.06 (12)Sn1—S2—C9—N1175.3 (3)
S4—Sn1—S2—C9−175.06 (12)Sn1—S2—C9—S1−4.59 (18)
C1—Sn1—S3—C18−76.12 (15)Sn1—S1—C9—N1−174.7 (3)
C5—Sn1—S3—C1879.37 (17)Sn1—S1—C9—S25.2 (2)
S1—Sn1—S3—C18−179.20 (11)C9—N1—C10—C11105.0 (4)
S4—Sn1—S3—C180.51 (11)C16—N1—C10—C11−74.7 (4)
S2—Sn1—S3—C18−176.08 (12)C9—N1—C10—C15−127.7 (4)
C1—Sn1—S4—C18106.08 (15)C16—N1—C10—C1552.6 (4)
C5—Sn1—S4—C18−106.54 (19)N1—C10—C11—C12−172.5 (4)
S3—Sn1—S4—C18−0.52 (12)C15—C10—C11—C1258.7 (5)
S1—Sn1—S4—C180.08 (15)C10—C11—C12—C13−56.3 (6)
S2—Sn1—S4—C18176.58 (12)C11—C12—C13—C1454.0 (6)
C5—Sn1—C1—C2−8.3 (11)C12—C13—C14—C15−54.1 (6)
S3—Sn1—C1—C2126.2 (10)N1—C10—C15—C14172.6 (3)
S1—Sn1—C1—C2−145.7 (10)C11—C10—C15—C14−58.8 (5)
S4—Sn1—C1—C263.0 (10)C13—C14—C15—C1056.3 (5)
S2—Sn1—C1—C2−83.3 (10)C9—N1—C16—C17−82.1 (4)
C5—Sn1—C1—C2'4.1 (11)C10—N1—C16—C1797.6 (4)
S3—Sn1—C1—C2'138.6 (10)C19—N2—C18—S4−0.9 (5)
S1—Sn1—C1—C2'−133.3 (10)C25—N2—C18—S4179.4 (3)
S4—Sn1—C1—C2'75.4 (10)C19—N2—C18—S3178.9 (3)
S2—Sn1—C1—C2'−70.9 (10)C25—N2—C18—S3−0.8 (5)
C2'—C1—C2—C385 (11)Sn1—S4—C18—N2−179.4 (3)
Sn1—C1—C2—C3−178.4 (15)Sn1—S4—C18—S30.79 (17)
C1—C2—C3—C4179 (2)Sn1—S3—C18—N2179.3 (3)
C2—C1—C2'—C3'−67 (11)Sn1—S3—C18—S4−0.9 (2)
Sn1—C1—C2'—C3'−155.8 (14)C18—N2—C19—C20−116.4 (5)
C1—C2'—C3'—C4'−175 (2)C25—N2—C19—C2063.2 (5)
C1—Sn1—C5—C6−4.2 (17)C18—N2—C19—C24117.0 (4)
S3—Sn1—C5—C6−138.5 (17)C25—N2—C19—C24−63.3 (5)
S1—Sn1—C5—C6133.6 (17)N2—C19—C20—C21175.2 (5)
S4—Sn1—C5—C6−74.8 (17)C24—C19—C20—C21−56.8 (7)
S2—Sn1—C5—C670.3 (17)C19—C20—C21—C2255.0 (8)
C1—Sn1—C5—C6'4.7 (14)C20—C21—C22—C23−53.6 (9)
S3—Sn1—C5—C6'−129.6 (14)C21—C22—C23—C2454.7 (9)
S1—Sn1—C5—C6'142.5 (14)N2—C19—C24—C23−174.8 (5)
S4—Sn1—C5—C6'−65.9 (14)C20—C19—C24—C2357.0 (7)
S2—Sn1—C5—C6'79.3 (14)C22—C23—C24—C19−55.9 (8)
C6'—C5—C6—C7142 (11)C18—N2—C25—C26−82.2 (5)
Sn1—C5—C6—C7179.4 (11)C19—N2—C25—C2698.1 (4)

Experimental details

Crystal data
Chemical formula[Sn(C4H9)2(C9H16NS2)2]
Mr637.67
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.2809 (4), 12.5462 (4), 13.3823 (5)
α, β, γ (°)103.103 (1), 108.125 (1), 90.655 (1)
V (Å3)1591.5 (1)
Z2
Radiation typeMo Kα
µ (mm−1)1.08
Crystal size (mm)0.35 × 0.25 × 0.25
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.703, 0.774
No. of measured, independent and
observed [I > 2σ(I)] reflections		20772, 7294, 6264
Rint0.024
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.125, 1.03
No. of reflections7294
No. of parameters316
No. of restraints56
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.65, −0.45

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top
Sn1—C12.128 (4)Sn1—S12.5425 (9)
Sn1—C52.134 (4)Sn1—S42.8927 (9)
Sn1—S32.5292 (9)Sn1—S22.9257 (10)
C1—Sn1—C5145.4 (2)
 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
 First citationBruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationNg, S. W., Chen, W., Kumar Das, V. G. & Mak, T. C. W. (1987). J. Organomet. Chem. 334, 295–305.  CSD CrossRef CAS Web of Science Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page m938
https://doi.org/10.1107/S1600536810027303
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