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

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{[(N-Butyl-N-methylcarbamo­thioyl)sulfanyl]acetato-κO}tris­(2-chloro­benz­yl)tin(IV)

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 10 February 2010; accepted 12 February 2010; online 17 February 2010)

The Sn atom in the title compound, [Sn(C7H6Cl)3(C8H14NO2S2)], is coordinated by three chlorobenzyl ligands and one carboxylate O atom of the substituted acetate ligand in a distorted tetra­hedral environment. Three of the C atoms of the n-butyl group are disordered over two sites with equal occupancies.

Related literature

Trialkyl­tin carboxyl­ates are generally carboxyl­ate-bridged polymers; see: Ng et al. (1988[Ng, S. W., Chen, W. & Kumar Das, V. G. (1988). J. Organomet. Chem. 345, 59-64.]). For the direct synthesis of substituted tribenzyl­tin chlorides, see: Sisido et al. (1961[Sisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc. 83, 538-541.]). For the synthesis of dithio­carbamoylacetic acids, see: Nachmias (1952[Nachmias, G. (1952). Ann. Chim. 12, 584-631.]). For background to the triorganotin derivatives of dithio­carbamylacetic acids, see: Ng & Kumar Das (1991[Ng, S. W. & Kumar Das, V. G. (1991). J. Organomet. Chem. 409, 143-156.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C7H6Cl)3(C8H14NO2S2)]

  • Mr = 715.72

  • Triclinic, [P \overline 1]

  • a = 10.2485 (2) Å

  • b = 11.7943 (2) Å

  • c = 13.1704 (3) Å

  • α = 84.417 (1)°

  • β = 84.113 (1)°

  • γ = 86.387 (1)°

  • V = 1573.79 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.23 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.710, Tmax = 0.887

  • 11006 measured reflections

  • 6949 independent reflections

  • 5708 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.078

  • S = 1.03

  • 6949 reflections

  • 353 parameters

  • 10 restraints

  • H-atom parameters constrained

  • Δρmax = 0.49 e Å−3

  • Δρmin = −0.69 e Å−3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. 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). publCIF. In preparation.]).

Supporting information


Comment top

The molecular structure of the title compound is shown in Fig. 1.

Related literature top

Trialkyltin carboxylates are generally carboxylate-bridged polymers; see: Ng et al. (1988). For the direct synthesis of substituted tribenzyltin chlorides, see: Sisido et al. (1961). For the synthesis of dithiocarbamoylacetic acids, see: Nachmias (1952). For background to the triorganotin derivatives of dithiocarbamylacetic acids, see: Ng & Kumar Das (1991).

Experimental top

n-Butylmethyldithiocarbomylacetic acid was synthesized from n-butylmethylamine, carbon disulfide and chloroacetic acid (Nachmias, 1952). Tri(o-chlorobenzyl)tin chloride was prepared by direct synthesis from o-chlorobenzyl chloride and tin powder in a mixture of toluene and water (Sisido et al., 1961). The triorganotin chloride was hydrolyzed with dilute sodium hydroxide solution to give tri(o-chlorobenzyl)tin hydroxide. The carboxylic acid (0.1 g, 0.45 mmol) and the organotin hydroxide (0.23 g, 0.45 mmol) were heated in ethanol (100 ml) for 1 hour. After filtering the mixture, colorless crystals were obtained upon slow evaporation of the filtrate.

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.93–0.97 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5 times Ueq(C).

The butyl chain is disordered over two positions in the three end carbon atoms. The occupancy could not be refined, and was assumed to be 0.5:0.5. The 1,2-related 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 restrained to those of the unprimed ones.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 Sn(C7H6Cl)3(C8H14N2O2S2) at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the butyl chain is not shown.
{[(N-Butyl-N-methylcarbamothioyl)sulfanyl]acetato- κO}tris(2-chlorobenzyl)tin(IV) top
Crystal data top
[Sn(C7H6Cl)3(C8H14NO2S2)]Z = 2
Mr = 715.72F(000) = 724
Triclinic, P1Dx = 1.510 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.2485 (2) ÅCell parameters from 3482 reflections
b = 11.7943 (2) Åθ = 2.4–24.9°
c = 13.1704 (3) ŵ = 1.23 mm1
α = 84.417 (1)°T = 293 K
β = 84.113 (1)°Block, colorless
γ = 86.387 (1)°0.30 × 0.20 × 0.10 mm
V = 1573.79 (5) Å3
Data collection top
Bruker SMART APEX
diffractometer
6949 independent reflections
Radiation source: fine-focus sealed tube5708 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.710, Tmax = 0.887k = 1515
11006 measured reflectionsl = 1517
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.032P)2 + 0.1764P]
where P = (Fo2 + 2Fc2)/3
6949 reflections(Δ/σ)max = 0.001
353 parametersΔρmax = 0.49 e Å3
10 restraintsΔρmin = 0.69 e Å3
Crystal data top
[Sn(C7H6Cl)3(C8H14NO2S2)]γ = 86.387 (1)°
Mr = 715.72V = 1573.79 (5) Å3
Triclinic, P1Z = 2
a = 10.2485 (2) ÅMo Kα radiation
b = 11.7943 (2) ŵ = 1.23 mm1
c = 13.1704 (3) ÅT = 293 K
α = 84.417 (1)°0.30 × 0.20 × 0.10 mm
β = 84.113 (1)°
Data collection top
Bruker SMART APEX
diffractometer
6949 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5708 reflections with I > 2σ(I)
Tmin = 0.710, Tmax = 0.887Rint = 0.023
11006 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03410 restraints
wR(F2) = 0.078H-atom parameters constrained
S = 1.03Δρmax = 0.49 e Å3
6949 reflectionsΔρmin = 0.69 e Å3
353 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.204624 (18)0.556101 (16)0.639187 (15)0.03536 (7)
Cl10.34853 (10)0.32147 (9)0.86752 (8)0.0813 (3)
Cl20.14093 (9)0.31598 (8)0.51718 (7)0.0639 (2)
Cl30.14793 (11)0.58144 (9)0.91177 (8)0.0797 (3)
S10.40006 (8)0.83118 (6)0.30222 (6)0.0476 (2)
S20.22340 (9)0.95231 (8)0.45925 (7)0.0589 (2)
O10.18941 (19)0.61434 (17)0.48768 (15)0.0440 (5)
O20.38538 (19)0.67862 (17)0.50007 (15)0.0447 (5)
N10.4466 (3)1.0273 (2)0.3635 (2)0.0517 (7)
C10.3727 (3)0.4388 (3)0.6482 (2)0.0460 (7)
H1A0.34280.36300.66990.055*
H1B0.41900.43660.58030.055*
C20.4663 (3)0.4680 (2)0.7200 (2)0.0418 (7)
C30.5614 (3)0.5462 (3)0.6885 (3)0.0490 (8)
H30.56360.58230.62240.059*
C40.6529 (4)0.5726 (3)0.7516 (3)0.0645 (10)
H40.71520.62540.72790.077*
C50.6513 (4)0.5205 (4)0.8489 (3)0.0723 (11)
H50.71290.53740.89160.087*
C60.5586 (4)0.4433 (3)0.8837 (3)0.0673 (11)
H60.55770.40740.94980.081*
C70.4664 (3)0.4186 (3)0.8204 (2)0.0498 (8)
C80.0185 (3)0.4777 (2)0.6709 (2)0.0393 (6)
H8A0.03510.51750.72280.047*
H8B0.02660.48660.60920.047*
C90.0306 (3)0.3539 (2)0.7071 (2)0.0393 (6)
C100.0111 (3)0.3140 (3)0.8071 (2)0.0543 (8)
H100.04570.36600.85280.065*
C110.0028 (4)0.1998 (4)0.8405 (3)0.0763 (12)
H110.03200.17520.90780.092*
C120.0493 (5)0.1219 (3)0.7732 (4)0.0847 (14)
H120.05440.04450.79540.102*
C130.0931 (4)0.1575 (3)0.6746 (3)0.0668 (10)
H130.12870.10510.62950.080*
C140.0838 (3)0.2722 (3)0.6428 (2)0.0464 (7)
C150.2045 (3)0.7154 (3)0.7065 (2)0.0503 (8)
H15A0.27420.71130.75150.060*
H15B0.22260.77610.65260.060*
C160.0771 (3)0.7435 (2)0.7657 (2)0.0402 (7)
C170.0152 (3)0.8235 (3)0.7272 (3)0.0549 (8)
H170.00370.86170.66270.066*
C180.1340 (4)0.8476 (3)0.7821 (3)0.0659 (10)
H180.19320.90210.75450.079*
C190.1655 (4)0.7923 (3)0.8764 (3)0.0666 (10)
H190.24550.80940.91320.080*
C200.0780 (3)0.7112 (3)0.9169 (3)0.0571 (9)
H200.09850.67280.98100.068*
C210.0404 (3)0.6876 (2)0.8614 (2)0.0431 (7)
C220.2903 (3)0.6740 (2)0.4527 (2)0.0369 (6)
C230.2751 (3)0.7353 (2)0.3481 (2)0.0416 (7)
H23A0.19080.77770.35050.050*
H23B0.27390.67890.29940.050*
C240.3591 (3)0.9463 (2)0.3791 (2)0.0427 (7)
C250.4238 (4)1.1315 (3)0.4164 (3)0.0721 (11)
H25A0.40441.11160.48860.108*
H25B0.35111.17640.39030.108*
H25C0.50111.17480.40510.108*
C260.5641 (3)1.0227 (3)0.2910 (3)0.0594 (9)
H26A0.59490.94360.28680.071*0.50
H26B0.63261.06190.31660.071*0.50
H26C0.58730.94380.27870.071*0.50
H26D0.63651.05170.32090.071*0.50
C270.541 (3)1.076 (3)0.1840 (11)0.070 (3)0.50
H27A0.50631.15410.18780.083*0.50
H27B0.47741.03400.15580.083*0.50
C280.670 (3)1.075 (3)0.1132 (11)0.097 (3)0.50
H28A0.72691.13070.13230.116*0.50
H28B0.71531.00040.12140.116*0.50
C290.644 (5)1.103 (3)0.0016 (9)0.140 (8)0.50
H29A0.72281.08850.04200.210*0.50
H29B0.61501.18180.00940.210*0.50
H29C0.57661.05600.01410.210*0.50
C27'0.545 (3)1.091 (3)0.1895 (11)0.070 (3)0.50
H27C0.54211.17210.19880.083*0.50
H27D0.46231.07430.16650.083*0.50
C28'0.658 (3)1.064 (3)0.1076 (11)0.097 (3)0.50
H28C0.74111.06560.13580.116*0.50
H28D0.64980.98750.08800.116*0.50
C29'0.654 (5)1.149 (3)0.0135 (10)0.140 (8)0.50
H29D0.72791.13360.03480.210*0.50
H29E0.65711.22510.03350.210*0.50
H29F0.57411.14310.01750.210*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03237 (11)0.03689 (11)0.03697 (11)0.00267 (7)0.00229 (8)0.00472 (8)
Cl10.0721 (6)0.0797 (7)0.0813 (7)0.0031 (5)0.0255 (5)0.0124 (5)
Cl20.0628 (5)0.0761 (6)0.0531 (5)0.0057 (4)0.0016 (4)0.0211 (4)
Cl30.0783 (7)0.0837 (7)0.0698 (6)0.0212 (6)0.0118 (5)0.0175 (5)
S10.0548 (5)0.0414 (4)0.0446 (4)0.0085 (4)0.0098 (4)0.0048 (3)
S20.0646 (6)0.0545 (5)0.0544 (5)0.0056 (4)0.0069 (4)0.0086 (4)
O10.0434 (11)0.0509 (12)0.0382 (11)0.0141 (10)0.0055 (9)0.0025 (9)
O20.0377 (11)0.0518 (13)0.0451 (12)0.0035 (9)0.0086 (10)0.0018 (10)
N10.0565 (17)0.0378 (14)0.0614 (18)0.0043 (12)0.0096 (14)0.0032 (12)
C10.0373 (16)0.0455 (17)0.0560 (19)0.0023 (13)0.0082 (14)0.0074 (14)
C20.0348 (15)0.0441 (17)0.0462 (18)0.0068 (13)0.0048 (13)0.0078 (14)
C30.0468 (18)0.0492 (18)0.0508 (19)0.0010 (15)0.0080 (15)0.0016 (15)
C40.055 (2)0.060 (2)0.082 (3)0.0074 (17)0.022 (2)0.006 (2)
C50.073 (3)0.078 (3)0.074 (3)0.004 (2)0.039 (2)0.015 (2)
C60.082 (3)0.074 (3)0.045 (2)0.018 (2)0.016 (2)0.0052 (18)
C70.0459 (18)0.053 (2)0.0474 (19)0.0085 (15)0.0000 (15)0.0025 (15)
C80.0331 (14)0.0414 (16)0.0442 (17)0.0026 (12)0.0032 (13)0.0086 (13)
C90.0338 (15)0.0433 (16)0.0426 (17)0.0076 (12)0.0079 (13)0.0057 (13)
C100.059 (2)0.061 (2)0.0442 (18)0.0208 (17)0.0066 (16)0.0004 (16)
C110.088 (3)0.081 (3)0.061 (2)0.037 (2)0.019 (2)0.021 (2)
C120.101 (3)0.048 (2)0.109 (4)0.019 (2)0.039 (3)0.012 (2)
C130.070 (2)0.046 (2)0.088 (3)0.0021 (18)0.023 (2)0.012 (2)
C140.0458 (17)0.0434 (17)0.0521 (19)0.0043 (14)0.0121 (15)0.0063 (14)
C150.0547 (19)0.0476 (18)0.0502 (19)0.0136 (15)0.0046 (15)0.0148 (15)
C160.0487 (17)0.0340 (15)0.0398 (16)0.0109 (13)0.0014 (13)0.0098 (12)
C170.070 (2)0.0461 (19)0.0468 (19)0.0034 (17)0.0067 (17)0.0046 (15)
C180.064 (2)0.057 (2)0.075 (3)0.0117 (18)0.014 (2)0.0041 (19)
C190.048 (2)0.072 (3)0.077 (3)0.0065 (18)0.0035 (19)0.012 (2)
C200.061 (2)0.068 (2)0.0411 (18)0.0057 (18)0.0018 (16)0.0061 (16)
C210.0488 (18)0.0421 (17)0.0386 (16)0.0002 (13)0.0068 (14)0.0038 (13)
C220.0368 (15)0.0360 (15)0.0382 (16)0.0021 (12)0.0009 (13)0.0075 (12)
C230.0445 (17)0.0417 (16)0.0391 (16)0.0054 (13)0.0062 (13)0.0020 (13)
C240.0523 (18)0.0371 (16)0.0387 (16)0.0017 (13)0.0095 (14)0.0006 (13)
C250.095 (3)0.044 (2)0.083 (3)0.0074 (19)0.023 (2)0.0156 (19)
C260.049 (2)0.053 (2)0.076 (3)0.0141 (16)0.0088 (18)0.0018 (18)
C270.064 (3)0.069 (6)0.074 (3)0.014 (3)0.007 (2)0.007 (3)
C280.072 (6)0.125 (7)0.090 (4)0.025 (4)0.003 (4)0.014 (3)
C290.153 (10)0.17 (3)0.094 (5)0.051 (17)0.005 (7)0.016 (8)
C27'0.064 (3)0.069 (6)0.074 (3)0.014 (3)0.007 (2)0.007 (3)
C28'0.072 (6)0.125 (7)0.090 (4)0.025 (4)0.003 (4)0.014 (3)
C29'0.153 (10)0.17 (3)0.094 (5)0.051 (17)0.005 (7)0.016 (8)
Geometric parameters (Å, º) top
Sn1—O12.0643 (19)C15—H15A0.9700
Sn1—C12.146 (3)C15—H15B0.9700
Sn1—C152.154 (3)C16—C211.391 (4)
Sn1—C82.157 (3)C16—C171.392 (4)
Cl1—C71.743 (4)C17—C181.379 (5)
Cl2—C141.738 (3)C17—H170.9300
Cl3—C211.743 (3)C18—C191.363 (5)
S1—C241.775 (3)C18—H180.9300
S1—C231.782 (3)C19—C201.376 (5)
S2—C241.659 (3)C19—H190.9300
O1—C221.307 (3)C20—C211.378 (4)
O2—C221.217 (3)C20—H200.9300
N1—C241.339 (4)C22—C231.510 (4)
N1—C261.460 (4)C23—H23A0.9700
N1—C251.466 (4)C23—H23B0.9700
C1—C21.491 (4)C25—H25A0.9600
C1—H1A0.9700C25—H25B0.9600
C1—H1B0.9700C25—H25C0.9600
C2—C31.389 (4)C26—C27'1.518 (8)
C2—C71.392 (4)C26—C271.521 (8)
C3—C41.383 (4)C26—H26A0.9700
C3—H30.9300C26—H26B0.9700
C4—C51.365 (5)C26—H26C0.9700
C4—H40.9300C26—H26D0.9700
C5—C61.371 (5)C27—C281.537 (9)
C5—H50.9300C27—H27A0.9700
C6—C71.384 (5)C27—H27B0.9700
C6—H60.9300C28—C291.522 (10)
C8—C91.492 (4)C28—H28A0.9700
C8—H8A0.9700C28—H28B0.9700
C8—H8B0.9700C29—H29A0.9600
C9—C101.389 (4)C29—H29B0.9600
C9—C141.393 (4)C29—H29C0.9600
C10—C111.376 (5)C27'—C28'1.536 (9)
C10—H100.9300C27'—H27C0.9700
C11—C121.384 (6)C27'—H27D0.9700
C11—H110.9300C28'—C29'1.522 (10)
C12—C131.366 (6)C28'—H28C0.9700
C12—H120.9300C28'—H28D0.9700
C13—C141.377 (5)C29'—H29D0.9600
C13—H130.9300C29'—H29E0.9600
C15—C161.487 (4)C29'—H29F0.9600
O1—Sn1—C1109.03 (10)C19—C20—C21119.3 (3)
O1—Sn1—C15100.56 (11)C19—C20—H20120.3
C1—Sn1—C15118.90 (12)C21—C20—H20120.3
O1—Sn1—C898.45 (10)C20—C21—C16122.8 (3)
C1—Sn1—C8114.34 (11)C20—C21—Cl3118.8 (2)
C15—Sn1—C8112.37 (11)C16—C21—Cl3118.3 (2)
C24—S1—C23101.94 (14)O2—C22—O1123.0 (3)
C22—O1—Sn1109.69 (17)O2—C22—C23124.4 (3)
C24—N1—C26124.0 (3)O1—C22—C23112.6 (2)
C24—N1—C25120.2 (3)C22—C23—S1114.9 (2)
C26—N1—C25115.7 (3)C22—C23—H23A108.5
C2—C1—Sn1113.91 (19)S1—C23—H23A108.5
C2—C1—H1A108.8C22—C23—H23B108.5
Sn1—C1—H1A108.8S1—C23—H23B108.5
C2—C1—H1B108.8H23A—C23—H23B107.5
Sn1—C1—H1B108.8N1—C24—S2124.3 (2)
H1A—C1—H1B107.7N1—C24—S1113.1 (2)
C3—C2—C7116.0 (3)S2—C24—S1122.57 (18)
C3—C2—C1120.8 (3)N1—C25—H25A109.5
C7—C2—C1123.2 (3)N1—C25—H25B109.5
C4—C3—C2122.6 (3)H25A—C25—H25B109.5
C4—C3—H3118.7N1—C25—H25C109.5
C2—C3—H3118.7H25A—C25—H25C109.5
C5—C4—C3119.6 (4)H25B—C25—H25C109.5
C5—C4—H4120.2N1—C26—C27'112.5 (10)
C3—C4—H4120.2N1—C26—C27113.3 (10)
C4—C5—C6119.9 (4)N1—C26—H26A108.9
C4—C5—H5120.0C27'—C26—H26A115.9
C6—C5—H5120.0C27—C26—H26A108.9
C5—C6—C7120.1 (4)N1—C26—H26B108.9
C5—C6—H6120.0C27'—C26—H26B102.5
C7—C6—H6120.0C27—C26—H26B108.9
C6—C7—C2121.8 (3)H26A—C26—H26B107.7
C6—C7—Cl1118.9 (3)N1—C26—H26C109.1
C2—C7—Cl1119.2 (3)C27'—C26—H26C109.1
C9—C8—Sn1113.64 (18)C27—C26—H26C101.9
C9—C8—H8A108.8N1—C26—H26D109.1
Sn1—C8—H8A108.8C27'—C26—H26D109.1
C9—C8—H8B108.8C27—C26—H26D115.2
Sn1—C8—H8B108.8H26C—C26—H26D107.8
H8A—C8—H8B107.7C26—C27—C28110.7 (8)
C10—C9—C14116.3 (3)C26—C27—H27A109.5
C10—C9—C8121.5 (3)C28—C27—H27A109.5
C14—C9—C8122.1 (3)C26—C27—H27B109.5
C11—C10—C9121.9 (3)C28—C27—H27B109.5
C11—C10—H10119.0H27A—C27—H27B108.1
C9—C10—H10119.0C29—C28—C27110.9 (10)
C10—C11—C12119.5 (4)C29—C28—H28A109.5
C10—C11—H11120.3C27—C28—H28A109.5
C12—C11—H11120.3C29—C28—H28B109.5
C13—C12—C11120.6 (4)C27—C28—H28B109.5
C13—C12—H12119.7H28A—C28—H28B108.1
C11—C12—H12119.7C28—C29—H29A109.5
C12—C13—C14118.9 (4)C28—C29—H29B109.5
C12—C13—H13120.5H29A—C29—H29B109.5
C14—C13—H13120.5C28—C29—H29C109.5
C13—C14—C9122.8 (3)H29A—C29—H29C109.5
C13—C14—Cl2118.3 (3)H29B—C29—H29C109.5
C9—C14—Cl2119.0 (2)C26—C27'—C28'111.1 (8)
C16—C15—Sn1112.23 (19)C26—C27'—H27C109.4
C16—C15—H15A109.2C28'—C27'—H27C109.4
Sn1—C15—H15A109.2C26—C27'—H27D109.4
C16—C15—H15B109.2C28'—C27'—H27D109.4
Sn1—C15—H15B109.2H27C—C27'—H27D108.0
H15A—C15—H15B107.9C29'—C28'—C27'110.8 (9)
C21—C16—C17115.8 (3)C29'—C28'—H28C109.5
C21—C16—C15122.0 (3)C27'—C28'—H28C109.5
C17—C16—C15122.2 (3)C29'—C28'—H28D109.5
C18—C17—C16121.7 (3)C27'—C28'—H28D109.5
C18—C17—H17119.1H28C—C28'—H28D108.1
C16—C17—H17119.1C28'—C29'—H29D109.5
C19—C18—C17120.7 (3)C28'—C29'—H29E109.5
C19—C18—H18119.7H29D—C29'—H29E109.5
C17—C18—H18119.7C28'—C29'—H29F109.5
C18—C19—C20119.6 (3)H29D—C29'—H29F109.5
C18—C19—H19120.2H29E—C29'—H29F109.5
C20—C19—H19120.2
C1—Sn1—O1—C2265.14 (19)C1—Sn1—C15—C16136.0 (2)
C15—Sn1—O1—C2260.61 (19)C8—Sn1—C15—C161.4 (3)
C8—Sn1—O1—C22175.38 (18)Sn1—C15—C16—C2174.5 (3)
O1—Sn1—C1—C2126.2 (2)Sn1—C15—C16—C17102.6 (3)
C15—Sn1—C1—C211.9 (3)C21—C16—C17—C181.7 (5)
C8—Sn1—C1—C2124.7 (2)C15—C16—C17—C18179.0 (3)
Sn1—C1—C2—C384.0 (3)C16—C17—C18—C190.7 (6)
Sn1—C1—C2—C797.2 (3)C17—C18—C19—C200.4 (6)
C7—C2—C3—C41.3 (4)C18—C19—C20—C210.3 (6)
C1—C2—C3—C4177.6 (3)C19—C20—C21—C160.9 (5)
C2—C3—C4—C50.0 (5)C19—C20—C21—Cl3178.0 (3)
C3—C4—C5—C60.5 (6)C17—C16—C21—C201.8 (4)
C4—C5—C6—C70.4 (6)C15—C16—C21—C20179.1 (3)
C5—C6—C7—C21.7 (5)C17—C16—C21—Cl3177.0 (2)
C5—C6—C7—Cl1179.1 (3)C15—C16—C21—Cl30.2 (4)
C3—C2—C7—C62.1 (4)Sn1—O1—C22—O29.4 (3)
C1—C2—C7—C6176.8 (3)Sn1—O1—C22—C23170.59 (17)
C3—C2—C7—Cl1178.7 (2)O2—C22—C23—S17.0 (4)
C1—C2—C7—Cl12.3 (4)O1—C22—C23—S1173.06 (19)
O1—Sn1—C8—C9122.2 (2)C24—S1—C23—C2273.4 (2)
C1—Sn1—C8—C96.8 (2)C26—N1—C24—S2178.4 (2)
C15—Sn1—C8—C9132.6 (2)C25—N1—C24—S22.0 (4)
Sn1—C8—C9—C10111.1 (3)C26—N1—C24—S10.0 (4)
Sn1—C8—C9—C1469.0 (3)C25—N1—C24—S1176.5 (2)
C14—C9—C10—C111.2 (5)C23—S1—C24—N1175.4 (2)
C8—C9—C10—C11178.7 (3)C23—S1—C24—S26.2 (2)
C9—C10—C11—C120.4 (6)C24—N1—C26—C27'98.0 (16)
C10—C11—C12—C130.5 (6)C25—N1—C26—C27'78.6 (16)
C11—C12—C13—C140.5 (6)C24—N1—C26—C2789.5 (16)
C12—C13—C14—C90.4 (5)C25—N1—C26—C2787.1 (16)
C12—C13—C14—Cl2179.7 (3)N1—C26—C27—C28176.6 (17)
C10—C9—C14—C131.2 (5)C27'—C26—C27—C2891 (14)
C8—C9—C14—C13178.6 (3)C26—C27—C28—C29167 (2)
C10—C9—C14—Cl2178.9 (2)N1—C26—C27'—C28'167.3 (17)
C8—C9—C14—Cl21.3 (4)C27—C26—C27'—C28'70 (13)
O1—Sn1—C15—C16105.2 (2)C26—C27'—C28'—C29'168 (2)

Experimental details

Crystal data
Chemical formula[Sn(C7H6Cl)3(C8H14NO2S2)]
Mr715.72
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.2485 (2), 11.7943 (2), 13.1704 (3)
α, β, γ (°)84.417 (1), 84.113 (1), 86.387 (1)
V3)1573.79 (5)
Z2
Radiation typeMo Kα
µ (mm1)1.23
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.710, 0.887
No. of measured, independent and
observed [I > 2σ(I)] reflections
11006, 6949, 5708
Rint0.023
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.078, 1.03
No. of reflections6949
No. of parameters353
No. of restraints10
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.49, 0.69

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

Acknowledgements

We thank the University of Malaya (RG020/09AFR and PS338/2009C) for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationNachmias, G. (1952). Ann. Chim. 12, 584–631.  Google Scholar
First citationNg, S. W., Chen, W. & Kumar Das, V. G. (1988). J. Organomet. Chem. 345, 59–64.  CrossRef CAS Web of Science Google Scholar
First citationNg, S. W. & Kumar Das, V. G. (1991). J. Organomet. Chem. 409, 143-156.  CAS 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 citationSisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc. 83, 538–541.  CrossRef Web of Science Google Scholar
First citationWestrip, S. P. (2010). publCIF. In preparation.  Google Scholar

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