PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): m307.
Published online 2010 February 17. doi:  10.1107/S1600536810005830
PMCID: PMC2983579

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

Abstract

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 [triangle]). For the direct synthesis of substituted tribenzyl­tin chlorides, see: Sisido et al. (1961 [triangle]). For the synthesis of dithio­carbamoylacetic acids, see: Nachmias (1952 [triangle]). For background to the triorganotin derivatives of dithio­carbamylacetic acids, see: Ng & Kumar Das (1991 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m307-scheme1.jpg

Experimental

Crystal data

  • [Sn(C7H6Cl)3(C8H14NO2S2)]
  • M r = 715.72
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m307-efi1.jpg
  • 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 [triangle]) T min = 0.710, T max = 0.887
  • 11006 measured reflections
  • 6949 independent reflections
  • 5708 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 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 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005830/lh2995sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005830/lh2995Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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

Experimental

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

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.

Figures

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.

Crystal data

[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

Bruker SMART APEX diffractometer6949 independent reflections
Radiation source: fine-focus sealed tube5708 reflections with I > 2σ(I)
graphiteRint = 0.023
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.710, Tmax = 0.887k = −15→15
11006 measured reflectionsl = −15→17

Refinement

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 = 1.03w = 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

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

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)
H8A−0.03510.51750.72280.047*
H8B−0.02660.48660.60920.047*
C90.0306 (3)0.3539 (2)0.7071 (2)0.0393 (6)
C10−0.0111 (3)0.3140 (3)0.8071 (2)0.0543 (8)
H10−0.04570.36600.85280.065*
C11−0.0028 (4)0.1998 (4)0.8405 (3)0.0763 (12)
H11−0.03200.17520.90780.092*
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)
C17−0.0152 (3)0.8235 (3)0.7272 (3)0.0549 (8)
H170.00370.86170.66270.066*
C18−0.1340 (4)0.8476 (3)0.7821 (3)0.0659 (10)
H18−0.19320.90210.75450.079*
C19−0.1655 (4)0.7923 (3)0.8764 (3)0.0666 (10)
H19−0.24550.80940.91320.080*
C20−0.0780 (3)0.7112 (3)0.9169 (3)0.0571 (9)
H20−0.09850.67280.98100.068*
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
H29A0.72281.0885−0.04200.210*0.50
H29B0.61501.1818−0.00940.210*0.50
H29C0.57661.0560−0.01410.210*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
H29D0.72791.1336−0.03480.210*0.50
H29E0.65711.22510.03350.210*0.50
H29F0.57411.1431−0.01750.210*0.50

Atomic displacement parameters (Å2)

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, °)

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—C22−65.14 (19)C1—Sn1—C15—C16−136.0 (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—C17−102.6 (3)
C15—Sn1—C1—C211.9 (3)C21—C16—C17—C181.7 (5)
C8—Sn1—C1—C2−124.7 (2)C15—C16—C17—C18179.0 (3)
Sn1—C1—C2—C3−84.0 (3)C16—C17—C18—C19−0.7 (6)
Sn1—C1—C2—C797.2 (3)C17—C18—C19—C20−0.4 (6)
C7—C2—C3—C41.3 (4)C18—C19—C20—C210.3 (6)
C1—C2—C3—C4−177.6 (3)C19—C20—C21—C160.9 (5)
C2—C3—C4—C50.0 (5)C19—C20—C21—Cl3−178.0 (3)
C3—C4—C5—C6−0.5 (6)C17—C16—C21—C20−1.8 (4)
C4—C5—C6—C7−0.4 (6)C15—C16—C21—C20−179.1 (3)
C5—C6—C7—C21.7 (5)C17—C16—C21—Cl3177.0 (2)
C5—C6—C7—Cl1−179.1 (3)C15—C16—C21—Cl3−0.2 (4)
C3—C2—C7—C6−2.1 (4)Sn1—O1—C22—O29.4 (3)
C1—C2—C7—C6176.8 (3)Sn1—O1—C22—C23−170.59 (17)
C3—C2—C7—Cl1178.7 (2)O2—C22—C23—S1−7.0 (4)
C1—C2—C7—Cl1−2.3 (4)O1—C22—C23—S1173.06 (19)
O1—Sn1—C8—C9122.2 (2)C24—S1—C23—C22−73.4 (2)
C1—Sn1—C8—C96.8 (2)C26—N1—C24—S2−178.4 (2)
C15—Sn1—C8—C9−132.6 (2)C25—N1—C24—S2−2.0 (4)
Sn1—C8—C9—C10111.1 (3)C26—N1—C24—S10.0 (4)
Sn1—C8—C9—C14−69.0 (3)C25—N1—C24—S1176.5 (2)
C14—C9—C10—C11−1.2 (5)C23—S1—C24—N1175.4 (2)
C8—C9—C10—C11178.7 (3)C23—S1—C24—S2−6.2 (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—C14−0.5 (6)C24—N1—C26—C2789.5 (16)
C12—C13—C14—C9−0.4 (5)C25—N1—C26—C27−87.1 (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—C13−178.6 (3)C26—C27—C28—C29167 (2)
C10—C9—C14—Cl2−178.9 (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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2995).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Nachmias, G. (1952). Ann. Chim.12, 584–631.
  • Ng, S. W., Chen, W. & Kumar Das, V. G. (1988). J. Organomet. Chem.345, 59–64.
  • Ng, S. W. & Kumar Das, V. G. (1991). J. Organomet. Chem.409, 143-156.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc.83, 538–541.
  • Westrip, S. P. (2010). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography