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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): m315.
Published online 2010 February 20. doi:  10.1107/S1600536810005921
PMCID: PMC2983718

Tris(o-chloro­benz­yl)[3-(4-meth­oxybenzoyl)­propionato-κO]tin(IV)

Abstract

The tin atom in the title compound, [Sn(C7H6Cl)3(C11H11O4)], exists in a distorted tetra­hedral coordination environment. The carboxyl­ate anion is equally disordered over two positions.

Related literature

Trialkyl­tin carboxyl­ates are generally carboxyl­ate-bridged polymers; see: Ng & Kumar Das (1991 [triangle]). For the direct synthesis of substituted tribenzyl­tin chlorides, see: Sisido et al. (1961 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m315-scheme1.jpg

Experimental

Crystal data

  • [Sn(C7H6Cl)3(C11H11O4)]
  • M r = 702.59
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m315-efi1.jpg
  • a = 8.4934 (6) Å
  • b = 9.2077 (7) Å
  • c = 21.3736 (16) Å
  • α = 82.592 (1)°
  • β = 85.654 (1)°
  • γ = 66.757 (1)°
  • V = 1522.47 (19) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.14 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 = 0.795, T max = 1.000
  • 14685 measured reflections
  • 6922 independent reflections
  • 5062 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.114
  • S = 1.03
  • 6922 reflections
  • 348 parameters
  • 116 restraints
  • H-atom parameters constrained
  • Δρmax = 0.39 e Å−3
  • Δρmin = −0.41 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/S1600536810005921/xu2728sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005921/xu2728Isup2.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

Experimental

3-(4-Methoxyl)benzoylpropionic acid (0.1 g, 0.5 mmol) and tri(o-chlorobenzyl)tin hydroxide (0.25 g, 0.5 mmol) were heated in ethanol (100 ml) for 1 h. After filtering of 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 aromatic rings of the benzyl group were refined as rigid hexagons of 1.39 Å sides.

The carboxylate anion is disordered over two positions; the occupancy could not be refined, and was assumed to be a 1:1 type of disorder.

The C–O distances were restrained to 1.25±0.01 Å; the 1,2-related carbon-carbon distances in the chain were restrained to 1.50±0.01 Å and the 1,3-related ones to 2.35±0.01 Å. For the methoxy portion, the carbon-oxygen distances were restrained to 1.35±0.01 Å. The four-atom unit for the carbony/carboxyl portions were restrained to be nearly flat. The temperature factors of the primed atoms were restrained to those of the unprimed ones, and the anisotropic temperature factors of the disordered atoms were restrained to be nearly isotropic. The aromatic rings were treated as rigid hexagons.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of Sn(C7H6Cl)3(C11H11O4) at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder component of the carboxylate anion is shown in the monodentate mode.
Fig. 2.
Thermal ellipsoid plot (Barbour, 2001) of Sn(C7H6Cl)3(C11H11O4) at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder component of the carboxylate anion is shown in the chelating mode.

Crystal data

[Sn(C7H6Cl)3(C11H11O4)]Z = 2
Mr = 702.59F(000) = 708
Triclinic, P1Dx = 1.533 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4934 (6) ÅCell parameters from 3994 reflections
b = 9.2077 (7) Åθ = 2.4–22.1°
c = 21.3736 (16) ŵ = 1.14 mm1
α = 82.592 (1)°T = 293 K
β = 85.654 (1)°Prism, colorless
γ = 66.757 (1)°0.30 × 0.20 × 0.10 mm
V = 1522.47 (19) Å3

Data collection

Bruker SMART APEX diffractometer6922 independent reflections
Radiation source: fine-focus sealed tube5062 reflections with I > 2σ(I)
graphiteRint = 0.027
ω scansθmax = 27.5°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→10
Tmin = 0.795, Tmax = 1.000k = −11→11
14685 measured reflectionsl = −27→27

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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0516P)2 + 0.397P] where P = (Fo2 + 2Fc2)/3
6922 reflections(Δ/σ)max = 0.001
348 parametersΔρmax = 0.39 e Å3
116 restraintsΔρmin = −0.41 e Å3

Special details

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.

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

xyzUiso*/UeqOcc. (<1)
Sn10.43681 (3)0.57720 (3)0.210995 (12)0.05681 (11)
Cl10.26514 (16)0.91485 (13)0.09610 (6)0.0829 (3)
Cl20.86070 (17)0.2126 (2)0.18407 (7)0.1150 (5)
Cl30.2567 (3)0.26908 (19)0.23276 (8)0.1215 (5)
C10.1641 (5)0.7088 (5)0.19945 (18)0.0605 (10)
H1A0.10260.66030.22940.073*
H1B0.13410.81670.20930.073*
C20.1068 (3)0.7144 (3)0.13357 (9)0.0509 (8)
C30.0112 (3)0.6280 (3)0.12270 (11)0.0618 (10)
H3−0.02050.56910.15620.074*
C4−0.0369 (3)0.6296 (3)0.06181 (13)0.0714 (11)
H4−0.10080.57170.05450.086*
C50.0105 (4)0.7176 (3)0.01178 (9)0.0733 (12)
H5−0.02160.7187−0.02900.088*
C60.1061 (3)0.8041 (3)0.02265 (10)0.0659 (10)
H60.13780.8630−0.01080.079*
C70.1542 (3)0.8025 (3)0.08354 (11)0.0549 (9)
C80.5728 (5)0.5071 (5)0.1235 (2)0.0676 (11)
H8A0.51500.58570.08910.081*
H8B0.68780.50440.12510.081*
C90.5835 (3)0.3466 (3)0.11058 (13)0.0559 (9)
C100.4632 (3)0.3387 (3)0.07197 (13)0.0745 (12)
H100.38060.43170.05330.089*
C110.4664 (4)0.1919 (4)0.06124 (15)0.0962 (16)
H110.38590.18660.03540.115*
C120.5899 (5)0.0529 (3)0.08913 (18)0.1005 (18)
H120.5920−0.04540.08200.121*
C130.7102 (4)0.0607 (3)0.12775 (16)0.0869 (15)
H130.7928−0.03230.14640.104*
C140.7070 (3)0.2076 (3)0.13847 (12)0.0664 (10)
C150.4920 (6)0.3911 (5)0.2881 (2)0.0772 (12)
H15A0.54360.28850.27180.093*
H15B0.57330.39950.31550.093*
C160.3305 (4)0.4030 (4)0.32513 (14)0.0729 (12)
C170.2955 (5)0.4740 (4)0.38092 (16)0.0969 (16)
H170.37440.50730.39590.116*
C180.1425 (6)0.4953 (5)0.41438 (15)0.132 (3)
H180.11910.54280.45170.159*
C190.0246 (4)0.4456 (5)0.3920 (2)0.136 (3)
H19−0.07780.45980.41440.164*
C200.0596 (4)0.3746 (5)0.3362 (2)0.122 (2)
H20−0.01930.34130.32130.146*
C210.2126 (5)0.3533 (4)0.30278 (15)0.0834 (13)
O10.4575 (9)0.7580 (9)0.2569 (3)0.0768 (14)0.50
O20.7217 (9)0.6062 (9)0.2436 (3)0.0887 (15)0.50
O30.588 (4)0.655 (3)0.4097 (15)0.104 (4)0.50
O40.0927 (11)0.9380 (10)0.6204 (4)0.1084 (18)0.50
C220.6118 (11)0.7264 (9)0.2664 (3)0.081 (2)0.50
C230.6705 (14)0.8200 (15)0.3018 (6)0.075 (3)0.50
H23A0.77520.74950.32270.090*0.50
H23B0.69820.89620.27220.090*0.50
C240.548 (2)0.9058 (18)0.3491 (7)0.071 (2)0.50
H24A0.43940.96840.32920.086*0.50
H24B0.58900.97880.36450.086*0.50
C250.5198 (18)0.802 (3)0.4030 (6)0.0772 (15)0.50
C260.403 (2)0.8541 (13)0.4597 (6)0.0708 (14)0.50
C270.4017 (15)0.7283 (9)0.5032 (5)0.081 (2)0.50
H270.47240.62450.49640.097*0.50
C280.2951 (11)0.7578 (7)0.5567 (4)0.082 (2)0.50
H280.29450.67360.58580.099*0.50
C290.1895 (9)0.9130 (8)0.5668 (3)0.072 (2)0.50
C300.1905 (12)1.0387 (7)0.5234 (4)0.081 (2)0.50
H300.11981.14260.53010.097*0.50
C310.2971 (18)1.0093 (11)0.4698 (5)0.078 (2)0.50
H310.29781.09340.44080.094*0.50
C32−0.022 (3)1.0886 (15)0.6320 (10)0.124 (4)0.50
H32A−0.07671.08310.67270.187*0.50
H32B−0.10721.12940.60010.187*0.50
H32C0.03831.15780.63110.187*0.50
O1'0.3878 (8)0.7681 (8)0.2923 (3)0.0768 (14)0.50
O2'0.5929 (9)0.7007 (9)0.2224 (3)0.0887 (15)0.50
O3'0.611 (4)0.677 (3)0.3979 (15)0.104 (4)0.50
O4'0.0474 (11)1.0989 (9)0.5980 (4)0.1084 (18)0.50
C22'0.5231 (10)0.7763 (8)0.2700 (3)0.081 (2)0.50
C23'0.6080 (14)0.8686 (15)0.2958 (6)0.075 (3)0.50
H23C0.61440.95140.26400.090*0.50
H23D0.72370.79910.30790.090*0.50
C24'0.506 (2)0.9411 (19)0.3522 (7)0.071 (2)0.50
H24C0.55281.01120.36660.086*0.50
H24D0.38831.00380.34070.086*0.50
C25'0.5114 (19)0.816 (3)0.4034 (6)0.0772 (15)0.50
C26'0.389 (2)0.8780 (13)0.4571 (6)0.0708 (14)0.50
C27'0.3492 (15)0.7807 (8)0.5055 (5)0.081 (2)0.50
H27'0.39910.67090.50550.097*0.50
C28'0.2352 (11)0.8477 (8)0.5540 (3)0.082 (2)0.50
H28'0.20880.78270.58640.099*0.50
C29'0.1607 (9)1.0120 (8)0.5540 (3)0.072 (2)0.50
C30'0.2002 (12)1.1092 (8)0.5055 (4)0.081 (2)0.50
H30'0.15041.21910.50550.097*0.50
C31'0.3142 (18)1.0422 (12)0.4571 (5)0.078 (2)0.50
H31'0.34061.10730.42470.094*0.50
C32'−0.004 (3)1.017 (2)0.6466 (9)0.124 (4)0.50
H32D0.05761.00850.68360.187*0.50
H32E0.01740.91260.63590.187*0.50
H32F−0.12491.07190.65490.187*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.05296 (17)0.06063 (18)0.05656 (17)−0.02085 (13)0.00286 (11)−0.01208 (12)
Cl10.0876 (8)0.0649 (6)0.1080 (9)−0.0445 (6)−0.0020 (7)−0.0017 (6)
Cl20.0662 (8)0.1523 (14)0.0965 (10)−0.0022 (8)−0.0191 (7)−0.0315 (9)
Cl30.1578 (16)0.1071 (11)0.1053 (11)−0.0565 (11)−0.0304 (10)0.0005 (9)
C10.057 (2)0.058 (2)0.059 (2)−0.0125 (18)0.0048 (18)−0.0129 (18)
C20.0423 (19)0.0439 (18)0.059 (2)−0.0094 (15)0.0026 (16)−0.0052 (16)
C30.054 (2)0.059 (2)0.071 (3)−0.0237 (19)0.0071 (19)−0.0021 (19)
C40.067 (3)0.076 (3)0.081 (3)−0.035 (2)−0.005 (2)−0.017 (2)
C50.071 (3)0.078 (3)0.061 (3)−0.016 (2)−0.013 (2)−0.012 (2)
C60.064 (3)0.057 (2)0.064 (3)−0.014 (2)0.004 (2)0.0029 (19)
C70.050 (2)0.0436 (19)0.067 (2)−0.0148 (16)0.0027 (18)−0.0048 (17)
C80.063 (3)0.071 (3)0.067 (3)−0.025 (2)0.015 (2)−0.011 (2)
C90.046 (2)0.064 (2)0.053 (2)−0.0173 (18)0.0114 (16)−0.0103 (18)
C100.064 (3)0.084 (3)0.073 (3)−0.027 (2)0.007 (2)−0.016 (2)
C110.072 (3)0.123 (5)0.109 (4)−0.049 (3)0.013 (3)−0.043 (4)
C120.094 (4)0.093 (4)0.131 (5)−0.054 (3)0.045 (4)−0.041 (4)
C130.077 (3)0.064 (3)0.096 (4)−0.010 (2)0.034 (3)−0.002 (3)
C140.051 (2)0.071 (3)0.062 (2)−0.009 (2)0.0118 (18)−0.009 (2)
C150.066 (3)0.079 (3)0.071 (3)−0.014 (2)−0.001 (2)0.002 (2)
C160.072 (3)0.061 (3)0.068 (3)−0.012 (2)0.006 (2)0.009 (2)
C170.107 (4)0.090 (4)0.075 (3)−0.023 (3)0.018 (3)−0.006 (3)
C180.141 (6)0.104 (5)0.112 (5)−0.016 (4)0.051 (5)−0.009 (4)
C190.098 (5)0.125 (6)0.151 (7)−0.022 (4)0.055 (5)0.004 (5)
C200.087 (4)0.109 (5)0.159 (6)−0.044 (4)0.003 (4)0.040 (4)
C210.085 (3)0.070 (3)0.087 (3)−0.028 (3)−0.002 (3)0.015 (2)
O10.067 (3)0.091 (3)0.085 (4)−0.038 (3)0.004 (2)−0.030 (3)
O20.088 (4)0.109 (4)0.082 (3)−0.047 (3)0.008 (3)−0.034 (3)
O30.102 (6)0.073 (5)0.103 (9)−0.007 (4)0.016 (5)0.012 (5)
O40.123 (5)0.105 (4)0.096 (4)−0.042 (4)0.001 (3)−0.019 (3)
C220.087 (7)0.088 (5)0.076 (4)−0.041 (5)−0.008 (5)−0.011 (4)
C230.070 (7)0.090 (6)0.078 (4)−0.040 (6)−0.010 (4)−0.017 (4)
C240.075 (7)0.065 (6)0.077 (3)−0.027 (5)−0.007 (4)−0.013 (3)
C250.073 (3)0.072 (4)0.078 (3)−0.018 (3)−0.016 (2)−0.006 (2)
C260.066 (3)0.073 (4)0.070 (3)−0.020 (3)−0.019 (2)−0.006 (3)
C270.082 (7)0.077 (6)0.074 (3)−0.017 (5)−0.009 (4)−0.015 (4)
C280.084 (6)0.074 (6)0.079 (4)−0.019 (5)−0.018 (4)−0.003 (5)
C290.070 (4)0.066 (5)0.080 (4)−0.018 (4)−0.012 (3)−0.027 (4)
C300.082 (4)0.072 (6)0.086 (6)−0.027 (4)−0.007 (4)−0.006 (5)
C310.076 (4)0.078 (5)0.077 (5)−0.024 (3)−0.011 (3)−0.006 (4)
C320.117 (6)0.163 (10)0.105 (8)−0.066 (8)−0.002 (5)−0.021 (7)
O1'0.067 (3)0.091 (3)0.085 (4)−0.038 (3)0.004 (2)−0.030 (3)
O2'0.088 (4)0.109 (4)0.082 (3)−0.047 (3)0.008 (3)−0.034 (3)
O3'0.102 (6)0.073 (5)0.103 (9)−0.007 (4)0.016 (5)0.012 (5)
O4'0.123 (5)0.105 (4)0.096 (4)−0.042 (4)0.001 (3)−0.019 (3)
C22'0.087 (7)0.088 (5)0.076 (4)−0.041 (5)−0.008 (5)−0.011 (4)
C23'0.070 (7)0.090 (6)0.078 (4)−0.040 (6)−0.010 (4)−0.017 (4)
C24'0.075 (7)0.065 (6)0.077 (3)−0.027 (5)−0.007 (4)−0.013 (3)
C25'0.073 (3)0.072 (4)0.078 (3)−0.018 (3)−0.016 (2)−0.006 (2)
C26'0.066 (3)0.073 (4)0.070 (3)−0.020 (3)−0.019 (2)−0.006 (3)
C27'0.082 (7)0.077 (6)0.074 (3)−0.017 (5)−0.009 (4)−0.015 (4)
C28'0.084 (6)0.074 (6)0.079 (4)−0.019 (5)−0.018 (4)−0.003 (5)
C29'0.070 (4)0.066 (5)0.080 (4)−0.018 (4)−0.012 (3)−0.027 (4)
C30'0.082 (4)0.072 (6)0.086 (6)−0.027 (4)−0.007 (4)−0.006 (5)
C31'0.076 (4)0.078 (5)0.077 (5)−0.024 (3)−0.011 (3)−0.006 (4)
C32'0.117 (6)0.163 (10)0.105 (8)−0.066 (8)−0.002 (5)−0.021 (7)

Geometric parameters (Å, °)

Sn1—O2'2.103 (7)O3—C251.236 (9)
Sn1—O12.108 (7)O4—C291.348 (7)
Sn1—C152.150 (4)O4—C321.385 (9)
Sn1—C82.155 (4)C22—C231.460 (9)
Sn1—C12.165 (4)C23—C241.457 (8)
Sn1—O1'2.527 (6)C23—H23A0.9700
Cl1—C71.706 (2)C23—H23B0.9700
Cl2—C141.705 (3)C24—C251.469 (9)
Cl3—C211.722 (3)C24—H24A0.9700
C1—C21.513 (4)C24—H24B0.9700
C1—H1A0.9700C25—C261.510 (8)
C1—H1B0.9700C26—C271.3900
C2—C31.3900C26—C311.3900
C2—C71.3900C27—C281.3900
C3—C41.3900C27—H270.9300
C3—H30.9300C28—C291.3900
C4—C51.3900C28—H280.9300
C4—H40.9300C29—C301.3900
C5—C61.3900C30—C311.3900
C5—H50.9300C30—H300.9300
C6—C71.3900C31—H310.9300
C6—H60.9300C32—H32A0.9600
C8—C91.505 (4)C32—H32B0.9600
C8—H8A0.9700C32—H32C0.9600
C8—H8B0.9700O1'—C22'1.237 (8)
C9—C101.3900O2'—C22'1.279 (8)
C9—C141.3900O3'—C25'1.240 (9)
C10—C111.3900O4'—C32'1.354 (9)
C10—H100.9300O4'—C29'1.379 (7)
C11—C121.3900C22'—C23'1.487 (9)
C11—H110.9300C23'—C24'1.496 (8)
C12—C131.3900C23'—H23C0.9700
C12—H120.9300C23'—H23D0.9700
C13—C141.3900C24'—C25'1.475 (9)
C13—H130.9300C24'—H24C0.9700
C15—C161.504 (5)C24'—H24D0.9700
C15—H15A0.9700C25'—C26'1.499 (8)
C15—H15B0.9700C26'—C27'1.3900
C16—C171.3900C26'—C31'1.3900
C16—C211.3900C27'—C28'1.3900
C17—C181.3900C27'—H27'0.9300
C17—H170.9300C28'—C29'1.3900
C18—C191.3900C28'—H28'0.9300
C18—H180.9300C29'—C30'1.3900
C19—C201.3900C30'—C31'1.3900
C19—H190.9300C30'—H30'0.9300
C20—C211.3900C31'—H31'0.9300
C20—H200.9300C32'—H32D0.9600
O1—C221.251 (8)C32'—H32E0.9600
O2—C221.260 (8)C32'—H32F0.9600
O2'—Sn1—O135.4 (2)C20—C21—Cl3120.8 (3)
O2'—Sn1—C15106.1 (2)C16—C21—Cl3119.2 (3)
O1—Sn1—C1599.8 (2)C22—O1—Sn1109.7 (6)
O2'—Sn1—C889.2 (2)C29—O4—C32121.6 (11)
O1—Sn1—C8122.1 (2)O1—C22—O2117.3 (8)
C15—Sn1—C8115.29 (17)O1—C22—C23124.0 (8)
O2'—Sn1—C1119.2 (2)O2—C22—C23118.7 (8)
O1—Sn1—C191.8 (2)C24—C23—C22114.9 (8)
C15—Sn1—C1112.27 (17)C24—C23—H23A108.5
C8—Sn1—C1112.93 (16)C22—C23—H23A108.5
O2'—Sn1—O1'54.5 (2)C24—C23—H23B108.5
O1—Sn1—O1'20.3 (2)C22—C23—H23B108.5
C15—Sn1—O1'87.3 (2)H23A—C23—H23B107.5
C8—Sn1—O1'142.43 (18)C23—C24—C25113.6 (8)
C1—Sn1—O1'81.82 (17)C23—C24—H24A108.8
C2—C1—Sn1113.2 (2)C25—C24—H24A108.8
C2—C1—H1A108.9C23—C24—H24B108.8
Sn1—C1—H1A108.9C25—C24—H24B108.8
C2—C1—H1B108.9H24A—C24—H24B107.7
Sn1—C1—H1B108.9O3—C25—C24125.8 (14)
H1A—C1—H1B107.7O3—C25—C26107.8 (18)
C3—C2—C7120.0C24—C25—C26126.4 (15)
C3—C2—C1120.1 (2)C27—C26—C31120.0
C7—C2—C1119.8 (2)C27—C26—C25113.4 (11)
C4—C3—C2120.0C31—C26—C25126.5 (11)
C4—C3—H3120.0C26—C27—C28120.0
C2—C3—H3120.0C26—C27—H27120.0
C3—C4—C5120.0C28—C27—H27120.0
C3—C4—H4120.0C29—C28—C27120.0
C5—C4—H4120.0C29—C28—H28120.0
C4—C5—C6120.0C27—C28—H28120.0
C4—C5—H5120.0O4—C29—C28118.5 (6)
C6—C5—H5120.0O4—C29—C30121.4 (6)
C7—C6—C5120.0C28—C29—C30120.0
C7—C6—H6120.0C29—C30—C31120.0
C5—C6—H6120.0C29—C30—H30120.0
C6—C7—C2120.0C31—C30—H30120.0
C6—C7—Cl1119.14 (15)C30—C31—C26120.0
C2—C7—Cl1120.82 (15)C30—C31—H31120.0
C9—C8—Sn1112.1 (2)C26—C31—H31120.0
C9—C8—H8A109.2C22'—O1'—Sn184.2 (5)
Sn1—C8—H8A109.2C22'—O2'—Sn1103.2 (6)
C9—C8—H8B109.2C32'—O4'—C29'117.2 (11)
Sn1—C8—H8B109.2O1'—C22'—O2'117.8 (8)
H8A—C8—H8B107.9O1'—C22'—C23'123.4 (8)
C10—C9—C14120.0O2'—C22'—C23'118.8 (8)
C10—C9—C8118.9 (3)C22'—C23'—C24'108.8 (7)
C14—C9—C8121.1 (3)C22'—C23'—H23C109.9
C9—C10—C11120.0C24'—C23'—H23C109.9
C9—C10—H10120.0C22'—C23'—H23D109.9
C11—C10—H10120.0C24'—C23'—H23D109.9
C12—C11—C10120.0H23C—C23'—H23D108.3
C12—C11—H11120.0C25'—C24'—C23'110.2 (8)
C10—C11—H11120.0C25'—C24'—H24C109.6
C11—C12—C13120.0C23'—C24'—H24C109.6
C11—C12—H12120.0C25'—C24'—H24D109.6
C13—C12—H12120.0C23'—C24'—H24D109.6
C12—C13—C14120.0H24C—C24'—H24D108.1
C12—C13—H13120.0O3'—C25'—C24'118.9 (14)
C14—C13—H13120.0O3'—C25'—C26'128.2 (19)
C13—C14—C9120.0C24'—C25'—C26'112.9 (15)
C13—C14—Cl2118.7 (2)C27'—C26'—C31'120.0
C9—C14—Cl2121.2 (2)C27'—C26'—C25'123.5 (11)
C16—C15—Sn1110.4 (3)C31'—C26'—C25'116.5 (11)
C16—C15—H15A109.6C28'—C27'—C26'120.0
Sn1—C15—H15A109.6C28'—C27'—H27'120.0
C16—C15—H15B109.6C26'—C27'—H27'120.0
Sn1—C15—H15B109.6C27'—C28'—C29'120.0
H15A—C15—H15B108.1C27'—C28'—H28'120.0
C17—C16—C21120.0C29'—C28'—H28'120.0
C17—C16—C15118.6 (3)O4'—C29'—C28'128.1 (6)
C21—C16—C15121.3 (3)O4'—C29'—C30'111.9 (6)
C18—C17—C16120.0C28'—C29'—C30'120.0
C18—C17—H17120.0C31'—C30'—C29'120.0
C16—C17—H17120.0C31'—C30'—H30'120.0
C17—C18—C19120.0C29'—C30'—H30'120.0
C17—C18—H18120.0C30'—C31'—C26'120.0
C19—C18—H18120.0C30'—C31'—H31'120.0
C18—C19—C20120.0C26'—C31'—H31'120.0
C18—C19—H19120.0O4'—C32'—H32D109.5
C20—C19—H19120.0O4'—C32'—H32E109.5
C21—C20—C19120.0H32D—C32'—H32E109.5
C21—C20—H20120.0O4'—C32'—H32F109.5
C19—C20—H20120.0H32D—C32'—H32F109.5
C20—C21—C16120.0H32E—C32'—H32F109.5
O2'—Sn1—C1—C2109.8 (3)Sn1—O1—C22—O25.3 (5)
O1—Sn1—C1—C2133.3 (3)Sn1—O1—C22—C23−174.8 (5)
C15—Sn1—C1—C2−125.3 (3)O1—C22—C23—C2426.9 (10)
C8—Sn1—C1—C27.1 (3)O2—C22—C23—C24−153.2 (10)
O1'—Sn1—C1—C2151.1 (3)C22—C23—C24—C2568.8 (14)
Sn1—C1—C2—C3108.5 (2)C23—C24—C25—O3−0.9 (14)
Sn1—C1—C2—C7−69.5 (3)C23—C24—C25—C26179.3 (14)
C7—C2—C3—C40.0O3—C25—C26—C27−0.1 (11)
C1—C2—C3—C4−178.1 (3)C24—C25—C26—C27179.8 (11)
C2—C3—C4—C50.0O3—C25—C26—C31−177.5 (17)
C3—C4—C5—C60.0C24—C25—C26—C312.4 (17)
C4—C5—C6—C70.0C31—C26—C27—C280.0
C5—C6—C7—C20.0C25—C26—C27—C28−177.6 (13)
C5—C6—C7—Cl1−177.78 (19)C26—C27—C28—C290.0
C3—C2—C7—C60.0C32—O4—C29—C28−176.6 (14)
C1—C2—C7—C6178.1 (3)C32—O4—C29—C306.1 (17)
C3—C2—C7—Cl1177.74 (19)C27—C28—C29—O4−177.4 (10)
C1—C2—C7—Cl1−4.2 (3)C27—C28—C29—C300.0
O2'—Sn1—C8—C9148.1 (3)O4—C29—C30—C31177.3 (10)
O1—Sn1—C8—C9161.9 (3)C28—C29—C30—C310.0
C15—Sn1—C8—C940.7 (3)C29—C30—C31—C260.0
C1—Sn1—C8—C9−90.2 (3)C27—C26—C31—C300.0
O1'—Sn1—C8—C9162.5 (3)C25—C26—C31—C30177.2 (15)
Sn1—C8—C9—C1096.0 (3)O2'—Sn1—O1'—C22'−2.6 (3)
Sn1—C8—C9—C14−81.6 (3)O1—Sn1—O1'—C22'−18.9 (7)
C14—C9—C10—C110.0C15—Sn1—O1'—C22'109.4 (3)
C8—C9—C10—C11−177.6 (3)C8—Sn1—O1'—C22'−20.4 (5)
C9—C10—C11—C120.0C1—Sn1—O1'—C22'−137.7 (3)
C10—C11—C12—C130.0O1—Sn1—O2'—C22'12.3 (4)
C11—C12—C13—C140.0C15—Sn1—O2'—C22'−72.0 (4)
C12—C13—C14—C90.0C8—Sn1—O2'—C22'171.8 (4)
C12—C13—C14—Cl2−177.9 (2)C1—Sn1—O2'—C22'55.8 (5)
C10—C9—C14—C130.0O1'—Sn1—O2'—C22'2.6 (3)
C8—C9—C14—C13177.5 (3)Sn1—O1'—C22'—O2'3.9 (4)
C10—C9—C14—Cl2177.9 (2)Sn1—O1'—C22'—C23'−175.9 (4)
C8—C9—C14—Cl2−4.6 (3)Sn1—O2'—C22'—O1'−4.8 (5)
O2'—Sn1—C15—C16123.7 (3)Sn1—O2'—C22'—C23'175.1 (5)
O1—Sn1—C15—C1687.9 (4)O1'—C22'—C23'—C24'1.8 (9)
C8—Sn1—C15—C16−139.4 (3)O2'—C22'—C23'—C24'−178.1 (9)
C1—Sn1—C15—C16−8.1 (4)C22'—C23'—C24'—C25'65.6 (13)
O1'—Sn1—C15—C1671.9 (3)C23'—C24'—C25'—O3'9.6 (14)
Sn1—C15—C16—C17−99.6 (3)C23'—C24'—C25'—C26'−170.3 (14)
Sn1—C15—C16—C2176.6 (3)O3'—C25'—C26'—C27'−11.1 (12)
C21—C16—C17—C180.0C24'—C25'—C26'—C27'168.8 (12)
C15—C16—C17—C18176.2 (3)O3'—C25'—C26'—C31'168.3 (14)
C16—C17—C18—C190.0C24'—C25'—C26'—C31'−11.8 (14)
C17—C18—C19—C200.0C31'—C26'—C27'—C28'0.0
C18—C19—C20—C210.0C25'—C26'—C27'—C28'179.4 (15)
C19—C20—C21—C160.0C26'—C27'—C28'—C29'0.0
C19—C20—C21—Cl3−178.7 (3)C32'—O4'—C29'—C28'−2.5 (17)
C17—C16—C21—C200.0C32'—O4'—C29'—C30'178.2 (14)
C15—C16—C21—C20−176.1 (3)C27'—C28'—C29'—O4'−179.2 (11)
C17—C16—C21—Cl3178.8 (3)C27'—C28'—C29'—C30'0.0
C15—C16—C21—Cl32.6 (3)O4'—C29'—C30'—C31'179.3 (9)
O2'—Sn1—O1—C22−30.9 (4)C28'—C29'—C30'—C31'0.0
C15—Sn1—O1—C2273.1 (4)C29'—C30'—C31'—C26'0.0
C8—Sn1—O1—C22−55.2 (5)C27'—C26'—C31'—C30'0.0
C1—Sn1—O1—C22−173.9 (4)C25'—C26'—C31'—C30'−179.4 (14)
O1'—Sn1—O1—C22125.8 (10)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2728).

References

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  • Sisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc.83, 538–541.
  • Westrip, S. P. (2010). publCIF In preparation.

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