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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m197–m198.
Published online 2007 December 18. doi:  10.1107/S1600536807066378
PMCID: PMC2915128

Di-μ3-oxido-bis­(μ2-quinaldato-κ2 O:O)­bis­(quinaldato-κ2 N,O)tetra­kis[di-n-butyl­tin(IV)]

Abstract

The title tetra­nuclear SnIV complex, [Sn4(C4H9)8(C10H6NO2)4O2], is a cluster built up by inversion symmetry around the central Sn2O2 ring. The coordination geometries of the Sn atoms involved can be classified into two types: the five-coordinate Sn atoms of the central Sn2O2 core have a trigonal–bipyramidal geometry, with axial positions occupied by a μ3-O atom and a μ2-O atom belonging to the nonchelating quinaldate ligand. The peripheral Sn atoms are six-coordinate, with a distorted octa­hedral geometry. The methyl group of an n-butyl ligand is disordered over two sites, with occupancies of 0.643 (12) and 0.357 (12).

Related literature

For related tin complexes, see: Ma et al. (2004 [triangle]); Tian et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m197-scheme1.jpg

Experimental

Crystal data

  • [Sn4(C4H9)8(C10H6NO2)4O2]
  • M r = 1652.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m197-efi1.jpg
  • a = 13.096 (5) Å
  • b = 12.551 (5) Å
  • c = 22.278 (9) Å
  • β = 93.971 (5)°
  • V = 3653 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.41 mm−1
  • T = 298 (2) K
  • 0.52 × 0.31 × 0.24 mm

Data collection

  • Bruker SMART diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.517, T max = 0.714
  • 18614 measured reflections
  • 6437 independent reflections
  • 4499 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.127
  • S = 1.00
  • 6437 reflections
  • 410 parameters
  • 169 restraints
  • H-atom parameters constrained
  • Δρmax = 0.92 e Å−3
  • Δρmin = −0.49 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Siemens, 1996 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807066378/bh2155sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066378/bh2155Isup2.hkl

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

Acknowledgments

We thank the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province (2005ZX09) for financial support.

supplementary crystallographic information

Comment

The title compound, (I), is a cluster containing four Sn atoms (Fig. 1). The whole molecule lies on an inversion center, with a central Sn2O2 core. The structure is similar to that previously characterized with 3-hydroxypyridine-2-carboxylate as main ligand (Tian et al., 2005). The three-coordinated µ3 atom O5 in the Sn2O2 ring is bonded to a Bu2SnO2N unit. Moreover, the C1 carboxylate group coordinates to each independent Sn atom in a bridging mode (Fig. 2). The geometry of the Sn1 atom in the Sn2O2 ring is distorted trigonal-bipyramidal with atoms O1 and O5i [symmetry code (i): -x + 1, -y + 2, -z] in axial positions, while two n-butyl groups and atom O5 form the equatorial plane. For the Sn2 atoms, six primary bonds are formed: three to the O atoms, two to the C atom of n-butyl groups, and one to the chelating quinoline N atom. Thus, the Sn2 centers display a distorted octahedral coordinated geometry. The Sn—O and Sn—N bond lengths (Table 1) are similar to those observed in related organotin carboxylates (Ma et al., 2004).

Experimental

The reaction was carried out under a nitrogen atmosphere. Quinaldic acid (1 mmol) and sodium ethoxide (1.2 mmol) were dissolved in ethanol (30 ml) in a Schlenk flask and stirred for 0.5 h. Dibutyltin dichloride (1 mmol) was then added and the reaction mixture was stirred for 12 h at 313 K. The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (1:1). Yield: 83%; m.p. 426 K. Analysis: calculated for C72H96N4O10Sn4: C 52.33, H 5.86, N 3.39%. found: C 52.27, H 5.95, N 3.47%.

Refinement

Atoms C24 was found to be disordered over two positions (C24 and C24'). Site occupation factors were refined and converged to 0.643 (12) and 0.357 (12) for C24 and C24', respectively. All C—C bonds lengths in n-butyl groups were restrained to 1.53 (2) Å. In n-butyl groups, C atoms closer than 1.7 Å were restrained, with deviation of 0.04 Å2, to have the same Uij components. H atoms were positioned geometrically, with C—H = 0.93, 0.96 and 0.97 Å for aromatic, methyl and methylene H atoms, respectively, and constrained to ride on their parent C atoms, with Uiso(H) = xUeq(carrier C) where x = 1.5 for methyl groups and x = 1.2 otherwise.

Figures

Fig. 1.
The molecular structure of (I), with 30% probability displacement ellipsoids (H atoms have been omitted for clarity). The 'A' labeled atoms are generated by the symmetry operation -x + 1, -y + 2, -z.
Fig. 2.
In this view the n-butyl groups have been omitted for clarity. Atoms with the suffix 'A' are generated by the symmetry operation -x + 1, -y + 2, -z.

Crystal data

[Sn4(C4H9)8(C10H6NO2)4O2]F000 = 1672
Mr = 1652.29Dx = 1.502 Mg m3
Monoclinic, P21/nMelting point: 426 K
Hall symbol: -P 2ynMo Kα radiation λ = 0.71073 Å
a = 13.096 (5) ÅCell parameters from 5520 reflections
b = 12.551 (5) Åθ = 2.4–22.8º
c = 22.278 (9) ŵ = 1.41 mm1
β = 93.971 (5)ºT = 298 (2) K
V = 3653 (3) Å3Block, colourless
Z = 20.52 × 0.31 × 0.24 mm

Data collection

Bruker SMART diffractometer6437 independent reflections
Radiation source: fine-focus sealed tube4499 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.042
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −15→15
Tmin = 0.517, Tmax = 0.714k = −14→13
18614 measured reflectionsl = −26→24

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.127  w = 1/[σ2(Fo2) + (0.070P)2 + 1.6257P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
6437 reflectionsΔρmax = 0.92 e Å3
410 parametersΔρmin = −0.49 e Å3
169 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/UeqOcc. (<1)
Sn10.58177 (3)0.91100 (3)0.031663 (18)0.04351 (14)
Sn20.40982 (3)1.01477 (3)0.134696 (18)0.04798 (15)
N10.7010 (4)0.7402 (4)0.1158 (2)0.0499 (12)
N20.2731 (4)1.0753 (4)0.2026 (2)0.0496 (12)
O10.5611 (3)0.8952 (3)0.13314 (18)0.0552 (11)
O20.5595 (4)0.8522 (4)0.2299 (2)0.0719 (14)
O30.3094 (3)1.1246 (3)0.08965 (17)0.0552 (11)
O40.1692 (4)1.2240 (4)0.0797 (2)0.0786 (15)
O50.4664 (3)1.0120 (3)0.05126 (16)0.0447 (9)
C10.5892 (4)0.8379 (5)0.1812 (3)0.0508 (16)
C20.6629 (4)0.7465 (5)0.1691 (3)0.0502 (15)
C30.6865 (5)0.6729 (6)0.2153 (3)0.0622 (18)
H30.65940.68080.25260.075*
C40.7488 (6)0.5906 (6)0.2050 (3)0.069 (2)
H40.76400.54120.23550.083*
C50.7915 (5)0.5774 (5)0.1495 (3)0.0598 (17)
C60.7649 (4)0.6572 (5)0.1053 (3)0.0526 (15)
C70.8052 (5)0.6484 (6)0.0482 (3)0.0696 (19)
H70.79040.69990.01890.083*
C80.8655 (6)0.5647 (7)0.0368 (4)0.079 (2)
H80.89040.5582−0.00110.095*
C90.8916 (6)0.4870 (7)0.0806 (4)0.085 (2)
H90.93330.43010.07140.102*
C100.8567 (6)0.4944 (6)0.1359 (4)0.081 (2)
H100.87620.44400.16500.097*
C110.2277 (5)1.1646 (5)0.1088 (3)0.0571 (16)
C120.2061 (5)1.1373 (5)0.1730 (3)0.0500 (15)
C130.1163 (5)1.1745 (5)0.1979 (3)0.0602 (17)
H130.07031.21850.17600.072*
C140.0994 (5)1.1438 (6)0.2547 (3)0.0667 (19)
H140.04061.16700.27200.080*
C150.1684 (5)1.0780 (6)0.2880 (3)0.0601 (17)
C160.2572 (5)1.0449 (5)0.2604 (3)0.0518 (15)
C170.3286 (6)0.9802 (6)0.2931 (3)0.0681 (19)
H170.38810.95980.27570.082*
C180.3127 (6)0.9473 (6)0.3487 (3)0.074 (2)
H180.36090.90400.36940.089*
C190.2245 (7)0.9772 (7)0.3759 (4)0.083 (2)
H190.21390.95320.41450.099*
C200.1536 (6)1.0415 (7)0.3465 (3)0.077 (2)
H200.09511.06130.36520.093*
C210.7297 (5)0.9809 (5)0.0427 (3)0.0567 (16)
H21A0.77740.93170.02610.068*
H21B0.72881.04460.01800.068*
C220.7727 (6)1.0111 (7)0.1038 (3)0.085 (2)
H22A0.78050.94710.12800.102*
H22B0.72371.05660.12220.102*
C230.8746 (7)1.0681 (8)0.1058 (4)0.103 (3)
H23A0.90241.07040.14730.124*0.643 (12)
H23B0.92121.02630.08340.124*0.643 (12)
H23C0.86021.14320.09920.124*0.357 (12)
H23D0.90631.06180.14630.124*0.357 (12)
C240.8726 (12)1.1728 (12)0.0829 (8)0.131 (5)0.643 (12)
H24A0.94071.19400.07470.196*0.643 (12)
H24B0.84651.22030.11190.196*0.643 (12)
H24C0.82931.17530.04640.196*0.643 (12)
C24'0.9529 (19)1.033 (2)0.0654 (12)0.131 (5)0.357 (12)
H24D0.92940.97070.04400.196*0.357 (12)
H24E1.01541.01760.08880.196*0.357 (12)
H24F0.96481.08920.03730.196*0.357 (12)
C250.5233 (5)0.7567 (5)0.0104 (3)0.0580 (16)
H25A0.57150.7200−0.01350.070*
H25B0.51930.71710.04750.070*
C260.4205 (5)0.7548 (6)−0.0231 (4)0.086 (2)
H26A0.42670.7831−0.06320.103*
H26B0.37470.8011−0.00280.103*
C270.3720 (7)0.6405 (7)−0.0285 (5)0.114 (3)
H27A0.37200.60900.01130.136*
H27B0.30140.6465−0.04440.136*
C280.4260 (9)0.5720 (9)−0.0665 (6)0.153 (5)
H28A0.41570.5958−0.10740.230*
H28B0.40090.5005−0.06340.230*
H28C0.49770.5737−0.05430.230*
C290.5124 (5)1.1132 (5)0.1885 (3)0.0577 (16)
H29A0.52681.07810.22690.069*
H29B0.57641.11730.16910.069*
C300.4775 (6)1.2250 (6)0.2003 (4)0.084 (2)
H30A0.41571.22270.22190.101*
H30B0.46141.26110.16230.101*
C310.5616 (7)1.2885 (7)0.2378 (4)0.100 (3)
H31A0.58001.24950.27450.119*
H31B0.62201.29270.21510.119*
C320.5318 (10)1.3937 (9)0.2531 (6)0.159 (5)
H32A0.51331.43310.21700.238*
H32B0.58781.42860.27520.238*
H32C0.47421.39040.27740.238*
C330.3270 (5)0.8681 (5)0.1364 (3)0.0619 (17)
H33A0.36130.81660.11230.074*
H33B0.33170.84200.17750.074*
C340.2147 (5)0.8700 (6)0.1144 (4)0.078 (2)
H34A0.17850.91670.14040.094*
H34B0.20870.90020.07420.094*
C350.1644 (6)0.7645 (7)0.1129 (5)0.108 (3)
H35A0.16670.73660.15350.130*
H35B0.20360.71660.08920.130*
C360.0566 (8)0.7635 (10)0.0878 (6)0.174 (5)
H36A0.02300.82750.09940.262*
H36B0.02210.70280.10310.262*
H36C0.05480.75950.04470.262*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.0420 (2)0.0421 (3)0.0458 (2)−0.00321 (18)−0.00117 (17)−0.00413 (18)
Sn20.0527 (3)0.0511 (3)0.0405 (2)−0.0060 (2)0.00546 (18)−0.00393 (18)
N10.053 (3)0.050 (3)0.046 (3)−0.009 (3)−0.005 (2)0.007 (2)
N20.054 (3)0.056 (3)0.040 (3)0.005 (3)0.007 (2)−0.005 (2)
O10.058 (3)0.062 (3)0.046 (2)0.007 (2)0.005 (2)0.005 (2)
O20.089 (4)0.086 (4)0.041 (3)0.006 (3)0.011 (2)0.004 (2)
O30.063 (3)0.062 (3)0.042 (2)0.006 (2)0.007 (2)0.002 (2)
O40.082 (3)0.094 (4)0.059 (3)0.030 (3)0.001 (3)0.012 (3)
O50.048 (2)0.050 (2)0.036 (2)0.0018 (18)0.0065 (17)0.0003 (17)
C10.045 (3)0.045 (4)0.059 (4)−0.009 (3)−0.024 (3)0.005 (3)
C20.044 (3)0.060 (4)0.045 (4)−0.012 (3)−0.006 (3)0.009 (3)
C30.060 (4)0.077 (5)0.049 (4)−0.005 (4)0.000 (3)0.012 (3)
C40.074 (5)0.069 (5)0.062 (5)0.000 (4)−0.008 (4)0.025 (4)
C50.052 (4)0.059 (4)0.066 (4)0.001 (3)−0.014 (3)0.006 (3)
C60.046 (3)0.056 (4)0.055 (4)−0.005 (3)−0.007 (3)0.001 (3)
C70.068 (5)0.077 (5)0.063 (5)0.001 (4)0.003 (4)−0.006 (4)
C80.068 (5)0.089 (6)0.082 (6)0.006 (4)0.010 (4)−0.015 (5)
C90.071 (5)0.076 (6)0.107 (7)0.011 (4)−0.009 (5)−0.003 (5)
C100.073 (5)0.077 (6)0.090 (6)0.008 (4)−0.020 (5)0.016 (5)
C110.061 (4)0.053 (4)0.056 (4)−0.002 (3)−0.004 (3)−0.010 (3)
C120.052 (4)0.053 (4)0.045 (3)0.004 (3)0.004 (3)0.002 (3)
C130.053 (4)0.061 (4)0.067 (4)0.011 (3)0.005 (3)−0.001 (3)
C140.055 (4)0.078 (5)0.069 (5)0.004 (4)0.022 (3)−0.006 (4)
C150.056 (4)0.067 (5)0.058 (4)−0.003 (3)0.011 (3)−0.007 (3)
C160.053 (4)0.056 (4)0.046 (3)0.000 (3)0.004 (3)−0.005 (3)
C170.077 (5)0.070 (5)0.059 (4)0.011 (4)0.009 (4)0.006 (4)
C180.088 (5)0.083 (5)0.053 (4)0.014 (4)0.005 (4)0.005 (4)
C190.096 (6)0.097 (6)0.057 (5)−0.006 (5)0.017 (4)0.012 (4)
C200.079 (5)0.094 (6)0.062 (5)−0.002 (5)0.029 (4)0.001 (4)
C210.049 (4)0.058 (4)0.061 (4)−0.011 (3)−0.005 (3)0.003 (3)
C220.073 (5)0.106 (6)0.075 (5)−0.034 (4)−0.001 (4)−0.002 (4)
C230.091 (6)0.116 (7)0.099 (6)−0.042 (5)−0.022 (5)0.004 (5)
C240.121 (9)0.125 (10)0.143 (10)−0.044 (8)−0.022 (8)0.028 (9)
C24'0.121 (9)0.125 (10)0.143 (10)−0.044 (8)−0.022 (8)0.028 (9)
C250.061 (4)0.045 (4)0.065 (4)−0.003 (3)−0.015 (3)−0.005 (3)
C260.069 (5)0.066 (5)0.118 (6)−0.011 (4)−0.024 (4)−0.011 (4)
C270.096 (6)0.093 (6)0.146 (8)−0.014 (5)−0.030 (6)−0.031 (6)
C280.160 (11)0.131 (10)0.165 (11)−0.028 (8)−0.016 (9)−0.038 (8)
C290.058 (4)0.057 (4)0.058 (4)−0.009 (3)−0.001 (3)−0.009 (3)
C300.068 (4)0.075 (5)0.109 (6)−0.008 (4)−0.002 (4)−0.027 (5)
C310.105 (6)0.070 (5)0.119 (6)−0.003 (5)−0.024 (5)−0.031 (5)
C320.164 (11)0.130 (10)0.177 (12)−0.007 (9)−0.023 (9)−0.050 (9)
C330.057 (4)0.053 (4)0.077 (4)−0.006 (3)0.010 (3)−0.002 (3)
C340.063 (4)0.077 (5)0.094 (5)−0.021 (4)−0.002 (4)0.009 (4)
C350.085 (6)0.085 (6)0.153 (8)−0.028 (5)0.000 (6)−0.004 (6)
C360.120 (9)0.159 (11)0.238 (14)−0.064 (8)−0.038 (9)−0.009 (10)

Geometric parameters (Å, °)

Sn1—O52.042 (4)C21—H21A0.9700
Sn1—C252.124 (6)C21—H21B0.9700
Sn1—C212.126 (6)C22—C231.512 (9)
Sn1—O5i2.141 (4)C22—H22A0.9700
Sn1—O12.304 (4)C22—H22B0.9700
Sn1—N13.184 (5)C23—C241.409 (13)
Sn2—O52.049 (4)C23—C24'1.476 (18)
Sn2—O32.111 (4)C23—H23A0.9700
Sn2—C292.131 (6)C23—H23B0.9700
Sn2—C332.138 (6)C23—H23C0.9700
Sn2—O12.488 (4)C23—H23D0.9700
Sn2—N22.539 (5)C24—H23C0.5516
N1—C21.322 (7)C24—H24A0.9600
N1—C61.367 (8)C24—H24B0.9600
N2—C121.315 (7)C24—H24C0.9600
N2—C161.373 (8)C24'—H24D0.9600
O1—C11.321 (7)C24'—H24E0.9600
O2—C11.191 (7)C24'—H24F0.9600
O3—C111.281 (8)C25—C261.493 (8)
O4—C111.223 (7)C25—H25A0.9700
O5—Sn1i2.141 (4)C25—H25B0.9700
C1—C21.535 (9)C26—C271.570 (10)
C2—C31.402 (8)C26—H26A0.9700
C3—C41.346 (9)C26—H26B0.9700
C3—H30.9300C27—C281.428 (12)
C4—C51.402 (10)C27—H27A0.9700
C4—H40.9300C27—H27B0.9700
C5—C101.395 (10)C28—H28A0.9600
C5—C61.429 (9)C28—H28B0.9600
C6—C71.415 (9)C28—H28C0.9600
C7—C81.348 (10)C29—C301.506 (8)
C7—H70.9300C29—H29A0.9700
C8—C91.406 (11)C29—H29B0.9700
C8—H80.9300C30—C311.555 (9)
C9—C101.345 (12)C30—H30A0.9700
C9—H90.9300C30—H30B0.9700
C10—H100.9300C31—C321.426 (11)
C11—C121.517 (9)C31—H31A0.9700
C12—C131.413 (8)C31—H31B0.9700
C13—C141.356 (9)C32—H32A0.9600
C13—H130.9300C32—H32B0.9600
C14—C151.398 (9)C32—H32C0.9600
C14—H140.9300C33—C341.518 (8)
C15—C201.408 (9)C33—H33A0.9700
C15—C161.416 (9)C33—H33B0.9700
C16—C171.403 (9)C34—C351.479 (9)
C17—C181.335 (9)C34—H34A0.9700
C17—H170.9300C34—H34B0.9700
C18—C191.394 (11)C35—C361.482 (11)
C18—H180.9300C35—H35A0.9700
C19—C201.363 (11)C35—H35B0.9700
C19—H190.9300C36—H36A0.9600
C20—H200.9300C36—H36B0.9600
C21—C221.486 (8)C36—H36C0.9600
O5—Sn1—C25110.7 (2)C21—C22—H22A108.5
O5—Sn1—C21113.6 (2)C23—C22—H22A108.5
C25—Sn1—C21135.5 (3)C21—C22—H22B108.5
O5—Sn1—O5i74.10 (15)C23—C22—H22B108.5
C25—Sn1—O5i98.0 (2)H22A—C22—H22B107.5
C21—Sn1—O5i97.2 (2)C24—C23—C24'92.9 (15)
O5—Sn1—O172.85 (14)C24—C23—C22115.9 (10)
C25—Sn1—O194.3 (2)C24'—C23—C22119.4 (14)
C21—Sn1—O195.2 (2)C24—C23—H23A108.3
O5i—Sn1—O1146.94 (14)C24'—C23—H23A111.0
O5—Sn1—N1129.19 (14)C22—C23—H23A108.3
C25—Sn1—N170.85 (19)C24—C23—H23B108.3
C21—Sn1—N178.7 (2)C22—C23—H23B108.3
O5i—Sn1—N1156.19 (13)H23A—C23—H23B107.4
O1—Sn1—N156.67 (14)C24'—C23—H23C109.2
O5—Sn2—O380.36 (15)C22—C23—H23C107.0
O5—Sn2—C29105.4 (2)H23A—C23—H23C100.0
O3—Sn2—C29103.7 (2)H23B—C23—H23C124.7
O5—Sn2—C33102.6 (2)C24—C23—H23D114.2
O3—Sn2—C33105.7 (2)C24'—C23—H23D105.8
C29—Sn2—C33142.1 (3)C22—C23—H23D108.0
O5—Sn2—O168.81 (14)H23B—C23—H23D101.0
O3—Sn2—O1149.11 (14)H23C—C23—H23D106.7
C29—Sn2—O183.4 (2)C23—C24—H24A109.5
C33—Sn2—O183.5 (2)H23C—C24—H24A129.2
O5—Sn2—N2149.32 (15)C23—C24—H24B109.5
O3—Sn2—N269.24 (16)H23C—C24—H24B80.8
C29—Sn2—N286.3 (2)H24A—C24—H24B109.5
C33—Sn2—N282.4 (2)C23—C24—H24C109.5
O1—Sn2—N2141.64 (14)H23C—C24—H24C113.3
C2—N1—C6118.2 (5)H24A—C24—H24C109.5
C2—N1—Sn1106.8 (4)H24B—C24—H24C109.5
C6—N1—Sn1134.0 (4)C23—C24'—H24D109.5
C12—N2—C16119.7 (5)C23—C24'—H24E109.5
C12—N2—Sn2110.7 (4)H24D—C24'—H24E109.5
C16—N2—Sn2129.4 (4)C23—C24'—H24F109.5
C1—O1—Sn1142.9 (4)H24D—C24'—H24F109.5
C1—O1—Sn2119.6 (4)H24E—C24'—H24F109.5
Sn1—O1—Sn296.27 (14)C26—C25—Sn1115.1 (5)
C11—O3—Sn2127.2 (4)C26—C25—H25A108.5
Sn1—O5—Sn2121.61 (18)Sn1—C25—H25A108.5
Sn1—O5—Sn1i105.90 (15)C26—C25—H25B108.5
Sn2—O5—Sn1i132.19 (19)Sn1—C25—H25B108.5
O2—C1—O1124.5 (6)H25A—C25—H25B107.5
O2—C1—C2121.5 (5)C25—C26—C27113.5 (7)
O1—C1—C2114.0 (6)C25—C26—H26A108.9
N1—C2—C3122.9 (6)C27—C26—H26A108.9
N1—C2—C1118.9 (5)C25—C26—H26B108.9
C3—C2—C1118.2 (6)C27—C26—H26B108.9
C4—C3—C2119.1 (6)H26A—C26—H26B107.7
C4—C3—H3120.5C28—C27—C26112.4 (9)
C2—C3—H3120.5C28—C27—H27A109.1
C3—C4—C5121.6 (6)C26—C27—H27A109.1
C3—C4—H4119.2C28—C27—H27B109.1
C5—C4—H4119.2C26—C27—H27B109.1
C10—C5—C4124.6 (7)H27A—C27—H27B107.9
C10—C5—C6119.8 (7)C27—C28—H28A109.5
C4—C5—C6115.6 (6)C27—C28—H28B109.5
N1—C6—C7118.9 (6)H28A—C28—H28B109.5
N1—C6—C5122.6 (6)C27—C28—H28C109.5
C7—C6—C5118.5 (6)H28A—C28—H28C109.5
C8—C7—C6119.3 (7)H28B—C28—H28C109.5
C8—C7—H7120.4C30—C29—Sn2116.8 (5)
C6—C7—H7120.4C30—C29—H29A108.1
C7—C8—C9121.8 (8)Sn2—C29—H29A108.1
C7—C8—H8119.1C30—C29—H29B108.1
C9—C8—H8119.1Sn2—C29—H29B108.1
C10—C9—C8120.4 (8)H29A—C29—H29B107.3
C10—C9—H9119.8C29—C30—C31111.0 (6)
C8—C9—H9119.8C29—C30—H30A109.4
C9—C10—C5120.2 (7)C31—C30—H30A109.4
C9—C10—H10119.9C29—C30—H30B109.4
C5—C10—H10119.9C31—C30—H30B109.4
O4—C11—O3124.7 (6)H30A—C30—H30B108.0
O4—C11—C12119.1 (6)C32—C31—C30114.1 (8)
O3—C11—C12116.2 (6)C32—C31—H31A108.7
N2—C12—C13123.0 (6)C30—C31—H31A108.7
N2—C12—C11116.3 (5)C32—C31—H31B108.7
C13—C12—C11120.7 (6)C30—C31—H31B108.7
C14—C13—C12117.8 (6)H31A—C31—H31B107.6
C14—C13—H13121.1C31—C32—H32A109.5
C12—C13—H13121.1C31—C32—H32B109.5
C13—C14—C15121.4 (6)H32A—C32—H32B109.5
C13—C14—H14119.3C31—C32—H32C109.5
C15—C14—H14119.3H32A—C32—H32C109.5
C14—C15—C20123.9 (7)H32B—C32—H32C109.5
C14—C15—C16117.6 (6)C34—C33—Sn2117.5 (5)
C20—C15—C16118.5 (7)C34—C33—H33A107.9
N2—C16—C17120.7 (6)Sn2—C33—H33A107.9
N2—C16—C15120.5 (6)C34—C33—H33B107.9
C17—C16—C15118.8 (6)Sn2—C33—H33B107.9
C18—C17—C16121.3 (7)H33A—C33—H33B107.2
C18—C17—H17119.3C35—C34—C33114.4 (7)
C16—C17—H17119.3C35—C34—H34A108.7
C17—C18—C19120.5 (8)C33—C34—H34A108.7
C17—C18—H18119.8C35—C34—H34B108.7
C19—C18—H18119.8C33—C34—H34B108.7
C20—C19—C18120.5 (7)H34A—C34—H34B107.6
C20—C19—H19119.7C34—C35—C36115.3 (9)
C18—C19—H19119.7C34—C35—H35A108.4
C19—C20—C15120.3 (7)C36—C35—H35A108.4
C19—C20—H20119.8C34—C35—H35B108.4
C15—C20—H20119.8C36—C35—H35B108.4
C22—C21—Sn1119.7 (5)H35A—C35—H35B107.5
C22—C21—H21A107.4C35—C36—H36A109.5
Sn1—C21—H21A107.4C35—C36—H36B109.5
C22—C21—H21B107.4H36A—C36—H36B109.5
Sn1—C21—H21B107.4C35—C36—H36C109.5
H21A—C21—H21B106.9H36A—C36—H36C109.5
C21—C22—C23115.2 (7)H36B—C36—H36C109.5

Symmetry codes: (i) −x+1, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2155).

References

  • Ma, C. L., Jiang, Q., Zhang, R. F. & Wang, D. Q. (2004). J. Chem. Soc. Dalton Trans. pp. 1832–1840.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Siemens (1996). SMART (Version 4.0), SAINT (Version 4.0) and SHELXTL (Version 5.1). Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Tian, G.-R., Zhang, R.-F., Ma, C.-L. & Ng, S. W. (2005). Acta Cryst. E61, m2528–m2530.

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