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

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ISSN: 2056-9890

Octa­butyl­bis­{(E)-2-[4-(2-hy­droxy­benzyl­­idene­amino)phen­yl]acetato}di-μ2-methoxo-di-μ3-oxido-tetra­tin(IV)

aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China.
*Correspondence e-mail: handongyin@163.com

(Received 16 September 2009; accepted 25 September 2009; online 3 October 2009)

The title compound, [Sn4(C4H9)8(C15H12NO3)2(CH3O)2O2], is a centrosymmetric dimer and displays a ladder type structural motif. There are four SnIV centres which can be divided into two sorts, viz. two endocyclic and two exocyclic. The endo- and exocyclic SnIV centres are linked by bidentate deprotonated methanol and μ3-O atoms. Each exocyclic SnIV centre is also coordinated by a monodentate 2-[4-(2-hydroxy­benzyl­idene­amino)phen­yl]acetate ligand. Parts of the butyl groups were found to be disordered over two sets of sites.

Related literature

For related structures, see: Berceanc et al. (2002[Berceanc, V., Crainic, C., Haiduc, I., Mahon, M. F., Molloy, K. C., Venter, M. M. & Wilson, P. J. (2002). J. Chem. Soc. Dalton Trans. pp. 1036-1045.]); Garcia-Zarracino & Hopfl (2005[Garcia-Zarracino, R. & Hopfl, H. (2005). J. Am. Chem. Soc. 127, 3120-3130.]); Wu et al. (2009[Wu, X., Kang, W., Zhu, D., Zhu, C. & Liu, S. (2009). J. Organomet. Chem. 694, 2981-2986.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn4(C4H9)8(C15H12NO3)2(CH3O)2O2]

  • Mr = 1534.32

  • Triclinic, [P \overline 1]

  • a = 10.6059 (14) Å

  • b = 12.2128 (17) Å

  • c = 14.522 (2) Å

  • α = 104.921 (2)°

  • β = 104.271 (2)°

  • γ = 91.991 (1)°

  • V = 1751.8 (4) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 1.46 mm−1

  • T = 298 K

  • 0.40 × 0.39 × 0.19 mm

Data collection
  • Siemens SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.593, Tmax = 0.769

  • 9161 measured reflections

  • 6067 independent reflections

  • 4114 reflections with I > 2σ(I)

  • Rint = 0.019

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.140

  • S = 1.04

  • 6067 reflections

  • 453 parameters

  • H-atom parameters constrained

  • Δρmax = 1.31 e Å−3

  • Δρmin = −0.56 e Å−3

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Recently, a large number of organotin compounds with different structural features have been reported in the literature (Berceanc et al., 2002; Garcia-Zarracino & Hopfl et al., 2005). In continuation of our study of organotin compounds, we present here the synthesis and crystal structure of the title compound (I).

The title compound (Fig. 1) is a centrosymmetric dimer, with three linearly fused four-membered Sn—O—Sn—O rings, resulting in a ladder type structural motif. There are two tri-coordinate O atoms in (I), and each of them links two endocyclic tin atoms and one exocyclic tin atom (Sn(1)—O(4) = 2.022 (4) Å; Sn(2)—O(4) = 2.051 (4) Å; Sn(1)—O(4 A) = 2.127 (4) Å)(Table. 1). The additional links between the endo- and exocyclic Sn are provided by bidentate deprotonated methanol. Each exocyclic Sn atom is also coordinated by monodentate carboxylato ligand. Part of butyl groups were found to be disordered over two sites. The crystal structure of a similiar compound has been reported recently (Wu et al., 2009).

Related literature top

For related structures, see: Berceanc et al. (2002); Garcia-Zarracino & Hopfl (2005); Wu et al. (2009).

Experimental top

The reaction was carried out under a nitrogen atmosphere. (E)-2-(4-(benzylideneamino)phenyl)acetic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to a stirred solution of benzene (30 ml) in a Schlenk flask and stirred for 0.5 h. Dibutyltin chloride (2 mmol) was then added to the reactor. After stirring for 6 h at 323 K, the yellow paste was obtained and then filtered. Yellow crystals suitable for X-ray analysis were obtained by slow evaporation of dichloromethane/methanol (1:1 V/V) solution over a period of six days (yield 86%. m.p.458 K). Anal. Calcd (%) for C64H98N2O10Sn4 (Mr = 1530.20): C, 50.23; H, 6.46; N, 1.83; O, 10.46; Sn, 31.03. Found (%): C, 50.19; H, 6.44; N, 1.85; O, 10.47; Sn, 31.05.

Refinement top

The atoms C18, C19, C20, C21, C22, C23, C29, C30 and C31 were found to be disordered over two sites, and the ratio of the occupancy factors refined to 0.70 (8):0.30 (8), 0.70 (8):0.30 (8), 0.66 (3):0.34 (3), 0.66 (3):0.34 (3), 0.66 (3):0.34 (3), 0.66 (3):0.34 (3), 0.66 (3):0.34 (3), 0.66 (3):0.34 (3) and 0.66 (3):0.34 (3) for atoms C18:c18', C19:c19', C20:c20', C21:C21', C22:C22', C23:C23', C29:C29', C30:C30' and C31:C31', respectively. H atoms were positioned geometrically, with C—H = 0.93, 0.96, 0.97 and 0.82 Å for aromatic, methyl, methylene and hydroxyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C, O) for the methyl and hydroxyl groups

Structure description top

Recently, a large number of organotin compounds with different structural features have been reported in the literature (Berceanc et al., 2002; Garcia-Zarracino & Hopfl et al., 2005). In continuation of our study of organotin compounds, we present here the synthesis and crystal structure of the title compound (I).

The title compound (Fig. 1) is a centrosymmetric dimer, with three linearly fused four-membered Sn—O—Sn—O rings, resulting in a ladder type structural motif. There are two tri-coordinate O atoms in (I), and each of them links two endocyclic tin atoms and one exocyclic tin atom (Sn(1)—O(4) = 2.022 (4) Å; Sn(2)—O(4) = 2.051 (4) Å; Sn(1)—O(4 A) = 2.127 (4) Å)(Table. 1). The additional links between the endo- and exocyclic Sn are provided by bidentate deprotonated methanol. Each exocyclic Sn atom is also coordinated by monodentate carboxylato ligand. Part of butyl groups were found to be disordered over two sites. The crystal structure of a similiar compound has been reported recently (Wu et al., 2009).

For related structures, see: Berceanc et al. (2002); Garcia-Zarracino & Hopfl (2005); Wu et al. (2009).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity. [Symmetry code: -x + 1,-y + 1,-z]
Octabutylbis{(E)-2-[4-(2-hydroxybenzylideneamino)phenyl]acetato}di- µ2-methoxo-di-µ3-oxido-tetratin(IV) top
Crystal data top
[Sn4(C4H9)8(C15H12NO3)2(CH3O)2O2]Z = 1
Mr = 1534.32F(000) = 780
Triclinic, P1Dx = 1.451 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.6059 (14) ÅCell parameters from 3867 reflections
b = 12.2128 (17) Åθ = 2.2–25.7°
c = 14.522 (2) ŵ = 1.46 mm1
α = 104.921 (2)°T = 298 K
β = 104.271 (2)°Block, colorless
γ = 91.991 (1)°0.40 × 0.39 × 0.19 mm
V = 1751.8 (4) Å3
Data collection top
Siemens SMART CCD area-detector
diffractometer
6067 independent reflections
Radiation source: fine-focus sealed tube4114 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 912
Tmin = 0.593, Tmax = 0.769k = 1413
9161 measured reflectionsl = 1717
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0706P)2 + 2.6157P]
where P = (Fo2 + 2Fc2)/3
6067 reflections(Δ/σ)max = 0.001
453 parametersΔρmax = 1.31 e Å3
0 restraintsΔρmin = 0.56 e Å3
Crystal data top
[Sn4(C4H9)8(C15H12NO3)2(CH3O)2O2]γ = 91.991 (1)°
Mr = 1534.32V = 1751.8 (4) Å3
Triclinic, P1Z = 1
a = 10.6059 (14) ÅMo Kα radiation
b = 12.2128 (17) ŵ = 1.46 mm1
c = 14.522 (2) ÅT = 298 K
α = 104.921 (2)°0.40 × 0.39 × 0.19 mm
β = 104.271 (2)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
6067 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4114 reflections with I > 2σ(I)
Tmin = 0.593, Tmax = 0.769Rint = 0.019
9161 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.140H-atom parameters constrained
S = 1.04Δρmax = 1.31 e Å3
6067 reflectionsΔρmin = 0.56 e Å3
453 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.65357 (4)0.35975 (4)0.14820 (3)0.05024 (16)
Sn20.52091 (4)0.59836 (4)0.10841 (3)0.04935 (16)
N10.9801 (6)0.0426 (5)0.2942 (4)0.0634 (15)
O10.6229 (5)0.2161 (4)0.0182 (3)0.0638 (13)
O20.7256 (6)0.1199 (5)0.1181 (4)0.0823 (16)
O31.0365 (6)0.1364 (5)0.4230 (5)0.0909 (18)
H30.99470.12330.38570.136*
O40.5571 (4)0.4355 (4)0.0470 (3)0.0547 (11)
O50.6272 (5)0.5360 (4)0.2274 (3)0.0595 (12)
C10.6645 (7)0.1245 (6)0.0363 (6)0.0583 (18)
C20.6344 (7)0.0194 (6)0.0508 (5)0.0623 (18)
H2A0.64350.04780.02680.075*
H2B0.54440.01540.08880.075*
C30.7237 (7)0.0198 (6)0.1167 (5)0.0560 (17)
C40.6932 (8)0.0674 (7)0.1940 (6)0.070 (2)
H40.61360.09750.20790.084*
C50.7779 (8)0.0717 (7)0.2520 (6)0.068 (2)
H50.75400.10370.30450.082*
C60.8976 (7)0.0290 (6)0.2330 (5)0.0591 (18)
C70.9282 (8)0.0209 (7)0.1563 (6)0.070 (2)
H71.00710.05230.14320.084*
C80.8430 (8)0.0247 (7)0.0990 (6)0.067 (2)
H80.86610.05790.04710.081*
C91.0880 (8)0.0011 (6)0.2867 (5)0.0654 (19)
H91.11270.04150.24180.079*
C101.1754 (7)0.0177 (6)0.3466 (5)0.0634 (19)
C111.1448 (8)0.0835 (7)0.4122 (6)0.069 (2)
C121.2303 (9)0.0984 (8)0.4689 (7)0.084 (2)
H121.20970.14150.51380.101*
C131.3438 (10)0.0486 (9)0.4572 (7)0.092 (3)
H131.40070.05860.49460.110*
C141.3772 (10)0.0163 (9)0.3913 (7)0.097 (3)
H141.45580.04890.38420.117*
C151.2924 (9)0.0321 (8)0.3362 (7)0.086 (3)
H151.31340.07610.29210.103*
C160.8584 (7)0.3962 (8)0.1767 (6)0.077 (2)
H16A0.87930.37520.11350.092*
H16B0.87810.47820.20250.092*
C170.9505 (10)0.3444 (10)0.2443 (9)0.111 (3)
H17A1.03930.37170.24860.133*0.70 (8)
H17B0.93970.26240.21610.133*0.70 (8)
H17C1.02350.40050.28410.133*0.30 (8)
H17D0.98540.28160.20560.133*0.30 (8)
C180.932 (5)0.370 (5)0.347 (4)0.108 (10)0.70 (8)
H18A0.84250.34520.34240.130*0.70 (8)
H18B0.94620.45210.37600.130*0.70 (8)
C191.026 (5)0.312 (4)0.413 (4)0.136 (11)0.70 (8)
H19A1.02850.23440.37770.203*0.70 (8)
H19B0.99560.31290.47070.203*0.70 (8)
H19C1.11200.35180.43370.203*0.70 (8)
C200.512 (3)0.289 (3)0.2016 (19)0.072 (7)0.66 (3)
H20A0.42700.30170.16500.087*0.66 (3)
H20B0.51680.20760.18630.087*0.66 (3)
C210.5211 (16)0.3327 (13)0.3105 (12)0.086 (6)0.66 (3)
H21A0.52490.41510.32790.103*0.66 (3)
H21B0.60210.31300.34770.103*0.66 (3)
C220.408 (3)0.286 (3)0.3417 (19)0.102 (8)0.66 (3)
H22A0.32820.31560.31290.122*0.66 (3)
H22B0.39540.20380.31630.122*0.66 (3)
C230.431 (4)0.318 (3)0.451 (2)0.145 (11)0.66 (3)
H23A0.50720.28550.47990.217*0.66 (3)
H23B0.35650.28920.46780.217*0.66 (3)
H23C0.44440.39930.47690.217*0.66 (3)
C18'0.914 (11)0.317 (9)0.329 (8)0.10 (2)0.30 (8)
H18C0.90370.23540.31800.116*0.30 (8)
H18D0.83040.34530.33370.116*0.30 (8)
C19'1.018 (10)0.371 (11)0.427 (8)0.13 (3)0.30 (8)
H19D0.97620.41410.47460.200*0.30 (8)
H19E1.08110.42120.41630.200*0.30 (8)
H19F1.06010.31240.45140.200*0.30 (8)
C20'0.552 (6)0.286 (7)0.238 (4)0.075 (13)0.34 (3)
H20C0.54500.20350.21380.090*0.34 (3)
H20D0.60540.30740.30550.090*0.34 (3)
C21'0.416 (3)0.322 (3)0.236 (2)0.096 (12)0.34 (3)
H21C0.36230.29960.16880.115*0.34 (3)
H21D0.42280.40460.25970.115*0.34 (3)
C22'0.347 (5)0.272 (6)0.300 (4)0.103 (14)0.34 (3)
H22C0.25350.26570.27230.123*0.34 (3)
H22D0.37190.19540.29760.123*0.34 (3)
C23'0.382 (7)0.343 (7)0.406 (5)0.14 (2)0.34 (3)
H23D0.47250.34000.43680.217*0.34 (3)
H23E0.32870.31340.44120.217*0.34 (3)
H23F0.36620.42040.40880.217*0.34 (3)
C240.3385 (7)0.6054 (7)0.1451 (6)0.069 (2)
H24A0.29050.65930.11550.083*
H24B0.28880.53110.11460.083*
C250.3425 (8)0.6382 (8)0.2542 (6)0.077 (2)
H25A0.38280.71590.28440.093*
H25B0.39650.58910.28620.093*
C260.2068 (9)0.6289 (9)0.2717 (8)0.102 (3)
H26A0.15300.67810.23960.122*
H26B0.16650.55130.24130.122*
C270.2089 (13)0.6614 (12)0.3807 (9)0.144 (5)
H27A0.25040.60600.41090.216*
H27B0.12090.66340.38680.216*
H27C0.25670.73510.41300.216*
C280.6575 (8)0.7411 (7)0.1316 (6)0.078 (2)
H28A0.60730.80610.13230.094*0.66 (3)
H28B0.71340.75410.19800.094*0.66 (3)
H28C0.61700.79860.10230.094*0.34 (3)
H28D0.69900.77530.20120.094*0.34 (3)
C290.7475 (19)0.7479 (17)0.0664 (13)0.089 (6)0.66 (3)
H29A0.69820.72640.00250.106*0.66 (3)
H29B0.78890.82500.08300.106*0.66 (3)
C300.849 (2)0.6678 (15)0.0837 (13)0.090 (6)0.66 (3)
H30A0.80630.59100.06740.109*0.66 (3)
H30B0.89670.68930.15290.109*0.66 (3)
C310.943 (3)0.670 (3)0.021 (2)0.109 (8)0.66 (3)
H31A0.89730.68270.04100.163*0.66 (3)
H31B0.97990.59890.00820.163*0.66 (3)
H31C1.01210.73080.05480.163*0.66 (3)
C29'0.757 (4)0.682 (3)0.077 (3)0.082 (10)0.34 (3)
H29C0.79330.62560.10930.098*0.34 (3)
H29D0.70850.64120.00990.098*0.34 (3)
C30'0.868 (3)0.758 (3)0.071 (2)0.085 (12)0.34 (3)
H30C0.92010.79080.13900.102*0.34 (3)
H30D0.82950.82030.04890.102*0.34 (3)
C31'0.965 (5)0.718 (4)0.011 (4)0.096 (13)0.34 (3)
H31D1.03050.68140.04690.143*0.34 (3)
H31E1.00500.78210.00160.143*0.34 (3)
H31F0.91900.66470.05070.143*0.34 (3)
C320.6961 (9)0.6034 (8)0.3245 (6)0.097 (3)
H32A0.78420.62530.32520.145*
H32B0.69740.55960.37090.145*
H32C0.65300.67040.34250.145*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0542 (3)0.0548 (3)0.0449 (3)0.0153 (2)0.0181 (2)0.0133 (2)
Sn20.0521 (3)0.0467 (3)0.0438 (3)0.0123 (2)0.0129 (2)0.0019 (2)
N10.063 (4)0.068 (4)0.062 (4)0.012 (3)0.024 (3)0.015 (3)
O10.081 (3)0.058 (3)0.054 (3)0.025 (3)0.022 (3)0.010 (2)
O20.100 (4)0.078 (4)0.072 (4)0.024 (3)0.016 (3)0.029 (3)
O30.089 (4)0.106 (5)0.102 (4)0.032 (4)0.043 (4)0.052 (4)
O40.066 (3)0.048 (3)0.046 (2)0.023 (2)0.013 (2)0.005 (2)
O50.068 (3)0.057 (3)0.045 (2)0.014 (2)0.009 (2)0.005 (2)
C10.061 (4)0.058 (4)0.066 (5)0.020 (4)0.031 (4)0.021 (4)
C20.068 (5)0.050 (4)0.075 (5)0.010 (3)0.030 (4)0.016 (4)
C30.064 (4)0.047 (4)0.060 (4)0.009 (3)0.028 (4)0.010 (3)
C40.067 (5)0.074 (5)0.074 (5)0.022 (4)0.026 (4)0.020 (4)
C50.074 (5)0.076 (5)0.064 (5)0.022 (4)0.024 (4)0.028 (4)
C60.066 (5)0.059 (4)0.058 (4)0.015 (4)0.024 (4)0.018 (3)
C70.066 (5)0.080 (5)0.075 (5)0.028 (4)0.032 (4)0.025 (4)
C80.074 (5)0.074 (5)0.067 (5)0.024 (4)0.029 (4)0.029 (4)
C90.073 (5)0.066 (5)0.062 (5)0.016 (4)0.024 (4)0.018 (4)
C100.068 (5)0.065 (5)0.059 (4)0.008 (4)0.023 (4)0.014 (4)
C110.066 (5)0.074 (5)0.067 (5)0.007 (4)0.026 (4)0.014 (4)
C120.086 (6)0.090 (6)0.082 (6)0.004 (5)0.032 (5)0.025 (5)
C130.088 (7)0.111 (8)0.089 (6)0.012 (6)0.047 (6)0.026 (6)
C140.083 (6)0.122 (8)0.095 (7)0.026 (6)0.038 (6)0.028 (6)
C150.076 (6)0.106 (7)0.083 (6)0.025 (5)0.032 (5)0.029 (5)
C160.060 (5)0.094 (6)0.082 (6)0.018 (4)0.018 (4)0.034 (5)
C170.085 (7)0.126 (9)0.122 (9)0.008 (6)0.010 (6)0.049 (8)
C180.090 (19)0.13 (3)0.10 (2)0.00 (2)0.002 (15)0.04 (2)
C190.140 (19)0.13 (3)0.12 (2)0.03 (2)0.012 (17)0.05 (2)
C200.082 (19)0.077 (11)0.063 (17)0.006 (13)0.040 (13)0.011 (14)
C210.094 (12)0.100 (11)0.069 (11)0.005 (8)0.042 (9)0.015 (8)
C220.11 (2)0.111 (16)0.079 (19)0.015 (16)0.047 (14)0.008 (16)
C230.15 (3)0.16 (3)0.11 (2)0.009 (19)0.027 (19)0.036 (18)
C18'0.09 (4)0.11 (5)0.09 (4)0.01 (5)0.01 (3)0.04 (5)
C19'0.12 (4)0.13 (7)0.12 (4)0.01 (5)0.00 (3)0.02 (6)
C20'0.09 (4)0.08 (2)0.06 (3)0.00 (2)0.03 (2)0.02 (3)
C21'0.10 (3)0.10 (2)0.08 (2)0.001 (18)0.03 (2)0.017 (17)
C22'0.11 (4)0.11 (3)0.09 (3)0.01 (3)0.03 (2)0.02 (3)
C23'0.15 (6)0.16 (5)0.11 (5)0.01 (4)0.03 (4)0.04 (4)
C240.062 (5)0.073 (5)0.070 (5)0.017 (4)0.022 (4)0.010 (4)
C250.076 (5)0.088 (6)0.085 (6)0.027 (4)0.040 (5)0.030 (5)
C260.095 (7)0.112 (8)0.115 (8)0.017 (6)0.058 (6)0.031 (6)
C270.165 (12)0.182 (13)0.139 (11)0.055 (10)0.110 (10)0.065 (10)
C280.073 (5)0.072 (5)0.084 (6)0.001 (4)0.014 (5)0.020 (5)
C290.092 (14)0.075 (11)0.095 (11)0.019 (10)0.004 (9)0.040 (10)
C300.091 (13)0.073 (11)0.108 (12)0.007 (10)0.023 (11)0.029 (9)
C310.106 (16)0.098 (19)0.123 (17)0.022 (14)0.050 (13)0.014 (15)
C29'0.08 (2)0.07 (2)0.10 (2)0.00 (2)0.018 (19)0.033 (18)
C30'0.08 (2)0.08 (2)0.10 (2)0.002 (16)0.025 (16)0.031 (16)
C31'0.09 (3)0.10 (4)0.11 (3)0.01 (3)0.05 (2)0.03 (3)
C320.089 (6)0.096 (7)0.062 (5)0.011 (5)0.005 (4)0.030 (5)
Geometric parameters (Å, º) top
Sn1—O42.022 (4)C21—H21B0.9700
Sn1—C202.10 (4)C22—C231.49 (4)
Sn1—C162.117 (8)C22—H22A0.9700
Sn1—O12.169 (4)C22—H22B0.9700
Sn1—C20'2.21 (7)C23—H23A0.9600
Sn1—O52.227 (4)C23—H23B0.9600
Sn2—O42.051 (4)C23—H23C0.9600
Sn2—O4i2.127 (4)C18'—C19'1.54 (16)
Sn2—C242.129 (7)C18'—H18C0.9700
Sn2—C282.129 (8)C18'—H18D0.9700
Sn2—O52.148 (5)C19'—H19D0.9600
N1—C91.260 (9)C19'—H19E0.9600
N1—C61.426 (9)C19'—H19F0.9600
O1—C11.281 (8)C20'—C21'1.52 (8)
O2—C11.222 (8)C20'—H20C0.9700
O3—C111.333 (9)C20'—H20D0.9700
O3—H30.8200C21'—C22'1.53 (7)
O4—Sn2i2.127 (4)C21'—H21C0.9700
O5—C321.432 (8)C21'—H21D0.9700
C1—C21.512 (10)C22'—C23'1.51 (7)
C2—C31.505 (9)C22'—H22C0.9700
C2—H2A0.9700C22'—H22D0.9700
C2—H2B0.9700C23'—H23D0.9600
C3—C41.368 (10)C23'—H23E0.9600
C3—C81.386 (10)C23'—H23F0.9600
C4—C51.382 (10)C24—C251.520 (10)
C4—H40.9300C24—H24A0.9700
C5—C61.380 (10)C24—H24B0.9700
C5—H50.9300C25—C261.527 (11)
C6—C71.379 (10)C25—H25A0.9700
C7—C81.379 (10)C25—H25B0.9700
C7—H70.9300C26—C271.523 (14)
C8—H80.9300C26—H26A0.9700
C9—C101.460 (10)C26—H26B0.9700
C9—H90.9300C27—H27A0.9600
C10—C111.385 (11)C27—H27B0.9600
C10—C151.393 (11)C27—H27C0.9600
C11—C121.403 (11)C28—C291.514 (19)
C12—C131.360 (12)C28—C29'1.56 (4)
C12—H120.9300C28—H28A0.9700
C13—C141.383 (13)C28—H28B0.9700
C13—H130.9300C28—H28C0.9700
C14—C151.382 (12)C28—H28D0.9700
C14—H140.9300C29—C301.50 (3)
C15—H150.9300C29—H29A0.9700
C16—C171.485 (12)C29—H29B0.9700
C16—H16A0.9700C30—C311.52 (3)
C16—H16B0.9700C30—H30A0.9700
C17—C18'1.49 (11)C30—H30B0.9700
C17—C181.50 (5)C31—H31A0.9600
C17—H17A0.9700C31—H31B0.9600
C17—H17B0.9700C31—H31C0.9600
C17—H17C0.9700C29'—C30'1.51 (6)
C17—H17D0.9700C29'—H29C0.9700
C18—C191.54 (7)C29'—H29D0.9700
C18—H18A0.9700C30'—C31'1.52 (6)
C18—H18B0.9700C30'—H30C0.9700
C19—H19A0.9600C30'—H30D0.9700
C19—H19B0.9600C31'—H31D0.9600
C19—H19C0.9600C31'—H31E0.9600
C20—C211.51 (3)C31'—H31F0.9600
C20—H20A0.9700C32—H32A0.9600
C20—H20B0.9700C32—H32B0.9600
C21—C221.53 (3)C32—H32C0.9600
C21—H21A0.9700
O4—Sn1—C20107.0 (8)C22—C21—H21A108.6
O4—Sn1—C16110.7 (3)C20—C21—H21B108.6
C20—Sn1—C16141.6 (7)C22—C21—H21B108.6
O4—Sn1—O181.82 (17)H21A—C21—H21B107.6
C20—Sn1—O193.4 (10)C23—C22—C21112 (2)
C16—Sn1—O198.6 (3)C23—C22—H22A109.2
O4—Sn1—C20'121.8 (15)C21—C22—H22A109.2
C20—Sn1—C20'15.7 (15)C23—C22—H22B109.2
C16—Sn1—C20'126.1 (14)C21—C22—H22B109.2
O1—Sn1—C20'100.2 (19)H22A—C22—H22B107.9
O4—Sn1—O571.85 (16)C17—C18'—C19'112 (8)
C20—Sn1—O591.6 (11)C17—C18'—H18C109.3
C16—Sn1—O593.4 (3)C19'—C18'—H18C109.3
O1—Sn1—O5153.52 (18)C17—C18'—H18D109.3
C20'—Sn1—O592 (2)C19'—C18'—H18D109.3
O4—Sn2—O4i73.39 (19)H18C—C18'—H18D108.0
O4—Sn2—C24113.0 (3)C18'—C19'—H19D109.5
O4i—Sn2—C2496.7 (2)C18'—C19'—H19E109.5
O4—Sn2—C28121.4 (3)H19D—C19'—H19E109.5
O4i—Sn2—C2898.7 (3)C18'—C19'—H19F109.5
C24—Sn2—C28125.6 (3)H19D—C19'—H19F109.5
O4—Sn2—O573.00 (17)H19E—C19'—H19F109.5
O4i—Sn2—O5146.34 (17)C21'—C20'—Sn1115 (4)
C24—Sn2—O598.0 (3)C21'—C20'—H20C108.6
C28—Sn2—O597.1 (3)Sn1—C20'—H20C108.6
C9—N1—C6121.4 (7)C21'—C20'—H20D108.6
C1—O1—Sn1114.1 (4)Sn1—C20'—H20D108.6
C11—O3—H3109.5H20C—C20'—H20D107.6
Sn1—O4—Sn2113.17 (19)C20'—C21'—C22'114 (4)
Sn1—O4—Sn2i140.2 (2)C20'—C21'—H21C108.7
Sn2—O4—Sn2i106.61 (19)C22'—C21'—H21C108.7
C32—O5—Sn2126.5 (5)C20'—C21'—H21D108.7
C32—O5—Sn1128.9 (5)C22'—C21'—H21D108.7
Sn2—O5—Sn1101.95 (17)H21C—C21'—H21D107.6
O2—C1—O1123.5 (7)C23'—C22'—C21'112 (5)
O2—C1—C2120.5 (7)C23'—C22'—H22C109.1
O1—C1—C2116.0 (7)C21'—C22'—H22C109.1
C3—C2—C1111.9 (6)C23'—C22'—H22D109.1
C3—C2—H2A109.2C21'—C22'—H22D109.1
C1—C2—H2A109.2H22C—C22'—H22D107.8
C3—C2—H2B109.2C22'—C23'—H23D109.5
C1—C2—H2B109.2C22'—C23'—H23E109.5
H2A—C2—H2B107.9H23D—C23'—H23E109.5
C4—C3—C8117.3 (6)C22'—C23'—H23F109.5
C4—C3—C2121.7 (7)H23D—C23'—H23F109.5
C8—C3—C2120.9 (7)H23E—C23'—H23F109.5
C3—C4—C5121.6 (7)C25—C24—Sn2117.3 (5)
C3—C4—H4119.2C25—C24—H24A108.0
C5—C4—H4119.2Sn2—C24—H24A108.0
C6—C5—C4120.9 (7)C25—C24—H24B108.0
C6—C5—H5119.6Sn2—C24—H24B108.0
C4—C5—H5119.6H24A—C24—H24B107.2
C7—C6—C5118.0 (7)C24—C25—C26112.7 (8)
C7—C6—N1125.7 (7)C24—C25—H25A109.1
C5—C6—N1116.4 (6)C26—C25—H25A109.1
C6—C7—C8120.6 (7)C24—C25—H25B109.1
C6—C7—H7119.7C26—C25—H25B109.1
C8—C7—H7119.7H25A—C25—H25B107.8
C7—C8—C3121.6 (7)C27—C26—C25113.5 (9)
C7—C8—H8119.2C27—C26—H26A108.9
C3—C8—H8119.2C25—C26—H26A108.9
N1—C9—C10121.9 (7)C27—C26—H26B108.9
N1—C9—H9119.0C25—C26—H26B108.9
C10—C9—H9119.0H26A—C26—H26B107.7
C11—C10—C15119.6 (7)C26—C27—H27A109.5
C11—C10—C9121.2 (7)C26—C27—H27B109.5
C15—C10—C9119.2 (7)H27A—C27—H27B109.5
O3—C11—C10122.4 (7)C26—C27—H27C109.5
O3—C11—C12117.5 (8)H27A—C27—H27C109.5
C10—C11—C12120.1 (8)H27B—C27—H27C109.5
C13—C12—C11118.9 (9)C29—C28—C29'32.6 (11)
C13—C12—H12120.6C29—C28—Sn2124.4 (9)
C11—C12—H12120.6C29'—C28—Sn2100.1 (15)
C12—C13—C14122.0 (9)C29—C28—H28A106.2
C12—C13—H13119.0C29'—C28—H28A138.2
C14—C13—H13119.0Sn2—C28—H28A106.2
C15—C14—C13119.1 (9)C29—C28—H28B106.2
C15—C14—H14120.4C29'—C28—H28B96.4
C13—C14—H14120.4Sn2—C28—H28B106.2
C14—C15—C10120.2 (9)H28A—C28—H28B106.4
C14—C15—H15119.9C29—C28—H28C81.9
C10—C15—H15119.9C29'—C28—H28C112.1
C17—C16—Sn1120.8 (6)Sn2—C28—H28C111.8
C17—C16—H16A107.1H28A—C28—H28C27.4
Sn1—C16—H16A107.1H28B—C28—H28C126.3
C17—C16—H16B107.1C29—C28—H28D112.8
Sn1—C16—H16B107.1C29'—C28—H28D111.2
H16A—C16—H16B106.8Sn2—C28—H28D112.0
C16—C17—C18'120 (5)H28A—C28—H28D88.3
C16—C17—C18114 (2)H28B—C28—H28D18.1
C18'—C17—C1824 (3)H28C—C28—H28D109.4
C16—C17—H17A108.8C30—C29—C28107.6 (16)
C18'—C17—H17A121.9C30—C29—H29A110.2
C18—C17—H17A108.8C28—C29—H29A110.2
C16—C17—H17B108.8C30—C29—H29B110.2
C18'—C17—H17B84.6C28—C29—H29B110.2
C18—C17—H17B108.8H29A—C29—H29B108.5
H17A—C17—H17B107.7C29—C30—C31110.5 (18)
C16—C17—H17C109.4C29—C30—H30A109.5
C18'—C17—H17C95.7C31—C30—H30A109.5
C18—C17—H17C75.9C29—C30—H30B109.5
H17A—C17—H17C36.6C31—C30—H30B109.5
H17B—C17—H17C135.0H30A—C30—H30B108.1
C16—C17—H17D109.4C30'—C29'—C28117 (3)
C18'—C17—H17D112.8C30'—C29'—H29C108.1
C18—C17—H17D132.5C28—C29'—H29C108.1
H17A—C17—H17D73.7C30'—C29'—H29D108.1
H17B—C17—H17D36.0C28—C29'—H29D108.1
H17C—C17—H17D107.6H29C—C29'—H29D107.3
C17—C18—C19112 (4)C29'—C30'—C31'124 (3)
C17—C18—H17C36.7C29'—C30'—H30C106.3
C19—C18—H17C100.4C31'—C30'—H30C106.3
C17—C18—H18A109.1C29'—C30'—H30D106.3
C19—C18—H18A109.1C31'—C30'—H30D106.3
H17C—C18—H18A143.1H30C—C30'—H30D106.4
C17—C18—H18B109.1C30'—C31'—H31D109.5
C19—C18—H18B109.1C30'—C31'—H31E109.5
H17C—C18—H18B81.9H31D—C31'—H31E109.5
H18A—C18—H18B107.8C30'—C31'—H31F109.5
C21—C20—Sn1118 (2)H31D—C31'—H31F109.5
C21—C20—H20A107.9H31E—C31'—H31F109.5
Sn1—C20—H20A107.9O5—C32—H32A109.5
C21—C20—H20B107.9O5—C32—H32B109.5
Sn1—C20—H20B107.9H32A—C32—H32B109.5
H20A—C20—H20B107.2O5—C32—H32C109.5
C20—C21—C22114.6 (19)H32A—C32—H32C109.5
C20—C21—H21A108.6H32B—C32—H32C109.5
Symmetry code: (i) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula[Sn4(C4H9)8(C15H12NO3)2(CH3O)2O2]
Mr1534.32
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)10.6059 (14), 12.2128 (17), 14.522 (2)
α, β, γ (°)104.921 (2), 104.271 (2), 91.991 (1)
V3)1751.8 (4)
Z1
Radiation typeMo Kα
µ (mm1)1.46
Crystal size (mm)0.40 × 0.39 × 0.19
Data collection
DiffractometerSiemens SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.593, 0.769
No. of measured, independent and
observed [I > 2σ(I)] reflections
9161, 6067, 4114
Rint0.019
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.140, 1.04
No. of reflections6067
No. of parameters453
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.31, 0.56

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

We acknowledge the financial support of the Natural Science Foundation of China (No. 20771053) and the Natural Science Foundation of Shandong Province (Y2008B48). This work was also supported by the `Students Technology Cultural Innovation Fund' of Liaocheng University (SRT08045HX2).

References

First citationBerceanc, V., Crainic, C., Haiduc, I., Mahon, M. F., Molloy, K. C., Venter, M. M. & Wilson, P. J. (2002). J. Chem. Soc. Dalton Trans. pp. 1036–1045.  Web of Science CSD CrossRef Google Scholar
First citationGarcia-Zarracino, R. & Hopfl, H. (2005). J. Am. Chem. Soc. 127, 3120–3130.  Web of Science CSD CrossRef PubMed 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 citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationWu, X., Kang, W., Zhu, D., Zhu, C. & Liu, S. (2009). J. Organomet. Chem. 694, 2981–2986.  Web of Science CSD CrossRef CAS Google Scholar

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