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Acta Cryst. (2010). E66, m495    [ doi:10.1107/S1600536810011670 ]

[[mu]-2,2'-Dimethyl-2,2'-(p-phenylene)dipropyl]bis[chloridobis(2-methyl-2-phenylpropyl)tin(IV)]

C. Sun, C. Liang, W. Kang and D. Zhu

Abstract top

The molecular structure of the title compound, [Sn2(C10H13)4(C14H20)Cl2], is a binuclear centrosymmetric complex, in which the Sn atoms are four-coordinated by three C atoms and one Cl atom in a distorted tetrahedral geometry.

Comment top

The increasing interest in organotin compounds that has arisen in the last few decades is attributed to their significantly important biological properties like antiviral and anticancer agents, in vitro antibacterial and antifungal agents, wood preservatives and pesticides, etc. (Chandrasekhar et al., 2002; & Wu et al., 2009). Therefore, synthesis of new organotin compounds with different structural features will be beneficial in the development of pharmaceutical organotin and in other properties and application. herein, we present the synthesis and crystal structure of the title compound (I).

The structure of the title compound (Fig.1) consists of two symmetry equivalent tin moieties, where the tin atoms are tetrahedrally coordinated by the three C atoms and one Cl atom. The bond lengths for Sn(1)—C(1), Sn(1)—C(8) and Sn(1)—C(18) are 2.146 (5), 2.152 (5) and 2.149 (5) Å, respectively, which are slightly shorter than the Bz3Sn(EtACDA) reported by Tarassoli et al. (Tarassoli et al., 2002). Around the tin, the angles C(1)—Sn(1)—C(8), C(1)—Sn(1)—C(18) and C(8)—Sn(1)—C(18) are wider while the C(1)—Sn(1)—Cl(1), C(8)—Sn(1)—Cl(1) and C(18)—Sn(1)—Cl(1) are narrower than the ideal tetrahedral angle. Thus, the environment of tin is best described as distorted tetrahedral.

Related literature top

For general background to organotin compounds, see: Chandrasekhar et al. (2002); Wu et al. (2009); For related structures, see: Tarassoli et al. (2002).

Experimental top

A small iodine grain, magnesium powder(0.24 g 10 mmol), and 1,4-bis(1- chloro-2-methylpropan-2-yl)benzene (0.52 g, 2 mmol) were added to 2 ml of anhydrous ether under stirring. The reaction mixture is then heated to 50 –60°C by hot-water bath and maintained slight boiling state. When the purplish red of iodine disappeared, which indicated the reaction were initiated, the hot-water bath was removed. The reaction were keeping the slight boiling state, then a solution of 1,4-bis(1-chloro-2-methylpropan- 2-yl)benzene (2.59 g, 10 mmol) in 10 ml anhydrous ether were added dropwise. After finished, the mixture was refluxed for 1 h to allow magnesium to proceed to completion, then cooled to 0–5°C by ice-salt bath. A solution of dichlorobis(2-methyl-2-phenylpropyl)stannane (4.56 g,10 mmol) in 15 mL THF were then added dropwise. After finished, the ice-salt bath was removed, and the reaction mixture were stirred for 0.5 h at room temprature then refluxed for another 1.5 h. Finally, the mixture were again cooled to 0°C, and acidified by dropwise adding a solution containing 2.5 g fuming HCl and 15 ml water. The layers were separated, the organic phase was dried over anhydrous calcium chloride. Following filtration and evaporation of the solvent, the residue was recrystallized by THF and the colorless block crystals of (I) were abtained.

Refinement top

All H atoms on C atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding, with Uiso(H)=1.2Ueq(carrier).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXTL-Plus (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity. Scheme 1. The chemical structure diagram of (I). Scheme 2. The reaction scheme for synthesis of (I).
[Figure 2] Fig. 2. The formation of the title compound.
[µ-2,2'-Dimethyl-2,2'-(p-phenylene)dipropyl]bis[chloridobis(2-\ methyl-2-phenylpropyl)tin(IV)] top
Crystal data top
[Sn2(C10H13)4(C14H20)Cl2]F(000) = 2120
Mr = 1029.40Dx = 1.354 Mg m−3
Monoclinic, C2/cMelting point: not measured K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 15.0769 (19) ÅCell parameters from 4976 reflections
b = 17.773 (2) Åθ = 1.8–26.1°
c = 18.914 (2) ŵ = 1.13 mm−1
β = 94.674 (2)°T = 185 K
V = 5051.4 (11) Å3Block, colorless
Z = 40.34 × 0.32 × 0.29 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4976 independent reflections
Radiation source: fine-focus sealed tube3284 reflections with I > 2σ(I)
graphiteRint = 0.073
phi and ω scansθmax = 26.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −17→18
Tmin = 0.688, Tmax = 0.721k = −21→10
14065 measured reflectionsl = −22→23
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.039P)2]
where P = (Fo2 + 2Fc2)/3
4976 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 0.78 e Å−3
0 restraintsΔρmin = −0.42 e Å−3
Crystal data top
[Sn2(C10H13)4(C14H20)Cl2]V = 5051.4 (11) Å3
Mr = 1029.40Z = 4
Monoclinic, C2/cMo Kα radiation
a = 15.0769 (19) ŵ = 1.13 mm−1
b = 17.773 (2) ÅT = 185 K
c = 18.914 (2) Å0.34 × 0.32 × 0.29 mm
β = 94.674 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4976 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3284 reflections with I > 2σ(I)
Tmin = 0.688, Tmax = 0.721Rint = 0.073
14065 measured reflectionsθmax = 26.1°
Refinement top
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.113Δρmax = 0.78 e Å−3
S = 1.02Δρmin = −0.42 e Å−3
4976 reflectionsAbsolute structure: ?
262 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.28085 (2)0.63191 (2)0.82050 (2)0.03363 (14)
Cl10.38105 (10)0.72044 (11)0.88005 (10)0.0654 (6)
C10.1798 (3)0.6193 (4)0.8932 (3)0.0452 (17)
H1A0.15530.56910.88700.054*
H1B0.20870.62180.94090.054*
C20.1012 (3)0.6751 (3)0.8892 (3)0.0379 (15)
C30.1392 (4)0.7525 (4)0.9106 (3)0.0584 (19)
H3A0.09190.78870.90900.088*
H3B0.18190.76720.87820.088*
H3C0.16770.75000.95780.088*
C40.0385 (4)0.6530 (4)0.9459 (3)0.0521 (19)
H4A−0.01050.68770.94450.078*
H4B0.07030.65460.99190.078*
H4C0.01630.60310.93660.078*
C50.0505 (3)0.6738 (4)0.8170 (3)0.0362 (14)
C60.0253 (4)0.6067 (4)0.7834 (3)0.0442 (16)
H6A0.04170.56120.80500.053*
C70.0247 (4)0.7404 (4)0.7826 (3)0.0476 (17)
H7A0.04110.78610.80380.057*
C80.3641 (3)0.5345 (3)0.8122 (3)0.0376 (15)
H8A0.35100.51320.76530.045*
H8B0.42540.55160.81500.045*
C90.3579 (3)0.4711 (4)0.8663 (3)0.0394 (15)
C100.3954 (4)0.4993 (4)0.9392 (3)0.062 (2)
H10A0.35990.54050.95370.093*
H10B0.45560.51590.93640.093*
H10C0.39420.45930.97310.093*
C110.4168 (4)0.4049 (4)0.8449 (4)0.060 (2)
H11A0.47720.42170.84390.090*
H11B0.39550.38690.79880.090*
H11C0.41430.36490.87890.090*
C120.2626 (3)0.4417 (3)0.8674 (3)0.0350 (14)
C130.2205 (4)0.4316 (3)0.9293 (3)0.0434 (16)
H13A0.25080.44310.97270.052*
C140.1342 (4)0.4048 (3)0.9273 (4)0.0462 (16)
H14A0.10730.39840.96940.055*
C150.0884 (4)0.3878 (4)0.8646 (4)0.0567 (19)
H15A0.03040.36980.86390.068*
C160.1283 (4)0.3974 (4)0.8018 (4)0.0570 (19)
H16A0.09740.38610.75850.068*
C170.2147 (4)0.4239 (4)0.8044 (3)0.0474 (17)
H17A0.24140.43000.76220.057*
C180.2457 (3)0.6893 (3)0.7222 (3)0.0373 (14)
H18A0.18170.68550.71210.045*
H18B0.25960.74220.72910.045*
C190.2896 (4)0.6625 (3)0.6566 (3)0.0355 (14)
C200.3905 (4)0.6750 (4)0.6689 (3)0.0496 (17)
H20A0.41400.64460.70810.074*
H20B0.40220.72700.67940.074*
H20C0.41850.66110.62700.074*
C210.2556 (4)0.7128 (3)0.5935 (3)0.0483 (17)
H21A0.19250.70630.58430.072*
H21B0.28480.69880.55220.072*
H21C0.26830.76450.60490.072*
C220.2664 (3)0.5811 (3)0.6383 (3)0.0332 (14)
C230.3288 (4)0.5275 (4)0.6238 (3)0.0404 (15)
H23A0.38850.54120.62590.048*
C240.3056 (5)0.4547 (4)0.6065 (3)0.0501 (17)
H24A0.34960.42040.59690.060*
C250.2180 (5)0.4319 (4)0.6032 (3)0.0541 (18)
H25A0.20230.38250.59180.065*
C260.1550 (4)0.4837 (4)0.6171 (3)0.0500 (17)
H26A0.09560.46930.61530.060*
C270.1778 (4)0.5575 (4)0.6339 (3)0.0412 (15)
H27A0.13340.59190.64240.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0262 (2)0.0405 (2)0.0342 (2)0.0021 (2)0.00262 (15)−0.0040 (2)
Cl10.0347 (8)0.0812 (14)0.0794 (13)−0.0075 (9)−0.0002 (8)−0.0371 (11)
C10.030 (3)0.072 (5)0.033 (3)0.003 (3)0.004 (2)0.008 (3)
C20.027 (3)0.037 (4)0.050 (4)0.001 (3)0.003 (3)−0.007 (3)
C30.042 (4)0.074 (5)0.059 (4)−0.004 (4)0.002 (3)−0.017 (4)
C40.033 (3)0.083 (6)0.041 (4)−0.003 (3)0.007 (3)−0.006 (4)
C50.023 (3)0.047 (4)0.040 (3)0.007 (3)0.009 (2)0.002 (3)
C60.039 (4)0.049 (4)0.047 (4)0.001 (3)0.014 (3)0.005 (3)
C70.039 (4)0.048 (4)0.056 (4)0.006 (3)0.003 (3)−0.001 (3)
C80.032 (3)0.048 (4)0.035 (3)0.003 (3)0.010 (3)−0.002 (3)
C90.033 (3)0.054 (4)0.032 (3)0.009 (3)0.007 (3)0.011 (3)
C100.047 (4)0.094 (6)0.044 (4)−0.005 (4)−0.009 (3)0.009 (4)
C110.044 (4)0.057 (5)0.079 (5)0.026 (4)0.009 (4)0.020 (4)
C120.031 (3)0.033 (4)0.041 (4)0.007 (3)0.003 (3)0.002 (3)
C130.050 (4)0.039 (4)0.042 (4)0.010 (3)0.007 (3)0.002 (3)
C140.047 (4)0.039 (4)0.055 (4)0.003 (3)0.018 (3)0.005 (3)
C150.037 (4)0.039 (4)0.093 (6)−0.002 (3)0.005 (4)−0.002 (4)
C160.054 (4)0.062 (5)0.053 (4)0.009 (4)−0.010 (3)−0.008 (4)
C170.045 (4)0.052 (4)0.044 (4)0.011 (3)0.003 (3)0.003 (3)
C180.033 (3)0.033 (3)0.046 (4)−0.003 (3)0.003 (3)−0.002 (3)
C190.035 (3)0.037 (4)0.036 (3)0.002 (3)0.006 (3)0.008 (3)
C200.042 (4)0.047 (4)0.061 (4)−0.011 (3)0.013 (3)0.004 (4)
C210.052 (4)0.044 (4)0.049 (4)−0.001 (3)0.005 (3)0.009 (3)
C220.032 (3)0.043 (4)0.025 (3)0.003 (3)0.003 (2)0.002 (3)
C230.038 (3)0.049 (4)0.034 (3)0.004 (3)0.002 (3)−0.001 (3)
C240.064 (4)0.047 (4)0.039 (4)0.010 (4)0.003 (3)−0.009 (3)
C250.089 (5)0.032 (4)0.040 (4)−0.005 (4)−0.001 (4)−0.002 (3)
C260.045 (4)0.048 (4)0.057 (4)−0.020 (4)0.002 (3)0.004 (4)
C270.032 (3)0.043 (4)0.049 (4)0.003 (3)0.007 (3)0.006 (3)
Geometric parameters (Å, °) top
Sn1—C12.146 (5)C12—C171.378 (7)
Sn1—C182.149 (5)C12—C131.387 (7)
Sn1—C82.152 (5)C13—C141.384 (8)
Sn1—Cl12.3978 (17)C13—H13A0.9300
C1—C21.541 (7)C14—C151.356 (8)
C1—H1A0.9700C14—H14A0.9300
C1—H1B0.9700C15—C161.386 (9)
C2—C51.511 (7)C15—H15A0.9300
C2—C31.532 (8)C16—C171.382 (8)
C2—C41.537 (7)C16—H16A0.9300
C3—H3A0.9600C17—H17A0.9300
C3—H3B0.9600C18—C191.529 (7)
C3—H3C0.9600C18—H18A0.9700
C4—H4A0.9600C18—H18B0.9700
C4—H4B0.9600C19—C221.522 (8)
C4—H4C0.9600C19—C201.536 (7)
C5—C61.389 (8)C19—C211.545 (7)
C5—C71.391 (8)C20—H20A0.9600
C6—C6i1.422 (11)C20—H20B0.9600
C6—H6A0.9300C20—H20C0.9600
C7—C7i1.387 (11)C21—H21A0.9600
C7—H7A0.9300C21—H21B0.9600
C8—C91.530 (7)C21—H21C0.9600
C8—H8A0.9700C22—C231.382 (7)
C8—H8B0.9700C22—C271.395 (7)
C9—C121.531 (7)C23—C241.373 (8)
C9—C101.531 (8)C23—H23A0.9300
C9—C111.548 (8)C24—C251.378 (8)
C10—H10A0.9600C24—H24A0.9300
C10—H10B0.9600C25—C261.365 (8)
C10—H10C0.9600C25—H25A0.9300
C11—H11A0.9600C26—C271.386 (8)
C11—H11B0.9600C26—H26A0.9300
C11—H11C0.9600C27—H27A0.9300
C1—Sn1—C18117.8 (2)H11B—C11—H11C109.5
C1—Sn1—C8114.3 (2)C17—C12—C13117.1 (5)
C18—Sn1—C8115.0 (2)C17—C12—C9119.5 (5)
C1—Sn1—Cl1102.73 (17)C13—C12—C9123.4 (5)
C18—Sn1—Cl1101.32 (16)C14—C13—C12121.0 (6)
C8—Sn1—Cl1102.30 (16)C14—C13—H13A119.5
C2—C1—Sn1119.0 (4)C12—C13—H13A119.5
C2—C1—H1A107.6C15—C14—C13120.8 (6)
Sn1—C1—H1A107.6C15—C14—H14A119.6
C2—C1—H1B107.6C13—C14—H14A119.6
Sn1—C1—H1B107.6C14—C15—C16119.7 (6)
H1A—C1—H1B107.0C14—C15—H15A120.1
C5—C2—C3113.7 (5)C16—C15—H15A120.1
C5—C2—C4109.4 (4)C17—C16—C15119.0 (6)
C3—C2—C4106.5 (5)C17—C16—H16A120.5
C5—C2—C1111.4 (5)C15—C16—H16A120.5
C3—C2—C1107.2 (5)C12—C17—C16122.3 (6)
C4—C2—C1108.4 (5)C12—C17—H17A118.8
C2—C3—H3A109.5C16—C17—H17A118.8
C2—C3—H3B109.5C19—C18—Sn1117.4 (4)
H3A—C3—H3B109.5C19—C18—H18A107.9
C2—C3—H3C109.5Sn1—C18—H18A107.9
H3A—C3—H3C109.5C19—C18—H18B107.9
H3B—C3—H3C109.5Sn1—C18—H18B107.9
C2—C4—H4A109.5H18A—C18—H18B107.2
C2—C4—H4B109.5C22—C19—C18112.0 (4)
H4A—C4—H4B109.5C22—C19—C20112.2 (5)
C2—C4—H4C109.5C18—C19—C20108.8 (5)
H4A—C4—H4C109.5C22—C19—C21108.5 (5)
H4B—C4—H4C109.5C18—C19—C21107.9 (5)
C6—C5—C7117.5 (5)C20—C19—C21107.2 (5)
C6—C5—C2121.7 (5)C19—C20—H20A109.5
C7—C5—C2120.8 (6)C19—C20—H20B109.5
C5—C6—C6i120.9 (3)H20A—C20—H20B109.5
C5—C6—H6A119.6C19—C20—H20C109.5
C6i—C6—H6A119.6H20A—C20—H20C109.5
C7i—C7—C5121.7 (4)H20B—C20—H20C109.5
C7i—C7—H7A119.2C19—C21—H21A109.5
C5—C7—H7A119.2C19—C21—H21B109.5
C9—C8—Sn1118.4 (3)H21A—C21—H21B109.5
C9—C8—H8A107.7C19—C21—H21C109.5
Sn1—C8—H8A107.7H21A—C21—H21C109.5
C9—C8—H8B107.7H21B—C21—H21C109.5
Sn1—C8—H8B107.7C23—C22—C27116.4 (6)
H8A—C8—H8B107.1C23—C22—C19123.5 (5)
C8—C9—C12111.7 (5)C27—C22—C19120.0 (5)
C8—C9—C10108.8 (5)C24—C23—C22122.2 (6)
C12—C9—C10112.2 (5)C24—C23—H23A118.9
C8—C9—C11108.5 (4)C22—C23—H23A118.9
C12—C9—C11107.6 (5)C23—C24—C25120.9 (6)
C10—C9—C11107.8 (5)C23—C24—H24A119.6
C9—C10—H10A109.5C25—C24—H24A119.6
C9—C10—H10B109.5C26—C25—C24118.1 (6)
H10A—C10—H10B109.5C26—C25—H25A120.9
C9—C10—H10C109.5C24—C25—H25A120.9
H10A—C10—H10C109.5C25—C26—C27121.3 (6)
H10B—C10—H10C109.5C25—C26—H26A119.4
C9—C11—H11A109.5C27—C26—H26A119.4
C9—C11—H11B109.5C26—C27—C22121.1 (6)
H11A—C11—H11B109.5C26—C27—H27A119.5
C9—C11—H11C109.5C22—C27—H27A119.5
H11A—C11—H11C109.5
C18—Sn1—C1—C2−23.9 (5)C17—C12—C13—C140.0 (9)
C8—Sn1—C1—C2−163.6 (4)C9—C12—C13—C14−180.0 (5)
Cl1—Sn1—C1—C286.4 (4)C12—C13—C14—C15−0.1 (9)
Sn1—C1—C2—C558.8 (6)C13—C14—C15—C16−0.1 (10)
Sn1—C1—C2—C3−66.2 (6)C14—C15—C16—C170.3 (10)
Sn1—C1—C2—C4179.2 (4)C13—C12—C17—C160.2 (9)
C3—C2—C5—C6168.2 (5)C9—C12—C17—C16−179.8 (6)
C4—C2—C5—C6−72.9 (7)C15—C16—C17—C12−0.4 (10)
C1—C2—C5—C646.9 (7)C1—Sn1—C18—C19−145.8 (4)
C3—C2—C5—C7−13.9 (7)C8—Sn1—C18—C19−6.4 (5)
C4—C2—C5—C7105.0 (6)Cl1—Sn1—C18—C19103.1 (4)
C1—C2—C5—C7−135.2 (5)Sn1—C18—C19—C2261.7 (5)
C7—C5—C6—C6i−0.3 (10)Sn1—C18—C19—C20−62.9 (6)
C2—C5—C6—C6i177.7 (6)Sn1—C18—C19—C21−179.0 (4)
C6—C5—C7—C7i0.4 (10)C18—C19—C22—C23−131.9 (5)
C2—C5—C7—C7i−177.6 (6)C20—C19—C22—C23−9.2 (7)
C1—Sn1—C8—C9−11.0 (5)C21—C19—C22—C23109.1 (6)
C18—Sn1—C8—C9−151.8 (4)C18—C19—C22—C2749.5 (7)
Cl1—Sn1—C8—C999.3 (4)C20—C19—C22—C27172.2 (5)
Sn1—C8—C9—C1256.1 (6)C21—C19—C22—C27−69.5 (6)
Sn1—C8—C9—C10−68.3 (5)C27—C22—C23—C24−0.5 (8)
Sn1—C8—C9—C11174.6 (4)C19—C22—C23—C24−179.1 (5)
C8—C9—C12—C1748.6 (7)C22—C23—C24—C25−0.3 (9)
C10—C9—C12—C17171.1 (6)C23—C24—C25—C260.4 (9)
C11—C9—C12—C17−70.4 (7)C24—C25—C26—C270.3 (9)
C8—C9—C12—C13−131.4 (6)C25—C26—C27—C22−1.1 (9)
C10—C9—C12—C13−8.9 (8)C23—C22—C27—C261.1 (8)
C11—C9—C12—C13109.6 (6)C19—C22—C27—C26179.8 (5)
Symmetry codes: (i) −x, y, −z+3/2.
Acknowledgements top

We thank the State Key Development Program for Basic Research of China (2005CB221304) for support.

references
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