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Acta Cryst. (2009). E65, m262    [ doi:10.1107/S1600536809004097 ]

catena-Poly[[dimethyltin(IV)]-[mu]-cis-cyclohexane-1,2-dicarboxylato]

Y. Wang, R. Zhang and Y. Li

Abstract top

The title complex, [Sn(CH3)2(C8H10O4)]n, was synthesized from cis-cyclohexane-1,2-dicarboxylic acid and dimethyltin dichloride. The complex has a bridging bis-bidentate carboxylate group resulting in a zig-zag chain structure parallel to [001]. The Sn atom is six-coordinated and displays a distorted octahedral geometry.

Comment top

Recently, organotin complexes have been attracting increasing attention partly owing to their determinately or potentially pharmic value, which have been reported many before (Gielen, 2002), and also for the versatile molecular structure and supramolecular architecture exhibited by these complexes (Han et al., 2007). In order to explore the relationships between the properties and structures, we report here the structure of the title complex. Fig. 1 the structure of (I) showing one-dimensional extended polymeric network, and the one-dimensional chain along [001] direction of complex is shown in Fig. 2. Sn atom is six coordinated and displays a octahedral distorted geometry.

Related literature top

For background to organotin complexes, see: Gielen (2002); Han et al. (2007). For related literature, see: Swisher et al. (1984).

Experimental top

The reaction was carried out under nitrogen atmoshpere. cis-cyclohexane-1,2-dicarboxylic acid (0.173 g, 1 mmol) was added to the solution of benzene(30 ml) with sodium ethoxide (0.136 g, 2 mmol) in a Schlenk flask. After stirring for 10 min, dimethyltin dichloride (0.220 g, 1 mmol) was added to the mixture. The mixture was kept at 328 K for 12 h. After cooling down to the room temperature, the solution was filtered. The solvent of the filtrate was gradually removed by evaporation under vacuum until a solid product was obtained. The solid was then recrystallized from aether. Colorless single crystals of the title complex were obtained after one week. Yield, 86%. Analysis calculated for C10H16O4Sn: C 48.76, H 6.55; found: C 48.66, H 6.68. The elemental analyses were performed with PERKIN ELMER MODEL 2400 SERIES II.

Refinement top

All H atoms were placed in geometrically idealized positions methyl (C—H = 0.96 Å), methylene (C—H = 0.97 Å), (C—H = 0.98 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.5Ueq(CH3), Uiso(H) = 1.2Ueq(CH2), Uiso(H) = 1.2Ueq(CH).

Computing details top

Data collection: SMART (Bruker, 1996); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT (Bruker, 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. Part of the structure of (I) showing one-dimensional extended polymeric network, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omitted for clarity. [Symmetry codes: (a) x, 1/2 - y, -1/2 + z; (b) x, 1/2 - x, 1/2 + z]
[Figure 2] Fig. 2. The one-dimensional zigzag chain of the title complex
catena-Poly[[dimethyltin(IV)]-µ-cis-cyclohexane-1,2- dicarboxylato] top
Crystal data top
[Sn(CH3)2(C8H10O4)]F(000) = 632
Mr = 318.92Dx = 1.759 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4238 reflections
a = 10.0880 (16) Åθ = 2.7–28.3°
b = 10.430 (2) ŵ = 2.11 mm−1
c = 11.592 (2) ÅT = 298 K
β = 99.041 (2)°Block, colourless
V = 1204.5 (4) Å30.32 × 0.19 × 0.17 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		2117 independent reflections
Radiation source: fine-focus sealed tube1822 reflections with I > 2σ(I)
graphiteRint = 0.022
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→12
Tmin = 0.551, Tmax = 0.715k = −11→12
6188 measured reflectionsl = −11→13
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H-atom parameters constrained
S = 1.19 w = 1/[σ2(Fo2) + (0.0181P)2 + 1.262P]
where P = (Fo2 + 2Fc2)/3
2117 reflections(Δ/σ)max = 0.001
136 parametersΔρmax = 0.52 e Å−3
0 restraintsΔρmin = −0.43 e Å−3
Crystal data top
[Sn(CH3)2(C8H10O4)]V = 1204.5 (4) Å3
Mr = 318.92Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.0880 (16) ŵ = 2.11 mm−1
b = 10.430 (2) ÅT = 298 K
c = 11.592 (2) Å0.32 × 0.19 × 0.17 mm
β = 99.041 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2117 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1822 reflections with I > 2σ(I)
Tmin = 0.551, Tmax = 0.715Rint = 0.022
6188 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.062Δρmax = 0.52 e Å−3
S = 1.19Δρmin = −0.43 e Å−3
2117 reflectionsAbsolute structure: ?
136 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
Sn10.67183 (3)0.15366 (3)0.10133 (2)0.03534 (10)
O10.8345 (3)0.2746 (3)0.1623 (2)0.0437 (7)
O20.6720 (3)0.3482 (3)0.2497 (3)0.0459 (7)
O30.8140 (3)0.0831 (3)0.0045 (2)0.0427 (7)
O40.6338 (3)−0.0337 (3)−0.0441 (2)0.0448 (7)
C10.8867 (4)0.4597 (4)0.2822 (3)0.0333 (9)
H10.95420.41750.33990.040*
C20.8184 (4)0.5633 (3)0.3471 (3)0.0330 (9)
H20.89060.61630.38880.040*
C30.7305 (4)0.6523 (4)0.2649 (4)0.0413 (10)
H3A0.69670.72020.30950.050*
H3B0.65420.60490.22460.050*
C40.8092 (5)0.7109 (4)0.1751 (4)0.0493 (11)
H4A0.74950.76370.12090.059*
H4B0.87970.76550.21490.059*
C50.8706 (5)0.6077 (5)0.1080 (4)0.0548 (12)
H5A0.79980.55750.06300.066*
H5B0.92240.64750.05390.066*
C60.9609 (4)0.5204 (4)0.1905 (4)0.0459 (11)
H6A1.03660.56940.22960.055*
H6B0.99560.45310.14570.055*
C70.7883 (4)0.3568 (4)0.2295 (3)0.0366 (9)
C80.7475 (4)−0.0040 (3)−0.0606 (3)0.0344 (9)
C90.5448 (4)0.2734 (4)−0.0107 (4)0.0503 (11)
H9A0.47730.30830.03020.075*
H9B0.50260.2249−0.07680.075*
H9C0.59620.3419−0.03690.075*
C100.6548 (5)0.0271 (4)0.2389 (4)0.0476 (11)
H10A0.58940.05940.28340.071*
H10B0.74010.01970.28850.071*
H10C0.6271−0.05560.20770.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03871 (17)0.03394 (16)0.03343 (16)0.00183 (14)0.00588 (11)0.00006 (13)
O10.0425 (16)0.0383 (17)0.0494 (18)0.0012 (14)0.0043 (14)−0.0157 (14)
O20.0424 (17)0.0444 (17)0.0523 (18)−0.0088 (14)0.0116 (14)−0.0093 (14)
O30.0429 (16)0.0443 (17)0.0414 (16)−0.0032 (14)0.0083 (13)−0.0124 (13)
O40.0463 (17)0.0475 (17)0.0436 (17)−0.0052 (14)0.0167 (14)0.0006 (13)
C10.031 (2)0.030 (2)0.038 (2)0.0017 (17)0.0040 (17)−0.0027 (17)
C20.035 (2)0.027 (2)0.036 (2)−0.0024 (16)0.0042 (17)0.0000 (16)
C30.042 (2)0.035 (2)0.048 (2)0.003 (2)0.0098 (19)0.0068 (19)
C40.051 (3)0.044 (3)0.054 (3)−0.003 (2)0.011 (2)0.016 (2)
C50.065 (3)0.058 (3)0.044 (3)−0.011 (2)0.018 (2)0.006 (2)
C60.042 (2)0.049 (3)0.050 (3)−0.009 (2)0.018 (2)−0.009 (2)
C70.042 (2)0.034 (2)0.032 (2)0.0055 (19)0.0026 (18)0.0016 (18)
C80.046 (2)0.025 (2)0.031 (2)0.0025 (18)0.0038 (18)0.0057 (16)
C90.047 (3)0.051 (3)0.052 (3)0.002 (2)0.003 (2)0.011 (2)
C100.058 (3)0.045 (3)0.041 (2)0.004 (2)0.009 (2)0.007 (2)
Geometric parameters (Å, °) top
Sn1—O32.089 (3)C3—H3A0.9700
Sn1—C92.089 (4)C3—H3B0.9700
Sn1—C102.098 (4)C4—C51.516 (6)
Sn1—O12.102 (3)C4—H4A0.9700
Sn1—O42.570 (3)C4—H4B0.9700
Sn1—O22.660 (3)C5—C61.517 (6)
O1—C71.294 (4)C5—H5A0.9700
O2—C71.235 (5)C5—H5B0.9700
O3—C81.298 (4)C6—H6A0.9700
O4—C81.232 (5)C6—H6B0.9700
C1—C71.523 (5)C8—C2ii1.509 (5)
C1—C61.530 (5)C9—H9A0.9600
C1—C21.540 (5)C9—H9B0.9600
C1—H10.9800C9—H9C0.9600
C2—C8i1.509 (5)C10—H10A0.9600
C2—C31.514 (5)C10—H10B0.9600
C2—H20.9800C10—H10C0.9600
C3—C41.532 (6)
O3—Sn1—C9106.41 (15)C5—C4—C3111.2 (4)
O3—Sn1—C10109.39 (15)C5—C4—H4A109.4
C9—Sn1—C10137.14 (18)C3—C4—H4A109.4
O3—Sn1—O180.02 (10)C5—C4—H4B109.4
C9—Sn1—O1102.72 (15)C3—C4—H4B109.4
C10—Sn1—O1105.95 (15)H4A—C4—H4B108.0
O3—Sn1—O454.83 (10)C6—C5—C4110.9 (4)
C9—Sn1—O491.89 (15)C6—C5—H5A109.5
C10—Sn1—O489.93 (14)C4—C5—H5A109.5
O1—Sn1—O4134.84 (9)C6—C5—H5B109.5
O3—Sn1—O2133.28 (9)C4—C5—H5B109.5
C9—Sn1—O283.34 (15)H5A—C5—H5B108.1
C10—Sn1—O288.85 (14)C5—C6—C1112.1 (3)
O1—Sn1—O253.39 (9)C5—C6—H6A109.2
O4—Sn1—O2171.54 (9)C1—C6—H6A109.2
C7—O1—Sn1105.3 (2)C5—C6—H6B109.2
C7—O2—Sn180.6 (2)C1—C6—H6B109.2
C8—O3—Sn1102.9 (2)H6A—C6—H6B107.9
C8—O4—Sn182.2 (2)O2—C7—O1120.5 (4)
C7—C1—C6111.9 (3)O2—C7—C1123.7 (4)
C7—C1—C2112.1 (3)O1—C7—C1115.8 (3)
C6—C1—C2110.8 (3)O4—C8—O3119.6 (4)
C7—C1—H1107.3O4—C8—C2ii124.3 (3)
C6—C1—H1107.3O3—C8—C2ii116.1 (3)
C2—C1—H1107.3Sn1—C9—H9A109.5
C8i—C2—C3113.7 (3)Sn1—C9—H9B109.5
C8i—C2—C1110.9 (3)H9A—C9—H9B109.5
C3—C2—C1112.7 (3)Sn1—C9—H9C109.5
C8i—C2—H2106.3H9A—C9—H9C109.5
C3—C2—H2106.3H9B—C9—H9C109.5
C1—C2—H2106.3Sn1—C10—H10A109.5
C2—C3—C4111.0 (3)Sn1—C10—H10B109.5
C2—C3—H3A109.4H10A—C10—H10B109.5
C4—C3—H3A109.4Sn1—C10—H10C109.5
C2—C3—H3B109.4H10A—C10—H10C109.5
C4—C3—H3B109.4H10B—C10—H10C109.5
H3A—C3—H3B108.0
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.
Table 1
Selected geometric parameters (Å, °) top
Sn1—O32.089 (3)Sn1—O12.102 (3)
Sn1—C92.089 (4)Sn1—O42.570 (3)
Sn1—C102.098 (4)Sn1—O22.660 (3)
C9—Sn1—C10137.14 (18)
Acknowledgements top

The authors thank the National Natural Science Foundation of China (20741008) for financial support.

references
References top

Bruker (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Gielen, M. (2002). Appl. Organomet. Chem. 16, 481–494.

Han, Y., Zhang, R. & Wang, D. (2007). Acta Cryst. E63, m776–m777.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Swisher, R. G., Vollano, J. F., Chandrasekhar, V., Day, R. O. & Holmes, R. R. (1984). Inorg. Chem. 23, 3147–3152.