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Acta Cryst. (2007). E63, m3050    [ doi:10.1107/S1600536807057613 ]

An organotin coordination polymer formed from 1,4-bis(pyridin-3-ylmethoxy)benzene and dibenzyldichlorostannane

S.-L. Li, J. Liu and J.-F. Ma

Abstract top

In the title compound, catena-poly[[dibenzyldichloridotin(IV)]-[mu]-1,4-bis(pyridin-3-ylmethoxy)benzene], [SnCl2(C7H7)2(C18H16N2O2)]n, the dibenzyldichlorostannane molecules are linked by the neutral 1,4-bis(pyridin-3-ylmethoxy)benzene ligands to generate an infinite coordination polymer. Both the Sn atom and the linking ligand reside on centers of inversion. The Sn atom displays a distorted octahedral geometry that consists of two benzyl groups, two chloride ions and two N atoms from different 1,4-bis(pyridin-3-ylmethoxy)benzene ligands.

Comment top

In recent years, metal-organic coordination polymers with aromatic N-donor ligands have attracted special attention owing to their interesting structural and chemical properties (Carlucci et al., 2004; Cui et al., 2005; Dobrzańska et al., 2005). Aromatic N-donor ligands with different character are selected for constructing new compounds with organotin (Li et al., 2006; Ma et al., 2004). In this case, 1,4-bis(pyridin-3-ylmethoxy)benzene and dibenzyldichlorostannane were selected to construct complexes with a polymeric structure.

In the title compound, {(C7H7)2SnCl2(C18H16O2N2)}n , the asymmetric unit contains one Sn(IV) atom located on a center of inversion. As shown in Figure 1, the Sn has a distorted octahedral coordination geometry that consists of two benzyl groups,two Cl− ions and two nitrogen atoms from different 1,4-bis(pyridin-3-ylmethoxy)benzene ligands. All the distances of Sn—N and Sn—Cl are in the reported ranges (Pettinari et al., 1998). In addition, the dihedral angle of the phenyl ring and pyridine ring is 49.5 (4)°. Each dibenzyldichlorostannane is linked by the neutral 1,4-bis(pyridin-3-ylmethoxy)benzene ligands to generate an infinite coordination polymeric chain, and all chains are parallel in the structure.

Related literature top

Metal-organic coordination polymers with aromatic N-donor ligands have attracted special attention owing to their interesting structural and chemical properties (Carlucci et al., 2004; Cui et al., 2005; Dobrzańska et al., 2005). Aromatic N-donor ligands with different character are selected for constructing new organotin compounds (Li et al., 2006; Ma et al., 2004). The Sn—N and Sn—Cl distances are in reported ranges (Pettinari et al., 1998).

Experimental top

A mixture of hydroquinone (1.0 g, 10 mmol) and NaOH (0.8 g, 20 mmol) in DMSO (20 ml) was stirred at 60°C for 1 h, then 3-(chloromethyl)pyridine (2.6 g, 20 mmol) was added. The mixture was cooled to room temperature after stirring at 60°C for 24 h, and then poured into 100 ml of water. A colorless solid of 1,4-bis(pyridin-3-ylmethoxy)benzene formed immediately, which was isolated by filtration in 68% yield after drying in air.

A mixture of dibenzyldichlorostannane (37 mg, 0.1 mmol) (obtained from commercial sources) with 1,4-bis(pyridin-3-ylmethoxy)benzene (29 mg, 0.1 mmol) in EtOH and CH2Cl2 (25 ml, v:v = 1:1) was stirred for a few minutes and then filtered. Single crystals suitable for X-ray analysis were obtained by slow evaporation of the filtrate at room temperature for several days (yield: 35%). Analysis calculated for C32H30Cl2N2O2Sn: C 57.86, H 4.55, N 4.22%; found: C 57.82, H 4.59, N 4.19%.

Refinement top

All H atoms on C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å for aromatic hydrogen atoms and C—H = 0.97 Å for methylene hydrogen atoms, and Uiso=1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. A view of the molecule of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Symmetry code: (i) = 1 − x, 1 − y, 1 − z; (ii) = 2 − x, 1 − y, −z.
catena-poly[[dibenzyldichloridotin(IV)]-µ-1,4-bis(pyridin-3-ylmethoxy)benzene] top
Crystal data top
[SnCl2(C7H7)2(C18H16N2O2)]Z = 2
Mr = 664.17F000 = 672
Monoclinic, P21/cDx = 1.451 Mg m−3
Hall symbol: -P 2ybcMo Kα radiation
λ = 0.71069 Å
a = 7.2380 (5) Åθ = 2.0–28.5º
b = 14.3560 (9) ŵ = 1.05 mm−1
c = 14.6290 (9) ÅT = 293 (2) K
β = 90.098 (1)ºBlock, colorless
V = 1520.08 (17) Å30.38 × 0.33 × 0.28 mm
Data collection top
Bruker APEX CCD area-detector
diffractometer		3558 independent reflections
Radiation source: fine-focus sealed tube3144 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.032
T = 293(2) Kθmax = 28.5º
ω scansθmin = 2.0º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −5→9
Tmin = 0.678, Tmax = 0.746k = −18→18
9019 measured reflectionsl = −18→16
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.062  w = 1/[σ2(Fo2) + (0.025P)2 + 0.426P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3558 reflectionsΔρmax = 0.31 e Å−3
178 parametersΔρmin = −0.80 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[SnCl2(C7H7)2(C18H16N2O2)]V = 1520.08 (17) Å3
Mr = 664.17Z = 2
Monoclinic, P21/cMo Kα
a = 7.2380 (5) ŵ = 1.05 mm−1
b = 14.3560 (9) ÅT = 293 (2) K
c = 14.6290 (9) Å0.38 × 0.33 × 0.28 mm
β = 90.098 (1)º
Data collection top
Bruker APEX CCD area-detector
diffractometer		3558 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3144 reflections with I > 2σ(I)
Tmin = 0.678, Tmax = 0.746Rint = 0.032
9019 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.026178 parameters
wR(F2) = 0.062H-atom parameters constrained
S = 1.06Δρmax = 0.31 e Å−3
3558 reflectionsΔρmin = −0.80 e Å−3
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 > 2sigma(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
Sn10.50000.50000.50000.03137 (6)
Cl10.20749 (7)0.43159 (4)0.57024 (3)0.05319 (13)
C10.8020 (3)0.29921 (14)0.38280 (14)0.0532 (5)
H10.90660.33220.40060.064*
C20.8068 (5)0.24379 (18)0.30446 (18)0.0773 (9)
H20.91400.24040.26970.093*
C30.6534 (6)0.19451 (18)0.27899 (18)0.0898 (11)
H30.65680.15760.22680.108*
C40.4961 (5)0.19903 (18)0.3293 (2)0.0842 (9)
H40.39290.16500.31130.101*
C50.4881 (4)0.25374 (15)0.40689 (17)0.0596 (6)
H50.37980.25620.44090.072*
C60.6417 (3)0.30517 (12)0.43423 (12)0.0415 (4)
C70.6336 (3)0.36578 (13)0.51685 (13)0.0450 (4)
H7A0.75890.37650.53800.054*
H7B0.56940.33200.56460.054*
C80.5061 (2)0.45295 (11)0.28016 (10)0.0322 (3)
H80.63210.46070.29010.039*
C90.4468 (2)0.42783 (12)0.19347 (11)0.0346 (3)
C100.2592 (3)0.41791 (16)0.17951 (13)0.0507 (5)
H100.21410.40040.12250.061*
C110.1393 (3)0.43422 (18)0.25106 (13)0.0556 (6)
H110.01240.42930.24230.067*
C120.2089 (2)0.45780 (15)0.33514 (12)0.0429 (4)
H120.12740.46800.38320.051*
C130.5846 (3)0.41269 (13)0.11814 (12)0.0410 (4)
H13A0.65070.35470.12760.049*
H13B0.52230.40980.05950.049*
C140.8871 (3)0.42179 (13)−0.00519 (12)0.0436 (4)
H140.81180.3695−0.00920.052*
C150.8503 (3)0.49061 (12)0.05819 (13)0.0396 (4)
C160.9622 (3)0.56830 (14)0.06280 (13)0.0460 (4)
H160.93620.61470.10520.055*
O10.7078 (2)0.48820 (10)0.12015 (12)0.0590 (5)
N10.39040 (19)0.46651 (11)0.35020 (9)0.0328 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02965 (9)0.03914 (10)0.02533 (9)0.00382 (6)0.00442 (6)−0.00170 (5)
Cl10.0395 (2)0.0754 (3)0.0447 (3)−0.0091 (2)0.00994 (19)−0.0005 (2)
C10.0660 (13)0.0428 (10)0.0509 (12)0.0122 (9)0.0140 (10)0.0053 (9)
C20.125 (2)0.0526 (13)0.0544 (14)0.0342 (15)0.0313 (15)0.0074 (11)
C30.180 (4)0.0434 (13)0.0463 (14)0.0161 (17)−0.0108 (18)−0.0093 (10)
C40.129 (3)0.0485 (14)0.0748 (18)−0.0162 (15)−0.0235 (18)−0.0062 (12)
C50.0737 (15)0.0441 (11)0.0610 (13)−0.0067 (10)−0.0047 (11)0.0067 (9)
C60.0542 (11)0.0330 (8)0.0373 (9)0.0084 (8)0.0019 (8)0.0047 (7)
C70.0515 (11)0.0466 (10)0.0368 (9)0.0134 (8)−0.0011 (8)0.0007 (8)
C80.0274 (7)0.0404 (9)0.0290 (8)−0.0003 (6)0.0033 (6)0.0018 (6)
C90.0352 (8)0.0431 (9)0.0255 (7)−0.0043 (7)0.0064 (6)0.0024 (6)
C100.0404 (10)0.0822 (15)0.0296 (9)−0.0124 (10)−0.0009 (7)−0.0004 (9)
C110.0296 (9)0.1006 (18)0.0367 (10)−0.0086 (10)0.0001 (7)0.0035 (10)
C120.0300 (8)0.0652 (12)0.0334 (9)0.0003 (8)0.0067 (7)0.0024 (8)
C130.0430 (9)0.0498 (10)0.0303 (8)−0.0100 (8)0.0094 (7)−0.0059 (7)
C140.0444 (10)0.0481 (10)0.0383 (9)−0.0156 (8)0.0119 (7)−0.0131 (8)
C150.0380 (9)0.0495 (10)0.0313 (9)−0.0067 (7)0.0113 (7)−0.0080 (7)
C160.0466 (10)0.0505 (10)0.0410 (10)−0.0130 (8)0.0171 (8)−0.0188 (8)
O10.0566 (9)0.0633 (9)0.0572 (10)−0.0258 (7)0.0344 (8)−0.0252 (7)
N10.0302 (7)0.0419 (7)0.0263 (7)0.0009 (6)0.0031 (5)0.0013 (6)
Geometric parameters (Å, °) top
Sn1—C72.1696 (18)C8—H80.9300
Sn1—N12.3784 (14)C9—C101.380 (2)
Sn1—Cl12.5515 (5)C9—C131.504 (2)
C1—C61.387 (3)C10—C111.381 (3)
C1—C21.396 (3)C10—H100.9300
C1—H10.9300C11—C121.371 (3)
C2—C31.368 (5)C11—H110.9300
C2—H20.9300C12—N11.338 (2)
C3—C41.358 (5)C12—H120.9300
C3—H30.9300C13—O11.404 (2)
C4—C51.382 (4)C13—H13A0.9700
C4—H40.9300C13—H13B0.9700
C5—C61.393 (3)C14—C151.381 (2)
C5—H50.9300C14—C16i1.387 (2)
C6—C71.491 (3)C14—H140.9300
C7—H7A0.9700C15—O11.375 (2)
C7—H7B0.9700C15—C161.380 (3)
C8—N11.339 (2)C16—C14i1.387 (2)
C8—C91.386 (2)C16—H160.9300
C7—Sn1—N194.19 (6)C10—C9—C13122.04 (15)
C7—Sn1—Cl188.98 (6)C8—C9—C13120.23 (15)
N1—Sn1—Cl191.01 (4)C9—C10—C11119.34 (17)
C6—C1—C2120.2 (2)C9—C10—H10120.3
C6—C1—H1119.9C11—C10—H10120.3
C2—C1—H1119.9C12—C11—C10119.43 (17)
C3—C2—C1119.8 (3)C12—C11—H11120.3
C3—C2—H2120.1C10—C11—H11120.3
C1—C2—H2120.1N1—C12—C11122.02 (16)
C4—C3—C2120.6 (2)N1—C12—H12119.0
C4—C3—H3119.7C11—C12—H12119.0
C2—C3—H3119.7O1—C13—C9107.17 (14)
C3—C4—C5120.6 (3)O1—C13—H13A110.3
C3—C4—H4119.7C9—C13—H13A110.3
C5—C4—H4119.7O1—C13—H13B110.3
C4—C5—C6120.2 (3)C9—C13—H13B110.3
C4—C5—H5119.9H13A—C13—H13B108.5
C6—C5—H5119.9C15—C14—C16i119.17 (17)
C1—C6—C5118.7 (2)C15—C14—H14120.4
C1—C6—C7120.68 (19)C16i—C14—H14120.4
C5—C6—C7120.66 (19)O1—C15—C16115.42 (15)
C6—C7—Sn1116.39 (12)O1—C15—C14124.78 (16)
C6—C7—H7A108.2C16—C15—C14119.80 (17)
Sn1—C7—H7A108.2C15—C16—C14i121.03 (16)
C6—C7—H7B108.2C15—C16—H16119.5
Sn1—C7—H7B108.2C14i—C16—H16119.5
H7A—C7—H7B107.3C15—O1—C13118.87 (14)
N1—C8—C9123.04 (15)C12—N1—C8118.41 (14)
N1—C8—H8118.5C12—N1—Sn1119.77 (11)
C9—C8—H8118.5C8—N1—Sn1121.78 (11)
C10—C9—C8117.73 (15)
C6—C1—C2—C3−0.7 (3)C8—C9—C13—O1−46.9 (2)
C1—C2—C3—C40.0 (4)C16i—C14—C15—O1−178.7 (2)
C2—C3—C4—C50.2 (4)C16i—C14—C15—C160.6 (3)
C3—C4—C5—C60.2 (4)O1—C15—C16—C14i178.7 (2)
C2—C1—C6—C51.1 (3)C14—C15—C16—C14i−0.6 (4)
C2—C1—C6—C7−178.63 (18)C16—C15—O1—C13178.23 (19)
C4—C5—C6—C1−0.8 (3)C14—C15—O1—C13−2.5 (3)
C4—C5—C6—C7178.9 (2)C9—C13—O1—C15179.19 (18)
C1—C6—C7—Sn1100.43 (18)C11—C12—N1—C81.0 (3)
C5—C6—C7—Sn1−79.3 (2)C11—C12—N1—Sn1−176.86 (17)
N1ii—Sn1—C7—C6−171.71 (16)C9—C8—N1—C12−1.8 (3)
N1—Sn1—C7—C68.29 (16)C9—C8—N1—Sn1175.98 (13)
Cl1ii—Sn1—C7—C6−80.77 (15)C7—Sn1—N1—C12112.89 (15)
Cl1—Sn1—C7—C699.23 (15)C7ii—Sn1—N1—C12−67.11 (15)
N1—C8—C9—C100.9 (3)Cl1ii—Sn1—N1—C12−156.17 (14)
N1—C8—C9—C13−179.33 (16)Cl1—Sn1—N1—C1223.83 (14)
C8—C9—C10—C110.8 (3)C7—Sn1—N1—C8−64.88 (14)
C13—C9—C10—C11−179.0 (2)C7ii—Sn1—N1—C8115.12 (14)
C9—C10—C11—C12−1.5 (4)Cl1ii—Sn1—N1—C826.06 (13)
C10—C11—C12—N10.7 (4)Cl1—Sn1—N1—C8−153.94 (13)
C10—C9—C13—O1132.9 (2)
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z+1.
Acknowledgements top

We thank the National Natural Science Foundation of China (No. 20471014), the Program for New Century Excellent Talents in Chinese Universities (NCET-05–0320), the Fok Ying Tung Education Foundation, and the Analysis and Testing Foundation of Northeast Normal University for support.

references
References top

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