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

In the title compound, catena-poly[[dibenzyl­dichlorido­tin(IV)]-μ-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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.026
• wR factor = 0.062
• Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.78 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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).

S2. Experimental

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%.

S3. Refinement

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 U_iso=1.2U_eq(C).

Computing details

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

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]

Crystal data

[SnCl2(C7H7)2(C18H16N2O2)]	Z = 2
Mr = 664.17	F(000) = 672
Monoclinic, P21/c	Dx = 1.451 Mg m^−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71069 Å
a = 7.2380 (5) Å	θ = 2.0–28.5°
b = 14.3560 (9) Å	µ = 1.05 mm^−1
c = 14.6290 (9) Å	T = 293 K
β = 90.098 (1)°	Block, colorless
V = 1520.08 (17) Å^3	0.38 × 0.33 × 0.28 mm

Data collection

Bruker APEX CCD area-detector diffractometer	3558 independent reflections
Radiation source: fine-focus sealed tube	3144 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scans	θmax = 28.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→9
Tmin = 0.678, Tmax = 0.746	k = −18→18
9019 measured reflections	l = −18→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.062	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.025P)^2 + 0.426P] where P = (Fo^2 + 2Fc^2)/3
3558 reflections	(Δ/σ)max < 0.001
178 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.80 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.5000	0.5000	0.5000	0.03137 (6)
Cl1	0.20749 (7)	0.43159 (4)	0.57024 (3)	0.05319 (13)
C1	0.8020 (3)	0.29921 (14)	0.38280 (14)	0.0532 (5)
H1	0.9066	0.3322	0.4006	0.064*
C2	0.8068 (5)	0.24379 (18)	0.30446 (18)	0.0773 (9)
H2	0.9140	0.2404	0.2697	0.093*
C3	0.6534 (6)	0.19451 (18)	0.27899 (18)	0.0898 (11)
H3	0.6568	0.1576	0.2268	0.108*
C4	0.4961 (5)	0.19903 (18)	0.3293 (2)	0.0842 (9)
H4	0.3929	0.1650	0.3113	0.101*
C5	0.4881 (4)	0.25374 (15)	0.40689 (17)	0.0596 (6)
H5	0.3798	0.2562	0.4409	0.072*
C6	0.6417 (3)	0.30517 (12)	0.43423 (12)	0.0415 (4)
C7	0.6336 (3)	0.36578 (13)	0.51685 (13)	0.0450 (4)
H7A	0.7589	0.3765	0.5380	0.054*
H7B	0.5694	0.3320	0.5646	0.054*
C8	0.5061 (2)	0.45295 (11)	0.28016 (10)	0.0322 (3)
H8	0.6321	0.4607	0.2901	0.039*
C9	0.4468 (2)	0.42783 (12)	0.19347 (11)	0.0346 (3)
C10	0.2592 (3)	0.41791 (16)	0.17951 (13)	0.0507 (5)
H10	0.2141	0.4004	0.1225	0.061*
C11	0.1393 (3)	0.43422 (18)	0.25106 (13)	0.0556 (6)
H11	0.0124	0.4293	0.2423	0.067*
C12	0.2089 (2)	0.45780 (15)	0.33514 (12)	0.0429 (4)
H12	0.1274	0.4680	0.3832	0.051*
C13	0.5846 (3)	0.41269 (13)	0.11814 (12)	0.0410 (4)
H13A	0.6507	0.3547	0.1276	0.049*
H13B	0.5223	0.4098	0.0595	0.049*
C14	0.8871 (3)	0.42179 (13)	−0.00519 (12)	0.0436 (4)
H14	0.8118	0.3695	−0.0092	0.052*
C15	0.8503 (3)	0.49061 (12)	0.05819 (13)	0.0396 (4)
C16	0.9622 (3)	0.56830 (14)	0.06280 (13)	0.0460 (4)
H16	0.9362	0.6147	0.1052	0.055*
O1	0.7078 (2)	0.48820 (10)	0.12015 (12)	0.0590 (5)
N1	0.39040 (19)	0.46651 (11)	0.35020 (9)	0.0328 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.02965 (9)	0.03914 (10)	0.02533 (9)	0.00382 (6)	0.00442 (6)	−0.00170 (5)
Cl1	0.0395 (2)	0.0754 (3)	0.0447 (3)	−0.0091 (2)	0.00994 (19)	−0.0005 (2)
C1	0.0660 (13)	0.0428 (10)	0.0509 (12)	0.0122 (9)	0.0140 (10)	0.0053 (9)
C2	0.125 (2)	0.0526 (13)	0.0544 (14)	0.0342 (15)	0.0313 (15)	0.0074 (11)
C3	0.180 (4)	0.0434 (13)	0.0463 (14)	0.0161 (17)	−0.0108 (18)	−0.0093 (10)
C4	0.129 (3)	0.0485 (14)	0.0748 (18)	−0.0162 (15)	−0.0235 (18)	−0.0062 (12)
C5	0.0737 (15)	0.0441 (11)	0.0610 (13)	−0.0067 (10)	−0.0047 (11)	0.0067 (9)
C6	0.0542 (11)	0.0330 (8)	0.0373 (9)	0.0084 (8)	0.0019 (8)	0.0047 (7)
C7	0.0515 (11)	0.0466 (10)	0.0368 (9)	0.0134 (8)	−0.0011 (8)	0.0007 (8)
C8	0.0274 (7)	0.0404 (9)	0.0290 (8)	−0.0003 (6)	0.0033 (6)	0.0018 (6)
C9	0.0352 (8)	0.0431 (9)	0.0255 (7)	−0.0043 (7)	0.0064 (6)	0.0024 (6)
C10	0.0404 (10)	0.0822 (15)	0.0296 (9)	−0.0124 (10)	−0.0009 (7)	−0.0004 (9)
C11	0.0296 (9)	0.1006 (18)	0.0367 (10)	−0.0086 (10)	0.0001 (7)	0.0035 (10)
C12	0.0300 (8)	0.0652 (12)	0.0334 (9)	0.0003 (8)	0.0067 (7)	0.0024 (8)
C13	0.0430 (9)	0.0498 (10)	0.0303 (8)	−0.0100 (8)	0.0094 (7)	−0.0059 (7)
C14	0.0444 (10)	0.0481 (10)	0.0383 (9)	−0.0156 (8)	0.0119 (7)	−0.0131 (8)
C15	0.0380 (9)	0.0495 (10)	0.0313 (9)	−0.0067 (7)	0.0113 (7)	−0.0080 (7)
C16	0.0466 (10)	0.0505 (10)	0.0410 (10)	−0.0130 (8)	0.0171 (8)	−0.0188 (8)
O1	0.0566 (9)	0.0633 (9)	0.0572 (10)	−0.0258 (7)	0.0344 (8)	−0.0252 (7)
N1	0.0302 (7)	0.0419 (7)	0.0263 (7)	0.0009 (6)	0.0031 (5)	0.0013 (6)

Geometric parameters (Å, º)

Sn1—C7	2.1696 (18)	C8—H8	0.9300
Sn1—N1	2.3784 (14)	C9—C10	1.380 (2)
Sn1—Cl1	2.5515 (5)	C9—C13	1.504 (2)
C1—C6	1.387 (3)	C10—C11	1.381 (3)
C1—C2	1.396 (3)	C10—H10	0.9300
C1—H1	0.9300	C11—C12	1.371 (3)
C2—C3	1.368 (5)	C11—H11	0.9300
C2—H2	0.9300	C12—N1	1.338 (2)
C3—C4	1.358 (5)	C12—H12	0.9300
C3—H3	0.9300	C13—O1	1.404 (2)
C4—C5	1.382 (4)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.393 (3)	C14—C15	1.381 (2)
C5—H5	0.9300	C14—C16^i	1.387 (2)
C6—C7	1.491 (3)	C14—H14	0.9300
C7—H7A	0.9700	C15—O1	1.375 (2)
C7—H7B	0.9700	C15—C16	1.380 (3)
C8—N1	1.339 (2)	C16—C14^i	1.387 (2)
C8—C9	1.386 (2)	C16—H16	0.9300
C7—Sn1—N1	94.19 (6)	C10—C9—C13	122.04 (15)
C7—Sn1—Cl1	88.98 (6)	C8—C9—C13	120.23 (15)
N1—Sn1—Cl1	91.01 (4)	C9—C10—C11	119.34 (17)
C6—C1—C2	120.2 (2)	C9—C10—H10	120.3
C6—C1—H1	119.9	C11—C10—H10	120.3
C2—C1—H1	119.9	C12—C11—C10	119.43 (17)
C3—C2—C1	119.8 (3)	C12—C11—H11	120.3
C3—C2—H2	120.1	C10—C11—H11	120.3
C1—C2—H2	120.1	N1—C12—C11	122.02 (16)
C4—C3—C2	120.6 (2)	N1—C12—H12	119.0
C4—C3—H3	119.7	C11—C12—H12	119.0
C2—C3—H3	119.7	O1—C13—C9	107.17 (14)
C3—C4—C5	120.6 (3)	O1—C13—H13A	110.3
C3—C4—H4	119.7	C9—C13—H13A	110.3
C5—C4—H4	119.7	O1—C13—H13B	110.3
C4—C5—C6	120.2 (3)	C9—C13—H13B	110.3
C4—C5—H5	119.9	H13A—C13—H13B	108.5
C6—C5—H5	119.9	C15—C14—C16^i	119.17 (17)
C1—C6—C5	118.7 (2)	C15—C14—H14	120.4
C1—C6—C7	120.68 (19)	C16^i—C14—H14	120.4
C5—C6—C7	120.66 (19)	O1—C15—C16	115.42 (15)
C6—C7—Sn1	116.39 (12)	O1—C15—C14	124.78 (16)
C6—C7—H7A	108.2	C16—C15—C14	119.80 (17)
Sn1—C7—H7A	108.2	C15—C16—C14^i	121.03 (16)
C6—C7—H7B	108.2	C15—C16—H16	119.5
Sn1—C7—H7B	108.2	C14^i—C16—H16	119.5
H7A—C7—H7B	107.3	C15—O1—C13	118.87 (14)
N1—C8—C9	123.04 (15)	C12—N1—C8	118.41 (14)
N1—C8—H8	118.5	C12—N1—Sn1	119.77 (11)
C9—C8—H8	118.5	C8—N1—Sn1	121.78 (11)
C10—C9—C8	117.73 (15)
C6—C1—C2—C3	−0.7 (3)	C8—C9—C13—O1	−46.9 (2)
C1—C2—C3—C4	0.0 (4)	C16^i—C14—C15—O1	−178.7 (2)
C2—C3—C4—C5	0.2 (4)	C16^i—C14—C15—C16	0.6 (3)
C3—C4—C5—C6	0.2 (4)	O1—C15—C16—C14^i	178.7 (2)
C2—C1—C6—C5	1.1 (3)	C14—C15—C16—C14^i	−0.6 (4)
C2—C1—C6—C7	−178.63 (18)	C16—C15—O1—C13	178.23 (19)
C4—C5—C6—C1	−0.8 (3)	C14—C15—O1—C13	−2.5 (3)
C4—C5—C6—C7	178.9 (2)	C9—C13—O1—C15	179.19 (18)
C1—C6—C7—Sn1	100.43 (18)	C11—C12—N1—C8	1.0 (3)
C5—C6—C7—Sn1	−79.3 (2)	C11—C12—N1—Sn1	−176.86 (17)
N1^ii—Sn1—C7—C6	−171.71 (16)	C9—C8—N1—C12	−1.8 (3)
N1—Sn1—C7—C6	8.29 (16)	C9—C8—N1—Sn1	175.98 (13)
Cl1^ii—Sn1—C7—C6	−80.77 (15)	C7—Sn1—N1—C12	112.89 (15)
Cl1—Sn1—C7—C6	99.23 (15)	C7^ii—Sn1—N1—C12	−67.11 (15)
N1—C8—C9—C10	0.9 (3)	Cl1^ii—Sn1—N1—C12	−156.17 (14)
N1—C8—C9—C13	−179.33 (16)	Cl1—Sn1—N1—C12	23.83 (14)
C8—C9—C10—C11	0.8 (3)	C7—Sn1—N1—C8	−64.88 (14)
C13—C9—C10—C11	−179.0 (2)	C7^ii—Sn1—N1—C8	115.12 (14)
C9—C10—C11—C12	−1.5 (4)	Cl1^ii—Sn1—N1—C8	26.06 (13)
C10—C11—C12—N1	0.7 (4)	Cl1—Sn1—N1—C8	−153.94 (13)
C10—C9—C13—O1	132.9 (2)

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z+1.