catena-Poly[[trimethyltin(IV)]-μ-2-methylbenzoato-κO:O'].

The polymeric structure of the title compound, [Sn(CH(3))(3)(C(8)H(7)O(2))](n), is composed of zigzag chains in which the tin(IV) atoms, coordinated by three methyl groups, are bridged by toluene-2-carboxyl-ate ligands via their O atoms. A slightly distorted trigonal-bipyramidal SnC(3)O(2) coordination geometry arises for the metal, with the O atoms in the axial sites. Weak C-H⋯O hydrogen bonds help to stabilize the packing.

Related literature

For biological activity of tin complexes with carboxyl­ate ligands, see, for example: Shahzadi et al. (2007 ▶). For a related structure, see: Danish et al. (2009 ▶). For a review of the structural chemistry of tin(IV) complexes with carboxyl­ate ligands, see: Tiekink (1991 ▶).

Experimental

Crystal data

[Sn(CH3)3(C8H7O2)]

M = 298.93

Monoclinic,

a = 10.618 (2) Å

b = 10.046 (2) Å

c = 12.833 (3) Å

β = 112.39 (3)°

V = 1265.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.00 mm−1

T = 293 K

0.42 × 0.12 × 0.09 mm

Data collection

Kuma KM-4 four circle diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.838, T max = 0.892

3389 measured reflections

3226 independent reflections

2090 reflections with I > 2σ(I)

R int = 0.022

3 standard reflections every 200 reflections

intensity decay: 6.4%

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.118

S = 1.04

3226 reflections

131 parameters

H-atom parameters constrained

Δρmax = 1.37 e Å−3

Δρmin = −1.69 e Å−3

Data collection: KM-4 Software (Kuma, 1996 ▶); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2001 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051587/hb5258sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051587/hb5258Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Sn(CH3)3(C8H7O2)]	F(000) = 592
Mr = 298.93	Dx = 1.569 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 10.618 (2) Å	θ = 6–15°
b = 10.046 (2) Å	µ = 2.00 mm−1
c = 12.833 (3) Å	T = 293 K
β = 112.39 (3)°	Block, colourless
V = 1265.7 (4) Å3	0.42 × 0.12 × 0.09 mm
Z = 4

Kuma KM-4 four circle diffractometer	2090 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
graphite	θmax = 30.1°, θmin = 2.1°
profile data from ω/2θ scans	h = 0→13
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	k = −13→0
Tmin = 0.838, Tmax = 0.892	l = −17→15
3389 measured reflections	3 standard reflections every 200 reflections
3226 independent reflections	intensity decay: 6.4%

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0777P)2 + 0.0604P] where P = (Fo2 + 2Fc2)/3
3226 reflections	(Δ/σ)max = 0.001
131 parameters	Δρmax = 1.37 e Å−3
0 restraints	Δρmin = −1.69 e Å−3

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.

	x	y	z	Uiso*/Ueq
Sn1	0.67213 (3)	0.58902 (3)	0.23186 (2)	0.04378 (12)
O1	0.8105 (3)	0.7804 (3)	0.2342 (4)	0.0645 (9)
C1	1.0203 (4)	0.7136 (4)	0.2204 (4)	0.0443 (8)
C7	0.9255 (4)	0.8130 (4)	0.2391 (3)	0.0429 (8)
C4	1.1974 (6)	0.5271 (6)	0.1924 (6)	0.0803 (17)
H4	1.2582	0.4665	0.1826	0.096*
C6	1.0906 (6)	0.6253 (6)	0.3062 (5)	0.0651 (13)
H6	1.0792	0.6290	0.3745	0.078*
C5	1.1780 (6)	0.5310 (7)	0.2904 (6)	0.0803 (17)
H5	1.2230	0.4707	0.3475	0.096*
C2	1.0385 (5)	0.7088 (5)	0.1204 (4)	0.0632 (12)
C3	1.1262 (7)	0.6142 (7)	0.1067 (6)	0.0825 (19)
H3	1.1374	0.6092	0.0383	0.099*
C8	0.9607 (9)	0.8037 (9)	0.0242 (6)	0.110 (3)
H8A	0.8646	0.7885	0.0011	0.165*
H8B	0.9873	0.7881	−0.0384	0.165*
H8C	0.9813	0.8940	0.0494	0.165*
O2	0.9682 (3)	0.9314 (3)	0.2610 (3)	0.0527 (7)
C12	0.5145 (5)	0.7309 (5)	0.1961 (6)	0.0780 (17)
H12A	0.5492	0.8098	0.2399	0.117*
H12B	0.4420	0.6947	0.2147	0.117*
H12C	0.4804	0.7529	0.1173	0.117*
C13	0.7115 (6)	0.5114 (6)	0.0940 (4)	0.0725 (15)
H13A	0.8034	0.5321	0.1031	0.109*
H13B	0.6495	0.5504	0.0253	0.109*
H13C	0.6994	0.4166	0.0909	0.109*
C11	0.7997 (7)	0.5631 (6)	0.4027 (5)	0.0814 (18)
H11A	0.8469	0.6448	0.4318	0.122*
H11B	0.8646	0.4940	0.4090	0.122*
H11C	0.7456	0.5388	0.4450	0.122*

	U11	U22	U33	U12	U13	U23
Sn1	0.04404 (18)	0.03127 (16)	0.05657 (19)	0.00215 (11)	0.01979 (13)	−0.00013 (11)
O1	0.0526 (18)	0.0341 (15)	0.118 (3)	−0.0025 (13)	0.0456 (18)	−0.0094 (17)
C1	0.0366 (18)	0.0333 (18)	0.063 (2)	−0.0039 (15)	0.0193 (17)	−0.0053 (16)
C7	0.045 (2)	0.0317 (18)	0.053 (2)	0.0008 (15)	0.0201 (17)	−0.0006 (16)
C4	0.057 (3)	0.063 (4)	0.122 (5)	0.017 (3)	0.036 (3)	−0.016 (3)
C6	0.061 (3)	0.059 (3)	0.072 (3)	0.018 (2)	0.022 (2)	0.006 (2)
C5	0.063 (3)	0.062 (4)	0.108 (5)	0.024 (3)	0.024 (3)	0.009 (3)
C2	0.066 (3)	0.059 (3)	0.073 (3)	0.012 (2)	0.036 (3)	0.006 (2)
C3	0.079 (4)	0.088 (4)	0.100 (5)	0.011 (3)	0.056 (4)	−0.015 (4)
C8	0.146 (7)	0.121 (6)	0.083 (4)	0.050 (5)	0.067 (4)	0.033 (4)
O2	0.0473 (17)	0.0323 (15)	0.082 (2)	−0.0026 (11)	0.0282 (16)	−0.0035 (13)
C12	0.055 (3)	0.043 (2)	0.135 (5)	0.003 (2)	0.034 (3)	0.017 (3)
C13	0.099 (4)	0.063 (3)	0.067 (3)	−0.021 (3)	0.044 (3)	−0.015 (3)
C11	0.084 (4)	0.087 (4)	0.055 (3)	−0.026 (3)	0.006 (3)	0.001 (3)

Sn1—C11	2.108 (6)	C2—C3	1.388 (7)
Sn1—C12	2.112 (5)	C2—C8	1.530 (8)
Sn1—C13	2.116 (5)	C3—H3	0.9300
Sn1—O2i	2.200 (3)	C8—H8A	0.9600
Sn1—O1	2.413 (3)	C8—H8B	0.9600
O1—C7	1.243 (5)	C8—H8C	0.9600
C1—C2	1.370 (7)	O2—Sn1ii	2.200 (3)
C1—C6	1.389 (7)	C12—H12A	0.9600
C1—C7	1.500 (5)	C12—H12B	0.9600
C7—O2	1.266 (5)	C12—H12C	0.9600
C4—C5	1.351 (10)	C13—H13A	0.9600
C4—C3	1.383 (10)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C6—C5	1.394 (8)	C11—H11A	0.9600
C6—H6	0.9300	C11—H11B	0.9600
C5—H5	0.9300	C11—H11C	0.9600
C11—Sn1—C12	116.8 (3)	C4—C3—C2	121.5 (6)
C11—Sn1—C13	124.8 (3)	C4—C3—H3	119.3
C12—Sn1—C13	117.3 (3)	C2—C3—H3	119.3
C11—Sn1—O2i	92.6 (2)	C2—C8—H8A	109.5
C12—Sn1—O2i	90.09 (17)	C2—C8—H8B	109.5
C13—Sn1—O2i	97.02 (17)	H8A—C8—H8B	109.5
C11—Sn1—O1	86.5 (2)	C2—C8—H8C	109.5
C12—Sn1—O1	83.88 (17)	H8A—C8—H8C	109.5
C13—Sn1—O1	89.46 (17)	H8B—C8—H8C	109.5
O2i—Sn1—O1	172.68 (11)	C7—O2—Sn1ii	119.7 (3)
C7—O1—Sn1	142.4 (3)	Sn1—C12—H12A	109.5
C2—C1—C6	119.6 (4)	Sn1—C12—H12B	109.5
C2—C1—C7	121.0 (4)	H12A—C12—H12B	109.5
C6—C1—C7	119.3 (4)	Sn1—C12—H12C	109.5
O1—C7—O2	121.4 (4)	H12A—C12—H12C	109.5
O1—C7—C1	121.5 (3)	H12B—C12—H12C	109.5
O2—C7—C1	117.1 (4)	Sn1—C13—H13A	109.5
C5—C4—C3	119.4 (5)	Sn1—C13—H13B	109.5
C5—C4—H4	120.3	H13A—C13—H13B	109.5
C3—C4—H4	120.3	Sn1—C13—H13C	109.5
C1—C6—C5	120.4 (6)	H13A—C13—H13C	109.5
C1—C6—H6	119.8	H13B—C13—H13C	109.5
C5—C6—H6	119.8	Sn1—C11—H11A	109.5
C4—C5—C6	120.1 (6)	Sn1—C11—H11B	109.5
C4—C5—H5	120.0	H11A—C11—H11B	109.5
C6—C5—H5	120.0	Sn1—C11—H11C	109.5
C1—C2—C3	119.0 (5)	H11A—C11—H11C	109.5
C1—C2—C8	120.6 (5)	H11B—C11—H11C	109.5
C3—C2—C8	120.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13C···O1i	0.96	2.66	3.271 (7)	122
C4—H4···O2iii	0.93	2.74	3.502 (6)	140

Table 1

Selected bond lengths (Å)

Sn1—C11	2.108 (6)
Sn1—C12	2.112 (5)
Sn1—C13	2.116 (5)
Sn1—O2i	2.200 (3)
Sn1—O1	2.413 (3)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13C⋯O1i	0.96	2.66	3.271 (7)	122
C4—H4⋯O2ii	0.93	2.74	3.502 (6)	140

Symmetry codes: (i) ; (ii) .