catena-Poly[[trimethyl­tin(IV)]-μ-2-thio­phene-2-acetato-κ²O:O′]

The title compound, [Sn(CH₃)₃(C₆H₅O₂S)]_n, has an infinite chain structure. The SnO₂C₃ centre has a slightly distorted trigonal bipyramidal geometry with the O atoms in the axial positions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.037
• wR factor = 0.127
• Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.89
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Sn1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         14

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.891
            Tmax scaled      0.441 Tmin scaled      0.340
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         18

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

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

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S1. Comment

The title compound, (I) (Fig. 1), possesses an infinite one-dimensional chain structure arising from Sn—O bridges to the ligand. The Sn—O distances in (I) (Table 1) are similar to those in related organotin carboxylates (Ma et al., 2006). The Sn atom has distorted trigonal-bipyramidal geometry, with the O atoms in axial positions [O1—Sn1—O2ⁱ = 173.28 (17) °] and the C atoms of the three methyl groups in equatorial positions. The sum of the equatorial C—Sn—C angles is 359.4 °, indicating near coplanarity for these atoms.

Related literature

For related materials, see Ma et al. (2006).

S2. Experimental

The reaction was carried out under a nitrogen atmosphere. 2-Thiopheneacetic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to 30 ml of benzene in a Schlenk flask and stirred for 0.5 h. Trimethyltin chloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at 313 K.The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (1:1 v/v) to yield colourless blocks of (I). Yield 80%; m.p. 452 K. Analysis calculated (%) for C₉H₁₄O₂SSn: C 35.44; H 4.63%. found: C 35.37; H 4.71%.

S3. Refinement

The H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity. Atom O2A is generated by the symmetry operation (1 - x, 1/2 + y, 3/2 - z).
	Fig. 2. Part of the chain structure of (I), H atoms have been omitted for clarity.

catena-Poly[[trimethyltin(IV)]-µ-2-thiophene-2-acetato-κ²O:O']

Crystal data

[Sn(CH3)3(C6H5O2S)]	F(000) = 600
Mr = 304.95	Dx = 1.642 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2389 reflections
a = 9.5179 (13) Å	θ = 2.6–25.8°
b = 10.1177 (14) Å	µ = 2.21 mm^−1
c = 13.2038 (18) Å	T = 298 K
β = 104.039 (2)°	Block, colourless
V = 1233.5 (3) Å^3	0.54 × 0.39 × 0.37 mm
Z = 4

Data collection

Siemens SMART CCD diffractometer	2168 independent reflections
Radiation source: fine-focus sealed tube	1622 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.381, Tmax = 0.495	k = −11→12
4898 measured reflections	l = −15→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.073P)^2 + 1.6901P] where P = (Fo^2 + 2Fc^2)/3
2168 reflections	(Δ/σ)max = 0.001
118 parameters	Δρmax = 1.10 e Å^−3
18 restraints	Δρmin = −0.63 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.56253 (5)	1.10603 (4)	0.72279 (3)	0.0566 (2)
O1	0.7129 (5)	0.9441 (5)	0.7131 (5)	0.0843 (15)
O2	0.5752 (5)	0.7961 (5)	0.7658 (4)	0.0794 (14)
S1	0.9638 (3)	0.8817 (2)	0.6287 (2)	0.1037 (8)
C1	0.6853 (9)	0.8260 (7)	0.7362 (6)	0.0735 (19)
C2	0.7962 (9)	0.7225 (8)	0.7295 (7)	0.093 (3)
H2A	0.7478	0.6374	0.7194	0.112*
H2B	0.8667	0.7193	0.7962	0.112*
C3	0.8771 (7)	0.7394 (7)	0.6452 (6)	0.0703 (18)
C4	0.8965 (11)	0.6402 (9)	0.5751 (9)	0.103 (3)
H4	0.8577	0.5554	0.5706	0.123*
C5	0.9859 (13)	0.6919 (12)	0.5122 (10)	0.125 (3)
H5	1.0093	0.6439	0.4585	0.150*
C6	1.0323 (11)	0.8122 (11)	0.5361 (9)	0.115 (3)
H6	1.0972	0.8550	0.5047	0.138*
C7	0.7008 (9)	1.2365 (8)	0.6666 (7)	0.086 (2)
H7A	0.6764	1.2347	0.5917	0.129*
H7B	0.7996	1.2092	0.6925	0.129*
H7C	0.6889	1.3246	0.6901	0.129*
C8	0.5859 (11)	1.0867 (8)	0.8854 (6)	0.090 (3)
H8A	0.6722	1.1315	0.9219	0.136*
H8B	0.5926	0.9947	0.9039	0.136*
H8C	0.5034	1.1250	0.9041	0.136*
C9	0.3859 (8)	1.0250 (9)	0.6101 (6)	0.087 (2)
H9A	0.3962	1.0458	0.5414	0.130*
H9B	0.2970	1.0617	0.6196	0.130*
H9C	0.3847	0.9308	0.6185	0.130*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0716 (3)	0.0419 (3)	0.0623 (3)	−0.0046 (2)	0.0279 (2)	−0.00282 (19)
O1	0.090 (3)	0.044 (3)	0.133 (5)	0.005 (3)	0.055 (3)	0.007 (3)
O2	0.090 (4)	0.052 (3)	0.109 (4)	−0.003 (3)	0.049 (3)	0.003 (3)
S1	0.0950 (16)	0.0907 (17)	0.129 (2)	−0.0182 (13)	0.0331 (15)	0.0003 (14)
C1	0.088 (5)	0.045 (4)	0.093 (5)	−0.001 (4)	0.033 (4)	0.004 (4)
C2	0.102 (6)	0.062 (5)	0.127 (7)	0.018 (4)	0.051 (5)	0.011 (5)
C3	0.058 (4)	0.054 (4)	0.100 (5)	0.012 (3)	0.020 (4)	0.006 (4)
C4	0.110 (6)	0.073 (5)	0.140 (6)	0.008 (4)	0.058 (5)	−0.001 (5)
C5	0.140 (6)	0.104 (6)	0.149 (6)	0.034 (6)	0.072 (5)	−0.001 (6)
C6	0.110 (5)	0.105 (6)	0.148 (6)	0.018 (5)	0.067 (5)	0.015 (6)
C7	0.108 (6)	0.050 (4)	0.112 (6)	−0.019 (4)	0.053 (5)	0.012 (4)
C8	0.128 (7)	0.080 (6)	0.064 (4)	0.001 (5)	0.024 (5)	−0.002 (4)
C9	0.096 (5)	0.089 (6)	0.074 (5)	−0.011 (5)	0.019 (4)	−0.018 (4)

Geometric parameters (Å, º)

Sn1—C8	2.113 (8)	C4—C5	1.425 (14)
Sn1—C9	2.120 (7)	C4—H4	0.9300
Sn1—C7	2.121 (7)	C5—C6	1.307 (14)
Sn1—O1	2.200 (5)	C5—H5	0.9300
Sn1—O2^i	2.353 (5)	C6—H6	0.9300
O1—C1	1.276 (9)	C7—H7A	0.9600
O2—C1	1.242 (8)	C7—H7B	0.9600
O2—Sn1^ii	2.353 (5)	C7—H7C	0.9600
S1—C6	1.674 (10)	C8—H8A	0.9600
S1—C3	1.699 (8)	C8—H8B	0.9600
C1—C2	1.505 (10)	C8—H8C	0.9600
C2—C3	1.509 (10)	C9—H9A	0.9600
C2—H2A	0.9700	C9—H9B	0.9600
C2—H2B	0.9700	C9—H9C	0.9600
C3—C4	1.408 (12)
C8—Sn1—C9	123.2 (4)	C3—C4—H4	125.9
C8—Sn1—C7	119.5 (4)	C5—C4—H4	125.9
C9—Sn1—C7	116.7 (3)	C6—C5—C4	114.6 (10)
C8—Sn1—O1	94.6 (3)	C6—C5—H5	122.7
C9—Sn1—O1	95.0 (3)	C4—C5—H5	122.7
C7—Sn1—O1	88.6 (3)	C5—C6—S1	113.5 (8)
C8—Sn1—O2^i	86.2 (3)	C5—C6—H6	123.3
C9—Sn1—O2^i	90.1 (3)	S1—C6—H6	123.3
C7—Sn1—O2^i	85.2 (3)	Sn1—C7—H7A	109.5
O1—Sn1—O2^i	173.28 (17)	Sn1—C7—H7B	109.5
C1—O1—Sn1	120.6 (4)	H7A—C7—H7B	109.5
C1—O2—Sn1^ii	138.2 (5)	Sn1—C7—H7C	109.5
C6—S1—C3	91.4 (5)	H7A—C7—H7C	109.5
O2—C1—O1	122.8 (7)	H7B—C7—H7C	109.5
O2—C1—C2	120.4 (7)	Sn1—C8—H8A	109.5
O1—C1—C2	116.8 (7)	Sn1—C8—H8B	109.5
C1—C2—C3	117.0 (7)	H8A—C8—H8B	109.5
C1—C2—H2A	108.0	Sn1—C8—H8C	109.5
C3—C2—H2A	108.0	H8A—C8—H8C	109.5
C1—C2—H2B	108.0	H8B—C8—H8C	109.5
C3—C2—H2B	108.0	Sn1—C9—H9A	109.5
H2A—C2—H2B	107.3	Sn1—C9—H9B	109.5
C4—C3—C2	125.1 (7)	H9A—C9—H9B	109.5
C4—C3—S1	112.0 (6)	Sn1—C9—H9C	109.5
C2—C3—S1	122.8 (6)	H9A—C9—H9C	109.5
C3—C4—C5	108.3 (9)	H9B—C9—H9C	109.5

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2.