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

The title compound, [Sn(CH₃)₂(C₆H₅O₂S)Cl]_n, forms an extended one-dimensional chain structure which propagates along the a-axis direction. The two independent SnO₂C₂Cl centres have distorted trigonal–bipyramidal environments with the coordinated O atoms in the axial positions. Both thio­phene groups are disordered over two sites, with approximate occupancies of 0.5:0.5 and 0.78:0.22.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.029
• wR factor = 0.086
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT301_ALERT_3_B Main Residue  Disorder .........................      27.00 Perc.

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.85
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.62 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        S1'
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C4'
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        Sn2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C3'

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      0.852
            Tmax scaled      0.375 Tmin scaled      0.291

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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

A series of new triorganotin(IV) pyridinedicarboxylates were synthesized by the reaction of trimethyltin(IV), triphenyltin(IV) or tribenzyltin(IV) chloride with 2,6(3,5 or 2,5)-H₂pdc (pdc = pyridinedicarboxylate) (Ma et al.,2006). The title compound, (I) (Fig. 1), has an extended one-dimensional chain structure formed from Sn—O bridges to the ligand with Sn—O distances close to those in reported organotin carboxylates (Ma et al., 2006). The two independent Sn atoms are in distorted trigonal-bipyramidal coordination geometries, with the O atoms in axial positions and atoms C13/C14/Cl1 and C15/C16/Cl2 in equatorial positions. The sum of the equatorial angles at Sn1 and Sn2 of 357.2 and 356.2° indicate approximate coplanarity for the atoms involved.

Related literature

For related literature, see: Ma et al. (2006)

S2. Experimental

The reaction was carried out under N₂. 2-Thiopheneacetic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to the solution of benzene(30 ml) in a Schlenk flask and stirred for 0.5 h. Dimethyltin dichloride (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).(yield 80%; m.p. 472 K). Analysis calculated (%) for C₁₆H₂₂C_l2O₄S₂Sn₂ (Mr = 650.74): C, 29.53; H, 3.41. found: C, 29.47; H, 3.52.

S3. Refinement

During the refinement both thiophene groups were found to be disordered over two sites corresponding to an approximate 180° rotation parallel to the ring plane. The ratio of the occupancy factors refined to 0.502 (9):0.498 (2) and 0.783 (8):0.217 (8) for atoms S1/C3—C6:S1'/C3'-6' and atoms S2/C9—C12:S2'/C9'-C12', repectively. H atoms were positioned geometrically, with C—H = 0.91–0.97 Å and constrained to ride on their parent atoms, with U_iso(H) = U_eq(C) where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

Figures

	Fig. 1. The asymmetric unit showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity. The disorder is not shown.
	Fig. 2. The 1-D extended chain structure propagating along the a axis. H atoms have been omitted for clarity.

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

Crystal data

[Sn(CH3)2(C6H5O2S)Cl]	Z = 4
Mr = 325.37	F(000) = 632
Triclinic, P1	Dx = 1.862 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2189 (18) Å	Cell parameters from 4001 reflections
b = 10.591 (2) Å	θ = 2.3–28.1°
c = 12.226 (2) Å	µ = 2.58 mm^−1
α = 97.898 (2)°	T = 298 K
β = 93.287 (2)°	Block, colourless
γ = 99.948 (2)°	0.53 × 0.42 × 0.38 mm
V = 1160.6 (4) Å^3

Data collection

Bruker SMART CCD diffractometer	4020 independent reflections
Radiation source: fine-focus sealed tube	3265 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ϕ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.342, Tmax = 0.441	k = −10→12
6038 measured reflections	l = −11→14

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 1.0989P] where P = (Fo^2 + 2Fc^2)/3
4020 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.53 e Å^−3
0 restraints	Δρmin = −0.87 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sn1	0.62273 (3)	0.74816 (3)	0.10589 (2)	0.03419 (11)
Sn2	1.14767 (3)	0.81755 (3)	0.23097 (3)	0.03814 (12)
Cl1	0.79330 (14)	0.67290 (15)	−0.01443 (11)	0.0558 (4)
Cl2	1.36682 (14)	0.88314 (17)	0.35067 (12)	0.0627 (4)
O1	0.8452 (4)	0.8005 (4)	0.2392 (3)	0.0470 (8)
O2	1.0249 (3)	0.8696 (4)	0.3698 (3)	0.0466 (8)
O3	0.4573 (3)	0.6910 (3)	−0.0316 (3)	0.0456 (8)
O4	0.3239 (4)	0.7682 (4)	0.0944 (3)	0.0525 (9)
C1	0.8870 (5)	0.8430 (5)	0.3377 (4)	0.0392 (11)
C2	0.7808 (6)	0.8625 (5)	0.4239 (4)	0.0496 (13)
H2A	0.6871	0.8714	0.3883	0.060*
H2B	0.8190	0.9420	0.4741	0.060*
S1	0.6822 (9)	0.7729 (8)	0.6105 (6)	0.094 (2)	0.502 (9)
C3	0.7564 (6)	0.7512 (6)	0.4887 (4)	0.0546 (14)	0.502 (9)
C4	0.782 (6)	0.628 (3)	0.465 (3)	0.090 (2)	0.502 (9)
H4	0.8232	0.5987	0.4007	0.108*	0.502 (9)
C5	0.742 (19)	0.552 (14)	0.544 (14)	0.09 (2)	0.502 (9)
H5	0.7519	0.4659	0.5390	0.107*	0.502 (9)
C6	0.68 (2)	0.617 (18)	0.631 (17)	0.10 (2)	0.502 (9)
H6	0.6522	0.5811	0.6931	0.116*	0.502 (9)
S1'	0.7801 (14)	0.5963 (7)	0.4449 (7)	0.090 (2)	0.498 (9)
C3'	0.7564 (6)	0.7512 (6)	0.4887 (4)	0.0546 (14)	0.498 (9)
C4'	0.709 (4)	0.750 (3)	0.591 (3)	0.094 (2)	0.498 (9)
H4'	0.6883	0.8234	0.6328	0.113*	0.498 (9)
C5'	0.69 (2)	0.634 (17)	0.630 (16)	0.09 (2)	0.498 (9)
H5'	0.6633	0.6238	0.6993	0.111*	0.498 (9)
C6'	0.73 (2)	0.535 (15)	0.560 (15)	0.093 (16)	0.498 (9)
H6'	0.7239	0.4497	0.5729	0.111*	0.498 (9)
C7	0.3332 (5)	0.7131 (5)	−0.0002 (4)	0.0383 (10)
C8	0.2003 (5)	0.6627 (6)	−0.0817 (4)	0.0523 (13)
H8A	0.1862	0.5688	−0.0949	0.063*
H8B	0.1139	0.6861	−0.0483	0.063*
S2	0.3625 (3)	0.7310 (4)	−0.2599 (3)	0.0613 (9)	0.783 (8)
C9	0.2088 (6)	0.7109 (5)	−0.1905 (4)	0.0457 (12)	0.783 (8)
C10	0.094 (4)	0.747 (4)	−0.246 (3)	0.069 (4)	0.783 (8)
H10	0.0008	0.7441	−0.2196	0.083*	0.783 (8)
C11	0.129 (6)	0.787 (5)	−0.345 (3)	0.087 (10)	0.783 (8)
H11	0.0620	0.8143	−0.3930	0.104*	0.783 (8)
C12	0.272 (7)	0.783 (7)	−0.367 (6)	0.081 (9)	0.783 (8)
H12	0.3149	0.8060	−0.4300	0.097*	0.783 (8)
S2'	0.063 (4)	0.739 (4)	−0.267 (3)	0.069 (4)	0.217 (8)
C9'	0.2088 (6)	0.7109 (5)	−0.1905 (4)	0.0457 (12)	0.217 (8)
C10'	0.318 (6)	0.711 (6)	−0.260 (5)	0.0613 (9)	0.217 (8)
H10'	0.4020	0.6758	−0.2461	0.074*	0.217 (8)
C11'	0.30 (2)	0.77 (2)	−0.35 (2)	0.08 (4)	0.217 (8)
H11'	0.3732	0.7960	−0.3941	0.091*	0.217 (8)
C12'	0.16 (2)	0.777 (19)	−0.378 (12)	0.08 (3)	0.217 (8)
H12'	0.1162	0.8001	−0.4428	0.100*	0.217 (8)
C13	0.5429 (6)	0.6015 (5)	0.1980 (4)	0.0505 (13)
H13A	0.5026	0.6387	0.2629	0.076*
H13B	0.6224	0.5600	0.2197	0.076*
H13C	0.4672	0.5387	0.1535	0.076*
C14	0.6487 (6)	0.9496 (5)	0.1136 (5)	0.0549 (14)
H14A	0.5993	0.9844	0.1746	0.082*
H14B	0.6068	0.9696	0.0458	0.082*
H14C	0.7520	0.9870	0.1239	0.082*
C15	1.0898 (7)	0.6159 (5)	0.2174 (5)	0.0594 (15)
H15A	1.0252	0.5940	0.2735	0.089*
H15B	1.1774	0.5797	0.2270	0.089*
H15C	1.0403	0.5814	0.1456	0.089*
C16	1.1208 (7)	0.9686 (6)	0.1402 (5)	0.0617 (15)
H16A	1.0683	0.9327	0.0696	0.093*
H16B	1.2160	1.0160	0.1291	0.093*
H16C	1.0658	1.0259	0.1805	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.03134 (18)	0.03700 (19)	0.03505 (19)	0.00966 (13)	0.00292 (13)	0.00393 (13)
Sn2	0.03394 (19)	0.0430 (2)	0.0377 (2)	0.00999 (14)	0.00003 (13)	0.00405 (14)
Cl1	0.0422 (7)	0.0801 (10)	0.0466 (7)	0.0228 (7)	0.0089 (6)	−0.0023 (6)
Cl2	0.0373 (7)	0.0929 (11)	0.0523 (8)	0.0124 (7)	−0.0067 (6)	−0.0057 (7)
O1	0.0382 (18)	0.062 (2)	0.038 (2)	0.0098 (16)	−0.0044 (15)	0.0012 (16)
O2	0.0342 (18)	0.067 (2)	0.0360 (18)	0.0096 (16)	0.0004 (14)	−0.0022 (16)
O3	0.0340 (17)	0.063 (2)	0.0393 (19)	0.0175 (16)	−0.0030 (14)	−0.0019 (16)
O4	0.043 (2)	0.067 (2)	0.047 (2)	0.0147 (18)	0.0086 (16)	−0.0021 (18)
C1	0.038 (3)	0.043 (3)	0.039 (3)	0.012 (2)	0.000 (2)	0.010 (2)
C2	0.044 (3)	0.065 (4)	0.046 (3)	0.024 (3)	0.009 (2)	0.010 (3)
S1	0.119 (4)	0.097 (4)	0.086 (4)	0.038 (3)	0.063 (2)	0.035 (3)
C3	0.048 (3)	0.069 (4)	0.049 (3)	0.014 (3)	0.007 (2)	0.014 (3)
C4	0.146 (3)	0.074 (5)	0.057 (4)	0.034 (4)	0.014 (3)	0.014 (3)
C5	0.12 (5)	0.08 (3)	0.08 (4)	0.02 (3)	0.00 (3)	0.03 (2)
C6	0.11 (5)	0.10 (4)	0.10 (4)	0.02 (3)	0.04 (3)	0.05 (3)
S1'	0.146 (3)	0.074 (5)	0.057 (4)	0.034 (4)	0.014 (3)	0.014 (3)
C3'	0.048 (3)	0.069 (4)	0.049 (3)	0.014 (3)	0.007 (2)	0.014 (3)
C4'	0.119 (4)	0.097 (4)	0.086 (4)	0.038 (3)	0.063 (2)	0.035 (3)
C5'	0.10 (3)	0.11 (5)	0.09 (3)	0.03 (4)	0.04 (2)	0.05 (4)
C6'	0.12 (3)	0.08 (4)	0.08 (4)	0.01 (3)	0.01 (2)	0.03 (2)
C7	0.033 (2)	0.040 (3)	0.042 (3)	0.007 (2)	0.002 (2)	0.008 (2)
C8	0.031 (3)	0.071 (4)	0.055 (3)	0.010 (2)	0.002 (2)	0.009 (3)
S2	0.072 (2)	0.0661 (18)	0.0522 (13)	0.0244 (15)	0.0142 (15)	0.0144 (11)
C9	0.046 (3)	0.042 (3)	0.047 (3)	0.011 (2)	−0.006 (2)	0.000 (2)
C10	0.059 (12)	0.072 (5)	0.075 (12)	0.010 (7)	−0.025 (7)	0.015 (7)
C11	0.099 (18)	0.083 (13)	0.08 (2)	0.012 (11)	−0.033 (15)	0.027 (17)
C12	0.12 (2)	0.076 (18)	0.049 (13)	0.016 (15)	−0.006 (17)	0.017 (10)
S2'	0.059 (12)	0.072 (5)	0.075 (12)	0.010 (7)	−0.025 (7)	0.015 (7)
C9'	0.046 (3)	0.042 (3)	0.047 (3)	0.011 (2)	−0.006 (2)	0.000 (2)
C10'	0.072 (2)	0.0661 (18)	0.0522 (13)	0.0244 (15)	0.0142 (15)	0.0144 (11)
C11'	0.10 (6)	0.07 (6)	0.06 (7)	0.01 (4)	0.00 (5)	0.02 (4)
C12'	0.10 (7)	0.08 (4)	0.06 (6)	0.00 (4)	−0.03 (5)	0.02 (5)
C13	0.055 (3)	0.048 (3)	0.050 (3)	0.009 (3)	0.005 (2)	0.011 (2)
C14	0.058 (3)	0.043 (3)	0.063 (4)	0.009 (3)	0.000 (3)	0.012 (3)
C15	0.061 (4)	0.046 (3)	0.073 (4)	0.015 (3)	0.006 (3)	0.010 (3)
C16	0.065 (4)	0.063 (4)	0.066 (4)	0.022 (3)	0.015 (3)	0.027 (3)

Geometric parameters (Å, º)

Sn1—C14	2.093 (5)	C6'—H6'	0.9300
Sn1—C13	2.098 (5)	C7—C8	1.506 (7)
Sn1—O3	2.151 (3)	C8—C9	1.490 (7)
Sn1—Cl1	2.3766 (13)	C8—H8A	0.9700
Sn1—O1	2.479 (3)	C8—H8B	0.9700
Sn2—C15	2.091 (5)	S2—C9	1.690 (6)
Sn2—C16	2.109 (5)	S2—C12	1.71 (6)
Sn2—O2	2.155 (3)	C9—C10	1.36 (3)
Sn2—Cl2	2.3670 (14)	C10—C11	1.38 (5)
Sn2—O4^i	2.463 (3)	C10—H10	0.9300
O1—C1	1.241 (5)	C11—C12	1.37 (8)
O2—C1	1.280 (6)	C11—H11	0.9300
O3—C7	1.276 (5)	C12—H12	0.9300
O4—C7	1.236 (6)	S2'—C12'	1.70 (16)
O4—Sn2^ii	2.463 (3)	C10'—C11'	1.4 (2)
C1—C2	1.497 (7)	C10'—H10'	0.9300
C2—C3	1.500 (7)	C11'—C12'	1.3 (3)
C2—H2A	0.9700	C11'—H11'	0.9200
C2—H2B	0.9700	C12'—H12'	0.9500
S1—C3	1.678 (7)	C13—H13A	0.9600
S1—C6	1.7 (2)	C13—H13B	0.9600
C3—C4	1.36 (3)	C13—H13C	0.9600
C4—C5	1.37 (12)	C14—H14A	0.9600
C4—H4	0.9300	C14—H14B	0.9600
C5—C6	1.4 (2)	C14—H14C	0.9600
C5—H5	0.9300	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
S1'—C6'	1.69 (13)	C15—H15C	0.9600
C4'—C5'	1.36 (19)	C16—H16A	0.9600
C4'—H4'	0.9300	C16—H16B	0.9600
C5'—C6'	1.3 (2)	C16—H16C	0.9600
C5'—H5'	0.9100
C14—Sn1—C13	140.1 (2)	S1'—C6'—H6'	126.9
C14—Sn1—O3	98.89 (18)	O4—C7—O3	120.8 (4)
C13—Sn1—O3	97.05 (18)	O4—C7—C8	122.5 (4)
C14—Sn1—Cl1	108.22 (17)	O3—C7—C8	116.6 (4)
C13—Sn1—Cl1	108.83 (15)	C9—C8—C7	115.2 (4)
O3—Sn1—Cl1	87.44 (9)	C9—C8—H8A	108.5
C14—Sn1—O1	84.14 (18)	C7—C8—H8A	108.5
C13—Sn1—O1	86.87 (17)	C9—C8—H8B	108.5
O3—Sn1—O1	169.29 (12)	C7—C8—H8B	108.5
Cl1—Sn1—O1	81.85 (9)	H8A—C8—H8B	107.5
C15—Sn2—C16	139.9 (3)	C9—S2—C12	92 (2)
C15—Sn2—O2	98.55 (19)	C10—C9—C8	124 (2)
C16—Sn2—O2	99.14 (19)	C10—C9—S2	111 (2)
C15—Sn2—Cl2	107.45 (17)	C8—C9—S2	124.6 (4)
C16—Sn2—Cl2	108.80 (19)	C9—C10—C11	113 (4)
O2—Sn2—Cl2	88.31 (9)	C9—C10—H10	123.4
C15—Sn2—O4^i	83.98 (19)	C11—C10—H10	123.4
C16—Sn2—O4^i	84.37 (19)	C12—C11—C10	113 (4)
O2—Sn2—O4^i	170.58 (12)	C12—C11—H11	123.6
Cl2—Sn2—O4^i	82.28 (9)	C10—C11—H11	123.6
C1—O1—Sn1	142.4 (3)	C11—C12—S2	110 (4)
C1—O2—Sn2	108.5 (3)	C11—C12—H12	124.8
C7—O3—Sn1	109.3 (3)	S2—C12—H12	124.8
C7—O4—Sn2^ii	143.5 (3)	C11'—C10'—H10'	122.6
O1—C1—O2	120.4 (4)	C12'—C11'—C10'	115 (10)
O1—C1—C2	122.3 (4)	C11'—C12'—S2'	105 (10)
O2—C1—C2	117.3 (4)	Sn1—C13—H13A	109.5
C1—C2—C3	111.6 (4)	Sn1—C13—H13B	109.5
C1—C2—H2A	109.3	H13A—C13—H13B	109.5
C3—C2—H2A	109.3	Sn1—C13—H13C	109.5
C1—C2—H2B	109.3	H13A—C13—H13C	109.5
C3—C2—H2B	109.3	H13B—C13—H13C	109.5
H2A—C2—H2B	108.0	Sn1—C14—H14A	109.5
C3—S1—C6	93 (6)	Sn1—C14—H14B	109.5
C4—C3—C2	130.6 (19)	H14A—C14—H14B	109.5
C4—C3—S1	110.9 (19)	Sn1—C14—H14C	109.5
C2—C3—S1	118.4 (5)	H14A—C14—H14C	109.5
C3—C4—C5	114 (7)	H14B—C14—H14C	109.5
C3—C4—H4	123.1	Sn2—C15—H15A	109.5
C5—C4—H4	123.1	Sn2—C15—H15B	109.5
C6—C5—C4	113 (10)	H15A—C15—H15B	109.5
C6—C5—H5	123.5	Sn2—C15—H15C	109.5
C4—C5—H5	123.5	H15A—C15—H15C	109.5
C5—C6—S1	110 (10)	H15B—C15—H15C	109.5
S1—C6—H6	127.0	Sn2—C16—H16A	109.5
C5'—C4'—H4'	121.9	Sn2—C16—H16B	109.5
C6'—C5'—C4'	116 (10)	H16A—C16—H16B	109.5
C6'—C5'—H5'	122.2	Sn2—C16—H16C	109.5
C4'—C5'—H5'	124.00	H16A—C16—H16C	109.5
C5'—C6'—S1'	106 (10)	H16B—C16—H16C	109.5
C5'—C6'—H6'	125.8

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