Bis(triphenyl-stann-yl) thio-phene-2,5-dicarboxyl-ate.

Mol-ecules of the title compound, [Sn(2)(C(6)H(5))(6)(C(6)H(2)O(4)S)], lie on inversion centres with the central thio-phene ring disordered equally over two orientations. The carboxyl-ate groups are approximately coplanar with the thio-phene ring [dihedral angle = 4.0 (1)°] and the Sn-O bond distance of 2.058 (4) Å is comparable to that in related organotin carboxyl-ates.

Related literature

For background literature concerning organotin chemisty, see: Prabusankar & Murugavel (2004 ▶); Holmes (1989 ▶). For related structures, see: Pellei et al. (2008 ▶).

Experimental

Crystal data

[Sn2(C6H5)6(C6H2O4S)]

M = 870.12

Monoclinic,

a = 10.1302 (10) Å

b = 18.699 (2) Å

c = 10.3584 (11) Å

β = 108.213 (2)°

V = 1863.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.44 mm−1

T = 298 K

0.21 × 0.11 × 0.06 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.752, T max = 0.919

9058 measured reflections

3281 independent reflections

2342 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.110

S = 1.02

3281 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.77 e Å−3

Δρmin = −0.63 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020273/bi2371sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020273/bi2371Isup2.hkl

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

[Sn2(C6H5)6(C6H2O4S)]	F(000) = 864
Mr = 870.12	Dx = 1.550 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3030 reflections
a = 10.1302 (10) Å	θ = 2.4–25.2°
b = 18.699 (2) Å	µ = 1.44 mm−1
c = 10.3584 (11) Å	T = 298 K
β = 108.213 (2)°	Needle, colorless
V = 1863.8 (3) Å3	0.21 × 0.11 × 0.06 mm
Z = 2

Bruker SMART APEX CCD diffractometer	3281 independent reflections
Radiation source: fine-focus sealed tube	2342 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→6
Tmin = 0.752, Tmax = 0.919	k = −22→20
9058 measured reflections	l = −11→12

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0214P)2 + 10.153P] where P = (Fo2 + 2Fc2)/3
3281 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.77 e Å−3
0 restraints	Δρmin = −0.63 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	Occ. (<1)
Sn1	0.66000 (5)	0.07183 (3)	0.78299 (5)	0.04647 (17)
S1	0.9299 (4)	0.0123 (2)	0.4533 (4)	0.0479 (9)	0.50
O1	0.7511 (5)	0.0595 (3)	0.6325 (5)	0.0547 (13)
O2	0.9220 (7)	0.0178 (4)	0.7991 (8)	0.110 (3)
C1	0.8710 (9)	0.0308 (4)	0.6808 (10)	0.061 (2)
C2	0.9687 (17)	−0.0005 (9)	0.6205 (18)	0.053 (4)	0.50
C3	1.0869 (15)	−0.0332 (8)	0.6787 (16)	0.056 (4)	0.50
H3	1.1227	−0.0425	0.7713	0.067*	0.50
C4	1.1513 (16)	−0.0519 (8)	0.5836 (15)	0.057 (4)	0.50
H4	1.2341	−0.0775	0.6067	0.068*	0.50
C5	1.0826 (16)	−0.0293 (8)	0.4493 (19)	0.048 (4)	0.50
C6	0.4678 (8)	0.1119 (5)	0.6546 (9)	0.074 (3)
C7	0.4344 (10)	0.1137 (5)	0.5168 (10)	0.089 (3)
H7	0.4985	0.0981	0.4752	0.107*
C8	0.3042 (12)	0.1388 (6)	0.4372 (12)	0.107 (4)
H8	0.2812	0.1401	0.3430	0.129*
C9	0.2123 (12)	0.1611 (6)	0.4998 (14)	0.113 (4)
H9	0.1275	0.1798	0.4471	0.136*
C10	0.2392 (11)	0.1573 (7)	0.6336 (14)	0.123 (5)
H10	0.1723	0.1709	0.6731	0.147*
C11	0.3691 (9)	0.1327 (6)	0.7143 (12)	0.107 (4)
H11	0.3894	0.1304	0.8082	0.128*
C12	0.7680 (8)	0.1508 (4)	0.9236 (7)	0.0532 (19)
C13	0.7151 (11)	0.2181 (5)	0.9169 (11)	0.100 (3)
H13	0.6362	0.2302	0.8457	0.120*
C14	0.7770 (12)	0.2686 (6)	1.0144 (12)	0.109 (4)
H14	0.7375	0.3138	1.0089	0.131*
C15	0.8898 (11)	0.2541 (6)	1.1140 (11)	0.091 (3)
H15	0.9309	0.2884	1.1793	0.109*
C16	0.9439 (12)	0.1896 (7)	1.1196 (12)	0.121 (4)
H16	1.0244	0.1788	1.1899	0.145*
C17	0.8848 (11)	0.1373 (5)	1.0241 (10)	0.102 (4)
H17	0.9267	0.0927	1.0301	0.123*
C18	0.6293 (11)	−0.0309 (5)	0.8534 (9)	0.072 (3)
C19	0.4946 (13)	−0.0581 (6)	0.8128 (10)	0.101 (3)
H19	0.4219	−0.0301	0.7600	0.121*
C20	0.4668 (15)	−0.1284 (7)	0.8514 (12)	0.115 (4)
H20	0.3770	−0.1465	0.8293	0.138*
C21	0.5790 (17)	−0.1672 (7)	0.9219 (13)	0.127 (5)
H21	0.5634	−0.2144	0.9418	0.152*
C22	0.7120 (16)	−0.1434 (7)	0.9663 (12)	0.130 (5)
H22	0.7840	−0.1725	1.0172	0.156*
C23	0.7362 (14)	−0.0732 (6)	0.9321 (10)	0.110 (4)
H23	0.8258	−0.0547	0.9629	0.132*

	U11	U22	U33	U12	U13	U23
Sn1	0.0405 (3)	0.0537 (3)	0.0483 (3)	0.0019 (3)	0.0182 (2)	−0.0062 (3)
S1	0.040 (2)	0.052 (2)	0.054 (3)	0.0089 (19)	0.0192 (19)	0.0058 (19)
O1	0.050 (3)	0.062 (3)	0.060 (3)	0.008 (3)	0.028 (3)	0.005 (3)
O2	0.092 (5)	0.082 (5)	0.118 (6)	0.012 (4)	−0.023 (5)	0.006 (4)
C1	0.048 (5)	0.061 (5)	0.080 (6)	−0.002 (4)	0.026 (5)	−0.017 (5)
C2	0.042 (10)	0.055 (10)	0.062 (11)	0.012 (8)	0.018 (9)	0.000 (8)
C3	0.049 (9)	0.065 (10)	0.057 (10)	0.017 (8)	0.020 (8)	0.002 (8)
C4	0.046 (9)	0.064 (10)	0.059 (10)	0.015 (8)	0.015 (8)	−0.002 (8)
C5	0.040 (9)	0.047 (10)	0.064 (12)	0.010 (8)	0.025 (9)	−0.005 (9)
C6	0.053 (5)	0.082 (6)	0.079 (6)	0.014 (5)	0.010 (5)	−0.042 (5)
C7	0.069 (6)	0.092 (7)	0.090 (7)	0.017 (5)	0.003 (6)	−0.041 (6)
C8	0.087 (8)	0.110 (9)	0.099 (8)	0.020 (7)	−0.008 (7)	−0.038 (7)
C9	0.080 (8)	0.111 (9)	0.121 (10)	0.026 (7)	−0.010 (8)	−0.038 (8)
C10	0.074 (7)	0.142 (11)	0.134 (11)	0.040 (7)	0.006 (8)	−0.056 (9)
C11	0.060 (6)	0.134 (9)	0.111 (8)	0.032 (6)	0.007 (6)	−0.055 (7)
C12	0.050 (4)	0.061 (5)	0.055 (5)	−0.002 (4)	0.025 (4)	−0.011 (4)
C13	0.090 (7)	0.081 (7)	0.104 (8)	0.019 (6)	−0.004 (6)	−0.039 (6)
C14	0.098 (8)	0.086 (7)	0.119 (9)	0.012 (7)	−0.001 (8)	−0.043 (7)
C15	0.082 (7)	0.092 (8)	0.092 (8)	−0.016 (6)	0.019 (6)	−0.046 (6)
C16	0.099 (9)	0.110 (9)	0.111 (9)	0.002 (8)	−0.031 (7)	−0.031 (8)
C17	0.089 (7)	0.081 (7)	0.096 (8)	0.015 (6)	−0.030 (6)	−0.024 (6)
C18	0.090 (7)	0.079 (6)	0.053 (5)	−0.033 (6)	0.033 (5)	−0.012 (5)
C19	0.121 (9)	0.104 (8)	0.080 (7)	−0.043 (7)	0.035 (7)	−0.015 (6)
C20	0.130 (11)	0.116 (10)	0.096 (9)	−0.064 (9)	0.033 (8)	−0.014 (7)
C21	0.149 (13)	0.119 (11)	0.102 (10)	−0.045 (10)	0.023 (10)	0.019 (8)
C22	0.151 (13)	0.113 (10)	0.103 (9)	−0.036 (9)	0.006 (9)	0.020 (8)
C23	0.146 (11)	0.092 (8)	0.072 (7)	−0.044 (8)	0.006 (7)	0.019 (6)

Sn1—O1	2.058 (4)	C10—H10	0.930
Sn1—C18	2.112 (9)	C11—H11	0.930
Sn1—C6	2.121 (9)	C12—C17	1.333 (11)
Sn1—C12	2.122 (7)	C12—C13	1.359 (11)
S1—C2	1.669 (18)	C13—C14	1.382 (12)
S1—C5	1.744 (15)	C13—H13	0.930
O1—C1	1.279 (9)	C14—C15	1.307 (13)
O2—C1	1.197 (10)	C14—H14	0.930
C1—C2	1.449 (17)	C15—C16	1.320 (14)
C2—C3	1.31 (2)	C15—H15	0.930
C3—C4	1.385 (19)	C16—C17	1.386 (13)
C3—H3	0.930	C16—H16	0.930
C4—C5	1.41 (2)	C17—H17	0.930
C4—H4	0.930	C18—C23	1.382 (14)
C5—C1i	1.560 (19)	C18—C19	1.392 (13)
C6—C7	1.361 (12)	C19—C20	1.428 (14)
C6—C11	1.386 (12)	C19—H19	0.930
C7—C8	1.400 (13)	C20—C21	1.354 (16)
C7—H7	0.930	C20—H20	0.930
C8—C9	1.356 (15)	C21—C22	1.355 (16)
C8—H8	0.930	C21—H21	0.930
C9—C10	1.328 (15)	C22—C23	1.402 (14)
C9—H9	0.930	C22—H22	0.930
C10—C11	1.399 (13)	C23—H23	0.930
O1—Sn1—C18	108.0 (3)	C6—C11—H11	120.0
O1—Sn1—C6	96.1 (3)	C10—C11—H11	120.0
C18—Sn1—C6	109.4 (4)	C17—C12—C13	117.1 (8)
O1—Sn1—C12	109.9 (2)	C17—C12—Sn1	123.0 (6)
C18—Sn1—C12	119.7 (3)	C13—C12—Sn1	119.9 (6)
C6—Sn1—C12	111.1 (3)	C12—C13—C14	120.9 (9)
C2—S1—C5	92.1 (7)	C12—C13—H13	119.6
C1—O1—Sn1	110.3 (5)	C14—C13—H13	119.6
O2—C1—O1	122.7 (8)	C15—C14—C13	121.4 (10)
O2—C1—C2	103.0 (11)	C15—C14—H14	119.3
O1—C1—C2	134.0 (11)	C13—C14—H14	119.3
C3—C2—C1	129.7 (16)	C14—C15—C16	118.2 (10)
C3—C2—S1	115.5 (12)	C14—C15—H15	120.9
C1—C2—S1	114.7 (12)	C16—C15—H15	120.9
C2—C3—C4	110.8 (15)	C15—C16—C17	122.2 (10)
C2—C3—H3	124.6	C15—C16—H16	118.9
C4—C3—H3	124.6	C17—C16—H16	118.9
C3—C4—C5	115.4 (15)	C12—C17—C16	120.2 (10)
C3—C4—H4	122.3	C12—C17—H17	119.9
C5—C4—H4	122.3	C16—C17—H17	119.9
C4—C5—S1	106.1 (13)	C23—C18—C19	118.9 (9)
C1i—C5—S1	122.5 (12)	C23—C18—Sn1	123.4 (7)
C7—C6—C11	118.9 (9)	C19—C18—Sn1	117.6 (8)
C7—C6—Sn1	123.0 (6)	C18—C19—C20	120.8 (12)
C11—C6—Sn1	117.9 (7)	C18—C19—H19	119.6
C6—C7—C8	120.4 (10)	C20—C19—H19	119.6
C6—C7—H7	119.8	C21—C20—C19	116.0 (12)
C8—C7—H7	119.8	C21—C20—H20	122.0
C9—C8—C7	118.9 (11)	C19—C20—H20	122.0
C9—C8—H8	120.6	C20—C21—C22	125.8 (13)
C7—C8—H8	120.6	C20—C21—H21	117.1
C10—C9—C8	122.3 (11)	C22—C21—H21	117.1
C10—C9—H9	118.8	C21—C22—C23	117.1 (13)
C8—C9—H9	118.8	C21—C22—H22	121.5
C9—C10—C11	119.3 (12)	C23—C22—H22	121.5
C9—C10—H10	120.4	C18—C23—C22	121.2 (12)
C11—C10—H10	120.4	C18—C23—H23	119.4
C6—C11—C10	120.1 (11)	C22—C23—H23	119.4