Tetra­kis(4-methyl-2-thien­yl)tin(IV)

Abstract

The mol­ecule of the title compound, [Sn(C₅H₅S)₄], lies on a special position of site symmetry. The Sn^IV atom shows a slightly distorted tetra­hedral coordination.

Related literature

For the structure of tetra­kis(2-thien­yl)tin, see: Karipides et al. (1977 ▶). For the synthesis, see: Kumar Das et al. (1987 ▶).

Experimental

Crystal data

• [Sn(C₅H₅S)₄]

• M _r = 507.29

• Tetragonal,

• a = 11.6286 (9) Å

• c = 7.5918 (6) Å

• V = 1026.6 (1) ų

• Z = 2

• Mo Kα radiation

• μ = 1.65 mm⁻¹

• T = 100 (2) K

• 0.30 × 0.25 × 0.10 mm

Data collection

• Bruker SMART APEX diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.637, T _max = 0.852

• 2948 measured reflections

• 1151 independent reflections

• 1149 reflections with I > 2σ(I)

• R _int = 0.014

Refinement

• R[F ² > 2σ(F ²)] = 0.012

• wR(F ²) = 0.028

• S = 1.01

• 1151 reflections

• 58 parameters

• H-atom parameters constrained

• Δρ_max = 0.45 e Å⁻³

• Δρ_min = −0.21 e Å⁻³

• Absolute structure: Flack (1983 ▶), 513 Friedel pairs

• Flack parameter: 0.005 (14)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Supplementary Material

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

supplementary crystallographic information

Experimental

The title compound was synthesized as reported previously (Kumar Das et al., 1987). Single crystals were obtained upon recrystallization from chloroform.

Refinement

H-atoms were placed in calculated positions (C-H = 0.95-0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U_eq(C).

Figures

Fig. 1.

Displacement ellipsoid plot (Barbour, 2001) of [Sn(C5H5S)4] at the 70% probability level. H atoms are drawn as spheres of arbitrary radii.

Crystal data

[Sn(C5H5S)4]	Dx = 1.641 Mg m−3
Mr = 507.29	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4	Cell parameters from 2958 reflections
Hall symbol: I -4	θ = 2.5–28.3°
a = 11.6286 (9) Å	µ = 1.65 mm−1
c = 7.5918 (6) Å	T = 100 K
V = 1026.6 (1) Å3	Prism, colourless
Z = 2	0.30 × 0.25 × 0.10 mm
F(000) = 508

Data collection

Bruker SMART APEX diffractometer	1151 independent reflections
Radiation source: fine-focus sealed tube	1149 reflections with I > 2σ(I)
graphite	Rint = 0.014
ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→14
Tmin = 0.637, Tmax = 0.852	k = −15→13
2948 measured reflections	l = −9→8

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.012	H-atom parameters constrained
wR(F2) = 0.028	w = 1/[σ2(Fo2) + (0.0145P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
1151 reflections	Δρmax = 0.45 e Å−3
58 parameters	Δρmin = −0.21 e Å−3
0 restraints	Absolute structure: Flack (1983), 513 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.005 (14)

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

	x	y	z	Uiso*/Ueq
Sn1	0.5000	0.5000	0.5000	0.01202 (5)
S1	0.36597 (3)	0.74692 (3)	0.61422 (5)	0.02012 (9)
C1	0.46144 (12)	0.63979 (12)	0.6694 (2)	0.0140 (3)
C2	0.50206 (12)	0.65832 (13)	0.8364 (2)	0.0134 (3)
H2	0.5562	0.6088	0.8914	0.016*
C3	0.45677 (14)	0.75770 (14)	0.9212 (2)	0.0154 (3)
C4	0.38176 (14)	0.81447 (13)	0.8139 (2)	0.0192 (3)
H4	0.3429	0.8832	0.8459	0.023*
C5	0.48542 (16)	0.79485 (16)	1.1056 (2)	0.0206 (4)
H5A	0.4919	0.8788	1.1097	0.031*
H5B	0.5586	0.7602	1.1414	0.031*
H5C	0.4244	0.7697	1.1859	0.031*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Sn1	0.01360 (6)	0.01360 (6)	0.00885 (9)	0.000	0.000	0.000
S1	0.0221 (2)	0.0223 (2)	0.0160 (2)	0.00775 (16)	−0.00468 (16)	0.00016 (16)
C1	0.0138 (7)	0.0138 (7)	0.0144 (8)	0.0010 (5)	0.0011 (6)	0.0019 (6)
C2	0.0133 (6)	0.0140 (7)	0.0129 (8)	0.0000 (5)	0.0011 (6)	0.0020 (6)
C3	0.0165 (8)	0.0151 (8)	0.0146 (8)	−0.0017 (6)	0.0023 (6)	0.0011 (6)
C4	0.0220 (8)	0.0172 (8)	0.0185 (9)	0.0055 (6)	0.0014 (7)	−0.0008 (7)
C5	0.0267 (9)	0.0213 (9)	0.0139 (9)	−0.0005 (7)	0.0007 (7)	−0.0030 (7)

Geometric parameters (Å, °)

Sn1—C1i	2.1209 (15)	C2—H2	0.95
Sn1—C1	2.1209 (15)	C3—C4	1.364 (2)
Sn1—C1ii	2.1209 (15)	C3—C5	1.502 (2)
Sn1—C1iii	2.1209 (15)	C4—H4	0.95
S1—C4	1.7173 (16)	C5—H5A	0.98
S1—C1	1.7206 (15)	C5—H5B	0.98
C1—C2	1.370 (2)	C5—H5C	0.98
C2—C3	1.424 (2)
C1i—Sn1—C1	111.58 (4)	C4—C3—C2	111.07 (15)
C1i—Sn1—C1ii	105.32 (8)	C4—C3—C5	124.00 (16)
C1—Sn1—C1ii	111.58 (4)	C2—C3—C5	124.92 (16)
C1i—Sn1—C1iii	111.58 (4)	C3—C4—S1	111.98 (12)
C1—Sn1—C1iii	105.32 (8)	C3—C4—H4	124.0
C1ii—Sn1—C1iii	111.58 (4)	S1—C4—H4	124.0
C4—S1—C1	92.70 (8)	C3—C5—H5A	109.5
C2—C1—S1	109.51 (12)	C3—C5—H5B	109.5
C2—C1—Sn1	127.51 (11)	H5A—C5—H5B	109.5
S1—C1—Sn1	122.93 (8)	C3—C5—H5C	109.5
C1—C2—C3	114.74 (14)	H5A—C5—H5C	109.5
C1—C2—H2	122.6	H5B—C5—H5C	109.5
C3—C2—H2	122.6
C4—S1—C1—C2	0.03 (12)	S1—C1—C2—C3	0.28 (17)
C4—S1—C1—Sn1	177.81 (9)	Sn1—C1—C2—C3	−177.37 (11)
C1i—Sn1—C1—C2	149.39 (12)	C1—C2—C3—C4	−0.54 (19)
C1ii—Sn1—C1—C2	−93.09 (10)	C1—C2—C3—C5	178.39 (14)
C1iii—Sn1—C1—C2	28.15 (11)	C2—C3—C4—S1	0.54 (17)
C1i—Sn1—C1—S1	−27.98 (10)	C5—C3—C4—S1	−178.40 (12)
C1ii—Sn1—C1—S1	89.54 (12)	C1—S1—C4—C3	−0.34 (13)
C1iii—Sn1—C1—S1	−149.22 (11)

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