Tetra­kis(4-methyl-2-thien­yl)tin(IV)

Yap, Q.L.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536808032790

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page m1410

doi:10.1107/S1600536808032790

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Tetrakis(4-methyl-2-thienyl)tin(IV)

Quai Ling Yap,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 10 September 2008; accepted 10 October 2008; online 15 October 2008)

The molecule of the title compound, [Sn(C₅H₅S)₄], lies on a special position of $[\overline{4}]$ 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, $[I \overline 4]$
a = 11.6286 (9) Å
c = 7.5918 (6) Å
V = 1026.6 (1) Å³
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[F² > 2σ(F²)] = 0.012
wR(F²) = 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032790/ci2670sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808032790/ci2670Isup2.hkl

checkCIF report

Related literature top

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

Experimental top

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

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

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.

Tetrakis(4-methyl-2-thienyl)tin(IV) top

Crystal data top

[Sn(C₅H₅S)₄]	D_x = 1.641 Mg m⁻³
M_r = 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 top

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

Refinement top

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(F_o²) + (0.0145P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
1151 reflections	Δρ_max = 0.45 e Å⁻³
58 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 513 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.005 (14)

Crystal data top

[Sn(C₅H₅S)₄]	Z = 2
M_r = 507.29	Mo Kα radiation
Tetragonal, I4	µ = 1.65 mm⁻¹
a = 11.6286 (9) Å	T = 100 K
c = 7.5918 (6) Å	0.30 × 0.25 × 0.10 mm
V = 1026.6 (1) Å³

Data collection top

Bruker SMART APEX diffractometer	1151 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1149 reflections with I > 2σ(I)
T_min = 0.637, T_max = 0.852	R_int = 0.014
2948 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.012	H-atom parameters constrained
wR(F²) = 0.028	Δρ_max = 0.45 e Å⁻³
S = 1.01	Δρ_min = −0.21 e Å⁻³
1151 reflections	Absolute structure: Flack (1983), 513 Friedel pairs
58 parameters	Absolute structure parameter: 0.005 (14)
0 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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.

Experimental details

Crystal data
Chemical formula	[Sn(C₅H₅S)₄]
M_r	507.29
Crystal system, space group	Tetragonal, I4
Temperature (K)	100
a, c (Å)	11.6286 (9), 7.5918 (6)
V (Å³)	1026.6 (1)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.65
Crystal size (mm)	0.30 × 0.25 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.637, 0.852
No. of measured, independent and observed [I > 2σ(I)] reflections	2948, 1151, 1149
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.012, 0.028, 1.01
No. of reflections	1151
No. of parameters	58
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.21
Absolute structure	Flack (1983), 513 Friedel pairs
Absolute structure parameter	0.005 (14)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Acknowledgements

The authors thank the University of Malaya for funding this study (grant No. FR155/2007A) and also for the purchase of the diffractometer.

References

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