catena-Poly[[trimethyl­tin(IV)]-μ-phenyl­seleninato-κ2O:O′]

Guo, M.; Ru, J.; Zhang, R.

doi:10.1107/S1600536810054243

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m152

doi:10.1107/S1600536810054243

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catena-Poly[[trimethyltin(IV)]-μ-phenylseleninato-κ²O:O′]

Mengjie Guo,^a Jing Ru ^a and Rufen Zhang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: macl@lcu.edu.cn.

(Received 16 December 2010; accepted 25 December 2010; online 12 January 2011)

In the title polymeric coordination compound, [Sn(CH₃)₃(C₆H₅O₂Se)]_n, the Sn^IV atom has a distorted trigonal–bipyramidal geometry, with two O atoms of two symmetry-related bridging phenylseleninate anions in axial positions and three methyl groups in equatorial positions. In the crystal, the complex exhibits a chain structure parallel to the b axis.

Related literature

For the applications and biological activity of organotin compounds, see: Dubey & Roy (2003 ). For a related structure, see: Chandrasekhar et al. (1992 ).

Experimental

Crystal data

[Sn(CH₃)₃(C₆H₅O₂Se)]
M_r = 351.85
Orthorhombic, P b c a
a = 13.0352 (12) Å
b = 10.0882 (13) Å
c = 18.709 (2) Å
V = 2460.3 (5) Å³
Z = 8
Mo Kα radiation
μ = 5.01 mm⁻¹
T = 298 K
0.42 × 0.33 × 0.29 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.228, T_max = 0.325
9382 measured reflections
2164 independent reflections
1681 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.069
S = 1.06
2164 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.45 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054243/rz2544sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054243/rz2544Isup2.hkl

checkCIF report

Comment top

In recent years, organotin compounds have been attracting more and more attention due to their wide range of industrial applications and biological activities (Dubey & Roy, 2003). As a part of our ongoing investigations in this field, we have synthesized the title compound and present its crystal structure here.

The asymmetric unit of the title compound is shown in Fig. 1. An extended one-dimensional zigzag chain structure running parallel to the b axis is formed by the bridging role of the phenylseleninato anions (Fig. 2). The Sn—O bond distances in the compound (Sn1—O1 = 2.243 (3) Å; Sn1—O2ⁱ = 2.258 (3) Å; symmetry code: (i): -x, y-1/2, -z+1/2) are comparable to those found in a related organotin compound (Chandrasekhar et al., 1992). The Sn atom is five-coordinate in a slightly distorted trigonal-bipyramidal coordination geometry, provided by the methyl groups in the equatorial positions and two O atoms of symmetry related phenylseleninato groups in the axial positions.

Related literature top

For the applications and biological activity of organotin compounds, see: Dubey et al. (2003). For a related structure, see: Chandrasekhar et al. (1992).

Experimental top

The reaction was carried out under a nitrogen atmosphere. Benzeneseleninic acid (1 mmol) and sodium ethoxide (1 mmol) were added to a stirred solution of methanol (30 ml) 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 at room temperature. The resulting clear solution was evaporated under vacuum. The product was crystallized from a solution of ether to yield colourless block crystals of the title compound (yield 65%). Anal. Calcd (%) for C₉H₁₄O₂Sn₁Se₁ (Mr = 351.85): C, 30.72; H, 4.01. Found (%): C, 30.93; H, 3.85.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The coordination geometry of the tin metal centre in the title compound, showing 50% probability displacement ellipsoids. H atoms are omitted for clarity. [Symmetry code: (A) -x, -1/2+y, 1/2-z]
	Fig. 2. View of the one-dimensional zigzag chain structure running parallel to the b axis in the title compound.

catena-Poly[[trimethyltin(IV)]-µ-phenylseleninato- κ²O:O'] top

Crystal data top

[Sn(CH₃)₃(C₆H₅O₂Se)]	F(000) = 1344
M_r = 351.85	D_x = 1.900 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3552 reflections
a = 13.0352 (12) Å	θ = 2.7–26.4°
b = 10.0882 (13) Å	µ = 5.01 mm⁻¹
c = 18.709 (2) Å	T = 298 K
V = 2460.3 (5) Å³	Block, colourless
Z = 8	0.42 × 0.33 × 0.29 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2164 independent reflections
Radiation source: fine-focus sealed tube	1681 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
phi and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→15
T_min = 0.228, T_max = 0.325	k = −12→11
9382 measured reflections	l = −22→22

Refinement top

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0321P)² + 0.1006P] where P = (F_o² + 2F_c²)/3
2164 reflections	(Δ/σ)_max = 0.001
118 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Sn(CH₃)₃(C₆H₅O₂Se)]	V = 2460.3 (5) Å³
M_r = 351.85	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.0352 (12) Å	µ = 5.01 mm⁻¹
b = 10.0882 (13) Å	T = 298 K
c = 18.709 (2) Å	0.42 × 0.33 × 0.29 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2164 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1681 reflections with I > 2σ(I)
T_min = 0.228, T_max = 0.325	R_int = 0.048
9382 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 1.06	Δρ_max = 0.39 e Å⁻³
2164 reflections	Δρ_min = −0.45 e Å⁻³
118 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	−0.06314 (2)	0.18100 (3)	0.263140 (17)	0.03827 (12)
Se1	−0.03615 (4)	0.46755 (5)	0.37539 (2)	0.03951 (15)
O1	−0.1012 (2)	0.3364 (3)	0.34469 (17)	0.0485 (8)
O2	0.0495 (3)	0.5076 (3)	0.31255 (19)	0.0568 (9)
C1	0.0573 (4)	0.3775 (5)	0.4398 (2)	0.0401 (11)
C2	0.0239 (5)	0.2699 (6)	0.4774 (3)	0.0612 (15)
H2	−0.0433	0.2404	0.4724	0.073*
C3	0.0902 (6)	0.2054 (6)	0.5228 (3)	0.078 (2)
H3	0.0680	0.1315	0.5482	0.094*
C4	0.1899 (6)	0.2502 (7)	0.5309 (3)	0.075 (2)
H4	0.2345	0.2070	0.5619	0.090*
C5	0.2223 (5)	0.3571 (7)	0.4933 (3)	0.0740 (18)
H5	0.2893	0.3873	0.4986	0.089*
C6	0.1567 (4)	0.4208 (6)	0.4477 (3)	0.0552 (14)
H6	0.1795	0.4937	0.4218	0.066*
C7	−0.1262 (5)	0.2998 (5)	0.1810 (3)	0.0647 (16)
H7A	−0.1806	0.3532	0.2002	0.097*
H7B	−0.1528	0.2438	0.1439	0.097*
H7C	−0.0738	0.3562	0.1616	0.097*
C8	0.0976 (4)	0.1852 (6)	0.2800 (3)	0.0678 (17)
H8A	0.1295	0.1162	0.2525	0.102*
H8B	0.1119	0.1716	0.3298	0.102*
H8C	0.1243	0.2696	0.2654	0.102*
C9	−0.1570 (4)	0.0505 (5)	0.3233 (3)	0.0614 (15)
H9A	−0.1983	0.1008	0.3560	0.092*
H9B	−0.1144	−0.0100	0.3496	0.092*
H9C	−0.2007	0.0016	0.2916	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03808 (19)	0.0389 (2)	0.0379 (2)	−0.00017 (15)	−0.00099 (14)	−0.00287 (15)
Se1	0.0485 (3)	0.0345 (3)	0.0356 (3)	0.0079 (2)	−0.0021 (2)	−0.0026 (2)
O1	0.0439 (18)	0.050 (2)	0.052 (2)	0.0053 (16)	−0.0044 (16)	−0.0186 (16)
O2	0.068 (2)	0.048 (2)	0.054 (2)	0.0072 (17)	0.0061 (19)	0.0209 (17)
C1	0.051 (3)	0.040 (3)	0.029 (2)	0.006 (2)	0.001 (2)	0.000 (2)
C2	0.062 (4)	0.064 (4)	0.058 (4)	0.000 (3)	−0.006 (3)	0.013 (3)
C3	0.115 (6)	0.065 (4)	0.056 (4)	0.016 (4)	−0.009 (4)	0.025 (3)
C4	0.087 (5)	0.086 (5)	0.052 (4)	0.041 (4)	−0.016 (3)	−0.003 (4)
C5	0.054 (4)	0.109 (6)	0.059 (4)	0.012 (3)	−0.014 (3)	−0.004 (4)
C6	0.056 (3)	0.068 (4)	0.042 (3)	−0.002 (3)	−0.003 (3)	0.002 (3)
C7	0.085 (4)	0.061 (4)	0.048 (3)	0.004 (3)	−0.003 (3)	0.009 (3)
C8	0.038 (3)	0.068 (4)	0.097 (5)	0.012 (3)	−0.006 (3)	−0.028 (3)
C9	0.076 (4)	0.056 (4)	0.052 (3)	−0.006 (3)	0.010 (3)	0.004 (3)

Geometric parameters (Å, º) top

Sn1—C7	2.115 (5)	C4—C5	1.355 (9)
Sn1—C8	2.119 (5)	C4—H4	0.9300
Sn1—C9	2.121 (5)	C5—C6	1.368 (7)
Sn1—O1	2.243 (3)	C5—H5	0.9300
Sn1—O2ⁱ	2.258 (3)	C6—H6	0.9300
Se1—O2	1.671 (3)	C7—H7A	0.9600
Se1—O1	1.673 (3)	C7—H7B	0.9600
Se1—C1	1.940 (5)	C7—H7C	0.9600
O2—Sn1ⁱⁱ	2.258 (3)	C8—H8A	0.9600
C1—C2	1.365 (7)	C8—H8B	0.9600
C1—C6	1.375 (7)	C8—H8C	0.9600
C2—C3	1.376 (8)	C9—H9A	0.9600
C2—H2	0.9300	C9—H9B	0.9600
C3—C4	1.384 (9)	C9—H9C	0.9600
C3—H3	0.9300

C7—Sn1—C8	118.8 (3)	C3—C4—H4	120.1
C7—Sn1—C9	120.9 (2)	C4—C5—C6	120.2 (6)
C8—Sn1—C9	120.2 (2)	C4—C5—H5	119.9
C7—Sn1—O1	90.72 (18)	C6—C5—H5	119.9
C8—Sn1—O1	95.92 (17)	C5—C6—C1	120.4 (6)
C9—Sn1—O1	86.86 (17)	C5—C6—H6	119.8
C7—Sn1—O2ⁱ	90.78 (18)	C1—C6—H6	119.8
C8—Sn1—O2ⁱ	91.79 (18)	Sn1—C7—H7A	109.5
C9—Sn1—O2ⁱ	84.11 (17)	Sn1—C7—H7B	109.5
O1—Sn1—O2ⁱ	170.25 (12)	H7A—C7—H7B	109.5
O2—Se1—O1	106.75 (18)	Sn1—C7—H7C	109.5
O2—Se1—C1	97.51 (18)	H7A—C7—H7C	109.5
O1—Se1—C1	99.28 (18)	H7B—C7—H7C	109.5
Se1—O1—Sn1	132.40 (18)	Sn1—C8—H8A	109.5
Se1—O2—Sn1ⁱⁱ	132.94 (18)	Sn1—C8—H8B	109.5
C2—C1—C6	119.9 (5)	H8A—C8—H8B	109.5
C2—C1—Se1	119.5 (4)	Sn1—C8—H8C	109.5
C6—C1—Se1	120.7 (4)	H8A—C8—H8C	109.5
C1—C2—C3	119.6 (6)	H8B—C8—H8C	109.5
C1—C2—H2	120.2	Sn1—C9—H9A	109.5
C3—C2—H2	120.2	Sn1—C9—H9B	109.5
C2—C3—C4	120.2 (6)	H9A—C9—H9B	109.5
C2—C3—H3	119.9	Sn1—C9—H9C	109.5
C4—C3—H3	119.9	H9A—C9—H9C	109.5
C5—C4—C3	119.7 (6)	H9B—C9—H9C	109.5
C5—C4—H4	120.1

O2—Se1—O1—Sn1	22.8 (3)	O1—Se1—C1—C6	143.5 (4)
C1—Se1—O1—Sn1	−78.0 (3)	C6—C1—C2—C3	−0.2 (8)
C7—Sn1—O1—Se1	−89.2 (3)	Se1—C1—C2—C3	179.6 (4)
C8—Sn1—O1—Se1	29.8 (3)	C1—C2—C3—C4	0.7 (9)
C9—Sn1—O1—Se1	149.9 (3)	C2—C3—C4—C5	−0.6 (10)
O1—Se1—O2—Sn1ⁱⁱ	110.1 (3)	C3—C4—C5—C6	0.1 (9)
C1—Se1—O2—Sn1ⁱⁱ	−147.8 (3)	C4—C5—C6—C1	0.4 (8)
O2—Se1—C1—C2	−144.7 (4)	C2—C1—C6—C5	−0.4 (8)
O1—Se1—C1—C2	−36.2 (4)	Se1—C1—C6—C5	179.8 (4)
O2—Se1—C1—C6	35.1 (4)

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

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₃(C₆H₅O₂Se)]
M_r	351.85
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	13.0352 (12), 10.0882 (13), 18.709 (2)
V (Å³)	2460.3 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.01
Crystal size (mm)	0.42 × 0.33 × 0.29

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.228, 0.325
No. of measured, independent and observed [I > 2σ(I)] reflections	9382, 2164, 1681
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.069, 1.06
No. of reflections	2164
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.45

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We thank the National Natural Science Foundation of China (20971096) for financial support.

References

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