Dibenzyl­dichloridotin(IV)

Lo, K.M.; Ng, S.W.

doi:10.1107/S160053680901513X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m596

doi:10.1107/S160053680901513X

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Dibenzyldichloridotin(IV)

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 21 April 2009; accepted 23 April 2009; online 30 April 2009)

The title compound, [Sn(C₇H₇)₂Cl₂], exists as a monomeric tetrahedral molecule. The Sn atom lies on a special position of site symmetry 2. Adjacent molecules are linked into a linear chain running along the b axis of the monoclinic unit cell by Sn⋯Cl bridges of 3.7275 (4) Å.

Related literature

For the synthesis of dibenzyltin dichloride by the direct reaction of benzyl chloride and metallic tin, see: Shishido et al. (1961 ). For an overview of crystallographic and theoretical structures of diorganotin dichlorides, see: Buntine et al. (2003 ).

Experimental

Crystal data

[Sn(C₇H₇)₂Cl₂]
M_r = 371.84
Monoclinic, C 2/c
a = 23.7710 (3) Å
b = 4.8019 (1) Å
c = 12.0808 (2) Å
β = 92.560 (1)°
V = 1377.60 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.22 mm⁻¹
T = 123 K
0.35 × 0.30 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.511, T_max = 0.732
6090 measured reflections
1580 independent reflections
1527 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.014
wR(F²) = 0.041
S = 1.03
1580 reflections
78 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901513X/tk2438sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901513X/tk2438Isup2.hkl

checkCIF report

Related literature top

For the synthesis of dibenzyltin dichloride by the direct reaction of benzyl chloride and metallic tin, see: Shishido et al. (1961). For an overview of crystallographic and theoretical structures of diorganotin dichlorides, see: Buntine et al. (2003).

Experimental top

Dibenzyltin dichloride was synthesized from benzyl chloride and metallic tin by a literature method (Shishido et al., 1961). Crystals were obtained by recrystallization from chloroform.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of part of the supramolecular chain in (C₆H₅CH₂)₂SnCl₂ drawn at the 70% probability level. Dashed lines denote the Sn···Cl bridges. Hydrogen atoms are drawn as spheres of arbitrary radius. Unlabelled atoms within the partially labelled molecule are related by the symmetry operation: -x+1, y, -z+1/2.

Dibenzyldichloridotin(IV) top

Crystal data top

[Sn(C₇H₇)₂Cl₂]	F(000) = 728
M_r = 371.84	D_x = 1.793 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5461 reflections
a = 23.7710 (3) Å	θ = 2.5–28.3°
b = 4.8019 (1) Å	µ = 2.22 mm⁻¹
c = 12.0808 (2) Å	T = 123 K
β = 92.560 (1)°	Block, colorless
V = 1377.60 (4) Å³	0.35 × 0.30 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	1580 independent reflections
Radiation source: fine-focus sealed tube	1527 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −30→30
T_min = 0.511, T_max = 0.732	k = −6→6
6090 measured reflections	l = −15→15

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)] = 0.014	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.041	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0238P)² + 1.6061P] where P = (F_o² + 2F_c²)/3
1580 reflections	(Δ/σ)_max = 0.001
78 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

[Sn(C₇H₇)₂Cl₂]	V = 1377.60 (4) Å³
M_r = 371.84	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 23.7710 (3) Å	µ = 2.22 mm⁻¹
b = 4.8019 (1) Å	T = 123 K
c = 12.0808 (2) Å	0.35 × 0.30 × 0.15 mm
β = 92.560 (1)°

Data collection top

Bruker SMART APEX diffractometer	1580 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1527 reflections with I > 2σ(I)
T_min = 0.511, T_max = 0.732	R_int = 0.021
6090 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.014	0 restraints
wR(F²) = 0.041	H-atom parameters constrained
S = 1.03	Δρ_max = 0.27 e Å⁻³
1580 reflections	Δρ_min = −0.60 e Å⁻³
78 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.5000	0.49246 (2)	0.2500	0.01354 (6)
Cl1	0.473226 (16)	0.81293 (8)	0.38720 (3)	0.01976 (9)
C1	0.57846 (6)	0.3263 (3)	0.31462 (14)	0.0206 (3)
H1A	0.5716	0.2146	0.3816	0.025*
H1B	0.5942	0.2008	0.2588	0.025*
C2	0.62055 (7)	0.5502 (3)	0.34383 (14)	0.0175 (3)
C3	0.65796 (6)	0.6448 (3)	0.26657 (13)	0.0197 (3)
H3	0.6563	0.5694	0.1938	0.024*
C4	0.69765 (7)	0.8477 (3)	0.29468 (14)	0.0225 (3)
H4	0.7228	0.9111	0.2411	0.027*
C5	0.70071 (8)	0.9580 (3)	0.40082 (17)	0.0253 (4)
H5	0.7282	1.0952	0.4204	0.030*
C6	0.66358 (7)	0.8673 (4)	0.47815 (14)	0.0260 (3)
H6	0.6654	0.9436	0.5508	0.031*
C7	0.62366 (7)	0.6650 (3)	0.44994 (13)	0.0222 (3)
H7	0.5983	0.6044	0.5035	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01130 (9)	0.01254 (9)	0.01666 (9)	0.000	−0.00051 (6)	0.000
Cl1	0.02142 (18)	0.02114 (18)	0.01692 (16)	−0.00076 (14)	0.00309 (13)	−0.00308 (13)
C1	0.0153 (7)	0.0142 (7)	0.0318 (8)	0.0000 (6)	−0.0049 (6)	0.0023 (6)
C2	0.0129 (7)	0.0138 (6)	0.0254 (8)	0.0020 (6)	−0.0044 (6)	0.0025 (6)
C3	0.0168 (7)	0.0191 (7)	0.0232 (7)	0.0026 (6)	0.0001 (6)	−0.0025 (6)
C4	0.0145 (7)	0.0216 (7)	0.0316 (8)	−0.0003 (6)	0.0022 (6)	0.0026 (6)
C5	0.0195 (8)	0.0193 (7)	0.0361 (10)	−0.0029 (6)	−0.0081 (7)	−0.0010 (7)
C6	0.0271 (8)	0.0281 (8)	0.0222 (8)	0.0000 (7)	−0.0075 (6)	−0.0023 (6)
C7	0.0204 (8)	0.0249 (8)	0.0210 (7)	−0.0011 (6)	−0.0016 (6)	0.0051 (6)

Geometric parameters (Å, º) top

Sn1—Cl1ⁱ	3.7275 (4)	C3—C4	1.388 (2)
Sn1—C1ⁱⁱ	2.143 (2)	C3—H3	0.9500
Sn1—C1	2.143 (2)	C4—C5	1.386 (3)
Sn1—Cl1	2.3695 (4)	C4—H4	0.9500
Sn1—Cl1ⁱⁱ	2.3695 (4)	C5—C6	1.384 (3)
C1—C2	1.500 (2)	C5—H5	0.9500
C1—H1A	0.9900	C6—C7	1.390 (2)
C1—H1B	0.9900	C6—H6	0.9500
C2—C3	1.394 (2)	C7—H7	0.9500
C2—C7	1.394 (2)

C1ⁱⁱ—Sn1—C1	136.30 (8)	C4—C3—C2	120.80 (15)
C1ⁱⁱ—Sn1—Cl1	103.88 (4)	C4—C3—H3	119.6
C1—Sn1—Cl1	104.09 (4)	C2—C3—H3	119.6
C1ⁱⁱ—Sn1—Cl1ⁱⁱ	104.09 (4)	C5—C4—C3	120.11 (15)
C1—Sn1—Cl1ⁱⁱ	103.88 (4)	C5—C4—H4	119.9
Cl1—Sn1—Cl1ⁱⁱ	99.001 (18)	C3—C4—H4	119.9
C2—C1—Sn1	112.29 (10)	C6—C5—C4	119.69 (16)
C2—C1—H1A	109.1	C6—C5—H5	120.2
Sn1—C1—H1A	109.1	C4—C5—H5	120.2
C2—C1—H1B	109.1	C5—C6—C7	120.24 (16)
Sn1—C1—H1B	109.1	C5—C6—H6	119.9
H1A—C1—H1B	107.9	C7—C6—H6	119.9
C3—C2—C7	118.52 (15)	C6—C7—C2	120.63 (15)
C3—C2—C1	120.99 (15)	C6—C7—H7	119.7
C7—C2—C1	120.48 (15)	C2—C7—H7	119.7

C1ⁱⁱ—Sn1—C1—C2	177.45 (13)	C2—C3—C4—C5	0.4 (2)
Cl1—Sn1—C1—C2	−54.18 (12)	C3—C4—C5—C6	−0.8 (3)
Cl1ⁱⁱ—Sn1—C1—C2	49.01 (12)	C4—C5—C6—C7	0.5 (3)
Sn1—C1—C2—C3	−90.75 (16)	C5—C6—C7—C2	0.2 (3)
Sn1—C1—C2—C7	90.34 (15)	C3—C2—C7—C6	−0.6 (2)
C7—C2—C3—C4	0.3 (2)	C1—C2—C7—C6	178.31 (15)
C1—C2—C3—C4	−178.60 (14)

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

Experimental details

Crystal data
Chemical formula	[Sn(C₇H₇)₂Cl₂]
M_r	371.84
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	123
a, b, c (Å)	23.7710 (3), 4.8019 (1), 12.0808 (2)
β (°)	92.560 (1)
V (Å³)	1377.60 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.22
Crystal size (mm)	0.35 × 0.30 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.511, 0.732
No. of measured, independent and observed [I > 2σ(I)] reflections	6090, 1580, 1527
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.014, 0.041, 1.03
No. of reflections	1580
No. of parameters	78
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.60

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank the University of Malaya (FS339/2008A) for supporting this study.

References

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