Dibenzyl­dichloridotin(IV)

Abstract

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,

• a = 23.7710 (3) Å

• b = 4.8019 (1) Å

• c = 12.0808 (2) Å

• β = 92.560 (1)°

• V = 1377.60 (4) ų

• 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[F ² > 2σ(F ²)] = 0.014

• wR(F ²) = 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 ▶).

Supplementary Material

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

supplementary crystallographic information

Experimental

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.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95–0.99 Å) and were included in the refinement in the riding model approximation with U(H) set to 1.2U(C).

Figures

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.

Crystal data

[Sn(C7H7)2Cl2]	F(000) = 728
Mr = 371.84	Dx = 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

Bruker SMART APEX diffractometer	1580 independent reflections
Radiation source: fine-focus sealed tube	1527 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −30→30
Tmin = 0.511, Tmax = 0.732	k = −6→6
6090 measured reflections	l = −15→15

Refinement

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(Fo2) + (0.0238P)2 + 1.6061P] where P = (Fo2 + 2Fc2)/3
1580 reflections	(Δ/σ)max = 0.001
78 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.60 e Å−3

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

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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.