Bis(chloro­acetato-κ2O,O′)bis­(2-fluoro­benzyl-κC1)tin(IV)

Deng, A.; Teng, M.; Xie, Q.; Yan, N.

doi:10.1107/S1600536811051002

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1905

https://doi.org/10.1107/S1600536811051002

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Bis(chloroacetato-κ²O,O′)bis(2-fluorobenzyl-κC¹)tin(IV)

Aixia Deng,^a ^* Mouyong Teng,^a Qian Xie ^a and Nana Yan ^a

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

(Received 4 November 2011; accepted 28 November 2011; online 30 November 2011)

In the title complex, [Sn(C₂H₂ClO₂)₂(C₇H₆F)₂], the Sn^IV atom is located on a twofold rotation axis and forms a strongly distorted trans-octahedral geometry. The equatorial plane is defined by two chelating chloroacetate ligands with asymmetrical Sn—O bond lengths, while the axial positions are occupied by the C atoms of two 2-fluorobenzyl groups. In the crystal, infinite chains in the [010] direction are formed through intermolecular Sn⋯O interactions [Sn⋯O separation = 3.682 (3) Å].

Related literature

For details of the synthesis, see: Zhang et al. (2007 ).

Experimental

Crystal data

[Sn(C₂H₂ClO₂)₂(C₇H₆F)₂]
M_r = 523.90
Monoclinic, C 2/c
a = 17.3841 (18) Å
b = 5.0480 (8) Å
c = 22.808 (2) Å
β = 93.760 (1)°
V = 1997.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.59 mm⁻¹
T = 298 K
0.29 × 0.15 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.656, T_max = 0.833
4738 measured reflections
1754 independent reflections
1551 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.071
S = 1.00
1754 reflections
123 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—O1	2.109 (2)
Sn1—C3	2.121 (4)
Sn1—O2	2.537 (3)

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811051002/bh2395sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811051002/bh2395Isup2.hkl

checkCIF report

Comment top

The title complex was obtained using a route similar to that used for the synthesis of a trinuclear tin complex (Zhang et al., 2007). The title complex has 2-fold symmetry, with the Sn atom placed on the crystallographic symmetry axis (Fig. 1). Selected bond lengths and angles are given in table 1. The coordination geometry of tin can be described as a distorted trans-octahedron geometry, with two C atoms of 2-fluorobenzyl groups occupying the axial positions. The C3—Sn1—C3ⁱ bond angle of 133.6 (2)° (symmetry code i: 1 - x, y, 1/2 - z) reflects the distortion from octahedral geometry. The equatorial plane is defined by four O atoms of two symmetry-related chloroacetate ligands. The bond lengths in the equatorial plane are Sn1—O1 = 2.109 (2) and Sn1—O2 = 2.537 (3) Å, reflecting the asymmetrical coordination of acetate groups.

The complex forms infinite chains containing Sn₂O₂ rings, through intermolecular Sn···O contacts, characterized by separations Sn···O = 3.682 (3) Å (Fig. 2).

Related literature top

For details of the synthesis, see: Zhang et al. (2007).

Experimental top

Chloroacetic acid (2 mmol) was added to a sodium ethoxide solution (2 mmol, 20 ml of ethanol), and the mixture was stirred for 30 min. Then, 1 mmol of bis(2-fluorobenzyl)tin(IV)dichloride (Zhang et al., 2007) was added to the mixture, continuing the reaction for 12 h at 318 K. After cooling down to room temperature, the reaction was filtered off. The solvent of the filtrate was gradually removed by evaporation under vacuum, until a solid product was obtained. The solid was recrystallized from ether-dichloromethane and colourless crystals suitable for X-ray diffraction were obtained (m.p. 464 K). Analysis calculated for C₁₈H₁₆Cl₂F₂O₄Sn: C 41.26, H 3.08%; found: C 41.29, H 3.06%.

Structure description top

The complex forms infinite chains containing Sn₂O₂ rings, through intermolecular Sn···O contacts, characterized by separations Sn···O = 3.682 (3) Å (Fig. 2).

For details of the synthesis, see: Zhang et al. (2007).

Computing details top

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The unit cell of the title compound.

Bis(chloroacetato-κ²O,O')bis(2-fluorobenzyl- κC¹)tin(IV) top

Crystal data top

[Sn(C₂H₂ClO₂)₂(C₇H₆F)₂]	F(000) = 1032
M_r = 523.90	D_x = 1.742 Mg m⁻³
Monoclinic, C2/c	Melting point: 464 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 17.3841 (18) Å	Cell parameters from 1705 reflections
b = 5.0480 (8) Å	θ = 2.9–25.0°
c = 22.808 (2) Å	µ = 1.59 mm⁻¹
β = 93.760 (1)°	T = 298 K
V = 1997.2 (4) Å³	Block, colourless
Z = 4	0.29 × 0.15 × 0.12 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1754 independent reflections
Radiation source: fine-focus sealed tube	1551 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −20→17
T_min = 0.656, T_max = 0.833	k = −5→6
4738 measured reflections	l = −27→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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0342P)²] where P = (F_o² + 2F_c²)/3
1754 reflections	(Δ/σ)_max < 0.001
123 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³
0 constraints

Crystal data top

[Sn(C₂H₂ClO₂)₂(C₇H₆F)₂]	V = 1997.2 (4) Å³
M_r = 523.90	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.3841 (18) Å	µ = 1.59 mm⁻¹
b = 5.0480 (8) Å	T = 298 K
c = 22.808 (2) Å	0.29 × 0.15 × 0.12 mm
β = 93.760 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1754 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1551 reflections with I > 2σ(I)
T_min = 0.656, T_max = 0.833	R_int = 0.032
4738 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.00	Δρ_max = 0.71 e Å⁻³
1754 reflections	Δρ_min = −0.26 e Å⁻³
123 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.5000	0.07163 (7)	0.2500	0.04380 (15)
Cl1	0.58874 (11)	0.2741 (3)	0.03745 (5)	0.1169 (6)
F1	0.29621 (15)	0.3089 (6)	0.24062 (11)	0.0831 (8)
O1	0.52467 (15)	0.3929 (5)	0.19515 (10)	0.0517 (7)
O2	0.55526 (17)	0.0310 (5)	0.15017 (12)	0.0602 (7)
C1	0.5493 (2)	0.2692 (9)	0.15046 (17)	0.0542 (10)
C2	0.5669 (4)	0.4449 (10)	0.0999 (2)	0.098 (2)
H2A	0.6101	0.5583	0.1120	0.117*
H2B	0.5227	0.5579	0.0903	0.117*
C3	0.3963 (2)	−0.0939 (7)	0.21189 (17)	0.0522 (10)
H3A	0.4080	−0.2616	0.1937	0.063*
H3B	0.3620	−0.1296	0.2428	0.063*
C4	0.3557 (2)	0.0799 (8)	0.16691 (16)	0.0465 (9)
C5	0.3052 (2)	0.2743 (9)	0.18211 (18)	0.0537 (10)
C6	0.2662 (3)	0.4379 (9)	0.1434 (2)	0.0703 (13)
H6	0.2318	0.5635	0.1561	0.084*
C7	0.2789 (3)	0.4122 (11)	0.0846 (2)	0.0820 (15)
H7	0.2537	0.5231	0.0570	0.098*
C8	0.3286 (3)	0.2242 (12)	0.0670 (2)	0.0863 (16)
H8	0.3370	0.2078	0.0273	0.104*
C9	0.3667 (3)	0.0579 (10)	0.10703 (19)	0.0683 (12)
H9	0.4000	−0.0703	0.0940	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0453 (2)	0.0360 (2)	0.0496 (2)	0.000	−0.00011 (16)	0.000
Cl1	0.1927 (17)	0.1008 (12)	0.0620 (8)	0.0479 (12)	0.0451 (10)	0.0020 (8)
F1	0.0875 (19)	0.084 (2)	0.0804 (18)	0.0152 (16)	0.0270 (15)	0.0010 (15)
O1	0.0685 (18)	0.0384 (16)	0.0496 (15)	0.0031 (13)	0.0147 (13)	0.0003 (12)
O2	0.078 (2)	0.0402 (17)	0.0635 (17)	0.0078 (14)	0.0121 (15)	0.0013 (13)
C1	0.065 (3)	0.046 (3)	0.052 (2)	0.003 (2)	0.010 (2)	0.001 (2)
C2	0.171 (6)	0.058 (3)	0.071 (3)	0.017 (4)	0.057 (4)	0.005 (3)
C3	0.049 (2)	0.039 (2)	0.068 (3)	−0.0047 (19)	−0.0033 (19)	−0.004 (2)
C4	0.043 (2)	0.043 (2)	0.053 (2)	−0.0078 (19)	−0.0053 (17)	−0.0040 (19)
C5	0.047 (2)	0.057 (3)	0.057 (3)	−0.003 (2)	0.003 (2)	−0.003 (2)
C6	0.058 (3)	0.062 (3)	0.089 (4)	0.014 (2)	−0.008 (2)	−0.002 (3)
C7	0.085 (4)	0.072 (4)	0.084 (4)	0.003 (3)	−0.032 (3)	0.012 (3)
C8	0.105 (4)	0.098 (4)	0.052 (3)	0.002 (4)	−0.022 (3)	−0.003 (3)
C9	0.071 (3)	0.072 (3)	0.060 (3)	0.008 (3)	−0.008 (2)	−0.016 (2)

Geometric parameters (Å, º) top

Sn1—O1ⁱ	2.109 (2)	C3—C4	1.492 (5)
Sn1—O1	2.109 (2)	C3—H3A	0.9700
Sn1—C3	2.121 (4)	C3—H3B	0.9700
Sn1—C3ⁱ	2.121 (4)	C4—C5	1.375 (5)
Sn1—O2ⁱ	2.537 (3)	C4—C9	1.396 (6)
Sn1—O2	2.537 (3)	C5—C6	1.359 (6)
Cl1—C2	1.728 (5)	C6—C7	1.380 (7)
F1—C5	1.365 (4)	C6—H6	0.9300
O1—C1	1.292 (4)	C7—C8	1.361 (7)
O2—C1	1.207 (4)	C7—H7	0.9300
C1—C2	1.503 (6)	C8—C9	1.377 (7)
C2—H2A	0.9700	C8—H8	0.9300
C2—H2B	0.9700	C9—H9	0.9300

O1ⁱ—Sn1—O1	79.50 (13)	H2A—C2—H2B	107.7
O1ⁱ—Sn1—C3	110.21 (13)	C4—C3—Sn1	113.7 (3)
O1—Sn1—C3	105.08 (12)	C4—C3—H3A	108.8
O1ⁱ—Sn1—C3ⁱ	105.08 (12)	Sn1—C3—H3A	108.8
O1—Sn1—C3ⁱ	110.21 (13)	C4—C3—H3B	108.8
C3—Sn1—C3ⁱ	133.6 (2)	Sn1—C3—H3B	108.8
O1ⁱ—Sn1—O2ⁱ	54.99 (9)	H3A—C3—H3B	107.7
O1—Sn1—O2ⁱ	134.28 (9)	C5—C4—C9	115.7 (4)
C3—Sn1—O2ⁱ	88.52 (13)	C5—C4—C3	121.8 (3)
C3ⁱ—Sn1—O2ⁱ	87.82 (13)	C9—C4—C3	122.5 (4)
O1ⁱ—Sn1—O2	134.28 (9)	C6—C5—F1	118.2 (4)
O1—Sn1—O2	54.99 (9)	C6—C5—C4	124.7 (4)
C3—Sn1—O2	87.82 (13)	F1—C5—C4	117.0 (4)
C3ⁱ—Sn1—O2	88.52 (13)	C5—C6—C7	118.0 (4)
O2ⁱ—Sn1—O2	170.72 (12)	C5—C6—H6	121.0
C1—O1—Sn1	100.8 (2)	C7—C6—H6	121.0
C1—O2—Sn1	82.9 (2)	C8—C7—C6	119.8 (5)
O2—C1—O1	121.3 (4)	C8—C7—H7	120.1
O2—C1—C2	124.2 (4)	C6—C7—H7	120.1
O1—C1—C2	114.5 (4)	C7—C8—C9	121.1 (5)
C1—C2—Cl1	113.9 (3)	C7—C8—H8	119.5
C1—C2—H2A	108.8	C9—C8—H8	119.5
Cl1—C2—H2A	108.8	C8—C9—C4	120.6 (4)
C1—C2—H2B	108.8	C8—C9—H9	119.7
Cl1—C2—H2B	108.8	C4—C9—H9	119.7

Symmetry code: (i) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Sn(C₂H₂ClO₂)₂(C₇H₆F)₂]
M_r	523.90
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	17.3841 (18), 5.0480 (8), 22.808 (2)
β (°)	93.760 (1)
V (Å³)	1997.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.59
Crystal size (mm)	0.29 × 0.15 × 0.12

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.656, 0.833
No. of measured, independent and observed [I > 2σ(I)] reflections	4738, 1754, 1551
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.071, 1.00
No. of reflections	1754
No. of parameters	123
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.26

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Sn1—O1	2.109 (2)	Sn1—O2	2.537 (3)
Sn1—C3	2.121 (4)

Acknowledgements

The authors thank the State Key Laboratory of Crystal Materials (SRT11055HX2), Liaocheng University, China, and the Liaocheng University Foundation (xo9013) for financial support.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, J.-H., Ma, C.-L. & Zhang, R.-F. (2007). Acta Cryst. E63, m2161. Web of Science CSD CrossRef IUCr Journals Google Scholar