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In the title complex, [Sn(C2H2ClO2)2(C7H6F)2], the SnIV 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].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811051002/bh2395sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536811051002/bh2395Isup2.hkl
Contains datablock I

CCDC reference: 763901

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.033
  • wR factor = 0.071
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.69 PLAT230_ALERT_2_C Hirshfeld Test Diff for F1 -- C5 .. 5.7 su PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 3
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still 75 Perc.
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

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%.

Refinement top

All H atoms were placed geometrically and treated as riding on their parent atoms with C—H bond lengths fixed to 0.93 Å for aromatic CH and 0.97 Å for methylene CH2. Isotropic displacement parameters for H atoms were calculated as Uiso(H) = 1.2Ueq(carrier C).

Structure description 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).

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
[Figure 2] 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
Mr = 523.90Dx = 1.742 Mg m3
Monoclinic, C2/cMelting point: 464 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 17.3841 (18) ÅCell parameters from 1705 reflections
b = 5.0480 (8) Åθ = 2.9–25.0°
c = 22.808 (2) ŵ = 1.59 mm1
β = 93.760 (1)°T = 298 K
V = 1997.2 (4) Å3Block, colourless
Z = 40.29 × 0.15 × 0.12 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1754 independent reflections
Radiation source: fine-focus sealed tube1551 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 2017
Tmin = 0.656, Tmax = 0.833k = 56
4738 measured reflectionsl = 2722
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0342P)2]
where P = (Fo2 + 2Fc2)/3
1754 reflections(Δ/σ)max < 0.001
123 parametersΔρmax = 0.71 e Å3
0 restraintsΔρmin = 0.26 e Å3
0 constraints
Crystal data top
[Sn(C2H2ClO2)2(C7H6F)2]V = 1997.2 (4) Å3
Mr = 523.90Z = 4
Monoclinic, C2/cMo Kα radiation
a = 17.3841 (18) ŵ = 1.59 mm1
b = 5.0480 (8) ÅT = 298 K
c = 22.808 (2) Å0.29 × 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)
Tmin = 0.656, Tmax = 0.833Rint = 0.032
4738 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.071H-atom parameters constrained
S = 1.00Δρmax = 0.71 e Å3
1754 reflectionsΔρmin = 0.26 e Å3
123 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.50000.07163 (7)0.25000.04380 (15)
Cl10.58874 (11)0.2741 (3)0.03745 (5)0.1169 (6)
F10.29621 (15)0.3089 (6)0.24062 (11)0.0831 (8)
O10.52467 (15)0.3929 (5)0.19515 (10)0.0517 (7)
O20.55526 (17)0.0310 (5)0.15017 (12)0.0602 (7)
C10.5493 (2)0.2692 (9)0.15046 (17)0.0542 (10)
C20.5669 (4)0.4449 (10)0.0999 (2)0.098 (2)
H2A0.61010.55830.11200.117*
H2B0.52270.55790.09030.117*
C30.3963 (2)0.0939 (7)0.21189 (17)0.0522 (10)
H3A0.40800.26160.19370.063*
H3B0.36200.12960.24280.063*
C40.3557 (2)0.0799 (8)0.16691 (16)0.0465 (9)
C50.3052 (2)0.2743 (9)0.18211 (18)0.0537 (10)
C60.2662 (3)0.4379 (9)0.1434 (2)0.0703 (13)
H60.23180.56350.15610.084*
C70.2789 (3)0.4122 (11)0.0846 (2)0.0820 (15)
H70.25370.52310.05700.098*
C80.3286 (3)0.2242 (12)0.0670 (2)0.0863 (16)
H80.33700.20780.02730.104*
C90.3667 (3)0.0579 (10)0.10703 (19)0.0683 (12)
H90.40000.07030.09400.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0453 (2)0.0360 (2)0.0496 (2)0.0000.00011 (16)0.000
Cl10.1927 (17)0.1008 (12)0.0620 (8)0.0479 (12)0.0451 (10)0.0020 (8)
F10.0875 (19)0.084 (2)0.0804 (18)0.0152 (16)0.0270 (15)0.0010 (15)
O10.0685 (18)0.0384 (16)0.0496 (15)0.0031 (13)0.0147 (13)0.0003 (12)
O20.078 (2)0.0402 (17)0.0635 (17)0.0078 (14)0.0121 (15)0.0013 (13)
C10.065 (3)0.046 (3)0.052 (2)0.003 (2)0.010 (2)0.001 (2)
C20.171 (6)0.058 (3)0.071 (3)0.017 (4)0.057 (4)0.005 (3)
C30.049 (2)0.039 (2)0.068 (3)0.0047 (19)0.0033 (19)0.004 (2)
C40.043 (2)0.043 (2)0.053 (2)0.0078 (19)0.0053 (17)0.0040 (19)
C50.047 (2)0.057 (3)0.057 (3)0.003 (2)0.003 (2)0.003 (2)
C60.058 (3)0.062 (3)0.089 (4)0.014 (2)0.008 (2)0.002 (3)
C70.085 (4)0.072 (4)0.084 (4)0.003 (3)0.032 (3)0.012 (3)
C80.105 (4)0.098 (4)0.052 (3)0.002 (4)0.022 (3)0.003 (3)
C90.071 (3)0.072 (3)0.060 (3)0.008 (3)0.008 (2)0.016 (2)
Geometric parameters (Å, º) top
Sn1—O1i2.109 (2)C3—C41.492 (5)
Sn1—O12.109 (2)C3—H3A0.9700
Sn1—C32.121 (4)C3—H3B0.9700
Sn1—C3i2.121 (4)C4—C51.375 (5)
Sn1—O2i2.537 (3)C4—C91.396 (6)
Sn1—O22.537 (3)C5—C61.359 (6)
Cl1—C21.728 (5)C6—C71.380 (7)
F1—C51.365 (4)C6—H60.9300
O1—C11.292 (4)C7—C81.361 (7)
O2—C11.207 (4)C7—H70.9300
C1—C21.503 (6)C8—C91.377 (7)
C2—H2A0.9700C8—H80.9300
C2—H2B0.9700C9—H90.9300
O1i—Sn1—O179.50 (13)H2A—C2—H2B107.7
O1i—Sn1—C3110.21 (13)C4—C3—Sn1113.7 (3)
O1—Sn1—C3105.08 (12)C4—C3—H3A108.8
O1i—Sn1—C3i105.08 (12)Sn1—C3—H3A108.8
O1—Sn1—C3i110.21 (13)C4—C3—H3B108.8
C3—Sn1—C3i133.6 (2)Sn1—C3—H3B108.8
O1i—Sn1—O2i54.99 (9)H3A—C3—H3B107.7
O1—Sn1—O2i134.28 (9)C5—C4—C9115.7 (4)
C3—Sn1—O2i88.52 (13)C5—C4—C3121.8 (3)
C3i—Sn1—O2i87.82 (13)C9—C4—C3122.5 (4)
O1i—Sn1—O2134.28 (9)C6—C5—F1118.2 (4)
O1—Sn1—O254.99 (9)C6—C5—C4124.7 (4)
C3—Sn1—O287.82 (13)F1—C5—C4117.0 (4)
C3i—Sn1—O288.52 (13)C5—C6—C7118.0 (4)
O2i—Sn1—O2170.72 (12)C5—C6—H6121.0
C1—O1—Sn1100.8 (2)C7—C6—H6121.0
C1—O2—Sn182.9 (2)C8—C7—C6119.8 (5)
O2—C1—O1121.3 (4)C8—C7—H7120.1
O2—C1—C2124.2 (4)C6—C7—H7120.1
O1—C1—C2114.5 (4)C7—C8—C9121.1 (5)
C1—C2—Cl1113.9 (3)C7—C8—H8119.5
C1—C2—H2A108.8C9—C8—H8119.5
Cl1—C2—H2A108.8C8—C9—C4120.6 (4)
C1—C2—H2B108.8C8—C9—H9119.7
Cl1—C2—H2B108.8C4—C9—H9119.7
Symmetry code: (i) x+1, y, z+1/2.

Experimental details

Crystal data
Chemical formula[Sn(C2H2ClO2)2(C7H6F)2]
Mr523.90
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)17.3841 (18), 5.0480 (8), 22.808 (2)
β (°) 93.760 (1)
V3)1997.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)1.59
Crystal size (mm)0.29 × 0.15 × 0.12
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.656, 0.833
No. of measured, independent and
observed [I > 2σ(I)] reflections
4738, 1754, 1551
Rint0.032
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.071, 1.00
No. of reflections1754
No. of parameters123
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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—O12.109 (2)Sn1—O22.537 (3)
Sn1—C32.121 (4)
 

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