



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811051002/bh2395sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536811051002/bh2395Isup2.hkl |
CCDC reference: 763901
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(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
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%.
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).
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).
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).
![]() | Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. |
![]() | Fig. 2. The unit cell of the title compound. |
[Sn(C2H2ClO2)2(C7H6F)2] | F(000) = 1032 |
Mr = 523.90 | Dx = 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 |
Bruker SMART 1000 CCD area-detector diffractometer | 1754 independent reflections |
Radiation source: fine-focus sealed tube | 1551 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −20→17 |
Tmin = 0.656, Tmax = 0.833 | k = −5→6 |
4738 measured reflections | l = −27→22 |
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(Fo2) + (0.0342P)2] where P = (Fo2 + 2Fc2)/3 |
1754 reflections | (Δ/σ)max < 0.001 |
123 parameters | Δρmax = 0.71 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
0 constraints |
[Sn(C2H2ClO2)2(C7H6F)2] | V = 1997.2 (4) Å3 |
Mr = 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)° |
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 = 0.833 | Rint = 0.032 |
4738 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.071 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.71 e Å−3 |
1754 reflections | Δρmin = −0.26 e Å−3 |
123 parameters |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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] |
Mr | 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) |
Tmin, Tmax | 0.656, 0.833 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4738, 1754, 1551 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.71, −0.26 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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).