Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048362/ci2474sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048362/ci2474Isup2.hkl |
CCDC reference: 643353
All reagents and solvents were used as obtained without further purification. The reaction was carried out under a nitrogen atmosphere. 2,3,4,5-Tetrafluorobenzoic acid (0.388 g, 2 mmol) was added to a solution of sodium ethoxide (0.272 g, 2 mmol) in benzene (30 ml) and the mixture was stirred for 10 min, after that dimethyltin dichloride (0.220 g, 1 mmol) and 1,10-phenanthroline (0.198 g, 1 mmol) were added. The reaction mixture was kept at 313 K for 12 h. After cooling to room temperature, the solution was filtered. The solvent was removed from the filtrate under vacuum. The solid residue was recrystallized from diethyl ether and colourless crystals of the title compound suitable for X-Ray diffraction studies were obtained (yield 0.724 g, 81%; m.p. 414 K). Analysis, calculated for C28H16N2O4Sn: C 59.72, H 2.86, N 4.97; found: C 59.53, H 2.68, N 5.17%.
H atoms were positioned geometrically and refined as riding, with C—H = 0.93 Å (aromatic) and 0.96 Å (methyl) and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).
Organotin carboxylate complexes have recently attracted much attention due to their biochemical and commercial applications (Narula et al., 1988). In order to explore the impact of the structure on properties of the complexes, as well as to analyze the structure–activity relationships, a large number of organotin carboxylates have been prepared and studied (Gielen, 2002). We report here the crystal structure of the title compound, Me2Sn(C6HF4CO2)2(C12H8N2), with 1,10-phenanthroline as a co-ligand.
The coordination geometry about the Sn atom is best described as distorted pentagonal bipyramidal with the axial positions occupied by methyl groups (Table 1). Three carboxylate O atoms (O1,O2,O3) from two tetrafluorobenzoate ligands and the two N atoms (N1,N2) of the 1,10-phenanthroline ligand occupy the basal plane (Fig. 1). The Sn—N distances (Table 1) are longer than the sum of the covalent radii of Sn and N atoms (2.15 Å), but much shorter than the sum of van der Waals radii of the two atoms (3.74 Å; Casas et al., 1997). The Sn1—O3 bond length of 2.146 (7) Å is close to the sum of the covalent radii of Sn and O atoms (2.13 Å), showing strong coordination interaction, which is in agreement with the monodentate coordination mode of the carboxylate group (Li et al., 2005). The Sn1—O2 [2.360 (7) Å] and Sn1—O1 [2.554 (8) Å] distances lie midway between the sums of the van der Waals and covalent radii of Sn and O atoms (2.13–3.68 Å; Ma et al., 2005).
In the crystal structure, C—H···F and C—H···O type hydrogen bonds link the molecules into cyclic centrosymmetric dimers (Table 2).
For applications of organotin carboxylate complexes, see: Narula et al. (1988). For related structures, see: Gielen (2002); Li et al. (2005). For van der Waals radii and covalent radii data, see: Casas et al. (1997); Ma et al. (2005).
Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity. |
[Sn(CH3)2(C7HF4O2)2(C12H8N2)] | Z = 2 |
Mr = 715.12 | F(000) = 704 |
Triclinic, P1 | Dx = 1.807 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.265 (4) Å | Cell parameters from 2191 reflections |
b = 10.174 (6) Å | θ = 2.4–25.8° |
c = 18.957 (11) Å | µ = 1.07 mm−1 |
α = 90.519 (10)° | T = 298 K |
β = 90.205 (9)° | Block, colourless |
γ = 110.247 (8)° | 0.18 × 0.13 × 0.09 mm |
V = 1314.5 (13) Å3 |
Siemens SMART CCD area-detector diffractometer | 4483 independent reflections |
Radiation source: fine-focus sealed tube | 3007 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.831, Tmax = 0.910 | k = −12→11 |
6410 measured reflections | l = −22→15 |
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)] = 0.081 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.222 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.132P)2] where P = (Fo2 + 2Fc2)/3 |
4483 reflections | (Δ/σ)max = 0.001 |
388 parameters | Δρmax = 1.64 e Å−3 |
0 restraints | Δρmin = −2.31 e Å−3 |
[Sn(CH3)2(C7HF4O2)2(C12H8N2)] | γ = 110.247 (8)° |
Mr = 715.12 | V = 1314.5 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.265 (4) Å | Mo Kα radiation |
b = 10.174 (6) Å | µ = 1.07 mm−1 |
c = 18.957 (11) Å | T = 298 K |
α = 90.519 (10)° | 0.18 × 0.13 × 0.09 mm |
β = 90.205 (9)° |
Siemens SMART CCD area-detector diffractometer | 4483 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3007 reflections with I > 2σ(I) |
Tmin = 0.831, Tmax = 0.910 | Rint = 0.054 |
6410 measured reflections |
R[F2 > 2σ(F2)] = 0.081 | 0 restraints |
wR(F2) = 0.222 | H-atom parameters constrained |
S = 1.01 | Δρmax = 1.64 e Å−3 |
4483 reflections | Δρmin = −2.31 e Å−3 |
388 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.23811 (11) | 0.21428 (7) | 0.24653 (4) | 0.0428 (3) | |
F1 | 0.6709 (13) | 0.3680 (8) | 0.4720 (4) | 0.089 (2) | |
F2 | 0.8879 (12) | 0.5751 (8) | 0.5510 (4) | 0.079 (2) | |
F3 | 0.9354 (12) | 0.8410 (7) | 0.5194 (4) | 0.085 (2) | |
F4 | 0.7645 (13) | 0.8986 (7) | 0.4031 (5) | 0.095 (3) | |
F5 | 0.1948 (11) | 0.5064 (7) | −0.0229 (3) | 0.0693 (19) | |
F6 | 0.2542 (13) | 0.7781 (8) | −0.0370 (4) | 0.080 (2) | |
F7 | 0.3925 (12) | 0.9560 (6) | 0.0717 (4) | 0.076 (2) | |
F8 | 0.4790 (11) | 0.8624 (7) | 0.1952 (4) | 0.0697 (19) | |
N1 | 0.2041 (13) | −0.0126 (9) | 0.3011 (4) | 0.048 (2) | |
N2 | 0.0471 (13) | 0.0191 (8) | 0.1755 (5) | 0.048 (2) | |
O1 | 0.4267 (13) | 0.2843 (8) | 0.3628 (4) | 0.065 (2) | |
O2 | 0.4062 (12) | 0.4435 (7) | 0.2891 (4) | 0.063 (2) | |
O3 | 0.1802 (11) | 0.3414 (7) | 0.1657 (4) | 0.0480 (17) | |
O4 | 0.3100 (14) | 0.3174 (8) | 0.0624 (4) | 0.068 (2) | |
C1 | 0.4652 (17) | 0.4077 (12) | 0.3462 (6) | 0.052 (3) | |
C2 | 0.5966 (14) | 0.5214 (10) | 0.3913 (5) | 0.042 (2) | |
C3 | 0.6878 (16) | 0.4988 (10) | 0.4510 (6) | 0.048 (3) | |
C4 | 0.8018 (17) | 0.6015 (12) | 0.4933 (5) | 0.054 (3) | |
C5 | 0.8270 (18) | 0.7387 (12) | 0.4780 (6) | 0.063 (3) | |
C6 | 0.7380 (17) | 0.7658 (10) | 0.4181 (6) | 0.053 (3) | |
C7 | 0.6231 (16) | 0.6614 (11) | 0.3753 (6) | 0.052 (3) | |
H7 | 0.5626 | 0.6825 | 0.3359 | 0.062* | |
C8 | 0.2614 (17) | 0.3861 (11) | 0.1077 (6) | 0.049 (3) | |
C9 | 0.2966 (14) | 0.5365 (10) | 0.0970 (5) | 0.042 (2) | |
C10 | 0.2667 (15) | 0.5912 (10) | 0.0332 (5) | 0.045 (2) | |
C11 | 0.2951 (18) | 0.7302 (12) | 0.0255 (6) | 0.057 (3) | |
C12 | 0.3661 (18) | 0.8207 (10) | 0.0793 (6) | 0.055 (3) | |
C13 | 0.4030 (15) | 0.7691 (10) | 0.1428 (6) | 0.046 (2) | |
C14 | 0.3653 (15) | 0.6309 (11) | 0.1512 (6) | 0.046 (2) | |
H14 | 0.3865 | 0.5986 | 0.1952 | 0.056* | |
C15 | 0.2854 (18) | −0.0276 (13) | 0.3634 (6) | 0.061 (3) | |
H15 | 0.3559 | 0.0518 | 0.3895 | 0.073* | |
C16 | 0.2661 (19) | −0.1588 (13) | 0.3892 (7) | 0.066 (3) | |
H16 | 0.3235 | −0.1667 | 0.4322 | 0.079* | |
C17 | 0.1632 (18) | −0.2761 (13) | 0.3516 (8) | 0.069 (4) | |
H17 | 0.1506 | −0.3639 | 0.3690 | 0.083* | |
C18 | 0.0780 (19) | −0.2653 (12) | 0.2883 (7) | 0.061 (3) | |
C19 | 0.1024 (14) | −0.1294 (9) | 0.2646 (5) | 0.040 (2) | |
C20 | 0.0178 (14) | −0.1119 (9) | 0.1983 (6) | 0.043 (2) | |
C21 | −0.0894 (15) | −0.2316 (10) | 0.1590 (6) | 0.051 (3) | |
C22 | −0.1680 (17) | −0.2121 (12) | 0.0942 (6) | 0.053 (3) | |
H22 | −0.2387 | −0.2886 | 0.0663 | 0.064* | |
C23 | −0.1392 (16) | −0.0783 (12) | 0.0726 (6) | 0.057 (3) | |
H23 | −0.1924 | −0.0625 | 0.0302 | 0.068* | |
C24 | −0.0302 (17) | 0.0321 (12) | 0.1148 (6) | 0.058 (3) | |
H24 | −0.0101 | 0.1223 | 0.0990 | 0.070* | |
C25 | −0.0352 (18) | −0.3825 (11) | 0.2462 (7) | 0.064 (3) | |
H25 | −0.0525 | −0.4723 | 0.2619 | 0.076* | |
C26 | −0.1164 (18) | −0.3679 (11) | 0.1858 (7) | 0.063 (3) | |
H26 | −0.1917 | −0.4470 | 0.1604 | 0.076* | |
C27 | 0.5007 (19) | 0.2137 (12) | 0.2044 (6) | 0.066 (3) | |
H27A | 0.5862 | 0.3085 | 0.1972 | 0.098* | |
H27B | 0.4758 | 0.1641 | 0.1601 | 0.098* | |
H27C | 0.5617 | 0.1684 | 0.2364 | 0.098* | |
C28 | −0.0154 (18) | 0.2079 (12) | 0.3005 (6) | 0.061 (3) | |
H28A | −0.0556 | 0.1281 | 0.3309 | 0.092* | |
H28B | −0.1182 | 0.2007 | 0.2672 | 0.092* | |
H28C | 0.0114 | 0.2919 | 0.3283 | 0.092* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0444 (4) | 0.0339 (4) | 0.0483 (4) | 0.0111 (3) | −0.0070 (3) | 0.0040 (3) |
F1 | 0.093 (6) | 0.073 (5) | 0.095 (6) | 0.020 (4) | −0.019 (5) | 0.006 (4) |
F2 | 0.088 (5) | 0.076 (5) | 0.061 (4) | 0.014 (4) | −0.027 (4) | 0.001 (4) |
F3 | 0.088 (6) | 0.057 (4) | 0.087 (5) | −0.004 (4) | −0.024 (4) | −0.021 (4) |
F4 | 0.115 (7) | 0.045 (4) | 0.112 (6) | 0.011 (4) | −0.020 (5) | 0.005 (4) |
F5 | 0.090 (5) | 0.055 (4) | 0.058 (4) | 0.021 (4) | −0.019 (4) | −0.008 (3) |
F6 | 0.110 (6) | 0.066 (5) | 0.073 (4) | 0.043 (4) | −0.012 (4) | 0.015 (4) |
F7 | 0.098 (6) | 0.038 (3) | 0.095 (5) | 0.026 (4) | 0.015 (4) | 0.011 (3) |
F8 | 0.075 (5) | 0.050 (4) | 0.078 (4) | 0.014 (3) | 0.003 (4) | −0.017 (3) |
N1 | 0.053 (5) | 0.043 (5) | 0.054 (5) | 0.023 (4) | 0.000 (4) | 0.015 (4) |
N2 | 0.051 (5) | 0.035 (4) | 0.060 (6) | 0.016 (4) | −0.008 (4) | 0.000 (4) |
O1 | 0.072 (6) | 0.041 (4) | 0.076 (5) | 0.013 (4) | −0.014 (4) | −0.002 (4) |
O2 | 0.069 (5) | 0.041 (4) | 0.060 (5) | −0.002 (4) | −0.023 (4) | −0.002 (4) |
O3 | 0.054 (4) | 0.042 (4) | 0.047 (4) | 0.016 (3) | −0.001 (4) | 0.009 (3) |
O4 | 0.089 (6) | 0.047 (5) | 0.066 (5) | 0.021 (4) | 0.009 (5) | 0.004 (4) |
C1 | 0.055 (7) | 0.051 (7) | 0.048 (6) | 0.017 (5) | −0.022 (5) | −0.005 (5) |
C2 | 0.036 (5) | 0.035 (5) | 0.054 (6) | 0.011 (4) | 0.002 (5) | −0.006 (5) |
C3 | 0.053 (6) | 0.031 (5) | 0.054 (6) | 0.006 (5) | 0.000 (5) | 0.007 (5) |
C4 | 0.057 (7) | 0.060 (7) | 0.041 (6) | 0.014 (6) | −0.004 (5) | −0.002 (5) |
C5 | 0.064 (8) | 0.051 (7) | 0.057 (7) | 0.000 (6) | −0.004 (6) | −0.012 (6) |
C6 | 0.054 (7) | 0.029 (5) | 0.068 (7) | 0.003 (5) | 0.003 (6) | 0.004 (5) |
C7 | 0.043 (6) | 0.044 (6) | 0.062 (7) | 0.006 (5) | −0.003 (5) | 0.001 (5) |
C8 | 0.055 (7) | 0.040 (6) | 0.046 (6) | 0.011 (5) | −0.012 (5) | −0.005 (5) |
C9 | 0.037 (5) | 0.042 (5) | 0.047 (6) | 0.012 (4) | −0.002 (5) | 0.005 (5) |
C10 | 0.044 (6) | 0.044 (6) | 0.045 (6) | 0.014 (5) | 0.004 (5) | 0.001 (5) |
C11 | 0.064 (7) | 0.050 (7) | 0.058 (7) | 0.019 (6) | 0.008 (6) | 0.014 (6) |
C12 | 0.063 (7) | 0.031 (5) | 0.071 (7) | 0.016 (5) | 0.010 (6) | 0.009 (5) |
C13 | 0.038 (6) | 0.040 (5) | 0.062 (7) | 0.016 (5) | 0.008 (5) | −0.004 (5) |
C14 | 0.037 (5) | 0.050 (6) | 0.052 (6) | 0.015 (5) | 0.007 (5) | 0.004 (5) |
C15 | 0.055 (7) | 0.069 (8) | 0.072 (8) | 0.037 (6) | −0.005 (6) | 0.012 (6) |
C16 | 0.063 (8) | 0.065 (8) | 0.081 (8) | 0.037 (7) | 0.006 (7) | 0.026 (7) |
C17 | 0.050 (7) | 0.060 (8) | 0.108 (11) | 0.032 (6) | 0.016 (7) | 0.034 (7) |
C18 | 0.066 (8) | 0.044 (6) | 0.071 (8) | 0.015 (6) | 0.018 (6) | 0.021 (6) |
C19 | 0.034 (5) | 0.024 (4) | 0.063 (6) | 0.012 (4) | 0.005 (5) | 0.009 (4) |
C20 | 0.032 (5) | 0.023 (5) | 0.065 (7) | 0.000 (4) | 0.008 (5) | 0.006 (4) |
C21 | 0.032 (5) | 0.038 (6) | 0.075 (8) | −0.001 (4) | 0.016 (5) | −0.001 (5) |
C22 | 0.049 (6) | 0.048 (6) | 0.056 (7) | 0.010 (5) | 0.005 (5) | −0.008 (5) |
C23 | 0.046 (6) | 0.051 (7) | 0.057 (7) | −0.003 (5) | −0.004 (5) | −0.001 (5) |
C24 | 0.064 (7) | 0.040 (6) | 0.055 (7) | 0.000 (5) | −0.011 (6) | 0.008 (5) |
C25 | 0.065 (8) | 0.031 (6) | 0.098 (10) | 0.021 (5) | 0.015 (7) | 0.013 (6) |
C26 | 0.059 (7) | 0.028 (5) | 0.095 (9) | 0.006 (5) | 0.021 (7) | 0.002 (6) |
C27 | 0.072 (8) | 0.050 (7) | 0.070 (8) | 0.016 (6) | −0.012 (7) | −0.010 (6) |
C28 | 0.068 (8) | 0.045 (6) | 0.065 (7) | 0.011 (6) | −0.004 (6) | 0.009 (5) |
Sn1—C27 | 2.072 (13) | C9—C10 | 1.382 (14) |
Sn1—C28 | 2.092 (13) | C10—C11 | 1.366 (15) |
Sn1—O3 | 2.146 (7) | C11—C12 | 1.344 (16) |
Sn1—O2 | 2.360 (7) | C12—C13 | 1.380 (16) |
Sn1—N2 | 2.389 (8) | C13—C14 | 1.348 (14) |
Sn1—N1 | 2.472 (8) | C14—H14 | 0.93 |
Sn1—O1 | 2.554 (8) | C15—C16 | 1.388 (16) |
F1—C3 | 1.356 (12) | C15—H15 | 0.93 |
F2—C4 | 1.332 (12) | C16—C17 | 1.361 (18) |
F3—C5 | 1.317 (12) | C16—H16 | 0.93 |
F4—C6 | 1.331 (12) | C17—C18 | 1.371 (17) |
F5—C10 | 1.347 (11) | C17—H17 | 0.93 |
F6—C11 | 1.355 (13) | C18—C19 | 1.410 (14) |
F7—C12 | 1.332 (11) | C18—C25 | 1.426 (17) |
F8—C13 | 1.345 (11) | C19—C20 | 1.436 (14) |
N1—C19 | 1.346 (12) | C20—C21 | 1.403 (13) |
N1—C15 | 1.351 (14) | C21—C22 | 1.397 (16) |
N2—C24 | 1.307 (13) | C21—C26 | 1.430 (16) |
N2—C20 | 1.350 (12) | C22—C23 | 1.370 (16) |
O1—C1 | 1.232 (13) | C22—H22 | 0.93 |
O2—C1 | 1.265 (12) | C23—C24 | 1.376 (14) |
O3—C8 | 1.261 (13) | C23—H23 | 0.93 |
O4—C8 | 1.229 (13) | C24—H24 | 0.93 |
C1—C2 | 1.481 (14) | C25—C26 | 1.319 (17) |
C2—C3 | 1.371 (14) | C25—H25 | 0.93 |
C2—C7 | 1.406 (14) | C26—H26 | 0.93 |
C3—C4 | 1.343 (14) | C27—H27A | 0.96 |
C4—C5 | 1.378 (16) | C27—H27B | 0.96 |
C5—C6 | 1.380 (16) | C27—H27C | 0.96 |
C6—C7 | 1.359 (14) | C28—H28A | 0.96 |
C7—H7 | 0.93 | C28—H28B | 0.96 |
C8—C9 | 1.478 (14) | C28—H28C | 0.96 |
C9—C14 | 1.370 (14) | ||
C27—Sn1—C28 | 173.1 (4) | C12—C11—F6 | 119.5 (10) |
C27—Sn1—O3 | 95.4 (4) | C12—C11—C10 | 120.4 (10) |
C28—Sn1—O3 | 91.1 (4) | F6—C11—C10 | 120.1 (10) |
C27—Sn1—O2 | 88.2 (4) | F7—C12—C11 | 120.2 (11) |
C28—Sn1—O2 | 90.9 (4) | F7—C12—C13 | 121.3 (10) |
O3—Sn1—O2 | 77.6 (3) | C11—C12—C13 | 118.4 (10) |
C27—Sn1—N2 | 93.0 (4) | F8—C13—C14 | 121.8 (10) |
C28—Sn1—N2 | 89.7 (4) | F8—C13—C12 | 117.3 (9) |
O3—Sn1—N2 | 85.6 (3) | C14—C13—C12 | 120.9 (10) |
O2—Sn1—N2 | 163.2 (3) | C13—C14—C9 | 121.9 (10) |
C27—Sn1—N1 | 87.6 (4) | C13—C14—H14 | 119.0 |
C28—Sn1—N1 | 87.6 (4) | C9—C14—H14 | 119.0 |
O3—Sn1—N1 | 153.2 (3) | N1—C15—C16 | 121.5 (12) |
O2—Sn1—N1 | 129.2 (3) | N1—C15—H15 | 119.3 |
N2—Sn1—N1 | 67.6 (3) | C16—C15—H15 | 119.3 |
C27—Sn1—O1 | 85.9 (4) | C17—C16—C15 | 119.9 (12) |
C28—Sn1—O1 | 88.1 (4) | C17—C16—H16 | 120.0 |
O3—Sn1—O1 | 130.3 (3) | C15—C16—H16 | 120.0 |
O2—Sn1—O1 | 52.8 (2) | C16—C17—C18 | 120.4 (11) |
N2—Sn1—O1 | 144.0 (3) | C16—C17—H17 | 119.8 |
N1—Sn1—O1 | 76.4 (3) | C18—C17—H17 | 119.8 |
C19—N1—C15 | 118.0 (9) | C17—C18—C19 | 117.3 (11) |
C19—N1—Sn1 | 117.1 (6) | C17—C18—C25 | 124.1 (11) |
C15—N1—Sn1 | 124.9 (8) | C19—C18—C25 | 118.6 (11) |
C24—N2—C20 | 117.6 (9) | N1—C19—C18 | 123.0 (10) |
C24—N2—Sn1 | 123.4 (7) | N1—C19—C20 | 117.3 (8) |
C20—N2—Sn1 | 119.1 (7) | C18—C19—C20 | 119.7 (9) |
C1—O1—Sn1 | 88.1 (6) | N2—C20—C21 | 122.4 (10) |
C1—O2—Sn1 | 96.3 (7) | N2—C20—C19 | 118.9 (8) |
C8—O3—Sn1 | 133.0 (7) | C21—C20—C19 | 118.7 (9) |
O1—C1—O2 | 122.8 (10) | C22—C21—C20 | 117.8 (10) |
O1—C1—C2 | 120.2 (9) | C22—C21—C26 | 122.2 (10) |
O2—C1—C2 | 116.9 (10) | C20—C21—C26 | 120.0 (11) |
C3—C2—C7 | 116.8 (9) | C23—C22—C21 | 118.9 (10) |
C3—C2—C1 | 123.8 (9) | C23—C22—H22 | 120.6 |
C7—C2—C1 | 119.3 (10) | C21—C22—H22 | 120.6 |
C4—C3—F1 | 114.1 (9) | C22—C23—C24 | 118.8 (11) |
C4—C3—C2 | 124.0 (10) | C22—C23—H23 | 120.6 |
F1—C3—C2 | 121.9 (9) | C24—C23—H23 | 120.6 |
F2—C4—C3 | 122.1 (11) | N2—C24—C23 | 124.6 (11) |
F2—C4—C5 | 118.6 (10) | N2—C24—H24 | 117.7 |
C3—C4—C5 | 119.2 (10) | C23—C24—H24 | 117.7 |
F3—C5—C4 | 120.2 (11) | C26—C25—C18 | 122.3 (11) |
F3—C5—C6 | 121.3 (11) | C26—C25—H25 | 118.9 |
C4—C5—C6 | 118.5 (10) | C18—C25—H25 | 118.9 |
F4—C6—C7 | 119.7 (11) | C25—C26—C21 | 120.6 (11) |
F4—C6—C5 | 118.3 (10) | C25—C26—H26 | 119.7 |
C7—C6—C5 | 122.0 (10) | C21—C26—H26 | 119.7 |
C6—C7—C2 | 119.4 (10) | Sn1—C27—H27A | 109.5 |
C6—C7—H7 | 120.3 | Sn1—C27—H27B | 109.5 |
C2—C7—H7 | 120.3 | H27A—C27—H27B | 109.5 |
O4—C8—O3 | 126.4 (10) | Sn1—C27—H27C | 109.5 |
O4—C8—C9 | 120.3 (10) | H27A—C27—H27C | 109.5 |
O3—C8—C9 | 113.2 (9) | H27B—C27—H27C | 109.5 |
C14—C9—C10 | 116.1 (10) | Sn1—C28—H28A | 109.5 |
C14—C9—C8 | 120.4 (9) | Sn1—C28—H28B | 109.5 |
C10—C9—C8 | 123.5 (9) | H28A—C28—H28B | 109.5 |
F5—C10—C11 | 117.2 (10) | Sn1—C28—H28C | 109.5 |
F5—C10—C9 | 120.6 (9) | H28A—C28—H28C | 109.5 |
C11—C10—C9 | 122.1 (10) | H28B—C28—H28C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···F5i | 0.93 | 2.48 | 3.217 (13) | 136 |
C22—H22···O4i | 0.93 | 2.49 | 3.191 (14) | 133 |
Symmetry code: (i) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Sn(CH3)2(C7HF4O2)2(C12H8N2)] |
Mr | 715.12 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 7.265 (4), 10.174 (6), 18.957 (11) |
α, β, γ (°) | 90.519 (10), 90.205 (9), 110.247 (8) |
V (Å3) | 1314.5 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.07 |
Crystal size (mm) | 0.18 × 0.13 × 0.09 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.831, 0.910 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6410, 4483, 3007 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.081, 0.222, 1.01 |
No. of reflections | 4483 |
No. of parameters | 388 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.64, −2.31 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
Sn1—C27 | 2.072 (13) | Sn1—N2 | 2.389 (8) |
Sn1—C28 | 2.092 (13) | Sn1—N1 | 2.472 (8) |
Sn1—O3 | 2.146 (7) | Sn1—O1 | 2.554 (8) |
Sn1—O2 | 2.360 (7) | ||
C27—Sn1—C28 | 173.1 (4) | C28—Sn1—N1 | 87.6 (4) |
C27—Sn1—O3 | 95.4 (4) | O3—Sn1—N1 | 153.2 (3) |
C28—Sn1—O3 | 91.1 (4) | O2—Sn1—N1 | 129.2 (3) |
C27—Sn1—O2 | 88.2 (4) | N2—Sn1—N1 | 67.6 (3) |
C28—Sn1—O2 | 90.9 (4) | C27—Sn1—O1 | 85.9 (4) |
O3—Sn1—O2 | 77.6 (3) | C28—Sn1—O1 | 88.1 (4) |
C27—Sn1—N2 | 93.0 (4) | O3—Sn1—O1 | 130.3 (3) |
C28—Sn1—N2 | 89.7 (4) | O2—Sn1—O1 | 52.8 (2) |
O3—Sn1—N2 | 85.6 (3) | N2—Sn1—O1 | 144.0 (3) |
O2—Sn1—N2 | 163.2 (3) | N1—Sn1—O1 | 76.4 (3) |
C27—Sn1—N1 | 87.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···F5i | 0.93 | 2.48 | 3.217 (13) | 136 |
C22—H22···O4i | 0.93 | 2.49 | 3.191 (14) | 133 |
Symmetry code: (i) −x, −y, −z. |
Organotin carboxylate complexes have recently attracted much attention due to their biochemical and commercial applications (Narula et al., 1988). In order to explore the impact of the structure on properties of the complexes, as well as to analyze the structure–activity relationships, a large number of organotin carboxylates have been prepared and studied (Gielen, 2002). We report here the crystal structure of the title compound, Me2Sn(C6HF4CO2)2(C12H8N2), with 1,10-phenanthroline as a co-ligand.
The coordination geometry about the Sn atom is best described as distorted pentagonal bipyramidal with the axial positions occupied by methyl groups (Table 1). Three carboxylate O atoms (O1,O2,O3) from two tetrafluorobenzoate ligands and the two N atoms (N1,N2) of the 1,10-phenanthroline ligand occupy the basal plane (Fig. 1). The Sn—N distances (Table 1) are longer than the sum of the covalent radii of Sn and N atoms (2.15 Å), but much shorter than the sum of van der Waals radii of the two atoms (3.74 Å; Casas et al., 1997). The Sn1—O3 bond length of 2.146 (7) Å is close to the sum of the covalent radii of Sn and O atoms (2.13 Å), showing strong coordination interaction, which is in agreement with the monodentate coordination mode of the carboxylate group (Li et al., 2005). The Sn1—O2 [2.360 (7) Å] and Sn1—O1 [2.554 (8) Å] distances lie midway between the sums of the van der Waals and covalent radii of Sn and O atoms (2.13–3.68 Å; Ma et al., 2005).
In the crystal structure, C—H···F and C—H···O type hydrogen bonds link the molecules into cyclic centrosymmetric dimers (Table 2).