Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043371/tk2193sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043371/tk2193Isup2.hkl |
CCDC reference: 663579
The Schiff-base ligand was synthesized by the reaction of salicylaldehyde and 4-aminothiophenol in ethanol solution. The syntheses of (I) was carried out under an N2 atmosphere. The Schiff-base (0.229 g, 1 mmol) and (CH3)3SnCl (0.199 g, 1 mmol) were added to a solution of dry benzene (30 ml) in a Schlenk flash and stirred under refux conditions (353 K) for 12 h. The solution was filtered and after a week yellow crystals suitable for X-ray diffraction study were obtained. Yield, 0.423 g, 85%. m.p. 412–414 K.
Analysis found: C 48.85, H 4.91, N 3.54, O 4.02, S 8.10%; C19H19NOSSn requires: C 49.01, H 4.88, N 3.57, O 4.08, S 8.18%.
The H-atoms were included in the riding-model approximation with C—H = 0.93 - 0.96 Å and O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C-aromatic) and Uiso(H) = 1.5Ueq(C-methyl and O).
Schiff-bases are well known chelating ligands in coordination chemistry (Garnovski et al., 1993). During the last decade, Schiff-base complexes have been applied in catalytic reactions and biological systems (Anderson et al., 1997). Organotin complexes containing Schiff-bases have attracted much attention owing to their potential biological activities (Nath et al., 1997). In this contribution, the title compound (I) was synthesized and its crystal structure determined (Fig. 1 and Table 1). The central tin atom exists in a distorted tetrahedron defined by a C3S donor set. The geometric parameters are in good agreement with those found in (1-phenyl-1H-tetrazole-5-thiolato)trimethyltin (Cea-Olivares et al., 1994). The mean planes of the two benzene rings in (I) make a dihedral angle of 41.8 (2)°.
For related literature, see: Anderson et al. (1997); Cea-Olivares et al. (1994); Garnovski et al. (1993); Nath et al. (1997).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (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 structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme. The H atoms are omitted for clarity. |
C16H19NOSSn | F(000) = 784 |
Mr = 392.07 | Dx = 1.497 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2868 reflections |
a = 11.1385 (16) Å | θ = 3.0–23.6° |
b = 6.4148 (12) Å | µ = 1.58 mm−1 |
c = 24.490 (2) Å | T = 298 K |
β = 96.254 (2)° | Block, yellow |
V = 1739.5 (4) Å3 | 0.15 × 0.12 × 0.10 mm |
Z = 4 |
Siemens SMART CCD area-detector diffractometer | 3104 independent reflections |
Radiation source: sealed tube | 2284 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
φ and ω scans | θmax = 25.1°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→13 |
Tmin = 0.797, Tmax = 0.858 | k = −7→7 |
8291 measured reflections | l = −22→29 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.088P)2 + 2.8254P] where P = (Fo2 + 2Fc2)/3 |
3104 reflections | (Δ/σ)max = 0.004 |
184 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.96 e Å−3 |
C16H19NOSSn | V = 1739.5 (4) Å3 |
Mr = 392.07 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.1385 (16) Å | µ = 1.58 mm−1 |
b = 6.4148 (12) Å | T = 298 K |
c = 24.490 (2) Å | 0.15 × 0.12 × 0.10 mm |
β = 96.254 (2)° |
Siemens SMART CCD area-detector diffractometer | 3104 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2284 reflections with I > 2σ(I) |
Tmin = 0.797, Tmax = 0.858 | Rint = 0.051 |
8291 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.38 e Å−3 |
3104 reflections | Δρmin = −0.96 e Å−3 |
184 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 | 0.19708 (4) | 0.26552 (7) | 0.617154 (19) | 0.0594 (2) | |
N1 | 0.1773 (4) | 0.6301 (8) | 0.3530 (2) | 0.0482 (12) | |
O1 | 0.0779 (4) | 0.9533 (7) | 0.30112 (19) | 0.0684 (14) | |
H1 | 0.1096 | 0.8859 | 0.3273 | 0.103* | |
S1 | 0.36707 (17) | 0.2139 (3) | 0.56463 (8) | 0.0702 (6) | |
C1 | 0.3083 (5) | 0.3377 (9) | 0.5024 (2) | 0.0501 (13) | |
C2 | 0.3372 (6) | 0.5430 (10) | 0.4916 (2) | 0.0565 (14) | |
H2 | 0.3859 | 0.6194 | 0.5177 | 0.068* | |
C3 | 0.2936 (5) | 0.6341 (11) | 0.4421 (2) | 0.0555 (14) | |
H3 | 0.3136 | 0.7717 | 0.4354 | 0.067* | |
C4 | 0.2206 (5) | 0.5249 (9) | 0.4022 (2) | 0.0459 (12) | |
C5 | 0.1911 (6) | 0.3221 (9) | 0.4132 (2) | 0.0518 (13) | |
H5 | 0.1416 | 0.2470 | 0.3872 | 0.062* | |
C6 | 0.2341 (6) | 0.2275 (10) | 0.4626 (2) | 0.0561 (14) | |
H6 | 0.2134 | 0.0901 | 0.4693 | 0.067* | |
C7 | 0.1657 (5) | 0.5321 (10) | 0.3073 (2) | 0.0479 (12) | |
H7 | 0.1893 | 0.3932 | 0.3066 | 0.057* | |
C8 | 0.1166 (5) | 0.6320 (9) | 0.2562 (2) | 0.0476 (12) | |
C9 | 0.0727 (5) | 0.8369 (10) | 0.2554 (3) | 0.0530 (13) | |
C10 | 0.0284 (6) | 0.9290 (11) | 0.2056 (2) | 0.0595 (14) | |
H10 | 0.0018 | 1.0666 | 0.2049 | 0.071* | |
C11 | 0.0238 (6) | 0.8166 (11) | 0.1574 (3) | 0.0631 (15) | |
H11 | −0.0086 | 0.8776 | 0.1246 | 0.076* | |
C12 | 0.0668 (6) | 0.6144 (10) | 0.1571 (3) | 0.0607 (14) | |
H12 | 0.0644 | 0.5403 | 0.1243 | 0.073* | |
C13 | 0.1135 (5) | 0.5237 (11) | 0.2063 (2) | 0.0553 (14) | |
H13 | 0.1432 | 0.3883 | 0.2062 | 0.066* | |
C14 | 0.0469 (6) | 0.1300 (14) | 0.5697 (3) | 0.0709 (19) | |
H14A | 0.0054 | 0.0390 | 0.5924 | 0.085* | |
H14B | 0.0743 | 0.0517 | 0.5400 | 0.085* | |
H14C | −0.0070 | 0.2380 | 0.5551 | 0.085* | |
C15 | 0.1731 (9) | 0.5949 (15) | 0.6232 (4) | 0.109 (3) | |
H15A | 0.1490 | 0.6512 | 0.5873 | 0.131* | |
H15B | 0.2477 | 0.6580 | 0.6381 | 0.131* | |
H15C | 0.1117 | 0.6236 | 0.6468 | 0.131* | |
C16 | 0.2493 (7) | 0.1208 (15) | 0.6947 (3) | 0.077 (2) | |
H16A | 0.1990 | 0.0016 | 0.6988 | 0.093* | |
H16B | 0.2404 | 0.2184 | 0.7237 | 0.093* | |
H16C | 0.3321 | 0.0772 | 0.6965 | 0.093* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0621 (3) | 0.0607 (4) | 0.0553 (3) | −0.0029 (2) | 0.0070 (2) | −0.0069 (2) |
N1 | 0.047 (3) | 0.054 (3) | 0.044 (3) | 0.003 (2) | 0.008 (2) | 0.000 (3) |
O1 | 0.087 (3) | 0.061 (3) | 0.057 (3) | 0.020 (3) | 0.005 (3) | −0.004 (2) |
S1 | 0.0544 (10) | 0.0942 (15) | 0.0622 (11) | 0.0173 (9) | 0.0081 (8) | 0.0232 (10) |
C1 | 0.043 (3) | 0.057 (3) | 0.051 (3) | 0.004 (2) | 0.012 (2) | 0.001 (3) |
C2 | 0.058 (3) | 0.062 (3) | 0.048 (3) | −0.008 (3) | 0.003 (3) | −0.004 (3) |
C3 | 0.060 (3) | 0.053 (3) | 0.053 (3) | −0.005 (3) | 0.007 (2) | 0.001 (3) |
C4 | 0.047 (2) | 0.050 (3) | 0.043 (3) | −0.001 (2) | 0.013 (2) | −0.002 (2) |
C5 | 0.056 (3) | 0.056 (3) | 0.046 (3) | −0.007 (2) | 0.013 (2) | −0.007 (2) |
C6 | 0.063 (3) | 0.055 (3) | 0.053 (3) | −0.002 (3) | 0.015 (3) | 0.000 (3) |
C7 | 0.045 (2) | 0.053 (3) | 0.047 (3) | 0.000 (2) | 0.010 (2) | 0.000 (2) |
C8 | 0.038 (2) | 0.058 (3) | 0.048 (3) | −0.002 (2) | 0.010 (2) | −0.001 (2) |
C9 | 0.041 (3) | 0.063 (3) | 0.056 (3) | −0.006 (2) | 0.009 (2) | −0.003 (3) |
C10 | 0.053 (3) | 0.065 (3) | 0.060 (3) | 0.000 (3) | 0.006 (3) | 0.010 (3) |
C11 | 0.049 (3) | 0.081 (4) | 0.059 (3) | −0.007 (3) | 0.005 (3) | 0.010 (3) |
C12 | 0.052 (3) | 0.078 (3) | 0.053 (3) | −0.009 (3) | 0.008 (2) | −0.009 (3) |
C13 | 0.052 (3) | 0.063 (3) | 0.052 (3) | −0.006 (3) | 0.010 (2) | −0.003 (3) |
C14 | 0.061 (4) | 0.088 (5) | 0.064 (4) | −0.009 (4) | 0.010 (3) | −0.019 (4) |
C15 | 0.114 (7) | 0.071 (6) | 0.141 (8) | 0.011 (5) | 0.005 (6) | −0.018 (6) |
C16 | 0.085 (5) | 0.093 (6) | 0.055 (4) | −0.012 (4) | 0.012 (4) | −0.001 (4) |
Sn1—S1 | 2.425 (2) | C7—H7 | 0.9300 |
Sn1—C14 | 2.117 (7) | C8—C13 | 1.402 (7) |
Sn1—C15 | 2.137 (9) | C8—C9 | 1.402 (7) |
Sn1—C16 | 2.138 (7) | C9—C10 | 1.397 (7) |
N1—C7 | 1.277 (8) | C10—C11 | 1.380 (7) |
N1—C4 | 1.420 (7) | C10—H10 | 0.9300 |
O1—C9 | 1.342 (7) | C11—C12 | 1.382 (7) |
O1—H1 | 0.8200 | C11—H11 | 0.9300 |
S1—C1 | 1.779 (6) | C12—C13 | 1.388 (7) |
C1—C2 | 1.388 (7) | C12—H12 | 0.9300 |
C1—C6 | 1.398 (7) | C13—H13 | 0.9300 |
C2—C3 | 1.385 (7) | C14—H14A | 0.9600 |
C2—H2 | 0.9300 | C14—H14B | 0.9600 |
C3—C4 | 1.391 (6) | C14—H14C | 0.9600 |
C3—H3 | 0.9300 | C15—H15A | 0.9600 |
C4—C5 | 1.376 (7) | C15—H15B | 0.9600 |
C5—C6 | 1.392 (7) | C15—H15C | 0.9600 |
C5—H5 | 0.9300 | C16—H16A | 0.9600 |
C6—H6 | 0.9300 | C16—H16B | 0.9600 |
C7—C8 | 1.459 (8) | C16—H16C | 0.9600 |
S1—Sn1—C14 | 105.6 (2) | O1—C9—C10 | 118.2 (6) |
S1—Sn1—C15 | 106.4 (3) | O1—C9—C8 | 121.8 (5) |
S1—Sn1—C16 | 105.0 (2) | C10—C9—C8 | 119.9 (6) |
C14—Sn1—C15 | 110.3 (3) | C11—C10—C9 | 120.2 (6) |
C14—Sn1—C16 | 115.6 (3) | C11—C10—H10 | 119.9 |
C15—Sn1—C16 | 113.1 (4) | C9—C10—H10 | 119.9 |
C7—N1—C4 | 120.2 (5) | C10—C11—C12 | 121.0 (6) |
C9—O1—H1 | 109.5 | C10—C11—H11 | 119.5 |
Sn1—S1—C1 | 99.1 (2) | C12—C11—H11 | 119.5 |
C2—C1—C6 | 118.7 (6) | C11—C12—C13 | 119.1 (6) |
C2—C1—S1 | 121.0 (5) | C11—C12—H12 | 120.5 |
C6—C1—S1 | 120.4 (5) | C13—C12—H12 | 120.5 |
C3—C2—C1 | 120.0 (6) | C12—C13—C8 | 121.4 (6) |
C3—C2—H2 | 120.0 | C12—C13—H13 | 119.3 |
C1—C2—H2 | 120.0 | C8—C13—H13 | 119.3 |
C2—C3—C4 | 121.7 (6) | Sn1—C14—H14A | 109.5 |
C2—C3—H3 | 119.1 | Sn1—C14—H14B | 109.5 |
C4—C3—H3 | 119.1 | H14A—C14—H14B | 109.5 |
C5—C4—C3 | 118.2 (6) | Sn1—C14—H14C | 109.5 |
C5—C4—N1 | 123.3 (5) | H14A—C14—H14C | 109.5 |
C3—C4—N1 | 118.5 (5) | H14B—C14—H14C | 109.5 |
C4—C5—C6 | 121.0 (6) | Sn1—C15—H15A | 109.5 |
C4—C5—H5 | 119.5 | Sn1—C15—H15B | 109.5 |
C6—C5—H5 | 119.5 | H15A—C15—H15B | 109.5 |
C5—C6—C1 | 120.4 (6) | Sn1—C15—H15C | 109.5 |
C5—C6—H6 | 119.8 | H15A—C15—H15C | 109.5 |
C1—C6—H6 | 119.8 | H15B—C15—H15C | 109.5 |
N1—C7—C8 | 121.9 (6) | Sn1—C16—H16A | 109.5 |
N1—C7—H7 | 119.1 | Sn1—C16—H16B | 109.5 |
C8—C7—H7 | 119.1 | H16A—C16—H16B | 109.5 |
C13—C8—C9 | 118.5 (6) | Sn1—C16—H16C | 109.5 |
C13—C8—C7 | 120.1 (5) | H16A—C16—H16C | 109.5 |
C9—C8—C7 | 121.4 (5) | H16B—C16—H16C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | C16H19NOSSn |
Mr | 392.07 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 11.1385 (16), 6.4148 (12), 24.490 (2) |
β (°) | 96.254 (2) |
V (Å3) | 1739.5 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.58 |
Crystal size (mm) | 0.15 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.797, 0.858 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8291, 3104, 2284 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.165, 1.01 |
No. of reflections | 3104 |
No. of parameters | 184 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.96 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
Sn1—S1 | 2.425 (2) | Sn1—C16 | 2.138 (7) |
Sn1—C14 | 2.117 (7) | N1—C7 | 1.277 (8) |
Sn1—C15 | 2.137 (9) | ||
S1—Sn1—C14 | 105.6 (2) | C14—Sn1—C16 | 115.6 (3) |
S1—Sn1—C15 | 106.4 (3) | C15—Sn1—C16 | 113.1 (4) |
S1—Sn1—C16 | 105.0 (2) | Sn1—S1—C1 | 99.1 (2) |
C14—Sn1—C15 | 110.3 (3) |
Schiff-bases are well known chelating ligands in coordination chemistry (Garnovski et al., 1993). During the last decade, Schiff-base complexes have been applied in catalytic reactions and biological systems (Anderson et al., 1997). Organotin complexes containing Schiff-bases have attracted much attention owing to their potential biological activities (Nath et al., 1997). In this contribution, the title compound (I) was synthesized and its crystal structure determined (Fig. 1 and Table 1). The central tin atom exists in a distorted tetrahedron defined by a C3S donor set. The geometric parameters are in good agreement with those found in (1-phenyl-1H-tetrazole-5-thiolato)trimethyltin (Cea-Olivares et al., 1994). The mean planes of the two benzene rings in (I) make a dihedral angle of 41.8 (2)°.