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Acta Cryst. (2007). E63, m2498    [ doi:10.1107/S1600536807043371 ]

2-{[4-(Trimethylstannylthio)phenylimino]methyl}phenol

J. Li, C. Ma and G. He

Abstract top

The mononuclear Schiff base compound C16H19NOSSn or [(CH3)3Sn(SC6H4-4-N=C(H)C6H4-OH-2)] features a slightly distorted C3S tetrahedral geometry for Sn. The mean planes of the two benzene rings make a dihedral angle of 41.8 (2)°, indicating nonplanarity of the molecule.

Comment top

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)°.

Related literature top

For related literature, see: Anderson et al. (1997); Cea-Olivares et al. (1994); Garnovski et al. (1993); Nath et al. (1997).

Experimental top

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%.

Refinement top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme. The H atoms are omitted for clarity.
2-{[4-(Trimethylstannylthio)phenylimino]methyl}phenol top
Crystal data top
C16H19NOSSnF000 = 784
Mr = 392.07Dx = 1.497 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2868 reflections
a = 11.1385 (16) Åθ = 3.0–23.6º
b = 6.4148 (12) ŵ = 1.58 mm−1
c = 24.490 (2) ÅT = 298 (2) K
β = 96.254 (2)ºBlock, yellow
V = 1739.5 (4) Å30.15 × 0.12 × 0.10 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer		3104 independent reflections
Radiation source: sealed tube2284 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.051
T = 298(2) Kθmax = 25.1º
φ and ω scansθmin = 1.7º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→13
Tmin = 0.797, Tmax = 0.858k = −7→7
8291 measured reflectionsl = −22→29
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.165  w = 1/[σ2(Fo2) + (0.088P)2 + 2.8254P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.004
3104 reflectionsΔρmax = 0.38 e Å−3
184 parametersΔρmin = −0.96 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C16H19NOSSnV = 1739.5 (4) Å3
Mr = 392.07Z = 4
Monoclinic, P21/nMo Kα
a = 11.1385 (16) ŵ = 1.58 mm−1
b = 6.4148 (12) ÅT = 298 (2) K
c = 24.490 (2) Å0.15 × 0.12 × 0.10 mm
β = 96.254 (2)º
Data collection top
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 = 0.858Rint = 0.051
8291 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.054184 parameters
wR(F2) = 0.165H-atom parameters constrained
S = 1.01Δρmax = 0.38 e Å−3
3104 reflectionsΔρmin = −0.96 e Å−3
Special details top

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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.19708 (4)0.26552 (7)0.617154 (19)0.0594 (2)
N10.1773 (4)0.6301 (8)0.3530 (2)0.0482 (12)
O10.0779 (4)0.9533 (7)0.30112 (19)0.0684 (14)
H10.10960.88590.32730.103*
S10.36707 (17)0.2139 (3)0.56463 (8)0.0702 (6)
C10.3083 (5)0.3377 (9)0.5024 (2)0.0501 (13)
C20.3372 (6)0.5430 (10)0.4916 (2)0.0565 (14)
H20.38590.61940.51770.068*
C30.2936 (5)0.6341 (11)0.4421 (2)0.0555 (14)
H30.31360.77170.43540.067*
C40.2206 (5)0.5249 (9)0.4022 (2)0.0459 (12)
C50.1911 (6)0.3221 (9)0.4132 (2)0.0518 (13)
H50.14160.24700.38720.062*
C60.2341 (6)0.2275 (10)0.4626 (2)0.0561 (14)
H60.21340.09010.46930.067*
C70.1657 (5)0.5321 (10)0.3073 (2)0.0479 (12)
H70.18930.39320.30660.057*
C80.1166 (5)0.6320 (9)0.2562 (2)0.0476 (12)
C90.0727 (5)0.8369 (10)0.2554 (3)0.0530 (13)
C100.0284 (6)0.9290 (11)0.2056 (2)0.0595 (14)
H100.00181.06660.20490.071*
C110.0238 (6)0.8166 (11)0.1574 (3)0.0631 (15)
H11−0.00860.87760.12460.076*
C120.0668 (6)0.6144 (10)0.1571 (3)0.0607 (14)
H120.06440.54030.12430.073*
C130.1135 (5)0.5237 (11)0.2063 (2)0.0553 (14)
H130.14320.38830.20620.066*
C140.0469 (6)0.1300 (14)0.5697 (3)0.0709 (19)
H14A0.00540.03900.59240.085*
H14B0.07430.05170.54000.085*
H14C−0.00700.23800.55510.085*
C150.1731 (9)0.5949 (15)0.6232 (4)0.109 (3)
H15A0.14900.65120.58730.131*
H15B0.24770.65800.63810.131*
H15C0.11170.62360.64680.131*
C160.2493 (7)0.1208 (15)0.6947 (3)0.077 (2)
H16A0.19900.00160.69880.093*
H16B0.24040.21840.72370.093*
H16C0.33210.07720.69650.093*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0621 (3)0.0607 (4)0.0553 (3)−0.0029 (2)0.0070 (2)−0.0069 (2)
N10.047 (3)0.054 (3)0.044 (3)0.003 (2)0.008 (2)0.000 (3)
O10.087 (3)0.061 (3)0.057 (3)0.020 (3)0.005 (3)−0.004 (2)
S10.0544 (10)0.0942 (15)0.0622 (11)0.0173 (9)0.0081 (8)0.0232 (10)
C10.043 (3)0.057 (3)0.051 (3)0.004 (2)0.012 (2)0.001 (3)
C20.058 (3)0.062 (3)0.048 (3)−0.008 (3)0.003 (3)−0.004 (3)
C30.060 (3)0.053 (3)0.053 (3)−0.005 (3)0.007 (2)0.001 (3)
C40.047 (2)0.050 (3)0.043 (3)−0.001 (2)0.013 (2)−0.002 (2)
C50.056 (3)0.056 (3)0.046 (3)−0.007 (2)0.013 (2)−0.007 (2)
C60.063 (3)0.055 (3)0.053 (3)−0.002 (3)0.015 (3)0.000 (3)
C70.045 (2)0.053 (3)0.047 (3)0.000 (2)0.010 (2)0.000 (2)
C80.038 (2)0.058 (3)0.048 (3)−0.002 (2)0.010 (2)−0.001 (2)
C90.041 (3)0.063 (3)0.056 (3)−0.006 (2)0.009 (2)−0.003 (3)
C100.053 (3)0.065 (3)0.060 (3)0.000 (3)0.006 (3)0.010 (3)
C110.049 (3)0.081 (4)0.059 (3)−0.007 (3)0.005 (3)0.010 (3)
C120.052 (3)0.078 (3)0.053 (3)−0.009 (3)0.008 (2)−0.009 (3)
C130.052 (3)0.063 (3)0.052 (3)−0.006 (3)0.010 (2)−0.003 (3)
C140.061 (4)0.088 (5)0.064 (4)−0.009 (4)0.010 (3)−0.019 (4)
C150.114 (7)0.071 (6)0.141 (8)0.011 (5)0.005 (6)−0.018 (6)
C160.085 (5)0.093 (6)0.055 (4)−0.012 (4)0.012 (4)−0.001 (4)
Geometric parameters (Å, °) top
Sn1—S12.425 (2)C7—H70.9300
Sn1—C142.117 (7)C8—C131.402 (7)
Sn1—C152.137 (9)C8—C91.402 (7)
Sn1—C162.138 (7)C9—C101.397 (7)
N1—C71.277 (8)C10—C111.380 (7)
N1—C41.420 (7)C10—H100.9300
O1—C91.342 (7)C11—C121.382 (7)
O1—H10.8200C11—H110.9300
S1—C11.779 (6)C12—C131.388 (7)
C1—C21.388 (7)C12—H120.9300
C1—C61.398 (7)C13—H130.9300
C2—C31.385 (7)C14—H14A0.9600
C2—H20.9300C14—H14B0.9600
C3—C41.391 (6)C14—H14C0.9600
C3—H30.9300C15—H15A0.9600
C4—C51.376 (7)C15—H15B0.9600
C5—C61.392 (7)C15—H15C0.9600
C5—H50.9300C16—H16A0.9600
C6—H60.9300C16—H16B0.9600
C7—C81.459 (8)C16—H16C0.9600
S1—Sn1—C14105.6 (2)O1—C9—C10118.2 (6)
S1—Sn1—C15106.4 (3)O1—C9—C8121.8 (5)
S1—Sn1—C16105.0 (2)C10—C9—C8119.9 (6)
C14—Sn1—C15110.3 (3)C11—C10—C9120.2 (6)
C14—Sn1—C16115.6 (3)C11—C10—H10119.9
C15—Sn1—C16113.1 (4)C9—C10—H10119.9
C7—N1—C4120.2 (5)C10—C11—C12121.0 (6)
C9—O1—H1109.5C10—C11—H11119.5
Sn1—S1—C199.1 (2)C12—C11—H11119.5
C2—C1—C6118.7 (6)C11—C12—C13119.1 (6)
C2—C1—S1121.0 (5)C11—C12—H12120.5
C6—C1—S1120.4 (5)C13—C12—H12120.5
C3—C2—C1120.0 (6)C12—C13—C8121.4 (6)
C3—C2—H2120.0C12—C13—H13119.3
C1—C2—H2120.0C8—C13—H13119.3
C2—C3—C4121.7 (6)Sn1—C14—H14A109.5
C2—C3—H3119.1Sn1—C14—H14B109.5
C4—C3—H3119.1H14A—C14—H14B109.5
C5—C4—C3118.2 (6)Sn1—C14—H14C109.5
C5—C4—N1123.3 (5)H14A—C14—H14C109.5
C3—C4—N1118.5 (5)H14B—C14—H14C109.5
C4—C5—C6121.0 (6)Sn1—C15—H15A109.5
C4—C5—H5119.5Sn1—C15—H15B109.5
C6—C5—H5119.5H15A—C15—H15B109.5
C5—C6—C1120.4 (6)Sn1—C15—H15C109.5
C5—C6—H6119.8H15A—C15—H15C109.5
C1—C6—H6119.8H15B—C15—H15C109.5
N1—C7—C8121.9 (6)Sn1—C16—H16A109.5
N1—C7—H7119.1Sn1—C16—H16B109.5
C8—C7—H7119.1H16A—C16—H16B109.5
C13—C8—C9118.5 (6)Sn1—C16—H16C109.5
C13—C8—C7120.1 (5)H16A—C16—H16C109.5
C9—C8—C7121.4 (5)H16B—C16—H16C109.5
Selected geometric parameters (Å, °) top
Sn1—S12.425 (2)Sn1—C162.138 (7)
Sn1—C142.117 (7)N1—C71.277 (8)
Sn1—C152.137 (9)
S1—Sn1—C14105.6 (2)C14—Sn1—C16115.6 (3)
S1—Sn1—C15106.4 (3)C15—Sn1—C16113.1 (4)
S1—Sn1—C16105.0 (2)Sn1—S1—C199.1 (2)
C14—Sn1—C15110.3 (3)
Acknowledgements top

The authors thank the Postgraduate Foundation of Taishan University (No. Y06–2-12) for financial support.

references
References top

Anderson, O. P., Cour, A. L., Findeisen, M., Hennig, L., Simonsen, O., Taylor, L. & Toflund, H. (1997). J. Chem. Soc. Dalton Trans. pp. 111–120.

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Garnovski, A. D., Nivorozhkin, A. L. & Minki, V. I. (1993). Coord. Chem. Rev. 126, 1–69.

Nath, M., Yadav, R., Gielen, M., Dalil, H., De Vos, D. & Eng, G. (1997). Appl. Organomet. Chem. 11, 727–736.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.

Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.