Bis{2-[(E)-(5-tert-butyl-2-hy­droxy­phen­yl)diazen­yl]benzoato}dimethyl­tin(IV)

Basu Baul, T.S.; Paul, A.; Tiekink, E.R.T.

doi:10.1107/S1600536811036543

Volume 67
Part 10
Pages m1383-m1384
October 2011

Received 5 September 2011
Accepted 8 September 2011
Online 14 September 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.033
wR = 0.071
Data-to-parameter ratio = 17.9
Details

Bis{2-[(E)-(5-tert-butyl-2-hydroxyphenyl)diazenyl]benzoato}dimethyltin(IV)

Tushar S. Basu Baul,^a ⁺ Anup Paul ^a and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, North-Eastern Hill University, NEHU Permanent Campus, Umshing, Shillong 793 022, India, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: Edward.Tiekink@gmail.com

In the title diorganotin dicarboxylate, [Sn(CH₃)₂(C₁₇H₁₇N₂O₃)₂], the tin(IV) atom is six-coordinated by four O atoms derived from asymmetrically coordinating carboxylate ligands, and two methyl-C atoms. The resulting C₂O₄ donor set defines a skew-trapezoidal bipyramid with the Sn-C bonds disposed over the weaker Sn-O bonds. Within each carboxylate ligand, the hydroxyl-H atom forms bifurcated O-H(O,N) hydrogen bonds with carboxylate-O and azo-N atoms. The dihedral angles between the benzene rings in the two ligands are 10.44 (11) and 34.24 (11)°. In the crystal, centrosymmetric dimers are formed through pairs of SnO interactions [2.8802 (16) Å], and the dimers are linked into supramolecular layers in the ac plane by C-H [pi] interactions.

Related literature

For background to the potential anti-cancer activity of related compounds, see: Basu Baul et al. (2011). For the synthesis of the ligand, see: Basu Baul et al. (2008). For related structural studies, see: Basu Baul et al. (2010). For a review of the structural chemistry of organotin carboxylates, see: Tiekink (1991).

Experimental

Crystal data

[Sn(CH₃)₂(C₁₇H₁₇N₂O₃)₂]
M_r = 743.43
Monoclinic, P 2₁ /c
a = 9.6298 (1) Å
b = 31.8788 (4) Å
c = 11.0963 (1) Å
= 93.502 (1)°
V = 3400.05 (6) Å³
Z = 4
Mo K radiation
= 0.80 mm^-1
T = 100 K
0.36 × 0.13 × 0.03 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.895, T_max = 1
26762 measured reflections
7749 independent reflections
6165 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.071
S = 1.04
7749 reflections
434 parameters
H-atom parameters constrained
_max = 0.55 e Å^-3
_min = -0.41 e Å^-3

Table 1
Selected bond lengths (Å)

Sn-O1	2.1118 (16)
Sn-O2	2.6967 (16)
Sn-O4	2.1120 (16)
Sn-O5	2.4482 (16)
Sn-C35	2.081 (3)
Sn-C36	2.098 (2)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C25-C30 ring.

D-HA	D-H	HA	DA	D-HA
O3-H3O1	0.84	2.49	3.142 (2)	136
O3-H3N1	0.84	1.87	2.573 (2)	140
O6-H6O5	0.84	2.20	2.877 (3)	137
O6-H6N3	0.84	1.93	2.620 (3)	139
C10-H10Cg1ⁱ	0.95	2.97	3.863 (2)	157
Symmetry code: (i) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6399 ).

Acknowledgements

The financial support of the Department of Science and Technology, New Delhi, India (grant No. SR/S1/IC-03/2005,TSBB), the Council of Scientific and Industrial Research, New Delhi, India [grant No. 09/347/(0197)/2011/EMR I, for the award of a Senior Research Fellowship to AP] and the University Grants Commission, New Delhi, India, through SAP-DSA, Phase-III, are gratefully acknowledged.

References

Basu Baul, T. S., Paul, A., Arman, H. D. & Tiekink, E. R. T. (2008). Acta Cryst. E64, o2125.
Basu Baul, T. S., Paul, A., Pellerito, L., Scopelliti, M., Singh, P., Verma, P., Duthie, A., de Vos, D. & Tiekink, E. R. T. (2011). Invest. New Drugs, 29, 285-299.
Basu Baul, T. S., Paul, A. & Tiekink, E. R. T. (2010). Z. Kristallogr. 225, 153-157.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1-23.

metal-organic compounds