[3-(Dimethyl­amino)benzoato]triphenyl­tin(IV)

Win, Y.F.; Teoh, S.G.; Ha, S.T.; Kia, R.; Fun, H.-K.

doi:10.1107/S1600536808036337

Volume 64
Part 12
Pages m1530-m1531
December 2008

Received 1 November 2008
Accepted 6 November 2008
Online 13 November 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.017
wR = 0.049
Data-to-parameter ratio = 18.6
Details

[3-(Dimethylamino)benzoato]triphenyltin(IV)

Yip Foo Win,^a ⁺ Siang Guan Teoh,^a Sie Tiong Ha,^b Reza Kia ^c and Hoong-Kun Fun ^c ^*

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bUniversiti Tunku Abdul Rahman, Faculty of Engineering and Science, Jalan Genting Kelang, Setapak 53300, Kuala Lumpur, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound, [Sn(C₆H₅)₃(C₉H₁₀NO₂)], the Sn atom is coordinated by three phenyl groups and a carboxylate anion in a distorted tetrahedral geometry. An intramolecular C-HO interaction forms an S(7) ring motif. The dihedral angles between the benzoate group and the other three phenyl rings are 76.94 (8), 66.82 (8) and 42.34 (9)°. The crystal structure is further stabilized by intermolecular C-H [pi] interactions.

Related literature

For hydrogen-bond motifs, see Bernstein et al. (1995). For values of bond lengths, see Allen et al. (1987). For related literature on triorganotin(IV) complexes see, for example: Willem et al. (1997); Novelli et al. (1999); Gielen et al. (2000); Tian et al. (2005); Baul et al. (2001); Win et al. (2006, 2007a,b); Yeap & Teoh (2003).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₉H₁₀NO₂)]
M_r = 514.17
Triclinic, $[P \overline 1]$
a = 9.1140 (2) Å
b = 10.0027 (2) Å
c = 14.5066 (4) Å
= 100.925 (1)°
= 103.106 (1)°
= 110.778 (1)°
V = 1150.13 (5) Å³
Z = 2
Mo K radiation
= 1.13 mm^-1
T = 100.0 (1) K
0.46 × 0.42 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.623, T_max = 0.830
18268 measured reflections
5259 independent reflections
5141 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.017
wR(F²) = 0.049
S = 1.08
5259 reflections
282 parameters
H-atom parameters constrained
_max = 0.53 e Å^-3
_min = -0.56 e Å^-3

Table 1
Selected bond lengths (Å)

Sn1-O1	2.0649 (11)
Sn1-C1	2.1239 (15)
Sn1-C13	2.1260 (14)
Sn1-C7	2.1290 (14)

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8AO2	0.93	2.43	3.126 (2)	132
C24-H24ACg1ⁱ	0.93	2.88	3.6772 (19)	144
C26-H26BCg2ⁱⁱ	0.96	2.74	3.672 (2)	164
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2195 ).

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the RU research grant 101/PKIMIA/815002 and facilities. HKF and RK thanks the Malaysian Government and Universiti sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Baul, T. S. B., Dhar, S., Pyke, S. M., Tiekink, E. R. T., Rivarola, E., Butcher, R. & Smith, F. E. (2001). J. Organomet. Chem. 633, 7-17.
Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Gielen, M., Biesemans, M., Vos, D. d. & Willem, R. (2000). J. Inorg. Biochem. 79, 139-145.
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Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
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Win, Y. F., Guan, T. S., Ismail, N. L. & Yamin, B. M. (2006). Acta Cryst. E62, m3146-m3148.
Win, Y. F., Teoh, S.-G., Ng, S.-L., Fun, H.-K. & Ahmad, S. (2007a). Acta Cryst. E63, m2220-m2221.
Win, Y. F., Teoh, S. G., Teh, J. B.-J., Fun, H.-K. & Zakaria, L. (2007b). Acta Cryst. E63, m323-m325.
Yeap, L.-L. & Teoh, S. G. (2003). J. Coord. Chem. 56, 701-708.

metal-organic compounds