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Volume 69 
Part 12 
Page m688  
December 2013  

Received 14 November 2013
Accepted 21 November 2013
Online 30 November 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
R = 0.040
wR = 0.107
Data-to-parameter ratio = 14.1
Details
Open access

{4-Chloro-N'-[(2-oxidonaphthalen-1-yl-[kappa]O)methyl­idene]benzohydrazidato-[kappa]2N',O}di­methyl­tin(IV)

aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
Correspondence e-mail: jchcui@163.com

In the title complex, [Sn(CH3)2(C18H11ClN2O2)], the SnIV ion is coordinated by two O atoms and an N atom from a 4-chloro-N'-[(2-oxidonaphthalen-1-yl)methyl­idene]benzohydrazidate ligand and two C atoms from two methyl ligands in a distorted trigonal-bipyramidal geometry [Sn-O = 2.092 (3) and 2.144 (3) Å; Sn-N = 2.160 (4) Å]. The dihedral angle between the naphthalene ring system and the benzene ring is 8.6 (2)°. In the crystal, adjacent mol­ecules are linked by weak C-H...O hydrogen bonds, forming a chain along the b-axis direction.

Related literature

For the biological activity and related structures of organotin compounds, see: Hong et al. (2013[Hong, M., Yin, H., Zhang, X., Li, C., Yue, C. & Cheng, S. (2013). J. Organomet. Chem., 724, 23-31.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(CH3)2(C18H11ClN2O2)]

  • Mr = 471.50

  • Monoclinic, P 21 /n

  • a = 8.7927 (8) Å

  • b = 17.4170 (15) Å

  • c = 12.5014 (12) Å

  • [beta] = 98.690 (9)°

  • V = 1892.5 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.51 mm-1

  • T = 293 K

  • 0.24 × 0.23 × 0.13 mm

Data collection
  • Siemens SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.714, Tmax = 0.828

  • 11127 measured reflections

  • 3343 independent reflections

  • 2584 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.107

  • S = 1.06

  • 3343 reflections

  • 237 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.83 e Å-3

  • [Delta][rho]min = -0.61 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O2i 0.93 2.54 3.388 (6) 152
Symmetry code: (i) [-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5669 ).


Acknowledgements

We acknowledge the Students Science and Technology Innovation Fund of Liaocheng University (SF2013096).

References

Hong, M., Yin, H., Zhang, X., Li, C., Yue, C. & Cheng, S. (2013). J. Organomet. Chem., 724, 23-31.  [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.


Acta Cryst (2013). E69, m688  [ doi:10.1107/S1600536813031826 ]

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