{4-Hydroxy-N 0 -[(2-oxido-1-naphthyl- jO)methylidene]benzohydrazidato- j 2 N 0 ,O}dimethyltin(IV) Md. Abu Affan, a ‡ Norrihan B. Sam, a Fasihuddin B. Ahmad a and Edward R. T. Tiekink b * a Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, and b Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia Correspondence e-mail: edward.tiekink@gmail.com Received 6 July 2010; accepted 8 July 2010 Key indicators: single-crystal X-ray study; T = 150 K; mean (C–C) = 0.005 A ˚ ; R factor = 0.031; wR factor = 0.069; data-to-parameter ratio = 14.0. Two independent but very similar molecules comprise the asymmetric unit of the title compound, [Sn(CH 3 ) 2 - (C 18 H 12 N 2 O 3 )]. Each Sn atom is coordinated by two methyl groups and two O atoms and an N atom from the dinegative tridentate ligand. The resultant C 2 NO 2 donor set defines a coordination geometry intermediate between square-pyra- midal and trigonal-pyramidal, with a small tendency towards the former. Zigzag chains running along the a axis mediated by O—HN hydrogen bonding characterize the crystal packing. These are connected into layers in the ab plane by a combination of C—HN and – [centroid–centroid distances = 3.658 (2) and 3.6740 (18) A ˚ ] interactions. The layers are connected along the c axis via C—HO inter- actions. Related literature For related studies on organotin compounds, see: Affan et al. (2009); Zukerman-Schpector et al. (2009). For the structure of the dichloromethane solvate of the title compound, see: Cui et al. (2007). For coordination geometry, see: Addison et al. (1984). Experimental Crystal data [Sn(CH 3 ) 2 (C 18 H 12 N 2 O 3 )] M r = 453.05 Monoclinic, P2 1 =c a = 12.9422 (4) A ˚ b = 16.5264 (5) A ˚ c = 16.9949 (5) A ˚  = 94.923 (3)  V = 3621.59 (19) A ˚ 3 Z =8 Mo K radiation  = 1.43 mm 1 T = 150 K 0.20  0.15  0.06 mm Data collection Oxford Diffraction Gemini E diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) T min = 0.863, T max = 1.000 12413 measured reflections 6668 independent reflections 5647 reflections with I >2(I) R int = 0.027 Refinement R[F 2 >2(F 2 )] = 0.031 wR(F 2 ) = 0.069 S = 1.05 6668 reflections 475 parameters H-atom parameters constrained Á max = 0.73 e A ˚ 3 Á min = 0.51 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚ ,  ). D—HA D—H HA DA D—HA O3—H3N3 i 0.84 1.91 2.749 (3) 178 O6—H6aN1 ii 0.84 1.91 2.738 (3) 167 C8—H8O5 iii 0.95 2.59 3.477 (4) 155 C21—H21aN1 iv 0.98 2.62 3.494 (4) 149 Symmetry codes: (i) x  1; y þ 3 2 ; z  1 2 ; (ii) x; y þ 3 2 ; z þ 1 2 ; (iii) x  1; y; z  1; (iv) x þ 1; y þ 1; z þ 1. Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (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 publi- cation: publCIF (Westrip, 2010). We thank MOSTI (grant No. 06–01-09-SF0046), Universiti Malaysia Sarawak, and Oxford Diffraction for supporting this study. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5292). References Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356. Affan, M. A., Foo, S. W., Jusoh, I., Hanapi, S. & Tiekink, E. R. T. (2009). Inorg. Chim. Acta, 362, 5031–5037. Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Cui, J., Yin, H. & Qiao, Y. (2007). Acta Cryst. E63, m3138. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Zukerman-Schpector, J., Affan, M. A., Foo, S. W. & Tiekink, E. R.T. (2009). Acta Cryst. E65, o2951. metal-organic compounds m924 Affan et al. doi:10.1107/S1600536810027078 Acta Cryst. (2010). E66, m924 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 ‡ Additional correspondence author, e-mail: maaffan@frst.unimas.my.