metal-organic papers m46 Yang Farina et al.  [Sn(C 6 H 5 ) 2 (C 5 H 10 NO 2 S 2 ) 2 ] DOI: 101107/S1600536800020407 Acta Cryst. (2001). E57, m46±m47 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Bis[N,N-bis(2-hydroxyethyl)dithiocarbamato-S,S 0 ]- diphenyltin(IV) Yang Farina, a A. Hamid Othman, a Ibrahim Abdul Razak, b Hoong-Kun Fun, b Seik Weng Ng c * and Ibrahim Baba a a School of Chemical Sciences, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia, b X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and c Institute of Postgraduate Studies, University of Malaya, 50603 Kuala Lumpur, Malaysia Correspondence e-mail: h1nswen@umcsd.um.edu.my Key indicators Single-crystal X-ray study T = 298 K Mean (C±C) = 0.007 A Ê R factor = 0.048 wR factor = 0.112 Data-to-parameter ratio = 20.5 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e. # 2001 International Union of Crystallography Printed in Great Britain ± all rights reserved The Sn atom in the title compound, [Sn(C 6 H 5 ) 2 - (C 5 H 10 NO 2 S 2 ) 2 ], is six-coordinate in a cis-C 2 SnS 4 octahedral environment. Comment Six-coordinate bis-chelated diaryltin compounds generally adopt a cis-octahedral geometry (Ng et al., 1987). In di- phenyltin bis(diethyldithiocarbamate), (II), the chelation by one dithiocarbamate group is relatively symmetrical [SnÐS = 2.613 (5) and 2.637 (5) A Ê ] whereas the chelation by the other is not [SnÐS = 2.548 (5) and 2.790 (6) A Ê ]; the CÐSnÐC angle is opened up to 101.4 (6) A Ê (Lindley & Carr, 1974). The bond dimensions in the title compound, (I), are similar to those in (II); in (I), the hydroxyl groups of each dithiocarbamate ligand are hydrogen bonded to each other. Adjacent molecules are linked by hydrogen bonds into a linear chain structure. The cis geometry contrasts with the skew-trapezoidal geometry [CÐ SnÐC = 139.3 (2)  ] adopted by the dimethyltin homolog (Yang Farina et al., 2000). Experimental A solution of carbon disul®de in methanol was added to a mixture of diphenyltin dichloride and diethanolamine (1:2 molar ratio) at 277 K. The mixture was stirred to afford a pale-yellow solid, which was recrystallized from a 3:2 methanol±chloroform mixture to afford (I) (m.p. 402±403 K). Elemental analysis, found (calculated) for C 22 H 30 - N 2 O 4 S 4 Sn: C 42.7 (41.7), H 4.6 (4.8), N 4.5 (4.4), Sn 18.3% (18.7%). Crystal data [Sn(C 6 H 5 ) 2 (C 5 H 10 NO 2 S 2 ) 2 ] M r = 633.41 Triclinic, P 1 a = 9.0118 (2) A Ê b = 12.4051 (1) A Ê c = 12.6024 (2) A Ê  = 86.889 (1)   = 69.575 (1)   = 88.293 (1)  V = 1318.24 (4) A Ê 3 Z =2 D x = 1.596 Mg m 3 Mo K radiation Cell parameters from 7568 re¯ections  = 1.6±29.5   = 1.32 mm 1 T = 298 (2) K Block, colorless 0.40  0.22  0.20 mm Received 7 December 2000 Accepted 15 December 2000 Online 22 December 2000