Experimental. Crystal data
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1 electronic papers Acta Crystallographica Section C Crystal Structure Communications ISSN catena-poly[fac-trichloromethyltin(iv)-l-[meso-1,2-bis(phenylsulfinyl)ethane-o:o 0 ]] Maria Teresa do Prado Gambardella, a * Regina Helena Porto Francisco, a Ana Maria G. Dias Rodrigues a and GerimaÂrio Freitas de Sousa b a Instituto de QuõÂmica de SaÄo Carlos, USP, Caixa Postal 780, SaÄo Carlos SP, Brazil, and b Departamento de QuõÂmica, UnB, Caixa Postal 04478, BrasõÂlia DF, Brazil Correspondence teca@iqsc.sc.usp.br Received 23 March 2000 Accepted 24 March 2000 Data validation number: IUC In the title compound, [SnCl 3 (CH 3 )(C 6 H 5 SOCH 2 ) 2 ] n, the octahedral Sn IV centres are bridged by meso-1,2-bis(phenylsul nyl)ethane ligands forming in nite chains along the [100] direction. Comment This study is part of structural studies on adducts of halide± organotin compounds with sulfoxide derivatives. The meso-1,2-bis(phenylsul nyl)ethane ligand, meso- (C 6 H 5 SOCH 2 ) 2, crystallizes with a centre of symmetry at the middle of the ethane CÐC bond (Cattalini et al., 1979). The occurrence of this centre of symmetry was also observed here, (I), and in the structures of [SnCl 2 (CH 3 ) 2 {meso-(c 6 H 5 SO- CH 2 ) 2 }] (Carvalho et al., 1996a), [SnCl 2 (CH 3 ) 2 {meso-(c 3 H 7 S- OCH 2 ) 2 }] (Carvalho et al., 1996b) and cis-[ptcl 2 - {P(C 2 H 5 ) 3 }{meso-(c 6 H 5 SOCH 2 ) 2 }] 2 (Francisco et al., 1995), where the Sn IV and Pt II cations have octahedral and squareplanar geometries, respectively. [SnÐCl (9) A Ê ]. Completing the coordination, there are two equivalent sulfoxide groups in a cis orientation [both with an SnÐO distance of (2) A Ê ] and a methyl group at a SnÐC distance of (3) A Ê. Each sulfoxide is bound to two Sn atoms in an in nite chain along the [100] direction. Similar cis-o 2 Sn geometries have been observed previously in the structures of [SnCl 2 (CH 3 ) 2 {meso-(c 6 H 5 SOCH 2 ) 2 }] and [SnCl 2 (CH 3 ) 2 {meso-(c 3 H 7 SOCH 2 ) 2 }]. The average SnÐO bond distances (2.359 A Ê ) in these structures compared with SnÐO [2.227 (2) A Ê ] in the title complex, follow the expected trends in the lower Lewis acidity of (CH 3 ) 2 SnCl 2 with respect to CH 3 SnCl 3. The crystal structures of the related adducts mer- [SnCl 3 (CH 3 )(C 5 H 4 NSOC 3 H 7 )] (Sousa et al., 1992), fac- [SnCl 3 {(C 6 H 5 )CH 2 }(C 12 H 8 N 2 )] (Hall & Tiekink, 1996) and facand mer-[sncl 3 (C 3 H 7 )(C 4 H 7 NO) 2 ] (Reuter & Puff, 1992) have been determined. All these examples, and also the results observed for the title compound, agree with the proposal of Reuter & Puff (1992) that the predominant formation of only a special stereoisomer, which is often observed in octahedral 1:1 and/or 1:2 adducts of monoorganotin trihalides, is caused by reaction conditions more than steric and/or electronic effects of the several complex ligands. Experimental Suitable single crystals of (I) were obtained by the 1:1 reaction of meso-(c 6 H 5 SOCH 2 ) 2 with CH 3 SnCl 3 in CH 2 Cl 2. Crystal data [SnCl 3 (CH 3 )(C 7 H 7 OS) 2 ] M r = Monoclinic, P2 1 =c a = (1) A Ê b = (4) A Ê c = (2) A Ê = (7) V = (3) A Ê 3 Z =4 Data collection Enraf±Nonius Turbo±CAD-4 diffractometer -geometry diffractometer Non-pro led!/2 scans Absorption correction: scan (North et al., 1968) T min = 0.670, T max = measured re ections 5748 independent re ections D x = Mg m 3 Mo K radiation Cell parameters from 25 re ections = 11.34±18.11 = 1.91 mm 1 T = 293 (2) K Prism, white mm 4177 re ections with I > 2(I) R int = max = h = 22! 0 k =0! 8 l = 27! 29 3 standard re ections frequency: 120 min intensity decay: 2% In the title structure, the Sn IV atom is hexacoordinate in a distorted octahedral geometry. The Cl atoms trans to the O atoms form SnÐCl bonds [SnÐCl (8) and SnÐCl (8) A Ê ] longer than the Cl atom trans to the C atom Re nement Re nement on F 2 R(F ) = wr(f 2 ) = S = re ections 210 parameters H-atom parameters constrained w = 1/[ 2 (F o 2 ) + (0.0409P) P] where P =(F o 2 +2F c 2 )/3 (/) max = max = 0.65 e A Ê 3 min = 0.54 e A Ê 3 Extinction correction: SHELXL97 Extinction coef cient: (2) e176 Maria Teresa do Prado Gambardella et al. [SnCl 3 (CH 3 )(C 7 H 7 OS) 2 ] Acta Cryst. (2000). C56, e176±e177
2 electronic papers Table 1 Selected geometric parameters (A Ê, ). SnÐC (3) SnÐO (2) SnÐO (2) SnÐCl (9) SnÐCl (8) SnÐCl (8) S1ÐO (2) CÐSnÐO (11) CÐSnÐO (11) O2ÐSnÐO (8) CÐSnÐCl (10) O2ÐSnÐCl (6) O1ÐSnÐCl (6) CÐSnÐCl (10) O2ÐSnÐCl (6) O1ÐSnÐCl (6) Cl1ÐSnÐCl (4) CÐSnÐCl (10) O2ÐSnÐCl (6) Symmetry codes: (i) 2 x; 1 y; 1 z; (ii) 1 x; 1 y; 1 z. S1ÐC (3) S1ÐC (3) S2ÐO (2) S2ÐC (3) S2ÐC (3) C13ÐC13 i (6) C14ÐC14 ii (6) O1ÐSnÐCl (6) Cl1ÐSnÐCl (3) Cl3ÐSnÐCl (3) O1ÐS1ÐC (13) O1ÐS1ÐC (12) C1ÐS1ÐC (14) O2ÐS2ÐC (14) O2ÐS2ÐC (13) C7ÐS2ÐC (14) S1ÐO1ÐSn (12) S2ÐO2ÐSn (13) H atoms were positioned geometrically and a riding model was used during the re nement process, with U iso amounting to 1.5 (for methyl H atoms) or 1.2 (for the remaining) of the value of the U eq of the atom to which they are attached. The CÐH distances range is 0.93±0.97 A Ê. Data collection: CAD-4 Software (Enraf±Nonius, 1989); cell re nement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to re ne structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: WinGX (Farrugia, 1998). The authors thank the Brazilian agences CAPES, CNPq, FINEP and FAPESP for nancial support. References Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343±350. Carvalho, C. C., Francisco, R. H. P., Gambardella, M. T. do P., de Sousa, G. F. & Filgueiras, A. C. L. (1996a). Acta Cryst. C52, 1629±1631. Carvalho, C. C., Francisco, R. H. P., Gambardella, M. T. do P., de Sousa, G. F. & Filgueiras, A. C. L. (1996b). Acta Cryst. C52, 1627±1629. Cattalini, L., Michelon, G. & Pelizzi, G. (1979). J. Chem. Soc. Dalton Trans. pp. 96±101. Enraf±Nonius (1989). CAD-4 Software. Version 5.0. Enraf±Nonius, Delft, The Netherlands. Farrugia, L. J. (1998). WinGX. University of Glasgow, Scotland. Francisco, R. H. P., Gambardella, M. T. dp P., Rodrigues, A. M. G. D., de Sousa, G. F. & Filgueiras, C. A. L. (1995). Acta Cryst. C51, 604±606. Hall, V. J. & Tiekink, E. R. T. (1996). Acta Cryst. C52, 2141±2143. Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. North, A. C., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351±359. Reuter, H. & Puff, H. (1992). J. Organomet. Chem. 424, 23±31. Sheldrick, G. M. (1997). SHELXL97. University of GoÈttingen, Germany. Sousa, G. F. de, Filgueiras, C. A. L., Darensbourg, M. Y. & Reibenspies, J. H. (1992). Inorg. Chem. 31, 3044±3049. Acta Cryst. (2000). C56, e176±e177 Maria Teresa do Prado Gambardella et al. [SnCl 3 (CH 3 )(C 7 H 7 OS) 2 ] e177
3 supporting information [doi: /s x] catena-poly[fac-trichloromethyltin(iv)-µ-[meso-1,2-bis(phenylsulfinyl)ethane- O:O ]] Maria Teresa do Prado Gambardella, Regina Helena Porto Francisco, Ana Maria G. Dias Rodrigues and Gerimário Freitas de Sousa Computing details Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: WinGX (Farrugia, 1998). (I) Crystal data [SnCl 3 (CH 3 )(C 7 H 7 OS) 2 ] M r = Monoclinic, P2 1 /c a = (1) Å b = (4) Å c = (2) Å β = (7) V = (3) Å 3 Z = 4 Data collection Enraf Nonius Turbo-CAD4 diffractometer non profiled ω/2θ scans Absorption correction: ψ scan (North et al., 1968) T min = 0.670, T max = measured reflections 5748 independent reflections Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 210 parameters 0 restraints H-atom parameters constrained F(000) = 1024 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from 25 reflections θ = µ = 1.91 mm 1 T = 293 K Prism, white mm 4177 reflections with I > 2σ(I) R int = θ max = 30.0, θ min = 2.7 h = 22 0 k = 0 8 l = standard reflections every 120 min intensity decay: 2% Calculated w = 1/[σ 2 (F o2 ) + (0.0409P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max = Δρ max = 0.65 e Å 3 Δρ min = 0.54 e Å 3 Extinction correction: SHELXL97, Fc * =kfc[ xfc 2 λ 3 /sin(2θ)] -1/4 Extinction coefficient: (2) sup-1
4 Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq Sn (12) (3) (10) (7) Cl (6) (16) (5) (3) Cl (5) (14) (4) (2) Cl (6) (14) (5) (2) S (5) (12) (4) (15) S (5) (12) (4) (16) O (13) (3) (11) (5) O (13) (4) (11) (5) C (2) (5) (17) (8) HA * HB * HC * C (19) (5) (15) (7) C (3) (6) (18) (10) H * C (3) (8) (18) (12) H * C (3) (8) (2) (13) H * C (3) (7) (2) (14) H * C (3) (6) (18) (10) H * C (2) (5) (15) (7) C (2) (6) (18) (8) H * C (3) (7) (2) (11) H * C (3) (8) (2) (14) H * C (3) (10) (2) (2) H * C (3) (8) (2) (13) H * C (19) (5) (15) (6) H * H * C (19) (5) (15) (6) H * sup-2
5 H * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Sn (10) (11) (12) (8) (8) (8) Cl (5) (6) (6) (4) (4) (5) Cl (4) (5) (4) (4) (4) (4) Cl (5) (5) (6) (4) (5) (4) S (3) (4) (4) (3) (3) (3) S (3) (4) (4) (3) (3) (3) O (10) (12) (12) (9) (9) (10) O (10) (13) (13) (9) (9) (10) C (18) (19) (2) (15) (16) (16) C (14) (18) (14) (13) (12) (12) C (2) (2) (18) (19) (17) (16) C (3) (3) (19) (3) (19) (2) C (3) (3) (2) (3) (2) (2) C (3) (3) (3) (3) (2) (2) C (2) (3) (19) (2) (18) (18) C (15) (19) (15) (14) (13) (14) C (19) (2) (19) (16) (15) (16) C (3) (3) (2) (2) (2) (19) C (3) (4) (3) (3) (2) (2) C (2) (5) (3) (3) (2) (3) C (2) (3) (3) (2) (18) (2) C (13) (17) (14) (12) (11) (12) C (14) (17) (16) (12) (12) (13) Geometric parameters (Å, º) Sn C (3) C4 H Sn O (2) C5 C (5) Sn O (2) C5 H Sn Cl (9) C6 H Sn Cl (8) C7 C (5) Sn Cl (8) C7 C (5) S1 O (2) C8 C (5) S1 C (3) C8 H S1 C (3) C9 C (6) S2 O (2) C9 H S2 C (3) C10 C (7) S2 C (3) C10 H C HA 0.96 C11 C (6) C HB 0.96 C11 H C HC 0.96 C12 H C1 C (5) C13 C13 i (6) C1 C (5) C13 H sup-3
6 C2 C (5) C13 H C2 H C14 C14 ii (6) C3 C (6) C14 H C3 H C14 H C4 C (6) C Sn O (11) C3 C4 H C Sn O (11) C5 C4 H O2 Sn O (8) C4 C5 C (4) C Sn Cl (10) C4 C5 H O2 Sn Cl (6) C6 C5 H O1 Sn Cl (6) C1 C6 C (4) C Sn Cl (10) C1 C6 H O2 Sn Cl (6) C5 C6 H O1 Sn Cl (6) C12 C7 C (3) Cl1 Sn Cl (4) C12 C7 S (3) C Sn Cl (10) C8 C7 S (2) O2 Sn Cl (6) C9 C8 C (4) O1 Sn Cl (6) C9 C8 H Cl1 Sn Cl (3) C7 C8 H Cl3 Sn Cl (3) C10 C9 C (4) O1 S1 C (13) C10 C9 H9 120 O1 S1 C (12) C8 C9 H9 120 C1 S1 C (14) C9 C10 C (4) O2 S2 C (14) C9 C10 H O2 S2 C (13) C11 C10 H C7 S2 C (14) C10 C11 C (4) S1 O1 Sn (12) C10 C11 H S2 O2 Sn (13) C12 C11 H Sn C HA C7 C12 C (4) Sn C HB C7 C12 H HA C HB C11 C12 H Sn C HC C13 i C13 S (3) HA C HC C13 i C13 H HB C HC S1 C13 H C2 C1 C (3) C13 i C13 H C2 C1 S (3) S1 C13 H C6 C1 S (3) H131 C13 H C1 C2 C (4) C14 ii C14 S (3) C1 C2 H C14 ii C14 H C3 C2 H S2 C14 H C4 C3 C (4) C14 ii C14 H C4 C3 H S2 C14 H C2 C3 H H141 C14 H C3 C4 C (4) Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y+1, z+1. sup-4
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