Acta Cryst. (2011). E67, m696 [ doi:10.1107/S1600536811013584 ]
Regular crystals of the title compound, (C2H8N)2[Sn(CH3)2Cl4], were obtained by reacting SnMe2Cl2 with (CH3)2NH·HCl in ethanol in a 1:1 ratio. The Sn atom lies on a center of symmetry and is six-coordinated. It has a distorted octahedral SnC2Cl4 environment with the Cl atoms in cis positions. The Cl atoms are connected to dimethylammonium cations through N-H
Cl hydrogen bonds, forming an infinite chain extending parallel to [010].
The title compound has been obtained as white crystalline solid by reacting dimethylammonium chloride (Merck) with dimethyltin dichloride (Aldrich) in ethanol (1/1 ratio, mp: 190°). After a slow solvent evaporation colourless crystals suitable for X-ray work were obtained. All the chemicals were used without any further purification.
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).
![[Figure 1]](./br2163fig1thm.gif)
| Fig. 1. Molecular packing around one anion implying hydrogen bonds (dashed lines) with the atom numbering used and 50% probability displacement elipsoids. Symmetry operations : ['] -x, -y, -z; [''] x, y+1,z, ['''] -x, -y, -z. |
| (C2H8N)2[SnCH3)2Cl4] | Z = 1 |
| Mr = 382.75 | F(000) = 190 |
| Triclinic, P1 | Dx = 1.663 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 6.6162 (9) Å | Cell parameters from 3675 reflections |
| b = 7.3703 (11) Å | θ = 2.9–31.3° |
| c = 8.4555 (12) Å | µ = 2.34 mm−1 |
| α = 109.625 (14)° | T = 297 K |
| β = 98.345 (12)° | Fragment of rounded block, colourless |
| γ = 92.812 (12)° | 0.5 × 0.3 × 0.2 mm |
| V = 382.13 (9) Å3 |
| Oxford Diffraction Xcalibur Sapphire2 diffractometer | 1871 independent reflections |
| Radiation source: sealed X-ray tube | 1839 reflections with I > 2σ(I) |
| graphite | Rint = 0.018 |
| Detector resolution: 8.3622 pixels mm-1 | θmax = 28.3°, θmin = 4.1° |
| 4 stepped ω–scans over 115 deg. with kappa –79 deg. (chi –58.3 deg.), phi 0, 90, 180, 270 deg. step 1 deg., exposure time 45 s detector distance 50 mm detector angle 30 deg. | h = −8→7 |
| Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2009) | k = −9→9 |
| Tmin = 0.352, Tmax = 0.652 | l = −11→11 |
| 3329 measured reflections |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.023 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.060 | H-atom parameters constrained |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0362P)2 + 0.2233P] where P = (Fo2 + 2Fc2)/3 |
| 1871 reflections | (Δ/σ)max < 0.001 |
| 64 parameters | Δρmax = 0.56 e Å−3 |
| 0 restraints | Δρmin = −0.43 e Å−3 |
| (C2H8N)2[SnCH3)2Cl4] | γ = 92.812 (12)° |
| Mr = 382.75 | V = 382.13 (9) Å3 |
| Triclinic, P1 | Z = 1 |
| a = 6.6162 (9) Å | Mo Kα radiation |
| b = 7.3703 (11) Å | µ = 2.34 mm−1 |
| c = 8.4555 (12) Å | T = 297 K |
| α = 109.625 (14)° | 0.5 × 0.3 × 0.2 mm |
| β = 98.345 (12)° |
| Oxford Diffraction Xcalibur Sapphire2 diffractometer | 1871 independent reflections |
| Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2009) | 1839 reflections with I > 2σ(I) |
| Tmin = 0.352, Tmax = 0.652 | Rint = 0.018 |
| 3329 measured reflections | θmax = 28.3° |
| R[F2 > 2σ(F2)] = 0.023 | H-atom parameters constrained |
| wR(F2) = 0.060 | Δρmax = 0.56 e Å−3 |
| S = 1.06 | Δρmin = −0.43 e Å−3 |
| 1871 reflections | Absolute structure: ? |
| 64 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.2689 (4) | 0.3818 (4) | 0.5967 (3) | 0.0404 (5) | |
| H1A | 0.2902 | 0.2502 | 0.5847 | 0.061* | |
| H1B | 0.1366 | 0.3849 | 0.5343 | 0.061* | |
| H1C | 0.275 | 0.4566 | 0.715 | 0.061* | |
| Cl1 | 0.25609 (10) | 0.40746 (9) | 0.20155 (7) | 0.04289 (14) | |
| Cl2 | 0.64584 (8) | 0.16207 (8) | 0.39707 (7) | 0.03603 (12) | |
| Sn1 | 0.5 | 0.5 | 0.5 | 0.02900 (8) | |
| C2 | 0.2993 (5) | 0.8184 (6) | 0.0309 (4) | 0.0621 (8) | |
| H2A | 0.4272 | 0.764 | 0.0166 | 0.093* | |
| H2B | 0.3073 | 0.9423 | 0.0167 | 0.093* | |
| H2C | 0.1905 | 0.7333 | −0.0527 | 0.093* | |
| C3 | 0.0570 (4) | 0.9131 (4) | 0.2302 (4) | 0.0479 (6) | |
| H3A | 0.0331 | 0.9174 | 0.3406 | 0.072* | |
| H3B | −0.0493 | 0.8274 | 0.1442 | 0.072* | |
| H3C | 0.0563 | 1.0407 | 0.2239 | 0.072* | |
| N1 | 0.2581 (3) | 0.8422 (3) | 0.2023 (3) | 0.0381 (4) | |
| H1D | 0.3576 | 0.9263 | 0.28 | 0.046* | |
| H1E | 0.2622 | 0.7276 | 0.2183 | 0.046* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0393 (11) | 0.0380 (11) | 0.0450 (12) | −0.0035 (9) | 0.0167 (10) | 0.0128 (10) |
| Cl1 | 0.0486 (3) | 0.0369 (3) | 0.0360 (3) | −0.0001 (2) | −0.0059 (2) | 0.0094 (2) |
| Cl2 | 0.0387 (3) | 0.0282 (2) | 0.0402 (3) | 0.00715 (19) | 0.0087 (2) | 0.0093 (2) |
| Sn1 | 0.03107 (11) | 0.02496 (11) | 0.03074 (11) | −0.00012 (7) | 0.00626 (7) | 0.00940 (8) |
| C2 | 0.0604 (18) | 0.078 (2) | 0.0417 (14) | −0.0007 (16) | 0.0195 (13) | 0.0098 (14) |
| C3 | 0.0387 (12) | 0.0550 (15) | 0.0478 (14) | 0.0036 (11) | 0.0083 (10) | 0.0151 (12) |
| N1 | 0.0382 (10) | 0.0390 (10) | 0.0351 (9) | 0.0007 (8) | 0.0029 (7) | 0.0120 (8) |
| C1—Sn1 | 2.116 (2) | C2—H2A | 0.96 |
| C1—H1A | 0.96 | C2—H2B | 0.96 |
| C1—H1B | 0.96 | C2—H2C | 0.96 |
| C1—H1C | 0.96 | C3—N1 | 1.475 (3) |
| Cl1—Sn1 | 2.6441 (7) | C3—H3A | 0.96 |
| Cl2—Sn1 | 2.6297 (7) | C3—H3B | 0.96 |
| Sn1—C1i | 2.116 (2) | C3—H3C | 0.96 |
| Sn1—Cl2i | 2.6297 (7) | N1—H1D | 0.9 |
| Sn1—Cl1i | 2.6441 (7) | N1—H1E | 0.9 |
| C2—N1 | 1.468 (4) | ||
| Sn1—C1—H1A | 109.5 | Cl1i—Sn1—Cl1 | 180 |
| Sn1—C1—H1B | 109.5 | N1—C2—H2A | 109.5 |
| H1A—C1—H1B | 109.5 | N1—C2—H2B | 109.5 |
| Sn1—C1—H1C | 109.5 | H2A—C2—H2B | 109.5 |
| H1A—C1—H1C | 109.5 | N1—C2—H2C | 109.5 |
| H1B—C1—H1C | 109.5 | H2A—C2—H2C | 109.5 |
| C1i—Sn1—C1 | 180.00 (13) | H2B—C2—H2C | 109.5 |
| C1i—Sn1—Cl2i | 90.42 (7) | N1—C3—H3A | 109.5 |
| C1—Sn1—Cl2i | 89.58 (7) | N1—C3—H3B | 109.5 |
| C1i—Sn1—Cl2 | 89.58 (7) | H3A—C3—H3B | 109.5 |
| C1—Sn1—Cl2 | 90.42 (7) | N1—C3—H3C | 109.5 |
| Cl2i—Sn1—Cl2 | 180 | H3A—C3—H3C | 109.5 |
| C1i—Sn1—Cl1i | 90.43 (8) | H3B—C3—H3C | 109.5 |
| C1—Sn1—Cl1i | 89.57 (8) | C2—N1—C3 | 112.7 (2) |
| Cl2i—Sn1—Cl1i | 89.90 (2) | C2—N1—H1D | 109.1 |
| Cl2—Sn1—Cl1i | 90.10 (2) | C3—N1—H1D | 109.1 |
| C1i—Sn1—Cl1 | 89.57 (8) | C2—N1—H1E | 109.1 |
| C1—Sn1—Cl1 | 90.43 (8) | C3—N1—H1E | 109.1 |
| Cl2i—Sn1—Cl1 | 90.10 (2) | H1D—N1—H1E | 107.8 |
| Cl2—Sn1—Cl1 | 89.90 (2) |
| Symmetry codes: (i) −x+1, −y+1, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1E···Cl1 | 0.9 | 2.31 | 3.201 (2) | 169 |
| N1—H1D···Cl2ii | 0.9 | 2.37 | 3.229 (2) | 160 |
| Symmetry codes: (ii) x, y+1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1E···Cl1 | 0.9 | 2.31 | 3.201 (2) | 169 |
| N1—H1D···Cl2i | 0.9 | 2.37 | 3.229 (2) | 160 |
| Symmetry codes: (i) x, y+1, z. |
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.
Casas, J., Castineiras, A., Couce, M. D., Martinez, G., Sordo, J. & Varela, J. M. (1996). J. Organomet. Chem. 517, 165–172.
Crowe, A. J. (1994). Metal Complexes in Cancer Chemotherapy, edited by S. P. Friccker. London: Chapman and Hall.
Diasse-Sarr, A., Diop, L., Mahon, M. F. & Molloy, K. C. (1997). Main Group Met. Chem. 20, 223–229.
Diop, T., Diop, L., Molloy, K. C. K. & Kocioc-Köhn, G. (2011). Acta Cryst. E67, m203-m204.
Diop, C. A. K., Diop, L. & Toscano, A. R. (2002). Main Group Met. Chem. 25, 327–328.
Diop, L., Mahieu, B., Mahon, M. F., Molloy, K. C. & Okio, K. Y. A. (2003). Appl. Organomet. Chem. 17, 881–882.
Evans, C. J. & Karpel, S. (1985). Organotin Compounds in Modern Technology, J. Organomet. Chem. Library, Vol. 16. Amsterdam: Elsevier.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gielen, M. (1996). Coord. Chem. Rev. 151, 41–51.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Valle, G., Plazzogna, G. & Ettore, R. (1985). J. Chem. Soc. Dalton Trans. pp. 1271–1274.
As some compounds belonging to organotin family have been screened and found to be very more active than cis platin towards some kinds of cancer, many groups have been involved in the seek of new organotin compounds (Gielen, 1996; Crowe, 1994). In another hand the various applications of compounds of this family have been outlined (Evans & Karpel, 1985). In our group we have yet published some papers in this field (Diop et al. 2002; Diop et al. 2003; Diasse-Sarr et al. 1997). In this paper we have initiated the study of the interactions between (CH3)3NH.Cl and SnMe2Cl2 which has yielded [(CH3)2NH2+]2[SnMe2Cl42-], X-ray structure determination of which has been carried out.
In the [SnMe2Cl4]2- anion the tin atom, which lies on a center of symmetry, is coordinated to the two methyl groups and four Cl atoms (Fig 1) in an octahedral geometry with trans methyl groups.
The Sn—C bond distances (2.116Å) are practically equal to those found in other octahedral dimethyltin(IV) diaquo-dichloro complexes SnMe2(H2O)2Cl2 (2.112 Å) reported by Valle et al. (1985) and longer than those in [Hthiamine][SnMe2(H2O)2Cl2]Cl (2.092 Å and 2.084 Å) reported by Casas et al. (1996).
The Cl—Sn—Cl and Cl—Sn—CH3 angles being very near to 90° indicates an almost perfect octahedron. The interactions between [(CH3)NH2+] and anion are hydrogen bonds type. The C—N—C angles of the cation is close to 109°, in agreement with the expected sp3 hybridation. The interactions between [(CH3)NH2+] and anion imply hydrogen bonds.