Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801017603/bt6086sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801017603/bt6086Isup2.hkl |
CCDC reference: 175986
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.004 Å
- Disorder in solvent or counterion
- R factor = 0.026
- wR factor = 0.050
- Data-to-parameter ratio = 35.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level B:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 32.01 From the CIF: _reflns_number_total 5357 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 6174 Completeness (_total/calc) 86.77% Alert B: < 90% complete (theta max?)
Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 20.00 Perc.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check
0,3 g (0,73 mmol) of 2,2-bis(chlorodimethylstannyl)propane (Austin et al., 1986; Karol et al., 1983) were dissolved in 2 ml of dry dimethyl sulfoxide and the mixture stirred for 30 min. The solution was left overnight at 278–288 K. The crystals were separated and dried carefully to remove the solvent from their surface; m.p. 391–392 K, yield 60% [literature (Austin et al., 1986) 389–390 K].
Two positions with occupancy factors of 0.596 (2) and 0.404 (2) for S1A and S1B, respectively, were refined for the S atom of the dimethyl sulfoxide moiety. H atoms were placed in calculated positions with Uiso constrained to be 1.5 times Ueq of the carrier atom. For the methyl groups containing atoms C11, C12, C21 and C22, the torsion angles were refined, whereas for the remaining methyl groups AFIX 33 (Sheldrick, 1997) was used. At C4 and at C5 there are two different orientations of the methyl groups having the same site occupation factors as the corresponding positions of the S atom.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
[Sn2(CH3)4(C3H6)Cl2]·C2H6OS | F(000) = 944 |
Mr = 488.62 | Dx = 1.824 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
a = 10.7602 (2) Å | Cell parameters from 14885 reflections |
b = 9.1559 (2) Å | θ = 3.0–32.0° |
c = 18.2953 (3) Å | µ = 3.21 mm−1 |
β = 99.2514 (12)° | T = 291 K |
V = 1779.00 (6) Å3 | Block, colourless |
Z = 4 | 0.44 × 0.42 × 0.40 mm |
Nonius KappaCCD diffractometer | 3091 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 32.0°, θmin = 3.0° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −15→15 |
258 frames via ω–rotation (Δω=1%) and two times 15 s per frame (three sets at different κ–angles) scans | k = −10→13 |
14885 measured reflections | l = −26→26 |
5357 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.050 | w = 1/[σ2(Fo2) + (0.0169P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.86 | (Δ/σ)max = 0.002 |
5357 reflections | Δρmax = 0.40 e Å−3 |
151 parameters | Δρmin = −0.45 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0230 (3) |
[Sn2(CH3)4(C3H6)Cl2]·C2H6OS | V = 1779.00 (6) Å3 |
Mr = 488.62 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.7602 (2) Å | µ = 3.21 mm−1 |
b = 9.1559 (2) Å | T = 291 K |
c = 18.2953 (3) Å | 0.44 × 0.42 × 0.40 mm |
β = 99.2514 (12)° |
Nonius KappaCCD diffractometer | 3091 reflections with I > 2σ(I) |
14885 measured reflections | Rint = 0.026 |
5357 independent reflections |
R[F2 > 2σ(F2)] = 0.026 | 0 restraints |
wR(F2) = 0.050 | H-atom parameters constrained |
S = 0.86 | Δρmax = 0.40 e Å−3 |
5357 reflections | Δρmin = −0.45 e Å−3 |
151 parameters |
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 | Occ. (<1) | |
Sn1 | 0.356075 (16) | 0.071328 (19) | 0.097190 (8) | 0.04487 (7) | |
Sn2 | 0.157803 (16) | 0.233913 (19) | 0.211282 (9) | 0.04547 (7) | |
Cl11 | 0.45611 (7) | −0.17218 (8) | 0.09939 (4) | 0.0694 (2) | |
Cl21 | 0.08098 (8) | 0.14610 (10) | 0.32298 (4) | 0.0764 (2) | |
C1 | 0.2766 (3) | 0.0501 (3) | 0.19780 (13) | 0.0512 (7) | |
C2 | 0.1974 (4) | −0.0899 (3) | 0.19404 (18) | 0.0936 (13) | |
H2A | 0.2505 | −0.1730 | 0.1905 | 0.140* | |
H2B | 0.1327 | −0.0863 | 0.1513 | 0.140* | |
H2C | 0.1595 | −0.0978 | 0.2379 | 0.140* | |
C3 | 0.3855 (3) | 0.0424 (4) | 0.26284 (15) | 0.0818 (11) | |
H3A | 0.3523 | 0.0353 | 0.3084 | 0.123* | |
H3B | 0.4360 | 0.1289 | 0.2635 | 0.123* | |
H3C | 0.4363 | −0.0419 | 0.2574 | 0.123* | |
C11 | 0.2348 (3) | 0.0423 (3) | −0.00536 (14) | 0.0679 (8) | |
H11A | 0.2646 | 0.1001 | −0.0428 | 0.102* | |
H11B | 0.1511 | 0.0725 | −0.0004 | 0.102* | |
H11C | 0.2340 | −0.0588 | −0.0193 | 0.102* | |
C12 | 0.5262 (3) | 0.1934 (3) | 0.10703 (16) | 0.0643 (8) | |
H12A | 0.5560 | 0.1941 | 0.0603 | 0.096* | |
H12B | 0.5885 | 0.1495 | 0.1439 | 0.096* | |
H12C | 0.5109 | 0.2919 | 0.1213 | 0.096* | |
C21 | −0.0168 (3) | 0.2368 (3) | 0.13822 (16) | 0.0683 (9) | |
H21A | −0.0702 | 0.1609 | 0.1519 | 0.102* | |
H21B | −0.0023 | 0.2210 | 0.0884 | 0.102* | |
H21C | −0.0568 | 0.3298 | 0.1414 | 0.102* | |
C22 | 0.2381 (3) | 0.4293 (3) | 0.25896 (15) | 0.0636 (8) | |
H22A | 0.2632 | 0.4158 | 0.3113 | 0.095* | |
H22B | 0.1771 | 0.5066 | 0.2504 | 0.095* | |
H22C | 0.3103 | 0.4544 | 0.2368 | 0.095* | |
S1A | 0.19098 (11) | 0.41712 (13) | 0.02845 (6) | 0.0509 (4) | 0.596 (2) |
S1B | 0.29907 (17) | 0.46745 (19) | 0.07461 (9) | 0.0543 (6) | 0.404 (2) |
O1 | 0.24943 (16) | 0.32413 (19) | 0.09404 (9) | 0.0537 (5) | |
C4 | 0.1686 (3) | 0.5890 (3) | 0.06263 (18) | 0.0760 (9) | |
H4A | 0.1002 | 0.5863 | 0.0905 | 0.114* | 0.596 (2) |
H4B | 0.1491 | 0.6564 | 0.0222 | 0.114* | 0.596 (2) |
H4C | 0.2440 | 0.6198 | 0.0942 | 0.114* | 0.596 (2) |
H4D | 0.1434 | 0.6078 | 0.1098 | 0.114* | 0.404 (2) |
H4E | 0.0997 | 0.5456 | 0.0299 | 0.114* | 0.404 (2) |
H4F | 0.1921 | 0.6790 | 0.0417 | 0.114* | 0.404 (2) |
C5 | 0.3202 (3) | 0.4571 (4) | −0.01897 (15) | 0.0728 (9) | |
H5A | 0.3451 | 0.3698 | −0.0418 | 0.109* | 0.596 (2) |
H5B | 0.3897 | 0.4935 | 0.0158 | 0.109* | 0.596 (2) |
H5C | 0.2949 | 0.5296 | −0.0563 | 0.109* | 0.596 (2) |
H5D | 0.3893 | 0.3931 | −0.0232 | 0.109* | 0.404 (2) |
H5E | 0.3378 | 0.5527 | −0.0362 | 0.109* | 0.404 (2) |
H5F | 0.2448 | 0.4199 | −0.0483 | 0.109* | 0.404 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.05202 (12) | 0.04540 (12) | 0.03905 (11) | −0.00190 (8) | 0.01297 (8) | −0.00513 (8) |
Sn2 | 0.04644 (12) | 0.05031 (13) | 0.04082 (11) | 0.00041 (8) | 0.01048 (8) | −0.00413 (8) |
Cl11 | 0.0801 (5) | 0.0543 (5) | 0.0759 (5) | 0.0135 (4) | 0.0195 (4) | −0.0078 (4) |
Cl21 | 0.0776 (5) | 0.1009 (7) | 0.0579 (4) | 0.0079 (5) | 0.0329 (4) | 0.0109 (4) |
C1 | 0.0681 (18) | 0.0420 (16) | 0.0473 (14) | 0.0059 (14) | 0.0205 (14) | 0.0035 (12) |
C2 | 0.134 (3) | 0.052 (2) | 0.115 (3) | −0.020 (2) | 0.081 (3) | −0.0053 (18) |
C3 | 0.101 (3) | 0.099 (3) | 0.0461 (16) | 0.045 (2) | 0.0157 (17) | 0.0113 (16) |
C11 | 0.076 (2) | 0.071 (2) | 0.0538 (16) | −0.0002 (17) | 0.0000 (15) | −0.0169 (14) |
C12 | 0.0597 (19) | 0.0600 (19) | 0.0751 (19) | −0.0066 (16) | 0.0166 (16) | 0.0001 (15) |
C21 | 0.0598 (19) | 0.083 (2) | 0.0589 (17) | −0.0092 (16) | −0.0011 (15) | −0.0018 (15) |
C22 | 0.072 (2) | 0.061 (2) | 0.0559 (16) | 0.0001 (16) | 0.0044 (15) | −0.0176 (14) |
S1A | 0.0519 (8) | 0.0569 (8) | 0.0446 (7) | −0.0077 (6) | 0.0098 (5) | 0.0025 (5) |
S1B | 0.0574 (12) | 0.0470 (11) | 0.0571 (11) | −0.0070 (9) | 0.0047 (9) | 0.0058 (8) |
O1 | 0.0692 (13) | 0.0460 (11) | 0.0498 (10) | 0.0018 (9) | 0.0215 (9) | 0.0058 (8) |
C4 | 0.083 (2) | 0.062 (2) | 0.087 (2) | 0.0162 (18) | 0.0231 (19) | 0.0145 (17) |
C5 | 0.082 (2) | 0.081 (2) | 0.0612 (18) | −0.0019 (18) | 0.0288 (17) | 0.0151 (15) |
Sn1—C11 | 2.123 (3) | C21—H21B | 0.9600 |
Sn1—C12 | 2.128 (3) | C21—H21C | 0.9600 |
Sn1—C1 | 2.159 (2) | C22—H22A | 0.9600 |
Sn1—Cl11 | 2.4733 (8) | C22—H22B | 0.9600 |
Sn2—C22 | 2.113 (3) | C22—H22C | 0.9600 |
Sn2—C21 | 2.123 (3) | S1A—O1 | 1.522 (2) |
Sn2—C1 | 2.152 (3) | S1A—C4 | 1.724 (3) |
Sn2—Cl21 | 2.4594 (7) | S1A—C5 | 1.791 (3) |
C1—C3 | 1.531 (4) | S1B—O1 | 1.481 (2) |
C1—C2 | 1.534 (4) | S1B—C5 | 1.765 (3) |
C2—H2A | 0.9600 | S1B—C4 | 1.777 (3) |
C2—H2B | 0.9600 | C4—H4A | 0.9600 |
C2—H2C | 0.9600 | C4—H4B | 0.9600 |
C3—H3A | 0.9600 | C4—H4C | 0.9600 |
C3—H3B | 0.9600 | C4—H4D | 0.9600 |
C3—H3C | 0.9600 | C4—H4E | 0.9600 |
C11—H11A | 0.9600 | C4—H4F | 0.9600 |
C11—H11B | 0.9600 | C5—H5A | 0.9600 |
C11—H11C | 0.9600 | C5—H5B | 0.9600 |
C12—H12A | 0.9600 | C5—H5C | 0.9600 |
C12—H12B | 0.9600 | C5—H5D | 0.9600 |
C12—H12C | 0.9600 | C5—H5E | 0.9600 |
C21—H21A | 0.9600 | C5—H5F | 0.9600 |
C11—Sn1—C12 | 122.60 (12) | C5—S1B—C4 | 97.82 (17) |
C11—Sn1—C1 | 118.09 (11) | S1B—O1—S1A | 55.58 (10) |
C12—Sn1—C1 | 115.37 (11) | S1A—C4—S1B | 47.14 (10) |
C11—Sn1—Cl11 | 96.06 (8) | S1A—C4—H4A | 109.5 |
C12—Sn1—Cl11 | 96.08 (8) | S1B—C4—H4A | 125.2 |
C1—Sn1—Cl11 | 97.80 (7) | S1A—C4—H4B | 109.5 |
C22—Sn2—C21 | 120.72 (12) | S1B—C4—H4B | 124.6 |
C22—Sn2—C1 | 119.91 (11) | H4A—C4—H4B | 109.5 |
C21—Sn2—C1 | 114.80 (11) | S1A—C4—H4C | 109.5 |
C22—Sn2—Cl21 | 95.94 (8) | S1B—C4—H4C | 62.3 |
C21—Sn2—Cl21 | 98.37 (8) | H4A—C4—H4C | 109.5 |
C1—Sn2—Cl21 | 97.17 (7) | H4B—C4—H4C | 109.5 |
C3—C1—C2 | 110.3 (2) | S1A—C4—H4D | 124.5 |
C3—C1—Sn2 | 109.95 (18) | S1B—C4—H4D | 109.5 |
C2—C1—Sn2 | 108.8 (2) | H4A—C4—H4D | 34.6 |
C3—C1—Sn1 | 107.97 (18) | H4B—C4—H4D | 121.2 |
C2—C1—Sn1 | 109.29 (17) | H4C—C4—H4D | 74.9 |
Sn2—C1—Sn1 | 110.56 (11) | S1A—C4—H4E | 62.3 |
C1—C2—H2A | 109.5 | S1B—C4—H4E | 109.5 |
C1—C2—H2B | 109.5 | H4A—C4—H4E | 74.9 |
H2A—C2—H2B | 109.5 | H4B—C4—H4E | 74.6 |
C1—C2—H2C | 109.5 | H4C—C4—H4E | 171.8 |
H2A—C2—H2C | 109.5 | H4D—C4—H4E | 109.5 |
H2B—C2—H2C | 109.5 | S1A—C4—H4F | 125.3 |
C1—C3—H3A | 109.5 | S1B—C4—H4F | 109.5 |
C1—C3—H3B | 109.5 | H4A—C4—H4F | 120.4 |
H3A—C3—H3B | 109.5 | H4B—C4—H4F | 34.9 |
C1—C3—H3C | 109.5 | H4C—C4—H4F | 74.7 |
H3A—C3—H3C | 109.5 | H4D—C4—H4F | 109.5 |
H3B—C3—H3C | 109.5 | H4E—C4—H4F | 109.5 |
Sn1—C11—H11A | 109.5 | S1B—C5—S1A | 46.39 (10) |
Sn1—C11—H11B | 109.5 | S1B—C5—H5A | 123.7 |
H11A—C11—H11B | 109.5 | S1A—C5—H5A | 109.5 |
Sn1—C11—H11C | 109.5 | S1B—C5—H5B | 63.1 |
H11A—C11—H11C | 109.5 | S1A—C5—H5B | 109.5 |
H11B—C11—H11C | 109.5 | H5A—C5—H5B | 109.5 |
Sn1—C12—H12A | 109.5 | S1B—C5—H5C | 126.0 |
Sn1—C12—H12B | 109.5 | S1A—C5—H5C | 109.5 |
H12A—C12—H12B | 109.5 | H5A—C5—H5C | 109.5 |
Sn1—C12—H12C | 109.5 | H5B—C5—H5C | 109.5 |
H12A—C12—H12C | 109.5 | S1B—C5—H5D | 109.5 |
H12B—C12—H12C | 109.5 | S1A—C5—H5D | 125.9 |
Sn2—C21—H21A | 109.5 | H5A—C5—H5D | 35.1 |
Sn2—C21—H21B | 109.5 | H5B—C5—H5D | 74.6 |
H21A—C21—H21B | 109.5 | H5C—C5—H5D | 119.9 |
Sn2—C21—H21C | 109.5 | S1B—C5—H5E | 109.5 |
H21A—C21—H21C | 109.5 | S1A—C5—H5E | 123.8 |
H21B—C21—H21C | 109.5 | H5A—C5—H5E | 122.2 |
Sn2—C22—H22A | 109.5 | H5B—C5—H5E | 74.2 |
Sn2—C22—H22B | 109.5 | H5C—C5—H5E | 35.3 |
H22A—C22—H22B | 109.5 | H5D—C5—H5E | 109.5 |
Sn2—C22—H22C | 109.5 | S1B—C5—H5F | 109.5 |
H22A—C22—H22C | 109.5 | S1A—C5—H5F | 63.1 |
H22B—C22—H22C | 109.5 | H5A—C5—H5F | 74.4 |
O1—S1A—C4 | 106.78 (14) | H5B—C5—H5F | 172.6 |
O1—S1A—C5 | 103.99 (14) | H5C—C5—H5F | 74.3 |
C4—S1A—C5 | 98.85 (16) | H5D—C5—H5F | 109.5 |
O1—S1B—C5 | 107.02 (16) | H5E—C5—H5F | 109.5 |
O1—S1B—C4 | 106.01 (16) |
Experimental details
Crystal data | |
Chemical formula | [Sn2(CH3)4(C3H6)Cl2]·C2H6OS |
Mr | 488.62 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 291 |
a, b, c (Å) | 10.7602 (2), 9.1559 (2), 18.2953 (3) |
β (°) | 99.2514 (12) |
V (Å3) | 1779.00 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.21 |
Crystal size (mm) | 0.44 × 0.42 × 0.40 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14885, 5357, 3091 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.746 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.050, 0.86 |
No. of reflections | 5357 |
No. of parameters | 151 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.45 |
Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1991), SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
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Organotin compounds of the type R3SnX, where X is an electronegative residue such as halide or trifluoromethanesulfonate, form complexes with donor ligands L in which the Sn atom becomes pentacoordinate. It might thus be expected that compounds of the type XSnR2(CR'R")nSnR2X would form similar complexes in which a ligand L is attached to each Sn atom. However, a study involving DMSO as ligand (Karol et al., 1983) shows that the compound ClSnMe2CH2SnMeCl2 forms a 1:1 complex with DMSO, which bridges the two Sn atoms via its O atom, (I).
It thus seemed of interest to determine whether the replacement of the H atoms of the CH2 group between the Sn atoms by methyl groups would cause the complex to take up another geometry. Also of interest are variations in the Sn—C—Sn angle, since previous NMR work (Mitchell et al., 1983) indicates that the coupling constant 2J(Sn—C—Sn) changes sign at an angle very close to the tetrahedral angle of 109.47°.
The present results show that 1:1 complexation of DMSO is present in the title compound (I) and that its geometry is broadly similar to that of ClSnMe2CH2SnMeCl2·DMSO, (II). There are however significant differences. While in (II) the angle Sn—C—Sn is 112.0 (6)°, it decreases in (I) to 110.39 (13)°. The Sn—CH2 bond lengths are of course considerably different in (II): ClMe2Sn—CH2 2.159 (3) and Cl2MeSn-CH2 2.097 (13) Å. In (I), the two bond lengths are as expected almost identical: 2.164 (3) and 2.152 (3) Å. The angle Sn—O—Sn is very similar in (I) and (II): 85.69 (6) and 86.6 (2)°, respectively. However, the Sn—O bond distances differ considerably: 2.578 (2) and 2.632 (2) Å in (I), and 2.568 (8) and 2.575 (8) Å in (II).