Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100015146/av1054sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100015146/av1054Isup2.hkl |
CCDC reference: 158238
Compound (I) was prepared from o-ClC6H4CH2SnCl3 (2.10 g, 6 mmol) in CHCl3 (100 ml) and NaSPy (2.40 g, 18 mmol) in MeOH (40 ml) at room temperature. Single crystals of (I) (m.p. 446 K) were obtained from a solution in CHCl3 containing some petroleum ether at 243 K. The compound was characterized by elemental analysis and by IR, Mössbauer, NMR and mass spectroscopies (Huber et al., 1997).
All H atoms were were placed in calculated positions using a riding model and refined with common isotropic displacement parameters for the different CH types [Hmethylene C—H 0.99 Å and Uiso 0.031 (9) Å2, and Haromatic C—H 0.95 Å and Uiso 0.039 (3) Å2].
Data collection: P3 Software (Siemens, 1989); cell refinement: P3 Software; data reduction: XDISK in P3 Software; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).
Fig. 1. The molecular view of (I) showing the atom-labelling scheme. Displacement ellipsoids are shown at the 50% probability level and H atoms are drawn as small spheres of arbitrary radii. |
[Sn(C5H4NS)3(C7H6Cl)] | F(000) = 572 |
Mr = 574.71 | Dx = 1.648 Mg m−3 Dm = not determined Mg m−3 Dm measured by not measured |
Triclinic, P1 | Melting point: 446 K |
a = 7.725 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.321 (3) Å | Cell parameters from 46 reflections |
c = 15.548 (5) Å | θ = 7.8–14.8° |
α = 80.26 (2)° | µ = 1.50 mm−1 |
β = 77.18 (2)° | T = 170 K |
γ = 74.82 (2)° | Plate, light yellow |
V = 1158.4 (7) Å3 | 0.50 × 0.14 × 0.05 mm |
Z = 2 |
Siemens R3m/V diffractometer | 3216 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 25.1°, θmin = 2.1° |
ω/2θ scans | h = −9→9 |
Absorption correction: ψ-scan (XEMP in P3 Software; Siemens, 1989) | k = −12→12 |
Tmin = 0.501, Tmax = 0.928 | l = −18→18 |
5674 measured reflections | 6 standard reflections every 300 reflections |
4098 independent reflections | intensity decay: 1.6% |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.073 | Only H-atom displacement parameters refined |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0356P)2] where P = (Fo2 + 2Fc2)/3 |
4098 reflections | (Δ/σ)max = 0.001 |
273 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
[Sn(C5H4NS)3(C7H6Cl)] | γ = 74.82 (2)° |
Mr = 574.71 | V = 1158.4 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.725 (3) Å | Mo Kα radiation |
b = 10.321 (3) Å | µ = 1.50 mm−1 |
c = 15.548 (5) Å | T = 170 K |
α = 80.26 (2)° | 0.50 × 0.14 × 0.05 mm |
β = 77.18 (2)° |
Siemens R3m/V diffractometer | 3216 reflections with I > 2σ(I) |
Absorption correction: ψ-scan (XEMP in P3 Software; Siemens, 1989) | Rint = 0.030 |
Tmin = 0.501, Tmax = 0.928 | 6 standard reflections every 300 reflections |
5674 measured reflections | intensity decay: 1.6% |
4098 independent reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.073 | Only H-atom displacement parameters refined |
S = 0.94 | Δρmax = 0.54 e Å−3 |
4098 reflections | Δρmin = −0.46 e Å−3 |
273 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 | ||
Sn1 | 0.20040 (4) | 0.11525 (3) | 0.231570 (19) | 0.02082 (9) | |
Cl1 | 0.17558 (17) | 0.26125 (13) | 0.47301 (7) | 0.0387 (3) | |
C1 | 0.3996 (6) | 0.1684 (4) | 0.2932 (3) | 0.0258 (10) | |
H1A | 0.4024 | 0.1149 | 0.3523 | 0.031 (9)* | |
H1B | 0.5225 | 0.1430 | 0.2562 | 0.031 (9)* | |
C2 | 0.3580 (6) | 0.3141 (4) | 0.3039 (3) | 0.0240 (9) | |
C3 | 0.2588 (6) | 0.3678 (4) | 0.3819 (3) | 0.0289 (10) | |
C4 | 0.2262 (7) | 0.5051 (5) | 0.3901 (4) | 0.0424 (13) | |
H4 | 0.1597 | 0.5388 | 0.4440 | 0.039 (3)* | |
C5 | 0.2904 (7) | 0.5914 (5) | 0.3203 (4) | 0.0503 (15) | |
H5 | 0.2664 | 0.6851 | 0.3255 | 0.039 (3)* | |
C6 | 0.3902 (8) | 0.5418 (5) | 0.2421 (4) | 0.0515 (15) | |
H6 | 0.4356 | 0.6012 | 0.1938 | 0.039 (3)* | |
C7 | 0.4231 (7) | 0.4055 (5) | 0.2348 (3) | 0.0367 (11) | |
H7 | 0.4925 | 0.3726 | 0.1811 | 0.039 (3)* | |
S1 | 0.16289 (17) | 0.33423 (11) | 0.11680 (7) | 0.0307 (3) | |
C11 | −0.0037 (6) | 0.2652 (4) | 0.0948 (3) | 0.0259 (10) | |
N11 | −0.0147 (5) | 0.1449 (3) | 0.1441 (2) | 0.0229 (8) | |
C13 | −0.1301 (6) | 0.0749 (4) | 0.1318 (3) | 0.0295 (10) | |
H13 | −0.1345 | −0.0096 | 0.1667 | 0.039 (3)* | |
C14 | −0.2408 (6) | 0.1224 (4) | 0.0707 (3) | 0.0309 (10) | |
H14 | −0.3203 | 0.0713 | 0.0621 | 0.039 (3)* | |
C15 | −0.2347 (7) | 0.2478 (5) | 0.0209 (3) | 0.0389 (12) | |
H15 | −0.3125 | 0.2832 | −0.0212 | 0.039 (3)* | |
C16 | −0.1165 (7) | 0.3207 (5) | 0.0324 (3) | 0.0335 (11) | |
H16 | −0.1121 | 0.4061 | −0.0011 | 0.039 (3)* | |
S2 | 0.03111 (17) | −0.02880 (10) | 0.35238 (7) | 0.0294 (3) | |
C21 | −0.1058 (6) | 0.1292 (4) | 0.3775 (3) | 0.0234 (9) | |
N21 | −0.0560 (5) | 0.2330 (3) | 0.3204 (2) | 0.0234 (8) | |
C23 | −0.1466 (6) | 0.3612 (4) | 0.3308 (3) | 0.0290 (10) | |
H23 | −0.1099 | 0.4327 | 0.2897 | 0.039 (3)* | |
C24 | −0.2912 (6) | 0.3911 (5) | 0.3996 (3) | 0.0355 (11) | |
H24 | −0.3551 | 0.4821 | 0.4061 | 0.039 (3)* | |
C25 | −0.3417 (7) | 0.2853 (5) | 0.4593 (3) | 0.0386 (12) | |
H25 | −0.4403 | 0.3046 | 0.5077 | 0.039 (3)* | |
C26 | −0.2521 (6) | 0.1533 (5) | 0.4499 (3) | 0.0319 (10) | |
H26 | −0.2873 | 0.0810 | 0.4906 | 0.039 (3)* | |
S3 | 0.36519 (16) | −0.05588 (11) | 0.12786 (7) | 0.0299 (3) | |
C31 | 0.5427 (6) | −0.1452 (4) | 0.1845 (3) | 0.0251 (10) | |
N31 | 0.5215 (5) | −0.1275 (3) | 0.2704 (2) | 0.0282 (8) | |
C33 | 0.6581 (7) | −0.1918 (4) | 0.3138 (3) | 0.0353 (11) | |
H33 | 0.6466 | −0.1774 | 0.3737 | 0.039 (3)* | |
C34 | 0.8151 (7) | −0.2783 (5) | 0.2749 (4) | 0.0399 (12) | |
H34 | 0.9075 | −0.3242 | 0.3080 | 0.039 (3)* | |
C35 | 0.8341 (7) | −0.2961 (4) | 0.1877 (3) | 0.0391 (12) | |
H35 | 0.9410 | −0.3543 | 0.1597 | 0.039 (3)* | |
C36 | 0.6989 (6) | −0.2299 (4) | 0.1407 (3) | 0.0336 (11) | |
H36 | 0.7108 | −0.2413 | 0.0801 | 0.039 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.02592 (17) | 0.01750 (14) | 0.02055 (15) | −0.00754 (12) | −0.00535 (12) | −0.00115 (10) |
Cl1 | 0.0390 (7) | 0.0516 (7) | 0.0264 (6) | −0.0108 (6) | −0.0050 (5) | −0.0081 (5) |
C1 | 0.028 (2) | 0.026 (2) | 0.028 (2) | −0.0081 (19) | −0.009 (2) | −0.0085 (18) |
C2 | 0.027 (2) | 0.022 (2) | 0.025 (2) | −0.0077 (19) | −0.0062 (19) | −0.0058 (17) |
C3 | 0.029 (3) | 0.031 (2) | 0.032 (2) | −0.006 (2) | −0.013 (2) | −0.0066 (19) |
C4 | 0.030 (3) | 0.040 (3) | 0.064 (4) | 0.001 (2) | −0.020 (3) | −0.023 (3) |
C5 | 0.040 (3) | 0.022 (2) | 0.097 (5) | −0.005 (2) | −0.031 (3) | −0.011 (3) |
C6 | 0.062 (4) | 0.039 (3) | 0.066 (4) | −0.030 (3) | −0.023 (3) | 0.004 (3) |
C7 | 0.041 (3) | 0.035 (3) | 0.041 (3) | −0.020 (2) | −0.012 (2) | 0.000 (2) |
S1 | 0.0421 (7) | 0.0249 (6) | 0.0299 (6) | −0.0168 (5) | −0.0131 (5) | 0.0060 (4) |
C11 | 0.032 (3) | 0.024 (2) | 0.022 (2) | −0.008 (2) | −0.004 (2) | −0.0025 (17) |
N11 | 0.030 (2) | 0.0206 (17) | 0.0178 (17) | −0.0098 (16) | −0.0026 (16) | 0.0008 (14) |
C13 | 0.038 (3) | 0.029 (2) | 0.024 (2) | −0.015 (2) | −0.002 (2) | −0.0018 (18) |
C14 | 0.035 (3) | 0.033 (2) | 0.031 (2) | −0.016 (2) | −0.011 (2) | −0.0026 (19) |
C15 | 0.042 (3) | 0.051 (3) | 0.025 (2) | −0.010 (3) | −0.015 (2) | 0.004 (2) |
C16 | 0.042 (3) | 0.031 (2) | 0.028 (2) | −0.010 (2) | −0.013 (2) | 0.0064 (19) |
S2 | 0.0379 (7) | 0.0196 (5) | 0.0287 (6) | −0.0090 (5) | −0.0035 (5) | 0.0028 (4) |
C21 | 0.023 (2) | 0.027 (2) | 0.022 (2) | −0.0090 (19) | −0.0065 (18) | 0.0009 (17) |
N21 | 0.027 (2) | 0.0194 (18) | 0.0241 (18) | −0.0053 (16) | −0.0060 (16) | −0.0006 (14) |
C23 | 0.034 (3) | 0.024 (2) | 0.032 (2) | −0.005 (2) | −0.014 (2) | −0.0037 (19) |
C24 | 0.033 (3) | 0.031 (3) | 0.042 (3) | 0.002 (2) | −0.010 (2) | −0.014 (2) |
C25 | 0.025 (3) | 0.053 (3) | 0.035 (3) | −0.005 (2) | 0.000 (2) | −0.013 (2) |
C26 | 0.028 (3) | 0.039 (3) | 0.027 (2) | −0.008 (2) | −0.001 (2) | −0.002 (2) |
S3 | 0.0347 (7) | 0.0287 (6) | 0.0283 (6) | −0.0045 (5) | −0.0079 (5) | −0.0107 (5) |
C31 | 0.031 (2) | 0.021 (2) | 0.026 (2) | −0.012 (2) | −0.004 (2) | −0.0050 (17) |
N31 | 0.035 (2) | 0.0222 (18) | 0.0284 (19) | −0.0065 (17) | −0.0062 (17) | −0.0046 (15) |
C33 | 0.043 (3) | 0.027 (2) | 0.035 (3) | −0.009 (2) | −0.011 (2) | 0.006 (2) |
C34 | 0.035 (3) | 0.027 (2) | 0.055 (3) | −0.004 (2) | −0.015 (3) | 0.006 (2) |
C35 | 0.027 (3) | 0.023 (2) | 0.056 (3) | 0.002 (2) | 0.009 (2) | −0.008 (2) |
C36 | 0.034 (3) | 0.024 (2) | 0.037 (3) | −0.007 (2) | 0.008 (2) | −0.009 (2) |
Sn1—C1 | 2.205 (4) | N11—C13 | 1.345 (5) |
Sn1—N11 | 2.303 (4) | C13—C14 | 1.364 (6) |
Sn1—N21 | 2.324 (3) | C14—C15 | 1.397 (6) |
Sn1—N31 | 3.113 (4) | C15—C16 | 1.382 (6) |
Sn1—S1 | 2.6264 (13) | S2—C21 | 1.749 (4) |
Sn1—S2 | 2.5362 (13) | C21—N21 | 1.351 (5) |
Sn1—S3 | 2.4931 (13) | C21—C26 | 1.410 (6) |
Sn1—Cl1 | 4.2240 (17) | N21—C23 | 1.342 (5) |
Cl1—C3 | 1.752 (5) | C23—C24 | 1.374 (6) |
C1—C2 | 1.483 (5) | C24—C25 | 1.388 (7) |
C2—C3 | 1.400 (6) | C25—C26 | 1.373 (6) |
C2—C7 | 1.401 (6) | S3—C31 | 1.762 (5) |
C3—C4 | 1.395 (6) | C31—N31 | 1.347 (5) |
C4—C5 | 1.373 (8) | C31—C36 | 1.403 (6) |
C5—C6 | 1.386 (8) | N31—C33 | 1.343 (6) |
C6—C7 | 1.382 (7) | C33—C34 | 1.387 (7) |
S1—C11 | 1.744 (4) | C34—C35 | 1.368 (7) |
C11—N11 | 1.357 (5) | C35—C36 | 1.374 (7) |
C11—C16 | 1.397 (6) | ||
C1—Sn1—N11 | 157.88 (13) | C4—C5—C6 | 120.0 (5) |
C1—Sn1—N21 | 95.32 (14) | C7—C6—C5 | 119.6 (5) |
N11—Sn1—N21 | 79.50 (12) | C6—C7—C2 | 122.4 (5) |
C1—Sn1—S3 | 109.11 (12) | C11—S1—Sn1 | 80.98 (14) |
N11—Sn1—S3 | 80.55 (9) | N11—C11—C16 | 120.5 (4) |
N21—Sn1—S3 | 154.28 (9) | N11—C11—S1 | 113.2 (3) |
C1—Sn1—S2 | 105.75 (12) | C16—C11—S1 | 126.3 (3) |
N11—Sn1—S2 | 91.50 (9) | C13—N11—C11 | 120.7 (4) |
N21—Sn1—S2 | 64.42 (9) | C13—N11—Sn1 | 136.8 (3) |
S3—Sn1—S2 | 100.16 (5) | C11—N11—Sn1 | 102.6 (3) |
C1—Sn1—S1 | 95.13 (12) | N11—C13—C14 | 121.6 (4) |
N11—Sn1—S1 | 63.20 (8) | C13—C14—C15 | 118.5 (4) |
N21—Sn1—S1 | 85.79 (9) | C16—C15—C14 | 120.6 (4) |
S3—Sn1—S1 | 99.49 (5) | C15—C16—C11 | 118.1 (4) |
S2—Sn1—S1 | 144.61 (4) | C21—S2—Sn1 | 82.38 (14) |
C1—Sn1—N31 | 66.36 (13) | N21—C21—C26 | 120.7 (4) |
N11—Sn1—N31 | 131.87 (10) | N21—C21—S2 | 113.2 (3) |
N21—Sn1—N31 | 133.72 (10) | C26—C21—S2 | 126.1 (3) |
S3—Sn1—N31 | 55.35 (7) | C23—N21—C21 | 120.6 (4) |
S2—Sn1—N31 | 79.66 (8) | C23—N21—Sn1 | 139.3 (3) |
S1—Sn1—N31 | 135.52 (7) | C21—N21—Sn1 | 99.9 (2) |
C1—Sn1—Cl1 | 45.37 (12) | N21—C23—C24 | 121.4 (4) |
N11—Sn1—Cl1 | 131.76 (9) | C23—C24—C25 | 118.4 (4) |
N21—Sn1—Cl1 | 52.54 (9) | C26—C25—C24 | 121.3 (4) |
S3—Sn1—Cl1 | 146.40 (4) | C25—C26—C21 | 117.5 (4) |
S2—Sn1—Cl1 | 73.82 (4) | C31—S3—Sn1 | 99.95 (14) |
S1—Sn1—Cl1 | 103.82 (4) | N31—C31—C36 | 122.3 (4) |
N31—Sn1—Cl1 | 91.20 (7) | N31—C31—S3 | 117.1 (3) |
C3—Cl1—Sn1 | 68.99 (14) | C36—C31—S3 | 120.6 (3) |
C2—C1—Sn1 | 113.3 (3) | C33—N31—C31 | 117.8 (4) |
C3—C2—C7 | 116.3 (4) | C33—N31—Sn1 | 152.9 (3) |
C3—C2—C1 | 123.4 (4) | C31—N31—Sn1 | 85.4 (2) |
C7—C2—C1 | 120.3 (4) | N31—C33—C34 | 122.9 (5) |
C4—C3—C2 | 121.7 (4) | C35—C34—C33 | 118.6 (5) |
C4—C3—Cl1 | 118.4 (4) | C34—C35—C36 | 120.2 (4) |
C2—C3—Cl1 | 119.9 (3) | C35—C36—C31 | 118.3 (4) |
C5—C4—C3 | 120.0 (5) | ||
C1—Sn1—Cl1—C3 | 55.8 (2) | S3—Sn1—S2—C21 | −160.02 (14) |
N11—Sn1—Cl1—C3 | −93.93 (19) | S1—Sn1—S2—C21 | −37.23 (16) |
N21—Sn1—Cl1—C3 | −101.19 (19) | N31—Sn1—S2—C21 | 148.28 (15) |
S3—Sn1—Cl1—C3 | 104.95 (17) | Cl1—Sn1—S2—C21 | 53.97 (14) |
S2—Sn1—Cl1—C3 | −171.07 (16) | Sn1—S2—C21—N21 | 3.0 (3) |
S1—Sn1—Cl1—C3 | −27.67 (16) | Sn1—S2—C21—C26 | −175.5 (4) |
N31—Sn1—Cl1—C3 | 110.06 (17) | C26—C21—N21—C23 | −1.0 (6) |
N11—Sn1—C1—C2 | 28.2 (6) | S2—C21—N21—C23 | −179.5 (3) |
N21—Sn1—C1—C2 | −46.9 (3) | C26—C21—N21—Sn1 | 175.3 (3) |
S3—Sn1—C1—C2 | 141.2 (3) | S2—C21—N21—Sn1 | −3.2 (3) |
S2—Sn1—C1—C2 | −111.8 (3) | C1—Sn1—N21—C23 | 72.5 (4) |
S1—Sn1—C1—C2 | 39.3 (3) | N11—Sn1—N21—C23 | −85.8 (4) |
N31—Sn1—C1—C2 | 177.3 (3) | S3—Sn1—N21—C23 | −125.5 (4) |
Cl1—Sn1—C1—C2 | −65.1 (3) | S2—Sn1—N21—C23 | 177.4 (5) |
Sn1—C1—C2—C3 | 94.4 (4) | S1—Sn1—N21—C23 | −22.3 (4) |
Sn1—C1—C2—C7 | −87.5 (4) | N31—Sn1—N21—C23 | 134.6 (4) |
C7—C2—C3—C4 | 0.2 (6) | Cl1—Sn1—N21—C23 | 88.7 (4) |
C1—C2—C3—C4 | 178.4 (4) | C1—Sn1—N21—C21 | −102.6 (3) |
C7—C2—C3—Cl1 | −178.6 (3) | N11—Sn1—N21—C21 | 99.1 (3) |
C1—C2—C3—Cl1 | −0.5 (6) | S3—Sn1—N21—C21 | 59.4 (3) |
Sn1—Cl1—C3—C4 | 150.6 (4) | S2—Sn1—N21—C21 | 2.3 (2) |
Sn1—Cl1—C3—C2 | −30.5 (3) | S1—Sn1—N21—C21 | 162.6 (2) |
C2—C3—C4—C5 | 0.7 (7) | N31—Sn1—N21—C21 | −40.6 (3) |
Cl1—C3—C4—C5 | 179.6 (4) | Cl1—Sn1—N21—C21 | −86.4 (2) |
C3—C4—C5—C6 | −1.1 (8) | C21—N21—C23—C24 | 0.5 (6) |
C4—C5—C6—C7 | 0.5 (8) | Sn1—N21—C23—C24 | −174.0 (3) |
C5—C6—C7—C2 | 0.5 (8) | N21—C23—C24—C25 | 0.5 (7) |
C3—C2—C7—C6 | −0.8 (7) | C23—C24—C25—C26 | −0.9 (7) |
C1—C2—C7—C6 | −179.1 (4) | C24—C25—C26—C21 | 0.4 (7) |
C1—Sn1—S1—C11 | −174.37 (18) | N21—C21—C26—C25 | 0.6 (6) |
N11—Sn1—S1—C11 | 0.96 (17) | S2—C21—C26—C25 | 178.9 (3) |
N21—Sn1—S1—C11 | −79.39 (17) | C1—Sn1—S3—C31 | 33.41 (18) |
S3—Sn1—S1—C11 | 75.24 (15) | N11—Sn1—S3—C31 | −167.15 (16) |
S2—Sn1—S1—C11 | −47.73 (16) | N21—Sn1—S3—C31 | −127.6 (2) |
N31—Sn1—S1—C11 | 124.52 (17) | S2—Sn1—S3—C31 | −77.32 (14) |
Cl1—Sn1—S1—C11 | −129.14 (14) | S1—Sn1—S3—C31 | 132.26 (14) |
Sn1—S1—C11—N11 | −1.6 (3) | N31—Sn1—S3—C31 | −7.53 (16) |
Sn1—S1—C11—C16 | 179.8 (4) | Cl1—Sn1—S3—C31 | −1.31 (16) |
C16—C11—N11—C13 | 2.1 (6) | Sn1—S3—C31—N31 | 16.3 (3) |
S1—C11—N11—C13 | −176.6 (3) | Sn1—S3—C31—C36 | −163.3 (3) |
C16—C11—N11—Sn1 | −179.4 (3) | C36—C31—N31—C33 | 1.5 (6) |
S1—C11—N11—Sn1 | 1.8 (3) | S3—C31—N31—C33 | −178.1 (3) |
C1—Sn1—N11—C13 | −170.8 (4) | C36—C31—N31—Sn1 | 166.8 (4) |
N21—Sn1—N11—C13 | −92.6 (4) | S3—C31—N31—Sn1 | −12.8 (3) |
S3—Sn1—N11—C13 | 71.0 (4) | C1—Sn1—N31—C33 | 22.7 (6) |
S2—Sn1—N11—C13 | −29.0 (4) | N11—Sn1—N31—C33 | −172.3 (6) |
S1—Sn1—N11—C13 | 176.8 (4) | N21—Sn1—N31—C33 | −51.1 (7) |
N31—Sn1—N11—C13 | 48.4 (4) | S3—Sn1—N31—C33 | 160.2 (7) |
Cl1—Sn1—N11—C13 | −98.5 (4) | S2—Sn1—N31—C33 | −89.7 (6) |
C1—Sn1—N11—C11 | 11.2 (5) | S1—Sn1—N31—C33 | 94.9 (6) |
N21—Sn1—N11—C11 | 89.3 (3) | Cl1—Sn1—N31—C33 | −16.4 (6) |
S3—Sn1—N11—C11 | −107.0 (3) | C1—Sn1—N31—C31 | −127.7 (3) |
S2—Sn1—N11—C11 | 153.0 (2) | N11—Sn1—N31—C31 | 37.2 (3) |
S1—Sn1—N11—C11 | −1.3 (2) | N21—Sn1—N31—C31 | 158.5 (2) |
N31—Sn1—N11—C11 | −129.6 (2) | S3—Sn1—N31—C31 | 9.8 (2) |
Cl1—Sn1—N11—C11 | 83.5 (3) | S2—Sn1—N31—C31 | 119.9 (2) |
C11—N11—C13—C14 | −0.7 (6) | S1—Sn1—N31—C31 | −55.6 (3) |
Sn1—N11—C13—C14 | −178.5 (3) | Cl1—Sn1—N31—C31 | −166.8 (2) |
N11—C13—C14—C15 | −1.0 (7) | C31—N31—C33—C34 | −2.3 (6) |
C13—C14—C15—C16 | 1.2 (7) | Sn1—N31—C33—C34 | −148.5 (5) |
C14—C15—C16—C11 | 0.2 (7) | N31—C33—C34—C35 | 1.8 (7) |
N11—C11—C16—C15 | −1.9 (7) | C33—C34—C35—C36 | −0.5 (7) |
S1—C11—C16—C15 | 176.7 (4) | C34—C35—C36—C31 | −0.2 (7) |
C1—Sn1—S2—C21 | 86.64 (18) | N31—C31—C36—C35 | −0.3 (6) |
N11—Sn1—S2—C21 | −79.35 (16) | S3—C31—C36—C35 | 179.3 (3) |
N21—Sn1—S2—C21 | −1.75 (16) |
Experimental details
Crystal data | |
Chemical formula | [Sn(C5H4NS)3(C7H6Cl)] |
Mr | 574.71 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 170 |
a, b, c (Å) | 7.725 (3), 10.321 (3), 15.548 (5) |
α, β, γ (°) | 80.26 (2), 77.18 (2), 74.82 (2) |
V (Å3) | 1158.4 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.50 |
Crystal size (mm) | 0.50 × 0.14 × 0.05 |
Data collection | |
Diffractometer | Siemens R3m/V diffractometer |
Absorption correction | ψ-scan (XEMP in P3 Software; Siemens, 1989) |
Tmin, Tmax | 0.501, 0.928 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5674, 4098, 3216 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.073, 0.94 |
No. of reflections | 4098 |
No. of parameters | 273 |
H-atom treatment | Only H-atom displacement parameters refined |
Δρmax, Δρmin (e Å−3) | 0.54, −0.46 |
Computer programs: P3 Software (Siemens, 1989), XDISK in P3 Software, SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXL97 and PLATON (Spek, 1990).
Sn1—C1 | 2.205 (4) | Sn1—S1 | 2.6264 (13) |
Sn1—N11 | 2.303 (4) | Sn1—S2 | 2.5362 (13) |
Sn1—N21 | 2.324 (3) | Sn1—S3 | 2.4931 (13) |
Sn1—N31 | 3.113 (4) | Sn1—Cl1 | 4.2240 (17) |
C1—Sn1—N11 | 157.88 (13) | S2—Sn1—S1 | 144.61 (4) |
N21—Sn1—S3 | 154.28 (9) |
In mono- and diorganotin(IV) complexes of 2-mercaptopyridine (HSPy) such as RSn(SPy)3 [R is Me or Ph (Huber et al., 1997), or p-tolyl (Schürmann & Huber, 1994)], Ph2Sn(SPy)2 (Schmiedgen et al., 1993) or Ph2SnCl(SPy) (Schmiedgen, Huber, Preut et al., 1994), SPy acts as a bidentate ligand. Thus, the Sn atom achieves coordination numbers of 7, 6 and 5, respectively. In Sn(SPy)4·HSPy, the Sn was found not to be eight-coordinate, as might have been expected, but only six-coordinate, two SPy ligands being bidentate and the other two monodentate (Damude et al., 1990). A study of the structure of the title compound, (I), showed that bidentate and monodentate SPy ligands are present also in this compound, the Sn atom, in contrast with other RSn(SPy)3 compounds, being six-coordinate. \sch
All three SPy ligands of (I) are bonded via S to Sn. The Sn—S bond distances are comparable with the sums of the covalent radii (2.42 Å; Bondi, 1964) and correspond to Sn—S bond distances observed in similar compounds. These were discussed in a previous paper on the structure of n-BuSn(SPym)3 (SPym is 2-mercaptopyrimidine; Schmiedgen, Huber & Schürmann, 1994).
Each of the three Sn—N distances in (I) [2.303 (4)–3.113 (4) Å] is distinctly shorter than the sum of the appropriate van der Waals distances (3.75 Å; Bondi, 1964). However, the Sn—N distances of two of the SPy ligands (average value 2.315 Å) are shorter than in comparable compounds [p-TolSn(SPy)3 2.466 Å (Schürmann & Huber, 1994), MeSn(SPy)3 2.483 Å and PhSn(SPy)3 2.432 Å (Huber et al., 1997), and Ph2Sn(SPy)2 2.667 Å (Schmiedgen et al., 1993)] and indicate, when compared with the sum of the covalent radii (2.15 Å; Bondi, 1964), the existence of Sn—N coordination and the bidentate nature of two of the SPy ligands. The Sn—N distance of the third ligand [3.113 (4) Å] is distinctly longer, thus excluding appreciable coordinative interaction. Accordingly, this ligand shows the shortest of the three Sn—S distances. Therefore, the coordination polyhedron around Sn can be described as a distorted octahedron.
The S—Sn—N bite angles [64.42 (9) and 63.20 (8)°] of the two bidentate ligands are similar to the appropriate angles in Sn(SPy)4·HSPy [64.2 (2) and 65.1 (2)°; Damude et al., 1990] and tend to be larger than in RSn(SPy)3 and Ph2Sn(SPy)2, which contain only bidentate SPy ligands. Intermolecular distances shorter than the sum of the van der Waals radii were not found.