metal-organic compounds
Bis(μ-disulfur dinitrido)bis[diphenyltin(IV)]
aDepartment of Chemistry, University of St Andrews, St Andrews, KY16 9ST, Scotland
*Correspondence e-mail: amzs@st-and.ac.uk
The title compound, [Sn2(C6H5)4(N2S2)2], exists as a centrosymmetric binuclear dimer with the SnIV centres in distorted trigonal bipyramidal geometry and a central Sn2N2 core.
Related literature
For related literature, see: Aucott et al. (2002, 2003); Bates et al. (1986); Chivers et al. (1986); Jones et al. (1985a,b, 1986, 1987, 1988); Kelly & Woollins (1986); Read et al. (2007); Slawin & Woollins (2006).
Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku, 2004); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808008957/bt2692sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008957/bt2692Isup2.hkl
Ammonia gas (400 ml) was condensed into a dry-ice/acetone cooled Schlenk flask.[S4N3]Cl (18.47 g, 0.019 moles) was then added, forming a dark red solution. After stirring for 30 minutes, Ph2SnCl2 (1.68 g, 4.88 mmoles) was added, and the mixture stirred at 195 K for 4 h, before removal of the lower cooling bath, allowing NH3(l) reflux, and eventually evaporation overnight. The solid products were transferred to a Sohxlet apparatus, containing dry, degassed petroleum ether (140 ml) and cycled for 4 h, by which point the extracts appeared almost colourless. The lower flask was then placed under N2(g) at 250 K for 12 h, yielding bright yellow-orange crystals of Ph2SnS2N2, collected by filtration under N2. Yield: 0.092 g, 5.15%. IR Spectrum (KBr Pellet, cm-1): 3063 (m), 2963 (m), 1428 (versus), 1070 (s), 1024 (s), 899 (s), 729 (s), 694 (s), 636(s), 440 (s) and 382 (s), 1H NMR: δH 7.56–7.53 (4H, m, Ph) and 7.40–7.37 (6H, m, Ph), EI m/z (%): 366.05 (Ph2SnS2N2, 5), 288.99 (PhSnS2N2, 2), 257.01 (PhSnSN2, 2), 197.01 (PhSn, 68), 77.06 (Ph, 25) and 63.96 (S2, 8), Melting Point: 411–13 K.
All H atoms were included in calculated positions (C—H distance 0.95Å) and were refined as riding atoms with Uiso(H) = 1.2 Ueq(parent atom, and aryl H atoms). The highest peak in the difference map is 0.95 Å from atom S(2) and the deepest hole is 0.96 Å from Sn(1)
Data collection: CrystalClear (Rigaku, 2004); cell
CrystalClear (Rigaku, 2004); data reduction: CrystalClear (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The structure of title compound with displacement ellipsoids drawn at the 50% probability level. Symmetry operator for generating equivalent atoms: (A) 1-x, 1-y, 1-z. |
[Sn2(C6H5)4(N2S2)2] | Z = 1 |
Mr = 730.06 | F(000) = 356 |
Triclinic, P1 | Dx = 1.892 Mg m−3 |
a = 8.9235 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.2285 (9) Å | Cell parameters from 2584 reflections |
c = 9.5881 (8) Å | θ = 2.5–28.3° |
α = 63.809 (2)° | µ = 2.30 mm−1 |
β = 67.309 (2)° | T = 93 K |
γ = 70.471 (2)° | Prism, yellow |
V = 640.72 (9) Å3 | 0.20 × 0.03 × 0.03 mm |
Rigaku Mercury diffractometer | 2267 independent reflections |
Radiation source: rotating anode | 2110 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.046 |
Detector resolution: 0.83 pixels mm-1 | θmax = 25.1°, θmin = 2.5° |
ω and ϕ scans | h = −9→10 |
Absorption correction: multi-scan (CrystalClear; Rigaku 2004) | k = −7→11 |
Tmin = 0.923, Tmax = 0.941 | l = −8→11 |
4110 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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0548P)2] where P = (Fo2 + 2Fc2)/3 |
2267 reflections | (Δ/σ)max = 0.001 |
155 parameters | Δρmax = 0.85 e Å−3 |
0 restraints | Δρmin = −1.19 e Å−3 |
[Sn2(C6H5)4(N2S2)2] | γ = 70.471 (2)° |
Mr = 730.06 | V = 640.72 (9) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.9235 (6) Å | Mo Kα radiation |
b = 9.2285 (9) Å | µ = 2.30 mm−1 |
c = 9.5881 (8) Å | T = 93 K |
α = 63.809 (2)° | 0.20 × 0.03 × 0.03 mm |
β = 67.309 (2)° |
Rigaku Mercury diffractometer | 2267 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku 2004) | 2110 reflections with I > 2σ(I) |
Tmin = 0.923, Tmax = 0.941 | Rint = 0.046 |
4110 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.85 e Å−3 |
2267 reflections | Δρmin = −1.19 e Å−3 |
155 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 | 0.42885 (3) | 0.54581 (3) | 0.68014 (3) | 0.01479 (16) | |
N1 | 0.6474 (5) | 0.4511 (4) | 0.5243 (4) | 0.0163 (8) | |
S1 | 0.81765 (14) | 0.40140 (14) | 0.55466 (14) | 0.0202 (3) | |
N2 | 0.8196 (5) | 0.4231 (5) | 0.7071 (5) | 0.0229 (9) | |
S2 | 0.64354 (15) | 0.49589 (15) | 0.82590 (15) | 0.0237 (3) | |
C1 | 0.3401 (5) | 0.8035 (5) | 0.6353 (5) | 0.0158 (9) | |
C2 | 0.2544 (6) | 0.9079 (5) | 0.5220 (6) | 0.0238 (11) | |
H2A | 0.2361 | 0.8658 | 0.4569 | 0.029* | |
C3 | 0.1945 (6) | 1.0741 (6) | 0.5022 (7) | 0.0288 (12) | |
H3A | 0.1352 | 1.1441 | 0.4246 | 0.035* | |
C4 | 0.2214 (6) | 1.1370 (6) | 0.5952 (7) | 0.0274 (12) | |
H4A | 0.1820 | 1.2503 | 0.5811 | 0.033* | |
C5 | 0.3050 (7) | 1.0347 (6) | 0.7075 (7) | 0.0301 (13) | |
H5A | 0.3227 | 1.0775 | 0.7725 | 0.036* | |
C6 | 0.3644 (6) | 0.8701 (6) | 0.7283 (6) | 0.0251 (11) | |
H6A | 0.4226 | 0.8013 | 0.8071 | 0.030* | |
C7 | 0.2886 (6) | 0.3648 (5) | 0.8626 (6) | 0.0176 (10) | |
C8 | 0.3637 (6) | 0.2265 (6) | 0.9698 (6) | 0.0234 (11) | |
H8A | 0.4760 | 0.2148 | 0.9628 | 0.028* | |
C9 | 0.2755 (7) | 0.1059 (6) | 1.0865 (6) | 0.0351 (13) | |
H9A | 0.3265 | 0.0130 | 1.1612 | 0.042* | |
C10 | 0.1130 (7) | 0.1206 (7) | 1.0945 (7) | 0.0346 (13) | |
H10A | 0.0540 | 0.0359 | 1.1725 | 0.042* | |
C11 | 0.0361 (7) | 0.2576 (7) | 0.9900 (7) | 0.0360 (14) | |
H11A | −0.0765 | 0.2697 | 0.9976 | 0.043* | |
C12 | 0.1259 (6) | 0.3773 (6) | 0.8739 (6) | 0.0241 (11) | |
H12A | 0.0742 | 0.4705 | 0.8000 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0162 (2) | 0.0132 (2) | 0.0155 (2) | −0.00201 (15) | −0.00536 (16) | −0.00553 (16) |
N1 | 0.0150 (19) | 0.0190 (19) | 0.018 (2) | −0.0018 (15) | −0.0066 (16) | −0.0089 (16) |
S1 | 0.0152 (6) | 0.0246 (6) | 0.0244 (7) | −0.0011 (5) | −0.0084 (5) | −0.0115 (5) |
N2 | 0.022 (2) | 0.026 (2) | 0.024 (2) | −0.0046 (17) | −0.0108 (18) | −0.0087 (18) |
S2 | 0.0237 (7) | 0.0309 (7) | 0.0229 (7) | −0.0028 (5) | −0.0107 (5) | −0.0135 (6) |
C1 | 0.015 (2) | 0.014 (2) | 0.017 (2) | −0.0048 (17) | −0.0007 (19) | −0.0066 (18) |
C2 | 0.032 (3) | 0.020 (2) | 0.020 (3) | −0.005 (2) | −0.008 (2) | −0.008 (2) |
C3 | 0.029 (3) | 0.021 (3) | 0.034 (3) | 0.002 (2) | −0.014 (2) | −0.008 (2) |
C4 | 0.030 (3) | 0.014 (2) | 0.035 (3) | −0.005 (2) | −0.007 (2) | −0.007 (2) |
C5 | 0.034 (3) | 0.030 (3) | 0.038 (3) | −0.005 (2) | −0.012 (3) | −0.021 (3) |
C6 | 0.026 (3) | 0.022 (3) | 0.028 (3) | −0.001 (2) | −0.009 (2) | −0.011 (2) |
C7 | 0.022 (3) | 0.015 (2) | 0.017 (2) | −0.0024 (18) | −0.0050 (19) | −0.0074 (19) |
C8 | 0.024 (3) | 0.023 (3) | 0.021 (3) | −0.005 (2) | −0.007 (2) | −0.005 (2) |
C9 | 0.049 (4) | 0.025 (3) | 0.020 (3) | −0.009 (2) | −0.010 (3) | 0.003 (2) |
C10 | 0.038 (3) | 0.037 (3) | 0.025 (3) | −0.018 (3) | −0.006 (3) | −0.002 (2) |
C11 | 0.032 (3) | 0.046 (3) | 0.023 (3) | −0.018 (3) | 0.002 (2) | −0.007 (3) |
C12 | 0.025 (3) | 0.023 (2) | 0.018 (3) | −0.002 (2) | −0.006 (2) | −0.004 (2) |
Sn1—C7 | 2.132 (5) | C4—H4A | 0.9500 |
Sn1—N1 | 2.137 (4) | C5—C6 | 1.380 (7) |
Sn1—C1 | 2.138 (4) | C5—H5A | 0.9500 |
Sn1—N1i | 2.296 (3) | C6—H6A | 0.9500 |
Sn1—S2 | 2.5967 (12) | C7—C12 | 1.382 (7) |
N1—S1 | 1.536 (4) | C7—C8 | 1.392 (6) |
N1—Sn1i | 2.296 (3) | C8—C9 | 1.385 (7) |
S1—N2 | 1.567 (4) | C8—H8A | 0.9500 |
N2—S2 | 1.675 (4) | C9—C10 | 1.385 (8) |
C1—C2 | 1.385 (6) | C9—H9A | 0.9500 |
C1—C6 | 1.394 (6) | C10—C11 | 1.381 (8) |
C2—C3 | 1.396 (6) | C10—H10A | 0.9500 |
C2—H2A | 0.9500 | C11—C12 | 1.385 (7) |
C3—C4 | 1.379 (7) | C11—H11A | 0.9500 |
C3—H3A | 0.9500 | C12—H12A | 0.9500 |
C4—C5 | 1.364 (8) | ||
C7—Sn1—N1 | 114.01 (15) | C5—C4—H4A | 120.3 |
C7—Sn1—C1 | 122.65 (16) | C3—C4—H4A | 120.3 |
N1—Sn1—C1 | 122.73 (15) | C4—C5—C6 | 121.0 (5) |
C7—Sn1—N1i | 93.55 (15) | C4—C5—H5A | 119.5 |
N1—Sn1—N1i | 72.82 (15) | C6—C5—H5A | 119.5 |
C1—Sn1—N1i | 95.25 (15) | C5—C6—C1 | 120.9 (5) |
C7—Sn1—S2 | 98.61 (12) | C5—C6—H6A | 119.6 |
N1—Sn1—S2 | 80.65 (9) | C1—C6—H6A | 119.6 |
C1—Sn1—S2 | 97.87 (12) | C12—C7—C8 | 118.6 (4) |
N1i—Sn1—S2 | 153.42 (10) | C12—C7—Sn1 | 121.8 (3) |
S1—N1—Sn1 | 121.6 (2) | C8—C7—Sn1 | 119.5 (3) |
S1—N1—Sn1i | 131.2 (2) | C9—C8—C7 | 120.3 (5) |
Sn1—N1—Sn1i | 107.18 (15) | C9—C8—H8A | 119.9 |
N1—S1—N2 | 115.8 (2) | C7—C8—H8A | 119.9 |
S1—N2—S2 | 120.4 (2) | C8—C9—C10 | 120.0 (5) |
N2—S2—Sn1 | 101.63 (14) | C8—C9—H9A | 120.0 |
C2—C1—C6 | 117.8 (4) | C10—C9—H9A | 120.0 |
C2—C1—Sn1 | 123.6 (3) | C11—C10—C9 | 120.5 (5) |
C6—C1—Sn1 | 118.6 (3) | C11—C10—H10A | 119.8 |
C1—C2—C3 | 120.9 (4) | C9—C10—H10A | 119.8 |
C1—C2—H2A | 119.6 | C10—C11—C12 | 118.8 (5) |
C3—C2—H2A | 119.6 | C10—C11—H11A | 120.6 |
C4—C3—C2 | 120.1 (5) | C12—C11—H11A | 120.6 |
C4—C3—H3A | 120.0 | C7—C12—C11 | 121.8 (4) |
C2—C3—H3A | 120.0 | C7—C12—H12A | 119.1 |
C5—C4—C3 | 119.4 (5) | C11—C12—H12A | 119.1 |
C7—Sn1—N1—S1 | −96.1 (3) | C6—C1—C2—C3 | −0.1 (7) |
C1—Sn1—N1—S1 | 92.6 (3) | Sn1—C1—C2—C3 | 177.8 (4) |
N1i—Sn1—N1—S1 | 177.8 (3) | C1—C2—C3—C4 | 0.5 (8) |
S2—Sn1—N1—S1 | −0.7 (2) | C2—C3—C4—C5 | −0.8 (8) |
C7—Sn1—N1—Sn1i | 86.17 (18) | C3—C4—C5—C6 | 0.6 (8) |
C1—Sn1—N1—Sn1i | −85.12 (19) | C4—C5—C6—C1 | −0.2 (8) |
N1i—Sn1—N1—Sn1i | 0.001 (2) | C2—C1—C6—C5 | −0.1 (7) |
S2—Sn1—N1—Sn1i | −178.51 (14) | Sn1—C1—C6—C5 | −178.0 (4) |
Sn1—N1—S1—N2 | 0.6 (3) | N1—Sn1—C7—C12 | −120.4 (4) |
Sn1i—N1—S1—N2 | 177.8 (2) | C1—Sn1—C7—C12 | 50.9 (4) |
N1—S1—N2—S2 | 0.2 (4) | N1i—Sn1—C7—C12 | −47.6 (4) |
S1—N2—S2—Sn1 | −0.6 (3) | S2—Sn1—C7—C12 | 156.1 (3) |
C7—Sn1—S2—N2 | 113.77 (18) | N1—Sn1—C7—C8 | 57.0 (4) |
N1—Sn1—S2—N2 | 0.68 (16) | C1—Sn1—C7—C8 | −131.7 (4) |
C1—Sn1—S2—N2 | −121.35 (18) | N1i—Sn1—C7—C8 | 129.7 (4) |
N1i—Sn1—S2—N2 | −2.5 (3) | S2—Sn1—C7—C8 | −26.6 (4) |
C7—Sn1—C1—C2 | −92.6 (4) | C12—C7—C8—C9 | −1.0 (7) |
N1—Sn1—C1—C2 | 77.9 (4) | Sn1—C7—C8—C9 | −178.5 (4) |
N1i—Sn1—C1—C2 | 5.0 (4) | C7—C8—C9—C10 | 1.6 (8) |
S2—Sn1—C1—C2 | 161.8 (4) | C8—C9—C10—C11 | −2.1 (9) |
C7—Sn1—C1—C6 | 85.2 (4) | C9—C10—C11—C12 | 2.0 (9) |
N1—Sn1—C1—C6 | −104.3 (4) | C8—C7—C12—C11 | 1.0 (7) |
N1i—Sn1—C1—C6 | −177.2 (4) | Sn1—C7—C12—C11 | 178.4 (4) |
S2—Sn1—C1—C6 | −20.4 (4) | C10—C11—C12—C7 | −1.5 (8) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Sn2(C6H5)4(N2S2)2] |
Mr | 730.06 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 93 |
a, b, c (Å) | 8.9235 (6), 9.2285 (9), 9.5881 (8) |
α, β, γ (°) | 63.809 (2), 67.309 (2), 70.471 (2) |
V (Å3) | 640.72 (9) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 2.30 |
Crystal size (mm) | 0.20 × 0.03 × 0.03 |
Data collection | |
Diffractometer | Rigaku Mercury diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku 2004) |
Tmin, Tmax | 0.923, 0.941 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4110, 2267, 2110 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.099, 1.14 |
No. of reflections | 2267 |
No. of parameters | 155 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.85, −1.19 |
Computer programs: CrystalClear (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Sn1—N1 | 2.137 (4) | N1—S1 | 1.536 (4) |
Sn1—N1i | 2.296 (3) | S1—N2 | 1.567 (4) |
Sn1—S2 | 2.5967 (12) | N2—S2 | 1.675 (4) |
N1—Sn1—N1i | 72.82 (15) | N1—S1—N2 | 115.8 (2) |
N1—Sn1—S2 | 80.65 (9) | S1—N2—S2 | 120.4 (2) |
S1—N1—Sn1 | 121.6 (2) | N2—S2—Sn1 | 101.63 (14) |
Sn1—N1—Sn1i | 107.18 (15) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
References
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The disulfurdinitride dianion is unknown in simple salts but can be isolated in metal complexes (Kelly and Woollins 1986, Jones et al. 1985a,b; Bates et al. 1986, Read et al. 2007) which may be protonated at the metal coordinated nitrogen (Jones et al. 1986, 1988) and we have previously commented on the structural consequences of this protonation (Jones et al. 1987). Recently, we developed a new route to disulfurdinitrido complexes from Bu2SnS2N2 (Aucott et al. 2002) and examined the metallation of the IrS2N2 and CoS2N2 rings using the AuPR3 cation as a species which is isolobal with a proton (Aucott et al. 2003, Slawin and Woollins 2006).
The structure of the title compound contains tin centres in distorted trigonal bipyramidal geometry and a central Sn2N2 ring (Figure 1). The binuclaear dimer is disposed about a centre of symmetry. The central core (excluding the phenyl rings) is planar with a mean deviation of 0.01 Å and a maximum deviation of 0.025 Å for N(1). The geometry is very similar to that of [n-Bu2SnS2N2]2 (Aucott et al. 2002). Comparison of the S—N bond lengths with platinum phosphine substituted complexes containing the S2N2 group reveals that the S—N bond lengths have a different motif to the PMe2Ph complex (Jones et al 1988) and one of the published PPh3 complexes (Chivers et al. 1986), but are comparable with most others systems containing the disulfurdinitrido anion (Jones et al. 1985a, Bates et al 1986).