Bis(μ-disulfur dinitrido)bis­[diphenyl­tin(IV)]

Robertson, A.P.M.; Slawin, A.M.Z.; Woollins, J.D.

doi:10.1107/S1600536808008957

metal-organic compounds

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Volume 64| Part 5| May 2008| Page m659

doi:10.1107/S1600536808008957

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Bis(μ-disulfur dinitrido)bis[diphenyltin(IV)]

Alasdair P. M. Robertson,^a Alexandra M. Z. Slawin ^a ^* and J. Derek Woollins ^a

^aDepartment of Chemistry, University of St Andrews, St Andrews, KY16 9ST, Scotland
^*Correspondence e-mail: amzs@st-and.ac.uk

(Received 1 April 2008; accepted 2 April 2008; online 10 April 2008)

The title compound, [Sn₂(C₆H₅)₄(N₂S₂)₂], exists as a centrosymmetric binuclear dimer with the Sn^IV 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

[Sn₂(C₆H₅)₄(N₂S₂)₂]
M_r = 730.06
Triclinic, $[P \overline 1]$
a = 8.9235 (6) Å
b = 9.2285 (9) Å
c = 9.5881 (8) Å
α = 63.809 (2)°
β = 67.309 (2)°
γ = 70.471 (2)°
V = 640.72 (9) Å³
Z = 1
Mo Kα radiation
μ = 2.30 mm⁻¹
T = 93 (2) K
0.20 × 0.03 × 0.03 mm

Data collection

Rigaku Mercury diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku 2004 ) T_min = 0.923, T_max = 0.941
4110 measured reflections
2267 independent reflections
2110 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.099
S = 1.14
2267 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −1.19 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—N1	2.137 (4)
Sn1—N1ⁱ	2.296 (3)
Sn1—S2	2.5967 (12)

N1—Sn1—N1ⁱ	72.82 (15)
N1—Sn1—S2	80.65 (9)
S1—N1—Sn1	121.6 (2)
Sn1—N1—Sn1ⁱ	107.18 (15)
N2—S2—Sn1	101.63 (14)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2004); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008957/bt2692sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008957/bt2692Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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 top

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), Mass Spectrum: 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.

Computing details top

Data collection: CrystalClear (Rigaku, 2004); cell refinement: 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).

Figures top

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.

Bis(µ-disulfur dinitrido)bis[diphenyltin(IV)] top

Crystal data top

[Sn₂(C₆H₅)₄(N₂S₂)₂]	Z = 1
M_r = 730.06	F(000) = 356
Triclinic, P1	D_x = 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

Data collection top

Rigaku Mercury diffractometer	2267 independent reflections
Radiation source: rotating anode	2110 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.046
Detector resolution: 0.83 pixels mm^-1	θ_max = 25.1°, θ_min = 2.5°
ω and ϕ scans	h = −9→10
Absorption correction: multi-scan (CrystalClear; Rigaku 2004)	k = −7→11
T_min = 0.923, T_max = 0.941	l = −8→11
4110 measured reflections

Refinement top

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(F_o²) + (0.0548P)²] where P = (F_o² + 2F_c²)/3
2267 reflections	(Δ/σ)_max = 0.001
155 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −1.19 e Å⁻³

Crystal data top

[Sn₂(C₆H₅)₄(N₂S₂)₂]	γ = 70.471 (2)°
M_r = 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)°

Data collection top

Rigaku Mercury diffractometer	2267 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku 2004)	2110 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.941	R_int = 0.046
4110 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.14	Δρ_max = 0.85 e Å⁻³
2267 reflections	Δρ_min = −1.19 e Å⁻³
155 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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]
M_r	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)
T_min, T_max	0.923, 0.941
No. of measured, independent and observed [I > 2σ(I)] reflections	4110, 2267, 2110
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.85, −1.19

Computer programs: CrystalClear (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

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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Volume 64| Part 5| May 2008| Page m659

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