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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): m418.
Published online 2010 March 17. doi:  10.1107/S1600536810009487
PMCID: PMC2983911

(Disulfur dinitrido)triphenyl­anti­mony(V)

Abstract

The title compound, [Sb(C6H5)3(N2S2)], contains a molecular entity that is very similar to that of the known polymorph of Sb(S2N2)Ph3 [Kunkel et al. (1997 [triangle]). Z. Naturforsch. Teil B, 52, 193–198], differing only in the orientation of the phenyl rings. The bond order in the SNSN unit is S—N=S=N, consisting of one long S—N bond, an inter­mediate length N=S bond and a short S=N bond.

Related literature

For the polymorph crystallizing in space group P21/n, see: Kunkel et al. (1997 [triangle]). For Pt(S2N2)(PR 3)2 complexes with a similar bond order in the SNSN unit, see: Bates et al. (1986 [triangle]); Read et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m418-scheme1.jpg

Experimental

Crystal data

  • [Sb(C6H5)3(N2S2)]
  • M r = 445.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m418-efi1.jpg
  • a = 16.997 (3) Å
  • b = 11.587 (2) Å
  • c = 18.166 (3) Å
  • β = 99.732 (7)°
  • V = 3526.3 (11) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.80 mm−1
  • T = 93 K
  • 0.08 × 0.05 × 0.05 mm

Data collection

  • Rigaku Mercury70 CCD diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.741, T max = 0.914
  • 11155 measured reflections
  • 3094 independent reflections
  • 2826 reflections with F 2 > 2σ(F 2)
  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.113
  • S = 1.37
  • 3094 reflections
  • 208 parameters
  • H-atom parameters constrained
  • Δρmax = 3.38 e Å−3
  • Δρmin = −1.67 e Å−3

Data collection: SCXMini (Rigaku, 2006 [triangle]); cell refinement: SCXMini; data reduction: SCXMini; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: CrystalStructure (Rigaku, 2009 [triangle]); software used to prepare material for publication: CrystalStructure.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009487/jh2136sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009487/jh2136Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Previously the title compound has been prepared from tetrasulfurteranitride. The synthesis described here uses a non explosive S—N starting material.

Experimental

Liquid ammonia (30 ml) was condensed under nitrogen using an ammonia condenser filled with dry ice and acetone into a dry Schlenk tube in a dry ice/acetone bath. To this, 0.102 g (0.5 mmol) [S4N3]Cl was added. After stirring for 30 min s, 0.212 g (0.5 mmol) of triphenylstibenedichloride was added rapidly. The solution was then allowed to warm to room temperature and the ammonia gas blown off under a stream of nitrogen. The residue was placed under vacuum to remove any excess ammonia, before being dissolved in dichloromethane and filtered through celite. The product was precipitated by slow addition of hexane to give a yellow powder. Crystals were grown via slow diffusion of hexane into a solution of the product in dichloromethane.

Refinement

All H atoms were included in calculated positions and refined as riding atoms with Uĩso~(H) = 1.5 U~eq~. The highest peak in the difference map is 0.83 Å from atom Sb1

Figures

Fig. 1.
The structure of (1) with displacement ellipsoids drawn at the 50% probability level, hydrogen atoms omitted for clarity.

Crystal data

[Sb(C6H5)3(N2S2)]F(000) = 1760.00
Mr = 445.20Dx = 1.677 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2ycCell parameters from 1987 reflections
a = 16.997 (3) Åθ = 2.1–25.4°
b = 11.587 (2) ŵ = 1.80 mm1
c = 18.166 (3) ÅT = 93 K
β = 99.732 (7)°Prism, yellow
V = 3526.3 (11) Å30.08 × 0.05 × 0.05 mm
Z = 8

Data collection

Rigaku Mercury70 CCD diffractometer2826 reflections with F2 > 2σ(F2)
ω scansRint = 0.053
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)θmax = 25.4°
Tmin = 0.741, Tmax = 0.914h = −20→19
11155 measured reflectionsk = −8→13
3094 independent reflectionsl = −21→16

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.37w = 1/[σ2(Fo2) + (0.0236P)2 + 20.1P] where P = (Fo2 + 2Fc2)/3
3094 reflections(Δ/σ)max = 0.002
208 parametersΔρmax = 3.38 e Å3
0 restraintsΔρmin = −1.67 e Å3
Primary atom site location: structure-invariant direct methods

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

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

xyzUiso*/Ueq
Sb(1)0.22035 (2)0.02024 (4)0.064344 (19)0.0189
S(1)0.39390 (10)0.02791 (16)0.16524 (9)0.0317
S(2)0.34568 (10)0.05730 (17)0.01298 (9)0.0326
N(1)0.3060 (3)0.0161 (5)0.1682 (3)0.0320
N(2)0.4187 (4)0.0478 (6)0.0857 (3)0.0402
C(1)0.1547 (4)0.1472 (5)0.1125 (3)0.0176
C(2)0.1924 (4)0.2490 (5)0.1401 (3)0.0187
C(3)0.1493 (4)0.3314 (6)0.1715 (3)0.0245
C(4)0.0709 (4)0.3115 (6)0.1773 (3)0.0283
C(5)0.0330 (4)0.2102 (6)0.1503 (3)0.0299
C(6)0.0750 (4)0.1279 (6)0.1179 (3)0.0242
C(7)0.1724 (4)−0.1403 (5)0.0867 (3)0.0210
C(8)0.1975 (4)−0.1975 (6)0.1561 (4)0.0266
C(9)0.1631 (4)−0.2976 (6)0.1714 (4)0.0327
C(10)0.1015 (4)−0.3454 (6)0.1208 (4)0.0312
C(11)0.0752 (4)−0.2915 (6)0.0538 (4)0.0319
C(12)0.1128 (4)−0.1908 (5)0.0364 (3)0.0223
C(13)0.1639 (4)0.0371 (5)−0.0517 (3)0.0192
C(14)0.1094 (4)0.1244 (5)−0.0747 (3)0.0202
C(15)0.0780 (4)0.1359 (6)−0.1512 (3)0.0266
C(16)0.1023 (4)0.0618 (6)−0.2029 (3)0.0271
C(17)0.1570 (4)−0.0245 (6)−0.1798 (3)0.0295
C(18)0.1880 (4)−0.0367 (6)−0.1046 (3)0.0257
H(2)0.24710.26160.13740.022*
H(3)0.17400.40200.18900.029*
H(4)0.04230.36780.20020.034*
H(5)−0.02140.19760.15400.036*
H(6)0.04960.05830.09920.029*
H(8)0.2388−0.16490.19190.032*
H(9)0.1813−0.33580.21740.039*
H(10)0.0774−0.41550.13250.037*
H(11)0.0319−0.32260.01970.038*
H(12)0.0970−0.1563−0.01130.027*
H(14)0.09340.1758−0.03930.024*
H(15)0.04000.1946−0.16740.032*
H(16)0.08130.0705−0.25450.033*
H(17)0.1734−0.0753−0.21540.035*
H(18)0.2259−0.0957−0.08890.031*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sb(1)0.02040.02060.01520.00390.0013−0.0005
S(1)0.02310.03600.0332−0.0013−0.00350.0030
S(2)0.02450.04620.0280−0.00550.00720.0023
N(1)0.02910.03980.0255−0.00140.00010.0023
N(2)0.02660.05760.0363−0.00080.00530.0008
C(1)0.01860.02330.01140.00190.00400.0012
C(2)0.01360.02340.0201−0.00210.00570.0017
C(3)0.02730.02420.02070.00280.0004−0.0023
C(4)0.03450.03280.01790.01220.0050−0.0038
C(5)0.01430.04930.02750.00210.0077−0.0031
C(6)0.02160.02890.0230−0.00160.0062−0.0022
C(7)0.01990.02030.02400.00140.00720.0010
C(8)0.02130.01910.03620.0045−0.0043−0.0004
C(9)0.03010.03480.03390.00660.00760.0102
C(10)0.02400.02730.04580.00190.01600.0052
C(11)0.02480.02700.0446−0.00520.0075−0.0039
C(12)0.03070.01860.0167−0.00610.00100.0043
C(13)0.02030.01880.0180−0.00180.00170.0019
C(14)0.01740.02430.0184−0.00100.00140.0010
C(15)0.02130.03130.02550.0030−0.00130.0053
C(16)0.02460.04110.0141−0.0056−0.00090.0033
C(17)0.02360.04290.0220−0.00540.0037−0.0067
C(18)0.02350.03580.01780.00510.0029−0.0016

Geometric parameters (Å, °)

Sb1—C72.098 (6)C8—C91.350 (9)
Sb1—C12.123 (6)C8—H80.9500
Sb1—C132.172 (5)C9—C101.387 (10)
Sb1—N12.180 (5)C9—H90.9500
Sb1—S22.5030 (17)C10—C111.375 (9)
S1—N11.510 (6)C10—H100.9500
S1—N21.589 (6)C11—C121.392 (9)
S2—N21.656 (6)C11—H110.9500
C1—C61.392 (8)C12—H120.9500
C1—C21.395 (8)C13—C141.387 (8)
C2—C31.383 (8)C13—C181.398 (8)
C2—H20.9500C14—C151.407 (8)
C3—C41.374 (9)C14—H140.9500
C3—H30.9500C15—C161.387 (9)
C4—C51.388 (10)C15—H150.9500
C4—H40.9500C16—C171.381 (10)
C5—C61.382 (9)C16—H160.9500
C5—H50.9500C17—C181.385 (8)
C6—H60.9500C17—H170.9500
C7—C121.375 (9)C18—H180.9500
C7—C81.425 (8)
C7—Sb1—C1106.6 (2)C8—C7—Sb1121.1 (5)
C7—Sb1—C1398.3 (2)C9—C8—C7120.5 (6)
C1—Sb1—C1399.3 (2)C9—C8—H8119.8
C7—Sb1—N192.2 (2)C7—C8—H8119.8
C1—Sb1—N188.8 (2)C8—C9—C10120.8 (6)
C13—Sb1—N1164.3 (2)C8—C9—H9119.6
C7—Sb1—S2127.40 (17)C10—C9—H9119.6
C1—Sb1—S2125.09 (17)C11—C10—C9120.1 (7)
C13—Sb1—S283.53 (16)C11—C10—H10120.0
N1—Sb1—S280.79 (15)C9—C10—H10120.0
N1—S1—N2117.5 (3)C10—C11—C12119.3 (6)
N2—S2—Sb1105.2 (2)C10—C11—H11120.3
S1—N1—Sb1119.2 (3)C12—C11—H11120.3
S1—N2—S2117.1 (4)C7—C12—C11121.4 (6)
C6—C1—C2120.3 (5)C7—C12—H12119.3
C6—C1—Sb1120.2 (4)C11—C12—H12119.3
C2—C1—Sb1119.5 (4)C14—C13—C18119.8 (5)
C3—C2—C1119.2 (6)C14—C13—Sb1121.4 (4)
C3—C2—H2120.4C18—C13—Sb1118.7 (4)
C1—C2—H2120.4C13—C14—C15119.3 (6)
C4—C3—C2120.3 (6)C13—C14—H14120.4
C4—C3—H3119.8C15—C14—H14120.4
C2—C3—H3119.8C16—C15—C14120.2 (6)
C3—C4—C5120.9 (6)C16—C15—H15119.9
C3—C4—H4119.6C14—C15—H15119.9
C5—C4—H4119.6C17—C16—C15120.3 (5)
C6—C5—C4119.5 (6)C17—C16—H16119.8
C6—C5—H5120.3C15—C16—H16119.8
C4—C5—H5120.3C16—C17—C18119.8 (6)
C5—C6—C1119.8 (6)C16—C17—H17120.1
C5—C6—H6120.1C18—C17—H17120.1
C1—C6—H6120.1C17—C18—C13120.6 (6)
C12—C7—C8117.8 (6)C17—C18—H18119.7
C12—C7—Sb1121.0 (4)C13—C18—H18119.7
C7—Sb1—S2—N2−81.8 (3)S2—Sb1—C7—C12−97.6 (5)
C1—Sb1—S2—N285.8 (3)C1—Sb1—C7—C8−83.7 (5)
C13—Sb1—S2—N2−177.4 (3)C13—Sb1—C7—C8174.0 (5)
N1—Sb1—S2—N23.8 (3)N1—Sb1—C7—C85.7 (5)
N2—S1—N1—Sb12.4 (5)S2—Sb1—C7—C885.8 (5)
C7—Sb1—N1—S1124.0 (4)C12—C7—C8—C9−0.4 (9)
C1—Sb1—N1—S1−129.4 (4)Sb1—C7—C8—C9176.4 (5)
C13—Sb1—N1—S1−8.1 (11)C7—C8—C9—C10−1.5 (10)
S2—Sb1—N1—S1−3.6 (3)C8—C9—C10—C110.7 (10)
N1—S1—N2—S21.6 (6)C9—C10—C11—C122.1 (10)
Sb1—S2—N2—S1−3.9 (5)C8—C7—C12—C113.2 (10)
C7—Sb1—C1—C6−30.4 (5)Sb1—C7—C12—C11−173.6 (5)
C13—Sb1—C1—C671.2 (5)C10—C11—C12—C7−4.1 (10)
N1—Sb1—C1—C6−122.3 (5)C7—Sb1—C13—C14115.8 (5)
S2—Sb1—C1—C6159.8 (4)C1—Sb1—C13—C147.3 (5)
C7—Sb1—C1—C2148.3 (4)N1—Sb1—C13—C14−112.8 (8)
C13—Sb1—C1—C2−110.0 (4)S2—Sb1—C13—C14−117.3 (5)
N1—Sb1—C1—C256.4 (4)C7—Sb1—C13—C18−69.1 (5)
S2—Sb1—C1—C2−21.5 (5)C1—Sb1—C13—C18−177.6 (5)
C6—C1—C2—C3−1.2 (8)N1—Sb1—C13—C1862.3 (10)
Sb1—C1—C2—C3−180.0 (4)S2—Sb1—C13—C1857.9 (5)
C1—C2—C3—C41.9 (9)C18—C13—C14—C151.2 (9)
C2—C3—C4—C5−1.7 (9)Sb1—C13—C14—C15176.2 (4)
C3—C4—C5—C60.8 (9)C13—C14—C15—C16−1.0 (9)
C4—C5—C6—C1−0.1 (9)C14—C15—C16—C170.6 (10)
C2—C1—C6—C50.3 (9)C15—C16—C17—C18−0.3 (10)
Sb1—C1—C6—C5179.1 (4)C16—C17—C18—C130.5 (10)
C1—Sb1—C7—C1293.0 (5)C14—C13—C18—C17−0.9 (10)
C13—Sb1—C7—C12−9.4 (6)Sb1—C13—C18—C17−176.1 (5)
N1—Sb1—C7—C12−177.6 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2136).

References

  • Bates, P. A., Hursthouse, M. B., Kelly, P. F. & Woollins, J. D. (1986). J. Chem. Soc. Dalton Trans. pp. 2367–2370.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Kunkel, F., Harms, K., Kang, H. C., Massa, W. & Dehnicke, K. (1997). Z. Naturforsch. Teil B, 52, 193–198.
  • Read, B. D., Slawin, A. M. Z. & Woollins, J. D. (2007). Acta Cryst. E63, m751–m752.
  • Rigaku (2006). SCXmini Benchtop Crystallography System software Rigaku Americas Corporation, The Woodlands, Texas, USA.
  • Rigaku (2009). Crystal Structure Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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