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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3268.
Published online 2009 November 28. doi:  10.1107/S1600536809050788
PMCID: PMC2972030

2,2′-[Ethane-1,2-diylbis(sulfanedi­yl)]bis­(pyridine N-oxide)

Abstract

The tile compound, C12H12N2O2S2, lies on an inversion center. The two pyridyl rings are parallel to each other. The structure is devoid of any classical hydrogen bonds due to lack of appropriate donors and acceptors for such bonds. However, non-classical hydrogen bonds of the types C—H(...)O and C—H(...)S stabilize the structure.

Related literature

For thio­ether-type complexes, see: Xie et al. (2006 [triangle]). For a related structure, see: Zhang et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o3268-scheme1.jpg

Experimental

Crystal data

  • C12H12N2O2S2
  • M r = 280.36
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3268-efi1.jpg
  • a = 8.2776 (17) Å
  • b = 6.9790 (14) Å
  • c = 10.791 (2) Å
  • β = 93.52 (3)°
  • V = 622.2 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.42 mm−1
  • T = 293 K
  • 0.28 × 0.26 × 0.24 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1998 [triangle]) T min = 0.889, T max = 0.904
  • 3068 measured reflections
  • 1098 independent reflections
  • 1007 reflections with I > 2(I)
  • R int = 0.013

Refinement

  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.070
  • S = 1.07
  • 1098 reflections
  • 82 parameters
  • H-atom parameters constrained
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: XSCANS (Bruker, 1998 [triangle]); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050788/pv2239sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050788/pv2239Isup2.hkl

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

Acknowledgments

This work was supported by the Beijing Municipal Natural Science Foundation (No. 2082004) and the Funding Project for Academic Human Resources Development in Institutions of Higher Learning under the Jurisdiction of Beijing Municipality (PHR 200907105).

supplementary crystallographic information

Comment

In the past decades, there were many reports about the thioether-type compounds with their flexibility and conformation freedoms (Xie et al., 2006). As a continuation of our series of research on thioether-type compounds (Zhang et al., 2009), we report herein the crystal structure of the title compound.

The title compound (Fig.1) was obtained by the reaction of 2-mercaptopyridine N-oxide and 1,2-dibromoethane. There exits a symmetrical center located at the midpoint of the two methylenes and the pyridyl rings of the title compound are parallel to each other. Thestructure is stabilized by non-classical hydrogen bonds of the types C—H···O and C—H···S.

Experimental

2-Mercaptopyridine N-oxide (1.2719 g, 10.0 mmol) was added to a stirred and heated solution of KOH (0.5837 g, 10.4 mmol) in ethanol (50 ml). After 30 min, 1,2-dibromoethane (0.9917 g, 5.3 mmol) was added and reacted for 10 h. The mixture was cooled to room temperature and the precipitate was filtered off and washed with water, giving a white powder. After slow diffusion of ether into the solution of the powder in CHCl3/CH3CH2OH, colorless block single crystals suitable for X-ray diffraction were collected.

Refinement

All H atoms were included at geometrically idealized positions with C—H = 0.96 Å and treated as riding with Uiso(H) = 1.2 and 1.5 Ueq(Caryl and Cmethylene, respectively).

Figures

Fig. 1.
The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level for non-hydrogen atoms.

Crystal data

C12H12N2O2S2F(000) = 292
Mr = 280.36Dx = 1.496 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3720 reflections
a = 8.2776 (17) Åθ = 2.5–27.9°
b = 6.9790 (14) ŵ = 0.42 mm1
c = 10.791 (2) ÅT = 293 K
β = 93.52 (3)°Block, colorless
V = 622.2 (2) Å30.28 × 0.26 × 0.24 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer1098 independent reflections
Radiation source: fine-focus sealed tube1007 reflections with I > 2(I)
graphiteRint = 0.013
ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)h = −9→7
Tmin = 0.889, Tmax = 0.904k = −8→8
3068 measured reflectionsl = −12→12

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0387P)2 + 0.1633P] where P = (Fo2 + 2Fc2)/3
1098 reflections(Δ/σ)max = 0.006
82 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = −0.22 e Å3

Special details

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)

xyzUiso*/Ueq
S10.15370 (5)0.18793 (5)0.61401 (3)0.03644 (16)
N10.32129 (13)0.50095 (17)0.63713 (10)0.0304 (3)
O10.33935 (13)0.43441 (16)0.75096 (9)0.0434 (3)
C50.22742 (15)0.39913 (19)0.55220 (12)0.0285 (3)
C60.04101 (17)0.0906 (2)0.47863 (13)0.0336 (3)
H7B−0.04230.17930.45120.050*
H7C0.11300.07080.41340.050*
C10.39499 (18)0.6652 (2)0.60369 (16)0.0377 (4)
H1A0.46320.73410.66350.045*
C40.20326 (17)0.4676 (2)0.43202 (13)0.0353 (3)
H4A0.13780.39620.37180.042*
C20.37221 (18)0.7344 (2)0.48487 (15)0.0417 (4)
H6A0.42350.85160.46220.050*
C30.27461 (19)0.6363 (2)0.39827 (15)0.0415 (4)
H5A0.25730.68510.31530.050*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0473 (3)0.0327 (2)0.0285 (2)−0.00976 (16)−0.00380 (16)0.00374 (14)
N10.0298 (6)0.0312 (6)0.0300 (6)0.0024 (5)0.0001 (5)−0.0051 (5)
O10.0515 (6)0.0479 (7)0.0295 (6)−0.0003 (5)−0.0092 (5)−0.0024 (5)
C50.0278 (7)0.0285 (7)0.0292 (7)−0.0003 (5)0.0019 (5)−0.0023 (6)
C60.0378 (8)0.0320 (8)0.0308 (7)−0.0061 (6)0.0008 (6)−0.0004 (6)
C10.0319 (7)0.0320 (7)0.0494 (9)−0.0040 (6)0.0038 (6)−0.0119 (7)
C40.0386 (8)0.0382 (8)0.0290 (7)−0.0056 (6)0.0011 (6)0.0003 (6)
C20.0412 (9)0.0325 (8)0.0528 (10)−0.0052 (7)0.0132 (7)−0.0007 (7)
C30.0469 (9)0.0408 (8)0.0375 (8)−0.0029 (7)0.0081 (7)0.0068 (7)

Geometric parameters (Å, °)

S1—C51.7436 (14)C6—H7C0.9600
S1—C61.8160 (15)C1—C21.372 (2)
N1—O11.3131 (16)C1—H1A0.9600
N1—C11.3578 (19)C4—C31.377 (2)
N1—C51.3642 (18)C4—H4A0.9600
C5—C41.385 (2)C2—C31.379 (2)
C6—C6i1.521 (3)C2—H6A0.9601
C6—H7B0.9600C3—H5A0.9601
C5—S1—C6100.54 (6)N1—C1—C2120.48 (14)
O1—N1—C1121.33 (12)N1—C1—H1A120.0
O1—N1—C5118.14 (12)C2—C1—H1A119.5
C1—N1—C5120.52 (12)C3—C4—C5120.21 (14)
N1—C5—C4119.53 (13)C3—C4—H4A119.9
N1—C5—S1112.44 (10)C5—C4—H4A119.9
C4—C5—S1128.02 (11)C1—C2—C3119.98 (15)
C6i—C6—S1106.50 (13)C1—C2—H6A120.0
C6i—C6—H7B107.7C3—C2—H6A120.0
S1—C6—H7B109.3C4—C3—C2119.23 (15)
C6i—C6—H7C114.3C4—C3—H5A120.5
S1—C6—H7C109.4C2—C3—H5A120.3
H7B—C6—H7C109.5
O1—N1—C5—C4178.66 (12)O1—N1—C1—C2−178.76 (13)
C1—N1—C5—C4−2.06 (19)C5—N1—C1—C22.0 (2)
O1—N1—C5—S1−2.27 (15)N1—C5—C4—C30.6 (2)
C1—N1—C5—S1177.01 (10)S1—C5—C4—C3−178.35 (12)
C6—S1—C5—N1−178.99 (10)N1—C1—C2—C3−0.4 (2)
C6—S1—C5—C4−0.02 (15)C5—C4—C3—C21.0 (2)
C5—S1—C6—C6i−176.25 (13)C1—C2—C3—C4−1.1 (2)

Symmetry codes: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1A···O1ii0.962.303.225 (2)161
C4—H4A···S1iii0.962.853.599 (2)135

Symmetry codes: (ii) −x+1, y+1/2, −z+3/2; (iii) x, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2239).

References

  • Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Xie, Y. B., Li, J. R. & Bu, X. H. (2006). J. Chem. Crystallogr. 3, 211–215.
  • Zhang, C.-Y., Gao, Q., Cui, Y. & Xie, Y.-B. (2009). Acta Cryst. E65, o1482. [PMC free article] [PubMed]

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