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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o506.
Published online 2008 January 23. doi:  10.1107/S1600536807057157
PMCID: PMC2960409

3,3′-(Ethane-1,2-di­yl)bis­(2-thioxo-1,3-oxazolidin-4-one)

Abstract

The asymmetric unit of the title compound, C8H8N2O4S2, contains one half of a centrosymmetric mol­ecule. A short C(...)O distance of 3.012 (4) Å between the carbonyl groups of neighbouring mol­ecules indicates the presence of dipole–dipole inter­actions. The crystal packing exhibits also weak inter­molecular O(...)S [3.239 (3) Å] and C—H(...)O inter­actions.

Related literature

For general background, see: Gupta et al. (1981 [triangle]); Cutshall et al. (2005 [triangle]). For details of the synthesis, see: Doğan et al. (1992 [triangle]);

An external file that holds a picture, illustration, etc.
Object name is e-64-0o506-scheme1.jpg

Experimental

Crystal data

  • C8H8N2O4S2
  • M r = 260.28
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o506-efi1.jpg
  • a = 6.2845 (12) Å
  • b = 12.3252 (19) Å
  • c = 7.080 (2) Å
  • β = 105.22 (2)°
  • V = 529.2 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.50 mm−1
  • T = 293 (2) K
  • 0.20 × 0.15 × 0.11 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.908, T max = 0.955
  • 1390 measured reflections
  • 1012 independent reflections
  • 761 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.127
  • S = 1.02
  • 1012 reflections
  • 73 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a [triangle]); molecular graphics: SHELXTL (Sheldrick, 1997b [triangle]); 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/S1600536807057157/cv2350sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807057157/cv2350Isup2.hkl

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

Acknowledgments

This project is supported by the Natural Science Foundation of the Education Bureau of Liaoning Province (grant No. 05 L159).

supplementary crystallographic information

Comment

The research on N-substitution 2-thioxooxazolidin-4-one compounds have been mushroomed for their interesting biological and spectral properties (Cutshall et al., 2005; Gupta et al., 1981).

The title compound is composed of two functional groups of 2-thioxooxazolidin-4-one which are bridged by ethane group (Fig.1). In the crystal, C1—C4, O1—O2, N1 and S1 atoms are almost coplanar with a highest deviation of 0.0440 Å for O2. As a derivative of ethane, the molecule has a perfect anti-linear conformation. Dihedral angle of N1—C1—C1A—N1A is -180.00 (19)°. The crystal packing exhibits weak intermolecular C—H···O hydrogen bonds (Table 1), O···S interaction (S1···O2iii 3.239 (3) Å [symmetry code: (iii) -1 + x, y, -1 + z]), and strong dipole-dipole interactions proved by short C···O distance of 3.012 (4) Å between the carbonyl groups of neighbouring molecules.

Experimental

The title compound was prepared according to the method of Doğan et al. (1992). Colourless block-shape crystal of (I) suitable for X-ray diffraction was obtained from ethanol/water (V: V = 4: 1).

Refinement

H atoms were found in difference map, placed in idealized positions (C—H 0.97 Å) and refined as riding, with Uiso(H) = 1.2 Ueq(C).

Figures

Fig. 1.
The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level and atomix numbering [symmetry code: (A) 1 - x, 1 - y, 1 - z].

Crystal data

C8H8N2O4S2F000 = 268
Mr = 260.28Dx = 1.634 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 554 reflections
a = 6.2845 (12) Åθ = 2.7–22.1º
b = 12.3252 (19) ŵ = 0.50 mm1
c = 7.080 (2) ÅT = 293 (2) K
β = 105.22 (2)ºBlock, colourless
V = 529.2 (2) Å30.20 × 0.15 × 0.11 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer1012 independent reflections
Radiation source: fine-focus sealed tube761 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
T = 293(2) Kθmax = 26.0º
phi and ω scansθmin = 3.3º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −7→7
Tmin = 0.908, Tmax = 0.955k = −15→1
1390 measured reflectionsl = −8→1

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.127  w = 1/[σ2(Fo2) + (0.0798P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
1012 reflectionsΔρmax = 0.27 e Å3
73 parametersΔρmin = −0.31 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
S10.33868 (11)0.36411 (6)0.00385 (12)0.0506 (3)
O10.7149 (3)0.33522 (16)0.0792 (3)0.0486 (6)
C20.5626 (4)0.36727 (18)0.1543 (4)0.0373 (6)
N10.6306 (3)0.40084 (16)0.3674 (3)0.0350 (5)
C10.5096 (4)0.4388 (2)0.5081 (4)0.0389 (6)
H1A0.58840.41820.64010.047*
H1B0.36410.40630.47810.047*
O20.9269 (3)0.40856 (17)0.6269 (4)0.0600 (7)
C40.8323 (4)0.3902 (2)0.4422 (5)0.0442 (7)
C30.8954 (4)0.3505 (3)0.2477 (6)0.0605 (9)
H3A0.99500.40340.21590.073*
H3B0.97520.28260.27640.073*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0373 (4)0.0552 (5)0.0535 (5)−0.0042 (3)0.0018 (3)−0.0021 (3)
O10.0338 (10)0.0488 (11)0.0634 (13)0.0019 (8)0.0132 (9)−0.0174 (10)
C20.0359 (13)0.0282 (12)0.0484 (16)−0.0001 (10)0.0118 (12)0.0005 (11)
N10.0300 (10)0.0300 (10)0.0440 (14)0.0011 (8)0.0077 (9)−0.0010 (9)
C10.0397 (13)0.0354 (13)0.0432 (15)0.0007 (11)0.0137 (11)−0.0002 (12)
O20.0412 (11)0.0528 (12)0.0730 (16)−0.0003 (9)−0.0083 (10)−0.0046 (11)
C40.0337 (13)0.0307 (13)0.0613 (19)0.0023 (10)0.0000 (13)−0.0036 (12)
C30.0315 (14)0.0564 (18)0.090 (3)0.0008 (12)0.0094 (15)−0.0195 (18)

Geometric parameters (Å, °)

S1—C21.526 (3)C1—H1A0.9700
O1—C21.274 (3)C1—H1B0.9700
O1—C31.427 (4)O2—C41.307 (4)
C2—N11.514 (4)C4—C31.606 (5)
N1—C41.246 (3)C3—H3A0.9700
N1—C11.479 (3)C3—H3B0.9700
C1—C1i1.514 (5)
C2—O1—C397.4 (2)C1i—C1—H1B110.1
O1—C2—N1117.0 (2)H1A—C1—H1B108.4
O1—C2—S1110.9 (2)N1—C4—O2123.5 (3)
N1—C2—S1132.0 (2)N1—C4—C396.9 (3)
C4—N1—C1113.1 (2)O2—C4—C3139.6 (3)
C4—N1—C2112.6 (2)O1—C3—C4115.9 (2)
C1—N1—C2134.2 (2)O1—C3—H3A108.3
N1—C1—C1i108.0 (3)C4—C3—H3A108.3
N1—C1—H1A110.1O1—C3—H3B108.3
C1i—C1—H1A110.1C4—C3—H3B108.3
N1—C1—H1B110.1H3A—C3—H3B107.4

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3A···O2ii0.972.563.215 (4)125
C3—H3B···O2iii0.972.573.325 (4)135

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2350).

References

  • Bruker (2001). SMART (Version 5.624), SAINT (Version 6.04) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cutshall, N. S., O’Day, C. & Prezhdo, M. (2005). Bioorg. Med. Chem. Lett.15, 3374–3379. [PubMed]
  • Doğan, Í., Burgemeister, T., Íçlic, S. & Mannschreck, A. (1992). Tetrahedron, 48, 7157–7164.
  • Gupta, R. K., Salzberg, B. M., Grinvald, A., Cohen, L. B., Kamino, K., Lesher, S., Boyle, M. B., Waggoner, A. S. & Wang, C. H. (1981). J. Membr. Biol.58, 123–137. [PubMed]
  • Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Sheldrick, G. M. (1997b). SHELXTL Bruker AXS Inc., Madison, Wisconsin, USA.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography