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

Ge, C.; Guo, Y.; Zhang, X.; Zhang, X.; Liu, Q.

doi:10.1107/S1600536807057157

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o506

doi:10.1107/S1600536807057157

Open

access

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

Chunhua Ge,^a ^* Ya'nan Guo,^a Xiangdong Zhang,^a Xiaoyan Zhang ^a and Qitao Liu ^a

^aCollege of Chemistry, Liaoning University, Shenyang 110036, People's Republic of China
^*Correspondence e-mail: chhge@lnu.edu.cn

(Received 6 November 2007; accepted 8 November 2007; online 23 January 2008)

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 ); Cutshall et al. (2005 ). For details of the synthesis, see: Doğan et al. (1992 );

Experimental

Crystal data

C₈H₈N₂O₄S₂
M_r = 260.28
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.127
S = 1.02
1012 reflections
73 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2ⁱ	0.97	2.56	3.215 (4)	125
C3—H3B⋯O2ⁱⁱ	0.97	2.57	3.325 (4)	135
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807057157/cv2350sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

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].

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

Crystal data top

C₈H₈N₂O₄S₂	F(000) = 268
M_r = 260.28	D_x = 1.634 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 554 reflections
a = 6.2845 (12) Å	θ = 2.7–22.1°
b = 12.3252 (19) Å	µ = 0.50 mm⁻¹
c = 7.080 (2) Å	T = 293 K
β = 105.22 (2)°	Block, colourless
V = 529.2 (2) Å³	0.20 × 0.15 × 0.11 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	1012 independent reflections
Radiation source: fine-focus sealed tube	761 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
phi and ω scans	θ_max = 26.0°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
T_min = 0.908, T_max = 0.955	k = −15→1
1390 measured reflections	l = −8→1

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0798P)²] where P = (F_o² + 2F_c²)/3
1012 reflections	(Δ/σ)_max < 0.001
73 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₈H₈N₂O₄S₂	V = 529.2 (2) Å³
M_r = 260.28	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.2845 (12) Å	µ = 0.50 mm⁻¹
b = 12.3252 (19) Å	T = 293 K
c = 7.080 (2) Å	0.20 × 0.15 × 0.11 mm
β = 105.22 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1012 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	761 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.955	R_int = 0.028
1390 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.02	Δρ_max = 0.27 e Å⁻³
1012 reflections	Δρ_min = −0.32 e Å⁻³
73 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
S1	0.33868 (11)	0.36411 (6)	0.00385 (12)	0.0506 (3)
O1	0.7149 (3)	0.33522 (16)	0.0792 (3)	0.0486 (6)
C2	0.5626 (4)	0.36727 (18)	0.1543 (4)	0.0373 (6)
N1	0.6306 (3)	0.40084 (16)	0.3674 (3)	0.0350 (5)
C1	0.5096 (4)	0.4388 (2)	0.5081 (4)	0.0389 (6)
H1A	0.5884	0.4182	0.6401	0.047*
H1B	0.3641	0.4063	0.4781	0.047*
O2	0.9269 (3)	0.40856 (17)	0.6269 (4)	0.0600 (7)
C4	0.8323 (4)	0.3902 (2)	0.4422 (5)	0.0442 (7)
C3	0.8954 (4)	0.3505 (3)	0.2477 (6)	0.0605 (9)
H3A	0.9950	0.4034	0.2159	0.073*
H3B	0.9752	0.2826	0.2764	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0373 (4)	0.0552 (5)	0.0535 (5)	−0.0042 (3)	0.0018 (3)	−0.0021 (3)
O1	0.0338 (10)	0.0488 (11)	0.0634 (13)	0.0019 (8)	0.0132 (9)	−0.0174 (10)
C2	0.0359 (13)	0.0282 (12)	0.0484 (16)	−0.0001 (10)	0.0118 (12)	0.0005 (11)
N1	0.0300 (10)	0.0300 (10)	0.0440 (14)	0.0011 (8)	0.0077 (9)	−0.0010 (9)
C1	0.0397 (13)	0.0354 (13)	0.0432 (15)	0.0007 (11)	0.0137 (11)	−0.0002 (12)
O2	0.0412 (11)	0.0528 (12)	0.0730 (16)	−0.0003 (9)	−0.0083 (10)	−0.0046 (11)
C4	0.0337 (13)	0.0307 (13)	0.0613 (19)	0.0023 (10)	0.0000 (13)	−0.0036 (12)
C3	0.0315 (14)	0.0564 (18)	0.090 (3)	0.0008 (12)	0.0094 (15)	−0.0195 (18)

Geometric parameters (Å, º) top

S1—C2	1.526 (3)	C1—H1A	0.9700
O1—C2	1.274 (3)	C1—H1B	0.9700
O1—C3	1.427 (4)	O2—C4	1.307 (4)
C2—N1	1.514 (4)	C4—C3	1.606 (5)
N1—C4	1.246 (3)	C3—H3A	0.9700
N1—C1	1.479 (3)	C3—H3B	0.9700
C1—C1ⁱ	1.514 (5)

C2—O1—C3	97.4 (2)	C1ⁱ—C1—H1B	110.1
O1—C2—N1	117.0 (2)	H1A—C1—H1B	108.4
O1—C2—S1	110.9 (2)	N1—C4—O2	123.5 (3)
N1—C2—S1	132.0 (2)	N1—C4—C3	96.9 (3)
C4—N1—C1	113.1 (2)	O2—C4—C3	139.6 (3)
C4—N1—C2	112.6 (2)	O1—C3—C4	115.9 (2)
C1—N1—C2	134.2 (2)	O1—C3—H3A	108.3
N1—C1—C1ⁱ	108.0 (3)	C4—C3—H3A	108.3
N1—C1—H1A	110.1	O1—C3—H3B	108.3
C1ⁱ—C1—H1A	110.1	C4—C3—H3B	108.3
N1—C1—H1B	110.1	H3A—C3—H3B	107.4

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2ⁱⁱ	0.97	2.56	3.215 (4)	125
C3—H3B···O2ⁱⁱⁱ	0.97	2.57	3.325 (4)	135

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

Experimental details

Crystal data
Chemical formula	C₈H₈N₂O₄S₂
M_r	260.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.2845 (12), 12.3252 (19), 7.080 (2)
β (°)	105.22 (2)
V (Å³)	529.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.50
Crystal size (mm)	0.20 × 0.15 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.908, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	1390, 1012, 761
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.127, 1.02
No. of reflections	1012
No. of parameters	73
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.32

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2ⁱ	0.97	2.56	3.215 (4)	125
C3—H3B···O2ⁱⁱ	0.97	2.57	3.325 (4)	135

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

Acknowledgements

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

References

Bruker (2001). SMART (Version 5.624), SAINT (Version 6.04) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cutshall, N. S., O'Day, C. & Prezhdo, M. (2005). Bioorg. Med. Chem. Lett. 15, 3374–3379. Web of Science CrossRef PubMed CAS Google Scholar
Doğan, Í., Burgemeister, T., Íçlic, S. & Mannschreck, A. (1992). Tetrahedron, 48, 7157–7164. Google Scholar
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. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997b). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar