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

Experimental

Crystal data

• C₈H₈N₂O₄S₂

• M _r = 260.28

• Monoclinic,

• a = 6.2845 (12) Å

• b = 12.3252 (19) Å

• c = 7.080 (2) Å

• β = 105.22 (2)°

• V = 529.2 (2) ų

• 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[F ² > 2σ(F ²)] = 0.043

• wR(F ²) = 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

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.

Supplementary Material

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

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) ; (ii) .

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 U_iso(H) = 1.2 U_eq(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

C8H8N2O4S2	F000 = 268
Mr = 260.28	Dx = 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 = 2.7–22.1º
b = 12.3252 (19) Å	µ = 0.50 mm−1
c = 7.080 (2) Å	T = 293 (2) K
β = 105.22 (2)º	Block, colourless
V = 529.2 (2) Å3	0.20 × 0.15 × 0.11 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	1012 independent reflections
Radiation source: fine-focus sealed tube	761 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 293(2) K	θmax = 26.0º
phi and ω scans	θmin = 3.3º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −7→7
Tmin = 0.908, Tmax = 0.955	k = −15→1
1390 measured reflections	l = −8→1

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-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 reflections	Δρmax = 0.27 e Å−3
73 parameters	Δρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction 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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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 codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

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.