8-Thia-1,6-diaza­bicyclo­[4.3.0]nonane-7,9-dione

Bin-bin Xi; Lu Shi; Hai Huang; Qin Wang; Hong-Jun Zhu

doi:10.1107/S1600536811038785

. 2011 Sep 30;67(Pt 10):o2771. doi: 10.1107/S1600536811038785

8-Thia-1,6-diazabicyclo[4.3.0]nonane-7,9-dione

Bin-bin Xi ^a, Lu Shi ^a, Hai Huang ^a, Qin Wang ^a, Hong-Jun Zhu ^b,^*

PMCID: PMC3201436 PMID: 22065138

Abstract

There are two independent molecules, A and B, in the asymmetric unit of the title compound, C₆H₈N₂O₂S. In the crystal, pairs of intermolecular S⋯O contacts [3.286 (1) Å] link the B molecules into inversion dimers.

Related literature

For applications of the title compound, see: Yamaguchi et al. (1989 ▶). For the synthesis, see: Zhu et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶). For a review of carbonyl–carbonyl interactions, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C₆H₈N₂O₂S
M _r = 172.20
Triclinic,
a = 7.8400 (16) Å
b = 10.464 (2) Å
c = 10.514 (2) Å
α = 63.84 (3)°
β = 79.62 (3)°
γ = 89.42 (3)°
V = 759.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.896, T _max = 0.964
3018 measured reflections
2795 independent reflections
2092 reflections with I > 2σ(I)
R _int = 0.041
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.125
S = 1.00
2795 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811038785/lx2196sup1.cif

e-67-o2771-sup1.cif^{(23.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038785/lx2196Isup2.hkl

e-67-o2771-Isup2.hkl^{(137.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811038785/lx2196Isup3.cml

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

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

The title compound, 8-thia-1,6-diazabicyclo[4.3.0]nonane-7,9-dione, is an important intermediate for a kind of manufacturing agrochemical, especially for Fluthiacet-methyl as a super-effective, wide-spectral and safe herbicide (Yamaguchi et al., 1989). We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound is shown in Fig. 1 and there are two independent unique molecules [labeled A & B]. The bond lengths and angles are within normal ranges (Allen et al., 1987). The crystal packing (Fig. 2) is stabilized by an intermolecular S···O interaction between the sulfur and the O atom of the carbonyl group interpreted as similar to type-II carbonyl–carbonyl interaction (Allen et al., 1998), with S1···O2ⁱ distance of 3.286 (1) Å.

Experimental

The title compound was prepared according to reported in literature (Zhu et al., 2011). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethanol at room temperature for ca. 6 d.