3-(1,3-Dithio­lan-2-yl­idene)-1-(4-meth­oxy­phen­yl)pyridine-2,4(1H,3H)-dione

Yan-Chun Ma; Jin-Long Song

doi:10.1107/S1600536811033009

. 2011 Aug 27;67(Pt 9):o2433. doi: 10.1107/S1600536811033009

3-(1,3-Dithiolan-2-ylidene)-1-(4-methoxyphenyl)pyridine-2,4(1H,3H)-dione

Yan-Chun Ma ^a,^*, Jin-Long Song ^b

PMCID: PMC3200629 PMID: 22064441

Abstract

In the title compound, C₁₅H₁₃NO₃S₂, the dithiolane ring adopts a twisted conformation. The molecule exhibits a V-shaped conformation, with a dihedral angle of 79.05 (7)° between the benzene ring and the pyridine ring. In the crystal, C—H⋯O interactions are observed.

Related literature

For the synthesis, see: Li et al. (2008 ▶). For background to N-substituted pyridine compounds and their potential use in medicinal chemistry, see: Kim et al. (2008 ▶); Zhu et al. (2006 ▶)

Experimental

Crystal data

C₁₅H₁₃NO₃S₂
M _r = 319.40
Monoclinic,
a = 5.322 (2) Å
b = 27.521 (11) Å
c = 10.065 (4) Å
β = 100.831 (5)°
V = 1448.0 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 293 K
0.35 × 0.29 × 0.28 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.892, T _max = 0.912
12346 measured reflections
2905 independent reflections
1973 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.121
S = 1.08
2905 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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) global, I. DOI: 10.1107/S1600536811033009/ff2024sup1.cif

e-67-o2433-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033009/ff2024Isup2.hkl

e-67-o2433-Isup2.hkl^{(142.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811033009/ff2024Isup3.cml

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
C8—H8⋯O2ⁱ	0.93	2.42	3.259 (3)	150

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Educational Institute of Jilin Province for supporting this work.

supplementary crystallographic information

Comment

Among the richness of heterocyclic compounds, N-substituted pyridone compounds (Zhu et al., 2006) have attracted an intense interest due to their potential for medicinal chemistry (Kim et al., 2008). Recently, a large number of N-substituted pyridone compounds have been prepared (Li et al., 2008). As a contribution to this field, the structure of the title crystal is presented here. The molecular structure of the title compound, together with the atom-numbering scheme, is illustrated in Fig.1. Selected bond lengths and angles are given in Table 1. The molecule exhibits a V-shaped conformation in the crystal with a dihedral angle of 79.05 (7)° between the benzene ring and the pyridine ring. The dithiolane ring has a twisted conformation.

Experimental

The title compound was synthesized according to the literature (Li et al., 2008). It was dissolved in ethyl acetate at room temperature and hexane was added. The solution was kept at room temperature in a sealed flask for a few days to give single crystals suitable for single-crystal X-ray analysis.