2-(Benzyl­sulfan­yl)pyridine N-oxide

B Ravindran Durai Nayagam; Samuel Robinson Jebas; H Johnson Jeyakumar; Dieter Schollmeyer

doi:10.1107/S1600536808011446

. 2008 Apr 26;64(Pt 5):o928. doi: 10.1107/S1600536808011446

2-(Benzylsulfanyl)pyridine N-oxide

B Ravindran Durai Nayagam ^a,^*, Samuel Robinson Jebas ^b, H Johnson Jeyakumar ^c, Dieter Schollmeyer ^d

PMCID: PMC2961086 PMID: 21202409

Abstract

In the title compound, C₁₂H₁₁NOS, the dihedral angle between the oxopyridinium and phenyl rings is 58.40 (1)°. The crystal structure is stabilized by C—H⋯O hydrogen bonds, π–π stacking interactions involving the pyridinium rings [centroid–centroid distance = 3.6891 (9) Å] and C—H⋯π interactions.

Related literature

For bond-length data, see: Allen et al.(1987 ▶). For biological activities of N-oxide derivatives, see: Bovin et al. (1992 ▶); Katsuyuki et al. (1991 ▶); Leonard et al. (1955 ▶); Lobana & Bhatia (1989 ▶); Symons & West (1985 ▶). For related literature, see: Jebas et al. (2005 ▶); Ravindran et al. (2008 ▶).

Experimental

Crystal data

C₁₂H₁₁NOS
M _r = 217.28
Monoclinic,
a = 5.7277 (2) Å
b = 15.8760 (3) Å
c = 11.6498 (4) Å
β = 97.816 (2)°
V = 1049.51 (6) Å³
Z = 4
Cu Kα radiation
μ = 2.49 mm⁻¹
T = 298 (2) K
0.6 × 0.32 × 0.16 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: numerical (CORINC; Draeger & Gattow, 1971 ▶) T _min = 0.423, T _max = 0.676
2183 measured reflections
1979 independent reflections
1865 reflections with I > 2σ(I)
R _int = 0.020
3 standard reflections frequency: 60 min intensity decay: 3%

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.088
S = 1.05
1979 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (Draeger & Gattow, 1971 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011446/ci2583sup1.cif

e-64-0o928-sup1.cif^{(15.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011446/ci2583Isup2.hkl

e-64-0o928-Isup2.hkl^{(95.4KB, hkl)}

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
C5—H5⋯O7ⁱ	0.93	2.42	3.323 (2)	164
C14—H14⋯Cg1ⁱⁱ	0.93	2.92	3.560 (2)	127
C4—H4⋯Cg2ⁱⁱⁱ	0.93	2.99	3.777 (2)	143

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 is the centroid of the ring C1–C5/N6 and Cg2 is the centroid of the ring C10–C15.

Acknowledgments

RDN thanks the University Grants Commission, India, for a Teacher Fellowship.

supplementary crystallographic information

Comment

N-Oxides and their derivatives show a broad spectrum of biological activity, such as antifungal, antibacterial, antimicrobial and antibacterial activities (Lobana & Bhatia, 1989; Symons et al., 1985). These compounds are also found to be involved in DNA strand scission under physiological conditions (Katsuyuki et al., 1991; Bovin et al., 1992). Pyridine N-oxides bearing a sulfur group in position 2 display significant antimicrobial activity (Leonard et al., 1955). In view of the importance of N-oxides, we have previously reported the crystal structures of N-oxide derivatives (Jebas et al., 2005; Ravindran Durai Nayagam et al., 2008). As an extension of our work on these derivatives, we report here the crystal structure of the title compound (Fig. 1).

The bond lengths and angles agree well with the N-oxide derivatives reported earlier (Jebas et al., 2005; Ravindran Durai Nayagam et al., 2008). The N—O bond length is in good agreement with the mean value of 1.304 (15) Å reported in the literature for pyridine N–oxides (Allen et al.,1987).

The oxopyridinium and benzene rings are planar to within ±0.002 (2) Å and ±0.005 (2) Å, respectively, and they form a dihedral angle of 58.40 (1)°. Atom O7 deviates from the plane of the pyridinium ring by -0.012 (1) Å.

In the crystal structure, inversion related molecules at (x, y, z) and (-1-x, 1-y, -z) are linked by C—H···O hydrogen bonds to form a R₂2(8) ring (Fig. 2). In addition, the crystal packing is stabilized by a π-π interaction between the pyridinium rings of adjacent molecules at (x, y, z) and (-x, 2-y, -z), with a ring centroid to centroid distance of 3.6891 (9) Å. Weak C—H···π interactions involving the two aromatic rings are also observed.

Experimental

A mixture of benzyl chloride, (0.126 g, 1 mmol) and 1-hydroxypyridine-2-thione sodium salt (0.149 g, 1 mmol) in water and methanol (30 ml each) was heated at 333 K with stirring for 30 min. The compound formed was filtered off, and dried (0.20 g, 92%). The compound was recrystallized from chloroform-methanol (1:1 v/v).