2-(Benzyl-sulfan-yl)pyridine N-oxide.

In the title compound, C(12)H(11)NOS, 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 inter-actions involving the pyridinium rings [centroid-centroid distance = 3.6891 (9) Å] and C-H⋯π inter-actions.

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 = 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

Δρmax = 0.23 e Å−3

Δρmin = −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.

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

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

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

C12H11NOS	F000 = 456
Mr = 217.28	Dx = 1.375 Mg m−3
Monoclinic, P21/c	Cu Kα radiation λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 5.7277 (2) Å	θ = 65–70º
b = 15.8760 (3) Å	µ = 2.49 mm−1
c = 11.6498 (4) Å	T = 298 (2) K
β = 97.816 (2)º	Plate, colourless
V = 1049.51 (6) Å3	0.6 × 0.32 × 0.16 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.020
Monochromator: graphite	θmax = 69.9º
T = 298(2) K	θmin = 4.7º
ω/2θ scans	h = 0→6
Absorption correction: numerical(CORINC; Draeger & Gattow, 1971)	k = 0→19
Tmin = 0.423, Tmax = 0.676	l = −14→14
2183 measured reflections	3 standard reflections
1979 independent reflections	every 60 min
1865 reflections with I > 2σ(I)	intensity decay: 3%

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0468P)2 + 0.3205P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.032	(Δ/σ)max = 0.001
wR(F2) = 0.088	Δρmax = 0.23 e Å−3
S = 1.05	Δρmin = −0.23 e Å−3
1979 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
137 parameters	Extinction coefficient: 0.0138 (9)

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.

	x	y	z	Uiso*/Ueq
C1	0.0305 (2)	0.50000 (9)	0.21475 (12)	0.0323 (3)
C2	0.2020 (3)	0.55970 (10)	0.20485 (13)	0.0397 (4)
H2	0.3446	0.5575	0.2536	0.048*
C3	0.1620 (3)	0.62241 (11)	0.12302 (14)	0.0462 (4)
H3	0.2768	0.6629	0.1165	0.055*
C4	−0.0502 (3)	0.62477 (11)	0.05064 (14)	0.0456 (4)
H4	−0.0788	0.6668	−0.005	0.055*
C5	−0.2179 (3)	0.56490 (11)	0.06128 (13)	0.0426 (4)
H5	−0.3605	0.5664	0.0125	0.051*
N6	−0.1782 (2)	0.50342 (8)	0.14226 (10)	0.0358 (3)
O7	−0.33607 (19)	0.44536 (8)	0.15290 (11)	0.0507 (3)
S8	0.04017 (6)	0.41513 (2)	0.31047 (3)	0.03918 (16)
C9	0.3207 (3)	0.43634 (10)	0.39937 (14)	0.0415 (4)
H9A	0.4475	0.4338	0.3522	0.05*
H9B	0.319	0.4923	0.4327	0.05*
C10	0.3594 (2)	0.37147 (9)	0.49432 (12)	0.0348 (3)
C11	0.5483 (3)	0.31656 (10)	0.50101 (13)	0.0404 (4)
H11	0.6517	0.3197	0.4462	0.049*
C12	0.5852 (3)	0.25699 (10)	0.58820 (15)	0.0465 (4)
H12	0.7138	0.2208	0.5919	0.056*
C13	0.4330 (3)	0.25101 (11)	0.66927 (14)	0.0481 (4)
H13	0.4565	0.2103	0.7271	0.058*
C14	0.2452 (3)	0.30575 (13)	0.66418 (15)	0.0527 (4)
H14	0.1426	0.3024	0.7194	0.063*
C15	0.2084 (3)	0.36542 (11)	0.57771 (14)	0.0461 (4)
H15	0.081	0.402	0.5752	0.055*

	U11	U22	U33	U12	U13	U23
C1	0.0293 (7)	0.0344 (7)	0.0321 (7)	0.0014 (5)	−0.0005 (5)	−0.0014 (5)
C2	0.0311 (7)	0.0454 (8)	0.0407 (8)	−0.0045 (6)	−0.0019 (6)	0.0043 (6)
C3	0.0422 (9)	0.0470 (9)	0.0482 (9)	−0.0091 (7)	0.0021 (7)	0.0095 (7)
C4	0.0481 (9)	0.0473 (9)	0.0397 (8)	0.0013 (7)	0.0004 (7)	0.0105 (7)
C5	0.0381 (8)	0.0479 (9)	0.0382 (8)	0.0026 (7)	−0.0073 (6)	0.0031 (7)
N6	0.0298 (6)	0.0378 (6)	0.0377 (6)	−0.0022 (5)	−0.0027 (5)	−0.0023 (5)
O7	0.0360 (6)	0.0504 (7)	0.0612 (7)	−0.0139 (5)	−0.0092 (5)	0.0073 (6)
S8	0.0355 (2)	0.0354 (2)	0.0437 (2)	−0.00537 (13)	−0.00524 (15)	0.00604 (14)
C9	0.0362 (8)	0.0388 (8)	0.0459 (8)	−0.0033 (6)	−0.0075 (6)	0.0058 (6)
C10	0.0342 (7)	0.0324 (7)	0.0355 (7)	−0.0012 (6)	−0.0035 (5)	−0.0015 (6)
C11	0.0370 (8)	0.0444 (8)	0.0397 (7)	0.0034 (6)	0.0044 (6)	−0.0004 (6)
C12	0.0460 (9)	0.0408 (8)	0.0502 (9)	0.0109 (7)	−0.0024 (7)	0.0025 (7)
C13	0.0590 (10)	0.0445 (9)	0.0374 (8)	−0.0046 (7)	−0.0054 (7)	0.0064 (7)
C14	0.0543 (10)	0.0660 (11)	0.0393 (8)	−0.0035 (9)	0.0121 (7)	0.0004 (8)
C15	0.0421 (9)	0.0505 (9)	0.0458 (8)	0.0107 (7)	0.0065 (7)	−0.0034 (7)

C1—N6	1.3678 (18)	C9—H9A	0.97
C1—C2	1.381 (2)	C9—H9B	0.97
C1—S8	1.7450 (14)	C10—C11	1.383 (2)
C2—C3	1.376 (2)	C10—C15	1.389 (2)
C2—H2	0.93	C11—C12	1.383 (2)
C3—C4	1.382 (2)	C11—H11	0.93
C3—H3	0.93	C12—C13	1.373 (2)
C4—C5	1.369 (2)	C12—H12	0.93
C4—H4	0.93	C13—C14	1.378 (3)
C5—N6	1.355 (2)	C13—H13	0.93
C5—H5	0.93	C14—C15	1.378 (2)
N6—O7	1.3090 (16)	C14—H14	0.93
S8—C9	1.8205 (15)	C15—H15	0.93
C9—C10	1.505 (2)
N6—C1—C2	119.53 (13)	C10—C9—H9B	109.9
N6—C1—S8	111.98 (10)	S8—C9—H9B	109.9
C2—C1—S8	128.49 (11)	H9A—C9—H9B	108.3
C3—C2—C1	120.09 (14)	C11—C10—C15	118.26 (14)
C3—C2—H2	120	C11—C10—C9	120.56 (14)
C1—C2—H2	120	C15—C10—C9	121.18 (14)
C2—C3—C4	119.47 (15)	C12—C11—C10	120.85 (14)
C2—C3—H3	120.3	C12—C11—H11	119.6
C4—C3—H3	120.3	C10—C11—H11	119.6
C5—C4—C3	119.71 (15)	C13—C12—C11	120.29 (15)
C5—C4—H4	120.1	C13—C12—H12	119.9
C3—C4—H4	120.1	C11—C12—H12	119.9
N6—C5—C4	120.65 (14)	C12—C13—C14	119.47 (15)
N6—C5—H5	119.7	C12—C13—H13	120.3
C4—C5—H5	119.7	C14—C13—H13	120.3
O7—N6—C5	121.37 (12)	C13—C14—C15	120.39 (16)
O7—N6—C1	118.08 (12)	C13—C14—H14	119.8
C5—N6—C1	120.55 (12)	C15—C14—H14	119.8
C1—S8—C9	99.76 (7)	C14—C15—C10	120.73 (15)
C10—C9—S8	108.78 (10)	C14—C15—H15	119.6
C10—C9—H9A	109.9	C10—C15—H15	119.6
S8—C9—H9A	109.9
N6—C1—C2—C3	0.4 (2)	C2—C1—S8—C9	5.82 (16)
S8—C1—C2—C3	179.80 (13)	C1—S8—C9—C10	177.00 (11)
C1—C2—C3—C4	−0.4 (3)	S8—C9—C10—C11	117.36 (14)
C2—C3—C4—C5	0.1 (3)	S8—C9—C10—C15	−63.08 (17)
C3—C4—C5—N6	0.1 (3)	C15—C10—C11—C12	0.2 (2)
C4—C5—N6—O7	−179.46 (15)	C9—C10—C11—C12	179.81 (14)
C4—C5—N6—C1	−0.1 (2)	C10—C11—C12—C13	0.5 (3)
C2—C1—N6—O7	179.21 (13)	C11—C12—C13—C14	−1.0 (3)
S8—C1—N6—O7	−0.28 (16)	C12—C13—C14—C15	0.8 (3)
C2—C1—N6—C5	−0.2 (2)	C13—C14—C15—C10	0.0 (3)
S8—C1—N6—C5	−179.65 (11)	C11—C10—C15—C14	−0.5 (2)
N6—C1—S8—C9	−174.73 (11)	C9—C10—C15—C14	179.91 (15)

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

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

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