2-(2,3,5,6-Tetra-methyl-benzyl-sulfan-yl)pyridine N-oxide.

In the title compound, C(16)H(19)NOS, the durene ring and the oxopyridyl ring form a dihedral angle of 82.26 (7)°. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonds, weak C-H⋯π inter-actions and π-π inter-actions [centroid-centroid distance of 3.4432 (19) Å], together with intra-molecular S⋯O [2.657 (2) Å] short contacts.

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 Durai Nayagam et al. (2008 ▶).

Experimental

Crystal data

C16H19NOS

M = 273.38

Monoclinic,

a = 16.601 (6) Å

b = 9.1562 (8) Å

c = 9.696 (4) Å

β = 106.098 (16)°

V = 1416.1 (7) Å3

Z = 4

Cu Kα radiation

μ = 1.95 mm−1

T = 193 (2) K

0.51 × 0.38 × 0.03 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971 ▶) T min = 0.480, T max = 0.960

2848 measured reflections

2672 independent reflections

2322 reflections with I > 2σ(I)

R int = 0.064

3 standard reflections frequency: 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.144

S = 1.05

2672 reflections

176 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & 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 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029747/sg2262sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029747/sg2262Isup2.hkl

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

C16H19NOS	F(000) = 584
Mr = 273.38	Dx = 1.282 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 16.601 (6) Å	θ = 36–45°
b = 9.1562 (8) Å	µ = 1.95 mm−1
c = 9.696 (4) Å	T = 193 K
β = 106.098 (16)°	Plate, colourless
V = 1416.1 (7) Å3	0.51 × 0.38 × 0.03 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2322 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.064
graphite	θmax = 69.9°, θmin = 2.8°
ω/2θ scans	h = −19→20
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971)	k = −11→0
Tmin = 0.48, Tmax = 0.96	l = −11→0
2848 measured reflections	3 standard reflections every 60 min
2672 independent reflections	intensity decay: 2%

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0919P)2 + 0.3984P] where P = (Fo2 + 2Fc2)/3
2672 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.37023 (12)	0.4717 (2)	0.5511 (2)	0.0350 (4)
C2	0.34830 (13)	0.5167 (2)	0.4094 (2)	0.0410 (5)
H2	0.3054	0.4668	0.3400	0.049*
C3	0.38878 (15)	0.6342 (3)	0.3689 (3)	0.0482 (6)
H3	0.3745	0.6647	0.2715	0.058*
C4	0.45024 (14)	0.7067 (2)	0.4716 (3)	0.0468 (5)
H4	0.4775	0.7892	0.4456	0.056*
C5	0.47167 (14)	0.6594 (2)	0.6111 (3)	0.0445 (5)
H5	0.5141	0.7092	0.6814	0.053*
N6	0.43286 (11)	0.54200 (19)	0.65006 (19)	0.0382 (4)
O7	0.45448 (11)	0.49322 (19)	0.78177 (17)	0.0531 (4)
S8	0.32907 (3)	0.32912 (5)	0.62989 (5)	0.0394 (2)
C9	0.24486 (13)	0.2652 (2)	0.4783 (2)	0.0392 (5)
H9A	0.2073	0.3471	0.4354	0.047*
H9B	0.2681	0.2226	0.4037	0.047*
C10	0.19752 (13)	0.1513 (2)	0.5361 (2)	0.0351 (4)
C11	0.13472 (12)	0.1944 (2)	0.5995 (2)	0.0381 (5)
C12	0.09035 (13)	0.0877 (3)	0.6508 (2)	0.0453 (5)
C13	0.11026 (15)	−0.0575 (3)	0.6389 (3)	0.0516 (6)
H13	0.0796	−0.1297	0.6733	0.062*
C14	0.17289 (15)	−0.1027 (2)	0.5791 (3)	0.0464 (5)
C15	0.21801 (13)	0.0032 (2)	0.5273 (2)	0.0389 (5)
C16	0.11488 (16)	0.3533 (3)	0.6159 (3)	0.0528 (6)
H16A	0.0581	0.3748	0.5559	0.079*
H16B	0.1553	0.4146	0.5857	0.079*
H16C	0.1183	0.3736	0.7166	0.079*
C17	0.02163 (17)	0.1289 (4)	0.7180 (3)	0.0671 (8)
H17A	−0.0016	0.0403	0.7488	0.101*
H17B	−0.0228	0.1812	0.6475	0.101*
H17C	0.0447	0.1920	0.8013	0.101*
C18	0.1893 (2)	−0.2643 (3)	0.5698 (4)	0.0711 (8)
H18A	0.1825	−0.2913	0.4694	0.107*
H18B	0.1494	−0.3197	0.6072	0.107*
H18C	0.2466	−0.2866	0.6267	0.107*
C19	0.28812 (17)	−0.0409 (3)	0.4648 (3)	0.0552 (6)
H19A	0.2969	−0.1467	0.4750	0.083*
H19B	0.3397	0.0099	0.5158	0.083*
H19C	0.2733	−0.0147	0.3628	0.083*

	U11	U22	U33	U12	U13	U23
C1	0.0376 (10)	0.0298 (9)	0.0427 (11)	0.0045 (8)	0.0200 (8)	−0.0011 (8)
C2	0.0424 (11)	0.0396 (11)	0.0453 (12)	0.0042 (9)	0.0192 (9)	0.0034 (9)
C3	0.0505 (12)	0.0450 (12)	0.0568 (14)	0.0085 (10)	0.0277 (11)	0.0131 (11)
C4	0.0454 (12)	0.0355 (11)	0.0695 (15)	0.0044 (9)	0.0327 (11)	0.0055 (11)
C5	0.0434 (11)	0.0348 (11)	0.0628 (14)	−0.0024 (8)	0.0272 (11)	−0.0073 (10)
N6	0.0417 (9)	0.0343 (9)	0.0433 (9)	0.0019 (7)	0.0198 (8)	−0.0047 (7)
O7	0.0648 (10)	0.0532 (10)	0.0401 (9)	−0.0085 (8)	0.0127 (8)	−0.0019 (7)
S8	0.0464 (3)	0.0368 (3)	0.0370 (3)	−0.0043 (2)	0.0148 (2)	0.00324 (19)
C9	0.0447 (11)	0.0371 (10)	0.0373 (11)	−0.0016 (9)	0.0136 (9)	0.0028 (8)
C10	0.0381 (10)	0.0317 (10)	0.0369 (10)	0.0011 (8)	0.0129 (8)	0.0012 (8)
C11	0.0357 (10)	0.0398 (11)	0.0387 (11)	0.0043 (8)	0.0102 (8)	−0.0032 (9)
C12	0.0383 (11)	0.0557 (13)	0.0437 (12)	−0.0067 (10)	0.0143 (9)	−0.0040 (10)
C13	0.0505 (13)	0.0501 (13)	0.0531 (14)	−0.0177 (10)	0.0128 (11)	0.0048 (11)
C14	0.0513 (13)	0.0323 (11)	0.0504 (13)	−0.0048 (9)	0.0054 (10)	0.0021 (9)
C15	0.0419 (10)	0.0345 (10)	0.0397 (11)	0.0052 (8)	0.0104 (9)	−0.0011 (8)
C16	0.0548 (13)	0.0453 (13)	0.0585 (15)	0.0141 (11)	0.0160 (12)	−0.0079 (11)
C17	0.0470 (13)	0.101 (2)	0.0612 (16)	−0.0133 (14)	0.0274 (12)	−0.0137 (16)
C18	0.084 (2)	0.0320 (12)	0.087 (2)	−0.0009 (12)	0.0070 (17)	0.0041 (13)
C19	0.0612 (14)	0.0486 (13)	0.0611 (15)	0.0143 (11)	0.0256 (12)	−0.0044 (12)

C1—N6	1.365 (3)	C12—C13	1.383 (4)
C1—C2	1.382 (3)	C12—C17	1.510 (3)
C1—S8	1.745 (2)	C13—C14	1.387 (4)
C2—C3	1.382 (3)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.401 (3)
C3—C4	1.382 (4)	C14—C18	1.511 (3)
C3—H3	0.9500	C15—C19	1.509 (3)
C4—C5	1.370 (3)	C16—H16A	0.9800
C4—H4	0.9500	C16—H16B	0.9800
C5—N6	1.360 (3)	C16—H16C	0.9800
C5—H5	0.9500	C17—H17A	0.9800
N6—O7	1.306 (2)	C17—H17B	0.9800
S8—C9	1.821 (2)	C17—H17C	0.9800
C9—C10	1.505 (3)	C18—H18A	0.9800
C9—H9A	0.9900	C18—H18B	0.9800
C9—H9B	0.9900	C18—H18C	0.9800
C10—C11	1.406 (3)	C19—H19A	0.9800
C10—C15	1.406 (3)	C19—H19B	0.9800
C11—C12	1.395 (3)	C19—H19C	0.9800
C11—C16	1.510 (3)
N6—C1—C2	119.84 (19)	C12—C13—C14	123.1 (2)
N6—C1—S8	111.06 (15)	C12—C13—H13	118.4
C2—C1—S8	129.10 (17)	C14—C13—H13	118.4
C3—C2—C1	120.0 (2)	C13—C14—C15	118.7 (2)
C3—C2—H2	120.0	C13—C14—C18	119.1 (2)
C1—C2—H2	120.0	C15—C14—C18	122.2 (2)
C2—C3—C4	119.3 (2)	C14—C15—C10	118.9 (2)
C2—C3—H3	120.4	C14—C15—C19	120.5 (2)
C4—C3—H3	120.4	C10—C15—C19	120.6 (2)
C5—C4—C3	119.8 (2)	C11—C16—H16A	109.5
C5—C4—H4	120.1	C11—C16—H16B	109.5
C3—C4—H4	120.1	H16A—C16—H16B	109.5
N6—C5—C4	120.7 (2)	C11—C16—H16C	109.5
N6—C5—H5	119.6	H16A—C16—H16C	109.5
C4—C5—H5	119.6	H16B—C16—H16C	109.5
O7—N6—C5	121.28 (19)	C12—C17—H17A	109.5
O7—N6—C1	118.40 (17)	C12—C17—H17B	109.5
C5—N6—C1	120.32 (19)	H17A—C17—H17B	109.5
C1—S8—C9	101.13 (10)	C12—C17—H17C	109.5
C10—C9—S8	106.60 (14)	H17A—C17—H17C	109.5
C10—C9—H9A	110.4	H17B—C17—H17C	109.5
S8—C9—H9A	110.4	C14—C18—H18A	109.5
C10—C9—H9B	110.4	C14—C18—H18B	109.5
S8—C9—H9B	110.4	H18A—C18—H18B	109.5
H9A—C9—H9B	108.6	C14—C18—H18C	109.5
C11—C10—C15	121.22 (19)	H18A—C18—H18C	109.5
C11—C10—C9	119.71 (19)	H18B—C18—H18C	109.5
C15—C10—C9	119.07 (19)	C15—C19—H19A	109.5
C12—C11—C10	119.2 (2)	C15—C19—H19B	109.5
C12—C11—C16	119.0 (2)	H19A—C19—H19B	109.5
C10—C11—C16	121.7 (2)	C15—C19—H19C	109.5
C13—C12—C11	118.7 (2)	H19A—C19—H19C	109.5
C13—C12—C17	120.2 (2)	H19B—C19—H19C	109.5
C11—C12—C17	121.1 (2)
N6—C1—C2—C3	−1.1 (3)	C15—C10—C11—C16	177.1 (2)
S8—C1—C2—C3	179.56 (16)	C9—C10—C11—C16	−1.9 (3)
C1—C2—C3—C4	−0.9 (3)	C10—C11—C12—C13	0.6 (3)
C2—C3—C4—C5	1.6 (3)	C16—C11—C12—C13	−178.4 (2)
C3—C4—C5—N6	−0.3 (3)	C10—C11—C12—C17	−179.2 (2)
C4—C5—N6—O7	177.93 (19)	C16—C11—C12—C17	1.8 (3)
C4—C5—N6—C1	−1.7 (3)	C11—C12—C13—C14	0.5 (4)
C2—C1—N6—O7	−177.22 (18)	C17—C12—C13—C14	−179.7 (2)
S8—C1—N6—O7	2.2 (2)	C12—C13—C14—C15	−0.4 (4)
C2—C1—N6—C5	2.5 (3)	C12—C13—C14—C18	−179.5 (2)
S8—C1—N6—C5	−178.13 (14)	C13—C14—C15—C10	−0.8 (3)
N6—C1—S8—C9	176.64 (14)	C18—C14—C15—C10	178.2 (2)
C2—C1—S8—C9	−4.0 (2)	C13—C14—C15—C19	178.5 (2)
C1—S8—C9—C10	−173.92 (14)	C18—C14—C15—C19	−2.5 (4)
S8—C9—C10—C11	83.9 (2)	C11—C10—C15—C14	2.0 (3)
S8—C9—C10—C15	−95.2 (2)	C9—C10—C15—C14	−178.98 (19)
C15—C10—C11—C12	−1.9 (3)	C11—C10—C15—C19	−177.3 (2)
C9—C10—C11—C12	179.06 (19)	C9—C10—C15—C19	1.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O7i	0.95	2.51	3.319 (3)	143.
C2—H2···Cg2ii	0.95	2.98	3.853 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O7i	0.95	2.51	3.319 (3)	143
C2—H2⋯Cg2ii	0.95	2.98	3.853 (3)	154

Symmetry codes: (i) ; (ii) . Cg2 is the centroid of the C10–C15 ring.