2-(Mesitylmethylsulfanyl)pyridine N-oxide monohydrate.

In the title compound, C(15)H(17)NOS·H(2)O, the benzene and pyridine rings form a dihedral angle of 71.18 (2)°. The intra-molecular S⋯O distance [2.737 (3) Å] is shorter than expected and, in terms of hybridization principles, the N-C-S angle [114.1 (2)°] is smaller than expected. The crystal structure is stabilized by inter-molecular O-H⋯O and weak C-H⋯O hydrogen bonds. In addition, weak π-π stacking inter-actions with a centroid-centroid distance of 3.778 (3) Å are also observed.

Related literature

For related structures, see: Jebas et al. (2005 ▶); Hartung et al. (1996 ▶); Ravindran Durai Nayagam et al. (2008 ▶). 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 bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H17NOS·H2O

M = 277.37

Monoclinic,

a = 12.358 (7) Å

b = 15.404 (6) Å

c = 7.748 (5) Å

β = 106.40 (2)°

V = 1415.0 (13) Å3

Z = 4

Cu Kα radiation

μ = 2.01 mm−1

T = 193 (2) K

0.50 × 0.20 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971 ▶) T min = 0.67, T max = 0.99 (expected range = 0.612–0.904)

2896 measured reflections

2684 independent reflections

2048 reflections with I > 2σ(I)

R int = 0.067

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

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.190

S = 1.06

2684 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.79 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; 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/S1600536808029255/lh2692sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029255/lh2692Isup2.hkl

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

C15H17NOS·H2O	F(000) = 592
Mr = 277.37	Dx = 1.302 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 12.358 (7) Å	θ = 36–50°
b = 15.404 (6) Å	µ = 2.01 mm−1
c = 7.748 (5) Å	T = 193 K
β = 106.40 (2)°	Plate, colourless
V = 1415.0 (13) Å3	0.50 × 0.20 × 0.05 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2048 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.067
graphite	θmax = 70.0°, θmin = 3.7°
ω/2θ scans	h = −14→15
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971)	k = −18→0
Tmin = 0.67, Tmax = 0.99	l = −9→0
2896 measured reflections	3 standard reflections every 60 min
2684 independent reflections	intensity decay: 3%

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1179P)2 + 0.1489P] where P = (Fo2 + 2Fc2)/3
2684 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.79 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	0.0724 (3)	−0.0867 (2)	0.3741 (4)	0.0305 (7)
C2	0.0757 (3)	−0.1748 (2)	0.4252 (4)	0.0336 (7)
C3	−0.0205 (3)	−0.2249 (2)	0.3573 (4)	0.0375 (8)
H3	−0.0199	−0.2837	0.3946	0.045*
C4	−0.1170 (3)	−0.1924 (2)	0.2377 (4)	0.0376 (8)
C5	−0.1186 (3)	−0.1053 (2)	0.1862 (4)	0.0355 (7)
H5	−0.1844	−0.0818	0.1045	0.043*
C6	−0.0247 (3)	−0.05268 (19)	0.2537 (4)	0.0314 (7)
C7	0.1771 (3)	−0.2149 (2)	0.5531 (5)	0.0469 (9)
H7A	0.1954	−0.1835	0.6678	0.070*
H7B	0.2411	−0.2117	0.5022	0.070*
H7C	0.1612	−0.2758	0.5733	0.070*
C8	−0.2178 (4)	−0.2507 (3)	0.1647 (6)	0.0561 (11)
H8A	−0.2837	−0.2153	0.1054	0.084*
H8B	−0.2332	−0.2833	0.2637	0.084*
H8C	−0.2020	−0.2913	0.0775	0.084*
C9	−0.0327 (3)	0.0412 (2)	0.1961 (5)	0.0379 (8)
H9A	0.0247	0.0534	0.1341	0.057*
H9B	−0.0202	0.0786	0.3022	0.057*
H9C	−0.1078	0.0526	0.1144	0.057*
C10	0.1718 (3)	−0.0290 (2)	0.4538 (4)	0.0354 (7)
H10A	0.2203	−0.0556	0.5653	0.042*
H10B	0.1454	0.0280	0.4850	0.042*
S11	0.25245 (7)	−0.01425 (5)	0.29196 (10)	0.0343 (3)
C12	0.3569 (3)	0.05537 (19)	0.4133 (4)	0.0300 (7)
C13	0.3783 (3)	0.0803 (2)	0.5928 (4)	0.0364 (7)
H13	0.3343	0.0567	0.6640	0.044*
C14	0.4623 (3)	0.1386 (2)	0.6672 (5)	0.0454 (9)
H14	0.4765	0.1552	0.7897	0.054*
C15	0.5265 (3)	0.1733 (2)	0.5633 (6)	0.0487 (9)
H15	0.5839	0.2147	0.6128	0.058*
C16	0.5057 (3)	0.1469 (2)	0.3886 (6)	0.0446 (9)
H16	0.5501	0.1697	0.3171	0.053*
N17	0.4236 (2)	0.08942 (17)	0.3157 (4)	0.0336 (6)
O18	0.4037 (2)	0.06592 (17)	0.1461 (3)	0.0446 (6)
O1W	0.6227 (3)	0.0815 (2)	0.0886 (4)	0.0610 (8)
H1W	0.5575	0.0690	0.0933	0.091*
H2W	0.6495	0.0394	0.0452	0.091*

	U11	U22	U33	U12	U13	U23
C1	0.0458 (18)	0.0265 (14)	0.0256 (14)	−0.0078 (13)	0.0208 (14)	−0.0057 (11)
C2	0.0497 (19)	0.0286 (16)	0.0288 (15)	−0.0017 (14)	0.0214 (14)	−0.0011 (13)
C3	0.057 (2)	0.0265 (15)	0.0356 (17)	−0.0102 (14)	0.0246 (16)	−0.0070 (13)
C4	0.0480 (19)	0.0392 (17)	0.0332 (16)	−0.0162 (15)	0.0239 (15)	−0.0141 (14)
C5	0.0420 (18)	0.0388 (18)	0.0300 (16)	−0.0035 (14)	0.0171 (14)	−0.0055 (13)
C6	0.0492 (19)	0.0263 (15)	0.0255 (14)	−0.0026 (13)	0.0217 (14)	−0.0050 (12)
C7	0.058 (2)	0.0377 (19)	0.048 (2)	0.0032 (17)	0.0194 (18)	0.0037 (16)
C8	0.062 (3)	0.058 (2)	0.055 (2)	−0.030 (2)	0.027 (2)	−0.020 (2)
C9	0.060 (2)	0.0264 (16)	0.0334 (16)	0.0007 (14)	0.0230 (16)	−0.0007 (12)
C10	0.0476 (19)	0.0363 (16)	0.0261 (15)	−0.0109 (14)	0.0167 (14)	−0.0030 (13)
S11	0.0424 (5)	0.0364 (5)	0.0281 (4)	−0.0087 (3)	0.0164 (3)	−0.0048 (3)
C12	0.0309 (15)	0.0228 (14)	0.0361 (16)	0.0022 (12)	0.0091 (13)	0.0048 (12)
C13	0.0443 (18)	0.0318 (16)	0.0312 (16)	0.0004 (14)	0.0075 (14)	0.0038 (13)
C14	0.046 (2)	0.0403 (19)	0.045 (2)	0.0026 (16)	0.0045 (17)	−0.0067 (16)
C15	0.0396 (19)	0.039 (2)	0.068 (3)	−0.0066 (15)	0.0159 (18)	−0.0110 (18)
C16	0.0367 (18)	0.0357 (18)	0.066 (2)	−0.0061 (15)	0.0230 (18)	−0.0009 (17)
N17	0.0343 (14)	0.0293 (13)	0.0402 (15)	0.0044 (11)	0.0154 (12)	0.0042 (11)
O18	0.0475 (15)	0.0501 (15)	0.0417 (14)	−0.0042 (11)	0.0213 (12)	0.0012 (11)
O1W	0.0589 (18)	0.085 (2)	0.0441 (15)	−0.0134 (16)	0.0233 (14)	−0.0132 (15)

C1—C6	1.397 (5)	C9—H9B	0.9800
C1—C2	1.411 (4)	C9—H9C	0.9800
C1—C10	1.500 (4)	C10—S11	1.823 (3)
C2—C3	1.390 (5)	C10—H10A	0.9900
C2—C7	1.494 (5)	C10—H10B	0.9900
C3—C4	1.381 (5)	S11—C12	1.736 (3)
C3—H3	0.9500	C12—N17	1.371 (4)
C4—C5	1.399 (5)	C12—C13	1.394 (4)
C4—C8	1.509 (5)	C13—C14	1.371 (5)
C5—C6	1.391 (5)	C13—H13	0.9500
C5—H5	0.9500	C14—C15	1.388 (6)
C6—C9	1.509 (4)	C14—H14	0.9500
C7—H7A	0.9800	C15—C16	1.367 (6)
C7—H7B	0.9800	C15—H15	0.9500
C7—H7C	0.9800	C16—N17	1.345 (4)
C8—H8A	0.9800	C16—H16	0.9500
C8—H8B	0.9800	N17—O18	1.318 (4)
C8—H8C	0.9800	O1W—H1W	0.8400
C9—H9A	0.9800	O1W—H2W	0.8400
C6—C1—C2	120.0 (3)	C6—C9—H9B	109.5
C6—C1—C10	120.1 (3)	H9A—C9—H9B	109.5
C2—C1—C10	119.9 (3)	C6—C9—H9C	109.5
C3—C2—C1	118.3 (3)	H9A—C9—H9C	109.5
C3—C2—C7	119.3 (3)	H9B—C9—H9C	109.5
C1—C2—C7	122.4 (3)	C1—C10—S11	109.5 (2)
C4—C3—C2	122.5 (3)	C1—C10—H10A	109.8
C4—C3—H3	118.7	S11—C10—H10A	109.8
C2—C3—H3	118.7	C1—C10—H10B	109.8
C3—C4—C5	118.6 (3)	S11—C10—H10B	109.8
C3—C4—C8	120.1 (3)	H10A—C10—H10B	108.2
C5—C4—C8	121.3 (4)	C12—S11—C10	99.89 (16)
C6—C5—C4	120.6 (3)	N17—C12—C13	118.1 (3)
C6—C5—H5	119.7	N17—C12—S11	114.1 (2)
C4—C5—H5	119.7	C13—C12—S11	127.8 (3)
C5—C6—C1	120.0 (3)	C14—C13—C12	120.5 (3)
C5—C6—C9	118.0 (3)	C14—C13—H13	119.7
C1—C6—C9	122.0 (3)	C12—C13—H13	119.7
C2—C7—H7A	109.5	C13—C14—C15	119.9 (4)
C2—C7—H7B	109.5	C13—C14—H14	120.1
H7A—C7—H7B	109.5	C15—C14—H14	120.1
C2—C7—H7C	109.5	C16—C15—C14	118.8 (3)
H7A—C7—H7C	109.5	C16—C15—H15	120.6
H7B—C7—H7C	109.5	C14—C15—H15	120.6
C4—C8—H8A	109.5	N17—C16—C15	121.4 (3)
C4—C8—H8B	109.5	N17—C16—H16	119.3
H8A—C8—H8B	109.5	C15—C16—H16	119.3
C4—C8—H8C	109.5	O18—N17—C16	120.4 (3)
H8A—C8—H8C	109.5	O18—N17—C12	118.2 (3)
H8B—C8—H8C	109.5	C16—N17—C12	121.3 (3)
C6—C9—H9A	109.5	H1W—O1W—H2W	109.5
C6—C1—C2—C3	−2.0 (4)	C6—C1—C10—S11	−80.1 (3)
C10—C1—C2—C3	176.0 (3)	C2—C1—C10—S11	101.9 (3)
C6—C1—C2—C7	179.9 (3)	C1—C10—S11—C12	178.5 (2)
C10—C1—C2—C7	−2.1 (5)	C10—S11—C12—N17	−170.9 (2)
C1—C2—C3—C4	2.3 (5)	C10—S11—C12—C13	8.2 (3)
C7—C2—C3—C4	−179.6 (3)	N17—C12—C13—C14	1.3 (5)
C2—C3—C4—C5	−1.5 (5)	S11—C12—C13—C14	−177.7 (3)
C2—C3—C4—C8	178.3 (3)	C12—C13—C14—C15	0.2 (5)
C3—C4—C5—C6	0.3 (5)	C13—C14—C15—C16	−1.3 (6)
C8—C4—C5—C6	−179.5 (3)	C14—C15—C16—N17	1.0 (6)
C4—C5—C6—C1	0.0 (4)	C15—C16—N17—O18	178.9 (3)
C4—C5—C6—C9	−178.7 (3)	C15—C16—N17—C12	0.5 (5)
C2—C1—C6—C5	0.9 (4)	C13—C12—N17—O18	179.9 (3)
C10—C1—C6—C5	−177.1 (3)	S11—C12—N17—O18	−0.9 (4)
C2—C1—C6—C9	179.5 (3)	C13—C12—N17—C16	−1.7 (5)
C10—C1—C6—C9	1.5 (4)	S11—C12—N17—C16	177.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O18	0.84	2.05	2.875 (4)	165.
O1W—H2W···O18i	0.84	2.17	2.869 (4)	141.
C16—H16···O1W	0.95	2.58	3.226 (6)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O18	0.84	2.05	2.875 (4)	165
O1W—H2W⋯O18i	0.84	2.17	2.869 (4)	141
C16—H16⋯O1W	0.95	2.58	3.226 (6)	125

Symmetry code: (i) .