2-(Pyridin-2-yl)-1,3-oxathiane.

The title compound, C(9)H(11)NOS, exhibits a unique structural motif, with free rotation of the aliphatic oxathiane ring about the C-C bond connecting this moiety to the aromatic pyridine ring. The structure elucidation was undertaken due to its potential as a bidentate ligand for organometallic complexes. The oxathiane ring adopts the expected chair conformation, with the S atom in proximity to the N atom on the pyridine ring. The corresponding S-C-C-N torsion angle is 69.07 (14)°. In the crystal, mol-ecules aggregate as centrosymmetric pairs connected by pairs of C-H⋯N hydrogen bonds.

Related literature

The corresponding organic compound, 2-(2-pyridyl)-1,3-oxathiane, forms dimers via weak inter­molecular C—H⋯N hydrogen bonds, exhibiting similar photophysical properties as previously observed (Rachford et al., 2005 ▶; Rachford & Rack, 2006 ▶).

Experimental

Crystal data

C9H11NOS

M = 181.26

Monoclinic,

a = 7.5329 (3) Å

b = 11.8099 (5) Å

c = 9.7632 (4) Å

β = 92.940 (3)°

V = 867.42 (6) Å3

Z = 4

Cu Kα radiation

μ = 2.89 mm−1

T = 110 K

0.48 × 0.46 × 0.36 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2010 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.344, T max = 0.519

3675 measured reflections

1708 independent reflections

1656 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.07

1708 reflections

154 parameters

All H-atom parameters refined

Δρmax = 0.32 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) ▶; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018661/nr2024sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018661/nr2024Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018661/nr2024Isup3.cml

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

C9H11NOS	F(000) = 384
Mr = 181.26	Dx = 1.388 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 3102 reflections
a = 7.5329 (3) Å	θ = 0.5–72.0°
b = 11.8099 (5) Å	µ = 2.89 mm−1
c = 9.7632 (4) Å	T = 110 K
β = 92.940 (3)°	Block, colourless
V = 867.42 (6) Å3	0.48 × 0.46 × 0.36 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1708 independent reflections
Radiation source: Enhance (Cu) xray source	1656 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 16.3384 pixels mm-1	θmax = 72.1°, θmin = 5.9°
ω scans	h = −6→9
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2010), based on expressions derived by Clark & Reid (1995)]	k = −12→14
Tmin = 0.344, Tmax = 0.519	l = −12→12
3675 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	All H-atom parameters refined
wR(F2) = 0.085	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.3816P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1708 reflections	Δρmax = 0.32 e Å−3
154 parameters	Δρmin = −0.30 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0187 (14)

Experimental. CrysAlis PRO (Oxford Diffraction, 2010). Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R. C. Clark & J. S. Reid (Clark & Reid, 1995).

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
S1	0.20151 (4)	0.36641 (3)	0.12188 (3)	0.01796 (16)
O1	0.39908 (13)	0.45308 (9)	0.33518 (10)	0.0168 (2)
N1	0.59533 (16)	0.33730 (11)	0.03808 (12)	0.0174 (3)
C1	0.40671 (19)	0.43156 (12)	0.19284 (14)	0.0153 (3)
H1	0.421 (2)	0.5024 (17)	0.1426 (18)	0.020 (4)*
C2	0.05140 (19)	0.47642 (13)	0.17565 (15)	0.0190 (3)
H2A	0.070 (3)	0.5468 (17)	0.1214 (19)	0.025 (5)*
H2B	−0.069 (3)	0.4511 (17)	0.1510 (19)	0.023 (5)*
C3	0.0792 (2)	0.49944 (14)	0.32842 (15)	0.0202 (3)
H3B	0.002 (3)	0.5605 (18)	0.354 (2)	0.032 (5)*
H3A	0.049 (3)	0.4302 (18)	0.381 (2)	0.029 (5)*
C4	0.2682 (2)	0.53679 (13)	0.36591 (16)	0.0209 (3)
H4A	0.295 (3)	0.6069 (18)	0.316 (2)	0.028 (5)*
H4B	0.283 (2)	0.5485 (16)	0.465 (2)	0.022 (5)*
C5	0.55562 (19)	0.35019 (12)	0.16969 (14)	0.0150 (3)
C6	0.64241 (19)	0.29098 (12)	0.27685 (15)	0.0173 (3)
H6	0.607 (3)	0.3005 (17)	0.368 (2)	0.025 (5)*
C7	0.7761 (2)	0.21501 (13)	0.24709 (16)	0.0196 (3)
H7	0.839 (3)	0.1741 (17)	0.322 (2)	0.024 (5)*
C8	0.81619 (19)	0.19959 (13)	0.11104 (16)	0.0192 (3)
H8	0.903 (3)	0.1456 (16)	0.089 (2)	0.023 (5)*
C9	0.72283 (19)	0.26255 (13)	0.01104 (15)	0.0182 (3)
H9	0.751 (2)	0.2565 (16)	−0.082 (2)	0.018 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.0163 (2)	0.0193 (2)	0.0182 (2)	0.00117 (12)	−0.00020 (14)	−0.00488 (12)
O1	0.0182 (5)	0.0197 (5)	0.0127 (5)	0.0034 (4)	0.0013 (4)	−0.0034 (4)
N1	0.0188 (6)	0.0182 (6)	0.0155 (6)	−0.0010 (5)	0.0038 (5)	−0.0002 (5)
C1	0.0175 (7)	0.0164 (7)	0.0120 (6)	−0.0013 (5)	0.0021 (5)	0.0006 (5)
C2	0.0171 (7)	0.0217 (7)	0.0183 (7)	0.0028 (6)	0.0006 (5)	0.0000 (6)
C3	0.0200 (7)	0.0224 (8)	0.0188 (7)	0.0057 (6)	0.0047 (5)	−0.0012 (6)
C4	0.0231 (7)	0.0193 (7)	0.0202 (7)	0.0046 (6)	0.0008 (6)	−0.0069 (6)
C5	0.0147 (7)	0.0149 (6)	0.0156 (7)	−0.0033 (5)	0.0033 (5)	−0.0009 (5)
C6	0.0167 (7)	0.0198 (7)	0.0154 (7)	−0.0004 (5)	0.0015 (5)	0.0002 (5)
C7	0.0184 (7)	0.0200 (7)	0.0202 (7)	0.0006 (6)	−0.0003 (6)	0.0011 (6)
C8	0.0151 (7)	0.0193 (7)	0.0234 (8)	−0.0001 (6)	0.0036 (6)	−0.0029 (6)
C9	0.0187 (7)	0.0201 (7)	0.0163 (7)	−0.0020 (6)	0.0050 (5)	−0.0020 (6)

S1—C2	1.8174 (15)	C3—H3B	0.97 (2)
S1—C1	1.8307 (14)	C3—H3A	1.00 (2)
O1—C1	1.4168 (16)	C4—H4A	0.99 (2)
O1—C4	1.4386 (17)	C4—H4B	0.973 (19)
N1—C9	1.3407 (19)	C5—C6	1.393 (2)
N1—C5	1.3428 (18)	C6—C7	1.390 (2)
C1—C5	1.5030 (19)	C6—H6	0.95 (2)
C1—H1	0.979 (19)	C7—C8	1.389 (2)
C2—C3	1.520 (2)	C7—H7	0.98 (2)
C2—H2A	1.00 (2)	C8—C9	1.389 (2)
C2—H2B	0.97 (2)	C8—H8	0.95 (2)
C3—C4	1.517 (2)	C9—H9	0.951 (19)
C2—S1—C1	96.66 (7)	O1—C4—C3	113.23 (12)
C1—O1—C4	112.99 (11)	O1—C4—H4A	108.2 (12)
C9—N1—C5	117.39 (13)	C3—C4—H4A	109.6 (12)
O1—C1—C5	109.29 (11)	O1—C4—H4B	105.1 (11)
O1—C1—S1	111.76 (9)	C3—C4—H4B	109.6 (11)
C5—C1—S1	107.25 (10)	H4A—C4—H4B	111.0 (16)
O1—C1—H1	110.5 (11)	N1—C5—C6	122.87 (13)
C5—C1—H1	111.6 (11)	N1—C5—C1	114.90 (12)
S1—C1—H1	106.5 (11)	C6—C5—C1	122.22 (13)
C3—C2—S1	110.78 (10)	C7—C6—C5	118.94 (14)
C3—C2—H2A	110.8 (11)	C7—C6—H6	120.8 (12)
S1—C2—H2A	109.6 (11)	C5—C6—H6	120.2 (12)
C3—C2—H2B	112.2 (11)	C8—C7—C6	118.67 (14)
S1—C2—H2B	107.1 (12)	C8—C7—H7	122.0 (12)
H2A—C2—H2B	106.2 (16)	C6—C7—H7	119.3 (12)
C4—C3—C2	111.67 (12)	C7—C8—C9	118.34 (14)
C4—C3—H3B	106.9 (12)	C7—C8—H8	119.3 (12)
C2—C3—H3B	109.6 (12)	C9—C8—H8	122.4 (12)
C4—C3—H3A	110.4 (12)	N1—C9—C8	123.77 (13)
C2—C3—H3A	109.6 (12)	N1—C9—H9	115.9 (11)
H3B—C3—H3A	108.6 (16)	C8—C9—H9	120.3 (11)
C4—O1—C1—C5	175.71 (11)	O1—C1—C5—N1	−169.60 (11)
C4—O1—C1—S1	−65.74 (13)	S1—C1—C5—N1	69.07 (14)
C2—S1—C1—O1	56.31 (11)	O1—C1—C5—C6	11.82 (18)
C2—S1—C1—C5	176.07 (9)	S1—C1—C5—C6	−109.50 (13)
C1—S1—C2—C3	−52.99 (12)	N1—C5—C6—C7	0.0 (2)
S1—C2—C3—C4	59.31 (15)	C1—C5—C6—C7	178.42 (13)
C1—O1—C4—C3	64.95 (16)	C5—C6—C7—C8	−1.0 (2)
C2—C3—C4—O1	−61.17 (17)	C6—C7—C8—C9	1.2 (2)
C9—N1—C5—C6	0.9 (2)	C5—N1—C9—C8	−0.8 (2)
C9—N1—C5—C1	−177.62 (12)	C7—C8—C9—N1	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N1i	0.979 (19)	2.586 (19)	3.5399 (19)	164.8 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N1i	0.979 (19)	2.586 (19)	3.5399 (19)	164.8 (14)

Symmetry code: (i) .