3-(Pyridin-4-yl-thio)-pentane-2,4-dione.

In the title compound, C(10)H(11)NO(2)S, the acetyl-acetone group crystallizes in the keto form with all the non-hydrogen atoms in the acetyl-acetone group approximately co-planar with a maximum atomic deviation 0.055 (2) Å; the dihedral angle between the acetyl-acetone group and the pyridine ring is 85.90 (6)°. An intra-molecular O-H⋯O hydrogen bond involving the acetyl-acetone group forms a six-membered ring.

Related literature

For applications of β-diketones and their derivatives in metallo-supra­molecular chemistry, see: Aromí et al. (2008 ▶); Chen et al. (2003 ▶; 2004 ▶); Domasevitch et al. (2006 ▶); Massue et al. (2005 ▶); Soldatov & Ripmeester (2001 ▶); Tabellion et al. (2001 ▶); Vigato et al. (2009 ▶); Vreshch et al. (2003 ▶, 2004 ▶); Won et al. (2007 ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

C10H11NO2S

M = 209.26

Monoclinic,

a = 8.3273 (7) Å

b = 9.5614 (8) Å

c = 13.0681 (11) Å

β = 92.698 (1)°

V = 1039.34 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 298 K

0.35 × 0.30 × 0.28 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.907, T max = 0.925

5011 measured reflections

1822 independent reflections

1351 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.120

S = 1.06

1822 reflections

130 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011330/zj2007sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011330/zj2007Isup2.hkl

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

C10H11NO2S	F(000) = 440
Mr = 209.26	Dx = 1.337 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2174 reflections
a = 8.3273 (7) Å	θ = 2.5–27.3°
b = 9.5614 (8) Å	µ = 0.28 mm−1
c = 13.0681 (11) Å	T = 298 K
β = 92.698 (1)°	Block, yellow
V = 1039.34 (15) Å3	0.35 × 0.30 × 0.28 mm
Z = 4

Siemens SMART CCD area-detector diffractometer	1822 independent reflections
Radiation source: fine-focus sealed tube	1351 reflections with I > 2σ(I)
graphite	Rint = 0.030
phi and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.907, Tmax = 0.925	k = −5→11
5011 measured reflections	l = −15→15

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0562P)2 + 0.3241P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1822 reflections	Δρmax = 0.17 e Å−3
130 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.136 (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.

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	0.87871 (8)	0.22005 (6)	0.95516 (6)	0.0688 (3)
O1	0.7336 (2)	0.60208 (19)	1.01493 (15)	0.0761 (6)
H1	0.7715	0.6213	0.9547	0.091*
O2	0.8608 (2)	0.60632 (19)	0.85162 (14)	0.0769 (6)
N1	0.4443 (3)	−0.0271 (2)	0.83293 (19)	0.0714 (6)
C1	0.6930 (4)	0.3985 (4)	1.1103 (2)	0.0863 (9)
H1A	0.7813	0.3688	1.1550	0.129*
H1B	0.6305	0.3185	1.0886	0.129*
H1C	0.6266	0.4623	1.1461	0.129*
C2	0.7557 (3)	0.4691 (3)	1.01961 (19)	0.0566 (6)
C3	0.8327 (3)	0.3980 (2)	0.94164 (17)	0.0495 (6)
C4	0.8804 (3)	0.4736 (3)	0.85562 (18)	0.0580 (6)
C5	0.9512 (4)	0.4065 (4)	0.7658 (2)	0.0890 (10)
H5A	1.0051	0.4759	0.7269	0.133*
H5B	0.8674	0.3639	0.7235	0.133*
H5C	1.0270	0.3363	0.7889	0.133*
C6	0.7057 (3)	0.1310 (2)	0.90682 (16)	0.0466 (5)
C7	0.7102 (3)	−0.0134 (2)	0.90713 (19)	0.0584 (6)
H7	0.8011	−0.0607	0.9327	0.070*
C8	0.5786 (3)	−0.0856 (3)	0.8692 (2)	0.0730 (8)
H8	0.5843	−0.1827	0.8690	0.088*
C9	0.4412 (3)	0.1119 (3)	0.8347 (2)	0.0630 (7)
H9	0.3474	0.1561	0.8107	0.076*
C10	0.5674 (3)	0.1949 (2)	0.86962 (18)	0.0542 (6)
H10	0.5591	0.2919	0.8680	0.065*

	U11	U22	U33	U12	U13	U23
S1	0.0565 (4)	0.0432 (4)	0.1043 (6)	0.0034 (3)	−0.0216 (3)	−0.0036 (3)
O1	0.0818 (13)	0.0532 (11)	0.0934 (14)	0.0072 (9)	0.0045 (10)	−0.0142 (9)
O2	0.0901 (14)	0.0563 (11)	0.0827 (13)	−0.0179 (10)	−0.0131 (10)	0.0166 (9)
N1	0.0674 (14)	0.0546 (13)	0.0923 (17)	−0.0155 (11)	0.0029 (12)	−0.0121 (11)
C1	0.090 (2)	0.095 (2)	0.0750 (19)	−0.0214 (18)	0.0168 (15)	−0.0053 (16)
C2	0.0498 (13)	0.0525 (14)	0.0668 (15)	−0.0059 (10)	−0.0058 (11)	−0.0064 (11)
C3	0.0459 (12)	0.0407 (12)	0.0610 (14)	−0.0075 (9)	−0.0053 (10)	−0.0053 (10)
C4	0.0484 (13)	0.0634 (16)	0.0614 (15)	−0.0137 (11)	−0.0080 (11)	−0.0028 (12)
C5	0.080 (2)	0.116 (3)	0.0717 (19)	−0.0176 (18)	0.0129 (15)	−0.0173 (17)
C6	0.0502 (13)	0.0403 (12)	0.0495 (12)	−0.0014 (9)	0.0039 (9)	−0.0023 (9)
C7	0.0605 (15)	0.0398 (12)	0.0751 (16)	0.0029 (10)	0.0060 (12)	0.0046 (11)
C8	0.076 (2)	0.0402 (13)	0.103 (2)	−0.0097 (13)	0.0085 (16)	−0.0015 (13)
C9	0.0570 (14)	0.0594 (16)	0.0720 (16)	−0.0022 (12)	−0.0043 (12)	−0.0048 (12)
C10	0.0577 (14)	0.0413 (12)	0.0630 (14)	−0.0010 (10)	−0.0044 (11)	−0.0041 (10)

S1—C3	1.752 (2)	C4—C5	1.484 (4)
S1—C6	1.764 (2)	C5—H5A	0.9600
O1—C2	1.286 (3)	C5—H5B	0.9600
O1—H1	0.8814	C5—H5C	0.9600
O2—C4	1.280 (3)	C6—C10	1.373 (3)
N1—C8	1.318 (3)	C6—C7	1.381 (3)
N1—C9	1.330 (3)	C7—C8	1.368 (4)
C1—C2	1.480 (4)	C7—H7	0.9300
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—C10	1.378 (3)
C1—H1C	0.9600	C9—H9	0.9300
C2—C3	1.404 (3)	C10—H10	0.9300
C3—C4	1.409 (3)
C3—S1—C6	105.16 (10)	H5A—C5—H5B	109.5
C2—O1—H1	101.1	C4—C5—H5C	109.5
C8—N1—C9	115.8 (2)	H5A—C5—H5C	109.5
C2—C1—H1A	109.5	H5B—C5—H5C	109.5
C2—C1—H1B	109.5	C10—C6—C7	117.9 (2)
H1A—C1—H1B	109.5	C10—C6—S1	124.71 (17)
C2—C1—H1C	109.5	C7—C6—S1	117.38 (17)
H1A—C1—H1C	109.5	C8—C7—C6	118.8 (2)
H1B—C1—H1C	109.5	C8—C7—H7	120.6
O1—C2—C3	120.9 (2)	C6—C7—H7	120.6
O1—C2—C1	115.7 (2)	N1—C8—C7	124.6 (2)
C3—C2—C1	123.4 (2)	N1—C8—H8	117.7
C2—C3—C4	119.1 (2)	C7—C8—H8	117.7
C2—C3—S1	120.14 (18)	N1—C9—C10	124.5 (2)
C4—C3—S1	120.67 (18)	N1—C9—H9	117.7
O2—C4—C3	120.0 (2)	C10—C9—H9	117.7
O2—C4—C5	116.8 (2)	C6—C10—C9	118.4 (2)
C3—C4—C5	123.1 (3)	C6—C10—H10	120.8
C4—C5—H5A	109.5	C9—C10—H10	120.8
C4—C5—H5B	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.88	1.58	2.427 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.88	1.58	2.427 (3)	161