5H-1-Benzothio-pyrano[2,3-b]pyridin-5-one.

Mol-ecules of the title compound, C(12)H(7)NOS, with one half-mol-ecule in the asymmetric unit, are disordered about a crystallographic centre of inversion. Refinement showed that the C=O group is disordered with the S atom and the N atom is disordered over four positions. Adjacent mol-ecules are connected through C-H⋯O hydrogen bonds and π⋯π inter-actions (centroid-centroid distances of 3.635 and 3.858 Å).

Related literature

For related literature, see: Hidetoshi (1997 ▶); Khan et al. (2008 ▶); Mann & Reid (1952 ▶).

Experimental

Crystal data

C12H7NOS

M = 213.26

Monoclinic,

a = 7.7308 (18) Å

b = 3.8585 (9) Å

c = 15.771 (3) Å

β = 99.333 (9)°

V = 464.20 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 296 (2) K

0.25 × 0.06 × 0.04 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.977, T max = 0.987

5384 measured reflections

1189 independent reflections

822 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.179

S = 1.17

1189 reflections

83 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); 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 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024628/bt2756sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024628/bt2756Isup2.hkl

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

C12H7NOS	F000 = 220
Mr = 213.26	Dx = 1.525 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1189 reflections
a = 7.7308 (18) Å	θ = 2.6–28.7º
b = 3.8585 (9) Å	µ = 0.31 mm−1
c = 15.771 (3) Å	T = 296 (2) K
β = 99.333 (9)º	Needle, light yellow
V = 464.20 (18) Å3	0.25 × 0.06 × 0.04 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	1189 independent reflections
Radiation source: fine-focus sealed tube	822 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.034
Detector resolution: 7.5 pixels mm-1	θmax = 28.7º
T = 296(2) K	θmin = 2.6º
ω scans	h = −10→10
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −5→3
Tmin = 0.977, Tmax = 0.987	l = −21→21
5384 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)] = 0.070	H-atom parameters constrained
wR(F2) = 0.179	w = 1/[σ2(Fo2) + (0.064P)2 + 0.435P] where P = (Fo2 + 2Fc2)/3
S = 1.17	(Δ/σ)max < 0.001
1189 reflections	Δρmax = 0.62 e Å−3
83 parameters	Δρmin = −0.26 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	Occ. (<1)
C6	0.3852 (15)	0.001 (3)	0.0576 (7)	0.044 (2)	0.50
O1	0.2856 (9)	−0.006 (2)	0.1093 (4)	0.083 (3)	0.50
C3B	0.1527 (4)	−0.2668 (8)	−0.05322 (19)	0.0508 (7)	0.75
H3B	0.0739	−0.2649	−0.0145	0.061*	0.75
N1B	0.3839 (4)	−0.2689 (8)	−0.17028 (19)	0.0530 (8)	0.25
S1	0.6613 (4)	−0.0009 (10)	−0.08029 (19)	0.0481 (6)	0.50
C3A	0.3839 (4)	−0.2689 (8)	−0.17028 (19)	0.0530 (8)	0.75
H3A	0.4605	−0.2676	−0.2100	0.064*	0.75
N1A	0.1527 (4)	−0.2668 (8)	−0.05322 (19)	0.0508 (7)	0.25
C1	0.4368 (4)	−0.1412 (8)	−0.08724 (19)	0.0444 (7)
C2	0.3204 (4)	−0.1406 (8)	−0.02885 (17)	0.0437 (7)
C4	0.1027 (4)	−0.3937 (9)	−0.1335 (2)	0.0577 (9)
H4	−0.0102	−0.4803	−0.1495	0.069*
C5	0.2178 (5)	−0.3955 (9)	−0.1919 (2)	0.0570 (9)
H5	0.1816	−0.4842	−0.2467	0.068*

	U11	U22	U33	U12	U13	U23
C6	0.045 (6)	0.038 (3)	0.047 (6)	0.002 (4)	0.002 (3)	0.008 (4)
O1	0.073 (4)	0.134 (6)	0.053 (4)	−0.023 (4)	0.047 (3)	−0.015 (4)
C3B	0.0496 (16)	0.0468 (16)	0.0563 (17)	−0.0002 (13)	0.0099 (13)	0.0016 (13)
N1B	0.0632 (19)	0.0482 (17)	0.0476 (15)	0.0023 (14)	0.0090 (13)	−0.0010 (13)
S1	0.0438 (17)	0.0620 (11)	0.0411 (16)	−0.0040 (13)	0.0145 (8)	−0.0032 (13)
C3A	0.0632 (19)	0.0482 (17)	0.0476 (15)	0.0023 (14)	0.0090 (13)	−0.0010 (13)
N1A	0.0496 (16)	0.0468 (16)	0.0563 (17)	−0.0002 (13)	0.0099 (13)	0.0016 (13)
C1	0.0434 (14)	0.0371 (14)	0.0512 (16)	0.0028 (12)	0.0031 (12)	0.0058 (12)
C2	0.0522 (16)	0.0361 (14)	0.0420 (14)	0.0059 (12)	0.0049 (12)	0.0037 (11)
C4	0.0501 (18)	0.0507 (19)	0.066 (2)	−0.0058 (14)	−0.0082 (15)	0.0034 (15)
C5	0.069 (2)	0.0495 (18)	0.0474 (17)	0.0000 (16)	−0.0075 (15)	−0.0048 (14)

C6—O1	1.209 (9)	S1—C2i	1.791 (4)
C6—C2	1.480 (13)	S1—C1	1.803 (4)
C6—C1i	1.481 (13)	C1—C2	1.388 (4)
C3B—C4	1.355 (4)	C1—C6i	1.481 (13)
C3B—C2	1.380 (4)	C2—S1i	1.791 (4)
C3B—H3B	0.9300	C4—C5	1.380 (5)
N1B—C5	1.364 (5)	C4—H4	0.9300
N1B—C1	1.398 (4)	C5—H5	0.9300
O1—C6—C2	117.2 (11)	C6i—C1—S1	15.5 (4)
O1—C6—C1i	117.1 (11)	C3B—C2—C1	119.7 (3)
C2—C6—C1i	125.7 (7)	C3B—C2—C6	123.3 (5)
C4—C3B—C2	120.0 (3)	C1—C2—C6	117.0 (5)
C4—C3B—H3B	120.0	C3B—C2—S1i	107.4 (2)
C2—C3B—H3B	120.0	C1—C2—S1i	132.9 (3)
C5—N1B—C1	118.7 (3)	C6—C2—S1i	15.9 (4)
C2i—S1—C1	94.30 (18)	C3B—C4—C5	120.6 (3)
C2—C1—N1B	120.0 (3)	C3B—C4—H4	119.7
C2—C1—C6i	117.3 (5)	C5—C4—H4	119.7
N1B—C1—C6i	122.7 (5)	N1B—C5—C4	120.9 (3)
C2—C1—S1	132.8 (3)	N1B—C5—H5	119.6
N1B—C1—S1	107.2 (2)	C4—C5—H5	119.6
C5—N1B—C1—C2	−0.8 (5)	S1—C1—C2—C6	0.2 (6)
C5—N1B—C1—C6i	179.5 (6)	N1B—C1—C2—S1i	−179.5 (3)
C5—N1B—C1—S1	179.4 (3)	C6i—C1—C2—S1i	0.2 (6)
C2i—S1—C1—C2	−0.2 (4)	S1—C1—C2—S1i	0.2 (6)
C2i—S1—C1—N1B	179.6 (2)	O1—C6—C2—C3B	2.2 (15)
C2i—S1—C1—C6i	0(2)	C1i—C6—C2—C3B	−179.7 (7)
C4—C3B—C2—C1	0.6 (5)	O1—C6—C2—C1	−178.2 (10)
C4—C3B—C2—C6	−179.8 (6)	C1i—C6—C2—C1	−0.1 (12)
C4—C3B—C2—S1i	−179.7 (3)	O1—C6—C2—S1i	2.0 (11)
N1B—C1—C2—C3B	0.1 (4)	C1i—C6—C2—S1i	−180 (3)
C6i—C1—C2—C3B	179.7 (6)	C2—C3B—C4—C5	−0.5 (5)
S1—C1—C2—C3B	179.8 (3)	C1—N1B—C5—C4	0.9 (5)
N1B—C1—C2—C6	−179.6 (6)	C3B—C4—C5—N1B	−0.2 (5)
C6i—C1—C2—C6	0.1 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ii	0.93	2.53	3.286 (7)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.93	2.53	3.286 (7)	139

Symmetry code: (i) .