7-Nitro-5H-1-benzothio-pyrano[2,3-b]pyridin-5-one.

In the mol-ecule of the title compound, C(12)H(6)N(2)O(3)S, the central heterocyclic ring is oriented at dihedral angles of 3.25 (6) and 2.28 (7)° with respect to the benzene and pyridine rings, respectively. The dihedral angle between the benzene and pyridine rings is 5.53 (7)°. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains.

Related literature

For general background, see: Acheson et al. (1976 ▶); Lesher et al. (1962 ▶); Archer et al. (1982 ▶, 1988 ▶); Showalter et al. (1988 ▶). For related structures, see: Atkinson et al. (2006 ▶). For related literature, see: Mann & Reid (1952 ▶); Hidetoshi (1997 ▶); Kurger & Mann (1955 ▶). For details of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C12H6N2O3S

M = 258.25

Orthorhombic,

a = 24.822 (2) Å

b = 3.8884 (2) Å

c = 10.8505 (7) Å

V = 1047.28 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 (2) K

0.25 × 0.12 × 0.08 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.927, T max = 0.976

6571 measured reflections

2491 independent reflections

2038 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.083

S = 1.02

2491 reflections

163 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1047 Friedel pairs

Flack parameter: 0.03 (8)

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/S1600536808007150/hk2433sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007150/hk2433Isup2.hkl

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

C12H6N2O3S	F000 = 528
Mr = 258.25	Dx = 1.638 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1444 reflections
a = 24.822 (2) Å	θ = 1.7–29.2º
b = 3.8884 (2) Å	µ = 0.31 mm−1
c = 10.8505 (7) Å	T = 296 (2) K
V = 1047.28 (12) Å3	Prismatic, light yellow
Z = 4	0.25 × 0.12 × 0.08 mm

Bruker KappaAPEXII CCD diffractometer	2491 independent reflections
Radiation source: fine-focus sealed tube	2038 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
Detector resolution: 7.5 pixels mm-1	θmax = 29.1º
T = 296(2) K	θmin = 2.5º
ω scans	h = −31→32
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −5→5
Tmin = 0.927, Tmax = 0.976	l = −14→13
6571 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036	w = 1/[σ2(Fo2) + (0.0408P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.083	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.21 e Å−3
2491 reflections	Δρmin = −0.21 e Å−3
163 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 1047 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (8)
Secondary atom site location: difference Fourier map

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	0.39024 (2)	0.42115 (12)	0.39781 (5)	0.03676 (14)
O1	0.12993 (7)	0.2278 (5)	0.3058 (2)	0.0694 (6)
O2	0.15811 (8)	−0.0812 (6)	0.1535 (2)	0.0660 (6)
O3	0.34609 (7)	−0.1679 (5)	0.06332 (15)	0.0491 (5)
N1	0.16584 (8)	0.1026 (5)	0.2436 (2)	0.0433 (5)
N2	0.48349 (8)	0.3607 (5)	0.3026 (2)	0.0452 (5)
C1	0.32646 (8)	0.3151 (5)	0.34578 (19)	0.0285 (4)
C2	0.28373 (9)	0.4190 (5)	0.4212 (2)	0.0353 (5)
H2	0.2910	0.5338	0.4946	0.042*
C3	0.23123 (8)	0.3542 (5)	0.3888 (2)	0.0354 (5)
H3	0.2029	0.4264	0.4384	0.042*
C4	0.22173 (9)	0.1777 (5)	0.2796 (2)	0.0336 (5)
C5	0.26260 (9)	0.0689 (5)	0.2047 (2)	0.0321 (5)
H5	0.2547	−0.0517	0.1329	0.039*
C6	0.31604 (8)	0.1380 (5)	0.23549 (19)	0.0282 (4)
C7	0.35825 (9)	0.0152 (5)	0.1503 (2)	0.0314 (5)
C8	0.41454 (9)	0.1140 (5)	0.17226 (19)	0.0313 (4)
C9	0.45386 (10)	0.0293 (6)	0.0858 (2)	0.0440 (6)
H9	0.4444	−0.0817	0.0130	0.053*
C10	0.50665 (11)	0.1111 (6)	0.1089 (3)	0.0522 (7)
H10	0.5334	0.0578	0.0519	0.063*
C11	0.51950 (10)	0.2730 (7)	0.2176 (3)	0.0528 (7)
H11	0.5555	0.3243	0.2326	0.063*
C12	0.43215 (9)	0.2827 (5)	0.27847 (19)	0.0333 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0323 (3)	0.0429 (3)	0.0350 (3)	−0.0032 (2)	−0.0032 (3)	−0.0060 (3)
O1	0.0317 (10)	0.0938 (13)	0.0825 (15)	0.0109 (11)	0.0082 (11)	−0.0090 (13)
O2	0.0366 (11)	0.0929 (15)	0.0685 (14)	−0.0117 (10)	−0.0072 (11)	−0.0173 (12)
O3	0.0395 (10)	0.0618 (11)	0.0458 (10)	−0.0038 (8)	0.0042 (8)	−0.0236 (9)
N1	0.0265 (11)	0.0552 (13)	0.0481 (12)	0.0024 (10)	0.0022 (9)	0.0093 (11)
N2	0.0309 (10)	0.0479 (11)	0.0569 (13)	−0.0041 (9)	−0.0028 (10)	0.0007 (10)
C1	0.0267 (10)	0.0267 (9)	0.0322 (10)	−0.0001 (8)	−0.0014 (9)	0.0027 (8)
C2	0.0412 (13)	0.0361 (10)	0.0285 (13)	0.0011 (9)	0.0020 (10)	−0.0011 (9)
C3	0.0311 (10)	0.0384 (10)	0.0366 (12)	0.0055 (8)	0.0114 (10)	0.0004 (12)
C4	0.0261 (11)	0.0352 (10)	0.0395 (12)	0.0001 (9)	−0.0012 (9)	0.0088 (10)
C5	0.0308 (12)	0.0350 (10)	0.0305 (10)	−0.0006 (9)	−0.0009 (9)	0.0020 (9)
C6	0.0282 (12)	0.0273 (9)	0.0290 (10)	−0.0011 (8)	−0.0007 (9)	0.0035 (8)
C7	0.0307 (12)	0.0349 (10)	0.0285 (11)	−0.0004 (9)	0.0023 (10)	0.0008 (9)
C8	0.0295 (11)	0.0308 (10)	0.0337 (11)	0.0023 (9)	0.0017 (10)	0.0027 (9)
C9	0.0391 (14)	0.0458 (12)	0.0471 (14)	0.0004 (11)	0.0097 (11)	0.0000 (11)
C10	0.0334 (15)	0.0552 (15)	0.0681 (18)	−0.0003 (11)	0.0193 (13)	−0.0021 (14)
C11	0.0279 (13)	0.0528 (14)	0.078 (2)	−0.0015 (11)	0.0018 (14)	0.0024 (15)
C12	0.0284 (12)	0.0301 (10)	0.0414 (12)	−0.0003 (9)	−0.0018 (10)	0.0033 (9)

S1—C1	1.731 (2)	C5—C6	1.394 (3)
S1—C12	1.746 (2)	C5—H5	0.9300
N1—O1	1.219 (3)	C7—O3	1.220 (3)
N1—O2	1.226 (3)	C7—C8	1.469 (3)
N1—C4	1.471 (3)	C7—C6	1.476 (3)
N2—C11	1.329 (3)	C8—C9	1.393 (3)
C1—C2	1.400 (3)	C9—C10	1.372 (4)
C1—C6	1.405 (3)	C9—H9	0.9300
C2—C3	1.373 (3)	C10—C11	1.374 (4)
C2—H2	0.9300	C10—H10	0.9300
C3—H3	0.9300	C11—H11	0.9300
C4—C3	1.389 (3)	C12—N2	1.336 (3)
C5—C4	1.367 (3)	C12—C8	1.396 (3)
C1—S1—C12	103.27 (10)	C5—C6—C7	117.57 (19)
O1—N1—O2	124.0 (2)	C1—C6—C7	124.14 (18)
O1—N1—C4	117.6 (2)	O3—C7—C8	120.90 (19)
O2—N1—C4	118.4 (2)	O3—C7—C6	119.84 (19)
C11—N2—C12	116.6 (2)	C8—C7—C6	119.27 (18)
C2—C1—C6	120.01 (19)	C9—C8—C12	116.6 (2)
C2—C1—S1	115.70 (16)	C9—C8—C7	119.7 (2)
C6—C1—S1	124.28 (16)	C12—C8—C7	123.69 (19)
C3—C2—C1	121.1 (2)	C10—C9—C8	119.4 (2)
C3—C2—H2	119.5	C10—C9—H9	120.3
C1—C2—H2	119.5	C8—C9—H9	120.3
C2—C3—C4	118.1 (2)	C9—C10—C11	119.0 (2)
C2—C3—H3	121.0	C9—C10—H10	120.5
C4—C3—H3	121.0	C11—C10—H10	120.5
C5—C4—C3	122.3 (2)	N2—C11—C10	123.8 (2)
C5—C4—N1	118.7 (2)	N2—C11—H11	118.1
C3—C4—N1	119.0 (2)	C10—C11—H11	118.1
C4—C5—C6	120.3 (2)	N2—C12—C8	124.5 (2)
C4—C5—H5	119.9	N2—C12—S1	110.68 (17)
C6—C5—H5	119.9	C8—C12—S1	124.79 (17)
C5—C6—C1	118.29 (19)
C12—S1—C1—C2	−175.98 (15)	C4—C5—C6—C1	1.2 (3)
C12—S1—C1—C6	3.75 (19)	C4—C5—C6—C7	−179.64 (18)
C1—S1—C12—N2	177.32 (15)	O3—C7—C6—C5	−6.9 (3)
C1—S1—C12—C8	−2.6 (2)	C8—C7—C6—C5	173.52 (18)
O1—N1—C4—C5	−173.6 (2)	O3—C7—C6—C1	172.23 (19)
O2—N1—C4—C5	6.4 (3)	C8—C7—C6—C1	−7.3 (3)
O1—N1—C4—C3	6.8 (3)	O3—C7—C8—C9	7.0 (3)
O2—N1—C4—C3	−173.2 (2)	C6—C7—C8—C9	−173.5 (2)
C12—N2—C11—C10	0.2 (4)	O3—C7—C8—C12	−171.0 (2)
C6—C1—C2—C3	−0.7 (3)	C6—C7—C8—C12	8.6 (3)
S1—C1—C2—C3	179.00 (16)	C7—C8—C9—C10	−177.6 (2)
S1—C1—C6—C5	179.95 (15)	C12—C8—C9—C10	0.5 (3)
C2—C1—C6—C5	−0.3 (3)	C8—C9—C10—C11	0.4 (4)
S1—C1—C6—C7	0.8 (3)	C9—C10—C11—N2	−0.8 (4)
C2—C1—C6—C7	−179.47 (18)	S1—C12—N2—C11	−179.05 (18)
C1—C2—C3—C4	1.0 (3)	C8—C12—N2—C11	0.8 (3)
C5—C4—C3—C2	−0.1 (3)	N2—C12—C8—C9	−1.2 (3)
N1—C4—C3—C2	179.43 (19)	S1—C12—C8—C9	178.70 (16)
C6—C5—C4—C3	−1.0 (3)	N2—C12—C8—C7	176.82 (19)
C6—C5—C4—N1	179.49 (18)	S1—C12—C8—C7	−3.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.93	2.41	3.275 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.93	2.41	3.275 (3)	155

Symmetry code: (i) .