8-Nitro-quinoline.

The molecule of the title compound, C(9)H(6)N(2)O(2), is almost planar, with a dihedral angle of 3.0 (9)° between the pyridine and benzene rings.

Related literature

For the first synthesis of 8-nitro­quinoline, see: Königs (1879 ▶). The crystal studied was synthesised according to the method of Yale & Bernstein (1948 ▶). For the pharmacological activity of quinoline derivatives, see: Franck et al. (2004 ▶); Zouhiri et al. (2005 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H6N2O2

M = 174.16

Monoclinic,

a = 7.2421 (11) Å

b = 16.688 (3) Å

c = 7.2089 (11) Å

β = 114.086 (4)°

V = 795.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.40 × 0.32 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

10084 measured reflections

2287 independent reflections

1827 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.147

S = 1.03

2287 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010014/hg5010sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010014/hg5010Isup2.hkl

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

C9H6N2O2	F(000) = 360
Mr = 174.16	Dx = 1.454 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3873 reflections
a = 7.2421 (11) Å	θ = 3.1–30.0°
b = 16.688 (3) Å	µ = 0.11 mm−1
c = 7.2089 (11) Å	T = 296 K
β = 114.086 (4)°	Block, yellow
V = 795.4 (2) Å3	0.40 × 0.32 × 0.25 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1827 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
graphite	θmax = 30.0°, θmin = 3.1°
φ and ω scans	h = −9→10
10084 measured reflections	k = −23→21
2287 independent reflections	l = −10→10

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0809P)2 + 0.1053P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2287 reflections	Δρmax = 0.27 e Å−3
119 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.133 (14)

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
C6	0.25070 (14)	0.69710 (6)	0.26068 (13)	0.0354 (2)
C1	0.25541 (15)	0.61239 (7)	0.26308 (15)	0.0380 (2)
N1	0.41946 (14)	0.73928 (6)	0.28382 (15)	0.0454 (3)
C5	0.06270 (16)	0.73360 (7)	0.22521 (16)	0.0422 (3)
N2	0.44722 (15)	0.57111 (6)	0.30592 (16)	0.0467 (3)
C4	−0.10800 (18)	0.68516 (9)	0.1935 (2)	0.0554 (3)
H4	−0.2304	0.7092	0.1738	0.066*
C2	0.08895 (19)	0.56627 (8)	0.2262 (2)	0.0502 (3)
H2	0.0973	0.5107	0.2241	0.060*
C9	0.0561 (2)	0.81833 (8)	0.21989 (19)	0.0560 (3)
H9	−0.0634	0.8452	0.1985	0.067*
C7	0.4030 (2)	0.81781 (8)	0.27567 (19)	0.0547 (3)
H7	0.5169	0.8474	0.2905	0.066*
C3	−0.09546 (19)	0.60401 (9)	0.1914 (2)	0.0595 (4)
H3	−0.2101	0.5732	0.1668	0.071*
O1	0.59089 (14)	0.58621 (7)	0.46328 (17)	0.0659 (3)
C8	0.2259 (2)	0.86002 (8)	0.2462 (2)	0.0600 (4)
H8	0.2248	0.9157	0.2448	0.072*
O2	0.45132 (17)	0.52226 (7)	0.18178 (19)	0.0742 (4)

	U11	U22	U33	U12	U13	U23
C6	0.0357 (5)	0.0374 (5)	0.0308 (4)	−0.0003 (3)	0.0114 (4)	0.0008 (3)
C1	0.0358 (5)	0.0380 (5)	0.0407 (5)	0.0011 (3)	0.0162 (4)	0.0008 (4)
N1	0.0429 (5)	0.0451 (5)	0.0466 (5)	−0.0068 (4)	0.0167 (4)	0.0050 (4)
C5	0.0399 (5)	0.0452 (6)	0.0362 (5)	0.0056 (4)	0.0101 (4)	−0.0023 (4)
N2	0.0459 (5)	0.0398 (5)	0.0594 (6)	0.0052 (4)	0.0266 (4)	0.0074 (4)
C4	0.0334 (5)	0.0679 (8)	0.0594 (7)	0.0041 (5)	0.0132 (5)	−0.0067 (6)
C2	0.0494 (6)	0.0408 (6)	0.0602 (7)	−0.0091 (4)	0.0222 (5)	−0.0052 (5)
C9	0.0630 (8)	0.0481 (7)	0.0494 (6)	0.0180 (5)	0.0154 (5)	−0.0001 (5)
C7	0.0633 (8)	0.0454 (7)	0.0502 (6)	−0.0134 (5)	0.0180 (6)	0.0035 (5)
C3	0.0374 (6)	0.0663 (8)	0.0721 (8)	−0.0153 (5)	0.0196 (6)	−0.0101 (6)
O1	0.0438 (5)	0.0715 (7)	0.0714 (7)	0.0104 (4)	0.0123 (5)	0.0066 (5)
C8	0.0829 (10)	0.0361 (6)	0.0523 (7)	0.0008 (6)	0.0187 (7)	0.0013 (4)
O2	0.0783 (7)	0.0651 (7)	0.0898 (8)	0.0166 (5)	0.0451 (6)	−0.0117 (5)

C6—N1	1.3604 (14)	C4—C3	1.358 (2)
C6—C1	1.4140 (15)	C4—H4	0.9300
C6—C5	1.4163 (14)	C2—C3	1.4035 (19)
C1—C2	1.3619 (16)	C2—H2	0.9300
C1—N2	1.4661 (14)	C9—C8	1.357 (2)
N1—C7	1.3151 (17)	C9—H9	0.9300
C5—C9	1.4148 (18)	C7—C8	1.401 (2)
C5—C4	1.4154 (18)	C7—H7	0.9300
N2—O1	1.2122 (14)	C3—H3	0.9300
N2—O2	1.2198 (15)	C8—H8	0.9300
N1—C6—C1	119.99 (9)	C1—C2—C3	118.90 (12)
N1—C6—C5	123.30 (10)	C1—C2—H2	120.6
C1—C6—C5	116.66 (9)	C3—C2—H2	120.5
C2—C1—C6	123.20 (10)	C8—C9—C5	119.35 (12)
C2—C1—N2	117.57 (10)	C8—C9—H9	120.3
C6—C1—N2	119.23 (9)	C5—C9—H9	120.3
C7—N1—C6	116.71 (10)	N1—C7—C8	124.64 (12)
C9—C5—C4	123.30 (11)	N1—C7—H7	117.7
C9—C5—C6	116.99 (11)	C8—C7—H7	117.7
C4—C5—C6	119.70 (11)	C4—C3—C2	120.57 (11)
O1—N2—O2	123.84 (11)	C4—C3—H3	119.7
O1—N2—C1	118.49 (10)	C2—C3—H3	119.7
O2—N2—C1	117.65 (11)	C9—C8—C7	118.98 (12)
C3—C4—C5	120.90 (11)	C9—C8—H8	120.5
C3—C4—H4	119.6	C7—C8—H8	120.5
C5—C4—H4	119.6
N1—C6—C1—C2	−175.08 (10)	C6—C1—N2—O2	−124.71 (12)
C5—C6—C1—C2	2.42 (15)	C9—C5—C4—C3	177.10 (13)
N1—C6—C1—N2	4.57 (14)	C6—C5—C4—C3	−1.69 (19)
C5—C6—C1—N2	−177.94 (9)	C6—C1—C2—C3	−2.46 (18)
C1—C6—N1—C7	178.58 (9)	N2—C1—C2—C3	177.89 (11)
C5—C6—N1—C7	1.26 (15)	C4—C5—C9—C8	−178.13 (12)
N1—C6—C5—C9	−1.77 (15)	C6—C5—C9—C8	0.68 (17)
C1—C6—C5—C9	−179.18 (9)	C6—N1—C7—C8	0.35 (18)
N1—C6—C5—C4	177.09 (10)	C5—C4—C3—C2	1.7 (2)
C1—C6—C5—C4	−0.32 (15)	C1—C2—C3—C4	0.3 (2)
C2—C1—N2—O1	−123.73 (13)	C5—C9—C8—C7	0.76 (19)
C6—C1—N2—O1	56.60 (14)	N1—C7—C8—C9	−1.4 (2)
C2—C1—N2—O2	54.95 (15)