6-(4-Nitro-benz-yloxy)quinoline.

In the mol-ecule of the title compound, C(16)H(12)N(2)O(3), the nitrobenzene benzene ring forms a dihedral angle of 23.8 (8)° with the plane of the quinoline ring system. The crystal structure is stabilized by an aromatic π-π stacking inter-action between centrosymmetrically related benzene rings [centroid-centroid distance 3.663 (2) Å].

Related literature

For related structures, see: Fu & Zhao (2007 ▶); Li & Chen (2008 ▶); Zhao (2008 ▶); Zhao et al. (2009 ▶).

Experimental

Crystal data

C16H12N2O3

M = 280.28

Monoclinic,

a = 12.296 (3) Å

b = 8.9146 (18) Å

c = 13.559 (3) Å

β = 115.25 (3)°

V = 1344.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.20 × 0.18 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.976, T max = 0.981

11965 measured reflections

2630 independent reflections

1372 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.152

S = 1.02

2630 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025823/rz2340sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025823/rz2340Isup2.hkl

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

C16H12N2O3	F(000) = 584
Mr = 280.28	Dx = 1.385 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8689 reflections
a = 12.296 (3) Å	θ = 3.0–27.8°
b = 8.9146 (18) Å	µ = 0.10 mm−1
c = 13.559 (3) Å	T = 293 K
β = 115.25 (3)°	Block, colourless
V = 1344.3 (6) Å3	0.20 × 0.18 × 0.15 mm
Z = 4

Rigaku SCXmini diffractometer	2630 independent reflections
Radiation source: fine-focus sealed tube	1372 reflections with I > 2σ(I)
graphite	Rint = 0.079
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.3°
CCD profile fitting scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.976, Tmax = 0.981	l = −16→16
11965 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0563P)2 + 0.1856P] where P = (Fo2 + 2Fc2)/3
2630 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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
C1	0.3786 (4)	0.3414 (4)	−0.1994 (3)	0.0901 (11)
H1A	0.3497	0.3839	−0.2686	0.108*
C2	0.4967 (4)	0.3728 (4)	−0.1275 (3)	0.0881 (11)
H2A	0.5444	0.4336	−0.1487	0.106*
C3	0.5411 (3)	0.3132 (4)	−0.0257 (3)	0.0735 (9)
H3A	0.6202	0.3321	0.0235	0.088*
C4	0.4671 (3)	0.2230 (3)	0.0046 (2)	0.0542 (7)
C5	0.5069 (2)	0.1580 (3)	0.1090 (2)	0.0557 (7)
H5A	0.5847	0.1750	0.1616	0.067*
C6	0.4303 (3)	0.0705 (3)	0.1319 (2)	0.0555 (8)
C7	0.3126 (3)	0.0454 (3)	0.0539 (2)	0.0657 (8)
H7A	0.2613	−0.0147	0.0711	0.079*
C8	0.2730 (3)	0.1074 (3)	−0.0460 (2)	0.0650 (8)
H8A	0.1943	0.0902	−0.0967	0.078*
C9	0.3483 (3)	0.1972 (3)	−0.0747 (2)	0.0572 (8)
C10	0.5763 (2)	0.0164 (3)	0.3124 (2)	0.0597 (8)
H10A	0.5943	0.1212	0.3318	0.072*
H10B	0.6332	−0.0211	0.2861	0.072*
C11	0.5866 (2)	−0.0718 (3)	0.4102 (2)	0.0502 (7)
C12	0.6722 (3)	−0.0323 (3)	0.5119 (2)	0.0620 (8)
H12A	0.7211	0.0504	0.5189	0.074*
C13	0.6870 (3)	−0.1124 (3)	0.6032 (2)	0.0605 (8)
H13A	0.7456	−0.0855	0.6715	0.073*
C14	0.6139 (2)	−0.2321 (3)	0.5916 (2)	0.0504 (7)
C15	0.5270 (3)	−0.2749 (3)	0.4919 (2)	0.0607 (8)
H15A	0.4777	−0.3568	0.4859	0.073*
C16	0.5142 (3)	−0.1945 (3)	0.4008 (2)	0.0627 (8)
H16A	0.4565	−0.2231	0.3325	0.075*
N1	0.3048 (2)	0.2567 (3)	−0.1773 (2)	0.0782 (8)
N2	0.6285 (3)	−0.3179 (3)	0.6883 (2)	0.0655 (7)
O1	0.45682 (16)	0.0016 (2)	0.22964 (15)	0.0699 (6)
O2	0.7111 (2)	−0.2867 (3)	0.77502 (18)	0.0885 (8)
O3	0.5578 (2)	−0.4184 (3)	0.67829 (19)	0.1026 (9)

	U11	U22	U33	U12	U13	U23
C1	0.105 (3)	0.111 (3)	0.062 (2)	0.029 (3)	0.043 (2)	0.032 (2)
C2	0.096 (3)	0.101 (3)	0.080 (3)	0.005 (2)	0.050 (2)	0.028 (2)
C3	0.074 (2)	0.083 (2)	0.070 (2)	0.0011 (18)	0.0365 (18)	0.0121 (19)
C4	0.0594 (18)	0.0558 (17)	0.0529 (17)	0.0062 (14)	0.0293 (15)	0.0049 (15)
C5	0.0499 (17)	0.0636 (19)	0.0504 (17)	0.0014 (14)	0.0182 (14)	0.0028 (15)
C6	0.0569 (18)	0.0606 (19)	0.0488 (17)	0.0038 (15)	0.0224 (15)	0.0096 (15)
C7	0.0593 (19)	0.075 (2)	0.061 (2)	−0.0085 (16)	0.0246 (17)	0.0075 (17)
C8	0.0535 (18)	0.078 (2)	0.0564 (19)	−0.0016 (16)	0.0167 (16)	−0.0063 (17)
C9	0.0624 (19)	0.064 (2)	0.0458 (17)	0.0152 (16)	0.0241 (15)	0.0030 (15)
C10	0.0556 (18)	0.0685 (19)	0.0551 (17)	−0.0006 (15)	0.0235 (15)	0.0073 (16)
C11	0.0513 (16)	0.0530 (17)	0.0498 (17)	0.0060 (14)	0.0249 (14)	0.0037 (14)
C12	0.065 (2)	0.0585 (19)	0.0581 (19)	−0.0059 (15)	0.0220 (16)	−0.0016 (16)
C13	0.0649 (19)	0.063 (2)	0.0443 (17)	0.0002 (16)	0.0144 (15)	−0.0018 (15)
C14	0.0552 (17)	0.0486 (17)	0.0475 (17)	0.0149 (14)	0.0219 (14)	0.0077 (14)
C15	0.0610 (18)	0.0558 (18)	0.0592 (19)	−0.0042 (14)	0.0196 (16)	0.0100 (16)
C16	0.0626 (19)	0.064 (2)	0.0515 (17)	−0.0022 (16)	0.0150 (15)	0.0042 (16)
N1	0.081 (2)	0.097 (2)	0.0538 (16)	0.0222 (16)	0.0264 (15)	0.0179 (15)
N2	0.0721 (18)	0.0630 (18)	0.0608 (18)	0.0157 (15)	0.0278 (15)	0.0106 (15)
O1	0.0584 (13)	0.0896 (15)	0.0573 (13)	−0.0055 (11)	0.0204 (11)	0.0238 (11)
O2	0.0970 (18)	0.0955 (18)	0.0544 (13)	0.0180 (14)	0.0145 (13)	0.0151 (13)
O3	0.114 (2)	0.106 (2)	0.0789 (17)	−0.0218 (17)	0.0334 (15)	0.0297 (15)

C1—N1	1.310 (4)	C10—O1	1.425 (3)
C1—C2	1.389 (4)	C10—C11	1.500 (3)
C1—H1A	0.9300	C10—H10A	0.9700
C2—C3	1.358 (4)	C10—H10B	0.9700
C2—H2A	0.9300	C11—C12	1.377 (4)
C3—C4	1.402 (4)	C11—C16	1.382 (4)
C3—H3A	0.9300	C12—C13	1.373 (4)
C4—C5	1.410 (4)	C12—H12A	0.9300
C4—C9	1.415 (4)	C13—C14	1.360 (4)
C5—C6	1.357 (4)	C13—H13A	0.9300
C5—H5A	0.9300	C14—C15	1.372 (4)
C6—O1	1.368 (3)	C14—N2	1.461 (3)
C6—C7	1.399 (4)	C15—C16	1.378 (4)
C7—C8	1.346 (4)	C15—H15A	0.9300
C7—H7A	0.9300	C16—H16A	0.9300
C8—C9	1.399 (4)	N2—O2	1.214 (3)
C8—H8A	0.9300	N2—O3	1.215 (3)
C9—N1	1.367 (3)
N1—C1—C2	125.1 (3)	O1—C10—H10A	110.0
N1—C1—H1A	117.5	C11—C10—H10A	110.0
C2—C1—H1A	117.5	O1—C10—H10B	110.0
C3—C2—C1	118.8 (3)	C11—C10—H10B	110.0
C3—C2—H2A	120.6	H10A—C10—H10B	108.4
C1—C2—H2A	120.6	C12—C11—C16	118.8 (3)
C2—C3—C4	119.5 (3)	C12—C11—C10	119.4 (3)
C2—C3—H3A	120.2	C16—C11—C10	121.7 (3)
C4—C3—H3A	120.2	C13—C12—C11	121.4 (3)
C3—C4—C5	122.6 (3)	C13—C12—H12A	119.3
C3—C4—C9	117.4 (3)	C11—C12—H12A	119.3
C5—C4—C9	120.0 (3)	C14—C13—C12	118.5 (3)
C6—C5—C4	119.2 (3)	C14—C13—H13A	120.8
C6—C5—H5A	120.4	C12—C13—H13A	120.8
C4—C5—H5A	120.4	C13—C14—C15	122.1 (3)
C5—C6—O1	125.3 (3)	C13—C14—N2	119.0 (3)
C5—C6—C7	120.9 (3)	C15—C14—N2	119.0 (3)
O1—C6—C7	113.8 (3)	C14—C15—C16	118.8 (3)
C8—C7—C6	120.6 (3)	C14—C15—H15A	120.6
C8—C7—H7A	119.7	C16—C15—H15A	120.6
C6—C7—H7A	119.7	C15—C16—C11	120.4 (3)
C7—C8—C9	121.1 (3)	C15—C16—H16A	119.8
C7—C8—H8A	119.5	C11—C16—H16A	119.8
C9—C8—H8A	119.5	C1—N1—C9	116.6 (3)
N1—C9—C8	119.2 (3)	O2—N2—O3	122.7 (3)
N1—C9—C4	122.6 (3)	O2—N2—C14	118.8 (3)
C8—C9—C4	118.2 (3)	O3—N2—C14	118.5 (3)
O1—C10—C11	108.5 (2)	C6—O1—C10	117.5 (2)