8-(4-Nitro-benz-yloxy)quinoline.

In the title compound, C(16)H(12)N(2)O(3), the planar quinoline ring system [maximum deviation = 0.025 (3) Å] is oriented at a dihedral angle of 61.76 (7)° with respect to the benzene ring. In the crystal structure, inter-molecular C-H⋯O inter-actions link the mol-ecules into chains parallel to the b axis. π-π contacts between the quinoline rings [centroid-centroid distance = 3.623 (1) Å] may further stabilize the structure.

Related literature

For related structures, see: Fu & Zhao (2007 ▶); Li & Chen (2008 ▶); Zhao (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H12N2O3

M = 280.28

Monoclinic,

a = 4.176 (3) Å

b = 7.395 (3) Å

c = 21.513 (18) Å

β = 94.08 (3)°

V = 662.7 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 294 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear, Rigaku, 2005 ▶)T min = 0.789, T max = 0.980

5732 measured reflections

2566 independent reflections

2134 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.086

S = 1.01

2566 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.16 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL/PC and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033212/hk2759sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033212/hk2759Isup2.hkl

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

C16H12N2O3	F(000) = 292
Mr = 280.28	Dx = 1.405 Mg m−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 1688 reflections
a = 4.176 (3) Å	θ = 2.8–27.5°
b = 7.395 (3) Å	µ = 0.10 mm−1
c = 21.513 (18) Å	T = 294 K
β = 94.08 (3)°	Block, pale yellow
V = 662.7 (8) Å3	0.20 × 0.20 × 0.20 mm
Z = 2

Rigaku SCXmini diffractometer	2566 independent reflections
Radiation source: fine-focus sealed tube	2134 reflections with I > 2σ(I)
graphite	Rint = 0.028
CCD_Profile_fitting scans	θmax = 26.0°, θmin = 2.9°
Absorption correction: multi-scan (CrystalClear, Rigaku, 2005)	h = −5→5
Tmin = 0.789, Tmax = 0.980	k = −9→9
5732 measured reflections	l = −26→26

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.0196P)2 + 0.15P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.086	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.17 e Å−3
2566 reflections	Δρmin = −0.16 e Å−3
191 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.036 (3)
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
O1	0.8658 (4)	0.5082 (2)	0.23916 (8)	0.0539 (4)
O2	0.1576 (6)	−0.2236 (3)	0.08570 (10)	0.1024 (8)
O3	0.3470 (9)	−0.1172 (4)	0.00328 (11)	0.1334 (11)
N1	1.2733 (5)	0.4283 (2)	0.33661 (9)	0.0531 (5)
N2	0.2926 (6)	−0.1057 (3)	0.05809 (11)	0.0727 (7)
C1	1.4711 (6)	0.3933 (4)	0.38541 (12)	0.0609 (7)
H1A	1.5451	0.2752	0.3903	0.073*
C2	1.5794 (6)	0.5201 (4)	0.43068 (12)	0.0654 (7)
H2A	1.7160	0.4858	0.4647	0.078*
C3	1.4798 (6)	0.6939 (4)	0.42365 (11)	0.0612 (7)
H3A	1.5518	0.7809	0.4526	0.073*
C4	1.2677 (5)	0.7427 (3)	0.37262 (11)	0.0525 (6)
C5	1.1593 (7)	0.9231 (4)	0.36205 (14)	0.0649 (7)
H5A	1.2225	1.0140	0.3902	0.078*
C6	0.9646 (6)	0.9620 (4)	0.31112 (14)	0.0665 (8)
H6A	0.8982	1.0807	0.3040	0.080*
C7	0.8594 (6)	0.8260 (3)	0.26827 (12)	0.0584 (7)
H7A	0.7238	0.8555	0.2336	0.070*
C8	0.9567 (5)	0.6509 (3)	0.27772 (11)	0.0482 (6)
C9	1.1702 (5)	0.6040 (3)	0.33024 (11)	0.0464 (5)
C10	0.6534 (6)	0.5515 (3)	0.18613 (12)	0.0561 (6)
H10A	0.7577	0.6328	0.1585	0.067*
H10B	0.4614	0.6100	0.1992	0.067*
C11	0.5679 (5)	0.3764 (3)	0.15321 (11)	0.0497 (6)
C12	0.6351 (5)	0.3513 (4)	0.09144 (11)	0.0582 (6)
H12A	0.7404	0.4417	0.0708	0.070*
C13	0.5469 (6)	0.1932 (3)	0.06027 (12)	0.0598 (6)
H13A	0.5918	0.1769	0.0189	0.072*
C14	0.3921 (6)	0.0609 (3)	0.09139 (11)	0.0518 (6)
C15	0.3210 (6)	0.0814 (3)	0.15294 (11)	0.0548 (6)
H15A	0.2155	−0.0096	0.1733	0.066*
C16	0.4104 (5)	0.2402 (3)	0.18354 (10)	0.0537 (6)
H16A	0.3646	0.2560	0.2249	0.064*

	U11	U22	U33	U12	U13	U23
O1	0.0583 (10)	0.0516 (9)	0.0505 (9)	0.0015 (8)	−0.0043 (7)	−0.0077 (7)
O2	0.149 (2)	0.0699 (13)	0.0880 (17)	−0.0360 (14)	0.0046 (15)	−0.0007 (13)
O3	0.228 (3)	0.1087 (19)	0.0649 (14)	−0.057 (2)	0.0222 (17)	−0.0289 (14)
N1	0.0568 (12)	0.0473 (11)	0.0548 (11)	−0.0060 (9)	0.0017 (10)	−0.0030 (10)
N2	0.0905 (18)	0.0683 (16)	0.0572 (14)	−0.0059 (13)	−0.0099 (13)	−0.0036 (12)
C1	0.0636 (17)	0.0560 (15)	0.0618 (16)	−0.0086 (13)	−0.0033 (13)	0.0008 (13)
C2	0.0620 (17)	0.080 (2)	0.0534 (15)	−0.0124 (15)	−0.0033 (13)	−0.0022 (14)
C3	0.0614 (16)	0.0704 (19)	0.0524 (15)	−0.0220 (14)	0.0078 (12)	−0.0170 (13)
C4	0.0507 (13)	0.0567 (15)	0.0520 (13)	−0.0156 (12)	0.0157 (11)	−0.0109 (12)
C5	0.0697 (18)	0.0510 (15)	0.0759 (18)	−0.0157 (13)	0.0195 (15)	−0.0188 (14)
C6	0.0714 (19)	0.0420 (15)	0.088 (2)	−0.0021 (12)	0.0233 (16)	−0.0033 (14)
C7	0.0585 (15)	0.0511 (16)	0.0665 (16)	0.0000 (12)	0.0101 (12)	0.0025 (13)
C8	0.0479 (13)	0.0472 (14)	0.0510 (13)	−0.0057 (11)	0.0133 (10)	−0.0037 (11)
C9	0.0484 (14)	0.0470 (13)	0.0449 (12)	−0.0104 (10)	0.0103 (10)	−0.0073 (10)
C10	0.0511 (15)	0.0613 (16)	0.0549 (15)	0.0019 (12)	−0.0036 (12)	0.0012 (12)
C11	0.0415 (12)	0.0599 (16)	0.0467 (13)	0.0017 (11)	−0.0030 (10)	0.0009 (11)
C12	0.0556 (14)	0.0696 (16)	0.0495 (14)	−0.0104 (12)	0.0040 (11)	0.0031 (13)
C13	0.0619 (15)	0.0740 (18)	0.0432 (13)	−0.0028 (14)	0.0021 (11)	0.0003 (13)
C14	0.0559 (14)	0.0521 (14)	0.0464 (13)	0.0021 (11)	−0.0046 (11)	0.0017 (11)
C15	0.0614 (16)	0.0559 (15)	0.0470 (13)	0.0009 (12)	0.0041 (11)	0.0102 (11)
C16	0.0545 (14)	0.0630 (16)	0.0438 (12)	0.0039 (11)	0.0043 (10)	0.0038 (11)

O1—C8	1.379 (3)	C8—C7	1.367 (3)
O1—C10	1.431 (3)	C9—N1	1.372 (3)
N1—C1	1.315 (3)	C9—C4	1.413 (3)
N2—O2	1.216 (3)	C9—C8	1.431 (3)
N2—O3	1.220 (3)	C10—C11	1.507 (3)
N2—C14	1.470 (3)	C10—H10A	0.9700
C1—C2	1.403 (3)	C10—H10B	0.9700
C1—H1A	0.9300	C11—C16	1.391 (3)
C2—H2A	0.9300	C12—C11	1.390 (3)
C3—C2	1.356 (4)	C12—C13	1.385 (3)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C3	1.408 (3)	C13—C14	1.373 (3)
C4—C5	1.422 (3)	C13—H13A	0.9300
C5—C6	1.348 (4)	C15—C14	1.386 (3)
C5—H5A	0.9300	C15—C16	1.385 (3)
C6—H6A	0.9300	C15—H15A	0.9300
C7—C6	1.413 (4)	C16—H16A	0.9300
C7—H7A	0.9300
C8—O1—C10	115.90 (19)	C7—C8—C9	120.6 (2)
C1—N1—C9	116.2 (2)	N1—C9—C4	123.3 (2)
O2—N2—C14	119.2 (2)	N1—C9—C8	118.80 (18)
O3—N2—O2	123.2 (3)	C4—C9—C8	117.9 (2)
O3—N2—C14	117.7 (3)	O1—C10—C11	107.2 (2)
N1—C1—C2	125.2 (3)	O1—C10—H10A	110.3
N1—C1—H1A	117.4	O1—C10—H10B	110.3
C2—C1—H1A	117.4	C11—C10—H10A	110.3
C1—C2—H2A	120.8	C11—C10—H10B	110.3
C3—C2—C1	118.3 (3)	H10A—C10—H10B	108.5
C3—C2—H2A	120.8	C12—C11—C10	120.5 (2)
C2—C3—C4	120.1 (2)	C12—C11—C16	119.1 (2)
C2—C3—H3A	120.0	C16—C11—C10	120.4 (2)
C4—C3—H3A	120.0	C11—C12—H12A	119.6
C3—C4—C9	117.0 (2)	C13—C12—C11	120.7 (2)
C3—C4—C5	122.7 (2)	C13—C12—H12A	119.6
C9—C4—C5	120.3 (2)	C12—C13—H13A	120.5
C4—C5—H5A	120.1	C14—C13—C12	118.9 (2)
C6—C5—C4	119.8 (2)	C14—C13—H13A	120.5
C6—C5—H5A	120.1	C13—C14—N2	119.1 (2)
C5—C6—C7	121.3 (3)	C13—C14—C15	121.9 (2)
C5—C6—H6A	119.3	C15—C14—N2	119.0 (2)
C7—C6—H6A	119.3	C14—C15—H15A	120.7
C6—C7—H7A	120.0	C16—C15—C14	118.6 (2)
C8—C7—C6	120.1 (2)	C16—C15—H15A	120.7
C8—C7—H7A	120.0	C11—C16—H16A	119.6
O1—C8—C9	114.75 (19)	C15—C16—C11	120.8 (2)
C7—C8—O1	124.7 (2)	C15—C16—H16A	119.6

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O2i	0.97	2.60	3.538 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O2i	0.97	2.60	3.538 (3)	164

Symmetry code: (i) .