6-(4-Nitro­benz­yloxy)quinoline

Zhao, M.M.; Li, Y.H.; Zhang, Y.

doi:10.1107/S1600536809025823

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1795

doi:10.1107/S1600536809025823

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6-(4-Nitrobenzyloxy)quinoline

Min Min Zhao,^a Yong Hua Li ^a ^* and Yuan Zhang ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: liyhnju@hotmail.com

(Received 23 June 2009; accepted 3 July 2009; online 8 July 2009)

In the molecule of the title compound, C₁₆H₁₂N₂O₃, 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 interaction 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_r = 280.28
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.065
wR(F²) = 0.152
S = 1.02
2630 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −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.

Supporting information

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

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

checkCIF report

Comment top

Recently, we have reported the synthesis and crystal structure of some benzonitrile compounds (Fu & Zhao, 2007; Li & Chen, 2008; Zhao, 2008; Zhao et al., 2009). As an extension of our work on the structural characterization of benzonitrile derivatives, we present herein the synthesis and crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), bond lengths and angles are within normal ranges. The C11–C16 benzene ring forms a dihedral angle of 23.8 (8)° with the plane of the quinoline ring system. No intra- or intermolecular hydrogen bonds are observed. The crystal structure is stabilized by an aromatic π-π stacking interaction involving centrosymmetrically related benzene rings at (x, y, z) and (1-x, -y, 1-z), with a centroid-centroid distance of 3.663 (2) Å.

Related literature top

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

Experimental top

Quinolin-6-ol (1 g,0.0069 mol) was added to a solution of sodium hydroxide (0.276 g, 0.0069 mol) in methanol (15 ml) and stirred for one hour. Then 4-(bromomethyl)benzonitrile (1.49 g, 0.0069 mol) was added and the mixture stirred at room temperature for 1 day. The title compound was isolated by column chromatography using petroleum ether/ethyl acetate (1:1 v/v) as eluent. Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of an ethyl acetate/tetrahydrofuran (3:1 v/v) solution.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

6-(4-Nitrobenzyloxy)quinoline top

Crystal data top

C₁₆H₁₂N₂O₃	F(000) = 584
M_r = 280.28	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0563P)² + 0.1856P] where P = (F_o² + 2F_c²)/3
2630 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₆H₁₂N₂O₃	V = 1344.3 (6) Å³
M_r = 280.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.296 (3) Å	µ = 0.10 mm⁻¹
b = 8.9146 (18) Å	T = 293 K
c = 13.559 (3) Å	0.20 × 0.18 × 0.15 mm
β = 115.25 (3)°

Data collection top

Rigaku SCXmini diffractometer	2630 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1372 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.981	R_int = 0.079
11965 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.02	Δρ_max = 0.15 e Å⁻³
2630 reflections	Δρ_min = −0.15 e Å⁻³
190 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₂O₃
M_r	280.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	12.296 (3), 8.9146 (18), 13.559 (3)
β (°)	115.25 (3)
V (Å³)	1344.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.976, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	11965, 2630, 1372
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.152, 1.02
No. of reflections	2630
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.15

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008).

Acknowledgements

This work was supported by a start-up grant (4007041028) and a Science and Technology grant (KJ2009375) from Southeast University to Professor Yong-Hua Li.

References

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