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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2270.
Published online 2009 August 29. doi:  10.1107/S1600536809033212
PMCID: PMC2970123

8-(4-Nitro­benz­yloxy)quinoline

Abstract

In the title compound, C16H12N2O3, 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, inter­molecular C—H(...)O inter­actions link the mol­ecules 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 [triangle]); Li & Chen (2008 [triangle]); Zhao (2008 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-o2270-scheme1.jpg

Experimental

Crystal data

  • C16H12N2O3
  • M r = 280.28
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2270-efi1.jpg
  • 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 [triangle])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 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL/PC (Sheldrick, 2008 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL/PC and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

This work was supported by a start-up grant (No. 4007041028) and a Science Technology grant (No. KJ2009375) from Southeast University to Professor Yong-Hua Li.

supplementary crystallographic information

Comment

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

In the molecule of the title compound, (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The quinoline ring system is planar with a maximum deviation of 0.025 (3) Å for atom C6, and it is oriented with respect to the benzene ring at a dihedral angle of 61.76 (7)°.

In the crystal structure, intermolecular C-H···O interactions (Table 1) link the molecules into chains paralel to the b axis (Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contact between the quinoline rings, Cg1—Cg2i [symmetry code: (i) 1 + x, y, z, where Cg1 and Cg2 are centroids of the rings (N1/C1-C4/C9) and (C4-C9), respectively] may further stabilize the structure, with centroid-centroid distance of 3.623 (1) Å.

Experimental

For the preparation of the title compound, quinolin-8-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 3 h. Then, 1-(bromomethyl)-4-nitrobenzene (1.5318 g, 0.0069 mol) was added. The mixture was stirred at room temperature for 2 d. The title compound was isolated using column chromatography (petroleum ether: ethyl acetate, 1:1). Crystals suitable for X-ray analysis were obtained from slow evaporation of an ethyl acetate and tetrahydrofuran solution.

Refinement

H atoms were positioned geometrically with C-H = 0.93 and 0.97 Å for aromatic and methylene H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C). The absolute structure could not be determined reliably, and 1267 Friedel pairs were averaged before the last cycle of refinement.

Figures

Fig. 1.
The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

C16H12N2O3F(000) = 292
Mr = 280.28Dx = 1.405 Mg m3
Monoclinic, PnMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yacCell parameters from 1688 reflections
a = 4.176 (3) Åθ = 2.8–27.5°
b = 7.395 (3) ŵ = 0.10 mm1
c = 21.513 (18) ÅT = 294 K
β = 94.08 (3)°Block, pale yellow
V = 662.7 (8) Å30.20 × 0.20 × 0.20 mm
Z = 2

Data collection

Rigaku SCXmini diffractometer2566 independent reflections
Radiation source: fine-focus sealed tube2134 reflections with I > 2σ(I)
graphiteRint = 0.028
CCD_Profile_fitting scansθmax = 26.0°, θmin = 2.9°
Absorption correction: multi-scan (CrystalClear, Rigaku, 2005)h = −5→5
Tmin = 0.789, Tmax = 0.980k = −9→9
5732 measured reflectionsl = −26→26

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042w = 1/[σ2(Fo2) + (0.0196P)2 + 0.15P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.086(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.17 e Å3
2566 reflectionsΔρmin = −0.16 e Å3
191 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.036 (3)
Secondary atom site location: difference Fourier map

Special details

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)

xyzUiso*/Ueq
O10.8658 (4)0.5082 (2)0.23916 (8)0.0539 (4)
O20.1576 (6)−0.2236 (3)0.08570 (10)0.1024 (8)
O30.3470 (9)−0.1172 (4)0.00328 (11)0.1334 (11)
N11.2733 (5)0.4283 (2)0.33661 (9)0.0531 (5)
N20.2926 (6)−0.1057 (3)0.05809 (11)0.0727 (7)
C11.4711 (6)0.3933 (4)0.38541 (12)0.0609 (7)
H1A1.54510.27520.39030.073*
C21.5794 (6)0.5201 (4)0.43068 (12)0.0654 (7)
H2A1.71600.48580.46470.078*
C31.4798 (6)0.6939 (4)0.42365 (11)0.0612 (7)
H3A1.55180.78090.45260.073*
C41.2677 (5)0.7427 (3)0.37262 (11)0.0525 (6)
C51.1593 (7)0.9231 (4)0.36205 (14)0.0649 (7)
H5A1.22251.01400.39020.078*
C60.9646 (6)0.9620 (4)0.31112 (14)0.0665 (8)
H6A0.89821.08070.30400.080*
C70.8594 (6)0.8260 (3)0.26827 (12)0.0584 (7)
H7A0.72380.85550.23360.070*
C80.9567 (5)0.6509 (3)0.27772 (11)0.0482 (6)
C91.1702 (5)0.6040 (3)0.33024 (11)0.0464 (5)
C100.6534 (6)0.5515 (3)0.18613 (12)0.0561 (6)
H10A0.75770.63280.15850.067*
H10B0.46140.61000.19920.067*
C110.5679 (5)0.3764 (3)0.15321 (11)0.0497 (6)
C120.6351 (5)0.3513 (4)0.09144 (11)0.0582 (6)
H12A0.74040.44170.07080.070*
C130.5469 (6)0.1932 (3)0.06027 (12)0.0598 (6)
H13A0.59180.17690.01890.072*
C140.3921 (6)0.0609 (3)0.09139 (11)0.0518 (6)
C150.3210 (6)0.0814 (3)0.15294 (11)0.0548 (6)
H15A0.2155−0.00960.17330.066*
C160.4104 (5)0.2402 (3)0.18354 (10)0.0537 (6)
H16A0.36460.25600.22490.064*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0583 (10)0.0516 (9)0.0505 (9)0.0015 (8)−0.0043 (7)−0.0077 (7)
O20.149 (2)0.0699 (13)0.0880 (17)−0.0360 (14)0.0046 (15)−0.0007 (13)
O30.228 (3)0.1087 (19)0.0649 (14)−0.057 (2)0.0222 (17)−0.0289 (14)
N10.0568 (12)0.0473 (11)0.0548 (11)−0.0060 (9)0.0017 (10)−0.0030 (10)
N20.0905 (18)0.0683 (16)0.0572 (14)−0.0059 (13)−0.0099 (13)−0.0036 (12)
C10.0636 (17)0.0560 (15)0.0618 (16)−0.0086 (13)−0.0033 (13)0.0008 (13)
C20.0620 (17)0.080 (2)0.0534 (15)−0.0124 (15)−0.0033 (13)−0.0022 (14)
C30.0614 (16)0.0704 (19)0.0524 (15)−0.0220 (14)0.0078 (12)−0.0170 (13)
C40.0507 (13)0.0567 (15)0.0520 (13)−0.0156 (12)0.0157 (11)−0.0109 (12)
C50.0697 (18)0.0510 (15)0.0759 (18)−0.0157 (13)0.0195 (15)−0.0188 (14)
C60.0714 (19)0.0420 (15)0.088 (2)−0.0021 (12)0.0233 (16)−0.0033 (14)
C70.0585 (15)0.0511 (16)0.0665 (16)0.0000 (12)0.0101 (12)0.0025 (13)
C80.0479 (13)0.0472 (14)0.0510 (13)−0.0057 (11)0.0133 (10)−0.0037 (11)
C90.0484 (14)0.0470 (13)0.0449 (12)−0.0104 (10)0.0103 (10)−0.0073 (10)
C100.0511 (15)0.0613 (16)0.0549 (15)0.0019 (12)−0.0036 (12)0.0012 (12)
C110.0415 (12)0.0599 (16)0.0467 (13)0.0017 (11)−0.0030 (10)0.0009 (11)
C120.0556 (14)0.0696 (16)0.0495 (14)−0.0104 (12)0.0040 (11)0.0031 (13)
C130.0619 (15)0.0740 (18)0.0432 (13)−0.0028 (14)0.0021 (11)0.0003 (13)
C140.0559 (14)0.0521 (14)0.0464 (13)0.0021 (11)−0.0046 (11)0.0017 (11)
C150.0614 (16)0.0559 (15)0.0470 (13)0.0009 (12)0.0041 (11)0.0102 (11)
C160.0545 (14)0.0630 (16)0.0438 (12)0.0039 (11)0.0043 (10)0.0038 (11)

Geometric parameters (Å, °)

O1—C81.379 (3)C8—C71.367 (3)
O1—C101.431 (3)C9—N11.372 (3)
N1—C11.315 (3)C9—C41.413 (3)
N2—O21.216 (3)C9—C81.431 (3)
N2—O31.220 (3)C10—C111.507 (3)
N2—C141.470 (3)C10—H10A0.9700
C1—C21.403 (3)C10—H10B0.9700
C1—H1A0.9300C11—C161.391 (3)
C2—H2A0.9300C12—C111.390 (3)
C3—C21.356 (4)C12—C131.385 (3)
C3—H3A0.9300C12—H12A0.9300
C4—C31.408 (3)C13—C141.373 (3)
C4—C51.422 (3)C13—H13A0.9300
C5—C61.348 (4)C15—C141.386 (3)
C5—H5A0.9300C15—C161.385 (3)
C6—H6A0.9300C15—H15A0.9300
C7—C61.413 (4)C16—H16A0.9300
C7—H7A0.9300
C8—O1—C10115.90 (19)C7—C8—C9120.6 (2)
C1—N1—C9116.2 (2)N1—C9—C4123.3 (2)
O2—N2—C14119.2 (2)N1—C9—C8118.80 (18)
O3—N2—O2123.2 (3)C4—C9—C8117.9 (2)
O3—N2—C14117.7 (3)O1—C10—C11107.2 (2)
N1—C1—C2125.2 (3)O1—C10—H10A110.3
N1—C1—H1A117.4O1—C10—H10B110.3
C2—C1—H1A117.4C11—C10—H10A110.3
C1—C2—H2A120.8C11—C10—H10B110.3
C3—C2—C1118.3 (3)H10A—C10—H10B108.5
C3—C2—H2A120.8C12—C11—C10120.5 (2)
C2—C3—C4120.1 (2)C12—C11—C16119.1 (2)
C2—C3—H3A120.0C16—C11—C10120.4 (2)
C4—C3—H3A120.0C11—C12—H12A119.6
C3—C4—C9117.0 (2)C13—C12—C11120.7 (2)
C3—C4—C5122.7 (2)C13—C12—H12A119.6
C9—C4—C5120.3 (2)C12—C13—H13A120.5
C4—C5—H5A120.1C14—C13—C12118.9 (2)
C6—C5—C4119.8 (2)C14—C13—H13A120.5
C6—C5—H5A120.1C13—C14—N2119.1 (2)
C5—C6—C7121.3 (3)C13—C14—C15121.9 (2)
C5—C6—H6A119.3C15—C14—N2119.0 (2)
C7—C6—H6A119.3C14—C15—H15A120.7
C6—C7—H7A120.0C16—C15—C14118.6 (2)
C8—C7—C6120.1 (2)C16—C15—H15A120.7
C8—C7—H7A120.0C11—C16—H16A119.6
O1—C8—C9114.75 (19)C15—C16—C11120.8 (2)
C7—C8—O1124.7 (2)C15—C16—H16A119.6

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C10—H10A···O2i0.972.603.538 (3)164

Symmetry codes: (i) x+1, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2759).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bruker (2000). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fu, D.-W. & Zhao, H. (2007). Acta Cryst. E63, o3206.
  • Li, M. & Chen, X. (2008). Acta Cryst. E64, o2291. [PMC free article] [PubMed]
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Zhao, Y.-Y. (2008). Acta Cryst. E64, o761. [PMC free article] [PubMed]

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