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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o710.
Published online 2009 March 6. doi:  10.1107/S1600536809007417
PMCID: PMC2968949

4-(4-Nitro­phenoxy)biphen­yl

Abstract

The two phenyl rings of the biphenyl unit of the title compound, C18H13NO3, are almost coplanar [dihedral angle 6.70 (9)°]. The nitro­phenyl ring, on the other hand, is significantly twisted out of the plane of the these two rings, making dihedral angles of 68.83 (4)° with the middle ring and 62.86 (4)° with the end ring. The nitro group is twisted by 12.1 (2)° out of the plane of the phenyl ring to which it is attached.

Related literature

The title compound is a precursor of amine which is a useful curing agent of ep­oxy resins. For the properties and applications of ep­oxy resins, see: Boey & Yap (2001 [triangle]); Bonnaud et al. (2004 [triangle]); de Moris et al. (2007 [triangle]); Van de Grampel et al. (2005 [triangle]); Agag & Takeichi (1999 [triangle]); Kagathera & Parsania (2001 [triangle]); Kagathera & Parsania (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o710-scheme1.jpg

Experimental

Crystal data

  • C18H13NO3
  • M r = 291.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o710-efi1.jpg
  • a = 9.6435 (7) Å
  • b = 5.8648 (3) Å
  • c = 24.6884 (18) Å
  • β = 95.704 (6)°
  • V = 1389.39 (16) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 173 K
  • 0.44 × 0.37 × 0.13 mm

Data collection

  • STOE IPDS II two-circle-diffractometer
  • Absorption correction: none
  • 16020 measured reflections
  • 2556 independent reflections
  • 2187 reflections with I > 2σ(I)
  • R int = 0.052

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.118
  • S = 1.07
  • 2556 reflections
  • 200 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 [triangle]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, Za12. DOI: 10.1107/S1600536809007417/ww2140sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007417/ww2140Isup2.hkl

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

Acknowledgments

The authors are grateful to the Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan, and the Institute for Inorganic Chemistry, University of Frankfurt, Germany, for providing laboratory and analytical facilities.

supplementary crystallographic information

Comment

Epoxy resins are a versatile group of crosslinked polymers that has excellent chemical resistance, good electrical insulating properties, good adhesion to glass and metal and can be easily fabricated (Boey & Yap, 2001). Variety of properties helps epoxy resins to meet performance requirements of some demanding applications (Bonnaud et al., 2004). These include areas as diverse as construction, electronics, adhesives and coatings (de Moris et al., 2007). The usefulness of epoxy resins is often limited due to their inherent brittleness arising from crosslinking structure (van de Grampel et al., 2005). Development of approaches for toughening epoxy resins without sacrificing modulus and glass transition temperature (Tg) would lead to an increase in their applications (Kagathera & Parsania, 2001). One such approach is the curing of epoxy resins with different curing agents (Agag & Takeichi, 1999). The title compound is a precursor of amine which is a useful curing agent of epoxy resins.

The two phenyl rings of the biphenyl moiety of the title compound are almost coplanar [dihedral angle 6.70 (9)°]. The nitrophenyl ring, on the other hand, is significantly twisted out of the plane of the these two rings [68.83 (4)° and 62.86 (4)°]. The nitro group is twisted by 12.1 (2)° out of the plane of the phenyl ring to which it is attached.

Experimental

A 500 ml two neck round bottom flask was equipped with condenser and thermometer and was charged with (0.059 moles) biphenyl-4-ol, (0.059 moles) anhydrous potassium carbonate and (0.059 moles) 4-chloronitrobenzene in 180 ml of DMF. Reaction mixture was heated for 24 h at 120°C. The reaction was carried out in the inert atmosphere of nitrogen. Progress of reaction was measured by TLC [1:1, ethyl acetae, n-hexane]. After completion, the reaction mixture was poured into 600 ml of water to give yellow precipitates. These precipitates were collected by filtration and washed with water several times. Recrystallization of the residue in n-hexane afforded the title compound (86%) (m.p 142–144°C)

Refinement

H atoms were located in a difference map, but geometrically positioned and refined using a riding model with fixed individual displacement parameters [Uiso(H) = 1.2 Ueq(C)] and with C—H = 0.95Å.

Figures

Fig. 1.
Perspective view of the title compound with the atom numbering scheme; displacement ellipsoids are at the 50% probability level.
Fig. 2.
Packing of the title compound with view onto the ac plane, hydrogen atoms are omitted for clarity.

Crystal data

C18H13NO3F(000) = 608
Mr = 291.29Dx = 1.393 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 16639 reflections
a = 9.6435 (7) Åθ = 2.2–25.8°
b = 5.8648 (3) ŵ = 0.10 mm1
c = 24.6884 (18) ÅT = 173 K
β = 95.704 (6)°Plate, colourless
V = 1389.39 (16) Å30.44 × 0.37 × 0.13 mm
Z = 4

Data collection

STOE IPDS II two-circle-diffractometer2187 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.052
graphiteθmax = 25.5°, θmin = 2.1°
ω scansh = −11→11
16020 measured reflectionsk = −7→6
2556 independent reflectionsl = −29→29

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.118w = 1/[σ2(Fo2) + (0.0735P)2 + 0.2032P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2556 reflectionsΔρmax = 0.24 e Å3
200 parametersΔρmin = −0.20 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.028 (4)

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
N10.24460 (14)1.3101 (2)0.49386 (5)0.0439 (3)
O10.11760 (13)1.3217 (2)0.48231 (5)0.0630 (4)
O20.32703 (14)1.4402 (2)0.47506 (5)0.0648 (4)
O30.44070 (9)0.60894 (15)0.63327 (4)0.0357 (3)
C10.29854 (14)1.1306 (2)0.53120 (5)0.0342 (3)
C20.43662 (14)1.1370 (2)0.55251 (5)0.0369 (3)
H20.49601.25690.54310.044*
C30.48706 (13)0.9659 (2)0.58781 (5)0.0335 (3)
H30.58160.96750.60300.040*
C40.39846 (12)0.7919 (2)0.60091 (5)0.0289 (3)
C50.26016 (13)0.7870 (3)0.57875 (5)0.0360 (3)
H50.20080.66610.58760.043*
C60.20939 (13)0.9577 (3)0.54400 (5)0.0379 (3)
H60.11480.95700.52900.045*
C110.55429 (12)0.6296 (2)0.67283 (5)0.0293 (3)
C120.65196 (14)0.4576 (2)0.67578 (6)0.0378 (3)
H120.64660.34080.64900.045*
C130.75837 (14)0.4557 (2)0.71807 (5)0.0369 (3)
H130.82490.33580.72000.044*
C140.76992 (12)0.6256 (2)0.75787 (5)0.0261 (3)
C150.66981 (13)0.7987 (2)0.75286 (5)0.0338 (3)
H150.67550.91820.77900.041*
C160.56253 (14)0.8018 (2)0.71109 (5)0.0358 (3)
H160.49550.92110.70880.043*
C210.88361 (12)0.6232 (2)0.80367 (5)0.0268 (3)
C220.97567 (14)0.4414 (2)0.81201 (6)0.0383 (3)
H220.96620.31430.78810.046*
C231.08153 (15)0.4416 (3)0.85470 (6)0.0418 (4)
H231.14320.31530.85940.050*
C241.09758 (13)0.6225 (2)0.89004 (5)0.0353 (3)
H241.16930.62180.91940.042*
C251.00812 (16)0.8051 (3)0.88227 (6)0.0470 (4)
H251.01830.93170.90630.056*
C260.90334 (16)0.8054 (3)0.83963 (6)0.0450 (4)
H260.84320.93370.83480.054*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0575 (8)0.0410 (7)0.0321 (6)0.0100 (6)−0.0010 (5)0.0015 (5)
O10.0585 (8)0.0712 (9)0.0559 (7)0.0191 (6)−0.0119 (6)0.0174 (6)
O20.0780 (8)0.0492 (7)0.0662 (8)−0.0006 (6)0.0028 (6)0.0237 (6)
O30.0332 (5)0.0306 (5)0.0403 (5)−0.0062 (4)−0.0109 (4)0.0041 (4)
C10.0421 (7)0.0337 (7)0.0261 (6)0.0059 (6)0.0007 (5)−0.0013 (5)
C20.0411 (7)0.0324 (7)0.0365 (7)−0.0064 (6)0.0002 (6)−0.0005 (5)
C30.0287 (6)0.0340 (7)0.0365 (7)−0.0041 (5)−0.0030 (5)−0.0016 (5)
C40.0298 (6)0.0298 (7)0.0263 (6)0.0001 (5)−0.0015 (5)−0.0017 (5)
C50.0284 (6)0.0446 (8)0.0344 (6)−0.0070 (5)−0.0001 (5)0.0049 (6)
C60.0288 (6)0.0523 (9)0.0316 (6)0.0024 (6)−0.0019 (5)0.0036 (6)
C110.0264 (6)0.0301 (7)0.0304 (6)−0.0044 (5)−0.0017 (5)0.0029 (5)
C120.0394 (7)0.0325 (7)0.0395 (7)0.0034 (6)−0.0067 (6)−0.0114 (6)
C130.0349 (7)0.0327 (7)0.0410 (7)0.0094 (5)−0.0062 (6)−0.0090 (6)
C140.0250 (6)0.0256 (6)0.0279 (6)−0.0012 (5)0.0038 (5)−0.0004 (4)
C150.0343 (7)0.0324 (7)0.0338 (6)0.0055 (5)−0.0017 (5)−0.0084 (5)
C160.0329 (7)0.0340 (7)0.0393 (7)0.0092 (5)−0.0020 (5)−0.0032 (5)
C210.0247 (6)0.0286 (6)0.0272 (6)−0.0013 (5)0.0039 (5)−0.0003 (5)
C220.0397 (7)0.0352 (8)0.0380 (7)0.0075 (6)−0.0052 (6)−0.0087 (6)
C230.0387 (7)0.0421 (8)0.0425 (7)0.0112 (6)−0.0071 (6)−0.0016 (6)
C240.0301 (6)0.0463 (8)0.0285 (6)−0.0018 (6)−0.0020 (5)0.0019 (5)
C250.0462 (8)0.0482 (9)0.0438 (8)0.0063 (7)−0.0098 (6)−0.0187 (7)
C260.0442 (8)0.0402 (8)0.0471 (8)0.0129 (6)−0.0122 (6)−0.0163 (6)

Geometric parameters (Å, °)

N1—O21.2260 (17)C13—C141.3962 (17)
N1—O11.2315 (17)C13—H130.9500
N1—C11.4608 (17)C14—C151.3978 (17)
O3—C41.3751 (15)C14—C211.4948 (17)
O3—C111.3984 (15)C15—C161.3864 (18)
C1—C21.3828 (19)C15—H150.9500
C1—C61.386 (2)C16—H160.9500
C2—C31.3851 (19)C21—C221.3895 (18)
C2—H20.9500C21—C261.3902 (18)
C3—C41.3897 (18)C22—C231.3924 (19)
C3—H30.9500C22—H220.9500
C4—C51.3906 (17)C23—C241.373 (2)
C5—C61.376 (2)C23—H230.9500
C5—H50.9500C24—C251.376 (2)
C6—H60.9500C24—H240.9500
C11—C121.3769 (18)C25—C261.385 (2)
C11—C161.3798 (18)C25—H250.9500
C12—C131.3893 (18)C26—H260.9500
C12—H120.9500
O2—N1—O1123.04 (13)C12—C13—H13119.2
O2—N1—C1118.95 (13)C14—C13—H13119.2
O1—N1—C1118.00 (13)C13—C14—C15116.74 (11)
C4—O3—C11120.29 (9)C13—C14—C21121.79 (11)
C2—C1—C6121.93 (12)C15—C14—C21121.47 (11)
C2—C1—N1119.31 (13)C16—C15—C14122.23 (12)
C6—C1—N1118.77 (12)C16—C15—H15118.9
C1—C2—C3118.97 (12)C14—C15—H15118.9
C1—C2—H2120.5C11—C16—C15119.17 (12)
C3—C2—H2120.5C11—C16—H16120.4
C2—C3—C4119.52 (12)C15—C16—H16120.4
C2—C3—H3120.2C22—C21—C26116.75 (12)
C4—C3—H3120.2C22—C21—C14121.95 (11)
O3—C4—C3123.69 (11)C26—C21—C14121.29 (11)
O3—C4—C5115.44 (11)C21—C22—C23121.41 (12)
C3—C4—C5120.76 (12)C21—C22—H22119.3
C6—C5—C4119.87 (12)C23—C22—H22119.3
C6—C5—H5120.1C24—C23—C22120.63 (13)
C4—C5—H5120.1C24—C23—H23119.7
C5—C6—C1118.94 (12)C22—C23—H23119.7
C5—C6—H6120.5C23—C24—C25118.90 (12)
C1—C6—H6120.5C23—C24—H24120.5
C12—C11—C16120.49 (12)C25—C24—H24120.5
C12—C11—O3117.24 (11)C24—C25—C26120.44 (13)
C16—C11—O3121.95 (11)C24—C25—H25119.8
C11—C12—C13119.74 (12)C26—C25—H25119.8
C11—C12—H12120.1C25—C26—C21121.86 (13)
C13—C12—H12120.1C25—C26—H26119.1
C12—C13—C14121.62 (12)C21—C26—H26119.1
O2—N1—C1—C212.16 (19)C11—C12—C13—C14−0.5 (2)
O1—N1—C1—C2−168.59 (13)C12—C13—C14—C15−0.5 (2)
O2—N1—C1—C6−167.52 (13)C12—C13—C14—C21179.53 (12)
O1—N1—C1—C611.73 (19)C13—C14—C15—C160.9 (2)
C6—C1—C2—C3−0.2 (2)C21—C14—C15—C16−179.06 (12)
N1—C1—C2—C3−179.88 (11)C12—C11—C16—C15−0.5 (2)
C1—C2—C3—C40.17 (19)O3—C11—C16—C15172.89 (11)
C11—O3—C4—C327.36 (17)C14—C15—C16—C11−0.5 (2)
C11—O3—C4—C5−156.29 (11)C13—C14—C21—C22−6.20 (19)
C2—C3—C4—O3176.54 (11)C15—C14—C21—C22173.79 (12)
C2—C3—C4—C50.38 (19)C13—C14—C21—C26172.90 (13)
O3—C4—C5—C6−177.36 (12)C15—C14—C21—C26−7.11 (19)
C3—C4—C5—C6−0.9 (2)C26—C21—C22—C230.6 (2)
C4—C5—C6—C10.8 (2)C14—C21—C22—C23179.73 (12)
C2—C1—C6—C5−0.3 (2)C21—C22—C23—C240.2 (2)
N1—C1—C6—C5179.37 (12)C22—C23—C24—C25−0.6 (2)
C4—O3—C11—C12−133.96 (13)C23—C24—C25—C260.3 (2)
C4—O3—C11—C1652.42 (16)C24—C25—C26—C210.5 (3)
C16—C11—C12—C131.0 (2)C22—C21—C26—C25−1.0 (2)
O3—C11—C12—C13−172.73 (12)C14—C21—C26—C25179.89 (13)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WW2140).

References

  • Agag, T. & Takeichi, T. (1999). Polymer, 40, 6557–6563.
  • Boey, F. Y. C. & Yap, B. H. (2001). Polym. Test.20, 837–845.
  • Bonnaud, L., Pascault, J. P., Sautereau, H., Zhao, J. Q. & Jia, D. M. (2004). Eur. Polym. J.40, 2637–3643.
  • Grampel, D. R. van de, Ming, W., van Gennip, W. J. H., van der Velden, F., Laven, J., Niemantsverdriet, J. W. & van der Linde, R. (2005). Polymer, 46, 10531-10537.
  • Kagathera, V. M. & Parsania, P. H. (2001). Polym. Test.20, 713–716.
  • Moris, A. B. de, Pereira, A. B., Teixeira, J. P. & Cavaleiro, N. C. (2007). Int. J. Adhes. Adhes.27, 679–686.
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