4,4′ Bis(4 nitro­phen­­oxy)biphen­yl

organic papers

o1710

24H16N2O6 doi:10.1107/S1600536807007428 Acta Cryst.(2007). E63, o1710–o1711

Acta Crystallographica Section E Structure Reports Online

ISSN 1600-5368

4,4

_{-Bis(4-nitrophenoxy)biphenyl}

Samia Sajid,aZareen Akhter,a Michael Bolteband Humaira M. Siddiqia*

a_{Department of Chemistry, Quaid-I-Azam}

University, Islamabad 45320, Pakistan, and

b

Institut fu¨r Anorganische Chemie, J.-W.-Goethe-Universita¨t Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 173 K

Mean(C–C) = 0.001 A˚

Rfactor = 0.024

wRfactor = 0.073

Data-to-parameter ratio = 12.2

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

Received 22 January 2007 Accepted 13 February 2007

#2007 International Union of Crystallography All rights reserved

The asymmetric unit of the title compound, C24H16N2O6,

contains one half-molecule; there is a crystallographic inversion centreat the mid-point of the central C—C bond, constraining the central biphenyl group to be planar.

Comment

Epoxy resins may be regarded as materials in which extensive chain cross-linking occurs through reactions of the epoxy groups with polyfunctional (functionality > 2) curing agents. Epoxy resins generally possess excellent characteristics: heat, moisture and chemical resistance, toughness, electrical and mechanical resistance, and good adhesion to many substrates (Shieh & Wang, 2002). The versatility of their properties results in a wide range of applications (Lee & Neville, 1976; Zong et al., 2003). One of the excellent properties of epoxy resins is that it is possible to tailor and improve their prop-erties for specific applications by choosing curing agents and the epoxy reagent (Blanco et al., 2005). One way to achieve this modification is by reacting a bifunctional epoxy resin with amines bearing different functionalities (Swier et al., 2004). Aromatic amines are reported to improve the properties of epoxy networks (Plateret al., 2000). The title compound, (I), has been synthesized in view of its conversion to an aromatic diamine to be used as a curing agent for epoxy pre-polymers.

A perspective view of (I) is given in Fig. 1. Bond lengths and angles can be regarded as normal (Cambridge Structural Database, Version 5.27, updated August 2006; Allen, 2002; Mogul, Version 1.1; Bruno et al., 2004). The molecule has crystallographic Ci symmetry. The biphenyl unit is exactly

planar due to the symmetry of the molecule. The dihedral angle between the biphenyl unit (atoms C11–C16) and the nitrophenyl ring (C21–C26) is 74.93 (2)_.

Experimental

A mixture of 10 g (0.054 mol) 4,40_{-dihydroxybiphenyl, 14.86 g}

(0.107 mol) of anhydrous K2CO3and 16.94 g (0.107 mol) ofp

Crystal data

C24H16N2O6

Mr= 428.39 Monoclinic,P21=c

a= 10.6245 (17) A˚

b= 9.0387 (14) A˚

c= 10.4509 (16) A˚

= 97.042 (13)

V= 996.0 (3) A˚3

Z= 2

MoKradiation

= 0.10 mm1

T= 173 (2) K 0.350.320.29 mm

Data collection

Stoe IPDS-II two-circle diffractometer

Absorption correction: none 3482 measured reflections

1766 independent reflections 1556 reflections withI> 2(I)

Rint= 0.029

Refinement

R[F2_{> 2(F}2_{)] = 0.024}

wR(F2) = 0.073

S= 1.05 1766 reflections

145 parameters

H-atom parameters constrained max= 0.13 e A˚

3

min=0.13 e A˚

3

H atoms were found in a difference map, but they were eventually refined using a riding model with bond lengths constrained to C—H = 0.95 A˚ and withUiso(H) = 1.2Ueq(C).

Data collection:X-AREA(Stoe & Cie, 2001); cell refinement: X-AREA; data reduction:X-AREA; program(s) used to solve structure:

SHELXS97(Sheldrick, 1997); program(s) used to refine structure:

SHELXL97 (Sheldrick, 1997); molecular graphics: XP in

SHELXTL-Plus(Sheldrick, 1991); software used to prepare material

for publication:SHELXL97andPLATON(Spek, 2003).

The authors are grateful to the Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan.

References

Allen, F. H. (2002).Acta Cryst.B58, 380–388.

Blanco, M., Corcuera, M. A., Riccardi, C. C. & Mondragon, I. (2005).Polymer,

46, 7989–8000.

Bruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E. & Orpen, A. G. (2004).J. Chem. Inf. Comput. Sci.44, 2133–2144.

Lee, H. & Neville, K. (1976). Handbook of Epoxy Resins. New York: McGraw–Hill.

Plater, M. J., McKay, M. & Jackson, T. (2000).J. Chem. Soc. Perkin Trans. 1, pp. 2695–2701.

Sheldrick, G. M. (1991).SHELXTL-Plus. Release 4.1. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97, University of Go¨ttingen, Germany.

Shieh, J. Y. & Wang, Ch. S. (2002).J. Appl. Polym. Sci. Polym. Chem.40, 369– 379.

Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.

Stoe & Cie (2001).X-AREA. Stoe & Cie, Darmstadt, Germany.

Swier, S., Van Assche, G. & Van Mele, B. (2004).J. Appl. Polym. Sci.91, 2798– 2813.

Zong, L., Zhou, S., Sgrricia, N., Hawley, M. C. & Kempel, L. C. (2003).J. Microw. Power Electromagn. Energ.38, 49–74.

Figure 1

supporting information

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Acta Cryst. (2007). E63, o1710–o1711

supporting information

Acta Cryst. (2007). E63, o1710–o1711 [https://doi.org/10.1107/S1600536807007428]

4,4

′

-Bis(4-nitrophenoxy)biphenyl

Samia Sajid, Zareen Akhter, Michael Bolte and Humaira M. Siddiqi

4,4′-Bis(4-nitrophenoxy)biphenyl

Crystal data C24H16N2O6

Mr = 428.39 Monoclinic, P21/c

Hall symbol: -P 2ybc a = 10.6245 (17) Å b = 9.0387 (14) Å c = 10.4509 (16) Å β = 97.042 (13)° V = 996.0 (3) Å3

Z = 2

F(000) = 444 Dx = 1.428 Mg m−3

Melting point: 418 K

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 2164 reflections θ = 3.8–25.4°

µ = 0.10 mm−1

T = 173 K

Block, light brown 0.35 × 0.32 × 0.29 mm

Data collection

Stoe IPDS-II two-circle diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

ω scans

3482 measured reflections 1766 independent reflections

1556 reflections with I > 2σ(I) Rint = 0.029

θmax = 25.0°, θmin = 1.9°

h = −12→12 k = 0→10 l = 0→12

Refinement Refinement on F2

Least-squares matrix: full R[F2 _{> 2σ(F}2_{)] = 0.024}

wR(F2_{) = 0.073}

S = 1.05 1766 reflections 145 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained w = 1/[σ2_(F

o2) + (0.0553P)2]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

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

x y z Uiso*/Ueq

C11 0.67598 (9) 0.34822 (6) 0.76328 (7) 0.0302 (2) C12 0.56139 (9) 0.28363 (6) 0.78233 (7) 0.0361 (2) H12 0.5299 0.2001 0.7333 0.043* C13 0.49339 (9) 0.34526 (6) 0.87603 (7) 0.0348 (2) H13 0.4143 0.3025 0.8892 0.042* C14 0.53699 (7) 0.46618 (5) 0.95022 (6) 0.0240 (2) C15 0.65561 (9) 0.52604 (6) 0.92945 (7) 0.0305 (2) H15 0.6893 0.6075 0.9800 0.037* C16 0.72385 (9) 0.46709 (6) 0.83579 (8) 0.0339 (2) H16 0.8031 0.5088 0.8221 0.041* C21 0.77757 (8) 0.36068 (6) 0.57130 (6) 0.0289 (2) C22 0.70996 (9) 0.48531 (5) 0.52442 (7) 0.0320 (2) H22 0.6412 0.5208 0.5659 0.038* C23 0.74410 (9) 0.55714 (6) 0.41632 (7) 0.0319 (2) H23 0.6994 0.6425 0.3828 0.038* C24 0.84550 (8) 0.50122 (6) 0.35796 (6) 0.0262 (2) C25 0.91284 (8) 0.37689 (5) 0.40397 (6) 0.0282 (2) H25 0.9813 0.3413 0.3621 0.034* C26 0.87901 (8) 0.30550 (5) 0.51147 (6) 0.0290 (2) H26 0.9239 0.2201 0.5445 0.035*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

O1 0.0499 (5) 0.0307 (2) 0.0312 (3) 0.0137 (2) 0.0184 (3) 0.00445 (17) N1 0.0311 (4) 0.0326 (3) 0.0316 (3) −0.0063 (3) 0.0065 (3) −0.0004 (2) O2 0.0469 (5) 0.0394 (2) 0.0466 (3) −0.0005 (2) 0.0126 (3) 0.0107 (2) O3 0.0455 (5) 0.0518 (3) 0.0453 (3) −0.0029 (3) 0.0261 (3) −0.0021 (2) C11 0.0355 (5) 0.0319 (3) 0.0248 (3) 0.0096 (3) 0.0098 (3) 0.0032 (2) C12 0.0371 (6) 0.0377 (3) 0.0338 (4) −0.0045 (4) 0.0052 (4) −0.0110 (3) C13 0.0307 (5) 0.0398 (3) 0.0350 (4) −0.0058 (3) 0.0086 (3) −0.0097 (3) C14 0.0270 (5) 0.0229 (3) 0.0220 (3) 0.0027 (3) 0.0029 (3) 0.0047 (2) C15 0.0311 (5) 0.0277 (3) 0.0340 (4) −0.0044 (3) 0.0088 (3) −0.0024 (2) C16 0.0318 (5) 0.0337 (3) 0.0384 (4) −0.0021 (3) 0.0138 (3) −0.0013 (3) C21 0.0325 (5) 0.0308 (2) 0.0242 (3) 0.0020 (3) 0.0062 (3) −0.0032 (2) C22 0.0338 (5) 0.0339 (3) 0.0299 (4) 0.0104 (3) 0.0108 (3) 0.0008 (2) C23 0.0352 (5) 0.0291 (2) 0.0322 (4) 0.0069 (3) 0.0067 (3) −0.0017 (2) C24 0.0271 (5) 0.0287 (3) 0.0229 (3) −0.0046 (3) 0.0037 (3) −0.0033 (2) C25 0.0249 (5) 0.0305 (3) 0.0301 (4) 0.0002 (3) 0.0064 (3) −0.0074 (2) C26 0.0288 (5) 0.0252 (3) 0.0332 (4) 0.0050 (3) 0.0043 (3) −0.0053 (2)

Geometric parameters (Å, º)

supporting information

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Acta Cryst. (2007). E63, o1710–o1711

C11—C16 1.3758 (10) C22—C23 1.3893 (11) C11—C12 1.3864 (13) C22—H22 0.9500 C12—C13 1.4017 (13) C23—C24 1.3961 (12) C12—H12 0.9500 C23—H23 0.9500 C13—C14 1.3865 (8) C24—C25 1.3862 (9) C13—H13 0.9500 C25—C26 1.3808 (11) C14—C15 1.4125 (12) C25—H25 0.9500 C14—C14i _{1.5081 (15) C26—H26 0.9500}

C21—O1—C11 117.86 (4) C11—C16—H16 120.1 O3—N1—O2 123.11 (7) C15—C16—H16 120.1 O3—N1—C24 117.95 (5) O1—C21—C22 123.28 (8) O2—N1—C24 118.94 (7) O1—C21—C26 115.16 (6) C16—C11—C12 121.44 (8) C22—C21—C26 121.49 (7) C16—C11—O1 121.32 (8) C23—C22—C21 119.30 (8) C12—C11—O1 116.99 (6) C23—C22—H22 120.4 C11—C12—C13 118.03 (5) C21—C22—H22 120.4 C11—C12—H12 121.0 C22—C23—C24 118.59 (6) C13—C12—H12 121.0 C22—C23—H23 120.7 C14—C13—C12 122.58 (8) C24—C23—H23 120.7 C14—C13—H13 118.7 C25—C24—C23 122.35 (7) C12—C13—H13 118.7 C25—C24—N1 119.85 (7) C13—C14—C15 117.34 (8) C23—C24—N1 117.81 (6) C13—C14—C14i _{122.60 (9) C26—C25—C24 119.10 (7)}

C15—C14—C14i _{120.07 (6) C26—C25—H25 120.5}

C16—C15—C14 120.82 (6) C24—C25—H25 120.5 C16—C15—H15 119.6 C25—C26—C21 119.17 (6) C14—C15—H15 119.6 C25—C26—H26 120.4 C11—C16—C15 119.77 (8) C21—C26—H26 120.4

C21—O1—C11—C16 −63.32 (8) O1—C21—C22—C23 −177.03 (6) C21—O1—C11—C12 122.38 (7) C26—C21—C22—C23 −0.32 (10) C16—C11—C12—C13 1.53 (10) C21—C22—C23—C24 0.14 (10) O1—C11—C12—C13 175.82 (5) C22—C23—C24—C25 0.09 (10) C11—C12—C13—C14 −0.66 (10) C22—C23—C24—N1 −179.77 (5) C12—C13—C14—C15 −0.79 (10) O3—N1—C24—C25 6.63 (9) C12—C13—C14—C14i _{179.14 (6) O2—N1—C24—C25 −173.51 (5)}

C13—C14—C15—C16 1.43 (9) O3—N1—C24—C23 −173.51 (6) C14i_{—C14—C15—C16 −178.49 (6) O2—N1—C24—C23 6.36 (9)}

C12—C11—C16—C15 −0.91 (10) C23—C24—C25—C26 −0.13 (9) O1—C11—C16—C15 −174.95 (5) N1—C24—C25—C26 179.72 (5) C14—C15—C16—C11 −0.62 (9) C24—C25—C26—C21 −0.05 (8) C11—O1—C21—C22 −22.77 (9) O1—C21—C26—C25 177.24 (5) C11—O1—C21—C26 160.33 (6) C22—C21—C26—C25 0.28 (9)