4-(4-Nitro-phenoxy)biphen-yl.

The two phenyl rings of the biphenyl unit of the title compound, C(18)H(13)NO(3), are almost coplanar [dihedral angle 6.70 (9)°]. The nitro-phenyl 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 ▶); Bonnaud et al. (2004 ▶); de Moris et al. (2007 ▶); Van de Grampel et al. (2005 ▶); Agag & Takeichi (1999 ▶); Kagathera & Parsania (2001 ▶); Kagathera & Parsania (2001 ▶).

Experimental

Crystal data

C18H13NO3

M = 291.29

Monoclinic,

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 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

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

C18H13NO3	F(000) = 608
Mr = 291.29	Dx = 1.393 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16639 reflections
a = 9.6435 (7) Å	θ = 2.2–25.8°
b = 5.8648 (3) Å	µ = 0.10 mm−1
c = 24.6884 (18) Å	T = 173 K
β = 95.704 (6)°	Plate, colourless
V = 1389.39 (16) Å3	0.44 × 0.37 × 0.13 mm
Z = 4

STOE IPDS II two-circle-diffractometer	2187 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.052
graphite	θmax = 25.5°, θmin = 2.1°
ω scans	h = −11→11
16020 measured reflections	k = −7→6
2556 independent reflections	l = −29→29

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

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
N1	0.24460 (14)	1.3101 (2)	0.49386 (5)	0.0439 (3)
O1	0.11760 (13)	1.3217 (2)	0.48231 (5)	0.0630 (4)
O2	0.32703 (14)	1.4402 (2)	0.47506 (5)	0.0648 (4)
O3	0.44070 (9)	0.60894 (15)	0.63327 (4)	0.0357 (3)
C1	0.29854 (14)	1.1306 (2)	0.53120 (5)	0.0342 (3)
C2	0.43662 (14)	1.1370 (2)	0.55251 (5)	0.0369 (3)
H2	0.4960	1.2569	0.5431	0.044*
C3	0.48706 (13)	0.9659 (2)	0.58781 (5)	0.0335 (3)
H3	0.5816	0.9675	0.6030	0.040*
C4	0.39846 (12)	0.7919 (2)	0.60091 (5)	0.0289 (3)
C5	0.26016 (13)	0.7870 (3)	0.57875 (5)	0.0360 (3)
H5	0.2008	0.6661	0.5876	0.043*
C6	0.20939 (13)	0.9577 (3)	0.54400 (5)	0.0379 (3)
H6	0.1148	0.9570	0.5290	0.045*
C11	0.55429 (12)	0.6296 (2)	0.67283 (5)	0.0293 (3)
C12	0.65196 (14)	0.4576 (2)	0.67578 (6)	0.0378 (3)
H12	0.6466	0.3408	0.6490	0.045*
C13	0.75837 (14)	0.4557 (2)	0.71807 (5)	0.0369 (3)
H13	0.8249	0.3358	0.7200	0.044*
C14	0.76992 (12)	0.6256 (2)	0.75787 (5)	0.0261 (3)
C15	0.66981 (13)	0.7987 (2)	0.75286 (5)	0.0338 (3)
H15	0.6755	0.9182	0.7790	0.041*
C16	0.56253 (14)	0.8018 (2)	0.71109 (5)	0.0358 (3)
H16	0.4955	0.9211	0.7088	0.043*
C21	0.88361 (12)	0.6232 (2)	0.80367 (5)	0.0268 (3)
C22	0.97567 (14)	0.4414 (2)	0.81201 (6)	0.0383 (3)
H22	0.9662	0.3143	0.7881	0.046*
C23	1.08153 (15)	0.4416 (3)	0.85470 (6)	0.0418 (4)
H23	1.1432	0.3153	0.8594	0.050*
C24	1.09758 (13)	0.6225 (2)	0.89004 (5)	0.0353 (3)
H24	1.1693	0.6218	0.9194	0.042*
C25	1.00812 (16)	0.8051 (3)	0.88227 (6)	0.0470 (4)
H25	1.0183	0.9317	0.9063	0.056*
C26	0.90334 (16)	0.8054 (3)	0.83963 (6)	0.0450 (4)
H26	0.8432	0.9337	0.8348	0.054*

	U11	U22	U33	U12	U13	U23
N1	0.0575 (8)	0.0410 (7)	0.0321 (6)	0.0100 (6)	−0.0010 (5)	0.0015 (5)
O1	0.0585 (8)	0.0712 (9)	0.0559 (7)	0.0191 (6)	−0.0119 (6)	0.0174 (6)
O2	0.0780 (8)	0.0492 (7)	0.0662 (8)	−0.0006 (6)	0.0028 (6)	0.0237 (6)
O3	0.0332 (5)	0.0306 (5)	0.0403 (5)	−0.0062 (4)	−0.0109 (4)	0.0041 (4)
C1	0.0421 (7)	0.0337 (7)	0.0261 (6)	0.0059 (6)	0.0007 (5)	−0.0013 (5)
C2	0.0411 (7)	0.0324 (7)	0.0365 (7)	−0.0064 (6)	0.0002 (6)	−0.0005 (5)
C3	0.0287 (6)	0.0340 (7)	0.0365 (7)	−0.0041 (5)	−0.0030 (5)	−0.0016 (5)
C4	0.0298 (6)	0.0298 (7)	0.0263 (6)	0.0001 (5)	−0.0015 (5)	−0.0017 (5)
C5	0.0284 (6)	0.0446 (8)	0.0344 (6)	−0.0070 (5)	−0.0001 (5)	0.0049 (6)
C6	0.0288 (6)	0.0523 (9)	0.0316 (6)	0.0024 (6)	−0.0019 (5)	0.0036 (6)
C11	0.0264 (6)	0.0301 (7)	0.0304 (6)	−0.0044 (5)	−0.0017 (5)	0.0029 (5)
C12	0.0394 (7)	0.0325 (7)	0.0395 (7)	0.0034 (6)	−0.0067 (6)	−0.0114 (6)
C13	0.0349 (7)	0.0327 (7)	0.0410 (7)	0.0094 (5)	−0.0062 (6)	−0.0090 (6)
C14	0.0250 (6)	0.0256 (6)	0.0279 (6)	−0.0012 (5)	0.0038 (5)	−0.0004 (4)
C15	0.0343 (7)	0.0324 (7)	0.0338 (6)	0.0055 (5)	−0.0017 (5)	−0.0084 (5)
C16	0.0329 (7)	0.0340 (7)	0.0393 (7)	0.0092 (5)	−0.0020 (5)	−0.0032 (5)
C21	0.0247 (6)	0.0286 (6)	0.0272 (6)	−0.0013 (5)	0.0039 (5)	−0.0003 (5)
C22	0.0397 (7)	0.0352 (8)	0.0380 (7)	0.0075 (6)	−0.0052 (6)	−0.0087 (6)
C23	0.0387 (7)	0.0421 (8)	0.0425 (7)	0.0112 (6)	−0.0071 (6)	−0.0016 (6)
C24	0.0301 (6)	0.0463 (8)	0.0285 (6)	−0.0018 (6)	−0.0020 (5)	0.0019 (5)
C25	0.0462 (8)	0.0482 (9)	0.0438 (8)	0.0063 (7)	−0.0098 (6)	−0.0187 (7)
C26	0.0442 (8)	0.0402 (8)	0.0471 (8)	0.0129 (6)	−0.0122 (6)	−0.0163 (6)

N1—O2	1.2260 (17)	C13—C14	1.3962 (17)
N1—O1	1.2315 (17)	C13—H13	0.9500
N1—C1	1.4608 (17)	C14—C15	1.3978 (17)
O3—C4	1.3751 (15)	C14—C21	1.4948 (17)
O3—C11	1.3984 (15)	C15—C16	1.3864 (18)
C1—C2	1.3828 (19)	C15—H15	0.9500
C1—C6	1.386 (2)	C16—H16	0.9500
C2—C3	1.3851 (19)	C21—C22	1.3895 (18)
C2—H2	0.9500	C21—C26	1.3902 (18)
C3—C4	1.3897 (18)	C22—C23	1.3924 (19)
C3—H3	0.9500	C22—H22	0.9500
C4—C5	1.3906 (17)	C23—C24	1.373 (2)
C5—C6	1.376 (2)	C23—H23	0.9500
C5—H5	0.9500	C24—C25	1.376 (2)
C6—H6	0.9500	C24—H24	0.9500
C11—C12	1.3769 (18)	C25—C26	1.385 (2)
C11—C16	1.3798 (18)	C25—H25	0.9500
C12—C13	1.3893 (18)	C26—H26	0.9500
C12—H12	0.9500
O2—N1—O1	123.04 (13)	C12—C13—H13	119.2
O2—N1—C1	118.95 (13)	C14—C13—H13	119.2
O1—N1—C1	118.00 (13)	C13—C14—C15	116.74 (11)
C4—O3—C11	120.29 (9)	C13—C14—C21	121.79 (11)
C2—C1—C6	121.93 (12)	C15—C14—C21	121.47 (11)
C2—C1—N1	119.31 (13)	C16—C15—C14	122.23 (12)
C6—C1—N1	118.77 (12)	C16—C15—H15	118.9
C1—C2—C3	118.97 (12)	C14—C15—H15	118.9
C1—C2—H2	120.5	C11—C16—C15	119.17 (12)
C3—C2—H2	120.5	C11—C16—H16	120.4
C2—C3—C4	119.52 (12)	C15—C16—H16	120.4
C2—C3—H3	120.2	C22—C21—C26	116.75 (12)
C4—C3—H3	120.2	C22—C21—C14	121.95 (11)
O3—C4—C3	123.69 (11)	C26—C21—C14	121.29 (11)
O3—C4—C5	115.44 (11)	C21—C22—C23	121.41 (12)
C3—C4—C5	120.76 (12)	C21—C22—H22	119.3
C6—C5—C4	119.87 (12)	C23—C22—H22	119.3
C6—C5—H5	120.1	C24—C23—C22	120.63 (13)
C4—C5—H5	120.1	C24—C23—H23	119.7
C5—C6—C1	118.94 (12)	C22—C23—H23	119.7
C5—C6—H6	120.5	C23—C24—C25	118.90 (12)
C1—C6—H6	120.5	C23—C24—H24	120.5
C12—C11—C16	120.49 (12)	C25—C24—H24	120.5
C12—C11—O3	117.24 (11)	C24—C25—C26	120.44 (13)
C16—C11—O3	121.95 (11)	C24—C25—H25	119.8
C11—C12—C13	119.74 (12)	C26—C25—H25	119.8
C11—C12—H12	120.1	C25—C26—C21	121.86 (13)
C13—C12—H12	120.1	C25—C26—H26	119.1
C12—C13—C14	121.62 (12)	C21—C26—H26	119.1
O2—N1—C1—C2	12.16 (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—C21	179.53 (12)
O1—N1—C1—C6	11.73 (19)	C13—C14—C15—C16	0.9 (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—C4	0.17 (19)	O3—C11—C16—C15	172.89 (11)
C11—O3—C4—C3	27.36 (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—O3	176.54 (11)	C15—C14—C21—C22	173.79 (12)
C2—C3—C4—C5	0.38 (19)	C13—C14—C21—C26	172.90 (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—C23	0.6 (2)
C4—C5—C6—C1	0.8 (2)	C14—C21—C22—C23	179.73 (12)
C2—C1—C6—C5	−0.3 (2)	C21—C22—C23—C24	0.2 (2)
N1—C1—C6—C5	179.37 (12)	C22—C23—C24—C25	−0.6 (2)
C4—O3—C11—C12	−133.96 (13)	C23—C24—C25—C26	0.3 (2)
C4—O3—C11—C16	52.42 (16)	C24—C25—C26—C21	0.5 (3)
C16—C11—C12—C13	1.0 (2)	C22—C21—C26—C25	−1.0 (2)
O3—C11—C12—C13	−172.73 (12)	C14—C21—C26—C25	179.89 (13)