4-Meth-oxy-2-nitro-4'-(trifluoro-meth-yl)biphen-yl.

The title compound, C(14)H(10)F(3)NO(3), was prepared by a palladium-catalysed Suzuki-Miyaura coupling reaction. The dihedral angle between the nitro group and its parent benzene ring is 66.85 (19)° while the dihedral angle between the two benzene rings is 49.98 (9)°. The CF(3) group is disordered over two sets of sites with occupancies of 0.457 (8) and 0.543 (8).

Related literature

For general background to the synthesis and properties of the title compound, see: Suzuki (1999 ▶); Razler et al. (2009 ▶). For the biological activity of biphenyl derivatives, see: Kimpe et al. (1996 ▶).

Experimental

Crystal data

C14H10F3NO3

M = 297.23

Monoclinic,

a = 8.1956 (13) Å

b = 20.777 (3) Å

c = 7.9715 (12) Å

β = 104.240 (2)°

V = 1315.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.26 × 0.24 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.966, T max = 0.974

10512 measured reflections

3235 independent reflections

1910 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.161

S = 1.05

3235 reflections

243 parameters

36 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039092/ff2027sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039092/ff2027Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039092/ff2027Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811039092/ff2027Isup4.cml

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

C14H10F3NO3	F(000) = 608
Mr = 297.23	Dx = 1.501 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1880 reflections
a = 8.1956 (13) Å	θ = 2.8–22.6°
b = 20.777 (3) Å	µ = 0.13 mm−1
c = 7.9715 (12) Å	T = 293 K
β = 104.240 (2)°	Block, colorless
V = 1315.7 (3) Å3	0.26 × 0.24 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3235 independent reflections
Radiation source: fine-focus sealed tube	1910 reflections with I > 2σ(I)
graphite	Rint = 0.029
phi and ω scans	θmax = 28.3°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.966, Tmax = 0.974	k = −27→27
10512 measured reflections	l = −10→10

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.161	w = 1/[σ2(Fo2) + (0.0741P)2 + 0.1504P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3235 reflections	Δρmax = 0.30 e Å−3
243 parameters	Δρmin = −0.21 e Å−3
36 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (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	Occ. (<1)
C1A	0.6447 (4)	0.19880 (14)	0.4301 (4)	0.0705 (7)	0.46
F1A	0.6131 (8)	0.1395 (3)	0.3972 (18)	0.147 (3)	0.46
F2A	0.7487 (9)	0.2001 (4)	0.5832 (6)	0.108 (2)	0.46
F3A	0.7514 (8)	0.2162 (4)	0.3299 (10)	0.1111 (16)	0.46
C1B	0.6447 (4)	0.19880 (14)	0.4301 (4)	0.0705 (7)	0.54
F1B	0.6331 (8)	0.1469 (3)	0.5270 (8)	0.1152 (18)	0.54
F2B	0.7864 (6)	0.2248 (3)	0.4985 (14)	0.142 (2)	0.54
F3B	0.6443 (9)	0.1723 (3)	0.2844 (5)	0.1143 (16)	0.54
O3	−0.3255 (2)	0.48543 (8)	0.4265 (2)	0.0667 (5)
N1	0.0999 (2)	0.42470 (11)	0.1294 (2)	0.0604 (5)
C2	0.4994 (3)	0.24308 (11)	0.4159 (3)	0.0549 (6)
C3	0.5169 (3)	0.30787 (12)	0.3869 (3)	0.0581 (6)
C4	0.3843 (3)	0.34936 (11)	0.3798 (3)	0.0551 (6)
C5	0.2308 (3)	0.32692 (10)	0.4005 (3)	0.0496 (5)
C6	0.2145 (3)	0.26131 (11)	0.4274 (3)	0.0573 (6)
C7	0.3473 (3)	0.21981 (12)	0.4348 (3)	0.0606 (6)
C8	0.0882 (3)	0.37089 (10)	0.4025 (3)	0.0485 (5)
C9	0.0257 (3)	0.41719 (10)	0.2790 (3)	0.0484 (5)
C10	−0.1091 (3)	0.45702 (10)	0.2791 (3)	0.0504 (5)
C11	−0.1881 (3)	0.45081 (10)	0.4134 (3)	0.0512 (5)
C12	−0.1259 (3)	0.40693 (11)	0.5441 (3)	0.0574 (6)
H12	−0.1751	0.4039	0.6372	0.069*
C13	0.0072 (3)	0.36797 (11)	0.5379 (3)	0.0568 (6)
C14	−0.4039 (3)	0.52531 (14)	0.2844 (4)	0.0754 (8)
H14A	−0.3272	0.5585	0.2700	0.113*
H14B	−0.5032	0.5445	0.3064	0.113*
H14C	−0.4343	0.4998	0.1810	0.113*
H10	−0.146 (3)	0.4878 (10)	0.188 (3)	0.053 (6)*
H4	0.401 (3)	0.3937 (11)	0.364 (3)	0.064 (7)*
H11	0.044 (3)	0.3381 (11)	0.630 (3)	0.063 (6)*
H6	0.112 (3)	0.2454 (11)	0.442 (3)	0.062 (6)*
H7	0.332 (3)	0.1735 (12)	0.454 (3)	0.067 (7)*
H3	0.622 (3)	0.3236 (11)	0.371 (3)	0.068 (7)*
O2	0.1707 (3)	0.47594 (11)	0.1180 (3)	0.0972 (7)
O1	0.0856 (3)	0.38237 (10)	0.0266 (3)	0.1025 (8)

	U11	U22	U33	U12	U13	U23
C1A	0.0697 (18)	0.0762 (18)	0.0648 (17)	0.0077 (14)	0.0150 (13)	−0.0032 (14)
F1A	0.114 (4)	0.079 (3)	0.239 (7)	0.007 (3)	0.025 (6)	−0.054 (5)
F2A	0.099 (4)	0.151 (6)	0.063 (2)	0.062 (4)	−0.001 (2)	0.004 (3)
F3A	0.089 (3)	0.141 (4)	0.123 (4)	0.043 (3)	0.061 (3)	0.041 (3)
C1B	0.0697 (18)	0.0762 (18)	0.0648 (17)	0.0077 (14)	0.0150 (13)	−0.0032 (14)
F1B	0.126 (4)	0.116 (4)	0.115 (3)	0.066 (3)	0.053 (3)	0.055 (3)
F2B	0.065 (2)	0.122 (4)	0.221 (6)	0.017 (2)	0.002 (4)	−0.038 (4)
F3B	0.151 (4)	0.128 (3)	0.070 (2)	0.067 (3)	0.039 (2)	−0.007 (2)
O3	0.0589 (10)	0.0774 (11)	0.0701 (11)	0.0099 (8)	0.0280 (8)	0.0027 (8)
N1	0.0601 (12)	0.0727 (13)	0.0524 (11)	0.0114 (10)	0.0215 (9)	0.0146 (10)
C2	0.0553 (13)	0.0601 (13)	0.0466 (12)	0.0065 (11)	0.0076 (10)	−0.0014 (9)
C3	0.0517 (13)	0.0662 (15)	0.0568 (13)	−0.0055 (11)	0.0139 (10)	−0.0024 (11)
C4	0.0562 (14)	0.0512 (13)	0.0586 (13)	−0.0068 (11)	0.0152 (10)	0.0017 (10)
C5	0.0518 (12)	0.0518 (12)	0.0436 (11)	−0.0029 (10)	0.0085 (9)	0.0027 (9)
C6	0.0535 (14)	0.0536 (13)	0.0655 (14)	−0.0051 (11)	0.0161 (11)	0.0067 (10)
C7	0.0651 (15)	0.0524 (13)	0.0637 (14)	0.0005 (12)	0.0148 (11)	0.0058 (11)
C8	0.0477 (12)	0.0475 (11)	0.0501 (12)	−0.0066 (9)	0.0115 (9)	0.0023 (9)
C9	0.0518 (12)	0.0519 (11)	0.0438 (11)	−0.0031 (9)	0.0166 (9)	0.0019 (9)
C10	0.0531 (12)	0.0499 (11)	0.0501 (12)	0.0002 (10)	0.0161 (10)	0.0056 (10)
C11	0.0489 (12)	0.0529 (12)	0.0545 (12)	−0.0062 (10)	0.0176 (10)	−0.0032 (10)
C12	0.0590 (14)	0.0657 (14)	0.0529 (12)	−0.0066 (11)	0.0243 (10)	0.0026 (10)
C13	0.0611 (14)	0.0604 (13)	0.0492 (12)	−0.0040 (11)	0.0144 (10)	0.0104 (10)
C14	0.0611 (16)	0.0862 (18)	0.0803 (18)	0.0158 (14)	0.0201 (13)	0.0066 (14)
O2	0.1010 (15)	0.1191 (17)	0.0805 (14)	−0.0256 (13)	0.0393 (12)	0.0224 (12)
O1	0.149 (2)	0.0977 (15)	0.0789 (13)	0.0180 (14)	0.0628 (14)	−0.0116 (11)

C1A—F1A	1.273 (6)	C5—C8	1.487 (3)
C1A—F2A	1.306 (6)	C6—C7	1.378 (3)
C1A—F3A	1.370 (5)	C6—H6	0.93 (2)
C1A—C2	1.487 (3)	C7—H7	0.99 (2)
O3—C11	1.361 (3)	C8—C9	1.381 (3)
O3—C14	1.423 (3)	C8—C13	1.401 (3)
N1—O1	1.188 (3)	C9—C10	1.381 (3)
N1—O2	1.226 (3)	C10—C11	1.387 (3)
N1—C9	1.474 (2)	C10—H10	0.96 (2)
C2—C3	1.379 (3)	C11—C12	1.384 (3)
C2—C7	1.380 (3)	C12—C13	1.369 (3)
C3—C4	1.377 (3)	C12—H12	0.9300
C3—H3	0.96 (2)	C13—H11	0.95 (2)
C4—C5	1.389 (3)	C14—H14A	0.9600
C4—H4	0.94 (2)	C14—H14B	0.9600
C5—C6	1.391 (3)	C14—H14C	0.9600
F1A—C1A—F2A	105.4 (6)	C6—C7—H7	119.2 (14)
F1A—C1A—F3A	105.2 (5)	C2—C7—H7	120.7 (14)
F2A—C1A—F3A	100.1 (5)	C9—C8—C13	114.61 (19)
F1A—C1A—C2	117.7 (4)	C9—C8—C5	125.07 (17)
F2A—C1A—C2	112.6 (3)	C13—C8—C5	120.31 (19)
F3A—C1A—C2	114.0 (3)	C10—C9—C8	124.99 (18)
C11—O3—C14	117.82 (17)	C10—C9—N1	115.23 (18)
O1—N1—O2	124.0 (2)	C8—C9—N1	119.73 (18)
O1—N1—C9	119.3 (2)	C9—C10—C11	118.1 (2)
O2—N1—C9	116.6 (2)	C9—C10—H10	120.4 (12)
C3—C2—C7	119.6 (2)	C11—C10—H10	121.5 (12)
C3—C2—C1A	120.2 (2)	O3—C11—C12	116.66 (18)
C7—C2—C1A	120.2 (2)	O3—C11—C10	124.2 (2)
C4—C3—C2	120.3 (2)	C12—C11—C10	119.1 (2)
C4—C3—H3	120.5 (14)	C13—C12—C11	120.76 (19)
C2—C3—H3	119.2 (14)	C13—C12—H12	119.6
C3—C4—C5	120.9 (2)	C11—C12—H12	119.6
C3—C4—H4	118.5 (15)	C12—C13—C8	122.4 (2)
C5—C4—H4	120.6 (15)	C12—C13—H11	117.6 (14)
C4—C5—C6	118.1 (2)	C8—C13—H11	120.1 (14)
C4—C5—C8	122.17 (19)	O3—C14—H14A	109.5
C6—C5—C8	119.66 (19)	O3—C14—H14B	109.5
C7—C6—C5	121.0 (2)	H14A—C14—H14B	109.5
C7—C6—H6	119.8 (14)	O3—C14—H14C	109.5
C5—C6—H6	119.2 (14)	H14A—C14—H14C	109.5
C6—C7—C2	120.1 (2)	H14B—C14—H14C	109.5
F1A—C1A—C2—C3	−156.3 (8)	C13—C8—C9—C10	−2.3 (3)
F2A—C1A—C2—C3	80.8 (6)	C5—C8—C9—C10	178.5 (2)
F3A—C1A—C2—C3	−32.4 (6)	C13—C8—C9—N1	−179.6 (2)
F1A—C1A—C2—C7	24.9 (8)	C5—C8—C9—N1	1.2 (3)
F2A—C1A—C2—C7	−98.0 (6)	O1—N1—C9—C10	−111.7 (2)
F3A—C1A—C2—C7	148.7 (5)	O2—N1—C9—C10	66.8 (3)
C7—C2—C3—C4	1.1 (3)	O1—N1—C9—C8	65.8 (3)
C1A—C2—C3—C4	−177.7 (2)	O2—N1—C9—C8	−115.6 (2)
C2—C3—C4—C5	−0.4 (3)	C8—C9—C10—C11	0.5 (3)
C3—C4—C5—C6	−0.4 (3)	N1—C9—C10—C11	177.87 (19)
C3—C4—C5—C8	176.8 (2)	C14—O3—C11—C12	−172.8 (2)
C4—C5—C6—C7	0.5 (3)	C14—O3—C11—C10	7.2 (3)
C8—C5—C6—C7	−176.7 (2)	C9—C10—C11—O3	−177.8 (2)
C5—C6—C7—C2	0.2 (4)	C9—C10—C11—C12	2.2 (3)
C3—C2—C7—C6	−1.0 (3)	O3—C11—C12—C13	177.1 (2)
C1A—C2—C7—C6	177.8 (2)	C10—C11—C12—C13	−2.9 (3)
C4—C5—C8—C9	50.9 (3)	C11—C12—C13—C8	0.9 (4)
C6—C5—C8—C9	−131.9 (2)	C9—C8—C13—C12	1.6 (3)
C4—C5—C8—C13	−128.2 (2)	C5—C8—C13—C12	−179.2 (2)
C6—C5—C8—C13	48.9 (3)