4,4'-Dibromo-2-nitro-biphen-yl.

The title compound, C(12)H(7)Br(2)NO(2), a biphenyl derivative, displays a twisted conformation with the two benzene rings making a dihedral angle of 55.34 (14)°. The dihedral angle between the nitro group and its parent benzene ring is 26.8 (2)°. The crystal structure is stabilized by inter-molecular C-H⋯Br and C-H⋯O inter-actions, which lead to the formation of chains propagating along the c-axis direction.

Related literature

For the use of dibromo-2-nitro-biphenyl as a crucial precursor in the formation of 2,7-disubstituted carbazole derivatives, see: Dierschke et al. (2003 ▶); Blouin et al. (2007 ▶). For details concerning 3,6-disubstituted analogs, see: Thomas et al. (2001 ▶). For related structures, see: Akhter et al. (2009 ▶); Hou et al. (2011 ▶); Kia et al. (2009 ▶); Rajnikant et al. (1995 ▶); Sim (1986 ▶).

Experimental

Crystal data

C12H7Br2NO2

M = 357.01

Orthorhombic,

a = 15.8761 (14) Å

b = 7.4350 (7) Å

c = 20.7517 (13) Å

V = 2449.5 (4) Å3

Z = 8

Mo Kα radiation

μ = 6.61 mm−1

T = 293 K

0.40 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.089, T max = 0.138

13009 measured reflections

2607 independent reflections

1521 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.095

S = 1.00

2607 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.70 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812000347/su2358sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000347/su2358Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000347/su2358Isup3.cml

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

C12H7Br2NO2	F(000) = 1376
Mr = 357.01	Dx = 1.936 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 25 reflections
a = 15.8761 (14) Å	θ = 20–30°
b = 7.4350 (7) Å	µ = 6.61 mm−1
c = 20.7517 (13) Å	T = 293 K
V = 2449.5 (4) Å3	Needle, yellow
Z = 8	0.40 × 0.35 × 0.30 mm

Bruker Kappa APEXII CCD diffractometer	2607 independent reflections
Radiation source: fine-focus sealed tube	1521 reflections with I > 2σ(I)
graphite	Rint = 0.045
ω and φ scan	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −18→20
Tmin = 0.089, Tmax = 0.138	k = −9→9
13009 measured reflections	l = −16→26

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.041P)2 + 1.6705P] where P = (Fo2 + 2Fc2)/3
2607 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.70 e Å−3

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
Br1	0.03710 (3)	0.09619 (7)	0.65877 (2)	0.05528 (18)
Br2	0.15585 (3)	0.40559 (8)	0.15916 (2)	0.06048 (19)
C7	0.1445 (2)	0.3592 (6)	0.24826 (17)	0.0382 (10)
C9	0.1668 (2)	0.1683 (6)	0.33822 (18)	0.0410 (10)
H9	0.1880	0.0618	0.3552	0.049*
C1	0.0668 (2)	0.1609 (5)	0.57419 (16)	0.0321 (9)
O1	0.30721 (17)	0.1125 (4)	0.51041 (14)	0.0524 (8)
C11	0.0974 (3)	0.4456 (6)	0.35168 (19)	0.0438 (11)
H11	0.0702	0.5287	0.3779	0.053*
N	0.26111 (19)	0.2075 (5)	0.47864 (15)	0.0342 (8)
C5	0.0275 (2)	0.2556 (5)	0.46893 (18)	0.0343 (10)
H5	−0.0144	0.2906	0.4403	0.041*
O2	0.28561 (16)	0.3083 (5)	0.43688 (14)	0.0518 (8)
C4	0.1106 (2)	0.2495 (5)	0.44718 (16)	0.0289 (9)
C2	0.1493 (2)	0.1555 (5)	0.55524 (17)	0.0329 (9)
H2	0.1910	0.1212	0.5842	0.039*
C10	0.1272 (2)	0.2897 (5)	0.37828 (16)	0.0292 (9)
C6	0.0050 (2)	0.2116 (5)	0.53120 (17)	0.0362 (10)
H6	−0.0511	0.2162	0.5440	0.043*
C8	0.1752 (2)	0.2031 (7)	0.27314 (19)	0.0467 (12)
H8	0.2018	0.1201	0.2465	0.056*
C3	0.1701 (2)	0.2011 (5)	0.49318 (17)	0.0280 (9)
C12	0.1067 (3)	0.4826 (6)	0.28703 (19)	0.0476 (11)
H12	0.0873	0.5908	0.2701	0.057*

	U11	U22	U33	U12	U13	U23
Br1	0.0631 (3)	0.0675 (4)	0.0352 (3)	−0.0030 (3)	0.01363 (19)	0.0059 (2)
Br2	0.0541 (3)	0.0981 (5)	0.0293 (2)	0.0006 (3)	0.00445 (18)	0.0110 (3)
C7	0.034 (2)	0.056 (3)	0.025 (2)	−0.002 (2)	−0.0014 (17)	0.002 (2)
C9	0.046 (3)	0.042 (3)	0.034 (2)	0.011 (2)	0.0008 (17)	0.003 (2)
C1	0.035 (2)	0.036 (3)	0.0254 (19)	−0.0034 (18)	0.0028 (16)	−0.0055 (18)
O1	0.0363 (16)	0.074 (2)	0.0470 (19)	0.0164 (17)	−0.0024 (13)	0.0104 (17)
C11	0.054 (3)	0.045 (3)	0.033 (2)	0.015 (2)	0.0106 (18)	0.001 (2)
N	0.0308 (18)	0.042 (2)	0.0297 (18)	−0.0003 (17)	−0.0018 (14)	−0.0033 (17)
C5	0.032 (2)	0.039 (3)	0.031 (2)	0.0032 (19)	−0.0054 (15)	−0.0030 (19)
O2	0.0366 (18)	0.066 (2)	0.0530 (19)	−0.0062 (15)	0.0047 (13)	0.0157 (18)
C4	0.031 (2)	0.029 (2)	0.027 (2)	0.0010 (17)	−0.0027 (15)	−0.0020 (17)
C2	0.031 (2)	0.037 (3)	0.030 (2)	0.0020 (18)	−0.0052 (16)	−0.0032 (18)
C10	0.029 (2)	0.035 (3)	0.0239 (18)	0.0014 (18)	−0.0032 (15)	−0.0006 (19)
C6	0.028 (2)	0.040 (3)	0.040 (2)	0.0018 (19)	0.0046 (17)	−0.005 (2)
C8	0.049 (3)	0.059 (3)	0.032 (2)	0.010 (2)	0.0054 (17)	−0.012 (2)
C3	0.024 (2)	0.032 (2)	0.029 (2)	0.0016 (17)	0.0005 (13)	−0.0016 (18)
C12	0.057 (3)	0.049 (3)	0.037 (2)	0.012 (2)	0.0012 (19)	0.013 (2)

Br1—C1	1.880 (3)	N—O2	1.210 (4)
Br2—C7	1.890 (4)	N—C3	1.477 (4)
C7—C8	1.361 (6)	C5—C6	1.380 (5)
C7—C12	1.361 (6)	C5—C4	1.395 (5)
C9—C10	1.378 (5)	C5—H5	0.9300
C9—C8	1.382 (5)	C4—C3	1.390 (5)
C9—H9	0.9300	C4—C10	1.484 (5)
C1—C2	1.368 (5)	C2—C3	1.372 (5)
C1—C6	1.380 (5)	C2—H2	0.9300
O1—N	1.212 (4)	C6—H6	0.9300
C11—C10	1.369 (5)	C8—H8	0.9300
C11—C12	1.377 (5)	C12—H12	0.9300
C11—H11	0.9300
C8—C7—C12	120.6 (4)	C5—C4—C10	118.2 (3)
C8—C7—Br2	119.5 (3)	C1—C2—C3	119.5 (3)
C12—C7—Br2	119.8 (3)	C1—C2—H2	120.2
C10—C9—C8	120.7 (4)	C3—C2—H2	120.2
C10—C9—H9	119.6	C11—C10—C9	118.0 (3)
C8—C9—H9	119.6	C11—C10—C4	119.8 (3)
C2—C1—C6	120.3 (3)	C9—C10—C4	122.0 (4)
C2—C1—Br1	120.1 (3)	C1—C6—C5	119.0 (3)
C6—C1—Br1	119.7 (3)	C1—C6—H6	120.5
C10—C11—C12	121.7 (4)	C5—C6—H6	120.5
C10—C11—H11	119.2	C7—C8—C9	119.7 (4)
C12—C11—H11	119.2	C7—C8—H8	120.1
O2—N—O1	123.8 (3)	C9—C8—H8	120.1
O2—N—C3	118.7 (3)	C2—C3—C4	123.1 (3)
O1—N—C3	117.5 (3)	C2—C3—N	115.8 (3)
C6—C5—C4	122.7 (3)	C4—C3—N	121.1 (3)
C6—C5—H5	118.6	C7—C12—C11	119.2 (4)
C4—C5—H5	118.6	C7—C12—H12	120.4
C3—C4—C5	115.4 (3)	C11—C12—H12	120.4
C3—C4—C10	126.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Br2i	0.93	2.89	3.798 (3)	165
C9—H9···O2ii	0.93	2.57	3.454 (5)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Br2i	0.93	2.89	3.798 (3)	165
C9—H9⋯O2ii	0.93	2.57	3.454 (5)	159

Symmetry codes: (i) ; (ii) .