1,3-Bis(bromo-meth-yl)-2-nitro-benzene.

In the title compound, C(8)H(7)Br(2)NO(2), an inter-mediate for the synthesis of macrocycles, the NO(2) group makes a dihedral angle of 65.07 (19)° with the arene ring, and the bromo-methyl substituents adopt a trans conformation about the ring such that the mol-ecule closely approximates C2 symmetry.

Related literature

For related structures, see: Li et al. (2006 ▶); Qin et al. (2005 ▶). For related compounds, see: Raatikainen et al. (2008 ▶); Mough et al. (2004 ▶). For the synthesis, see: Boeckmann & Vögtle (1981 ▶).

Experimental

Crystal data

C8H7Br2NO2

M = 308.97

Monoclinic,

a = 7.7837 (13) Å

b = 7.7573 (13) Å

c = 15.938 (3) Å

β = 90.933 (3)°

V = 962.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 8.39 mm−1

T = 185 K

0.20 × 0.20 × 0.08 mm

Data collection

Bruker SMART 1K diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.285, T max = 0.553

8228 measured reflections

2259 independent reflections

1812 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.083

S = 1.06

2259 reflections

118 parameters

H-atom parameters constrained

Δρmax = 1.35 e Å−3

Δρmin = −1.31 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), PLATON (Spek, 2009 ▶) and X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681000718X/ng2729sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000718X/ng2729Isup2.hkl

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

C8H7Br2NO2	F(000) = 592
Mr = 308.97	Dx = 2.133 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1024 reflections
a = 7.7837 (13) Å	θ = 2.6–28.0°
b = 7.7573 (13) Å	µ = 8.39 mm−1
c = 15.938 (3) Å	T = 185 K
β = 90.933 (3)°	Needles, colorless
V = 962.2 (3) Å3	0.20 × 0.20 × 0.08 mm
Z = 4

Bruker SMART 1K diffractometer	2259 independent reflections
Radiation source: fine-focus sealed tube	1812 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω scan	θmax = 28.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.285, Tmax = 0.553	k = −10→10
8228 measured reflections	l = −21→20

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0289P)2 + 1.9462P] where P = (Fo2 + 2Fc2)/3
2259 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 1.35 e Å−3
0 restraints	Δρmin = −1.31 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.20766 (5)	0.59088 (5)	0.74548 (2)	0.03326 (13)
Br2	0.26732 (6)	0.86865 (6)	0.32665 (3)	0.04186 (15)
C1	0.2474 (4)	0.6504 (4)	0.5246 (2)	0.0211 (7)
N1	0.2391 (4)	0.8324 (4)	0.55227 (19)	0.0245 (7)
C2	0.1776 (4)	0.6087 (4)	0.4461 (2)	0.0203 (7)
C3	0.1891 (5)	0.4378 (5)	0.4212 (2)	0.0238 (8)
H3	0.1450	0.4051	0.3676	0.029*
O1	0.3753 (4)	0.9089 (4)	0.5617 (2)	0.0434 (8)
C6	0.3228 (4)	0.5301 (5)	0.5786 (2)	0.0205 (7)
C5	0.3295 (5)	0.3604 (5)	0.5504 (2)	0.0249 (8)
H5	0.3807	0.2750	0.5855	0.030*
C7	0.3935 (5)	0.5748 (5)	0.6637 (2)	0.0281 (8)
H7A	0.4550	0.6864	0.6610	0.034*
H7B	0.4768	0.4854	0.6820	0.034*
O2	0.0993 (4)	0.8953 (4)	0.5634 (2)	0.0426 (8)
C4	0.2638 (5)	0.3131 (5)	0.4729 (2)	0.0260 (8)
H4	0.2695	0.1965	0.4550	0.031*
C8	0.0943 (5)	0.7371 (5)	0.3889 (2)	0.0259 (8)
H8A	0.0239	0.8174	0.4222	0.031*
H8B	0.0170	0.6766	0.3487	0.031*

	U11	U22	U33	U12	U13	U23
Br1	0.0391 (2)	0.0396 (2)	0.0212 (2)	−0.00245 (18)	0.00494 (16)	−0.00610 (16)
Br2	0.0346 (2)	0.0541 (3)	0.0370 (3)	−0.0017 (2)	0.00213 (18)	0.0232 (2)
C1	0.0198 (17)	0.0187 (17)	0.0247 (18)	−0.0006 (14)	0.0027 (14)	−0.0005 (14)
N1	0.0324 (18)	0.0223 (16)	0.0188 (15)	0.0027 (13)	−0.0022 (13)	0.0000 (12)
C2	0.0161 (16)	0.0231 (18)	0.0218 (18)	−0.0003 (14)	0.0033 (14)	0.0018 (14)
C3	0.0227 (18)	0.030 (2)	0.0190 (18)	−0.0043 (15)	0.0030 (15)	−0.0041 (15)
O1	0.0381 (17)	0.0343 (16)	0.058 (2)	−0.0126 (14)	0.0095 (15)	−0.0141 (15)
C6	0.0153 (16)	0.0287 (18)	0.0175 (17)	−0.0005 (14)	0.0020 (14)	0.0005 (14)
C5	0.0254 (19)	0.0218 (17)	0.028 (2)	0.0038 (15)	0.0060 (16)	0.0076 (15)
C7	0.0247 (19)	0.038 (2)	0.0215 (19)	0.0002 (16)	−0.0013 (15)	0.0014 (16)
O2	0.0310 (16)	0.0359 (16)	0.061 (2)	0.0146 (13)	−0.0064 (15)	−0.0158 (15)
C4	0.0258 (19)	0.0215 (18)	0.031 (2)	−0.0022 (15)	0.0074 (16)	−0.0021 (15)
C8	0.0228 (19)	0.031 (2)	0.0236 (19)	−0.0007 (16)	0.0001 (15)	0.0058 (15)

Br1—C7	1.967 (4)	C3—H3	0.9500
Br2—C8	1.971 (4)	C6—C5	1.392 (5)
C1—C6	1.392 (5)	C6—C7	1.497 (5)
C1—C2	1.395 (5)	C5—C4	1.379 (5)
C1—N1	1.480 (5)	C5—H5	0.9500
N1—O2	1.209 (4)	C7—H7A	0.9900
N1—O1	1.222 (4)	C7—H7B	0.9900
C2—C3	1.387 (5)	C4—H4	0.9500
C2—C8	1.491 (5)	C8—H8A	0.9900
C3—C4	1.392 (5)	C8—H8B	0.9900
C6—C1—C2	123.6 (3)	C6—C5—H5	119.2
C6—C1—N1	118.4 (3)	C6—C7—Br1	110.6 (2)
C2—C1—N1	118.0 (3)	C6—C7—H7A	109.5
O2—N1—O1	124.5 (3)	Br1—C7—H7A	109.5
O2—N1—C1	118.2 (3)	C6—C7—H7B	109.5
O1—N1—C1	117.3 (3)	Br1—C7—H7B	109.5
C3—C2—C1	116.9 (3)	H7A—C7—H7B	108.1
C3—C2—C8	119.6 (3)	C5—C4—C3	119.4 (3)
C1—C2—C8	123.5 (3)	C5—C4—H4	120.3
C2—C3—C4	121.6 (3)	C3—C4—H4	120.3
C2—C3—H3	119.2	C2—C8—Br2	111.1 (2)
C4—C3—H3	119.2	C2—C8—H8A	109.4
C1—C6—C5	116.9 (3)	Br2—C8—H8A	109.4
C1—C6—C7	123.3 (3)	C2—C8—H8B	109.4
C5—C6—C7	119.7 (3)	Br2—C8—H8B	109.4
C4—C5—C6	121.7 (3)	H8A—C8—H8B	108.0
C4—C5—H5	119.2
C6—C1—N1—O2	−115.0 (4)	N1—C1—C6—C5	−179.6 (3)
C2—C1—N1—O2	64.5 (5)	C2—C1—C6—C7	−178.4 (3)
C6—C1—N1—O1	65.5 (5)	N1—C1—C6—C7	1.0 (5)
C2—C1—N1—O1	−115.1 (4)	C1—C6—C5—C4	−0.3 (5)
C6—C1—C2—C3	−1.5 (5)	C7—C6—C5—C4	179.1 (3)
N1—C1—C2—C3	179.1 (3)	C1—C6—C7—Br1	80.1 (4)
C6—C1—C2—C8	179.0 (3)	C5—C6—C7—Br1	−99.3 (3)
N1—C1—C2—C8	−0.4 (5)	C6—C5—C4—C3	0.2 (5)
C1—C2—C3—C4	1.2 (5)	C2—C3—C4—C5	−0.6 (5)
C8—C2—C3—C4	−179.2 (3)	C3—C2—C8—Br2	−98.9 (3)
C2—C1—C6—C5	1.0 (5)	C1—C2—C8—Br2	80.6 (4)