1-Dibromo-methyl-4-meth-oxy-2-nitro-benzene.

The asymmetric unit of the title compound, C(8)H(7)Br(2)NO(3), comprises two crystallographically independent mol-ecules (A and B). The nitro groups are twisted from the attached benzene rings, making dihedral angles of 39.26 (9) and 35.90 (9)° in mol-ecules A and B, respectively. In each mol-ecule, the dibromo-methyl group is orientated in such a way that the two Br atoms are tilted away from the benzene ring. An inter-esting features of the crystal structure is the two short Br⋯Br inter-actions which, together with inter-molecular C-H⋯O hydrogen bonds, link the mol-ecules into an extended three-dimensional network. The crystal structure is further stabilized by weak C-H⋯π inter-actions.

Related literature

For general background to and applications of brominated organic compounds, see Augustine et al. (2007 ▶); Derdau et al. (2003 ▶); Khatuya (2001 ▶); Tyeklar et al. (1993 ▶). For related structures, see: Fun, Chantrapromma, Maity et al. (2009 ▶); Fun, Chantrapromma, Sujith et al. (2009 ▶); Yeap et al. (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C8H7Br2NO3

M = 324.97

Triclinic,

a = 7.9591 (1) Å

b = 11.1949 (2) Å

c = 12.2509 (2) Å

α = 106.285 (1)°

β = 99.691 (1)°

γ = 102.401 (1)°

V = 992.45 (3) Å3

Z = 4

Mo Kα radiation

μ = 8.15 mm−1

T = 100 K

0.28 × 0.25 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.210, T max = 0.311 (expected range = 0.147–0.218)

32659 measured reflections

8800 independent reflections

7332 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.066

S = 1.01

8800 reflections

261 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.78 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031833/wn2343sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031833/wn2343Isup2.hkl

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

C8H7Br2NO3	Z = 4
Mr = 324.97	F(000) = 624
Triclinic, P1	Dx = 2.175 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9591 (1) Å	Cell parameters from 9885 reflections
b = 11.1949 (2) Å	θ = 2.2–35.1°
c = 12.2509 (2) Å	µ = 8.15 mm−1
α = 106.285 (1)°	T = 100 K
β = 99.691 (1)°	Block, colourless
γ = 102.401 (1)°	0.28 × 0.25 × 0.19 mm
V = 992.45 (3) Å3

Bruker SMART APEXII CCD area-detector diffractometer	8800 independent reflections
Radiation source: fine-focus sealed tube	7332 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 35.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.210, Tmax = 0.311	k = −17→18
32659 measured reflections	l = −19→19

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0361P)2 + 0.2346P] where P = (Fo2 + 2Fc2)/3
8800 reflections	(Δ/σ)max = 0.004
261 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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 > 2sigma(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
Br1A	0.79537 (2)	1.230776 (16)	0.197580 (14)	0.02458 (4)
Br2A	0.90786 (2)	1.101536 (16)	0.387687 (13)	0.02180 (4)
O1A	0.76010 (16)	0.62902 (12)	−0.10724 (10)	0.0229 (2)
O2A	0.30267 (16)	0.76549 (13)	0.10327 (11)	0.0265 (2)
O3A	0.37293 (16)	0.96938 (13)	0.11963 (11)	0.0257 (2)
N1A	0.40781 (17)	0.86506 (14)	0.10586 (11)	0.0208 (2)
C1A	0.8937 (2)	0.94163 (16)	0.11837 (13)	0.0209 (3)
H1AA	0.9990	1.0061	0.1578	0.025*
C2A	0.8985 (2)	0.83283 (16)	0.03310 (13)	0.0216 (3)
H2AA	1.0052	0.8260	0.0142	0.026*
C3A	0.7427 (2)	0.73241 (15)	−0.02523 (13)	0.0195 (3)
C4A	0.58321 (19)	0.74374 (15)	0.00283 (13)	0.0188 (2)
H4AA	0.4792	0.6770	−0.0335	0.023*
C5A	0.58299 (19)	0.85699 (15)	0.08631 (13)	0.0185 (2)
C6A	0.73536 (19)	0.95856 (15)	0.14790 (13)	0.0184 (2)
C7A	0.7370 (2)	1.07568 (15)	0.24351 (13)	0.0196 (3)
C8A	0.6054 (2)	0.52136 (17)	−0.16335 (15)	0.0256 (3)
H8AA	0.6344	0.4546	−0.2193	0.038*
H8AB	0.5141	0.5491	−0.2029	0.038*
H8AC	0.5640	0.4883	−0.1055	0.038*
Br1B	−0.20637 (2)	0.726206 (17)	0.325018 (14)	0.02462 (4)
Br2B	−0.10244 (2)	0.523519 (16)	0.125556 (13)	0.02342 (4)
O1B	0.50849 (16)	0.63292 (12)	0.60857 (11)	0.0243 (2)
O2B	0.49443 (16)	0.92884 (12)	0.36858 (11)	0.0252 (2)
O3B	0.22098 (17)	0.93622 (12)	0.34859 (12)	0.0261 (2)
N1B	0.33898 (17)	0.88484 (13)	0.36914 (11)	0.0197 (2)
C1B	0.1045 (2)	0.56681 (15)	0.38962 (13)	0.0206 (3)
H1BA	−0.0019	0.5017	0.3575	0.025*
C2B	0.2309 (2)	0.55536 (16)	0.47501 (14)	0.0215 (3)
H2BA	0.2081	0.4840	0.5005	0.026*
C3B	0.3935 (2)	0.65079 (16)	0.52360 (13)	0.0200 (3)
C4B	0.4281 (2)	0.75603 (15)	0.48395 (13)	0.0199 (3)
H4BA	0.5370	0.8186	0.5131	0.024*
C5B	0.29538 (19)	0.76575 (15)	0.39929 (13)	0.0180 (2)
C6B	0.13101 (19)	0.67357 (15)	0.34948 (13)	0.0185 (2)
C7B	−0.0114 (2)	0.68337 (16)	0.25833 (13)	0.0203 (3)
C8B	0.6731 (2)	0.73163 (19)	0.66117 (16)	0.0289 (3)
H8BA	0.7436	0.7088	0.7196	0.043*
H8BB	0.6504	0.8126	0.6971	0.043*
H8BC	0.7359	0.7397	0.6021	0.043*
H7A	0.627 (3)	1.0704 (19)	0.2645 (17)	0.013 (4)*
H7B	0.022 (3)	0.747 (2)	0.226 (2)	0.028 (6)*

	U11	U22	U33	U12	U13	U23
Br1A	0.03013 (8)	0.01907 (7)	0.02323 (7)	0.00585 (6)	0.00401 (6)	0.00714 (6)
Br2A	0.01964 (7)	0.02534 (8)	0.01851 (6)	0.00619 (5)	0.00280 (5)	0.00539 (5)
O1A	0.0221 (5)	0.0217 (5)	0.0231 (5)	0.0078 (4)	0.0056 (4)	0.0033 (4)
O2A	0.0185 (5)	0.0262 (6)	0.0315 (6)	0.0021 (4)	0.0067 (4)	0.0068 (5)
O3A	0.0211 (5)	0.0255 (6)	0.0293 (6)	0.0111 (4)	0.0033 (4)	0.0052 (5)
N1A	0.0171 (5)	0.0232 (6)	0.0198 (5)	0.0060 (5)	0.0029 (4)	0.0043 (5)
C1A	0.0167 (6)	0.0229 (7)	0.0215 (6)	0.0049 (5)	0.0037 (5)	0.0060 (5)
C2A	0.0180 (6)	0.0255 (7)	0.0210 (6)	0.0071 (5)	0.0051 (5)	0.0062 (5)
C3A	0.0206 (6)	0.0198 (7)	0.0185 (6)	0.0076 (5)	0.0039 (5)	0.0061 (5)
C4A	0.0173 (6)	0.0179 (6)	0.0196 (6)	0.0050 (5)	0.0020 (5)	0.0051 (5)
C5A	0.0158 (6)	0.0200 (7)	0.0199 (6)	0.0062 (5)	0.0037 (5)	0.0063 (5)
C6A	0.0173 (6)	0.0189 (6)	0.0186 (6)	0.0051 (5)	0.0036 (5)	0.0060 (5)
C7A	0.0191 (6)	0.0186 (6)	0.0189 (6)	0.0034 (5)	0.0034 (5)	0.0046 (5)
C8A	0.0278 (8)	0.0205 (7)	0.0260 (7)	0.0066 (6)	0.0064 (6)	0.0042 (6)
Br1B	0.01982 (7)	0.02733 (8)	0.02389 (7)	0.00989 (6)	0.00277 (5)	0.00308 (6)
Br2B	0.02590 (7)	0.02424 (8)	0.01841 (6)	0.00830 (6)	0.00365 (5)	0.00441 (5)
O1B	0.0208 (5)	0.0264 (6)	0.0264 (5)	0.0062 (4)	0.0013 (4)	0.0125 (5)
O2B	0.0205 (5)	0.0262 (6)	0.0282 (6)	0.0014 (4)	0.0061 (4)	0.0118 (5)
O3B	0.0262 (6)	0.0224 (6)	0.0327 (6)	0.0100 (5)	0.0059 (5)	0.0122 (5)
N1B	0.0209 (6)	0.0174 (6)	0.0202 (5)	0.0043 (5)	0.0045 (4)	0.0065 (4)
C1B	0.0197 (6)	0.0189 (7)	0.0225 (6)	0.0038 (5)	0.0042 (5)	0.0076 (5)
C2B	0.0211 (6)	0.0197 (7)	0.0251 (7)	0.0055 (5)	0.0058 (5)	0.0094 (5)
C3B	0.0187 (6)	0.0211 (7)	0.0216 (6)	0.0073 (5)	0.0049 (5)	0.0077 (5)
C4B	0.0181 (6)	0.0200 (7)	0.0211 (6)	0.0050 (5)	0.0040 (5)	0.0065 (5)
C5B	0.0191 (6)	0.0165 (6)	0.0196 (6)	0.0055 (5)	0.0057 (5)	0.0066 (5)
C6B	0.0170 (6)	0.0190 (6)	0.0192 (6)	0.0051 (5)	0.0042 (5)	0.0058 (5)
C7B	0.0193 (6)	0.0199 (7)	0.0208 (6)	0.0048 (5)	0.0039 (5)	0.0065 (5)
C8B	0.0228 (7)	0.0303 (9)	0.0301 (8)	0.0047 (6)	−0.0012 (6)	0.0112 (7)

Br1A—C7A	1.9587 (15)	Br1B—C7B	1.9576 (16)
Br2A—C7A	1.9462 (15)	Br2B—C7B	1.9460 (16)
O1A—C3A	1.3535 (19)	O1B—C3B	1.3547 (19)
O1A—C8A	1.433 (2)	O1B—C8B	1.431 (2)
O2A—N1A	1.2306 (18)	O2B—N1B	1.2314 (17)
O3A—N1A	1.2305 (19)	O3B—N1B	1.2288 (18)
N1A—C5A	1.4710 (19)	N1B—C5B	1.4680 (19)
C1A—C2A	1.377 (2)	C1B—C2B	1.378 (2)
C1A—C6A	1.405 (2)	C1B—C6B	1.404 (2)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.402 (2)	C2B—C3B	1.401 (2)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.392 (2)	C3B—C4B	1.388 (2)
C4A—C5A	1.388 (2)	C4B—C5B	1.395 (2)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.397 (2)	C5B—C6B	1.395 (2)
C6A—C7A	1.489 (2)	C6B—C7B	1.497 (2)
C7A—H7A	0.948 (19)	C7B—H7B	0.92 (2)
C8A—H8AA	0.9600	C8B—H8BA	0.9600
C8A—H8AB	0.9600	C8B—H8BB	0.9600
C8A—H8AC	0.9600	C8B—H8BC	0.9600
Br1A···Br2Bi	3.5915 (3)	Br2A···Br1Bii	3.6279 (2)
C3A—O1A—C8A	117.29 (13)	C3B—O1B—C8B	116.75 (13)
O3A—N1A—O2A	123.97 (14)	O3B—N1B—O2B	123.87 (14)
O3A—N1A—C5A	118.23 (13)	O3B—N1B—C5B	118.83 (12)
O2A—N1A—C5A	117.75 (14)	O2B—N1B—C5B	117.28 (13)
C2A—C1A—C6A	122.27 (14)	C2B—C1B—C6B	122.16 (14)
C2A—C1A—H1AA	118.9	C2B—C1B—H1BA	118.9
C6A—C1A—H1AA	118.9	C6B—C1B—H1BA	118.9
C1A—C2A—C3A	120.06 (14)	C1B—C2B—C3B	120.25 (14)
C1A—C2A—H2AA	120.0	C1B—C2B—H2BA	119.9
C3A—C2A—H2AA	120.0	C3B—C2B—H2BA	119.9
O1A—C3A—C4A	124.35 (14)	O1B—C3B—C4B	124.10 (14)
O1A—C3A—C2A	115.97 (13)	O1B—C3B—C2B	116.25 (14)
C4A—C3A—C2A	119.68 (14)	C4B—C3B—C2B	119.65 (14)
C5A—C4A—C3A	118.44 (14)	C3B—C4B—C5B	118.43 (14)
C5A—C4A—H4AA	120.8	C3B—C4B—H4BA	120.8
C3A—C4A—H4AA	120.8	C5B—C4B—H4BA	120.8
C4A—C5A—C6A	123.78 (14)	C4B—C5B—C6B	123.70 (14)
C4A—C5A—N1A	115.23 (13)	C4B—C5B—N1B	114.52 (13)
C6A—C5A—N1A	120.98 (14)	C6B—C5B—N1B	121.73 (13)
C5A—C6A—C1A	115.70 (14)	C5B—C6B—C1B	115.76 (14)
C5A—C6A—C7A	123.71 (13)	C5B—C6B—C7B	123.88 (14)
C1A—C6A—C7A	120.52 (13)	C1B—C6B—C7B	120.36 (13)
C6A—C7A—Br2A	111.59 (11)	C6B—C7B—Br2B	111.47 (11)
C6A—C7A—Br1A	110.77 (10)	C6B—C7B—Br1B	110.83 (10)
Br2A—C7A—Br1A	108.66 (7)	Br2B—C7B—Br1B	109.65 (7)
C6A—C7A—H7A	113.2 (12)	C6B—C7B—H7B	115.7 (15)
Br2A—C7A—H7A	104.8 (12)	Br2B—C7B—H7B	105.1 (15)
Br1A—C7A—H7A	107.5 (12)	Br1B—C7B—H7B	103.7 (15)
O1A—C8A—H8AA	109.5	O1B—C8B—H8BA	109.5
O1A—C8A—H8AB	109.5	O1B—C8B—H8BB	109.5
H8AA—C8A—H8AB	109.5	H8BA—C8B—H8BB	109.5
O1A—C8A—H8AC	109.5	O1B—C8B—H8BC	109.5
H8AA—C8A—H8AC	109.5	H8BA—C8B—H8BC	109.5
H8AB—C8A—H8AC	109.5	H8BB—C8B—H8BC	109.5
C6A—C1A—C2A—C3A	−1.9 (2)	C6B—C1B—C2B—C3B	−1.1 (2)
C8A—O1A—C3A—C4A	−3.9 (2)	C8B—O1B—C3B—C4B	1.5 (2)
C8A—O1A—C3A—C2A	176.29 (14)	C8B—O1B—C3B—C2B	−178.30 (15)
C1A—C2A—C3A—O1A	−179.68 (14)	C1B—C2B—C3B—O1B	178.77 (15)
C1A—C2A—C3A—C4A	0.5 (2)	C1B—C2B—C3B—C4B	−1.1 (2)
O1A—C3A—C4A—C5A	−178.01 (14)	O1B—C3B—C4B—C5B	−177.36 (15)
C2A—C3A—C4A—C5A	1.8 (2)	C2B—C3B—C4B—C5B	2.4 (2)
C3A—C4A—C5A—C6A	−2.9 (2)	C3B—C4B—C5B—C6B	−1.9 (2)
C3A—C4A—C5A—N1A	176.35 (13)	C3B—C4B—C5B—N1B	175.71 (14)
O3A—N1A—C5A—C4A	−139.68 (14)	O3B—N1B—C5B—C4B	−142.98 (15)
O2A—N1A—C5A—C4A	37.79 (19)	O2B—N1B—C5B—C4B	35.46 (19)
O3A—N1A—C5A—C6A	39.6 (2)	O3B—N1B—C5B—C6B	34.7 (2)
O2A—N1A—C5A—C6A	−142.94 (15)	O2B—N1B—C5B—C6B	−146.90 (14)
C4A—C5A—C6A—C1A	1.6 (2)	C4B—C5B—C6B—C1B	−0.1 (2)
N1A—C5A—C6A—C1A	−177.63 (13)	N1B—C5B—C6B—C1B	−177.56 (14)
C4A—C5A—C6A—C7A	−175.35 (14)	C4B—C5B—C6B—C7B	−179.76 (15)
N1A—C5A—C6A—C7A	5.5 (2)	N1B—C5B—C6B—C7B	2.8 (2)
C2A—C1A—C6A—C5A	0.9 (2)	C2B—C1B—C6B—C5B	1.6 (2)
C2A—C1A—C6A—C7A	177.90 (14)	C2B—C1B—C6B—C7B	−178.73 (15)
C5A—C6A—C7A—Br2A	124.47 (14)	C5B—C6B—C7B—Br2B	130.42 (13)
C1A—C6A—C7A—Br2A	−52.30 (17)	C1B—C6B—C7B—Br2B	−49.18 (17)
C5A—C6A—C7A—Br1A	−114.33 (14)	C5B—C6B—C7B—Br1B	−107.15 (14)
C1A—C6A—C7A—Br1A	68.89 (16)	C1B—C6B—C7B—Br1B	73.24 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7A···O2B	0.95 (2)	2.47 (2)	3.134 (2)	126.8 (17)
C8B—H8BA···O1Aiii	0.96	2.52	3.370 (2)	148
C8A—H8AA···Cg2iv	0.96	2.95	3.839 (2)	155

Table 1

Selected interatomic distances (Å)

Br1A⋯Br2Bi	3.5915 (3)
Br2A⋯Br1Bii	3.6279 (2)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7A—H7A⋯O2B	0.95 (2)	2.47 (2)	3.134 (2)	126.8 (17)
C8B—H8BA⋯O1Aiii	0.96	2.52	3.370 (2)	148
C8A—H8AA⋯Cg2iv	0.96	2.95	3.839 (2)	155

Symmetry codes: (iii) ; (iv) . Cg2 is the centroid of the C1B–C6B benzene ring.