1-Bromo-2,3,5,6-tetra-fluoro-4-nitro-benzene.

In the title compound, C(6)BrF(4)NO(2), the nitro group is twisted by 41.7 (3)° with reference to the arene ring mean plane. The main inter-actions stabilizing the crystal structure include O⋯Br contacts [3.150 (2) and 3.201 (2) Å], while F⋯F inter-actions are minor [2.863 (3)-2.908 (3) Å].

Related literature

For halogen inter­actions in mol­ecular crystal structures, see: Awwadi et al. (2006 ▶); Brammer et al. (2001 ▶); Metrangolo et al. (2008 ▶). For fluorine-involved inter­actions, see: Schwarzer et al. (2010 ▶); Merz & Vasylyeva (2010 ▶); Schwarzer & Weber (2008 ▶); Reichenbächer et al. (2005 ▶). For the synthesis, see: Shtark & Shteingarts (1976 ▶).

Experimental

Crystal data

C6BrF4NO2

M = 273.98

Orthorhombic,

a = 5.6718 (3) Å

b = 10.9476 (6) Å

c = 12.2652 (8) Å

V = 761.58 (8) Å3

Z = 4

Mo Kα radiation

μ = 5.44 mm−1

T = 93 K

0.13 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.536, T max = 0.612

4314 measured reflections

1550 independent reflections

1447 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.053

S = 1.00

1550 reflections

127 parameters

1 restraint

Δρmax = 0.32 e Å−3

Δρmin = −0.53 e Å−3

Absolute structure: Flack (1983) ▶, 636 Friedel pairs

Flack parameter: 0.026 (10)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681102201X/su2278sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102201X/su2278Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681102201X/su2278Isup3.cml

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

C6BrF4NO2	F(000) = 520
Mr = 273.98	Dx = 2.390 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2319 reflections
a = 5.6718 (3) Å	θ = 3.7–32.8°
b = 10.9476 (6) Å	µ = 5.44 mm−1
c = 12.2652 (8) Å	T = 93 K
V = 761.58 (8) Å3	Needle, colourless
Z = 4	0.13 × 0.13 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	1550 independent reflections
Radiation source: fine-focus sealed tube	1447 reflections with I > 2σ(I)
graphite	Rint = 0.026
phi and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −7→7
Tmin = 0.536, Tmax = 0.612	k = −14→12
4314 measured reflections	l = −15→15

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)] = 0.023	w = 1/[σ2(Fo2) + (0.0208P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.053	(Δ/σ)max = 0.008
S = 1.00	Δρmax = 0.32 e Å−3
1550 reflections	Δρmin = −0.53 e Å−3
127 parameters	Absolute structure: Flack (1983), 636 Friedel pairs
1 restraint	Flack parameter: 0.026 (10)

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	1.16169 (4)	0.62891 (2)	0.12241 (5)	0.01760 (10)
F1	0.9560 (3)	0.69267 (15)	−0.10033 (17)	0.0188 (4)
F2	0.6066 (3)	0.58458 (16)	−0.20909 (18)	0.0178 (4)
F3	0.5004 (3)	0.30738 (15)	0.08418 (15)	0.0181 (4)
F4	0.8565 (3)	0.41466 (18)	0.19058 (19)	0.0192 (4)
N1	0.3610 (4)	0.3813 (2)	−0.1276 (3)	0.0148 (6)
O1	0.3925 (4)	0.36408 (18)	−0.2245 (2)	0.0181 (5)
O2	0.1833 (3)	0.3518 (2)	−0.0760 (2)	0.0207 (6)
C1	0.8465 (4)	0.5971 (3)	−0.0542 (3)	0.0134 (7)
C2	0.6671 (4)	0.5405 (3)	−0.1118 (3)	0.0136 (7)
C3	0.5498 (4)	0.4424 (3)	−0.0658 (3)	0.0128 (7)
C4	0.6105 (5)	0.4023 (3)	0.0374 (3)	0.0146 (7)
C5	0.7936 (4)	0.4574 (3)	0.0933 (3)	0.0129 (8)
C6	0.9119 (4)	0.5558 (3)	0.0468 (3)	0.0146 (7)

	U11	U22	U33	U12	U13	U23
Br1	0.01516 (11)	0.01875 (15)	0.01890 (19)	−0.00140 (8)	−0.00323 (18)	−0.0046 (2)
F1	0.0214 (7)	0.0153 (9)	0.0198 (13)	−0.0066 (6)	0.0011 (8)	0.0038 (8)
F2	0.0241 (8)	0.0159 (9)	0.0135 (13)	−0.0005 (7)	−0.0031 (9)	0.0027 (9)
F3	0.0224 (7)	0.0155 (9)	0.0164 (12)	−0.0057 (6)	0.0040 (8)	0.0017 (7)
F4	0.0256 (9)	0.0177 (10)	0.0142 (14)	0.0018 (7)	−0.0024 (8)	0.0009 (9)
N1	0.0150 (12)	0.0158 (15)	0.014 (2)	−0.0005 (8)	−0.0002 (11)	−0.0015 (13)
O1	0.0205 (8)	0.0206 (12)	0.0133 (16)	−0.0014 (7)	−0.0005 (10)	−0.0048 (10)
O2	0.0134 (9)	0.0245 (14)	0.0241 (17)	−0.0025 (7)	0.0025 (10)	−0.0016 (11)
C1	0.0165 (12)	0.0082 (15)	0.016 (2)	−0.0009 (10)	0.0038 (13)	0.0006 (13)
C2	0.0160 (12)	0.0125 (16)	0.012 (2)	0.0048 (9)	0.0001 (12)	−0.0004 (14)
C3	0.0099 (10)	0.0143 (15)	0.014 (2)	0.0018 (10)	0.0001 (12)	−0.0040 (13)
C4	0.0169 (12)	0.0107 (15)	0.016 (2)	0.0019 (10)	0.0045 (13)	0.0003 (13)
C5	0.0150 (10)	0.0158 (15)	0.008 (2)	0.0030 (9)	0.0001 (11)	−0.0003 (12)
C6	0.0110 (10)	0.0169 (15)	0.016 (2)	0.0014 (10)	−0.0020 (12)	−0.0065 (13)

Br1—C6	1.874 (3)	F4—F3iii	2.877 (2)
Br1—O1i	3.150 (2)	F4—F2vii	2.901 (2)
Br1—O1ii	3.201 (2)	N1—O1	1.217 (4)
F3—O2iii	2.823 (3)	N1—O2	1.234 (3)
F1—C1	1.342 (3)	N1—C3	1.472 (4)
F1—F2iv	2.908 (3)	O1—Br1ix	3.150 (2)
F2—C2	1.332 (4)	O1—Br1x	3.201 (2)
F2—F3v	2.863 (3)	O2—F3viii	2.823 (3)
F2—F4v	2.901 (2)	C1—C6	1.369 (5)
F2—F1vi	2.908 (3)	C1—C2	1.385 (4)
F3—C4	1.341 (3)	C2—C3	1.385 (4)
F3—F2vii	2.863 (3)	C3—C4	1.383 (5)
F3—F4viii	2.877 (2)	C4—C5	1.382 (4)
F4—C5	1.331 (4)	C5—C6	1.391 (4)
C6—Br1—O1i	155.87 (10)	N1—O1—Br1ix	134.13 (18)
C6—Br1—O1ii	124.16 (9)	N1—O1—Br1x	133.10 (18)
O1i—Br1—O1ii	73.03 (6)	Br1ix—O1—Br1x	75.36 (6)
C1—F1—F2iv	169.53 (15)	N1—O2—F3viii	144.98 (19)
C2—F2—F3v	176.03 (17)	F1—C1—C6	120.9 (3)
C2—F2—F4v	127.90 (16)	F1—C1—C2	118.2 (3)
F3v—F2—F4v	55.33 (6)	C6—C1—C2	120.8 (3)
C2—F2—F1vi	88.19 (17)	F2—C2—C3	121.5 (3)
F3v—F2—F1vi	89.86 (7)	F2—C2—C1	119.0 (3)
F4v—F2—F1vi	85.76 (7)	C3—C2—C1	119.5 (3)
C4—F3—O2iii	90.56 (18)	C4—C3—C2	120.0 (3)
C4—F3—F2vii	99.04 (18)	C4—C3—N1	120.6 (3)
O2iii—F3—F2vii	161.63 (9)	C2—C3—N1	119.5 (3)
C4—F3—F4viii	168.70 (16)	F3—C4—C5	118.4 (3)
O2iii—F3—F4viii	84.17 (8)	F3—C4—C3	121.4 (3)
F2vii—F3—F4viii	83.52 (8)	C5—C4—C3	120.1 (3)
C5—F4—F3iii	88.06 (17)	F4—C5—C4	119.5 (3)
C5—F4—F2vii	97.86 (13)	F4—C5—C6	120.7 (3)
F3iii—F4—F2vii	116.85 (8)	C4—C5—C6	119.8 (3)
O1—N1—O2	125.5 (3)	C1—C6—C5	119.7 (3)
O1—N1—C3	117.8 (2)	C1—C6—Br1	120.8 (2)
O2—N1—C3	116.6 (3)	C5—C6—Br1	119.5 (2)
O2—N1—O1—Br1ix	−164.81 (19)	F4viii—F3—C4—C5	−50.3 (12)
C3—N1—O1—Br1ix	15.2 (4)	O2iii—F3—C4—C3	65.5 (3)
O2—N1—O1—Br1x	−49.6 (4)	F2vii—F3—C4—C3	−130.3 (3)
C3—N1—O1—Br1x	130.4 (2)	F4viii—F3—C4—C3	127.4 (9)
O1—N1—O2—F3viii	110.3 (4)	C2—C3—C4—F3	−179.9 (3)
C3—N1—O2—F3viii	−69.7 (4)	N1—C3—C4—F3	0.0 (4)
F2iv—F1—C1—C6	−133.4 (10)	C2—C3—C4—C5	−2.2 (4)
F2iv—F1—C1—C2	47.2 (13)	N1—C3—C4—C5	177.7 (3)
F3v—F2—C2—C3	174 (2)	F3iii—F4—C5—C4	65.3 (3)
F4v—F2—C2—C3	30.2 (4)	F2vii—F4—C5—C4	−51.5 (3)
F1vi—F2—C2—C3	113.4 (3)	F3iii—F4—C5—C6	−113.9 (3)
F3v—F2—C2—C1	−4(3)	F2vii—F4—C5—C6	129.2 (2)
F4v—F2—C2—C1	−147.6 (2)	F3—C4—C5—F4	0.5 (4)
F1vi—F2—C2—C1	−64.4 (3)	C3—C4—C5—F4	−177.2 (2)
F1—C1—C2—F2	−1.5 (4)	F3—C4—C5—C6	179.8 (3)
C6—C1—C2—F2	179.1 (3)	C3—C4—C5—C6	2.0 (4)
F1—C1—C2—C3	−179.4 (3)	F1—C1—C6—C5	179.2 (3)
C6—C1—C2—C3	1.2 (4)	C2—C1—C6—C5	−1.4 (4)
F2—C2—C3—C4	−177.2 (3)	F1—C1—C6—Br1	−1.6 (4)
C1—C2—C3—C4	0.6 (4)	C2—C1—C6—Br1	177.8 (2)
F2—C2—C3—N1	2.9 (4)	F4—C5—C6—C1	179.0 (3)
C1—C2—C3—N1	−179.2 (3)	C4—C5—C6—C1	−0.2 (4)
O1—N1—C3—C4	−138.6 (3)	F4—C5—C6—Br1	−0.2 (4)
O2—N1—C3—C4	41.4 (4)	C4—C5—C6—Br1	−179.4 (2)
O1—N1—C3—C2	41.3 (4)	O1i—Br1—C6—C1	−143.2 (2)
O2—N1—C3—C2	−138.7 (3)	O1ii—Br1—C6—C1	86.1 (3)
O2iii—F3—C4—C5	−112.3 (3)	O1i—Br1—C6—C5	36.0 (4)
F2vii—F3—C4—C5	52.0 (3)	O1ii—Br1—C6—C5	−94.7 (2)