Crystal structure of (E)-1,2-bis-(4-bromo-2,6-di-fluoro-phen-yl)diazene.

In the crystal, mol-ecules of the centrosymmetric title compound, C12H4Br2F4N2, are linked into strands along [011] by weak C-H⋯F contacts. Furthermore, the mol-ecules are π-π stacked with perpendicular ring distances of 3.4530 (9) Å.

Related literature

For background on azo­benzenes, see: Mitscherlich (1834 ▸); Fehrentz et al. (2011 ▸); Banghart et al. (2004 ▸); Levitz et al. (2013 ▸); Broichhagen et al. (2014 ▸); Velema et al. (2013 ▸); Bléger et al. (2012 ▸). For the synthesis, see: Bléger et al. (2012 ▸). For related structures, see: Wragg et al. (2011 ▸); Gabe et al. (1981 ▸); Crispini et al. (1998 ▸); Elder & Vargas-Baca (2012 ▸); Komeyama et al. (1973 ▸); Ferguson et al. (1998 ▸); Reichenbächer et al. (2007 ▸).

Experimental

Crystal data

C12H4Br2F4N2

M = 411.98

Monoclinic,

a = 10.3274 (5) Å

b = 4.5667 (2) Å

c = 13.1039 (6) Å

β = 90.340 (3)°

V = 618.00 (5) Å3

Z = 2

Mo Kα radiation

μ = 6.60 mm−1

T = 173 K

0.14 × 0.07 × 0.02 mm

Data collection

Bruker D8 Quest diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▸) T min = 0.572, T max = 0.746

9803 measured reflections

1523 independent reflections

1218 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.055

S = 1.02

1523 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.30 e Å−3

Data collection: Bruker Instrument Service (Bruker, 2007 ▸); cell refinement: APEX2 (Bruker, 2007 ▸); data reduction: SAINT (Bruker, 2007 ▸); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-III (Burnett & Johnson, 1996 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015010622/nr2060sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015010622/nr2060Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015010622/nr2060Isup3.cml

Click here for additional data file.

x y z . DOI: 10.1107/S2056989015010622/nr2060fig1.tif

The mol­ecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 30% probability level) for non-H atoms. Symmetry code: (i) 1 − x, 2 − y, 1 − z.

Click here for additional data file.

. DOI: 10.1107/S2056989015010622/nr2060fig2.tif

Weak C—H⋯F contacts (dotted lines) linking the title compound into strands along [011].

Click here for additional data file.

. DOI: 10.1107/S2056989015010622/nr2060fig3.tif

The unit cell of the title compound (displacement ellipsoids drawn at 30% probability level).

CCDC reference: 1404445

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H4Br2F4N2	F(000) = 392
Mr = 411.98	Dx = 2.214 (1) Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 95 reflections
a = 10.3274 (5) Å	θ = 5.4–24.6°
b = 4.5667 (2) Å	µ = 6.60 mm−1
c = 13.1039 (6) Å	T = 173 K
β = 90.340 (3)°	Platelet, orange
V = 618.00 (5) Å3	0.14 × 0.07 × 0.02 mm
Z = 2

Bruker D8 Quest diffractometer	1523 independent reflections
Radiation source: Microfocus source, Bruker IµS	1218 reflections with I > 2σ(I)
Focusing mirrors monochromator	Rint = 0.051
Detector resolution: 10.4167 pixels mm-1	θmax = 28.4°, θmin = 3.1°
mix of phi and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −6→6
Tmin = 0.572, Tmax = 0.746	l = −17→17
9803 measured reflections

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.055	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0231P)2 + 0.2317P] where P = (Fo2 + 2Fc2)/3
1523 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.30 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 > 2σ(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
C1	0.3771 (2)	0.7379 (5)	0.52174 (17)	0.0188 (5)
C2	0.2748 (2)	0.6243 (6)	0.46388 (18)	0.0232 (5)
C3	0.1860 (2)	0.4296 (6)	0.49948 (18)	0.0233 (5)
H3	0.1179	0.3594	0.4570	0.028*
C4	0.1983 (2)	0.3376 (5)	0.59963 (18)	0.0197 (5)
C5	0.2992 (2)	0.4325 (5)	0.66162 (18)	0.0216 (5)
H5	0.3084	0.3629	0.7296	0.026*
C6	0.3856 (2)	0.6304 (5)	0.62162 (18)	0.0205 (5)
N1	0.45691 (19)	0.9452 (5)	0.47266 (15)	0.0234 (4)
F1	0.26329 (15)	0.7158 (4)	0.36666 (10)	0.0382 (4)
F2	0.48197 (15)	0.7201 (4)	0.68235 (11)	0.0373 (4)
Br1	0.07408 (2)	0.08357 (6)	0.656884 (19)	0.02666 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0172 (11)	0.0184 (13)	0.0208 (12)	−0.0001 (10)	0.0014 (9)	−0.0017 (10)
C2	0.0266 (13)	0.0257 (14)	0.0173 (12)	−0.0002 (10)	−0.0020 (9)	0.0017 (10)
C3	0.0206 (12)	0.0262 (14)	0.0230 (12)	−0.0035 (11)	−0.0047 (9)	−0.0029 (12)
C4	0.0173 (12)	0.0150 (12)	0.0270 (13)	0.0020 (9)	0.0046 (9)	−0.0014 (10)
C5	0.0239 (12)	0.0215 (13)	0.0193 (11)	0.0016 (11)	−0.0011 (9)	0.0003 (11)
C6	0.0203 (12)	0.0199 (13)	0.0214 (12)	0.0000 (10)	−0.0052 (9)	−0.0049 (10)
N1	0.0221 (11)	0.0239 (11)	0.0243 (11)	−0.0046 (9)	−0.0016 (8)	0.0014 (10)
F1	0.0385 (9)	0.0555 (11)	0.0205 (8)	−0.0178 (8)	−0.0093 (6)	0.0125 (8)
F2	0.0372 (9)	0.0479 (10)	0.0268 (8)	−0.0201 (8)	−0.0142 (7)	0.0079 (8)
Br1	0.02328 (14)	0.02389 (15)	0.03287 (15)	−0.00452 (11)	0.00594 (9)	0.00056 (13)

C1—C2	1.397 (3)	C4—C5	1.387 (3)
C1—C6	1.400 (3)	C4—Br1	1.888 (2)
C1—N1	1.412 (3)	C5—C6	1.376 (3)
C2—F1	1.345 (3)	C5—H5	0.9500
C2—C3	1.362 (3)	C6—F2	1.335 (3)
C3—C4	1.383 (3)	N1—N1i	1.244 (4)
C3—H3	0.9500
C2—C1—C6	114.8 (2)	C3—C4—Br1	120.30 (18)
C2—C1—N1	116.3 (2)	C5—C4—Br1	117.97 (18)
C6—C1—N1	128.9 (2)	C6—C5—C4	117.9 (2)
F1—C2—C3	118.1 (2)	C6—C5—H5	121.0
F1—C2—C1	117.5 (2)	C4—C5—H5	121.0
C3—C2—C1	124.4 (2)	F2—C6—C5	117.2 (2)
C2—C3—C4	117.7 (2)	F2—C6—C1	119.4 (2)
C2—C3—H3	121.2	C5—C6—C1	123.3 (2)
C4—C3—H3	121.2	N1i—N1—C1	115.1 (2)
C3—C4—C5	121.7 (2)
C6—C1—C2—F1	−178.8 (2)	Br1—C4—C5—C6	−176.42 (17)
N1—C1—C2—F1	1.6 (3)	C4—C5—C6—F2	179.8 (2)
C6—C1—C2—C3	1.7 (4)	C4—C5—C6—C1	−0.5 (4)
N1—C1—C2—C3	−177.9 (2)	C2—C1—C6—F2	178.4 (2)
F1—C2—C3—C4	−179.7 (2)	N1—C1—C6—F2	−2.1 (4)
C1—C2—C3—C4	−0.2 (4)	C2—C1—C6—C5	−1.2 (4)
C2—C3—C4—C5	−1.7 (4)	N1—C1—C6—C5	178.3 (2)
C2—C3—C4—Br1	176.76 (18)	C2—C1—N1—N1i	176.3 (3)
C3—C4—C5—C6	2.1 (4)	C6—C1—N1—N1i	−3.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···F2ii	0.95	2.53	3.190 (3)	126

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C5H5F2i	0.95	2.53	3.190(3)	126

Symmetry code: (i) .