2,2-Dibromo-N-(4-fluoro-phen-yl)acetamide.

In the crystal structure of the title compound, C(8)H(6)Br(2)FNO, C-H⋯O and N-H⋯O hydrogen bonding results in six-membered rings and links the mol-ecules into chains running parallel to the c axis. The dihedral angle between the fluoro-phenyl ring and the acetamide group is 29.5 (5)°.

Related literature

For background information, see: Feng et al. (2012 ▶). For related crystal structures, see: Gowda et al. (2009 ▶); Feng et al. (2012 ▶).

Experimental

Crystal data

C8H6Br2FNO

M = 310.96

Monoclinic,

a = 9.746 (2) Å

b = 10.980 (2) Å

c = 9.426 (2) Å

β = 96.33 (3)°

V = 1002.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 8.06 mm−1

T = 293 K

0.10 × 0.10 × 0.10 mm

Data collection

Enraf–Nonious CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.975, T max = 0.991

1937 measured reflections

1827 independent reflections

900 reflections with I > 2σ(I)

R int = 0.068

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.094

S = 1.00

1827 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021174/pv2533sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021174/pv2533Isup2.hkl

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

C8H6Br2FNO	F(000) = 592
Mr = 310.96	Dx = 2.060 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.746 (2) Å	θ = 9–12°
b = 10.980 (2) Å	µ = 8.06 mm−1
c = 9.426 (2) Å	T = 293 K
β = 96.33 (3)°	Block, colorless
V = 1002.5 (3) Å3	0.10 × 0.10 × 0.10 mm
Z = 4

Enraf–Nonious CAD-4 diffractometer	900 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.068
Graphite monochromator	θmax = 25.3°, θmin = 2.1°
ω/2θ scans	h = −11→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→13
Tmin = 0.975, Tmax = 0.991	l = −11→11
1937 measured reflections	3 standard reflections every 200 reflections
1827 independent reflections	intensity decay: 1%

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.024P)2] where P = (Fo2 + 2Fc2)/3
1827 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.50 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
F	0.4558 (5)	0.2056 (4)	0.4060 (6)	0.0868 (17)
Br1	0.27410 (10)	0.98435 (8)	0.42192 (10)	0.0675 (3)
Br2	−0.02715 (10)	0.90635 (10)	0.29891 (11)	0.0840 (4)
O	0.2133 (6)	0.7340 (5)	0.2350 (5)	0.0635 (17)
N	0.2193 (6)	0.6579 (5)	0.4588 (6)	0.0439 (17)
H0A	0.1995	0.6743	0.5434	0.053*
C1	0.1342 (8)	0.8605 (6)	0.4178 (8)	0.048 (2)
H1A	0.1111	0.8455	0.5149	0.058*
C2	0.1936 (8)	0.7438 (7)	0.3585 (8)	0.046 (2)
C3	0.2775 (8)	0.5405 (6)	0.4353 (8)	0.0390 (19)
C4	0.2452 (8)	0.4467 (7)	0.5254 (8)	0.052 (2)
H4A	0.1850	0.4610	0.5936	0.062*
C5	0.3007 (9)	0.3355 (8)	0.5140 (9)	0.059 (3)
H5A	0.2770	0.2713	0.5708	0.070*
C6	0.3943 (8)	0.3195 (8)	0.4150 (10)	0.054 (2)
C7	0.4260 (8)	0.4084 (8)	0.3246 (8)	0.056 (2)
H7A	0.4856	0.3933	0.2561	0.067*
C8	0.3694 (8)	0.5186 (7)	0.3364 (7)	0.046 (2)
H8A	0.3923	0.5815	0.2771	0.055*

	U11	U22	U33	U12	U13	U23
F	0.081 (4)	0.047 (3)	0.135 (5)	0.008 (3)	0.025 (3)	−0.004 (3)
Br1	0.0902 (7)	0.0504 (6)	0.0640 (6)	−0.0033 (6)	0.0179 (5)	−0.0068 (5)
Br2	0.0681 (7)	0.1079 (10)	0.0749 (8)	0.0201 (7)	0.0034 (5)	0.0095 (7)
O	0.116 (5)	0.052 (4)	0.026 (3)	0.013 (4)	0.020 (3)	−0.002 (3)
N	0.067 (5)	0.037 (4)	0.030 (4)	−0.005 (4)	0.016 (3)	−0.003 (3)
C1	0.075 (6)	0.037 (5)	0.035 (5)	−0.001 (4)	0.017 (4)	0.007 (4)
C2	0.063 (6)	0.046 (5)	0.029 (5)	0.001 (5)	−0.002 (4)	−0.007 (5)
C3	0.050 (5)	0.036 (5)	0.028 (5)	−0.006 (4)	−0.010 (4)	−0.001 (4)
C4	0.079 (7)	0.042 (6)	0.036 (5)	−0.004 (5)	0.009 (5)	0.004 (4)
C5	0.063 (6)	0.039 (6)	0.075 (7)	−0.014 (5)	0.012 (5)	0.014 (5)
C6	0.043 (5)	0.040 (6)	0.078 (7)	0.004 (5)	0.007 (5)	−0.004 (5)
C7	0.064 (6)	0.054 (6)	0.051 (6)	−0.005 (5)	0.014 (5)	−0.011 (5)
C8	0.056 (5)	0.044 (5)	0.037 (5)	0.000 (5)	0.009 (4)	0.010 (4)

F—C6	1.394 (8)	C3—C4	1.392 (9)
Br1—C1	1.923 (7)	C4—C5	1.344 (9)
Br2—C1	1.896 (7)	C4—H4A	0.9300
O—C2	1.205 (7)	C5—C6	1.386 (10)
N—C2	1.339 (8)	C5—H5A	0.9300
N—C3	1.436 (8)	C6—C7	1.354 (10)
N—H0A	0.8600	C7—C8	1.340 (9)
C1—C2	1.536 (10)	C7—H7A	0.9300
C1—H1A	0.9800	C8—H8A	0.9300
C3—C8	1.384 (9)
C2—N—C3	124.8 (6)	C5—C4—C3	120.2 (8)
C2—N—H0A	117.6	C5—C4—H4A	119.9
C3—N—H0A	117.6	C3—C4—H4A	119.9
C2—C1—Br2	109.1 (5)	C4—C5—C6	118.0 (8)
C2—C1—Br1	107.6 (5)	C4—C5—H5A	121.0
Br2—C1—Br1	111.3 (3)	C6—C5—H5A	121.0
C2—C1—H1A	109.6	C7—C6—C5	123.1 (8)
Br2—C1—H1A	109.6	C7—C6—F	118.6 (8)
Br1—C1—H1A	109.6	C5—C6—F	118.3 (8)
O—C2—N	125.6 (8)	C8—C7—C6	118.3 (8)
O—C2—C1	122.2 (7)	C8—C7—H7A	120.8
N—C2—C1	112.3 (6)	C6—C7—H7A	120.8
C8—C3—C4	119.3 (7)	C7—C8—C3	121.0 (7)
C8—C3—N	123.7 (7)	C7—C8—H8A	119.5
C4—C3—N	116.8 (7)	C3—C8—H8A	119.5
C3—N—C2—O	1.4 (13)	N—C3—C4—C5	−177.0 (7)
C3—N—C2—C1	−178.8 (6)	C3—C4—C5—C6	2.7 (13)
Br2—C1—C2—O	50.2 (9)	C4—C5—C6—C7	−3.8 (14)
Br1—C1—C2—O	−70.7 (9)	C4—C5—C6—F	177.9 (7)
Br2—C1—C2—N	−129.7 (6)	C5—C6—C7—C8	3.4 (13)
Br1—C1—C2—N	109.4 (6)	F—C6—C7—C8	−178.3 (7)
C2—N—C3—C8	30.9 (11)	C6—C7—C8—C3	−2.0 (12)
C2—N—C3—C4	−153.6 (7)	C4—C3—C8—C7	1.0 (11)
C8—C3—C4—C5	−1.4 (12)	N—C3—C8—C7	176.4 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···Oi	0.86	2.06	2.868 (7)	156
C1—H1A···Oi	0.98	2.37	3.178 (9)	140
C8—H8A···O	0.93	2.42	2.916 (9)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯Oi	0.86	2.06	2.868 (7)	156
C1—H1A⋯Oi	0.98	2.37	3.178 (9)	140

Symmetry code: (i) .