2-Bromo-N-(4-bromo-phen-yl)acetamide.

In the title compound, C(8)H(7)Br(2)NO, the conformation of the N-H bond is anti to both the carbonyl and C-Br bonds in the side chain. In the crystal structure, mol-ecules are packed into supra-molecular chains along the c axis by N-H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For related structures, see: Andreetti et al. (1968 ▶); Gowda et al. (2007 ▶,c ▶).

Experimental

Crystal data

C8H7Br2NO

M = 292.97

Monoclinic,

a = 4.4987 (3) Å

b = 23.152 (1) Å

c = 9.1098 (5) Å

β = 99.713 (6)°

V = 935.22 (9) Å3

Z = 4

Mo Kα radiation

μ = 8.62 mm−1

T = 303 K

0.50 × 0.20 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.078, T max = 0.299

3065 measured reflections

1661 independent reflections

1415 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.127

S = 0.99

1661 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.68 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data n class="Disease">reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028219/tk2505sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028219/tk2505Isup2.hkl

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

C8H7Br2NO	F(000) = 560
Mr = 292.97	Dx = 2.081 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2250 reflections
a = 4.4987 (3) Å	θ = 2.9–27.8°
b = 23.152 (1) Å	µ = 8.62 mm−1
c = 9.1098 (5) Å	T = 303 K
β = 99.713 (6)°	Needle, colourless
V = 935.22 (9) Å3	0.50 × 0.20 × 0.14 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1661 independent reflections
Radiation source: fine-focus sealed tube	1415 reflections with I > 2σ(I)
graphite	Rint = 0.023
Rotation method data acquisition using ω and φ scans	θmax = 25.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −5→4
Tmin = 0.078, Tmax = 0.299	k = −16→27
3065 measured reflections	l = −10→9

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0581P)2 + 4.1384P] where P = (Fo2 + 2Fc2)/3
1661 reflections	(Δ/σ)max = 0.001
109 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.68 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
C1	0.7460 (14)	0.2109 (3)	0.3871 (6)	0.0489 (15)
H1A	0.6432	0.2287	0.4610	0.059*
H1B	0.9218	0.1909	0.4395	0.059*
C2	0.8475 (13)	0.2577 (3)	0.2905 (6)	0.0400 (13)
C3	1.1568 (13)	0.3474 (2)	0.3295 (6)	0.0388 (12)
C4	1.0573 (14)	0.3743 (3)	0.1927 (6)	0.0445 (14)
H4	0.9070	0.3573	0.1236	0.053*
C5	1.1831 (16)	0.4263 (3)	0.1603 (7)	0.0535 (16)
H5	1.1158	0.4444	0.0697	0.064*
C6	1.4056 (14)	0.4510 (3)	0.2609 (7)	0.0473 (15)
C7	1.5067 (15)	0.4251 (3)	0.3949 (7)	0.0538 (16)
H7	1.6576	0.4424	0.4631	0.065*
C8	1.3832 (14)	0.3731 (3)	0.4283 (7)	0.0476 (14)
H8	1.4542	0.3553	0.5189	0.057*
N1	1.0306 (11)	0.2954 (2)	0.3747 (5)	0.0397 (11)
H1N	1.0770	0.2870	0.4677	0.048*
O1	0.7725 (10)	0.26109 (19)	0.1567 (4)	0.0529 (11)
Br1	0.48101 (16)	0.15590 (3)	0.27451 (8)	0.0576 (3)
Br2	1.5669 (2)	0.52368 (3)	0.21830 (9)	0.0722 (3)

	U11	U22	U33	U12	U13	U23
C1	0.048 (3)	0.063 (4)	0.033 (3)	−0.015 (3)	0.000 (3)	−0.002 (3)
C2	0.038 (3)	0.044 (3)	0.038 (3)	0.007 (3)	0.007 (2)	−0.001 (3)
C3	0.044 (3)	0.037 (3)	0.037 (3)	0.004 (2)	0.012 (2)	−0.005 (2)
C4	0.053 (4)	0.050 (3)	0.029 (3)	0.004 (3)	0.004 (3)	0.003 (3)
C5	0.072 (4)	0.048 (4)	0.042 (3)	0.007 (3)	0.014 (3)	0.006 (3)
C6	0.058 (4)	0.038 (3)	0.053 (4)	−0.001 (3)	0.027 (3)	−0.003 (3)
C7	0.054 (4)	0.057 (4)	0.052 (4)	−0.012 (3)	0.012 (3)	−0.008 (3)
C8	0.048 (3)	0.052 (4)	0.041 (3)	−0.001 (3)	0.003 (3)	0.001 (3)
N1	0.051 (3)	0.039 (2)	0.028 (2)	−0.001 (2)	0.007 (2)	0.006 (2)
O1	0.072 (3)	0.054 (3)	0.030 (2)	−0.012 (2)	−0.001 (2)	−0.0005 (19)
Br1	0.0632 (5)	0.0541 (4)	0.0528 (4)	−0.0127 (3)	0.0024 (3)	−0.0073 (3)
Br2	0.1010 (7)	0.0456 (4)	0.0785 (6)	−0.0099 (4)	0.0392 (5)	−0.0006 (3)

C1—C2	1.513 (8)	C4—H4	0.9300
C1—Br1	1.919 (6)	C5—C6	1.363 (9)
C1—H1A	0.9700	C5—H5	0.9300
C1—H1B	0.9700	C6—C7	1.367 (9)
C2—O1	1.211 (7)	C6—Br2	1.898 (6)
C2—N1	1.349 (7)	C7—C8	1.381 (9)
C3—C8	1.376 (8)	C7—H7	0.9300
C3—C4	1.398 (8)	C8—H8	0.9300
C3—N1	1.421 (7)	N1—H1N	0.8600
C4—C5	1.382 (9)
C2—C1—Br1	112.6 (4)	C6—C5—C4	120.2 (6)
C2—C1—H1A	109.1	C6—C5—H5	119.9
Br1—C1—H1A	109.1	C4—C5—H5	119.9
C2—C1—H1B	109.1	C5—C6—C7	120.8 (6)
Br1—C1—H1B	109.1	C5—C6—Br2	119.8 (5)
H1A—C1—H1B	107.8	C7—C6—Br2	119.3 (5)
O1—C2—N1	124.7 (6)	C6—C7—C8	119.6 (6)
O1—C2—C1	124.9 (5)	C6—C7—H7	120.2
N1—C2—C1	110.4 (5)	C8—C7—H7	120.2
C8—C3—C4	118.8 (6)	C3—C8—C7	120.9 (6)
C8—C3—N1	117.7 (5)	C3—C8—H8	119.6
C4—C3—N1	123.5 (5)	C7—C8—H8	119.6
C5—C4—C3	119.8 (6)	C2—N1—C3	128.3 (5)
C5—C4—H4	120.1	C2—N1—H1N	115.8
C3—C4—H4	120.1	C3—N1—H1N	115.8
Br1—C1—C2—O1	0.2 (8)	Br2—C6—C7—C8	178.0 (5)
Br1—C1—C2—N1	179.5 (4)	C4—C3—C8—C7	1.3 (9)
C8—C3—C4—C5	−1.2 (9)	N1—C3—C8—C7	−176.9 (6)
N1—C3—C4—C5	177.0 (5)	C6—C7—C8—C3	−0.9 (10)
C3—C4—C5—C6	0.6 (9)	O1—C2—N1—C3	4.1 (9)
C4—C5—C6—C7	−0.3 (10)	C1—C2—N1—C3	−175.1 (5)
C4—C5—C6—Br2	−177.8 (5)	C8—C3—N1—C2	−167.5 (6)
C5—C6—C7—C8	0.4 (10)	C4—C3—N1—C2	14.3 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.11	2.925 (6)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.11	2.925 (6)	157

Symmetry code: (i) .