2,2,2-Tribromo-N-phenyl-acetamide.

In the title compound, C(8)H(6)Br(3)NO, the N-H bond is anti to the carbonyl bond in the side chain. The N-H hydrogen atom is involved in a two-centered bond as it shows simultaneous N-H⋯Br intra- and N-H⋯O inter-molecular inter-actions in the structure. In the crystal, mol-ecules are packed into column-like chains along the b axis through the N-H⋯O hydrogen bonds.

Related literature

For the preparation of the compound, see: Gowda et al. (2003 ▶). For related structures, see: Brown et al. (1966 ▶); Dou et al. (1994 ▶); Gowda et al. (2007 ▶, 2009 ▶).

Experimental

Crystal data

C8H6Br3NO

M = 371.87

Orthorhombic,

a = 10.1863 (8) Å

b = 9.1483 (7) Å

c = 11.8856 (9) Å

V = 1107.59 (15) Å3

Z = 4

Cu Kα radiation

μ = 13.22 mm−1

T = 299 K

0.50 × 0.18 × 0.13 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.037, T max = 0.178

2653 measured reflections

1311 independent reflections

1237 reflections with I > 2σ(I)

R int = 0.052

3 standard reflections frequency: 120 min intensity decay: 1.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.237

S = 1.05

1311 reflections

119 parameters

25 restraints

H-atom parameters constrained

Δρmax = 1.86 e Å−3

Δρmin = −1.18 e Å−3

Absolute structure: Flack (1983 ▶), 276 Friedel pairs

Flack parameter: 0.00 (13)

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); 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/S160053680903298X/fl2260sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903298X/fl2260Isup2.hkl

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

C8H6Br3NO	F(000) = 696
Mr = 371.87	Dx = 2.230 Mg m−3
Orthorhombic, Pca21	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2c -2ac	Cell parameters from 25 reflections
a = 10.1863 (8) Å	θ = 4.8–20.7°
b = 9.1483 (7) Å	µ = 13.22 mm−1
c = 11.8856 (9) Å	T = 299 K
V = 1107.59 (15) Å3	Needle, colourless
Z = 4	0.50 × 0.18 × 0.13 mm

Enraf–Nonius CAD-4 diffractometer	1237 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.052
graphite	θmax = 67.0°, θmin = 4.8°
ω/2θ scans	h = −12→0
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.037, Tmax = 0.178	l = −11→14
2653 measured reflections	3 standard reflections every 120 min
1311 independent reflections	intensity decay: 1.5%

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.079	w = 1/[σ2(Fo2) + (0.1659P)2 + 2.9656P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.237	(Δ/σ)max = 0.002
S = 1.05	Δρmax = 1.86 e Å−3
1311 reflections	Δρmin = −1.18 e Å−3
119 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
25 restraints	Extinction coefficient: 0.0035 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 276 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.00 (13)

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	0.2439 (16)	0.3139 (13)	0.6091 (14)	0.057 (3)
C2	0.1483 (19)	0.2891 (18)	0.6869 (19)	0.078 (4)
H2	0.0753	0.3500	0.6914	0.094*
C3	0.162 (3)	0.169 (3)	0.761 (3)	0.110 (7)
H3	0.1010	0.1557	0.8185	0.132*
C4	0.256 (3)	0.077 (2)	0.751 (2)	0.095 (5)
H4	0.2575	−0.0070	0.7947	0.114*
C5	0.3521 (19)	0.1043 (17)	0.6774 (19)	0.079 (4)
H5	0.4247	0.0427	0.6773	0.095*
C6	0.3495 (16)	0.2176 (13)	0.6019 (17)	0.065 (4)
H6	0.4153	0.2297	0.5484	0.078*
C7	0.3328 (12)	0.5181 (14)	0.5056 (12)	0.053 (3)
C8	0.3002 (15)	0.6556 (17)	0.4339 (16)	0.069 (4)
N1	0.2341 (10)	0.4331 (11)	0.5359 (12)	0.058 (2)
H1N	0.1579	0.4526	0.5085	0.069*
O1	0.4489 (8)	0.5008 (11)	0.5332 (12)	0.076 (4)
Br1	0.1668 (3)	0.6121 (3)	0.3197 (2)	0.0988 (9)
Br2	0.2294 (3)	0.80125 (17)	0.5320 (2)	0.1007 (10)
Br3	0.4497 (2)	0.7263 (3)	0.3550 (3)	0.1230 (14)

	U11	U22	U33	U12	U13	U23
C1	0.049 (6)	0.064 (7)	0.059 (8)	−0.012 (6)	−0.003 (6)	0.003 (6)
C2	0.075 (8)	0.080 (7)	0.079 (8)	−0.011 (6)	0.014 (7)	0.021 (6)
C3	0.112 (11)	0.110 (9)	0.108 (11)	−0.016 (8)	0.014 (9)	0.020 (8)
C4	0.106 (9)	0.085 (7)	0.095 (10)	−0.013 (8)	−0.013 (8)	0.014 (7)
C5	0.082 (8)	0.069 (6)	0.087 (9)	−0.002 (6)	−0.016 (7)	0.004 (6)
C6	0.060 (8)	0.052 (6)	0.083 (10)	0.004 (5)	−0.022 (7)	0.001 (6)
C7	0.038 (5)	0.066 (6)	0.054 (7)	0.001 (4)	0.005 (5)	0.017 (6)
C8	0.057 (8)	0.068 (7)	0.081 (11)	0.014 (6)	0.006 (7)	0.020 (7)
N1	0.037 (5)	0.068 (5)	0.068 (7)	0.005 (4)	−0.007 (5)	0.008 (6)
O1	0.035 (4)	0.085 (6)	0.109 (10)	−0.008 (4)	−0.007 (5)	0.042 (7)
Br1	0.1101 (17)	0.1157 (14)	0.0705 (12)	−0.0051 (11)	−0.0328 (12)	0.0179 (10)
Br2	0.164 (2)	0.0664 (9)	0.0719 (12)	0.0155 (10)	0.0171 (14)	0.0000 (8)
Br3	0.0680 (11)	0.1321 (19)	0.169 (3)	0.0095 (10)	0.0356 (14)	0.091 (2)

C1—C2	1.36 (3)	C5—H5	0.9300
C1—C6	1.39 (2)	C6—H6	0.9300
C1—N1	1.399 (19)	C7—O1	1.237 (16)
C2—C3	1.42 (3)	C7—N1	1.321 (16)
C2—H2	0.9300	C7—C8	1.555 (18)
C3—C4	1.27 (4)	C8—Br3	1.902 (16)
C3—H3	0.9300	C8—Br2	1.913 (17)
C4—C5	1.34 (4)	C8—Br1	1.960 (19)
C4—H4	0.9300	N1—H1N	0.8600
C5—C6	1.37 (2)
C2—C1—C6	119.3 (15)	C5—C6—C1	116.9 (18)
C2—C1—N1	120.1 (15)	C5—C6—H6	121.6
C6—C1—N1	120.6 (15)	C1—C6—H6	121.6
C1—C2—C3	118.7 (19)	O1—C7—N1	125.5 (11)
C1—C2—H2	120.6	O1—C7—C8	117.0 (11)
C3—C2—H2	120.6	N1—C7—C8	117.5 (11)
C4—C3—C2	122 (3)	C7—C8—Br3	111.9 (9)
C4—C3—H3	119.2	C7—C8—Br2	108.1 (11)
C2—C3—H3	119.2	Br3—C8—Br2	111.4 (9)
C3—C4—C5	119 (2)	C7—C8—Br1	111.3 (11)
C3—C4—H4	120.3	Br3—C8—Br1	106.4 (9)
C5—C4—H4	120.3	Br2—C8—Br1	107.6 (7)
C4—C5—C6	123.6 (18)	C7—N1—C1	125.0 (11)
C4—C5—H5	118.2	C7—N1—H1N	117.5
C6—C5—H5	118.2	C1—N1—H1N	117.5
C6—C1—C2—C3	2(3)	N1—C7—C8—Br3	−159.7 (12)
N1—C1—C2—C3	−179.1 (19)	O1—C7—C8—Br2	−100.0 (14)
C1—C2—C3—C4	−5(4)	N1—C7—C8—Br2	77.2 (16)
C2—C3—C4—C5	8(4)	O1—C7—C8—Br1	142.1 (13)
C3—C4—C5—C6	−7(4)	N1—C7—C8—Br1	−40.7 (17)
C4—C5—C6—C1	4(3)	O1—C7—N1—C1	4(3)
C2—C1—C6—C5	−2(2)	C8—C7—N1—C1	−173.4 (14)
N1—C1—C6—C5	179.6 (15)	C2—C1—N1—C7	139.6 (18)
O1—C7—C8—Br3	23.1 (19)	C6—C1—N1—C7	−42 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.19	2.967 (13)	150
N1—H1N···Br1	0.86	2.68	3.123 (13)	114

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.19	2.967 (13)	150
N1—H1N⋯Br1	0.86	2.68	3.123 (13)	114

Symmetry code: (i) .