2,2,2-Tribromo-N-(3-chloro-phen-yl)acetamide.

In the title compound, C(8)H(5)Br(3)ClNO, the conformation of the N-H bond is anti to the 3-chloro substituent in the benzene ring. An intra-molecular N-H⋯Br hydrogen bond occurs. In the crystal, mol-ecules are packed into infinite chains in the a-axis direction by N-H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For background and related structures, see: Brown (1966 ▶); Gowda et al. (2008 ▶, 2009 ▶, 2010 ▶).

Experimental

Crystal data

C8H5Br3ClNO

M = 406.31

Orthorhombic,

a = 12.803 (1) Å

b = 9.146 (1) Å

c = 20.221 (3) Å

V = 2367.8 (5) Å3

Z = 8

Cu Kα radiation

μ = 14.47 mm−1

T = 299 K

0.53 × 0.33 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.049, T max = 0.123

3870 measured reflections

2114 independent reflections

1646 reflections with I > 2σ(I)

R int = 0.110

3 standard reflections every 120 min intensity decay: 1.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.086

wR(F 2) = 0.387

S = 1.59

2114 reflections

127 parameters

H-atom parameters constrained

Δρmax = 2.07 e Å−3

Δρmin = −1.56 e Å−3

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/S160053681001411X/fl2301sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001411X/fl2301Isup2.hkl

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

C8H5Br3ClNO	F(000) = 1520
Mr = 406.31	Dx = 2.280 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 12.803 (1) Å	θ = 4.4–20.5°
b = 9.146 (1) Å	µ = 14.47 mm−1
c = 20.221 (3) Å	T = 299 K
V = 2367.8 (5) Å3	Rod, colourless
Z = 8	0.53 × 0.33 × 0.25 mm

Enraf–Nonius CAD-4 diffractometer	1646 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.110
graphite	θmax = 67.0°, θmin = 4.4°
ω/2θ scans	h = −15→11
Absorption correction: ψ scan (North et al., 1968)	k = −10→0
Tmin = 0.049, Tmax = 0.123	l = −24→0
3870 measured reflections	3 standard reflections every 120 min
2114 independent reflections	intensity decay: 1.5%

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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.387	H-atom parameters constrained
S = 1.59	w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
2114 reflections	(Δ/σ)max = 0.006
127 parameters	Δρmax = 2.07 e Å−3
0 restraints	Δρmin = −1.56 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.8142 (8)	0.2739 (12)	0.3141 (5)	0.042 (2)
C2	0.7763 (8)	0.3768 (12)	0.2709 (6)	0.043 (2)
H2	0.7101	0.4167	0.2769	0.051*
C3	0.8383 (13)	0.4204 (15)	0.2184 (6)	0.057 (3)
C4	0.9361 (13)	0.3617 (16)	0.2099 (8)	0.071 (4)
H4	0.9773	0.3902	0.1743	0.085*
C5	0.9715 (11)	0.2635 (18)	0.2533 (9)	0.077 (5)
H5	1.0374	0.2231	0.2467	0.092*
C6	0.9141 (11)	0.2199 (13)	0.3074 (8)	0.059 (3)
H6	0.9419	0.1559	0.3385	0.071*
C7	0.6833 (9)	0.2898 (11)	0.4008 (5)	0.042 (2)
C8	0.6221 (8)	0.2020 (11)	0.4511 (6)	0.043 (2)
Br1	0.55384 (15)	0.04007 (19)	0.40907 (9)	0.0787 (8)
Br2	0.52069 (17)	0.31822 (18)	0.49631 (11)	0.0893 (9)
Br3	0.71709 (15)	0.1263 (3)	0.51772 (8)	0.0856 (8)
Cl1	0.7921 (4)	0.5505 (5)	0.16439 (19)	0.0817 (13)
N1	0.7560 (8)	0.2201 (11)	0.3684 (5)	0.050 (2)
H1N	0.7701	0.1327	0.3814	0.060*
O1	0.6555 (7)	0.4164 (8)	0.3902 (4)	0.0494 (19)

	U11	U22	U33	U12	U13	U23
C1	0.032 (5)	0.046 (5)	0.047 (6)	−0.008 (4)	0.008 (4)	−0.005 (5)
C2	0.036 (5)	0.045 (5)	0.048 (6)	−0.006 (4)	0.000 (4)	0.005 (4)
C3	0.069 (8)	0.065 (7)	0.039 (5)	−0.018 (6)	0.006 (5)	0.001 (5)
C4	0.082 (10)	0.051 (7)	0.079 (10)	−0.009 (7)	0.041 (8)	−0.003 (7)
C5	0.045 (8)	0.070 (9)	0.116 (12)	−0.003 (7)	0.040 (8)	0.004 (10)
C6	0.060 (7)	0.040 (5)	0.076 (8)	0.003 (5)	0.017 (6)	0.004 (6)
C7	0.044 (6)	0.037 (5)	0.044 (5)	−0.002 (4)	−0.001 (4)	0.000 (4)
C8	0.032 (5)	0.037 (5)	0.061 (6)	0.006 (4)	0.004 (5)	−0.005 (4)
Br1	0.0826 (13)	0.0758 (12)	0.0776 (12)	−0.0431 (9)	0.0248 (8)	−0.0149 (8)
Br2	0.0953 (15)	0.0610 (12)	0.1114 (16)	0.0226 (9)	0.0628 (12)	0.0087 (9)
Br3	0.0700 (12)	0.1248 (18)	0.0619 (12)	0.0134 (10)	−0.0027 (7)	0.0327 (10)
Cl1	0.117 (3)	0.079 (2)	0.0498 (19)	−0.006 (2)	0.0019 (18)	0.0161 (16)
N1	0.056 (6)	0.041 (4)	0.052 (5)	0.000 (4)	0.016 (5)	0.015 (4)
O1	0.042 (4)	0.037 (3)	0.069 (5)	0.000 (3)	0.008 (4)	0.009 (3)

C1—C2	1.372 (16)	C5—H5	0.9300
C1—C6	1.378 (17)	C6—H6	0.9300
C1—N1	1.416 (13)	C7—O1	1.229 (14)
C2—C3	1.385 (16)	C7—N1	1.305 (16)
C2—H2	0.9300	C7—C8	1.515 (15)
C3—C4	1.37 (2)	C8—Br2	1.911 (10)
C3—Cl1	1.720 (15)	C8—Br1	1.918 (11)
C4—C5	1.33 (2)	C8—Br3	1.943 (11)
C4—H4	0.9300	N1—H1N	0.8600
C5—C6	1.377 (18)
C2—C1—C6	120.8 (10)	C5—C6—C1	118.0 (14)
C2—C1—N1	123.1 (10)	C5—C6—H6	121.0
C6—C1—N1	116.1 (11)	C1—C6—H6	121.0
C1—C2—C3	118.8 (11)	O1—C7—N1	125.4 (10)
C1—C2—H2	120.6	O1—C7—C8	117.8 (10)
C3—C2—H2	120.6	N1—C7—C8	116.5 (9)
C4—C3—C2	120.4 (13)	C7—C8—Br2	112.2 (7)
C4—C3—Cl1	120.3 (10)	C7—C8—Br1	110.4 (8)
C2—C3—Cl1	119.3 (12)	Br2—C8—Br1	109.4 (5)
C5—C4—C3	119.4 (12)	C7—C8—Br3	109.3 (7)
C5—C4—H4	120.3	Br2—C8—Br3	107.0 (6)
C3—C4—H4	120.3	Br1—C8—Br3	108.5 (5)
C4—C5—C6	122.4 (14)	C7—N1—C1	126.5 (10)
C4—C5—H5	118.8	C7—N1—H1N	116.8
C6—C5—H5	118.8	C1—N1—H1N	116.8
C6—C1—C2—C3	3.2 (17)	O1—C7—C8—Br2	−6.9 (13)
N1—C1—C2—C3	−178.6 (11)	N1—C7—C8—Br2	178.6 (9)
C1—C2—C3—C4	−0.3 (19)	O1—C7—C8—Br1	115.4 (10)
C1—C2—C3—Cl1	−179.4 (9)	N1—C7—C8—Br1	−59.1 (12)
C2—C3—C4—C5	−1(2)	O1—C7—C8—Br3	−125.4 (9)
Cl1—C3—C4—C5	178.3 (13)	N1—C7—C8—Br3	60.1 (12)
C3—C4—C5—C6	−1(3)	O1—C7—N1—C1	−2(2)
C4—C5—C6—C1	4(2)	C8—C7—N1—C1	171.9 (11)
C2—C1—C6—C5	−5(2)	C2—C1—N1—C7	−28.2 (19)
N1—C1—C6—C5	176.7 (13)	C6—C1—N1—C7	150.0 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.20	3.032 (13)	162
N1—H1N···Br3	0.86	2.84	3.177 (9)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.20	3.032 (13)	162
N1—H1N⋯Br3	0.86	2.84	3.177 (9)	105

Symmetry code: (i) .