2,2,2-Tribromo-N-(4-chloro-phen-yl)acetamide.

The crystal structure of the title compound, C(8)H(5)Br(3)ClNO, shows both intra-molecular N-H⋯Br and inter-molecular N-H⋯O hydrogen bonding. In the crystal, the mol-ecules are packed into column-like chains in the c-axis direction via the N-H⋯O hydrogen bonds.

Related literature

For the preparation of the compound, see: Gowda et al. (2003 ▶). For our study of the effect of ring and side-chain substituents on the solid state structures of N-aromatic amides, see: Gowda et al. (2000 ▶, 2007 ▶, 2009 ▶).

Experimental

Crystal data

C8H5Br3ClNO

M = 406.31

Orthorhombic,

a = 9.7332 (8) Å

b = 10.2462 (9) Å

c = 23.898 (2) Å

V = 2383.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 10.35 mm−1

T = 299 K

0.40 × 0.16 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.104, T max = 0.355

5692 measured reflections

2353 independent reflections

1643 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.205

S = 1.04

2353 reflections

130 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 2.04 e Å−3

Δρmin = −0.95 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data 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/S1600536809032139/pk2183sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032139/pk2183Isup2.hkl

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

C8H5Br3ClNO	F(000) = 1520
Mr = 406.31	Dx = 2.265 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2849 reflections
a = 9.7332 (8) Å	θ = 2.6–27.8°
b = 10.2462 (9) Å	µ = 10.35 mm−1
c = 23.898 (2) Å	T = 299 K
V = 2383.3 (3) Å3	Long needle, colourless
Z = 8	0.40 × 0.16 × 0.10 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2353 independent reflections
Radiation source: fine-focus sealed tube	1643 reflections with I > 2σ(I)
graphite	Rint = 0.033
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −12→8
Tmin = 0.104, Tmax = 0.355	k = −12→9
5692 measured reflections	l = −29→21

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.205	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0891P)2 + 22.8289P] where P = (Fo2 + 2Fc2)/3
2353 reflections	(Δ/σ)max = 0.005
130 parameters	Δρmax = 2.04 e Å−3
1 restraint	Δρmin = −0.95 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.4391 (10)	0.4634 (8)	0.1037 (4)	0.038 (2)
C2	0.4633 (11)	0.3604 (9)	0.0673 (5)	0.048 (2)
H2	0.3990	0.2939	0.0633	0.058*
C3	0.5841 (10)	0.3580 (10)	0.0369 (5)	0.051 (3)
H3	0.6017	0.2885	0.0129	0.062*
C4	0.6786 (10)	0.4569 (10)	0.0418 (4)	0.051 (3)
C5	0.6549 (10)	0.5578 (10)	0.0790 (5)	0.053 (3)
H5	0.7196	0.6240	0.0829	0.064*
C6	0.5357 (11)	0.5609 (9)	0.1103 (4)	0.048 (2)
H6	0.5206	0.6282	0.1357	0.058*
C7	0.2449 (10)	0.5644 (8)	0.1518 (4)	0.039 (2)
C8	0.1178 (10)	0.5312 (8)	0.1876 (4)	0.043 (2)
N1	0.3172 (8)	0.4601 (6)	0.1361 (3)	0.0425 (19)
H1N	0.283 (10)	0.386 (6)	0.140 (4)	0.051*
O1	0.2715 (7)	0.6760 (5)	0.1408 (3)	0.0521 (18)
Cl1	0.8276 (3)	0.4561 (4)	0.00254 (14)	0.0775 (10)
Br1	−0.00883 (11)	0.42751 (13)	0.14426 (6)	0.0737 (5)
Br2	0.02425 (15)	0.68618 (11)	0.21207 (7)	0.0817 (5)
Br3	0.17735 (16)	0.43813 (13)	0.25385 (5)	0.0792 (5)

	U11	U22	U33	U12	U13	U23
C1	0.053 (5)	0.028 (4)	0.033 (5)	0.007 (4)	0.005 (4)	0.006 (4)
C2	0.054 (6)	0.036 (5)	0.054 (6)	0.003 (4)	0.005 (5)	−0.001 (5)
C3	0.047 (6)	0.053 (6)	0.054 (6)	0.017 (5)	0.009 (5)	−0.006 (5)
C4	0.040 (5)	0.073 (7)	0.040 (5)	0.011 (5)	0.004 (4)	0.004 (5)
C5	0.040 (5)	0.050 (6)	0.070 (7)	−0.004 (4)	0.008 (5)	−0.006 (5)
C6	0.055 (6)	0.042 (5)	0.046 (6)	0.001 (5)	0.000 (5)	−0.014 (5)
C7	0.042 (4)	0.035 (5)	0.040 (5)	−0.001 (4)	0.009 (4)	0.007 (4)
C8	0.053 (5)	0.023 (4)	0.052 (6)	0.002 (4)	0.011 (5)	−0.005 (4)
N1	0.051 (5)	0.025 (4)	0.052 (5)	0.002 (3)	0.013 (4)	0.007 (3)
O1	0.056 (4)	0.024 (3)	0.077 (5)	0.003 (3)	0.022 (4)	0.003 (3)
Cl1	0.0468 (15)	0.117 (3)	0.069 (2)	0.0073 (16)	0.0172 (14)	−0.0168 (19)
Br1	0.0450 (6)	0.0856 (9)	0.0904 (10)	−0.0022 (6)	−0.0020 (6)	−0.0336 (8)
Br2	0.0900 (9)	0.0439 (6)	0.1112 (12)	0.0043 (6)	0.0532 (8)	−0.0141 (7)
Br3	0.0860 (9)	0.0990 (10)	0.0527 (7)	−0.0108 (7)	0.0088 (7)	0.0255 (7)

C1—C6	1.380 (13)	C5—H5	0.9300
C1—C2	1.389 (13)	C6—H6	0.9300
C1—N1	1.416 (12)	C7—O1	1.202 (10)
C2—C3	1.382 (14)	C7—N1	1.334 (11)
C2—H2	0.9300	C7—C8	1.542 (13)
C3—C4	1.374 (14)	C8—Br2	1.921 (8)
C3—H3	0.9300	C8—Br1	1.929 (10)
C4—C5	1.383 (14)	C8—Br3	1.937 (10)
C4—Cl1	1.727 (10)	N1—H1N	0.84 (5)
C5—C6	1.382 (14)
C6—C1—C2	120.4 (9)	C1—C6—C5	119.5 (9)
C6—C1—N1	121.7 (8)	C1—C6—H6	120.2
C2—C1—N1	117.8 (8)	C5—C6—H6	120.2
C3—C2—C1	119.2 (9)	O1—C7—N1	126.0 (8)
C3—C2—H2	120.4	O1—C7—C8	120.2 (8)
C1—C2—H2	120.4	N1—C7—C8	113.8 (7)
C4—C3—C2	120.8 (9)	C7—C8—Br2	111.5 (6)
C4—C3—H3	119.6	C7—C8—Br1	109.6 (6)
C2—C3—H3	119.6	Br2—C8—Br1	108.4 (5)
C3—C4—C5	119.6 (9)	C7—C8—Br3	108.8 (7)
C3—C4—Cl1	120.8 (8)	Br2—C8—Br3	107.4 (5)
C5—C4—Cl1	119.5 (8)	Br1—C8—Br3	111.0 (4)
C6—C5—C4	120.4 (9)	C7—N1—C1	125.2 (7)
C6—C5—H5	119.8	C7—N1—H1N	119 (7)
C4—C5—H5	119.8	C1—N1—H1N	115 (7)
C6—C1—C2—C3	−1.2 (15)	O1—C7—C8—Br2	−2.7 (12)
N1—C1—C2—C3	−177.3 (9)	N1—C7—C8—Br2	176.9 (7)
C1—C2—C3—C4	−1.1 (15)	O1—C7—C8—Br1	117.4 (9)
C2—C3—C4—C5	2.3 (16)	N1—C7—C8—Br1	−63.0 (10)
C2—C3—C4—Cl1	−178.3 (8)	O1—C7—C8—Br3	−121.0 (9)
C3—C4—C5—C6	−1.3 (16)	N1—C7—C8—Br3	58.6 (9)
Cl1—C4—C5—C6	179.3 (8)	O1—C7—N1—C1	0.5 (16)
C2—C1—C6—C5	2.2 (15)	C8—C7—N1—C1	−179.1 (9)
N1—C1—C6—C5	178.1 (9)	C6—C1—N1—C7	36.9 (14)
C4—C5—C6—C1	−1.0 (16)	C2—C1—N1—C7	−147.1 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Br1	0.84 (5)	2.87 (10)	3.197 (8)	105 (8)
N1—H1N···O1i	0.84 (5)	2.21 (5)	3.038 (9)	168 (10)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Br1	0.84 (5)	2.87 (10)	3.197 (8)	105 (8)
N1—H1N⋯O1i	0.84 (5)	2.21 (5)	3.038 (9)	168 (10)

Symmetry code: (i) .