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

In the title compound, C(8)H(5)Br(3)ClNO, the conformation of the N-H bond is syn to the 2-chloro substituent in the benzene ring. There are no classical inter-molecular hydrogen bonds, but intra-molecular N-H⋯Br and N-H⋯Cl contacts occur.

Related literature

For preparation of the title compound, see: Gowda et al. (2003 ▶). For background to our studies on the effect of the ring and the side-chain substituents on the crystal structures of N-aromatic amides, see: Gowda et al. (2007 ▶, 2009 ▶). For the conformations of other n class="Chemical">amides, see: Brown (1966 ▶).

Experimental

Crystal data

C8H5Br3ClNO

M = 406.31

Orthorhombic,

a = 9.1947 (6) Å

b = 12.9645 (7) Å

c = 9.5213 (6) Å

V = 1134.98 (12) Å3

Z = 4

Mo Kα radiation

μ = 10.86 mm−1

T = 299 K

0.40 × 0.40 × 0.34 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.098, T max = 0.120

4524 measured reflections

1645 independent reflections

1491 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.066

S = 1.07

1645 reflections

131 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.77 e Å−3

Δρmin = −0.56 e Å−3

Absolute structure: Flack (1983 ▶), 416 Friedel pairs

Flack parameter: 0.049 (18)

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/S1600536810001467/bt5167sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001467/bt5167Isup2.hkl

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

C8H5Br3ClNO	F(000) = 760
Mr = 406.31	Dx = 2.378 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3507 reflections
a = 9.1947 (6) Å	θ = 2.7–27.8°
b = 12.9645 (7) Å	µ = 10.86 mm−1
c = 9.5213 (6) Å	T = 299 K
V = 1134.98 (12) Å3	Rod, colourless
Z = 4	0.40 × 0.40 × 0.34 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1645 independent reflections
Radiation source: fine-focus sealed tube	1491 reflections with I > 2σ(I)
graphite	Rint = 0.022
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 = −11→11
Tmin = 0.098, Tmax = 0.120	k = −16→15
4524 measured reflections	l = −11→6

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.027	w = 1/[σ2(Fo2) + (0.0357P)2 + 1.2795P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.066	(Δ/σ)max = 0.004
S = 1.07	Δρmax = 0.77 e Å−3
1645 reflections	Δρmin = −0.56 e Å−3
131 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraints	Extinction coefficient: 0.0072 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 416 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.049 (18)

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
Br1	0.56049 (8)	0.28366 (5)	1.15778 (8)	0.0510 (2)
Br2	0.43394 (7)	0.06152 (5)	1.19542 (7)	0.0483 (2)
Br3	0.70743 (6)	0.09279 (5)	1.00260 (9)	0.0474 (2)
Cl1	0.5017 (2)	0.46215 (12)	0.7770 (2)	0.0536 (5)
O1	0.3140 (5)	0.1287 (4)	0.9233 (5)	0.0521 (13)
N1	0.4832 (5)	0.2390 (4)	0.8407 (6)	0.0366 (12)
H1N	0.554 (5)	0.277 (4)	0.866 (9)	0.044*
C1	0.4101 (6)	0.2689 (4)	0.7164 (7)	0.0311 (12)
C2	0.4114 (6)	0.3709 (4)	0.6763 (7)	0.0360 (14)
C3	0.3435 (8)	0.4026 (5)	0.5526 (7)	0.0475 (17)
H3	0.3476	0.4712	0.5244	0.057*
C4	0.2701 (8)	0.3305 (6)	0.4724 (8)	0.0573 (19)
H4	0.2235	0.3506	0.3901	0.069*
C5	0.2660 (9)	0.2308 (6)	0.5136 (9)	0.063 (2)
H5	0.2152	0.1829	0.4598	0.076*
C6	0.3362 (8)	0.1987 (5)	0.6347 (7)	0.0471 (17)
H6	0.3335	0.1296	0.6607	0.057*
C7	0.4282 (6)	0.1716 (4)	0.9346 (6)	0.0278 (12)
C8	0.5253 (6)	0.1542 (4)	1.0638 (7)	0.0288 (12)

	U11	U22	U33	U12	U13	U23
Br1	0.0744 (5)	0.0373 (3)	0.0411 (4)	−0.0059 (3)	−0.0169 (4)	−0.0036 (3)
Br2	0.0476 (4)	0.0509 (4)	0.0464 (4)	−0.0058 (3)	0.0000 (3)	0.0248 (3)
Br3	0.0328 (3)	0.0471 (4)	0.0623 (5)	0.0097 (3)	0.0018 (3)	0.0139 (4)
Cl1	0.0620 (10)	0.0384 (8)	0.0604 (12)	−0.0142 (8)	−0.0155 (9)	0.0153 (8)
O1	0.047 (3)	0.067 (3)	0.043 (3)	−0.025 (2)	−0.009 (2)	0.011 (3)
N1	0.040 (3)	0.035 (3)	0.035 (3)	−0.007 (2)	−0.008 (2)	0.013 (3)
C1	0.035 (3)	0.032 (3)	0.026 (3)	0.008 (2)	0.000 (2)	0.004 (2)
C2	0.032 (3)	0.036 (3)	0.040 (4)	0.004 (2)	0.004 (3)	0.004 (3)
C3	0.057 (4)	0.052 (4)	0.033 (4)	0.018 (3)	0.004 (3)	0.018 (3)
C4	0.074 (5)	0.070 (5)	0.028 (4)	0.010 (4)	−0.017 (4)	0.012 (4)
C5	0.092 (5)	0.065 (5)	0.033 (4)	0.011 (4)	−0.020 (4)	−0.016 (4)
C6	0.068 (4)	0.039 (3)	0.034 (4)	0.011 (3)	−0.005 (4)	−0.002 (3)
C7	0.028 (3)	0.027 (3)	0.029 (3)	0.002 (2)	0.000 (2)	0.000 (2)
C8	0.032 (3)	0.027 (3)	0.027 (3)	0.001 (2)	−0.001 (2)	0.008 (2)

Br1—C8	1.929 (6)	C2—C3	1.395 (9)
Br2—C8	1.929 (6)	C3—C4	1.383 (10)
Br3—C8	1.944 (6)	C3—H3	0.9300
Cl1—C2	1.735 (7)	C4—C5	1.351 (11)
O1—C7	1.193 (6)	C4—H4	0.9300
N1—C7	1.349 (7)	C5—C6	1.385 (10)
N1—C1	1.415 (8)	C5—H5	0.9300
N1—H1N	0.85 (3)	C6—H6	0.9300
C1—C6	1.377 (9)	C7—C8	1.537 (8)
C1—C2	1.376 (8)
C7—N1—C1	123.6 (5)	C4—C5—C6	121.1 (7)
C7—N1—H1N	118 (6)	C4—C5—H5	119.5
C1—N1—H1N	116 (5)	C6—C5—H5	119.5
C6—C1—C2	118.8 (6)	C1—C6—C5	120.1 (6)
C6—C1—N1	121.7 (5)	C1—C6—H6	119.9
C2—C1—N1	119.4 (6)	C5—C6—H6	119.9
C1—C2—C3	120.9 (6)	O1—C7—N1	124.9 (6)
C1—C2—Cl1	120.4 (5)	O1—C7—C8	121.0 (5)
C3—C2—Cl1	118.7 (5)	N1—C7—C8	114.1 (4)
C4—C3—C2	119.0 (6)	C7—C8—Br1	110.0 (4)
C4—C3—H3	120.5	C7—C8—Br2	111.0 (4)
C2—C3—H3	120.5	Br1—C8—Br2	108.3 (3)
C5—C4—C3	120.0 (6)	C7—C8—Br3	108.7 (4)
C5—C4—H4	120.0	Br1—C8—Br3	110.5 (3)
C3—C4—H4	120.0	Br2—C8—Br3	108.3 (3)
C7—N1—C1—C6	−41.6 (9)	N1—C1—C6—C5	−179.9 (6)
C7—N1—C1—C2	137.9 (6)	C4—C5—C6—C1	0.9 (12)
C6—C1—C2—C3	−2.1 (9)	C1—N1—C7—O1	1.1 (9)
N1—C1—C2—C3	178.4 (6)	C1—N1—C7—C8	−177.9 (5)
C6—C1—C2—Cl1	179.4 (5)	O1—C7—C8—Br1	−121.3 (5)
N1—C1—C2—Cl1	−0.1 (8)	N1—C7—C8—Br1	57.7 (6)
C1—C2—C3—C4	2.2 (10)	O1—C7—C8—Br2	−1.5 (7)
Cl1—C2—C3—C4	−179.4 (5)	N1—C7—C8—Br2	177.5 (4)
C2—C3—C4—C5	−0.7 (11)	O1—C7—C8—Br3	117.5 (5)
C3—C4—C5—C6	−0.9 (12)	N1—C7—C8—Br3	−63.4 (5)
C2—C1—C6—C5	0.6 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Br1	0.85 (3)	2.78 (8)	3.155 (6)	109 (6)
N1—H1N···Cl1	0.85 (3)	2.59 (7)	2.961 (5)	107 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Br1	0.85 (3)	2.78 (8)	3.155 (6)	109 (6)
N1—H1N⋯Cl1	0.85 (3)	2.59 (7)	2.961 (5)	107 (5)