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

The asymmetric unit of the title compound, C(9)H(8)Br(3)NO, contains two independent mol-ecules. The conformation of the N-H bond is anti to the 3-methyl substituent in the benzene ring in each mol-ecule. The structure shows both intra-molecular N-H⋯Br and inter-molecular N-H⋯O hydrogen bonding, the latter leading to the formation of helical supra-molecular chains along the b axis.

Related literature

For 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. (2007 ▶, 2009 ▶). For the structures of other n class="Chemical">amides, see: Brown (1966 ▶).

Experimental

Crystal data

C9H8Br3NO

M = 385.89

Monoclinic,

a = 11.360 (1) Å

b = 10.280 (1) Å

c = 20.298 (3) Å

β = 100.23 (1)°

V = 2332.7 (5) Å3

Z = 8

Cu Kα radiation

μ = 12.58 mm−1

T = 299 K

0.28 × 0.13 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.127, T max = 0.433

4358 measured reflections

4147 independent reflections

2939 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.249

S = 1.04

4147 reflections

255 parameters

H-atom parameters constrained

Δρmax = 1.60 e Å−3

Δρmin = −1.66 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: n class="CellLine">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/S160053680905048X/tk2583sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905048X/tk2583Isup2.hkl

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

C9H8Br3NO	F(000) = 1456
Mr = 385.89	Dx = 2.198 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 11.360 (1) Å	θ = 4.9–20.6°
b = 10.280 (1) Å	µ = 12.58 mm−1
c = 20.298 (3) Å	T = 299 K
β = 100.23 (1)°	Rod, colourless
V = 2332.7 (5) Å3	0.28 × 0.13 × 0.08 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	2939 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
graphite	θmax = 67.0°, θmin = 4.2°
ω/2θ scans	h = −13→1
Absorption correction: ψ scan (North et al., 1968)	k = −12→0
Tmin = 0.127, Tmax = 0.433	l = −23→24
4358 measured reflections	3 standard reflections every 120 min
4147 independent reflections	intensity decay: 1.0%

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) = 0.249	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1741P)2 + 2.28P] where P = (Fo2 + 2Fc2)/3
4147 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 1.60 e Å−3
0 restraints	Δρmin = −1.66 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	0.6706 (9)	0.5084 (11)	−0.0373 (5)	0.042 (2)
C2	0.6595 (10)	0.4132 (11)	−0.0870 (5)	0.049 (3)
H2	0.7156	0.3465	−0.0832	0.059*
C3	0.5676 (11)	0.4153 (13)	−0.1414 (6)	0.059 (3)
C4	0.4854 (11)	0.5134 (15)	−0.1451 (7)	0.068 (3)
H4	0.4246	0.5196	−0.1822	0.082*
C5	0.4922 (13)	0.6036 (15)	−0.0939 (8)	0.078 (4)
H5	0.4324	0.6660	−0.0959	0.094*
C6	0.5834 (11)	0.6036 (12)	−0.0409 (7)	0.060 (3)
H6	0.5874	0.6663	−0.0076	0.072*
C7	0.8238 (9)	0.4032 (9)	0.0454 (5)	0.038 (2)
C8	0.9316 (9)	0.4273 (9)	0.1025 (5)	0.041 (2)
C9	0.5614 (13)	0.3160 (14)	−0.1948 (6)	0.068 (4)
H9A	0.5043	0.2503	−0.1886	0.082*
H9B	0.6387	0.2768	−0.1928	0.082*
H9C	0.5373	0.3565	−0.2377	0.082*
Br1	1.01398 (11)	0.58885 (12)	0.09396 (6)	0.0534 (4)
Br2	0.86902 (12)	0.42753 (12)	0.18531 (5)	0.0544 (4)
Br3	1.04582 (12)	0.28886 (14)	0.10312 (7)	0.0645 (4)
N1	0.7674 (7)	0.5085 (8)	0.0170 (4)	0.0396 (18)
H1N	0.7923	0.5829	0.0332	0.047*
O1	0.7944 (8)	0.2926 (7)	0.0314 (4)	0.055 (2)
C10	0.1952 (9)	−0.0100 (10)	0.0500 (5)	0.041 (2)
C11	0.2737 (10)	0.0681 (10)	0.0959 (5)	0.047 (2)
H11	0.3299	0.1209	0.0808	0.056*
C12	0.2665 (13)	0.0654 (12)	0.1619 (5)	0.060 (3)
C13	0.1874 (14)	−0.0199 (13)	0.1849 (6)	0.070 (4)
H13	0.1880	−0.0289	0.2305	0.084*
C14	0.1082 (14)	−0.0910 (12)	0.1392 (7)	0.068 (4)
H14	0.0501	−0.1408	0.1543	0.082*
C15	0.1128 (12)	−0.0905 (11)	0.0720 (6)	0.056 (3)
H15	0.0619	−0.1428	0.0422	0.067*
C16	0.2210 (9)	0.0901 (9)	−0.0539 (5)	0.041 (2)
C17	0.2661 (11)	0.0687 (11)	−0.1209 (6)	0.051 (3)
C18	0.3472 (14)	0.1501 (18)	0.2107 (7)	0.084 (5)
H18A	0.3064	0.2295	0.2174	0.101*
H18B	0.4184	0.1696	0.1933	0.101*
H18C	0.3682	0.1052	0.2526	0.101*
Br4	0.22259 (14)	0.21315 (14)	−0.17949 (7)	0.0697 (5)
Br5	0.44004 (14)	0.05889 (19)	−0.09624 (9)	0.0877 (6)
Br6	0.21012 (18)	−0.08796 (14)	−0.16568 (7)	0.0792 (5)
N2	0.2067 (9)	−0.0130 (8)	−0.0181 (4)	0.047 (2)
H2N	0.2041	−0.0876	−0.0375	0.056*
O2	0.2111 (8)	0.2020 (7)	−0.0359 (4)	0.0539 (19)

	U11	U22	U33	U12	U13	U23
C1	0.043 (5)	0.053 (6)	0.031 (5)	0.005 (5)	0.007 (4)	0.005 (4)
C2	0.041 (5)	0.068 (7)	0.035 (5)	0.000 (5)	0.002 (4)	0.003 (5)
C3	0.052 (6)	0.083 (9)	0.041 (6)	−0.015 (6)	0.009 (5)	0.008 (6)
C4	0.051 (7)	0.089 (10)	0.059 (8)	−0.008 (7)	−0.006 (6)	0.007 (7)
C5	0.064 (8)	0.084 (10)	0.083 (11)	0.020 (8)	0.000 (7)	0.020 (8)
C6	0.056 (7)	0.052 (7)	0.070 (8)	−0.010 (5)	0.007 (6)	0.005 (6)
C7	0.046 (5)	0.037 (5)	0.031 (5)	0.005 (4)	0.007 (4)	0.004 (4)
C8	0.048 (6)	0.043 (5)	0.030 (5)	0.001 (4)	0.003 (4)	0.002 (4)
C9	0.083 (9)	0.087 (9)	0.033 (6)	−0.020 (7)	0.007 (6)	−0.004 (6)
Br1	0.0538 (7)	0.0568 (7)	0.0478 (7)	−0.0096 (5)	0.0043 (5)	−0.0019 (5)
Br2	0.0668 (8)	0.0680 (8)	0.0295 (6)	0.0008 (6)	0.0110 (5)	0.0026 (5)
Br3	0.0608 (8)	0.0645 (8)	0.0660 (8)	0.0231 (6)	0.0057 (6)	0.0021 (6)
N1	0.036 (4)	0.035 (4)	0.045 (5)	−0.001 (3)	0.000 (3)	0.002 (3)
O1	0.078 (5)	0.037 (4)	0.043 (4)	−0.003 (4)	−0.009 (4)	−0.003 (3)
C10	0.057 (6)	0.036 (5)	0.031 (5)	0.013 (4)	0.010 (4)	0.003 (4)
C11	0.055 (6)	0.052 (6)	0.033 (5)	0.014 (5)	0.005 (4)	0.002 (4)
C12	0.080 (8)	0.070 (8)	0.026 (5)	0.020 (6)	−0.004 (5)	−0.004 (5)
C13	0.110 (11)	0.067 (8)	0.037 (6)	0.019 (8)	0.029 (7)	−0.001 (6)
C14	0.108 (11)	0.050 (7)	0.059 (8)	−0.007 (7)	0.051 (8)	0.004 (5)
C15	0.077 (8)	0.048 (6)	0.046 (6)	−0.003 (6)	0.024 (6)	−0.010 (5)
C16	0.052 (6)	0.042 (5)	0.028 (5)	0.000 (4)	0.006 (4)	−0.007 (4)
C17	0.058 (7)	0.055 (6)	0.043 (6)	0.001 (5)	0.016 (5)	0.005 (5)
C18	0.086 (10)	0.118 (13)	0.042 (7)	0.010 (9)	−0.007 (7)	−0.016 (8)
Br4	0.0915 (10)	0.0705 (9)	0.0531 (8)	0.0183 (7)	0.0289 (7)	0.0263 (6)
Br5	0.0563 (8)	0.1225 (15)	0.0868 (12)	0.0133 (8)	0.0192 (8)	0.0250 (10)
Br6	0.1327 (15)	0.0674 (9)	0.0405 (7)	−0.0189 (8)	0.0231 (8)	−0.0114 (6)
N2	0.072 (6)	0.035 (4)	0.035 (4)	−0.001 (4)	0.015 (4)	−0.003 (3)
O2	0.079 (5)	0.033 (4)	0.050 (4)	0.003 (4)	0.013 (4)	0.002 (3)

C1—C6	1.385 (16)	C10—C15	1.382 (16)
C1—C2	1.394 (15)	C10—N2	1.411 (12)
C1—N1	1.412 (12)	C10—C11	1.419 (15)
C2—C3	1.379 (16)	C11—C12	1.357 (15)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.367 (19)	C12—C13	1.39 (2)
C3—C9	1.482 (17)	C12—C18	1.503 (18)
C4—C5	1.38 (2)	C13—C14	1.38 (2)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.354 (18)	C14—C15	1.373 (16)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300
C7—O1	1.205 (12)	C16—O2	1.218 (12)
C7—N1	1.336 (12)	C16—N2	1.311 (13)
C7—C8	1.548 (14)	C16—C17	1.553 (14)
C8—Br3	1.925 (10)	C17—Br6	1.902 (12)
C8—Br1	1.929 (10)	C17—Br4	1.912 (11)
C8—Br2	1.938 (10)	C17—Br5	1.953 (12)
C9—H9A	0.9600	C18—H18A	0.9600
C9—H9B	0.9600	C18—H18B	0.9600
C9—H9C	0.9600	C18—H18C	0.9600
N1—H1N	0.8600	N2—H2N	0.8600
C6—C1—C2	119.0 (10)	C15—C10—N2	119.4 (9)
C6—C1—N1	119.4 (10)	C15—C10—C11	120.6 (10)
C2—C1—N1	121.5 (9)	N2—C10—C11	119.9 (10)
C3—C2—C1	121.8 (11)	C12—C11—C10	119.7 (12)
C3—C2—H2	119.1	C12—C11—H11	120.1
C1—C2—H2	119.1	C10—C11—H11	120.1
C4—C3—C2	117.9 (12)	C11—C12—C13	119.9 (12)
C4—C3—C9	121.7 (12)	C11—C12—C18	120.2 (14)
C2—C3—C9	120.4 (12)	C13—C12—C18	119.8 (12)
C3—C4—C5	120.5 (12)	C14—C13—C12	119.3 (11)
C3—C4—H4	119.8	C14—C13—H13	120.3
C5—C4—H4	119.8	C12—C13—H13	120.3
C6—C5—C4	121.9 (13)	C15—C14—C13	122.0 (12)
C6—C5—H5	119.1	C15—C14—H14	119.0
C4—C5—H5	119.1	C13—C14—H14	119.0
C5—C6—C1	118.8 (13)	C14—C15—C10	118.1 (11)
C5—C6—H6	120.6	C14—C15—H15	120.9
C1—C6—H6	120.6	C10—C15—H15	120.9
O1—C7—N1	124.8 (9)	O2—C16—N2	124.8 (9)
O1—C7—C8	118.5 (8)	O2—C16—C17	117.3 (9)
N1—C7—C8	116.6 (8)	N2—C16—C17	117.6 (9)
C7—C8—Br3	109.2 (6)	C16—C17—Br6	113.8 (7)
C7—C8—Br1	113.8 (6)	C16—C17—Br4	110.2 (7)
Br3—C8—Br1	107.4 (5)	Br6—C17—Br4	109.5 (6)
C7—C8—Br2	106.6 (7)	C16—C17—Br5	105.0 (7)
Br3—C8—Br2	110.2 (5)	Br6—C17—Br5	108.4 (6)
Br1—C8—Br2	109.6 (5)	Br4—C17—Br5	109.7 (6)
C3—C9—H9A	109.5	C12—C18—H18A	109.5
C3—C9—H9B	109.5	C12—C18—H18B	109.5
H9A—C9—H9B	109.5	H18A—C18—H18B	109.5
C3—C9—H9C	109.5	C12—C18—H18C	109.5
H9A—C9—H9C	109.5	H18A—C18—H18C	109.5
H9B—C9—H9C	109.5	H18B—C18—H18C	109.5
C7—N1—C1	125.7 (9)	C16—N2—C10	124.5 (8)
C7—N1—H1N	117.1	C16—N2—H2N	117.7
C1—N1—H1N	117.1	C10—N2—H2N	117.7
C6—C1—C2—C3	3.6 (17)	C15—C10—C11—C12	−1.1 (16)
N1—C1—C2—C3	−177.6 (10)	N2—C10—C11—C12	−176.5 (10)
C1—C2—C3—C4	−1.0 (17)	C10—C11—C12—C13	4.1 (17)
C1—C2—C3—C9	177.3 (10)	C10—C11—C12—C18	−178.5 (11)
C2—C3—C4—C5	−3(2)	C11—C12—C13—C14	−7(2)
C9—C3—C4—C5	178.9 (12)	C18—C12—C13—C14	175.8 (13)
C3—C4—C5—C6	4(2)	C12—C13—C14—C15	7(2)
C4—C5—C6—C1	−2(2)	C13—C14—C15—C10	−4(2)
C2—C1—C6—C5	−2.3 (18)	N2—C10—C15—C14	176.3 (11)
N1—C1—C6—C5	178.9 (11)	C11—C10—C15—C14	0.9 (17)
O1—C7—C8—Br3	33.1 (12)	O2—C16—C17—Br6	−151.8 (9)
N1—C7—C8—Br3	−149.3 (7)	N2—C16—C17—Br6	34.1 (13)
O1—C7—C8—Br1	153.1 (8)	O2—C16—C17—Br4	−28.4 (13)
N1—C7—C8—Br1	−29.2 (11)	N2—C16—C17—Br4	157.5 (8)
O1—C7—C8—Br2	−86.0 (10)	O2—C16—C17—Br5	89.7 (10)
N1—C7—C8—Br2	91.6 (9)	N2—C16—C17—Br5	−84.4 (10)
O1—C7—N1—C1	−5.2 (17)	O2—C16—N2—C10	−9.8 (18)
C8—C7—N1—C1	177.3 (9)	C17—C16—N2—C10	163.8 (10)
C6—C1—N1—C7	146.8 (11)	C15—C10—N2—C16	139.2 (11)
C2—C1—N1—C7	−32.0 (15)	C11—C10—N2—C16	−45.4 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86	2.21	3.005 (11)	153
N1—H1N···Br1	0.86	2.60	3.068 (8)	115
N2—H2N···O1ii	0.86	2.11	2.886 (11)	150
N2—H2N···Br6	0.86	2.61	3.100 (8)	117

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86	2.21	3.005 (11)	153
N1—H1N⋯Br1	0.86	2.60	3.068 (8)	115
N2—H2N⋯O1ii	0.86	2.11	2.886 (11)	150
N2—H2N⋯Br6	0.86	2.61	3.100 (8)	117

Symmetry codes: (i) ; (ii) .