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

The asymmetric unit of the title compound, C(9)H(8)Br(3)NO, contains two independent mol-ecules. Intra-molecular N-H⋯Br hydrogen bonds are present in both mol-ecules. In the crystal, mol-ecules are packed into columnar chains by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For preparation of the title compound, see: Gowda et al. (2003 ▶). For background to our study of the effect of ring and side-chain substituents on the solid state structures of N-aromatic amides and for related structures, see: Brown (1966 ▶); Gowda et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C9H8Br3NO

M = 385.89

Monoclinic,

a = 9.949 (2) Å

b = 21.429 (4) Å

c = 11.653 (2) Å

β = 107.69 (1)°

V = 2366.9 (8) Å3

Z = 8

Cu Kα radiation

μ = 12.40 mm−1

T = 299 K

0.55 × 0.28 × 0.28 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.056, T max = 0.129

5721 measured reflections

4204 independent reflections

3666 reflections with I > 2σ(I)

R int = 0.149

3 standard reflections every 120 min intensity decay: 1.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.212

S = 1.05

4204 reflections

260 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.77 e Å−3

Δρmin = −1.34 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/S1600536810009852/pk2229sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009852/pk2229Isup2.hkl

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

C9H8Br3NO	F(000) = 1456
Mr = 385.89	Dx = 2.166 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.949 (2) Å	θ = 4.1–18.8°
b = 21.429 (4) Å	µ = 12.40 mm−1
c = 11.653 (2) Å	T = 299 K
β = 107.69 (1)°	Rod, colourless
V = 2366.9 (8) Å3	0.55 × 0.28 × 0.28 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	3666 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.149
graphite	θmax = 67.0°, θmin = 4.1°
ω/2θ scans	h = −11→3
Absorption correction: ψ scan (North et al., 1968)	k = −25→0
Tmin = 0.056, Tmax = 0.129	l = −13→13
5721 measured reflections	3 standard reflections every 120 min
4204 independent reflections	intensity decay: 1.5%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.073	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.212	w = 1/[σ2(Fo2) + (0.1206P)2 + 14.5272P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
4204 reflections	Δρmax = 1.77 e Å−3
260 parameters	Δρmin = −1.33 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00203 (19)

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	−0.0153 (8)	0.3501 (4)	0.6789 (7)	0.0360 (16)
C2	0.0276 (9)	0.3149 (4)	0.7841 (7)	0.0428 (18)
C3	0.0010 (11)	0.2519 (5)	0.7730 (10)	0.059 (2)
H3	0.0286	0.2272	0.8418	0.071*
C4	−0.0656 (12)	0.2238 (5)	0.6631 (12)	0.063 (3)
H4	−0.0811	0.1809	0.6587	0.076*
C5	−0.1078 (11)	0.2593 (5)	0.5620 (11)	0.061 (3)
H5	−0.1535	0.2410	0.4881	0.073*
C6	−0.0822 (9)	0.3234 (4)	0.5694 (8)	0.0453 (19)
H6	−0.1104	0.3480	0.5004	0.054*
C7	−0.0894 (7)	0.4574 (3)	0.6711 (7)	0.0335 (15)
C8	−0.0422 (8)	0.5264 (4)	0.6954 (6)	0.0356 (15)
C9	0.0957 (12)	0.3450 (6)	0.9028 (9)	0.065 (3)
H9A	0.0317	0.3747	0.9196	0.078*
H9B	0.1800	0.3661	0.9006	0.078*
H9C	0.1191	0.3138	0.9647	0.078*
N1	0.0124 (6)	0.4153 (3)	0.6855 (6)	0.0369 (14)
H1N	0.095 (5)	0.429 (4)	0.700 (9)	0.044*
O1	−0.2153 (6)	0.4451 (3)	0.6442 (7)	0.0537 (16)
Br1	0.14164 (9)	0.54417 (4)	0.68400 (10)	0.0519 (3)
Br2	−0.04344 (14)	0.54241 (6)	0.85827 (9)	0.0703 (4)
Br3	−0.17695 (10)	0.57952 (5)	0.58669 (10)	0.0581 (4)
C10	0.5167 (7)	0.4983 (4)	0.7302 (7)	0.0350 (15)
C11	0.5752 (9)	0.5236 (4)	0.8425 (8)	0.0464 (19)
C12	0.5630 (12)	0.5873 (6)	0.8526 (11)	0.068 (3)
H12	0.6000	0.6059	0.9277	0.082*
C13	0.4978 (12)	0.6242 (5)	0.7546 (13)	0.069 (3)
H13	0.4913	0.6671	0.7636	0.082*
C14	0.4424 (10)	0.5969 (5)	0.6435 (11)	0.059 (3)
H14	0.3986	0.6215	0.5769	0.070*
C15	0.4512 (9)	0.5338 (4)	0.6306 (8)	0.0439 (18)
H15	0.4136	0.5152	0.5555	0.053*
C16	0.4364 (7)	0.3930 (3)	0.7382 (7)	0.0338 (15)
C17	0.4640 (7)	0.3218 (4)	0.7325 (7)	0.0354 (16)
C18	0.6471 (13)	0.4835 (7)	0.9492 (10)	0.075 (3)
H18A	0.7243	0.4616	0.9341	0.090*
H18B	0.5809	0.4539	0.9624	0.090*
H18C	0.6822	0.5093	1.0194	0.090*
N2	0.5275 (7)	0.4317 (3)	0.7144 (6)	0.0370 (14)
H2N	0.591 (8)	0.416 (4)	0.689 (8)	0.044*
O2	0.3318 (7)	0.4088 (3)	0.7643 (7)	0.0539 (16)
Br4	0.48061 (16)	0.28822 (6)	0.88797 (10)	0.0740 (4)
Br5	0.63133 (11)	0.30070 (5)	0.68942 (12)	0.0628 (4)
Br6	0.30461 (11)	0.28588 (5)	0.61417 (12)	0.0677 (4)

	U11	U22	U33	U12	U13	U23
C1	0.033 (3)	0.036 (4)	0.042 (4)	0.005 (3)	0.016 (3)	0.006 (3)
C2	0.046 (4)	0.045 (5)	0.044 (4)	0.005 (4)	0.024 (3)	0.004 (3)
C3	0.070 (6)	0.045 (5)	0.072 (7)	0.013 (5)	0.034 (5)	0.019 (5)
C4	0.079 (7)	0.028 (5)	0.096 (8)	−0.001 (4)	0.046 (6)	−0.004 (5)
C5	0.064 (6)	0.043 (5)	0.079 (7)	−0.008 (4)	0.029 (5)	−0.022 (5)
C6	0.049 (4)	0.046 (5)	0.040 (4)	0.006 (4)	0.013 (3)	0.004 (3)
C7	0.035 (4)	0.027 (4)	0.041 (4)	−0.002 (3)	0.015 (3)	0.007 (3)
C8	0.038 (4)	0.040 (4)	0.032 (3)	0.001 (3)	0.015 (3)	0.000 (3)
C9	0.069 (6)	0.078 (8)	0.043 (5)	−0.004 (6)	0.010 (4)	0.010 (5)
N1	0.026 (3)	0.039 (4)	0.044 (4)	−0.002 (3)	0.008 (2)	0.008 (3)
O1	0.038 (3)	0.036 (3)	0.087 (5)	0.002 (2)	0.019 (3)	0.004 (3)
Br1	0.0403 (5)	0.0394 (6)	0.0790 (7)	−0.0034 (3)	0.0227 (4)	0.0118 (4)
Br2	0.1006 (9)	0.0767 (8)	0.0412 (6)	−0.0170 (6)	0.0330 (5)	−0.0102 (5)
Br3	0.0506 (5)	0.0381 (6)	0.0706 (7)	0.0069 (4)	−0.0041 (4)	0.0126 (4)
C10	0.032 (3)	0.030 (4)	0.045 (4)	−0.005 (3)	0.015 (3)	0.000 (3)
C11	0.041 (4)	0.045 (5)	0.052 (5)	−0.006 (4)	0.011 (3)	−0.005 (4)
C12	0.070 (6)	0.060 (7)	0.071 (7)	−0.017 (5)	0.014 (5)	−0.035 (5)
C13	0.068 (6)	0.029 (5)	0.107 (9)	−0.008 (4)	0.025 (6)	−0.006 (5)
C14	0.055 (5)	0.037 (5)	0.085 (7)	0.008 (4)	0.023 (5)	0.019 (5)
C15	0.044 (4)	0.040 (5)	0.047 (4)	−0.004 (3)	0.015 (3)	0.001 (3)
C16	0.033 (3)	0.027 (4)	0.042 (4)	0.009 (3)	0.012 (3)	0.001 (3)
C17	0.030 (3)	0.027 (4)	0.049 (4)	0.002 (3)	0.012 (3)	0.003 (3)
C18	0.074 (7)	0.090 (9)	0.046 (5)	−0.002 (6)	−0.003 (5)	0.006 (5)
N2	0.041 (3)	0.023 (3)	0.053 (4)	0.005 (3)	0.023 (3)	0.001 (3)
O2	0.049 (3)	0.031 (3)	0.091 (5)	0.003 (3)	0.036 (3)	0.000 (3)
Br4	0.1248 (11)	0.0556 (7)	0.0497 (6)	0.0301 (6)	0.0387 (6)	0.0187 (5)
Br5	0.0549 (6)	0.0364 (6)	0.1123 (9)	0.0086 (4)	0.0482 (6)	−0.0001 (5)
Br6	0.0544 (6)	0.0506 (7)	0.0818 (8)	0.0001 (4)	−0.0036 (5)	−0.0176 (5)

C1—C6	1.371 (12)	C10—C11	1.372 (12)
C1—C2	1.391 (11)	C10—C15	1.375 (12)
C1—N1	1.423 (11)	C10—N2	1.446 (10)
C2—C3	1.374 (14)	C11—C12	1.377 (15)
C2—C9	1.490 (14)	C11—C18	1.503 (14)
C3—C4	1.389 (17)	C12—C13	1.378 (18)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.358 (17)	C13—C14	1.374 (17)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.396 (14)	C14—C15	1.366 (13)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300
C7—O1	1.224 (9)	C16—O2	1.217 (9)
C7—N1	1.329 (10)	C16—N2	1.320 (10)
C7—C8	1.552 (11)	C16—C17	1.554 (10)
C8—Br1	1.912 (7)	C17—Br4	1.910 (8)
C8—Br3	1.914 (8)	C17—Br6	1.918 (8)
C8—Br2	1.932 (7)	C17—Br5	1.933 (7)
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	0.84 (4)	N2—H2N	0.85 (4)
C6—C1—C2	121.8 (8)	C11—C10—C15	122.7 (8)
C6—C1—N1	119.4 (7)	C11—C10—N2	119.0 (7)
C2—C1—N1	118.8 (7)	C15—C10—N2	118.3 (7)
C3—C2—C1	116.8 (8)	C10—C11—C12	116.8 (9)
C3—C2—C9	122.2 (9)	C10—C11—C18	121.3 (9)
C1—C2—C9	121.0 (9)	C12—C11—C18	121.9 (10)
C2—C3—C4	122.5 (9)	C11—C12—C13	121.9 (10)
C2—C3—H3	118.7	C11—C12—H12	119.0
C4—C3—H3	118.7	C13—C12—H12	119.0
C5—C4—C3	119.5 (9)	C14—C13—C12	119.3 (9)
C5—C4—H4	120.3	C14—C13—H13	120.4
C3—C4—H4	120.3	C12—C13—H13	120.4
C4—C5—C6	119.7 (10)	C15—C14—C13	120.3 (10)
C4—C5—H5	120.1	C15—C14—H14	119.9
C6—C5—H5	120.1	C13—C14—H14	119.9
C1—C6—C5	119.7 (9)	C14—C15—C10	119.0 (9)
C1—C6—H6	120.2	C14—C15—H15	120.5
C5—C6—H6	120.2	C10—C15—H15	120.5
O1—C7—N1	124.6 (7)	O2—C16—N2	124.8 (7)
O1—C7—C8	118.8 (7)	O2—C16—C17	117.4 (7)
N1—C7—C8	116.5 (6)	N2—C16—C17	117.8 (6)
C7—C8—Br1	114.8 (5)	C16—C17—Br4	107.1 (5)
C7—C8—Br3	109.5 (5)	C16—C17—Br6	107.8 (5)
Br1—C8—Br3	109.2 (4)	Br4—C17—Br6	110.2 (4)
C7—C8—Br2	104.8 (5)	C16—C17—Br5	114.7 (5)
Br1—C8—Br2	109.0 (4)	Br4—C17—Br5	109.0 (4)
Br3—C8—Br2	109.4 (4)	Br6—C17—Br5	108.0 (4)
C2—C9—H9A	109.5	C11—C18—H18A	109.5
C2—C9—H9B	109.5	C11—C18—H18B	109.5
H9A—C9—H9B	109.5	H18A—C18—H18B	109.5
C2—C9—H9C	109.5	C11—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	122.2 (6)	C16—N2—C10	120.8 (6)
C7—N1—H1N	117 (7)	C16—N2—H2N	117 (7)
C1—N1—H1N	120 (7)	C10—N2—H2N	122 (7)
C6—C1—C2—C3	0.6 (12)	C15—C10—C11—C12	1.4 (12)
N1—C1—C2—C3	−178.8 (7)	N2—C10—C11—C12	179.5 (8)
C6—C1—C2—C9	−177.9 (8)	C15—C10—C11—C18	−179.4 (9)
N1—C1—C2—C9	2.7 (11)	N2—C10—C11—C18	−1.3 (12)
C1—C2—C3—C4	−0.1 (14)	C10—C11—C12—C13	−1.2 (15)
C9—C2—C3—C4	178.4 (9)	C18—C11—C12—C13	179.7 (11)
C2—C3—C4—C5	−0.6 (16)	C11—C12—C13—C14	0.3 (17)
C3—C4—C5—C6	0.8 (15)	C12—C13—C14—C15	0.4 (16)
C2—C1—C6—C5	−0.4 (12)	C13—C14—C15—C10	−0.2 (14)
N1—C1—C6—C5	179.0 (8)	C11—C10—C15—C14	−0.7 (12)
C4—C5—C6—C1	−0.3 (14)	N2—C10—C15—C14	−178.9 (7)
O1—C7—C8—Br1	−160.3 (6)	O2—C16—C17—Br4	−59.3 (8)
N1—C7—C8—Br1	21.9 (8)	N2—C16—C17—Br4	120.7 (6)
O1—C7—C8—Br3	−37.2 (9)	O2—C16—C17—Br6	59.3 (8)
N1—C7—C8—Br3	145.1 (6)	N2—C16—C17—Br6	−120.7 (6)
O1—C7—C8—Br2	80.1 (8)	O2—C16—C17—Br5	179.6 (6)
N1—C7—C8—Br2	−97.6 (6)	N2—C16—C17—Br5	−0.3 (9)
O1—C7—N1—C1	−4.5 (12)	O2—C16—N2—C10	6.5 (12)
C8—C7—N1—C1	173.0 (6)	C17—C16—N2—C10	−173.5 (7)
C6—C1—N1—C7	71.7 (10)	C11—C10—N2—C16	83.9 (9)
C2—C1—N1—C7	−108.9 (8)	C15—C10—N2—C16	−97.9 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.84 (4)	2.28 (6)	3.031 (8)	149 (9)
N1—H1N···Br1	0.84 (4)	2.53 (9)	3.048 (7)	120 (8)
N2—H2N···O1i	0.85 (4)	2.23 (7)	2.928 (9)	139 (9)
N2—H2N···Br5	0.85 (4)	2.50 (9)	3.036 (6)	122 (8)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2	0.84 (4)	2.28 (6)	3.031 (8)	149 (9)
N1—H1N⋯Br1	0.84 (4)	2.53 (9)	3.048 (7)	120 (8)
N2—H2N⋯O1i	0.85 (4)	2.23 (7)	2.928 (9)	139 (9)
N2—H2N⋯Br5	0.85 (4)	2.50 (9)	3.036 (6)	122 (8)

Symmetry code: (i) .