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

The asymmetric unit of the title compound, C(9)H(8)Br(3)NO, contains two independent mol-ecules which differ in the orientation of the tribromo group. A weak intra-molecular N-H⋯Br hydrogen bond is observed in each mol-ecule. In the crystal, the independent mol-ecules are linked into chains along the b axis by inter-molecular N-H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C9H8Br3NO

M = 385.89

Monoclinic,

a = 9.6926 (6) Å

b = 20.531 (1) Å

c = 11.8139 (8) Å

β = 102.664 (7)°

V = 2293.8 (2) Å3

Z = 8

Mo Kα radiation

μ = 10.52 mm−1

T = 299 K

0.48 × 0.40 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.081, T max = 0.145

14714 measured reflections

4121 independent reflections

3375 reflections with I > 2σ(I)

R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.082

wR(F 2) = 0.151

S = 1.28

4121 reflections

255 parameters

H-atom parameters constrained

Δρmax = 1.34 e Å−3

Δρmin = −0.88 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/S1600536810009177/ci5053sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009177/ci5053Isup2.hkl

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

C9H8Br3NO	F(000) = 1456
Mr = 385.89	Dx = 2.235 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5162 reflections
a = 9.6926 (6) Å	θ = 2.7–27.8°
b = 20.531 (1) Å	µ = 10.52 mm−1
c = 11.8139 (8) Å	T = 299 K
β = 102.664 (7)°	Prism, colourless
V = 2293.8 (2) Å3	0.48 × 0.40 × 0.30 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4121 independent reflections
Radiation source: fine-focus sealed tube	3375 reflections with I > 2σ(I)
graphite	Rint = 0.089
Rotation method data acquisition using ω and φ scans.	θmax = 25.4°, θmin = 4.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→11
Tmin = 0.081, Tmax = 0.145	k = −21→24
14714 measured reflections	l = −13→14

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.28	w = 1/[σ2(Fo2) + (0.P)2 + 26.8682P] where P = (Fo2 + 2Fc2)/3
4121 reflections	(Δ/σ)max = 0.001
255 parameters	Δρmax = 1.34 e Å−3
0 restraints	Δρmin = −0.88 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	0.7165 (11)	0.2486 (4)	0.6954 (9)	0.029 (2)
C2	0.7414 (11)	0.1962 (5)	0.6292 (10)	0.035 (3)
H2	0.6948	0.1569	0.6335	0.043*
C3	0.8348 (12)	0.2017 (5)	0.5568 (11)	0.043 (3)
H3	0.8516	0.1658	0.5136	0.051*
C4	0.9039 (11)	0.2598 (5)	0.5475 (9)	0.034 (2)
C5	0.8797 (12)	0.3110 (5)	0.6175 (10)	0.039 (3)
H5	0.9279	0.3500	0.6149	0.047*
C6	0.7875 (12)	0.3065 (5)	0.6901 (10)	0.037 (3)
H6	0.7730	0.3419	0.7353	0.044*
C7	0.5389 (11)	0.2876 (4)	0.7992 (9)	0.028 (2)
C8	0.4213 (11)	0.2643 (4)	0.8592 (9)	0.029 (2)
C9	1.0009 (12)	0.2673 (6)	0.4652 (10)	0.043 (3)
H9A	0.9464	0.2667	0.3869	0.052*
H9B	1.0675	0.2320	0.4762	0.052*
H9C	1.0507	0.3079	0.4800	0.052*
Br1	0.37301 (14)	0.33225 (5)	0.95617 (12)	0.0480 (4)
Br2	0.46539 (15)	0.18686 (5)	0.95318 (12)	0.0510 (4)
Br3	0.25450 (14)	0.24690 (6)	0.73598 (12)	0.0531 (4)
N1	0.6157 (9)	0.2404 (4)	0.7652 (8)	0.033 (2)
H1N	0.6029	0.2015	0.7877	0.039*
O1	0.5509 (8)	0.3449 (3)	0.7822 (7)	0.042 (2)
C10	0.3798 (10)	0.0087 (4)	0.6530 (9)	0.025 (2)
C11	0.3488 (11)	−0.0253 (5)	0.5503 (10)	0.036 (3)
H11	0.4045	−0.0606	0.5390	0.044*
C12	0.2340 (11)	−0.0068 (5)	0.4633 (10)	0.034 (3)
H12	0.2144	−0.0297	0.3937	0.041*
C13	0.1478 (10)	0.0452 (5)	0.4785 (9)	0.029 (2)
C14	0.1792 (12)	0.0765 (5)	0.5829 (11)	0.038 (3)
H14	0.1220	0.1108	0.5960	0.046*
C15	0.2935 (12)	0.0590 (5)	0.6701 (10)	0.035 (3)
H15	0.3117	0.0813	0.7403	0.042*
C16	0.5967 (10)	0.0331 (5)	0.7916 (10)	0.030 (2)
C17	0.7240 (12)	0.0074 (5)	0.8818 (10)	0.036 (3)
C18	0.0294 (13)	0.0685 (5)	0.3837 (10)	0.042 (3)
H18A	0.0032	0.0346	0.3270	0.050*
H18B	0.0595	0.1062	0.3475	0.050*
H18C	−0.0504	0.0795	0.4157	0.050*
Br4	0.75931 (14)	−0.08465 (6)	0.87190 (14)	0.0582 (4)
Br5	0.89309 (14)	0.05436 (7)	0.86845 (12)	0.0540 (4)
Br6	0.69036 (17)	0.02579 (8)	1.03563 (12)	0.0661 (4)
N2	0.5023 (9)	−0.0097 (4)	0.7398 (8)	0.032 (2)
H2N	0.5144	−0.0501	0.7586	0.038*
O2	0.5901 (9)	0.0912 (3)	0.7746 (8)	0.049 (2)

	U11	U22	U33	U12	U13	U23
C1	0.024 (5)	0.027 (5)	0.037 (7)	0.003 (4)	0.006 (5)	0.004 (4)
C2	0.032 (6)	0.025 (5)	0.049 (8)	0.002 (4)	0.007 (6)	−0.001 (5)
C3	0.039 (7)	0.034 (6)	0.057 (9)	0.005 (5)	0.015 (6)	−0.011 (5)
C4	0.031 (6)	0.045 (6)	0.020 (6)	0.008 (5)	−0.004 (5)	0.007 (5)
C5	0.032 (6)	0.036 (6)	0.049 (8)	−0.008 (5)	0.006 (6)	−0.003 (5)
C6	0.035 (6)	0.033 (5)	0.043 (7)	−0.006 (5)	0.008 (6)	−0.009 (5)
C7	0.030 (6)	0.027 (5)	0.028 (6)	0.001 (4)	0.006 (5)	0.001 (4)
C8	0.030 (6)	0.022 (5)	0.029 (6)	0.005 (4)	−0.008 (5)	−0.002 (4)
C9	0.035 (7)	0.055 (7)	0.035 (7)	−0.003 (6)	−0.004 (6)	−0.009 (6)
Br1	0.0487 (7)	0.0402 (6)	0.0610 (9)	−0.0018 (5)	0.0251 (7)	−0.0155 (6)
Br2	0.0660 (9)	0.0386 (6)	0.0484 (8)	0.0034 (6)	0.0128 (7)	0.0101 (6)
Br3	0.0423 (7)	0.0586 (8)	0.0496 (9)	−0.0124 (6)	−0.0086 (6)	−0.0035 (6)
N1	0.035 (5)	0.015 (4)	0.049 (6)	0.000 (4)	0.009 (5)	−0.002 (4)
O1	0.042 (5)	0.021 (4)	0.064 (6)	0.004 (3)	0.017 (4)	0.001 (3)
C10	0.024 (5)	0.022 (5)	0.027 (6)	−0.003 (4)	0.001 (5)	0.004 (4)
C11	0.027 (6)	0.030 (5)	0.051 (8)	0.001 (5)	0.007 (6)	−0.002 (5)
C12	0.032 (6)	0.037 (6)	0.032 (7)	0.000 (5)	0.004 (5)	−0.003 (5)
C13	0.024 (5)	0.028 (5)	0.034 (7)	0.000 (4)	0.007 (5)	0.008 (5)
C14	0.035 (6)	0.028 (5)	0.053 (8)	0.007 (5)	0.014 (6)	0.003 (5)
C15	0.048 (7)	0.026 (5)	0.030 (7)	−0.001 (5)	0.002 (6)	−0.010 (5)
C16	0.023 (5)	0.026 (5)	0.044 (7)	−0.001 (4)	0.012 (5)	−0.003 (5)
C17	0.034 (6)	0.026 (5)	0.044 (7)	−0.009 (5)	0.001 (6)	−0.004 (5)
C18	0.045 (7)	0.046 (6)	0.031 (7)	0.006 (6)	0.002 (6)	0.009 (5)
Br4	0.0472 (8)	0.0352 (6)	0.0788 (11)	0.0055 (5)	−0.0149 (7)	0.0032 (6)
Br5	0.0393 (7)	0.0677 (8)	0.0523 (9)	−0.0199 (6)	0.0043 (6)	−0.0008 (7)
Br6	0.0644 (10)	0.0966 (11)	0.0391 (8)	−0.0102 (8)	0.0150 (7)	−0.0027 (7)
N2	0.033 (5)	0.018 (4)	0.040 (6)	−0.002 (4)	−0.001 (4)	−0.001 (4)
O2	0.044 (5)	0.022 (4)	0.076 (7)	−0.008 (3)	−0.001 (5)	0.005 (4)

C1—C2	1.383 (14)	C10—C15	1.371 (13)
C1—C6	1.382 (13)	C10—C11	1.374 (14)
C1—N1	1.420 (12)	C10—N2	1.439 (13)
C2—C3	1.380 (15)	C11—C12	1.392 (15)
C2—H2	0.93	C11—H11	0.93
C3—C4	1.384 (15)	C12—C13	1.392 (13)
C3—H3	0.93	C12—H12	0.93
C4—C5	1.389 (14)	C13—C14	1.366 (15)
C4—C9	1.501 (15)	C13—C18	1.495 (15)
C5—C6	1.371 (15)	C14—C15	1.384 (16)
C5—H5	0.93	C14—H14	0.93
C6—H6	0.93	C15—H15	0.93
C7—O1	1.201 (11)	C16—O2	1.209 (11)
C7—N1	1.337 (12)	C16—N2	1.318 (13)
C7—C8	1.545 (14)	C16—C17	1.536 (15)
C8—Br1	1.927 (9)	C17—Br4	1.928 (10)
C8—Br2	1.932 (9)	C17—Br5	1.938 (10)
C8—Br3	1.957 (10)	C17—Br6	1.953 (11)
C9—H9A	0.96	C18—H18A	0.96
C9—H9B	0.96	C18—H18B	0.96
C9—H9C	0.96	C18—H18C	0.96
N1—H1N	0.86	N2—H2N	0.86
C2—C1—C6	119.6 (9)	C15—C10—C11	119.3 (10)
C2—C1—N1	117.7 (8)	C15—C10—N2	121.8 (9)
C6—C1—N1	122.8 (9)	C11—C10—N2	118.8 (9)
C3—C2—C1	120.5 (9)	C10—C11—C12	119.9 (10)
C3—C2—H2	119.8	C10—C11—H11	120.1
C1—C2—H2	119.8	C12—C11—H11	120.1
C2—C3—C4	120.9 (10)	C13—C12—C11	121.3 (10)
C2—C3—H3	119.5	C13—C12—H12	119.4
C4—C3—H3	119.5	C11—C12—H12	119.4
C3—C4—C5	117.2 (10)	C14—C13—C12	117.2 (10)
C3—C4—C9	121.5 (10)	C14—C13—C18	120.6 (9)
C5—C4—C9	121.3 (10)	C12—C13—C18	122.2 (10)
C6—C5—C4	122.7 (10)	C13—C14—C15	122.2 (10)
C6—C5—H5	118.7	C13—C14—H14	118.9
C4—C5—H5	118.7	C15—C14—H14	118.9
C5—C6—C1	119.1 (10)	C10—C15—C14	120.1 (10)
C5—C6—H6	120.5	C10—C15—H15	120.0
C1—C6—H6	120.5	C14—C15—H15	120.0
O1—C7—N1	125.4 (9)	O2—C16—N2	125.0 (11)
O1—C7—C8	119.2 (8)	O2—C16—C17	117.4 (9)
N1—C7—C8	115.3 (8)	N2—C16—C17	117.6 (8)
C7—C8—Br1	110.4 (6)	C16—C17—Br4	114.9 (7)
C7—C8—Br2	115.2 (6)	C16—C17—Br5	109.7 (7)
Br1—C8—Br2	107.8 (5)	Br4—C17—Br5	108.5 (5)
C7—C8—Br3	106.7 (7)	C16—C17—Br6	107.9 (7)
Br1—C8—Br3	107.8 (5)	Br4—C17—Br6	108.3 (5)
Br2—C8—Br3	108.7 (5)	Br5—C17—Br6	107.2 (5)
C4—C9—H9A	109.5	C13—C18—H18A	109.5
C4—C9—H9B	109.5	C13—C18—H18B	109.5
H9A—C9—H9B	109.5	H18A—C18—H18B	109.5
C4—C9—H9C	109.5	C13—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	126.0 (8)	C16—N2—C10	122.4 (8)
C7—N1—H1N	117.0	C16—N2—H2N	118.8
C1—N1—H1N	117.0	C10—N2—H2N	118.8
C6—C1—C2—C3	−1.0 (17)	C15—C10—C11—C12	2.5 (14)
N1—C1—C2—C3	178.0 (10)	N2—C10—C11—C12	−177.6 (9)
C1—C2—C3—C4	−1.0 (18)	C10—C11—C12—C13	−0.8 (15)
C2—C3—C4—C5	2.7 (17)	C11—C12—C13—C14	−1.2 (14)
C2—C3—C4—C9	−177.3 (11)	C11—C12—C13—C18	176.1 (10)
C3—C4—C5—C6	−2.6 (17)	C12—C13—C14—C15	1.5 (15)
C9—C4—C5—C6	177.4 (11)	C18—C13—C14—C15	−175.8 (10)
C4—C5—C6—C1	0.7 (18)	C11—C10—C15—C14	−2.2 (15)
C2—C1—C6—C5	1.2 (17)	N2—C10—C15—C14	177.9 (9)
N1—C1—C6—C5	−177.8 (11)	C13—C14—C15—C10	0.1 (16)
O1—C7—C8—Br1	−26.3 (12)	O2—C16—C17—Br4	−162.1 (8)
N1—C7—C8—Br1	156.8 (8)	N2—C16—C17—Br4	18.7 (12)
O1—C7—C8—Br2	−148.7 (9)	O2—C16—C17—Br5	−39.5 (12)
N1—C7—C8—Br2	34.4 (12)	N2—C16—C17—Br5	141.3 (8)
O1—C7—C8—Br3	90.6 (10)	O2—C16—C17—Br6	77.0 (10)
N1—C7—C8—Br3	−86.3 (9)	N2—C16—C17—Br6	−102.2 (9)
O1—C7—N1—C1	−5.5 (18)	O2—C16—N2—C10	1.6 (16)
C8—C7—N1—C1	171.2 (10)	C17—C16—N2—C10	−179.3 (9)
C2—C1—N1—C7	−153.2 (11)	C15—C10—N2—C16	−49.1 (14)
C6—C1—N1—C7	25.8 (17)	C11—C10—N2—C16	130.9 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.86	2.27	3.078 (10)	156
N1—H1N···Br2	0.86	2.61	3.111 (8)	118
N2—H2N···O1i	0.86	2.27	3.032 (10)	148
N2—H2N···Br4	0.86	2.56	3.051 (9)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2	0.86	2.27	3.078 (10)	156
N1—H1N⋯Br2	0.86	2.61	3.111 (8)	118
N2—H2N⋯O1i	0.86	2.27	3.032 (10)	148
N2—H2N⋯Br4	0.86	2.56	3.051 (9)	118

Symmetry code: (i) .