N-(3-Bromo-phen-yl)acetamide.

The conformation of the N-H bond in the structure of the title compound, C(8)H(8)BrNO, is anti to the C=O bond and to the meta-bromo substituent of the aromatic ring in both independent mol-ecules comprising the asymmetric unit. Mol-ecules are linked through N-H⋯O hydrogen bonding into supra-molecular chains with a twisted topology.

Related literature

For the preparation of the compound, see: Gowda et al. (2006 ▶). For related structures, see: Gowda et al. (2007 ▶, 2008 ▶, 2009 ▶).

Experimental

Crystal data

C8H8BrNO

M = 214.06

Orthorhombic,

a = 4.7836 (6) Å

b = 18.765 (1) Å

c = 19.379 (2) Å

V = 1739.5 (3) Å3

Z = 8

Mo Kα radiation

μ = 4.67 mm−1

T = 299 K

0.44 × 0.10 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.226, T max = 0.685

9612 measured reflections

3449 independent reflections

2043 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.093

S = 0.99

3449 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.49 e Å−3

Absolute structure: Flack (1983 ▶), 1366 Friedel pairs

Flack parameter: −0.008 (13)

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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/S1600536809013294/tk2417sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013294/tk2417Isup2.hkl

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

C8H8BrNO	F(000) = 848
Mr = 214.06	Dx = 1.635 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3601 reflections
a = 4.7836 (6) Å	θ = 2.4–27.6°
b = 18.765 (1) Å	µ = 4.67 mm−1
c = 19.379 (2) Å	T = 299 K
V = 1739.5 (3) Å3	Long needle, colourless
Z = 8	0.44 × 0.10 × 0.08 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3449 independent reflections
Radiation source: fine-focus sealed tube	2043 reflections with I > 2σ(I)
graphite	Rint = 0.034
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −5→5
Tmin = 0.226, Tmax = 0.685	k = −22→23
9612 measured reflections	l = −20→24

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0455P)2 + 0.0252P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
3449 reflections	Δρmax = 0.31 e Å−3
201 parameters	Δρmin = −0.49 e Å−3
0 restraints	Absolute structure: Flack (1983), 1366 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.008 (13)

Experimental. Absorption correction: CrysAlis RED, Oxford Diffraction Ltd. (2007). 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	0.64658 (17)	0.36438 (3)	0.40336 (3)	0.0961 (3)
O1	1.0611 (8)	0.22271 (18)	0.20168 (19)	0.0786 (12)
N1	0.9531 (7)	0.13129 (19)	0.27225 (19)	0.0531 (10)
H1N	0.9782	0.0863	0.2779	0.064*
C1	0.7804 (10)	0.1647 (2)	0.3206 (2)	0.0492 (12)
C2	0.7903 (10)	0.2377 (2)	0.3338 (2)	0.0524 (12)
H2	0.9111	0.2670	0.3092	0.063*
C3	0.6192 (12)	0.2656 (3)	0.3838 (2)	0.0606 (14)
C4	0.4398 (12)	0.2247 (4)	0.4216 (3)	0.0740 (17)
H4	0.3269	0.2450	0.4553	0.089*
C5	0.4300 (12)	0.1519 (3)	0.4084 (3)	0.0848 (18)
H5	0.3068	0.1234	0.4331	0.102*
C6	0.6000 (11)	0.1215 (3)	0.3592 (3)	0.0691 (15)
H6	0.5951	0.0726	0.3516	0.083*
C7	1.0850 (10)	0.1608 (3)	0.2180 (2)	0.0546 (13)
C8	1.2664 (11)	0.1102 (2)	0.1767 (2)	0.0726 (17)
H8A	1.2240	0.0620	0.1895	0.087*
H8B	1.4597	0.1199	0.1861	0.087*
H8C	1.2303	0.1166	0.1284	0.087*
Br2	0.30944 (16)	0.49664 (3)	−0.03009 (3)	0.0919 (3)
O2	0.9050 (8)	0.48750 (17)	0.18809 (18)	0.0709 (10)
N2	0.8933 (8)	0.36972 (18)	0.16644 (18)	0.0475 (9)
H2N	0.9634	0.3294	0.1785	0.057*
C9	0.6865 (9)	0.3675 (2)	0.11456 (19)	0.0397 (10)
C10	0.6162 (10)	0.4252 (2)	0.0737 (2)	0.0464 (11)
H10	0.7039	0.4690	0.0799	0.056*
C11	0.4147 (10)	0.4168 (2)	0.0239 (2)	0.0499 (12)
C12	0.2819 (9)	0.3533 (3)	0.0127 (2)	0.0528 (12)
H12	0.1476	0.3489	−0.0218	0.063*
C13	0.3519 (12)	0.2959 (3)	0.0536 (2)	0.0576 (13)
H13	0.2619	0.2525	0.0473	0.069*
C14	0.5532 (9)	0.3025 (2)	0.1035 (2)	0.0490 (12)
H14	0.6013	0.2632	0.1302	0.059*
C15	0.9939 (9)	0.4277 (3)	0.1993 (2)	0.0490 (12)
C16	1.2135 (10)	0.4133 (3)	0.2521 (3)	0.0652 (14)
H16A	1.2663	0.3640	0.2502	0.078*
H16B	1.1416	0.4242	0.2971	0.078*
H16C	1.3739	0.4426	0.2429	0.078*

	U11	U22	U33	U12	U13	U23
Br1	0.1400 (6)	0.0715 (4)	0.0768 (4)	0.0319 (4)	−0.0121 (4)	−0.0259 (3)
O1	0.110 (3)	0.046 (2)	0.080 (2)	0.013 (2)	0.022 (2)	0.0251 (19)
N1	0.067 (3)	0.035 (2)	0.057 (2)	0.0055 (19)	0.003 (2)	0.012 (2)
C1	0.058 (3)	0.045 (3)	0.044 (3)	0.005 (2)	−0.005 (2)	0.006 (2)
C2	0.065 (3)	0.045 (3)	0.047 (2)	0.004 (2)	−0.003 (3)	0.003 (2)
C3	0.075 (4)	0.064 (3)	0.043 (3)	0.021 (3)	−0.007 (3)	−0.006 (3)
C4	0.068 (4)	0.108 (5)	0.046 (3)	0.021 (3)	0.008 (3)	−0.009 (3)
C5	0.089 (5)	0.096 (5)	0.070 (4)	−0.020 (3)	0.014 (4)	0.002 (4)
C6	0.083 (4)	0.059 (3)	0.065 (3)	−0.009 (3)	0.003 (3)	0.009 (3)
C7	0.067 (4)	0.045 (3)	0.052 (3)	0.007 (2)	0.002 (3)	0.008 (2)
C8	0.086 (5)	0.065 (3)	0.066 (3)	0.005 (3)	0.012 (3)	0.002 (3)
Br2	0.1222 (5)	0.0670 (4)	0.0866 (4)	0.0074 (4)	−0.0273 (4)	0.0277 (3)
O2	0.091 (3)	0.0351 (18)	0.086 (2)	0.0039 (19)	−0.014 (2)	−0.0108 (17)
N2	0.058 (3)	0.0299 (19)	0.054 (2)	0.0034 (19)	0.000 (2)	0.0001 (18)
C9	0.044 (3)	0.035 (2)	0.040 (2)	0.000 (2)	0.004 (2)	−0.003 (2)
C10	0.051 (3)	0.035 (2)	0.053 (3)	−0.002 (2)	−0.001 (3)	0.005 (2)
C11	0.059 (3)	0.044 (3)	0.047 (3)	0.008 (2)	0.003 (3)	0.007 (2)
C12	0.048 (3)	0.058 (3)	0.052 (3)	−0.002 (2)	−0.003 (2)	−0.006 (2)
C13	0.056 (3)	0.051 (3)	0.066 (3)	−0.002 (3)	−0.007 (3)	−0.011 (3)
C14	0.053 (3)	0.035 (3)	0.058 (3)	0.000 (2)	0.006 (3)	−0.002 (2)
C15	0.050 (3)	0.047 (3)	0.050 (3)	−0.001 (3)	−0.001 (3)	−0.007 (3)
C16	0.065 (4)	0.062 (3)	0.069 (3)	−0.009 (3)	−0.007 (3)	−0.012 (3)

Br1—C3	1.897 (5)	Br2—C11	1.895 (4)
O1—C7	1.209 (5)	O2—C15	1.220 (5)
N1—C7	1.346 (5)	N2—C15	1.349 (5)
N1—C1	1.398 (5)	N2—C9	1.411 (5)
N1—H1N	0.8600	N2—H2N	0.8600
C1—C2	1.394 (6)	C9—C10	1.383 (5)
C1—C6	1.400 (6)	C9—C14	1.392 (6)
C2—C3	1.372 (6)	C10—C11	1.374 (6)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.364 (7)	C11—C12	1.369 (6)
C4—C5	1.390 (7)	C12—C13	1.377 (6)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.377 (7)	C13—C14	1.371 (6)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.514 (6)	C15—C16	1.490 (6)
C8—H8A	0.9600	C16—H16A	0.9600
C8—H8B	0.9600	C16—H16B	0.9600
C8—H8C	0.9600	C16—H16C	0.9600
C7—N1—C1	128.1 (4)	C15—N2—C9	127.6 (4)
C7—N1—H1N	116.0	C15—N2—H2N	116.2
C1—N1—H1N	116.0	C9—N2—H2N	116.2
C2—C1—N1	123.0 (4)	C10—C9—C14	119.1 (4)
C2—C1—C6	119.5 (5)	C10—C9—N2	123.7 (4)
N1—C1—C6	117.5 (4)	C14—C9—N2	117.2 (4)
C3—C2—C1	119.0 (5)	C11—C10—C9	118.9 (4)
C3—C2—H2	120.5	C11—C10—H10	120.5
C1—C2—H2	120.5	C9—C10—H10	120.5
C4—C3—C2	122.7 (5)	C12—C11—C10	122.5 (4)
C4—C3—Br1	119.1 (4)	C12—C11—Br2	118.5 (4)
C2—C3—Br1	118.2 (4)	C10—C11—Br2	119.0 (3)
C3—C4—C5	118.3 (5)	C11—C12—C13	118.4 (4)
C3—C4—H4	120.8	C11—C12—H12	120.8
C5—C4—H4	120.8	C13—C12—H12	120.8
C6—C5—C4	121.0 (5)	C14—C13—C12	120.4 (4)
C6—C5—H5	119.5	C14—C13—H13	119.8
C4—C5—H5	119.5	C12—C13—H13	119.8
C5—C6—C1	119.6 (5)	C13—C14—C9	120.6 (4)
C5—C6—H6	120.2	C13—C14—H14	119.7
C1—C6—H6	120.2	C9—C14—H14	119.7
O1—C7—N1	123.7 (4)	O2—C15—N2	122.2 (4)
O1—C7—C8	121.3 (4)	O2—C15—C16	122.3 (4)
N1—C7—C8	115.0 (4)	N2—C15—C16	115.5 (4)
C7—C8—H8A	109.5	C15—C16—H16A	109.5
C7—C8—H8B	109.5	C15—C16—H16B	109.5
H8A—C8—H8B	109.5	H16A—C16—H16B	109.5
C7—C8—H8C	109.5	C15—C16—H16C	109.5
H8A—C8—H8C	109.5	H16A—C16—H16C	109.5
H8B—C8—H8C	109.5	H16B—C16—H16C	109.5
C7—N1—C1—C2	−22.3 (7)	C15—N2—C9—C10	21.5 (6)
C7—N1—C1—C6	160.8 (4)	C15—N2—C9—C14	−160.2 (4)
N1—C1—C2—C3	−177.9 (4)	C14—C9—C10—C11	0.7 (6)
C6—C1—C2—C3	−1.0 (7)	N2—C9—C10—C11	178.9 (4)
C1—C2—C3—C4	0.4 (7)	C9—C10—C11—C12	−0.5 (7)
C1—C2—C3—Br1	177.6 (3)	C9—C10—C11—Br2	178.0 (3)
C2—C3—C4—C5	−0.4 (8)	C10—C11—C12—C13	0.7 (7)
Br1—C3—C4—C5	−177.6 (4)	Br2—C11—C12—C13	−177.8 (4)
C3—C4—C5—C6	1.0 (8)	C11—C12—C13—C14	−1.1 (7)
C4—C5—C6—C1	−1.7 (8)	C12—C13—C14—C9	1.2 (7)
C2—C1—C6—C5	1.7 (7)	C10—C9—C14—C13	−1.0 (6)
N1—C1—C6—C5	178.7 (4)	N2—C9—C14—C13	−179.4 (4)
C1—N1—C7—O1	−3.1 (8)	C9—N2—C15—O2	2.2 (7)
C1—N1—C7—C8	177.9 (4)	C9—N2—C15—C16	−179.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86	2.05	2.887 (5)	166
N2—H2N···O1	0.86	2.10	2.953 (5)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86	2.05	2.887 (5)	166
N2—H2N⋯O1	0.86	2.10	2.953 (5)	169

Symmetry code: (i) .