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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1955.
Published online 2009 July 22. doi:  10.1107/S1600536809028219
PMCID: PMC2977473

2-Bromo-N-(4-bromo­phen­yl)acetamide

Abstract

In the title compound, C8H7Br2NO, the conformation of the N—H bond is anti to both the carbonyl and C—Br bonds in the side chain. In the crystal structure, mol­ecules are packed into supra­molecular chains along the c axis by N—H(...)O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 [triangle]). For related structures, see: Andreetti et al. (1968 [triangle]); Gowda et al. (2007a [triangle],b [triangle],c [triangle]).

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Object name is e-65-o1955-scheme1.jpg

Experimental

Crystal data

  • C8H7Br2NO
  • M r = 292.97
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1955-efi1.jpg
  • a = 4.4987 (3) Å
  • b = 23.152 (1) Å
  • c = 9.1098 (5) Å
  • β = 99.713 (6)°
  • V = 935.22 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 8.62 mm−1
  • T = 303 K
  • 0.50 × 0.20 × 0.14 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 [triangle]) T min = 0.078, T max = 0.299
  • 3065 measured reflections
  • 1661 independent reflections
  • 1415 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.127
  • S = 0.99
  • 1661 reflections
  • 109 parameters
  • H-atom parameters constrained
  • Δρmax = 0.73 e Å−3
  • Δρmin = −0.68 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028219/tk2505sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028219/tk2505Isup2.hkl

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

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

supplementary crystallographic information

Comment

As part of a study of the effect of the ring and the side chain substituents on the structures of N-aromatic amides (Gowda et al., 2007a, b, c), in the present work, the structure of 2-bromo-N-(4-bromophenyl)acetamide (I) has been determined (Fig. 1). The conformation of the N—H bond is anti to both the C=O and the C—Br bonds in the side chain, similar to that observed in 2-chloro-N-(4-chlorophenyl)acetamide (Gowda et al., 2007c), N-(4-bromophenyl)acetamide (Andreetti et al., 1968), and other amides (Gowda et al., 2007a, b).

The crystal packing shows N1—H1N···O1 hydrogen bonds (Table 1) that lead to the formation of molecular chain along the c-axis (Fig. 2).

Experimental

Compound (I) was prepared from 4-bromoaniline and bromoacetylchloride according to the literature method (Gowda et al., 2003). Single crystals were obtained by slow evaporation of an ethanolic solution of (I) held at room temperature.

Refinement

The H atoms were positioned with idealized geometry using a riding model [N—H = 0.86 Å, C—H = 0.93—0.97 Å], and were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

Figures

Fig. 1.
Molecular structure of (I), showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented as small spheres of arbitrary radii.
Fig. 2.
Molecular packing of (I) with hydrogen bonds shown as dashed lines.

Crystal data

C8H7Br2NOF(000) = 560
Mr = 292.97Dx = 2.081 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2250 reflections
a = 4.4987 (3) Åθ = 2.9–27.8°
b = 23.152 (1) ŵ = 8.62 mm1
c = 9.1098 (5) ÅT = 303 K
β = 99.713 (6)°Needle, colourless
V = 935.22 (9) Å30.50 × 0.20 × 0.14 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector1661 independent reflections
Radiation source: fine-focus sealed tube1415 reflections with I > 2σ(I)
graphiteRint = 0.023
Rotation method data acquisition using ω and [var phi] scansθmax = 25.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)h = −5→4
Tmin = 0.078, Tmax = 0.299k = −16→27
3065 measured reflectionsl = −10→9

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.0581P)2 + 4.1384P] where P = (Fo2 + 2Fc2)/3
1661 reflections(Δ/σ)max = 0.001
109 parametersΔρmax = 0.73 e Å3
0 restraintsΔρmin = −0.68 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.7460 (14)0.2109 (3)0.3871 (6)0.0489 (15)
H1A0.64320.22870.46100.059*
H1B0.92180.19090.43950.059*
C20.8475 (13)0.2577 (3)0.2905 (6)0.0400 (13)
C31.1568 (13)0.3474 (2)0.3295 (6)0.0388 (12)
C41.0573 (14)0.3743 (3)0.1927 (6)0.0445 (14)
H40.90700.35730.12360.053*
C51.1831 (16)0.4263 (3)0.1603 (7)0.0535 (16)
H51.11580.44440.06970.064*
C61.4056 (14)0.4510 (3)0.2609 (7)0.0473 (15)
C71.5067 (15)0.4251 (3)0.3949 (7)0.0538 (16)
H71.65760.44240.46310.065*
C81.3832 (14)0.3731 (3)0.4283 (7)0.0476 (14)
H81.45420.35530.51890.057*
N11.0306 (11)0.2954 (2)0.3747 (5)0.0397 (11)
H1N1.07700.28700.46770.048*
O10.7725 (10)0.26109 (19)0.1567 (4)0.0529 (11)
Br10.48101 (16)0.15590 (3)0.27451 (8)0.0576 (3)
Br21.5669 (2)0.52368 (3)0.21830 (9)0.0722 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.048 (3)0.063 (4)0.033 (3)−0.015 (3)0.000 (3)−0.002 (3)
C20.038 (3)0.044 (3)0.038 (3)0.007 (3)0.007 (2)−0.001 (3)
C30.044 (3)0.037 (3)0.037 (3)0.004 (2)0.012 (2)−0.005 (2)
C40.053 (4)0.050 (3)0.029 (3)0.004 (3)0.004 (3)0.003 (3)
C50.072 (4)0.048 (4)0.042 (3)0.007 (3)0.014 (3)0.006 (3)
C60.058 (4)0.038 (3)0.053 (4)−0.001 (3)0.027 (3)−0.003 (3)
C70.054 (4)0.057 (4)0.052 (4)−0.012 (3)0.012 (3)−0.008 (3)
C80.048 (3)0.052 (4)0.041 (3)−0.001 (3)0.003 (3)0.001 (3)
N10.051 (3)0.039 (2)0.028 (2)−0.001 (2)0.007 (2)0.006 (2)
O10.072 (3)0.054 (3)0.030 (2)−0.012 (2)−0.001 (2)−0.0005 (19)
Br10.0632 (5)0.0541 (4)0.0528 (4)−0.0127 (3)0.0024 (3)−0.0073 (3)
Br20.1010 (7)0.0456 (4)0.0785 (6)−0.0099 (4)0.0392 (5)−0.0006 (3)

Geometric parameters (Å, °)

C1—C21.513 (8)C4—H40.9300
C1—Br11.919 (6)C5—C61.363 (9)
C1—H1A0.9700C5—H50.9300
C1—H1B0.9700C6—C71.367 (9)
C2—O11.211 (7)C6—Br21.898 (6)
C2—N11.349 (7)C7—C81.381 (9)
C3—C81.376 (8)C7—H70.9300
C3—C41.398 (8)C8—H80.9300
C3—N11.421 (7)N1—H1N0.8600
C4—C51.382 (9)
C2—C1—Br1112.6 (4)C6—C5—C4120.2 (6)
C2—C1—H1A109.1C6—C5—H5119.9
Br1—C1—H1A109.1C4—C5—H5119.9
C2—C1—H1B109.1C5—C6—C7120.8 (6)
Br1—C1—H1B109.1C5—C6—Br2119.8 (5)
H1A—C1—H1B107.8C7—C6—Br2119.3 (5)
O1—C2—N1124.7 (6)C6—C7—C8119.6 (6)
O1—C2—C1124.9 (5)C6—C7—H7120.2
N1—C2—C1110.4 (5)C8—C7—H7120.2
C8—C3—C4118.8 (6)C3—C8—C7120.9 (6)
C8—C3—N1117.7 (5)C3—C8—H8119.6
C4—C3—N1123.5 (5)C7—C8—H8119.6
C5—C4—C3119.8 (6)C2—N1—C3128.3 (5)
C5—C4—H4120.1C2—N1—H1N115.8
C3—C4—H4120.1C3—N1—H1N115.8
Br1—C1—C2—O10.2 (8)Br2—C6—C7—C8178.0 (5)
Br1—C1—C2—N1179.5 (4)C4—C3—C8—C71.3 (9)
C8—C3—C4—C5−1.2 (9)N1—C3—C8—C7−176.9 (6)
N1—C3—C4—C5177.0 (5)C6—C7—C8—C3−0.9 (10)
C3—C4—C5—C60.6 (9)O1—C2—N1—C34.1 (9)
C4—C5—C6—C7−0.3 (10)C1—C2—N1—C3−175.1 (5)
C4—C5—C6—Br2−177.8 (5)C8—C3—N1—C2−167.5 (6)
C5—C6—C7—C80.4 (10)C4—C3—N1—C214.3 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.862.112.925 (6)157

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2505).

References

  • Andreetti, G. D., Cavalca, L., Domiano, P. & Musatti, A. (1968). Acta Cryst. B24, 1195–1198.
  • Gowda, B. T., Foro, S. & Fuess, H. (2007a). Acta Cryst. E63, o2333–o2334.
  • Gowda, B. T., Foro, S. & Fuess, H. (2007b). Acta Cryst. E63, o2335–o2336.
  • Gowda, B. T., Foro, S. & Fuess, H. (2007c). Acta Cryst. E63, o4488.
  • Gowda, B. T., Usha, K. M. & Jayalakshmi, K. L. (2003). Z. Naturforsch. Teil A, 58, 801–806.
  • Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Yarnton, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography