2-Bromo-N-(4-bromo­phen­yl)acetamide

Gowda, B.T.; Svoboda, I.; Foro, S.; Suchetan, P.A.; Fuess, H.

doi:10.1107/S1600536809028219

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1955

doi:10.1107/S1600536809028219

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2-Bromo-N-(4-bromophenyl)acetamide

B. Thimme Gowda,^a ^* Ingrid Svoboda,^b Sabine Foro,^b P. A. Suchetan ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 16 July 2009; accepted 17 July 2009; online 22 July 2009)

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 ). For related structures, see: Andreetti et al. (1968 ); Gowda et al. (2007a ,b ,c ).

Experimental

Crystal data

C₈H₇Br₂NO
M_r = 292.97
Monoclinic, P 2₁ /n
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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.127
S = 0.99
1661 reflections
109 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.86	2.11	2.925 (6)	157
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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 (Sheldrick, 2008).

Figures top

	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.

2-Bromo-N-(4-bromophenyl)acetamide top

Crystal data top

C₈H₇Br₂NO	F(000) = 560
M_r = 292.97	D_x = 2.081 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2250 reflections
a = 4.4987 (3) Å	θ = 2.9–27.8°
b = 23.152 (1) Å	µ = 8.62 mm⁻¹
c = 9.1098 (5) Å	T = 303 K
β = 99.713 (6)°	Needle, colourless
V = 935.22 (9) Å³	0.50 × 0.20 × 0.14 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1661 independent reflections
Radiation source: fine-focus sealed tube	1415 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Rotation method data acquisition using ω and ϕ scans	θ_max = 25.4°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −5→4
T_min = 0.078, T_max = 0.299	k = −16→27
3065 measured reflections	l = −10→9

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0581P)² + 4.1384P] where P = (F_o² + 2F_c²)/3
1661 reflections	(Δ/σ)_max = 0.001
109 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

C₈H₇Br₂NO	V = 935.22 (9) Å³
M_r = 292.97	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.4987 (3) Å	µ = 8.62 mm⁻¹
b = 23.152 (1) Å	T = 303 K
c = 9.1098 (5) Å	0.50 × 0.20 × 0.14 mm
β = 99.713 (6)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1661 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1415 reflections with I > 2σ(I)
T_min = 0.078, T_max = 0.299	R_int = 0.023
3065 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 0.99	Δρ_max = 0.73 e Å⁻³
1661 reflections	Δρ_min = −0.68 e Å⁻³
109 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
C1	0.7460 (14)	0.2109 (3)	0.3871 (6)	0.0489 (15)
H1A	0.6432	0.2287	0.4610	0.059*
H1B	0.9218	0.1909	0.4395	0.059*
C2	0.8475 (13)	0.2577 (3)	0.2905 (6)	0.0400 (13)
C3	1.1568 (13)	0.3474 (2)	0.3295 (6)	0.0388 (12)
C4	1.0573 (14)	0.3743 (3)	0.1927 (6)	0.0445 (14)
H4	0.9070	0.3573	0.1236	0.053*
C5	1.1831 (16)	0.4263 (3)	0.1603 (7)	0.0535 (16)
H5	1.1158	0.4444	0.0697	0.064*
C6	1.4056 (14)	0.4510 (3)	0.2609 (7)	0.0473 (15)
C7	1.5067 (15)	0.4251 (3)	0.3949 (7)	0.0538 (16)
H7	1.6576	0.4424	0.4631	0.065*
C8	1.3832 (14)	0.3731 (3)	0.4283 (7)	0.0476 (14)
H8	1.4542	0.3553	0.5189	0.057*
N1	1.0306 (11)	0.2954 (2)	0.3747 (5)	0.0397 (11)
H1N	1.0770	0.2870	0.4677	0.048*
O1	0.7725 (10)	0.26109 (19)	0.1567 (4)	0.0529 (11)
Br1	0.48101 (16)	0.15590 (3)	0.27451 (8)	0.0576 (3)
Br2	1.5669 (2)	0.52368 (3)	0.21830 (9)	0.0722 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.048 (3)	0.063 (4)	0.033 (3)	−0.015 (3)	0.000 (3)	−0.002 (3)
C2	0.038 (3)	0.044 (3)	0.038 (3)	0.007 (3)	0.007 (2)	−0.001 (3)
C3	0.044 (3)	0.037 (3)	0.037 (3)	0.004 (2)	0.012 (2)	−0.005 (2)
C4	0.053 (4)	0.050 (3)	0.029 (3)	0.004 (3)	0.004 (3)	0.003 (3)
C5	0.072 (4)	0.048 (4)	0.042 (3)	0.007 (3)	0.014 (3)	0.006 (3)
C6	0.058 (4)	0.038 (3)	0.053 (4)	−0.001 (3)	0.027 (3)	−0.003 (3)
C7	0.054 (4)	0.057 (4)	0.052 (4)	−0.012 (3)	0.012 (3)	−0.008 (3)
C8	0.048 (3)	0.052 (4)	0.041 (3)	−0.001 (3)	0.003 (3)	0.001 (3)
N1	0.051 (3)	0.039 (2)	0.028 (2)	−0.001 (2)	0.007 (2)	0.006 (2)
O1	0.072 (3)	0.054 (3)	0.030 (2)	−0.012 (2)	−0.001 (2)	−0.0005 (19)
Br1	0.0632 (5)	0.0541 (4)	0.0528 (4)	−0.0127 (3)	0.0024 (3)	−0.0073 (3)
Br2	0.1010 (7)	0.0456 (4)	0.0785 (6)	−0.0099 (4)	0.0392 (5)	−0.0006 (3)

Geometric parameters (Å, º) top

C1—C2	1.513 (8)	C4—H4	0.9300
C1—Br1	1.919 (6)	C5—C6	1.363 (9)
C1—H1A	0.9700	C5—H5	0.9300
C1—H1B	0.9700	C6—C7	1.367 (9)
C2—O1	1.211 (7)	C6—Br2	1.898 (6)
C2—N1	1.349 (7)	C7—C8	1.381 (9)
C3—C8	1.376 (8)	C7—H7	0.9300
C3—C4	1.398 (8)	C8—H8	0.9300
C3—N1	1.421 (7)	N1—H1N	0.8600
C4—C5	1.382 (9)

C2—C1—Br1	112.6 (4)	C6—C5—C4	120.2 (6)
C2—C1—H1A	109.1	C6—C5—H5	119.9
Br1—C1—H1A	109.1	C4—C5—H5	119.9
C2—C1—H1B	109.1	C5—C6—C7	120.8 (6)
Br1—C1—H1B	109.1	C5—C6—Br2	119.8 (5)
H1A—C1—H1B	107.8	C7—C6—Br2	119.3 (5)
O1—C2—N1	124.7 (6)	C6—C7—C8	119.6 (6)
O1—C2—C1	124.9 (5)	C6—C7—H7	120.2
N1—C2—C1	110.4 (5)	C8—C7—H7	120.2
C8—C3—C4	118.8 (6)	C3—C8—C7	120.9 (6)
C8—C3—N1	117.7 (5)	C3—C8—H8	119.6
C4—C3—N1	123.5 (5)	C7—C8—H8	119.6
C5—C4—C3	119.8 (6)	C2—N1—C3	128.3 (5)
C5—C4—H4	120.1	C2—N1—H1N	115.8
C3—C4—H4	120.1	C3—N1—H1N	115.8

Br1—C1—C2—O1	0.2 (8)	Br2—C6—C7—C8	178.0 (5)
Br1—C1—C2—N1	179.5 (4)	C4—C3—C8—C7	1.3 (9)
C8—C3—C4—C5	−1.2 (9)	N1—C3—C8—C7	−176.9 (6)
N1—C3—C4—C5	177.0 (5)	C6—C7—C8—C3	−0.9 (10)
C3—C4—C5—C6	0.6 (9)	O1—C2—N1—C3	4.1 (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—C8	0.4 (10)	C4—C3—N1—C2	14.3 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.11	2.925 (6)	157

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

Experimental details

Crystal data
Chemical formula	C₈H₇Br₂NO
M_r	292.97
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	303
a, b, c (Å)	4.4987 (3), 23.152 (1), 9.1098 (5)
β (°)	99.713 (6)
V (Å³)	935.22 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	8.62
Crystal size (mm)	0.50 × 0.20 × 0.14

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.078, 0.299
No. of measured, independent and observed [I > 2σ(I)] reflections	3065, 1661, 1415
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.127, 0.99
No. of reflections	1661
No. of parameters	109
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.68

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.11	2.925 (6)	157

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

Acknowledgements

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

References

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